Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_tmp1 _database_code_CSD 182194 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Meng, Qingjin' 'Gao, Song' 'He, Cheng' 'Liu, Wenlong' 'Ren, Xiaoming' 'Song, You' 'Xie, Jingli' 'Zhang, Wenwei' _publ_contact_author_name 'Prof Meng Qingjin' _publ_contact_author_address ; State Key Laboratory of Coordination Chemistry Nanjing University Coordination Chemistry Institute Nanjing 210093 CHINA ; _publ_contact_author_email 'NJUJLXIE@YAHOO.COM' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Peculiar magnetic behavior in ion-pair complex [1-(4'-fluorobenzyl)pyridinium][Ni(mnt)2] (mnt2- = maleonitriledithiolate) ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H11 F N5 Ni S4' _chemical_formula_weight 527.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 P2(1)/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 12.1500(4) _cell_length_b 25.9523(6) _cell_length_c 7.3397(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.74 _cell_angle_gamma 90.00 _cell_volume 2265.95(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 6 _cell_measurement_theta_max 12 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1068 _exptl_absorpt_coefficient_mu 1.251 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.830 _exptl_absorpt_correction_T_max 0.883 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7854 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4013 _reflns_number_gt 2636 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material ; 'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)' ; _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^)+(0.0939P)^2^+1.0999P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0021(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4013 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0994 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1804 _refine_ls_wR_factor_gt 0.1535 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.27209(5) 0.27888(2) 0.52337(10) 0.0563(3) Uani 1 1 d . . . S2 S 0.38477(11) 0.21564(5) 0.6060(2) 0.0632(4) Uani 1 1 d . . . S1 S 0.13383(11) 0.22822(5) 0.4207(2) 0.0638(4) Uani 1 1 d . . . S3 S 0.16347(11) 0.34351(6) 0.4347(2) 0.0652(4) Uani 1 1 d . . . S4 S 0.41268(12) 0.32772(6) 0.6287(2) 0.0669(4) Uani 1 1 d . . . N1 N 0.0608(5) 0.0909(2) 0.3597(9) 0.1013(19) Uani 1 1 d . . . N2 N 0.4001(5) 0.0745(2) 0.6003(8) 0.0991(18) Uani 1 1 d . . . N3 N 0.1685(5) 0.4853(2) 0.3920(9) 0.104(2) Uani 1 1 d . . . N4 N 0.5112(6) 0.4593(2) 0.6636(10) 0.114(2) Uani 1 1 d . . . C1 C 0.1199(5) 0.1244(2) 0.4036(8) 0.0707(15) Uani 1 1 d . . . C2 C 0.1917(4) 0.1683(2) 0.4572(7) 0.0582(13) Uani 1 1 d . . . C3 C 0.3015(4) 0.1628(2) 0.5413(7) 0.0547(12) Uani 1 1 d . . . C4 C 0.3552(5) 0.1135(2) 0.5717(8) 0.0703(15) Uani 1 1 d . . . C5 C 0.2067(5) 0.4462(2) 0.4367(9) 0.0774(17) Uani 1 1 d . . . C6 C 0.2519(5) 0.3956(2) 0.4894(7) 0.0600(13) Uani 1 1 d . . . C7 C 0.3618(4) 0.3886(2) 0.5758(7) 0.0615(14) Uani 1 1 d . . . C8 C 0.4410(5) 0.4295(2) 0.6241(9) 0.0803(18) Uani 1 1 d . . . F1 F -0.2428(4) 0.32812(14) 0.9921(5) 0.1081(13) Uani 1 1 d . . . C14 C -0.2278(5) 0.1124(2) 1.0485(8) 0.0806(18) Uani 1 1 d . . . H14A H -0.1619 0.1030 1.1410 0.097 Uiso 1 1 calc R . . H14B H -0.2936 0.1013 1.0938 0.097 Uiso 1 1 calc R . . C15 C -0.2310(4) 0.1706(2) 1.0263(7) 0.0617(14) Uani 1 1 d . . . C16 C -0.3289(5) 0.1956(3) 0.9475(8) 0.0762(17) Uani 1 1 d . . . H16A H -0.3932 0.1764 0.9019 0.091 Uiso 1 1 calc R . . C19 C -0.1396(5) 0.2531(2) 1.0794(8) 0.0745(16) Uani 1 1 d . . . H19A H -0.0758 0.2728 1.1239 0.089 Uiso 1 1 calc R . . C20 C -0.1365(5) 0.1998(2) 1.0908(8) 0.0756(17) Uani 1 1 d . . . H20A H -0.0693 0.1835 1.1430 0.091 Uiso 1 1 calc R . . C18 C -0.2384(5) 0.2756(2) 1.0016(8) 0.0728(17) Uani 1 1 d . . . C17 C -0.3338(5) 0.2486(3) 0.9347(8) 0.0807(18) Uani 1 1 d . . . H17A H -0.4003 0.2653 0.8819 0.097 Uiso 1 1 calc R . . N5 N -0.2247(4) 0.08524(17) 0.8727(6) 0.0665(12) Uani 1 1 d . . . C11 C -0.2188(10) 0.0354(3) 0.5503(11) 0.113(3) Uani 1 1 d . . . H11A H -0.2173 0.0186 0.4390 0.136 Uiso 1 1 calc R . . C10 C -0.1220(9) 0.0550(3) 0.6588(16) 0.123(3) Uani 1 1 d . . . H10A H -0.0536 0.0516 0.6217 0.147 Uiso 1 1 calc R . . C12 C -0.3169(7) 0.0414(3) 0.6109(12) 0.101(2) Uani 1 1 d . . . H12A H -0.3833 0.0282 0.5407 0.121 Uiso 1 1 calc R . . C13 C -0.3187(5) 0.0661(2) 0.7697(11) 0.089(2) Uani 1 1 d . . . H13A H -0.3864 0.0699 0.8089 0.107 Uiso 1 1 calc R . . C9 C -0.1274(6) 0.0793(3) 0.8204(11) 0.092(2) Uani 1 1 d . . . H9A H -0.0619 0.0918 0.8955 0.111 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 0.0478(4) 0.0614(4) 0.0545(5) -0.0061(3) -0.0021(3) 0.0062(3) S2 0.0467(7) 0.0667(8) 0.0687(9) -0.0052(7) -0.0059(6) 0.0073(6) S1 0.0454(7) 0.0710(9) 0.0683(9) -0.0026(7) -0.0042(6) 0.0027(6) S3 0.0523(8) 0.0674(9) 0.0701(9) -0.0063(7) -0.0009(6) 0.0101(6) S4 0.0532(8) 0.0688(9) 0.0713(10) -0.0030(7) -0.0046(7) 0.0026(7) N1 0.085(4) 0.085(4) 0.127(5) 0.001(4) 0.003(4) -0.021(3) N2 0.099(4) 0.073(4) 0.114(5) 0.008(3) -0.003(4) 0.013(3) N3 0.110(5) 0.076(4) 0.112(5) 0.005(3) -0.011(4) 0.021(3) N4 0.113(5) 0.096(4) 0.121(5) 0.008(4) -0.005(4) -0.037(4) C1 0.060(3) 0.072(4) 0.075(4) 0.006(3) 0.003(3) -0.005(3) C2 0.056(3) 0.067(3) 0.051(3) -0.004(3) 0.009(2) 0.002(3) C3 0.058(3) 0.059(3) 0.049(3) 0.003(2) 0.013(2) 0.004(2) C4 0.064(4) 0.069(4) 0.074(4) 0.002(3) 0.007(3) 0.003(3) C5 0.071(4) 0.070(4) 0.084(4) -0.004(3) -0.002(3) 0.006(3) C6 0.068(3) 0.059(3) 0.052(3) 0.003(2) 0.009(3) 0.006(3) C7 0.063(3) 0.066(3) 0.054(3) -0.007(3) 0.007(3) 0.003(3) C8 0.076(4) 0.074(4) 0.084(5) 0.009(3) -0.003(3) -0.001(3) F1 0.144(4) 0.069(2) 0.106(3) -0.009(2) 0.012(3) 0.014(2) C14 0.089(4) 0.079(4) 0.069(4) 0.006(3) 0.005(3) -0.010(3) C15 0.056(3) 0.072(4) 0.053(3) 0.004(3) 0.003(3) 0.002(3) C16 0.050(3) 0.095(5) 0.077(4) -0.015(4) -0.003(3) -0.007(3) C19 0.063(4) 0.076(4) 0.079(4) -0.003(3) 0.002(3) -0.012(3) C20 0.051(3) 0.088(4) 0.080(4) -0.006(4) -0.003(3) -0.001(3) C18 0.080(4) 0.076(4) 0.060(4) -0.006(3) 0.008(3) 0.007(3) C17 0.062(4) 0.096(5) 0.078(4) -0.012(4) -0.001(3) 0.018(4) N5 0.062(3) 0.062(3) 0.068(3) 0.005(2) -0.003(2) -0.007(2) C11 0.184(10) 0.074(5) 0.084(5) -0.007(4) 0.034(6) 0.011(6) C10 0.128(8) 0.090(6) 0.169(9) -0.016(6) 0.074(7) -0.005(5) C12 0.113(6) 0.077(5) 0.094(6) -0.015(4) -0.025(5) 0.008(4) C13 0.069(4) 0.076(4) 0.108(6) -0.009(4) -0.013(4) -0.003(3) C9 0.064(4) 0.092(5) 0.120(6) -0.008(5) 0.017(4) -0.010(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 S4 2.1412(15) . ? Ni1 S2 2.1441(14) . ? Ni1 S1 2.1454(14) . ? Ni1 S3 2.1516(14) . ? S2 C3 1.714(5) . ? S1 C2 1.706(5) . ? S3 C6 1.724(6) . ? S4 C7 1.713(6) . ? N1 C1 1.133(7) . ? N2 C4 1.147(7) . ? N3 C5 1.136(7) . ? N4 C8 1.145(8) . ? C1 C2 1.439(8) . ? C2 C3 1.359(7) . ? C3 C4 1.433(8) . ? C5 C6 1.445(8) . ? C6 C7 1.368(7) . ? C7 C8 1.428(8) . ? F1 C18 1.365(6) . ? C14 N5 1.478(7) . ? C14 C15 1.518(8) . ? C15 C16 1.375(8) . ? C15 C20 1.378(7) . ? C16 C17 1.379(9) . ? C19 C18 1.352(8) . ? C19 C20 1.385(8) . ? C18 C17 1.358(8) . ? N5 C9 1.324(8) . ? N5 C13 1.331(7) . ? C11 C12 1.363(11) . ? C11 C10 1.377(12) . ? C10 C9 1.356(11) . ? C12 C13 1.333(9) . ? 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 S4 Ni1 S2 86.24(6) . . ? S4 Ni1 S1 178.50(6) . . ? S2 Ni1 S1 92.27(6) . . ? S4 Ni1 S3 92.46(6) . . ? S2 Ni1 S3 177.83(7) . . ? S1 Ni1 S3 89.04(6) . . ? C3 S2 Ni1 103.16(18) . . ? C2 S1 Ni1 103.61(19) . . ? C6 S3 Ni1 103.09(18) . . ? C7 S4 Ni1 103.87(19) . . ? N1 C1 C2 178.0(7) . . ? C3 C2 C1 121.7(5) . . ? C3 C2 S1 120.2(4) . . ? C1 C2 S1 118.1(4) . . ? C2 C3 C4 122.6(5) . . ? C2 C3 S2 120.7(4) . . ? C4 C3 S2 116.6(4) . . ? N2 C4 C3 178.1(7) . . ? N3 C5 C6 178.0(7) . . ? C7 C6 C5 121.8(5) . . ? C7 C6 S3 120.4(4) . . ? C5 C6 S3 117.7(4) . . ? C6 C7 C8 124.1(5) . . ? C6 C7 S4 120.1(4) . . ? C8 C7 S4 115.8(4) . . ? N4 C8 C7 174.5(7) . . ? N5 C14 C15 112.7(5) . . ? C16 C15 C20 118.2(6) . . ? C16 C15 C14 121.1(5) . . ? C20 C15 C14 120.6(5) . . ? C15 C16 C17 121.4(5) . . ? C18 C19 C20 117.8(6) . . ? C15 C20 C19 121.3(5) . . ? C19 C18 C17 123.3(6) . . ? C19 C18 F1 118.3(6) . . ? C17 C18 F1 118.4(6) . . ? C18 C17 C16 117.9(6) . . ? C9 N5 C13 120.3(6) . . ? C9 N5 C14 119.5(5) . . ? C13 N5 C14 120.2(6) . . ? C12 C11 C10 118.0(8) . . ? C9 C10 C11 119.3(8) . . ? C13 C12 C11 120.7(8) . . ? N5 C13 C12 120.7(7) . . ? N5 C9 C10 120.9(7) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.879 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.084