# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/2113 data_tnis1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H41.50 Cl2 N4 Ni2 O8.75 S2' _chemical_formula_weight 862.62 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' 'Ni' 'Ni' 0.3393 1.1124 '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 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 20.517(2) _cell_length_b 27.241(3) _cell_length_c 15.7733(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8815.6(17) _cell_formula_units_Z 8 _cell_measurement_temperature 158(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.73 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3580 _exptl_absorpt_coefficient_mu 1.117 _exptl_absorpt_correction_type Semi-empirical(SADABS) _exptl_absorpt_correction_T_min 0.56 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 158(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART area detector ' _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 55909 _diffrn_reflns_av_R_equivalents 0.1189 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7768 _reflns_number_gt 4607 _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^)+(0.1664P)^2^+114.5085P] 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 7768 _refine_ls_number_parameters 440 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1927 _refine_ls_R_factor_gt 0.1374 _refine_ls_wR_factor_ref 0.4096 _refine_ls_wR_factor_gt 0.3812 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_restrained_S_all 1.173 _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 0.13861(9) 0.31823(6) 0.98699(9) 0.0410(5) Uani 1 1 d . . . Ni2 Ni 0.24794(9) 0.23724(6) 0.99647(9) 0.0397(5) Uani 1 1 d . . . S1 S 0.17758(18) 0.26932(12) 1.08316(18) 0.0406(8) Uani 1 1 d . . . C1 C 0.2285(7) 0.3107(5) 1.1416(7) 0.043(3) Uani 1 1 d . . . C2 C 0.2047(7) 0.3567(4) 1.1657(7) 0.038(3) Uani 1 1 d . . . C3 C 0.2415(7) 0.3859(5) 1.2201(8) 0.044(3) Uani 1 1 d . . . H3 H 0.2242 0.4164 1.2389 0.053 Uiso 1 1 calc R . . C4 C 0.3028(8) 0.3715(5) 1.2474(8) 0.047(4) Uani 1 1 d . . . C5 C 0.3247(7) 0.3254(5) 1.2263(7) 0.045(3) Uani 1 1 d . . . H5 H 0.3647 0.3138 1.2489 0.054 Uiso 1 1 calc R . . C6 C 0.2875(7) 0.2946(4) 1.1706(7) 0.035(3) Uani 1 1 d . . . C7 C 0.3449(7) 0.4050(5) 1.3015(9) 0.052(4) Uani 1 1 d . . . C25 C 0.4025(11) 0.4235(9) 1.2482(15) 0.113(8) Uani 1 1 d . . . H25A H 0.4420 0.4053 1.2635 0.169 Uiso 1 1 calc R . . H25B H 0.4093 0.4586 1.2591 0.169 Uiso 1 1 calc R . . H25C H 0.3931 0.4186 1.1879 0.169 Uiso 1 1 calc R . . C26 C 0.3080(10) 0.4488(7) 1.3376(12) 0.089(6) Uani 1 1 d . . . H26A H 0.2866 0.4666 1.2914 0.134 Uiso 1 1 calc R . . H26B H 0.3385 0.4707 1.3667 0.134 Uiso 1 1 calc R . . H26C H 0.2750 0.4372 1.3778 0.134 Uiso 1 1 calc R . . C27 C 0.3744(11) 0.3753(7) 1.3785(13) 0.097(8) Uani 1 1 d . . . H27A H 0.3390 0.3616 1.4127 0.145 Uiso 1 1 calc R . . H27B H 0.4008 0.3974 1.4137 0.145 Uiso 1 1 calc R . . H27C H 0.4019 0.3486 1.3570 0.145 Uiso 1 1 calc R . . C8 C 0.3168(7) 0.2464(5) 1.1524(8) 0.043(3) Uani 1 1 d . . . H8 H 0.3475 0.2343 1.1924 0.052 Uiso 1 1 calc R . . N1 N 0.1100(6) 0.3649(4) 1.0707(6) 0.043(3) Uani 1 1 d . . . C9 C 0.3358(7) 0.1705(5) 1.0840(8) 0.046(3) Uani 1 1 d . . . H9A H 0.3018 0.1448 1.0870 0.055 Uiso 1 1 calc R . . H9B H 0.3647 0.1666 1.1338 0.055 Uiso 1 1 calc R . . C10 C 0.3762(7) 0.1635(5) 1.0019(8) 0.051(4) Uani 1 1 d . . . H10A H 0.4087 0.1903 0.9978 0.061 Uiso 1 1 calc R . . H10B H 0.4004 0.1321 1.0058 0.061 Uiso 1 1 calc R . . C11 C 0.3362(8) 0.1631(5) 0.9240(8) 0.055(4) Uani 1 1 d . . . H11A H 0.3018 0.1378 0.9291 0.067 Uiso 1 1 calc R . . H11B H 0.3639 0.1546 0.8748 0.067 Uiso 1 1 calc R . . N2 N 0.1136(6) 0.3599(4) 0.8930(7) 0.044(3) Uani 1 1 d . . . C12 C 0.3187(7) 0.2339(5) 0.8422(8) 0.043(3) Uani 1 1 d . . . H12 H 0.3470 0.2173 0.8041 0.052 Uiso 1 1 calc R . . S2 S 0.17973(18) 0.26364(12) 0.90135(19) 0.0426(9) Uani 1 1 d . . . C13 C 0.2325(7) 0.3006(4) 0.8403(7) 0.039(3) Uani 1 1 d . . . C14 C 0.2952(8) 0.2827(5) 0.8148(7) 0.049(4) Uani 1 1 d . . . C15 C 0.3355(8) 0.3103(5) 0.7630(7) 0.052(4) Uani 1 1 d . . . H15 H 0.3765 0.2972 0.7463 0.063 Uiso 1 1 calc R . . C16 C 0.3171(8) 0.3572(6) 0.7345(8) 0.052(4) Uani 1 1 d . A . C17 C 0.2557(8) 0.3730(5) 0.7584(7) 0.048(4) Uani 1 1 d . . . H17 H 0.2410 0.4040 0.7384 0.057 Uiso 1 1 calc R . . C18 C 0.2150(8) 0.3460(5) 0.8098(7) 0.049(4) Uani 1 1 d . . . C19 C 0.3645(8) 0.3897(6) 0.6843(9) 0.058(4) Uani 1 1 d . . . C28 C 0.407(2) 0.4184(15) 0.749(2) 0.087(11) Uiso 0.55 1 d P A 1 H28A H 0.4428 0.4347 0.7185 0.131 Uiso 0.55 1 calc PR A 1 H28B H 0.4250 0.3956 0.7906 0.131 Uiso 0.55 1 calc PR A 1 H28C H 0.3802 0.4431 0.7774 0.131 Uiso 0.55 1 calc PR A 1 C29 C 0.3312(17) 0.4325(12) 0.632(2) 0.073(9) Uiso 0.55 1 d P A 1 H29A H 0.2973 0.4188 0.5953 0.109 Uiso 0.55 1 calc PR A 1 H29B H 0.3642 0.4491 0.5974 0.109 Uiso 0.55 1 calc PR A 1 H29C H 0.3116 0.4562 0.6713 0.109 Uiso 0.55 1 calc PR A 1 C30 C 0.4117(18) 0.3620(13) 0.629(2) 0.075(9) Uiso 0.55 1 d P A 1 H30A H 0.4391 0.3855 0.5978 0.113 Uiso 0.55 1 calc PR A 1 H30B H 0.3874 0.3419 0.5880 0.113 Uiso 0.55 1 calc PR A 1 H30C H 0.4392 0.3408 0.6638 0.113 Uiso 0.55 1 calc PR A 1 C31 C 0.377(3) 0.4342(18) 0.725(3) 0.094(15) Uiso 0.45 1 d P A 2 H31A H 0.4067 0.4539 0.6904 0.141 Uiso 0.45 1 calc PR A 2 H31B H 0.3974 0.4277 0.7804 0.141 Uiso 0.45 1 calc PR A 2 H31C H 0.3362 0.4520 0.7336 0.141 Uiso 0.45 1 calc PR A 2 C32 C 0.328(2) 0.3927(17) 0.593(3) 0.088(13) Uiso 0.45 1 d P A 2 H32A H 0.3543 0.4126 0.5538 0.132 Uiso 0.45 1 calc PR A 2 H32B H 0.2851 0.4078 0.5998 0.132 Uiso 0.45 1 calc PR A 2 H32C H 0.3231 0.3596 0.5695 0.132 Uiso 0.45 1 calc PR A 2 C33 C 0.437(3) 0.359(2) 0.676(4) 0.13(2) Uiso 0.45 1 d P A 2 H33A H 0.4289 0.3257 0.6549 0.192 Uiso 0.45 1 calc PR A 2 H33B H 0.4575 0.3571 0.7322 0.192 Uiso 0.45 1 calc PR A 2 H33C H 0.4657 0.3765 0.6371 0.192 Uiso 0.45 1 calc PR A 2 C20 C 0.1502(8) 0.3673(5) 0.8274(9) 0.053(4) Uani 1 1 d . . . H20 H 0.1333 0.3890 0.7857 0.064 Uiso 1 1 calc R . . N3 N 0.3055(6) 0.2121(4) 0.9098(6) 0.044(3) Uani 1 1 d . . . C21 C 0.0491(9) 0.3819(6) 0.8982(10) 0.063(4) Uani 1 1 d . . . H21A H 0.0161 0.3555 0.9010 0.075 Uiso 1 1 calc R . . H21B H 0.0409 0.4011 0.8459 0.075 Uiso 1 1 calc R . . C22 C 0.0413(8) 0.4144(6) 0.9726(9) 0.057(4) Uani 1 1 d . . . H22A H -0.0017 0.4308 0.9692 0.069 Uiso 1 1 calc R . . H22B H 0.0752 0.4403 0.9706 0.069 Uiso 1 1 calc R . . C23 C 0.0463(8) 0.3867(5) 1.0594(9) 0.053(4) Uani 1 1 d . . . H23A H 0.0378 0.4100 1.1062 0.063 Uiso 1 1 calc R . . H23B H 0.0127 0.3606 1.0616 0.063 Uiso 1 1 calc R . . N4 N 0.3048(5) 0.2190(4) 1.0869(6) 0.040(3) Uani 1 1 d . . . C24 C 0.1419(7) 0.3756(5) 1.1374(9) 0.044(3) Uani 1 1 d . . . H24 H 0.1221 0.3991 1.1737 0.053 Uiso 1 1 calc R . . Cl1 Cl 0.1424(3) 0.46936(17) 0.6223(4) 0.0963(18) Uani 1 1 d . . . O11 O 0.1863(9) 0.4862(6) 0.6875(13) 0.144(7) Uani 1 1 d . . . O12 O 0.1783(12) 0.4481(6) 0.5459(12) 0.157(8) Uani 1 1 d . . . O13 O 0.1059(8) 0.4308(4) 0.6554(9) 0.095(4) Uani 1 1 d . . . O14 O 0.1091(10) 0.5093(6) 0.5968(13) 0.149(7) Uani 1 1 d . . . Cl2 Cl 0.0000 0.2843(3) 1.2500 0.0805(19) Uani 1 2 d S . . O21 O -0.020(2) 0.2657(16) 1.160(3) 0.157(15) Uiso 0.50 1 d P . . O22 O -0.0589(14) 0.2988(10) 1.2812(17) 0.078(8) Uiso 0.50 1 d P . . O23 O 0.010(3) 0.2380(15) 1.283(3) 0.162(17) Uiso 0.50 1 d P . . O24 O 0.0522(12) 0.3186(9) 1.2431(15) 0.064(6) Uiso 0.50 1 d P . . Cl3 Cl -0.0032(6) 0.2604(3) 0.7720(4) 0.057(2) Uani 0.50 1 d P . . O31 O -0.0213(18) 0.2679(13) 0.861(2) 0.131(12) Uiso 0.50 1 d P . . O32 O 0.0530(8) 0.2861(5) 0.7644(9) 0.100(4) Uiso 1 1 d . . . O33 O 0.0000 0.2154(13) 0.7500 0.176(12) Uiso 1 2 d S . . O40 O 0.0346(14) 0.2671(9) 0.9977(15) 0.085(7) Uiso 0.50 1 d P . . H40A H 0.0176 0.2671 1.0486 0.102 Uiso 0.50 1 d P . . H40B H 0.0207 0.2714 0.9477 0.102 Uiso 0.50 1 d P . . O50 O 0.0000 0.4578(15) 1.2500 0.102(12) Uiso 0.50 2 d SP . . C51 C -0.042(2) 0.4868(14) 1.193(3) 0.088(12) Uiso 0.50 1 d P . . H51A H -0.0634 0.5134 1.2258 0.105 Uiso 0.50 1 calc PR . . H51B H -0.0154 0.5021 1.1483 0.105 Uiso 0.50 1 calc PR . . C52 C -0.0937(16) 0.4565(11) 1.1525(19) 0.058(8) Uiso 0.50 1 d P . . H52A H -0.0926 0.4233 1.1763 0.070 Uiso 0.50 1 calc PR . . H52B H -0.0859 0.4549 1.0913 0.070 Uiso 0.50 1 calc PR . . H52C H -0.1365 0.4713 1.1631 0.070 Uiso 0.50 1 calc PR . . 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 0.0490(11) 0.0463(10) 0.0277(8) -0.0005(7) -0.0009(7) 0.0011(8) Ni2 0.0531(11) 0.0432(10) 0.0227(7) -0.0026(6) 0.0012(7) 0.0000(8) S1 0.052(2) 0.0414(17) 0.0285(15) -0.0001(12) 0.0035(14) -0.0026(16) C1 0.058(10) 0.054(8) 0.017(5) -0.001(5) -0.001(5) -0.013(7) C2 0.048(9) 0.037(7) 0.030(6) 0.001(5) -0.003(6) 0.002(6) C3 0.063(10) 0.036(7) 0.034(6) -0.007(5) 0.001(6) 0.003(7) C4 0.068(11) 0.041(7) 0.032(6) 0.001(6) -0.006(7) -0.002(7) C5 0.051(9) 0.063(9) 0.021(6) -0.001(5) -0.011(6) 0.001(7) C6 0.044(8) 0.035(6) 0.027(6) 0.005(5) 0.001(6) 0.003(6) C7 0.049(10) 0.054(8) 0.053(8) -0.005(7) -0.016(7) -0.001(7) C25 0.090(17) 0.122(18) 0.127(19) -0.052(16) 0.032(15) -0.028(15) C26 0.105(17) 0.079(12) 0.084(13) -0.044(11) -0.020(12) 0.002(12) C27 0.115(18) 0.079(12) 0.095(14) -0.015(10) -0.080(13) -0.014(12) C8 0.059(10) 0.039(7) 0.032(7) 0.006(5) 0.004(6) -0.002(7) N1 0.055(8) 0.047(6) 0.027(5) 0.004(4) -0.001(5) 0.006(6) C9 0.060(10) 0.045(7) 0.031(6) 0.001(5) 0.000(6) 0.004(7) C10 0.056(9) 0.042(7) 0.053(8) 0.000(6) 0.024(7) 0.007(7) C11 0.079(12) 0.054(8) 0.034(7) -0.009(6) 0.004(7) 0.019(8) N2 0.040(7) 0.055(7) 0.038(6) -0.009(5) -0.004(5) -0.003(6) C12 0.051(9) 0.042(7) 0.037(7) -0.009(6) -0.002(6) 0.009(7) S2 0.053(2) 0.0480(19) 0.0274(15) -0.0041(13) -0.0048(14) -0.0001(17) C13 0.051(9) 0.040(7) 0.027(6) -0.006(5) -0.002(6) -0.004(6) C14 0.068(11) 0.057(8) 0.021(6) -0.005(6) 0.003(6) 0.010(8) C15 0.071(11) 0.069(9) 0.018(6) -0.002(6) -0.004(6) 0.010(8) C16 0.057(10) 0.066(9) 0.032(7) -0.007(6) -0.004(7) -0.003(8) C17 0.064(11) 0.049(8) 0.029(6) 0.001(6) -0.007(7) 0.009(8) C18 0.060(10) 0.061(9) 0.024(6) -0.004(6) -0.010(6) 0.003(8) C19 0.062(11) 0.071(10) 0.042(8) 0.008(7) 0.022(7) 0.005(9) C20 0.080(12) 0.041(8) 0.038(7) 0.001(6) -0.008(7) -0.004(8) N3 0.061(8) 0.050(6) 0.022(5) -0.007(4) 0.004(5) -0.005(6) C21 0.071(12) 0.058(9) 0.059(9) -0.008(7) -0.003(8) 0.016(9) C22 0.045(9) 0.059(9) 0.068(10) -0.002(7) -0.013(7) 0.014(8) C23 0.056(10) 0.053(8) 0.049(8) 0.004(6) -0.008(7) 0.018(8) N4 0.048(7) 0.042(6) 0.029(5) -0.001(4) -0.002(5) 0.002(5) C24 0.035(8) 0.045(7) 0.052(8) -0.001(6) -0.002(6) -0.002(7) Cl1 0.125(5) 0.055(3) 0.109(4) 0.012(3) -0.041(4) -0.005(3) O11 0.130(15) 0.116(13) 0.187(18) -0.040(12) -0.074(14) 0.003(11) O12 0.26(2) 0.101(12) 0.116(13) -0.041(11) 0.047(15) -0.018(14) O13 0.125(12) 0.064(8) 0.097(10) 0.023(7) -0.026(9) -0.010(8) O14 0.181(19) 0.092(11) 0.174(17) 0.042(11) -0.027(15) 0.051(12) Cl2 0.052(4) 0.082(4) 0.107(5) 0.000 0.019(4) 0.000 Cl3 0.061(5) 0.062(4) 0.047(6) 0.004(3) 0.006(6) -0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 1.926(10) . y Ni1 N2 1.936(11) . y Ni1 S1 2.171(4) . y Ni1 S2 2.179(4) . y Ni2 N4 1.909(10) . y Ni2 N3 1.932(10) . y Ni2 S1 2.172(4) . y Ni2 S2 2.174(4) . y S1 C1 1.792(13) . ? C1 C6 1.368(18) . ? C1 C2 1.398(18) . ? C2 C3 1.392(18) . ? C2 C24 1.459(19) . ? C3 C4 1.39(2) . ? C4 C5 1.375(19) . ? C4 C7 1.518(19) . ? C5 C6 1.433(17) . ? C6 C8 1.471(17) . ? C7 C26 1.52(2) . ? C7 C25 1.54(3) . ? C7 C27 1.58(2) . ? C8 N4 1.300(15) . ? N1 C24 1.273(17) . ? N1 C23 1.445(18) . ? C9 N4 1.466(16) . ? C9 C10 1.550(17) . ? C10 C11 1.48(2) . ? C11 N3 1.493(17) . ? N2 C20 1.295(18) . ? N2 C21 1.454(19) . ? C12 N3 1.250(16) . ? C12 C14 1.478(18) . ? S2 C13 1.765(13) . ? C13 C18 1.376(18) . ? C13 C14 1.43(2) . ? C14 C15 1.39(2) . ? C15 C16 1.41(2) . ? C16 C17 1.38(2) . ? C16 C19 1.53(2) . ? C17 C18 1.38(2) . ? C18 C20 1.48(2) . ? C19 C31 1.40(5) . ? C19 C30 1.51(4) . ? C19 C28 1.55(4) . ? C19 C29 1.58(3) . ? C19 C32 1.63(5) . ? C19 C33 1.71(6) . ? C21 C22 1.48(2) . ? C22 C23 1.567(19) . ? Cl1 O14 1.347(15) . ? Cl1 O13 1.393(13) . ? Cl1 O11 1.442(17) . ? Cl1 O12 1.527(18) . ? Cl2 O22 1.36(3) . ? Cl2 O22 1.36(3) 3_557 ? Cl2 O23 1.38(4) 3_557 ? Cl2 O23 1.38(4) . ? Cl2 O24 1.43(2) . ? Cl2 O24 1.43(2) 3_557 ? Cl2 O21 1.57(5) . ? Cl2 O21 1.57(4) 3_557 ? O21 O23 1.20(5) 3_557 ? O22 O24 0.67(3) 3_557 ? O23 O23 1.12(8) 3_557 ? O23 O21 1.20(5) 3_557 ? O24 O22 0.67(3) 3_557 ? Cl3 Cl3 0.708(12) 3_556 ? Cl3 O33 1.27(3) . ? Cl3 O32 1.355(18) . ? Cl3 O32 1.365(18) 3_556 ? Cl3 O31 1.46(4) . ? O32 Cl3 1.365(18) 3_556 ? O33 Cl3 1.27(3) 3_556 ? O50 C51 1.48(4) 3_557 ? O50 C51 1.48(4) . ? C51 C52 1.48(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N2 93.3(4) . . y N1 Ni1 S1 92.2(3) . . y N2 Ni1 S1 172.8(4) . . y N1 Ni1 S2 173.8(4) . . y N2 Ni1 S2 91.6(3) . . y S1 Ni1 S2 82.63(13) . . y N4 Ni2 N3 93.6(5) . . y N4 Ni2 S1 92.3(3) . . y N3 Ni2 S1 173.9(4) . . y N4 Ni2 S2 174.5(3) . . y N3 Ni2 S2 91.3(3) . . y S1 Ni2 S2 82.74(14) . . y C1 S1 Ni1 100.8(4) . . y C1 S1 Ni2 100.9(5) . . y Ni1 S1 Ni2 92.97(13) . . y C6 C1 C2 120.4(12) . . ? C6 C1 S1 119.1(10) . . ? C2 C1 S1 120.1(11) . . ? C3 C2 C1 119.4(12) . . ? C3 C2 C24 117.7(12) . . ? C1 C2 C24 122.8(12) . . ? C4 C3 C2 121.4(12) . . ? C5 C4 C3 118.6(13) . . ? C5 C4 C7 120.0(13) . . ? C3 C4 C7 121.4(12) . . ? C4 C5 C6 120.7(13) . . ? C1 C6 C5 119.2(12) . . ? C1 C6 C8 125.7(12) . . ? C5 C6 C8 115.1(12) . . ? C4 C7 C26 113.4(13) . . ? C4 C7 C25 109.1(13) . . ? C26 C7 C25 109.3(15) . . ? C4 C7 C27 110.1(12) . . ? C26 C7 C27 107.7(14) . . ? C25 C7 C27 107.1(16) . . ? N4 C8 C6 126.2(12) . . ? C24 N1 C23 118.3(12) . . ? C24 N1 Ni1 124.1(10) . . ? C23 N1 Ni1 117.5(9) . . ? N4 C9 C10 111.7(10) . . ? C11 C10 C9 113.4(13) . . ? C10 C11 N3 110.7(11) . . ? C20 N2 C21 120.5(13) . . ? C20 N2 Ni1 123.4(10) . . ? C21 N2 Ni1 116.1(10) . . ? N3 C12 C14 127.2(12) . . ? C13 S2 Ni2 99.8(5) . . y C13 S2 Ni1 100.8(4) . . y Ni2 S2 Ni1 92.70(13) . . y C18 C13 C14 116.3(13) . . ? C18 C13 S2 122.9(11) . . ? C14 C13 S2 120.7(10) . . ? C15 C14 C13 121.1(13) . . ? C15 C14 C12 117.7(13) . . ? C13 C14 C12 121.2(13) . . ? C14 C15 C16 121.4(14) . . ? C17 C16 C15 116.1(14) . . ? C17 C16 C19 122.6(14) . . ? C15 C16 C19 121.2(14) . . ? C18 C17 C16 123.1(13) . . ? C13 C18 C17 121.9(14) . . ? C13 C18 C20 121.5(13) . . ? C17 C18 C20 116.6(13) . . ? C31 C19 C30 126(3) . . ? C31 C19 C16 112(2) . . ? C30 C19 C16 114.8(18) . . ? C31 C19 C28 32(2) . . ? C30 C19 C28 106(2) . . ? C16 C19 C28 108.1(18) . . ? C31 C19 C29 71(3) . . ? C30 C19 C29 110(2) . . ? C16 C19 C29 114.9(18) . . ? C28 C19 C29 102(2) . . ? C31 C19 C32 117(3) . . ? C30 C19 C32 79(2) . . ? C16 C19 C32 101(2) . . ? C28 C19 C32 144(3) . . ? C29 C19 C32 45.8(18) . . ? C31 C19 C33 107(3) . . ? C30 C19 C33 32(2) . . ? C16 C19 C33 108(2) . . ? C28 C19 C33 79(3) . . ? C29 C19 C33 134(3) . . ? C32 C19 C33 111(3) . . ? N2 C20 C18 127.7(13) . . ? C12 N3 C11 117.5(11) . . ? C12 N3 Ni2 124.6(10) . . ? C11 N3 Ni2 117.9(8) . . ? N2 C21 C22 113.0(13) . . ? C21 C22 C23 113.4(13) . . ? N1 C23 C22 111.5(12) . . ? C8 N4 C9 117.5(11) . . ? C8 N4 Ni2 124.1(9) . . ? C9 N4 Ni2 118.4(8) . . ? N1 C24 C2 128.8(13) . . ? O14 Cl1 O13 116.7(12) . . ? O14 Cl1 O11 105.8(12) . . ? O13 Cl1 O11 107.9(11) . . ? O14 Cl1 O12 108.4(13) . . ? O13 Cl1 O12 105.6(10) . . ? O11 Cl1 O12 112.6(14) . . ? O22 Cl2 O22 146(2) . 3_557 ? O22 Cl2 O23 106(3) . 3_557 ? O22 Cl2 O23 105(3) 3_557 3_557 ? O22 Cl2 O23 105(3) . . ? O22 Cl2 O23 106(3) 3_557 . ? O23 Cl2 O23 48(3) 3_557 . ? O22 Cl2 O24 120.2(18) . . ? O22 Cl2 O24 27.8(13) 3_557 . ? O23 Cl2 O24 133(2) 3_557 . ? O23 Cl2 O24 121(2) . . ? O22 Cl2 O24 27.8(13) . 3_557 ? O22 Cl2 O24 120.2(18) 3_557 3_557 ? O23 Cl2 O24 121(2) 3_557 3_557 ? O23 Cl2 O24 133(2) . 3_557 ? O24 Cl2 O24 98(2) . 3_557 ? O22 Cl2 O21 101(2) . . ? O22 Cl2 O21 90(2) 3_557 . ? O23 Cl2 O21 47.3(19) 3_557 . ? O23 Cl2 O21 95(3) . . ? O24 Cl2 O21 109.8(19) . . ? O24 Cl2 O21 94.8(19) 3_557 . ? O22 Cl2 O21 90(2) . 3_557 ? O22 Cl2 O21 101(2) 3_557 3_557 ? O23 Cl2 O21 95(3) 3_557 3_557 ? O23 Cl2 O21 47.3(19) . 3_557 ? O24 Cl2 O21 94.8(19) . 3_557 ? O24 Cl2 O21 109.8(19) 3_557 3_557 ? O21 Cl2 O21 142(3) . 3_557 ? O23 O21 Cl2 58(3) 3_557 . ? O24 O22 Cl2 81(4) 3_557 . ? O23 O23 O21 140(3) 3_557 3_557 ? O23 O23 Cl2 66.1(17) 3_557 . ? O21 O23 Cl2 75(3) 3_557 . ? O22 O24 Cl2 71(4) 3_557 . ? Cl3 Cl3 O33 73.9(5) 3_556 . ? Cl3 Cl3 O32 75.7(17) 3_556 . ? O33 Cl3 O32 115.3(10) . . ? Cl3 Cl3 O32 74.1(17) 3_556 3_556 ? O33 Cl3 O32 114.7(10) . 3_556 ? O32 Cl3 O32 109.5(12) . 3_556 ? Cl3 Cl3 O31 170.9(18) 3_556 . ? O33 Cl3 O31 114.2(15) . . ? O32 Cl3 O31 103.2(17) . . ? O32 Cl3 O31 98.1(17) 3_556 . ? Cl3 O32 Cl3 30.2(6) . 3_556 ? Cl3 O33 Cl3 32.2(10) . 3_556 ? C51 O50 C51 116(4) 3_557 . ? C52 C51 O50 112(3) . . ? 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 N1 Ni1 S1 C1 -52.5(6) . . . . ? N2 Ni1 S1 C1 87(3) . . . . ? S2 Ni1 S1 C1 124.1(5) . . . . ? N1 Ni1 S1 Ni2 -154.2(4) . . . . ? N2 Ni1 S1 Ni2 -15(3) . . . . ? S2 Ni1 S1 Ni2 22.42(14) . . . . ? N4 Ni2 S1 C1 53.5(5) . . . . ? N3 Ni2 S1 C1 -114(3) . . . . ? S2 Ni2 S1 C1 -124.1(4) . . . . ? N4 Ni2 S1 Ni1 155.1(3) . . . . ? N3 Ni2 S1 Ni1 -12(3) . . . . ? S2 Ni2 S1 Ni1 -22.46(14) . . . . ? Ni1 S1 C1 C6 -140.9(9) . . . . ? Ni2 S1 C1 C6 -45.7(10) . . . . ? Ni1 S1 C1 C2 46.7(10) . . . . ? Ni2 S1 C1 C2 141.9(9) . . . . ? C6 C1 C2 C3 -0.5(18) . . . . ? S1 C1 C2 C3 171.8(9) . . . . ? C6 C1 C2 C24 -179.4(12) . . . . ? S1 C1 C2 C24 -7.0(17) . . . . ? C1 C2 C3 C4 3.5(19) . . . . ? C24 C2 C3 C4 -177.6(12) . . . . ? C2 C3 C4 C5 -6(2) . . . . ? C2 C3 C4 C7 175.5(13) . . . . ? C3 C4 C5 C6 5.8(19) . . . . ? C7 C4 C5 C6 -175.7(12) . . . . ? C2 C1 C6 C5 0.3(18) . . . . ? S1 C1 C6 C5 -172.1(9) . . . . ? C2 C1 C6 C8 177.8(11) . . . . ? S1 C1 C6 C8 5.4(17) . . . . ? C4 C5 C6 C1 -3.0(18) . . . . ? C4 C5 C6 C8 179.3(12) . . . . ? C5 C4 C7 C26 -165.5(14) . . . . ? C3 C4 C7 C26 13(2) . . . . ? C5 C4 C7 C25 72.5(18) . . . . ? C3 C4 C7 C25 -109.1(17) . . . . ? C5 C4 C7 C27 -45(2) . . . . ? C3 C4 C7 C27 133.6(15) . . . . ? C1 C6 C8 N4 25(2) . . . . ? C5 C6 C8 N4 -157.4(13) . . . . ? N2 Ni1 N1 C24 -136.8(11) . . . . ? S1 Ni1 N1 C24 38.5(11) . . . . ? S2 Ni1 N1 C24 5(4) . . . . ? N2 Ni1 N1 C23 47.2(10) . . . . ? S1 Ni1 N1 C23 -137.5(9) . . . . ? S2 Ni1 N1 C23 -170(3) . . . . ? N4 C9 C10 C11 -65.3(16) . . . . ? C9 C10 C11 N3 65.9(16) . . . . ? N1 Ni1 N2 C20 135.1(11) . . . . ? S1 Ni1 N2 C20 -4(4) . . . . ? S2 Ni1 N2 C20 -41.1(11) . . . . ? N1 Ni1 N2 C21 -46.8(10) . . . . ? S1 Ni1 N2 C21 174(2) . . . . ? S2 Ni1 N2 C21 136.9(9) . . . . ? N4 Ni2 S2 C13 98(4) . . . . ? N3 Ni2 S2 C13 -55.1(5) . . . . ? S1 Ni2 S2 C13 123.8(4) . . . . ? N4 Ni2 S2 Ni1 -4(4) . . . . ? N3 Ni2 S2 Ni1 -156.5(3) . . . . ? S1 Ni2 S2 Ni1 22.38(14) . . . . ? N1 Ni1 S2 C13 -90(3) . . . . ? N2 Ni1 S2 C13 52.8(6) . . . . ? S1 Ni1 S2 C13 -122.9(5) . . . . ? N1 Ni1 S2 Ni2 11(3) . . . . ? N2 Ni1 S2 Ni2 153.3(4) . . . . ? S1 Ni1 S2 Ni2 -22.39(14) . . . . ? Ni2 S2 C13 C18 -138.0(10) . . . . ? Ni1 S2 C13 C18 -43.3(11) . . . . ? Ni2 S2 C13 C14 46.5(10) . . . . ? Ni1 S2 C13 C14 141.2(9) . . . . ? C18 C13 C14 C15 0.6(18) . . . . ? S2 C13 C14 C15 176.4(10) . . . . ? C18 C13 C14 C12 -178.8(11) . . . . ? S2 C13 C14 C12 -3.0(17) . . . . ? N3 C12 C14 C15 149.8(14) . . . . ? N3 C12 C14 C13 -31(2) . . . . ? C13 C14 C15 C16 1(2) . . . . ? C12 C14 C15 C16 -179.6(12) . . . . ? C14 C15 C16 C17 -2.5(19) . . . . ? C14 C15 C16 C19 174.0(13) . . . . ? C15 C16 C17 C18 2.5(19) . . . . ? C19 C16 C17 C18 -174.0(13) . . . . ? C14 C13 C18 C17 -0.7(18) . . . . ? S2 C13 C18 C17 -176.4(10) . . . . ? C14 C13 C18 C20 176.4(11) . . . . ? S2 C13 C18 C20 0.8(17) . . . . ? C16 C17 C18 C13 -1(2) . . . . ? C16 C17 C18 C20 -178.2(12) . . . . ? C17 C16 C19 C31 56(3) . . . . ? C15 C16 C19 C31 -120(3) . . . . ? C17 C16 C19 C30 -152(2) . . . . ? C15 C16 C19 C30 32(2) . . . . ? C17 C16 C19 C28 91(2) . . . . ? C15 C16 C19 C28 -86(2) . . . . ? C17 C16 C19 C29 -23(2) . . . . ? C15 C16 C19 C29 161.1(17) . . . . ? C17 C16 C19 C32 -69(2) . . . . ? C15 C16 C19 C32 115(2) . . . . ? C17 C16 C19 C33 174(3) . . . . ? C15 C16 C19 C33 -2(3) . . . . ? C21 N2 C20 C18 -176.7(13) . . . . ? Ni1 N2 C20 C18 1(2) . . . . ? C13 C18 C20 N2 29(2) . . . . ? C17 C18 C20 N2 -153.4(14) . . . . ? C14 C12 N3 C11 -179.1(14) . . . . ? C14 C12 N3 Ni2 1(2) . . . . ? C10 C11 N3 C12 120.6(14) . . . . ? C10 C11 N3 Ni2 -59.8(15) . . . . ? N4 Ni2 N3 C12 -136.3(12) . . . . ? S1 Ni2 N3 C12 31(4) . . . . ? S2 Ni2 N3 C12 41.2(11) . . . . ? N4 Ni2 N3 C11 44.2(10) . . . . ? S1 Ni2 N3 C11 -149(3) . . . . ? S2 Ni2 N3 C11 -138.3(10) . . . . ? C20 N2 C21 C22 -120.7(15) . . . . ? Ni1 N2 C21 C22 61.1(16) . . . . ? N2 C21 C22 C23 -64.4(18) . . . . ? C24 N1 C23 C22 125.1(13) . . . . ? Ni1 N1 C23 C22 -58.7(14) . . . . ? C21 C22 C23 N1 62.8(18) . . . . ? C6 C8 N4 C9 -175.6(12) . . . . ? C6 C8 N4 Ni2 2.8(19) . . . . ? C10 C9 N4 C8 -124.1(13) . . . . ? C10 C9 N4 Ni2 57.3(14) . . . . ? N3 Ni2 N4 C8 138.0(11) . . . . ? S1 Ni2 N4 C8 -40.6(11) . . . . ? S2 Ni2 N4 C8 -15(4) . . . . ? N3 Ni2 N4 C9 -43.5(10) . . . . ? S1 Ni2 N4 C9 137.9(9) . . . . ? S2 Ni2 N4 C9 164(3) . . . . ? C23 N1 C24 C2 176.3(13) . . . . ? Ni1 N1 C24 C2 0(2) . . . . ? C3 C2 C24 N1 155.4(14) . . . . ? C1 C2 C24 N1 -26(2) . . . . ? O22 Cl2 O21 O23 -102(4) . . . 3_557 ? O22 Cl2 O21 O23 110(4) 3_557 . . 3_557 ? O23 Cl2 O21 O23 4(6) . . . 3_557 ? O24 Cl2 O21 O23 130(4) . . . 3_557 ? O24 Cl2 O21 O23 -129(4) 3_557 . . 3_557 ? O21 Cl2 O21 O23 2(3) 3_557 . . 3_557 ? O22 Cl2 O22 O24 27(3) 3_557 . . 3_557 ? O23 Cl2 O22 O24 -128(4) 3_557 . . 3_557 ? O23 Cl2 O22 O24 -178(4) . . . 3_557 ? O24 Cl2 O22 O24 41(5) . . . 3_557 ? O21 Cl2 O22 O24 -79(4) . . . 3_557 ? O21 Cl2 O22 O24 137(4) 3_557 . . 3_557 ? O22 Cl2 O23 O23 98(5) . . . 3_557 ? O22 Cl2 O23 O23 -96(5) 3_557 . . 3_557 ? O24 Cl2 O23 O23 -121(5) . . . 3_557 ? O24 Cl2 O23 O23 97(5) 3_557 . . 3_557 ? O21 Cl2 O23 O23 -4(6) . . . 3_557 ? O21 Cl2 O23 O23 174(8) 3_557 . . 3_557 ? O22 Cl2 O23 O21 -76(4) . . . 3_557 ? O22 Cl2 O23 O21 90(4) 3_557 . . 3_557 ? O23 Cl2 O23 O21 -174(8) 3_557 . . 3_557 ? O24 Cl2 O23 O21 65(4) . . . 3_557 ? O24 Cl2 O23 O21 -77(4) 3_557 . . 3_557 ? O21 Cl2 O23 O21 -178(2) . . . 3_557 ? O22 Cl2 O24 O22 -163(2) . . . 3_557 ? O23 Cl2 O24 O22 3(5) 3_557 . . 3_557 ? O23 Cl2 O24 O22 63(4) . . . 3_557 ? O24 Cl2 O24 O22 -145(4) 3_557 . . 3_557 ? O21 Cl2 O24 O22 -47(4) . . . 3_557 ? O21 Cl2 O24 O22 104(4) 3_557 . . 3_557 ? O33 Cl3 O32 Cl3 64.0(10) . . . 3_556 ? O32 Cl3 O32 Cl3 -67.1(13) 3_556 . . 3_556 ? O31 Cl3 O32 Cl3 -171(2) . . . 3_556 ? O32 Cl3 O33 Cl3 -65.1(17) . . . 3_556 ? O32 Cl3 O33 Cl3 63.5(17) 3_556 . . 3_556 ? O31 Cl3 O33 Cl3 176(3) . . . 3_556 ? C51 O50 C51 C52 -167(4) 3_557 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.430 _refine_diff_density_min -0.876 _refine_diff_density_rms 0.214 data_nisbj _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H30 I12 N4 S2' _chemical_formula_weight 1985.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.854(7) _cell_length_b 15.450(7) _cell_length_c 25.559(14) _cell_angle_alpha 90.00 _cell_angle_beta 91.291(10) _cell_angle_gamma 90.00 _cell_volume 4680(4) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour chocolate-brown _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.818 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3528 _exptl_absorpt_coefficient_mu 8.053 _exptl_absorpt_correction_type Semi-empirical _exptl_absorpt_correction_T_min 0.60 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART area detector' _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 29085 _diffrn_reflns_av_R_equivalents 0.1066 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.82 _reflns_number_total 4775 _reflns_number_gt 2969 _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^)+(0.0800P)^2^+172.5624P] 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 4775 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1144 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1854 _refine_ls_wR_factor_gt 0.1587 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 I1 I 0.74479(8) 0.66984(7) 0.59960(4) 0.0391(3) Uani 1 1 d . . . I2 I 0.57095(9) 0.68507(7) 0.70814(4) 0.0417(3) Uani 1 1 d . . . I3 I 0.92904(10) 0.55107(7) 0.53011(4) 0.0447(3) Uani 1 1 d . . . I4 I 0.92481(10) 0.66834(9) 0.70690(6) 0.0597(4) Uani 1 1 d . . . I5 I 0.56463(11) 0.50693(8) 0.58458(5) 0.0529(3) Uani 1 1 d . . . I6 I 0.42080(12) 0.36513(9) 0.57745(6) 0.0614(4) Uani 1 1 d . . . S1 S 0.9069(3) 0.4187(3) 0.66624(17) 0.0412(10) Uani 1 1 d . . . C1 C 0.8574(15) 0.3333(11) 0.6289(7) 0.044(4) Uani 1 1 d . . . C2 C 0.7545(15) 0.2924(11) 0.6319(6) 0.045(4) Uani 1 1 d . . . C3 C 0.7292(18) 0.2266(12) 0.5985(8) 0.064(6) Uani 1 1 d . . . H3 H 0.6562 0.2014 0.5997 0.077 Uiso 1 1 calc R . . C4 C 0.8044(16) 0.1942(13) 0.5626(7) 0.052(5) Uani 1 1 d . . . C5 C 0.9105(17) 0.2361(11) 0.5578(7) 0.052(5) Uani 1 1 d . . . H5 H 0.9612 0.2180 0.5317 0.063 Uiso 1 1 calc R . . C6 C 0.9398(12) 0.3033(10) 0.5912(6) 0.035(4) Uani 1 1 d . . . C7 C 0.7728(18) 0.1202(13) 0.5259(8) 0.062(5) Uani 1 1 d . . . H7A H 0.7799 0.0651 0.5447 0.074 Uiso 1 1 calc R . . H7B H 0.8234 0.1202 0.4961 0.074 Uiso 1 1 calc R . . H7C H 0.6948 0.1277 0.5132 0.074 Uiso 1 1 calc R . . C8 C 1.0406(15) 0.3528(11) 0.5978(6) 0.043(4) Uani 1 1 d . . . H8 H 1.1064 0.3429 0.5781 0.052 Uiso 1 1 calc R . . N1 N 1.0344(11) 0.4129(8) 0.6335(5) 0.038(3) Uani 1 1 d . . . C9 C 1.1302(13) 0.4647(15) 0.6501(7) 0.054(5) Uani 1 1 d . . . H9A H 1.1034 0.5220 0.6618 0.065 Uiso 1 1 calc R . . H9B H 1.1798 0.4739 0.6199 0.065 Uiso 1 1 calc R . . C10 C 1.1966(16) 0.4228(13) 0.6936(7) 0.052(5) Uiso 1 1 d . . . H10A H 1.2342 0.3706 0.6798 0.063 Uiso 1 1 calc R . . H10B H 1.1438 0.4037 0.7207 0.063 Uiso 1 1 calc R . . C11 C 1.2858(14) 0.4813(13) 0.7190(7) 0.051(5) Uani 1 1 d . . . H11A H 1.3379 0.5019 0.6920 0.061 Uiso 1 1 calc R . . H11B H 1.2486 0.5325 0.7342 0.061 Uiso 1 1 calc R . . C12 C 1.3520(14) 0.4346(13) 0.7612(7) 0.049(5) Uani 1 1 d . . . H12A H 1.3990 0.3895 0.7449 0.059 Uiso 1 1 calc R . . H12B H 1.4034 0.4763 0.7790 0.059 Uiso 1 1 calc R . . N2 N 1.2799(12) 0.3932(9) 0.8009(5) 0.042(3) Uani 1 1 d . . . C13 C 1.3195(12) 0.3281(12) 0.8291(7) 0.047(4) Uani 1 1 d . . . H13 H 1.3931 0.3057 0.8242 0.057 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 I1 0.0339(5) 0.0349(6) 0.0488(6) -0.0080(5) 0.0080(4) 0.0015(4) I2 0.0446(6) 0.0339(6) 0.0466(6) 0.0049(5) 0.0029(5) 0.0004(5) I3 0.0559(7) 0.0413(7) 0.0371(6) 0.0070(5) 0.0076(5) 0.0094(5) I4 0.0447(7) 0.0411(7) 0.0944(10) -0.0033(7) 0.0251(7) -0.0060(5) I5 0.0659(8) 0.0423(7) 0.0506(7) 0.0014(6) 0.0016(6) 0.0032(6) I6 0.0597(8) 0.0516(8) 0.0729(9) -0.0049(7) 0.0025(7) -0.0029(6) S1 0.035(2) 0.040(2) 0.049(2) 0.0037(19) 0.0059(18) 0.0013(18) C1 0.050(10) 0.037(10) 0.045(10) 0.013(8) 0.000(8) 0.017(8) C2 0.054(11) 0.041(10) 0.040(9) 0.005(8) -0.007(8) -0.012(8) C3 0.070(14) 0.038(11) 0.083(15) 0.015(11) -0.032(12) -0.024(10) C4 0.052(11) 0.048(12) 0.056(11) 0.005(9) 0.000(9) 0.018(9) C5 0.073(13) 0.031(10) 0.053(11) -0.011(8) -0.012(10) 0.012(9) C6 0.030(8) 0.033(9) 0.044(9) 0.017(7) 0.016(7) 0.012(7) C7 0.075(14) 0.055(13) 0.055(12) -0.011(10) -0.011(10) 0.005(11) C8 0.052(10) 0.036(10) 0.041(9) 0.015(8) 0.011(8) 0.015(8) N1 0.050(8) 0.024(7) 0.042(8) 0.001(6) -0.003(6) 0.003(6) C9 0.024(8) 0.091(16) 0.049(10) 0.006(10) 0.010(7) -0.016(9) C11 0.032(9) 0.051(12) 0.068(12) -0.006(9) 0.002(8) -0.006(8) C12 0.034(9) 0.058(12) 0.057(11) 0.003(9) 0.014(8) -0.011(8) N2 0.047(8) 0.037(8) 0.041(8) 0.000(6) 0.003(6) 0.005(7) C13 0.018(7) 0.057(12) 0.067(12) -0.008(10) 0.007(7) 0.008(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I2 I2 2.751(2) 2_656 y I3 I3 2.794(2) 5_766 y I4 I4 2.803(3) 2_756 y I5 I6 2.780(2) . y S1 C1 1.724(19) . y S1 N1 1.746(14) . y C1 C2 1.38(2) . ? C1 C6 1.46(2) . ? C2 C3 1.36(3) . ? C2 C13 1.45(2) 2_756 ? C3 C4 1.39(3) . ? C4 C5 1.42(3) . ? C4 C7 1.52(3) . ? C5 C6 1.38(2) . ? C6 C8 1.43(2) . y C8 N1 1.31(2) . y N1 C9 1.44(2) . ? C9 C10 1.49(2) . ? C10 C11 1.52(2) . ? C11 C12 1.50(3) . ? C12 N2 1.49(2) . ? N2 C13 1.32(2) . y C13 C2 1.45(2) 2_756 y 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 C1 S1 N1 89.0(7) . . y C2 C1 C6 119.8(17) . . y C2 C1 S1 127.6(14) . . y C6 C1 S1 112.6(13) . . y C3 C2 C1 119.4(19) . . ? C3 C2 C13 126.1(18) . 2_756 ? C1 C2 C13 114.5(16) . 2_756 ? C2 C3 C4 123.4(19) . . ? C3 C4 C5 118.3(18) . . ? C3 C4 C7 121.8(18) . . ? C5 C4 C7 119.7(17) . . ? C6 C5 C4 120.0(18) . . ? C5 C6 C8 132.4(16) . . y C5 C6 C1 118.8(16) . . y C8 C6 C1 108.8(15) . . y N1 C8 C6 113.8(15) . . y C8 N1 C9 122.8(15) . . y C8 N1 S1 115.8(12) . . y C9 N1 S1 121.0(11) . . y N1 C9 C10 112.1(16) . . ? C9 C10 C11 114.2(16) . . ? C12 C11 C10 111.6(16) . . ? N2 C12 C11 113.4(14) . . ? C13 N2 C12 119.9(14) . . ? N2 C13 C2 116.9(14) . 2_756 ? 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 N1 S1 C1 C2 177.6(16) . . . . ? N1 S1 C1 C6 -1.1(11) . . . . ? C6 C1 C2 C3 -2(2) . . . . ? S1 C1 C2 C3 179.0(14) . . . . ? C6 C1 C2 C13 179.9(14) . . . 2_756 ? S1 C1 C2 C13 1(2) . . . 2_756 ? C1 C2 C3 C4 4(3) . . . . ? C13 C2 C3 C4 -178.9(18) 2_756 . . . ? C2 C3 C4 C5 -5(3) . . . . ? C2 C3 C4 C7 179.9(18) . . . . ? C3 C4 C5 C6 5(3) . . . . ? C7 C4 C5 C6 -179.9(16) . . . . ? C4 C5 C6 C8 175.4(16) . . . . ? C4 C5 C6 C1 -4(2) . . . . ? C2 C1 C6 C5 2(2) . . . . ? S1 C1 C6 C5 -178.8(12) . . . . ? C2 C1 C6 C8 -176.8(15) . . . . ? S1 C1 C6 C8 2.0(16) . . . . ? C5 C6 C8 N1 178.8(17) . . . . ? C1 C6 C8 N1 -2.1(18) . . . . ? C6 C8 N1 C9 173.7(14) . . . . ? C6 C8 N1 S1 1.4(17) . . . . ? C1 S1 N1 C8 -0.1(12) . . . . ? C1 S1 N1 C9 -172.6(14) . . . . ? C8 N1 C9 C10 -87.9(19) . . . . ? S1 N1 C9 C10 84.1(18) . . . . ? N1 C9 C10 C11 -169.7(15) . . . . ? C9 C10 C11 C12 -178.2(16) . . . . ? C10 C11 C12 N2 -53(2) . . . . ? C11 C12 N2 C13 157.4(16) . . . . ? C12 N2 C13 C2 178.4(15) . . . 2_756 ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 26.82 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 4.821 _refine_diff_density_min -2.240 _refine_diff_density_rms 0.306 data_nis6i _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H30 I6 N4 S2' _chemical_formula_weight 1224.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 '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 8.9104(19) _cell_length_b 9.1521(19) _cell_length_c 12.172(3) _cell_angle_alpha 70.605(3) _cell_angle_beta 85.336(3) _cell_angle_gamma 68.074(3) _cell_volume 867.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 168(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 5.514 _exptl_absorpt_correction_type SADABS(Semi-empirical) _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 168(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART area detector ' _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 11120 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 26.42 _reflns_number_total 3511 _reflns_number_gt 3008 _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^)+(0.0385P)^2^+0.5342P] 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 3511 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0715 _refine_ls_wR_factor_gt 0.0692 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.002 _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 I1 I 0.29718(4) -0.56599(3) 1.18279(2) 0.03448(9) Uani 1 1 d . . . I2 I 0.42581(3) -0.93034(3) 1.29881(2) 0.02651(8) Uani 1 1 d . . . I3 I 0.53648(4) -1.28966(3) 1.41846(2) 0.03581(9) Uani 1 1 d . . . S1 S 0.07847(11) -0.25910(11) 0.87863(8) 0.02277(19) Uani 1 1 d . . . C1 C 0.0479(4) -0.0816(4) 0.7599(3) 0.0209(7) Uani 1 1 d . . . C2 C -0.0703(4) 0.0758(5) 0.7490(3) 0.0230(7) Uani 1 1 d . . . C3 C -0.0780(4) 0.2068(5) 0.6462(3) 0.0244(8) Uani 1 1 d . . . H3 H -0.1573 0.3143 0.6374 0.029 Uiso 1 1 calc R . . C4 C 0.0276(5) 0.1848(5) 0.5556(3) 0.0244(8) Uani 1 1 d . . . C5 C 0.1441(5) 0.0272(5) 0.5688(3) 0.0254(8) Uani 1 1 d . . . H5 H 0.2169 0.0100 0.5088 0.030 Uiso 1 1 calc R . . C6 C 0.1539(5) -0.1065(5) 0.6710(3) 0.0230(7) Uani 1 1 d . . . C7 C 0.0170(5) 0.3298(5) 0.4469(3) 0.0305(9) Uani 1 1 d . . . H7A H 0.0987 0.3748 0.4535 0.037 Uiso 1 1 calc R . . H7B H -0.0911 0.4169 0.4380 0.037 Uiso 1 1 calc R . . H7C H 0.0365 0.2920 0.3788 0.037 Uiso 1 1 calc R . . C8 C 0.2605(5) -0.2763(5) 0.7022(3) 0.0256(8) Uani 1 1 d . . . H8 H 0.3426 -0.3192 0.6540 0.031 Uiso 1 1 calc R . . N1 N 0.2331(4) -0.3675(4) 0.8050(3) 0.0222(6) Uani 1 1 d . . . C9 C 0.3252(4) -0.5483(4) 0.8590(3) 0.0240(8) Uani 1 1 d . . . H9A H 0.3808 -0.5672 0.9325 0.029 Uiso 1 1 calc R . . H9B H 0.4093 -0.5870 0.8059 0.029 Uiso 1 1 calc R . . C10 C 0.2176(4) -0.6510(4) 0.8853(3) 0.0246(8) Uani 1 1 d . . . H10A H 0.1588 -0.6310 0.8129 0.030 Uiso 1 1 calc R . . H10B H 0.1370 -0.6183 0.9421 0.030 Uiso 1 1 calc R . . C11 C 0.3250(4) -0.8352(4) 0.9355(3) 0.0221(7) Uani 1 1 d . . . H11A H 0.3797 -0.8531 1.0091 0.026 Uiso 1 1 calc R . . H11B H 0.4101 -0.8629 0.8801 0.026 Uiso 1 1 calc R . . C12 C 0.2346(5) -0.9554(5) 0.9601(3) 0.0249(8) Uani 1 1 d . . . H12A H 0.1615 -0.9234 0.8920 0.030 Uiso 1 1 calc R . . H12B H 0.3137 -1.0698 0.9715 0.030 Uiso 1 1 calc R . . N2 N 0.1399(4) -0.9533(4) 1.0638(3) 0.0223(6) Uani 1 1 d . . . C13 C 0.1705(4) -1.0871(4) 1.1513(3) 0.0221(7) Uani 1 1 d . . . H13 H 0.2543 -1.1885 1.1511 0.027 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 I1 0.04149(17) 0.02977(15) 0.03299(16) -0.00740(12) 0.00426(12) -0.01700(13) I2 0.02836(15) 0.03125(15) 0.02425(14) -0.01264(11) 0.00529(10) -0.01338(11) I3 0.03895(17) 0.02937(16) 0.03381(16) -0.01133(12) 0.00469(12) -0.00653(12) S1 0.0241(5) 0.0196(4) 0.0230(4) -0.0052(3) 0.0054(4) -0.0088(4) C1 0.0211(18) 0.0199(17) 0.0245(18) -0.0066(14) 0.0011(14) -0.0113(15) C2 0.0209(18) 0.0214(18) 0.0294(19) -0.0075(15) 0.0014(14) -0.0114(15) C3 0.0210(18) 0.0211(18) 0.032(2) -0.0091(15) 0.0020(15) -0.0080(15) C4 0.027(2) 0.0217(18) 0.0244(18) -0.0047(15) -0.0012(15) -0.0104(16) C5 0.029(2) 0.0231(19) 0.0250(19) -0.0081(15) 0.0088(15) -0.0125(16) C6 0.0251(19) 0.0220(18) 0.0231(18) -0.0070(15) 0.0026(14) -0.0105(16) C7 0.036(2) 0.0237(19) 0.027(2) -0.0031(16) 0.0019(17) -0.0108(17) C8 0.026(2) 0.0251(19) 0.028(2) -0.0116(16) 0.0089(15) -0.0103(16) N1 0.0221(16) 0.0177(15) 0.0248(15) -0.0075(12) 0.0052(12) -0.0054(13) C9 0.0209(18) 0.0175(17) 0.0287(19) -0.0073(15) 0.0041(15) -0.0026(15) C10 0.0197(18) 0.0214(18) 0.0288(19) -0.0074(15) 0.0028(15) -0.0042(15) C11 0.0201(18) 0.0214(18) 0.0219(18) -0.0063(15) 0.0015(14) -0.0054(15) C12 0.030(2) 0.0227(18) 0.0252(18) -0.0106(15) 0.0067(15) -0.0122(16) N2 0.0224(16) 0.0217(15) 0.0276(16) -0.0121(13) 0.0068(13) -0.0110(13) C13 0.0206(18) 0.0190(17) 0.0292(19) -0.0116(15) 0.0049(14) -0.0073(14) _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 I1 I2 2.9510(7) . y I2 I3 2.9221(7) . y S1 C1 1.725(4) . y S1 N1 1.748(3) . y C1 C6 1.397(5) . y C1 C2 1.402(5) . ? C2 C3 1.401(5) . ? C2 C13 1.456(5) 2_547 ? C3 C4 1.407(5) . ? C4 C5 1.392(5) . ? C4 C7 1.511(5) . ? C5 C6 1.406(5) . ? C6 C8 1.423(5) . y C8 N1 1.315(5) . y N1 C9 1.482(4) . ? C9 C10 1.526(5) . ? C10 C11 1.529(5) . ? C11 C12 1.534(5) . ? C12 N2 1.462(5) . ? N2 C13 1.281(5) . y C13 C2 1.456(5) 2_547 ? 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 I3 I2 I1 177.004(11) . . y C1 S1 N1 88.18(16) . . y C6 C1 C2 121.0(3) . . . C6 C1 S1 113.8(3) . . y C2 C1 S1 125.3(3) . . ? C3 C2 C1 117.7(4) . . ? C3 C2 C13 126.5(3) . 2_547 ? C1 C2 C13 115.8(3) . 2_547 ? C2 C3 C4 122.4(4) . . ? C5 C4 C3 118.7(3) . . ? C5 C4 C7 120.5(4) . . ? C3 C4 C7 120.7(3) . . ? C4 C5 C6 120.0(4) . . ? C1 C6 C5 120.2(3) . . ? C1 C6 C8 110.2(3) . . y C5 C6 C8 129.6(4) . . ? N1 C8 C6 112.8(3) . . y C8 N1 C9 124.4(3) . . ? C8 N1 S1 115.1(3) . . y C9 N1 S1 120.6(2) . . ? N1 C9 C10 112.7(3) . . ? C9 C10 C11 108.4(3) . . ? C10 C11 C12 114.5(3) . . ? N2 C12 C11 111.3(3) . . ? C13 N2 C12 119.7(3) . . y N2 C13 C2 116.6(3) . 2_547 ? 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 N1 S1 C1 C6 -1.2(3) . . . . ? N1 S1 C1 C2 178.8(3) . . . . ? C6 C1 C2 C3 -0.1(5) . . . . ? S1 C1 C2 C3 179.9(3) . . . . ? C6 C1 C2 C13 -178.3(3) . . . 2_547 ? S1 C1 C2 C13 1.7(5) . . . 2_547 ? C1 C2 C3 C4 0.0(5) . . . . ? C13 C2 C3 C4 178.1(3) 2_547 . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? C2 C3 C4 C7 -179.1(3) . . . . ? C3 C4 C5 C6 0.4(5) . . . . ? C7 C4 C5 C6 179.3(3) . . . . ? C2 C1 C6 C5 0.3(5) . . . . ? S1 C1 C6 C5 -179.7(3) . . . . ? C2 C1 C6 C8 -179.3(3) . . . . ? S1 C1 C6 C8 0.6(4) . . . . ? C4 C5 C6 C1 -0.5(5) . . . . ? C4 C5 C6 C8 179.1(4) . . . . ? C1 C6 C8 N1 0.5(5) . . . . ? C5 C6 C8 N1 -179.1(4) . . . . ? C6 C8 N1 C9 179.7(3) . . . . ? C6 C8 N1 S1 -1.5(4) . . . . ? C1 S1 N1 C8 1.5(3) . . . . ? C1 S1 N1 C9 -179.6(3) . . . . ? C8 N1 C9 C10 -120.8(4) . . . . ? S1 N1 C9 C10 60.4(4) . . . . ? N1 C9 C10 C11 177.5(3) . . . . ? C9 C10 C11 C12 -176.8(3) . . . . ? C10 C11 C12 N2 -74.3(4) . . . . ? C11 C12 N2 C13 -119.2(4) . . . . ? C12 N2 C13 C2 -179.5(3) . . . 2_547 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.473 _refine_diff_density_min -1.858 _refine_diff_density_rms 0.183 data_nis6w _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H40 F6 N4 Ni2 O7 S4' _chemical_formula_weight 952.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.0993(16) _cell_length_b 10.9758(7) _cell_length_c 17.1135(11) _cell_angle_alpha 90.00 _cell_angle_beta 122.5740(10) _cell_angle_gamma 90.00 _cell_volume 3972.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 158(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1960 _exptl_absorpt_coefficient_mu 1.236 _exptl_absorpt_correction_type Semi-empirical(SADABS) _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 158(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART area detector' _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 13534 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3887 _reflns_number_gt 3275 _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^)+(0.0523P)^2^+7.1480P] 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 3887 _refine_ls_number_parameters 249 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0917 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.048 _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 0.071127(13) 0.50866(3) 0.33406(2) 0.02293(11) Uani 1 1 d . . . S1 S 0.02042(3) 0.46446(5) 0.18864(4) 0.02400(15) Uani 1 1 d . . . C1 C 0.02821(11) 0.5913(2) 0.13202(17) 0.0249(5) Uani 1 1 d . . . C2 C -0.02080(11) 0.6207(2) 0.04140(17) 0.0266(5) Uani 1 1 d . . . C3 C -0.01140(12) 0.7091(3) -0.00903(18) 0.0315(6) Uani 1 1 d . . . H3 H -0.0441 0.7253 -0.0714 0.038 Uiso 1 1 calc R . . C4 C 0.04521(13) 0.7736(3) 0.0308(2) 0.0366(6) Uani 1 1 d . . . C5 C 0.09235(13) 0.7467(3) 0.1220(2) 0.0344(6) Uani 1 1 d . . . H5 H 0.1309 0.7911 0.1503 0.041 Uiso 1 1 calc R . . C6 C 0.08525(11) 0.6569(2) 0.17354(18) 0.0285(5) Uani 1 1 d . . . C7 C 0.05508(16) 0.8673(3) -0.0247(2) 0.0552(9) Uani 1 1 d . . . H7A H 0.0285 0.9386 -0.0353 0.066 Uiso 1 1 calc R . . H7B H 0.0436 0.8321 -0.0845 0.066 Uiso 1 1 calc R . . H7C H 0.0996 0.8920 0.0095 0.066 Uiso 1 1 calc R . . C8 C 0.13921(12) 0.6399(2) 0.26856(18) 0.0306(6) Uani 1 1 d . . . H8 H 0.1780 0.6737 0.2816 0.037 Uiso 1 1 calc R . . N1 N 0.14148(9) 0.5857(2) 0.33695(15) 0.0284(5) Uani 1 1 d . . . C9 C 0.20359(12) 0.5916(3) 0.42652(19) 0.0399(7) Uani 1 1 d . . . H9A H 0.1979 0.6296 0.4740 0.048 Uiso 1 1 calc R . . H9B H 0.2328 0.6434 0.4190 0.048 Uiso 1 1 calc R . . C10 C 0.23255(13) 0.4660(3) 0.4595(2) 0.0468(8) Uani 1 1 d . . . H10A H 0.2399 0.4302 0.4130 0.056 Uiso 1 1 calc R . . H10B H 0.2741 0.4747 0.5182 0.056 Uiso 1 1 calc R . . C11 C 0.19225(13) 0.3787(3) 0.4750(2) 0.0406(7) Uani 1 1 d . . . H11A H 0.1569 0.3496 0.4141 0.049 Uiso 1 1 calc R . . H11B H 0.2182 0.3071 0.5099 0.049 Uiso 1 1 calc R . . C12 C 0.16538(12) 0.4348(3) 0.52736(19) 0.0346(6) Uani 1 1 d . . . H12A H 0.1548 0.3692 0.5565 0.042 Uiso 1 1 calc R . . H12B H 0.1979 0.4874 0.5775 0.042 Uiso 1 1 calc R . . N2 N 0.10726(9) 0.50930(19) 0.46575(14) 0.0261(4) Uani 1 1 d . . . C13 C 0.08195(11) 0.5576(2) 0.50644(17) 0.0270(5) Uani 1 1 d . . . H13 H 0.1044 0.5521 0.5721 0.032 Uiso 1 1 calc R . . S50 S 0.20248(3) 0.26940(7) 0.22505(5) 0.03982(19) Uani 1 1 d . . . O51 O 0.15392(9) 0.3445(2) 0.21926(14) 0.0485(6) Uani 1 1 d . . . O52 O 0.26191(10) 0.2718(2) 0.31283(17) 0.0585(7) Uani 1 1 d . . . O53 O 0.20718(15) 0.2767(3) 0.1454(2) 0.0784(9) Uani 1 1 d . . . C50 C 0.1760(2) 0.1162(4) 0.2229(3) 0.0818(15) Uani 1 1 d . . . F51 F 0.17258(15) 0.0918(4) 0.2939(2) 0.1425(17) Uani 1 1 d . . . F52 F 0.11923(14) 0.0949(2) 0.1467(2) 0.1283(14) Uani 1 1 d . . . F53 F 0.21693(18) 0.0363(3) 0.2239(3) 0.1391(16) Uani 1 1 d . . . C60 C 0.1058(5) 1.1056(13) -0.1296(9) 0.112(4) Uiso 0.50 1 d PD A 1 H60A H 0.1077 1.0164 -0.1288 0.134 Uiso 0.50 1 calc PR A 1 H60B H 0.1316 1.1367 -0.0661 0.134 Uiso 0.50 1 calc PR A 1 H60C H 0.1221 1.1375 -0.1664 0.134 Uiso 0.50 1 calc PR A 1 C61 C 0.0433(4) 1.1430(9) -0.1690(5) 0.077(2) Uiso 0.50 1 d PD A 1 H61A H 0.0380 1.2276 -0.1921 0.093 Uiso 0.50 1 calc PR A 1 H61B H 0.0319 1.1405 -0.1220 0.093 Uiso 0.50 1 calc PR A 1 O62 O 0.0000 1.0564(16) -0.2500 0.161(6) Uiso 0.50 2 d SPD . 1 C70 C 0.0955(5) 1.1412(12) -0.1011(7) 0.095(3) Uiso 0.50 1 d PD B 2 H70A H 0.0912 1.2297 -0.1100 0.113 Uiso 0.50 1 calc PR B 2 H70B H 0.1403 1.1187 -0.0693 0.113 Uiso 0.50 1 calc PR B 2 H70C H 0.0787 1.1158 -0.0637 0.113 Uiso 0.50 1 calc PR B 2 C71 C 0.0593(4) 1.0789(15) -0.1940(9) 0.143(5) Uiso 0.50 1 d PD B 2 H71A H 0.0839 1.0791 -0.2237 0.172 Uiso 0.50 1 calc PR B 2 H71B H 0.0498 0.9934 -0.1871 0.172 Uiso 0.50 1 calc PR B 2 O72 O 0.0000 1.1500(15) -0.2500 0.143(5) Uiso 0.50 2 d SPD . 2 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 0.01672(17) 0.02783(18) 0.02217(18) -0.00083(12) 0.00910(14) 0.00062(11) S1 0.0193(3) 0.0268(3) 0.0242(3) -0.0023(2) 0.0106(2) -0.0002(2) C1 0.0234(11) 0.0283(12) 0.0263(12) -0.0026(10) 0.0156(10) 0.0002(9) C2 0.0227(11) 0.0317(13) 0.0270(12) -0.0027(10) 0.0145(10) 0.0000(10) C3 0.0309(13) 0.0387(15) 0.0283(13) 0.0022(11) 0.0181(11) 0.0021(11) C4 0.0368(15) 0.0419(16) 0.0369(15) 0.0034(12) 0.0236(13) -0.0037(12) C5 0.0281(13) 0.0415(15) 0.0386(15) -0.0038(12) 0.0212(12) -0.0084(11) C6 0.0234(12) 0.0356(14) 0.0303(13) -0.0031(11) 0.0171(11) -0.0018(10) C7 0.0521(19) 0.064(2) 0.050(2) 0.0122(17) 0.0282(17) -0.0146(16) C8 0.0221(12) 0.0388(14) 0.0330(14) -0.0057(11) 0.0163(11) -0.0053(10) N1 0.0177(9) 0.0366(12) 0.0282(11) -0.0058(9) 0.0106(9) -0.0027(8) C9 0.0208(12) 0.0618(19) 0.0288(14) -0.0032(13) 0.0079(11) -0.0100(12) C10 0.0227(13) 0.078(2) 0.0354(16) 0.0057(15) 0.0132(12) 0.0132(14) C11 0.0340(14) 0.0456(17) 0.0355(15) 0.0035(13) 0.0142(12) 0.0156(12) C12 0.0250(13) 0.0428(16) 0.0287(14) 0.0085(12) 0.0096(11) 0.0104(11) N2 0.0179(10) 0.0316(11) 0.0237(10) 0.0018(8) 0.0078(9) 0.0018(8) C13 0.0221(12) 0.0326(13) 0.0230(12) 0.0005(10) 0.0100(10) -0.0021(10) S50 0.0327(4) 0.0476(4) 0.0388(4) 0.0089(3) 0.0191(3) 0.0151(3) O51 0.0324(10) 0.0695(15) 0.0363(11) -0.0033(10) 0.0138(9) 0.0187(10) O52 0.0275(11) 0.0637(15) 0.0617(16) 0.0167(12) 0.0092(10) 0.0094(10) O53 0.100(2) 0.096(2) 0.0691(18) 0.0264(16) 0.0649(17) 0.0489(18) C50 0.065(3) 0.056(2) 0.068(3) 0.014(2) -0.002(2) 0.000(2) F51 0.096(2) 0.167(3) 0.107(2) 0.073(2) 0.0166(18) -0.054(2) F52 0.096(2) 0.0654(16) 0.101(2) 0.0048(15) -0.0279(17) -0.0139(15) F53 0.142(3) 0.0554(16) 0.139(3) 0.0062(17) 0.022(2) 0.0438(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 Ni1 N2 1.924(2) . y Ni1 N1 1.934(2) . y Ni1 S1 2.1535(7) . y Ni1 S1 2.1690(7) 2 y S1 C1 1.766(3) . y S1 Ni1 2.1690(7) 2 ? C1 C2 1.403(3) . ? C1 C6 1.406(3) . ? C2 C3 1.401(4) . ? C2 C13 1.467(3) 2 ? C3 C4 1.393(4) . ? C4 C5 1.390(4) . ? C4 C7 1.509(4) . ? C5 C6 1.397(4) . ? C6 C8 1.464(4) . ? C8 N1 1.287(3) . ? N1 C9 1.487(3) . ? C9 C10 1.518(5) . ? C10 C11 1.516(5) . ? C11 C12 1.513(4) . ? C12 N2 1.500(3) . ? N2 C13 1.283(3) . ? C13 C2 1.467(3) 2 ? S50 O51 1.430(2) . ? S50 O53 1.433(3) . ? S50 O52 1.439(2) . ? S50 C50 1.801(4) . ? C50 F51 1.292(6) . ? C50 F52 1.336(5) . ? C50 F53 1.344(6) . ? C60 C61 1.396(12) . ? C61 O62 1.543(12) . ? O62 C61 1.543(12) 2_554 ? C70 C71 1.504(13) . ? C71 O72 1.486(12) . ? O72 C71 1.486(12) 2_554 ? 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 N2 Ni1 N1 96.91(9) . . y N2 Ni1 S1 165.27(7) . . y N1 Ni1 S1 95.25(7) . . y N2 Ni1 S1 89.79(6) . 2 y N1 Ni1 S1 165.19(7) . 2 y S1 Ni1 S1 80.36(3) . 2 y C1 S1 Ni1 106.57(8) . . y C1 S1 Ni1 98.33(8) . 2 y Ni1 S1 Ni1 93.82(3) . 2 y C2 C1 C6 119.3(2) . . ? C2 C1 S1 119.83(18) . . ? C6 C1 S1 120.65(19) . . ? C3 C2 C1 120.1(2) . . ? C3 C2 C13 117.1(2) . 2 ? C1 C2 C13 122.7(2) . 2 ? C4 C3 C2 121.1(2) . . ? C5 C4 C3 118.0(3) . . ? C5 C4 C7 121.5(3) . . ? C3 C4 C7 120.5(3) . . ? C4 C5 C6 122.5(2) . . ? C5 C6 C1 118.9(2) . . ? C5 C6 C8 115.8(2) . . ? C1 C6 C8 125.3(2) . . ? N1 C8 C6 129.1(2) . . ? C8 N1 C9 115.2(2) . . ? C8 N1 Ni1 125.89(17) . . ? C9 N1 Ni1 118.77(18) . . ? N1 C9 C10 111.7(2) . . ? C11 C10 C9 114.0(2) . . ? C12 C11 C10 113.5(3) . . ? N2 C12 C11 112.4(2) . . ? C13 N2 C12 114.9(2) . . ? C13 N2 Ni1 125.35(17) . . ? C12 N2 Ni1 119.20(17) . . ? N2 C13 C2 124.5(2) . 2 ? O51 S50 O53 113.93(15) . . ? O51 S50 O52 115.32(15) . . ? O53 S50 O52 114.98(18) . . ? O51 S50 C50 104.2(2) . . ? O53 S50 C50 104.6(2) . . ? O52 S50 C50 101.66(16) . . ? F51 C50 F52 107.8(5) . . ? F51 C50 F53 106.9(4) . . ? F52 C50 F53 107.7(4) . . ? F51 C50 S50 112.6(4) . . ? F52 C50 S50 111.8(3) . . ? F53 C50 S50 109.7(4) . . ? C60 C61 O62 108.5(9) . . ? C61 O62 C61 104.0(12) . 2_554 ? O72 C71 C70 105.6(10) . . ? C71 O72 C71 116.6(15) 2_554 . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.958 _refine_diff_density_min -0.570 _refine_diff_density_rms 0.084 data_nsce _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H40 N8 Ni2 O8 S2' _chemical_formula_weight 822.24 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' '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.884(6) _cell_length_b 9.948(3) _cell_length_c 18.441(5) _cell_angle_alpha 90.00 _cell_angle_beta 117.713(3) _cell_angle_gamma 90.00 _cell_volume 3554.0(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.88 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 1.237 _exptl_absorpt_correction_type Semi-empirical _exptl_absorpt_correction_T_min 1.00 _exptl_absorpt_correction_T_max 0.92 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Bruker SMART _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 12389 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 26.40 _reflns_number_total 3593 _reflns_number_gt 2636 _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^)+(0.0325P)^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 3593 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0602 _refine_ls_wR_factor_gt 0.0582 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _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 0.081071(13) 0.59318(3) 0.313131(14) 0.02052(8) Uani 1 1 d . . . S1 S -0.01538(3) 0.63542(5) 0.31661(3) 0.02082(12) Uani 1 1 d . . . C1 C -0.02954(10) 0.49026(19) 0.36274(11) 0.0198(4) Uani 1 1 d . . . C2 C -0.09730(10) 0.44782(19) 0.33921(11) 0.0210(4) Uani 1 1 d . . . C3 C -0.10902(11) 0.3430(2) 0.38271(11) 0.0242(5) Uani 1 1 d . . . H3 H -0.1552 0.3178 0.3682 0.029 Uiso 1 1 calc R . . C4 C -0.05487(10) 0.2756(2) 0.44638(11) 0.0235(5) Uani 1 1 d . . . C5 C 0.01220(11) 0.3183(2) 0.46829(11) 0.0232(5) Uani 1 1 d . . . H5 H 0.0498 0.2740 0.5119 0.028 Uiso 1 1 calc R . . C6 C 0.02588(10) 0.42508(19) 0.42779(11) 0.0207(4) Uani 1 1 d . . . C7 C -0.06775(12) 0.1592(2) 0.49015(12) 0.0310(5) Uani 1 1 d . . . H7A H -0.0939 0.1908 0.5179 0.037 Uiso 1 1 calc R . . H7B H -0.0235 0.1220 0.5307 0.037 Uiso 1 1 calc R . . H7C H -0.0942 0.0895 0.4503 0.037 Uiso 1 1 calc R . . C8 C 0.09833(10) 0.4646(2) 0.46125(11) 0.0227(4) Uani 1 1 d . . . H8 H 0.1282 0.4358 0.5155 0.027 Uiso 1 1 calc R . . N1 N 0.12617(8) 0.53431(16) 0.42545(9) 0.0218(4) Uani 1 1 d . . . C9 C 0.19966(10) 0.5721(2) 0.47736(12) 0.0287(5) Uani 1 1 d . . . H9A H 0.2163 0.5308 0.5322 0.034 Uiso 1 1 calc R . . H9B H 0.2030 0.6709 0.4845 0.034 Uiso 1 1 calc R . . C10 C 0.24576(11) 0.5271(2) 0.44052(12) 0.0303(5) Uani 1 1 d . . . H10A H 0.2406 0.4289 0.4308 0.036 Uiso 1 1 calc R . . H10B H 0.2945 0.5451 0.4802 0.036 Uiso 1 1 calc R . . C11 C 0.22866(10) 0.5983(2) 0.36028(12) 0.0281(5) Uani 1 1 d . . . H11A H 0.2288 0.6968 0.3682 0.034 Uiso 1 1 calc R . . H11B H 0.2643 0.5769 0.3433 0.034 Uiso 1 1 calc R . . N2 N 0.15967(8) 0.55549(16) 0.29503(9) 0.0225(4) Uani 1 1 d . . . C12 C 0.15848(10) 0.5026(2) 0.23115(11) 0.0231(5) Uani 1 1 d . . . H12 H 0.2010 0.4984 0.2290 0.028 Uiso 1 1 calc R . . C53 C 0.12249(13) 0.9122(3) 0.31199(14) 0.0427(6) Uani 1 1 d . . . H53 H 0.1298 0.8752 0.2691 0.051 Uiso 1 1 calc R . . N51 N 0.11310(11) 1.0444(2) 0.31071(11) 0.0414(5) Uani 1 1 d . . . O51 O 0.12266(8) 0.83378(15) 0.36327(9) 0.0391(4) Uani 1 1 d . . . N60 N 0.19070(12) 0.7827(2) 0.15514(13) 0.0457(5) Uani 1 1 d . . . O60 O 0.14101(11) 0.8587(2) 0.11571(13) 0.0808(7) Uani 1 1 d . . . O61 O 0.20672(12) 0.6931(2) 0.11999(12) 0.0771(7) Uani 1 1 d . . . O62 O 0.22552(9) 0.79662(18) 0.23041(9) 0.0516(5) Uani 1 1 d . . . C52 C 0.11763(17) 1.1276(3) 0.24852(18) 0.0766(10) Uani 1 1 d . . . H52A H 0.1585 1.1853 0.2743 0.092 Uiso 1 1 calc R . . H52B H 0.0762 1.1836 0.2218 0.092 Uiso 1 1 calc R . . H52C H 0.1213 1.0700 0.2076 0.092 Uiso 1 1 calc R . . C51 C 0.1030(2) 1.1105(3) 0.37339(18) 0.0823(11) Uani 1 1 d . . . H51A H 0.0945 1.0433 0.4065 0.099 Uiso 1 1 calc R . . H51B H 0.0633 1.1711 0.3480 0.099 Uiso 1 1 calc R . . H51C H 0.1444 1.1624 0.4085 0.099 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 Ni1 0.01864(15) 0.02356(15) 0.01985(13) 0.00022(11) 0.00937(11) -0.00176(12) S1 0.0219(3) 0.0201(3) 0.0214(2) -0.0007(2) 0.0108(2) -0.0009(2) C1 0.0243(12) 0.0197(11) 0.0186(9) -0.0024(8) 0.0125(9) -0.0009(9) C2 0.0218(12) 0.0215(11) 0.0227(10) -0.0039(8) 0.0130(9) -0.0011(9) C3 0.0233(12) 0.0286(12) 0.0240(11) -0.0057(9) 0.0137(10) -0.0070(9) C4 0.0275(12) 0.0253(12) 0.0213(10) -0.0039(9) 0.0144(10) -0.0047(10) C5 0.0269(12) 0.0248(12) 0.0192(10) -0.0005(8) 0.0118(9) 0.0003(9) C6 0.0234(11) 0.0222(11) 0.0180(9) -0.0044(8) 0.0107(9) -0.0024(9) C7 0.0327(14) 0.0331(13) 0.0291(11) 0.0020(10) 0.0160(11) -0.0063(11) C8 0.0235(12) 0.0244(11) 0.0188(10) -0.0017(8) 0.0089(9) 0.0000(9) N1 0.0188(9) 0.0239(10) 0.0208(8) -0.0022(7) 0.0077(8) -0.0033(7) C9 0.0206(12) 0.0381(14) 0.0221(10) 0.0008(9) 0.0055(9) -0.0077(10) C10 0.0174(12) 0.0391(14) 0.0282(11) 0.0003(10) 0.0054(10) -0.0047(10) C11 0.0173(11) 0.0359(13) 0.0296(11) -0.0019(10) 0.0096(9) -0.0047(10) N2 0.0185(10) 0.0243(10) 0.0229(8) 0.0016(7) 0.0083(8) -0.0015(7) C12 0.0190(12) 0.0241(12) 0.0282(11) 0.0040(9) 0.0126(10) 0.0014(9) C53 0.0474(16) 0.0442(16) 0.0432(14) -0.0030(12) 0.0268(13) -0.0050(13) N51 0.0540(14) 0.0303(12) 0.0407(11) 0.0084(9) 0.0227(11) 0.0001(10) O51 0.0549(11) 0.0304(9) 0.0399(9) 0.0052(7) 0.0287(9) -0.0034(8) N60 0.0458(15) 0.0428(14) 0.0382(12) 0.0031(11) 0.0108(11) -0.0182(12) O60 0.0583(15) 0.0647(15) 0.0752(14) 0.0152(12) -0.0061(12) -0.0034(12) O61 0.0851(17) 0.0754(16) 0.0618(13) -0.0342(12) 0.0266(12) -0.0168(13) O62 0.0521(12) 0.0618(12) 0.0308(9) -0.0029(8) 0.0108(9) -0.0179(10) C52 0.077(2) 0.073(2) 0.075(2) 0.0397(18) 0.0312(19) -0.0058(18) C51 0.124(3) 0.055(2) 0.064(2) 0.0086(16) 0.040(2) 0.031(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 Ni1 N1 1.9250(16) . y Ni1 N2 1.9351(16) . y Ni1 S1 2.1820(8) . y Ni1 S1 2.1837(7) 2 y S1 C1 1.7750(19) . ? S1 Ni1 2.1837(7) 2 ? C1 C2 1.402(3) . ? C1 C6 1.406(3) . ? C2 C3 1.410(3) . ? C2 C12 1.469(3) 2 ? C3 C4 1.393(3) . ? C4 C5 1.395(3) . ? C4 C7 1.511(3) . ? C5 C6 1.409(3) . ? C6 C8 1.463(3) . ? C8 N1 1.289(2) . ? N1 C9 1.487(3) . ? C9 C10 1.522(3) . ? C10 C11 1.522(3) . ? C11 N2 1.490(3) . ? N2 C12 1.279(2) . ? C12 C2 1.469(3) 2 ? C53 O51 1.225(3) . ? C53 N51 1.329(3) . ? N51 C51 1.434(3) . ? N51 C52 1.455(3) . ? N60 O62 1.242(2) . ? N60 O60 1.244(3) . ? N60 O61 1.244(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 N1 Ni1 N2 94.28(7) . . y N1 Ni1 S1 92.63(5) . . y N2 Ni1 S1 172.70(5) . . y N1 Ni1 S1 169.83(5) . 2 y N2 Ni1 S1 91.91(5) . 2 y S1 Ni1 S1 80.92(2) . 2 y C1 S1 Ni1 104.14(7) . . y C1 S1 Ni1 101.29(7) . 2 y Ni1 S1 Ni1 94.80(2) . 2 y C2 C1 C6 119.57(17) . . ? C2 C1 S1 119.46(15) . . ? C6 C1 S1 120.69(15) . . ? C1 C2 C3 119.51(18) . . ? C1 C2 C12 124.05(17) . 2 ? C3 C2 C12 116.40(17) . 2 ? C4 C3 C2 121.82(19) . . ? C3 C4 C5 117.75(18) . . ? C3 C4 C7 121.50(18) . . ? C5 C4 C7 120.75(18) . . ? C4 C5 C6 122.04(19) . . ? C1 C6 C5 119.24(18) . . ? C1 C6 C8 124.85(17) . . ? C5 C6 C8 115.80(17) . . ? N1 C8 C6 127.33(18) . . ? C8 N1 C9 115.68(16) . . ? C8 N1 Ni1 125.92(14) . . ? C9 N1 Ni1 118.40(12) . . ? N1 C9 C10 112.41(16) . . ? C9 C10 C11 112.51(18) . . ? N2 C11 C10 110.53(16) . . ? C12 N2 C11 116.13(16) . . ? C12 N2 Ni1 126.83(14) . . ? C11 N2 Ni1 116.97(12) . . ? N2 C12 C2 125.86(17) . 2 ? O51 C53 N51 126.1(2) . . ? C53 N51 C51 121.4(2) . . ? C53 N51 C52 120.7(2) . . ? C51 N51 C52 117.8(2) . . ? O62 N60 O60 120.0(2) . . ? O62 N60 O61 119.1(2) . . ? O60 N60 O61 120.8(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 N1 Ni1 S1 C1 -47.21(8) . . . . ? N2 Ni1 S1 C1 114.0(4) . . . . ? S1 Ni1 S1 C1 124.88(6) 2 . . . ? N1 Ni1 S1 Ni1 -150.15(5) . . . 2 ? N2 Ni1 S1 Ni1 11.0(4) . . . 2 ? S1 Ni1 S1 Ni1 21.94(3) 2 . . 2 ? Ni1 S1 C1 C2 -147.33(13) . . . . ? Ni1 S1 C1 C2 -49.38(15) 2 . . . ? Ni1 S1 C1 C6 38.69(15) . . . . ? Ni1 S1 C1 C6 136.64(13) 2 . . . ? C6 C1 C2 C3 1.9(3) . . . . ? S1 C1 C2 C3 -172.14(13) . . . . ? C6 C1 C2 C12 -175.75(17) . . . 2 ? S1 C1 C2 C12 10.2(2) . . . 2 ? C1 C2 C3 C4 -3.1(3) . . . . ? C12 C2 C3 C4 174.76(17) 2 . . . ? C2 C3 C4 C5 2.3(3) . . . . ? C2 C3 C4 C7 -177.17(17) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C7 C4 C5 C6 179.00(17) . . . . ? C2 C1 C6 C5 -0.2(3) . . . . ? S1 C1 C6 C5 173.82(13) . . . . ? C2 C1 C6 C8 -176.22(17) . . . . ? S1 C1 C6 C8 -2.2(3) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C4 C5 C6 C8 175.86(17) . . . . ? C1 C6 C8 N1 -21.8(3) . . . . ? C5 C6 C8 N1 161.99(18) . . . . ? C6 C8 N1 C9 173.66(18) . . . . ? C6 C8 N1 Ni1 -5.8(3) . . . . ? N2 Ni1 N1 C8 -139.09(16) . . . . ? S1 Ni1 N1 C8 38.56(16) . . . . ? S1 Ni1 N1 C8 -11.8(4) 2 . . . ? N2 Ni1 N1 C9 41.47(15) . . . . ? S1 Ni1 N1 C9 -140.89(14) . . . . ? S1 Ni1 N1 C9 168.8(2) 2 . . . ? C8 N1 C9 C10 124.73(19) . . . . ? Ni1 N1 C9 C10 -55.8(2) . . . . ? N1 C9 C10 C11 65.3(2) . . . . ? C9 C10 C11 N2 -68.1(2) . . . . ? C10 C11 N2 C12 -121.54(19) . . . . ? C10 C11 N2 Ni1 61.3(2) . . . . ? N1 Ni1 N2 C12 138.92(17) . . . . ? S1 Ni1 N2 C12 -22.2(5) . . . . ? S1 Ni1 N2 C12 -33.00(16) 2 . . . ? N1 Ni1 N2 C11 -44.33(14) . . . . ? S1 Ni1 N2 C11 154.5(3) . . . . ? S1 Ni1 N2 C11 143.75(13) 2 . . . ? C11 N2 C12 C2 177.21(18) . . . 2 ? Ni1 N2 C12 C2 -6.0(3) . . . 2 ? O51 C53 N51 C51 1.2(4) . . . . ? O51 C53 N51 C52 176.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.279 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.050