Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_section_title ;ENOLS AND THIOENOLS OF SUBSTITUTED CYANO MONOTHIOCARBONYLMALONAMIDES. STRUCTURES, ENOLIZATION VS. THIOENOLIZATION, EQUILIBRIA AND CONFORMATIONS ; _publ_contact_author_name 'Prof. Zvi Rappoport' _publ_contact_author_email ZR@VMS.HUJI.AC.IL loop_ _publ_author_name Z.Rappoport A.Basheer # Attachment '11j.cif' data_11j _database_code_depnum_ccdc_archive 'CCDC 667545' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O S' _chemical_formula_sum 'C15 H13 N3 O S' _chemical_formula_weight 283.34 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 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 4.9892(4) _cell_length_b 19.2928(14) _cell_length_c 14.7103(11) _cell_angle_alpha 90.00 _cell_angle_beta 99.0450(10) _cell_angle_gamma 90.00 _cell_volume 1398.34(18) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(1) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15798 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3056 _reflns_number_gt 1921 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 w=1/[\s^2^(Fo^2^)+(0.0348P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3056 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0979 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0865 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _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 0.5585(5) 0.53839(12) 0.65328(15) 0.0429(6) Uani 1 1 d . . . C2 C 0.4324(4) 0.59868(11) 0.61233(15) 0.0396(5) Uani 1 1 d . . . C3 C 0.5336(4) 0.66731(11) 0.62774(15) 0.0402(6) Uani 1 1 d . . . C4 C 0.1935(5) 0.58900(11) 0.54750(17) 0.0446(6) Uani 1 1 d . . . C5 C 0.5735(5) 0.41225(12) 0.67495(17) 0.0654(8) Uani 1 1 d . . . H5A H 0.7546 0.4076 0.6613 0.098 Uiso 1 1 calc R . . H5B H 0.4660 0.3736 0.6495 0.098 Uiso 1 1 calc R . . H5C H 0.5788 0.4133 0.7405 0.098 Uiso 1 1 calc R . . C6 C 0.4564(4) 0.79001(11) 0.58252(17) 0.0445(6) Uani 1 1 d . . . C7 C 0.3508(5) 0.83574(12) 0.63731(17) 0.0525(7) Uani 1 1 d . . . H7 H 0.2350 0.8202 0.6767 0.063 Uiso 1 1 calc R . . C8 C 0.4149(5) 0.90607(12) 0.63491(17) 0.0570(7) Uani 1 1 d . . . H8 H 0.3443 0.9371 0.6733 0.068 Uiso 1 1 calc R . . C9 C 0.5805(5) 0.92899(12) 0.57648(17) 0.0533(7) Uani 1 1 d . . . H9 H 0.6248 0.9758 0.5760 0.064 Uiso 1 1 calc R . . C10 C 0.6867(4) 0.88337(11) 0.51651(16) 0.0450(6) Uani 1 1 d . . . C11 C 0.8497(5) 0.90598(14) 0.45193(19) 0.0618(7) Uani 1 1 d . . . H11 H 0.8896 0.9529 0.4485 0.074 Uiso 1 1 calc R . . C12 C 0.9485(5) 0.86119(16) 0.39531(19) 0.0701(8) Uani 1 1 d . . . H12 H 1.0557 0.8774 0.3535 0.084 Uiso 1 1 calc R . . C13 C 0.8910(5) 0.79058(15) 0.39906(19) 0.0677(8) Uani 1 1 d . . . H13 H 0.9614 0.7599 0.3601 0.081 Uiso 1 1 calc R . . C14 C 0.7318(5) 0.76622(13) 0.45956(17) 0.0548(7) Uani 1 1 d . . . H14 H 0.6931 0.7191 0.4611 0.066 Uiso 1 1 calc R . . C15 C 0.6257(4) 0.81187(11) 0.51976(15) 0.0433(6) Uani 1 1 d . . . N1 N 0.4542(4) 0.47616(10) 0.63498(15) 0.0522(6) Uani 1 1 d . . . H1N1 H 0.303(4) 0.4733(11) 0.5961(15) 0.054(8) Uiso 1 1 d . . . N2 N 0.0021(4) 0.58234(10) 0.49364(14) 0.0608(6) Uani 1 1 d . . . N3 N 0.3825(4) 0.71846(10) 0.58388(16) 0.0525(6) Uani 1 1 d . . . H1N3 H 0.234(4) 0.7093(11) 0.5613(15) 0.045(7) Uiso 1 1 d . . . O1 O 0.7846(3) 0.53993(9) 0.71177(11) 0.0553(5) Uani 1 1 d . . . H1O H 0.845(5) 0.5883(14) 0.7156(17) 0.092(9) Uiso 1 1 d . . . S1 S 0.82752(12) 0.68746(3) 0.69709(4) 0.0509(2) 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 0.0400(14) 0.0466(15) 0.0426(14) -0.0015(12) 0.0079(11) -0.0061(11) C2 0.0343(12) 0.0395(14) 0.0448(14) -0.0003(11) 0.0052(10) -0.0050(10) C3 0.0362(12) 0.0438(14) 0.0431(14) 0.0020(11) 0.0136(11) -0.0030(11) C4 0.0460(15) 0.0323(13) 0.0563(16) 0.0002(11) 0.0110(13) -0.0053(11) C5 0.0815(19) 0.0450(16) 0.0661(18) 0.0056(14) 0.0001(15) -0.0017(14) C6 0.0357(13) 0.0376(14) 0.0572(16) 0.0030(12) -0.0017(12) -0.0062(11) C7 0.0471(15) 0.0518(16) 0.0589(17) 0.0015(13) 0.0094(13) -0.0042(12) C8 0.0631(16) 0.0467(16) 0.0606(18) -0.0077(13) 0.0077(14) 0.0041(13) C9 0.0562(16) 0.0352(14) 0.0634(18) 0.0005(13) -0.0063(14) -0.0071(12) C10 0.0401(13) 0.0420(14) 0.0500(15) 0.0053(12) -0.0024(11) -0.0068(11) C11 0.0622(17) 0.0570(17) 0.0644(19) 0.0119(15) 0.0039(15) -0.0121(14) C12 0.0680(19) 0.084(2) 0.0620(19) 0.0131(17) 0.0206(15) -0.0076(16) C13 0.0680(19) 0.076(2) 0.0608(19) -0.0096(15) 0.0152(15) 0.0016(15) C14 0.0508(15) 0.0520(16) 0.0599(18) -0.0026(13) 0.0032(13) -0.0051(12) C15 0.0363(12) 0.0429(14) 0.0484(15) -0.0032(12) -0.0004(11) -0.0051(11) N1 0.0517(14) 0.0426(13) 0.0585(15) 0.0022(11) -0.0033(12) -0.0036(11) N2 0.0542(13) 0.0497(13) 0.0729(16) -0.0055(11) -0.0077(12) -0.0054(11) N3 0.0329(12) 0.0436(13) 0.0776(16) 0.0029(11) -0.0016(12) -0.0093(10) O1 0.0518(11) 0.0464(11) 0.0621(12) 0.0064(9) -0.0081(9) -0.0056(8) S1 0.0422(4) 0.0512(4) 0.0570(4) -0.0005(3) 0.0011(3) -0.0116(3) _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 C1 O1 1.307(2) . ? C1 N1 1.319(3) . ? C1 C2 1.412(3) . ? C2 C4 1.417(3) . ? C2 C3 1.423(3) . ? C3 N3 1.344(3) . ? C3 S1 1.694(2) . ? C4 N2 1.148(3) . ? C5 N1 1.453(3) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.356(3) . ? C6 C15 1.410(3) . ? C6 N3 1.430(3) . ? C7 C8 1.396(3) . ? C7 H7 0.9300 . ? C8 C9 1.356(3) . ? C8 H8 0.9300 . ? C9 C10 1.407(3) . ? C9 H9 0.9300 . ? C10 C11 1.413(3) . ? C10 C15 1.415(3) . ? C11 C12 1.346(3) . ? C11 H11 0.9300 . ? C12 C13 1.395(4) . ? C12 H12 0.9300 . ? C13 C14 1.366(3) . ? C13 H13 0.9300 . ? C14 C15 1.410(3) . ? C14 H14 0.9300 . ? N1 H1N1 0.87(2) . ? N3 H1N3 0.78(2) . ? O1 H1O 0.98(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 O1 C1 N1 115.3(2) . . ? O1 C1 C2 122.9(2) . . ? N1 C1 C2 121.8(2) . . ? C1 C2 C4 116.7(2) . . ? C1 C2 C3 125.1(2) . . ? C4 C2 C3 118.0(2) . . ? N3 C3 C2 116.7(2) . . ? N3 C3 S1 119.20(17) . . ? C2 C3 S1 124.15(17) . . ? N2 C4 C2 178.4(3) . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C15 121.5(2) . . ? C7 C6 N3 119.6(2) . . ? C15 C6 N3 118.7(2) . . ? C6 C7 C8 120.4(2) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 119.9(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 121.3(2) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C9 C10 C11 122.8(2) . . ? C9 C10 C15 119.0(2) . . ? C11 C10 C15 118.2(2) . . ? C12 C11 C10 121.6(3) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C13 120.3(3) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 120.6(2) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C6 123.2(2) . . ? C14 C15 C10 118.9(2) . . ? C6 C15 C10 117.9(2) . . ? C1 N1 C5 124.5(2) . . ? C1 N1 H1N1 117.6(14) . . ? C5 N1 H1N1 117.9(14) . . ? C3 N3 C6 126.1(2) . . ? C3 N3 H1N3 117.4(16) . . ? C6 N3 H1N3 116.2(16) . . ? C1 O1 H1O 106.6(15) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O S1 0.98(3) 1.93(3) 2.8651(18) 158(2) . N1 H1N1 N2 0.87(2) 2.14(2) 2.947(3) 153.3(19) 3_566 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.262 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.038 # Attachment '12d.cif' data_12d _database_code_depnum_ccdc_archive 'CCDC 667546' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H11 N3 O S' _chemical_formula_sum 'C7 H11 N3 O S' _chemical_formula_weight 185.25 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)/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 14.6537(11) _cell_length_b 14.1922(11) _cell_length_c 14.9966(12) _cell_angle_alpha 90.00 _cell_angle_beta 108.8310(10) _cell_angle_gamma 90.00 _cell_volume 2951.9(4) _cell_formula_units_Z 12 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description shapeless _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.289 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9365 _exptl_absorpt_correction_T_max 0.9662 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(1) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29673 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.0527 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5779 _reflns_number_gt 4178 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 w=1/[\s^2^(Fo^2^)+(0.0756P)^2^+2.1955P] 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 5779 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1425 _refine_ls_R_factor_gt 0.1047 _refine_ls_wR_factor_ref 0.2133 _refine_ls_wR_factor_gt 0.1972 _refine_ls_goodness_of_fit_ref 1.245 _refine_ls_restrained_S_all 1.245 _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 0.2750(3) 0.2587(3) 0.0198(3) 0.0373(10) Uani 1 1 d . . . C2 C 0.2175(3) 0.2480(3) 0.0885(3) 0.0359(10) Uani 1 1 d . . . H2 H 0.1493 0.2600 0.0543 0.043 Uiso 1 1 calc R . . C3 C 0.2517(3) 0.3182(3) 0.1708(3) 0.0357(10) Uani 1 1 d . . . C4 C 0.2271(3) 0.1522(4) 0.1254(3) 0.0460(11) Uani 1 1 d . . . C5 C 0.1994(4) 0.4189(4) 0.2760(3) 0.0572(13) Uani 1 1 d . . . H5A H 0.2366 0.3897 0.3341 0.086 Uiso 1 1 calc R . . H5B H 0.1386 0.4393 0.2806 0.086 Uiso 1 1 calc R . . H5C H 0.2339 0.4723 0.2638 0.086 Uiso 1 1 calc R . . C6 C 0.1857(4) 0.4047(4) -0.0369(4) 0.0776(18) Uani 1 1 d . . . H6A H 0.1471 0.3844 0.0004 0.116 Uiso 1 1 calc R . . H6B H 0.1450 0.4157 -0.1005 0.116 Uiso 1 1 calc R . . H6C H 0.2186 0.4620 -0.0112 0.116 Uiso 1 1 calc R . . C7 C 0.3130(5) 0.3482(5) -0.0982(4) 0.088(2) Uani 1 1 d . . . H7A H 0.3605 0.3960 -0.0717 0.132 Uiso 1 1 calc R . . H7B H 0.2717 0.3684 -0.1589 0.132 Uiso 1 1 calc R . . H7C H 0.3447 0.2907 -0.1049 0.132 Uiso 1 1 calc R . . N1 N 0.2558(3) 0.3324(3) -0.0363(3) 0.0528(10) Uani 1 1 d . . . N2 N 0.2311(4) 0.0794(3) 0.1567(3) 0.0729(14) Uani 1 1 d . . . N3 N 0.1830(3) 0.3518(3) 0.1998(3) 0.0422(9) Uani 1 1 d . . . H3N H 0.128(4) 0.339(3) 0.169(3) 0.055(16) Uiso 1 1 d . . . O1 O 0.3349(2) 0.1977(2) 0.0191(2) 0.0495(8) Uani 1 1 d . . . S1 S 0.36660(8) 0.34463(11) 0.21812(10) 0.0635(4) Uani 1 1 d . . . C1' C 0.5983(3) 0.2262(3) 0.2627(3) 0.0360(10) Uani 1 1 d . . . C2' C 0.5545(3) 0.2488(3) 0.1573(3) 0.0314(9) Uani 1 1 d . . . H2' H 0.4845 0.2405 0.1386 0.038 Uiso 1 1 calc R . . C3' C 0.5943(3) 0.1842(3) 0.0959(3) 0.0350(10) Uani 1 1 d . . . C4' C 0.5752(3) 0.3465(4) 0.1392(3) 0.0448(11) Uani 1 1 d . . . C5' C 0.5511(4) 0.0933(4) -0.0490(3) 0.0592(14) Uani 1 1 d . . . H5'1 H 0.5902 0.1279 -0.0781 0.089 Uiso 1 1 calc R . . H5'2 H 0.4925 0.0739 -0.0963 0.089 Uiso 1 1 calc R . . H5'3 H 0.5857 0.0387 -0.0180 0.089 Uiso 1 1 calc R . . C6' C 0.4911(4) 0.0876(4) 0.2379(3) 0.0606(14) Uani 1 1 d . . . H6'1 H 0.4566 0.1178 0.1795 0.091 Uiso 1 1 calc R . . H6'2 H 0.4472 0.0726 0.2715 0.091 Uiso 1 1 calc R . . H6'3 H 0.5203 0.0307 0.2253 0.091 Uiso 1 1 calc R . . C7' C 0.6085(4) 0.1255(4) 0.3940(3) 0.0709(16) Uani 1 1 d . . . H7'1 H 0.6699 0.0959 0.4037 0.106 Uiso 1 1 calc R . . H7'2 H 0.5665 0.0827 0.4115 0.106 Uiso 1 1 calc R . . H7'3 H 0.6172 0.1813 0.4320 0.106 Uiso 1 1 calc R . . N1' N 0.5660(3) 0.1509(3) 0.2948(2) 0.0425(9) Uani 1 1 d . . . N2' N 0.5899(4) 0.4212(3) 0.1213(3) 0.0719(14) Uani 1 1 d . . . N3' N 0.5281(3) 0.1529(3) 0.0196(2) 0.0413(9) Uani 1 1 d . . . H3N' H 0.469(3) 0.170(3) 0.009(3) 0.043(13) Uiso 1 1 d . . . O1' O 0.6614(2) 0.2785(2) 0.3127(2) 0.0501(8) Uani 1 1 d . . . S1' S 0.71012(9) 0.16277(11) 0.12597(10) 0.0671(5) Uani 1 1 d . . . C1" C 0.9415(3) 0.2716(3) 0.5371(3) 0.0382(10) Uani 1 1 d . . . C2" C 0.8818(3) 0.2484(3) 0.4352(3) 0.0465(12) Uani 1 1 d . . . H2" H 0.8140 0.2625 0.4263 0.056 Uiso 1 1 calc R . . C3" C 0.9134(3) 0.3050(3) 0.3627(3) 0.0388(10) Uani 1 1 d . . . C4" C 0.8905(4) 0.1483(4) 0.4165(4) 0.0696(17) Uani 1 1 d . . . C5" C 0.8540(4) 0.3883(4) 0.2129(3) 0.0600(14) Uani 1 1 d . . . H5"1 H 0.8746 0.4510 0.2340 0.090 Uiso 1 1 calc R . . H5"2 H 0.7938 0.3910 0.1625 0.090 Uiso 1 1 calc R . . H5"3 H 0.9017 0.3585 0.1911 0.090 Uiso 1 1 calc R . . C6" C 0.8705(4) 0.4310(4) 0.5137(4) 0.0639(15) Uani 1 1 d . . . H6"1 H 0.9109 0.4702 0.4901 0.096 Uiso 1 1 calc R . . H6"2 H 0.8429 0.4680 0.5521 0.096 Uiso 1 1 calc R . . H6"3 H 0.8198 0.4048 0.4618 0.096 Uiso 1 1 calc R . . C7" C 0.9815(4) 0.3777(4) 0.6677(4) 0.0738(16) Uani 1 1 d . . . H7"1 H 1.0110 0.3217 0.7002 0.111 Uiso 1 1 calc R . . H7"2 H 0.9382 0.4034 0.6977 0.111 Uiso 1 1 calc R . . H7"3 H 1.0305 0.4232 0.6694 0.111 Uiso 1 1 calc R . . N1" N 0.9280(3) 0.3547(3) 0.5701(3) 0.0490(10) Uani 1 1 d . . . N2" N 0.8956(5) 0.0714(4) 0.4008(4) 0.119(2) Uani 1 1 d . . . N3" N 0.8417(3) 0.3343(3) 0.2903(3) 0.0474(10) Uani 1 1 d . . . H3N" H 0.784(4) 0.322(3) 0.290(4) 0.066(17) Uiso 1 1 d . . . O1" O 0.9959(2) 0.2108(2) 0.5842(2) 0.0513(8) Uani 1 1 d . . . S1" S 1.02885(9) 0.32335(10) 0.37913(9) 0.0600(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 0.035(2) 0.047(3) 0.026(2) -0.003(2) 0.0046(17) -0.006(2) C2 0.025(2) 0.048(3) 0.030(2) -0.0080(19) 0.0018(16) -0.0070(18) C3 0.037(2) 0.041(3) 0.031(2) 0.0004(18) 0.0145(18) -0.0040(19) C4 0.051(3) 0.047(3) 0.040(3) -0.009(2) 0.015(2) -0.015(2) C5 0.058(3) 0.063(3) 0.059(3) -0.016(3) 0.030(3) -0.002(3) C6 0.102(5) 0.055(4) 0.071(4) 0.020(3) 0.021(4) 0.013(3) C7 0.123(6) 0.093(5) 0.065(4) 0.012(3) 0.053(4) -0.012(4) N1 0.070(3) 0.050(3) 0.040(2) 0.0033(19) 0.020(2) -0.005(2) N2 0.094(4) 0.057(3) 0.063(3) -0.001(2) 0.019(3) -0.023(3) N3 0.035(2) 0.048(2) 0.045(2) -0.0096(18) 0.0138(18) -0.0054(18) O1 0.0460(18) 0.063(2) 0.0425(18) -0.0071(15) 0.0189(15) 0.0022(16) S1 0.0337(6) 0.0903(11) 0.0678(9) -0.0442(8) 0.0180(6) -0.0164(6) C1' 0.031(2) 0.051(3) 0.028(2) -0.007(2) 0.0121(18) 0.0045(19) C2' 0.029(2) 0.035(2) 0.031(2) -0.0026(17) 0.0098(16) 0.0036(17) C3' 0.045(2) 0.030(2) 0.033(2) 0.0027(18) 0.0158(19) 0.0024(18) C4' 0.053(3) 0.044(3) 0.039(2) -0.004(2) 0.017(2) 0.010(2) C5' 0.078(4) 0.063(3) 0.041(3) -0.018(2) 0.027(3) -0.009(3) C6' 0.074(4) 0.055(3) 0.053(3) 0.000(3) 0.020(3) -0.016(3) C7' 0.081(4) 0.090(4) 0.039(3) 0.015(3) 0.017(3) -0.001(3) N1' 0.043(2) 0.051(2) 0.0345(19) 0.0071(17) 0.0134(16) 0.0019(18) N2' 0.102(4) 0.041(3) 0.081(3) 0.002(2) 0.042(3) 0.004(3) N3' 0.045(2) 0.048(2) 0.032(2) -0.0064(17) 0.0126(18) -0.0024(19) O1' 0.0440(18) 0.072(2) 0.0324(16) -0.0088(16) 0.0098(14) -0.0109(17) S1' 0.0433(7) 0.0896(11) 0.0645(9) -0.0269(8) 0.0121(6) 0.0198(7) C1" 0.029(2) 0.048(3) 0.040(2) 0.009(2) 0.0136(19) -0.004(2) C2" 0.033(2) 0.050(3) 0.049(3) 0.013(2) 0.004(2) -0.009(2) C3" 0.043(2) 0.037(2) 0.035(2) 0.0022(19) 0.009(2) -0.0027(19) C4" 0.085(4) 0.052(4) 0.056(3) 0.003(3) 0.001(3) -0.027(3) C5" 0.065(3) 0.068(4) 0.045(3) 0.017(3) 0.016(3) -0.002(3) C6" 0.076(4) 0.055(3) 0.074(4) 0.019(3) 0.042(3) 0.016(3) C7" 0.077(4) 0.085(4) 0.057(3) -0.013(3) 0.019(3) 0.001(3) N1" 0.046(2) 0.059(3) 0.046(2) 0.004(2) 0.0188(18) 0.0028(19) N2" 0.170(7) 0.056(4) 0.101(5) -0.003(3) 0.002(4) -0.029(4) N3" 0.043(2) 0.053(3) 0.042(2) 0.0074(18) 0.0078(19) -0.006(2) O1" 0.0418(18) 0.063(2) 0.0442(18) 0.0177(16) 0.0064(14) 0.0100(16) S1" 0.0384(7) 0.0869(11) 0.0532(8) 0.0184(7) 0.0126(6) -0.0090(6) _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 C1 O1 1.236(5) . ? C1 N1 1.315(5) . ? C1 C2 1.535(6) . ? C2 C4 1.456(7) . ? C2 C3 1.540(5) . ? C2 H2 0.9800 . ? C3 N3 1.308(5) . ? C3 S1 1.646(4) . ? C4 N2 1.129(6) . ? C5 N3 1.447(6) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N1 1.450(7) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N1 1.456(7) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? N3 H3N 0.81(5) . ? O1 H3N' 2.06(5) . ? C1' O1' 1.232(5) . ? C1' N1' 1.322(5) . ? C1' C2' 1.536(5) . ? C2' C4' 1.462(6) . ? C2' C3' 1.540(5) . ? C2' H2' 0.9800 . ? C3' N3' 1.317(5) . ? C3' S1' 1.638(4) . ? C4' N2' 1.133(6) . ? C5' N3' 1.453(6) . ? C5' H5'1 0.9600 . ? C5' H5'2 0.9600 . ? C5' H5'3 0.9600 . ? C6' N1' 1.461(6) . ? C6' H6'1 0.9600 . ? C6' H6'2 0.9600 . ? C6' H6'3 0.9600 . ? C7' N1' 1.459(6) . ? C7' H7'1 0.9600 . ? C7' H7'2 0.9600 . ? C7' H7'3 0.9600 . ? N3' H3N' 0.86(4) . ? O1' H3N" 2.03(5) . ? C1" O1" 1.230(5) . ? C1" N1" 1.319(6) . ? C1" C2" 1.532(6) . ? C2" C4" 1.462(8) . ? C2" C3" 1.539(6) . ? C2" H2" 0.9800 . ? C3" N3" 1.311(5) . ? C3" S1" 1.650(4) . ? C4" N2" 1.124(7) . ? C5" N3" 1.448(6) . ? C5" H5"1 0.9600 . ? C5" H5"2 0.9600 . ? C5" H5"3 0.9600 . ? C6" N1" 1.462(6) . ? C6" H6"1 0.9600 . ? C6" H6"2 0.9600 . ? C6" H6"3 0.9600 . ? C7" N1" 1.456(6) . ? C7" H7"1 0.9600 . ? C7" H7"2 0.9600 . ? C7" H7"3 0.9600 . ? N3" H3N" 0.87(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 O1 C1 N1 123.9(4) . . ? O1 C1 C2 118.8(4) . . ? N1 C1 C2 117.3(4) . . ? C4 C2 C1 109.9(4) . . ? C4 C2 C3 109.5(3) . . ? C1 C2 C3 111.6(3) . . ? C4 C2 H2 108.6 . . ? C1 C2 H2 108.6 . . ? C3 C2 H2 108.6 . . ? N3 C3 C2 114.6(4) . . ? N3 C3 S1 124.4(3) . . ? C2 C3 S1 121.0(3) . . ? N2 C4 C2 176.1(5) . . ? N3 C5 H5A 109.5 . . ? N3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 N1 C6 124.9(4) . . ? C1 N1 C7 118.8(4) . . ? C6 N1 C7 116.1(4) . . ? C3 N3 C5 123.5(4) . . ? C3 N3 H3N 117(4) . . ? C5 N3 H3N 119(4) . . ? C1 O1 H3N' 146.3(12) . . ? O1' C1' N1' 123.5(4) . . ? O1' C1' C2' 118.8(4) . . ? N1' C1' C2' 117.6(4) . . ? C4' C2' C1' 110.3(3) . . ? C4' C2' C3' 108.2(3) . . ? C1' C2' C3' 112.2(3) . . ? C4' C2' H2' 108.7 . . ? C1' C2' H2' 108.7 . . ? C3' C2' H2' 108.7 . . ? N3' C3' C2' 113.9(4) . . ? N3' C3' S1' 125.7(3) . . ? C2' C3' S1' 120.3(3) . . ? N2' C4' C2' 177.1(5) . . ? N3' C5' H5'1 109.5 . . ? N3' C5' H5'2 109.5 . . ? H5'1 C5' H5'2 109.5 . . ? N3' C5' H5'3 109.5 . . ? H5'1 C5' H5'3 109.5 . . ? H5'2 C5' H5'3 109.5 . . ? N1' C6' H6'1 109.5 . . ? N1' C6' H6'2 109.5 . . ? H6'1 C6' H6'2 109.5 . . ? N1' C6' H6'3 109.5 . . ? H6'1 C6' H6'3 109.5 . . ? H6'2 C6' H6'3 109.5 . . ? N1' C7' H7'1 109.5 . . ? N1' C7' H7'2 109.5 . . ? H7'1 C7' H7'2 109.5 . . ? N1' C7' H7'3 109.5 . . ? H7'1 C7' H7'3 109.5 . . ? H7'2 C7' H7'3 109.5 . . ? C1' N1' C7' 119.0(4) . . ? C1' N1' C6' 125.1(4) . . ? C7' N1' C6' 115.9(4) . . ? C3' N3' C5' 122.5(4) . . ? C3' N3' H3N' 118(3) . . ? C5' N3' H3N' 119(3) . . ? C1' O1' H3N" 127.8(15) . . ? O1" C1" N1" 124.0(4) . . ? O1" C1" C2" 118.6(4) . . ? N1" C1" C2" 117.4(4) . . ? C4" C2" C1" 110.0(4) . . ? C4" C2" C3" 107.9(4) . . ? C1" C2" C3" 112.8(3) . . ? C4" C2" H2" 108.7 . . ? C1" C2" H2" 108.7 . . ? C3" C2" H2" 108.7 . . ? N3" C3" C2" 114.1(4) . . ? N3" C3" S1" 125.6(3) . . ? C2" C3" S1" 120.3(3) . . ? N2" C4" C2" 178.7(7) . . ? N3" C5" H5"1 109.5 . . ? N3" C5" H5"2 109.5 . . ? H5"1 C5" H5"2 109.5 . . ? N3" C5" H5"3 109.5 . . ? H5"1 C5" H5"3 109.5 . . ? H5"2 C5" H5"3 109.5 . . ? N1" C6" H6"1 109.5 . . ? N1" C6" H6"2 109.5 . . ? H6"1 C6" H6"2 109.5 . . ? N1" C6" H6"3 109.5 . . ? H6"1 C6" H6"3 109.5 . . ? H6"2 C6" H6"3 109.5 . . ? N1" C7" H7"1 109.5 . . ? N1" C7" H7"2 109.5 . . ? H7"1 C7" H7"2 109.5 . . ? N1" C7" H7"3 109.5 . . ? H7"1 C7" H7"3 109.5 . . ? H7"2 C7" H7"3 109.5 . . ? C1" N1" C7" 118.7(4) . . ? C1" N1" C6" 125.0(4) . . ? C7" N1" C6" 116.0(4) . . ? C3" N3" C5" 123.9(4) . . ? C3" N3" H3N" 117(4) . . ? C5" N3" H3N" 119(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3" H3N" O1' 0.87(5) 2.03(5) 2.881(5) 169(5) . N3' H3N' O1 0.86(4) 2.06(5) 2.898(5) 165(4) . N3 H3N O1" 0.81(5) 2.07(5) 2.871(5) 172(5) 4_465 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.372 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.067 # Attachment '11i.cif' data_11i _database_code_depnum_ccdc_archive 'CCDC 667547' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 N3 O2 S' _chemical_formula_sum 'C12 H13 N3 O2 S' _chemical_formula_weight 263.31 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)/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 10.5904(6) _cell_length_b 26.0342(14) _cell_length_c 9.6563(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.0470(10) _cell_angle_gamma 90.00 _cell_volume 2629.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour light _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.244 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(1) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30522 _diffrn_reflns_av_R_equivalents 0.0845 _diffrn_reflns_av_sigmaI/netI 0.0815 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.97 _reflns_number_total 6255 _reflns_number_gt 3191 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. The methyl H-atom coordinates of C5 and C17 were derived with "HFIX 137" of the SHELXTL program. The positions of these H-atoms may not be totally reliable. ; _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^)+(0.0402P)^2^+1.6336P] 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 6255 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1764 _refine_ls_R_factor_gt 0.0883 _refine_ls_wR_factor_ref 0.1644 _refine_ls_wR_factor_gt 0.1344 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.9448(3) 0.37468(15) 0.5382(4) 0.0523(9) Uani 1 1 d . . . C2 C 0.8659(3) 0.39346(13) 0.4156(3) 0.0446(8) Uani 1 1 d . . . C3 C 0.7858(3) 0.36235(13) 0.3165(4) 0.0467(8) Uani 1 1 d . . . C4 C 0.8662(3) 0.44683(15) 0.3960(4) 0.0536(10) Uani 1 1 d . . . C5 C 1.0979(4) 0.38743(16) 0.7532(4) 0.0764(13) Uani 1 1 d . . . H5A H 1.1582 0.3625 0.7303 0.115 Uiso 1 1 calc R . . H5B H 1.0447 0.3721 0.8136 0.115 Uiso 1 1 calc R . . H5C H 1.1430 0.4161 0.8000 0.115 Uiso 1 1 calc R . . C6 C 0.6209(3) 0.36303(13) 0.1036(4) 0.0476(9) Uani 1 1 d . . . C7 C 0.6662(4) 0.33245(15) 0.0069(4) 0.0653(11) Uani 1 1 d . . . H7 H 0.7538 0.3271 0.0131 0.078 Uiso 1 1 calc R . . C8 C 0.5831(4) 0.30954(15) -0.0997(4) 0.0687(12) Uani 1 1 d . . . H8 H 0.6147 0.2888 -0.1648 0.082 Uiso 1 1 calc R . . C9 C 0.4546(4) 0.31738(14) -0.1098(4) 0.0560(10) Uani 1 1 d . . . C10 C 0.4093(3) 0.34953(14) -0.0148(4) 0.0570(10) Uani 1 1 d . . . H10 H 0.3221 0.3560 -0.0233 0.068 Uiso 1 1 calc R . . C11 C 0.4922(3) 0.37201(13) 0.0922(4) 0.0534(9) Uani 1 1 d . . . H11 H 0.4609 0.3932 0.1565 0.064 Uiso 1 1 calc R . . C12 C 0.4093(4) 0.25737(17) -0.2972(5) 0.0931(16) Uani 1 1 d . . . H12A H 0.4495 0.2301 -0.2396 0.140 Uiso 1 1 calc R . . H12B H 0.4701 0.2725 -0.3492 0.140 Uiso 1 1 calc R . . H12C H 0.3385 0.2439 -0.3612 0.140 Uiso 1 1 calc R . . C13 C 0.3421(4) 0.56329(15) 0.2221(4) 0.0573(10) Uani 1 1 d . . . C14 C 0.4738(3) 0.55835(14) 0.2785(4) 0.0525(9) Uani 1 1 d . . . C15 C 0.5346(4) 0.58351(15) 0.4037(4) 0.0569(10) Uani 1 1 d . . . C16 C 0.5488(4) 0.52743(15) 0.2051(4) 0.0536(10) Uani 1 1 d . . . C17 C 0.1584(4) 0.54544(17) 0.0421(4) 0.0767(13) Uani 1 1 d . . . H17A H 0.1049 0.5337 0.1073 0.115 Uiso 1 1 calc R . . H17B H 0.1420 0.5252 -0.0419 0.115 Uiso 1 1 calc R . . H17C H 0.1400 0.5809 0.0198 0.115 Uiso 1 1 calc R . . C18 C 0.7347(3) 0.59614(15) 0.5683(4) 0.0509(9) Uani 1 1 d . . . C19 C 0.7635(4) 0.64739(16) 0.5735(4) 0.0646(11) Uani 1 1 d . . . H19 H 0.7342 0.6681 0.4967 0.078 Uiso 1 1 calc R . . C20 C 0.8353(4) 0.66884(15) 0.6907(4) 0.0635(11) Uani 1 1 d . . . H20 H 0.8538 0.7038 0.6933 0.076 Uiso 1 1 calc R . . C21 C 0.8789(3) 0.63842(15) 0.8027(4) 0.0561(10) Uani 1 1 d . . . C22 C 0.8529(4) 0.58722(17) 0.7974(4) 0.0775(13) Uani 1 1 d . . . H22 H 0.8839 0.5665 0.8735 0.093 Uiso 1 1 calc R . . C23 C 0.7810(4) 0.56580(15) 0.6798(4) 0.0698(12) Uani 1 1 d . . . H23 H 0.7641 0.5307 0.6768 0.084 Uiso 1 1 calc R . . C24 C 0.9708(4) 0.70853(16) 0.9437(5) 0.0896(15) Uani 1 1 d . . . H24A H 1.0180 0.7210 0.8735 0.134 Uiso 1 1 calc R . . H24B H 1.0184 0.7150 1.0351 0.134 Uiso 1 1 calc R . . H24C H 0.8899 0.7259 0.9346 0.134 Uiso 1 1 calc R . . N1 N 1.0183(3) 0.40514(15) 0.6246(3) 0.0550(8) Uani 1 1 d . . . H1N1 H 1.024(3) 0.4359(13) 0.605(4) 0.055(12) Uiso 1 1 d . . . N2 N 0.8671(3) 0.49056(13) 0.3787(4) 0.0806(11) Uani 1 1 d . . . N3 N 0.7081(3) 0.38688(13) 0.2138(3) 0.0530(8) Uani 1 1 d . . . H1N3 H 0.701(4) 0.4188(15) 0.221(4) 0.073(14) Uiso 1 1 d . . . N4 N 0.2925(3) 0.54015(13) 0.1049(4) 0.0602(9) Uani 1 1 d . . . H1N4 H 0.343(4) 0.5249(14) 0.055(4) 0.065(14) Uiso 1 1 d . . . N5 N 0.6113(3) 0.50246(14) 0.1451(4) 0.0761(11) Uani 1 1 d . . . N6 N 0.6590(3) 0.57386(14) 0.4462(3) 0.0589(9) Uani 1 1 d . . . H1N6 H 0.694(3) 0.5510(13) 0.411(4) 0.055(12) Uiso 1 1 d . . . O1 O 0.9471(3) 0.32647(11) 0.5741(3) 0.0741(8) Uani 1 1 d . . . H1O1 H 0.880(4) 0.3062(16) 0.481(5) 0.113(15) Uiso 1 1 d . . . O2 O 0.3645(3) 0.29559(11) -0.2104(3) 0.0787(9) Uani 1 1 d . . . O3 O 0.2627(3) 0.59010(13) 0.2819(3) 0.0846(10) Uani 1 1 d . . . H1O3 H 0.324(5) 0.6096(18) 0.376(5) 0.134(18) Uiso 1 1 d . . . O4 O 0.9504(3) 0.65531(11) 0.9258(3) 0.0811(9) Uani 1 1 d . . . S1 S 0.78247(11) 0.29769(4) 0.32570(13) 0.0767(4) Uani 1 1 d . . . S2 S 0.45606(11) 0.62385(6) 0.49878(13) 0.0953(5) 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 0.047(2) 0.055(2) 0.055(2) 0.004(2) 0.0081(18) 0.0018(19) C2 0.0408(19) 0.041(2) 0.050(2) 0.0035(16) 0.0014(16) 0.0037(16) C3 0.0403(19) 0.047(2) 0.052(2) 0.0038(17) 0.0056(16) 0.0021(17) C4 0.048(2) 0.051(2) 0.053(2) -0.0016(19) -0.0157(17) 0.0025(19) C5 0.077(3) 0.091(3) 0.055(2) 0.009(2) -0.009(2) 0.004(2) C6 0.047(2) 0.044(2) 0.050(2) -0.0025(17) 0.0014(17) 0.0024(17) C7 0.049(2) 0.070(3) 0.074(3) -0.015(2) -0.002(2) 0.011(2) C8 0.060(3) 0.065(3) 0.075(3) -0.028(2) -0.007(2) 0.018(2) C9 0.055(2) 0.048(2) 0.059(2) -0.0023(19) -0.012(2) 0.0051(19) C10 0.042(2) 0.063(2) 0.063(2) 0.004(2) -0.0026(19) 0.0099(19) C11 0.051(2) 0.053(2) 0.054(2) -0.0012(18) 0.0019(18) 0.0133(18) C12 0.091(3) 0.079(3) 0.096(4) -0.038(3) -0.025(3) 0.006(3) C13 0.054(2) 0.069(3) 0.050(2) 0.000(2) 0.011(2) -0.008(2) C14 0.049(2) 0.064(2) 0.044(2) -0.0057(18) 0.0054(18) -0.0029(19) C15 0.052(2) 0.075(3) 0.046(2) -0.0051(19) 0.0122(18) -0.006(2) C16 0.053(2) 0.053(2) 0.048(2) -0.0045(19) -0.0122(19) 0.0028(19) C17 0.054(3) 0.096(3) 0.074(3) -0.001(2) -0.009(2) -0.010(2) C18 0.050(2) 0.059(2) 0.042(2) -0.0081(18) 0.0028(17) -0.0001(18) C19 0.071(3) 0.057(3) 0.061(3) 0.006(2) -0.003(2) 0.005(2) C20 0.073(3) 0.047(2) 0.068(3) -0.003(2) 0.002(2) -0.006(2) C21 0.057(2) 0.054(2) 0.056(2) -0.004(2) 0.0043(19) -0.0049(19) C22 0.100(3) 0.065(3) 0.058(3) 0.012(2) -0.019(2) -0.012(3) C23 0.090(3) 0.048(2) 0.064(3) 0.003(2) -0.010(2) -0.016(2) C24 0.083(3) 0.077(3) 0.101(4) -0.037(3) -0.012(3) -0.002(3) N1 0.052(2) 0.057(2) 0.053(2) 0.0053(18) -0.0010(15) 0.0049(18) N2 0.090(3) 0.047(2) 0.089(3) -0.0048(19) -0.035(2) 0.0044(19) N3 0.0523(19) 0.044(2) 0.058(2) -0.0069(16) -0.0050(15) 0.0044(16) N4 0.052(2) 0.069(2) 0.056(2) -0.0034(18) -0.0021(18) -0.0063(18) N5 0.072(2) 0.078(3) 0.069(2) -0.0273(19) -0.0186(19) 0.024(2) N6 0.055(2) 0.070(2) 0.051(2) -0.0148(18) 0.0040(17) 0.0057(18) O1 0.081(2) 0.0530(17) 0.080(2) 0.0214(15) -0.0129(16) -0.0058(15) O2 0.0644(18) 0.076(2) 0.085(2) -0.0219(17) -0.0206(16) 0.0098(15) O3 0.0476(17) 0.137(3) 0.070(2) -0.0279(19) 0.0142(15) -0.0024(18) O4 0.096(2) 0.073(2) 0.0651(18) -0.0139(15) -0.0168(16) -0.0119(17) S1 0.0793(8) 0.0434(6) 0.0975(9) 0.0082(6) -0.0165(6) -0.0103(5) S2 0.0578(7) 0.1558(13) 0.0735(8) -0.0503(8) 0.0142(6) 0.0031(8) _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 C1 O1 1.301(4) . ? C1 N1 1.314(4) . ? C1 C2 1.424(5) . ? C2 C4 1.402(5) . ? C2 C3 1.427(4) . ? C3 N3 1.346(4) . ? C3 S1 1.687(3) . ? C4 N2 1.151(4) . ? C5 N1 1.460(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.370(5) . ? C6 C11 1.371(4) . ? C6 N3 1.435(4) . ? C7 C8 1.380(5) . ? C7 H7 0.9300 . ? C8 C9 1.364(5) . ? C8 H8 0.9300 . ? C9 O2 1.373(4) . ? C9 C10 1.382(5) . ? C10 C11 1.377(5) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 O2 1.429(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O3 1.296(4) . ? C13 N4 1.317(5) . ? C13 C14 1.421(5) . ? C14 C16 1.399(5) . ? C14 C15 1.436(5) . ? C15 N6 1.340(5) . ? C15 S2 1.696(4) . ? C16 N5 1.148(4) . ? C17 N4 1.461(5) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C23 1.363(5) . ? C18 C19 1.368(5) . ? C18 N6 1.439(4) . ? C19 C20 1.379(5) . ? C19 H19 0.9300 . ? C20 C21 1.361(5) . ? C20 H20 0.9300 . ? C21 C22 1.360(5) . ? C21 O4 1.377(4) . ? C22 C23 1.381(5) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 O4 1.409(5) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? N1 H1N1 0.83(3) . ? N3 H1N3 0.84(4) . ? N4 H1N4 0.87(3) . ? N6 H1N6 0.81(3) . ? O1 H1O1 1.18(5) . ? O3 H1O3 1.15(5) . ? S1 H1O1 1.70(5) . ? S2 H1O3 1.73(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 O1 C1 N1 115.4(3) . . ? O1 C1 C2 122.5(3) . . ? N1 C1 C2 122.2(3) . . ? C4 C2 C1 116.0(3) . . ? C4 C2 C3 119.0(3) . . ? C1 C2 C3 124.9(3) . . ? N3 C3 C2 117.1(3) . . ? N3 C3 S1 119.8(3) . . ? C2 C3 S1 123.1(3) . . ? N2 C4 C2 179.3(5) . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C11 119.6(3) . . ? C7 C6 N3 120.2(3) . . ? C11 C6 N3 120.1(3) . . ? C6 C7 C8 120.6(4) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 120.0(4) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 O2 124.3(4) . . ? C8 C9 C10 119.4(3) . . ? O2 C9 C10 116.4(3) . . ? C11 C10 C9 120.5(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C6 C11 C10 119.8(3) . . ? C6 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 N4 115.5(4) . . ? O3 C13 C14 123.0(3) . . ? N4 C13 C14 121.5(4) . . ? C16 C14 C13 117.3(3) . . ? C16 C14 C15 118.3(3) . . ? C13 C14 C15 124.4(3) . . ? N6 C15 C14 117.5(3) . . ? N6 C15 S2 119.5(3) . . ? C14 C15 S2 123.0(3) . . ? N5 C16 C14 179.2(4) . . ? N4 C17 H17A 109.5 . . ? N4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C18 C19 119.0(3) . . ? C23 C18 N6 119.9(3) . . ? C19 C18 N6 121.0(3) . . ? C18 C19 C20 121.1(4) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C21 C20 C19 119.4(4) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C22 C21 C20 119.9(4) . . ? C22 C21 O4 115.2(3) . . ? C20 C21 O4 124.9(4) . . ? C21 C22 C23 120.6(4) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C18 C23 C22 119.9(4) . . ? C18 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? O4 C24 H24A 109.5 . . ? O4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C1 N1 C5 123.6(4) . . ? C1 N1 H1N1 120(3) . . ? C5 N1 H1N1 116(3) . . ? C4 N2 H1N6 126.1(9) . . ? C3 N3 C6 126.0(3) . . ? C3 N3 H1N3 117(3) . . ? C6 N3 H1N3 116(3) . . ? C13 N4 C17 123.0(4) . . ? C13 N4 H1N4 119(3) . . ? C17 N4 H1N4 117(3) . . ? C16 N5 H1N3 125.6(9) . . ? C15 N6 C18 124.7(3) . . ? C15 N6 H1N6 121(3) . . ? C18 N6 H1N6 114(3) . . ? C1 O1 H1O1 104(2) . . ? C9 O2 C12 116.4(3) . . ? C13 O3 H1O3 105(2) . . ? C21 O4 C24 118.2(3) . . ? C3 S1 H1O1 84.3(14) . . ? C15 S2 H1O3 84.8(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H1O3 S2 1.15(5) 1.73(5) 2.829(3) 159(4) . O1 H1O1 S1 1.18(5) 1.70(5) 2.836(3) 161(3) . N4 H1N4 N5 0.87(3) 2.19(4) 2.978(5) 152(3) 3_665 N1 H1N1 N2 0.83(3) 2.23(4) 2.976(5) 151(3) 3_766 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.397 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.042 # Attachment '12f.cif' data_12f _database_code_depnum_ccdc_archive 'CCDC 667548' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H15 N3 O S' _chemical_formula_sum 'C9 H15 N3 O S' _chemical_formula_weight 213.30 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)/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 7.3690(4) _cell_length_b 15.9322(8) _cell_length_c 10.1036(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.6260(10) _cell_angle_gamma 90.00 _cell_volume 1172.79(10) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 8224 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.99 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8932 _exptl_absorpt_correction_T_max 0.9150 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(1) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12869 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2557 _reflns_number_gt 2385 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+0.2605P] 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 0.015(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2557 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.42578(17) 0.25176(8) 0.47306(11) 0.0394(3) Uani 1 1 d . . . C2 C 0.57648(16) 0.26790(8) 0.59358(12) 0.0384(3) Uani 1 1 d . . . H2 H 0.5285 0.2554 0.6768 0.046 Uiso 1 1 calc R . . C3 C 0.64777(16) 0.35914(8) 0.59752(12) 0.0374(3) Uani 1 1 d . . . C4 C 0.7319(2) 0.21224(9) 0.58167(14) 0.0486(3) Uani 1 1 d . . . C5 C 0.7347(2) 0.47940(9) 0.74871(15) 0.0531(3) Uani 1 1 d . . . H5 H 0.7034 0.5145 0.6689 0.064 Uiso 1 1 calc R . . C6 C 0.9407(3) 0.47830(13) 0.7869(3) 0.0825(6) Uani 1 1 d . . . H6A H 0.9736 0.4408 0.8609 0.124 Uiso 1 1 calc R . . H6B H 0.9833 0.5338 0.8121 0.124 Uiso 1 1 calc R . . H6C H 0.9962 0.4596 0.7120 0.124 Uiso 1 1 calc R . . C7 C 0.6393(3) 0.51403(12) 0.8590(2) 0.0772(5) Uani 1 1 d . . . H7A H 0.5089 0.5125 0.8314 0.116 Uiso 1 1 calc R . . H7B H 0.6776 0.5710 0.8774 0.116 Uiso 1 1 calc R . . H7C H 0.6707 0.4807 0.9383 0.116 Uiso 1 1 calc R . . C8 C 0.2236(2) 0.35158(9) 0.56969(14) 0.0499(3) Uani 1 1 d . . . H8A H 0.2997 0.3411 0.6538 0.075 Uiso 1 1 calc R . . H8B H 0.0969 0.3464 0.5804 0.075 Uiso 1 1 calc R . . H8C H 0.2463 0.4073 0.5398 0.075 Uiso 1 1 calc R . . C9 C 0.1264(2) 0.27966(12) 0.35385(16) 0.0628(4) Uani 1 1 d . . . H9A H 0.1706 0.3018 0.2763 0.094 Uiso 1 1 calc R . . H9B H 0.0165 0.3088 0.3671 0.094 Uiso 1 1 calc R . . H9C H 0.1001 0.2210 0.3410 0.094 Uiso 1 1 calc R . . N1 N 0.26615(15) 0.29097(7) 0.47131(11) 0.0448(3) Uani 1 1 d . . . H1N1 H 0.641(2) 0.3651(11) 0.7788(17) 0.056(5) Uiso 1 1 d . . . N2 N 0.8560(2) 0.17136(10) 0.57303(16) 0.0721(4) Uani 1 1 d . . . N3 N 0.66738(17) 0.39365(7) 0.71700(11) 0.0446(3) Uani 1 1 d . . . O1 O 0.45547(13) 0.20305(7) 0.38443(9) 0.0523(3) Uani 1 1 d . . . S1 S 0.69439(5) 0.40276(2) 0.45742(3) 0.05091(15) 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 0.0414(6) 0.0443(6) 0.0325(5) -0.0025(5) 0.0056(5) -0.0007(5) C2 0.0425(6) 0.0408(6) 0.0314(5) -0.0003(4) 0.0041(4) 0.0004(5) C3 0.0355(5) 0.0405(6) 0.0358(6) 0.0012(5) 0.0043(4) 0.0027(5) C4 0.0527(7) 0.0446(7) 0.0444(7) -0.0002(5) -0.0063(6) 0.0047(6) C5 0.0731(9) 0.0394(7) 0.0473(7) -0.0057(6) 0.0110(7) -0.0040(6) C6 0.0745(12) 0.0645(10) 0.1081(16) -0.0309(11) 0.0127(11) -0.0203(9) C7 0.1090(15) 0.0604(10) 0.0662(10) -0.0148(8) 0.0263(10) 0.0072(10) C8 0.0496(7) 0.0553(8) 0.0453(7) -0.0056(6) 0.0091(6) 0.0093(6) C9 0.0453(7) 0.0880(12) 0.0513(8) -0.0138(8) -0.0052(6) 0.0076(7) N1 0.0394(5) 0.0556(6) 0.0387(5) -0.0071(5) 0.0035(4) 0.0032(5) N2 0.0669(9) 0.0644(8) 0.0787(10) -0.0058(7) -0.0100(7) 0.0252(7) N3 0.0570(7) 0.0421(6) 0.0350(5) -0.0013(4) 0.0081(5) -0.0065(5) O1 0.0513(5) 0.0640(6) 0.0405(5) -0.0164(4) 0.0031(4) 0.0068(4) S1 0.0618(3) 0.0532(2) 0.0403(2) 0.00725(13) 0.01643(16) 0.00048(15) _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 C1 O1 1.2292(15) . ? C1 N1 1.3297(17) . ? C1 C2 1.5416(16) . ? C2 C4 1.4674(19) . ? C2 C3 1.5442(17) . ? C2 H2 0.9800 . ? C3 N3 1.3145(16) . ? C3 S1 1.6586(12) . ? C4 N2 1.137(2) . ? C5 N3 1.4723(17) . ? C5 C7 1.508(2) . ? C5 C6 1.509(3) . ? C5 H5 0.9800 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N1 1.4532(16) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.4613(17) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? N3 H1N1 0.819(18) . ? 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 O1 C1 N1 122.73(11) . . ? O1 C1 C2 119.67(11) . . ? N1 C1 C2 117.59(10) . . ? C4 C2 C1 108.24(10) . . ? C4 C2 C3 107.72(10) . . ? C1 C2 C3 112.30(10) . . ? C4 C2 H2 109.5 . . ? C1 C2 H2 109.5 . . ? C3 C2 H2 109.5 . . ? N3 C3 C2 114.05(11) . . ? N3 C3 S1 126.88(10) . . ? C2 C3 S1 119.06(9) . . ? N2 C4 C2 177.72(17) . . ? N3 C5 C7 108.72(13) . . ? N3 C5 C6 109.77(13) . . ? C7 C5 C6 112.20(16) . . ? N3 C5 H5 108.7 . . ? C7 C5 H5 108.7 . . ? C6 C5 H5 108.7 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 N1 C8 125.74(11) . . ? C1 N1 C9 117.86(11) . . ? C8 N1 C9 116.07(11) . . ? C3 N3 C5 125.10(12) . . ? C3 N3 H1N1 117.5(12) . . ? C5 N3 H1N1 117.4(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H1N1 O1 0.819(18) 2.150(19) 2.9097(15) 154.2(16) 4_566 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.230 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.045 # Attachment '12r.cif' data_12r _database_code_depnum_ccdc_archive 'CCDC 667549' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 N3 S2, C7 H10 N3 O S, H2 O' _chemical_formula_sum 'C17 H28 N6 O2 S3' _chemical_formula_weight 444.63 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _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 8.4053(5) _cell_length_b 14.8272(9) _cell_length_c 18.2296(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2271.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.351 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9113 _exptl_absorpt_correction_T_max 0.9268 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(1) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26066 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.99 _reflns_number_total 4961 _reflns_number_gt 4629 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 w=1/[\s^2^(Fo^2^)+(0.0436P)^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 mixed _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 -0.02(5) _refine_ls_number_reflns 4961 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0697 _refine_ls_wR_factor_gt 0.0689 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 C3 C 0.40712(18) 0.48399(11) 0.98794(9) 0.0332(3) Uani 1 1 d . . . C2 C 0.56076(19) 0.49101(10) 1.02044(8) 0.0332(3) Uani 1 1 d . . . C1 C 0.70853(19) 0.49773(12) 0.98009(9) 0.0390(4) Uani 1 1 d . . . C4 C 0.57182(18) 0.49508(10) 1.09802(9) 0.0338(3) Uani 1 1 d . . . C5 C 0.2521(2) 0.49398(14) 0.87145(10) 0.0454(4) Uani 1 1 d . . . H5 H 0.182(3) 0.4579(13) 0.8935(10) 0.045(5) Uiso 1 1 d . . . C6 C 0.1862(4) 0.58868(19) 0.87067(18) 0.0702(7) Uani 1 1 d . . . H6A H 0.096(3) 0.5880(15) 0.8385(13) 0.068(7) Uiso 1 1 d . . . H6B H 0.261(3) 0.6278(19) 0.8526(15) 0.089(9) Uiso 1 1 d . . . H6C H 0.161(4) 0.6081(19) 0.9181(17) 0.094(10) Uiso 1 1 d . . . C7 C 0.2869(4) 0.4597(3) 0.79482(13) 0.0708(7) Uani 1 1 d . . . H7A H 0.189(4) 0.469(2) 0.7617(17) 0.104(9) Uiso 1 1 d . . . H7B H 0.326(4) 0.405(2) 0.7977(15) 0.084(10) Uiso 1 1 d . . . H7C H 0.372(3) 0.4895(16) 0.7720(12) 0.065(7) Uiso 1 1 d . . . C11 C 0.4617(2) 0.76840(11) 0.77990(9) 0.0360(4) Uani 1 1 d . . . C12 C 0.3992(2) 0.72685(11) 0.71703(9) 0.0350(4) Uani 1 1 d . . . C13 C 0.2586(2) 0.76205(10) 0.68699(9) 0.0360(3) Uani 1 1 d . . . C14 C 0.47954(19) 0.65336(12) 0.68306(9) 0.0366(4) Uani 1 1 d . . . C15 C 0.6535(3) 0.79158(13) 0.88088(10) 0.0476(4) Uani 1 1 d . . . H15 H 0.624(2) 0.8548(14) 0.8771(11) 0.054(6) Uiso 1 1 d . . . C16 C 0.5862(6) 0.7462(3) 0.94724(16) 0.0886(10) Uani 1 1 d . . . H16A H 0.624(3) 0.7757(19) 0.9873(17) 0.087(9) Uiso 1 1 d . . . H16B H 0.626(4) 0.689(2) 0.9519(16) 0.090(11) Uiso 1 1 d . . . H16C H 0.492(4) 0.743(3) 0.9452(18) 0.116(15) Uiso 1 1 d . . . C17 C 0.8323(3) 0.7947(2) 0.87922(17) 0.0678(7) Uani 1 1 d . . . H17A H 0.873(3) 0.8283(18) 0.9214(15) 0.087(8) Uiso 1 1 d . . . H17B H 0.868(3) 0.7379(19) 0.8828(14) 0.081(9) Uiso 1 1 d . . . H17C H 0.868(4) 0.813(2) 0.834(2) 0.122(13) Uiso 1 1 d . . . C18 C 0.0433(2) 0.77808(12) 0.59627(10) 0.0417(4) Uani 1 1 d . . . H18 H 0.055(2) 0.8432(12) 0.6065(9) 0.040(5) Uiso 1 1 d . . . C19 C -0.1072(3) 0.74447(17) 0.63211(15) 0.0566(5) Uani 1 1 d . . . H19A H -0.104(3) 0.7421(16) 0.6865(14) 0.074(8) Uiso 1 1 d . . . H19B H -0.192(3) 0.7764(16) 0.6146(12) 0.062(6) Uiso 1 1 d . . . H19C H -0.127(3) 0.6805(18) 0.6162(14) 0.081(8) Uiso 1 1 d . . . C20 C 0.0441(3) 0.76535(19) 0.51421(12) 0.0585(5) Uani 1 1 d . . . H20A H 0.019(4) 0.701(2) 0.4995(17) 0.109(11) Uiso 1 1 d . . . H20B H 0.139(3) 0.7930(16) 0.4943(14) 0.066(7) Uiso 1 1 d . . . H20C H -0.044(3) 0.7984(16) 0.4935(13) 0.066(7) Uiso 1 1 d . . . N3 N 0.39655(18) 0.48927(12) 0.91511(8) 0.0441(4) Uani 1 1 d . . . H1N3 H 0.478(2) 0.4956(12) 0.8917(10) 0.035(5) Uiso 1 1 d . . . N2 N 0.59264(18) 0.49964(10) 1.16018(8) 0.0442(3) Uani 1 1 d . . . N1 N 0.8448(2) 0.50507(13) 1.01781(10) 0.0503(4) Uani 1 1 d . . . H1N1 H 0.847(3) 0.4887(14) 1.0609(11) 0.049(6) Uiso 1 1 d . . . H2N1 H 0.926(3) 0.5029(12) 0.9953(11) 0.037(5) Uiso 1 1 d . . . N4 N 0.5444(2) 0.59478(11) 0.65589(9) 0.0542(4) Uani 1 1 d . . . N5 N 0.59375(19) 0.74673(11) 0.81362(8) 0.0406(3) Uani 1 1 d . . . H1N5 H 0.644(2) 0.7039(13) 0.7986(10) 0.037(5) Uiso 1 1 d . . . N6 N 0.18533(18) 0.73356(10) 0.62794(8) 0.0391(3) Uani 1 1 d . . . H1N6 H 0.209(3) 0.6836(15) 0.6085(12) 0.059(6) Uiso 1 1 d . . . O1 O 0.71338(15) 0.49817(12) 0.91140(7) 0.0609(4) Uani 1 1 d . . . O1W O 0.7882(2) 0.59960(12) 0.78997(9) 0.0593(4) Uani 1 1 d . . . H1W H 0.773(3) 0.5681(18) 0.8193(15) 0.070(9) Uiso 1 1 d . . . H2W H 0.816(3) 0.5701(16) 0.7526(14) 0.062(7) Uiso 1 1 d . . . S1 S 0.24191(5) 0.46824(3) 1.04145(2) 0.03886(11) Uani 1 1 d . . . S2 S 0.34997(6) 0.85835(3) 0.81417(3) 0.04743(12) Uani 1 1 d . . . S3 S 0.17737(6) 0.85354(3) 0.73401(3) 0.04460(12) 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 C3 0.0298(8) 0.0336(8) 0.0363(8) 0.0028(7) 0.0020(6) 0.0006(6) C2 0.0286(8) 0.0397(9) 0.0314(8) 0.0043(7) 0.0023(6) 0.0016(6) C1 0.0307(8) 0.0482(10) 0.0382(9) 0.0061(8) 0.0044(6) 0.0036(7) C4 0.0273(7) 0.0347(8) 0.0395(9) 0.0002(7) 0.0016(7) 0.0010(6) C5 0.0385(9) 0.0565(10) 0.0413(9) 0.0037(8) -0.0060(8) -0.0115(9) C6 0.0654(16) 0.0705(16) 0.0747(18) 0.0085(14) -0.0179(14) 0.0095(14) C7 0.0760(18) 0.092(2) 0.0443(12) -0.0056(12) -0.0073(12) -0.0113(17) C11 0.0377(9) 0.0337(8) 0.0365(9) -0.0014(7) 0.0056(7) 0.0013(7) C12 0.0352(9) 0.0361(8) 0.0336(8) -0.0019(7) 0.0035(7) 0.0037(7) C13 0.0394(9) 0.0326(8) 0.0359(8) -0.0006(6) 0.0071(7) 0.0023(7) C14 0.0338(8) 0.0435(9) 0.0326(8) -0.0041(8) -0.0048(7) 0.0022(7) C15 0.0547(11) 0.0444(10) 0.0438(10) -0.0102(8) -0.0092(9) 0.0013(9) C16 0.112(3) 0.113(3) 0.0406(13) -0.0112(15) 0.0003(15) -0.029(2) C17 0.0546(13) 0.0767(17) 0.0722(17) -0.0195(14) -0.0189(13) 0.0001(13) C18 0.0415(9) 0.0358(9) 0.0477(10) -0.0003(8) -0.0054(8) 0.0060(8) C19 0.0412(11) 0.0576(14) 0.0711(16) 0.0012(11) -0.0004(10) 0.0019(10) C20 0.0642(15) 0.0638(15) 0.0475(11) 0.0055(11) -0.0095(11) 0.0164(12) N3 0.0297(7) 0.0673(11) 0.0353(8) 0.0048(7) 0.0020(6) -0.0032(7) N2 0.0426(8) 0.0535(9) 0.0367(8) -0.0040(7) -0.0034(6) 0.0030(7) N1 0.0263(8) 0.0795(12) 0.0451(9) 0.0094(9) 0.0030(7) 0.0027(7) N4 0.0497(9) 0.0613(10) 0.0518(9) -0.0193(8) -0.0078(8) 0.0157(8) N5 0.0422(8) 0.0401(8) 0.0395(8) -0.0078(7) -0.0027(7) 0.0059(7) N6 0.0415(8) 0.0365(7) 0.0394(8) -0.0050(6) -0.0028(6) 0.0111(6) O1 0.0384(7) 0.1076(12) 0.0367(7) 0.0087(7) 0.0060(5) -0.0023(7) O1W 0.0799(12) 0.0576(9) 0.0405(8) -0.0002(7) 0.0035(8) 0.0195(8) S1 0.02725(18) 0.0476(2) 0.0417(2) 0.00445(18) 0.00482(17) -0.00051(18) S2 0.0505(3) 0.0444(2) 0.0474(2) -0.0153(2) -0.0033(2) 0.0099(2) S3 0.0451(2) 0.0418(2) 0.0469(2) -0.0089(2) -0.0018(2) 0.0124(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C3 N3 1.333(2) . ? C3 C2 1.425(2) . ? C3 S1 1.7131(16) . ? C2 C4 1.418(2) . ? C2 C1 1.447(2) . ? C1 O1 1.253(2) . ? C1 N1 1.340(2) . ? C4 N2 1.149(2) . ? C5 N3 1.453(2) . ? C5 C6 1.510(3) . ? C5 C7 1.515(3) . ? C5 H5 0.89(2) . ? C6 H6A 0.96(3) . ? C6 H6B 0.92(3) . ? C6 H6C 0.93(3) . ? C7 H7A 1.03(3) . ? C7 H7B 0.88(3) . ? C7 H7C 0.94(3) . ? C11 N5 1.309(2) . ? C11 C12 1.403(2) . ? C11 S2 1.7467(17) . ? C12 C13 1.403(2) . ? C12 C14 1.424(2) . ? C13 N6 1.310(2) . ? C13 S3 1.7438(16) . ? C14 N4 1.139(2) . ? C15 N5 1.483(2) . ? C15 C16 1.495(4) . ? C15 C17 1.504(3) . ? C15 H15 0.97(2) . ? C16 H16A 0.91(3) . ? C16 H16B 0.91(3) . ? C16 H16C 0.80(4) . ? C17 H17A 0.98(3) . ? C17 H17B 0.90(3) . ? C17 H17C 0.91(4) . ? C18 N6 1.481(2) . ? C18 C20 1.508(3) . ? C18 C19 1.508(3) . ? C18 H18 0.989(18) . ? C19 H19A 0.99(2) . ? C19 H19B 0.91(3) . ? C19 H19C 1.01(3) . ? C20 H20A 1.01(3) . ? C20 H20B 0.97(3) . ? C20 H20C 0.97(3) . ? N3 H1N3 0.82(2) . ? N1 H1N1 0.82(2) . ? N1 H2N1 0.80(2) . ? N5 H1N5 0.81(2) . ? N6 H1N6 0.84(2) . ? O1 H1N3 2.01(2) . ? O1 H1W 2.04(3) . ? O1W H1N5 1.97(2) . ? O1W H1W 0.72(3) . ? O1W H2W 0.84(3) . ? S2 S3 2.0604(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 N3 C3 C2 118.06(14) . . ? N3 C3 S1 121.42(13) . . ? C2 C3 S1 120.52(12) . . ? C4 C2 C3 118.50(14) . . ? C4 C2 C1 116.59(14) . . ? C3 C2 C1 124.86(14) . . ? O1 C1 N1 118.98(15) . . ? O1 C1 C2 122.44(15) . . ? N1 C1 C2 118.58(15) . . ? N2 C4 C2 174.90(17) . . ? N3 C5 C6 110.89(18) . . ? N3 C5 C7 109.13(19) . . ? C6 C5 C7 112.0(2) . . ? N3 C5 H5 106.0(13) . . ? C6 C5 H5 108.6(13) . . ? C7 C5 H5 110.0(12) . . ? C5 C6 H6A 106.6(14) . . ? C5 C6 H6B 109.8(18) . . ? H6A C6 H6B 109(2) . . ? C5 C6 H6C 111.1(18) . . ? H6A C6 H6C 113(2) . . ? H6B C6 H6C 107(3) . . ? C5 C7 H7A 110.0(17) . . ? C5 C7 H7B 109.1(19) . . ? H7A C7 H7B 117(3) . . ? C5 C7 H7C 113.5(14) . . ? H7A C7 H7C 107(2) . . ? H7B C7 H7C 100(2) . . ? N5 C11 C12 126.39(16) . . ? N5 C11 S2 118.39(13) . . ? C12 C11 S2 115.22(13) . . ? C11 C12 C13 118.08(15) . . ? C11 C12 C14 120.91(15) . . ? C13 C12 C14 120.96(15) . . ? N6 C13 C12 126.62(15) . . ? N6 C13 S3 118.09(13) . . ? C12 C13 S3 115.29(13) . . ? N4 C14 C12 179.7(2) . . ? N5 C15 C16 109.82(19) . . ? N5 C15 C17 109.60(18) . . ? C16 C15 C17 114.1(3) . . ? N5 C15 H15 106.7(12) . . ? C16 C15 H15 113.2(12) . . ? C17 C15 H15 103.0(12) . . ? C15 C16 H16A 107.5(19) . . ? C15 C16 H16B 111(2) . . ? H16A C16 H16B 104(3) . . ? C15 C16 H16C 112(3) . . ? H16A C16 H16C 115(3) . . ? H16B C16 H16C 108(4) . . ? C15 C17 H17A 110.6(16) . . ? C15 C17 H17B 107.9(18) . . ? H17A C17 H17B 108(2) . . ? C15 C17 H17C 111(2) . . ? H17A C17 H17C 116(3) . . ? H17B C17 H17C 103(3) . . ? N6 C18 C20 109.11(16) . . ? N6 C18 C19 111.09(16) . . ? C20 C18 C19 113.09(19) . . ? N6 C18 H18 106.5(11) . . ? C20 C18 H18 108.0(10) . . ? C19 C18 H18 108.8(11) . . ? C18 C19 H19A 114.8(15) . . ? C18 C19 H19B 109.4(15) . . ? H19A C19 H19B 113(2) . . ? C18 C19 H19C 108.9(15) . . ? H19A C19 H19C 105(2) . . ? H19B C19 H19C 105(2) . . ? C18 C20 H20A 112.4(18) . . ? C18 C20 H20B 108.9(15) . . ? H20A C20 H20B 118(2) . . ? C18 C20 H20C 108.6(14) . . ? H20A C20 H20C 102(2) . . ? H20B C20 H20C 105.8(19) . . ? C3 N3 C5 127.15(16) . . ? C3 N3 H1N3 118.1(13) . . ? C5 N3 H1N3 114.4(13) . . ? C1 N1 H1N1 119.0(16) . . ? C1 N1 H2N1 117.8(14) . . ? H1N1 N1 H2N1 117(2) . . ? C11 N5 C15 124.44(16) . . ? C11 N5 H1N5 118.4(13) . . ? C15 N5 H1N5 117.1(13) . . ? C13 N6 C18 123.73(15) . . ? C13 N6 H1N6 121.2(15) . . ? C18 N6 H1N6 114.6(15) . . ? C1 O1 H1N3 98.4(5) . . ? C1 O1 H1W 146.6(8) . . ? H1N3 O1 H1W 95.9(9) . . ? H1N5 O1W H1W 110(2) . . ? H1N5 O1W H2W 129.9(16) . . ? H1W O1W H2W 108(3) . . ? C11 S2 S3 95.66(6) . . ? C13 S3 S2 95.74(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H1N3 O1 0.82(2) 2.01(2) 2.6672(19) 137.7(17) . N1 H1N1 N4 0.82(2) 2.32(2) 3.065(2) 152(2) 2_665 N1 H2N1 S1 0.80(2) 2.83(2) 3.4098(17) 131.2(17) 1_655 N5 H1N5 O1W 0.81(2) 1.97(2) 2.760(2) 164.2(18) . N6 H1N6 S1 0.84(2) 2.59(2) 3.4368(16) 175(2) 2_564 O1W H1W O1 0.72(3) 2.04(3) 2.749(2) 170(3) . O1W H2W N2 0.84(3) 2.12(3) 2.961(2) 174(2) 2_664 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.229 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.045 # Attachment '11h.cif' data_11h _database_code_depnum_ccdc_archive 'CCDC 667550' # start Validation Reply Form _vrf_PLAT771_11h ; PROBLEM: Suspect N-H Bond in CIF: N2 -H21N .. 2.30 Ang. PROBLEM: Suspect N-H Bond in CIF: N22 -H1N .. 2.23 Ang. RESPONSE: ... It is rather a nice case of 2 two independent molecules attaching each other through two hydrogen bonds thus closing a ten-membered ring with a graph-set notation R^2^~2`~ (12). ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 N3 O S' _chemical_formula_sum 'C11 H11 N3 O S' _chemical_formula_weight 233.29 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4637(5) _cell_length_b 9.9527(6) _cell_length_c 13.2117(8) _cell_angle_alpha 81.3100(10) _cell_angle_beta 79.1780(10) _cell_angle_gamma 68.9710(10) _cell_volume 1136.10(11) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description shapeless _exptl_crystal_colour pale _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.266 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8895 _exptl_absorpt_correction_T_max 0.9196 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(1) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12684 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4900 _reflns_number_gt 4194 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 w=1/[\s^2^(Fo^2^)+(0.0813P)^2^+0.1492P] 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 0.014(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4900 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1267 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.22619(16) 0.60887(15) 0.47638(11) 0.0420(3) Uani 1 1 d . . . C2 C 0.26947(16) 0.67761(15) 0.37885(10) 0.0407(3) Uani 1 1 d . . . C3 C 0.21936(16) 0.67366(15) 0.28437(11) 0.0405(3) Uani 1 1 d . . . C4 C 0.37623(17) 0.74783(16) 0.37706(11) 0.0437(3) Uani 1 1 d . . . C5 C 0.2408(2) 0.5405(2) 0.66032(11) 0.0567(4) Uani 1 1 d . . . H5A H 0.1415 0.5983 0.6914 0.085 Uiso 1 1 calc R . . H5B H 0.3150 0.5291 0.7044 0.085 Uiso 1 1 calc R . . H5C H 0.2391 0.4472 0.6512 0.085 Uiso 1 1 calc R . . C6 C 0.25260(16) 0.75340(16) 0.09615(11) 0.0436(3) Uani 1 1 d . . . C7 C 0.19660(17) 0.88430(16) 0.03859(11) 0.0481(3) Uani 1 1 d . . . H7 H 0.1610 0.9702 0.0701 0.058 Uiso 1 1 calc R . . C8 C 0.19374(18) 0.88690(18) -0.06594(11) 0.0543(4) Uani 1 1 d . . . H8 H 0.1564 0.9750 -0.1046 0.065 Uiso 1 1 calc R . . C9 C 0.2454(2) 0.7611(2) -0.11334(12) 0.0593(4) Uani 1 1 d . . . H9 H 0.2428 0.7637 -0.1837 0.071 Uiso 1 1 calc R . . C10 C 0.3013(2) 0.6301(2) -0.05561(13) 0.0622(4) Uani 1 1 d . . . H10 H 0.3359 0.5444 -0.0872 0.075 Uiso 1 1 calc R . . C11 C 0.30606(18) 0.62611(17) 0.04884(12) 0.0538(4) Uani 1 1 d . . . H11 H 0.3451 0.5380 0.0872 0.065 Uiso 1 1 calc R . . C21 C 0.77013(16) 0.88314(15) 0.51871(11) 0.0428(3) Uani 1 1 d . . . C22 C 0.71669(16) 0.82442(15) 0.61741(10) 0.0403(3) Uani 1 1 d . . . C23 C 0.76513(15) 0.82858(14) 0.71254(10) 0.0391(3) Uani 1 1 d . . . C24 C 0.60328(17) 0.76205(16) 0.61967(11) 0.0451(3) Uani 1 1 d . . . C25 C 0.7657(2) 0.9425(2) 0.33356(12) 0.0597(4) Uani 1 1 d . . . H25A H 0.7750 1.0339 0.3392 0.090 Uiso 1 1 calc R . . H25B H 0.6934 0.9556 0.2876 0.090 Uiso 1 1 calc R . . H25C H 0.8634 0.8767 0.3068 0.090 Uiso 1 1 calc R . . C26 C 0.72466(17) 0.76270(16) 0.90255(11) 0.0435(3) Uani 1 1 d . . . C27 C 0.60352(19) 0.8123(2) 0.97806(13) 0.0709(5) Uani 1 1 d . . . H27 H 0.5052 0.8562 0.9609 0.085 Uiso 1 1 calc R . . C28 C 0.6270(2) 0.7972(3) 1.08004(14) 0.0845(7) Uani 1 1 d . . . H28 H 0.5441 0.8307 1.1312 0.101 Uiso 1 1 calc R . . C29 C 0.7702(2) 0.7338(2) 1.10642(13) 0.0620(4) Uani 1 1 d . . . H29 H 0.7854 0.7241 1.1751 0.074 Uiso 1 1 calc R . . C30 C 0.8915(2) 0.68451(18) 1.03095(12) 0.0599(4) Uani 1 1 d . . . H30 H 0.9898 0.6423 1.0483 0.072 Uiso 1 1 calc R . . C31 C 0.86933(19) 0.69681(18) 0.92894(12) 0.0563(4) Uani 1 1 d . . . H31 H 0.9521 0.6606 0.8783 0.068 Uiso 1 1 calc R . . N1 N 0.28145(16) 0.61128(15) 0.56027(9) 0.0485(3) Uani 1 1 d . . . H1N H 0.339(2) 0.6579(19) 0.5564(14) 0.051(5) Uiso 1 1 d . . . N2 N 0.46512(17) 0.80228(17) 0.37658(11) 0.0584(4) Uani 1 1 d . . . N3 N 0.26510(18) 0.75378(16) 0.20155(10) 0.0532(3) Uani 1 1 d . . . H3N H 0.288(2) 0.813(2) 0.2135(14) 0.063(6) Uiso 1 1 d . . . N21 N 0.71302(17) 0.88368(15) 0.43508(10) 0.0502(3) Uani 1 1 d . . . H21N H 0.650(2) 0.851(2) 0.4415(14) 0.054(5) Uiso 1 1 d . . . N22 N 0.51044(18) 0.71182(18) 0.62253(11) 0.0625(4) Uani 1 1 d . . . N23 N 0.69489(16) 0.77588(15) 0.79910(10) 0.0490(3) Uani 1 1 d . . . H23N H 0.630(2) 0.751(2) 0.7937(14) 0.065(6) Uiso 1 1 d . . . O1 O 0.13047(14) 0.53900(14) 0.48896(9) 0.0572(3) Uani 1 1 d . . . H1O H 0.100(3) 0.541(3) 0.415(2) 0.116(9) Uiso 1 1 d . . . O21 O 0.87717(14) 0.94031(14) 0.50453(9) 0.0583(3) Uani 1 1 d . . . H21O H 0.909(3) 0.928(3) 0.578(2) 0.114(9) Uiso 1 1 d . . . S1 S 0.10766(5) 0.57809(5) 0.27319(3) 0.05300(15) Uani 1 1 d . . . S21 S 0.90048(5) 0.90077(5) 0.71964(3) 0.05141(15) 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 0.0424(7) 0.0504(7) 0.0411(7) -0.0037(6) -0.0081(5) -0.0245(6) C2 0.0443(7) 0.0482(7) 0.0382(7) -0.0010(5) -0.0109(5) -0.0248(6) C3 0.0428(7) 0.0442(7) 0.0404(7) -0.0024(5) -0.0113(5) -0.0198(6) C4 0.0511(8) 0.0521(8) 0.0364(7) 0.0018(6) -0.0137(6) -0.0263(6) C5 0.0707(10) 0.0718(10) 0.0372(8) 0.0004(7) -0.0080(7) -0.0378(9) C6 0.0458(7) 0.0558(8) 0.0379(7) -0.0014(6) -0.0102(6) -0.0266(6) C7 0.0520(8) 0.0511(8) 0.0445(8) -0.0041(6) -0.0075(6) -0.0214(6) C8 0.0583(9) 0.0624(9) 0.0441(8) 0.0055(7) -0.0140(7) -0.0236(7) C9 0.0645(10) 0.0828(12) 0.0373(8) -0.0078(7) -0.0109(7) -0.0303(9) C10 0.0696(11) 0.0661(10) 0.0549(9) -0.0197(8) -0.0082(8) -0.0225(8) C11 0.0603(9) 0.0515(8) 0.0512(9) -0.0031(6) -0.0150(7) -0.0180(7) C21 0.0460(7) 0.0492(7) 0.0407(7) -0.0040(6) -0.0098(6) -0.0237(6) C22 0.0456(7) 0.0444(7) 0.0399(7) -0.0022(5) -0.0121(5) -0.0240(6) C23 0.0439(7) 0.0385(6) 0.0398(7) -0.0036(5) -0.0118(5) -0.0169(5) C24 0.0540(8) 0.0548(8) 0.0364(7) 0.0010(6) -0.0156(6) -0.0280(7) C25 0.0723(11) 0.0772(11) 0.0377(8) -0.0005(7) -0.0085(7) -0.0367(9) C26 0.0536(8) 0.0501(8) 0.0378(7) 0.0023(6) -0.0134(6) -0.0300(6) C27 0.0471(9) 0.1201(17) 0.0506(9) -0.0010(10) -0.0082(7) -0.0365(10) C28 0.0684(12) 0.146(2) 0.0429(9) -0.0083(11) 0.0033(8) -0.0471(13) C29 0.0836(12) 0.0791(11) 0.0395(8) 0.0037(7) -0.0192(8) -0.0457(10) C30 0.0648(10) 0.0679(10) 0.0522(9) 0.0028(7) -0.0256(8) -0.0233(8) C31 0.0556(9) 0.0627(10) 0.0468(8) -0.0043(7) -0.0145(7) -0.0124(7) N1 0.0578(7) 0.0646(8) 0.0371(6) 0.0006(5) -0.0113(5) -0.0375(7) N2 0.0658(9) 0.0744(9) 0.0559(8) 0.0059(6) -0.0221(6) -0.0468(7) N3 0.0780(9) 0.0617(8) 0.0401(7) 0.0016(6) -0.0186(6) -0.0454(7) N21 0.0600(8) 0.0655(8) 0.0384(7) 0.0002(5) -0.0122(6) -0.0368(7) N22 0.0704(9) 0.0861(10) 0.0553(8) 0.0041(7) -0.0218(7) -0.0535(8) N23 0.0562(8) 0.0652(8) 0.0414(7) 0.0025(5) -0.0170(5) -0.0377(7) O1 0.0662(7) 0.0848(8) 0.0433(6) 0.0029(5) -0.0119(5) -0.0543(6) O21 0.0646(7) 0.0868(8) 0.0440(6) 0.0011(5) -0.0101(5) -0.0519(6) S1 0.0615(3) 0.0681(3) 0.0485(2) -0.00040(18) -0.01979(18) -0.0409(2) S21 0.0573(3) 0.0651(3) 0.0492(2) -0.00266(17) -0.01827(17) -0.0373(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.3009(17) . ? C1 N1 1.3181(18) . ? C1 C2 1.4257(19) . ? C2 C4 1.4151(18) . ? C2 C3 1.4265(18) . ? C3 N3 1.3516(18) . ? C3 S1 1.6932(14) . ? C4 N2 1.1513(19) . ? C5 N1 1.4540(19) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C11 1.383(2) . ? C6 C7 1.383(2) . ? C6 N3 1.4202(18) . ? C7 C8 1.382(2) . ? C7 H7 0.9300 . ? C8 C9 1.372(2) . ? C8 H8 0.9300 . ? C9 C10 1.385(3) . ? C9 H9 0.9300 . ? C10 C11 1.383(2) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C21 O21 1.3020(17) . ? C21 N21 1.3165(18) . ? C21 C22 1.4254(19) . ? C22 C24 1.4138(18) . ? C22 C23 1.4273(18) . ? C23 N23 1.3448(18) . ? C23 S21 1.7004(13) . ? C24 N22 1.1491(19) . ? C25 N21 1.4529(19) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.366(2) . ? C26 C31 1.375(2) . ? C26 N23 1.4243(18) . ? C27 C28 1.384(2) . ? C27 H27 0.9300 . ? C28 C29 1.361(3) . ? C28 H28 0.9300 . ? C29 C30 1.366(3) . ? C29 H29 0.9300 . ? C30 C31 1.383(2) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? N1 H1N 0.821(19) . ? N2 H21N 2.304(19) . ? N3 H3N 0.748(19) . ? N21 H21N 0.767(19) . ? N22 H1N 2.234(19) . ? N23 H23N 0.76(2) . ? O1 H1O 1.06(3) . ? O21 H21O 1.05(3) . ? S1 H1O 1.85(3) . ? S21 H21O 1.84(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 O1 C1 N1 115.29(13) . . ? O1 C1 C2 122.67(12) . . ? N1 C1 C2 122.04(12) . . ? C4 C2 C1 116.13(12) . . ? C4 C2 C3 118.93(12) . . ? C1 C2 C3 124.86(12) . . ? N3 C3 C2 115.81(12) . . ? N3 C3 S1 120.46(10) . . ? C2 C3 S1 123.73(10) . . ? N2 C4 C2 178.53(16) . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 119.90(14) . . ? C11 C6 N3 121.18(14) . . ? C7 C6 N3 118.73(14) . . ? C8 C7 C6 119.69(14) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C9 C8 C7 120.81(15) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 119.44(15) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 120.32(16) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C6 C11 C10 119.84(15) . . ? C6 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? O21 C21 N21 115.28(13) . . ? O21 C21 C22 122.98(13) . . ? N21 C21 C22 121.73(13) . . ? C24 C22 C21 116.26(12) . . ? C24 C22 C23 118.62(12) . . ? C21 C22 C23 125.08(12) . . ? N23 C23 C22 116.74(12) . . ? N23 C23 S21 120.30(10) . . ? C22 C23 S21 122.93(10) . . ? N22 C24 C22 179.28(17) . . ? N21 C25 H25A 109.5 . . ? N21 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N21 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C31 119.48(14) . . ? C27 C26 N23 118.23(14) . . ? C31 C26 N23 122.23(14) . . ? C26 C27 C28 120.01(16) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C29 C28 C27 120.76(17) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C28 C29 C30 119.28(16) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C29 C30 C31 120.57(16) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C26 C31 C30 119.88(15) . . ? C26 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C1 N1 C5 123.14(13) . . ? C1 N1 H1N 118.4(13) . . ? C5 N1 H1N 118.4(13) . . ? C4 N2 H21N 155.5(5) . . ? C3 N3 C6 127.90(12) . . ? C3 N3 H3N 115.7(14) . . ? C6 N3 H3N 115.6(14) . . ? C21 N21 C25 122.84(14) . . ? C21 N21 H21N 117.2(14) . . ? C25 N21 H21N 119.9(14) . . ? C24 N22 H1N 154.6(5) . . ? C23 N23 C26 128.10(12) . . ? C23 N23 H23N 117.6(14) . . ? C26 N23 H23N 114.3(14) . . ? C1 O1 H1O 107.5(15) . . ? C21 O21 H21O 104.3(15) . . ? C3 S1 H1O 84.3(9) . . ? C23 S21 H21O 83.2(8) . . ? H21O S21 H21O 0(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O21 H21O S21 1.05(3) 1.84(3) 2.8488(12) 160(2) . O1 H1O S1 1.06(3) 1.85(3) 2.8567(12) 156(2) . N21 H21N N2 0.767(19) 2.304(19) 2.9987(19) 151.1(18) . N1 H1N N22 0.821(19) 2.234(19) 2.9745(18) 150.1(17) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.245 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.076 # Attachment '12v.cif' data_12v _database_code_depnum_ccdc_archive 'CCDC 667551' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 N3 O S' _chemical_formula_sum 'C20 H21 N3 O S' _chemical_formula_weight 351.46 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 _symmetry_space_group_name_Hall 'C -2yc' 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 12.321(2) _cell_length_b 18.376(3) _cell_length_c 9.3465(16) _cell_angle_alpha 90.00 _cell_angle_beta 116.339(3) _cell_angle_gamma 90.00 _cell_volume 1896.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9679 _exptl_absorpt_correction_T_max 0.9855 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(1) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10385 _diffrn_reflns_av_R_equivalents 0.1157 _diffrn_reflns_av_sigmaI/netI 0.1722 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.99 _reflns_number_total 4082 _reflns_number_gt 2061 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 w=1/[\s^2^(Fo^2^)+(0.0200P)^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 mixed _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 0.05(13) _refine_ls_number_reflns 4082 _refine_ls_number_parameters 234 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1637 _refine_ls_R_factor_gt 0.0815 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.940 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.002 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 0.4755(5) 1.0233(3) 0.2978(6) 0.0342(13) Uani 1 1 d . . . C2 C 0.5909(4) 1.0296(3) 0.4576(5) 0.0304(12) Uani 1 1 d . . . H2 H 0.5673 1.0273 0.5448 0.037 Uiso 1 1 calc R . . C3 C 0.6705(4) 0.9640(3) 0.4708(6) 0.0388(14) Uani 1 1 d . . . C4 C 0.6504(5) 1.0994(4) 0.4668(6) 0.0440(15) Uani 1 1 d . . . C5 C 0.2761(4) 0.9627(3) 0.1714(5) 0.0338(13) Uani 1 1 d . . . H5 H 0.2397 1.0062 0.1074 0.041 Uiso 1 1 calc R . . C6 C 0.2969(5) 0.9073(3) 0.0641(6) 0.0377(14) Uani 1 1 d . . . C7 C 0.4029(5) 0.8688(3) 0.1099(6) 0.0427(15) Uani 1 1 d . . . H7 H 0.4668 0.8774 0.2099 0.051 Uiso 1 1 calc R . . C8 C 0.4167(7) 0.8173(3) 0.0098(8) 0.0622(18) Uani 1 1 d . . . H8 H 0.4891 0.7919 0.0419 0.075 Uiso 1 1 calc R . . C9 C 0.3212(8) 0.8047(4) -0.1375(9) 0.079(2) Uani 1 1 d . . . H9 H 0.3286 0.7709 -0.2066 0.095 Uiso 1 1 calc R . . C10 C 0.2147(8) 0.8426(4) -0.1819(8) 0.083(2) Uani 1 1 d . . . H10 H 0.1497 0.8333 -0.2805 0.100 Uiso 1 1 calc R . . C11 C 0.2027(6) 0.8937(3) -0.0833(6) 0.0579(18) Uani 1 1 d . . . H11 H 0.1305 0.9193 -0.1163 0.070 Uiso 1 1 calc R . . C12 C 0.1877(5) 0.9325(3) 0.2291(6) 0.0374(14) Uani 1 1 d . . . C13 C 0.2229(5) 0.8756(3) 0.3392(7) 0.0486(16) Uani 1 1 d . . . H13 H 0.3011 0.8570 0.3789 0.058 Uiso 1 1 calc R . . C14 C 0.1420(6) 0.8467(3) 0.3894(7) 0.0592(18) Uani 1 1 d . . . H14 H 0.1652 0.8085 0.4622 0.071 Uiso 1 1 calc R . . C15 C 0.0281(6) 0.8746(4) 0.3312(8) 0.070(2) Uani 1 1 d . . . H15 H -0.0258 0.8557 0.3665 0.084 Uiso 1 1 calc R . . C16 C -0.0080(6) 0.9285(4) 0.2246(8) 0.072(2) Uani 1 1 d . . . H16 H -0.0867 0.9461 0.1853 0.087 Uiso 1 1 calc R . . C17 C 0.0710(5) 0.9581(3) 0.1723(7) 0.0602(19) Uani 1 1 d . . . H17 H 0.0451 0.9958 0.0981 0.072 Uiso 1 1 calc R . . C18 C 0.7067(7) 0.8373(3) 0.5685(8) 0.065(2) Uani 1 1 d . . . H18 H 0.7173 0.8269 0.4726 0.078 Uiso 1 1 calc R . . C19 C 0.8329(7) 0.8349(5) 0.7122(8) 0.108(3) Uani 1 1 d . . . H19A H 0.8253 0.8432 0.8088 0.162 Uiso 1 1 calc R . . H19B H 0.8833 0.8720 0.7004 0.162 Uiso 1 1 calc R . . H19C H 0.8689 0.7881 0.7172 0.162 Uiso 1 1 calc R . . C20 C 0.6236(8) 0.7824(3) 0.5779(8) 0.093(3) Uani 1 1 d . . . H20A H 0.6055 0.7937 0.6653 0.140 Uiso 1 1 calc R . . H20B H 0.6608 0.7353 0.5944 0.140 Uiso 1 1 calc R . . H20C H 0.5501 0.7823 0.4801 0.140 Uiso 1 1 calc R . . N1 N 0.3881(4) 0.9849(2) 0.3097(5) 0.0344(12) Uani 1 1 d . . . H1N1 H 0.398(4) 0.964(3) 0.392(5) 0.041 Uiso 1 1 d . . . N2 N 0.6954(5) 1.1545(3) 0.4818(7) 0.0688(17) Uani 1 1 d . . . N3 N 0.6548(4) 0.9103(3) 0.5501(6) 0.0432(14) Uani 1 1 d . . . H1N3 H 0.625(5) 0.912(3) 0.592(7) 0.052 Uiso 1 1 d . . . O1 O 0.4701(3) 1.04650(18) 0.1715(4) 0.0376(10) Uani 1 1 d . . . S1 S 0.75625(13) 0.96251(9) 0.37685(15) 0.0575(5) 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 0.039(3) 0.038(4) 0.026(3) 0.005(3) 0.015(2) 0.015(3) C2 0.037(3) 0.030(3) 0.027(3) 0.004(3) 0.016(3) 0.002(3) C3 0.028(3) 0.049(4) 0.027(3) -0.010(3) 0.002(3) 0.007(3) C4 0.046(4) 0.056(4) 0.032(3) -0.014(3) 0.019(3) -0.008(3) C5 0.039(3) 0.032(3) 0.025(3) 0.003(3) 0.009(3) 0.002(3) C6 0.050(4) 0.034(4) 0.034(3) 0.009(3) 0.023(3) -0.011(3) C7 0.043(4) 0.040(4) 0.044(4) -0.008(3) 0.019(3) -0.008(3) C8 0.086(5) 0.056(5) 0.062(5) -0.006(4) 0.049(4) 0.002(4) C9 0.126(7) 0.064(6) 0.073(6) -0.027(4) 0.066(6) -0.013(5) C10 0.121(8) 0.097(7) 0.036(4) -0.022(4) 0.039(5) -0.017(5) C11 0.054(4) 0.089(5) 0.028(3) -0.011(4) 0.015(3) -0.015(4) C12 0.041(3) 0.042(4) 0.033(3) -0.010(3) 0.019(3) -0.009(3) C13 0.053(4) 0.047(4) 0.053(4) -0.008(3) 0.030(3) 0.004(3) C14 0.084(5) 0.052(4) 0.064(5) -0.018(4) 0.054(4) -0.019(4) C15 0.066(5) 0.082(6) 0.087(6) -0.010(4) 0.057(5) -0.024(4) C16 0.046(4) 0.097(6) 0.080(6) 0.018(4) 0.032(4) -0.008(4) C17 0.047(4) 0.073(5) 0.063(5) 0.015(4) 0.026(4) 0.010(4) C18 0.115(6) 0.039(4) 0.053(4) 0.010(4) 0.048(5) 0.024(4) C19 0.101(7) 0.150(8) 0.059(5) 0.013(5) 0.022(5) 0.071(6) C20 0.187(8) 0.037(4) 0.071(5) 0.009(4) 0.072(6) 0.001(6) N1 0.033(3) 0.046(3) 0.025(2) 0.013(2) 0.013(2) 0.000(2) N2 0.074(4) 0.053(4) 0.084(4) -0.013(3) 0.039(3) -0.022(3) N3 0.052(3) 0.049(3) 0.035(3) -0.001(3) 0.025(3) 0.003(3) O1 0.039(2) 0.047(3) 0.027(2) -0.0002(19) 0.0157(18) 0.0018(19) S1 0.0470(9) 0.0933(13) 0.0444(10) 0.0077(10) 0.0314(8) 0.0198(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 C1 O1 1.228(5) . ? C1 N1 1.333(6) . ? C1 C2 1.543(6) . ? C2 C4 1.460(7) . ? C2 C3 1.524(6) . ? C2 H2 0.9800 . ? C3 N3 1.300(7) . ? C3 S1 1.646(5) . ? C4 N2 1.133(6) . ? C5 N1 1.469(6) . ? C5 C12 1.520(6) . ? C5 C6 1.527(7) . ? C5 H5 0.9800 . ? C6 C11 1.375(7) . ? C6 C7 1.377(7) . ? C7 C8 1.393(7) . ? C7 H7 0.9300 . ? C8 C9 1.378(9) . ? C8 H8 0.9300 . ? C9 C10 1.377(8) . ? C9 H9 0.9300 . ? C10 C11 1.368(8) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C17 1.377(7) . ? C12 C13 1.394(6) . ? C13 C14 1.383(7) . ? C13 H13 0.9300 . ? C14 C15 1.361(8) . ? C14 H14 0.9300 . ? C15 C16 1.333(8) . ? C15 H15 0.9300 . ? C16 C17 1.380(8) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 N3 1.464(7) . ? C18 C20 1.468(8) . ? C18 C19 1.540(9) . ? C18 H18 0.9800 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N1 H1N1 0.82(4) . ? N3 H1N3 0.65(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 O1 C1 N1 124.2(5) . . ? O1 C1 C2 122.6(5) . . ? N1 C1 C2 112.9(4) . . ? C4 C2 C3 113.6(4) . . ? C4 C2 C1 110.2(4) . . ? C3 C2 C1 107.6(4) . . ? C4 C2 H2 108.4 . . ? C3 C2 H2 108.4 . . ? C1 C2 H2 108.4 . . ? N3 C3 C2 113.1(4) . . ? N3 C3 S1 125.8(4) . . ? C2 C3 S1 120.8(4) . . ? N2 C4 C2 175.8(6) . . ? N1 C5 C12 109.3(4) . . ? N1 C5 C6 113.4(4) . . ? C12 C5 C6 110.2(4) . . ? N1 C5 H5 107.9 . . ? C12 C5 H5 107.9 . . ? C6 C5 H5 107.9 . . ? C11 C6 C7 118.7(5) . . ? C11 C6 C5 117.9(5) . . ? C7 C6 C5 123.4(5) . . ? C6 C7 C8 121.5(5) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C9 C8 C7 118.7(6) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C10 C9 C8 119.6(7) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C11 C10 C9 121.1(7) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C6 120.3(6) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C17 C12 C13 118.1(5) . . ? C17 C12 C5 121.9(5) . . ? C13 C12 C5 119.9(5) . . ? C14 C13 C12 120.2(5) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 119.4(6) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C16 C15 C14 121.4(6) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 120.3(7) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 120.5(6) . . ? C12 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? N3 C18 C20 110.9(6) . . ? N3 C18 C19 110.4(6) . . ? C20 C18 C19 112.9(6) . . ? N3 C18 H18 107.5 . . ? C20 C18 H18 107.5 . . ? C19 C18 H18 107.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1 N1 C5 123.5(4) . . ? C1 N1 H1N1 122(4) . . ? C5 N1 H1N1 113(4) . . ? C3 N3 C18 126.5(5) . . ? C3 N3 H1N3 125(6) . . ? C18 N3 H1N3 109(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H1N3 O1 0.65(5) 2.45(5) 3.064(5) 158(7) 2_575 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.309 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.044