# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 1145/260 data_(NMe3-Tempo)2I2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,N-trimethyl-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)ammonium iodide ; _chemical_name_common 'trimethylammonio-tempo iodide' _chemical_melting_point ? _chemical_formula_moiety '2(C12 H26 N2 O), 2(I)' _chemical_formula_sum 'C24 H52 I2 N4 O2' _chemical_formula_weight 682.50 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' '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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.437(4) _cell_length_b 13.763(4) _cell_length_c 17.278(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.45(2) _cell_angle_gamma 90.00 _cell_volume 3172.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.02 _cell_measurement_theta_max 9.89 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 2.006 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8919 _exptl_absorpt_correction_T_max 0.9989 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 9 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CAD4 Enraf-Nonius' _diffrn_measurement_method Omega-theta-scans _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 11 _diffrn_reflns_number 9478 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.1577 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 29.95 _reflns_number_total 9161 _reflns_number_gt 3013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 EXPRESS (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Prout & Pearce, 1996)' _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^)+(0.0521P)^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 9161 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2193 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.37047(2) 0.10309(2) 0.597460(19) 0.04757(11) Uani 1 1 d . . . I2 I 0.39384(3) 0.39379(3) 0.27576(2) 0.06268(13) Uani 1 1 d . . . O11 O 0.2068(3) 0.5655(3) 0.4663(2) 0.0797(14) Uani 1 1 d . . . N12 N 0.1934(3) 0.4829(3) 0.4309(2) 0.0467(10) Uani 1 1 d . . . N13 N 0.1257(3) 0.1948(3) 0.3230(2) 0.0356(8) Uani 1 1 d . . . C14 C 0.1068(3) 0.4740(3) 0.3501(3) 0.0450(12) Uani 1 1 d . . . C15 C 0.1124(4) 0.3783(3) 0.3064(3) 0.0427(12) Uani 1 1 d . . . H151 H 0.0491 0.3671 0.2600 0.051 Uiso 1 1 calc R . . H152 H 0.1643 0.3832 0.2838 0.051 Uiso 1 1 calc R . . C16 C 0.1349(3) 0.2937(3) 0.3661(3) 0.0334(10) Uani 1 1 d . . . H16 H 0.0864 0.2951 0.3932 0.040 Uiso 1 1 calc R . . C17 C 0.2371(3) 0.3097(3) 0.4325(3) 0.0414(11) Uani 1 1 d . . . H171 H 0.2851 0.3170 0.4061 0.050 Uiso 1 1 calc R . . H172 H 0.2561 0.2528 0.4684 0.050 Uiso 1 1 calc R . . C18 C 0.2421(4) 0.3989(4) 0.4862(3) 0.0469(12) Uani 1 1 d . . . C19 C 0.3523(4) 0.4266(4) 0.5330(4) 0.0741(19) Uani 1 1 d . . . H191 H 0.3565 0.4829 0.5670 0.089 Uiso 1 1 calc R . . H192 H 0.3823 0.4407 0.4934 0.089 Uiso 1 1 calc R . . H193 H 0.3872 0.3735 0.5681 0.089 Uiso 1 1 calc R . . C20 C 0.1913(5) 0.3807(4) 0.5477(3) 0.0713(18) Uani 1 1 d . . . H201 H 0.1953 0.4383 0.5802 0.086 Uiso 1 1 calc R . . H202 H 0.2244 0.3281 0.5844 0.086 Uiso 1 1 calc R . . H203 H 0.1223 0.3641 0.5174 0.086 Uiso 1 1 calc R . . C21 C 0.1129(5) 0.5563(4) 0.2943(4) 0.0724(18) Uani 1 1 d . . . H211 H 0.1747 0.5518 0.2858 0.087 Uiso 1 1 calc R . . H212 H 0.1103 0.6173 0.3204 0.087 Uiso 1 1 calc R . . H213 H 0.0576 0.5521 0.2413 0.087 Uiso 1 1 calc R . . C22 C 0.0094(4) 0.4819(4) 0.3646(4) 0.0678(16) Uani 1 1 d . . . H221 H 0.0051 0.4290 0.3993 0.081 Uiso 1 1 calc R . . H222 H -0.0464 0.4791 0.3118 0.081 Uiso 1 1 calc R . . H223 H 0.0081 0.5424 0.3917 0.081 Uiso 1 1 calc R . . C23 C 0.1263(4) 0.1161(3) 0.3836(3) 0.0499(13) Uani 1 1 d . . . H231 H 0.0732 0.1273 0.4030 0.060 Uiso 1 1 calc R . . H232 H 0.1894 0.1166 0.4304 0.060 Uiso 1 1 calc R . . H233 H 0.1168 0.0541 0.3561 0.060 Uiso 1 1 calc R . . C24 C 0.2077(4) 0.1755(4) 0.2929(4) 0.0665(16) Uani 1 1 d . . . H241 H 0.2080 0.2253 0.2540 0.080 Uiso 1 1 calc R . . H242 H 0.1972 0.1134 0.2655 0.080 Uiso 1 1 calc R . . H243 H 0.2709 0.1754 0.3396 0.080 Uiso 1 1 calc R . . C25 C 0.0270(3) 0.1862(4) 0.2501(3) 0.0539(14) Uani 1 1 d . . . H251 H -0.0267 0.1980 0.2688 0.065 Uiso 1 1 calc R . . H252 H 0.0204 0.1220 0.2269 0.065 Uiso 1 1 calc R . . H253 H 0.0241 0.2330 0.2081 0.065 Uiso 1 1 calc R . . O31 O 0.5849(3) 0.7414(3) 0.1216(2) 0.0720(11) Uani 1 1 d . . . N32 N 0.6539(3) 0.7333(3) 0.0938(2) 0.0451(10) Uani 1 1 d . . . N33 N 0.8918(3) 0.6890(3) 0.0034(2) 0.0389(9) Uani 1 1 d . . . C34 C 0.7583(4) 0.7490(4) 0.1552(3) 0.0467(12) Uani 1 1 d . . . C35 C 0.8294(3) 0.7610(3) 0.1092(3) 0.0433(12) Uani 1 1 d . . . H351 H 0.8203 0.8250 0.0839 0.052 Uiso 1 1 calc R . . H352 H 0.8981 0.7563 0.1492 0.052 Uiso 1 1 calc R . . C36 C 0.8115(3) 0.6848(3) 0.0420(3) 0.0363(10) Uani 1 1 d . . . H36 H 0.8154 0.6208 0.0679 0.044 Uiso 1 1 calc R . . C37 C 0.7068(3) 0.6972(4) -0.0232(3) 0.0411(11) Uani 1 1 d . . . H371 H 0.6965 0.6520 -0.0688 0.049 Uiso 1 1 calc R . . H372 H 0.6992 0.7626 -0.0458 0.049 Uiso 1 1 calc R . . C38 C 0.6286(3) 0.6796(3) 0.0137(3) 0.0453(12) Uani 1 1 d . . . C39 C 0.5293(3) 0.7188(4) -0.0475(3) 0.0708(17) Uani 1 1 d . . . H391 H 0.4783 0.7082 -0.0255 0.085 Uiso 1 1 calc R . . H392 H 0.5113 0.6858 -0.1002 0.085 Uiso 1 1 calc R . . H393 H 0.5355 0.7871 -0.0555 0.085 Uiso 1 1 calc R . . C40 C 0.6179(4) 0.5712(4) 0.0311(4) 0.0695(17) Uani 1 1 d . . . H401 H 0.6809 0.5469 0.0699 0.083 Uiso 1 1 calc R . . H402 H 0.5982 0.5353 -0.0203 0.083 Uiso 1 1 calc R . . H403 H 0.5678 0.5638 0.0546 0.083 Uiso 1 1 calc R . . C41 C 0.7891(4) 0.6634(5) 0.2165(3) 0.0775(19) Uani 1 1 d . . . H411 H 0.7423 0.6571 0.2435 0.093 Uiso 1 1 calc R . . H412 H 0.8550 0.6748 0.2579 0.093 Uiso 1 1 calc R . . H413 H 0.7892 0.6047 0.1865 0.093 Uiso 1 1 calc R . . C42 C 0.7590(4) 0.8421(4) 0.2027(4) 0.0737(18) Uani 1 1 d . . . H421 H 0.7394 0.8956 0.1643 0.088 Uiso 1 1 calc R . . H422 H 0.8252 0.8533 0.2436 0.088 Uiso 1 1 calc R . . H423 H 0.7128 0.8361 0.2303 0.088 Uiso 1 1 calc R . . C43 C 0.9028(4) 0.7866(4) -0.0285(4) 0.0662(16) Uani 1 1 d . . . H431 H 0.8396 0.8067 -0.0700 0.079 Uiso 1 1 calc R . . H432 H 0.9521 0.7840 -0.0532 0.079 Uiso 1 1 calc R . . H433 H 0.9236 0.8323 0.0169 0.079 Uiso 1 1 calc R . . C44 C 0.9917(3) 0.6597(4) 0.0684(3) 0.0535(14) Uani 1 1 d . . . H441 H 0.9863 0.5963 0.0894 0.064 Uiso 1 1 calc R . . H442 H 1.0115 0.7057 0.1136 0.064 Uiso 1 1 calc R . . H443 H 1.0409 0.6585 0.0436 0.064 Uiso 1 1 calc R . . C45 C 0.8679(4) 0.6166(4) -0.0664(3) 0.0584(15) Uani 1 1 d . . . H451 H 0.8621 0.5530 -0.0458 0.070 Uiso 1 1 calc R . . H452 H 0.9206 0.6164 -0.0874 0.070 Uiso 1 1 calc R . . H453 H 0.8058 0.6339 -0.1106 0.070 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 0.04289(17) 0.04378(18) 0.04705(18) 0.00345(17) 0.00711(13) -0.00377(17) I2 0.0534(2) 0.0612(2) 0.0668(2) 0.0256(2) 0.01548(18) 0.00063(19) O11 0.089(3) 0.0314(19) 0.085(3) -0.0114(19) -0.005(2) -0.002(2) N12 0.045(2) 0.032(2) 0.052(2) -0.0051(19) 0.006(2) -0.0032(19) N13 0.036(2) 0.033(2) 0.035(2) -0.0016(16) 0.0110(16) -0.0017(17) C14 0.043(3) 0.031(3) 0.053(3) 0.005(2) 0.008(2) 0.000(2) C15 0.048(3) 0.036(3) 0.035(2) 0.001(2) 0.005(2) -0.001(2) C16 0.038(2) 0.030(2) 0.034(2) -0.0047(19) 0.0147(19) -0.002(2) C17 0.044(3) 0.034(2) 0.041(3) 0.000(2) 0.010(2) 0.000(2) C18 0.055(3) 0.038(3) 0.037(2) -0.002(2) 0.005(2) -0.002(3) C19 0.063(4) 0.058(4) 0.068(4) -0.008(3) -0.013(3) -0.002(3) C20 0.115(5) 0.055(4) 0.053(3) -0.007(3) 0.043(3) -0.007(3) C21 0.095(5) 0.042(3) 0.065(4) 0.016(3) 0.014(3) -0.001(3) C22 0.056(3) 0.045(3) 0.100(5) -0.010(3) 0.027(3) 0.004(3) C23 0.068(3) 0.031(3) 0.049(3) 0.006(2) 0.021(3) -0.001(3) C24 0.068(4) 0.057(4) 0.095(4) -0.022(3) 0.053(3) -0.009(3) C25 0.053(3) 0.044(3) 0.048(3) -0.008(2) 0.002(2) -0.004(3) O31 0.058(2) 0.079(3) 0.102(3) -0.013(2) 0.057(2) 0.001(2) N32 0.043(2) 0.041(2) 0.063(3) -0.004(2) 0.033(2) 0.0036(19) N33 0.034(2) 0.044(2) 0.042(2) -0.0007(18) 0.0181(18) -0.0019(18) C34 0.052(3) 0.049(3) 0.043(3) -0.003(2) 0.023(2) 0.006(2) C35 0.033(2) 0.052(3) 0.049(3) -0.007(2) 0.020(2) -0.007(2) C36 0.032(2) 0.037(2) 0.046(3) 0.004(2) 0.022(2) 0.000(2) C37 0.032(2) 0.044(3) 0.045(3) -0.006(2) 0.011(2) -0.001(2) C38 0.035(2) 0.042(3) 0.062(3) -0.008(3) 0.023(2) -0.002(2) C39 0.035(3) 0.087(5) 0.087(4) -0.016(4) 0.020(3) 0.003(3) C40 0.058(3) 0.047(3) 0.118(5) -0.017(3) 0.050(4) -0.014(3) C41 0.090(5) 0.091(5) 0.062(4) 0.020(3) 0.040(4) 0.018(4) C42 0.076(4) 0.077(4) 0.079(4) -0.028(3) 0.042(3) -0.004(3) C43 0.066(4) 0.063(4) 0.087(4) 0.015(3) 0.048(3) -0.001(3) C44 0.033(3) 0.070(4) 0.051(3) -0.012(3) 0.009(2) 0.005(3) C45 0.042(3) 0.088(4) 0.049(3) -0.018(3) 0.022(2) 0.005(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 O11 N12 1.271(5) . ? N12 C14 1.482(6) . ? N12 C18 1.493(6) . ? N13 C24 1.489(6) . ? N13 C25 1.503(5) . ? N13 C23 1.503(5) . ? N13 C16 1.533(5) . ? C14 C21 1.512(6) . ? C14 C22 1.523(7) . ? C14 C15 1.537(6) . ? C15 C16 1.507(6) . ? C15 H151 0.9700 . ? C15 H152 0.9700 . ? C16 C17 1.499(5) . ? C16 H16 0.9800 . ? C17 C18 1.524(6) . ? C17 H171 0.9700 . ? C17 H172 0.9700 . ? C18 C20 1.525(7) . ? C18 C19 1.533(7) . ? C19 H191 0.9600 . ? C19 H192 0.9600 . ? C19 H193 0.9600 . ? C20 H201 0.9600 . ? C20 H202 0.9600 . ? C20 H203 0.9600 . ? C21 H211 0.9600 . ? C21 H212 0.9600 . ? C21 H213 0.9600 . ? C22 H221 0.9600 . ? C22 H222 0.9600 . ? C22 H223 0.9600 . ? C23 H231 0.9600 . ? C23 H232 0.9600 . ? C23 H233 0.9600 . ? C24 H241 0.9600 . ? C24 H242 0.9600 . ? C24 H243 0.9600 . ? C25 H251 0.9600 . ? C25 H252 0.9600 . ? C25 H253 0.9600 . ? O31 N32 1.265(5) . ? N32 C38 1.486(6) . ? N32 C34 1.490(6) . ? N33 C43 1.484(6) . ? N33 C45 1.499(6) . ? N33 C44 1.505(5) . ? N33 C36 1.544(5) . ? C34 C42 1.520(7) . ? C34 C35 1.527(6) . ? C34 C41 1.532(7) . ? C35 C36 1.513(6) . ? C35 H351 0.9700 . ? C35 H352 0.9700 . ? C36 C37 1.511(5) . ? C36 H36 0.9800 . ? C37 C38 1.512(6) . ? C37 H371 0.9700 . ? C37 H372 0.9700 . ? C38 C39 1.518(6) . ? C38 C40 1.542(7) . ? C39 H391 0.9600 . ? C39 H392 0.9600 . ? C39 H393 0.9600 . ? C40 H401 0.9600 . ? C40 H402 0.9600 . ? C40 H403 0.9600 . ? C41 H411 0.9600 . ? C41 H412 0.9600 . ? C41 H413 0.9600 . ? C42 H421 0.9600 . ? C42 H422 0.9600 . ? C42 H423 0.9600 . ? C43 H431 0.9600 . ? C43 H432 0.9600 . ? C43 H433 0.9600 . ? C44 H441 0.9600 . ? C44 H442 0.9600 . ? C44 H443 0.9600 . ? C45 H451 0.9600 . ? C45 H452 0.9600 . ? C45 H453 0.9600 . ? 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 O11 N12 C14 116.5(4) . . ? O11 N12 C18 115.9(4) . . ? C14 N12 C18 124.1(4) . . ? C24 N13 C25 108.6(4) . . ? C24 N13 C23 108.7(4) . . ? C25 N13 C23 106.2(4) . . ? C24 N13 C16 113.2(3) . . ? C25 N13 C16 110.9(3) . . ? C23 N13 C16 109.0(3) . . ? N12 C14 C21 107.8(4) . . ? N12 C14 C22 109.8(4) . . ? C21 C14 C22 109.5(4) . . ? N12 C14 C15 110.5(4) . . ? C21 C14 C15 107.6(4) . . ? C22 C14 C15 111.5(4) . . ? C16 C15 C14 111.3(4) . . ? C16 C15 H151 109.4 . . ? C14 C15 H151 109.4 . . ? C16 C15 H152 109.4 . . ? C14 C15 H152 109.4 . . ? H151 C15 H152 108.0 . . ? C17 C16 C15 107.6(4) . . ? C17 C16 N13 112.4(3) . . ? C15 C16 N13 113.4(3) . . ? C17 C16 H16 107.7 . . ? C15 C16 H16 107.7 . . ? N13 C16 H16 107.7 . . ? C16 C17 C18 112.9(4) . . ? C16 C17 H171 109.0 . . ? C18 C17 H171 109.0 . . ? C16 C17 H172 109.0 . . ? C18 C17 H172 109.0 . . ? H171 C17 H172 107.8 . . ? N12 C18 C17 109.5(4) . . ? N12 C18 C20 109.8(4) . . ? C17 C18 C20 111.6(4) . . ? N12 C18 C19 106.6(4) . . ? C17 C18 C19 108.7(4) . . ? C20 C18 C19 110.6(4) . . ? C18 C19 H191 109.5 . . ? C18 C19 H192 109.5 . . ? H191 C19 H192 109.5 . . ? C18 C19 H193 109.5 . . ? H191 C19 H193 109.5 . . ? H192 C19 H193 109.5 . . ? C18 C20 H201 109.5 . . ? C18 C20 H202 109.5 . . ? H201 C20 H202 109.5 . . ? C18 C20 H203 109.5 . . ? H201 C20 H203 109.5 . . ? H202 C20 H203 109.5 . . ? C14 C21 H211 109.5 . . ? C14 C21 H212 109.5 . . ? H211 C21 H212 109.5 . . ? C14 C21 H213 109.5 . . ? H211 C21 H213 109.5 . . ? H212 C21 H213 109.5 . . ? C14 C22 H221 109.5 . . ? C14 C22 H222 109.5 . . ? H221 C22 H222 109.5 . . ? C14 C22 H223 109.5 . . ? H221 C22 H223 109.5 . . ? H222 C22 H223 109.5 . . ? N13 C23 H231 109.5 . . ? N13 C23 H232 109.5 . . ? H231 C23 H232 109.5 . . ? N13 C23 H233 109.5 . . ? H231 C23 H233 109.5 . . ? H232 C23 H233 109.5 . . ? N13 C24 H241 109.5 . . ? N13 C24 H242 109.5 . . ? H241 C24 H242 109.5 . . ? N13 C24 H243 109.5 . . ? H241 C24 H243 109.5 . . ? H242 C24 H243 109.5 . . ? N13 C25 H251 109.5 . . ? N13 C25 H252 109.5 . . ? H251 C25 H252 109.5 . . ? N13 C25 H253 109.5 . . ? H251 C25 H253 109.5 . . ? H252 C25 H253 109.5 . . ? O31 N32 C38 116.6(4) . . ? O31 N32 C34 116.4(4) . . ? C38 N32 C34 123.9(4) . . ? C43 N33 C45 109.1(4) . . ? C43 N33 C44 108.2(4) . . ? C45 N33 C44 106.4(4) . . ? C43 N33 C36 113.5(4) . . ? C45 N33 C36 110.0(3) . . ? C44 N33 C36 109.4(3) . . ? N32 C34 C42 107.7(4) . . ? N32 C34 C35 110.1(4) . . ? C42 C34 C35 108.8(4) . . ? N32 C34 C41 109.2(4) . . ? C42 C34 C41 109.5(4) . . ? C35 C34 C41 111.5(4) . . ? C36 C35 C34 111.9(4) . . ? C36 C35 H351 109.2 . . ? C34 C35 H351 109.2 . . ? C36 C35 H352 109.2 . . ? C34 C35 H352 109.2 . . ? H351 C35 H352 107.9 . . ? C37 C36 C35 108.8(4) . . ? C37 C36 N33 112.1(3) . . ? C35 C36 N33 111.7(3) . . ? C37 C36 H36 108.0 . . ? C35 C36 H36 108.0 . . ? N33 C36 H36 108.0 . . ? C36 C37 C38 111.3(4) . . ? C36 C37 H371 109.4 . . ? C38 C37 H371 109.4 . . ? C36 C37 H372 109.4 . . ? C38 C37 H372 109.4 . . ? H371 C37 H372 108.0 . . ? N32 C38 C37 110.8(4) . . ? N32 C38 C39 107.6(4) . . ? C37 C38 C39 107.9(4) . . ? N32 C38 C40 107.9(4) . . ? C37 C38 C40 112.6(4) . . ? C39 C38 C40 110.0(4) . . ? C38 C39 H391 109.5 . . ? C38 C39 H392 109.5 . . ? H391 C39 H392 109.5 . . ? C38 C39 H393 109.5 . . ? H391 C39 H393 109.5 . . ? H392 C39 H393 109.5 . . ? C38 C40 H401 109.5 . . ? C38 C40 H402 109.5 . . ? H401 C40 H402 109.5 . . ? C38 C40 H403 109.5 . . ? H401 C40 H403 109.5 . . ? H402 C40 H403 109.5 . . ? C34 C41 H411 109.5 . . ? C34 C41 H412 109.5 . . ? H411 C41 H412 109.5 . . ? C34 C41 H413 109.5 . . ? H411 C41 H413 109.5 . . ? H412 C41 H413 109.5 . . ? C34 C42 H421 109.5 . . ? C34 C42 H422 109.5 . . ? H421 C42 H422 109.5 . . ? C34 C42 H423 109.5 . . ? H421 C42 H423 109.5 . . ? H422 C42 H423 109.5 . . ? N33 C43 H431 109.5 . . ? N33 C43 H432 109.5 . . ? H431 C43 H432 109.5 . . ? N33 C43 H433 109.5 . . ? H431 C43 H433 109.5 . . ? H432 C43 H433 109.5 . . ? N33 C44 H441 109.5 . . ? N33 C44 H442 109.5 . . ? H441 C44 H442 109.5 . . ? N33 C44 H443 109.5 . . ? H441 C44 H443 109.5 . . ? H442 C44 H443 109.5 . . ? N33 C45 H451 109.5 . . ? N33 C45 H452 109.5 . . ? H451 C45 H452 109.5 . . ? N33 C45 H453 109.5 . . ? H451 C45 H453 109.5 . . ? H452 C45 H453 109.5 . . ? 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 O11 N12 C14 C21 51.1(6) . . . . ? C18 N12 C14 C21 -150.9(5) . . . . ? O11 N12 C14 C22 -68.1(6) . . . . ? C18 N12 C14 C22 89.9(5) . . . . ? O11 N12 C14 C15 168.4(4) . . . . ? C18 N12 C14 C15 -33.6(6) . . . . ? N12 C14 C15 C16 47.2(5) . . . . ? C21 C14 C15 C16 164.6(4) . . . . ? C22 C14 C15 C16 -75.3(5) . . . . ? C14 C15 C16 C17 -63.9(5) . . . . ? C14 C15 C16 N13 171.2(3) . . . . ? C24 N13 C16 C17 -50.8(5) . . . . ? C25 N13 C16 C17 -173.1(4) . . . . ? C23 N13 C16 C17 70.4(5) . . . . ? C24 N13 C16 C15 71.6(5) . . . . ? C25 N13 C16 C15 -50.8(5) . . . . ? C23 N13 C16 C15 -167.3(4) . . . . ? C15 C16 C17 C18 64.7(5) . . . . ? N13 C16 C17 C18 -169.8(4) . . . . ? O11 N12 C18 C17 -168.7(4) . . . . ? C14 N12 C18 C17 33.1(6) . . . . ? O11 N12 C18 C20 68.4(5) . . . . ? C14 N12 C18 C20 -89.7(5) . . . . ? O11 N12 C18 C19 -51.4(6) . . . . ? C14 N12 C18 C19 150.5(5) . . . . ? C16 C17 C18 N12 -47.2(5) . . . . ? C16 C17 C18 C20 74.6(5) . . . . ? C16 C17 C18 C19 -163.2(4) . . . . ? O31 N32 C34 C42 -48.0(6) . . . . ? C38 N32 C34 C42 152.6(4) . . . . ? O31 N32 C34 C35 -166.5(4) . . . . ? C38 N32 C34 C35 34.1(6) . . . . ? O31 N32 C34 C41 70.8(5) . . . . ? C38 N32 C34 C41 -88.7(5) . . . . ? N32 C34 C35 C36 -46.0(5) . . . . ? C42 C34 C35 C36 -163.8(4) . . . . ? C41 C34 C35 C36 75.3(5) . . . . ? C34 C35 C36 C37 62.9(5) . . . . ? C34 C35 C36 N33 -172.8(4) . . . . ? C43 N33 C36 C37 68.5(5) . . . . ? C45 N33 C36 C37 -54.1(5) . . . . ? C44 N33 C36 C37 -170.6(4) . . . . ? C43 N33 C36 C35 -54.0(5) . . . . ? C45 N33 C36 C35 -176.6(4) . . . . ? C44 N33 C36 C35 66.9(5) . . . . ? C35 C36 C37 C38 -63.5(5) . . . . ? N33 C36 C37 C38 172.4(4) . . . . ? O31 N32 C38 C37 165.4(4) . . . . ? C34 N32 C38 C37 -35.1(6) . . . . ? O31 N32 C38 C39 47.7(6) . . . . ? C34 N32 C38 C39 -152.9(4) . . . . ? O31 N32 C38 C40 -70.9(5) . . . . ? C34 N32 C38 C40 88.5(5) . . . . ? C36 C37 C38 N32 47.7(5) . . . . ? C36 C37 C38 C39 165.2(4) . . . . ? C36 C37 C38 C40 -73.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 29.95 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.722 _refine_diff_density_min -1.451 _refine_diff_density_rms 0.119 #===END data_(NMe3-Tempo)PF6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,N-trimethyl-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)ammonium hexafluorophosphate ; _chemical_name_common 'trimethylammonio-tempo hexafluorophosphate' _chemical_melting_point ? _chemical_formula_moiety 'F6 P, C12 H26 N2 O' _chemical_formula_sum 'C12 H26 F6 N2 O P' _chemical_formula_weight 359.32 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' 'P' 'P' 0.1023 0.0942 '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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z+1/2' 'x, -y+1/2, z' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z-1/2' '-x, y-1/2, -z' 'x-1/2, y, -z-1/2' _cell_length_a 11.4000(10) _cell_length_b 10.8520(10) _cell_length_c 13.3540(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1652.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 26 _exptl_crystal_description 'block' _exptl_crystal_colour 'orange-brown' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The data were collected on a Stoe Imaging Plate Diffraction System (IPDS) equipped with an Oxford Cryosystems cooler device. The crystal-to-detector distance was 70 mm. 100 exposures (3 min per exposure) were obtained with 0 < \f < 200\% and with the crystals rotated through 2\% in \f. Crystal decay was monitored by measuring 200 reflexions per image. ; _diffrn_ambient_temperature 160(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 'STOE Imaging Plate Diffraction System' _diffrn_measurement_method '\f scan ' _diffrn_standards_decay_% 'negligible' _diffrn_reflns_number 15600 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.98 _reflns_number_total 1676 _reflns_number_gt 1437 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS software (Stoe, 1996)' _computing_cell_refinement 'IPDS software (Stoe, 1996)' _computing_data_reduction 'XRED (Stoe, X-Red 1.08, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Prout & Pearce, 1996)' _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. The PF6 unit is disordered over three positions (for which two are symmetry related): the first one (occupancy 60%)is built on P, F1, F2, F3 and F4,(and the two missing F are generated from F3 and F4 with the mirror plane); the second unit (occupancy 20%) is built with F11, F12, F13, F14, F15 and F16 and distances between P and F were restrained to be equal (around 1.6 \%A), as well as the distances between apical F (F11 and F12) and equatorial F (F13, F14, F15 and F16). These latter were also restrained to lie in a common plane. the third unit (occupancy 20%) is the image of the second one through the mirror plane. ; _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^)+(0.0525P)^2^+1.3258P] 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 1676 _refine_ls_number_parameters 166 _refine_ls_number_restraints 53 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1170 _refine_ls_wR_factor_gt 0.1130 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.071 _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 C1 C 0.93449(15) 0.12925(15) 0.31466(13) 0.0239(4) Uani 1 1 d . . . C2 C 0.8733(2) 0.13851(18) 0.41656(16) 0.0376(5) Uani 1 1 d . . . H2A H 0.8242 0.0643 0.4268 0.045 Uiso 1 1 calc R . . H2B H 0.9334 0.1402 0.4701 0.045 Uiso 1 1 calc R . . C3 C 0.7984(2) 0.2500 0.42511(19) 0.0251(6) Uani 1 2 d S . . H3 H 0.7478 0.2500 0.3639 0.030 Uiso 1 2 calc SR . . C4 C 0.63592(18) 0.13871(18) 0.50848(16) 0.0347(5) Uani 1 1 d . . . H4A H 0.5760 0.1438 0.5610 0.042 Uiso 1 1 calc R . . H4B H 0.6831 0.0642 0.5183 0.042 Uiso 1 1 calc R . . H4C H 0.5977 0.1355 0.4428 0.042 Uiso 1 1 calc R . . C5 C 0.7762(3) 0.2500 0.6124(2) 0.0407(7) Uani 1 2 d S . . H5A H 0.7185 0.2502 0.6668 0.049 Uiso 1 2 calc SR . . H5B H 0.8256 0.3236 0.6174 0.049 Uiso 0.50 1 calc PR . . H5C H 0.8253 0.1762 0.6175 0.049 Uiso 0.50 1 calc PR . . C11 C 1.03132(18) 0.03340(18) 0.32463(16) 0.0355(5) Uani 1 1 d . . . H11A H 1.0667 0.0184 0.2588 0.043 Uiso 1 1 calc R . . H11B H 0.9982 -0.0436 0.3505 0.043 Uiso 1 1 calc R . . H11C H 1.0915 0.0637 0.3709 0.043 Uiso 1 1 calc R . . C12 C 0.85213(19) 0.0925(2) 0.22985(17) 0.0408(5) Uani 1 1 d . . . H12A H 0.7894 0.1537 0.2238 0.049 Uiso 1 1 calc R . . H12B H 0.8179 0.0116 0.2443 0.049 Uiso 1 1 calc R . . H12C H 0.8962 0.0884 0.1669 0.049 Uiso 1 1 calc R . . N1 N 0.98959(18) 0.2500 0.29068(14) 0.0208(4) Uani 1 2 d S . . N2 N 0.71380(18) 0.2500 0.51374(15) 0.0220(5) Uani 1 2 d S . . O1 O 1.06641(17) 0.2500 0.22061(14) 0.0325(5) Uani 1 2 d S . . P1 P 0.76827(7) 0.2500 0.92000(5) 0.0270(2) Uani 1 2 d SD . . F1 F 0.6636(7) 0.2500 0.8419(5) 0.078(3) Uani 0.60 2 d SP A 1 F2 F 0.8738(6) 0.2500 0.9972(6) 0.070(3) Uani 0.60 2 d SP A 1 F3 F 0.7035(6) 0.3522(6) 0.9873(5) 0.0553(15) Uani 0.60 1 d P A 1 F4 F 0.8317(9) 0.3493(8) 0.8540(7) 0.086(3) Uani 0.60 1 d P A 1 F11 F 0.8586(12) 0.1891(15) 0.9898(10) 0.101(8) Uani 0.20 1 d PD . 2 F12 F 0.6828(13) 0.3074(16) 0.8470(10) 0.140(11) Uani 0.20 1 d PD . 2 F13 F 0.7842(16) 0.1395(13) 0.8471(12) 0.066(6) Uani 0.20 1 d PDU . 2 F14 F 0.6726(14) 0.1745(18) 0.9673(16) 0.111(9) Uani 0.20 1 d PDU . 2 F15 F 0.8687(16) 0.326(3) 0.8740(19) 0.183(16) Uani 0.20 1 d PDU . 2 F16 F 0.755(2) 0.3562(18) 0.9911(15) 0.111(11) Uani 0.20 1 d PDU . 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 C1 0.0236(9) 0.0207(8) 0.0274(9) -0.0018(7) 0.0056(7) 0.0000(7) C2 0.0453(13) 0.0263(10) 0.0412(11) 0.0049(8) 0.0210(10) 0.0043(8) C3 0.0268(14) 0.0247(12) 0.0239(12) 0.000 0.0095(10) 0.000 C4 0.0316(11) 0.0303(10) 0.0421(11) 0.0004(8) 0.0112(8) -0.0069(8) C5 0.0394(17) 0.064(2) 0.0187(13) 0.000 0.0000(12) 0.000 C11 0.0340(11) 0.0259(9) 0.0467(12) 0.0001(8) 0.0005(9) 0.0057(8) C12 0.0358(12) 0.0351(11) 0.0514(13) -0.0071(9) -0.0098(9) -0.0058(9) N1 0.0189(10) 0.0236(10) 0.0199(10) 0.000 0.0047(8) 0.000 N2 0.0231(11) 0.0251(10) 0.0179(10) 0.000 0.0037(8) 0.000 O1 0.0281(10) 0.0384(10) 0.0308(10) 0.000 0.0132(8) 0.000 P1 0.0354(4) 0.0230(4) 0.0226(4) 0.000 -0.0013(3) 0.000 F1 0.061(3) 0.132(9) 0.039(3) 0.000 -0.020(2) 0.000 F2 0.037(3) 0.118(9) 0.056(3) 0.000 -0.016(2) 0.000 F3 0.075(4) 0.036(2) 0.055(2) -0.0135(18) 0.013(2) 0.018(3) F4 0.093(6) 0.092(5) 0.074(3) 0.042(3) 0.019(3) -0.039(4) F11 0.071(9) 0.13(2) 0.101(11) 0.046(12) -0.053(8) 0.011(10) F12 0.171(17) 0.15(2) 0.097(10) -0.050(10) -0.095(11) 0.144(19) F13 0.113(19) 0.034(5) 0.052(7) -0.016(5) 0.017(9) -0.005(8) F14 0.070(10) 0.125(15) 0.139(15) 0.067(9) 0.033(9) -0.019(8) F15 0.091(12) 0.27(3) 0.184(19) 0.162(18) -0.044(10) -0.103(14) F16 0.20(3) 0.049(8) 0.088(10) -0.041(7) -0.008(17) -0.005(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.4880(18) . ? C1 C11 1.523(2) . ? C1 C12 1.524(3) . ? C1 C2 1.532(2) . ? C2 C3 1.485(2) . ? C3 C2 1.485(2) 3 ? C3 N2 1.527(3) . ? C4 N2 1.501(2) . ? C5 N2 1.497(3) . ? N1 O1 1.282(3) . ? N1 C1 1.4880(18) 3 ? N2 C4 1.501(2) 3 ? P1 F16 1.501(14) . ? P1 F16 1.501(14) 3 ? P1 F14 1.503(13) 3 ? P1 F14 1.503(13) . ? P1 F12 1.512(11) 3 ? P1 F12 1.512(11) . ? P1 F15 1.538(14) . ? P1 F15 1.538(14) 3 ? P1 F11 1.538(11) 3 ? P1 F11 1.538(11) . ? P1 F13 1.555(13) . ? P1 F13 1.555(13) 3 ? P1 F4 1.569(7) 3 ? P1 F4 1.569(7) . ? P1 F2 1.584(8) . ? P1 F1 1.585(8) . ? P1 F3 1.607(6) . ? P1 F3 1.607(6) 3 ? F11 F16 1.28(2) 3 ? F11 F11 1.32(3) 3 ? F11 F15 1.56(3) 3 ? F12 F12 1.25(3) 3 ? F12 F13 1.29(3) 3 ? F12 F14 1.62(2) 3 ? F13 F15 1.10(3) 3 ? F13 F12 1.29(3) 3 ? F14 F16 1.04(3) 3 ? F14 F12 1.62(2) 3 ? F14 F14 1.64(4) 3 ? F15 F13 1.10(3) 3 ? F15 F11 1.56(3) 3 ? F15 F15 1.65(5) 3 ? F16 F14 1.04(3) 3 ? F16 F11 1.28(2) 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 C1 C11 108.32(15) . . ? N1 C1 C12 109.31(16) . . ? C11 C1 C12 109.43(15) . . ? N1 C1 C2 109.00(15) . . ? C11 C1 C2 107.29(16) . . ? C12 C1 C2 113.36(16) . . ? C3 C2 C1 112.54(17) . . ? C2 C3 C2 109.1(2) 3 . ? C2 C3 N2 115.00(13) 3 . ? C2 C3 N2 115.00(13) . . ? O1 N1 C1 116.46(9) . . ? O1 N1 C1 116.46(9) . 3 ? C1 N1 C1 123.43(18) . 3 ? C5 N2 C4 108.81(14) . . ? C5 N2 C4 108.81(14) . 3 ? C4 N2 C4 107.2(2) . 3 ? C5 N2 C3 112.4(2) . . ? C4 N2 C3 109.73(13) . . ? C4 N2 C3 109.73(13) 3 . ? F16 P1 F16 100(2) . 3 ? F16 P1 F14 40.7(10) . 3 ? F16 P1 F14 94.5(12) 3 3 ? F16 P1 F14 94.5(12) . . ? F16 P1 F14 40.7(10) 3 . ? F14 P1 F14 66.1(18) 3 . ? F16 P1 F12 131.2(11) . 3 ? F16 P1 F12 91.5(7) 3 3 ? F14 P1 F12 91.6(7) 3 3 ? F14 P1 F12 65.1(9) . 3 ? F16 P1 F12 91.5(7) . . ? F16 P1 F12 131.2(11) 3 . ? F14 P1 F12 65.1(9) 3 . ? F14 P1 F12 91.6(7) . . ? F12 P1 F12 48.6(14) 3 . ? F16 P1 F15 85.3(17) . . ? F16 P1 F15 137.7(12) 3 . ? F14 P1 F15 114.6(15) 3 . ? F14 P1 F15 178.3(8) . . ? F12 P1 F15 116.3(11) 3 . ? F12 P1 F15 90.1(7) . . ? F16 P1 F15 137.7(12) . 3 ? F16 P1 F15 85.3(17) 3 3 ? F14 P1 F15 178.3(8) 3 3 ? F14 P1 F15 114.6(15) . 3 ? F12 P1 F15 90.1(7) 3 3 ? F12 P1 F15 116.3(11) . 3 ? F15 P1 F15 65(2) . 3 ? F16 P1 F11 49.8(9) . 3 ? F16 P1 F11 90.8(7) 3 3 ? F14 P1 F11 89.8(6) 3 3 ? F14 P1 F11 117.7(10) . 3 ? F12 P1 F11 177.2(7) 3 3 ? F12 P1 F11 130.2(10) . 3 ? F15 P1 F11 60.9(11) . 3 ? F15 P1 F11 88.5(7) 3 3 ? F16 P1 F11 90.8(7) . . ? F16 P1 F11 49.8(9) 3 . ? F14 P1 F11 117.7(10) 3 . ? F14 P1 F11 89.8(6) . . ? F12 P1 F11 130.2(10) 3 . ? F12 P1 F11 177.2(7) . . ? F15 P1 F11 88.5(7) . . ? F15 P1 F11 60.9(11) 3 . ? F11 P1 F11 50.9(12) 3 . ? F16 P1 F13 179.1(9) . . ? F16 P1 F13 79.4(12) 3 . ? F14 P1 F13 140.2(10) 3 . ? F14 P1 F13 85.8(12) . . ? F12 P1 F13 49.8(11) 3 . ? F12 P1 F13 89.4(6) . . ? F15 P1 F13 94.3(14) . . ? F15 P1 F13 41.5(10) 3 . ? F11 P1 F13 129.2(10) 3 . ? F11 P1 F13 88.3(6) . . ? F16 P1 F13 79.4(12) . 3 ? F16 P1 F13 179.1(9) 3 3 ? F14 P1 F13 85.8(12) 3 3 ? F14 P1 F13 140.2(10) . 3 ? F12 P1 F13 89.4(6) 3 3 ? F12 P1 F13 49.8(11) . 3 ? F15 P1 F13 41.5(10) . 3 ? F15 P1 F13 94.3(14) 3 3 ? F11 P1 F13 88.3(6) 3 3 ? F11 P1 F13 129.2(10) . 3 ? F13 P1 F13 100.9(13) . 3 ? F16 P1 F4 158.4(9) . 3 ? F16 P1 F4 82.8(11) 3 3 ? F14 P1 F4 160.9(7) 3 3 ? F14 P1 F4 101.3(10) . 3 ? F12 P1 F4 69.6(7) 3 3 ? F12 P1 F4 102.6(7) . 3 ? F15 P1 F4 78.4(12) . 3 ? F15 P1 F4 20.8(8) 3 3 ? F11 P1 F4 109.1(7) 3 3 ? F11 P1 F4 74.7(7) . 3 ? F13 P1 F4 20.8(8) . 3 ? F13 P1 F4 97.1(5) 3 3 ? F16 P1 F4 82.8(12) . . ? F16 P1 F4 158.4(9) 3 . ? F14 P1 F4 101.3(10) 3 . ? F14 P1 F4 160.9(7) . . ? F12 P1 F4 102.6(7) 3 . ? F12 P1 F4 69.6(7) . . ? F15 P1 F4 20.8(8) . . ? F15 P1 F4 78.4(12) 3 . ? F11 P1 F4 74.7(7) 3 . ? F11 P1 F4 109.1(7) . . ? F13 P1 F4 97.1(5) . . ? F13 P1 F4 20.8(8) 3 . ? F4 P1 F4 86.7(7) 3 . ? F16 P1 F2 70.5(7) . . ? F16 P1 F2 70.5(7) 3 . ? F14 P1 F2 106.1(8) 3 . ? F14 P1 F2 106.1(8) . . ? F12 P1 F2 155.3(7) 3 . ? F12 P1 F2 155.3(7) . . ? F15 P1 F2 72.2(7) . . ? F15 P1 F2 72.2(7) 3 . ? F11 P1 F2 25.5(6) 3 . ? F11 P1 F2 25.5(6) . . ? F13 P1 F2 108.6(7) . . ? F13 P1 F2 108.6(7) 3 . ? F4 P1 F2 90.9(4) 3 . ? F4 P1 F2 90.9(4) . . ? F16 P1 F1 109.8(7) . . ? F16 P1 F1 109.8(7) 3 . ? F14 P1 F1 74.3(8) 3 . ? F14 P1 F1 74.3(8) . . ? F12 P1 F1 24.6(7) 3 . ? F12 P1 F1 24.6(7) . . ? F15 P1 F1 107.3(7) . . ? F15 P1 F1 107.3(7) 3 . ? F11 P1 F1 154.5(6) 3 . ? F11 P1 F1 154.5(6) . . ? F13 P1 F1 71.1(6) . . ? F13 P1 F1 71.1(6) 3 . ? F4 P1 F1 88.7(4) 3 . ? F4 P1 F1 88.7(4) . . ? F2 P1 F1 179.4(4) . . ? F16 P1 F3 21.5(9) . . ? F16 P1 F3 97.4(10) 3 . ? F14 P1 F3 19.2(7) 3 . ? F14 P1 F3 79.0(9) . . ? F12 P1 F3 110.4(8) 3 . ? F12 P1 F3 77.3(6) . . ? F15 P1 F3 101.3(13) . . ? F15 P1 F3 159.1(7) 3 . ? F11 P1 F3 70.8(6) 3 . ? F11 P1 F3 105.4(7) . . ? F13 P1 F3 159.4(7) . . ? F13 P1 F3 82.6(7) 3 . ? F4 P1 F3 179.7(5) 3 . ? F4 P1 F3 93.0(4) . . ? F2 P1 F3 89.1(3) . . ? F1 P1 F3 91.3(3) . . ? F16 P1 F3 97.4(10) . 3 ? F16 P1 F3 21.5(9) 3 3 ? F14 P1 F3 79.0(9) 3 3 ? F14 P1 F3 19.2(7) . 3 ? F12 P1 F3 77.3(6) 3 3 ? F12 P1 F3 110.4(8) . 3 ? F15 P1 F3 159.1(7) . 3 ? F15 P1 F3 101.3(13) 3 3 ? F11 P1 F3 105.4(7) 3 3 ? F11 P1 F3 70.8(6) . 3 ? F13 P1 F3 82.6(7) . 3 ? F13 P1 F3 159.4(7) 3 3 ? F4 P1 F3 93.0(4) 3 3 ? F4 P1 F3 179.7(5) . 3 ? F2 P1 F3 89.1(3) . 3 ? F1 P1 F3 91.3(3) . 3 ? F3 P1 F3 87.3(5) . 3 ? F16 F11 F11 112.6(13) 3 3 ? F16 F11 P1 63.6(8) 3 . ? F11 F11 P1 64.6(6) 3 . ? F16 F11 F15 92.4(18) 3 3 ? F11 F11 F15 96.0(13) 3 3 ? P1 F11 F15 59.6(7) . 3 ? F12 F12 F13 116.5(9) 3 3 ? F12 F12 P1 65.7(7) 3 . ? F13 F12 P1 66.8(8) 3 . ? F12 F12 F14 97.0(10) 3 3 ? F13 F12 F14 90.5(14) 3 3 ? P1 F12 F14 57.2(7) . 3 ? F15 F13 F12 129.4(15) 3 3 ? F15 F13 P1 68.4(8) 3 . ? F12 F13 P1 63.4(8) 3 . ? F16 F14 P1 69.5(9) 3 . ? F16 F14 F12 106(2) 3 3 ? P1 F14 F12 57.7(6) . 3 ? F16 F14 F14 108.6(16) 3 3 ? P1 F14 F14 57.0(9) . 3 ? F12 F14 F14 83.0(10) 3 3 ? F13 F15 P1 70.1(9) 3 . ? F13 F15 F11 107(2) 3 3 ? P1 F15 F11 59.6(7) . 3 ? F13 F15 F15 110.1(15) 3 3 ? P1 F15 F15 57.7(12) . 3 ? F11 F15 F15 84.0(13) 3 3 ? F14 F16 F11 134.7(17) 3 3 ? F14 F16 P1 69.8(10) 3 . ? F11 F16 P1 66.6(8) 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 C1 C2 C3 48.1(2) . . . . ? C11 C1 C2 C3 165.19(18) . . . . ? C12 C1 C2 C3 -73.9(2) . . . . ? C1 C2 C3 C2 -62.6(3) . . . 3 ? C1 C2 C3 N2 166.48(18) . . . . ? C11 C1 N1 O1 47.7(2) . . . . ? C12 C1 N1 O1 -71.4(2) . . . . ? C2 C1 N1 O1 164.16(18) . . . . ? C11 C1 N1 C1 -154.60(16) . . . 3 ? C12 C1 N1 C1 86.2(2) . . . 3 ? C2 C1 N1 C1 -38.2(3) . . . 3 ? C2 C3 N2 C5 -64.04(18) 3 . . . ? C2 C3 N2 C5 64.04(18) . . . . ? C2 C3 N2 C4 174.72(19) 3 . . . ? C2 C3 N2 C4 -57.2(3) . . . . ? C2 C3 N2 C4 57.2(3) 3 . . 3 ? C2 C3 N2 C4 -174.72(19) . . . 3 ? F16 P1 F11 F16 103(3) . . . 3 ? F14 P1 F11 F16 70.9(17) 3 . . 3 ? F14 P1 F11 F16 8(2) . . . 3 ? F12 P1 F11 F16 -48.1(18) 3 . . 3 ? F12 P1 F11 F16 -112(16) . . . 3 ? F15 P1 F11 F16 -172(2) . . . 3 ? F15 P1 F11 F16 -110(2) 3 . . 3 ? F11 P1 F11 F16 135.3(15) 3 . . 3 ? F13 P1 F11 F16 -77.5(17) . . . 3 ? F13 P1 F11 F16 179.8(16) 3 . . 3 ? F4 P1 F11 F16 -93.5(16) 3 . . 3 ? F4 P1 F11 F16 -174.5(15) . . . 3 ? F2 P1 F11 F16 139(3) . . . 3 ? F1 P1 F11 F16 -42(2) . . . 3 ? F3 P1 F11 F16 86.8(15) . . . 3 ? F3 P1 F11 F16 5.2(16) 3 . . 3 ? F16 P1 F11 F11 -32.5(11) . . . 3 ? F16 P1 F11 F11 -135.3(15) 3 . . 3 ? F14 P1 F11 F11 -64.4(10) 3 . . 3 ? F14 P1 F11 F11 -127.0(10) . . . 3 ? F12 P1 F11 F11 176.6(10) 3 . . 3 ? F12 P1 F11 F11 113(17) . . . 3 ? F15 P1 F11 F11 52.7(13) . . . 3 ? F15 P1 F11 F11 114.4(13) 3 . . 3 ? F13 P1 F11 F11 147.1(8) . . . 3 ? F13 P1 F11 F11 44.5(10) 3 . . 3 ? F4 P1 F11 F11 131.2(4) 3 . . 3 ? F4 P1 F11 F11 50.2(4) . . . 3 ? F2 P1 F11 F11 4(2) . . . 3 ? F1 P1 F11 F11 -177.7(16) . . . 3 ? F3 P1 F11 F11 -48.6(3) . . . 3 ? F3 P1 F11 F11 -130.1(3) 3 . . 3 ? F16 P1 F11 F15 -146.9(17) . . . 3 ? F16 P1 F11 F15 110(2) 3 . . 3 ? F14 P1 F11 F15 -178.8(15) 3 . . 3 ? F14 P1 F11 F15 118.5(16) . . . 3 ? F12 P1 F11 F15 62.2(15) 3 . . 3 ? F12 P1 F11 F15 -2(17) . . . 3 ? F15 P1 F11 F15 -62(3) . . . 3 ? F11 P1 F11 F15 -114.4(13) 3 . . 3 ? F13 P1 F11 F15 32.7(16) . . . 3 ? F13 P1 F11 F15 -70.0(18) 3 . . 3 ? F4 P1 F11 F15 16.8(15) 3 . . 3 ? F4 P1 F11 F15 -64.2(13) . . . 3 ? F2 P1 F11 F15 -111(2) . . . 3 ? F1 P1 F11 F15 68(2) . . . 3 ? F3 P1 F11 F15 -163.0(14) . . . 3 ? F3 P1 F11 F15 115.5(14) 3 . . 3 ? F16 P1 F12 F12 -148.7(11) . . . 3 ? F16 P1 F12 F12 -43.6(15) 3 . . 3 ? F14 P1 F12 F12 -116.7(9) 3 . . 3 ? F14 P1 F12 F12 -54.1(10) . . . 3 ? F15 P1 F12 F12 126.0(13) . . . 3 ? F15 P1 F12 F12 64.4(13) 3 . . 3 ? F11 P1 F12 F12 176.6(10) 3 . . 3 ? F11 P1 F12 F12 66(16) . . . 3 ? F13 P1 F12 F12 31.7(7) . . . 3 ? F13 P1 F12 F12 136.5(10) 3 . . 3 ? F4 P1 F12 F12 47.8(4) 3 . . 3 ? F4 P1 F12 F12 129.5(4) . . . 3 ? F2 P1 F12 F12 169.3(17) . . . 3 ? F1 P1 F12 F12 -9.3(18) . . . 3 ? F3 P1 F12 F12 -132.4(3) . . . 3 ? F3 P1 F12 F12 -50.2(4) 3 . . 3 ? F16 P1 F12 F13 74.7(15) . . . 3 ? F16 P1 F12 F13 179.9(16) 3 . . 3 ? F14 P1 F12 F13 106.7(15) 3 . . 3 ? F14 P1 F12 F13 169.3(14) . . . 3 ? F12 P1 F12 F13 -136.5(10) 3 . . 3 ? F15 P1 F12 F13 -10.5(17) . . . 3 ? F15 P1 F12 F13 -72.1(17) 3 . . 3 ? F11 P1 F12 F13 40.1(13) 3 . . 3 ? F11 P1 F12 F13 -71(17) . . . 3 ? F13 P1 F12 F13 -104.9(16) . . . 3 ? F4 P1 F12 F13 -88.7(9) 3 . . 3 ? F4 P1 F12 F13 -7.0(12) . . . 3 ? F2 P1 F12 F13 32.8(19) . . . 3 ? F1 P1 F12 F13 -146(2) . . . 3 ? F3 P1 F12 F13 91.0(11) . . . 3 ? F3 P1 F12 F13 173.2(9) 3 . . 3 ? F16 P1 F12 F14 -32.0(16) . . . 3 ? F16 P1 F12 F14 73.1(17) 3 . . 3 ? F14 P1 F12 F14 62.6(19) . . . 3 ? F12 P1 F12 F14 116.7(10) 3 . . 3 ? F15 P1 F12 F14 -117.2(17) . . . 3 ? F15 P1 F12 F14 -178.8(15) 3 . . 3 ? F11 P1 F12 F14 -66.7(13) 3 . . 3 ? F11 P1 F12 F14 -177(16) . . . 3 ? F13 P1 F12 F14 148.4(12) . . . 3 ? F13 P1 F12 F14 -106.7(15) 3 . . 3 ? F4 P1 F12 F14 164.6(10) 3 . . 3 ? F4 P1 F12 F14 -113.8(11) . . . 3 ? F2 P1 F12 F14 -74(2) . . . 3 ? F1 P1 F12 F14 107(2) . . . 3 ? F3 P1 F12 F14 -15.7(10) . . . 3 ? F3 P1 F12 F14 66.5(10) 3 . . 3 ? F16 P1 F13 F15 -23(82) . . . 3 ? F16 P1 F13 F15 -95(2) 3 . . 3 ? F14 P1 F13 F15 -179(2) 3 . . 3 ? F14 P1 F13 F15 -135(2) . . . 3 ? F12 P1 F13 F15 164(2) 3 . . 3 ? F12 P1 F13 F15 133(2) . . . 3 ? F15 P1 F13 F15 43(2) . . . 3 ? F11 P1 F13 F15 -13(2) 3 . . 3 ? F11 P1 F13 F15 -45(2) . . . 3 ? F13 P1 F13 F15 84(2) 3 . . 3 ? F4 P1 F13 F15 3(3) 3 . . 3 ? F4 P1 F13 F15 64(2) . . . 3 ? F2 P1 F13 F15 -30(2) . . . 3 ? F1 P1 F13 F15 150(2) . . . 3 ? F3 P1 F13 F15 -178(2) . . . 3 ? F3 P1 F13 F15 -116(2) 3 . . 3 ? F16 P1 F13 F12 173(100) . . . 3 ? F16 P1 F13 F12 101.1(11) 3 . . 3 ? F14 P1 F13 F12 17(2) 3 . . 3 ? F14 P1 F13 F12 60.6(12) . . . 3 ? F12 P1 F13 F12 -31.1(12) . . . 3 ? F15 P1 F13 F12 -121.1(11) . . . 3 ? F15 P1 F13 F12 -164(2) 3 . . 3 ? F11 P1 F13 F12 -176.5(9) 3 . . 3 ? F11 P1 F13 F12 150.5(11) . . . 3 ? F13 P1 F13 F12 -79.8(12) 3 . . 3 ? F4 P1 F13 F12 -161(3) 3 . . 3 ? F4 P1 F13 F12 -100.5(10) . . . 3 ? F2 P1 F13 F12 166.2(8) . . . 3 ? F1 P1 F13 F12 -14.3(9) . . . 3 ? F3 P1 F13 F12 18(2) . . . 3 ? F3 P1 F13 F12 79.6(9) 3 . . 3 ? F16 P1 F14 F16 -101(3) . . . 3 ? F14 P1 F14 F16 -130.4(19) 3 . . 3 ? F12 P1 F14 F16 126(2) 3 . . 3 ? F12 P1 F14 F16 168(2) . . . 3 ? F15 P1 F14 F16 -17(57) . . . 3 ? F15 P1 F14 F16 48(2) 3 . . 3 ? F11 P1 F14 F16 -54(2) 3 . . 3 ? F11 P1 F14 F16 -10(2) . . . 3 ? F13 P1 F14 F16 79(2) . . . 3 ? F13 P1 F14 F16 -179.4(17) 3 . . 3 ? F4 P1 F14 F16 65(2) 3 . . 3 ? F4 P1 F14 F16 178(2) . . . 3 ? F2 P1 F14 F16 -30(2) . . . 3 ? F1 P1 F14 F16 150(2) . . . 3 ? F3 P1 F14 F16 -115(2) . . . 3 ? F3 P1 F14 F16 -1(2) 3 . . 3 ? F16 P1 F14 F12 133.7(12) . . . 3 ? F16 P1 F14 F12 -126(2) 3 . . 3 ? F14 P1 F14 F12 103.9(9) 3 . . 3 ? F12 P1 F14 F12 42.1(13) . . . 3 ? F15 P1 F14 F12 -143(56) . . . 3 ? F15 P1 F14 F12 -77.9(12) 3 . . 3 ? F11 P1 F14 F12 -179.8(9) 3 . . 3 ? F11 P1 F14 F12 -135.4(12) . . . 3 ? F13 P1 F14 F12 -47.2(12) . . . 3 ? F13 P1 F14 F12 54.9(18) 3 . . 3 ? F4 P1 F14 F12 -61.0(10) 3 . . 3 ? F4 P1 F14 F12 53(3) . . . 3 ? F2 P1 F14 F12 -155.3(9) . . . 3 ? F1 P1 F14 F12 24.4(9) . . . 3 ? F3 P1 F14 F12 118.9(10) . . . 3 ? F3 P1 F14 F12 -127(3) 3 . . 3 ? F16 P1 F14 F14 29.9(8) . . . 3 ? F16 P1 F14 F14 130.4(19) 3 . . 3 ? F12 P1 F14 F14 -103.9(9) 3 . . 3 ? F12 P1 F14 F14 -61.8(8) . . . 3 ? F15 P1 F14 F14 113(56) . . . 3 ? F15 P1 F14 F14 178.3(11) 3 . . 3 ? F11 P1 F14 F14 76.3(9) 3 . . 3 ? F11 P1 F14 F14 120.7(8) . . . 3 ? F13 P1 F14 F14 -151.0(9) . . . 3 ? F13 P1 F14 F14 -49.0(13) 3 . . 3 ? F4 P1 F14 F14 -164.9(6) 3 . . 3 ? F4 P1 F14 F14 -51(3) . . . 3 ? F2 P1 F14 F14 100.8(7) . . . 3 ? F1 P1 F14 F14 -79.5(7) . . . 3 ? F3 P1 F14 F14 15.0(7) . . . 3 ? F3 P1 F14 F14 129(3) 3 . . 3 ? F16 P1 F15 F13 -79.3(19) . . . 3 ? F16 P1 F15 F13 -179.5(17) 3 . . 3 ? F14 P1 F15 F13 -50(2) 3 . . 3 ? F14 P1 F15 F13 -163(55) . . . 3 ? F12 P1 F15 F13 55(2) 3 . . 3 ? F12 P1 F15 F13 12.2(19) . . . 3 ? F15 P1 F15 F13 131.4(15) 3 . . 3 ? F11 P1 F15 F13 -125(2) 3 . . 3 ? F11 P1 F15 F13 -170.3(19) . . . 3 ? F13 P1 F15 F13 102(2) . . . 3 ? F4 P1 F15 F13 115.0(18) 3 . . 3 ? F4 P1 F15 F13 3(3) . . . 3 ? F2 P1 F15 F13 -150(2) . . . 3 ? F1 P1 F15 F13 30(2) . . . 3 ? F3 P1 F15 F13 -64.9(18) . . . 3 ? F3 P1 F15 F13 -178(2) 3 . . 3 ? F16 P1 F15 F11 46.0(14) . . . 3 ? F16 P1 F15 F11 -54(2) 3 . . 3 ? F14 P1 F15 F11 75.0(11) 3 . . 3 ? F14 P1 F15 F11 -38(56) . . . 3 ? F12 P1 F15 F11 -179.9(9) 3 . . 3 ? F12 P1 F15 F11 137.5(12) . . . 3 ? F15 P1 F15 F11 -103.3(12) 3 . . 3 ? F11 P1 F15 F11 -45.0(14) . . . 3 ? F13 P1 F15 F11 -133.1(13) . . . 3 ? F13 P1 F15 F11 125(2) 3 . . 3 ? F4 P1 F15 F11 -119.7(10) 3 . . 3 ? F4 P1 F15 F11 128(5) . . . 3 ? F2 P1 F15 F11 -25.0(8) . . . 3 ? F1 P1 F15 F11 155.3(8) . . . 3 ? F3 P1 F15 F11 60.4(10) . . . 3 ? F3 P1 F15 F11 -52(4) 3 . . 3 ? F16 P1 F15 F15 149.3(9) . . . 3 ? F16 P1 F15 F15 49.1(17) 3 . . 3 ? F14 P1 F15 F15 178.3(11) 3 . . 3 ? F14 P1 F15 F15 66(55) . . . 3 ? F12 P1 F15 F15 -76.6(12) 3 . . 3 ? F12 P1 F15 F15 -119.3(8) . . . 3 ? F11 P1 F15 F15 103.3(12) 3 . . 3 ? F11 P1 F15 F15 58.3(8) . . . 3 ? F13 P1 F15 F15 -29.9(7) . . . 3 ? F13 P1 F15 F15 -131.4(15) 3 . . 3 ? F4 P1 F15 F15 -16.4(8) 3 . . 3 ? F4 P1 F15 F15 -128(4) . . . 3 ? F2 P1 F15 F15 78.3(8) . . . 3 ? F1 P1 F15 F15 -101.4(8) . . . 3 ? F3 P1 F15 F15 163.7(6) . . . 3 ? F3 P1 F15 F15 51(3) 3 . . 3 ? F16 P1 F16 F14 -85(2) 3 . . 3 ? F14 P1 F16 F14 -44(2) . . . 3 ? F12 P1 F16 F14 16(3) 3 . . 3 ? F12 P1 F16 F14 47(2) . . . 3 ? F15 P1 F16 F14 137(2) . . . 3 ? F15 P1 F16 F14 -179(2) 3 . . 3 ? F11 P1 F16 F14 -167(3) 3 . . 3 ? F11 P1 F16 F14 -134(2) . . . 3 ? F13 P1 F16 F14 -157(80) . . . 3 ? F13 P1 F16 F14 96(2) 3 . . 3 ? F4 P1 F16 F14 178.5(19) 3 . . 3 ? F4 P1 F16 F14 117(2) . . . 3 ? F2 P1 F16 F14 -150(2) . . . 3 ? F1 P1 F16 F14 31(2) . . . 3 ? F3 P1 F16 F14 -1(2) . . . 3 ? F3 P1 F16 F14 -63(2) 3 . . 3 ? F16 P1 F16 F11 82.3(18) 3 . . 3 ? F14 P1 F16 F11 167(3) 3 . . 3 ? F14 P1 F16 F11 123.0(14) . . . 3 ? F12 P1 F16 F11 -176.5(9) 3 . . 3 ? F12 P1 F16 F11 -145.3(15) . . . 3 ? F15 P1 F16 F11 -55.3(15) . . . 3 ? F15 P1 F16 F11 -12(3) 3 . . 3 ? F11 P1 F16 F11 33.1(14) . . . 3 ? F13 P1 F16 F11 10(82) . . . 3 ? F13 P1 F16 F11 -96.8(14) 3 . . 3 ? F4 P1 F16 F11 -14(4) 3 . . 3 ? F4 P1 F16 F11 -76.1(13) . . . 3 ? F2 P1 F16 F11 17.5(12) . . . 3 ? F1 P1 F16 F11 -162.1(10) . . . 3 ? F3 P1 F16 F11 166(4) . . . 3 ? F3 P1 F16 F11 103.9(13) 3 . . 3 ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.694 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.050 #===END data_(NMe3-tempo)2-Ni(dmit)2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis[(N,N,N-trimethyl-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)ammonium] bis(2-thioxo-1,3-dithiole-4,5-dithiolato-S4,S5)nickelate(II) ; _chemical_name_common 'bis(Me3N-Tempo)Ni(dmit)2' _chemical_melting_point ? _chemical_formula_moiety 'C6 Ni S10, 2(C12 H26 N2 O)' _chemical_formula_sum 'C30 H52 N4 Ni O2 S10' _chemical_formula_weight 880.15 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' 'Ni' 'Ni' 0.3393 1.1124 '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' '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 14.5213(17) _cell_length_b 15.982(3) _cell_length_c 18.150(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4212.3(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 11.5 _exptl_crystal_description block _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 0.989 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.6713 _exptl_absorpt_correction_T_max 0.8105 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 5 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CAD4 Enraf-Nonius' _diffrn_measurement_method Omega-theta-scans _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 3 _diffrn_reflns_number 7420 _diffrn_reflns_av_R_equivalents 0.0645 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 19.98 _reflns_number_total 1957 _reflns_number_gt 1332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 EXPRESS (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms, 1996)' _computing_structure_solution 'SIR92 (A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Prout & Pearce, 1996)' _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^)+(0.0310P)^2^+0.4914P] 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 1957 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0609 _refine_ls_wR_factor_gt 0.0525 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.5000 0.5000 0.5000 0.0364(2) Uani 1 2 d S . . S1 S 0.56881(7) 0.59280(6) 0.56978(6) 0.0462(3) Uani 1 1 d . . . C1 C 0.5506(3) 0.5496(2) 0.6564(2) 0.0398(10) Uani 1 1 d . . . S2 S 0.43411(7) 0.43796(6) 0.59367(6) 0.0480(3) Uani 1 1 d . . . C2 C 0.4935(2) 0.4843(2) 0.6663(2) 0.0382(10) Uani 1 1 d . . . S3 S 0.60662(7) 0.58503(6) 0.73536(6) 0.0535(3) Uani 1 1 d . . . C3 C 0.5627(2) 0.5136(2) 0.7971(2) 0.0477(12) Uani 1 1 d . . . S4 S 0.48589(7) 0.44609(6) 0.75592(6) 0.0528(3) Uani 1 1 d . . . S5 S 0.59076(8) 0.50832(7) 0.88533(6) 0.0623(4) Uani 1 1 d . . . O11 O 0.2842(2) 0.77194(19) 0.31682(18) 0.0811(10) Uani 1 1 d . . . N12 N 0.2862(2) 0.76523(19) 0.3866(2) 0.0442(9) Uani 1 1 d . . . N13 N 0.3126(2) 0.7292(2) 0.62210(17) 0.0404(9) Uani 1 1 d . . . C14 C 0.3549(3) 0.8185(2) 0.4253(2) 0.0413(10) Uani 1 1 d . . . C15 C 0.3352(3) 0.8181(2) 0.5072(2) 0.0473(11) Uani 1 1 d . . . H151 H 0.3869 0.8429 0.5329 0.078(15) Uiso 1 1 calc R . . H152 H 0.2815 0.8526 0.5167 0.057(13) Uiso 1 1 calc R . . C16 C 0.3182(3) 0.7319(2) 0.5377(2) 0.0383(10) Uani 1 1 d . . . H16 H 0.3706 0.6970 0.5232 0.049(12) Uiso 1 1 calc R . . C17 C 0.2343(3) 0.6966(3) 0.5004(2) 0.0497(12) Uani 1 1 d . . . H171 H 0.1821 0.7327 0.5105 0.080(16) Uiso 1 1 calc R . . H172 H 0.2208 0.6421 0.5212 0.072(14) Uiso 1 1 calc R . . C18 C 0.2451(3) 0.6876(2) 0.4172(2) 0.0418(10) Uani 1 1 d . . . C19 C 0.1494(3) 0.6774(3) 0.3834(3) 0.0682(14) Uani 1 1 d . . . H191 H 0.1115 0.7240 0.3972 0.102(19) Uiso 1 1 calc R . . H192 H 0.1221 0.6265 0.4010 0.074(15) Uiso 1 1 calc R . . H193 H 0.1546 0.6752 0.3307 0.14(3) Uiso 1 1 calc R . . C20 C 0.3047(3) 0.6134(3) 0.3955(3) 0.0695(14) Uani 1 1 d . . . H201 H 0.3095 0.6107 0.3428 0.11(2) Uiso 1 1 calc R . . H202 H 0.2773 0.5627 0.4136 0.092(17) Uiso 1 1 calc R . . H203 H 0.3650 0.6198 0.4165 0.066(15) Uiso 1 1 calc R . . C21 C 0.3434(3) 0.9071(2) 0.3958(3) 0.0576(13) Uani 1 1 d . . . H211 H 0.3558 0.9077 0.3439 0.10(2) Uiso 1 1 calc R . . H212 H 0.3856 0.9438 0.4206 0.049(12) Uiso 1 1 calc R . . H213 H 0.2814 0.9257 0.4045 0.062(14) Uiso 1 1 calc R . . C22 C 0.4524(3) 0.7870(3) 0.4078(3) 0.0624(13) Uani 1 1 d . . . H221 H 0.4618 0.7874 0.3555 0.079(17) Uiso 1 1 calc R . . H222 H 0.4596 0.7311 0.4261 0.061(13) Uiso 1 1 calc R . . H223 H 0.4968 0.8230 0.4309 0.082(17) Uiso 1 1 calc R . . C23 C 0.3972(3) 0.7655(3) 0.6554(3) 0.0707(15) Uani 1 1 d . . . H231 H 0.4502 0.7359 0.6375 0.10(2) Uiso 1 1 calc R . . H232 H 0.3941 0.7605 0.7081 0.086(17) Uiso 1 1 calc R . . H233 H 0.4019 0.8235 0.6422 0.095(19) Uiso 1 1 calc R . . C24 C 0.2306(4) 0.7755(4) 0.6504(3) 0.0843(18) Uani 1 1 d . . . H241 H 0.1757 0.7523 0.6291 0.09(2) Uiso 1 1 calc R . . H242 H 0.2356 0.8335 0.6372 0.11(2) Uiso 1 1 calc R . . H243 H 0.2279 0.7704 0.7030 0.064(14) Uiso 1 1 calc R . . C25 C 0.3088(3) 0.6399(3) 0.6468(2) 0.0571(13) Uani 1 1 d . . . H251 H 0.3616 0.6105 0.6282 0.086(17) Uiso 1 1 calc R . . H252 H 0.2537 0.6143 0.6284 0.074(16) Uiso 1 1 calc R . . H253 H 0.3089 0.6378 0.6997 0.056(13) 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 0.0345(4) 0.0300(4) 0.0446(5) 0.0014(4) -0.0024(4) -0.0020(3) S1 0.0549(7) 0.0372(6) 0.0465(8) 0.0045(5) -0.0042(6) -0.0128(5) C1 0.038(2) 0.030(2) 0.050(3) 0.002(2) -0.004(2) -0.003(2) S2 0.0472(7) 0.0450(7) 0.0517(8) 0.0013(6) 0.0013(6) -0.0155(5) C2 0.037(2) 0.036(2) 0.042(3) 0.007(2) -0.001(2) 0.001(2) S3 0.0634(8) 0.0489(7) 0.0482(8) 0.0030(6) -0.0103(6) -0.0137(6) C3 0.049(3) 0.038(2) 0.056(3) 0.003(2) 0.001(2) 0.005(2) S4 0.0582(7) 0.0489(7) 0.0514(8) 0.0095(6) 0.0026(6) -0.0092(6) S5 0.0778(8) 0.0605(8) 0.0486(8) 0.0070(6) -0.0091(6) 0.0028(7) O11 0.118(3) 0.086(2) 0.040(2) 0.0040(18) -0.009(2) -0.015(2) N12 0.061(2) 0.047(2) 0.024(2) -0.0002(19) -0.0048(19) 0.000(2) N13 0.043(2) 0.048(2) 0.030(2) 0.0015(18) -0.0008(18) 0.0035(19) C14 0.045(3) 0.040(3) 0.039(3) 0.002(2) -0.001(2) -0.005(2) C15 0.061(3) 0.039(3) 0.042(3) -0.002(2) -0.004(2) -0.007(3) C16 0.039(3) 0.038(2) 0.038(3) 0.000(2) 0.000(2) -0.003(2) C17 0.050(3) 0.047(3) 0.051(3) 0.007(3) -0.004(3) -0.015(3) C18 0.047(3) 0.035(3) 0.044(3) -0.005(2) -0.008(2) -0.005(2) C19 0.060(3) 0.060(4) 0.085(5) -0.008(3) -0.024(3) -0.004(3) C20 0.068(4) 0.049(3) 0.092(5) -0.016(3) -0.006(3) 0.008(3) C21 0.063(4) 0.040(3) 0.070(4) 0.012(3) -0.005(3) -0.005(3) C22 0.056(3) 0.056(3) 0.075(5) 0.012(3) 0.004(3) -0.002(3) C23 0.088(4) 0.071(4) 0.054(4) 0.004(3) -0.026(3) -0.021(3) C24 0.094(5) 0.120(6) 0.039(4) -0.002(3) 0.008(3) 0.059(4) C25 0.069(4) 0.054(3) 0.047(4) 0.017(3) -0.001(3) 0.002(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 S2 2.1884(11) 5_666 ? Ni1 S2 2.1884(11) . ? Ni1 S1 2.1914(10) 5_666 ? Ni1 S1 2.1914(10) . ? S1 C1 1.737(4) . ? C1 C2 1.345(5) . ? C1 S3 1.743(4) . ? S2 C2 1.740(4) . ? C2 S4 1.741(4) . ? S3 C3 1.723(4) . ? C3 S5 1.655(4) . ? C3 S4 1.722(4) . ? O11 N12 1.272(4) . ? N12 C18 1.484(5) . ? N12 C14 1.488(5) . ? N13 C23 1.487(4) . ? N13 C24 1.492(5) . ? N13 C25 1.497(4) . ? N13 C16 1.534(5) . ? C14 C15 1.514(5) . ? C14 C21 1.523(5) . ? C14 C22 1.536(5) . ? C15 C16 1.506(5) . ? C15 H151 0.9700 . ? C15 H152 0.9700 . ? C16 C17 1.505(5) . ? C16 H16 0.9800 . ? C17 C18 1.523(5) . ? C17 H171 0.9700 . ? C17 H172 0.9700 . ? C18 C20 1.522(5) . ? C18 C19 1.528(5) . ? C19 H191 0.9600 . ? C19 H192 0.9600 . ? C19 H193 0.9600 . ? C20 H201 0.9600 . ? C20 H202 0.9600 . ? C20 H203 0.9600 . ? C21 H211 0.9600 . ? C21 H212 0.9600 . ? C21 H213 0.9600 . ? C22 H221 0.9600 . ? C22 H222 0.9600 . ? C22 H223 0.9600 . ? C23 H231 0.9600 . ? C23 H232 0.9600 . ? C23 H233 0.9600 . ? C24 H241 0.9600 . ? C24 H242 0.9600 . ? C24 H243 0.9600 . ? C25 H251 0.9600 . ? C25 H252 0.9600 . ? C25 H253 0.9600 . ? 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 Ni1 S2 180.0 5_666 . ? S2 Ni1 S1 93.27(4) 5_666 5_666 ? S2 Ni1 S1 86.73(4) . 5_666 ? S2 Ni1 S1 86.73(4) 5_666 . ? S2 Ni1 S1 93.27(4) . . ? S1 Ni1 S1 180.00(4) 5_666 . ? C1 S1 Ni1 100.63(13) . . ? C2 C1 S1 121.6(3) . . ? C2 C1 S3 115.5(3) . . ? S1 C1 S3 123.0(2) . . ? C2 S2 Ni1 100.31(13) . . ? C1 C2 S2 122.3(3) . . ? C1 C2 S4 115.9(3) . . ? S2 C2 S4 121.8(2) . . ? C3 S3 C1 98.43(19) . . ? S5 C3 S4 123.2(2) . . ? S5 C3 S3 124.9(2) . . ? S4 C3 S3 111.9(2) . . ? C3 S4 C2 98.33(19) . . ? O11 N12 C18 115.7(3) . . ? O11 N12 C14 115.9(3) . . ? C18 N12 C14 124.9(3) . . ? C23 N13 C24 109.0(4) . . ? C23 N13 C25 106.2(3) . . ? C24 N13 C25 109.9(4) . . ? C23 N13 C16 110.5(3) . . ? C24 N13 C16 111.8(3) . . ? C25 N13 C16 109.1(3) . . ? N12 C14 C15 109.5(3) . . ? N12 C14 C21 107.0(3) . . ? C15 C14 C21 109.1(3) . . ? N12 C14 C22 109.5(3) . . ? C15 C14 C22 112.1(4) . . ? C21 C14 C22 109.5(3) . . ? C16 C15 C14 113.4(3) . . ? C16 C15 H151 108.9 . . ? C14 C15 H151 108.9 . . ? C16 C15 H152 108.9 . . ? C14 C15 H152 108.9 . . ? H151 C15 H152 107.7 . . ? C17 C16 C15 108.0(3) . . ? C17 C16 N13 113.4(3) . . ? C15 C16 N13 113.7(3) . . ? C17 C16 H16 107.1 . . ? C15 C16 H16 107.1 . . ? N13 C16 H16 107.1 . . ? C16 C17 C18 113.5(3) . . ? C16 C17 H171 108.9 . . ? C18 C17 H171 108.9 . . ? C16 C17 H172 108.9 . . ? C18 C17 H172 108.9 . . ? H171 C17 H172 107.7 . . ? N12 C18 C20 109.0(3) . . ? N12 C18 C17 109.5(3) . . ? C20 C18 C17 112.9(4) . . ? N12 C18 C19 107.7(3) . . ? C20 C18 C19 109.3(4) . . ? C17 C18 C19 108.4(4) . . ? C18 C19 H191 109.5 . . ? C18 C19 H192 109.5 . . ? H191 C19 H192 109.5 . . ? C18 C19 H193 109.5 . . ? H191 C19 H193 109.5 . . ? H192 C19 H193 109.5 . . ? C18 C20 H201 109.5 . . ? C18 C20 H202 109.5 . . ? H201 C20 H202 109.5 . . ? C18 C20 H203 109.5 . . ? H201 C20 H203 109.5 . . ? H202 C20 H203 109.5 . . ? C14 C21 H211 109.5 . . ? C14 C21 H212 109.5 . . ? H211 C21 H212 109.5 . . ? C14 C21 H213 109.5 . . ? H211 C21 H213 109.5 . . ? H212 C21 H213 109.5 . . ? C14 C22 H221 109.5 . . ? C14 C22 H222 109.5 . . ? H221 C22 H222 109.5 . . ? C14 C22 H223 109.5 . . ? H221 C22 H223 109.5 . . ? H222 C22 H223 109.5 . . ? N13 C23 H231 109.5 . . ? N13 C23 H232 109.5 . . ? H231 C23 H232 109.5 . . ? N13 C23 H233 109.5 . . ? H231 C23 H233 109.5 . . ? H232 C23 H233 109.5 . . ? N13 C24 H241 109.5 . . ? N13 C24 H242 109.5 . . ? H241 C24 H242 109.5 . . ? N13 C24 H243 109.5 . . ? H241 C24 H243 109.5 . . ? H242 C24 H243 109.5 . . ? N13 C25 H251 109.5 . . ? N13 C25 H252 109.5 . . ? H251 C25 H252 109.5 . . ? N13 C25 H253 109.5 . . ? H251 C25 H253 109.5 . . ? H252 C25 H253 109.5 . . ? 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 S2 Ni1 S1 C1 -168.12(13) 5_666 . . . ? S2 Ni1 S1 C1 11.88(13) . . . . ? S1 Ni1 S1 C1 42(100) 5_666 . . . ? Ni1 S1 C1 C2 -9.7(3) . . . . ? Ni1 S1 C1 S3 168.4(2) . . . . ? S2 Ni1 S2 C2 -96(100) 5_666 . . . ? S1 Ni1 S2 C2 168.26(12) 5_666 . . . ? S1 Ni1 S2 C2 -11.74(12) . . . . ? S1 C1 C2 S2 0.2(5) . . . . ? S3 C1 C2 S2 -177.98(19) . . . . ? S1 C1 C2 S4 177.86(19) . . . . ? S3 C1 C2 S4 -0.3(4) . . . . ? Ni1 S2 C2 C1 9.4(3) . . . . ? Ni1 S2 C2 S4 -168.12(19) . . . . ? C2 C1 S3 C3 1.2(3) . . . . ? S1 C1 S3 C3 -176.9(2) . . . . ? C1 S3 C3 S5 177.6(3) . . . . ? C1 S3 C3 S4 -1.7(2) . . . . ? S5 C3 S4 C2 -177.7(2) . . . . ? S3 C3 S4 C2 1.5(2) . . . . ? C1 C2 S4 C3 -0.7(3) . . . . ? S2 C2 S4 C3 176.9(2) . . . . ? O11 N12 C14 C15 167.7(3) . . . . ? C18 N12 C14 C15 -34.5(5) . . . . ? O11 N12 C14 C21 49.5(4) . . . . ? C18 N12 C14 C21 -152.6(4) . . . . ? O11 N12 C14 C22 -69.1(4) . . . . ? C18 N12 C14 C22 88.8(4) . . . . ? N12 C14 C15 C16 46.8(4) . . . . ? C21 C14 C15 C16 163.7(3) . . . . ? C22 C14 C15 C16 -74.9(4) . . . . ? C14 C15 C16 C17 -61.9(5) . . . . ? C14 C15 C16 N13 171.3(3) . . . . ? C23 N13 C16 C17 -179.6(3) . . . . ? C24 N13 C16 C17 -57.9(5) . . . . ? C25 N13 C16 C17 63.9(4) . . . . ? C23 N13 C16 C15 -55.7(5) . . . . ? C24 N13 C16 C15 66.0(5) . . . . ? C25 N13 C16 C15 -172.2(3) . . . . ? C15 C16 C17 C18 61.3(4) . . . . ? N13 C16 C17 C18 -171.8(3) . . . . ? O11 N12 C18 C20 67.9(4) . . . . ? C14 N12 C18 C20 -90.0(4) . . . . ? O11 N12 C18 C17 -168.2(3) . . . . ? C14 N12 C18 C17 33.9(5) . . . . ? O11 N12 C18 C19 -50.6(5) . . . . ? C14 N12 C18 C19 151.5(4) . . . . ? C16 C17 C18 N12 -45.8(4) . . . . ? C16 C17 C18 C20 75.9(4) . . . . ? C16 C17 C18 C19 -163.0(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 19.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.308 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.066 #===END data_(NMe3-tempo)2-Pd(dmit)2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis[(N,N,N-trimethyl-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)ammonium] bis(2-thioxo-1,3-dithiole-4,5-dithiolato-S4,S5)palladate(II) ; _chemical_name_common 'bis(Me3N-Tempo)Pd(dmit)2' _chemical_melting_point ? _chemical_formula_moiety 'C6 Pd S10, 2(C12 H26 N2 O)' _chemical_formula_sum 'C30 H52 N4 O2 Pd S10' _chemical_formula_weight 927.76 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' 'Pd' 'Pd' -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 14.646(3) _cell_length_b 16.012(4) _cell_length_c 18.126(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4250.8(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 106 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1928 _exptl_absorpt_coefficient_mu 0.960 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.2518 _exptl_absorpt_correction_T_max 0.8356 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 5 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CAD4 Enraf-Nonius' _diffrn_measurement_method Omega-theta-scans _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1 _diffrn_reflns_number 5550 _diffrn_reflns_av_R_equivalents 0.0113 _diffrn_reflns_av_sigmaI/netI 0.1091 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 29.96 _reflns_number_total 5527 _reflns_number_gt 2283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 EXPRESS (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms, 1996)' _computing_structure_solution 'SIR92 (A. Altomare, G. Cascarano, C. Giacovazzo & A. Guagliardi, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Prout & Pearce, 1996)' _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^)+(0.0730P)^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 5527 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1712 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1445 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _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 Pd1 Pd 0.5000 0.5000 0.5000 0.03378(13) Uani 1 2 d S . . S1 S 0.57450(9) 0.59490(7) 0.57446(7) 0.0434(3) Uani 1 1 d . . . S2 S 0.43454(8) 0.43625(8) 0.60098(7) 0.0444(3) Uani 1 1 d . . . S3 S 0.60985(10) 0.58566(8) 0.73902(7) 0.0505(3) Uani 1 1 d . . . S4 S 0.48968(9) 0.44774(8) 0.76079(7) 0.0486(3) Uani 1 1 d . . . S5 S 0.59422(11) 0.51018(9) 0.88984(8) 0.0598(4) Uani 1 1 d . . . C1 C 0.5535(3) 0.5501(3) 0.6600(3) 0.0381(11) Uani 1 1 d . . . C2 C 0.4969(3) 0.4850(3) 0.6701(3) 0.0395(11) Uani 1 1 d . . . C3 C 0.5663(3) 0.5144(3) 0.8017(3) 0.0459(12) Uani 1 1 d . . . O11 O 0.2859(3) 0.7725(3) 0.3112(2) 0.0774(14) Uani 1 1 d . . . N12 N 0.2886(3) 0.7655(2) 0.3811(2) 0.0414(10) Uani 1 1 d . . . N13 N 0.3147(3) 0.7293(3) 0.6168(2) 0.0394(9) Uani 1 1 d . . . C14 C 0.3567(3) 0.8181(3) 0.4200(3) 0.0406(11) Uani 1 1 d . . . C15 C 0.3364(4) 0.8187(3) 0.5029(2) 0.0437(11) Uani 1 1 d . . . H15A H 0.3872 0.8441 0.5289 0.052 Uiso 1 1 calc R . . H15B H 0.2825 0.8524 0.5121 0.052 Uiso 1 1 calc R . . C16 C 0.3209(3) 0.7319(3) 0.5327(3) 0.0360(10) Uani 1 1 d . . . H16 H 0.3730 0.6973 0.5178 0.043 Uiso 1 1 calc R . . C17 C 0.2363(3) 0.6969(3) 0.4953(2) 0.0466(12) Uani 1 1 d . . . H17A H 0.1850 0.7336 0.5053 0.056 Uiso 1 1 calc R . . H17B H 0.2224 0.6427 0.5164 0.056 Uiso 1 1 calc R . . C18 C 0.2472(3) 0.6876(3) 0.4124(2) 0.0378(10) Uani 1 1 d . . . C19 C 0.1527(4) 0.6783(4) 0.3793(3) 0.0627(16) Uani 1 1 d . . . H19A H 0.1157 0.7252 0.3933 0.075 Uiso 1 1 calc R . . H19B H 0.1252 0.6277 0.3970 0.075 Uiso 1 1 calc R . . H19C H 0.1574 0.6761 0.3265 0.075 Uiso 1 1 calc R . . C20 C 0.3072(4) 0.6135(3) 0.3911(4) 0.0655(17) Uani 1 1 d . . . H20A H 0.3664 0.6197 0.4131 0.079 Uiso 1 1 calc R . . H20B H 0.3133 0.6114 0.3384 0.079 Uiso 1 1 calc R . . H20C H 0.2795 0.5627 0.4083 0.079 Uiso 1 1 calc R . . C21 C 0.3459(4) 0.9071(3) 0.3905(3) 0.0574(15) Uani 1 1 d . . . H21A H 0.3576 0.9077 0.3384 0.069 Uiso 1 1 calc R . . H21B H 0.3885 0.9433 0.4151 0.069 Uiso 1 1 calc R . . H21C H 0.2848 0.9262 0.3996 0.069 Uiso 1 1 calc R . . C22 C 0.4525(3) 0.7863(3) 0.4025(3) 0.0591(15) Uani 1 1 d . . . H22A H 0.4594 0.7305 0.4212 0.071 Uiso 1 1 calc R . . H22B H 0.4968 0.8221 0.4252 0.071 Uiso 1 1 calc R . . H22C H 0.4615 0.7861 0.3500 0.071 Uiso 1 1 calc R . . C23 C 0.3112(4) 0.6399(3) 0.6426(3) 0.0571(15) Uani 1 1 d . . . H23A H 0.2583 0.6131 0.6223 0.069 Uiso 1 1 calc R . . H23B H 0.3081 0.6385 0.6955 0.069 Uiso 1 1 calc R . . H23C H 0.3652 0.6111 0.6264 0.069 Uiso 1 1 calc R . . C24 C 0.3982(4) 0.7656(4) 0.6503(3) 0.0670(17) Uani 1 1 d . . . H24A H 0.4509 0.7361 0.6326 0.080 Uiso 1 1 calc R . . H24B H 0.3949 0.7607 0.7030 0.080 Uiso 1 1 calc R . . H24C H 0.4029 0.8235 0.6369 0.080 Uiso 1 1 calc R . . C25 C 0.2324(4) 0.7753(5) 0.6456(3) 0.081(2) Uani 1 1 d . . . H25A H 0.1781 0.7519 0.6243 0.097 Uiso 1 1 calc R . . H25B H 0.2369 0.8332 0.6325 0.097 Uiso 1 1 calc R . . H25C H 0.2299 0.7700 0.6983 0.097 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 Pd1 0.0309(2) 0.0324(2) 0.0380(3) 0.0002(2) -0.0031(2) -0.0020(2) S1 0.0503(7) 0.0401(6) 0.0397(7) 0.0012(6) -0.0042(6) -0.0135(6) S2 0.0420(7) 0.0452(6) 0.0461(7) 0.0013(6) -0.0006(6) -0.0132(5) S3 0.0608(8) 0.0503(7) 0.0404(7) 0.0027(6) -0.0085(6) -0.0137(7) S4 0.0537(8) 0.0509(7) 0.0410(7) 0.0082(6) 0.0038(6) -0.0078(6) S5 0.0752(10) 0.0634(9) 0.0408(7) 0.0063(7) -0.0096(7) 0.0011(8) C1 0.043(3) 0.035(2) 0.036(3) 0.002(2) 0.000(2) 0.000(2) C2 0.039(2) 0.040(3) 0.039(2) 0.0008(19) -0.001(2) 0.001(2) C3 0.049(3) 0.046(3) 0.043(3) -0.002(2) -0.002(2) 0.006(2) O11 0.111(4) 0.094(3) 0.027(2) 0.002(2) -0.008(2) -0.016(3) N12 0.053(3) 0.043(2) 0.029(2) 0.0023(19) -0.0039(18) -0.0031(19) N13 0.041(2) 0.051(2) 0.026(2) -0.0021(19) -0.0022(17) 0.0057(18) C14 0.051(3) 0.039(2) 0.031(3) -0.002(2) -0.003(2) -0.003(2) C15 0.055(3) 0.041(2) 0.035(3) -0.007(2) -0.005(2) -0.009(2) C16 0.041(3) 0.041(2) 0.025(2) 0.000(2) -0.001(2) -0.003(2) C17 0.044(3) 0.055(3) 0.041(3) 0.012(3) -0.003(2) -0.010(2) C18 0.044(2) 0.035(2) 0.034(2) -0.006(2) -0.012(2) 0.000(2) C19 0.056(4) 0.064(3) 0.068(4) -0.006(3) -0.023(3) 0.000(3) C20 0.068(4) 0.046(3) 0.082(5) -0.009(3) -0.012(3) 0.008(3) C21 0.069(4) 0.045(3) 0.058(4) 0.007(3) -0.002(3) 0.000(3) C22 0.050(3) 0.059(3) 0.068(4) 0.005(3) 0.010(3) -0.003(3) C23 0.066(4) 0.061(3) 0.044(3) 0.023(3) -0.001(3) -0.004(3) C24 0.079(4) 0.072(4) 0.050(4) -0.003(3) -0.026(3) -0.014(3) C25 0.075(5) 0.121(6) 0.046(4) -0.007(4) 0.006(3) 0.049(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 Pd1 S2 2.3047(13) 5_666 ? Pd1 S2 2.3047(13) . ? Pd1 S1 2.3068(12) . ? Pd1 S1 2.3068(12) 5_666 ? S1 C1 1.736(5) . ? S2 C2 1.736(5) . ? S3 C3 1.731(5) . ? S3 C1 1.748(5) . ? S4 C3 1.717(5) . ? S4 C2 1.751(5) . ? S5 C3 1.651(5) . ? C1 C2 1.345(6) . ? O11 N12 1.273(5) . ? N12 C14 1.484(6) . ? N12 C18 1.498(6) . ? N13 C24 1.484(6) . ? N13 C25 1.505(6) . ? N13 C23 1.507(6) . ? N13 C16 1.529(6) . ? C14 C22 1.526(7) . ? C14 C21 1.531(6) . ? C14 C15 1.533(6) . ? C15 C16 1.507(6) . ? C16 C17 1.519(6) . ? C17 C18 1.519(6) . ? C18 C19 1.516(7) . ? C18 C20 1.527(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S2 Pd1 S2 180.00(6) 5_666 . ? S2 Pd1 S1 88.63(5) 5_666 . ? S2 Pd1 S1 91.37(5) . . ? S2 Pd1 S1 91.37(5) 5_666 5_666 ? S2 Pd1 S1 88.63(5) . 5_666 ? S1 Pd1 S1 180.00(4) . 5_666 ? C1 S1 Pd1 99.60(16) . . ? C2 S2 Pd1 98.94(17) . . ? C3 S3 C1 98.5(2) . . ? C3 S4 C2 98.8(2) . . ? C2 C1 S1 123.5(4) . . ? C2 C1 S3 115.6(4) . . ? S1 C1 S3 120.9(3) . . ? C1 C2 S2 125.1(4) . . ? C1 C2 S4 115.4(4) . . ? S2 C2 S4 119.5(3) . . ? S5 C3 S4 123.6(3) . . ? S5 C3 S3 124.8(3) . . ? S4 C3 S3 111.6(3) . . ? O11 N12 C14 116.3(4) . . ? O11 N12 C18 116.0(4) . . ? C14 N12 C18 124.4(4) . . ? C24 N13 C25 109.0(4) . . ? C24 N13 C23 105.9(4) . . ? C25 N13 C23 109.3(4) . . ? C24 N13 C16 110.4(4) . . ? C25 N13 C16 112.3(4) . . ? C23 N13 C16 109.7(4) . . ? N12 C14 C22 109.3(4) . . ? N12 C14 C21 107.1(4) . . ? C22 C14 C21 109.5(4) . . ? N12 C14 C15 109.8(4) . . ? C22 C14 C15 112.6(4) . . ? C21 C14 C15 108.4(4) . . ? C16 C15 C14 112.0(4) . . ? C15 C16 C17 107.7(4) . . ? C15 C16 N13 113.0(4) . . ? C17 C16 N13 112.7(4) . . ? C16 C17 C18 113.0(4) . . ? N12 C18 C19 107.5(4) . . ? N12 C18 C17 109.6(4) . . ? C19 C18 C17 107.8(4) . . ? N12 C18 C20 108.6(4) . . ? C19 C18 C20 110.4(4) . . ? C17 C18 C20 112.8(4) . . ? _diffrn_measured_fraction_theta_max 0.895 _diffrn_reflns_theta_full 29.96 _diffrn_measured_fraction_theta_full 0.895 _refine_diff_density_max 0.741 _refine_diff_density_min -0.857 _refine_diff_density_rms 0.125 #===END data_(NMe3-tempo)-Ni(dmit)2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [(N,N,N-trimethyl-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)ammonium] bis(2-thioxo-1,3-dithiole-4,5-dithiolato-S4,S5)nickelate(III) ; _chemical_name_common '(Me3N-Tempo)Ni(dmit)2' _chemical_melting_point ? _chemical_formula_moiety 'C6 Ni S10, C12 H26 N2 O' _chemical_formula_sum 'C18 H26 N2 Ni O S10' _chemical_formula_weight 665.72 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 P21/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 8.3716(11) _cell_length_b 11.9980(19) _cell_length_c 28.592(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.251(16) _cell_angle_gamma 90.00 _cell_volume 2871.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3253 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 26.15 _exptl_crystal_description 'narrow plate' _exptl_crystal_colour black _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 1.419 _exptl_absorpt_correction_type 'numerical' _exptl_absorpt_correction_T_min 0.27 _exptl_absorpt_correction_T_max 0.72 _exptl_absorpt_process_details ? _exptl_special_details ; The data were collected on a Stoe Imaging Plate Diffraction System (IPDS).The crystal-to-detector distance was 70 mm. 227 exposures (7 min per exposure) were obtained with 0 < \f < 250\% and with the crystals rotated through 1.1\% in \f. Crystal decay was monitored by measuring 200 reflexions per image. ; _diffrn_ambient_temperature 293(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 'STOE Imaging Plate Diffraction System' _diffrn_measurement_method '\f scan ' _diffrn_standards_decay_% 'negligible' _diffrn_reflns_number 27237 _diffrn_reflns_av_R_equivalents 0.2928 _diffrn_reflns_av_sigmaI/netI 0.3232 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.15 _reflns_number_total 5644 _reflns_number_gt 985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS software (Stoe, 1996)' _computing_cell_refinement 'IPDS software (Stoe, 1996)' _computing_data_reduction 'XRED (Stoe, X-Red 1.08, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Prout & Pearce, 1996)' _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^)+(0.0889P)^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 5644 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3304 _refine_ls_R_factor_gt 0.0715 _refine_ls_wR_factor_ref 0.2509 _refine_ls_wR_factor_gt 0.1551 _refine_ls_goodness_of_fit_ref 0.716 _refine_ls_restrained_S_all 0.716 _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 0.1413(3) 0.50019(17) 0.45353(6) 0.0868(6) Uani 1 1 d . . . S1 S 0.3079(6) 0.4328(3) 0.50486(14) 0.1060(16) Uani 1 1 d . . . S6 S -0.0286(6) 0.5704(3) 0.40510(15) 0.1065(15) Uani 1 1 d . . . S2 S 0.0394(6) 0.3380(3) 0.43881(15) 0.1000(14) Uani 1 1 d . . . S7 S 0.2673(6) 0.6550(3) 0.46207(15) 0.1051(15) Uani 1 1 d . . . S3 S 0.3684(6) 0.1963(4) 0.53734(15) 0.1131(16) Uani 1 1 d . . . S8 S -0.0625(6) 0.8062(4) 0.36638(16) 0.1180(17) Uani 1 1 d . . . S4 S 0.1167(6) 0.1098(3) 0.47845(15) 0.1044(15) Uani 1 1 d . . . S9 S 0.2134(6) 0.8812(3) 0.41724(16) 0.1113(16) Uani 1 1 d . . . S5 S 0.3112(7) -0.0456(4) 0.53555(18) 0.1315(19) Uani 1 1 d . . . S10 S 0.0397(7) 1.0421(4) 0.35656(17) 0.1214(17) Uani 1 1 d . . . C1 C 0.2588(18) 0.2965(12) 0.5045(5) 0.087(4) Uiso 1 1 d . . . C2 C 0.1492(17) 0.2542(10) 0.4760(4) 0.073(4) Uiso 1 1 d . . . C3 C 0.2653(19) 0.0801(12) 0.5187(5) 0.090(4) Uiso 1 1 d . . . C4 C 0.0315(18) 0.7072(11) 0.4012(5) 0.083(4) Uiso 1 1 d . . . C5 C 0.1602(18) 0.7415(11) 0.4263(4) 0.080(4) Uiso 1 1 d . . . C6 C 0.0635(19) 0.9174(12) 0.3780(5) 0.087(4) Uiso 1 1 d . . . C14 C 0.653(3) 0.4915(18) 0.2709(7) 0.146(7) Uiso 1 1 d . . . C15 C 0.671(3) 0.4320(17) 0.3186(7) 0.148(7) Uiso 1 1 d . . . H15A H 0.7649 0.3843 0.3184 0.177 Uiso 1 1 calc R . . H15B H 0.6869 0.4870 0.3431 0.177 Uiso 1 1 calc R . . C16 C 0.528(2) 0.3639(13) 0.3285(5) 0.098(5) Uiso 1 1 d . . . H16 H 0.5003 0.3204 0.3004 0.118 Uiso 1 1 calc R . . C17 C 0.394(2) 0.4421(15) 0.3374(6) 0.125(6) Uiso 1 1 d . . . H17A H 0.4274 0.4977 0.3602 0.150 Uiso 1 1 calc R . . H17B H 0.3037 0.4017 0.3497 0.150 Uiso 1 1 calc R . . C18 C 0.343(3) 0.502(2) 0.2884(8) 0.166(8) Uiso 1 1 d . . . C19 C 0.249(3) 0.608(2) 0.3053(8) 0.201(11) Uiso 1 1 d . . . H19A H 0.3139 0.6491 0.3273 0.241 Uiso 1 1 calc R . . H19B H 0.1520 0.5853 0.3198 0.241 Uiso 1 1 calc R . . H19C H 0.2233 0.6548 0.2788 0.241 Uiso 1 1 calc R . . C20 C 0.260(3) 0.4299(19) 0.2538(8) 0.189(10) Uiso 1 1 d . . . H20A H 0.3278 0.3687 0.2459 0.226 Uiso 1 1 calc R . . H20B H 0.2339 0.4722 0.2262 0.226 Uiso 1 1 calc R . . H20C H 0.1631 0.4017 0.2670 0.226 Uiso 1 1 calc R . . C21 C 0.780(3) 0.5880(19) 0.2694(8) 0.194(10) Uiso 1 1 d . . . H21A H 0.7755 0.6310 0.2977 0.232 Uiso 1 1 calc R . . H21B H 0.7570 0.6353 0.2430 0.232 Uiso 1 1 calc R . . H21C H 0.8849 0.5567 0.2666 0.232 Uiso 1 1 calc R . . C22 C 0.650(3) 0.418(2) 0.2270(9) 0.216(11) Uiso 1 1 d . . . H22A H 0.6380 0.4641 0.1997 0.259 Uiso 1 1 calc R . . H22B H 0.5612 0.3672 0.2284 0.259 Uiso 1 1 calc R . . H22C H 0.7475 0.3765 0.2255 0.259 Uiso 1 1 calc R . . C23 C 0.6997(19) 0.2117(12) 0.3575(5) 0.105(5) Uiso 1 1 d . . . H23A H 0.7924 0.2583 0.3553 0.125 Uiso 1 1 calc R . . H23B H 0.6805 0.1748 0.3281 0.125 Uiso 1 1 calc R . . H23C H 0.7170 0.1572 0.3816 0.125 Uiso 1 1 calc R . . C24 C 0.418(2) 0.2074(13) 0.3715(5) 0.114(5) Uiso 1 1 d . . . H24A H 0.4001 0.1721 0.3417 0.137 Uiso 1 1 calc R . . H24B H 0.3245 0.2495 0.3794 0.137 Uiso 1 1 calc R . . H24C H 0.4376 0.1516 0.3949 0.137 Uiso 1 1 calc R . . C25 C 0.581(2) 0.3357(13) 0.4156(5) 0.114(5) Uiso 1 1 d . . . H25A H 0.6711 0.3851 0.4146 0.136 Uiso 1 1 calc R . . H25B H 0.6008 0.2791 0.4388 0.136 Uiso 1 1 calc R . . H25C H 0.4873 0.3771 0.4235 0.136 Uiso 1 1 calc R . . N12 N 0.4961(19) 0.5476(11) 0.2698(4) 0.109(4) Uiso 1 1 d . . . N13 N 0.5562(14) 0.2826(9) 0.3691(3) 0.078(3) Uiso 1 1 d . . . O11 O 0.4789(16) 0.6281(11) 0.2384(4) 0.142(4) Uiso 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 0.1082(16) 0.0676(10) 0.0843(10) -0.0011(9) -0.0055(9) 0.0004(11) S1 0.140(5) 0.070(3) 0.107(3) 0.000(2) -0.030(3) -0.003(3) S6 0.114(4) 0.083(3) 0.122(3) 0.006(2) -0.024(3) -0.010(3) S2 0.108(4) 0.072(3) 0.119(3) 0.003(2) -0.023(3) -0.003(2) S7 0.126(4) 0.068(3) 0.119(3) 0.005(2) -0.041(3) 0.000(2) S3 0.142(4) 0.090(3) 0.106(3) 0.015(2) -0.028(3) -0.002(3) S8 0.126(4) 0.096(3) 0.130(4) 0.017(3) -0.034(3) 0.006(3) S4 0.122(4) 0.071(3) 0.120(3) 0.013(2) -0.022(3) -0.009(3) S9 0.130(4) 0.069(3) 0.133(3) 0.006(2) -0.034(3) 0.000(3) S5 0.162(6) 0.087(3) 0.144(4) 0.041(3) -0.018(4) 0.002(3) S10 0.138(5) 0.091(3) 0.134(4) 0.025(3) -0.004(3) 0.015(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 S6 2.137(5) . ? Ni1 S7 2.147(5) . ? Ni1 S1 2.160(5) . ? Ni1 S2 2.162(4) . ? S1 C1 1.686(15) . ? S6 C4 1.721(14) . ? S2 C2 1.717(13) . ? S7 C5 1.699(13) . ? S3 C3 1.718(15) . ? S3 C1 1.768(14) . ? S8 C6 1.728(15) . ? S8 C4 1.729(14) . ? S4 C3 1.715(15) . ? S4 C2 1.755(13) . ? S9 C6 1.722(15) . ? S9 C5 1.754(14) . ? S5 C3 1.626(15) . ? S10 C6 1.627(15) . ? C1 C2 1.316(17) . ? C4 C5 1.346(17) . ? C14 N12 1.48(2) . ? C14 C22 1.53(3) . ? C14 C15 1.54(2) . ? C14 C21 1.57(3) . ? C15 C16 1.49(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.49(2) . ? C16 N13 1.531(16) . ? C16 H16 0.9800 . ? C17 C18 1.62(2) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C20 1.48(3) . ? C18 N12 1.50(2) . ? C18 C19 1.58(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 N13 1.514(16) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 N13 1.473(17) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 N13 1.486(16) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? N12 O11 1.323(15) . ? 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 S6 Ni1 S7 92.94(17) . . ? S6 Ni1 S1 177.6(2) . . ? S7 Ni1 S1 86.46(17) . . ? S6 Ni1 S2 88.51(17) . . ? S7 Ni1 S2 172.4(2) . . ? S1 Ni1 S2 92.39(17) . . ? C1 S1 Ni1 101.9(5) . . ? C4 S6 Ni1 103.1(5) . . ? C2 S2 Ni1 101.7(5) . . ? C5 S7 Ni1 102.0(5) . . ? C3 S3 C1 97.8(7) . . ? C6 S8 C4 98.8(7) . . ? C3 S4 C2 96.9(7) . . ? C6 S9 C5 98.9(7) . . ? C2 C1 S1 123.0(11) . . ? C2 C1 S3 114.4(11) . . ? S1 C1 S3 122.2(9) . . ? C1 C2 S2 121.0(11) . . ? C1 C2 S4 117.6(10) . . ? S2 C2 S4 121.4(8) . . ? S5 C3 S4 123.7(9) . . ? S5 C3 S3 123.2(9) . . ? S4 C3 S3 113.0(8) . . ? C5 C4 S6 119.3(11) . . ? C5 C4 S8 116.5(11) . . ? S6 C4 S8 124.2(9) . . ? C4 C5 S7 122.7(11) . . ? C4 C5 S9 114.6(10) . . ? S7 C5 S9 122.7(8) . . ? S10 C6 S9 124.0(9) . . ? S10 C6 S8 124.7(9) . . ? S9 C6 S8 111.3(8) . . ? N12 C14 C22 103.9(17) . . ? N12 C14 C15 107.4(17) . . ? C22 C14 C15 117.1(19) . . ? N12 C14 C21 105.4(18) . . ? C22 C14 C21 114(2) . . ? C15 C14 C21 108.3(18) . . ? C16 C15 C14 111.1(16) . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C17 107.5(16) . . ? C15 C16 N13 112.4(13) . . ? C17 C16 N13 112.2(13) . . ? C15 C16 H16 108.2 . . ? C17 C16 H16 108.2 . . ? N13 C16 H16 108.2 . . ? C16 C17 C18 108.6(15) . . ? C16 C17 H17A 110.0 . . ? C18 C17 H17A 110.0 . . ? C16 C17 H17B 110.0 . . ? C18 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? C20 C18 N12 111.6(19) . . ? C20 C18 C19 117(2) . . ? N12 C18 C19 105(2) . . ? C20 C18 C17 115(2) . . ? N12 C18 C17 104.8(17) . . ? C19 C18 C17 102.7(17) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C14 C21 H21A 109.5 . . ? C14 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C14 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C14 C22 H22A 109.5 . . ? C14 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C14 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N13 C23 H23A 109.5 . . ? N13 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N13 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N13 C24 H24A 109.5 . . ? N13 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N13 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N13 C25 H25A 109.5 . . ? N13 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N13 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O11 N12 C14 115.5(15) . . ? O11 N12 C18 115.0(15) . . ? C14 N12 C18 126.5(17) . . ? C24 N13 C25 108.4(11) . . ? C24 N13 C23 107.2(11) . . ? C25 N13 C23 109.9(11) . . ? C24 N13 C16 108.4(11) . . ? C25 N13 C16 115.0(11) . . ? C23 N13 C16 107.6(11) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.15 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.574 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.090