Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Dr Ross Harrington' _publ_contact_author_address ; School of Natural Sciences (Chemistry) University of Newcastle Bedson Building University of Newcastle Newcastle upon Tyne Tyne and Wear NE1 7RU ; _publ_contact_author_email R.W.HARRINGTON@NCL.AC.UK _publ_section_title ; The structural influence of ligand coordination and hydrogen bonding capabilities in the crystal engineering of metal thiosemicarbazide compounds with malonate ; loop_ _publ_author_name 'Ross Harrington' 'A. D. Burrows' 'M. Mahon' 'S. J. Teat' data_1 _database_code_depnum_ccdc_archive 'CCDC 270065' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H36 N14 Ni3 O20 S4' _chemical_formula_sum 'C10 H36 N14 Ni3 O20 S4' _chemical_formula_weight 976.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.1440(2) _cell_length_b 12.2530(2) _cell_length_c 13.0390(3) _cell_angle_alpha 94.872(2) _cell_angle_beta 111.431(2) _cell_angle_gamma 110.706(2) _cell_volume 1637.52(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 524 _cell_measurement_theta_min 3.59 _cell_measurement_theta_max 27.65 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.981 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1004 _exptl_absorpt_coefficient_mu 2.064 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6482 _exptl_absorpt_correction_T_max 0.6830 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45507 _diffrn_reflns_av_R_equivalents 0.1112 _diffrn_reflns_av_sigmaI/netI 0.0815 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 27.65 _reflns_number_total 7524 _reflns_number_gt 4541 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'HKL DENZO' _computing_data_reduction 'HKL DENZO and SCALEPACK' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0343P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0023(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7524 _refine_ls_number_parameters 589 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.0971 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.981 _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 Ni1 Ni 0.09555(4) 0.50187(4) 0.14285(4) 0.01498(13) Uani 1 1 d . . . Ni2 Ni 0.40884(4) 0.49666(4) 0.34858(4) 0.01568(13) Uani 1 1 d . . . Ni3 Ni 0.23606(5) 0.98817(5) 0.74409(4) 0.01489(13) Uani 1 1 d . . . S1 S 0.21400(9) 0.63243(8) 0.08254(8) 0.0162(2) Uani 1 1 d . . . S2 S 0.14914(9) 0.36548(8) 0.08703(8) 0.0163(2) Uani 1 1 d . . . S3 S 0.36108(9) 0.63760(8) 0.40409(8) 0.0168(2) Uani 1 1 d . . . S4 S 0.29245(9) 0.37364(8) 0.41484(8) 0.0163(2) Uani 1 1 d . . . N1 N 0.0426(3) 0.6213(3) 0.1878(3) 0.0185(7) Uani 1 1 d D . . H1A H -0.039(2) 0.596(3) 0.140(2) 0.016(10) Uiso 1 1 d D . . H1B H 0.047(4) 0.624(4) 0.2580(17) 0.045(15) Uiso 1 1 d D . . N2 N 0.1120(3) 0.7404(3) 0.1827(3) 0.0187(7) Uani 1 1 d D . . H2 H 0.082(3) 0.796(2) 0.191(3) 0.005(9) Uiso 1 1 d D . . N3 N 0.2408(3) 0.8585(3) 0.1075(3) 0.0219(8) Uani 1 1 d D . . H3A H 0.226(4) 0.920(2) 0.124(3) 0.025(12) Uiso 1 1 d D . . H3B H 0.302(4) 0.869(4) 0.084(4) 0.066(19) Uiso 1 1 d D . . N4 N -0.0063(3) 0.3875(3) 0.2020(3) 0.0172(7) Uani 1 1 d D . . H4A H -0.085(2) 0.389(4) 0.182(3) 0.030(12) Uiso 1 1 d D . . H4B H 0.038(3) 0.419(4) 0.2766(18) 0.061(17) Uiso 1 1 d D . . N5 N -0.0177(3) 0.2680(3) 0.1728(3) 0.0209(8) Uani 1 1 d D . . H5 H -0.060(4) 0.209(4) 0.197(4) 0.062(17) Uiso 1 1 d D . . N6 N 0.0548(3) 0.1413(3) 0.1063(3) 0.0235(8) Uani 1 1 d D . . H6A H 0.014(4) 0.089(3) 0.135(4) 0.047(15) Uiso 1 1 d D . . H6B H 0.100(4) 0.120(4) 0.077(4) 0.045(15) Uiso 1 1 d D . . N7 N 0.5086(3) 0.6057(3) 0.2848(3) 0.0202(7) Uani 1 1 d D . . H7A H 0.471(3) 0.579(3) 0.2089(16) 0.027(12) Uiso 1 1 d D . . H7B H 0.584(2) 0.598(3) 0.309(3) 0.020(11) Uiso 1 1 d D . . N8 N 0.5237(3) 0.7265(3) 0.3111(3) 0.0206(8) Uani 1 1 d D . . H8 H 0.562(4) 0.776(3) 0.278(3) 0.031(12) Uiso 1 1 d D . . N9 N 0.4536(3) 0.8571(3) 0.3746(3) 0.0255(8) Uani 1 1 d D . . H9A H 0.487(3) 0.911(3) 0.341(3) 0.022(11) Uiso 1 1 d D . . H9B H 0.409(4) 0.879(4) 0.406(4) 0.061(18) Uiso 1 1 d D . . N10 N 0.4589(3) 0.3726(3) 0.3078(3) 0.0180(7) Uani 1 1 d D . . H10A H 0.445(3) 0.371(4) 0.2373(16) 0.048(15) Uiso 1 1 d D . . H10B H 0.5443(19) 0.395(3) 0.352(2) 0.010(9) Uiso 1 1 d D . . N11 N 0.3876(3) 0.2563(3) 0.3166(3) 0.0195(7) Uani 1 1 d D . . H11 H 0.410(4) 0.196(3) 0.303(4) 0.032(13) Uiso 1 1 d D . . N12 N 0.2645(3) 0.1491(3) 0.4022(3) 0.0212(8) Uani 1 1 d D . . H12A H 0.273(4) 0.083(2) 0.389(3) 0.027(12) Uiso 1 1 d D . . H12B H 0.216(3) 0.147(3) 0.438(3) 0.010(10) Uiso 1 1 d D . . N13 N 0.3742(3) 0.3942(3) 0.0038(3) 0.0195(7) Uani 1 1 d . . . N14 N 0.1276(3) 0.6066(3) 0.4851(3) 0.0213(8) Uani 1 1 d . . . O1 O 0.3906(2) 0.5003(2) 0.0360(2) 0.0221(6) Uani 1 1 d . . . O1W O 0.2448(3) 0.4333(3) 0.6477(2) 0.0258(7) Uani 1 1 d D . . H101 H 0.191(4) 0.3559(18) 0.610(4) 0.061(18) Uiso 1 1 d D . . H102 H 0.216(5) 0.480(3) 0.607(4) 0.068(19) Uiso 1 1 d D . . O2 O 0.3097(3) 0.3401(2) -0.0987(2) 0.0286(7) Uani 1 1 d . . . O2W O 0.2170(3) 0.5444(3) 0.8328(3) 0.0301(7) Uani 1 1 d D . . H201 H 0.213(4) 0.502(3) 0.773(2) 0.028(12) Uiso 1 1 d D . . H202 H 0.272(5) 0.542(5) 0.896(2) 0.09(2) Uiso 1 1 d D . . O3 O 0.4227(3) 0.3413(2) 0.0748(2) 0.0247(7) Uani 1 1 d . . . O3W O 0.2802(3) 0.9044(3) 0.4563(2) 0.0259(7) Uani 1 1 d D . . H301 H 0.312(4) 0.940(3) 0.5284(19) 0.043(14) Uiso 1 1 d D . . H302 H 0.217(3) 0.834(2) 0.439(3) 0.038(14) Uiso 1 1 d D . . O4 O 0.0820(3) 0.6656(2) 0.4207(2) 0.0235(6) Uani 1 1 d . . . O4W O 0.2375(3) 0.0967(3) 0.0388(2) 0.0267(7) Uani 1 1 d D . . H401 H 0.283(4) 0.1712(19) 0.038(4) 0.043(15) Uiso 1 1 d D . . H402 H 0.220(5) 0.047(3) -0.025(3) 0.069(19) Uiso 1 1 d D . . O5 O 0.1981(3) 0.6551(3) 0.5886(2) 0.0307(7) Uani 1 1 d . . . O6 O 0.1042(3) 0.5000(2) 0.4471(2) 0.0264(7) Uani 1 1 d . . . O7 O 0.1842(2) 1.0603(2) 0.6117(2) 0.0207(6) Uani 1 1 d . . . O8 O 0.1183(2) 1.1852(2) 0.5221(2) 0.0238(6) Uani 1 1 d . . . O9 O 0.1004(2) 1.0072(2) 0.7874(2) 0.0195(6) Uani 1 1 d . . . O10 O -0.0330(3) 1.0852(2) 0.8003(2) 0.0245(7) Uani 1 1 d . . . O11 O 0.2861(2) 0.9205(2) 0.8790(2) 0.0202(6) Uani 1 1 d . . . O12 O 0.4158(2) 0.8658(2) 1.0118(2) 0.0222(6) Uani 1 1 d . . . O13 O 0.3732(2) 0.9688(2) 0.7030(2) 0.0175(6) Uani 1 1 d . . . O14 O 0.5239(3) 0.9082(2) 0.7077(2) 0.0246(7) Uani 1 1 d . . . O15 O 0.3815(3) 1.1623(2) 0.8428(2) 0.0175(6) Uani 1 1 d D . . H15A H 0.450(4) 1.162(5) 0.900(4) 0.08(2) Uiso 1 1 d D . . H15B H 0.361(3) 1.218(3) 0.869(3) 0.015(10) Uiso 1 1 d D . . O16 O 0.0966(3) 0.8141(2) 0.6475(2) 0.0177(6) Uani 1 1 d D . . H16A H 0.131(5) 0.773(4) 0.624(4) 0.063(18) Uiso 1 1 d D . . H16B H 0.033(4) 0.820(5) 0.590(4) 0.08(2) Uiso 1 1 d D . . C1 C 0.1865(3) 0.7537(3) 0.1276(3) 0.0166(8) Uani 1 1 d . . . C2 C 0.0551(3) 0.2487(3) 0.1249(3) 0.0172(8) Uani 1 1 d . . . C3 C 0.4529(3) 0.7496(3) 0.3590(3) 0.0168(8) Uani 1 1 d . . . C4 C 0.3174(3) 0.2492(3) 0.3748(3) 0.0165(8) Uani 1 1 d . . . C5 C 0.1233(3) 1.1264(3) 0.5975(3) 0.0177(8) Uani 1 1 d . . . C6 C 0.0525(4) 1.1415(4) 0.6680(4) 0.0268(10) Uani 1 1 d . . . H6C H 0.0934 1.2281 0.7066 0.032 Uiso 1 1 calc R . . H6D H -0.0372 1.1240 0.6136 0.032 Uiso 1 1 calc R . . C7 C 0.0404(3) 1.0736(3) 0.7574(3) 0.0159(8) Uani 1 1 d . . . C8 C 0.3748(3) 0.8815(3) 0.9131(3) 0.0162(8) Uani 1 1 d . . . C9 C 0.4275(4) 0.8459(4) 0.8341(3) 0.0223(9) Uani 1 1 d . . . H9C H 0.3713 0.7600 0.7950 0.027 Uiso 1 1 calc R . . H9D H 0.5144 0.8505 0.8823 0.027 Uiso 1 1 calc R . . C10 C 0.4422(3) 0.9117(3) 0.7428(3) 0.0174(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0161(2) 0.0167(3) 0.0146(3) 0.0051(2) 0.0079(2) 0.0078(2) Ni2 0.0163(2) 0.0181(3) 0.0152(3) 0.0053(2) 0.0085(2) 0.0078(2) Ni3 0.0173(3) 0.0181(3) 0.0146(2) 0.00703(19) 0.0088(2) 0.0105(2) S1 0.0192(5) 0.0164(5) 0.0171(5) 0.0050(4) 0.0099(4) 0.0091(4) S2 0.0168(5) 0.0156(5) 0.0186(5) 0.0060(4) 0.0092(4) 0.0068(4) S3 0.0174(5) 0.0171(5) 0.0183(5) 0.0076(4) 0.0091(4) 0.0073(4) S4 0.0200(5) 0.0156(5) 0.0177(5) 0.0048(4) 0.0104(4) 0.0095(4) N1 0.0143(17) 0.0199(18) 0.0189(19) 0.0028(15) 0.0076(15) 0.0043(14) N2 0.0181(16) 0.0178(17) 0.0216(18) 0.0033(14) 0.0088(15) 0.0088(14) N3 0.0259(19) 0.0162(18) 0.0240(19) 0.0068(15) 0.0099(16) 0.0093(16) N4 0.0126(16) 0.0227(18) 0.0157(18) 0.0054(15) 0.0054(14) 0.0072(14) N5 0.0196(17) 0.0161(17) 0.0251(19) 0.0060(15) 0.0114(15) 0.0034(14) N6 0.0251(19) 0.0198(19) 0.030(2) 0.0110(16) 0.0136(17) 0.0108(16) N7 0.0188(18) 0.0255(19) 0.0191(19) 0.0052(15) 0.0094(15) 0.0109(15) N8 0.0171(17) 0.0218(18) 0.0205(18) 0.0089(15) 0.0086(15) 0.0039(15) N9 0.0247(19) 0.0181(19) 0.027(2) 0.0095(16) 0.0099(17) 0.0026(16) N10 0.0177(17) 0.0207(18) 0.0160(18) 0.0048(15) 0.0070(15) 0.0084(15) N11 0.0260(18) 0.0175(17) 0.0204(18) 0.0051(14) 0.0121(15) 0.0123(15) N12 0.0276(19) 0.0199(19) 0.0200(19) 0.0056(15) 0.0110(16) 0.0129(16) N13 0.0208(17) 0.0239(18) 0.0191(18) 0.0093(15) 0.0116(15) 0.0111(15) N14 0.0205(17) 0.0235(19) 0.0211(19) 0.0045(15) 0.0108(15) 0.0087(15) O1 0.0252(15) 0.0178(14) 0.0248(15) 0.0006(12) 0.0133(13) 0.0088(12) O1W 0.0271(16) 0.0331(18) 0.0233(16) 0.0101(14) 0.0125(13) 0.0166(15) O2 0.0359(17) 0.0282(16) 0.0163(15) -0.0028(13) 0.0032(13) 0.0174(14) O2W 0.0315(17) 0.046(2) 0.0216(17) 0.0079(15) 0.0119(15) 0.0249(15) O3 0.0306(15) 0.0273(16) 0.0254(16) 0.0119(13) 0.0147(13) 0.0177(13) O3W 0.0264(16) 0.0235(16) 0.0214(17) 0.0014(13) 0.0073(14) 0.0073(14) O4 0.0278(15) 0.0281(16) 0.0210(15) 0.0099(13) 0.0108(13) 0.0171(13) O4W 0.0277(16) 0.0266(17) 0.0224(17) 0.0037(14) 0.0097(14) 0.0089(14) O5 0.0384(17) 0.0320(17) 0.0162(16) 0.0021(13) 0.0041(13) 0.0172(14) O6 0.0411(17) 0.0195(15) 0.0244(16) 0.0058(12) 0.0173(14) 0.0156(13) O7 0.0260(14) 0.0233(15) 0.0191(14) 0.0099(12) 0.0104(12) 0.0150(12) O8 0.0251(15) 0.0333(16) 0.0228(15) 0.0191(13) 0.0124(13) 0.0174(13) O9 0.0199(13) 0.0250(15) 0.0212(15) 0.0106(12) 0.0118(12) 0.0132(12) O10 0.0290(15) 0.0256(15) 0.0342(17) 0.0128(13) 0.0216(14) 0.0182(13) O11 0.0211(14) 0.0225(14) 0.0196(14) 0.0103(12) 0.0097(12) 0.0097(12) O12 0.0175(14) 0.0310(16) 0.0168(14) 0.0127(12) 0.0070(12) 0.0074(12) O13 0.0219(14) 0.0193(14) 0.0211(15) 0.0102(12) 0.0140(12) 0.0130(12) O14 0.0245(14) 0.0240(15) 0.0376(17) 0.0135(13) 0.0196(14) 0.0155(13) O15 0.0195(14) 0.0194(14) 0.0154(14) 0.0052(12) 0.0061(12) 0.0112(12) O16 0.0176(14) 0.0215(15) 0.0166(15) 0.0046(12) 0.0079(12) 0.0101(12) C1 0.0146(18) 0.018(2) 0.0120(19) 0.0039(16) -0.0008(15) 0.0081(16) C2 0.0146(18) 0.018(2) 0.0139(19) 0.0048(16) 0.0022(16) 0.0057(16) C3 0.0127(18) 0.015(2) 0.0137(19) 0.0055(16) 0.0008(16) 0.0007(16) C4 0.0158(18) 0.021(2) 0.0116(19) 0.0024(16) 0.0038(16) 0.0087(16) C5 0.0133(18) 0.0168(19) 0.018(2) 0.0046(16) 0.0029(16) 0.0039(16) C6 0.038(2) 0.033(2) 0.029(2) 0.019(2) 0.020(2) 0.027(2) C7 0.0164(18) 0.0152(19) 0.0128(19) 0.0004(15) 0.0040(16) 0.0059(16) C8 0.0140(18) 0.0111(18) 0.022(2) 0.0063(16) 0.0061(16) 0.0041(15) C9 0.025(2) 0.024(2) 0.023(2) 0.0126(18) 0.0091(18) 0.0149(18) C10 0.0177(19) 0.0133(19) 0.019(2) 0.0022(16) 0.0053(17) 0.0070(16) _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 Ni1 N1 1.921(3) . ? Ni1 N4 1.935(3) . ? Ni1 S2 2.1574(11) . ? Ni1 S1 2.1586(10) . ? Ni2 N10 1.928(3) . ? Ni2 N7 1.930(3) . ? Ni2 S4 2.1502(10) . ? Ni2 S3 2.1554(12) . ? Ni3 O11 1.994(3) . ? Ni3 O7 2.004(3) . ? Ni3 O9 2.005(3) . ? Ni3 O13 2.007(3) . ? Ni3 O16 2.105(3) . ? Ni3 O15 2.130(3) . ? S1 C1 1.735(4) . ? S2 C2 1.724(4) . ? S3 C3 1.734(4) . ? S4 C4 1.730(4) . ? N1 N2 1.425(4) . ? N1 H1A 0.880(17) . ? N1 H1B 0.894(18) . ? N2 C1 1.323(5) . ? N2 H2 0.895(18) . ? N3 C1 1.318(5) . ? N3 H3A 0.864(18) . ? N3 H3B 0.876(18) . ? N4 N5 1.425(5) . ? N4 H4A 0.899(18) . ? N4 H4B 0.890(19) . ? N5 C2 1.324(5) . ? N5 H5 0.885(19) . ? N6 C2 1.316(5) . ? N6 H6A 0.867(18) . ? N6 H6B 0.869(18) . ? N7 N8 1.420(5) . ? N7 H7A 0.897(18) . ? N7 H7B 0.895(18) . ? N8 C3 1.321(5) . ? N8 H8 0.874(19) . ? N9 C3 1.312(5) . ? N9 H9A 0.882(18) . ? N9 H9B 0.880(19) . ? N10 N11 1.422(4) . ? N10 H10A 0.869(18) . ? N10 H10B 0.904(17) . ? N11 C4 1.320(5) . ? N11 H11 0.900(19) . ? N12 C4 1.315(5) . ? N12 H12A 0.868(18) . ? N12 H12B 0.871(17) . ? N13 O2 1.247(4) . ? N13 O1 1.253(4) . ? N13 O3 1.264(4) . ? N14 O6 1.248(4) . ? N14 O5 1.252(4) . ? N14 O4 1.258(4) . ? O1W H101 0.902(19) . ? O1W H102 0.884(19) . ? O2W H201 0.875(18) . ? O2W H202 0.864(19) . ? O3W H301 0.877(18) . ? O3W H302 0.864(18) . ? O4W H401 0.887(18) . ? O4W H402 0.891(19) . ? O7 C5 1.259(5) . ? O8 C5 1.263(4) . ? O9 C7 1.269(4) . ? O10 C7 1.253(4) . ? O11 C8 1.279(4) . ? O12 C8 1.258(4) . ? O13 C10 1.272(4) . ? O14 C10 1.246(4) . ? O15 H15A 0.89(2) . ? O15 H15B 0.881(19) . ? O16 H16A 0.86(2) . ? O16 H16B 0.88(2) . ? C5 C6 1.510(5) . ? C6 C7 1.508(5) . ? C6 H6C 0.9900 . ? C6 H6D 0.9900 . ? C8 C9 1.505(5) . ? C9 C10 1.523(5) . ? C9 H9C 0.9900 . ? C9 H9D 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 N1 Ni1 N4 90.96(14) . . ? N1 Ni1 S2 178.06(11) . . ? N4 Ni1 S2 88.93(11) . . ? N1 Ni1 S1 88.61(10) . . ? N4 Ni1 S1 178.09(10) . . ? S2 Ni1 S1 91.56(4) . . ? N10 Ni2 N7 91.79(14) . . ? N10 Ni2 S4 88.43(10) . . ? N7 Ni2 S4 178.25(11) . . ? N10 Ni2 S3 176.71(11) . . ? N7 Ni2 S3 88.88(11) . . ? S4 Ni2 S3 91.00(4) . . ? O11 Ni3 O7 177.86(12) . . ? O11 Ni3 O9 87.06(11) . . ? O7 Ni3 O9 91.17(11) . . ? O11 Ni3 O13 92.12(11) . . ? O7 Ni3 O13 89.65(11) . . ? O9 Ni3 O13 179.15(12) . . ? O11 Ni3 O16 88.86(11) . . ? O7 Ni3 O16 92.25(11) . . ? O9 Ni3 O16 87.32(11) . . ? O13 Ni3 O16 92.88(11) . . ? O11 Ni3 O15 90.30(11) . . ? O7 Ni3 O15 88.64(11) . . ? O9 Ni3 O15 94.11(11) . . ? O13 Ni3 O15 85.68(10) . . ? O16 Ni3 O15 178.30(13) . . ? C1 S1 Ni1 97.40(13) . . ? C2 S2 Ni1 97.77(14) . . ? C3 S3 Ni2 97.39(14) . . ? C4 S4 Ni2 97.70(13) . . ? N2 N1 Ni1 115.8(2) . . ? N2 N1 H1A 109(2) . . ? Ni1 N1 H1A 104(3) . . ? N2 N1 H1B 108(3) . . ? Ni1 N1 H1B 111(3) . . ? H1A N1 H1B 108(2) . . ? C1 N2 N1 117.3(3) . . ? C1 N2 H2 119(2) . . ? N1 N2 H2 119(2) . . ? C1 N3 H3A 124(3) . . ? C1 N3 H3B 119(3) . . ? H3A N3 H3B 117(3) . . ? N5 N4 Ni1 114.4(2) . . ? N5 N4 H4A 111(3) . . ? Ni1 N4 H4A 110(3) . . ? N5 N4 H4B 111(3) . . ? Ni1 N4 H4B 102(3) . . ? H4A N4 H4B 107(3) . . ? C2 N5 N4 119.0(3) . . ? C2 N5 H5 118(4) . . ? N4 N5 H5 122(4) . . ? C2 N6 H6A 117(3) . . ? C2 N6 H6B 127(3) . . ? H6A N6 H6B 116(3) . . ? N8 N7 Ni2 115.1(2) . . ? N8 N7 H7A 108(3) . . ? Ni2 N7 H7A 110(3) . . ? N8 N7 H7B 113(2) . . ? Ni2 N7 H7B 104(2) . . ? H7A N7 H7B 106(2) . . ? C3 N8 N7 118.2(3) . . ? C3 N8 H8 123(3) . . ? N7 N8 H8 117(3) . . ? C3 N9 H9A 122(2) . . ? C3 N9 H9B 126(3) . . ? H9A N9 H9B 112(3) . . ? N11 N10 Ni2 115.4(2) . . ? N11 N10 H10A 110(3) . . ? Ni2 N10 H10A 104(3) . . ? N11 N10 H10B 109(2) . . ? Ni2 N10 H10B 109(2) . . ? H10A N10 H10B 111(3) . . ? C4 N11 N10 117.3(3) . . ? C4 N11 H11 120(3) . . ? N10 N11 H11 120(3) . . ? C4 N12 H12A 126(2) . . ? C4 N12 H12B 119(2) . . ? H12A N12 H12B 115(3) . . ? O2 N13 O1 120.0(3) . . ? O2 N13 O3 119.7(3) . . ? O1 N13 O3 120.3(3) . . ? O6 N14 O5 119.3(4) . . ? O6 N14 O4 120.8(3) . . ? O5 N14 O4 119.9(3) . . ? H101 O1W H102 108(3) . . ? H201 O2W H202 113(3) . . ? H301 O3W H302 111(3) . . ? H401 O4W H402 108(3) . . ? C5 O7 Ni3 127.5(2) . . ? C7 O9 Ni3 128.5(2) . . ? C8 O11 Ni3 127.8(2) . . ? C10 O13 Ni3 128.6(2) . . ? Ni3 O15 H15A 115(4) . . ? Ni3 O15 H15B 121(2) . . ? H15A O15 H15B 107(5) . . ? Ni3 O16 H16A 111(3) . . ? Ni3 O16 H16B 109(4) . . ? H16A O16 H16B 111(5) . . ? N3 C1 N2 120.6(4) . . ? N3 C1 S1 119.7(3) . . ? N2 C1 S1 119.7(3) . . ? N6 C2 N5 120.1(3) . . ? N6 C2 S2 120.7(3) . . ? N5 C2 S2 119.2(3) . . ? N9 C3 N8 120.5(3) . . ? N9 C3 S3 119.9(3) . . ? N8 C3 S3 119.5(3) . . ? N12 C4 N11 121.5(4) . . ? N12 C4 S4 119.0(3) . . ? N11 C4 S4 119.5(3) . . ? O7 C5 O8 121.3(4) . . ? O7 C5 C6 123.1(3) . . ? O8 C5 C6 115.6(4) . . ? C7 C6 C5 123.7(4) . . ? C7 C6 H6C 106.4 . . ? C5 C6 H6C 106.4 . . ? C7 C6 H6D 106.4 . . ? C5 C6 H6D 106.4 . . ? H6C C6 H6D 106.5 . . ? O10 C7 O9 121.3(3) . . ? O10 C7 C6 116.6(4) . . ? O9 C7 C6 122.1(3) . . ? O12 C8 O11 121.1(4) . . ? O12 C8 C9 117.9(3) . . ? O11 C8 C9 120.9(3) . . ? C8 C9 C10 121.8(3) . . ? C8 C9 H9C 106.9 . . ? C10 C9 H9C 106.9 . . ? C8 C9 H9D 106.9 . . ? C10 C9 H9D 106.9 . . ? H9C C9 H9D 106.7 . . ? O14 C10 O13 120.7(3) . . ? O14 C10 C9 118.2(3) . . ? O13 C10 C9 121.1(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O2W 0.880(17) 2.40(3) 2.983(4) 124(3) 2_566 N1 H1A S2 0.880(17) 2.92(3) 3.544(4) 129(3) 2_565 N1 H1B O4 0.894(18) 1.99(2) 2.867(4) 168(4) . N2 H2 O10 0.895(18) 1.765(19) 2.658(4) 174(3) 2_576 N3 H3A O4W 0.864(18) 2.49(3) 3.134(5) 132(3) 1_565 N3 H3B O12 0.876(18) 1.944(19) 2.811(4) 170(5) 1_554 N4 H4A O2W 0.899(18) 2.00(2) 2.858(4) 159(4) 2_566 N4 H4B O6 0.890(19) 2.08(2) 2.952(4) 167(4) . N5 H5 O16 0.885(19) 2.25(4) 2.963(4) 138(4) 2_566 N5 H5 O11 0.885(19) 2.39(4) 3.036(4) 130(4) 2_566 N5 H5 O9 0.885(19) 2.56(4) 3.306(4) 143(5) 2_566 N6 H6A O9 0.867(18) 2.098(19) 2.948(4) 166(4) 2_566 N6 H6A O10 0.867(18) 2.41(4) 3.090(4) 135(3) 2_566 N6 H6B O4W 0.869(18) 2.01(2) 2.864(5) 168(4) . N7 H7A O1 0.897(18) 2.08(2) 2.972(4) 173(4) . N7 H7B O1W 0.895(18) 2.13(2) 3.022(5) 175(3) 2_666 N8 H8 O15 0.874(19) 2.04(2) 2.873(4) 160(4) 2_676 N9 H9A O13 0.882(18) 2.12(2) 2.958(4) 159(3) 2_676 N9 H9A O14 0.882(18) 2.39(3) 3.112(4) 139(3) 2_676 N9 H9B O3W 0.880(19) 2.01(2) 2.880(5) 170(5) . N10 H10A O3 0.869(18) 2.02(2) 2.876(4) 170(5) . N11 H11 O14 0.900(19) 1.75(2) 2.644(4) 172(4) 2_666 N12 H12A O3W 0.868(18) 2.44(3) 3.193(5) 145(3) 1_545 N12 H12B O8 0.871(17) 2.022(18) 2.874(4) 166(3) 1_545 O15 H15A O12 0.89(2) 1.79(2) 2.660(4) 166(6) 2_677 O15 H15B O2 0.881(19) 1.89(2) 2.763(4) 171(4) 1_566 O15 H15B N13 0.881(19) 2.59(2) 3.433(4) 160(3) 1_566 O16 H16A O5 0.86(2) 1.98(2) 2.835(4) 168(5) . O16 H16A N14 0.86(2) 2.58(3) 3.381(4) 154(5) . O16 H16A O4 0.86(2) 2.61(4) 3.250(4) 132(4) . O16 H16B O8 0.88(2) 1.87(2) 2.740(4) 171(5) 2_576 O1W H101 O8 0.902(19) 2.00(2) 2.880(4) 164(5) 1_545 O1W H102 O6 0.884(19) 2.13(3) 2.918(4) 149(4) . O1W H102 O5 0.884(19) 2.26(3) 3.071(4) 153(4) . O1W H102 N14 0.884(19) 2.54(2) 3.424(5) 178(4) . O2W H201 O1W 0.875(18) 2.00(2) 2.856(4) 167(4) . O2W H202 O1 0.864(19) 2.10(2) 2.954(4) 169(5) 1_556 O2W H202 S1 0.864(19) 3.00(5) 3.359(3) 107(4) 1_556 O3W H301 O13 0.877(18) 2.07(2) 2.921(4) 162(4) . O3W H302 O4 0.864(18) 2.07(2) 2.923(4) 172(4) . O4W H401 O3 0.887(18) 2.05(2) 2.912(4) 165(4) . O4W H401 N13 0.887(18) 2.70(2) 3.578(4) 169(4) . O4W H402 O9 0.891(19) 2.25(4) 2.971(4) 138(5) 1_544 O4W H402 O11 0.891(19) 2.43(3) 3.223(4) 148(5) 1_544 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.593 _refine_diff_density_min -0.620 _refine_diff_density_rms 0.113 #=== END data_2 _database_code_depnum_ccdc_archive 'CCDC 270066' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H34 N6 Ni2 O14 S2' _chemical_formula_weight 667.99 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1390(14) _cell_length_b 31.196(6) _cell_length_c 11.575(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.865(10) _cell_angle_gamma 90.00 _cell_volume 2572.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 1.701 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7845 _exptl_absorpt_correction_T_max 0.9832 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.69410 _diffrn_radiation_type ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13317 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0693 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4815 _reflns_number_gt 3371 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+14.3728P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0019(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4815 _refine_ls_number_parameters 406 _refine_ls_number_restraints 66 _refine_ls_R_factor_all 0.1067 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_ref 0.1262 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.71798(14) 0.11001(2) 0.46096(8) 0.0183(2) Uani 1 1 d . . . Ni2 Ni 0.21457(11) 0.24926(3) 0.20652(7) 0.00867(18) Uani 1 1 d . . . S1 S 0.9084(3) 0.06191(5) 0.53362(15) 0.0216(4) Uani 1 1 d . . . S2 S 0.5211(3) 0.06235(5) 0.39514(16) 0.0236(4) Uani 1 1 d . . . N1 N 0.9043(9) 0.15337(17) 0.5000(5) 0.0223(13) Uani 1 1 d D . . H1A H 0.857(10) 0.1745(13) 0.541(5) 0.03(2) Uiso 1 1 d D . . H1B H 0.944(10) 0.1639(17) 0.435(3) 0.04(2) Uiso 1 1 d D . . N2 N 1.0680(9) 0.13783(18) 0.5611(5) 0.0280(14) Uani 1 1 d D . . H2 H 1.139(9) 0.1582(18) 0.595(6) 0.04(2) Uiso 1 1 d D . . N3 N 1.2433(9) 0.08274(19) 0.6374(5) 0.0257(14) Uani 1 1 d D . . H3 H 1.346(7) 0.099(2) 0.649(7) 0.04(3) Uiso 1 1 d D . . N4 N 0.5404(10) 0.15308(17) 0.4161(5) 0.0276(15) Uani 1 1 d D . . H4A H 0.509(11) 0.1639(17) 0.484(3) 0.033 Uiso 1 1 d D . . H4B H 0.577(10) 0.1744(13) 0.372(4) 0.033 Uiso 1 1 d D . . N5 N 0.3723(9) 0.13907(18) 0.3565(5) 0.0274(14) Uani 1 1 d D . . H5 H 0.286(7) 0.1574(16) 0.328(5) 0.013(17) Uiso 1 1 d D . . N6 N 0.1910(9) 0.08319(18) 0.2888(6) 0.0292(15) Uani 1 1 d D . . H6 H 0.120(10) 0.1049(18) 0.262(7) 0.05(3) Uiso 1 1 d D . . C1 C 1.0866(10) 0.0958(2) 0.5820(6) 0.0200(15) Uani 1 1 d . . . C2 C 1.2866(11) 0.0391(2) 0.6709(7) 0.0274(16) Uani 1 1 d U . . H2A H 1.4119 0.0314 0.6455 0.033 Uiso 1 1 calc R . . H2B H 1.1933 0.0196 0.6314 0.033 Uiso 1 1 calc R . . C3 C 1.2854(13) 0.0327(3) 0.8002(7) 0.041(2) Uani 1 1 d U . . H3A H 1.3813 0.0511 0.8394 0.062 Uiso 1 1 calc R . . H3B H 1.3125 0.0027 0.8192 0.062 Uiso 1 1 calc R . . H3C H 1.1617 0.0404 0.8258 0.062 Uiso 1 1 calc R . . C4 C 0.3473(10) 0.0970(2) 0.3423(6) 0.0227(16) Uani 1 1 d . . . C5 C 0.1513(12) 0.0391(2) 0.2552(7) 0.0367(19) Uani 1 1 d U . . H5A H 0.0162 0.0331 0.2617 0.044 Uiso 1 1 calc R . . H5B H 0.2237 0.0196 0.3089 0.044 Uiso 1 1 calc R . . C6 C 0.2012(15) 0.0302(3) 0.1330(8) 0.056(3) Uani 1 1 d U . . H6A H 0.1422 0.0517 0.0808 0.083 Uiso 1 1 calc R . . H6B H 0.1560 0.0016 0.1095 0.083 Uiso 1 1 calc R . . H6C H 0.3378 0.0314 0.1293 0.083 Uiso 1 1 calc R . . C7 C -0.0489(8) 0.17548(18) 0.1934(5) 0.0103(12) Uani 1 1 d U . . C8 C -0.1653(9) 0.19878(18) 0.0982(5) 0.0129(13) Uani 1 1 d U . . H8A H -0.1179 0.1900 0.0232 0.015 Uiso 1 1 calc R . . H8B H -0.2958 0.1881 0.0989 0.015 Uiso 1 1 calc R . . C9 C -0.1729(9) 0.2471(2) 0.0999(5) 0.0124(12) Uani 1 1 d U . . C10 C 0.4807(8) 0.32310(19) 0.2193(5) 0.0119(13) Uani 1 1 d U . . C11 C 0.5945(9) 0.30030(19) 0.3164(5) 0.0134(13) Uani 1 1 d U . . H11A H 0.5442 0.3091 0.3905 0.016 Uiso 1 1 calc R . . H11B H 0.7250 0.3111 0.3172 0.016 Uiso 1 1 calc R . . C12 C 0.6025(8) 0.2515(2) 0.3147(4) 0.0102(12) Uani 1 1 d U . . O1 O 0.1006(6) 0.19175(12) 0.2398(3) 0.0121(9) Uani 1 1 d . . . O2 O -0.1044(6) 0.13894(14) 0.2207(4) 0.0207(10) Uani 1 1 d . . . O3 O -0.3294(6) 0.26520(12) 0.0758(3) 0.0122(9) Uani 1 1 d . . . O4 O -0.0223(6) 0.26855(13) 0.1173(4) 0.0131(9) Uani 1 1 d . . . O5 O 0.3300(6) 0.30675(13) 0.1735(4) 0.0137(9) Uani 1 1 d . . . O6 O 0.5368(6) 0.35933(13) 0.1904(4) 0.0189(10) Uani 1 1 d . . . O7 O 0.7576(6) 0.23383(13) 0.3383(3) 0.0127(9) Uani 1 1 d . . . O8 O 0.4514(6) 0.23044(12) 0.2961(4) 0.0125(9) Uani 1 1 d . . . O1W O 0.0987(6) 0.27157(14) 0.3559(4) 0.0145(9) Uani 1 1 d D . . H1WA H 0.170(8) 0.273(2) 0.422(3) 0.016(17) Uiso 1 1 d D . . H1WB H 0.086(13) 0.2989(8) 0.336(7) 0.05(3) Uiso 1 1 d D . . O2W O 0.3324(6) 0.22669(13) 0.0576(4) 0.0125(9) Uani 1 1 d D . . H2WA H 0.36(2) 0.203(3) 0.018(12) 0.18(7) Uiso 1 1 d D . . H2WB H 0.448(4) 0.237(2) 0.062(6) 0.03(2) Uiso 1 1 d D . . O3W O 0.6664(9) 0.41064(19) 0.5617(6) 0.0425(15) Uani 1 1 d D . . H3WA H 0.724(17) 0.395(4) 0.618(8) 0.12(5) Uiso 1 1 d D . . H3WB H 0.70(5) 0.406(10) 0.490(10) 0.4(2) Uiso 1 1 d D . . O4W O 0.7794(8) 0.41060(18) 0.3161(6) 0.0373(14) Uani 1 1 d D . . H4WA H 0.694(7) 0.3925(18) 0.286(6) 0.02(2) Uiso 1 1 d D . . H4WB H 0.839(13) 0.417(3) 0.254(6) 0.07(4) Uiso 1 1 d D . . O5W O 0.3322(9) 0.1372(2) 0.0579(5) 0.0477(17) Uani 1 1 d D . . H5WA H 0.433(6) 0.124(2) 0.090(6) 0.03(2) Uiso 1 1 d D . . H5WB H 0.260(11) 0.133(3) -0.007(5) 0.05(3) Uiso 1 1 d D . . O6W O 0.0981(9) 0.35943(19) 0.3650(6) 0.0443(15) Uani 1 1 d D . . H6WA H -0.002(7) 0.376(2) 0.359(7) 0.04(3) Uiso 1 1 d D . . H6WB H 0.07(2) 0.346(5) 0.430(8) 0.15(7) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0256(5) 0.0098(4) 0.0192(4) 0.0008(4) -0.0008(3) 0.0014(4) Ni2 0.0049(3) 0.0107(3) 0.0103(3) 0.0001(3) 0.0001(2) -0.0005(3) S1 0.0222(10) 0.0117(8) 0.0298(10) -0.0019(7) -0.0055(7) -0.0006(7) S2 0.0218(10) 0.0142(8) 0.0337(10) 0.0019(7) -0.0061(8) 0.0032(7) N1 0.037(4) 0.015(3) 0.015(3) 0.000(2) -0.004(3) -0.003(3) N2 0.033(4) 0.015(3) 0.034(4) -0.007(3) -0.010(3) -0.006(3) N3 0.020(4) 0.026(3) 0.030(3) -0.003(3) -0.005(3) -0.003(3) N4 0.051(5) 0.011(3) 0.020(3) 0.002(2) -0.003(3) 0.010(3) N5 0.037(4) 0.017(3) 0.027(3) 0.003(3) -0.006(3) 0.008(3) N6 0.026(4) 0.019(3) 0.041(4) 0.008(3) -0.007(3) 0.006(3) C1 0.029(4) 0.015(3) 0.017(3) -0.003(3) 0.008(3) -0.003(3) C2 0.025(4) 0.016(3) 0.041(4) -0.001(3) 0.003(3) 0.002(3) C3 0.046(6) 0.027(4) 0.050(5) 0.001(4) 0.002(4) 0.003(4) C4 0.027(4) 0.022(4) 0.019(4) 0.006(3) 0.002(3) 0.010(3) C5 0.029(5) 0.032(4) 0.047(5) 0.013(4) -0.010(4) -0.004(3) C6 0.070(7) 0.037(5) 0.061(6) -0.018(5) 0.013(5) -0.008(5) C7 0.009(3) 0.011(3) 0.011(3) 0.000(2) 0.004(2) 0.000(2) C8 0.011(3) 0.014(3) 0.013(3) -0.003(2) -0.002(2) -0.003(2) C9 0.014(3) 0.015(3) 0.008(3) 0.000(2) 0.000(2) -0.002(3) C10 0.008(3) 0.017(3) 0.011(3) -0.004(2) 0.000(2) 0.003(2) C11 0.009(3) 0.019(3) 0.013(3) 0.003(2) 0.004(2) -0.004(3) C12 0.012(3) 0.017(3) 0.002(3) 0.000(2) 0.002(2) 0.001(3) O1 0.014(2) 0.012(2) 0.010(2) 0.0002(17) -0.0020(17) -0.0008(17) O2 0.016(3) 0.017(2) 0.028(3) 0.007(2) -0.005(2) -0.0046(19) O3 0.008(2) 0.014(2) 0.014(2) 0.0009(17) 0.0022(17) 0.0021(17) O4 0.006(2) 0.016(2) 0.018(2) 0.0026(17) 0.0013(17) -0.0005(17) O5 0.010(2) 0.014(2) 0.016(2) 0.0031(17) -0.0017(17) 0.0005(18) O6 0.015(3) 0.015(2) 0.027(3) 0.0067(19) -0.0058(19) -0.0049(19) O7 0.008(2) 0.018(2) 0.012(2) 0.0031(17) 0.0005(17) 0.0022(17) O8 0.009(2) 0.012(2) 0.015(2) 0.0035(17) -0.0057(17) -0.0021(17) O1W 0.015(3) 0.016(2) 0.012(2) -0.0010(19) -0.0014(18) -0.0006(18) O2W 0.007(3) 0.015(2) 0.016(2) -0.0067(18) 0.0024(18) -0.0016(17) O3W 0.029(3) 0.035(3) 0.062(4) 0.008(3) -0.004(3) 0.007(3) O4W 0.023(3) 0.033(3) 0.056(4) -0.008(3) 0.001(3) -0.008(2) O5W 0.051(5) 0.045(4) 0.044(4) 0.006(3) -0.013(3) 0.021(3) O6W 0.044(4) 0.035(3) 0.052(4) 0.002(3) -0.003(3) 0.014(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 Ni1 N4 1.896(6) . ? Ni1 N1 1.929(6) . ? Ni1 S2 2.150(2) . ? Ni1 S1 2.1572(19) . ? Ni2 O8 2.010(4) . ? Ni2 O4 2.013(4) . ? Ni2 O1 2.018(4) . ? Ni2 O5 2.021(4) . ? Ni2 O1W 2.087(4) . ? Ni2 O2W 2.090(4) . ? S1 C1 1.718(7) . ? S2 C4 1.726(7) . ? N1 N2 1.411(9) . ? N1 H1A 0.890(10) . ? N1 H1B 0.888(10) . ? N2 C1 1.339(9) . ? N2 H2 0.890(10) . ? N3 C1 1.316(9) . ? N3 C2 1.445(9) . ? N3 H3 0.890(10) . ? N4 N5 1.412(9) . ? N4 H4A 0.893(10) . ? N4 H4B 0.890(10) . ? N5 C4 1.332(9) . ? N5 H5 0.889(10) . ? N6 C4 1.312(9) . ? N6 C5 1.453(9) . ? N6 H6 0.889(10) . ? C2 C3 1.509(11) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 C6 1.507(12) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 O2 1.254(7) . ? C7 O1 1.269(7) . ? C7 C8 1.520(8) . ? C8 C9 1.507(8) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O3 1.266(7) . ? C9 O4 1.272(7) . ? C10 O6 1.252(7) . ? C10 O5 1.274(7) . ? C10 C11 1.519(8) . ? C11 C12 1.525(8) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O7 1.250(7) . ? C12 O8 1.268(7) . ? O1W H1WA 0.888(10) . ? O1W H1WB 0.888(10) . ? O2W H2WA 0.890(10) . ? O2W H2WB 0.886(10) . ? O3W H3WA 0.889(10) . ? O3W H3WB 0.890(11) . ? O4W H4WA 0.889(10) . ? O4W H4WB 0.890(10) . ? O5W H5WA 0.890(10) . ? O5W H5WB 0.890(10) . ? O6W H6WA 0.888(10) . ? O6W H6WB 0.888(10) . ? 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 N4 Ni1 N1 90.3(2) . . ? N4 Ni1 S2 89.1(2) . . ? N1 Ni1 S2 172.68(19) . . ? N4 Ni1 S1 172.8(2) . . ? N1 Ni1 S1 89.42(18) . . ? S2 Ni1 S1 92.12(6) . . ? O8 Ni2 O4 179.57(19) . . ? O8 Ni2 O1 88.72(17) . . ? O4 Ni2 O1 91.62(17) . . ? O8 Ni2 O5 90.99(17) . . ? O4 Ni2 O5 88.67(17) . . ? O1 Ni2 O5 179.7(2) . . ? O8 Ni2 O1W 92.09(17) . . ? O4 Ni2 O1W 87.67(17) . . ? O1 Ni2 O1W 87.16(17) . . ? O5 Ni2 O1W 92.89(17) . . ? O8 Ni2 O2W 87.48(17) . . ? O4 Ni2 O2W 92.76(17) . . ? O1 Ni2 O2W 92.75(16) . . ? O5 Ni2 O2W 87.20(17) . . ? O1W Ni2 O2W 179.6(2) . . ? C1 S1 Ni1 97.6(2) . . ? C4 S2 Ni1 97.4(3) . . ? N2 N1 Ni1 114.3(4) . . ? N2 N1 H1A 108(5) . . ? Ni1 N1 H1A 112(5) . . ? N2 N1 H1B 105(5) . . ? Ni1 N1 H1B 108(5) . . ? H1A N1 H1B 109.1(17) . . ? C1 N2 N1 119.7(6) . . ? C1 N2 H2 125(5) . . ? N1 N2 H2 114(5) . . ? C1 N3 C2 125.6(6) . . ? C1 N3 H3 124(5) . . ? C2 N3 H3 109(5) . . ? N5 N4 Ni1 116.4(4) . . ? N5 N4 H4A 107(5) . . ? Ni1 N4 H4A 103(5) . . ? N5 N4 H4B 103(5) . . ? Ni1 N4 H4B 118(5) . . ? H4A N4 H4B 108.9(17) . . ? C4 N5 N4 117.9(6) . . ? C4 N5 H5 120(4) . . ? N4 N5 H5 122(4) . . ? C4 N6 C5 125.6(6) . . ? C4 N6 H6 111(6) . . ? C5 N6 H6 122(6) . . ? N3 C1 N2 117.5(6) . . ? N3 C1 S1 123.7(5) . . ? N2 C1 S1 118.8(6) . . ? N3 C2 C3 111.9(6) . . ? N3 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? N3 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N6 C4 N5 119.0(6) . . ? N6 C4 S2 121.9(5) . . ? N5 C4 S2 119.1(6) . . ? N6 C5 C6 111.8(7) . . ? N6 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? N6 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O2 C7 O1 121.9(5) . . ? O2 C7 C8 116.8(5) . . ? O1 C7 C8 121.3(5) . . ? C9 C8 C7 119.1(5) . . ? C9 C8 H8A 107.5 . . ? C7 C8 H8A 107.5 . . ? C9 C8 H8B 107.5 . . ? C7 C8 H8B 107.5 . . ? H8A C8 H8B 107.0 . . ? O3 C9 O4 121.5(6) . . ? O3 C9 C8 118.4(5) . . ? O4 C9 C8 119.8(5) . . ? O6 C10 O5 121.8(5) . . ? O6 C10 C11 117.1(5) . . ? O5 C10 C11 121.0(5) . . ? C10 C11 C12 118.5(5) . . ? C10 C11 H11A 107.7 . . ? C12 C11 H11A 107.7 . . ? C10 C11 H11B 107.7 . . ? C12 C11 H11B 107.7 . . ? H11A C11 H11B 107.1 . . ? O7 C12 O8 122.7(6) . . ? O7 C12 C11 118.1(5) . . ? O8 C12 C11 119.2(5) . . ? C7 O1 Ni2 127.8(4) . . ? C9 O4 Ni2 126.6(4) . . ? C10 O5 Ni2 128.3(4) . . ? C12 O8 Ni2 127.8(4) . . ? Ni2 O1W H1WA 120(4) . . ? Ni2 O1W H1WB 98(6) . . ? H1WA O1W H1WB 102(7) . . ? Ni2 O2W H2WA 144(10) . . ? Ni2 O2W H2WB 105(5) . . ? H2WA O2W H2WB 96(10) . . ? H3WA O3W H3WB 118(10) . . ? H4WA O4W H4WB 100(8) . . ? H5WA O5W H5WB 134(8) . . ? H6WA O6W H6WB 97(10) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O4 0.890(10) 2.14(5) 2.821(7) 133(6) 4_666 N1 H1A O3 0.890(10) 2.36(3) 3.194(7) 157(6) 4_666 N1 H1B O2 0.888(10) 2.60(5) 3.261(7) 132(6) 1_655 N2 H2 O5 0.890(10) 1.92(2) 2.802(7) 168(8) 4_666 N2 H2 O4 0.890(10) 2.58(7) 3.070(7) 116(6) 4_666 N3 H3 O6 0.890(10) 1.92(2) 2.803(7) 169(8) 4_666 N4 H4A O6 0.893(10) 2.50(4) 3.200(8) 136(5) 4_566 N4 H4B O8 0.890(10) 2.13(5) 2.835(7) 136(6) . N4 H4B O7 0.890(10) 2.30(3) 3.122(7) 153(6) . N5 H5 O1 0.889(10) 1.938(17) 2.817(7) 170(6) . N6 H6 O2 0.889(10) 1.95(3) 2.805(7) 160(8) . O1W H1WA O2W 0.888(10) 1.891(13) 2.777(5) 176(6) 4_566 O1W H1WB O6W 0.888(10) 1.92(4) 2.743(7) 154(8) . O2W H2WA O5W 0.890(10) 2.12(12) 2.792(8) 131(14) . O2W H2WB O3 0.886(10) 1.812(15) 2.693(6) 173(7) 1_655 O3W H3WA O2 0.889(10) 1.96(3) 2.837(8) 168(13) 4_666 O3W H3WB O4W 0.890(11) 2.13(7) 3.007(10) 168(29) . O4W H4WA O6 0.889(10) 1.84(2) 2.709(7) 166(7) . O4W H4WB S1 0.890(10) 2.71(4) 3.562(7) 162(9) 4_565 O5W H5WA O3W 0.890(10) 2.03(4) 2.812(9) 146(7) 4_565 O5W H5WB O6W 0.890(10) 1.83(3) 2.699(8) 165(9) 4_565 O6W H6WA O4W 0.888(10) 1.93(2) 2.806(8) 169(8) 1_455 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.694 _refine_diff_density_min -1.076 _refine_diff_density_rms 0.121 #=== END data_3 _database_code_depnum_ccdc_archive 'CCDC 270067' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H34 N10 Ni O9 S3' _chemical_formula_sum 'C12 H34 N10 Ni O9 S3' _chemical_formula_weight 617.38 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 13.711(2) _cell_length_b 10.2151(15) _cell_length_c 18.702(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.868(10) _cell_angle_gamma 90.00 _cell_volume 2600.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 34278 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 28.65 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 1.048 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8338 _exptl_absorpt_correction_T_max 0.9793 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.69410 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method 'thin-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 20 _diffrn_reflns_number 33308 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 29.27 _reflns_number_total 7138 _reflns_number_gt 6145 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0319P)^2^+1.1527P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7138 _refine_ls_number_parameters 387 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0763 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _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 Ni1 Ni 0.246421(14) 0.265340(19) 0.167514(10) 0.01702(6) Uani 1 1 d . . . S1 S 0.33235(3) 0.22359(4) 0.06633(2) 0.02297(8) Uani 1 1 d . . . S2 S 0.34229(3) 0.11340(4) 0.24511(2) 0.02206(8) Uani 1 1 d . . . S3 S 0.34939(3) 0.44753(4) 0.20511(2) 0.02278(9) Uani 1 1 d . . . N1 N 0.14794(10) 0.12274(13) 0.11828(7) 0.0195(2) Uani 1 1 d . . . H1A H 0.0853(15) 0.149(2) 0.1104(11) 0.024(5) Uiso 1 1 d . . . H1B H 0.1482(16) 0.055(2) 0.1475(13) 0.037(6) Uiso 1 1 d . . . N2 N 0.17076(12) 0.07757(16) 0.05099(9) 0.0320(3) Uani 1 1 d . . . H2 H 0.1366(17) 0.017(2) 0.0306(13) 0.042(6) Uiso 1 1 d . . . N3 N 0.26384(12) 0.06164(18) -0.03973(9) 0.0341(4) Uani 1 1 d . . . H3 H 0.2169(17) 0.009(2) -0.0584(13) 0.039(6) Uiso 1 1 d . . . N4 N 0.16307(10) 0.27825(13) 0.25420(7) 0.0193(2) Uani 1 1 d . . . H4A H 0.1031(17) 0.256(2) 0.2416(12) 0.026(5) Uiso 1 1 d . . . H4B H 0.1623(15) 0.354(2) 0.2704(11) 0.026(5) Uiso 1 1 d . . . N5 N 0.19638(11) 0.19975(14) 0.31439(8) 0.0242(3) Uani 1 1 d . . . H5 H 0.1623(15) 0.200(2) 0.3470(12) 0.024(5) Uiso 1 1 d . . . N6 N 0.29860(11) 0.05668(16) 0.37672(8) 0.0286(3) Uani 1 1 d . . . H6 H 0.2590(16) 0.062(2) 0.4079(12) 0.031(6) Uiso 1 1 d . . . N7 N 0.15447(10) 0.41392(13) 0.11667(8) 0.0219(3) Uani 1 1 d . . . H7A H 0.0944(16) 0.405(2) 0.1269(11) 0.028(5) Uiso 1 1 d . . . H7B H 0.1562(18) 0.406(3) 0.0696(15) 0.051(7) Uiso 1 1 d . . . N8 N 0.18320(11) 0.54375(14) 0.13508(8) 0.0270(3) Uani 1 1 d . . . H8 H 0.1574(17) 0.603(2) 0.1065(13) 0.041(6) Uiso 1 1 d . . . N9 N 0.29534(12) 0.69427(15) 0.17804(10) 0.0325(3) Uani 1 1 d . . . H9 H 0.2512(18) 0.745(2) 0.1635(13) 0.043(7) Uiso 1 1 d . . . N10 N -0.08129(11) 0.22718(14) 0.00954(8) 0.0261(3) Uani 1 1 d . . . O1 O 0.14846(9) 0.52933(11) 0.32978(7) 0.0284(3) Uani 1 1 d . . . O1W O 0.04340(12) 0.31591(16) 0.39117(8) 0.0372(3) Uani 1 1 d . . . H1WA H -0.016(3) 0.314(3) 0.3735(17) 0.069(10) Uiso 1 1 d . . . H1WB H 0.079(4) 0.386(6) 0.382(3) 0.20(3) Uiso 1 1 d . . . O2 O 0.01960(9) 0.63247(11) 0.27140(7) 0.0279(3) Uani 1 1 d . . . O2W O -0.13084(11) 0.57762(17) 0.04292(8) 0.0352(3) Uani 1 1 d . . . H2WA H -0.099(2) 0.506(3) 0.0450(15) 0.055(8) Uiso 1 1 d . . . H2WB H -0.090(2) 0.637(3) 0.0519(15) 0.057(8) Uiso 1 1 d . . . O3 O 0.04256(9) 0.93327(12) 0.29693(7) 0.0263(2) Uani 1 1 d . . . H3O H 0.018(2) 1.001(3) 0.2666(17) 0.073(9) Uiso 1 1 d . . . O4 O 0.13273(9) 0.88229(12) 0.20914(7) 0.0279(3) Uani 1 1 d . . . O5 O -0.14916(13) 0.23345(16) -0.03990(11) 0.0578(5) Uani 1 1 d . . . O6 O -0.03445(11) 0.32747(15) 0.03152(9) 0.0456(4) Uani 1 1 d . . . O7 O -0.05900(10) 0.12026(13) 0.03775(7) 0.0324(3) Uani 1 1 d . . . C1 C 0.25220(11) 0.11457(16) 0.02376(9) 0.0219(3) Uani 1 1 d . . . C2 C 0.35149(13) 0.07061(18) -0.07633(9) 0.0280(3) Uani 1 1 d . . . H2A H 0.3972 0.1357 -0.0515 0.034 Uiso 1 1 calc R . . H2B H 0.3331 0.1008 -0.1264 0.034 Uiso 1 1 calc R . . C3 C 0.40192(16) -0.0598(2) -0.07705(14) 0.0453(5) Uani 1 1 d . . . H3A H 0.4227 -0.0879 -0.0275 0.068 Uiso 1 1 calc R . . H3B H 0.4596 -0.0522 -0.1031 0.068 Uiso 1 1 calc R . . H3C H 0.3564 -0.1245 -0.1010 0.068 Uiso 1 1 calc R . . C4 C 0.27607(11) 0.12396(15) 0.31582(8) 0.0205(3) Uani 1 1 d . . . C5 C 0.38505(14) -0.02588(19) 0.39286(10) 0.0329(4) Uani 1 1 d . . . H5A H 0.4452 0.0265 0.3899 0.040 Uiso 1 1 calc R . . H5B H 0.3835 -0.0977 0.3572 0.040 Uiso 1 1 calc R . . C6 C 0.38664(16) -0.0822(2) 0.46754(11) 0.0383(4) Uani 1 1 d . . . H6A H 0.3875 -0.0107 0.5026 0.057 Uiso 1 1 calc R . . H6B H 0.4455 -0.1363 0.4787 0.057 Uiso 1 1 calc R . . H6C H 0.3280 -0.1361 0.4698 0.057 Uiso 1 1 calc R . . C7 C 0.27357(12) 0.56786(15) 0.17018(9) 0.0213(3) Uani 1 1 d . . . C8 C 0.39011(14) 0.74820(17) 0.20725(10) 0.0303(4) Uani 1 1 d . . . H8A H 0.4322 0.6771 0.2297 0.036 Uiso 1 1 calc R . . H8B H 0.3804 0.8130 0.2451 0.036 Uiso 1 1 calc R . . C9 C 0.44054(17) 0.8126(3) 0.14998(12) 0.0478(5) Uani 1 1 d . . . H9A H 0.4566 0.7467 0.1152 0.072 Uiso 1 1 calc R . . H9B H 0.5011 0.8546 0.1720 0.072 Uiso 1 1 calc R . . H9C H 0.3970 0.8788 0.1253 0.072 Uiso 1 1 calc R . . C10 C 0.10507(12) 0.62949(15) 0.30593(8) 0.0199(3) Uani 1 1 d . . . C11 C 0.15736(12) 0.76052(15) 0.31859(9) 0.0219(3) Uani 1 1 d . . . H11A H 0.1561 0.7872 0.3694 0.026 Uiso 1 1 calc R . . H11B H 0.2269 0.7506 0.3102 0.026 Uiso 1 1 calc R . . C12 C 0.11017(11) 0.86569(15) 0.26982(9) 0.0211(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01716(10) 0.01497(9) 0.01876(9) -0.00010(7) 0.00151(7) -0.00068(7) S1 0.02132(18) 0.02417(19) 0.02416(18) -0.00494(14) 0.00581(14) -0.00635(14) S2 0.02090(18) 0.02258(18) 0.02280(18) 0.00130(14) 0.00304(14) 0.00489(14) S3 0.02110(18) 0.01779(18) 0.02809(19) -0.00099(14) -0.00269(14) -0.00103(13) N1 0.0194(6) 0.0191(6) 0.0200(6) 0.0013(5) 0.0028(5) -0.0012(5) N2 0.0295(8) 0.0357(8) 0.0325(8) -0.0163(7) 0.0111(6) -0.0160(6) N3 0.0292(8) 0.0440(9) 0.0304(8) -0.0173(7) 0.0085(6) -0.0109(7) N4 0.0198(6) 0.0158(6) 0.0220(6) 0.0009(5) 0.0013(5) 0.0021(5) N5 0.0270(7) 0.0246(7) 0.0220(7) 0.0054(5) 0.0079(6) 0.0068(5) N6 0.0311(8) 0.0315(8) 0.0237(7) 0.0069(6) 0.0058(6) 0.0084(6) N7 0.0218(7) 0.0198(6) 0.0234(7) 0.0017(5) 0.0005(5) -0.0024(5) N8 0.0256(7) 0.0182(7) 0.0351(8) 0.0051(6) -0.0042(6) 0.0006(5) N9 0.0284(8) 0.0172(7) 0.0501(10) 0.0027(6) -0.0028(7) -0.0003(6) N10 0.0256(7) 0.0238(7) 0.0291(7) -0.0001(5) 0.0037(6) -0.0033(5) O1 0.0355(6) 0.0180(5) 0.0303(6) 0.0009(5) -0.0020(5) 0.0072(5) O1W 0.0366(8) 0.0442(8) 0.0308(7) 0.0024(6) 0.0043(6) 0.0061(6) O2 0.0237(6) 0.0158(5) 0.0422(7) -0.0020(5) -0.0041(5) 0.0004(4) O2W 0.0331(7) 0.0423(8) 0.0309(7) 0.0040(6) 0.0072(6) -0.0041(7) O3 0.0319(6) 0.0181(5) 0.0295(6) 0.0022(5) 0.0063(5) 0.0029(5) O4 0.0327(6) 0.0240(6) 0.0279(6) 0.0073(5) 0.0073(5) 0.0018(5) O5 0.0496(10) 0.0439(9) 0.0711(12) 0.0248(8) -0.0288(9) -0.0087(7) O6 0.0412(8) 0.0322(7) 0.0652(10) -0.0180(7) 0.0142(7) -0.0148(6) O7 0.0327(7) 0.0300(7) 0.0325(7) 0.0084(5) -0.0037(5) -0.0027(5) C1 0.0205(7) 0.0211(7) 0.0240(7) -0.0023(6) 0.0023(6) -0.0009(6) C2 0.0293(8) 0.0309(9) 0.0245(8) -0.0043(6) 0.0066(6) -0.0001(7) C3 0.0344(10) 0.0368(11) 0.0662(15) 0.0100(10) 0.0122(10) 0.0082(8) C4 0.0216(7) 0.0173(7) 0.0221(7) -0.0008(5) 0.0006(6) -0.0006(5) C5 0.0344(9) 0.0343(10) 0.0290(9) 0.0056(7) -0.0003(7) 0.0105(7) C6 0.0503(12) 0.0312(10) 0.0306(9) 0.0065(7) -0.0065(8) 0.0058(8) C7 0.0225(7) 0.0182(7) 0.0238(7) 0.0014(5) 0.0058(6) -0.0004(5) C8 0.0333(9) 0.0213(8) 0.0351(9) -0.0018(7) -0.0011(7) -0.0069(7) C9 0.0395(11) 0.0650(15) 0.0394(11) 0.0008(10) 0.0064(9) -0.0178(11) C10 0.0236(7) 0.0164(7) 0.0202(7) 0.0001(5) 0.0045(5) 0.0022(5) C11 0.0223(7) 0.0190(7) 0.0233(7) 0.0027(6) -0.0017(6) -0.0015(6) C12 0.0221(7) 0.0155(7) 0.0250(7) 0.0012(5) 0.0002(6) -0.0048(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N4 2.0963(14) . ? Ni1 N1 2.1203(13) . ? Ni1 N7 2.1237(14) . ? Ni1 S1 2.3841(5) . ? Ni1 S3 2.3903(5) . ? Ni1 S2 2.4055(5) . ? S1 C1 1.6949(16) . ? S2 C4 1.6948(17) . ? S3 C7 1.6900(16) . ? N1 N2 1.410(2) . ? N2 C1 1.336(2) . ? N3 C1 1.331(2) . ? N3 C2 1.455(2) . ? N4 N5 1.4127(18) . ? N5 C4 1.337(2) . ? N6 C4 1.334(2) . ? N6 C5 1.457(2) . ? N7 N8 1.4143(19) . ? N8 C7 1.354(2) . ? N9 C7 1.330(2) . ? N9 C8 1.456(2) . ? N10 O5 1.233(2) . ? N10 O7 1.2353(19) . ? N10 O6 1.2522(19) . ? O1 C10 1.2394(18) . ? O2 C10 1.2690(19) . ? O3 C12 1.306(2) . ? O4 C12 1.223(2) . ? C2 C3 1.502(3) . ? C5 C6 1.508(3) . ? C8 C9 1.495(3) . ? C10 C11 1.524(2) . ? C11 C12 1.504(2) . ? 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 N4 Ni1 N1 90.07(5) . . ? N4 Ni1 N7 87.25(6) . . ? N1 Ni1 N7 89.05(5) . . ? N4 Ni1 S1 172.70(4) . . ? N1 Ni1 S1 83.22(4) . . ? N7 Ni1 S1 95.49(4) . . ? N4 Ni1 S3 94.65(4) . . ? N1 Ni1 S3 170.30(4) . . ? N7 Ni1 S3 82.73(4) . . ? S1 Ni1 S3 92.417(17) . . ? N4 Ni1 S2 83.29(4) . . ? N1 Ni1 S2 95.30(4) . . ? N7 Ni1 S2 169.58(4) . . ? S1 Ni1 S2 94.425(18) . . ? S3 Ni1 S2 93.670(19) . . ? C1 S1 Ni1 97.83(6) . . ? C4 S2 Ni1 97.16(6) . . ? C7 S3 Ni1 97.95(6) . . ? N2 N1 Ni1 114.50(10) . . ? C1 N2 N1 122.16(14) . . ? C1 N3 C2 125.99(15) . . ? N5 N4 Ni1 115.23(10) . . ? C4 N5 N4 122.03(14) . . ? C4 N6 C5 125.08(15) . . ? N8 N7 Ni1 115.34(10) . . ? C7 N8 N7 120.05(14) . . ? C7 N9 C8 125.97(16) . . ? O5 N10 O7 119.49(15) . . ? O5 N10 O6 121.03(16) . . ? O7 N10 O6 119.49(15) . . ? N3 C1 N2 114.82(15) . . ? N3 C1 S1 123.07(13) . . ? N2 C1 S1 122.09(13) . . ? N3 C2 C3 110.81(16) . . ? N6 C4 N5 114.89(15) . . ? N6 C4 S2 122.83(13) . . ? N5 C4 S2 122.28(12) . . ? N6 C5 C6 109.51(16) . . ? N9 C7 N8 114.25(15) . . ? N9 C7 S3 122.96(13) . . ? N8 C7 S3 122.70(12) . . ? N9 C8 C9 111.48(16) . . ? O1 C10 O2 125.26(15) . . ? O1 C10 C11 118.21(14) . . ? O2 C10 C11 116.53(13) . . ? C12 C11 C10 111.90(13) . . ? O4 C12 O3 123.84(15) . . ? O4 C12 C11 121.55(15) . . ? O3 C12 C11 114.58(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O7 0.89(2) 2.28(2) 3.0492(19) 143.9(17) . N1 H1B O4 0.88(2) 2.13(2) 3.0082(18) 173(2) 1_545 N2 H2 O7 0.84(2) 2.10(3) 2.929(2) 170(2) 3 N3 H3 O1 0.88(2) 2.22(2) 2.898(2) 133(2) 4_565 N3 H3 O7 0.88(2) 2.60(2) 3.371(2) 147(2) 3 N4 H4A O2 0.86(2) 2.09(2) 2.9038(19) 157.0(19) 2_545 N4 H4B O1 0.83(2) 2.13(2) 2.9470(18) 168(2) . N5 H5 O1W 0.81(2) 2.25(2) 2.931(2) 141.6(19) . N4 H4A O2 0.86(2) 2.09(2) 2.9038(19) 157.0(19) 2_545 N5 H5 O2W 0.81(2) 2.49(2) 3.172(2) 142.5(19) 2_545 N6 H6 O2W 0.84(2) 2.09(2) 2.902(2) 163(2) 2_545 N7 H7A O3 0.87(2) 2.51(2) 3.315(2) 154.8(19) 2_545 N7 H7A O6 0.87(2) 2.49(2) 3.006(2) 118.9(17) . N7 H7B O2W 0.89(3) 2.10(3) 2.965(2) 165(2) 3_565 N8 H8 O5 0.86(3) 2.08(3) 2.893(2) 159(2) 3_565 N9 H9 O4 0.82(3) 2.38(3) 3.051(2) 140(2) . N9 H9 O5 0.82(3) 2.56(2) 3.162(2) 131(2) 3_565 O1W H1WA O4 0.84(3) 2.20(3) 2.954(2) 149(3) 2_545 O1W H1WA O5 0.84(3) 2.63(3) 3.115(3) 118(3) 4_566 O3 H3O O2 0.93(3) 1.58(3) 2.4980(17) 169(3) 2 O2W H2WA O6 0.85(3) 2.06(3) 2.896(2) 170(3) . O2W H2WB O1W 0.82(3) 2.18(3) 2.920(2) 150(3) 2 O2W H2WB O6 0.82(3) 2.48(3) 2.961(2) 119(2) 3_565 O1W H1WB O1 0.89(6) 2.05(6) 2.923(2) 163(6) . _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.550 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.058 #=== END data_4 _database_code_depnum_ccdc_archive 'CCDC 270068' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H9 N3 O5 S Zn' _chemical_formula_sum 'C4 H9 N3 O5 S Zn' _chemical_formula_weight 276.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 9.1940(5) _cell_length_b 11.0370(7) _cell_length_c 9.2830(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.528(4) _cell_angle_gamma 90.00 _cell_volume 898.25(9) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 1995 _cell_measurement_theta_min 3.69 _cell_measurement_theta_max 27.43 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.045 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 2.968 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4696 _exptl_absorpt_correction_T_max 0.5241 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15901 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 27.44 _reflns_number_total 2041 _reflns_number_gt 1924 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'HKL DENZO' _computing_data_reduction 'HKL DENZO and SCALEPACK' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0484P)^2^+0.3693P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0163(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2041 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0796 _refine_ls_wR_factor_gt 0.0778 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.59046(2) 0.69060(2) 0.38972(2) 0.01891(13) Uani 1 1 d . . . S2 S 0.74122(5) 0.59517(4) 0.60736(5) 0.02132(15) Uani 1 1 d . . . O1 O 0.36795(15) 0.71702(14) 0.35925(16) 0.0226(3) Uani 1 1 d . . . O3 O 0.54035(15) 0.53654(12) 0.25659(15) 0.0207(3) Uani 1 1 d . . . O4 O 0.38114(15) 0.43258(13) 0.06854(16) 0.0227(3) Uani 1 1 d . . . O5 O 0.12779(15) 0.71068(13) 0.21878(17) 0.0223(3) Uani 1 1 d . . . O6 O -0.1038(2) 0.52617(15) 0.1742(2) 0.0354(4) Uani 1 1 d . . . H6A H -0.178(5) 0.556(4) 0.113(5) 0.080(13) Uiso 1 1 d . . . H6B H -0.045(5) 0.579(4) 0.163(4) 0.072(12) Uiso 1 1 d . . . N1 N 0.9639(2) 0.71407(19) 0.8043(2) 0.0264(4) Uani 1 1 d . . . H1A H 1.004(3) 0.780(3) 0.852(3) 0.035(7) Uiso 1 1 d . . . H1B H 1.004(4) 0.645(3) 0.820(3) 0.040(8) Uiso 1 1 d . . . N2 N 0.77338(19) 0.83426(17) 0.6624(2) 0.0224(3) Uani 1 1 d . . . H2 H 0.837(3) 0.899(3) 0.699(3) 0.035(7) Uiso 1 1 d . . . N3 N 0.63738(18) 0.84999(16) 0.5426(2) 0.0216(3) Uani 1 1 d . . . H3C H 0.564(3) 0.874(3) 0.584(3) 0.026(6) Uiso 1 1 d . . . H3D H 0.653(3) 0.911(3) 0.485(3) 0.033(7) Uiso 1 1 d . . . C1 C 0.8326(2) 0.72340(18) 0.6958(2) 0.0194(4) Uani 1 1 d . . . C2 C 0.4178(2) 0.52532(18) 0.1468(2) 0.0185(4) Uani 1 1 d . . . C3 C 0.3114(2) 0.63553(19) 0.1074(2) 0.0233(4) Uani 1 1 d . . . H3A H 0.3616 0.6989 0.0637 0.028 Uiso 1 1 calc R . . H3B H 0.2170 0.6113 0.0283 0.028 Uiso 1 1 calc R . . C4 C 0.2676(2) 0.69001(16) 0.2374(2) 0.0192(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01386(17) 0.01799(18) 0.02255(18) -0.00019(7) 0.00199(11) -0.00082(7) S2 0.0217(2) 0.0160(3) 0.0225(3) 0.00049(17) 0.00112(18) -0.00207(17) O1 0.0146(6) 0.0274(7) 0.0243(7) -0.0067(6) 0.0036(5) -0.0020(5) O3 0.0168(6) 0.0191(7) 0.0234(7) -0.0011(5) 0.0018(5) 0.0026(5) O4 0.0211(6) 0.0196(7) 0.0246(7) -0.0026(6) 0.0025(5) 0.0012(5) O5 0.0146(6) 0.0202(7) 0.0301(8) -0.0021(6) 0.0035(5) 0.0017(5) O6 0.0257(8) 0.0226(8) 0.0474(10) -0.0012(7) -0.0049(7) -0.0013(7) N1 0.0224(8) 0.0222(9) 0.0282(9) -0.0033(8) -0.0018(7) -0.0006(7) N2 0.0182(8) 0.0197(8) 0.0258(9) -0.0034(7) 0.0012(6) -0.0011(6) N3 0.0191(8) 0.0188(8) 0.0253(8) 0.0008(7) 0.0042(6) 0.0000(6) C1 0.0178(9) 0.0186(9) 0.0219(9) -0.0012(7) 0.0061(7) -0.0018(7) C2 0.0169(8) 0.0179(9) 0.0210(9) -0.0001(7) 0.0063(6) 0.0005(7) C3 0.0218(9) 0.0225(10) 0.0215(9) -0.0028(7) 0.0006(7) 0.0056(7) C4 0.0166(9) 0.0148(9) 0.0250(10) 0.0005(6) 0.0043(7) 0.0001(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 S2 2.3293(5) . ? Zn1 O1 2.0004(14) . ? Zn1 O3 2.0707(14) . ? Zn1 O5 2.0374(15) 4_675 ? Zn1 N3 2.2195(18) . ? S2 C1 1.723(2) . ? O1 C4 1.261(2) . ? O3 C2 1.277(2) . ? O4 C2 1.242(2) . ? O5 Zn1 2.0374(15) 4_575 ? O5 C4 1.265(2) . ? O6 H6A 0.82(4) . ? O6 H6B 0.83(4) . ? N1 H1A 0.87(3) . ? N1 H1B 0.84(4) . ? N1 C1 1.323(3) . ? N2 H2 0.92(3) . ? N2 N3 1.412(2) . ? N2 C1 1.337(3) . ? N3 H3C 0.92(3) . ? N3 H3D 0.89(3) . ? C2 C3 1.534(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.508(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S2 Zn1 O1 120.31(5) . . ? S2 Zn1 O3 96.53(4) . . ? S2 Zn1 O5 136.18(4) . 4_675 ? S2 Zn1 N3 81.58(5) . . ? O1 Zn1 O3 90.06(6) . . ? O1 Zn1 O5 102.53(6) . 4_675 ? O1 Zn1 N3 88.19(6) . . ? O3 Zn1 O5 91.93(6) . 4_675 ? O3 Zn1 N3 176.31(6) . . ? O5 Zn1 N3 91.62(6) 4_675 . ? Zn1 S2 C1 96.85(7) . . ? Zn1 O1 C4 122.21(13) . . ? Zn1 O3 C2 122.68(12) . . ? Zn1 O5 C4 113.11(13) 4_575 . ? H6A O6 H6B 94(4) . . ? H1A N1 H1B 125(3) . . ? H1A N1 C1 118(2) . . ? H1B N1 C1 117(2) . . ? H2 N2 N3 120.6(18) . . ? H2 N2 C1 117.1(18) . . ? N3 N2 C1 119.83(17) . . ? Zn1 N3 N2 111.21(12) . . ? Zn1 N3 H3C 118.3(17) . . ? Zn1 N3 H3D 104.4(18) . . ? N2 N3 H3C 107.1(15) . . ? N2 N3 H3D 107.2(17) . . ? H3C N3 H3D 108(2) . . ? S2 C1 N1 120.08(16) . . ? S2 C1 N2 122.35(15) . . ? N1 C1 N2 117.54(18) . . ? O3 C2 O4 124.44(17) . . ? O3 C2 C3 117.33(17) . . ? O4 C2 C3 118.20(16) . . ? C2 C3 H3A 108.4 . . ? C2 C3 H3B 108.4 . . ? C2 C3 C4 115.47(16) . . ? H3A C3 H3B 107.5 . . ? H3A C3 C4 108.4 . . ? H3B C3 C4 108.4 . . ? O1 C4 O5 121.25(19) . . ? O1 C4 C3 120.83(17) . . ? O5 C4 C3 117.89(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6A O4 0.82(4) 2.10(4) 2.886(2) 160(4) 3_565 O6 H6B O5 0.83(4) 2.10(4) 2.884(2) 160(4) . N1 H1A O4 0.87(3) 2.00(3) 2.868(2) 169(3) 2_656 N1 H1B O6 0.84(4) 2.09(4) 2.927(3) 172(3) 3_666 N2 H2 O3 0.92(3) 1.86(3) 2.776(2) 171(3) 2_656 N3 H3C N1 0.92(3) 2.66(3) 3.358(3) 134(2) 4_575 N3 H3D S2 0.89(3) 2.52(3) 3.3826(19) 163(2) 2_656 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.618 _refine_diff_density_min -0.604 _refine_diff_density_rms 0.097 #=== END data_5 _database_code_depnum_ccdc_archive 'CCDC 270069' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H31 N11 O11 S3 Zn2' _chemical_formula_sum 'C12 H31 N11 O11 S3 Zn2' _chemical_formula_weight 732.40 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3550(2) _cell_length_b 12.1490(2) _cell_length_c 16.8090(4) _cell_angle_alpha 105.7450(9) _cell_angle_beta 96.956(2) _cell_angle_gamma 104.237(2) _cell_volume 1372.53(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2205 _cell_measurement_theta_min 3.74 _cell_measurement_theta_max 27.43 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.772 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 2.047 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6850 _exptl_absorpt_correction_T_max 0.8215 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20841 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 27.54 _reflns_number_total 6299 _reflns_number_gt 5009 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'HKL DENZO' _computing_data_reduction 'HKL DENZO and SCALEPACK' _computing_structure_solution SHELXS86 _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0281P)^2^+0.5341P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6299 _refine_ls_number_parameters 412 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0764 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 0.57743(4) 0.88779(2) 0.122141(17) 0.01630(9) Uani 1 1 d . . . Zn2 Zn 0.34299(4) 0.60150(2) 0.262767(17) 0.01554(9) Uani 1 1 d . . . S1 S 0.78002(9) 1.01055(6) 0.25305(4) 0.02119(14) Uani 1 1 d . . . S3 S 0.18723(9) 0.51258(6) 0.35371(4) 0.01969(14) Uani 1 1 d . . . S4 S 0.60297(9) 0.74760(6) 0.37165(4) 0.02038(15) Uani 1 1 d . . . O1 O 0.3304(2) 0.88320(17) 0.05738(11) 0.0235(4) Uani 1 1 d . . . O2 O 0.0137(2) 0.83340(16) 0.02211(11) 0.0237(4) Uani 1 1 d . . . O3 O 0.1822(2) 0.70620(14) 0.23447(10) 0.0158(3) Uani 1 1 d . . . O4 O 0.4234(2) 0.77472(16) 0.17837(11) 0.0201(4) Uani 1 1 d . . . O5 O 0.6621(3) 0.74528(16) 0.06261(11) 0.0189(4) Uani 1 1 d . . . H5C H 0.567(5) 0.692(3) 0.023(2) 0.045(10) Uiso 1 1 d . . . H5D H 0.757(6) 0.758(3) 0.047(2) 0.050(12) Uiso 1 1 d . . . O6 O 0.4329(3) 0.31371(17) 0.20605(13) 0.0335(5) Uani 1 1 d . . . O7 O 0.2886(3) 0.1639(3) 0.09697(13) 0.0651(9) Uani 1 1 d . . . O8 O 0.5918(3) 0.20423(16) 0.13875(12) 0.0272(4) Uani 1 1 d . . . O9 O 0.6625(3) 0.39790(16) 0.05533(11) 0.0229(4) Uani 1 1 d . . . O10 O 0.8934(2) 0.56122(15) 0.07919(11) 0.0223(4) Uani 1 1 d . . . O11 O 0.6853(3) 0.48986(16) -0.03928(11) 0.0243(4) Uani 1 1 d . . . N1 N 1.1022(3) 1.1752(2) 0.25966(14) 0.0224(5) Uani 1 1 d . . . H1 H 1.170(4) 1.216(2) 0.2397(17) 0.017(8) Uiso 1 1 d . . . N2 N 0.9121(3) 1.0870(2) 0.12944(14) 0.0191(5) Uani 1 1 d . . . H2 H 0.991(4) 1.126(2) 0.1136(17) 0.014(7) Uiso 1 1 d . . . N3 N 0.7497(3) 1.0056(2) 0.07113(14) 0.0196(5) Uani 1 1 d . . . H3A H 0.790(4) 0.967(2) 0.0327(18) 0.016(7) Uiso 1 1 d . . . H3B H 0.688(4) 1.047(3) 0.0506(18) 0.027(8) Uiso 1 1 d . . . N4 N 0.9648(3) 0.77252(19) 0.35728(13) 0.0185(4) Uani 1 1 d . . . H4 H 1.050(5) 0.754(3) 0.327(2) 0.039(9) Uiso 1 1 d . . . N5 N 0.7487(3) 0.64023(19) 0.24367(13) 0.0172(4) Uani 1 1 d . . . H5 H 0.829(4) 0.633(2) 0.2188(17) 0.011(7) Uiso 1 1 d . . . N6 N 0.5618(3) 0.5764(2) 0.19720(13) 0.0179(4) Uani 1 1 d . . . H6A H 0.544(4) 0.599(3) 0.155(2) 0.029(8) Uiso 1 1 d . . . H6B H 0.559(5) 0.500(3) 0.178(2) 0.039(9) Uiso 1 1 d . . . N7 N -0.1644(3) 0.3622(2) 0.30489(15) 0.0285(5) Uani 1 1 d . . . H7 H -0.265(5) 0.327(3) 0.265(2) 0.039(9) Uiso 1 1 d . . . N8 N -0.0237(3) 0.3957(2) 0.19773(14) 0.0211(5) Uani 1 1 d . . . H8 H -0.129(5) 0.360(3) 0.165(2) 0.033(9) Uiso 1 1 d . . . N9 N 0.1290(3) 0.4492(2) 0.16449(14) 0.0180(4) Uani 1 1 d . . . H9A H 0.087(4) 0.478(3) 0.1323(19) 0.024(8) Uiso 1 1 d . . . H9B H 0.165(4) 0.387(3) 0.1358(19) 0.028(8) Uiso 1 1 d . . . N10 N 0.4377(3) 0.22629(19) 0.14650(13) 0.0206(5) Uani 1 1 d . . . N11 N 0.7478(3) 0.48318(18) 0.03134(12) 0.0179(4) Uani 1 1 d . . . C1 C 0.9400(4) 1.0958(2) 0.21146(15) 0.0176(5) Uani 1 1 d . . . C2 C 1.1645(4) 1.1977(2) 0.35019(16) 0.0253(6) Uani 1 1 d . . . H2A H 1.0504 1.1816 0.3758 0.030 Uiso 1 1 calc R . . H2B H 1.2376 1.2830 0.3769 0.030 Uiso 1 1 calc R . . C3 C 1.2880(5) 1.1210(3) 0.36800(19) 0.0366(7) Uani 1 1 d . . . H3C H 1.3338 1.1430 0.4290 0.055 Uiso 1 1 calc R . . H3D H 1.3978 1.1337 0.3404 0.055 Uiso 1 1 calc R . . H3E H 1.2125 1.0366 0.3462 0.055 Uiso 1 1 calc R . . C4 C 0.1640(3) 0.8530(2) 0.07310(16) 0.0181(5) Uani 1 1 d . . . C5 C 0.1483(4) 0.8464(2) 0.16181(16) 0.0194(5) Uani 1 1 d . . . H5A H 0.1938 0.9286 0.2019 0.023 Uiso 1 1 calc R . . H5B H 0.0116 0.8136 0.1627 0.023 Uiso 1 1 calc R . . C6 C 0.2595(3) 0.7714(2) 0.19255(14) 0.0147(5) Uani 1 1 d . . . C7 C 0.7813(3) 0.7186(2) 0.32115(14) 0.0158(5) Uani 1 1 d . . . C8 C 1.0321(4) 0.8604(3) 0.44076(17) 0.0293(6) Uani 1 1 d . . . H8A H 0.9536 0.8346 0.4799 0.035 Uiso 1 1 calc R . . H8B H 1.0174 0.9382 0.4381 0.035 Uiso 1 1 calc R . . C9 C 1.2398(4) 0.8747(3) 0.47353(18) 0.0318(7) Uani 1 1 d . . . H9C H 1.2823 0.9338 0.5299 0.048 Uiso 1 1 calc R . . H9D H 1.3178 0.9019 0.4354 0.048 Uiso 1 1 calc R . . H9E H 1.2541 0.7978 0.4765 0.048 Uiso 1 1 calc R . . C10 C -0.0124(4) 0.4192(2) 0.28154(16) 0.0193(5) Uani 1 1 d . . . C11 C -0.1933(4) 0.3817(3) 0.39169(17) 0.0294(6) Uani 1 1 d . . . H11A H -0.0678 0.4049 0.4303 0.035 Uiso 1 1 calc R . . H11B H -0.2725 0.3061 0.3967 0.035 Uiso 1 1 calc R . . C12 C -0.2895(5) 0.4768(4) 0.4176(2) 0.0479(9) Uani 1 1 d . . . H12A H -0.3140 0.4837 0.4745 0.072 Uiso 1 1 calc R . . H12B H -0.4111 0.4559 0.3780 0.072 Uiso 1 1 calc R . . H12C H -0.2065 0.5533 0.4174 0.072 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 0.01181(15) 0.02182(16) 0.02019(16) 0.01200(12) 0.00624(11) 0.00616(11) Zn2 0.01216(15) 0.01837(15) 0.01650(15) 0.00661(11) 0.00296(11) 0.00390(11) S1 0.0225(3) 0.0246(3) 0.0183(3) 0.0107(3) 0.0075(2) 0.0041(3) S3 0.0167(3) 0.0236(3) 0.0168(3) 0.0091(2) 0.0007(2) 0.0006(2) S4 0.0134(3) 0.0262(3) 0.0165(3) -0.0006(3) 0.0046(2) 0.0041(3) O1 0.0135(9) 0.0381(11) 0.0296(10) 0.0246(9) 0.0082(7) 0.0092(8) O2 0.0142(9) 0.0356(11) 0.0279(10) 0.0200(8) 0.0065(7) 0.0067(8) O3 0.0153(8) 0.0179(8) 0.0163(8) 0.0083(7) 0.0055(7) 0.0039(7) O4 0.0152(9) 0.0278(9) 0.0289(10) 0.0196(8) 0.0124(7) 0.0111(8) O5 0.0130(9) 0.0209(9) 0.0207(10) 0.0042(8) 0.0062(8) 0.0027(8) O6 0.0339(12) 0.0248(10) 0.0435(12) 0.0066(9) 0.0196(10) 0.0104(9) O7 0.0157(11) 0.125(2) 0.0198(11) -0.0106(13) -0.0001(9) -0.0019(13) O8 0.0169(9) 0.0271(10) 0.0360(11) 0.0054(8) 0.0040(8) 0.0091(8) O9 0.0231(10) 0.0233(9) 0.0227(9) 0.0108(8) 0.0039(7) 0.0037(8) O10 0.0167(9) 0.0236(9) 0.0211(9) 0.0036(8) -0.0034(7) 0.0032(7) O11 0.0215(10) 0.0362(11) 0.0145(9) 0.0101(8) 0.0013(7) 0.0060(8) N1 0.0212(12) 0.0242(12) 0.0219(12) 0.0106(10) 0.0061(9) 0.0023(10) N2 0.0149(11) 0.0244(12) 0.0213(11) 0.0139(10) 0.0064(9) 0.0028(9) N3 0.0179(11) 0.0226(11) 0.0201(12) 0.0099(10) 0.0046(9) 0.0050(9) N4 0.0122(10) 0.0231(11) 0.0171(11) 0.0015(9) 0.0048(8) 0.0038(9) N5 0.0115(10) 0.0242(11) 0.0140(10) 0.0026(9) 0.0036(8) 0.0049(9) N6 0.0158(11) 0.0209(12) 0.0145(11) 0.0023(9) -0.0002(8) 0.0061(9) N7 0.0162(12) 0.0403(14) 0.0235(12) 0.0116(11) 0.0013(10) -0.0019(10) N8 0.0131(11) 0.0257(12) 0.0208(11) 0.0090(9) -0.0006(9) -0.0009(9) N9 0.0182(11) 0.0184(11) 0.0189(11) 0.0073(9) 0.0037(9) 0.0062(9) N10 0.0162(11) 0.0294(12) 0.0182(11) 0.0126(9) 0.0031(9) 0.0046(9) N11 0.0154(10) 0.0221(11) 0.0163(11) 0.0039(9) 0.0031(8) 0.0078(9) C1 0.0182(12) 0.0176(12) 0.0220(13) 0.0091(10) 0.0079(10) 0.0092(10) C2 0.0295(15) 0.0238(14) 0.0183(13) 0.0041(11) 0.0011(11) 0.0049(12) C3 0.0410(18) 0.0424(18) 0.0254(15) 0.0093(13) -0.0004(13) 0.0150(15) C4 0.0152(12) 0.0201(12) 0.0255(13) 0.0134(11) 0.0071(10) 0.0079(10) C5 0.0172(13) 0.0238(13) 0.0254(13) 0.0129(11) 0.0100(10) 0.0119(11) C6 0.0161(12) 0.0147(11) 0.0132(11) 0.0028(9) 0.0048(9) 0.0052(9) C7 0.0175(12) 0.0156(11) 0.0155(12) 0.0055(10) 0.0034(9) 0.0061(10) C8 0.0160(13) 0.0370(16) 0.0233(14) -0.0045(12) 0.0031(11) 0.0029(12) C9 0.0188(14) 0.0380(16) 0.0285(15) 0.0002(13) -0.0007(11) 0.0042(12) C10 0.0154(12) 0.0228(13) 0.0220(13) 0.0112(11) 0.0033(10) 0.0050(10) C11 0.0224(14) 0.0406(16) 0.0274(15) 0.0187(13) 0.0059(11) 0.0035(12) C12 0.049(2) 0.078(3) 0.0313(18) 0.0247(18) 0.0124(15) 0.034(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 Zn1 S1 2.3703(7) . ? Zn1 O1 1.9819(17) . ? Zn1 O4 2.0644(17) . ? Zn1 O5 2.0317(17) . ? Zn1 N3 2.104(2) . ? Zn2 S3 2.3512(7) . ? Zn2 S4 2.4242(7) . ? Zn2 O3 2.0433(16) . ? Zn2 N6 2.094(2) . ? Zn2 N9 2.216(2) . ? S1 C1 1.714(3) . ? S3 C10 1.708(3) . ? S4 C7 1.703(2) . ? O1 C4 1.270(3) . ? O2 C4 1.242(3) . ? O3 C6 1.275(3) . ? O4 C6 1.250(3) . ? O5 H5C 0.88(4) . ? O5 H5D 0.77(4) . ? O6 N10 1.258(3) . ? O7 N10 1.224(3) . ? O8 N10 1.241(3) . ? O9 N11 1.264(3) . ? O10 N11 1.253(3) . ? O11 N11 1.251(3) . ? N1 H1 0.79(3) . ? N1 C1 1.336(3) . ? N1 C2 1.464(3) . ? N2 H2 0.78(3) . ? N2 N3 1.405(3) . ? N2 C1 1.340(3) . ? N3 H3A 0.82(3) . ? N3 H3B 0.86(3) . ? N4 H4 0.89(3) . ? N4 C7 1.331(3) . ? N4 C8 1.453(3) . ? N5 H5 0.77(3) . ? N5 N6 1.410(3) . ? N5 C7 1.341(3) . ? N6 H6A 0.84(3) . ? N6 H6B 0.89(3) . ? N7 H7 0.86(3) . ? N7 C10 1.326(3) . ? N7 C11 1.464(4) . ? N8 H8 0.83(3) . ? N8 N9 1.409(3) . ? N8 C10 1.347(3) . ? N9 H9A 0.80(3) . ? N9 H9B 0.89(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.512(4) . ? C3 H3C 0.9800 . ? C3 H3D 0.9800 . ? C3 H3E 0.9800 . ? C4 C5 1.531(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.512(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.511(4) . ? C9 H9C 0.9800 . ? C9 H9D 0.9800 . ? C9 H9E 0.9800 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.493(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 Zn1 O1 135.39(6) . . ? S1 Zn1 O4 91.98(5) . . ? S1 Zn1 O5 114.50(6) . . ? S1 Zn1 N3 84.75(6) . . ? O1 Zn1 O4 87.99(7) . . ? O1 Zn1 O5 109.97(8) . . ? O1 Zn1 N3 95.56(8) . . ? O4 Zn1 O5 85.65(7) . . ? O4 Zn1 N3 176.30(8) . . ? O5 Zn1 N3 94.12(9) . . ? S3 Zn2 S4 96.06(2) . . ? S3 Zn2 O3 104.67(5) . . ? S3 Zn2 N6 135.39(7) . . ? S3 Zn2 N9 82.47(6) . . ? S4 Zn2 O3 101.49(5) . . ? S4 Zn2 N6 83.89(6) . . ? S4 Zn2 N9 171.65(6) . . ? O3 Zn2 N6 119.12(8) . . ? O3 Zn2 N9 86.82(8) . . ? N6 Zn2 N9 91.38(8) . . ? Zn1 S1 C1 96.01(9) . . ? Zn2 S3 C10 98.03(9) . . ? Zn2 S4 C7 95.73(8) . . ? Zn1 O1 C4 128.55(16) . . ? Zn2 O3 C6 112.56(14) . . ? Zn1 O4 C6 125.48(15) . . ? Zn1 O5 H5C 110(2) . . ? Zn1 O5 H5D 118(3) . . ? H5C O5 H5D 113(3) . . ? H1 N1 C1 119(2) . . ? H1 N1 C2 115(2) . . ? C1 N1 C2 125.3(2) . . ? H2 N2 N3 119(2) . . ? H2 N2 C1 118(2) . . ? N3 N2 C1 122.0(2) . . ? Zn1 N3 N2 113.58(16) . . ? Zn1 N3 H3A 109.1(19) . . ? Zn1 N3 H3B 113(2) . . ? N2 N3 H3A 106.2(19) . . ? N2 N3 H3B 107.4(19) . . ? H3A N3 H3B 108(3) . . ? H4 N4 C7 116(2) . . ? H4 N4 C8 119(2) . . ? C7 N4 C8 124.4(2) . . ? H5 N5 N6 115(2) . . ? H5 N5 C7 123(2) . . ? N6 N5 C7 122.0(2) . . ? Zn2 N6 N5 114.82(15) . . ? Zn2 N6 H6A 107(2) . . ? Zn2 N6 H6B 113(2) . . ? N5 N6 H6A 108(2) . . ? N5 N6 H6B 107(2) . . ? H6A N6 H6B 106(3) . . ? H7 N7 C10 115(2) . . ? H7 N7 C11 117(2) . . ? C10 N7 C11 125.7(2) . . ? H8 N8 N9 118(2) . . ? H8 N8 C10 119(2) . . ? N9 N8 C10 121.5(2) . . ? Zn2 N9 N8 111.72(15) . . ? Zn2 N9 H9A 105(2) . . ? Zn2 N9 H9B 119.8(19) . . ? N8 N9 H9A 107(2) . . ? N8 N9 H9B 104(2) . . ? H9A N9 H9B 109(3) . . ? O6 N10 O7 118.9(2) . . ? O6 N10 O8 120.1(2) . . ? O7 N10 O8 121.0(2) . . ? O9 N11 O10 119.5(2) . . ? O9 N11 O11 119.9(2) . . ? O10 N11 O11 120.6(2) . . ? S1 C1 N1 121.4(2) . . ? S1 C1 N2 122.7(2) . . ? N1 C1 N2 115.8(2) . . ? N1 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? N1 C2 C3 112.3(2) . . ? H2A C2 H2B 107.9 . . ? H2A C2 C3 109.1 . . ? H2B C2 C3 109.1 . . ? C2 C3 H3C 109.5 . . ? C2 C3 H3D 109.5 . . ? C2 C3 H3E 109.5 . . ? H3C C3 H3D 109.5 . . ? H3C C3 H3E 109.5 . . ? H3D C3 H3E 109.5 . . ? O1 C4 O2 124.0(2) . . ? O1 C4 C5 117.9(2) . . ? O2 C4 C5 118.0(2) . . ? C4 C5 H5A 108.5 . . ? C4 C5 H5B 108.5 . . ? C4 C5 C6 115.01(19) . . ? H5A C5 H5B 107.5 . . ? H5A C5 C6 108.5 . . ? H5B C5 C6 108.5 . . ? O3 C6 O4 121.1(2) . . ? O3 C6 C5 118.0(2) . . ? O4 C6 C5 120.9(2) . . ? S4 C7 N4 121.42(18) . . ? S4 C7 N5 123.22(18) . . ? N4 C7 N5 115.4(2) . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? N4 C8 C9 110.6(2) . . ? H8A C8 H8B 108.1 . . ? H8A C8 C9 109.5 . . ? H8B C8 C9 109.5 . . ? C8 C9 H9C 109.5 . . ? C8 C9 H9D 109.5 . . ? C8 C9 H9E 109.5 . . ? H9C C9 H9D 109.5 . . ? H9C C9 H9E 109.5 . . ? H9D C9 H9E 109.5 . . ? S3 C10 N7 121.6(2) . . ? S3 C10 N8 122.6(2) . . ? N7 C10 N8 115.7(2) . . ? N7 C11 H11A 109.3 . . ? N7 C11 H11B 109.3 . . ? N7 C11 C12 111.8(2) . . ? H11A C11 H11B 107.9 . . ? H11A C11 C12 109.3 . . ? H11B C11 C12 109.3 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5C O9 0.88(4) 1.88(4) 2.756(3) 169(3) 2_665 O5 H5C N11 0.88(4) 2.60(4) 3.412(3) 154(3) 2_665 O5 H5C O11 0.88(4) 2.61(4) 3.225(3) 127(3) 2_665 O5 H5D O2 0.77(4) 2.03(4) 2.785(3) 166(4) 1_655 N1 H1 O6 0.79(3) 2.23(3) 2.983(3) 161(3) 1_665 N1 H1 O7 0.79(3) 2.62(3) 3.190(3) 130(2) 1_665 N1 H1 N10 0.79(3) 2.66(3) 3.335(3) 145(2) 1_665 N2 H2 O7 0.78(3) 2.19(3) 2.865(3) 145(3) 1_665 N2 H2 O2 0.78(3) 2.46(3) 3.022(3) 130(2) 2_675 N3 H3A O7 0.82(3) 2.23(3) 2.944(3) 145(2) 2_665 N3 H3A O2 0.82(3) 2.57(3) 3.206(3) 135(2) 1_655 N3 H3B O1 0.86(3) 2.21(3) 2.916(3) 139(3) 2_675 N3 H3B O8 0.86(3) 2.40(3) 2.945(3) 122(2) 1_565 N4 H4 O3 0.89(3) 1.96(3) 2.828(3) 165(3) 1_655 N5 H5 O10 0.77(3) 2.42(3) 3.078(3) 144(3) . N5 H5 O3 0.77(3) 2.49(3) 3.124(3) 141(2) 1_655 N6 H6A O11 0.84(3) 2.23(3) 2.819(3) 128(3) 2_665 N6 H6A O4 0.84(3) 2.46(3) 2.912(3) 115(2) . N6 H6B O9 0.89(3) 2.41(3) 3.058(3) 130(3) . N6 H6A O5 0.84(3) 2.71(3) 3.471(3) 151(3) . N6 H6B O6 0.89(3) 2.43(3) 3.148(3) 139(3) . N7 H7 O8 0.86(3) 2.20(3) 2.980(3) 151(3) 1_455 N7 H7 O6 0.86(3) 2.27(3) 3.049(3) 150(3) 1_455 N7 H7 N10 0.86(3) 2.56(3) 3.425(3) 178(3) 1_455 N8 H8 O8 0.83(3) 2.32(3) 3.037(3) 144(3) 1_455 N8 H8 O9 0.83(3) 2.47(3) 3.128(3) 137(3) 1_455 N9 H9A O10 0.80(3) 2.17(3) 2.921(3) 157(3) 1_455 N9 H9B O6 0.89(3) 2.64(3) 3.201(3) 122(2) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.545 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.087