# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 886055' #TrackingRef '1_iam.cif' _audit_creation_method SHELXL-97 # 4. Text _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C10 H9 N4 O2 S), C6 H24 N6 Zn, H2 O' _chemical_formula_sum 'C26 H44 N14 O5 S2 Zn' _chemical_formula_weight 762.24 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.7895(4) _cell_length_b 15.8937(9) _cell_length_c 27.6960(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3428.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6121 _cell_measurement_theta_min 2.5630 _cell_measurement_theta_max 29.1813 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.897 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7685 _exptl_absorpt_correction_T_max 0.8203 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Incoatec microsource' _diffrn_radiation_monochromator 'Multilayer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 213634 _diffrn_reflns_av_R_equivalents 0.0812 _diffrn_reflns_av_sigmaI/netI 0.0633 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -61 _diffrn_reflns_limit_l_max 61 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 51.77 _reflns_number_total 19247 _reflns_number_gt 12930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0300P)^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 19247 _refine_ls_number_parameters 227 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0826 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1190 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 Zn1 Zn 0.0000 0.161031(9) 0.2500 0.01081(2) Uani 1 2 d S . . S1 S 0.47958(3) 0.262234(14) 0.138764(8) 0.01221(3) Uani 1 1 d . . . O1 O 0.66041(9) 0.25470(5) 0.15127(3) 0.01763(12) Uani 1 1 d . . . O2 O 0.38675(11) 0.32345(5) 0.16844(3) 0.01852(12) Uani 1 1 d . . . O3 O 0.5000 0.40136(8) 0.2500 0.0340(4) Uani 1 2 d SD . . H3O H 0.525(3) 0.3723(12) 0.2730(6) 0.051 Uiso 1 1 d D . . N1 N 0.29770(15) 0.04445(7) 0.12441(5) 0.0290(2) Uani 1 1 d . . . N2 N 0.54270(10) 0.10558(5) 0.08593(3) 0.01491(11) Uani 1 1 d . . . N3 N 0.37168(11) 0.17879(5) 0.14343(3) 0.01539(11) Uani 1 1 d . . . N4 N 0.45024(16) 0.37794(10) -0.06458(4) 0.0323(3) Uani 1 1 d D . . H4A H 0.528(2) 0.4096(12) -0.0773(7) 0.039 Uiso 1 1 d D . . H4B H 0.360(2) 0.3651(13) -0.0811(7) 0.039 Uiso 1 1 d D . . N5 N -0.27659(9) 0.14720(5) 0.24384(3) 0.01301(10) Uani 1 1 d . . . H5A H -0.3265 0.1482 0.2739 0.016 Uiso 1 1 calc R . . H5B H -0.3217 0.1904 0.2258 0.016 Uiso 1 1 calc R . . N6 N -0.00971(9) 0.06258(5) 0.19438(3) 0.01372(10) Uani 1 1 d . . . H6A H 0.0616 0.0763 0.1691 0.016 Uiso 1 1 calc R . . H6B H 0.0258 0.0120 0.2071 0.016 Uiso 1 1 calc R . . N7 N -0.01484(10) 0.26566(5) 0.30098(3) 0.01675(12) Uani 1 1 d . . . H7A H -0.1250 0.2708 0.3126 0.020 Uiso 1 1 calc R . . H7B H 0.0575 0.2562 0.3267 0.020 Uiso 1 1 calc R . . C1 C 0.40862(11) 0.10877(6) 0.11679(3) 0.01465(12) Uani 1 1 d . . . C2 C 0.32707(18) -0.02705(8) 0.10058(6) 0.0298(3) Uani 1 1 d . . . H2 H 0.2532 -0.0736 0.1062 0.036 Uiso 1 1 calc R . . C3 C 0.46029(15) -0.03641(7) 0.06801(4) 0.02234(18) Uani 1 1 d . . . H3 H 0.4792 -0.0874 0.0509 0.027 Uiso 1 1 calc R . . C4 C 0.56426(13) 0.03339(7) 0.06191(4) 0.01874(15) Uani 1 1 d . . . H4 H 0.6560 0.0298 0.0394 0.022 Uiso 1 1 calc R . . C5 C 0.46986(11) 0.29864(6) 0.07879(3) 0.01244(11) Uani 1 1 d . . . C6 C 0.32884(12) 0.27888(6) 0.04997(3) 0.01646(14) Uani 1 1 d . . . H6 H 0.2381 0.2457 0.0627 0.020 Uiso 1 1 calc R . . C7 C 0.32082(14) 0.30752(7) 0.00285(4) 0.01907(16) Uani 1 1 d . . . H7 H 0.2238 0.2943 -0.0165 0.023 Uiso 1 1 calc R . . C8 C 0.45438(14) 0.35593(7) -0.01661(3) 0.01946(16) Uani 1 1 d . . . C9 C 0.59196(14) 0.37872(8) 0.01336(4) 0.02163(18) Uani 1 1 d . . . H9 H 0.6803 0.4141 0.0013 0.026 Uiso 1 1 calc R . . C10 C 0.59966(12) 0.34984(7) 0.06064(4) 0.01750(14) Uani 1 1 d . . . H10 H 0.6937 0.3651 0.0806 0.021 Uiso 1 1 calc R . . C11 C -0.30964(11) 0.06566(6) 0.22005(3) 0.01451(12) Uani 1 1 d . . . H11A H -0.4301 0.0633 0.2087 0.017 Uiso 1 1 calc R . . H11B H -0.2914 0.0192 0.2433 0.017 Uiso 1 1 calc R . . C12 C -0.18806(12) 0.05602(7) 0.17745(3) 0.01598(13) Uani 1 1 d . . . H12A H -0.2064 0.0007 0.1618 0.019 Uiso 1 1 calc R . . H12B H -0.2114 0.1005 0.1533 0.019 Uiso 1 1 calc R . . C13 C 0.03599(16) 0.34349(7) 0.27552(5) 0.02390(19) Uani 1 1 d . . . H13A H 0.1628 0.3474 0.2743 0.029 Uiso 1 1 calc R . . H13B H -0.0078 0.3931 0.2933 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.00903(4) 0.01270(5) 0.01070(4) 0.000 0.00029(4) 0.000 S1 0.01223(7) 0.01494(8) 0.00946(6) -0.00057(6) -0.00124(5) 0.00106(6) O1 0.0145(2) 0.0227(3) 0.0158(3) 0.0029(2) -0.00544(19) 0.0003(2) O2 0.0226(3) 0.0199(3) 0.0130(2) -0.0049(2) -0.0007(2) 0.0041(2) O3 0.0692(11) 0.0150(4) 0.0178(4) 0.000 -0.0156(6) 0.000 N1 0.0277(4) 0.0207(4) 0.0386(6) -0.0074(4) 0.0192(4) -0.0098(3) N2 0.0133(2) 0.0177(3) 0.0138(3) -0.0023(2) 0.0036(2) -0.0017(2) N3 0.0162(3) 0.0159(3) 0.0141(3) -0.0011(2) 0.0049(2) -0.0009(2) N4 0.0256(4) 0.0570(8) 0.0142(3) 0.0124(4) -0.0009(3) 0.0068(5) N5 0.0112(2) 0.0160(3) 0.0118(2) -0.00029(18) 0.00066(17) 0.00012(19) N6 0.0122(2) 0.0174(3) 0.0115(2) -0.00079(19) 0.00133(19) 0.0005(2) N7 0.0141(3) 0.0178(3) 0.0184(3) -0.0038(2) -0.0003(2) 0.0005(2) C1 0.0140(3) 0.0162(3) 0.0137(3) 0.0001(2) 0.0029(2) -0.0015(2) C2 0.0290(5) 0.0199(4) 0.0405(7) -0.0076(4) 0.0141(5) -0.0100(4) C3 0.0218(4) 0.0188(4) 0.0264(5) -0.0073(3) 0.0035(3) -0.0031(3) C4 0.0170(3) 0.0209(4) 0.0183(4) -0.0052(3) 0.0044(3) -0.0022(3) C5 0.0126(2) 0.0149(3) 0.0099(2) 0.0000(2) -0.00172(19) 0.0004(2) C6 0.0154(3) 0.0200(4) 0.0140(3) 0.0009(3) -0.0046(2) -0.0016(3) C7 0.0191(4) 0.0245(4) 0.0136(3) 0.0003(3) -0.0059(3) 0.0014(3) C8 0.0190(3) 0.0274(4) 0.0120(3) 0.0036(3) -0.0006(3) 0.0068(3) C9 0.0177(4) 0.0299(5) 0.0172(4) 0.0089(3) -0.0005(3) -0.0012(3) C10 0.0150(3) 0.0223(4) 0.0152(3) 0.0038(3) -0.0025(2) -0.0029(3) C11 0.0121(3) 0.0176(3) 0.0138(3) -0.0014(2) 0.0008(2) -0.0025(2) C12 0.0143(3) 0.0226(4) 0.0110(3) -0.0031(3) -0.0005(2) -0.0007(3) C13 0.0238(4) 0.0161(4) 0.0318(5) -0.0034(4) -0.0041(4) -0.0023(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 Zn1 N5 2.1724(7) . ? Zn1 N5 2.1724(7) 3 ? Zn1 N7 2.1845(8) . ? Zn1 N7 2.1846(8) 3 ? Zn1 N6 2.1971(8) 3 ? Zn1 N6 2.1971(8) . ? S1 O1 1.4555(7) . ? S1 O2 1.4646(8) . ? S1 N3 1.5754(9) . ? S1 C5 1.7605(8) . ? O3 H3O 0.812(14) . ? N1 C2 1.3340(16) . ? N1 C1 1.3550(13) . ? N2 C4 1.3368(12) . ? N2 C1 1.3505(11) . ? N3 C1 1.3659(12) . ? N4 C8 1.3742(13) . ? N4 H4A 0.861(14) . ? N4 H4B 0.864(14) . ? N5 C11 1.4763(12) . ? N5 H5A 0.9200 . ? N5 H5B 0.9200 . ? N6 C12 1.4700(12) . ? N6 H6A 0.9200 . ? N6 H6B 0.9200 . ? N7 C13 1.4779(15) . ? N7 H7A 0.9200 . ? N7 H7B 0.9200 . ? C2 C3 1.3831(17) . ? C2 H2 0.9500 . ? C3 C4 1.3839(14) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 C10 1.3917(13) . ? C5 C6 1.3936(12) . ? C6 C7 1.3836(13) . ? C6 H6 0.9500 . ? C7 C8 1.4018(16) . ? C7 H7 0.9500 . ? C8 C9 1.4032(15) . ? C9 C10 1.3889(14) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.5208(12) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C13 1.521(3) 3 ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Zn1 N5 168.38(4) . 3 ? N5 Zn1 N7 94.32(3) . . ? N5 Zn1 N7 94.52(3) 3 . ? N5 Zn1 N7 94.52(3) . 3 ? N5 Zn1 N7 94.32(3) 3 3 ? N7 Zn1 N7 80.85(5) . 3 ? N5 Zn1 N6 90.98(3) . 3 ? N5 Zn1 N6 80.72(3) 3 3 ? N7 Zn1 N6 95.21(3) . 3 ? N7 Zn1 N6 173.45(3) 3 3 ? N5 Zn1 N6 80.72(3) . . ? N5 Zn1 N6 90.98(3) 3 . ? N7 Zn1 N6 173.45(3) . . ? N7 Zn1 N6 95.21(3) 3 . ? N6 Zn1 N6 89.17(4) 3 . ? O1 S1 O2 113.50(5) . . ? O1 S1 N3 115.31(5) . . ? O2 S1 N3 104.47(5) . . ? O1 S1 C5 107.05(4) . . ? O2 S1 C5 106.85(4) . . ? N3 S1 C5 109.33(4) . . ? C2 N1 C1 117.14(9) . . ? C4 N2 C1 116.38(8) . . ? C1 N3 S1 121.95(6) . . ? C8 N4 H4A 121.9(14) . . ? C8 N4 H4B 118.0(13) . . ? H4A N4 H4B 119.6(18) . . ? C11 N5 Zn1 107.27(5) . . ? C11 N5 H5A 110.3 . . ? Zn1 N5 H5A 110.3 . . ? C11 N5 H5B 110.3 . . ? Zn1 N5 H5B 110.3 . . ? H5A N5 H5B 108.5 . . ? C12 N6 Zn1 107.86(5) . . ? C12 N6 H6A 110.1 . . ? Zn1 N6 H6A 110.1 . . ? C12 N6 H6B 110.1 . . ? Zn1 N6 H6B 110.1 . . ? H6A N6 H6B 108.4 . . ? C13 N7 Zn1 108.34(7) . . ? C13 N7 H7A 110.0 . . ? Zn1 N7 H7A 110.0 . . ? C13 N7 H7B 110.0 . . ? Zn1 N7 H7B 110.0 . . ? H7A N7 H7B 108.4 . . ? N2 C1 N1 124.30(9) . . ? N2 C1 N3 122.37(8) . . ? N1 C1 N3 113.34(8) . . ? N1 C2 C3 122.90(10) . . ? N1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C2 C3 C4 115.62(10) . . ? C2 C3 H3 122.2 . . ? C4 C3 H3 122.2 . . ? N2 C4 C3 123.63(9) . . ? N2 C4 H4 118.2 . . ? C3 C4 H4 118.2 . . ? C10 C5 C6 119.84(8) . . ? C10 C5 S1 120.11(6) . . ? C6 C5 S1 120.01(7) . . ? C7 C6 C5 120.11(9) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.65(9) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? N4 C8 C7 119.61(11) . . ? N4 C8 C9 121.62(11) . . ? C7 C8 C9 118.75(9) . . ? C10 C9 C8 120.37(10) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C5 120.16(9) . . ? C9 C10 H10 119.9 . . ? C5 C10 H10 119.9 . . ? N5 C11 C12 109.03(7) . . ? N5 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? N5 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? N6 C12 C11 109.50(7) . . ? N6 C12 H12A 109.8 . . ? C11 C12 H12A 109.8 . . ? N6 C12 H12B 109.8 . . ? C11 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? N7 C13 C13 110.16(7) . 3 ? N7 C13 H13A 109.6 . . ? C13 C13 H13A 109.6 3 . ? N7 C13 H13B 109.6 . . ? C13 C13 H13B 109.6 3 . ? H13A C13 H13B 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N3 C1 -61.27(9) . . . . ? O2 S1 N3 C1 173.44(8) . . . . ? C5 S1 N3 C1 59.37(9) . . . . ? N5 Zn1 N5 C11 -26.84(5) 3 . . . ? N7 Zn1 N5 C11 -166.27(6) . . . . ? N7 Zn1 N5 C11 112.59(6) 3 . . . ? N6 Zn1 N5 C11 -70.96(6) 3 . . . ? N6 Zn1 N5 C11 18.04(5) . . . . ? N5 Zn1 N6 C12 11.63(6) . . . . ? N5 Zn1 N6 C12 -176.54(6) 3 . . . ? N7 Zn1 N6 C12 -29.4(3) . . . . ? N7 Zn1 N6 C12 -82.11(6) 3 . . . ? N6 Zn1 N6 C12 102.76(6) 3 . . . ? N5 Zn1 N7 C13 -107.80(7) . . . . ? N5 Zn1 N7 C13 79.76(7) 3 . . . ? N7 Zn1 N7 C13 -13.91(5) 3 . . . ? N6 Zn1 N7 C13 160.82(7) 3 . . . ? N6 Zn1 N7 C13 -67.3(3) . . . . ? C4 N2 C1 N1 -0.11(16) . . . . ? C4 N2 C1 N3 -179.75(9) . . . . ? C2 N1 C1 N2 1.8(2) . . . . ? C2 N1 C1 N3 -178.50(12) . . . . ? S1 N3 C1 N2 2.08(14) . . . . ? S1 N3 C1 N1 -177.59(9) . . . . ? C1 N1 C2 C3 -2.1(2) . . . . ? N1 C2 C3 C4 0.8(2) . . . . ? C1 N2 C4 C3 -1.39(16) . . . . ? C2 C3 C4 N2 1.08(19) . . . . ? O1 S1 C5 C10 -30.02(9) . . . . ? O2 S1 C5 C10 91.90(9) . . . . ? N3 S1 C5 C10 -155.58(8) . . . . ? O1 S1 C5 C6 152.43(8) . . . . ? O2 S1 C5 C6 -85.64(9) . . . . ? N3 S1 C5 C6 26.87(9) . . . . ? C10 C5 C6 C7 2.35(15) . . . . ? S1 C5 C6 C7 179.91(8) . . . . ? C5 C6 C7 C8 0.58(16) . . . . ? C6 C7 C8 N4 174.76(11) . . . . ? C6 C7 C8 C9 -3.48(17) . . . . ? N4 C8 C9 C10 -174.71(12) . . . . ? C7 C8 C9 C10 3.49(18) . . . . ? C8 C9 C10 C5 -0.62(17) . . . . ? C6 C5 C10 C9 -2.33(15) . . . . ? S1 C5 C10 C9 -179.88(9) . . . . ? Zn1 N5 C11 C12 -44.56(8) . . . . ? Zn1 N6 C12 C11 -39.05(9) . . . . ? N5 C11 C12 N6 57.55(10) . . . . ? Zn1 N7 C13 C13 39.28(13) . . . 3 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 51.77 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.275 _refine_diff_density_min -1.028 _refine_diff_density_rms 0.104 data_2 _database_code_depnum_ccdc_archive 'CCDC 886056' #TrackingRef '2_iam.cif' _audit_creation_method SHELXL-97 # 4. Text _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N4 O2 S' _chemical_formula_sum 'C10 H10 N4 O2 S' _chemical_formula_weight 250.28 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.6948(16) _cell_length_b 5.8197(7) _cell_length_c 14.8245(17) _cell_angle_alpha 90.00 _cell_angle_beta 115.0914(15) _cell_angle_gamma 90.00 _cell_volume 1070.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6481 _cell_measurement_theta_min 2.7710 _cell_measurement_theta_max 53.2831 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.298 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9266 _exptl_absorpt_correction_T_max 0.9539 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Incoatec microsource' _diffrn_radiation_monochromator 'multilayer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49280 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0694 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 54.16 _reflns_number_total 12966 _reflns_number_gt 8707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0440P)^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 12966 _refine_ls_number_parameters 163 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1431 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 S1 S 0.263453(14) 0.86777(3) 0.557793(14) 0.01278(3) Uani 1 1 d . . . O1 O 0.29198(5) 0.63477(12) 0.58841(5) 0.01781(9) Uani 1 1 d . . . O2 O 0.28878(5) 1.04456(13) 0.63225(5) 0.01898(10) Uani 1 1 d . . . N1 N -0.04151(5) 0.75526(12) 0.41882(5) 0.01339(8) Uani 1 1 d . . . N2 N 0.10193(5) 0.57267(13) 0.39414(5) 0.01581(9) Uani 1 1 d . . . N3 N 0.13116(5) 0.89248(12) 0.49793(5) 0.01477(9) Uani 1 1 d D . . H3A H 0.1066(12) 0.994(2) 0.5256(11) 0.018 Uiso 1 1 d D . . N4 N 0.44002(6) 1.11440(14) 0.26937(5) 0.01722(10) Uani 1 1 d D . . H4A H 0.4529(12) 0.997(2) 0.2418(11) 0.021 Uiso 1 1 d D . . H4B H 0.4031(12) 1.212(3) 0.2263(11) 0.021 Uiso 1 1 d D . . C1 C 0.06225(5) 0.73142(12) 0.43422(5) 0.01222(8) Uani 1 1 d . . . C2 C -0.11080(6) 0.60063(14) 0.35856(6) 0.01510(10) Uani 1 1 d . . . H2 H -0.1848 0.6117 0.3455 0.018 Uiso 1 1 calc R . . C3 C -0.07809(7) 0.42434(15) 0.31440(6) 0.01758(11) Uani 1 1 d . . . H3 H -0.1274 0.3135 0.2725 0.021 Uiso 1 1 calc R . . C4 C 0.03054(7) 0.41939(15) 0.33501(6) 0.01765(11) Uani 1 1 d . . . H4 H 0.0556 0.3015 0.3057 0.021 Uiso 1 1 calc R . . C5 C 0.31525(5) 0.94094(12) 0.47297(5) 0.01259(9) Uani 1 1 d . . . C6 C 0.29616(6) 1.15963(13) 0.43013(6) 0.01459(10) Uani 1 1 d . . . H6 H 0.2560 1.2693 0.4479 0.018 Uiso 1 1 calc R . . C7 C 0.33648(6) 1.21501(14) 0.36144(6) 0.01502(10) Uani 1 1 d . . . H7 H 0.3226 1.3626 0.3312 0.018 Uiso 1 1 calc R . . C8 C 0.39784(5) 1.05499(13) 0.33597(5) 0.01346(9) Uani 1 1 d . . . C9 C 0.41804(7) 0.83853(14) 0.38191(6) 0.01630(11) Uani 1 1 d . . . H9 H 0.4605 0.7300 0.3664 0.020 Uiso 1 1 calc R . . C10 C 0.37687(6) 0.78118(13) 0.44961(6) 0.01521(10) Uani 1 1 d . . . H10 H 0.3905 0.6338 0.4800 0.018 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.00996(5) 0.01482(7) 0.01444(6) -0.00105(5) 0.00604(4) -0.00028(5) O1 0.0158(2) 0.0177(2) 0.0211(2) 0.00534(19) 0.00894(17) 0.00213(17) O2 0.0152(2) 0.0242(3) 0.0181(2) -0.0075(2) 0.00755(17) -0.00270(19) N1 0.01024(16) 0.0148(2) 0.01633(19) -0.00202(16) 0.00674(14) -0.00067(14) N2 0.01321(19) 0.0159(2) 0.0199(2) -0.00410(19) 0.00852(17) 0.00072(17) N3 0.00988(16) 0.0154(2) 0.0200(2) -0.00475(18) 0.00733(16) -0.00080(15) N4 0.0156(2) 0.0207(3) 0.0174(2) 0.0020(2) 0.00898(18) -0.00009(19) C1 0.01052(18) 0.0127(2) 0.0148(2) -0.00120(17) 0.00668(15) -0.00005(15) C2 0.0119(2) 0.0159(3) 0.0180(2) -0.0019(2) 0.00683(18) -0.00180(18) C3 0.0164(3) 0.0157(3) 0.0203(3) -0.0041(2) 0.0076(2) -0.0023(2) C4 0.0178(3) 0.0156(3) 0.0203(3) -0.0043(2) 0.0088(2) 0.0003(2) C5 0.01087(18) 0.0118(2) 0.0166(2) -0.00052(17) 0.00728(17) 0.00043(15) C6 0.0135(2) 0.0127(2) 0.0191(2) 0.00063(19) 0.00835(19) 0.00249(17) C7 0.0146(2) 0.0129(2) 0.0186(2) 0.00161(19) 0.00791(19) 0.00142(18) C8 0.01179(19) 0.0147(2) 0.0145(2) -0.00033(18) 0.00620(16) -0.00080(17) C9 0.0178(3) 0.0140(3) 0.0218(3) 0.0008(2) 0.0131(2) 0.0026(2) C10 0.0165(2) 0.0120(2) 0.0211(3) 0.0011(2) 0.0118(2) 0.00214(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4307(7) . ? S1 O2 1.4396(7) . ? S1 N3 1.6513(7) . ? S1 C5 1.7384(7) . ? N1 C2 1.3377(10) . ? N1 C1 1.3473(9) . ? N2 C1 1.3326(9) . ? N2 C4 1.3391(11) . ? N3 C1 1.3804(9) . ? N3 H3A 0.864(12) . ? N4 C8 1.3826(10) . ? N4 H4A 0.853(12) . ? N4 H4B 0.845(12) . ? C2 C3 1.3895(12) . ? C2 H2 0.9500 . ? C3 C4 1.3862(12) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 C10 1.3944(10) . ? C5 C6 1.3967(11) . ? C6 C7 1.3866(11) . ? C6 H6 0.9500 . ? C7 C8 1.4089(11) . ? C7 H7 0.9500 . ? C8 C9 1.4027(11) . ? C9 C10 1.3843(11) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 119.31(4) . . ? O1 S1 N3 110.05(4) . . ? O2 S1 N3 101.68(4) . . ? O1 S1 C5 108.75(4) . . ? O2 S1 C5 109.88(4) . . ? N3 S1 C5 106.33(4) . . ? C2 N1 C1 116.26(6) . . ? C1 N2 C4 115.54(7) . . ? C1 N3 S1 125.77(5) . . ? C1 N3 H3A 119.9(10) . . ? S1 N3 H3A 111.3(10) . . ? C8 N4 H4A 112.1(10) . . ? C8 N4 H4B 114.3(11) . . ? H4A N4 H4B 110.9(14) . . ? N2 C1 N1 126.59(7) . . ? N2 C1 N3 119.08(6) . . ? N1 C1 N3 114.33(6) . . ? N1 C2 C3 122.16(7) . . ? N1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C4 C3 C2 116.22(7) . . ? C4 C3 H3 121.9 . . ? C2 C3 H3 121.9 . . ? N2 C4 C3 123.22(7) . . ? N2 C4 H4 118.4 . . ? C3 C4 H4 118.4 . . ? C10 C5 C6 120.72(7) . . ? C10 C5 S1 119.47(6) . . ? C6 C5 S1 119.81(5) . . ? C7 C6 C5 119.32(7) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 120.78(7) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? N4 C8 C9 121.02(7) . . ? N4 C8 C7 120.22(7) . . ? C9 C8 C7 118.73(7) . . ? C10 C9 C8 120.76(7) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C5 119.65(7) . . ? C9 C10 H10 120.2 . . ? C5 C10 H10 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N3 C1 -36.66(8) . . . . ? O2 S1 N3 C1 -164.07(7) . . . . ? C5 S1 N3 C1 80.94(7) . . . . ? C4 N2 C1 N1 -1.96(12) . . . . ? C4 N2 C1 N3 178.51(8) . . . . ? C2 N1 C1 N2 1.33(12) . . . . ? C2 N1 C1 N3 -179.12(7) . . . . ? S1 N3 C1 N2 -19.88(11) . . . . ? S1 N3 C1 N1 160.54(6) . . . . ? C1 N1 C2 C3 0.26(12) . . . . ? N1 C2 C3 C4 -0.99(13) . . . . ? C1 N2 C4 C3 1.07(13) . . . . ? C2 C3 C4 N2 0.29(14) . . . . ? O1 S1 C5 C10 -2.34(7) . . . . ? O2 S1 C5 C10 129.91(7) . . . . ? N3 S1 C5 C10 -120.81(6) . . . . ? O1 S1 C5 C6 178.61(6) . . . . ? O2 S1 C5 C6 -49.14(7) . . . . ? N3 S1 C5 C6 60.14(7) . . . . ? C10 C5 C6 C7 1.92(11) . . . . ? S1 C5 C6 C7 -179.04(6) . . . . ? C5 C6 C7 C8 -1.16(12) . . . . ? C6 C7 C8 N4 -178.27(7) . . . . ? C6 C7 C8 C9 -0.38(11) . . . . ? N4 C8 C9 C10 179.08(8) . . . . ? C7 C8 C9 C10 1.20(12) . . . . ? C8 C9 C10 C5 -0.46(12) . . . . ? C6 C5 C10 C9 -1.12(12) . . . . ? S1 C5 C10 C9 179.84(6) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 54.16 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.002 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.106 data_3a _database_code_depnum_ccdc_archive 'CCDC 886057' #TrackingRef '3a_iam.cif' _audit_creation_method SHELXL-97 # 4. Text _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C10 H11 N4 O2 S), C2 H6 O, 2(Cl)' _chemical_formula_sum 'C22 H28 Cl2 N8 O5 S2' _chemical_formula_weight 619.54 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.62060(10) _cell_length_b 11.3099(3) _cell_length_c 11.9166(3) _cell_angle_alpha 64.0570(10) _cell_angle_beta 79.2662(12) _cell_angle_gamma 77.3428(12) _cell_volume 661.09(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7601 _cell_measurement_theta_min 3.5087 _cell_measurement_theta_max 53.3528 _exptl_crystal_description Brick _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 0.455 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8947 _exptl_absorpt_correction_T_max 0.9432 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Incoatec microsource' _diffrn_radiation_monochromator 'multilayer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39700 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0764 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 54.28 _reflns_number_total 15483 _reflns_number_gt 11829 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0216P)^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 15483 _refine_ls_number_parameters 203 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 Cl1 Cl 0.75443(3) 0.881557(18) 0.141990(18) 0.01361(3) Uani 1 1 d . . . S1 S 0.40495(3) 0.225494(16) 0.226137(14) 0.00928(3) Uani 1 1 d . . . O1 O 0.65724(10) 0.18529(6) 0.18627(5) 0.01309(7) Uani 1 1 d . . . O2 O 0.22000(11) 0.20719(6) 0.16864(5) 0.01437(8) Uani 1 1 d . . . N1 N 0.18054(10) 0.05706(6) 0.56987(5) 0.01050(7) Uani 1 1 d D . . H1A H 0.317(3) -0.0043(18) 0.5899(19) 0.037(6) Uiso 1 1 d D . . N2 N -0.02777(11) 0.23981(6) 0.41163(5) 0.01218(7) Uani 1 1 d . . . N3 N 0.38668(10) 0.14510(6) 0.37580(5) 0.01064(7) Uani 1 1 d . . . N4 N 0.31157(11) 0.81336(6) 0.05725(6) 0.01206(7) Uani 1 1 d D . . H4A H 0.428(3) 0.8408(16) 0.0783(15) 0.018 Uiso 1 1 d D . . H4B H 0.326(3) 0.8469(16) -0.0255(12) 0.018 Uiso 1 1 d D . . H4C H 0.164(3) 0.8529(16) 0.0781(15) 0.018 Uiso 1 1 d D . . C1 C 0.17602(11) 0.15104(6) 0.44882(5) 0.00952(7) Uani 1 1 d . . . C2 C -0.01369(12) 0.04988(7) 0.65652(6) 0.01192(8) Uani 1 1 d . . . H2 H -0.0048 -0.0157 0.7402 0.014 Uiso 1 1 calc R . . C3 C -0.22519(13) 0.13876(8) 0.62223(7) 0.01406(9) Uani 1 1 d . . . H3 H -0.3669 0.1368 0.6803 0.017 Uiso 1 1 calc R . . C4 C -0.22043(13) 0.23214(8) 0.49740(7) 0.01382(9) Uani 1 1 d . . . H4 H -0.3648 0.2946 0.4718 0.017 Uiso 1 1 calc R . . C5 C 0.37105(11) 0.39828(6) 0.18586(5) 0.00955(7) Uani 1 1 d . . . C6 C 0.17428(12) 0.48169(6) 0.12051(6) 0.01112(8) Uani 1 1 d . . . H6 H 0.0535 0.4451 0.1050 0.013 Uiso 1 1 calc R . . C7 C 0.15561(12) 0.61875(6) 0.07811(6) 0.01142(8) Uani 1 1 d . . . H7 H 0.0245 0.6770 0.0318 0.014 Uiso 1 1 calc R . . C8 C 0.33202(11) 0.66913(6) 0.10463(6) 0.00990(7) Uani 1 1 d . . . C9 C 0.52681(12) 0.58667(7) 0.17162(6) 0.01179(8) Uani 1 1 d . . . H9 H 0.6433 0.6233 0.1902 0.014 Uiso 1 1 calc R . . C10 C 0.54883(12) 0.44951(7) 0.21108(6) 0.01158(8) Uani 1 1 d . . . H10 H 0.6834 0.3916 0.2547 0.014 Uiso 1 1 calc R . . O3 O -0.2158(3) 0.66050(17) 0.42088(15) 0.0245(3) Uani 0.50 1 d PD A -1 H3O H -0.2227 0.7148 0.3455 0.037 Uiso 0.50 1 calc PR A -1 C11 C -0.0105(7) 0.5538(4) 0.4299(3) 0.0213(5) Uani 0.50 1 d PD A -1 H111 H -0.0533 0.5114 0.3804 0.026 Uiso 0.50 1 d PR A -1 H112 H 0.1396 0.5891 0.3894 0.026 Uiso 0.50 1 d PR A -1 C12 C -0.0027(14) 0.4592(6) 0.5648(6) 0.0430(14) Uani 0.50 1 d P A -1 H121 H -0.1505 0.4222 0.5799 0.052 Uiso 0.50 1 d PR A -1 H122 H -0.0092 0.4995 0.6243 0.052 Uiso 0.50 1 d PR A -1 H123 H 0.1416 0.3906 0.5745 0.052 Uiso 0.50 1 d PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01152(5) 0.01251(6) 0.01616(6) -0.00551(5) -0.00067(4) -0.00215(4) S1 0.01050(5) 0.00792(5) 0.00735(4) -0.00124(4) -0.00102(4) -0.00146(4) O1 0.01242(16) 0.01204(16) 0.01076(15) -0.00305(13) 0.00128(12) 0.00035(13) O2 0.0177(2) 0.01231(17) 0.01331(17) -0.00316(14) -0.00539(15) -0.00426(15) N1 0.01006(15) 0.00989(16) 0.00810(14) -0.00102(12) -0.00031(12) -0.00116(13) N2 0.01049(16) 0.01185(18) 0.01053(16) -0.00201(14) -0.00149(13) 0.00013(14) N3 0.00975(15) 0.01050(16) 0.00789(14) -0.00102(12) -0.00004(11) -0.00094(13) N4 0.01311(18) 0.00896(16) 0.01212(17) -0.00275(14) -0.00103(14) -0.00152(14) C1 0.00948(17) 0.00889(16) 0.00804(15) -0.00152(13) -0.00086(13) -0.00156(14) C2 0.01144(19) 0.0123(2) 0.00918(17) -0.00210(15) 0.00051(14) -0.00278(16) C3 0.0116(2) 0.0159(2) 0.0120(2) -0.00419(18) 0.00038(16) -0.00149(18) C4 0.01060(19) 0.0149(2) 0.0127(2) -0.00368(18) -0.00104(16) -0.00001(17) C5 0.00950(16) 0.00847(16) 0.00862(15) -0.00140(13) -0.00164(13) -0.00137(13) C6 0.01018(18) 0.00983(18) 0.01192(18) -0.00246(15) -0.00338(14) -0.00124(14) C7 0.01061(18) 0.00959(18) 0.01199(18) -0.00217(15) -0.00369(15) -0.00037(15) C8 0.01001(17) 0.00868(17) 0.00910(16) -0.00196(14) -0.00121(13) -0.00122(14) C9 0.01111(18) 0.01013(18) 0.01300(19) -0.00279(16) -0.00351(15) -0.00182(15) C10 0.01019(18) 0.01010(18) 0.01231(19) -0.00189(15) -0.00387(15) -0.00104(15) O3 0.0249(6) 0.0227(6) 0.0189(5) -0.0048(5) -0.0008(4) 0.0008(5) C11 0.0325(12) 0.0189(10) 0.0113(7) -0.0053(6) 0.0032(7) -0.0081(9) C12 0.077(4) 0.0189(12) 0.0287(18) -0.0054(11) -0.0136(19) -0.0020(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 S1 O2 1.4410(6) . ? S1 O1 1.4487(6) . ? S1 N3 1.6037(5) . ? S1 C5 1.7708(6) . ? N1 C2 1.3455(8) . ? N1 C1 1.3681(8) . ? N1 H1A 0.902(14) . ? N2 C4 1.3327(9) . ? N2 C1 1.3462(8) . ? N3 C1 1.3402(8) . ? N4 C8 1.4591(9) . ? N4 H4A 0.898(13) . ? N4 H4B 0.883(13) . ? N4 H4C 0.900(13) . ? C2 C3 1.3742(10) . ? C2 H2 0.9500 . ? C3 C4 1.3971(10) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 C6 1.3929(9) . ? C5 C10 1.3937(9) . ? C6 C7 1.3901(9) . ? C6 H6 0.9500 . ? C7 C8 1.3891(9) . ? C7 H7 0.9500 . ? C8 C9 1.3901(9) . ? C9 C10 1.3936(9) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? O3 C11 1.457(4) . ? O3 H3O 0.8400 . ? C11 C12 1.494(4) . ? C11 H111 0.9939 . ? C11 H112 0.9652 . ? C12 H121 0.9628 . ? C12 H122 0.9891 . ? C12 H123 0.9764 . ? 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 O2 S1 O1 116.30(4) . . ? O2 S1 N3 113.90(3) . . ? O1 S1 N3 103.37(3) . . ? O2 S1 C5 106.84(3) . . ? O1 S1 C5 106.42(3) . . ? N3 S1 C5 109.71(3) . . ? C2 N1 C1 122.25(6) . . ? C2 N1 H1A 119.8(13) . . ? C1 N1 H1A 117.8(13) . . ? C4 N2 C1 117.23(6) . . ? C1 N3 S1 122.13(5) . . ? C8 N4 H4A 114.5(10) . . ? C8 N4 H4B 108.1(11) . . ? H4A N4 H4B 106.6(15) . . ? C8 N4 H4C 113.6(11) . . ? H4A N4 H4C 108.8(15) . . ? H4B N4 H4C 104.5(14) . . ? N3 C1 N2 125.28(5) . . ? N3 C1 N1 114.27(5) . . ? N2 C1 N1 120.45(5) . . ? N1 C2 C3 119.05(6) . . ? N1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 116.38(6) . . ? C2 C3 H3 121.8 . . ? C4 C3 H3 121.8 . . ? N2 C4 C3 124.64(7) . . ? N2 C4 H4 117.7 . . ? C3 C4 H4 117.7 . . ? C6 C5 C10 121.23(6) . . ? C6 C5 S1 118.52(5) . . ? C10 C5 S1 120.07(5) . . ? C7 C6 C5 119.62(6) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 C7 C6 118.86(6) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C7 C8 C9 121.97(6) . . ? C7 C8 N4 117.98(6) . . ? C9 C8 N4 120.04(6) . . ? C8 C9 C10 119.06(6) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C9 C10 C5 119.22(6) . . ? C9 C10 H10 120.4 . . ? C5 C10 H10 120.4 . . ? C11 O3 H3O 109.5 . . ? O3 C11 C12 108.2(2) . . ? O3 C11 H111 103.5 . . ? C12 C11 H111 111.0 . . ? O3 C11 H112 111.0 . . ? C12 C11 H112 114.8 . . ? H111 C11 H112 107.7 . . ? C11 C12 H121 100.7 . . ? C11 C12 H122 115.9 . . ? H121 C12 H122 109.4 . . ? C11 C12 H123 110.0 . . ? H121 C12 H123 110.9 . . ? H122 C12 H123 109.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 N3 C1 -50.10(7) . . . . ? O1 S1 N3 C1 -177.21(6) . . . . ? C5 S1 N3 C1 69.59(6) . . . . ? S1 N3 C1 N2 -12.78(10) . . . . ? S1 N3 C1 N1 167.49(5) . . . . ? C4 N2 C1 N3 -179.25(7) . . . . ? C4 N2 C1 N1 0.46(10) . . . . ? C2 N1 C1 N3 178.90(6) . . . . ? C2 N1 C1 N2 -0.84(10) . . . . ? C1 N1 C2 C3 0.82(11) . . . . ? N1 C2 C3 C4 -0.45(11) . . . . ? C1 N2 C4 C3 -0.12(12) . . . . ? C2 C3 C4 N2 0.11(12) . . . . ? O2 S1 C5 C6 5.45(6) . . . . ? O1 S1 C5 C6 130.32(5) . . . . ? N3 S1 C5 C6 -118.47(5) . . . . ? O2 S1 C5 C10 -169.74(5) . . . . ? O1 S1 C5 C10 -44.87(6) . . . . ? N3 S1 C5 C10 66.34(6) . . . . ? C10 C5 C6 C7 0.80(10) . . . . ? S1 C5 C6 C7 -174.33(5) . . . . ? C5 C6 C7 C8 -1.42(10) . . . . ? C6 C7 C8 C9 0.34(10) . . . . ? C6 C7 C8 N4 178.88(6) . . . . ? C7 C8 C9 C10 1.39(10) . . . . ? N4 C8 C9 C10 -177.12(6) . . . . ? C8 C9 C10 C5 -2.00(10) . . . . ? C6 C5 C10 C9 0.94(10) . . . . ? S1 C5 C10 C9 175.99(5) . . . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 54.28 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 1.017 _refine_diff_density_min -0.536 _refine_diff_density_rms 0.111 data_3b _database_code_depnum_ccdc_archive 'CCDC 886058' #TrackingRef '3b_iam.cif' _audit_creation_method SHELXL-97 # 4. Text _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '10 H11 N4 O2 S, 0.5(C2 H6 O2), Cl' _chemical_formula_sum 'C11 H14 Cl N4 O3 S' _chemical_formula_weight 317.77 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.62460(10) _cell_length_b 11.3239(2) _cell_length_c 11.9912(2) _cell_angle_alpha 63.8005(7) _cell_angle_beta 79.0909(10) _cell_angle_gamma 76.8061(9) _cell_volume 663.76(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4945 _cell_measurement_theta_min 3.3132 _cell_measurement_theta_max 52.9829 _exptl_crystal_description Brick _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 330 _exptl_absorpt_coefficient_mu 0.458 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8672 _exptl_absorpt_correction_T_max 0.9386 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Incoatec microsource' _diffrn_radiation_monochromator 'Multilayer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39887 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0728 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 54.10 _reflns_number_total 15441 _reflns_number_gt 11852 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0425P)^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 15441 _refine_ls_number_parameters 193 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1364 _refine_ls_wR_factor_gt 0.1242 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 Cl1 Cl 0.75817(3) 0.879198(18) 0.140898(18) 0.01269(3) Uani 1 1 d . . . S1 S 0.39982(3) 0.223884(16) 0.226937(16) 0.00911(3) Uani 1 1 d . . . O1 O 0.65151(11) 0.18182(6) 0.18659(5) 0.01301(8) Uani 1 1 d . . . O2 O 0.21331(13) 0.20727(6) 0.16991(6) 0.01428(8) Uani 1 1 d . . . N1 N 0.17909(11) 0.05788(6) 0.56963(5) 0.01049(7) Uani 1 1 d D . . H1A H 0.322(3) 0.0005(15) 0.5909(15) 0.013 Uiso 1 1 d D . . N2 N -0.03185(12) 0.24071(6) 0.41160(6) 0.01182(8) Uani 1 1 d . . . N3 N 0.38344(11) 0.14404(6) 0.37561(5) 0.01048(7) Uani 1 1 d . . . N4 N 0.31691(12) 0.81220(6) 0.05484(6) 0.01137(8) Uani 1 1 d D . . H4A H 0.320(3) 0.8433(17) -0.0266(13) 0.014 Uiso 1 1 d D . . H4B H 0.447(3) 0.8426(17) 0.0677(16) 0.014 Uiso 1 1 d D . . H4C H 0.163(3) 0.8499(17) 0.0750(16) 0.014 Uiso 1 1 d D . . C1 C 0.17294(12) 0.15133(6) 0.44867(6) 0.00939(7) Uani 1 1 d . . . C2 C -0.01433(14) 0.05189(7) 0.65636(6) 0.01192(9) Uani 1 1 d . . . H2 H -0.0043 -0.0134 0.7399 0.014 Uiso 1 1 calc R . . C3 C -0.22616(15) 0.14158(8) 0.62223(7) 0.01397(10) Uani 1 1 d . . . H3 H -0.3671 0.1407 0.6803 0.017 Uiso 1 1 calc R . . C4 C -0.22349(14) 0.23454(8) 0.49715(7) 0.01340(10) Uani 1 1 d . . . H4 H -0.3684 0.2975 0.4716 0.016 Uiso 1 1 calc R . . C5 C 0.36887(12) 0.39702(6) 0.18572(6) 0.00945(8) Uani 1 1 d . . . C6 C 0.17314(13) 0.48204(7) 0.11966(7) 0.01110(8) Uani 1 1 d . . . H6 H 0.0515 0.4466 0.1042 0.013 Uiso 1 1 calc R . . C7 C 0.15721(13) 0.61935(7) 0.07640(7) 0.01117(8) Uani 1 1 d . . . H7 H 0.0274 0.6789 0.0292 0.013 Uiso 1 1 calc R . . C8 C 0.33443(13) 0.66772(6) 0.10342(6) 0.00970(8) Uani 1 1 d . . . C9 C 0.52775(14) 0.58346(7) 0.17123(7) 0.01191(9) Uani 1 1 d . . . H9 H 0.6448 0.6189 0.1900 0.014 Uiso 1 1 calc R . . C10 C 0.54750(13) 0.44617(7) 0.21132(7) 0.01154(9) Uani 1 1 d . . . H10 H 0.6811 0.3869 0.2555 0.014 Uiso 1 1 calc R . . O3 O -0.20273(17) 0.65356(8) 0.42119(8) 0.02365(14) Uani 1 1 d . . . H3O H -0.2043 0.7097 0.3464 0.035 Uiso 1 1 calc R . . C11 C 0.0020(2) 0.54926(9) 0.43207(9) 0.01916(14) Uani 1 1 d . . . H111 H -0.0407 0.5068 0.3825 0.023 Uiso 1 1 d R . . H112 H 0.1521 0.5846 0.3915 0.023 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01129(6) 0.01105(6) 0.01495(6) -0.00545(5) -0.00110(4) -0.00051(4) S1 0.01045(6) 0.00694(5) 0.00831(5) -0.00213(4) -0.00180(4) 0.00012(4) O1 0.0126(2) 0.01120(17) 0.01155(17) -0.00396(13) 0.00061(13) 0.00180(13) O2 0.0179(2) 0.01161(17) 0.01406(19) -0.00379(15) -0.00626(16) -0.00318(15) N1 0.01027(19) 0.00892(16) 0.00921(16) -0.00182(13) -0.00115(13) 0.00021(13) N2 0.01005(19) 0.01083(18) 0.01147(18) -0.00300(14) -0.00230(14) 0.00172(14) N3 0.00971(18) 0.00958(16) 0.00860(15) -0.00156(13) -0.00106(12) 0.00051(13) N4 0.0125(2) 0.00760(15) 0.01247(18) -0.00330(14) -0.00146(14) -0.00041(13) C1 0.0093(2) 0.00790(17) 0.00919(17) -0.00236(14) -0.00154(14) -0.00020(13) C2 0.0117(2) 0.0113(2) 0.01010(19) -0.00282(16) -0.00008(15) -0.00108(16) C3 0.0110(2) 0.0150(2) 0.0132(2) -0.00494(19) 0.00002(17) 0.00001(18) C4 0.0098(2) 0.0138(2) 0.0140(2) -0.00498(19) -0.00162(17) 0.00146(17) C5 0.0094(2) 0.00770(17) 0.00937(17) -0.00212(14) -0.00236(14) 0.00025(13) C6 0.0105(2) 0.00882(18) 0.0129(2) -0.00302(16) -0.00438(16) -0.00006(15) C7 0.0106(2) 0.00831(18) 0.0129(2) -0.00267(15) -0.00440(16) 0.00070(14) C8 0.0097(2) 0.00771(17) 0.01015(18) -0.00276(14) -0.00179(14) 0.00001(14) C9 0.0110(2) 0.00949(19) 0.0146(2) -0.00380(17) -0.00451(17) -0.00045(15) C10 0.0099(2) 0.00920(19) 0.0139(2) -0.00307(16) -0.00469(16) 0.00058(15) O3 0.0244(3) 0.0192(3) 0.0187(3) -0.0037(2) -0.0024(2) 0.0039(2) C11 0.0239(4) 0.0146(3) 0.0155(3) -0.0053(2) -0.0009(2) 0.0002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4418(6) . ? S1 O1 1.4497(6) . ? S1 N3 1.5990(6) . ? S1 C5 1.7719(7) . ? N1 C2 1.3464(9) . ? N1 C1 1.3681(8) . ? N1 H1A 0.908(13) . ? N2 C4 1.3310(10) . ? N2 C1 1.3465(9) . ? N3 C1 1.3427(9) . ? N4 C8 1.4602(9) . ? N4 H4A 0.878(13) . ? N4 H4B 0.939(13) . ? N4 H4C 0.911(13) . ? C2 C3 1.3725(11) . ? C2 H2 0.9500 . ? C3 C4 1.4009(11) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 C10 1.3916(10) . ? C5 C6 1.3925(9) . ? C6 C7 1.3916(10) . ? C6 H6 0.9500 . ? C7 C8 1.3881(10) . ? C7 H7 0.9500 . ? C8 C9 1.3892(9) . ? C9 C10 1.3935(10) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? O3 C11 1.4277(13) . ? O3 H3O 0.8400 . ? C11 C11 1.5139(19) 2_566 ? C11 H111 1.0002 . ? C11 H112 0.9675 . ? 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 O2 S1 O1 115.95(4) . . ? O2 S1 N3 114.31(4) . . ? O1 S1 N3 103.47(3) . . ? O2 S1 C5 106.85(3) . . ? O1 S1 C5 106.28(3) . . ? N3 S1 C5 109.65(3) . . ? C2 N1 C1 122.28(6) . . ? C2 N1 H1A 120.2(11) . . ? C1 N1 H1A 117.5(11) . . ? C4 N2 C1 117.35(6) . . ? C1 N3 S1 122.05(5) . . ? C8 N4 H4A 106.5(12) . . ? C8 N4 H4B 116.3(11) . . ? H4A N4 H4B 105.0(15) . . ? C8 N4 H4C 110.5(11) . . ? H4A N4 H4C 101.3(15) . . ? H4B N4 H4C 115.5(15) . . ? N3 C1 N2 125.37(6) . . ? N3 C1 N1 114.21(6) . . ? N2 C1 N1 120.42(6) . . ? N1 C2 C3 119.01(6) . . ? N1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 116.46(7) . . ? C2 C3 H3 121.8 . . ? C4 C3 H3 121.8 . . ? N2 C4 C3 124.48(7) . . ? N2 C4 H4 117.8 . . ? C3 C4 H4 117.8 . . ? C10 C5 C6 121.46(6) . . ? C10 C5 S1 119.98(5) . . ? C6 C5 S1 118.39(5) . . ? C7 C6 C5 119.47(6) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C8 C7 C6 118.80(6) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C7 C8 C9 122.06(6) . . ? C7 C8 N4 117.83(6) . . ? C9 C8 N4 120.08(6) . . ? C8 C9 C10 119.07(6) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C5 C10 C9 119.11(6) . . ? C5 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C11 O3 H3O 109.5 . . ? O3 C11 C11 107.71(10) . 2_566 ? O3 C11 H111 102.1 . . ? C11 C11 H111 108.8 2_566 . ? O3 C11 H112 111.5 . . ? C11 C11 H112 117.9 2_566 . ? H111 C11 H112 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 N3 C1 -49.91(7) . . . . ? O1 S1 N3 C1 -176.92(6) . . . . ? C5 S1 N3 C1 70.02(7) . . . . ? S1 N3 C1 N2 -12.39(10) . . . . ? S1 N3 C1 N1 167.80(5) . . . . ? C4 N2 C1 N3 -179.17(7) . . . . ? C4 N2 C1 N1 0.63(11) . . . . ? C2 N1 C1 N3 178.89(7) . . . . ? C2 N1 C1 N2 -0.94(11) . . . . ? C1 N1 C2 C3 0.73(12) . . . . ? N1 C2 C3 C4 -0.25(12) . . . . ? C1 N2 C4 C3 -0.18(12) . . . . ? C2 C3 C4 N2 -0.01(13) . . . . ? O2 S1 C5 C10 -170.21(6) . . . . ? O1 S1 C5 C10 -45.83(7) . . . . ? N3 S1 C5 C10 65.40(7) . . . . ? O2 S1 C5 C6 5.12(7) . . . . ? O1 S1 C5 C6 129.51(6) . . . . ? N3 S1 C5 C6 -119.27(6) . . . . ? C10 C5 C6 C7 1.04(11) . . . . ? S1 C5 C6 C7 -174.23(6) . . . . ? C5 C6 C7 C8 -1.71(11) . . . . ? C6 C7 C8 C9 0.56(11) . . . . ? C6 C7 C8 N4 178.73(7) . . . . ? C7 C8 C9 C10 1.31(11) . . . . ? N4 C8 C9 C10 -176.82(7) . . . . ? C6 C5 C10 C9 0.84(11) . . . . ? S1 C5 C10 C9 176.03(6) . . . . ? C8 C9 C10 C5 -1.98(11) . . . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 54.10 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 1.201 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.121 data_L1- _database_code_depnum_ccdc_archive 'CCDC 886454' #TrackingRef '1_multi.cif' _audit_creation_date '30-Sep-09 T14:29:00-00:00' _audit_creation_method 'XD routine XDCIF' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_moiety '2(C10 H9 N4 O2 S), C6 H24 N6 Zn, H2 O' _chemical_formula_sum 'C26 H44 N14 O5 S2 Zn' _chemical_formula_weight 762.24 _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn _symmetry_space_group_name_Hall '-P 2n 2ab' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,1/2-Y,1/2+Z 3 -X,+Y,1/2-Z 4 1/2+X,1/2-Y,-Z 5 -X,-Y,-Z 6 1/2+X,1/2+Y,1/2-Z 7 +X,-Y,1/2+Z 8 1/2-X,1/2+Y,+Z _cell_length_a 7.7895(4) _cell_length_b 15.8937(9) _cell_length_c 27.6960(15) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3428.9(3) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.897 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7685 _exptl_absorpt_correction_T_max 0.8203 _exptl_absorpt_process_details SADABS #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Incoatec microsource' _diffrn_radiation_monochromator 'multilayer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 213634 _diffrn_reflns_av_R_equivalents 0.0812 _diffrn_reflns_av_sigmaI/netI 0.0633 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -61 _diffrn_reflns_limit_l_max 61 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 51.77 _reflns_number_total 18334 _reflns_number_gt 12930 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = q/[s^2^(Fo^2^) + (0.01 P)^2^ + 0.00 P + 0.00 + 0.00 sin(th)] where P = (0.3333 Fo^2^ + 0.6667 Fc^2^) q = 1.0 ; _refine_ls_extinction_method none _refine_ls_number_reflns 18334 _refine_ls_number_parameters 682 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.073 _refine_ls_R_factor_gt 0.044 _refine_ls_wR_factor_ref 0.085 _refine_ls_goodness_of_fit_ref 0.96 _refine_ls_shift/su_max 0.00002 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refu _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 51.77 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.431 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.118 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity ZN(1) 0 0.161079(12) 0.25 0.011 1 4 S(1) 0.47951(2) 0.262233(13) 0.138763(7) 0.012 1 8 O(1) 0.66032(14) 0.25465(8) 0.15132(4) 0.017 1 8 O(2) 0.38599(16) 0.32332(8) 0.16847(4) 0.018 1 8 O(3) 0.5 0.40138(13) 0.25 0.034 1 4 N(1) 0.2978(2) 0.04439(10) 0.12435(7) 0.03 1 8 N(2) 0.54267(12) 0.10540(7) 0.08596(4) 0.015 1 8 N(3) 0.37170(13) 0.17860(7) 0.14337(4) 0.015 1 8 N(4) 0.4496(2) 0.37791(16) -0.06452(5) 0.032 1 8 N(5) -0.27691(11) 0.14714(6) 0.24386(3) 0.013 1 8 N(6) -0.00990(12) 0.06261(6) 0.19437(3) 0.014 1 8 N(7) -0.01499(13) 0.26582(7) 0.30099(4) 0.017 1 8 C(1) 0.40868(12) 0.10882(6) 0.11683(3) 0.015 1 8 C(2) 0.3267(2) -0.02712(10) 0.10059(7) 0.03 1 8 C(3) 0.46042(17) -0.03658(8) 0.06792(5) 0.022 1 8 C(4) 0.56452(14) 0.03349(8) 0.06184(4) 0.019 1 8 C(5) 0.46977(11) 0.29863(6) 0.07883(3) 0.012 1 8 C(6) 0.32860(13) 0.27880(7) 0.05002(4) 0.017 1 8 C(7) 0.32040(15) 0.30749(8) 0.00287(4) 0.019 1 8 C(8) 0.45450(15) 0.35606(9) -0.01671(4) 0.019 1 8 C(9) 0.59230(16) 0.37875(9) 0.01333(4) 0.022 1 8 C(10) 0.59990(13) 0.34994(7) 0.06072(4) 0.018 1 8 C(11) -0.30966(12) 0.06577(7) 0.22006(3) 0.014 1 8 C(12) -0.18772(12) 0.05590(8) 0.17751(3) 0.016 1 8 C(13) 0.03648(18) 0.34360(8) 0.27562(6) 0.024 1 8 H(3O) 0.529773 0.365773 0.277785 0.023(7) 1 8 H(4A) 0.53993 0.415402 -0.079387 0.037(10) 1 8 H(4B) 0.343612 0.363583 -0.083861 0.035(9) 1 8 H(5A) -0.331431 0.148351 0.276938 0.017(6) 1 8 H(5B) -0.326043 0.194676 0.223992 0.010(5) 1 8 H(6A) 0.068541 0.077615 0.166634 0.010(6) 1 8 H(6B) 0.029201 0.0071 0.208307 0.029(7) 1 8 H(7A) -0.135954 0.271266 0.313738 0.018(8) 1 8 H(7B) 0.064497 0.255218 0.329149 0.021(7) 1 8 H(2) 0.242715 -0.08027 0.107003 0.076(14) 1 8 H(3) 0.481964 -0.094752 0.04848 0.056(10) 1 8 H(4) 0.669279 0.029264 0.03624 0.053(9) 1 8 H(6) 0.225074 0.241047 0.064577 0.043(8) 1 8 H(7) 0.210123 0.292257 -0.019282 0.041(8) 1 8 H(9) 0.69297 0.419072 -0.000522 0.032(8) 1 8 H(10) 0.707053 0.367355 0.083547 0.038(8) 1 8 H(11A) -0.442336 0.063049 0.207542 0.025(7) 1 8 H(11B) -0.289564 0.014446 0.245607 0.015(6) 1 8 H(12A) -0.208284 -0.004953 0.160226 0.025(7) 1 8 H(12B) -0.213697 0.104895 0.150905 0.019 1 8 H(13A) 0.176183 0.347755 0.2741 0.031(8) 1 8 H(13B) -0.012324 0.398204 0.295142 0.052(9) 1 8 DUM0 0 0 0 0 0 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 ZN(1) 0.00901(5) 0.01219(6) 0.01066(5) 0 0.00032(5) 0 S(1) 0.01207(6) 0.01486(7) 0.00937(6) -0.00062(5) -0.00125(5) 0.00107(5) O(1) 0.0144(3) 0.0218(4) 0.0157(3) 0.0028(3) -0.0051(3) 0.0005(3) O(2) 0.0224(4) 0.0194(4) 0.0128(3) -0.0042(3) -0.0006(3) 0.0038(3) O(3) 0.0698(15) 0.0148(6) 0.0176(6) 0 -0.0167(9) 0 N(1) 0.0283(5) 0.0203(5) 0.0410(7) -0.0093(5) 0.0219(5) -0.0110(4) N(2) 0.0134(3) 0.0170(3) 0.0140(3) -0.0028(3) 0.0041(2) -0.0022(3) N(3) 0.0165(3) 0.0156(3) 0.0140(3) -0.0014(3) 0.0050(2) -0.0009(3) N(4) 0.0254(5) 0.0572(10) 0.0147(4) 0.0137(5) -0.0005(4) 0.0072(6) N(5) 0.0108(2) 0.0159(3) 0.0119(3) -0.0005(2) 0.00054(19) 0.0005(2) N(6) 0.0123(3) 0.0174(3) 0.0114(2) -0.0012(2) 0.0014(2) 0.0008(2) N(7) 0.0140(3) 0.0174(3) 0.0189(3) -0.0046(3) -0.0002(3) 0.0005(3) C(1) 0.0140(3) 0.0157(3) 0.0141(3) -0.0004(3) 0.0040(2) -0.0018(3) C(2) 0.0293(6) 0.0192(5) 0.0427(8) -0.0091(5) 0.0165(6) -0.0103(4) C(3) 0.0216(4) 0.0182(4) 0.0276(5) -0.0078(4) 0.0045(4) -0.0036(3) C(4) 0.0175(3) 0.0194(4) 0.0194(4) -0.0060(3) 0.0052(3) -0.0029(3) C(5) 0.0122(3) 0.0152(3) 0.0099(2) -0.0001(2) -0.0017(2) -0.0003(2) C(6) 0.0154(3) 0.0206(4) 0.0136(3) 0.0013(3) -0.0051(3) -0.0023(3) C(7) 0.0192(4) 0.0251(5) 0.0131(3) 0.0010(3) -0.0059(3) 0.0007(3) C(8) 0.0188(4) 0.0282(5) 0.0115(3) 0.0041(3) -0.0009(3) 0.0059(4) C(9) 0.0180(4) 0.0305(5) 0.0167(4) 0.0093(4) -0.0007(3) -0.0017(4) C(10) 0.0150(3) 0.0228(4) 0.0148(3) 0.0046(3) -0.0026(3) -0.0034(3) C(11) 0.0121(3) 0.0176(3) 0.0135(3) -0.0013(3) 0.0007(2) -0.0025(2) C(12) 0.0146(3) 0.0229(4) 0.0107(3) -0.0032(3) -0.0005(2) -0.0007(3) C(13) 0.0228(4) 0.0163(4) 0.0324(6) -0.0036(4) -0.0048(4) -0.0023(3) #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 ZN(1) 6.02(2) 0 0 0 0.46(10) -0.064(12) 0 0 -0.03(12) -0.09(2) 0.03(7) 0 0 -0.011(17) -0.05(8) 0 0 0.054(14) 0 0 -0.01(7) 0.000(17) 0 0 -0.08(4) -0.01(12) 1 1 1 1 1 1 6 2.9826 6 2.9826 6 2.9826 6 2.9826 6 2.9826 S(1) 6.05(6) 0 0.08(3) -0.01(3) 0.12(3) 0.03(3) -0.03(3) -0.04(3) -0.09(3) 0.06(3) 0.36(3) -0.02(3) -0.01(3) 0.10(3) -0.01(3) 0.04(3) -0.31(3) 0.06(3) 0.03(3) -0.02(3) -0.03(3) 0.01(3) 0.03(3) 0.12(3) -0.07(3) -0.07(3) 0.992523 1 1 1 1 1 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 O(1) 6.41(3) 0 -0.02(2) -0.01(2) -0.03(2) -0.03(3) 0.00(2) 0.03(3) 0.00(2) -0.01(2) 0.09(2) -0.04(2) 0.00(2) 0.00(2) -0.02(2) 0.00(2) 0.02(2) 0 0 0 0 0 0 0 0 0 0.969971 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2) 6.44(3) 0 0.06(2) -0.13(2) 0.01(2) -0.09(3) 0.01(2) 0.01(3) -0.01(3) 0.03(3) 0.05(2) 0.01(2) 0.03(2) 0.00(2) 0.03(2) 0.01(2) 0.01(2) 0 0 0 0 0 0 0 0 0 0.969971 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(3) 3.32(4) 0 0 0 0.02(3) 0.06(5) 0 0 -0.02(4) 0.03(5) -0.03(3) 0 0 0.12(3) -0.07(6) 0 0 0 0 0 0 0 0 0 0 0 0.969971 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 5.26(5) 0 -0.01(3) -0.02(3) -0.06(3) 0.11(4) 0.04(4) 0.04(3) -0.22(3) -0.02(3) 0.05(3) 0.05(3) 0.00(3) 0.12(3) -0.01(3) -0.01(3) 0.01(3) 0 0 0 0 0 0 0 0 0 0.978145 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 5.18(5) 0 -0.06(2) -0.08(2) -0.09(3) 0.08(3) -0.01(3) 0.01(3) -0.12(2) 0.02(2) 0.09(3) -0.05(3) 0.01(3) 0.13(3) 0.02(2) -0.04(2) -0.01(2) 0 0 0 0 0 0 0 0 0 0.978145 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(3) 5.45(4) 0 -0.03(2) -0.01(2) -0.10(3) 0.05(3) 0.02(2) -0.03(3) 0.00(2) 0.02(2) 0.17(3) 0.02(3) 0.07(3) 0.11(2) 0.00(2) 0.02(2) -0.03(2) 0 0 0 0 0 0 0 0 0 0.978145 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(4) 5.38(7) 0 -0.04(3) 0.12(4) -0.07(4) -0.02(4) 0.10(3) -0.08(3) -0.07(4) 0.05(3) 0.14(4) 0.00(3) 0.04(3) 0.20(3) 0.01(3) -0.02(3) 0.01(3) 0 0 0 0 0 0 0 0 0 0.978145 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(5) 5.37(5) 0 -0.11(2) -0.05(2) 0.01(3) 0.00(3) 0.04(2) 0.07(2) -0.01(2) 0.00(2) 0.13(3) 0.01(2) -0.02(2) -0.01(2) 0.06(2) 0.02(2) -0.14(2) 0 0 0 0 0 0 0 0 0 0.970278 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(6) 5.46(5) 0 0.06(2) 0.03(3) 0.02(3) -0.01(3) -0.07(2) 0.05(2) -0.02(2) -0.06(2) 0.19(3) -0.01(2) 0.12(2) 0.07(2) -0.06(2) 0.01(2) -0.12(2) 0 0 0 0 0 0 0 0 0 0.970278 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(7) 5.57(6) 0 0.09(2) 0.03(3) 0.01(3) 0.03(3) -0.04(2) -0.01(2) 0.05(3) -0.07(2) 0.20(3) 0.00(2) -0.02(2) -0.01(3) -0.02(2) -0.01(2) -0.15(2) 0 0 0 0 0 0 0 0 0 0.970278 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 3.97(5) 0 0.00(2) 0.04(3) 0.04(3) 0.15(3) -0.02(3) 0.02(3) -0.19(3) 0.02(3) 0.30(4) 0.02(3) 0.04(4) 0.23(3) -0.04(3) 0.00(3) 0.04(3) 0 0 0 0 0 0 0 0 0 1.000533 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 4.04(9) 0 0.03(3) -0.01(4) -0.08(4) 0.12(4) -0.02(3) 0.01(4) -0.22(4) -0.04(4) 0.28(4) -0.03(3) -0.02(4) 0.28(4) 0.00(4) -0.07(4) -0.06(4) 0 0 0 0 0 0 0 0 0 1.000533 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 3.96(8) 0 -0.03(3) 0.01(4) -0.07(4) 0.10(4) 0.02(3) 0.05(4) -0.15(4) 0.00(4) 0.19(4) 0.00(3) -0.07(4) 0.16(3) 0.02(4) 0.06(4) -0.01(3) 0 0 0 0 0 0 0 0 0 1.000533 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 3.93(8) 0 -0.04(3) -0.01(3) -0.09(4) 0.04(3) -0.01(3) 0.00(3) -0.28(3) 0.02(3) 0.30(4) 0.05(3) 0.17(3) 0.22(3) 0.05(3) 0.10(3) -0.02(3) 0 0 0 0 0 0 0 0 0 1.000533 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 4.09(6) 0 0.02(2) 0.05(3) 0.04(3) 0.15(3) -0.02(3) -0.10(3) -0.07(3) 0.07(3) 0.21(3) -0.04(3) 0.07(4) 0.14(3) 0.00(3) 0.02(3) 0.03(3) 0 0 0 0 0 0 0 0 0 1.000533 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 3.97(8) 0 -0.03(2) 0.00(3) -0.08(4) 0.11(4) -0.05(3) 0.03(3) -0.13(3) -0.01(3) 0.22(4) -0.01(3) -0.04(3) 0.19(3) 0.02(3) -0.01(3) 0.02(3) 0 0 0 0 0 0 0 0 0 1.000533 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 4.11(8) 0 0.02(3) -0.02(4) -0.03(4) 0.04(4) 0.02(3) -0.03(3) -0.17(3) 0.01(3) 0.24(4) -0.01(3) -0.04(4) 0.21(3) 0.05(3) 0.01(3) -0.02(3) 0 0 0 0 0 0 0 0 0 1.000533 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(8) 4.07(7) 0 0.03(3) 0.02(4) -0.08(3) 0.10(3) 0.02(3) -0.02(4) -0.17(3) 0.02(3) 0.38(4) 0.01(3) -0.01(4) 0.17(4) 0.01(4) 0.02(3) -0.06(3) 0 0 0 0 0 0 0 0 0 1.000533 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(9) 4.03(8) 0 0.05(3) -0.01(4) -0.02(4) 0.08(4) 0.00(3) -0.02(3) -0.06(3) 0.00(3) 0.15(4) -0.05(3) 0.00(4) 0.16(3) -0.02(3) 0.01(4) 0.04(3) 0 0 0 0 0 0 0 0 0 1.000533 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(10) 4.06(8) 0 0.03(3) 0.05(3) -0.07(4) 0.05(4) 0.02(3) -0.01(3) -0.19(3) -0.03(3) 0.24(4) 0.03(3) -0.03(3) 0.18(3) -0.03(3) -0.02(3) -0.03(3) 0 0 0 0 0 0 0 0 0 1.000533 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(11) 4.07(7) 0 0.04(2) 0.11(3) 0.04(3) 0.02(3) 0.01(2) 0.00(2) -0.04(3) 0.00(3) 0.31(3) 0.06(3) 0.05(3) 0.03(3) -0.01(3) 0.02(3) -0.24(3) 0 0 0 0 0 0 0 0 0 0.994163 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(12) 4.28(7) 0 -0.08(3) 0.07(3) 0.11(3) 0.05(3) 0.02(3) 0.02(2) -0.07(3) 0.05(3) 0.33(3) 0.00(3) -0.08(3) -0.04(3) -0.01(3) 0.09(3) -0.29(3) 0 0 0 0 0 0 0 0 0 0.994163 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(13) 3.84(8) 0 -0.08(3) -0.11(4) -0.04(4) -0.06(4) -0.02(3) -0.01(3) -0.14(4) 0.07(3) 0.19(4) -0.02(3) 0.14(3) -0.02(3) 0.02(3) 0.04(4) -0.13(4) 0 0 0 0 0 0 0 0 0 0.994163 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(3O) 0.68(5) 0 0.05(2) 0.01(2) 0.15(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(4A) 0.68(6) 0 0 0 0.11(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(4B) 0.71(6) 0 0 0 0.18(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(5A) 0.75(5) 0 0 0 0.18(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(5B) 0.74(5) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(6A) 0.64(5) 0 0 0 0.12(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(6B) 0.81(5) 0 0 0 0.15(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(7A) 0.60(5) 0 0 0 0.09(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(7B) 0.66(5) 0 0 0 0.15(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(2) 0.90(8) 0 0 0 0.24(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(3) 1.00(7) 0 0 0 0.24(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(4) 0.97(7) 0 0 0 0.28(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(6) 0.94(7) 0 0 0 0.21(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(7) 0.91(7) 0 0 0 0.19(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(9) 0.83(6) 0 0 0 0.14(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(10) 0.88(6) 0 0 0 0.20(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(11A) 0.84(6) 0 0 0 0.10(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(11B) 0.78(5) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(12A) 0.80(6) 0 0 0 0.12(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(12B) 0.71(4) 0 0 0 0.07(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(13A) 0.82(7) 0 0 0 0.15(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(13B) 1.03(7) 0 0 0 0.26(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 ZN(1) N(5) Z ZN(1) N(7) Y S(1) O(1) Z S(1) O(2) Y O(1) S(1) Z O(1) O(2) Y O(2) S(1) Z O(2) N(3) Y O(3) H(3O) Z O(3) O(2) Y N(1) C(2) Z N(1) C(1) Y N(2) C(4) Z N(2) C(1) Y N(3) C(1) Z N(3) S(1) Y N(4) H(4B) Z N(4) H(4A) Y N(5) H(5B) Z N(5) H(5A) Y N(6) H(6A) Z N(6) H(6B) Y N(7) H(7A) Z N(7) H(7B) Y C(1) N(2) Z C(1) N(1) Y C(2) H(2) Z C(2) N(1) Y C(3) H(3) Z C(3) C(2) Y C(4) H(4) Z C(4) N(2) Y C(5) C(10) Z C(5) C(6) Y C(6) H(6) Z C(6) C(7) Y C(7) H(7) Z C(7) C(6) Y C(8) N(4) Z C(8) C(9) Y C(9) H(9) Z C(9) C(10) Y C(10) H(10) Z C(10) C(9) Y C(11) H(11A) Z C(11) H(11B) Y C(12) H(12B) Z C(12) H(12A) Y C(13) H(13B) Z C(13) H(13A) Y H(3O) O(3) Z H(3O) H(13A) Y H(4A) N(4) Z H(4A) H(4B) Y H(4B) N(4) Z H(4B) H(4A) Y H(5A) N(5) Z H(5A) H(5B) Y H(5B) N(5) Z H(5B) H(5A) Y H(6A) N(6) Z H(6A) H(6B) Y H(6B) N(6) Z H(6B) H(6A) Y H(7A) N(7) Z H(7A) H(7B) Y H(7B) N(7) Z H(7B) H(7A) Y H(2) C(2) Z H(2) N(1) Y H(3) C(3) Z H(3) C(2) Y H(4) C(4) Z H(4) N(2) Y H(6) C(6) Z H(6) C(7) Y H(7) C(7) Z H(7) C(6) Y H(9) C(9) Z H(9) C(10) Y H(10) C(10) Z H(10) C(9) Y H(11A) C(11) Z H(11A) H(11B) Y H(11B) C(11) Z H(11B) H(11A) Y H(12A) C(12) Z H(12A) H(12B) Y H(12B) C(12) Z H(12B) H(12A) Y H(13A) C(13) Z H(13A) H(13B) Y H(13B) C(13) Z H(13B) H(13A) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S(1) O(1) 1.4557(10) 1_555 1_555 yes S(1) O(2) 1.4663(11) 1_555 1_555 yes S(1) N(3) 1.5775(10) 1_555 1_555 yes S(1) C(5) 1.7595(9) 1_555 1_555 yes O(3) H(3O) 0.9830(12) 1_555 1_555 yes O(3) H(3O) 0.9830(12) 1_555 3_655 yes N(1) C(1) 1.3558(15) 1_555 1_555 yes N(1) C(2) 1.3326(19) 1_555 1_555 yes N(2) C(1) 1.3502(12) 1_555 1_555 yes N(2) C(4) 1.3349(14) 1_555 1_555 yes N(3) C(1) 1.3614(13) 1_555 1_555 yes N(4) C(8) 1.3693(16) 1_555 1_555 yes N(4) H(4A) 1.010(2) 1_555 1_555 yes N(4) H(4B) 1.0100(19) 1_555 1_555 yes N(5) H(5A) 1.0100(9) 1_555 1_555 yes N(5) H(5B) 1.0100(9) 1_555 1_555 yes N(6) C(12) 1.4656(13) 1_555 1_555 yes N(6) H(6A) 1.0100(9) 1_555 1_555 yes N(6) H(6B) 1.0100(10) 1_555 1_555 yes N(7) H(7A) 1.0100(10) 1_555 1_555 yes N(7) H(7B) 1.0100(11) 1_555 1_555 yes C(2) C(3) 1.3880(19) 1_555 1_555 yes C(2) H(2) 1.0830(13) 1_555 1_555 yes C(3) C(4) 1.3878(16) 1_555 1_555 yes C(3) H(3) 1.0830(12) 1_555 1_555 yes C(4) H(4) 1.0830(11) 1_555 1_555 yes C(5) C(6) 1.3947(12) 1_555 1_555 yes C(5) C(10) 1.3942(13) 1_555 1_555 yes C(6) C(7) 1.3847(14) 1_555 1_555 yes C(6) H(6) 1.0830(11) 1_555 1_555 yes C(7) C(8) 1.4076(17) 1_555 1_555 yes C(7) H(7) 1.0830(11) 1_555 1_555 yes C(8) C(9) 1.4052(17) 1_555 1_555 yes C(9) C(10) 1.3913(14) 1_555 1_555 yes C(9) H(9) 1.0830(13) 1_555 1_555 yes C(10) H(10) 1.0830(10) 1_555 1_555 yes C(11) C(12) 1.5217(13) 1_555 1_555 yes C(11) H(11A) 1.0910(9) 1_555 1_555 yes C(11) H(11B) 1.0910(11) 1_555 1_555 yes C(12) H(12A) 1.0910(11) 1_555 1_555 yes C(12) H(12B) 1.0910(11) 1_555 1_555 yes C(13) C(13) 1.528(3) 1_555 3_555 yes C(13) H(13A) 1.0910(14) 1_555 1_555 yes C(13) H(13B) 1.0910(14) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O(1) S(1) O(2) 113.67(7) 1_555 1_555 1_555 yes O(1) S(1) N(3) 115.22(6) 1_555 1_555 1_555 yes O(1) S(1) C(5) 107.11(5) 1_555 1_555 1_555 yes O(2) S(1) N(3) 104.36(6) 1_555 1_555 1_555 yes O(2) S(1) C(5) 106.87(6) 1_555 1_555 1_555 yes N(3) S(1) C(5) 109.29(5) 1_555 1_555 1_555 yes H(3O) O(3) H(3O) 109.69(19) 1_555 1_555 3_655 yes C(1) N(1) C(2) 117.43(12) 1_555 1_555 1_555 yes C(1) N(2) C(4) 116.74(10) 1_555 1_555 1_555 yes S(1) N(3) C(1) 122.01(7) 1_555 1_555 1_555 yes C(8) N(4) H(4A) 121.62(18) 1_555 1_555 1_555 yes C(8) N(4) H(4B) 118.60(17) 1_555 1_555 1_555 yes H(4A) N(4) H(4B) 119.09(13) 1_555 1_555 1_555 yes H(5A) N(5) H(5B) 108.70(8) 1_555 1_555 1_555 yes C(12) N(6) H(6A) 110.29(8) 1_555 1_555 1_555 yes C(12) N(6) H(6B) 110.08(9) 1_555 1_555 1_555 yes H(6A) N(6) H(6B) 108.34(8) 1_555 1_555 1_555 yes H(7A) N(7) H(7B) 108.43(10) 1_555 1_555 1_555 yes N(1) C(1) N(2) 124.02(10) 1_555 1_555 1_555 yes N(1) C(1) N(3) 113.42(10) 1_555 1_555 1_555 yes N(2) C(1) N(3) 122.56(9) 1_555 1_555 1_555 yes N(1) C(2) C(3) 122.76(12) 1_555 1_555 1_555 yes N(1) C(2) H(2) 118.83(13) 1_555 1_555 1_555 yes C(3) C(2) H(2) 118.41(13) 1_555 1_555 1_555 yes C(2) C(3) C(4) 115.52(11) 1_555 1_555 1_555 yes C(2) C(3) H(3) 122.19(12) 1_555 1_555 1_555 yes C(4) C(3) H(3) 122.29(12) 1_555 1_555 1_555 yes N(2) C(4) C(3) 123.49(10) 1_555 1_555 1_555 yes N(2) C(4) H(4) 118.48(10) 1_555 1_555 1_555 yes C(3) C(4) H(4) 118.03(10) 1_555 1_555 1_555 yes S(1) C(5) C(6) 119.96(7) 1_555 1_555 1_555 yes S(1) C(5) C(10) 120.01(7) 1_555 1_555 1_555 yes C(6) C(5) C(10) 119.98(9) 1_555 1_555 1_555 yes C(5) C(6) C(7) 120.09(10) 1_555 1_555 1_555 yes C(5) C(6) H(6) 119.96(9) 1_555 1_555 1_555 yes C(7) C(6) H(6) 119.95(9) 1_555 1_555 1_555 yes C(6) C(7) C(8) 120.65(10) 1_555 1_555 1_555 yes C(6) C(7) H(7) 119.81(12) 1_555 1_555 1_555 yes C(8) C(7) H(7) 119.54(10) 1_555 1_555 1_555 yes N(4) C(8) C(7) 119.39(14) 1_555 1_555 1_555 yes N(4) C(8) C(9) 121.94(14) 1_555 1_555 1_555 yes C(7) C(8) C(9) 118.65(10) 1_555 1_555 1_555 yes C(8) C(9) C(10) 120.45(11) 1_555 1_555 1_555 yes C(8) C(9) H(9) 119.68(10) 1_555 1_555 1_555 yes C(10) C(9) H(9) 119.88(11) 1_555 1_555 1_555 yes C(5) C(10) C(9) 120.05(10) 1_555 1_555 1_555 yes C(5) C(10) H(10) 119.99(9) 1_555 1_555 1_555 yes C(9) C(10) H(10) 119.95(10) 1_555 1_555 1_555 yes C(12) C(11) H(11A) 109.94(8) 1_555 1_555 1_555 yes C(12) C(11) H(11B) 109.61(9) 1_555 1_555 1_555 yes H(11A) C(11) H(11B) 108.21(8) 1_555 1_555 1_555 yes N(6) C(12) C(11) 109.62(8) 1_555 1_555 1_555 yes N(6) C(12) H(12A) 110.06(9) 1_555 1_555 1_555 yes N(6) C(12) H(12B) 109.79(9) 1_555 1_555 1_555 yes C(11) C(12) H(12A) 109.85(9) 1_555 1_555 1_555 yes C(11) C(12) H(12B) 109.50(9) 1_555 1_555 1_555 yes H(12A) C(12) H(12B) 108.01(8) 1_555 1_555 1_555 yes C(13) C(13) H(13A) 109.58(17) 3_555 1_555 1_555 yes C(13) C(13) H(13B) 109.30(10) 3_555 1_555 1_555 yes H(13A) C(13) H(13B) 108.57(11) 1_555 1_555 1_555 yes data_L1H _database_code_depnum_ccdc_archive 'CCDC 886668' #TrackingRef '2_multi.cif' _audit_creation_date '30-Sep-09 T14:58:04-00:00' _audit_creation_method 'XD routine XDCIF' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_moiety 'C10 H10 N4 O2 S' _chemical_formula_sum 'C10 H10 N4 O2 S' _chemical_formula_weight 250.28 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z _cell_length_a 13.6948(16) _cell_length_b 5.8197(7) _cell_length_c 14.8245(17) _cell_angle_alpha 90 _cell_angle_beta 115.091(2) _cell_angle_gamma 90 _cell_volume 1070.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6481 _cell_measurement_theta_min 2.771 _cell_measurement_theta_max 53.2831 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description brick _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.298 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9266 _exptl_absorpt_correction_T_max 0.9539 _exptl_absorpt_process_details SADABS #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Incoatec microsource' _diffrn_radiation_monochromator 'multilayer optics' _diffrn_measurement_device_type 'SMART APEX CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49280 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0694 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 54.30 _reflns_number_total 12306 _reflns_number_gt 8707 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = q/[s^2^(Fo^2^) + (0.01 P)^2^ + 0.00 P + 0.00 + 0.00 sin(th)] where P = (0.3333 Fo^2^ + 0.6667 Fc^2^) q = 1.0 ; _refine_ls_extinction_method none _refine_ls_number_reflns 12306 _refine_ls_number_parameters 478 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.070 _refine_ls_R_factor_gt 0.042 _refine_ls_wR_factor_ref 0.095 _refine_ls_goodness_of_fit_ref 0.91 _refine_ls_shift/su_max 0.00002 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 54.16 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.475 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.100 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity S(1) 0.26338(3) 0.86775(8) 0.55780(3) 0.012 1 4 O(1) 0.29198(6) 0.63474(17) 0.58841(7) 0.018 1 4 O(2) 0.28874(6) 1.04468(19) 0.63216(7) 0.019 1 4 N(1) -0.04140(5) 0.75504(13) 0.41882(5) 0.013 1 4 N(2) 0.10177(6) 0.57281(14) 0.39400(6) 0.016 1 4 N(3) 0.13113(5) 0.89262(13) 0.49798(6) 0.015 1 4 N(4) 0.44000(6) 1.11421(17) 0.26940(6) 0.017 1 4 C(1) 0.06223(5) 0.73146(12) 0.43432(5) 0.012 1 4 C(2) -0.11094(6) 0.60091(14) 0.35855(6) 0.015 1 4 C(3) -0.07820(7) 0.42413(15) 0.31424(6) 0.018 1 4 C(4) 0.03055(7) 0.41945(15) 0.33480(6) 0.018 1 4 C(5) 0.31525(5) 0.94079(12) 0.47308(5) 0.012 1 4 C(6) 0.29605(6) 1.15988(13) 0.43007(6) 0.014 1 4 C(7) 0.33654(6) 1.21523(14) 0.36143(6) 0.015 1 4 C(8) 0.39787(5) 1.05515(13) 0.33597(5) 0.013 1 4 C(9) 0.41835(6) 0.83856(14) 0.38208(6) 0.016 1 4 C(10) 0.37685(6) 0.78119(13) 0.44959(6) 0.015 1 4 H(3A) 0.101981 1.013165 0.530892 0.008(5) 1 4 H(4A) 0.45531 0.975209 0.236666 0.028(6) 1 4 H(4B) 0.39595 1.231232 0.217886 0.026(7) 1 4 H(2) -0.195314 0.613285 0.343674 0.022(6) 1 4 H(3) -0.134392 0.297677 0.266485 0.025(6) 1 4 H(4) 0.059102 0.284757 0.3016 0.021(6) 1 4 H(6) 0.250275 1.284869 0.450389 0.029(6) 1 4 H(7) 0.320599 1.383422 0.326912 0.028(6) 1 4 H(9) 0.466475 0.714659 0.364194 0.036(6) 1 4 H(10) 0.392433 0.613132 0.484236 0.037(7) 1 4 DUM0 0 0 0 0 0 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S(1) 0.00968(4) 0.01440(6) 0.01412(5) -0.00105(5) 0.00589(4) -0.00027(4) O(1) 0.0155(2) 0.0177(3) 0.0211(3) 0.0052(2) 0.0092(2) 0.0021(2) O(2) 0.0149(2) 0.0238(3) 0.0185(3) -0.0072(3) 0.0078(2) -0.0029(2) N(1) 0.01008(17) 0.0145(2) 0.0168(2) -0.00265(18) 0.00700(16) -0.00083(15) N(2) 0.01235(19) 0.0161(3) 0.0203(2) -0.0047(2) 0.00838(18) 0.00044(18) N(3) 0.00995(17) 0.0150(2) 0.0203(2) -0.00487(19) 0.00762(17) -0.00080(16) N(4) 0.0152(2) 0.0207(3) 0.0175(2) 0.0021(2) 0.00886(19) -0.0002(2) C(1) 0.00981(17) 0.0126(2) 0.01521(19) -0.00191(17) 0.00659(15) -0.00026(15) C(2) 0.01120(19) 0.0157(3) 0.0185(2) -0.0026(2) 0.00678(17) -0.00196(17) C(3) 0.0157(2) 0.0160(3) 0.0206(3) -0.0050(2) 0.0075(2) -0.0026(2) C(4) 0.0168(2) 0.0159(3) 0.0208(3) -0.0053(2) 0.0087(2) 0.0002(2) C(5) 0.01069(17) 0.0114(2) 0.0168(2) -0.00037(17) 0.00737(16) 0.00077(15) C(6) 0.0138(2) 0.0123(2) 0.0193(2) 0.00100(19) 0.00896(18) 0.00272(17) C(7) 0.0146(2) 0.0127(2) 0.0187(2) 0.00189(19) 0.00835(19) 0.00178(18) C(8) 0.01209(18) 0.0142(2) 0.0147(2) 0.00007(18) 0.00674(16) -0.00038(17) C(9) 0.0182(2) 0.0137(2) 0.0219(3) 0.0012(2) 0.0137(2) 0.00286(19) C(10) 0.0166(2) 0.0118(2) 0.0217(3) 0.0013(2) 0.0125(2) 0.00235(18) loop_ _atom_site_anharm_GC_C_label _atom_site_anharm_GC_C_111 _atom_site_anharm_GC_C_222 _atom_site_anharm_GC_C_333 _atom_site_anharm_GC_C_112 _atom_site_anharm_GC_C_122 _atom_site_anharm_GC_C_113 _atom_site_anharm_GC_C_133 _atom_site_anharm_GC_C_223 _atom_site_anharm_GC_C_233 _atom_site_anharm_GC_C_123 S(1) 0.000011(12) 0.00001(18) 0.000015(12) 0.000016(16) -0.00019(4) 0.000006(8) -0.000011(8) -0.00011(4) -0.000007(16) 0.000020(12) #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 S(1) 5.83(5) 0 0.03(2) 0.03(3) 0.04(3) 0.10(3) -0.04(2) -0.10(3) 0.11(2) -0.08(2) 0.48(3) -0.01(3) 0.11(3) 0.04(3) 0.03(3) -0.10(2) -0.32(2) 0.11(3) -0.05(3) -0.03(3) -0.07(3) 0.03(3) 0.08(3) 0.29(3) -0.20(2) 0.22(2) 1.04616 1 1 1 1 1 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 O(1) 6.50(3) 0 -0.013(17) 0.004(19) -0.02(2) -0.04(2) 0.00(2) 0.03(2) 0.05(2) 0.04(2) 0.00(2) -0.013(19) 0.00(2) -0.01(2) 0.03(2) -0.011(18) -0.019(18) 0 0 0 0 0 0 0 0 0 0.975886 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2) 6.59(3) 0 0.04(2) -0.028(17) -0.02(2) -0.08(2) 0.06(2) -0.02(2) 0.01(2) 0.04(2) 0.03(2) 0.02(2) -0.04(2) -0.02(2) -0.06(2) 0.007(19) 0.024(19) 0 0 0 0 0 0 0 0 0 0.975886 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 5.19(4) 0 0.009(18) -0.119(19) -0.03(2) 0.05(2) -0.06(2) 0.03(2) -0.126(19) 0.021(19) 0.13(2) -0.04(2) 0.00(2) 0.11(2) 0.01(2) 0.02(2) -0.02(2) 0 0 0 0 0 0 0 0 0 0.99111 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 5.24(4) 0 -0.015(19) -0.10(2) -0.05(2) 0.06(2) -0.02(2) 0.04(2) -0.17(2) -0.03(2) 0.06(2) 0.00(2) 0.04(2) 0.05(2) -0.04(2) -0.04(2) 0.01(2) 0 0 0 0 0 0 0 0 0 0.99111 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(3) 5.37(4) 0 0.007(18) 0.002(19) 0.09(2) 0.09(2) 0.01(2) 0.02(2) 0.02(2) -0.07(2) 0.17(2) 0.05(2) 0.02(2) 0.09(2) -0.02(2) 0.05(2) -0.02(2) 0 0 0 0 0 0 0 0 0 0.99111 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(4) 5.32(5) 0 0.041(18) -0.01(3) 0.07(3) 0.00(3) -0.01(2) -0.04(2) 0.02(2) 0.02(2) 0.15(3) 0.00(2) -0.03(2) -0.01(2) -0.05(2) -0.02(2) -0.08(2) 0 0 0 0 0 0 0 0 0 0.99111 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 4.04(4) 0 -0.009(19) 0.05(2) 0.06(2) 0.16(3) 0.00(2) -0.06(2) -0.25(2) 0.04(2) 0.37(3) -0.01(3) 0.05(3) 0.27(3) -0.03(3) -0.01(3) -0.03(2) 0 0 0 0 0 0 0 0 0 1.02113 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 3.99(6) 0 0.03(2) 0.00(3) -0.04(3) 0.19(3) 0.03(2) 0.05(3) -0.24(3) -0.03(2) 0.33(3) 0.02(2) 0.07(3) 0.20(3) 0.04(3) 0.05(3) -0.03(3) 0 0 0 0 0 0 0 0 0 1.02113 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 3.97(6) 0 -0.01(2) 0.02(3) -0.03(3) 0.14(3) -0.04(2) -0.03(3) -0.16(3) 0.05(3) 0.20(3) 0.06(3) 0.03(3) 0.15(3) 0.02(3) 0.02(3) -0.01(3) 0 0 0 0 0 0 0 0 0 1.02113 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 4.07(6) 0 -0.06(2) 0.01(3) -0.01(3) 0.17(3) 0.03(2) 0.04(3) -0.22(3) -0.01(2) 0.31(3) -0.03(3) 0.11(3) 0.24(3) -0.02(3) -0.04(3) -0.01(3) 0 0 0 0 0 0 0 0 0 1.02113 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 4.08(5) 0 -0.004(19) 0.05(2) 0.07(2) 0.13(3) -0.05(2) -0.08(3) -0.06(2) 0.00(2) 0.23(3) -0.02(3) -0.04(3) 0.11(3) 0.01(3) 0.00(3) -0.03(3) 0 0 0 0 0 0 0 0 0 1.02113 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 4.07(6) 0 0.03(2) -0.01(3) -0.02(3) 0.13(3) -0.04(2) -0.03(3) -0.21(3) 0.05(2) 0.25(3) 0.00(2) 0.04(3) 0.14(3) 0.03(3) 0.01(3) -0.01(3) 0 0 0 0 0 0 0 0 0 1.02113 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 4.03(6) 0 0.02(2) 0.06(3) -0.01(3) 0.08(3) -0.01(2) 0.02(3) -0.14(2) 0.05(2) 0.26(3) 0.02(2) -0.01(3) 0.17(3) -0.05(3) 0.00(3) -0.04(3) 0 0 0 0 0 0 0 0 0 1.02113 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(8) 3.95(5) 0 -0.03(2) -0.02(3) -0.05(2) 0.12(3) 0.05(2) -0.02(3) -0.25(2) -0.01(2) 0.30(3) -0.01(3) 0.05(4) 0.21(3) -0.02(3) 0.02(3) 0.04(3) 0 0 0 0 0 0 0 0 0 1.02113 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(9) 3.95(6) 0 -0.08(2) -0.01(3) -0.09(3) 0.07(3) 0.03(2) -0.05(3) -0.17(3) -0.06(3) 0.17(3) -0.04(2) 0.02(3) 0.21(3) 0.03(3) 0.00(3) 0.03(3) 0 0 0 0 0 0 0 0 0 1.02113 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(10) 3.98(6) 0 0.01(2) 0.03(3) -0.02(3) 0.06(3) 0.07(2) 0.00(3) -0.21(2) -0.10(2) 0.25(3) -0.02(2) -0.04(3) 0.17(3) 0.08(3) -0.04(3) -0.02(3) 0 0 0 0 0 0 0 0 0 1.02113 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(3A) 0.60(4) 0 -0.016(17) 0.019(18) 0.09(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(4A) 0.78(5) 0 0 0 0.17(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(4B) 0.73(5) 0 -0.02(2) 0.00(2) 0.15(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(2) 0.74(5) 0 0 0 0.18(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(3) 0.75(5) 0 0 0 0.18(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(4) 0.71(5) 0 0 0 0.13(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(6) 0.85(5) 0 0 0 0.16(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(7) 0.86(5) 0 0 0 0.14(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(9) 0.94(5) 0 0 0 0.25(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(10) 0.90(6) 0 0 0 0.21(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 S(1) O(1) Z S(1) O(2) Y O(1) S(1) Z O(1) O(2) Y O(2) S(1) Z O(2) H(3A) Y N(1) C(2) Z N(1) C(1) Y N(2) C(1) Z N(2) C(4) Y N(3) H(3A) Z N(3) C(1) Y N(4) H(4B) Z N(4) H(4A) Y C(1) N(2) Z C(1) N(1) Y C(2) H(2) Z C(2) N(1) Y C(3) H(3) Z C(3) C(4) Y C(4) H(4) Z C(4) N(2) Y C(5) C(10) Z C(5) C(6) Y C(6) H(6) Z C(6) C(7) Y C(7) H(7) Z C(7) C(6) Y C(8) N(4) Z C(8) C(9) Y C(9) H(9) Z C(9) C(10) Y C(10) H(10) Z C(10) C(9) Y H(3A) N(3) Z H(3A) C(1) Y H(4A) N(4) Z H(4A) H(4B) Y H(4B) N(4) Z H(4B) H(4A) Y H(2) C(2) Z H(2) N(1) Y H(3) C(3) Z H(3) C(4) Y H(4) C(4) Z H(4) N(2) Y H(6) C(6) Z H(6) C(7) Y H(7) C(7) Z H(7) C(6) Y H(9) C(9) Z H(9) C(10) Y H(10) C(10) Z H(10) C(9) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S(1) O(1) 1.4309(10) 1_555 1_555 yes S(1) O(2) 1.4392(9) 1_555 1_555 yes S(1) N(3) 1.6508(7) 1_555 1_555 yes S(1) C(5) 1.7377(8) 1_555 1_555 yes N(1) C(1) 1.3451(8) 1_555 1_555 yes N(1) C(2) 1.3373(10) 1_555 1_555 yes N(2) C(1) 1.3332(9) 1_555 1_555 yes N(2) C(4) 1.3387(11) 1_555 1_555 yes N(3) C(1) 1.3803(9) 1_555 1_555 yes N(3) H(3A) 1.0270(7) 1_555 1_555 yes N(4) C(8) 1.3813(10) 1_555 1_555 yes N(4) H(4A) 1.0100(10) 1_555 1_555 yes N(4) H(4B) 1.0100(9) 1_555 1_555 yes C(2) C(3) 1.3930(11) 1_555 1_555 yes C(2) H(2) 1.0830(7) 1_555 1_555 yes C(3) C(4) 1.3881(11) 1_555 1_555 yes C(3) H(3) 1.0830(8) 1_555 1_555 yes C(4) H(4) 1.0830(8) 1_555 1_555 yes C(5) C(6) 1.3997(10) 1_555 1_555 yes C(5) C(10) 1.3945(9) 1_555 1_555 yes C(6) C(7) 1.3875(10) 1_555 1_555 yes C(6) H(6) 1.0830(7) 1_555 1_555 yes C(7) C(8) 1.4089(10) 1_555 1_555 yes C(7) H(7) 1.0830(8) 1_555 1_555 yes C(8) C(9) 1.4043(11) 1_555 1_555 yes C(9) C(10) 1.3851(10) 1_555 1_555 yes C(9) H(9) 1.0830(7) 1_555 1_555 yes C(10) H(10) 1.0830(8) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O(1) S(1) O(2) 119.37(6) 1_555 1_555 1_555 yes O(1) S(1) N(3) 110.11(5) 1_555 1_555 1_555 yes O(1) S(1) C(5) 108.68(5) 1_555 1_555 1_555 yes O(2) S(1) N(3) 101.67(5) 1_555 1_555 1_555 yes O(2) S(1) C(5) 109.80(5) 1_555 1_555 1_555 yes N(3) S(1) C(5) 106.37(4) 1_555 1_555 1_555 yes C(1) N(1) C(2) 116.52(6) 1_555 1_555 1_555 yes C(1) N(2) C(4) 115.73(7) 1_555 1_555 1_555 yes S(1) N(3) C(1) 125.72(6) 1_555 1_555 1_555 yes S(1) N(3) H(3A) 111.32(5) 1_555 1_555 1_555 yes C(1) N(3) H(3A) 119.88(6) 1_555 1_555 1_555 yes C(8) N(4) H(4A) 112.25(8) 1_555 1_555 1_555 yes C(8) N(4) H(4B) 114.30(7) 1_555 1_555 1_555 yes H(4A) N(4) H(4B) 110.85(8) 1_555 1_555 1_555 yes N(1) C(1) N(2) 126.42(7) 1_555 1_555 1_555 yes N(1) C(1) N(3) 114.41(6) 1_555 1_555 1_555 yes N(2) C(1) N(3) 119.16(6) 1_555 1_555 1_555 yes N(1) C(2) C(3) 122.01(7) 1_555 1_555 1_555 yes N(1) C(2) H(2) 119.17(7) 1_555 1_555 1_555 yes C(3) C(2) H(2) 118.82(7) 1_555 1_555 1_555 yes C(2) C(3) C(4) 116.16(7) 1_555 1_555 1_555 yes C(2) C(3) H(3) 121.91(7) 1_555 1_555 1_555 yes C(4) C(3) H(3) 121.94(8) 1_555 1_555 1_555 yes N(2) C(4) C(3) 123.13(7) 1_555 1_555 1_555 yes N(2) C(4) H(4) 118.51(7) 1_555 1_555 1_555 yes C(3) C(4) H(4) 118.36(8) 1_555 1_555 1_555 yes S(1) C(5) C(6) 119.78(5) 1_555 1_555 1_555 yes S(1) C(5) C(10) 119.57(6) 1_555 1_555 1_555 yes C(6) C(5) C(10) 120.65(6) 1_555 1_555 1_555 yes C(5) C(6) C(7) 119.29(6) 1_555 1_555 1_555 yes C(5) C(6) H(6) 120.28(7) 1_555 1_555 1_555 yes C(7) C(6) H(6) 120.43(7) 1_555 1_555 1_555 yes C(6) C(7) C(8) 120.80(7) 1_555 1_555 1_555 yes C(6) C(7) H(7) 119.56(7) 1_555 1_555 1_555 yes C(8) C(7) H(7) 119.64(7) 1_555 1_555 1_555 yes N(4) C(8) C(7) 120.27(7) 1_555 1_555 1_555 yes N(4) C(8) C(9) 120.90(7) 1_555 1_555 1_555 yes C(7) C(8) C(9) 118.80(6) 1_555 1_555 1_555 yes C(8) C(9) C(10) 120.64(7) 1_555 1_555 1_555 yes C(8) C(9) H(9) 119.67(7) 1_555 1_555 1_555 yes C(10) C(9) H(9) 119.68(7) 1_555 1_555 1_555 yes C(5) C(10) C(9) 119.79(7) 1_555 1_555 1_555 yes C(5) C(10) H(10) 120.10(7) 1_555 1_555 1_555 yes C(9) C(10) H(10) 120.11(7) 1_555 1_555 1_555 yes data_L1H2 _database_code_depnum_ccdc_archive 'CCDC 886669' #TrackingRef '3b_multi.cif' _audit_creation_date '30-Sep-09 T15:12:29-00:00' _audit_creation_method 'XD routine XDCIF' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_moiety 'C10 H11 N4 O2 S, 0.5(C2 H6 O2), Cl' _chemical_formula_sum 'C11 H14 Cl N4 O3 S' _chemical_formula_weight 317.77 _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z _cell_length_a 5.62460(10) _cell_length_b 11.3239(2) _cell_length_c 11.9912(2) _cell_angle_alpha 63.8000(10) _cell_angle_beta 79.0910(10) _cell_angle_gamma 76.8060(10) _cell_volume 663.76(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4945 _cell_measurement_theta_min 3.3132 _cell_measurement_theta_max 52.9829 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 330 _exptl_absorpt_coefficient_mu 0.458 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8940 _exptl_absorpt_correction_T_max 0.9428 _exptl_absorpt_process_details SADABS #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Incoatec microsource' _diffrn_radiation_monochromator 'multilayer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39887 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0728 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 54.24 _reflns_number_total 15167 _reflns_number_gt 11852 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = q/[s^2^(Fo^2^) + (0.01 P)^2^ + 0.00 P + 0.00 + 0.00 sin(th)] where P = (0.3333 Fo^2^ + 0.6667 Fc^2^) q = 1.0 ; _refine_ls_extinction_method none _refine_ls_number_reflns 15167 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.060 _refine_ls_R_factor_gt 0.041 _refine_ls_wR_factor_ref 0.106 _refine_ls_goodness_of_fit_ref 0.99 _refine_ls_shift/su_max 0.00001 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 54.10 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.529 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.109 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity CL(1) 0.75825(7) 0.87922(4) 0.14071(3) 0.012 1 2 S(1) 0.39973(7) 0.22406(3) 0.22676(3) 0.009 1 2 O(1) 0.65103(10) 0.18189(5) 0.18640(5) 0.013 1 2 O(2) 0.21359(11) 0.20742(5) 0.16974(5) 0.014 1 2 O(3) -0.20201(15) 0.65354(7) 0.42093(7) 0.023 1 2 N(1) 0.17897(10) 0.05783(5) 0.56972(5) 0.01 1 2 N(2) -0.03178(11) 0.24052(6) 0.41160(5) 0.012 1 2 N(3) 0.38316(10) 0.14423(5) 0.37548(5) 0.01 1 2 N(4) 0.31690(11) 0.81229(5) 0.05471(5) 0.011 1 2 C(1) 0.17287(11) 0.15139(6) 0.44868(5) 0.009 1 2 C(2) -0.01419(12) 0.05183(6) 0.65653(6) 0.012 1 2 C(3) -0.22658(13) 0.14151(7) 0.62235(6) 0.014 1 2 C(4) -0.22380(13) 0.23444(7) 0.49712(7) 0.013 1 2 C(5) 0.36872(11) 0.39702(6) 0.18561(5) 0.009 1 2 C(6) 0.17312(12) 0.48206(6) 0.11962(6) 0.011 1 2 C(7) 0.15702(12) 0.61937(6) 0.07629(6) 0.011 1 2 C(8) 0.33455(11) 0.66790(6) 0.10330(5) 0.01 1 2 C(9) 0.52810(12) 0.58357(6) 0.17101(6) 0.012 1 2 C(10) 0.54765(12) 0.44622(6) 0.21119(6) 0.011 1 2 C(11) 0.00185(18) 0.54925(8) 0.43185(8) 0.019 1 2 H(1A) 0.340556 -0.006847 0.593606 0.020(6) 1 2 H(4A) 0.321105 0.84895 -0.041325 0.011(4) 1 2 H(4B) 0.460278 0.845841 0.069018 0.007(4) 1 2 H(4C) 0.142261 0.854957 0.077844 0.010(4) 1 2 H(2) -0.002929 -0.022528 0.75157 0.037(5) 1 2 H(3) -0.386921 0.140542 0.688505 0.034(5) 1 2 H(4) -0.388811 0.306371 0.468044 0.044(6) 1 2 H(6) 0.034454 0.441628 0.102088 0.006(3) 1 2 H(7) 0.009101 0.68729 0.022588 0.021(4) 1 2 H(9) 0.661416 0.623954 0.192662 0.016(4) 1 2 H(10) 0.700004 0.378557 0.261789 0.023(4) 1 2 H(3O) -0.204533 0.71901 0.33398 0.040(7) 1 2 H(111) -0.044655 0.502935 0.377965 0.045(8) 1 2 H(112) 0.171019 0.589047 0.386419 0.042(6) 1 2 DUM0 0 0 0 0 0 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 CL(1) 0.01109(5) 0.01092(5) 0.01475(5) -0.00545(4) -0.00113(4) -0.00042(4) S(1) 0.01014(5) 0.00678(4) 0.00812(4) -0.00211(3) -0.00174(3) 0.00019(3) O(1) 0.01314(18) 0.01078(15) 0.01127(15) -0.00396(12) 0.00004(12) 0.00174(12) O(2) 0.0177(2) 0.01179(16) 0.01378(17) -0.00385(13) -0.00639(15) -0.00315(14) O(3) 0.0233(3) 0.0183(2) 0.0190(2) -0.00420(19) -0.0026(2) 0.0034(2) N(1) 0.00983(17) 0.00891(14) 0.00934(14) -0.00189(12) -0.00130(12) 0.00036(12) N(2) 0.00969(17) 0.01106(16) 0.01101(16) -0.00275(13) -0.00229(13) 0.00189(12) N(3) 0.00930(16) 0.00948(15) 0.00867(14) -0.00157(12) -0.00117(11) 0.00062(12) N(4) 0.01229(18) 0.00757(14) 0.01232(16) -0.00325(12) -0.00161(13) -0.00030(12) C(1) 0.00885(18) 0.00799(15) 0.00900(16) -0.00218(12) -0.00146(12) 0.00010(12) C(2) 0.0112(2) 0.01108(18) 0.00996(17) -0.00251(14) -0.00017(14) -0.00055(14) C(3) 0.0106(2) 0.0151(2) 0.0129(2) -0.00469(17) 0.00018(15) 0.00017(16) C(4) 0.0094(2) 0.0141(2) 0.0135(2) -0.00475(17) -0.00155(15) 0.00187(15) C(5) 0.00919(18) 0.00756(15) 0.00943(16) -0.00208(12) -0.00267(13) 0.00029(12) C(6) 0.01039(19) 0.00868(16) 0.01286(18) -0.00293(14) -0.00487(14) 0.00008(13) C(7) 0.0107(2) 0.00792(16) 0.01311(19) -0.00264(14) -0.00484(15) 0.00077(13) C(8) 0.00952(18) 0.00773(15) 0.01015(16) -0.00274(13) -0.00221(13) 0.00015(12) C(9) 0.0110(2) 0.00900(17) 0.0150(2) -0.00372(15) -0.00490(16) -0.00038(14) C(10) 0.00995(19) 0.00873(17) 0.01428(19) -0.00307(15) -0.00521(15) 0.00084(13) C(11) 0.0238(3) 0.0146(2) 0.0156(2) -0.00554(19) -0.0012(2) 0.0002(2) loop_ _atom_site_anharm_GC_C_label _atom_site_anharm_GC_C_111 _atom_site_anharm_GC_C_222 _atom_site_anharm_GC_C_333 _atom_site_anharm_GC_C_112 _atom_site_anharm_GC_C_122 _atom_site_anharm_GC_C_113 _atom_site_anharm_GC_C_133 _atom_site_anharm_GC_C_223 _atom_site_anharm_GC_C_233 _atom_site_anharm_GC_C_123 Cl(1) -0.00025(18) -0.00003(2) -0.00011(2) 0.00015(5) 0.00007(2) -0.00014(5) 0.00005(2) 0.000000(15) 0.000009(14) -0.000028(17) S(1) -0.00068(17) 0.00004(2) -0.000128(18) 0.00021(4) 0.00003(2) 0.00008(4) 0.00003(2) -0.000052(12) 0.000062(12) -0.000045(15) #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 CL(1) 7.7342 0 -0.044 -0.0004 0.001 0.2257 0.1359 -0.1209 0.0213 0.066 -0.0001 -0.003 0.0189 -0.0217 -0.0319 0.0026 -0.0324 0.0083 0.0677 0.0006 0.0317 0.0509 -0.0396 -0.2658 -0.091 0.0659 1.038873 1 1 1 1 1 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714 S(1) 5.8697 0 -0.0125 0.1973 0.0549 0.2762 0.1326 -0.0738 -0.1855 -0.0071 0.4619 -0.0131 0.0347 0.142 -0.0213 0.0734 -0.3865 0.0178 -0.0314 0.0599 -0.0131 0.0285 -0.0408 0.4421 0.1237 0.1107 1.064386 1 1 1 1 1 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 O(1) 6.3974 0 -0.0323 -0.0003 -0.1668 -0.1877 -0.0438 -0.0652 0.016 -0.0767 -0.0231 -0.0318 -0.0114 0.0087 -0.0061 -0.0118 0.0125 0 0 0 0 0 0 0 0 0 0.983522 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2) 6.4652 0 0.0004 0.0027 -0.0583 0.0649 0.0389 -0.0082 -0.0155 -0.0088 0.007 0.036 -0.0236 0.0135 -0.0212 -0.026 0.0164 0 0 0 0 0 0 0 0 0 0.983522 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(3) 6.4893 0 -0.0639 -0.1333 0.0299 -0.0845 -0.0497 -0.0108 0.1006 -0.014 0.0771 0.075 -0.0159 -0.0014 -0.0005 -0.09 -0.0107 0 0 0 0 0 0 0 0 0 0.941083 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 5.3882 0 -0.0021 -0.0088 0.0647 0.1011 0.0737 -0.0179 0.0285 0.0156 0.1984 0.0284 -0.0042 0.1092 -0.0469 -0.0455 -0.001 0 0 0 0 0 0 0 0 0 0.987832 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 5.3253 0 -0.0345 -0.1091 -0.0366 0.0475 0.0017 0.0243 -0.1118 -0.0837 0.0822 -0.0155 0.0354 0.0425 0.0122 0.0042 -0.0601 0 0 0 0 0 0 0 0 0 0.987832 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(3) 5.3856 0 0.0008 -0.089 -0.0939 -0.0403 -0.0457 0.0742 -0.0268 -0.0206 0.1035 0.0127 -0.0424 0.0131 -0.0485 -0.0146 -0.0057 0 0 0 0 0 0 0 0 0 0.987832 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(4) 5.5629 0 -0.0207 0.0245 0.0089 0.0112 0.0418 0.0567 -0.0427 0.0381 0.1978 -0.0325 -0.0401 -0.0249 -0.0227 0.018 -0.2063 0 0 0 0 0 0 0 0 0 0.987832 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 3.9546 0 0.0292 0.0218 0.041 0.1089 -0.0157 -0.0496 -0.1851 0.0624 0.3388 -0.0214 0.1156 0.22 -0.0475 0.0114 0.0784 0 0 0 0 0 0 0 0 0 1.028585 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 3.8425 0 0.0367 -0.0206 -0.0199 0.0992 -0.0427 0.1341 -0.1974 0.012 0.3052 0.0582 0.1191 0.2346 0.0331 0.0026 -0.0505 0 0 0 0 0 0 0 0 0 1.028585 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 4.0201 0 -0.0096 0.0232 -0.0617 0.096 0.0162 -0.0175 -0.0981 -0.054 0.2047 0.0316 0.0044 0.1931 -0.0052 -0.0007 -0.0256 0 0 0 0 0 0 0 0 0 1.028585 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 3.9115 0 0.0463 -0.0236 -0.0237 0.1299 -0.0758 0.0142 -0.1897 -0.0883 0.2662 -0.0065 0.0398 0.198 -0.0004 0.0029 0.0454 0 0 0 0 0 0 0 0 0 1.028585 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 4.0732 0 -0.0002 -0.0319 0.011 0.1636 -0.0447 -0.1086 -0.1129 -0.0069 0.1824 -0.0403 -0.0482 0.1314 -0.0001 -0.0125 0.0032 0 0 0 0 0 0 0 0 0 1.028585 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 3.9284 0 -0.0218 -0.0572 0.0098 0.114 -0.1008 0.1194 -0.1424 -0.0246 0.2593 -0.0353 -0.0153 0.2119 0.0099 0.0054 -0.0218 0 0 0 0 0 0 0 0 0 1.028585 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 4.0319 0 0.0063 -0.0425 -0.0398 0.1216 -0.0268 -0.0248 -0.2046 0.048 0.2555 0.0531 -0.0022 0.168 0.0182 0.0521 -0.0007 0 0 0 0 0 0 0 0 0 1.028585 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(8) 4.068 0 0.0104 0.1621 0.0719 0.1448 0.0497 -0.1702 -0.1166 -0.0142 0.2595 -0.0035 0.0529 0.2178 0.0431 0.0225 0.0107 0 0 0 0 0 0 0 0 0 1.028585 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(9) 3.9921 0 -0.008 -0.0215 0.0411 0.1601 -0.0267 0.0404 -0.1816 -0.0054 0.3126 0.0053 -0.0442 0.1871 -0.0468 0.0039 0.0386 0 0 0 0 0 0 0 0 0 1.028585 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(10) 3.9362 0 -0.0455 0.0443 0.0322 0.1678 -0.0094 -0.0359 -0.1723 -0.0677 0.2723 -0.0233 0.0265 0.1545 0.0001 -0.015 0.0134 0 0 0 0 0 0 0 0 0 1.028585 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(11) 4.2229 0 0.0676 0.0825 -0.0372 -0.0801 0.0639 -0.0683 -0.092 -0.0202 0.1574 -0.0117 -0.2675 -0.1294 0.0086 -0.139 -0.2315 0 0 0 0 0 0 0 0 0 0.944269 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(1A) 0.5849 0 -0.1144 0.0224 0.0734 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(4A) 0.6374 0 0.0759 -0.0307 0.125 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(4B) 0.598 0 -0.0186 -0.1374 0.1034 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(4C) 0.6282 0 -0.0515 -0.0933 0.1004 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(2) 0.8272 0 0 0 0.2666 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(3) 0.9119 0 0 0 0.1664 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(4) 0.7882 0 0 0 0.2122 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(6) 0.7123 0 0 0 0.1871 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(7) 0.871 0 0 0 0.1949 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(9) 0.7575 0 0 0 0.0982 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(10) 0.7956 0 0 0 0.1686 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(3O) 0.774 0 0.0562 0.0366 0.072 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(111) 0.6861 0 0 0 -0.0086 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(112) 0.8276 0 0 0 0.1104 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.176139 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 CL(1) H(4B) Z CL(1) H(9) Y S(1) O(2) Z S(1) O(1) Y O(1) S(1) Z O(1) N(3) Y O(2) S(1) Z O(2) O(1) Y O(3) H(3O) Z O(3) C(11) Y N(1) H(1A) Z N(1) C(2) Y N(2) C(4) Z N(2) C(1) Y N(3) C(1) Z N(3) S(1) Y N(4) H(4A) Z N(4) H(4C) Y C(1) N(3) Z C(1) N(2) Y C(2) H(2) Z C(2) N(1) Y C(3) H(3) Z C(3) C(2) Y C(4) H(4) Z C(4) N(2) Y C(5) C(10) Z C(5) C(6) Y C(6) H(6) Z C(6) C(7) Y C(7) H(7) Z C(7) C(8) Y C(8) C(7) Z C(8) C(9) Y C(9) H(9) Z C(9) C(8) Y C(10) H(10) Z C(10) C(5) Y C(11) H(112) Z C(11) H(111) Y H(1A) N(1) Z H(1A) C(1) Y H(4A) N(4) Z H(4A) H(4C) Y H(4B) N(4) Z H(4B) H(4A) Y H(4C) N(4) Z H(4C) H(4A) Y H(2) C(2) Z H(2) N(1) Y H(3) C(3) Z H(3) C(2) Y H(4) C(4) Z H(4) N(2) Y H(6) C(6) Z H(6) C(7) Y H(7) C(7) Z H(7) C(8) Y H(9) C(9) Z H(9) C(8) Y H(10) C(10) Z H(10) C(5) Y H(3O) O(3) Z H(3O) C(11) Y H(111) C(11) Z H(111) H(112) Y H(112) C(11) Z H(112) H(111) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S(1) O(1) 1.4481(6) 1_555 1_555 yes S(1) O(2) 1.4401(6) 1_555 1_555 yes S(1) N(3) 1.5994(6) 1_555 1_555 yes S(1) C(5) 1.7702(7) 1_555 1_555 yes O(3) C(11) 1.4243(11) 1_555 1_555 yes O(3) H(3O) 0.9774(7) 1_555 1_555 yes N(1) C(1) 1.3692(7) 1_555 1_555 yes N(1) C(2) 1.3460(8) 1_555 1_555 yes N(1) H(1A) 1.0266(5) 1_555 1_555 yes N(2) C(1) 1.3448(8) 1_555 1_555 yes N(2) C(4) 1.3323(9) 1_555 1_555 yes N(3) C(1) 1.3424(8) 1_555 1_555 yes N(4) C(8) 1.4592(8) 1_555 1_555 yes N(4) H(4A) 1.0350(6) 1_555 1_555 yes N(4) H(4B) 1.0363(6) 1_555 1_555 yes N(4) H(4C) 1.0362(6) 1_555 1_555 yes C(2) C(3) 1.3749(9) 1_555 1_555 yes C(2) H(2) 1.0805(6) 1_555 1_555 yes C(3) C(4) 1.4021(10) 1_555 1_555 yes C(3) H(3) 1.0811(7) 1_555 1_555 yes C(4) H(4) 1.0831(6) 1_555 1_555 yes C(5) C(6) 1.3917(8) 1_555 1_555 yes C(5) C(10) 1.3932(9) 1_555 1_555 yes C(6) C(7) 1.3913(9) 1_555 1_555 yes C(6) H(6) 1.0827(6) 1_555 1_555 yes C(7) C(8) 1.3908(9) 1_555 1_555 yes C(7) H(7) 1.0825(6) 1_555 1_555 yes C(8) C(9) 1.3898(8) 1_555 1_555 yes C(9) C(10) 1.3941(9) 1_555 1_555 yes C(9) H(9) 1.0835(6) 1_555 1_555 yes C(10) H(10) 1.0845(6) 1_555 1_555 yes C(11) C(11) 1.5179(16) 1_555 2_566 yes C(11) H(111) 1.0894(9) 1_555 1_555 yes C(11) H(112) 1.0899(10) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O(1) S(1) O(2) 115.82(4) 1_555 1_555 1_555 yes O(1) S(1) N(3) 103.53(3) 1_555 1_555 1_555 yes O(1) S(1) C(5) 106.37(4) 1_555 1_555 1_555 yes O(2) S(1) N(3) 114.31(4) 1_555 1_555 1_555 yes O(2) S(1) C(5) 106.86(3) 1_555 1_555 1_555 yes N(3) S(1) C(5) 109.62(3) 1_555 1_555 1_555 yes C(11) O(3) H(3O) 109.75(7) 1_555 1_555 1_555 yes C(1) N(1) C(2) 122.33(5) 1_555 1_555 1_555 yes C(1) N(1) H(1A) 117.34(5) 1_555 1_555 1_555 yes C(2) N(1) H(1A) 120.29(5) 1_555 1_555 1_555 yes C(1) N(2) C(4) 117.42(5) 1_555 1_555 1_555 yes S(1) N(3) C(1) 122.18(4) 1_555 1_555 1_555 yes C(8) N(4) H(4A) 106.45(5) 1_555 1_555 1_555 yes C(8) N(4) H(4B) 116.19(5) 1_555 1_555 1_555 yes C(8) N(4) H(4C) 110.41(5) 1_555 1_555 1_555 yes H(4A) N(4) H(4B) 105.08(5) 1_555 1_555 1_555 yes H(4A) N(4) H(4C) 101.40(5) 1_555 1_555 1_555 yes H(4B) N(4) H(4C) 115.58(5) 1_555 1_555 1_555 yes N(1) C(1) N(2) 120.42(6) 1_555 1_555 1_555 yes N(1) C(1) N(3) 114.30(5) 1_555 1_555 1_555 yes N(2) C(1) N(3) 125.28(5) 1_555 1_555 1_555 yes N(1) C(2) C(3) 118.99(6) 1_555 1_555 1_555 yes N(1) C(2) H(2) 120.56(6) 1_555 1_555 1_555 yes C(3) C(2) H(2) 120.45(6) 1_555 1_555 1_555 yes C(2) C(3) C(4) 116.38(6) 1_555 1_555 1_555 yes C(2) C(3) H(3) 121.80(6) 1_555 1_555 1_555 yes C(4) C(3) H(3) 121.81(6) 1_555 1_555 1_555 yes N(2) C(4) C(3) 124.45(6) 1_555 1_555 1_555 yes N(2) C(4) H(4) 117.81(6) 1_555 1_555 1_555 yes C(3) C(4) H(4) 117.74(6) 1_555 1_555 1_555 yes S(1) C(5) C(6) 118.44(5) 1_555 1_555 1_555 yes S(1) C(5) C(10) 119.97(4) 1_555 1_555 1_555 yes C(6) C(5) C(10) 121.43(5) 1_555 1_555 1_555 yes C(5) C(6) C(7) 119.56(6) 1_555 1_555 1_555 yes C(5) C(6) H(6) 120.21(6) 1_555 1_555 1_555 yes C(7) C(6) H(6) 120.23(5) 1_555 1_555 1_555 yes C(6) C(7) C(8) 118.77(5) 1_555 1_555 1_555 yes C(6) C(7) H(7) 120.71(6) 1_555 1_555 1_555 yes C(8) C(7) H(7) 120.52(6) 1_555 1_555 1_555 yes N(4) C(8) C(7) 117.82(5) 1_555 1_555 1_555 yes N(4) C(8) C(9) 120.14(6) 1_555 1_555 1_555 yes C(7) C(8) C(9) 122.01(5) 1_555 1_555 1_555 yes C(8) C(9) C(10) 119.06(6) 1_555 1_555 1_555 yes C(8) C(9) H(9) 120.48(6) 1_555 1_555 1_555 yes C(10) C(9) H(9) 120.46(6) 1_555 1_555 1_555 yes C(5) C(10) C(9) 119.12(5) 1_555 1_555 1_555 yes C(5) C(10) H(10) 120.44(6) 1_555 1_555 1_555 yes C(9) C(10) H(10) 120.44(6) 1_555 1_555 1_555 yes O(3) C(11) C(11) 107.73(9) 1_555 1_555 2_566 yes O(3) C(11) H(111) 102.21(8) 1_555 1_555 1_555 yes O(3) C(11) H(112) 111.32(7) 1_555 1_555 1_555 yes C(11) C(11) H(111) 108.88(10) 2_566 1_555 1_555 yes C(11) C(11) H(112) 117.63(11) 2_566 1_555 1_555 yes H(111) C(11) H(112) 107.95(7) 1_555 1_555 1_555 yes