# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'En-Qing Gao' _publ_contact_author_email eqgao@chem.ecnu.edu.cn _publ_section_title ; Long-range ordering or not: magnetic properties modulated by second ligands in flexible three-dimensional metal-organic frameworks ; loop_ _publ_author_name 'Hua Tian.' 'En-Qing Gao.' data_1 _database_code_depnum_ccdc_archive 'CCDC 767209' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H12 N4 Ni O8' _chemical_formula_weight 519.05 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' Ni Ni 0.3393 1.1124 '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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.8537(9) _cell_length_b 11.2886(5) _cell_length_c 9.5983(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.3390(10) _cell_angle_gamma 90.00 _cell_volume 2053.42(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9532 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 28.36 _exptl_crystal_description Prism _exptl_crystal_colour Green _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 1.007 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7323 _exptl_absorpt_correction_T_max 0.9148 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12399 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0135 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2013 _reflns_number_gt 1920 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0433P)^2^+4.0915P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2013 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 0.0000 -0.03864(3) 0.2500 0.01729(13) Uani 1 2 d S . . C1 C 0.09838(10) -0.03277(16) 0.0543(2) 0.0205(4) Uani 1 1 d . . . C2 C 0.15876(11) -0.09951(19) 0.0243(2) 0.0253(4) Uani 1 1 d . . . C3 C 0.19493(12) -0.04706(19) -0.0659(3) 0.0301(5) Uani 1 1 d . . . H3A H 0.1836 0.0292 -0.1021 0.036 Uiso 1 1 calc R . . C4 C 0.17748(11) -0.2097(2) 0.0804(2) 0.0285(5) Uani 1 1 d . . . H4A H 0.1541 -0.2429 0.1418 0.034 Uiso 1 1 calc R . . C5 C 0.24669(12) -0.1097(2) -0.0995(3) 0.0319(5) Uani 1 1 d . . . C6 C 0.23212(11) -0.2749(2) 0.0471(2) 0.0277(5) Uani 1 1 d . . . C7 C 0.05131(13) 0.2102(2) 0.2205(3) 0.0338(5) Uani 1 1 d . . . H7A H 0.0873 0.1689 0.1980 0.041 Uiso 1 1 calc R . . C8 C 0.05380(13) 0.3320(2) 0.2215(3) 0.0370(6) Uani 1 1 d . . . H8A H 0.0915 0.3711 0.2031 0.044 Uiso 1 1 calc R . . C9 C 0.0000 0.3962(3) 0.2500 0.0275(6) Uani 1 2 d S . . C10 C 0.0000 0.5274(2) 0.2500 0.0278(6) Uani 1 2 d S . . C11 C -0.05933(13) 0.5914(2) 0.1749(3) 0.0374(6) Uani 1 1 d . . . H11A H -0.1004 0.5523 0.1234 0.045 Uiso 1 1 calc R . . C12 C -0.05700(13) 0.7135(2) 0.1771(3) 0.0340(5) Uani 1 1 d . . . H12A H -0.0971 0.7548 0.1252 0.041 Uiso 1 1 calc R . . N1 N 0.27980(13) -0.0538(2) -0.2008(3) 0.0499(7) Uani 1 1 d . . . N2 N 0.0000 0.1481(2) 0.2500 0.0222(5) Uani 1 2 d S . . N3 N 0.0000 0.7754(2) 0.2500 0.0226(5) Uani 1 2 d S . . O1 O 0.08614(8) -0.05735(12) 0.17182(16) 0.0236(3) Uani 1 1 d . . . O2 O 0.06715(8) 0.04324(11) -0.03678(16) 0.0233(3) Uani 1 1 d . . . O3 O 0.28141(16) -0.1095(3) -0.3096(3) 0.0828(9) Uani 1 1 d . . . O4 O 0.29915(14) 0.0474(2) -0.1765(4) 0.0794(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0221(2) 0.00964(19) 0.0235(2) 0.000 0.01185(14) 0.000 C1 0.0200(9) 0.0178(9) 0.0254(10) -0.0025(7) 0.0094(8) 0.0001(7) C2 0.0242(10) 0.0275(11) 0.0267(10) 0.0001(8) 0.0114(8) 0.0068(8) C3 0.0298(11) 0.0273(11) 0.0376(13) 0.0067(9) 0.0167(10) 0.0075(8) C4 0.0294(11) 0.0307(11) 0.0305(11) 0.0054(9) 0.0168(9) 0.0080(9) C5 0.0329(11) 0.0318(12) 0.0384(12) 0.0109(10) 0.0218(10) 0.0085(9) C6 0.0291(11) 0.0291(11) 0.0288(11) 0.0062(9) 0.0142(9) 0.0074(9) C7 0.0386(13) 0.0180(10) 0.0541(15) -0.0022(9) 0.0278(11) 0.0011(9) C8 0.0388(13) 0.0183(11) 0.0641(17) -0.0007(10) 0.0311(12) -0.0040(9) C9 0.0345(16) 0.0133(14) 0.0359(17) 0.000 0.0123(13) 0.000 C10 0.0348(16) 0.0135(14) 0.0388(18) 0.000 0.0167(14) 0.000 C11 0.0372(13) 0.0204(11) 0.0519(15) -0.0031(10) 0.0090(11) -0.0037(9) C12 0.0339(12) 0.0212(11) 0.0441(14) 0.0007(9) 0.0072(10) 0.0024(9) N1 0.0478(14) 0.0499(15) 0.0668(17) 0.0313(12) 0.0395(13) 0.0220(11) N2 0.0274(12) 0.0124(11) 0.0296(13) 0.000 0.0128(10) 0.000 N3 0.0293(13) 0.0130(11) 0.0282(13) 0.000 0.0125(10) 0.000 O1 0.0259(7) 0.0225(7) 0.0266(8) 0.0031(5) 0.0145(6) 0.0057(6) O2 0.0272(7) 0.0183(7) 0.0258(8) 0.0026(5) 0.0098(6) 0.0047(5) O3 0.118(2) 0.0877(19) 0.0696(16) 0.0367(14) 0.0695(16) 0.0533(17) O4 0.0666(16) 0.0700(18) 0.114(2) 0.0287(15) 0.0456(16) -0.0120(12) _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 O1 2.0730(14) . ? Ni1 O1 2.0730(14) 2 ? Ni1 O2 2.0837(15) 6_556 ? Ni1 O2 2.0837(15) 5 ? Ni1 N3 2.100(2) 1_545 ? Ni1 N2 2.108(2) . ? C1 O2 1.250(2) . ? C1 O1 1.254(3) . ? C1 C2 1.514(3) . ? C2 C4 1.362(3) . ? C2 C3 1.409(3) . ? C3 C5 1.363(3) . ? C3 H3A 0.9300 . ? C4 C6 1.424(3) . ? C4 H4A 0.9300 . ? C5 C6 1.414(3) 7_545 ? C5 N1 1.469(3) . ? C6 C5 1.414(3) 7_545 ? C6 C6 1.421(4) 7_545 ? C7 N2 1.335(3) . ? C7 C8 1.376(3) . ? C7 H7A 0.9300 . ? C8 C9 1.384(3) . ? C8 H8A 0.9300 . ? C9 C8 1.384(3) 2 ? C9 C10 1.482(4) . ? C10 C11 1.387(3) 2 ? C10 C11 1.387(3) . ? C11 C12 1.378(3) . ? C11 H11A 0.9300 . ? C12 N3 1.337(3) . ? C12 H12A 0.9300 . ? N1 O4 1.206(4) . ? N1 O3 1.228(4) . ? N2 C7 1.335(3) 2 ? N3 C12 1.337(3) 2 ? N3 Ni1 2.100(2) 1_565 ? O2 Ni1 2.0837(15) 5 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ni1 O1 168.31(8) . 2 ? O1 Ni1 O2 89.86(6) . 6_556 ? O1 Ni1 O2 89.85(6) 2 6_556 ? O1 Ni1 O2 89.85(6) . 5 ? O1 Ni1 O2 89.86(6) 2 5 ? O2 Ni1 O2 177.15(7) 6_556 5 ? O1 Ni1 N3 84.15(4) . 1_545 ? O1 Ni1 N3 84.15(4) 2 1_545 ? O2 Ni1 N3 88.57(4) 6_556 1_545 ? O2 Ni1 N3 88.57(4) 5 1_545 ? O1 Ni1 N2 95.85(4) . . ? O1 Ni1 N2 95.85(4) 2 . ? O2 Ni1 N2 91.43(4) 6_556 . ? O2 Ni1 N2 91.43(4) 5 . ? N3 Ni1 N2 180.0 1_545 . ? O2 C1 O1 126.32(18) . . ? O2 C1 C2 117.68(18) . . ? O1 C1 C2 115.96(17) . . ? C4 C2 C3 119.85(19) . . ? C4 C2 C1 121.12(19) . . ? C3 C2 C1 119.01(19) . . ? C5 C3 C2 119.0(2) . . ? C5 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C2 C4 C6 121.3(2) . . ? C2 C4 H4A 119.4 . . ? C6 C4 H4A 119.4 . . ? C3 C5 C6 124.0(2) . 7_545 ? C3 C5 N1 116.8(2) . . ? C6 C5 N1 119.13(19) 7_545 . ? C5 C6 C6 116.0(2) 7_545 7_545 ? C5 C6 C4 124.2(2) 7_545 . ? C6 C6 C4 119.8(2) 7_545 . ? N2 C7 C8 123.5(2) . . ? N2 C7 H7A 118.3 . . ? C8 C7 H7A 118.3 . . ? C7 C8 C9 119.8(2) . . ? C7 C8 H8A 120.1 . . ? C9 C8 H8A 120.1 . . ? C8 C9 C8 116.9(3) . 2 ? C8 C9 C10 121.57(14) . . ? C8 C9 C10 121.57(14) 2 . ? C11 C10 C11 117.2(3) 2 . ? C11 C10 C9 121.40(14) 2 . ? C11 C10 C9 121.40(14) . . ? C12 C11 C10 119.6(2) . . ? C12 C11 H11A 120.2 . . ? C10 C11 H11A 120.2 . . ? N3 C12 C11 123.4(2) . . ? N3 C12 H12A 118.3 . . ? C11 C12 H12A 118.3 . . ? O4 N1 O3 124.2(3) . . ? O4 N1 C5 117.3(3) . . ? O3 N1 C5 118.3(3) . . ? C7 N2 C7 116.7(3) 2 . ? C7 N2 Ni1 121.67(13) 2 . ? C7 N2 Ni1 121.67(13) . . ? C12 N3 C12 117.0(3) . 2 ? C12 N3 Ni1 121.52(13) . 1_565 ? C12 N3 Ni1 121.52(13) 2 1_565 ? C1 O1 Ni1 134.84(13) . . ? C1 O2 Ni1 135.13(13) . 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 O2 C1 C2 C4 -154.4(2) . . . . ? O1 C1 C2 C4 27.7(3) . . . . ? O2 C1 C2 C3 24.3(3) . . . . ? O1 C1 C2 C3 -153.6(2) . . . . ? C4 C2 C3 C5 2.2(4) . . . . ? C1 C2 C3 C5 -176.4(2) . . . . ? C3 C2 C4 C6 -1.5(3) . . . . ? C1 C2 C4 C6 177.1(2) . . . . ? C2 C3 C5 C6 -1.1(4) . . . 7_545 ? C2 C3 C5 N1 176.5(2) . . . . ? C2 C4 C6 C5 -178.8(2) . . . 7_545 ? C2 C4 C6 C6 -0.3(4) . . . 7_545 ? N2 C7 C8 C9 -2.0(4) . . . . ? C7 C8 C9 C8 0.93(18) . . . 2 ? C7 C8 C9 C10 -179.07(18) . . . . ? C8 C9 C10 C11 -48.34(19) . . . 2 ? C8 C9 C10 C11 131.66(19) 2 . . 2 ? C8 C9 C10 C11 131.66(19) . . . . ? C8 C9 C10 C11 -48.34(19) 2 . . . ? C11 C10 C11 C12 0.33(18) 2 . . . ? C9 C10 C11 C12 -179.67(18) . . . . ? C10 C11 C12 N3 -0.7(4) . . . . ? C3 C5 N1 O4 48.5(4) . . . . ? C6 C5 N1 O4 -133.7(3) 7_545 . . . ? C3 C5 N1 O3 -126.3(3) . . . . ? C6 C5 N1 O3 51.4(4) 7_545 . . . ? C8 C7 N2 C7 1.0(2) . . . 2 ? C8 C7 N2 Ni1 -179.0(2) . . . . ? O1 Ni1 N2 C7 173.46(14) . . . 2 ? O1 Ni1 N2 C7 -6.54(14) 2 . . 2 ? O2 Ni1 N2 C7 -96.53(14) 6_556 . . 2 ? O2 Ni1 N2 C7 83.47(14) 5 . . 2 ? N3 Ni1 N2 C7 103(100) 1_545 . . 2 ? O1 Ni1 N2 C7 -6.54(14) . . . . ? O1 Ni1 N2 C7 173.46(14) 2 . . . ? O2 Ni1 N2 C7 83.47(14) 6_556 . . . ? O2 Ni1 N2 C7 -96.53(14) 5 . . . ? N3 Ni1 N2 C7 -77(84) 1_545 . . . ? C11 C12 N3 C12 0.35(19) . . . 2 ? C11 C12 N3 Ni1 -179.65(19) . . . 1_565 ? O2 C1 O1 Ni1 23.1(3) . . . . ? C2 C1 O1 Ni1 -159.22(14) . . . . ? O1 Ni1 O1 C1 114.55(18) 2 . . . ? O2 Ni1 O1 C1 -156.87(19) 6_556 . . . ? O2 Ni1 O1 C1 25.97(19) 5 . . . ? N3 Ni1 O1 C1 114.55(18) 1_545 . . . ? N2 Ni1 O1 C1 -65.45(18) . . . . ? O1 C1 O2 Ni1 -112.7(2) . . . 5 ? C2 C1 O2 Ni1 69.6(2) . . . 5 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.412 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.069 data_2 _database_code_depnum_ccdc_archive 'CCDC 767210' #TrackingRef '2.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H14 N4 Ni O8' _chemical_formula_weight 545.08 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' Ni Ni 0.3393 1.1124 '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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.7216(8) _cell_length_b 13.5231(8) _cell_length_c 9.8718(6) _cell_angle_alpha 90.00 _cell_angle_beta 115.707(2) _cell_angle_gamma 90.00 _cell_volume 2131.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6124 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 28.15 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.974 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7587 _exptl_absorpt_correction_T_max 0.9088 _exptl_absorpt_process_details SADABS _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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.5 _diffrn_reflns_number 14126 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2619 _reflns_number_gt 2243 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _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 bis(4-pyridyl)ethene (bpe) ligand in the structure has been treated as being disordered over two C2-symmetry-related positions with equal occupancies (0.5), and the PART -n instruction in SHELXL was used to avoid incorrect connectivity. The 1,5-dinitronaphthalene moiety located at an inversion center is allowed to be disordered over two independent positions with the occupancies refined to be 0.87 and 0.13, and the PART n instruction was used. The disordered nitro groups have been modeled used DFIX and DANG restraints with default estimated standard deviations: N-O to 1.20 \%A, O-O to 2.10 \%A, C-N to 1.48 \%A. The disordered C(carboxylate)-C(benzene) bonds were also restrained using DFIX, and the planarity restraint FLAT was applied to the benzene ring with occupancy 0.13. The structure can also be solved in the lower-symmetry Cc space group, but the disorder remained, with no improvements in refinement data. ; _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^)+(0.0519P)^2^+1.7109P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2619 _refine_ls_number_parameters 242 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.056 _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 0.0000 -0.02693(2) 0.2500 0.02251(12) Uani 1 2 d S . . O1 O 0.10296(8) -0.04921(10) 0.19393(15) 0.0293(3) Uani 1 1 d . A . O2 O 0.07821(8) 0.02784(8) -0.02126(14) 0.0268(3) Uani 1 1 d . . . C1 C 0.11252(11) -0.03778(12) 0.0768(2) 0.0241(4) Uani 1 1 d D . . C2 C 0.17239(16) -0.10517(18) 0.0474(3) 0.0266(5) Uani 0.872(3) 1 d PD A 1 C3 C 0.21248(14) -0.06778(17) -0.0386(3) 0.0300(5) Uani 0.872(3) 1 d P A 1 H3A H 0.2086 -0.0011 -0.0637 0.036 Uiso 0.872(3) 1 calc PR A 1 C4 C 0.25671(14) -0.13098(17) -0.0839(3) 0.0321(5) Uani 0.872(3) 1 d PD . 1 C5 C 0.23147(15) -0.26712(18) 0.0467(3) 0.0293(5) Uani 0.872(3) 1 d P . 1 C6 C 0.18330(14) -0.20185(16) 0.0910(3) 0.0301(5) Uani 0.872(3) 1 d P A 1 H6A H 0.1588 -0.2256 0.1510 0.036 Uiso 0.872(3) 1 calc PR A 1 N1 N 0.28634(18) -0.0882(2) -0.1885(4) 0.0501(7) Uani 0.872(3) 1 d PD A 1 O3 O 0.3216(2) -0.0099(2) -0.1568(4) 0.0783(9) Uani 0.872(3) 1 d PD A 1 O4 O 0.2667(2) -0.1314(3) -0.3080(3) 0.0748(8) Uani 0.872(3) 1 d PD A 1 C2' C 0.1652(12) -0.1306(13) 0.071(2) 0.0266(5) Uani 0.128(3) 1 d PD A 2 C3' C 0.1692(9) -0.2165(11) 0.1495(19) 0.0300(5) Uani 0.128(3) 1 d PD A 2 H3B H 0.1432 -0.2201 0.2134 0.036 Uiso 0.128(3) 1 calc PR A 2 C4' C 0.2118(10) -0.2963(11) 0.1324(19) 0.040(4) Uani 0.128(3) 1 d PD . 2 C5' C 0.2518(12) -0.2024(14) -0.041(2) 0.0293(5) Uani 0.128(3) 1 d PD . 2 C6' C 0.2006(10) -0.1191(14) -0.0229(18) 0.0301(5) Uani 0.128(3) 1 d PD A 2 H6B H 0.1938 -0.0606 -0.0764 0.036 Uiso 0.128(3) 1 calc PR A 2 N1' N 0.2006(16) -0.3908(15) 0.201(3) 0.0501(7) Uani 0.128(3) 1 d PD A 2 O3' O 0.1534(16) -0.4579(17) 0.128(3) 0.0783(9) Uani 0.128(3) 1 d PD A 2 O4' O 0.223(2) -0.380(2) 0.338(3) 0.0748(8) Uani 0.128(3) 1 d PD A 2 C7 C 0.0372(10) 0.1838(8) 0.1866(16) 0.0339(9) Uani 0.50 1 d PD B -1 H7A H 0.0690 0.1539 0.1439 0.041 Uiso 0.50 1 calc PR B -1 C8 C 0.0300(4) 0.2862(6) 0.1822(12) 0.0370(17) Uani 0.50 1 d PD B -1 H8A H 0.0587 0.3234 0.1404 0.044 Uiso 0.50 1 calc PR B -1 C9 C -0.0485(10) 0.1746(8) 0.3048(16) 0.0339(9) Uani 0.50 1 d PD B -1 H9A H -0.0752 0.1365 0.3494 0.041 Uiso 0.50 1 calc PR B -1 C10 C -0.0605(4) 0.2751(6) 0.2986(10) 0.0319(15) Uani 0.50 1 d PD B -1 H10A H -0.0963 0.3031 0.3344 0.038 Uiso 0.50 1 calc PR B -1 C11 C -0.0193(2) 0.3337(2) 0.2391(9) 0.0316(12) Uani 0.50 1 d P B -1 C12 C -0.0298(3) 0.4422(3) 0.2330(6) 0.0401(10) Uani 0.50 1 d P B -1 H12A H -0.0835 0.4670 0.2044 0.048 Uiso 0.50 1 calc PR B -1 C13 C 0.0306(3) 0.5054(3) 0.2645(6) 0.0436(11) Uani 0.50 1 d P B -1 H13A H 0.0838 0.4804 0.2893 0.052 Uiso 0.50 1 calc PR B -1 C14 C 0.0213(3) 0.6142(3) 0.2642(9) 0.0357(14) Uani 0.50 1 d P B -1 C15 C 0.0863(4) 0.6733(6) 0.3612(10) 0.0391(16) Uani 0.50 1 d PD B -1 H15A H 0.1363 0.6459 0.4306 0.047 Uiso 0.50 1 calc PR B -1 C16 C 0.0738(6) 0.7771(7) 0.3506(9) 0.0403(8) Uani 0.50 1 d PD B -1 H16A H 0.1169 0.8180 0.4137 0.048 Uiso 0.50 1 calc PR B -1 C17 C -0.0523(5) 0.6604(5) 0.1659(10) 0.0375(15) Uani 0.50 1 d PD B -1 H17A H -0.0970 0.6221 0.1010 0.045 Uiso 0.50 1 calc PR B -1 C18 C -0.0602(7) 0.7609(7) 0.1626(9) 0.0403(8) Uani 0.50 1 d PD B -1 H18A H -0.1106 0.7889 0.0955 0.048 Uiso 0.50 1 calc PR B -1 N2 N 0.0000 0.12729(14) 0.2500 0.0250(4) Uani 1 2 d SD . . N3 N 0.0000 0.81958(15) 0.2500 0.0342(5) Uani 1 2 d SD . . 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 0.03103(19) 0.01206(16) 0.0298(2) 0.000 0.01825(15) 0.000 O1 0.0327(7) 0.0288(6) 0.0317(7) 0.0034(5) 0.0190(6) 0.0065(5) O2 0.0320(7) 0.0216(6) 0.0301(7) -0.0003(5) 0.0166(6) 0.0018(5) C1 0.0239(8) 0.0208(8) 0.0312(9) -0.0038(6) 0.0152(7) 0.0010(6) C2 0.0274(10) 0.0264(13) 0.0301(12) 0.0015(9) 0.0163(9) 0.0063(9) C3 0.0318(11) 0.0251(11) 0.0386(12) 0.0051(9) 0.0206(10) 0.0075(9) C4 0.0380(12) 0.0307(11) 0.0385(12) 0.0083(9) 0.0268(10) 0.0089(9) C5 0.0325(12) 0.0255(13) 0.0342(11) 0.0061(10) 0.0185(10) 0.0101(9) C6 0.0351(11) 0.0297(11) 0.0353(12) 0.0069(9) 0.0243(10) 0.0089(9) N1 0.0556(16) 0.0512(15) 0.0688(16) 0.0275(13) 0.0505(13) 0.0275(12) O3 0.084(2) 0.0636(19) 0.117(2) 0.0175(17) 0.071(2) 0.0004(14) O4 0.112(2) 0.0748(17) 0.068(2) 0.0255(14) 0.0670(16) 0.0366(15) C2' 0.0274(10) 0.0264(13) 0.0301(12) 0.0015(9) 0.0163(9) 0.0063(9) C3' 0.0318(11) 0.0251(11) 0.0386(12) 0.0051(9) 0.0206(10) 0.0075(9) C4' 0.046(9) 0.039(8) 0.048(10) 0.026(7) 0.033(8) 0.024(7) C5' 0.0325(12) 0.0255(13) 0.0342(11) 0.0061(10) 0.0185(10) 0.0101(9) C6' 0.0351(11) 0.0297(11) 0.0353(12) 0.0069(9) 0.0243(10) 0.0089(9) N1' 0.0556(16) 0.0512(15) 0.0688(16) 0.0275(13) 0.0505(13) 0.0275(12) O3' 0.084(2) 0.0636(19) 0.117(2) 0.0175(17) 0.071(2) 0.0004(14) O4' 0.112(2) 0.0748(17) 0.068(2) 0.0255(14) 0.0670(16) 0.0366(15) C7 0.049(3) 0.0193(16) 0.0445(16) 0.000(2) 0.030(2) 0.002(2) C8 0.044(4) 0.017(2) 0.064(4) 0.006(2) 0.036(4) 0.001(3) C9 0.049(3) 0.0193(16) 0.0445(16) 0.000(2) 0.030(2) 0.002(2) C10 0.043(4) 0.021(3) 0.044(3) -0.001(2) 0.031(4) -0.001(3) C11 0.041(4) 0.0150(14) 0.048(3) -0.0005(19) 0.028(4) -0.0005(13) C12 0.051(3) 0.0179(19) 0.065(3) 0.0038(18) 0.038(3) 0.0046(15) C13 0.054(3) 0.0153(19) 0.076(3) 0.0024(19) 0.042(3) 0.0055(16) C14 0.045(4) 0.0155(16) 0.054(4) 0.003(2) 0.028(5) 0.0009(17) C15 0.042(4) 0.023(3) 0.055(4) 0.001(2) 0.023(4) -0.001(3) C16 0.063(3) 0.013(2) 0.0535(17) 0.0022(17) 0.0337(19) 0.0030(17) C17 0.045(4) 0.015(3) 0.053(4) -0.004(3) 0.022(4) -0.002(3) C18 0.063(3) 0.013(2) 0.0535(17) 0.0022(17) 0.0337(19) 0.0030(17) N2 0.0333(11) 0.0140(9) 0.0304(11) 0.000 0.0164(9) 0.000 N3 0.0552(15) 0.0148(9) 0.0452(14) 0.000 0.0335(12) 0.000 _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 O2 2.0748(13) 6_556 ? Ni1 O2 2.0748(13) 5 ? Ni1 N3 2.076(2) 1_545 ? Ni1 N2 2.085(2) . ? Ni1 O1 2.1453(12) . ? Ni1 O1 2.1453(12) 2 ? O1 C1 1.249(2) . ? O2 C1 1.258(2) . ? O2 Ni1 2.0748(13) 5 ? C1 C2 1.519(3) . ? C1 C2' 1.580(16) . ? C2 C6 1.364(3) . ? C2 C3 1.416(3) . ? C3 C4 1.360(3) . ? C3 H3A 0.9300 . ? C4 C5 1.418(3) 7_545 ? C4 N1 1.465(3) . ? C5 C4 1.418(3) 7_545 ? C5 C6 1.422(3) . ? C5 C5 1.423(5) 7_545 ? C6 H6A 0.9300 . ? N1 O3 1.200(4) . ? N1 O4 1.224(4) . ? C2' C6' 1.34(2) . ? C2' C3' 1.38(2) . ? C3' C4' 1.37(2) . ? C3' H3B 0.9300 . ? C4' C5' 1.32(2) 7_545 ? C4' N1' 1.497(17) . ? C5' C4' 1.32(2) 7_545 ? C5' C6' 1.50(2) . ? C5' C5' 1.54(4) 7_545 ? C6' H6B 0.9300 . ? N1' O3' 1.232(18) . ? N1' O4' 1.245(18) . ? C7 N2 1.330(12) . ? C7 C8 1.390(11) . ? C7 H7A 0.9300 . ? C8 C11 1.385(8) . ? C8 H8A 0.9300 . ? C9 N2 1.357(12) . ? C9 C10 1.373(12) . ? C9 H9A 0.9300 . ? C10 C11 1.370(7) . ? C10 H10A 0.9300 . ? C11 C12 1.478(5) . ? C12 C13 1.297(6) . ? C12 H12A 0.9300 . ? C13 C14 1.480(5) . ? C13 H13A 0.9300 . ? C14 C15 1.389(8) . ? C14 C17 1.391(9) . ? C15 C16 1.417(11) . ? C15 H15A 0.9300 . ? C16 N3 1.379(12) . ? C16 H16A 0.9300 . ? C17 C18 1.366(10) . ? C17 H17A 0.9300 . ? C18 N3 1.309(13) . ? C18 H18A 0.9300 . ? N2 C7 1.330(12) 2 ? N2 C9 1.357(12) 2 ? N3 C18 1.309(13) 2 ? N3 C16 1.379(12) 2 ? N3 Ni1 2.076(2) 1_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Ni1 O2 179.32(6) 6_556 5 ? O2 Ni1 N3 89.66(3) 6_556 1_545 ? O2 Ni1 N3 89.66(3) 5 1_545 ? O2 Ni1 N2 90.34(3) 6_556 . ? O2 Ni1 N2 90.34(3) 5 . ? N3 Ni1 N2 180.0 1_545 . ? O2 Ni1 O1 92.21(5) 6_556 . ? O2 Ni1 O1 87.70(5) 5 . ? N3 Ni1 O1 81.93(4) 1_545 . ? N2 Ni1 O1 98.07(4) . . ? O2 Ni1 O1 87.70(5) 6_556 2 ? O2 Ni1 O1 92.21(5) 5 2 ? N3 Ni1 O1 81.93(4) 1_545 2 ? N2 Ni1 O1 98.07(4) . 2 ? O1 Ni1 O1 163.85(7) . 2 ? C1 O1 Ni1 133.92(12) . . ? C1 O2 Ni1 134.81(11) . 5 ? O1 C1 O2 125.80(15) . . ? O1 C1 C2 119.28(16) . . ? O2 C1 C2 114.89(16) . . ? O1 C1 C2' 104.7(7) . . ? O2 C1 C2' 129.0(7) . . ? C6 C2 C3 119.5(2) . . ? C6 C2 C1 122.00(19) . . ? C3 C2 C1 118.29(19) . . ? C4 C3 C2 118.9(2) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 124.6(2) . 7_545 ? C3 C4 N1 114.7(2) . . ? C5 C4 N1 120.5(2) 7_545 . ? C4 C5 C6 124.4(2) 7_545 . ? C4 C5 C5 115.2(3) 7_545 7_545 ? C6 C5 C5 120.3(3) . 7_545 ? C2 C6 C5 121.3(2) . . ? C2 C6 H6A 119.3 . . ? C5 C6 H6A 119.3 . . ? O3 N1 O4 124.8(3) . . ? O3 N1 C4 118.0(3) . . ? O4 N1 C4 116.9(3) . . ? C6' C2' C3' 124.2(16) . . ? C6' C2' C1 113.3(14) . . ? C3' C2' C1 122.4(14) . . ? C4' C3' C2' 119.4(16) . . ? C4' C3' H3B 120.3 . . ? C2' C3' H3B 120.3 . . ? C5' C4' C3' 123.7(15) 7_545 . ? C5' C4' N1' 119.8(16) 7_545 . ? C3' C4' N1' 115.4(15) . . ? C4' C5' C6' 126.2(17) 7_545 . ? C4' C5' C5' 120(2) 7_545 7_545 ? C6' C5' C5' 113.6(19) . 7_545 ? C2' C6' C5' 119.0(16) . . ? C2' C6' H6B 120.5 . . ? C5' C6' H6B 120.5 . . ? O3' N1' O4' 122(2) . . ? O3' N1' C4' 124(2) . . ? O4' N1' C4' 111(2) . . ? N2 C7 C8 122.0(7) . . ? N2 C7 H7A 119.0 . . ? C8 C7 H7A 119.0 . . ? C11 C8 C7 121.0(7) . . ? C11 C8 H8A 119.5 . . ? C7 C8 H8A 119.5 . . ? N2 C9 C10 124.2(7) . . ? N2 C9 H9A 117.9 . . ? C10 C9 H9A 117.9 . . ? C11 C10 C9 119.4(7) . . ? C11 C10 H10A 120.3 . . ? C9 C10 H10A 120.3 . . ? C10 C11 C8 116.9(3) . . ? C10 C11 C12 120.8(5) . . ? C8 C11 C12 122.3(5) . . ? C13 C12 C11 124.6(4) . . ? C13 C12 H12A 117.7 . . ? C11 C12 H12A 117.7 . . ? C12 C13 C14 125.0(4) . . ? C12 C13 H13A 117.5 . . ? C14 C13 H13A 117.5 . . ? C15 C14 C17 118.0(4) . . ? C15 C14 C13 120.8(5) . . ? C17 C14 C13 121.2(6) . . ? C14 C15 C16 117.6(6) . . ? C14 C15 H15A 121.2 . . ? C16 C15 H15A 121.2 . . ? N3 C16 C15 122.4(6) . . ? N3 C16 H16A 118.8 . . ? C15 C16 H16A 118.8 . . ? C18 C17 C14 121.3(7) . . ? C18 C17 H17A 119.4 . . ? C14 C17 H17A 119.4 . . ? N3 C18 C17 122.8(7) . . ? N3 C18 H18A 118.6 . . ? C17 C18 H18A 118.6 . . ? C7 N2 C7 109.9(7) . 2 ? C7 N2 C9 116.5(3) 2 2 ? C7 N2 C9 116.5(3) . . ? C9 N2 C9 123.8(7) 2 . ? C7 N2 Ni1 125.1(4) . . ? C7 N2 Ni1 125.1(4) 2 . ? C9 N2 Ni1 118.1(4) 2 . ? C9 N2 Ni1 118.1(4) . . ? C18 N3 C18 105.4(5) . 2 ? C18 N3 C16 118.0(3) . . ? C18 N3 C16 118.0(3) 2 2 ? C16 N3 C16 130.7(6) . 2 ? C18 N3 Ni1 127.3(3) . 1_565 ? C18 N3 Ni1 127.3(3) 2 1_565 ? C16 N3 Ni1 114.6(3) . 1_565 ? C16 N3 Ni1 114.6(3) 2 1_565 ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.645 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.069