# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Tony Keene' 'Michel Bonin' 'Silvio Decurtins' 'Jurg Hauser' 'Mike Hursthouse' 'Antonia Neels' 'Daniel Price' 'Olha Sereda' 'Iwan Zimmermann' _publ_contact_author_name 'Tony Keene' _publ_contact_author_email TDK199@GMAIL.COM _publ_section_title ; Heterocyclic amine directed synthesis of metal(II)-oxalates: investigating the magnetic properties of two complete series of chains with S = 5/2 to S = 1/2 ; # Attachment 'dalton_cif.cif' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 760875' #TrackingRef 'dalton_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-[(\m~2~oxalato)-bis(benzimidazole)-manganese(II)] ; _chemical_name_common ; Manganese(II) bis-benzimidazole oxalate ; _chemical_melting_point N/A _chemical_formula_moiety 'C48 H36 Mn3 N12 O12' _chemical_formula_sum 'C48 H36 Mn3 N12 O12' _chemical_formula_weight 1137.71 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2 /c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.430(4) _cell_length_b 12.185(2) _cell_length_c 18.746(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.62(3) _cell_angle_gamma 90.00 _cell_volume 4871.3(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8541 _cell_measurement_theta_min 1.91 _cell_measurement_theta_max 29.37 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.551 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2316 _exptl_absorpt_coefficient_mu 0.842 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7894 _exptl_absorpt_correction_T_max 0.8214 _exptl_absorpt_process_details 'MULscanABS, (PLATON, Speck, 2003)' _exptl_special_details ; PLEASE NOTE cell_measurement_fields are not relavent to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 150(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 IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 31782 _diffrn_reflns_av_R_equivalents 0.0908 _diffrn_reflns_av_sigmaI/netI 0.1040 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 29.34 _reflns_number_total 6589 _reflns_number_gt 2553 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2 (Brandenberg, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All hydrogen atoms were fixed in calculated positions and refined in riding mode. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0797P)^2^] 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 6589 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1422 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1500 _refine_ls_wR_factor_gt 0.1290 _refine_ls_goodness_of_fit_ref 0.778 _refine_ls_restrained_S_all 0.778 _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 Mn1 Mn 0.5000 0.86439(7) 0.2500 0.0240(2) Uani 1 2 d S . . Mn2 Mn 0.66587(3) 0.63351(4) 0.08259(3) 0.02023(14) Uani 1 1 d . . . O5 O 0.76507(12) 0.6462(2) 0.06280(13) 0.0244(6) Uani 1 1 d . . . O3 O 0.56567(12) 0.6504(2) 0.09741(14) 0.0245(6) Uani 1 1 d . . . O2 O 0.59754(12) 0.8495(2) 0.23144(14) 0.0275(7) Uani 1 1 d . . . C1 C 0.60875(17) 0.7836(3) 0.1825(2) 0.0236(9) Uani 1 1 d . . . C3 C 0.77760(17) 0.7143(3) 0.01668(19) 0.0210(9) Uani 1 1 d . . . C2 C 0.55383(17) 0.7161(3) 0.1458(2) 0.0227(9) Uani 1 1 d . . . O1 O 0.66187(12) 0.7680(2) 0.16196(14) 0.0304(7) Uani 1 1 d . . . O4 O 0.50093(11) 0.7321(2) 0.16710(14) 0.0273(7) Uani 1 1 d . . . N11 N 0.64282(14) 0.5060(3) 0.00053(16) 0.0268(8) Uani 1 1 d . . . N21 N 0.69788(15) 0.5265(3) 0.17331(17) 0.0295(8) Uani 1 1 d . . . N31 N 0.47470(16) 0.9852(3) 0.16345(18) 0.0319(8) Uani 1 1 d . . . C11 C 0.6829(2) 0.4362(4) -0.0324(2) 0.0366(11) Uani 1 1 d . . . C31 C 0.51037(18) 1.0774(4) 0.1481(2) 0.0289(9) Uani 1 1 d . . . O6 O 0.66986(11) 0.7706(2) 0.00503(14) 0.0269(7) Uani 1 1 d . . . C21 C 0.6655(2) 0.4725(4) 0.2235(2) 0.0341(10) Uani 1 1 d . . . C33 C 0.5040(3) 1.2316(5) 0.0638(3) 0.0568(14) Uani 1 1 d . . . H33 H 0.4836 1.2694 0.0253 0.068 Uiso 1 1 calc R . . C22 C 0.7087(2) 0.4144(4) 0.2688(2) 0.0396(11) Uani 1 1 d . . . C13 C 0.6753(3) 0.2982(5) -0.1276(3) 0.0666(18) Uani 1 1 d . . . H13 H 0.6517 0.2587 -0.1631 0.080 Uiso 1 1 calc R . . C12 C 0.6477(2) 0.3717(4) -0.0829(2) 0.0372(11) Uani 1 1 d . . . C34 C 0.5611(2) 1.2653(4) 0.0977(3) 0.0528(13) Uani 1 1 d . . . H34 H 0.5803 1.3268 0.0801 0.063 Uiso 1 1 calc R . . C36 C 0.5666(2) 1.1158(4) 0.1817(2) 0.0396(11) Uani 1 1 d . . . H36 H 0.5874 1.0781 0.2200 0.048 Uiso 1 1 calc R . . C23 C 0.6919(2) 0.3513(4) 0.3257(2) 0.0540(14) Uani 1 1 d . . . H23 H 0.7215 0.3141 0.3562 0.065 Uiso 1 1 calc R . . C26 C 0.6021(2) 0.4690(4) 0.2333(2) 0.0385(10) Uani 1 1 d . . . H26 H 0.5724 0.5073 0.2035 0.046 Uiso 1 1 calc R . . N22 N 0.76578(18) 0.4368(3) 0.24723(19) 0.0435(10) Uani 1 1 d . . . H22 H 0.8012 0.4122 0.2661 0.052 Uiso 1 1 calc R . . N12 N 0.58748(16) 0.4040(3) -0.08040(17) 0.0344(9) Uani 1 1 d . . . H12 H 0.5553 0.3782 -0.1060 0.041 Uiso 1 1 calc R . . C25 C 0.5852(2) 0.4057(4) 0.2897(2) 0.0482(12) Uani 1 1 d . . . H25 H 0.5432 0.4024 0.2981 0.058 Uiso 1 1 calc R . . C24 C 0.6293(2) 0.3468(4) 0.3343(3) 0.0527(14) Uani 1 1 d . . . H24 H 0.6158 0.3035 0.3706 0.063 Uiso 1 1 calc R . . C35 C 0.5908(2) 1.2118(4) 0.1565(3) 0.0483(12) Uani 1 1 d . . . H35 H 0.6277 1.2407 0.1794 0.058 Uiso 1 1 calc R . . C14 C 0.7386(3) 0.2876(6) -0.1162(4) 0.103(3) Uani 1 1 d . . . H14 H 0.7586 0.2375 -0.1436 0.124 Uiso 1 1 calc R . . C16 C 0.7475(2) 0.4244(5) -0.0218(3) 0.0679(19) Uani 1 1 d . . . H16 H 0.7716 0.4651 0.0126 0.081 Uiso 1 1 calc R . . C15 C 0.7745(3) 0.3490(6) -0.0649(4) 0.111(3) Uani 1 1 d . . . H15 H 0.8178 0.3393 -0.0594 0.133 Uiso 1 1 calc R . . N32 N 0.4242(2) 1.0816(4) 0.0740(2) 0.0526(12) Uani 1 1 d . . . H32 H 0.3952 1.0997 0.0412 0.063 Uiso 1 1 calc R . . C32 C 0.4794(2) 1.1363(4) 0.0919(2) 0.0442(12) Uani 1 1 d . . . C27 C 0.7566(2) 0.5040(4) 0.1914(2) 0.0355(11) Uani 1 1 d . . . H27 H 0.7891 0.5323 0.1675 0.043 Uiso 1 1 calc R . . C17 C 0.58698(19) 0.4831(4) -0.0309(2) 0.0336(10) Uani 1 1 d . . . H17 H 0.5506 0.5183 -0.0199 0.040 Uiso 1 1 calc R . . C37 C 0.4242(2) 0.9941(5) 0.1179(3) 0.0510(14) Uani 1 1 d . . . H37 H 0.3913 0.9442 0.1161 0.061 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 Mn1 0.0219(5) 0.0212(5) 0.0306(5) 0.000 0.0111(4) 0.000 Mn2 0.0172(3) 0.0228(3) 0.0212(3) 0.0001(3) 0.00437(19) 0.0004(3) O5 0.0202(14) 0.0265(17) 0.0271(14) 0.0008(13) 0.0047(11) 0.0000(12) O3 0.0205(14) 0.0247(16) 0.0288(14) -0.0057(13) 0.0049(11) 0.0006(12) O2 0.0212(14) 0.0292(17) 0.0333(16) -0.0098(14) 0.0091(12) -0.0058(13) C1 0.0160(19) 0.026(2) 0.031(2) -0.0016(19) 0.0124(17) 0.0026(17) C3 0.022(2) 0.021(2) 0.0201(19) -0.0008(18) 0.0067(16) -0.0042(17) C2 0.019(2) 0.023(2) 0.025(2) 0.0023(18) 0.0014(16) -0.0047(17) O1 0.0203(14) 0.0367(19) 0.0350(16) -0.0080(14) 0.0066(12) -0.0056(13) O4 0.0179(14) 0.0310(17) 0.0343(15) -0.0097(13) 0.0090(12) -0.0038(12) N11 0.0213(17) 0.031(2) 0.0283(17) -0.0031(16) 0.0026(14) -0.0014(15) N21 0.0277(18) 0.035(2) 0.0263(16) 0.0076(16) 0.0032(14) 0.0078(16) N31 0.0285(19) 0.032(2) 0.036(2) 0.0055(17) 0.0069(16) -0.0032(17) C11 0.031(2) 0.037(3) 0.042(2) -0.018(2) 0.0053(19) -0.003(2) C31 0.027(2) 0.029(2) 0.032(2) 0.0048(19) 0.0086(16) -0.0009(17) O6 0.0161(14) 0.0301(18) 0.0356(16) 0.0053(14) 0.0082(12) 0.0015(12) C21 0.040(2) 0.034(2) 0.030(2) 0.0054(19) 0.0066(18) 0.0096(19) C33 0.067(4) 0.053(4) 0.050(3) 0.024(3) 0.005(3) -0.004(3) C22 0.047(3) 0.043(3) 0.029(2) 0.013(2) 0.0018(19) 0.012(2) C13 0.058(4) 0.070(4) 0.073(4) -0.046(3) 0.011(3) -0.010(3) C12 0.037(3) 0.036(3) 0.037(2) -0.010(2) 0.0005(19) -0.005(2) C34 0.063(3) 0.043(3) 0.054(3) 0.015(3) 0.013(3) -0.013(3) C36 0.031(2) 0.042(3) 0.047(2) 0.014(2) 0.0052(19) -0.0021(19) C23 0.056(3) 0.064(4) 0.043(3) 0.023(3) 0.012(2) 0.020(3) C26 0.041(2) 0.037(3) 0.039(2) 0.005(2) 0.0060(19) 0.004(2) N22 0.042(2) 0.052(3) 0.0352(19) 0.0028(19) -0.0020(17) 0.024(2) N12 0.0309(19) 0.039(2) 0.0321(18) -0.0078(17) -0.0020(15) -0.0186(17) C25 0.047(3) 0.051(3) 0.049(3) 0.007(2) 0.016(2) 0.004(2) C24 0.062(3) 0.055(3) 0.042(3) 0.021(2) 0.012(2) 0.009(3) C35 0.045(3) 0.045(3) 0.054(3) 0.011(3) 0.002(2) -0.013(2) C14 0.061(4) 0.110(6) 0.141(7) -0.095(6) 0.026(4) -0.009(4) C16 0.031(3) 0.071(4) 0.101(5) -0.059(4) 0.004(3) 0.004(3) C15 0.043(3) 0.105(6) 0.186(8) -0.104(6) 0.018(4) 0.004(4) N32 0.053(3) 0.062(3) 0.040(2) 0.020(2) -0.011(2) -0.007(2) C32 0.046(3) 0.049(3) 0.037(2) 0.010(2) 0.004(2) -0.003(2) C27 0.030(2) 0.042(3) 0.033(2) 0.006(2) -0.0025(18) 0.014(2) C17 0.024(2) 0.037(3) 0.040(2) 0.001(2) 0.0028(18) -0.0057(19) C37 0.042(3) 0.057(4) 0.052(3) 0.008(3) 0.000(2) -0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O2 2.160(3) . ? Mn1 O2 2.160(3) 2_655 ? Mn1 N31 2.219(4) 2_655 ? Mn1 N31 2.219(4) . ? Mn1 O4 2.240(3) 2_655 ? Mn1 O4 2.240(3) . ? Mn2 N21 2.199(3) . ? Mn2 O5 2.199(3) . ? Mn2 O3 2.202(3) . ? Mn2 N11 2.208(3) . ? Mn2 O1 2.220(3) . ? Mn2 O6 2.221(3) . ? O5 C3 1.246(4) . ? O3 C2 1.255(4) . ? O2 C1 1.261(4) . ? C1 O1 1.251(4) . ? C1 C2 1.541(5) . ? C3 O6 1.248(4) 7_665 ? C3 C3 1.550(8) 7_665 ? C2 O4 1.253(4) . ? N11 C17 1.311(5) . ? N11 C11 1.395(5) . ? N21 C27 1.300(5) . ? N21 C21 1.388(5) . ? N31 C37 1.316(6) . ? N31 C31 1.405(5) . ? C11 C16 1.387(6) . ? C11 C12 1.394(6) . ? C31 C36 1.385(6) . ? C31 C32 1.388(6) . ? O6 C3 1.248(4) 7_665 ? C21 C22 1.388(6) . ? C21 C26 1.390(6) . ? C33 C34 1.384(7) . ? C33 C32 1.400(7) . ? C33 H33 0.9300 . ? C22 N22 1.353(6) . ? C22 C23 1.391(6) . ? C13 C14 1.359(8) . ? C13 C12 1.396(6) . ? C13 H13 0.9300 . ? C12 N12 1.355(5) . ? C34 C35 1.382(7) . ? C34 H34 0.9300 . ? C36 C35 1.381(6) . ? C36 H36 0.9300 . ? C23 C24 1.367(7) . ? C23 H23 0.9300 . ? C26 C25 1.383(6) . ? C26 H26 0.9300 . ? N22 C27 1.329(5) . ? N22 H22 0.8600 . ? N12 C17 1.339(5) . ? N12 H12 0.8600 . ? C25 C24 1.397(7) . ? C25 H25 0.9300 . ? C24 H24 0.9300 . ? C35 H35 0.9300 . ? C14 C15 1.389(8) . ? C14 H14 0.9300 . ? C16 C15 1.387(7) . ? C16 H16 0.9300 . ? C15 H15 0.9300 . ? N32 C37 1.346(6) . ? N32 C32 1.369(6) . ? N32 H32 0.8600 . ? C27 H27 0.9300 . ? C17 H17 0.9300 . ? C37 H37 0.9300 . ? 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 Mn1 O2 170.40(16) . 2_655 ? O2 Mn1 N31 90.14(11) . 2_655 ? O2 Mn1 N31 96.24(12) 2_655 2_655 ? O2 Mn1 N31 96.24(12) . . ? O2 Mn1 N31 90.14(11) 2_655 . ? N31 Mn1 N31 96.84(19) 2_655 . ? O2 Mn1 O4 97.24(10) . 2_655 ? O2 Mn1 O4 75.73(10) 2_655 2_655 ? N31 Mn1 O4 89.33(12) 2_655 2_655 ? N31 Mn1 O4 165.15(11) . 2_655 ? O2 Mn1 O4 75.73(10) . . ? O2 Mn1 O4 97.24(10) 2_655 . ? N31 Mn1 O4 165.15(11) 2_655 . ? N31 Mn1 O4 89.33(12) . . ? O4 Mn1 O4 87.99(15) 2_655 . ? N21 Mn2 O5 86.48(11) . . ? N21 Mn2 O3 101.08(11) . . ? O5 Mn2 O3 170.29(10) . . ? N21 Mn2 N11 98.80(13) . . ? O5 Mn2 N11 94.93(11) . . ? O3 Mn2 N11 89.97(11) . . ? N21 Mn2 O1 87.07(12) . . ? O5 Mn2 O1 99.36(10) . . ? O3 Mn2 O1 75.18(10) . . ? N11 Mn2 O1 164.88(11) . . ? N21 Mn2 O6 157.36(12) . . ? O5 Mn2 O6 74.75(10) . . ? O3 Mn2 O6 96.47(10) . . ? N11 Mn2 O6 95.37(11) . . ? O1 Mn2 O6 83.70(10) . . ? C3 O5 Mn2 116.2(2) . . ? C2 O3 Mn2 114.8(2) . . ? C1 O2 Mn1 115.3(2) . . ? O1 C1 O2 124.4(4) . . ? O1 C1 C2 117.4(3) . . ? O2 C1 C2 118.2(3) . . ? O5 C3 O6 126.0(4) . 7_665 ? O5 C3 C3 116.5(4) . 7_665 ? O6 C3 C3 117.5(4) 7_665 7_665 ? O4 C2 O3 125.6(4) . . ? O4 C2 C1 116.8(3) . . ? O3 C2 C1 117.6(3) . . ? C1 O1 Mn2 114.4(3) . . ? C2 O4 Mn1 113.7(2) . . ? C17 N11 C11 104.3(4) . . ? C17 N11 Mn2 126.5(3) . . ? C11 N11 Mn2 129.2(3) . . ? C27 N21 C21 105.0(3) . . ? C27 N21 Mn2 123.2(3) . . ? C21 N21 Mn2 131.8(3) . . ? C37 N31 C31 103.3(4) . . ? C37 N31 Mn1 131.0(3) . . ? C31 N31 Mn1 125.6(3) . . ? C16 C11 C12 120.3(4) . . ? C16 C11 N11 130.5(4) . . ? C12 C11 N11 109.2(4) . . ? C36 C31 C32 120.1(4) . . ? C36 C31 N31 130.1(4) . . ? C32 C31 N31 109.8(4) . . ? C3 O6 Mn2 114.7(2) 7_665 . ? N21 C21 C22 108.0(4) . . ? N21 C21 C26 131.6(4) . . ? C22 C21 C26 120.4(4) . . ? C34 C33 C32 115.1(5) . . ? C34 C33 H33 122.5 . . ? C32 C33 H33 122.5 . . ? N22 C22 C21 106.4(4) . . ? N22 C22 C23 130.6(4) . . ? C21 C22 C23 122.9(4) . . ? C14 C13 C12 116.2(5) . . ? C14 C13 H13 121.9 . . ? C12 C13 H13 121.9 . . ? N12 C12 C11 105.4(4) . . ? N12 C12 C13 131.9(4) . . ? C11 C12 C13 122.4(4) . . ? C35 C34 C33 122.9(5) . . ? C35 C34 H34 118.6 . . ? C33 C34 H34 118.6 . . ? C35 C36 C31 118.0(4) . . ? C35 C36 H36 121.0 . . ? C31 C36 H36 121.0 . . ? C24 C23 C22 116.4(5) . . ? C24 C23 H23 121.8 . . ? C22 C23 H23 121.8 . . ? C25 C26 C21 116.8(4) . . ? C25 C26 H26 121.6 . . ? C21 C26 H26 121.6 . . ? C27 N22 C22 107.0(4) . . ? C27 N22 H22 126.5 . . ? C22 N22 H22 126.5 . . ? C17 N12 C12 107.8(3) . . ? C17 N12 H12 126.1 . . ? C12 N12 H12 126.1 . . ? C26 C25 C24 122.1(5) . . ? C26 C25 H25 118.9 . . ? C24 C25 H25 118.9 . . ? C23 C24 C25 121.5(4) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? C34 C35 C36 120.9(5) . . ? C34 C35 H35 119.6 . . ? C36 C35 H35 119.6 . . ? C13 C14 C15 122.3(5) . . ? C13 C14 H14 118.8 . . ? C15 C14 H14 118.8 . . ? C11 C16 C15 117.0(5) . . ? C11 C16 H16 121.5 . . ? C15 C16 H16 121.5 . . ? C16 C15 C14 121.7(6) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C37 N32 C32 106.7(4) . . ? C37 N32 H32 126.6 . . ? C32 N32 H32 126.6 . . ? N32 C32 C31 105.8(4) . . ? N32 C32 C33 131.3(5) . . ? C31 C32 C33 122.9(5) . . ? N21 C27 N22 113.6(4) . . ? N21 C27 H27 123.2 . . ? N22 C27 H27 123.2 . . ? N11 C17 N12 113.3(4) . . ? N11 C17 H17 123.4 . . ? N12 C17 H17 123.4 . . ? N31 C37 N32 114.4(4) . . ? N31 C37 H37 122.8 . . ? N32 C37 H37 122.8 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 29.34 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.875 _refine_diff_density_min -0.597 _refine_diff_density_rms 0.083 #---END data_compound2 _database_code_depnum_ccdc_archive 'CCDC 760876' #TrackingRef 'dalton_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-[(\m~2~oxalato)-bis(benzimidazole)-iron(II)] ; _chemical_name_common ; Iron(II) bis-benzimidazole oxalate ; _chemical_melting_point n/a _chemical_formula_moiety 'C48 H36 Fe3 N12 O12' _chemical_formula_sum 'C48 H36 Fe3 N12 O12' _chemical_formula_weight 1140.44 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2 /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 20.945(2) _cell_length_b 12.3461(9) _cell_length_c 18.550(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.530(12) _cell_angle_gamma 90.00 _cell_volume 4781.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6413 _cell_measurement_theta_min 1.91 _cell_measurement_theta_max 29.37 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2328 _exptl_absorpt_coefficient_mu 0.976 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. R.H. Blessing, Acta Cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.5417 _exptl_absorpt_correction_T_max 0.5647 _exptl_special_details ; PLEASE NOTE cell_measurement_fields are not relavent to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 223(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 IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18399 _diffrn_reflns_av_R_equivalents 0.0607 _diffrn_reflns_av_sigmaI/netI 0.0817 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 26.09 _reflns_number_total 4673 _reflns_number_gt 2131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2 (Brandenberg, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All hydrogen atoms were fixed in calculated positions and refined in riding mode. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0674P)^2^] 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 4673 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1150 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1294 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 0.856 _refine_ls_restrained_S_all 0.856 _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 Fe1 Fe 0.5000 0.86329(8) 0.2500 0.0297(3) Uani 1 2 d S . . Fe2 Fe 0.66678(3) 0.63376(5) 0.08367(3) 0.02174(17) Uani 1 1 d . . . O5 O 0.76667(13) 0.6465(2) 0.06176(15) 0.0251(7) Uani 1 1 d . . . O3 O 0.56599(13) 0.6491(2) 0.09861(15) 0.0262(7) Uani 1 1 d . . . O2 O 0.59706(14) 0.8483(3) 0.23087(15) 0.0299(8) Uani 1 1 d . . . C1 C 0.6098(2) 0.7816(4) 0.1829(2) 0.0248(10) Uani 1 1 d . . . C3 C 0.7780(2) 0.7153(4) 0.0162(2) 0.0222(10) Uani 1 1 d . . . C2 C 0.5530(2) 0.7157(4) 0.1460(2) 0.0243(10) Uani 1 1 d . . . O1 O 0.66358(13) 0.7639(3) 0.16280(15) 0.0297(8) Uani 1 1 d . . . O4 O 0.49902(13) 0.7350(3) 0.16644(16) 0.0310(8) Uani 1 1 d . . . N11 N 0.64572(16) 0.5095(3) 0.00451(18) 0.0265(9) Uani 1 1 d . . . N21 N 0.69818(17) 0.5307(3) 0.17270(18) 0.0277(9) Uani 1 1 d . . . N31 N 0.47873(19) 0.9808(3) 0.1648(2) 0.0376(10) Uani 1 1 d . . . C11 C 0.6847(2) 0.4390(4) -0.0298(2) 0.0332(12) Uani 1 1 d . . . C31 C 0.5124(2) 1.0748(4) 0.1507(2) 0.0307(11) Uani 1 1 d . . . O6 O 0.66818(13) 0.7668(2) 0.00762(14) 0.0268(7) Uani 1 1 d . . . C21 C 0.6656(2) 0.4757(4) 0.2242(2) 0.0252(9) Uani 1 1 d . . . C33 C 0.5055(3) 1.2243(5) 0.0649(3) 0.0597(17) Uani 1 1 d . . . H33 H 0.4853 1.2591 0.0249 0.072 Uiso 1 1 calc R . . C22 C 0.7094(2) 0.4169(4) 0.2688(2) 0.0297(10) Uani 1 1 d . . . C13 C 0.6749(3) 0.3025(5) -0.1254(3) 0.0687(19) Uani 1 1 d . . . H13 H 0.6499 0.2635 -0.1600 0.082 Uiso 1 1 calc R . . C12 C 0.6482(2) 0.3775(4) -0.0801(3) 0.0390(13) Uani 1 1 d . . . C34 C 0.5597(3) 1.2645(4) 0.1005(3) 0.0537(15) Uani 1 1 d . . . H34 H 0.5776 1.3276 0.0836 0.064 Uiso 1 1 calc R . . C36 C 0.5669(2) 1.1191(4) 0.1868(3) 0.0404(12) Uani 1 1 d . . . H36 H 0.5876 1.0853 0.2269 0.048 Uiso 1 1 calc R . . C23 C 0.6920(2) 0.3541(4) 0.3257(2) 0.0433(13) Uani 1 1 d . . . H23 H 0.7221 0.3165 0.3556 0.052 Uiso 1 1 calc R . . C26 C 0.6010(2) 0.4723(4) 0.2356(2) 0.0332(11) Uani 1 1 d . . . H26 H 0.5708 0.5108 0.2065 0.040 Uiso 1 1 calc R . . N22 N 0.76799(18) 0.4400(3) 0.24430(19) 0.0365(10) Uani 1 1 d . . . H22 H 0.8044 0.4161 0.2623 0.044 Uiso 1 1 calc R . . N12 N 0.58672(19) 0.4099(3) -0.07457(19) 0.0381(10) Uani 1 1 d . . . H12 H 0.5532 0.3845 -0.0984 0.046 Uiso 1 1 calc R . . C25 C 0.5836(2) 0.4092(4) 0.2922(2) 0.0384(12) Uani 1 1 d . . . H25 H 0.5407 0.4062 0.3016 0.046 Uiso 1 1 calc R . . C24 C 0.6279(2) 0.3501(4) 0.3356(2) 0.0421(13) Uani 1 1 d . . . H24 H 0.6138 0.3070 0.3723 0.050 Uiso 1 1 calc R . . C35 C 0.5888(2) 1.2149(4) 0.1606(3) 0.0438(13) Uani 1 1 d . . . H35 H 0.6247 1.2473 0.1844 0.053 Uiso 1 1 calc R . . C14 C 0.7394(4) 0.2897(6) -0.1163(4) 0.102(3) Uani 1 1 d . . . H14 H 0.7590 0.2395 -0.1447 0.122 Uiso 1 1 calc R . . C16 C 0.7511(2) 0.4251(5) -0.0211(3) 0.0587(17) Uani 1 1 d . . . H16 H 0.7765 0.4646 0.0128 0.070 Uiso 1 1 calc R . . C15 C 0.7770(3) 0.3499(6) -0.0654(4) 0.101(3) Uani 1 1 d . . . H15 H 0.8211 0.3389 -0.0612 0.121 Uiso 1 1 calc R . . N32 N 0.4297(3) 1.0659(5) 0.0707(2) 0.0764(18) Uani 1 1 d . . . H32 H 0.4018 1.0793 0.0353 0.092 Uiso 1 1 calc R . . C32 C 0.4820(3) 1.1280(5) 0.0919(3) 0.0484(15) Uani 1 1 d . . . C27 C 0.7585(2) 0.5063(4) 0.1875(2) 0.0315(11) Uani 1 1 d . . . H27 H 0.7914 0.5322 0.1612 0.038 Uiso 1 1 calc R . . C17 C 0.5882(2) 0.4887(4) -0.0251(2) 0.0335(11) Uani 1 1 d . . . H17 H 0.5519 0.5254 -0.0128 0.040 Uiso 1 1 calc R . . C37 C 0.4300(3) 0.9808(6) 0.1151(3) 0.0637(18) Uani 1 1 d . . . H37 H 0.3990 0.9268 0.1114 0.076 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 Fe1 0.0249(5) 0.0264(6) 0.0399(6) 0.000 0.0170(4) 0.000 Fe2 0.0170(3) 0.0266(3) 0.0220(3) 0.0001(3) 0.0040(2) -0.0007(3) O5 0.0221(16) 0.0283(18) 0.0255(16) 0.0022(14) 0.0051(13) -0.0035(15) O3 0.0185(16) 0.0304(19) 0.0297(17) -0.0076(15) 0.0026(13) -0.0010(15) O2 0.0234(17) 0.033(2) 0.0352(18) -0.0089(16) 0.0123(14) -0.0057(16) C1 0.021(2) 0.027(3) 0.027(2) -0.001(2) 0.004(2) -0.002(2) C3 0.024(2) 0.024(3) 0.019(2) -0.008(2) 0.0057(18) -0.007(2) C2 0.018(2) 0.026(3) 0.030(3) 0.002(2) 0.0044(19) -0.008(2) O1 0.0170(16) 0.038(2) 0.0344(18) -0.0084(15) 0.0067(13) -0.0052(15) O4 0.0175(16) 0.036(2) 0.0412(19) -0.0094(15) 0.0112(14) -0.0019(15) N11 0.0219(19) 0.031(2) 0.0272(19) -0.0015(17) 0.0046(15) -0.0044(18) N21 0.025(2) 0.031(2) 0.0269(19) 0.0073(17) -0.0001(15) 0.0025(18) N31 0.041(2) 0.033(2) 0.040(2) 0.002(2) 0.014(2) -0.004(2) C11 0.032(3) 0.030(3) 0.038(3) -0.009(2) 0.006(2) -0.003(2) C31 0.030(2) 0.031(3) 0.032(2) 0.004(2) 0.011(2) 0.001(2) O6 0.0196(16) 0.032(2) 0.0292(17) 0.0009(14) 0.0074(13) -0.0008(15) C21 0.030(2) 0.025(2) 0.021(2) 0.0023(18) 0.0018(17) 0.003(2) C33 0.064(4) 0.071(4) 0.044(3) 0.026(3) 0.002(3) -0.005(4) C22 0.032(3) 0.033(3) 0.024(2) 0.005(2) -0.0005(19) 0.001(2) C13 0.078(5) 0.062(4) 0.067(4) -0.042(4) 0.017(4) -0.016(4) C12 0.040(3) 0.041(3) 0.036(3) -0.009(2) 0.002(2) -0.010(3) C34 0.071(4) 0.036(3) 0.057(3) 0.011(3) 0.023(3) -0.006(3) C36 0.035(3) 0.045(3) 0.042(3) 0.011(2) 0.009(2) -0.002(2) C23 0.043(3) 0.052(3) 0.035(3) 0.018(2) 0.005(2) 0.015(3) C26 0.029(2) 0.039(3) 0.032(2) 0.004(2) 0.0016(19) 0.006(2) N22 0.031(2) 0.042(3) 0.035(2) 0.0111(18) -0.0014(17) 0.010(2) N12 0.037(2) 0.041(3) 0.035(2) -0.0042(19) -0.0068(18) -0.023(2) C25 0.033(3) 0.044(3) 0.038(3) 0.006(2) 0.006(2) 0.007(2) C24 0.051(3) 0.045(3) 0.031(2) 0.014(2) 0.010(2) 0.009(3) C35 0.045(3) 0.039(3) 0.048(3) -0.001(3) 0.009(2) -0.012(3) C14 0.076(5) 0.088(6) 0.145(7) -0.083(6) 0.038(5) -0.012(5) C16 0.032(3) 0.056(4) 0.088(4) -0.044(3) 0.005(3) 0.005(3) C15 0.051(4) 0.097(6) 0.158(8) -0.085(6) 0.022(5) 0.010(4) N32 0.073(4) 0.106(5) 0.046(3) 0.031(3) -0.018(3) -0.049(4) C32 0.052(3) 0.061(4) 0.034(3) 0.010(3) 0.007(3) -0.014(3) C27 0.028(2) 0.039(3) 0.028(2) 0.009(2) 0.0031(19) 0.005(2) C17 0.024(2) 0.039(3) 0.038(3) -0.003(2) 0.001(2) -0.009(2) C37 0.067(4) 0.083(5) 0.041(3) 0.001(3) 0.000(3) -0.038(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 Fe1 O2 2.099(3) . ? Fe1 O2 2.099(3) 2_655 ? Fe1 N31 2.166(4) 2_655 ? Fe1 N31 2.166(4) . ? Fe1 O4 2.215(3) . ? Fe1 O4 2.215(3) 2_655 ? Fe2 N11 2.145(4) . ? Fe2 N21 2.147(4) . ? Fe2 O3 2.159(3) . ? Fe2 O6 2.167(3) . ? Fe2 O5 2.168(3) . ? Fe2 O1 2.181(3) . ? O5 C3 1.235(5) . ? O3 C2 1.249(5) . ? O2 C1 1.256(5) . ? C1 O1 1.233(5) . ? C1 C2 1.556(5) . ? C3 O6 1.263(5) 7_665 ? C3 C3 1.534(9) 7_665 ? C2 O4 1.243(5) . ? N11 C17 1.308(5) . ? N11 C11 1.383(5) . ? N21 C27 1.307(5) . ? N21 C21 1.394(5) . ? N31 C37 1.320(6) . ? N31 C31 1.394(6) . ? C11 C12 1.385(6) . ? C11 C16 1.397(7) . ? C31 C32 1.385(7) . ? C31 C36 1.389(6) . ? O6 C3 1.263(5) 7_665 ? C21 C26 1.385(6) . ? C21 C22 1.391(6) . ? C33 C34 1.362(8) . ? C33 C32 1.394(8) . ? C33 H33 0.9300 . ? C22 N22 1.373(5) . ? C22 C23 1.382(6) . ? C13 C14 1.357(9) . ? C13 C12 1.397(7) . ? C13 H13 0.9300 . ? C12 N12 1.360(6) . ? C34 C35 1.371(7) . ? C34 H34 0.9300 . ? C36 C35 1.371(6) . ? C36 H36 0.9300 . ? C23 C24 1.369(7) . ? C23 H23 0.9300 . ? C26 C25 1.379(6) . ? C26 H26 0.9300 . ? N22 C27 1.337(5) . ? N22 H22 0.8600 . ? N12 C17 1.337(6) . ? N12 H12 0.8600 . ? C25 C24 1.387(6) . ? C25 H25 0.9300 . ? C24 H24 0.9300 . ? C35 H35 0.9300 . ? C14 C15 1.395(9) . ? C14 H14 0.9300 . ? C16 C15 1.381(7) . ? C16 H16 0.9300 . ? C15 H15 0.9300 . ? N32 C37 1.335(7) . ? N32 C32 1.369(7) . ? N32 H32 0.8600 . ? C27 H27 0.9300 . ? C17 H17 0.9300 . ? C37 H37 0.9300 . ? 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 Fe1 O2 169.87(18) . 2_655 ? O2 Fe1 N31 92.09(13) . 2_655 ? O2 Fe1 N31 94.70(13) 2_655 2_655 ? O2 Fe1 N31 94.70(13) . . ? O2 Fe1 N31 92.09(13) 2_655 . ? N31 Fe1 N31 95.9(2) 2_655 . ? O2 Fe1 O4 76.95(11) . . ? O2 Fe1 O4 95.71(11) 2_655 . ? N31 Fe1 O4 168.44(13) 2_655 . ? N31 Fe1 O4 88.76(14) . . ? O2 Fe1 O4 95.71(11) . 2_655 ? O2 Fe1 O4 76.95(11) 2_655 2_655 ? N31 Fe1 O4 88.76(14) 2_655 2_655 ? N31 Fe1 O4 168.44(13) . 2_655 ? O4 Fe1 O4 88.72(17) . 2_655 ? N11 Fe2 N21 97.85(14) . . ? N11 Fe2 O3 90.01(12) . . ? N21 Fe2 O3 101.33(12) . . ? N11 Fe2 O6 96.26(12) . . ? N21 Fe2 O6 158.62(13) . . ? O3 Fe2 O6 94.63(11) . . ? N11 Fe2 O5 94.19(12) . . ? N21 Fe2 O5 86.90(12) . . ? O3 Fe2 O5 170.18(11) . . ? O6 Fe2 O5 76.11(11) . . ? N11 Fe2 O1 166.40(12) . . ? N21 Fe2 O1 86.71(13) . . ? O3 Fe2 O1 76.51(11) . . ? O6 Fe2 O1 83.26(11) . . ? O5 Fe2 O1 98.85(11) . . ? C3 O5 Fe2 114.7(3) . . ? C2 O3 Fe2 114.7(3) . . ? C1 O2 Fe1 116.2(3) . . ? O1 C1 O2 125.5(4) . . ? O1 C1 C2 117.3(4) . . ? O2 C1 C2 117.1(4) . . ? O5 C3 O6 125.8(4) . 7_665 ? O5 C3 C3 118.0(5) . 7_665 ? O6 C3 C3 116.2(5) 7_665 7_665 ? O4 C2 O3 126.5(4) . . ? O4 C2 C1 116.6(4) . . ? O3 C2 C1 116.9(3) . . ? C1 O1 Fe2 114.3(3) . . ? C2 O4 Fe1 113.1(3) . . ? C17 N11 C11 103.9(4) . . ? C17 N11 Fe2 124.0(3) . . ? C11 N11 Fe2 131.9(3) . . ? C27 N21 C21 105.2(3) . . ? C27 N21 Fe2 122.0(3) . . ? C21 N21 Fe2 132.8(3) . . ? C37 N31 C31 104.1(4) . . ? C37 N31 Fe1 127.8(4) . . ? C31 N31 Fe1 128.1(3) . . ? N11 C11 C12 109.9(4) . . ? N11 C11 C16 129.9(4) . . ? C12 C11 C16 120.2(4) . . ? C32 C31 C36 120.2(5) . . ? C32 C31 N31 109.5(4) . . ? C36 C31 N31 130.3(4) . . ? C3 O6 Fe2 114.7(3) 7_665 . ? C26 C21 C22 120.0(4) . . ? C26 C21 N21 131.0(4) . . ? C22 C21 N21 109.0(4) . . ? C34 C33 C32 116.2(5) . . ? C34 C33 H33 121.9 . . ? C32 C33 H33 121.9 . . ? N22 C22 C23 131.8(4) . . ? N22 C22 C21 105.0(4) . . ? C23 C22 C21 123.1(4) . . ? C14 C13 C12 116.4(6) . . ? C14 C13 H13 121.8 . . ? C12 C13 H13 121.8 . . ? N12 C12 C11 105.3(4) . . ? N12 C12 C13 131.9(5) . . ? C11 C12 C13 122.8(5) . . ? C33 C34 C35 122.1(5) . . ? C33 C34 H34 118.9 . . ? C35 C34 H34 118.9 . . ? C35 C36 C31 117.0(5) . . ? C35 C36 H36 121.5 . . ? C31 C36 H36 121.5 . . ? C24 C23 C22 116.3(4) . . ? C24 C23 H23 121.9 . . ? C22 C23 H23 121.9 . . ? C25 C26 C21 116.9(4) . . ? C25 C26 H26 121.5 . . ? C21 C26 H26 121.5 . . ? C27 N22 C22 108.0(4) . . ? C27 N22 H22 126.0 . . ? C22 N22 H22 126.0 . . ? C17 N12 C12 107.2(4) . . ? C17 N12 H12 126.4 . . ? C12 N12 H12 126.4 . . ? C26 C25 C24 122.3(4) . . ? C26 C25 H25 118.8 . . ? C24 C25 H25 118.8 . . ? C23 C24 C25 121.4(4) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? C36 C35 C34 122.2(5) . . ? C36 C35 H35 118.9 . . ? C34 C35 H35 118.9 . . ? C13 C14 C15 121.7(6) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C15 C16 C11 116.7(5) . . ? C15 C16 H16 121.7 . . ? C11 C16 H16 121.7 . . ? C16 C15 C14 122.2(6) . . ? C16 C15 H15 118.9 . . ? C14 C15 H15 118.9 . . ? C37 N32 C32 107.4(5) . . ? C37 N32 H32 126.3 . . ? C32 N32 H32 126.3 . . ? N32 C32 C31 105.6(5) . . ? N32 C32 C33 132.2(5) . . ? C31 C32 C33 122.2(5) . . ? N21 C27 N22 112.7(4) . . ? N21 C27 H27 123.6 . . ? N22 C27 H27 123.6 . . ? N11 C17 N12 113.7(4) . . ? N11 C17 H17 123.2 . . ? N12 C17 H17 123.2 . . ? N31 C37 N32 113.4(5) . . ? N31 C37 H37 123.3 . . ? N32 C37 H37 123.3 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.572 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.073 #---END data_compound4 _database_code_depnum_ccdc_archive 'CCDC 760877' #TrackingRef 'dalton_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-[(\m~2~oxalato)-bis(benzimidazole)-nickel(II)] ; _chemical_name_common ; nickel bis-benzimidazole oxalate ; _chemical_melting_point N/A _chemical_formula_moiety 'C48 H36 N12 Ni3 O12' _chemical_formula_sum 'C48 H36 N12 Ni3 O12' _chemical_formula_weight 1148.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'C 2/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 20.4700(19) _cell_length_b 12.4768(15) _cell_length_c 18.3523(19) _cell_angle_alpha 90.00 _cell_angle_beta 92.469(5) _cell_angle_gamma 90.00 _cell_volume 4682.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4995 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2352 _exptl_absorpt_coefficient_mu 1.274 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95135 _exptl_absorpt_correction_T_max 0.98481 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; PLEASE NOTE cell_measurement_fields are not relavent to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD Area Detector' _diffrn_measurement_method '\f and \w scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14198 _diffrn_reflns_av_R_equivalents 0.1220 _diffrn_reflns_av_sigmaI/netI 0.2342 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.63 _reflns_number_total 5059 _reflns_number_gt 1476 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski and Minor, 1997)' _computing_cell_refinement 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_structure_solution ;SHELXS-97 (Sheldrick, 1997a) in WINGX (L.J. Farrugia, J. Appl. Cryst., 1999, 32, 837-838 ; _computing_structure_refinement ;SHELXS-97 (Sheldrick, 1997a) in WINGX (L.J. Farrugia, J. Appl. Cryst., 1999, 32, 837-838 ; _computing_molecular_graphics 'Diamond (Brandenburg, 1997)' _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. All hydrogen atoms were fixed in calculated positions and refined in riding mode ; _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^)+(0.0767P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5059 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2741 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.2090 _refine_ls_wR_factor_gt 0.1486 _refine_ls_goodness_of_fit_ref 0.853 _refine_ls_restrained_S_all 0.853 _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 0.86062(17) 0.2500 0.0374(6) Uani 1 2 d S . . Ni2 Ni 0.66786(8) 0.63627(9) 0.08586(8) 0.0297(3) Uani 1 1 d . . . O5 O 0.7663(3) 0.6474(6) 0.0629(3) 0.0294(17) Uani 1 1 d . . . O3 O 0.5673(3) 0.6478(6) 0.1038(3) 0.0326(18) Uani 1 1 d . . . O2 O 0.5992(4) 0.8491(6) 0.2338(4) 0.0408(19) Uani 1 1 d . . . C1 C 0.6114(5) 0.7804(8) 0.1852(6) 0.029(3) Uani 1 1 d . . . C3 C 0.7807(5) 0.7179(9) 0.0159(5) 0.031(3) Uani 1 1 d . . . C2 C 0.5550(5) 0.7159(9) 0.1495(6) 0.036(3) Uani 1 1 d . . . O1 O 0.6673(3) 0.7589(6) 0.1641(3) 0.0369(19) Uani 1 1 d . . . O4 O 0.4984(4) 0.7371(6) 0.1696(4) 0.041(2) Uani 1 1 d . . . N11 N 0.6473(4) 0.5200(7) 0.0076(4) 0.037(2) Uani 1 1 d . . . N21 N 0.6961(4) 0.5312(7) 0.1700(4) 0.034(2) Uani 1 1 d . . . N31 N 0.4823(5) 0.9702(8) 0.1684(5) 0.045(2) Uani 1 1 d . . . C11 C 0.6835(5) 0.4457(11) -0.0282(6) 0.052(3) Uani 1 1 d . . . C31 C 0.5151(6) 1.0668(9) 0.1535(6) 0.045(3) Uani 1 1 d . . . O6 O 0.6648(3) 0.7615(6) 0.0083(3) 0.0307(18) Uani 1 1 d . . . C21 C 0.6622(5) 0.4761(9) 0.2221(5) 0.041(3) Uani 1 1 d . . . C33 C 0.5069(8) 1.2117(12) 0.0629(7) 0.071(4) Uani 1 1 d . . . H33 H 0.4874 1.2434 0.0216 0.086 Uiso 1 1 calc R . . C22 C 0.7090(6) 0.4171(9) 0.2656(5) 0.042(3) Uani 1 1 d . . . C13 C 0.6723(8) 0.3098(12) -0.1225(8) 0.083(5) Uani 1 1 d . . . H13 H 0.6463 0.2718 -0.1564 0.100 Uiso 1 1 calc R . . C12 C 0.6451(5) 0.3876(10) -0.0771(6) 0.046(3) Uani 1 1 d . . . C34 C 0.5604(7) 1.2592(11) 0.1013(8) 0.069(4) Uani 1 1 d . . . H34 H 0.5776 1.3229 0.0840 0.083 Uiso 1 1 calc R . . C36 C 0.5666(5) 1.1190(8) 0.1874(6) 0.048(3) Uani 1 1 d . . . H36 H 0.5880 1.0887 0.2281 0.058 Uiso 1 1 calc R . . C23 C 0.6891(6) 0.3531(9) 0.3227(6) 0.054(3) Uani 1 1 d . . . H23 H 0.7196 0.3161 0.3521 0.064 Uiso 1 1 calc R . . C26 C 0.5967(4) 0.4720(8) 0.2371(5) 0.038(2) Uani 1 1 d . . . H26 H 0.5656 0.5115 0.2101 0.046 Uiso 1 1 calc R . . N22 N 0.7678(4) 0.4407(7) 0.2398(5) 0.046(2) Uani 1 1 d . . . H22 H 0.8050 0.4169 0.2561 0.055 Uiso 1 1 calc R . . N12 N 0.5847(5) 0.4249(8) -0.0689(5) 0.053(3) Uani 1 1 d . . . H12 H 0.5499 0.4018 -0.0916 0.064 Uiso 1 1 calc R . . C25 C 0.5793(5) 0.4071(9) 0.2935(5) 0.047(3) Uani 1 1 d . . . H25 H 0.5354 0.4039 0.3047 0.056 Uiso 1 1 calc R . . C24 C 0.6240(5) 0.3458(9) 0.3347(5) 0.049(3) Uani 1 1 d . . . H24 H 0.6095 0.2998 0.3704 0.059 Uiso 1 1 calc R . . C35 C 0.5869(6) 1.2159(9) 0.1614(7) 0.060(3) Uani 1 1 d . . . H35 H 0.6203 1.2523 0.1869 0.072 Uiso 1 1 calc R . . C14 C 0.7368(9) 0.2923(14) -0.1153(11) 0.131(8) Uani 1 1 d . . . H14 H 0.7560 0.2424 -0.1453 0.157 Uiso 1 1 calc R . . C16 C 0.7519(6) 0.4265(12) -0.0184(8) 0.093(5) Uani 1 1 d . . . H16 H 0.7780 0.4641 0.0156 0.111 Uiso 1 1 calc R . . C15 C 0.7766(8) 0.3490(16) -0.0622(12) 0.148(9) Uani 1 1 d . . . H15 H 0.8209 0.3325 -0.0573 0.177 Uiso 1 1 calc R . . N32 N 0.4360(6) 1.0437(11) 0.0685(5) 0.091(4) Uani 1 1 d . . . H32 H 0.4098 1.0511 0.0308 0.109 Uiso 1 1 calc R . . C32 C 0.4851(7) 1.1155(13) 0.0898(6) 0.064(4) Uani 1 1 d . . . C27 C 0.7572(5) 0.5089(9) 0.1832(6) 0.041(3) Uani 1 1 d . . . H27 H 0.7907 0.5372 0.1564 0.049 Uiso 1 1 calc R . . C17 C 0.5872(5) 0.5022(10) -0.0206(5) 0.044(3) Uani 1 1 d . . . H17 H 0.5507 0.5409 -0.0074 0.052 Uiso 1 1 calc R . . C37 C 0.4354(7) 0.9603(11) 0.1157(7) 0.075(4) Uani 1 1 d . . . H37 H 0.4061 0.9033 0.1120 0.090 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 0.0300(12) 0.0347(13) 0.0486(12) 0.000 0.0156(10) 0.000 Ni2 0.0256(6) 0.0314(7) 0.0323(6) -0.0004(7) 0.0053(5) -0.0012(8) O5 0.031(4) 0.032(4) 0.026(3) 0.000(3) 0.011(3) 0.001(4) O3 0.020(4) 0.040(5) 0.038(4) -0.011(4) 0.000(3) 0.003(3) O2 0.026(4) 0.044(5) 0.053(5) -0.014(4) 0.014(4) -0.007(4) C1 0.014(6) 0.029(7) 0.043(6) 0.001(5) -0.003(5) -0.005(5) C3 0.036(7) 0.035(7) 0.022(5) -0.017(5) 0.008(5) 0.006(5) C2 0.034(8) 0.029(7) 0.045(7) -0.005(5) 0.016(6) 0.007(5) O1 0.019(4) 0.052(5) 0.040(4) -0.003(3) 0.009(3) -0.011(4) O4 0.031(5) 0.040(5) 0.053(5) -0.005(4) 0.009(4) -0.001(4) N11 0.037(5) 0.035(6) 0.038(5) -0.008(4) -0.004(4) -0.002(5) N21 0.022(4) 0.043(6) 0.038(5) 0.010(4) 0.003(4) 0.007(4) N31 0.047(6) 0.034(6) 0.055(6) 0.005(5) 0.017(5) -0.006(5) C11 0.029(6) 0.063(9) 0.065(8) -0.021(7) 0.021(6) 0.001(6) C31 0.043(7) 0.045(7) 0.047(6) -0.006(5) 0.011(5) 0.007(6) O6 0.021(4) 0.037(5) 0.035(4) 0.004(3) 0.009(3) -0.002(3) C21 0.043(6) 0.041(7) 0.041(6) 0.013(5) 0.009(5) 0.018(5) C33 0.096(12) 0.061(9) 0.060(8) 0.016(7) 0.029(8) 0.023(8) C22 0.050(7) 0.035(6) 0.043(6) 0.012(5) 0.002(6) -0.002(5) C13 0.084(12) 0.066(10) 0.102(11) -0.053(9) 0.031(10) -0.023(9) C12 0.036(7) 0.049(8) 0.054(7) -0.024(6) -0.003(6) -0.010(6) C34 0.076(10) 0.058(9) 0.076(9) 0.001(7) 0.027(8) -0.010(7) C36 0.049(7) 0.040(7) 0.056(6) 0.006(5) 0.007(5) -0.002(5) C23 0.053(7) 0.051(7) 0.058(7) 0.010(6) 0.008(6) 0.016(6) C26 0.032(5) 0.042(6) 0.040(5) 0.001(5) -0.001(4) 0.010(5) N22 0.030(5) 0.044(6) 0.064(6) 0.012(5) -0.001(4) 0.007(4) N12 0.050(6) 0.073(8) 0.037(5) -0.004(5) 0.000(5) -0.021(6) C25 0.039(6) 0.056(7) 0.046(6) 0.013(5) 0.021(5) 0.013(5) C24 0.040(6) 0.061(8) 0.047(6) 0.015(5) 0.015(5) 0.004(6) C35 0.071(9) 0.045(8) 0.066(7) -0.005(7) 0.016(7) -0.024(7) C14 0.088(13) 0.113(15) 0.19(2) -0.103(15) 0.022(14) -0.009(12) C16 0.052(8) 0.095(12) 0.130(13) -0.063(10) -0.001(9) 0.024(8) C15 0.074(11) 0.138(17) 0.23(2) -0.118(16) 0.000(13) 0.033(12) N32 0.086(9) 0.139(13) 0.044(6) 0.037(7) -0.022(6) -0.042(9) C32 0.068(10) 0.087(12) 0.039(7) 0.011(7) 0.017(7) 0.012(9) C27 0.034(6) 0.044(7) 0.044(6) 0.022(5) 0.000(5) -0.012(5) C17 0.041(6) 0.051(8) 0.039(6) 0.008(5) 0.000(5) -0.023(6) C37 0.077(10) 0.082(11) 0.065(8) 0.010(8) 0.001(8) -0.035(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N31 2.049(9) 2_655 ? Ni1 N31 2.049(9) . ? Ni1 O2 2.071(7) 2_655 ? Ni1 O2 2.071(7) . ? Ni1 O4 2.133(8) . ? Ni1 O4 2.133(8) 2_655 ? Ni2 N11 2.071(9) . ? Ni2 O5 2.081(7) . ? Ni2 N21 2.087(8) . ? Ni2 O1 2.098(7) . ? Ni2 O3 2.104(7) . ? Ni2 O6 2.113(7) . ? O5 C3 1.277(12) . ? O3 C2 1.227(12) . ? O2 C1 1.268(11) . ? C1 O1 1.254(11) . ? C1 C2 1.531(12) . ? C3 O6 1.243(12) 7_665 ? C3 C3 1.58(2) 7_665 ? C2 O4 1.260(11) . ? N11 C17 1.333(12) . ? N11 C11 1.372(13) . ? N21 C27 1.295(12) . ? N21 C21 1.387(12) . ? N31 C37 1.338(14) . ? N31 C31 1.412(14) . ? C11 C12 1.374(15) . ? C11 C16 1.424(16) . ? C31 C36 1.366(15) . ? C31 C32 1.432(15) . ? O6 C3 1.243(13) 7_665 ? C21 C26 1.383(13) . ? C21 C22 1.426(13) . ? C33 C32 1.380(19) . ? C33 C34 1.407(19) . ? C33 H33 0.9300 . ? C22 N22 1.344(13) . ? C22 C23 1.392(14) . ? C13 C14 1.34(2) . ? C13 C12 1.409(16) . ? C13 H13 0.9300 . ? C12 N12 1.335(14) . ? C34 C35 1.324(17) . ? C34 H34 0.9300 . ? C36 C35 1.370(14) . ? C36 H36 0.9300 . ? C23 C24 1.364(15) . ? C23 H23 0.9300 . ? C26 C25 1.374(13) . ? C26 H26 0.9300 . ? N22 C27 1.353(12) . ? N22 H22 0.8600 . ? N12 C17 1.309(14) . ? N12 H12 0.8600 . ? C25 C24 1.391(14) . ? C25 H25 0.9300 . ? C24 H24 0.9300 . ? C35 H35 0.9300 . ? C14 C15 1.43(2) . ? C14 H14 0.9300 . ? C16 C15 1.369(18) . ? C16 H16 0.9300 . ? C15 H15 0.9300 . ? N32 C37 1.355(16) . ? N32 C32 1.391(17) . ? N32 H32 0.8600 . ? C27 H27 0.9300 . ? C17 H17 0.9300 . ? C37 H37 0.9300 . ? 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 N31 Ni1 N31 96.3(6) 2_655 . ? N31 Ni1 O2 94.9(3) 2_655 2_655 ? N31 Ni1 O2 90.4(3) . 2_655 ? N31 Ni1 O2 90.4(3) 2_655 . ? N31 Ni1 O2 94.9(3) . . ? O2 Ni1 O2 172.0(5) 2_655 . ? N31 Ni1 O4 170.1(3) 2_655 . ? N31 Ni1 O4 88.8(3) . . ? O2 Ni1 O4 93.6(3) 2_655 . ? O2 Ni1 O4 80.6(3) . . ? N31 Ni1 O4 88.8(3) 2_655 2_655 ? N31 Ni1 O4 170.1(3) . 2_655 ? O2 Ni1 O4 80.6(3) 2_655 2_655 ? O2 Ni1 O4 93.6(3) . 2_655 ? O4 Ni1 O4 87.5(4) . 2_655 ? N11 Ni2 O5 94.3(3) . . ? N11 Ni2 N21 96.6(3) . . ? O5 Ni2 N21 87.2(3) . . ? N11 Ni2 O1 167.9(3) . . ? O5 Ni2 O1 97.1(3) . . ? N21 Ni2 O1 87.8(3) . . ? N11 Ni2 O3 89.2(3) . . ? O5 Ni2 O3 171.8(3) . . ? N21 Ni2 O3 99.7(3) . . ? O1 Ni2 O3 79.0(3) . . ? N11 Ni2 O6 93.0(3) . . ? O5 Ni2 O6 79.3(3) . . ? N21 Ni2 O6 164.1(3) . . ? O1 Ni2 O6 85.5(2) . . ? O3 Ni2 O6 93.1(3) . . ? C3 O5 Ni2 115.9(7) . . ? C2 O3 Ni2 112.6(7) . . ? C1 O2 Ni1 111.8(6) . . ? O1 C1 O2 124.8(9) . . ? O1 C1 C2 115.8(8) . . ? O2 C1 C2 119.3(8) . . ? O6 C3 O5 128.3(10) 7_665 . ? O6 C3 C3 118.4(12) 7_665 7_665 ? O5 C3 C3 113.3(12) . 7_665 ? O3 C2 O4 124.3(11) . . ? O3 C2 C1 119.0(9) . . ? O4 C2 C1 116.7(9) . . ? C1 O1 Ni2 113.6(7) . . ? C2 O4 Ni1 111.5(7) . . ? C17 N11 C11 102.1(9) . . ? C17 N11 Ni2 122.8(8) . . ? C11 N11 Ni2 135.1(8) . . ? C27 N21 C21 105.7(8) . . ? C27 N21 Ni2 120.5(7) . . ? C21 N21 Ni2 133.7(6) . . ? C37 N31 C31 105.7(9) . . ? C37 N31 Ni1 124.4(8) . . ? C31 N31 Ni1 129.8(8) . . ? N11 C11 C12 111.3(10) . . ? N11 C11 C16 126.9(11) . . ? C12 C11 C16 121.8(11) . . ? C36 C31 N31 133.1(11) . . ? C36 C31 C32 117.7(12) . . ? N31 C31 C32 109.2(11) . . ? C3 O6 Ni2 113.1(7) 7_665 . ? C26 C21 N21 132.3(9) . . ? C26 C21 C22 120.3(9) . . ? N21 C21 C22 107.4(9) . . ? C32 C33 C34 116.4(13) . . ? C32 C33 H33 121.8 . . ? C34 C33 H33 121.8 . . ? N22 C22 C23 133.4(10) . . ? N22 C22 C21 106.2(9) . . ? C23 C22 C21 120.4(10) . . ? C14 C13 C12 117.7(14) . . ? C14 C13 H13 121.1 . . ? C12 C13 H13 121.1 . . ? N12 C12 C11 104.4(10) . . ? N12 C12 C13 134.2(11) . . ? C11 C12 C13 121.3(12) . . ? C35 C34 C33 121.8(13) . . ? C35 C34 H34 119.1 . . ? C33 C34 H34 119.1 . . ? C31 C36 C35 120.1(11) . . ? C31 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C24 C23 C22 118.7(10) . . ? C24 C23 H23 120.7 . . ? C22 C23 H23 120.7 . . ? C25 C26 C21 117.2(9) . . ? C25 C26 H26 121.4 . . ? C21 C26 H26 121.4 . . ? C22 N22 C27 107.0(9) . . ? C22 N22 H22 126.5 . . ? C27 N22 H22 126.5 . . ? C17 N12 C12 108.9(10) . . ? C17 N12 H12 125.5 . . ? C12 N12 H12 125.5 . . ? C26 C25 C24 123.2(9) . . ? C26 C25 H25 118.4 . . ? C24 C25 H25 118.4 . . ? C23 C24 C25 120.0(10) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C34 C35 C36 122.0(12) . . ? C34 C35 H35 119.0 . . ? C36 C35 H35 119.0 . . ? C13 C14 C15 121.2(14) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C15 C16 C11 115.5(13) . . ? C15 C16 H16 122.3 . . ? C11 C16 H16 122.3 . . ? C16 C15 C14 122.4(15) . . ? C16 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? C37 N32 C32 109.9(10) . . ? C37 N32 H32 125.1 . . ? C32 N32 H32 125.1 . . ? C33 C32 N32 134.5(13) . . ? C33 C32 C31 121.8(14) . . ? N32 C32 C31 103.7(12) . . ? N21 C27 N22 113.6(9) . . ? N21 C27 H27 123.2 . . ? N22 C27 H27 123.2 . . ? N12 C17 N11 113.2(11) . . ? N12 C17 H17 123.4 . . ? N11 C17 H17 123.4 . . ? N31 C37 N32 111.5(11) . . ? N31 C37 H37 124.3 . . ? N32 C37 H37 124.3 . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 1.408 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.100 #---END data_compound5 _database_code_depnum_ccdc_archive 'CCDC 760878' #TrackingRef 'dalton_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-[(\m~2~oxalato)-bis(benzimidazole)-copper(II)] ; _chemical_name_common ; Copper(II) bis-benzimidazole oxalate ; _chemical_melting_point N/A _chemical_formula_moiety 'C48 H36 Cu3 N12 O12' _chemical_formula_sum 'C48 H36 Cu3 N12 O12' _chemical_formula_weight 1163.54 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2 /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 20.657(4) _cell_length_b 12.578(3) _cell_length_c 18.299(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.74(3) _cell_angle_gamma 90.00 _cell_volume 4744.3(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11059 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 25.61 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2364 _exptl_absorpt_coefficient_mu 1.411 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.867 _exptl_absorpt_correction_T_max 0.918 _exptl_absorpt_process_details 'MULscanABS, (PLATON, Speck, 2003)' _exptl_special_details ; PLEASE NOTE cell_measurement_fields are not relavent to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 150(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 IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22437 _diffrn_reflns_av_R_equivalents 0.1487 _diffrn_reflns_av_sigmaI/netI 0.0922 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.20 _reflns_number_total 4246 _reflns_number_gt 2604 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2 (Brandenberg, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All hydrogen atoms were fixed in calculated positions and refined in riding mode. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1275P)^2^+166.2795P] 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 SHELXL _refine_ls_extinction_coef 0.0016(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4246 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1734 _refine_ls_R_factor_gt 0.1331 _refine_ls_wR_factor_ref 0.3666 _refine_ls_wR_factor_gt 0.3432 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Cu1 Cu 0.5000 0.8743(2) 0.2500 0.0569(8) Uani 1 2 d S . . Cu2 Cu 0.66849(7) 0.63101(13) 0.08812(7) 0.0442(6) Uani 1 1 d . . . O5 O 0.7778(4) 0.6501(7) 0.0594(4) 0.047(2) Uani 1 1 d . . . O3 O 0.5522(4) 0.6531(8) 0.1043(5) 0.053(2) Uani 1 1 d . . . O2 O 0.6063(4) 0.8498(8) 0.2296(5) 0.055(2) Uani 1 1 d . . . C1 C 0.6130(6) 0.7764(11) 0.1850(6) 0.047(3) Uani 1 1 d . . . C3 C 0.7804(5) 0.7209(11) 0.0128(6) 0.046(3) Uani 1 1 d . . . C2 C 0.5476(6) 0.7253(11) 0.1507(7) 0.049(3) Uani 1 1 d . . . O1 O 0.6646(3) 0.7439(8) 0.1626(4) 0.046(2) Uani 1 1 d . . . O4 O 0.4950(5) 0.7598(9) 0.1735(6) 0.068(3) Uani 1 1 d . . . N11 N 0.6474(5) 0.5189(9) 0.0143(5) 0.045(3) Uani 1 1 d . . . N21 N 0.6976(5) 0.5317(9) 0.1673(5) 0.044(2) Uani 1 1 d . . . N31 N 0.4840(6) 0.9827(10) 0.1695(6) 0.057(3) Uani 1 1 d . . . C11 C 0.6825(6) 0.4482(11) -0.0254(7) 0.047(3) Uani 1 1 d . . . C31 C 0.5150(6) 1.0745(11) 0.1548(6) 0.048(3) Uani 1 1 d . . . O6 O 0.6659(4) 0.7478(7) 0.0137(5) 0.052(2) Uani 1 1 d . . . C21 C 0.6649(6) 0.4779(10) 0.2213(6) 0.043(3) Uani 1 1 d . . . C33 C 0.5106(8) 1.2120(17) 0.0658(9) 0.088(6) Uani 1 1 d . . . H33 H 0.4920 1.2400 0.0223 0.105 Uiso 1 1 calc R . . C22 C 0.7089(5) 0.4195(11) 0.2651(6) 0.043(3) Uani 1 1 d . . . C13 C 0.6634(8) 0.3117(15) -0.1200(8) 0.076(5) Uani 1 1 d . . . H13 H 0.6355 0.2734 -0.1520 0.091 Uiso 1 1 calc R . . C12 C 0.6422(6) 0.3895(11) -0.0720(6) 0.049(3) Uani 1 1 d . . . C34 C 0.5637(7) 1.2632(13) 0.1025(8) 0.065(4) Uani 1 1 d . . . H34 H 0.5793 1.3273 0.0854 0.078 Uiso 1 1 calc R . . C36 C 0.5724(6) 1.1256(13) 0.1927(7) 0.059(4) Uani 1 1 d . . . H36 H 0.5933 1.0952 0.2342 0.071 Uiso 1 1 calc R . . C23 C 0.6925(7) 0.3536(12) 0.3226(6) 0.057(4) Uani 1 1 d . . . H23 H 0.7232 0.3136 0.3500 0.068 Uiso 1 1 calc R . . C26 C 0.6000(6) 0.4743(12) 0.2351(6) 0.051(3) Uani 1 1 d . . . H26 H 0.5687 0.5108 0.2062 0.062 Uiso 1 1 calc R . . N22 N 0.7696(5) 0.4379(9) 0.2384(5) 0.050(3) Uani 1 1 d . . . H22 H 0.8062 0.4128 0.2556 0.060 Uiso 1 1 calc R . . N12 N 0.5806(5) 0.4241(10) -0.0638(5) 0.052(3) Uani 1 1 d . . . H12 H 0.5452 0.4008 -0.0856 0.062 Uiso 1 1 calc R . . C25 C 0.5839(6) 0.4127(11) 0.2949(6) 0.048(3) Uani 1 1 d . . . H25 H 0.5411 0.4130 0.3075 0.057 Uiso 1 1 calc R . . C24 C 0.6274(7) 0.3525(12) 0.3356(7) 0.061(4) Uani 1 1 d . . . H24 H 0.6131 0.3099 0.3729 0.073 Uiso 1 1 calc R . . C35 C 0.5925(7) 1.2154(12) 0.1655(7) 0.058(4) Uani 1 1 d . . . H35 H 0.6278 1.2491 0.1895 0.069 Uiso 1 1 calc R . . C14 C 0.7315(8) 0.2974(15) -0.1149(10) 0.086(6) Uani 1 1 d . . . H14 H 0.7499 0.2495 -0.1463 0.103 Uiso 1 1 calc R . . C16 C 0.7490(6) 0.4278(13) -0.0198(8) 0.064(4) Uani 1 1 d . . . H16 H 0.7770 0.4641 0.0133 0.077 Uiso 1 1 calc R . . C15 C 0.7711(8) 0.3519(15) -0.0653(10) 0.092(7) Uani 1 1 d . . . H15 H 0.8152 0.3365 -0.0624 0.110 Uiso 1 1 calc R . . N32 N 0.4373(8) 1.0534(15) 0.0718(6) 0.112(7) Uani 1 1 d . . . H32 H 0.4106 1.0599 0.0340 0.134 Uiso 1 1 calc R . . C32 C 0.4868(8) 1.1228(16) 0.0937(7) 0.082(6) Uani 1 1 d . . . C27 C 0.7595(7) 0.5032(11) 0.1797(7) 0.053(3) Uani 1 1 d . . . H27 H 0.7924 0.5259 0.1511 0.063 Uiso 1 1 calc R . . C17 C 0.5873(6) 0.5040(11) -0.0132(6) 0.049(3) Uani 1 1 d . . . H17 H 0.5524 0.5445 0.0007 0.059 Uiso 1 1 calc R . . C37 C 0.4391(11) 0.9751(19) 0.1202(9) 0.103(7) Uani 1 1 d . . . H37 H 0.4095 0.9192 0.1178 0.123 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 Cu1 0.0502(14) 0.0617(16) 0.0630(15) 0.000 0.0360(11) 0.000 Cu2 0.0404(9) 0.0646(11) 0.0290(8) 0.0006(7) 0.0137(6) -0.0011(8) O5 0.037(5) 0.067(6) 0.037(4) 0.003(4) 0.011(3) -0.007(4) O3 0.041(5) 0.071(6) 0.046(5) -0.017(4) 0.014(4) -0.003(4) O2 0.055(6) 0.064(6) 0.050(5) -0.010(4) 0.030(4) -0.003(5) C1 0.048(7) 0.060(9) 0.035(6) 0.005(6) 0.012(5) -0.012(6) C3 0.032(6) 0.072(9) 0.034(6) -0.004(6) 0.012(5) 0.002(6) C2 0.032(7) 0.067(9) 0.050(7) 0.007(6) 0.019(5) 0.003(6) O1 0.023(4) 0.084(7) 0.033(4) 0.001(4) 0.012(3) 0.004(4) O4 0.048(6) 0.075(7) 0.084(7) -0.003(6) 0.035(5) 0.000(5) N11 0.039(6) 0.073(7) 0.025(5) 0.009(5) 0.015(4) 0.007(5) N21 0.034(5) 0.059(7) 0.037(5) -0.010(5) 0.007(4) -0.003(5) N31 0.055(7) 0.062(8) 0.057(7) -0.012(6) 0.023(6) -0.018(6) C11 0.039(7) 0.055(8) 0.047(7) 0.005(6) 0.009(5) -0.003(6) C31 0.049(7) 0.060(8) 0.038(6) 0.002(6) 0.022(5) -0.002(6) O6 0.041(5) 0.062(6) 0.055(5) 0.004(4) 0.019(4) -0.002(4) C21 0.056(7) 0.049(7) 0.026(5) 0.006(5) 0.007(5) 0.002(6) C33 0.062(10) 0.144(18) 0.057(9) 0.041(11) -0.001(8) -0.001(11) C22 0.035(6) 0.069(9) 0.023(5) 0.000(5) -0.010(4) 0.010(6) C13 0.068(10) 0.107(14) 0.054(8) -0.027(9) 0.014(8) -0.005(9) C12 0.050(7) 0.064(9) 0.034(6) 0.000(6) 0.009(5) -0.006(6) C34 0.064(9) 0.073(10) 0.061(9) 0.017(8) 0.029(8) -0.004(8) C36 0.041(7) 0.089(11) 0.049(7) 0.000(7) 0.018(6) -0.001(7) C23 0.068(9) 0.070(10) 0.033(6) 0.017(6) 0.017(6) 0.015(7) C26 0.047(7) 0.073(10) 0.036(6) -0.001(6) 0.018(5) -0.001(7) N22 0.043(6) 0.080(8) 0.029(5) 0.008(5) 0.012(4) 0.004(5) N12 0.036(6) 0.087(9) 0.033(5) -0.001(5) 0.010(4) -0.002(5) C25 0.037(6) 0.076(9) 0.031(6) 0.009(6) 0.005(5) 0.011(6) C24 0.070(9) 0.077(10) 0.038(7) 0.020(6) 0.024(6) 0.030(8) C35 0.049(8) 0.078(10) 0.048(7) 0.002(7) 0.021(6) -0.008(7) C14 0.056(10) 0.105(14) 0.096(13) -0.054(11) -0.004(9) 0.006(9) C16 0.031(7) 0.086(11) 0.078(10) -0.015(8) 0.007(6) 0.020(7) C15 0.047(9) 0.117(16) 0.113(14) -0.071(12) 0.008(9) 0.003(9) N32 0.104(11) 0.195(19) 0.034(6) 0.028(9) -0.016(7) -0.099(12) C32 0.072(10) 0.136(17) 0.038(7) 0.013(9) 0.006(7) -0.046(11) C27 0.059(8) 0.062(9) 0.039(6) 0.003(6) 0.014(6) 0.008(7) C17 0.038(7) 0.076(10) 0.034(6) -0.001(6) 0.005(5) 0.018(6) C37 0.123(17) 0.138(19) 0.049(9) -0.010(11) 0.019(11) -0.053(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 Cu1 O4 2.007(11) . ? Cu1 O4 2.007(11) 2_655 ? Cu1 N31 2.018(13) 2_655 ? Cu1 N31 2.018(13) . ? Cu1 O2 2.272(9) . ? Cu1 O2 2.272(9) 2_655 ? Cu2 O1 1.973(9) . ? Cu2 N21 1.977(11) . ? Cu2 N11 1.981(11) . ? Cu2 O6 2.001(9) . ? Cu2 O5 2.363(8) . ? O5 C3 1.236(15) . ? O3 C2 1.252(15) . ? O2 C1 1.246(15) . ? C1 O1 1.237(14) . ? C1 C2 1.588(18) . ? C3 O6 1.302(14) 7_665 ? C3 C3 1.50(2) 7_665 ? C2 O4 1.264(14) . ? N11 C17 1.324(15) . ? N11 C11 1.383(15) . ? N21 C27 1.332(16) . ? N21 C21 1.407(14) . ? N31 C37 1.26(2) . ? N31 C31 1.357(17) . ? C11 C12 1.370(18) . ? C11 C16 1.394(17) . ? C31 C32 1.37(2) . ? C31 C36 1.480(19) . ? O6 C3 1.302(14) 7_665 ? C21 C26 1.381(17) . ? C21 C22 1.383(16) . ? C33 C32 1.34(2) . ? C33 C34 1.41(2) . ? C33 H33 0.9300 . ? C22 N22 1.396(15) . ? C22 C23 1.398(17) . ? C13 C12 1.403(19) . ? C13 C14 1.42(2) . ? C13 H13 0.9300 . ? C12 N12 1.363(16) . ? C34 C35 1.40(2) . ? C34 H34 0.9300 . ? C36 C35 1.31(2) . ? C36 H36 0.9300 . ? C23 C24 1.38(2) . ? C23 H23 0.9300 . ? C26 C25 1.397(16) . ? C26 H26 0.9300 . ? N22 C27 1.357(16) . ? N22 H22 0.8600 . ? N12 C17 1.366(16) . ? N12 H12 0.8600 . ? C25 C24 1.361(17) . ? C25 H25 0.9300 . ? C24 H24 0.9300 . ? C35 H35 0.9300 . ? C14 C15 1.37(2) . ? C14 H14 0.9300 . ? C16 C15 1.36(2) . ? C16 H16 0.9300 . ? C15 H15 0.9300 . ? N32 C37 1.32(2) . ? N32 C32 1.38(2) . ? N32 H32 0.8600 . ? C27 H27 0.9300 . ? C17 H17 0.9300 . ? C37 H37 0.9300 . ? 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 O4 Cu1 O4 88.3(6) . 2_655 ? O4 Cu1 N31 172.9(5) . 2_655 ? O4 Cu1 N31 88.7(4) 2_655 2_655 ? O4 Cu1 N31 88.7(4) . . ? O4 Cu1 N31 172.9(4) 2_655 . ? N31 Cu1 N31 95.0(7) 2_655 . ? O4 Cu1 O2 78.1(4) . . ? O4 Cu1 O2 90.7(4) 2_655 . ? N31 Cu1 O2 95.6(4) 2_655 . ? N31 Cu1 O2 94.9(4) . . ? O4 Cu1 O2 90.7(4) . 2_655 ? O4 Cu1 O2 78.1(4) 2_655 2_655 ? N31 Cu1 O2 94.9(4) 2_655 2_655 ? N31 Cu1 O2 95.6(4) . 2_655 ? O2 Cu1 O2 164.4(5) . 2_655 ? O1 Cu2 N21 88.5(4) . . ? O1 Cu2 N11 165.0(3) . . ? N21 Cu2 N11 95.3(4) . . ? O1 Cu2 O6 86.6(4) . . ? N21 Cu2 O6 162.9(4) . . ? N11 Cu2 O6 93.6(4) . . ? O1 Cu2 O5 99.4(3) . . ? N21 Cu2 O5 88.7(3) . . ? N11 Cu2 O5 95.2(3) . . ? O6 Cu2 O5 76.0(3) . . ? C3 O5 Cu2 108.2(7) . . ? C1 O2 Cu1 111.0(8) . . ? O1 C1 O2 126.7(12) . . ? O1 C1 C2 117.7(11) . . ? O2 C1 C2 115.5(11) . . ? O5 C3 O6 123.5(11) . 7_665 ? O5 C3 C3 119.6(13) . 7_665 ? O6 C3 C3 116.9(14) 7_665 7_665 ? O3 C2 O4 125.2(13) . . ? O3 C2 C1 117.5(10) . . ? O4 C2 C1 117.3(12) . . ? C1 O1 Cu2 122.8(8) . . ? C2 O4 Cu1 118.0(9) . . ? C17 N11 C11 102.7(10) . . ? C17 N11 Cu2 121.3(8) . . ? C11 N11 Cu2 135.7(8) . . ? C27 N21 C21 104.5(10) . . ? C27 N21 Cu2 122.6(8) . . ? C21 N21 Cu2 132.9(8) . . ? C37 N31 C31 104.9(15) . . ? C37 N31 Cu1 123.5(12) . . ? C31 N31 Cu1 131.5(10) . . ? C12 C11 N11 110.8(11) . . ? C12 C11 C16 120.2(13) . . ? N11 C11 C16 128.9(13) . . ? N31 C31 C32 111.0(13) . . ? N31 C31 C36 130.5(13) . . ? C32 C31 C36 118.4(13) . . ? C3 O6 Cu2 119.3(8) 7_665 . ? C26 C21 C22 119.0(11) . . ? C26 C21 N21 131.4(12) . . ? C22 C21 N21 109.6(11) . . ? C32 C33 C34 119.7(14) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C21 C22 N22 106.3(10) . . ? C21 C22 C23 124.7(12) . . ? N22 C22 C23 129.0(11) . . ? C12 C13 C14 113.4(14) . . ? C12 C13 H13 123.3 . . ? C14 C13 H13 123.3 . . ? N12 C12 C11 107.1(11) . . ? N12 C12 C13 128.6(13) . . ? C11 C12 C13 124.3(13) . . ? C35 C34 C33 118.3(14) . . ? C35 C34 H34 120.9 . . ? C33 C34 H34 120.9 . . ? C35 C36 C31 117.3(13) . . ? C35 C36 H36 121.4 . . ? C31 C36 H36 121.4 . . ? C24 C23 C22 115.0(12) . . ? C24 C23 H23 122.5 . . ? C22 C23 H23 122.5 . . ? C21 C26 C25 116.4(12) . . ? C21 C26 H26 121.8 . . ? C25 C26 H26 121.8 . . ? C27 N22 C22 106.3(10) . . ? C27 N22 H22 126.8 . . ? C22 N22 H22 126.8 . . ? C12 N12 C17 104.8(11) . . ? C12 N12 H12 127.6 . . ? C17 N12 H12 127.6 . . ? C24 C25 C26 123.8(12) . . ? C24 C25 H25 118.1 . . ? C26 C25 H25 118.1 . . ? C25 C24 C23 121.0(12) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C36 C35 C34 123.7(15) . . ? C36 C35 H35 118.1 . . ? C34 C35 H35 118.1 . . ? C15 C14 C13 121.9(15) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C15 C16 C11 116.8(15) . . ? C15 C16 H16 121.6 . . ? C11 C16 H16 121.6 . . ? C16 C15 C14 123.2(15) . . ? C16 C15 H15 118.4 . . ? C14 C15 H15 118.4 . . ? C37 N32 C32 106.7(15) . . ? C37 N32 H32 126.6 . . ? C32 N32 H32 126.6 . . ? C33 C32 C31 122.4(15) . . ? C33 C32 N32 134.4(16) . . ? C31 C32 N32 103.0(14) . . ? N21 C27 N22 113.3(11) . . ? N21 C27 H27 123.4 . . ? N22 C27 H27 123.4 . . ? N11 C17 N12 114.4(11) . . ? N11 C17 H17 122.8 . . ? N12 C17 H17 122.8 . . ? N31 C37 N32 114.3(18) . . ? N31 C37 H37 122.8 . . ? N32 C37 H37 122.8 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.384 _refine_diff_density_min -1.122 _refine_diff_density_rms 0.174 #---END data_compound7 _database_code_depnum_ccdc_archive 'CCDC 760879' #TrackingRef 'dalton_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-[(\m~2~-oxalato)-bis(benzotriazole)-manganese(II)] ; _chemical_name_common '[Mn(ox)(btz)2]n' _chemical_melting_point N/A _chemical_formula_moiety 'C14 H10 Mn N6 O4' _chemical_formula_sum 'C14 H10 Mn N6 O4' _chemical_formula_weight 381.22 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 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' _cell_length_a 14.551(3) _cell_length_b 12.549(3) _cell_length_c 9.4577(19) _cell_angle_alpha 90.00 _cell_angle_beta 109.50(3) _cell_angle_gamma 90.00 _cell_volume 1627.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4334 _cell_measurement_theta_min 4.2 _cell_measurement_theta_max 51.8 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.844 _exptl_absorpt_correction_type sphere _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_absorpt_correction_T_min 0.5558 _exptl_absorpt_correction_T_max 0.5612 _exptl_absorpt_correction_T_ave 0.5589 _exptl_crystal_size_rad 0.4200 _exptl_special_details ; PLEASE NOTE cell_measurement_fields are not relavent to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6319 _diffrn_reflns_av_R_equivalents 0.1014 _diffrn_reflns_av_sigmaI/netI 0.1147 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 26.17 _reflns_number_total 3045 _reflns_number_gt 2222 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SIR92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1a (Brandenberg, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All hydrogen atoms were fixed in calculated positions and refined in riding mode on the parent atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0569P)^2^] 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 SHELXL _refine_ls_extinction_coef 0.0058(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(3) _refine_ls_number_reflns 3045 _refine_ls_number_parameters 227 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1090 _refine_ls_goodness_of_fit_ref 0.919 _refine_ls_restrained_S_all 0.918 _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 C16 C 0.2587(5) 0.2498(5) 0.4325(7) 0.0361(14) Uani 1 1 d . . . H16 H 0.2015 0.2103 0.3953 0.043 Uiso 1 1 calc R . . Mn1 Mn 0.16772(8) 0.12452(5) 0.73992(10) 0.0202(2) Uani 1 1 d . . . O4 O 0.2440(4) -0.1081(3) 0.4796(5) 0.0246(11) Uani 1 1 d . . . O1 O 0.0833(3) 0.0926(4) 0.5051(5) 0.0234(10) Uani 1 1 d . . . O2 O 0.0787(3) -0.0110(3) 0.3123(5) 0.0244(10) Uani 1 1 d . . . O3 O 0.2436(3) -0.0108(3) 0.6766(5) 0.0268(10) Uani 1 1 d . . . N12 N 0.3485(4) 0.2638(4) 0.8304(6) 0.0249(13) Uani 1 1 d . . . N22 N -0.0173(4) 0.2561(4) 0.6500(7) 0.0322(15) Uani 1 1 d . . . C1 C 0.1158(5) 0.0192(5) 0.4448(7) 0.0200(14) Uani 1 1 d . . . C2 C 0.2101(5) -0.0373(5) 0.5438(7) 0.0210(14) Uani 1 1 d . . . N13 N 0.2822(4) 0.2291(4) 0.7077(6) 0.0273(12) Uani 1 1 d . . . N21 N -0.0627(4) 0.3464(4) 0.6652(7) 0.0315(13) Uani 1 1 d . . . H21 H -0.1222 0.3615 0.6142 0.038 Uiso 1 1 calc R . . N23 N 0.0720(4) 0.2608(4) 0.7431(6) 0.0263(11) Uani 1 1 d . . . N11 N 0.4134(4) 0.3219(4) 0.7930(6) 0.0301(13) Uani 1 1 d . . . H11 H 0.4633 0.3525 0.8559 0.036 Uiso 1 1 calc R . . C25 C 0.1561(7) 0.4943(7) 0.9849(12) 0.0432(16) Uani 1 1 d . . . H25 H 0.2094 0.5253 1.0572 0.052 Uiso 1 1 calc R . . C13 C 0.4313(5) 0.3766(5) 0.5430(7) 0.0418(15) Uani 1 1 d . . . H13 H 0.4870 0.4185 0.5781 0.050 Uiso 1 1 calc R . . C21 C 0.0860(4) 0.3545(4) 0.8208(6) 0.0243(11) Uani 1 1 d . . . C26 C 0.1675(4) 0.3960(5) 0.9305(7) 0.0344(13) Uani 1 1 d . . . H26 H 0.2262 0.3591 0.9648 0.041 Uiso 1 1 calc R . . C23 C -0.0120(5) 0.5107(5) 0.8284(7) 0.0393(15) Uani 1 1 d . . . H23 H -0.0703 0.5484 0.7941 0.047 Uiso 1 1 calc R . . C22 C -0.0022(4) 0.4110(4) 0.7721(6) 0.0276(12) Uani 1 1 d . . . C12 C 0.3896(4) 0.3261(4) 0.6393(6) 0.0264(12) Uani 1 1 d . . . C15 C 0.3014(5) 0.2972(5) 0.3400(7) 0.0452(16) Uani 1 1 d . . . H15 H 0.2737 0.2871 0.2370 0.054 Uiso 1 1 calc R . . C14 C 0.3840(5) 0.3593(6) 0.3935(7) 0.0481(18) Uani 1 1 d . . . H14 H 0.4086 0.3910 0.3247 0.058 Uiso 1 1 calc R . . C24 C 0.0679(5) 0.5506(5) 0.9364(8) 0.0444(16) Uani 1 1 d . . . H24 H 0.0638 0.6165 0.9790 0.053 Uiso 1 1 calc R . . C11 C 0.3057(4) 0.2641(4) 0.5851(6) 0.0248(12) 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 C16 0.034(3) 0.044(3) 0.026(3) -0.006(3) 0.004(3) -0.018(3) Mn1 0.0202(4) 0.0217(3) 0.0167(3) 0.0002(5) 0.0036(3) -0.0003(5) O4 0.024(3) 0.029(2) 0.020(2) -0.0014(19) 0.006(2) 0.0091(19) O1 0.022(3) 0.0252(19) 0.020(2) -0.0044(19) 0.003(2) 0.0048(19) O2 0.023(2) 0.028(2) 0.019(2) -0.0050(18) 0.002(2) 0.0030(18) O3 0.025(3) 0.035(2) 0.016(2) -0.0034(18) 0.000(2) 0.0079(18) N12 0.023(3) 0.028(3) 0.017(3) 0.001(2) -0.003(3) -0.007(2) N22 0.029(4) 0.029(3) 0.038(4) -0.002(3) 0.011(4) 0.004(3) C1 0.019(3) 0.022(3) 0.018(3) 0.002(2) 0.004(3) 0.002(2) C2 0.016(3) 0.023(3) 0.020(4) 0.007(3) 0.001(3) 0.002(2) N13 0.028(3) 0.034(2) 0.017(2) 0.000(2) 0.003(2) -0.010(2) N21 0.026(3) 0.026(2) 0.037(3) -0.005(2) 0.003(3) 0.007(2) N23 0.022(3) 0.028(2) 0.023(3) -0.001(2) 0.000(2) 0.007(2) N11 0.023(3) 0.037(3) 0.027(3) 0.003(2) 0.004(2) -0.009(2) C25 0.035(4) 0.042(3) 0.040(3) -0.018(3) -0.004(3) -0.005(3) C13 0.042(4) 0.048(4) 0.036(3) -0.012(3) 0.014(3) -0.030(3) C21 0.020(3) 0.029(3) 0.021(3) -0.003(2) 0.004(2) 0.002(2) C26 0.027(3) 0.040(3) 0.031(3) -0.006(2) 0.003(3) 0.003(2) C23 0.036(4) 0.033(3) 0.047(4) -0.010(3) 0.013(3) 0.011(3) C22 0.025(3) 0.029(3) 0.025(3) -0.005(2) 0.003(3) 0.004(2) C12 0.024(3) 0.033(3) 0.018(3) -0.006(2) 0.000(3) -0.006(2) C15 0.055(4) 0.053(4) 0.028(3) -0.002(3) 0.015(3) -0.020(3) C14 0.052(4) 0.063(4) 0.034(4) -0.004(3) 0.020(4) -0.023(4) C24 0.037(4) 0.038(3) 0.052(4) -0.021(3) 0.005(3) 0.003(3) C11 0.026(3) 0.027(3) 0.022(3) 0.003(2) 0.008(3) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C16 C15 1.367(8) . ? C16 C11 1.387(8) . ? C16 H16 0.9300 . ? Mn1 O4 2.176(5) 2 ? Mn1 O2 2.184(4) 2 ? Mn1 O1 2.186(5) . ? Mn1 N23 2.212(5) . ? Mn1 O3 2.214(4) . ? Mn1 N13 2.221(5) . ? O4 C2 1.266(7) . ? O4 Mn1 2.176(5) 2_554 ? O1 C1 1.257(7) . ? O2 C1 1.246(8) . ? O2 Mn1 2.184(4) 2_554 ? O3 C2 1.231(8) . ? N12 N13 1.311(7) . ? N12 N11 1.331(7) . ? N22 N23 1.305(8) . ? N22 N21 1.343(8) . ? C1 C2 1.550(6) . ? N13 C11 1.386(7) . ? N21 C22 1.364(8) . ? N21 H21 0.8600 . ? N23 C21 1.365(7) . ? N11 C12 1.378(8) . ? N11 H11 0.8600 . ? C25 C26 1.369(10) . ? C25 C24 1.402(11) . ? C25 H25 0.9300 . ? C13 C14 1.367(9) . ? C13 C12 1.403(8) . ? C13 H13 0.9300 . ? C21 C26 1.390(8) . ? C21 C22 1.402(8) . ? C26 H26 0.9300 . ? C23 C24 1.362(9) . ? C23 C22 1.385(8) . ? C23 H23 0.9300 . ? C12 C11 1.393(8) . ? C15 C14 1.380(9) . ? C15 H15 0.9300 . ? C14 H14 0.9300 . ? C24 H24 0.9300 . ? 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 C15 C16 C11 115.9(5) . . ? C15 C16 H16 122.0 . . ? C11 C16 H16 122.0 . . ? O4 Mn1 O2 76.19(18) 2 2 ? O4 Mn1 O1 163.59(12) 2 . ? O2 Mn1 O1 90.46(18) 2 . ? O4 Mn1 N23 99.42(18) 2 . ? O2 Mn1 N23 93.32(18) 2 . ? O1 Mn1 N23 90.74(18) . . ? O4 Mn1 O3 94.70(17) 2 . ? O2 Mn1 O3 89.18(15) 2 . ? O1 Mn1 O3 75.31(17) . . ? N23 Mn1 O3 165.85(18) . . ? O4 Mn1 N13 93.07(18) 2 . ? O2 Mn1 N13 168.4(2) 2 . ? O1 Mn1 N13 99.31(18) . . ? N23 Mn1 N13 92.8(2) . . ? O3 Mn1 N13 87.24(18) . . ? C2 O4 Mn1 114.9(4) . 2_554 ? C1 O1 Mn1 115.2(4) . . ? C1 O2 Mn1 114.2(4) . 2_554 ? C2 O3 Mn1 114.8(4) . . ? N13 N12 N11 108.9(5) . . ? N23 N22 N21 107.7(6) . . ? O2 C1 O1 125.2(6) . . ? O2 C1 C2 117.9(4) . . ? O1 C1 C2 116.9(5) . . ? O3 C2 O4 126.4(6) . . ? O3 C2 C1 117.5(5) . . ? O4 C2 C1 116.0(5) . . ? N12 N13 C11 108.8(5) . . ? N12 N13 Mn1 116.0(4) . . ? C11 N13 Mn1 135.1(4) . . ? N22 N21 C22 111.2(6) . . ? N22 N21 H21 124.4 . . ? C22 N21 H21 124.4 . . ? N22 N23 C21 109.7(5) . . ? N22 N23 Mn1 116.4(4) . . ? C21 N23 Mn1 133.8(4) . . ? N12 N11 C12 110.5(5) . . ? N12 N11 H11 124.7 . . ? C12 N11 H11 124.7 . . ? C26 C25 C24 123.0(8) . . ? C26 C25 H25 118.5 . . ? C24 C25 H25 118.5 . . ? C14 C13 C12 115.0(5) . . ? C14 C13 H13 122.5 . . ? C12 C13 H13 122.5 . . ? N23 C21 C26 131.3(5) . . ? N23 C21 C22 107.7(5) . . ? C26 C21 C22 121.0(5) . . ? C25 C26 C21 116.0(6) . . ? C25 C26 H26 122.0 . . ? C21 C26 H26 122.0 . . ? C24 C23 C22 116.6(6) . . ? C24 C23 H23 121.7 . . ? C22 C23 H23 121.7 . . ? N21 C22 C23 134.2(5) . . ? N21 C22 C21 103.7(5) . . ? C23 C22 C21 122.1(5) . . ? N11 C12 C11 104.3(4) . . ? N11 C12 C13 133.7(5) . . ? C11 C12 C13 121.9(5) . . ? C16 C15 C14 122.6(6) . . ? C16 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? C13 C14 C15 123.0(6) . . ? C13 C14 H14 118.5 . . ? C15 C14 H14 118.5 . . ? C23 C24 C25 121.3(6) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? N13 C11 C16 131.0(5) . . ? N13 C11 C12 107.4(5) . . ? C16 C11 C12 121.5(5) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 26.17 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.734 _refine_diff_density_min -0.712 _refine_diff_density_rms 0.098 #---END data_compound9 _database_code_depnum_ccdc_archive 'CCDC 760880' #TrackingRef 'dalton_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-[(\m~2~-oxalato)-bis(benzotriazole)-cobalt(II)] ; _chemical_name_common Co(ox)(btz)2 _chemical_melting_point N/A _chemical_formula_moiety 'C14 H10 Co N6 O4' _chemical_formula_sum 'C14 H10 Co N6 O4' _chemical_formula_weight 385.21 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 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' _cell_length_a 14.436(5) _cell_length_b 12.353(3) _cell_length_c 9.245(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.25(3) _cell_angle_gamma 90.00 _cell_volume 1556.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2922 _cell_measurement_theta_min 1.41 _cell_measurement_theta_max 26.02 _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 1.137 _exptl_absorpt_correction_type sphere _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_absorpt_correction_T_min 0.7431 _exptl_absorpt_correction_T_max 0.7448 _exptl_absorpt_correction_T_ave 0.7441 _exptl_crystal_size_rad 0.1830 _exptl_special_details ; PLEASE NOTE cell_measurement_fields are not relavent to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5842 _diffrn_reflns_av_R_equivalents 0.0812 _diffrn_reflns_av_sigmaI/netI 0.0991 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.64 _reflns_number_total 2726 _reflns_number_gt 2088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SIR92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1a (Brandenberg, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All hydrogen atoms were fixed in calculated positions and refined in riding mode on the parent atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0630P)^2^] 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 SHELXL _refine_ls_extinction_coef 0.0124(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(3) _refine_ls_number_reflns 2726 _refine_ls_number_parameters 227 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 0.933 _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 C16 C 0.2519(6) 0.2467(6) 0.4256(7) 0.0336(18) Uani 1 1 d . . . H16 H 0.1943 0.2039 0.3869 0.040 Uiso 1 1 calc R . . Co1 Co 0.16807(10) 0.12104(5) 0.73972(13) 0.0195(2) Uani 1 1 d . . . O4 O 0.2450(5) -0.1112(4) 0.4794(6) 0.0220(14) Uani 1 1 d . . . O1 O 0.0842(4) 0.0933(4) 0.5085(6) 0.0233(13) Uani 1 1 d . . . O2 O 0.0798(4) -0.0089(4) 0.3059(6) 0.0241(14) Uani 1 1 d . . . O3 O 0.2434(4) -0.0127(4) 0.6809(6) 0.0257(14) Uani 1 1 d . . . N12 N 0.3459(5) 0.2559(5) 0.8358(8) 0.0269(17) Uani 1 1 d . . . N22 N -0.0152(5) 0.2466(6) 0.6500(8) 0.0256(17) Uani 1 1 d . . . C1 C 0.1173(6) 0.0190(6) 0.4437(9) 0.0202(18) Uani 1 1 d . . . C2 C 0.2093(6) -0.0397(6) 0.5435(9) 0.0212(18) Uani 1 1 d . . . N13 N 0.2786(5) 0.2212(5) 0.7099(7) 0.0225(15) Uani 1 1 d . . . N21 N -0.0611(6) 0.3376(5) 0.6671(8) 0.0296(17) Uani 1 1 d . . . H21 H -0.1230 0.3523 0.6161 0.035 Uiso 1 1 calc R . . N23 N 0.0754(5) 0.2510(5) 0.7454(7) 0.0220(14) Uani 1 1 d . . . N11 N 0.4096(5) 0.3167(5) 0.7939(8) 0.0283(16) Uani 1 1 d . . . H11 H 0.4608 0.3490 0.8588 0.034 Uiso 1 1 calc R . . C25 C 0.1592(9) 0.4921(8) 0.9891(14) 0.0358(18) Uani 1 1 d . . . H25 H 0.2130 0.5245 1.0658 0.043 Uiso 1 1 calc R . . C13 C 0.4263(6) 0.3770(6) 0.5409(8) 0.0411(19) Uani 1 1 d . . . H13 H 0.4836 0.4204 0.5789 0.049 Uiso 1 1 calc R . . C21 C 0.0884(5) 0.3482(5) 0.8229(7) 0.0227(14) Uani 1 1 d . . . C26 C 0.1724(5) 0.3929(5) 0.9332(7) 0.0287(15) Uani 1 1 d . . . H26 H 0.2337 0.3565 0.9663 0.034 Uiso 1 1 calc R . . C23 C -0.0111(6) 0.5069(6) 0.8306(8) 0.0376(19) Uani 1 1 d . . . H23 H -0.0715 0.5451 0.7961 0.045 Uiso 1 1 calc R . . C22 C 0.0002(5) 0.4046(5) 0.7737(7) 0.0283(16) Uani 1 1 d . . . C12 C 0.3851(5) 0.3227(5) 0.6364(6) 0.0244(15) Uani 1 1 d . . . C15 C 0.2933(7) 0.2987(6) 0.3308(9) 0.046(2) Uani 1 1 d . . . H15 H 0.2636 0.2906 0.2232 0.055 Uiso 1 1 calc R . . C14 C 0.3770(6) 0.3627(6) 0.3853(8) 0.041(2) Uani 1 1 d . . . H14 H 0.4012 0.3979 0.3136 0.049 Uiso 1 1 calc R . . C24 C 0.0700(6) 0.5481(6) 0.9385(8) 0.0401(19) Uani 1 1 d . . . H24 H 0.0659 0.6172 0.9808 0.048 Uiso 1 1 calc R . . C11 C 0.3003(5) 0.2608(5) 0.5840(7) 0.0236(14) 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 C16 0.036(5) 0.041(4) 0.019(3) -0.003(3) 0.002(3) -0.013(3) Co1 0.0205(4) 0.0162(3) 0.0207(4) 0.0003(5) 0.0054(3) -0.0007(6) O4 0.022(3) 0.017(2) 0.026(3) 0.002(2) 0.006(3) 0.006(2) O1 0.021(3) 0.016(2) 0.034(3) -0.002(2) 0.010(3) 0.007(2) O2 0.027(3) 0.023(3) 0.016(3) -0.005(2) -0.003(2) -0.002(2) O3 0.023(3) 0.030(3) 0.021(3) -0.005(2) 0.003(2) 0.006(2) N12 0.025(4) 0.024(3) 0.030(4) 0.004(3) 0.006(3) -0.005(3) N22 0.020(4) 0.028(4) 0.032(4) 0.002(3) 0.012(3) 0.002(3) C1 0.018(4) 0.009(3) 0.037(5) 0.000(3) 0.013(3) -0.001(3) C2 0.020(4) 0.018(3) 0.018(4) 0.005(3) -0.004(3) -0.001(3) N13 0.023(3) 0.019(3) 0.023(3) -0.002(2) 0.004(3) -0.004(3) N21 0.030(4) 0.022(3) 0.037(4) 0.000(3) 0.010(3) 0.011(3) N23 0.019(3) 0.020(3) 0.023(3) -0.002(2) 0.002(2) -0.006(3) N11 0.018(3) 0.033(3) 0.031(3) -0.002(3) 0.004(3) -0.008(3) C25 0.033(5) 0.031(3) 0.038(3) -0.011(3) 0.005(3) -0.005(3) C13 0.040(4) 0.044(4) 0.041(4) -0.003(4) 0.016(4) -0.024(4) C21 0.029(4) 0.019(3) 0.020(3) -0.003(2) 0.007(3) 0.000(3) C26 0.026(4) 0.029(3) 0.025(3) -0.003(3) 0.001(3) -0.001(3) C23 0.037(4) 0.032(4) 0.036(4) -0.007(3) 0.001(3) 0.013(3) C22 0.029(4) 0.019(3) 0.035(4) -0.003(3) 0.008(3) 0.002(3) C12 0.029(4) 0.030(3) 0.012(3) 0.001(3) 0.004(3) -0.011(3) C15 0.058(6) 0.049(5) 0.035(4) -0.002(4) 0.022(4) -0.021(4) C14 0.048(5) 0.054(5) 0.021(3) -0.004(3) 0.014(3) -0.019(4) C24 0.030(4) 0.040(4) 0.043(4) -0.018(3) 0.003(3) 0.008(3) C11 0.024(4) 0.020(3) 0.030(3) 0.000(3) 0.013(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 C16 C15 1.372(10) . ? C16 C11 1.411(9) . ? C16 H16 0.9500 . ? Co1 N23 2.102(7) . ? Co1 O2 2.105(6) 2 ? Co1 N13 2.108(7) . ? Co1 O1 2.109(6) . ? Co1 O4 2.129(6) 2 ? Co1 O3 2.145(5) . ? O4 C2 1.265(10) . ? O4 Co1 2.129(6) 2_554 ? O1 C1 1.272(9) . ? O2 C1 1.257(10) . ? O2 Co1 2.105(6) 2_554 ? O3 C2 1.247(10) . ? N12 N13 1.318(9) . ? N12 N11 1.339(10) . ? N22 N23 1.315(9) . ? N22 N21 1.340(9) . ? C1 C2 1.527(7) . ? N13 C11 1.390(9) . ? N21 C22 1.366(9) . ? N21 H21 0.8800 . ? N23 C21 1.380(8) . ? N11 C12 1.382(9) . ? N11 H11 0.8800 . ? C25 C26 1.368(12) . ? C25 C24 1.399(14) . ? C25 H25 0.9500 . ? C13 C12 1.389(9) . ? C13 C14 1.390(10) . ? C13 H13 0.9500 . ? C21 C22 1.389(9) . ? C21 C26 1.414(9) . ? C26 H26 0.9500 . ? C23 C24 1.362(10) . ? C23 C22 1.399(9) . ? C23 H23 0.9500 . ? C12 C11 1.388(9) . ? C15 C14 1.392(11) . ? C15 H15 0.9500 . ? C14 H14 0.9500 . ? C24 H24 0.9500 . ? 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 C15 C16 C11 115.8(7) . . ? C15 C16 H16 122.1 . . ? C11 C16 H16 122.1 . . ? N23 Co1 O2 92.5(2) . 2 ? N23 Co1 N13 94.1(3) . . ? O2 Co1 N13 168.9(2) 2 . ? N23 Co1 O1 89.5(2) . . ? O2 Co1 O1 89.3(2) 2 . ? N13 Co1 O1 99.7(2) . . ? N23 Co1 O4 97.8(2) . 2 ? O2 Co1 O4 79.5(2) 2 2 ? N13 Co1 O4 90.7(2) . 2 ? O1 Co1 O4 166.86(17) . 2 ? N23 Co1 O3 167.2(2) . . ? O2 Co1 O3 88.44(19) 2 . ? N13 Co1 O3 87.1(2) . . ? O1 Co1 O3 77.7(2) . . ? O4 Co1 O3 94.9(2) 2 . ? C2 O4 Co1 112.0(5) . 2_554 ? C1 O1 Co1 114.5(5) . . ? C1 O2 Co1 112.0(5) . 2_554 ? C2 O3 Co1 113.6(5) . . ? N13 N12 N11 107.6(6) . . ? N23 N22 N21 107.9(7) . . ? O2 C1 O1 124.9(8) . . ? O2 C1 C2 118.7(6) . . ? O1 C1 C2 116.4(6) . . ? O3 C2 O4 125.4(8) . . ? O3 C2 C1 117.5(6) . . ? O4 C2 C1 117.2(5) . . ? N12 N13 C11 108.7(6) . . ? N12 N13 Co1 116.4(5) . . ? C11 N13 Co1 134.9(5) . . ? N22 N21 C22 111.4(7) . . ? N22 N21 H21 124.3 . . ? C22 N21 H21 124.3 . . ? N22 N23 C21 108.6(6) . . ? N22 N23 Co1 116.9(5) . . ? C21 N23 Co1 134.4(5) . . ? N12 N11 C12 111.9(6) . . ? N12 N11 H11 124.0 . . ? C12 N11 H11 124.0 . . ? C26 C25 C24 122.9(9) . . ? C26 C25 H25 118.5 . . ? C24 C25 H25 118.5 . . ? C12 C13 C14 114.5(6) . . ? C12 C13 H13 122.7 . . ? C14 C13 H13 122.7 . . ? N23 C21 C22 108.3(6) . . ? N23 C21 C26 130.7(6) . . ? C22 C21 C26 121.1(5) . . ? C25 C26 C21 115.4(8) . . ? C25 C26 H26 122.3 . . ? C21 C26 H26 122.3 . . ? C24 C23 C22 115.7(7) . . ? C24 C23 H23 122.1 . . ? C22 C23 H23 122.1 . . ? N21 C22 C21 103.8(5) . . ? N21 C22 C23 133.6(7) . . ? C21 C22 C23 122.5(6) . . ? N11 C12 C11 103.1(6) . . ? N11 C12 C13 132.9(6) . . ? C11 C12 C13 123.9(6) . . ? C16 C15 C14 122.9(7) . . ? C16 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? C13 C14 C15 122.3(7) . . ? C13 C14 H14 118.9 . . ? C15 C14 H14 118.9 . . ? C23 C24 C25 122.3(8) . . ? C23 C24 H24 118.8 . . ? C25 C24 H24 118.8 . . ? C12 C11 N13 108.6(5) . . ? C12 C11 C16 120.5(6) . . ? N13 C11 C16 130.9(6) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.64 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.446 _refine_diff_density_min -0.613 _refine_diff_density_rms 0.093 #---END data_compound10 _database_code_depnum_ccdc_archive 'CCDC 760881' #TrackingRef 'dalton_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-[(\m~2~-oxalato)-bis(benzotriazole)-manganese(II)] ; _chemical_name_common '[Cu(ox)(btz)2]n' _chemical_melting_point N/A _chemical_formula_moiety 'C14 H10 Cu N6 O4' _chemical_formula_sum 'C14 H10 Cu N6 O4' _chemical_formula_weight 389.82 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 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' _cell_length_a 14.2379(2) _cell_length_b 12.28010(10) _cell_length_c 9.38300(10) _cell_angle_alpha 90.00 _cell_angle_beta 108.7210(10) _cell_angle_gamma 90.00 _cell_volume 1553.75(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9950 _cell_measurement_theta_min 2.243 _cell_measurement_theta_max 34.062 _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.533 _exptl_crystal_size_mid 0.089 _exptl_crystal_size_min 0.062 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 1.440 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8067 _exptl_absorpt_correction_T_max 0.9110 _exptl_absorpt_process_details 'SADABS 2008-1 (Sheldrick, 1996)' _exptl_special_details ; PLEASE NOTE cell_measurement_fields are not relavent to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _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 ;BRUKER APEXII CCD area-detector diffractometer ; _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35225 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 36.09 _reflns_number_total 6553 _reflns_number_gt 5830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND 2.1a (Brandenberg, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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. All hydrogen atoms were fixed in calculated positions and refined in riding mode on the parent atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.603(8) _refine_ls_number_reflns 6553 _refine_ls_number_parameters 227 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 1.177 _refine_ls_restrained_S_all 1.177 _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 C16 C 0.24790(18) 0.2502(2) 0.4328(2) 0.0395(5) Uani 1 1 d . . . H16 H 0.1899 0.2098 0.3955 0.047 Uiso 1 1 calc R . . Cu1 Cu 0.16841(2) 0.124191(13) 0.73839(3) 0.01896(5) Uani 1 1 d . . . O4 O 0.24995(13) -0.11099(13) 0.4988(2) 0.0305(4) Uani 1 1 d . . . O1 O 0.07518(11) 0.08895(14) 0.49139(18) 0.0251(3) Uani 1 1 d . . . O2 O 0.08508(11) -0.01950(13) 0.30768(17) 0.0245(3) Uani 1 1 d . . . O3 O 0.23962(12) -0.00190(13) 0.68333(18) 0.0265(3) Uani 1 1 d . . . N12 N 0.34287(14) 0.25663(16) 0.8344(2) 0.0283(4) Uani 1 1 d . . . N22 N -0.01265(13) 0.24506(15) 0.6538(2) 0.0287(4) Uani 1 1 d . . . C1 C 0.11479(13) 0.01505(14) 0.4402(2) 0.0190(3) Uani 1 1 d . . . C2 C 0.20985(14) -0.03697(15) 0.5506(2) 0.0214(3) Uani 1 1 d . . . N13 N 0.27439(12) 0.22352(14) 0.71130(19) 0.0243(3) Uani 1 1 d . . . N21 N -0.05944(14) 0.33458(16) 0.6733(2) 0.0307(4) Uani 1 1 d . . . H21 H -0.1200 0.3498 0.6234 0.037 Uiso 1 1 calc R . . N23 N 0.07836(12) 0.24831(14) 0.74735(19) 0.0239(3) Uani 1 1 d . . . N11 N 0.40702(13) 0.31720(17) 0.7930(2) 0.0297(4) Uani 1 1 d . . . H11 H 0.4580 0.3483 0.8549 0.036 Uiso 1 1 calc R . . C25 C 0.1607(2) 0.4847(2) 1.0006(4) 0.0475(7) Uani 1 1 d . . . H25 H 0.2137 0.5164 1.0743 0.057 Uiso 1 1 calc R . . C13 C 0.4240(2) 0.3780(2) 0.5448(3) 0.0456(6) Uani 1 1 d . . . H13 H 0.4804 0.4212 0.5814 0.055 Uiso 1 1 calc R . . C21 C 0.09082(13) 0.34173(15) 0.8303(2) 0.0250(3) Uani 1 1 d . . . C26 C 0.17367(18) 0.38488(18) 0.9428(3) 0.0353(5) Uani 1 1 d . . . H26 H 0.2338 0.3480 0.9761 0.042 Uiso 1 1 calc R . . C23 C -0.01177(19) 0.5002(2) 0.8422(3) 0.0430(6) Uani 1 1 d . . . H23 H -0.0715 0.5379 0.8097 0.052 Uiso 1 1 calc R . . C22 C 0.00093(16) 0.39891(18) 0.7825(2) 0.0305(4) Uani 1 1 d . . . C12 C 0.38211(15) 0.32386(17) 0.6409(2) 0.0303(4) Uani 1 1 d . . . C15 C 0.2908(2) 0.3006(2) 0.3391(3) 0.0526(7) Uani 1 1 d . . . H15 H 0.2619 0.2930 0.2356 0.063 Uiso 1 1 calc R . . C14 C 0.3781(3) 0.3641(3) 0.3958(3) 0.0551(8) Uani 1 1 d . . . H14 H 0.4045 0.3972 0.3281 0.066 Uiso 1 1 calc R . . C24 C 0.0696(2) 0.5399(2) 0.9514(3) 0.0522(7) Uani 1 1 d . . . H24 H 0.0644 0.6066 0.9952 0.063 Uiso 1 1 calc R . . C11 C 0.29561(14) 0.26235(16) 0.5878(2) 0.0270(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C16 0.0439(12) 0.0463(11) 0.0247(9) -0.0013(8) 0.0059(8) -0.0195(9) Cu1 0.01832(8) 0.01876(8) 0.01923(8) 0.00012(8) 0.00523(5) -0.00068(8) O4 0.0272(8) 0.0355(8) 0.0241(7) -0.0068(6) 0.0016(6) 0.0121(6) O1 0.0229(6) 0.0276(7) 0.0215(6) -0.0039(5) 0.0026(5) 0.0073(5) O2 0.0240(6) 0.0273(6) 0.0183(6) -0.0032(5) 0.0015(5) 0.0053(5) O3 0.0246(7) 0.0308(7) 0.0200(6) -0.0025(5) 0.0013(5) 0.0079(5) N12 0.0246(8) 0.0345(9) 0.0231(8) -0.0004(6) 0.0036(6) -0.0078(7) N22 0.0231(7) 0.0278(8) 0.0303(9) -0.0034(7) 0.0019(6) 0.0037(6) C1 0.0171(7) 0.0198(7) 0.0190(7) 0.0002(5) 0.0041(5) 0.0007(5) C2 0.0178(7) 0.0226(7) 0.0220(8) -0.0007(6) 0.0039(6) 0.0018(6) N13 0.0211(7) 0.0277(8) 0.0227(7) 0.0010(6) 0.0050(5) -0.0061(6) N21 0.0221(7) 0.0303(8) 0.0340(9) -0.0031(7) 0.0009(7) 0.0054(6) N23 0.0190(7) 0.0247(7) 0.0245(8) -0.0004(6) 0.0020(6) 0.0024(5) N11 0.0235(8) 0.0373(9) 0.0258(8) -0.0019(7) 0.0045(6) -0.0107(7) C25 0.0404(12) 0.0465(15) 0.0492(14) -0.0222(13) 0.0056(10) -0.0029(11) C13 0.0449(13) 0.0586(16) 0.0368(12) -0.0046(9) 0.0181(10) -0.0276(11) C21 0.0226(7) 0.0252(7) 0.0248(8) -0.0015(6) 0.0042(6) 0.0038(6) C26 0.0292(10) 0.0387(11) 0.0307(10) -0.0090(7) -0.0006(8) 0.0035(7) C23 0.0391(11) 0.0351(11) 0.0516(14) -0.0119(10) 0.0100(10) 0.0118(9) C22 0.0265(9) 0.0307(8) 0.0309(9) -0.0042(7) 0.0044(7) 0.0047(7) C12 0.0277(8) 0.0354(9) 0.0282(9) -0.0033(7) 0.0093(7) -0.0105(7) C15 0.0660(16) 0.0661(17) 0.0246(10) -0.0012(10) 0.0130(10) -0.0280(14) C14 0.0668(19) 0.0660(18) 0.0393(14) 0.0010(11) 0.0265(13) -0.0283(14) C24 0.0519(14) 0.0393(12) 0.0599(17) -0.0235(12) 0.0103(12) 0.0051(11) C11 0.0257(8) 0.0295(9) 0.0257(8) -0.0001(6) 0.0081(6) -0.0075(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C16 C15 1.369(3) . ? C16 C11 1.402(3) . ? C16 H16 0.9300 . ? Cu1 O2 1.9946(15) 2 ? Cu1 O3 2.0072(16) . ? Cu1 N23 2.0108(17) . ? Cu1 N13 2.0187(17) . ? Cu1 O1 2.3121(16) . ? Cu1 O4 2.3503(17) 2 ? O4 C2 1.252(3) . ? O4 Cu1 2.3503(17) 2_554 ? O1 C1 1.243(2) . ? O2 C1 1.252(2) . ? O2 Cu1 1.9946(15) 2_554 ? O3 C2 1.256(3) . ? N12 N13 1.314(3) . ? N12 N11 1.329(3) . ? N22 N23 1.312(2) . ? N22 N21 1.328(3) . ? C1 C2 1.553(2) . ? N13 C11 1.373(3) . ? N21 C22 1.359(3) . ? N21 H21 0.8600 . ? N23 C21 1.366(3) . ? N11 C12 1.358(3) . ? N11 H11 0.8600 . ? C25 C26 1.377(3) . ? C25 C24 1.404(4) . ? C25 H25 0.9300 . ? C13 C14 1.351(4) . ? C13 C12 1.399(3) . ? C13 H13 0.9300 . ? C21 C22 1.401(3) . ? C21 C26 1.410(3) . ? C26 H26 0.9300 . ? C23 C24 1.367(4) . ? C23 C22 1.399(3) . ? C23 H23 0.9300 . ? C12 C11 1.393(3) . ? C15 C14 1.418(4) . ? C15 H15 0.9300 . ? C14 H14 0.9300 . ? C24 H24 0.9300 . ? 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 C15 C16 C11 116.8(2) . . ? C15 C16 H16 121.6 . . ? C11 C16 H16 121.6 . . ? O2 Cu1 O3 89.38(7) 2 . ? O2 Cu1 N23 91.20(7) 2 . ? O3 Cu1 N23 167.71(7) . . ? O2 Cu1 N13 167.78(7) 2 . ? O3 Cu1 N13 88.51(7) . . ? N23 Cu1 N13 93.42(8) . . ? O2 Cu1 O1 89.76(6) 2 . ? O3 Cu1 O1 76.85(6) . . ? N23 Cu1 O1 90.87(6) . . ? N13 Cu1 O1 101.46(7) . . ? O2 Cu1 O4 76.33(6) 2 2 ? O3 Cu1 O4 95.31(6) . 2 ? N23 Cu1 O4 96.75(7) . 2 ? N13 Cu1 O4 91.88(6) . 2 ? O1 Cu1 O4 164.22(5) . 2 ? C2 O4 Cu1 108.61(13) . 2_554 ? C1 O1 Cu1 109.75(12) . . ? C1 O2 Cu1 119.70(13) . 2_554 ? C2 O3 Cu1 118.82(14) . . ? N13 N12 N11 107.55(18) . . ? N23 N22 N21 108.28(17) . . ? O1 C1 O2 125.47(17) . . ? O1 C1 C2 116.68(15) . . ? O2 C1 C2 117.84(15) . . ? O4 C2 O3 125.67(18) . . ? O4 C2 C1 116.64(15) . . ? O3 C2 C1 117.69(15) . . ? N12 N13 C11 109.40(16) . . ? N12 N13 Cu1 116.73(14) . . ? C11 N13 Cu1 133.77(13) . . ? N22 N21 C22 111.19(18) . . ? N22 N21 H21 124.4 . . ? C22 N21 H21 124.4 . . ? N22 N23 C21 109.07(16) . . ? N22 N23 Cu1 117.06(13) . . ? C21 N23 Cu1 133.85(12) . . ? N12 N11 C12 111.64(16) . . ? N12 N11 H11 124.2 . . ? C12 N11 H11 124.2 . . ? C26 C25 C24 121.8(3) . . ? C26 C25 H25 119.1 . . ? C24 C25 H25 119.1 . . ? C14 C13 C12 116.2(2) . . ? C14 C13 H13 121.9 . . ? C12 C13 H13 121.9 . . ? N23 C21 C22 107.48(15) . . ? N23 C21 C26 131.83(17) . . ? C22 C21 C26 120.68(18) . . ? C25 C26 C21 116.3(2) . . ? C25 C26 H26 121.8 . . ? C21 C26 H26 121.8 . . ? C24 C23 C22 115.5(2) . . ? C24 C23 H23 122.3 . . ? C22 C23 H23 122.3 . . ? N21 C22 C23 133.4(2) . . ? N21 C22 C21 103.98(17) . . ? C23 C22 C21 122.64(19) . . ? N11 C12 C11 104.24(17) . . ? N11 C12 C13 133.20(19) . . ? C11 C12 C13 122.5(2) . . ? C16 C15 C14 121.7(2) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C13 C14 C15 122.2(2) . . ? C13 C14 H14 118.9 . . ? C15 C14 H14 118.9 . . ? C23 C24 C25 123.0(2) . . ? C23 C24 H24 118.5 . . ? C25 C24 H24 118.5 . . ? N13 C11 C12 107.16(16) . . ? N13 C11 C16 132.35(17) . . ? C12 C11 C16 120.49(18) . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 36.09 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.356 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.060 #---END data_compound11 _database_code_depnum_ccdc_archive 'CCDC 760882' #TrackingRef 'dalton_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-[(\m~2~-oxalato)-bis(benzotriazole)-zinc(II)] ; _chemical_name_common Zn(ox)(btz)2 _chemical_melting_point N/A _chemical_formula_moiety 'C14 H10 N6 O4 Zn' _chemical_formula_sum 'C14 H10 N6 O4 Zn' _chemical_formula_weight 391.65 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 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' _cell_length_a 14.3720(14) _cell_length_b 12.3909(16) _cell_length_c 9.2272(9) _cell_angle_alpha 90.00 _cell_angle_beta 108.751(7) _cell_angle_gamma 90.00 _cell_volume 1556.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6347 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 26.03 _exptl_crystal_description needle _exptl_crystal_colour white _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 1.613 _exptl_absorpt_correction_type cylinder _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_absorpt_correction_T_min 0.7139 _exptl_absorpt_correction_T_max 0.7159 _exptl_absorpt_correction_T_ave 0.7150 _exptl_crystal_size_rad 0.2000 _exptl_special_details ; PLEASE NOTE cell_measurement_fields are not relavent to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6423 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.62 _reflns_number_total 2715 _reflns_number_gt 2284 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SIR92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1a (Brandenberg, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All hydrogen atoms were fixed in calculated positions and refined in riding mode on the parent atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^] 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 SHELXL _refine_ls_extinction_coef 0.0090(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(2) _refine_ls_number_reflns 2715 _refine_ls_number_parameters 227 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 C16 C 0.2536(4) 0.2489(5) 0.4271(6) 0.0263(13) Uani 1 1 d . . . H16 H 0.1961 0.2059 0.3893 0.032 Uiso 1 1 calc R . . Zn1 Zn 0.16796(7) 0.12284(4) 0.73987(10) 0.01428(17) Uani 1 1 d . . . O4 O 0.2448(4) -0.1106(4) 0.4787(6) 0.0191(12) Uani 1 1 d . . . O1 O 0.0848(4) 0.0948(4) 0.5078(6) 0.0170(11) Uani 1 1 d . . . O2 O 0.0798(4) -0.0098(3) 0.3091(6) 0.0187(11) Uani 1 1 d . . . O3 O 0.2438(3) -0.0127(4) 0.6813(6) 0.0190(11) Uani 1 1 d . . . N12 N 0.3474(4) 0.2566(5) 0.8360(7) 0.0182(14) Uani 1 1 d . . . N22 N -0.0159(5) 0.2471(5) 0.6485(7) 0.0224(15) Uani 1 1 d . . . C1 C 0.1177(5) 0.0206(5) 0.4461(8) 0.0174(15) Uani 1 1 d . . . C2 C 0.2104(5) -0.0382(5) 0.5460(8) 0.0163(15) Uani 1 1 d . . . N13 N 0.2806(4) 0.2227(4) 0.7098(6) 0.0158(11) Uani 1 1 d . . . N21 N -0.0622(4) 0.3387(4) 0.6645(7) 0.0210(14) Uani 1 1 d . . . H21 H -0.1237 0.3539 0.6127 0.025 Uiso 1 1 calc R . . N23 N 0.0750(4) 0.2524(4) 0.7424(6) 0.0151(11) Uani 1 1 d . . . N11 N 0.4108(4) 0.3181(5) 0.7940(7) 0.0214(13) Uani 1 1 d . . . H11 H 0.4619 0.3507 0.8584 0.026 Uiso 1 1 calc R . . C25 C 0.1578(7) 0.4926(7) 0.9854(13) 0.0321(15) Uani 1 1 d . . . H25 H 0.2121 0.5259 1.0594 0.038 Uiso 1 1 calc R . . C13 C 0.4275(5) 0.3785(5) 0.5403(7) 0.0303(13) Uani 1 1 d . . . H13 H 0.4853 0.4210 0.5775 0.036 Uiso 1 1 calc R . . C21 C 0.0873(4) 0.3480(4) 0.8213(6) 0.0175(11) Uani 1 1 d . . . C26 C 0.1703(4) 0.3924(4) 0.9325(6) 0.0249(12) Uani 1 1 d . . . H26 H 0.2311 0.3549 0.9685 0.030 Uiso 1 1 calc R . . C23 C -0.0128(4) 0.5068(5) 0.8280(7) 0.0278(13) Uani 1 1 d . . . H23 H -0.0732 0.5452 0.7944 0.033 Uiso 1 1 calc R . . C22 C -0.0017(4) 0.4040(4) 0.7707(6) 0.0183(11) Uani 1 1 d . . . C12 C 0.3861(4) 0.3240(4) 0.6389(6) 0.0200(12) Uani 1 1 d . . . C15 C 0.2938(5) 0.3009(5) 0.3304(7) 0.0365(16) Uani 1 1 d . . . H15 H 0.2641 0.2929 0.2230 0.044 Uiso 1 1 calc R . . C14 C 0.3784(5) 0.3660(6) 0.3865(7) 0.0348(15) Uani 1 1 d . . . H14 H 0.4024 0.4026 0.3152 0.042 Uiso 1 1 calc R . . C24 C 0.0685(5) 0.5479(5) 0.9347(7) 0.0337(15) Uani 1 1 d . . . H24 H 0.0643 0.6171 0.9764 0.040 Uiso 1 1 calc R . . C11 C 0.3012(4) 0.2622(4) 0.5842(6) 0.0193(11) 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 C16 0.030(3) 0.030(3) 0.018(3) -0.002(2) 0.006(3) -0.015(3) Zn1 0.0142(3) 0.0143(2) 0.0137(3) 0.0002(4) 0.00359(17) -0.0005(4) O4 0.015(2) 0.020(2) 0.021(3) -0.002(2) 0.005(2) 0.0052(19) O1 0.017(3) 0.016(2) 0.017(3) -0.003(2) 0.005(2) 0.0030(19) O2 0.018(2) 0.020(2) 0.016(3) -0.0032(18) 0.002(2) 0.0002(18) O3 0.017(2) 0.024(2) 0.014(3) -0.0053(18) 0.002(2) 0.0035(18) N12 0.013(3) 0.024(3) 0.016(3) 0.001(2) 0.003(3) -0.003(2) N22 0.019(3) 0.020(3) 0.026(4) 0.002(3) 0.005(3) 0.006(3) C1 0.015(3) 0.019(3) 0.019(4) -0.001(3) 0.006(3) -0.002(2) C2 0.012(3) 0.018(3) 0.019(4) 0.004(3) 0.005(3) 0.005(2) N13 0.014(3) 0.019(2) 0.013(3) 0.0006(19) 0.002(2) -0.0003(19) N21 0.018(3) 0.019(3) 0.024(3) -0.004(2) 0.004(2) 0.008(2) N23 0.013(2) 0.016(2) 0.016(3) 0.001(2) 0.006(2) -0.001(2) N11 0.017(3) 0.026(3) 0.020(3) -0.002(2) 0.005(2) -0.004(2) C25 0.028(4) 0.029(3) 0.034(3) -0.016(2) 0.003(3) -0.007(3) C13 0.034(3) 0.034(3) 0.028(3) -0.002(3) 0.017(3) -0.016(3) C21 0.016(3) 0.015(3) 0.024(3) 0.000(2) 0.009(2) 0.0022(19) C26 0.016(3) 0.024(3) 0.028(3) -0.004(2) -0.002(2) 0.003(2) C23 0.024(3) 0.026(3) 0.031(3) -0.003(2) 0.007(3) 0.008(2) C22 0.015(3) 0.016(3) 0.020(3) -0.0041(19) 0.001(2) 0.0007(19) C12 0.020(3) 0.025(3) 0.016(3) -0.003(2) 0.008(2) -0.004(2) C15 0.045(4) 0.043(4) 0.019(3) -0.003(3) 0.008(3) -0.015(3) C14 0.034(3) 0.048(4) 0.025(3) -0.003(3) 0.014(3) -0.019(3) C24 0.028(3) 0.024(3) 0.046(4) -0.015(3) 0.007(3) 0.004(2) C11 0.020(3) 0.018(3) 0.019(3) -0.001(2) 0.005(2) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C16 C15 1.370(9) . ? C16 C11 1.400(7) . ? C16 H16 0.9500 . ? Zn1 N23 2.093(5) . ? Zn1 O1 2.119(5) . ? Zn1 O2 2.120(5) 2 ? Zn1 N13 2.125(5) . ? Zn1 O4 2.129(6) 2 ? Zn1 O3 2.163(4) . ? O4 C2 1.278(9) . ? O4 Zn1 2.129(6) 2_554 ? O1 C1 1.252(8) . ? O2 C1 1.263(9) . ? O2 Zn1 2.120(5) 2_554 ? O3 C2 1.227(9) . ? N12 N13 1.318(8) . ? N12 N11 1.337(8) . ? N22 N23 1.317(8) . ? N22 N21 1.347(8) . ? C1 C2 1.538(6) . ? N13 C11 1.375(7) . ? N21 C22 1.350(8) . ? N21 H21 0.8800 . ? N23 C21 1.372(7) . ? N11 C12 1.361(8) . ? N11 H11 0.8800 . ? C25 C26 1.366(10) . ? C25 C24 1.397(12) . ? C25 H25 0.9500 . ? C13 C14 1.376(9) . ? C13 C12 1.408(8) . ? C13 H13 0.9500 . ? C21 C22 1.397(7) . ? C21 C26 1.411(7) . ? C26 H26 0.9500 . ? C23 C24 1.361(8) . ? C23 C22 1.408(7) . ? C23 H23 0.9500 . ? C12 C11 1.392(7) . ? C15 C14 1.411(9) . ? C15 H15 0.9500 . ? C14 H14 0.9500 . ? C24 H24 0.9500 . ? 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 C15 C16 C11 116.8(5) . . ? C15 C16 H16 121.6 . . ? C11 C16 H16 121.6 . . ? N23 Zn1 O1 88.98(19) . . ? N23 Zn1 O2 93.32(19) . 2 ? O1 Zn1 O2 89.9(2) . 2 ? N23 Zn1 N13 94.0(2) . . ? O1 Zn1 N13 99.7(2) . . ? O2 Zn1 N13 168.0(2) 2 . ? N23 Zn1 O4 99.4(2) . 2 ? O1 Zn1 O4 166.10(14) . 2 ? O2 Zn1 O4 78.6(2) 2 2 ? N13 Zn1 O4 90.8(2) . 2 ? N23 Zn1 O3 166.6(2) . . ? O1 Zn1 O3 77.66(19) . . ? O2 Zn1 O3 87.72(17) 2 . ? N13 Zn1 O3 87.34(18) . . ? O4 Zn1 O3 93.89(19) 2 . ? C2 O4 Zn1 113.6(5) . 2_554 ? C1 O1 Zn1 114.0(5) . . ? C1 O2 Zn1 113.0(5) . 2_554 ? C2 O3 Zn1 113.0(4) . . ? N13 N12 N11 107.3(5) . . ? N23 N22 N21 107.9(6) . . ? O1 C1 O2 124.8(7) . . ? O1 C1 C2 117.2(5) . . ? O2 C1 C2 118.1(5) . . ? O3 C2 O4 126.1(7) . . ? O3 C2 C1 118.0(5) . . ? O4 C2 C1 115.9(5) . . ? N12 N13 C11 109.7(5) . . ? N12 N13 Zn1 116.1(4) . . ? C11 N13 Zn1 134.2(4) . . ? N22 N21 C22 111.0(6) . . ? N22 N21 H21 124.5 . . ? C22 N21 H21 124.5 . . ? N22 N23 C21 108.9(5) . . ? N22 N23 Zn1 117.1(4) . . ? C21 N23 Zn1 134.0(4) . . ? N12 N11 C12 111.4(6) . . ? N12 N11 H11 124.3 . . ? C12 N11 H11 124.3 . . ? C26 C25 C24 122.6(7) . . ? C26 C25 H25 118.7 . . ? C24 C25 H25 118.7 . . ? C14 C13 C12 115.4(5) . . ? C14 C13 H13 122.3 . . ? C12 C13 H13 122.3 . . ? N23 C21 C22 107.7(4) . . ? N23 C21 C26 131.1(5) . . ? C22 C21 C26 121.3(5) . . ? C25 C26 C21 115.9(6) . . ? C25 C26 H26 122.1 . . ? C21 C26 H26 122.1 . . ? C24 C23 C22 115.9(5) . . ? C24 C23 H23 122.1 . . ? C22 C23 H23 122.1 . . ? N21 C22 C21 104.6(5) . . ? N21 C22 C23 133.7(5) . . ? C21 C22 C23 121.7(5) . . ? N11 C12 C11 104.7(5) . . ? N11 C12 C13 133.1(5) . . ? C11 C12 C13 122.2(5) . . ? C16 C15 C14 121.6(6) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C13 C14 C15 122.6(6) . . ? C13 C14 H14 118.7 . . ? C15 C14 H14 118.7 . . ? C23 C24 C25 122.8(6) . . ? C23 C24 H24 118.6 . . ? C25 C24 H24 118.6 . . ? N13 C11 C12 107.0(4) . . ? N13 C11 C16 131.7(5) . . ? C12 C11 C16 121.3(5) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.62 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.419 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.089 #---END data_compound12 _database_code_depnum_ccdc_archive 'CCDC 760883' #TrackingRef 'dalton_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-[(tetrakis(benzimidazole)-zinc(II))-(tris(\m~2~-oxalato)- di-zinc(II))] ; _chemical_name_common '[Zn(bnz)4][Zn2(ox)3]' _chemical_melting_point N/A _chemical_formula_moiety 'C28 H24 N8 Zn, 2(C3 O6 Zn)' _chemical_formula_sum 'C34 H24 N8 O12 Zn3' _chemical_formula_weight 932.72 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.642(3) _cell_length_b 8.8961(18) _cell_length_c 24.002(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3553.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 33719 _cell_measurement_theta_min 1.70 _cell_measurement_theta_max 29.62 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.743 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1880 _exptl_absorpt_coefficient_mu 2.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.671 _exptl_absorpt_correction_T_max 0.805 _exptl_absorpt_process_details 'MULscanABS, (PLATON03, Speck, 2003)' _exptl_special_details ; PLEASE NOTE cell_measurement_fields are not relavent to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 150(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 IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 58306 _diffrn_reflns_av_R_equivalents 0.0752 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 29.31 _reflns_number_total 4810 _reflns_number_gt 3665 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2 (Brandenberg, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All hydrogen atoms were fixed in calculated positions and refined in riding mode. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0361P)^2^] 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 4810 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0272 _refine_ls_wR_factor_ref 0.0608 _refine_ls_wR_factor_gt 0.0572 _refine_ls_goodness_of_fit_ref 0.916 _refine_ls_restrained_S_all 0.916 _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 C2 C 0.25813(10) 0.18305(18) 0.02938(7) 0.0142(3) Uani 1 1 d . . . C3 C 0.22162(10) 0.13601(19) -0.02737(7) 0.0143(3) Uani 1 1 d . . . C1 C -0.00601(10) 0.45525(18) 0.02766(7) 0.0155(3) Uani 1 1 d . . . Zn1 Zn 0.155261(11) 0.41843(2) -0.002757(8) 0.01474(5) Uani 1 1 d . . . Zn2 Zn 0.5000 0.79608(3) 0.2500 0.01661(7) Uani 1 2 d S . . O6 O 0.17043(7) 0.22260(14) -0.04761(5) 0.0184(3) Uani 1 1 d . . . O4 O 0.31427(7) 0.10236(13) 0.04765(5) 0.0171(2) Uani 1 1 d . . . O3 O 0.22915(7) 0.29502(14) 0.05250(5) 0.0184(3) Uani 1 1 d . . . O5 O 0.24437(8) 0.01366(13) -0.04776(5) 0.0179(3) Uani 1 1 d . . . O1 O -0.07293(8) 0.46654(15) 0.05103(5) 0.0211(3) Uani 1 1 d . . . O2 O 0.05263(7) 0.37955(14) 0.04434(5) 0.0187(3) Uani 1 1 d . . . N2 N 0.61504(9) 0.57851(17) 0.11919(7) 0.0211(3) Uani 1 1 d . . . H2 H 0.6570 0.5581 0.0997 0.025 Uiso 1 1 calc R . . N1 N 0.53926(9) 0.67496(18) 0.18615(6) 0.0201(3) Uani 1 1 d . . . N4 N 0.35109(10) 1.06999(18) 0.15757(7) 0.0236(3) Uani 1 1 d . . . H4 H 0.3325 1.0987 0.1259 0.028 Uiso 1 1 calc R . . N3 N 0.41606(9) 0.93368(17) 0.21977(6) 0.0195(3) Uani 1 1 d . . . C22 C 0.33813(11) 1.1394(2) 0.20828(8) 0.0206(4) Uani 1 1 d . . . C12 C 0.53757(11) 0.5284(2) 0.10910(8) 0.0184(4) Uani 1 1 d . . . C26 C 0.38026(12) 1.0932(2) 0.30343(8) 0.0241(4) Uani 1 1 d . . . H26 H 0.4071 1.0357 0.3299 0.029 Uiso 1 1 calc R . . C11 C 0.61246(11) 0.6646(2) 0.16494(8) 0.0231(4) Uani 1 1 d . . . H11 H 0.6572 0.7119 0.1801 0.028 Uiso 1 1 calc R . . C17 C 0.49052(11) 0.5898(2) 0.15131(7) 0.0181(3) Uani 1 1 d . . . C14 C 0.42363(12) 0.4163(2) 0.06915(9) 0.0280(4) Uani 1 1 d . . . H15 H 0.3996 0.3583 0.0416 0.034 Uiso 1 1 calc R . . C27 C 0.37959(11) 1.05335(19) 0.24732(8) 0.0192(3) Uani 1 1 d . . . C15 C 0.37575(12) 0.4764(2) 0.11135(9) 0.0264(4) Uani 1 1 d . . . H16 H 0.3208 0.4576 0.1111 0.032 Uiso 1 1 calc R . . C16 C 0.40805(11) 0.5629(2) 0.15339(9) 0.0230(4) Uani 1 1 d . . . H17 H 0.3763 0.6016 0.1818 0.028 Uiso 1 1 calc R . . C24 C 0.29796(12) 1.3079(2) 0.27852(10) 0.0291(4) Uani 1 1 d . . . H24 H 0.2711 1.3941 0.2900 0.035 Uiso 1 1 calc R . . C23 C 0.29593(12) 1.2684(2) 0.22287(9) 0.0261(4) Uani 1 1 d . . . H23 H 0.2679 1.3249 0.1967 0.031 Uiso 1 1 calc R . . C25 C 0.33903(13) 1.2225(2) 0.31789(9) 0.0294(4) Uani 1 1 d . . . H25 H 0.3388 1.2532 0.3549 0.035 Uiso 1 1 calc R . . C21 C 0.39786(12) 0.9501(2) 0.16661(8) 0.0222(4) Uani 1 1 d . . . H21 H 0.4155 0.8857 0.1386 0.027 Uiso 1 1 calc R . . C13 C 0.50532(12) 0.4401(2) 0.06708(8) 0.0243(4) Uani 1 1 d . . . H14 H 0.5371 0.3992 0.0390 0.029 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 C2 0.0139(7) 0.0138(7) 0.0149(8) 0.0011(6) -0.0020(6) -0.0034(6) C3 0.0107(7) 0.0173(7) 0.0147(8) 0.0001(7) -0.0011(6) -0.0029(6) C1 0.0133(7) 0.0183(7) 0.0149(8) 0.0003(6) -0.0008(7) 0.0001(6) Zn1 0.01218(9) 0.01639(9) 0.01565(10) -0.00063(8) -0.00042(8) 0.00085(8) Zn2 0.01592(13) 0.02187(13) 0.01205(13) 0.000 0.00062(11) 0.000 O6 0.0192(6) 0.0193(6) 0.0168(6) -0.0023(5) -0.0067(5) 0.0025(5) O4 0.0186(6) 0.0167(6) 0.0160(6) -0.0014(5) -0.0054(5) 0.0029(5) O3 0.0197(6) 0.0178(6) 0.0177(6) -0.0036(5) -0.0056(5) 0.0032(5) O5 0.0166(6) 0.0196(6) 0.0174(7) -0.0053(5) -0.0055(5) 0.0029(5) O1 0.0148(6) 0.0310(7) 0.0176(7) 0.0065(5) 0.0019(5) 0.0031(5) O2 0.0139(6) 0.0243(6) 0.0181(6) 0.0053(5) 0.0001(5) 0.0013(5) N2 0.0154(7) 0.0266(8) 0.0214(8) -0.0072(7) 0.0041(6) 0.0003(6) N1 0.0157(7) 0.0260(8) 0.0184(8) -0.0061(6) 0.0022(6) -0.0011(6) N4 0.0256(8) 0.0311(8) 0.0141(7) 0.0020(6) -0.0053(6) 0.0030(7) N3 0.0209(7) 0.0249(8) 0.0126(7) 0.0000(6) -0.0008(6) 0.0031(6) C22 0.0190(8) 0.0259(9) 0.0168(9) 0.0020(7) -0.0004(7) -0.0011(7) C12 0.0168(9) 0.0213(8) 0.0172(9) -0.0012(7) 0.0009(7) 0.0005(7) C26 0.0256(9) 0.0306(10) 0.0160(9) -0.0007(8) -0.0007(7) -0.0005(8) C11 0.0166(8) 0.0287(9) 0.0240(10) -0.0066(8) 0.0013(7) -0.0031(7) C17 0.0174(8) 0.0196(8) 0.0175(8) -0.0003(7) 0.0002(7) -0.0024(7) C14 0.0273(10) 0.0279(9) 0.0288(11) -0.0061(9) -0.0070(8) -0.0050(8) C27 0.0185(8) 0.0238(8) 0.0153(8) 0.0000(7) 0.0011(7) -0.0009(7) C15 0.0182(9) 0.0310(10) 0.0301(12) -0.0001(9) -0.0028(8) -0.0055(8) C16 0.0165(8) 0.0289(10) 0.0237(10) -0.0014(8) 0.0032(7) -0.0020(7) C24 0.0261(10) 0.0271(9) 0.0342(12) -0.0048(9) 0.0085(9) 0.0018(8) C23 0.0210(9) 0.0285(10) 0.0289(11) 0.0034(8) 0.0007(8) 0.0024(8) C25 0.0314(10) 0.0359(11) 0.0210(10) -0.0069(8) 0.0059(9) -0.0020(9) C21 0.0248(9) 0.0270(10) 0.0146(9) -0.0004(7) -0.0017(7) 0.0012(7) C13 0.0259(9) 0.0254(9) 0.0215(9) -0.0065(7) -0.0014(8) 0.0006(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 O3 1.238(2) . ? C2 O4 1.257(2) . ? C2 C3 1.549(2) . ? C3 O6 1.247(2) . ? C3 O5 1.252(2) . ? C1 O1 1.251(2) . ? C1 O2 1.251(2) . ? C1 C1 1.561(3) 5_565 ? Zn1 O6 2.0634(13) . ? Zn1 O1 2.0657(13) 5_565 ? Zn1 O2 2.0772(13) . ? Zn1 O4 2.0972(12) 8_665 ? Zn1 O3 2.1157(13) . ? Zn1 O5 2.1621(13) 8_665 ? Zn2 N1 1.9840(15) . ? Zn2 N1 1.9840(15) 3_655 ? Zn2 N3 1.9942(15) 3_655 ? Zn2 N3 1.9942(15) . ? O4 Zn1 2.0972(12) 8_655 ? O5 Zn1 2.1621(13) 8_655 ? O1 Zn1 2.0657(13) 5_565 ? N2 C11 1.339(2) . ? N2 C12 1.385(2) . ? N2 H2 0.8600 . ? N1 C11 1.324(2) . ? N1 C17 1.390(2) . ? N4 C21 1.338(2) . ? N4 C22 1.382(2) . ? N4 H4 0.8600 . ? N3 C21 1.319(2) . ? N3 C27 1.393(2) . ? C22 C23 1.391(3) . ? C22 C27 1.393(3) . ? C12 C13 1.386(3) . ? C12 C17 1.392(3) . ? C26 C25 1.384(3) . ? C26 C27 1.393(3) . ? C26 H26 0.9300 . ? C11 H11 0.9300 . ? C17 C16 1.394(2) . ? C14 C13 1.377(3) . ? C14 C15 1.395(3) . ? C14 H15 0.9300 . ? C15 C16 1.378(3) . ? C15 H16 0.9300 . ? C16 H17 0.9300 . ? C24 C23 1.382(3) . ? C24 C25 1.392(3) . ? C24 H24 0.9300 . ? C23 H23 0.9300 . ? C25 H25 0.9300 . ? C21 H21 0.9300 . ? C13 H14 0.9300 . ? 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 O3 C2 O4 126.34(16) . . ? O3 C2 C3 117.30(14) . . ? O4 C2 C3 116.35(14) . . ? O6 C3 O5 126.25(16) . . ? O6 C3 C2 116.33(15) . . ? O5 C3 C2 117.38(14) . . ? O1 C1 O2 126.43(16) . . ? O1 C1 C1 117.04(19) . 5_565 ? O2 C1 C1 116.53(19) . 5_565 ? O6 Zn1 O1 101.93(5) . 5_565 ? O6 Zn1 O2 104.12(5) . . ? O1 Zn1 O2 80.93(5) 5_565 . ? O6 Zn1 O4 158.46(5) . 8_665 ? O1 Zn1 O4 95.59(5) 5_565 8_665 ? O2 Zn1 O4 90.85(5) . 8_665 ? O6 Zn1 O3 79.50(5) . . ? O1 Zn1 O3 173.82(5) 5_565 . ? O2 Zn1 O3 92.89(5) . . ? O4 Zn1 O3 84.42(5) 8_665 . ? O6 Zn1 O5 88.61(5) . 8_665 ? O1 Zn1 O5 92.18(5) 5_565 8_665 ? O2 Zn1 O5 166.50(5) . 8_665 ? O4 Zn1 O5 78.21(5) 8_665 8_665 ? O3 Zn1 O5 93.87(5) . 8_665 ? N1 Zn2 N1 114.21(10) . 3_655 ? N1 Zn2 N3 112.57(6) . 3_655 ? N1 Zn2 N3 106.44(6) 3_655 3_655 ? N1 Zn2 N3 106.44(6) . . ? N1 Zn2 N3 112.57(6) 3_655 . ? N3 Zn2 N3 104.26(9) 3_655 . ? C3 O6 Zn1 113.70(11) . . ? C2 O4 Zn1 115.09(11) . 8_655 ? C2 O3 Zn1 111.29(11) . . ? C3 O5 Zn1 112.27(11) . 8_655 ? C1 O1 Zn1 112.25(11) . 5_565 ? C1 O2 Zn1 112.18(11) . . ? C11 N2 C12 107.31(15) . . ? C11 N2 H2 126.3 . . ? C12 N2 H2 126.3 . . ? C11 N1 C17 105.52(15) . . ? C11 N1 Zn2 129.66(13) . . ? C17 N1 Zn2 124.66(12) . . ? C21 N4 C22 107.69(16) . . ? C21 N4 H4 126.2 . . ? C22 N4 H4 126.2 . . ? C21 N3 C27 105.94(15) . . ? C21 N3 Zn2 125.50(13) . . ? C27 N3 Zn2 126.99(12) . . ? N4 C22 C23 132.02(18) . . ? N4 C22 C27 105.66(16) . . ? C23 C22 C27 122.31(18) . . ? N2 C12 C13 132.05(17) . . ? N2 C12 C17 105.67(16) . . ? C13 C12 C17 122.26(17) . . ? C25 C26 C27 116.77(18) . . ? C25 C26 H26 121.6 . . ? C27 C26 H26 121.6 . . ? N1 C11 N2 112.63(16) . . ? N1 C11 H11 123.7 . . ? N2 C11 H11 123.7 . . ? N1 C17 C12 108.87(15) . . ? N1 C17 C16 130.27(17) . . ? C12 C17 C16 120.86(17) . . ? C13 C14 C15 122.08(19) . . ? C13 C14 H15 119.0 . . ? C15 C14 H15 119.0 . . ? N3 C27 C26 130.58(17) . . ? N3 C27 C22 108.45(16) . . ? C26 C27 C22 120.97(17) . . ? C16 C15 C14 121.51(18) . . ? C16 C15 H16 119.2 . . ? C14 C15 H16 119.2 . . ? C15 C16 C17 116.96(18) . . ? C15 C16 H17 121.5 . . ? C17 C16 H17 121.5 . . ? C23 C24 C25 121.99(19) . . ? C23 C24 H24 119.0 . . ? C25 C24 H24 119.0 . . ? C24 C23 C22 116.16(19) . . ? C24 C23 H23 121.9 . . ? C22 C23 H23 121.9 . . ? C26 C25 C24 121.80(19) . . ? C26 C25 H25 119.1 . . ? C24 C25 H25 119.1 . . ? N3 C21 N4 112.25(17) . . ? N3 C21 H21 123.9 . . ? N4 C21 H21 123.9 . . ? C14 C13 C12 116.31(18) . . ? C14 C13 H14 121.8 . . ? C12 C13 H14 121.8 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 29.31 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.500 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.072 #---END data_compound13 _database_code_depnum_ccdc_archive 'CCDC 760884' #TrackingRef 'dalton_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (oxalato)-di(benzimidazole)-copper(II) hydrate/methanol solvate ; _chemical_name_common ; Copper(II) bis-benzimidazole oxalate ; _chemical_melting_point N/A _chemical_formula_moiety 'C16.50 H14.88 Cu N4 O5' _chemical_formula_sum 'C16.50 H14.88 Cu N4 O5' _chemical_formula_weight 412.74 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/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 20.046(4) _cell_length_b 10.587(2) _cell_length_c 17.484(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.30(3) _cell_angle_gamma 90.00 _cell_volume 3561.5(12) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8006 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 25.48 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1687 _exptl_absorpt_coefficient_mu 1.262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5237 _exptl_absorpt_correction_T_max 0.6513 _exptl_absorpt_process_details 'MULscanABS, (PLATON, Speck, 2003)' _exptl_special_details ; PLEASE NOTE cell_measurement_fields are not relavent to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 150(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 IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13619 _diffrn_reflns_av_R_equivalents 0.0910 _diffrn_reflns_av_sigmaI/netI 0.0695 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.16 _reflns_number_total 3187 _reflns_number_gt 2075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2 (Brandenberg, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All hydrogen atoms were fixed in calculated positions and refined in riding mode. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0601P)^2^] 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 3187 _refine_ls_number_parameters 239 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1105 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.919 _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 Cu1 Cu 0.21157(3) 0.52787(4) 0.12355(3) 0.04748(17) Uani 1 1 d . . . O4 O 0.25363(15) 0.4905(2) 0.03732(16) 0.0519(7) Uani 1 1 d . A . O1 O 0.33088(15) 0.7869(2) 0.07032(16) 0.0531(7) Uani 1 1 d . . . O2 O 0.26799(15) 0.6815(2) 0.13605(15) 0.0520(7) Uani 1 1 d . A . N1 N 0.16811(18) 0.3590(3) 0.10771(19) 0.0515(8) Uani 1 1 d . A . N3 N 0.19218(17) 0.5534(3) 0.22733(18) 0.0469(8) Uani 1 1 d . A . N4 N 0.17092(19) 0.4933(3) 0.33884(19) 0.0530(8) Uani 1 1 d . A . H4 H 0.1691 0.4456 0.3780 0.064 Uiso 1 1 calc R . . C21 C 0.1972(2) 0.2596(4) 0.0843(2) 0.0539(10) Uani 1 1 d . . . H21 H 0.2393 0.2626 0.0719 0.065 Uiso 1 1 calc R A . N2 N 0.15955(19) 0.1544(3) 0.08034(19) 0.0543(8) Uani 1 1 d . A . H2 H 0.1702 0.0806 0.0670 0.065 Uiso 1 1 calc R . . O3 O 0.32765(16) 0.5775(3) -0.02198(17) 0.0580(7) Uani 1 1 d . A . C11 C 0.1956(2) 0.4611(4) 0.2787(2) 0.0520(10) Uani 1 1 d . . . H11 H 0.2135 0.3816 0.2734 0.062 Uiso 1 1 calc R A . C2 C 0.2936(2) 0.5776(4) 0.0267(2) 0.0480(9) Uani 1 1 d . . . C13 C 0.1475(2) 0.7775(4) 0.2287(2) 0.0586(11) Uani 1 1 d . A . H13 H 0.1562 0.8049 0.1819 0.070 Uiso 1 1 calc R . . C12 C 0.1624(2) 0.6542(3) 0.2566(2) 0.0463(9) Uani 1 1 d . . . C27 C 0.1010(2) 0.1858(4) 0.1014(2) 0.0533(10) Uani 1 1 d . . . C17 C 0.1488(2) 0.6163(4) 0.3274(2) 0.0503(9) Uani 1 1 d . A . C1 C 0.2984(2) 0.6930(3) 0.0822(2) 0.0457(9) Uani 1 1 d . A . C22 C 0.1062(2) 0.3146(4) 0.1191(2) 0.0514(10) Uani 1 1 d . A . C16 C 0.1187(3) 0.6961(5) 0.3711(3) 0.0690(12) Uani 1 1 d . . . H16 H 0.1084 0.6691 0.4171 0.083 Uiso 1 1 calc R A . C14 C 0.1191(3) 0.8565(4) 0.2738(3) 0.0753(14) Uani 1 1 d . . . H14 H 0.1091 0.9395 0.2572 0.090 Uiso 1 1 calc R A . C26 C 0.0448(3) 0.1143(5) 0.1069(3) 0.0747(14) Uani 1 1 d . A . H26 H 0.0416 0.0285 0.0950 0.090 Uiso 1 1 calc R . . C23 C 0.0540(2) 0.3756(5) 0.1424(3) 0.0709(13) Uani 1 1 d . . . H23 H 0.0565 0.4617 0.1534 0.085 Uiso 1 1 calc R A . C24 C -0.0014(3) 0.3047(6) 0.1486(4) 0.0848(16) Uani 1 1 d . A . H24 H -0.0368 0.3432 0.1650 0.102 Uiso 1 1 calc R . . C15 C 0.1049(3) 0.8166(5) 0.3431(3) 0.0828(16) Uani 1 1 d . A . H15 H 0.0854 0.8734 0.3713 0.099 Uiso 1 1 calc R . . C25 C -0.0058(3) 0.1760(5) 0.1308(4) 0.0876(17) Uani 1 1 d . . . H25 H -0.0443 0.1309 0.1353 0.105 Uiso 1 1 calc R A . O11 O 0.1188(4) 0.6515(9) 0.0551(5) 0.055(2) Uiso 0.55(2) 1 d P A 1 O31 O 0.1095(5) 0.6227(10) 0.0422(6) 0.058(3) Uiso 0.45(2) 1 d PD A 2 C31 C 0.0462(7) 0.6699(19) 0.0530(12) 0.153(10) Uiso 0.45(2) 1 d PD A 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 Cu1 0.0681(3) 0.0318(2) 0.0474(3) -0.0025(2) 0.0242(2) -0.0012(2) O4 0.0734(18) 0.0318(14) 0.0579(15) -0.0045(11) 0.0308(14) -0.0055(13) O1 0.0721(19) 0.0340(14) 0.0585(16) -0.0061(12) 0.0271(14) -0.0062(13) O2 0.0742(19) 0.0384(14) 0.0490(14) -0.0065(11) 0.0265(14) -0.0032(13) N1 0.065(2) 0.0378(17) 0.0571(19) -0.0069(15) 0.0266(17) 0.0025(16) N3 0.064(2) 0.0329(17) 0.0468(17) 0.0008(13) 0.0210(15) 0.0016(14) N4 0.073(2) 0.043(2) 0.0460(17) 0.0118(14) 0.0214(16) -0.0032(15) C21 0.071(3) 0.043(2) 0.057(2) 0.0018(18) 0.033(2) 0.000(2) N2 0.076(2) 0.0313(17) 0.061(2) -0.0060(15) 0.0293(18) -0.0024(16) O3 0.083(2) 0.0391(14) 0.0638(17) -0.0100(13) 0.0407(16) -0.0068(14) C11 0.070(3) 0.033(2) 0.053(2) 0.0078(18) 0.0177(19) -0.0001(19) C2 0.067(3) 0.0313(19) 0.048(2) 0.0014(16) 0.019(2) 0.0047(19) C13 0.086(3) 0.041(2) 0.052(2) 0.0039(18) 0.025(2) 0.008(2) C12 0.061(2) 0.036(2) 0.044(2) -0.0002(16) 0.0183(18) 0.0015(17) C27 0.061(3) 0.042(2) 0.058(2) -0.0051(18) 0.019(2) -0.0066(19) C17 0.060(2) 0.045(2) 0.048(2) -0.0009(17) 0.0189(19) -0.0029(19) C1 0.056(2) 0.035(2) 0.047(2) -0.0024(16) 0.0154(19) 0.0040(18) C22 0.059(3) 0.043(2) 0.055(2) -0.0091(18) 0.022(2) -0.0050(19) C16 0.077(3) 0.079(3) 0.060(3) -0.004(2) 0.033(2) 0.007(3) C14 0.105(4) 0.048(3) 0.078(3) -0.002(2) 0.034(3) 0.021(3) C26 0.079(3) 0.053(3) 0.093(4) -0.008(3) 0.024(3) -0.011(3) C23 0.066(3) 0.062(3) 0.086(3) -0.018(3) 0.025(3) 0.002(2) C24 0.062(3) 0.089(4) 0.112(4) -0.015(3) 0.039(3) -0.002(3) C15 0.104(4) 0.073(4) 0.080(3) -0.009(3) 0.040(3) 0.022(3) C25 0.064(3) 0.083(4) 0.121(5) -0.010(3) 0.035(3) -0.022(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 Cu1 O2 1.958(3) . ? Cu1 O4 1.963(3) . ? Cu1 N1 1.974(3) . ? Cu1 N3 1.978(3) . ? Cu1 O11 2.314(7) . ? Cu1 O31 2.364(9) . ? O4 C2 1.269(5) . ? O1 C1 1.238(4) . ? O2 C1 1.263(5) . ? N1 C21 1.322(5) . ? N1 C22 1.393(5) . ? N3 C11 1.316(5) . ? N3 C12 1.389(5) . ? N4 C11 1.326(5) . ? N4 C17 1.372(5) . ? N4 H4 0.8600 . ? C21 N2 1.336(5) . ? C21 H21 0.9300 . ? N2 C27 1.366(5) . ? N2 H2 0.8600 . ? O3 C2 1.232(5) . ? C11 H11 0.9300 . ? C2 C1 1.546(5) . ? C13 C14 1.378(6) . ? C13 C12 1.397(5) . ? C13 H13 0.9300 . ? C12 C17 1.398(5) . ? C27 C26 1.383(6) . ? C27 C22 1.395(5) . ? C17 C16 1.386(6) . ? C22 C23 1.384(6) . ? C16 C15 1.367(7) . ? C16 H16 0.9300 . ? C14 C15 1.386(7) . ? C14 H14 0.9300 . ? C26 C25 1.366(7) . ? C26 H26 0.9300 . ? C23 C24 1.370(7) . ? C23 H23 0.9300 . ? C24 C25 1.395(7) . ? C24 H24 0.9300 . ? C15 H15 0.9300 . ? C25 H25 0.9300 . ? O31 C31 1.4248(11) . ? 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 Cu1 O4 83.93(11) . . ? O2 Cu1 N1 170.55(13) . . ? O4 Cu1 N1 88.70(12) . . ? O2 Cu1 N3 92.31(12) . . ? O4 Cu1 N3 165.78(13) . . ? N1 Cu1 N3 93.42(13) . . ? O2 Cu1 O11 86.7(3) . . ? O4 Cu1 O11 99.9(2) . . ? N1 Cu1 O11 100.4(3) . . ? N3 Cu1 O11 93.5(2) . . ? O2 Cu1 O31 95.2(3) . . ? O4 Cu1 O31 96.3(2) . . ? N1 Cu1 O31 91.5(3) . . ? N3 Cu1 O31 97.7(2) . . ? O11 Cu1 O31 9.6(3) . . ? C2 O4 Cu1 113.0(2) . . ? C1 O2 Cu1 112.4(2) . . ? C21 N1 C22 105.2(3) . . ? C21 N1 Cu1 123.3(3) . . ? C22 N1 Cu1 131.5(3) . . ? C11 N3 C12 105.3(3) . . ? C11 N3 Cu1 122.6(3) . . ? C12 N3 Cu1 131.2(2) . . ? C11 N4 C17 107.8(3) . . ? C11 N4 H4 126.1 . . ? C17 N4 H4 126.1 . . ? N1 C21 N2 112.9(4) . . ? N1 C21 H21 123.6 . . ? N2 C21 H21 123.6 . . ? C21 N2 C27 107.4(3) . . ? C21 N2 H2 126.3 . . ? C27 N2 H2 126.3 . . ? N3 C11 N4 113.0(4) . . ? N3 C11 H11 123.5 . . ? N4 C11 H11 123.5 . . ? O3 C2 O4 126.5(4) . . ? O3 C2 C1 119.0(4) . . ? O4 C2 C1 114.4(3) . . ? C14 C13 C12 116.7(4) . . ? C14 C13 H13 121.7 . . ? C12 C13 H13 121.7 . . ? N3 C12 C13 131.4(4) . . ? N3 C12 C17 108.5(3) . . ? C13 C12 C17 120.1(4) . . ? N2 C27 C26 131.6(4) . . ? N2 C27 C22 106.3(4) . . ? C26 C27 C22 122.1(4) . . ? N4 C17 C16 132.1(4) . . ? N4 C17 C12 105.4(3) . . ? C16 C17 C12 122.5(4) . . ? O1 C1 O2 126.1(3) . . ? O1 C1 C2 118.2(3) . . ? O2 C1 C2 115.7(3) . . ? C23 C22 N1 131.4(4) . . ? C23 C22 C27 120.4(4) . . ? N1 C22 C27 108.2(4) . . ? C15 C16 C17 116.6(4) . . ? C15 C16 H16 121.7 . . ? C17 C16 H16 121.7 . . ? C13 C14 C15 122.4(4) . . ? C13 C14 H14 118.8 . . ? C15 C14 H14 118.8 . . ? C25 C26 C27 116.6(4) . . ? C25 C26 H26 121.7 . . ? C27 C26 H26 121.7 . . ? C24 C23 C22 117.6(4) . . ? C24 C23 H23 121.2 . . ? C22 C23 H23 121.2 . . ? C23 C24 C25 121.2(5) . . ? C23 C24 H24 119.4 . . ? C25 C24 H24 119.4 . . ? C16 C15 C14 121.8(5) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C26 C25 C24 122.0(5) . . ? C26 C25 H25 119.0 . . ? C24 C25 H25 119.0 . . ? C31 O31 Cu1 136.2(10) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.16 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.356 _refine_diff_density_min -0.531 _refine_diff_density_rms 0.065