# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'S.Brooker ' _publ_contact_author_email 'sbrooker@alkali.otago.ac.nz ' _publ_author_name S.Brooker data_rs23 _database_code_depnum_ccdc_archive 'CCDC 804221' #TrackingRef 'rs23.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 B F4 N4 Ni' _chemical_formula_weight 436.89 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 7.2737(15) _cell_length_b 10.6471(18) _cell_length_c 11.3778(15) _cell_angle_alpha 90.00 _cell_angle_beta 94.181(3) _cell_angle_gamma 90.00 _cell_volume 878.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 2109 _cell_measurement_theta_min 2.626 _cell_measurement_theta_max 21.107 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 1.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6614 _exptl_absorpt_correction_T_max 0.9132 _exptl_absorpt_process_details 'SCALE (Bruker AXS Inc.)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(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 Kappa Apex II area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11732 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.0737 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3339 _reflns_number_gt 2392 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Nickel complex of [1+1] macrocycle of 2,2'-iminobisbenzaldehyde with diethylenetriamine, tetrafluoroborate salt. Entire macrocycle in asymmetric unit. All non-H ANIS. No solvent. No disorder. All H's calc and ride except for the amine hydrogen atom (H3x) which was freely refined (x,y,z) and where U(H3x)=1.2xU(N3). Initial refinement with no twin law gave flack x=0.74(3). Inversion of the structure gave flack x=0.22(2). Addition of twin law (-1 0 0 0 1 0 0 0 -1) gave better refinement with BASF= 0.77021, and R1=5.04%. Given the structure had a large number of correlations between ligand atoms that could be related by a C2 axis through N1 and Ni1 and N3, the higher symmetry space group P2/n was tried, but resulted in disorder of both the tetrafluoroborate anion (over two superimposed sites) and the aliphatic arms of the macrocycle (up and down). The refinement reached only R1=9.93%. Hence the structure was completed in Pn, with twin law and BASF as above. H-bond present between BF4 and N3-H. ; _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^)+(0.0539P)^2^+0.3182P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_number_reflns 3339 _refine_ls_number_parameters 257 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.25013(12) 0.20369(5) 0.24974(9) 0.0371(2) Uani 1 1 d . . . N1 N 0.2554(10) 0.0284(3) 0.2568(6) 0.0285(8) Uani 1 1 d . . . C1 C 0.2262(9) -0.0354(6) 0.3623(6) 0.0301(17) Uani 1 1 d . . . C2 C 0.1451(9) -0.1581(7) 0.3619(6) 0.0342(16) Uani 1 1 d . . . H2 H 0.1050 -0.1963 0.2890 0.041 Uiso 1 1 calc R . . C3 C 0.1250(10) -0.2204(7) 0.4642(8) 0.043(2) Uani 1 1 d . . . H3 H 0.0732 -0.3023 0.4603 0.052 Uiso 1 1 calc R . . C4 C 0.1751(11) -0.1713(7) 0.5719(7) 0.0425(19) Uani 1 1 d . . . H4 H 0.1612 -0.2183 0.6417 0.051 Uiso 1 1 calc R . . C5 C 0.2475(10) -0.0500(7) 0.5771(6) 0.0380(18) Uani 1 1 d . . . H5 H 0.2817 -0.0136 0.6517 0.046 Uiso 1 1 calc R . . C6 C 0.2713(9) 0.0203(7) 0.4730(6) 0.0318(17) Uani 1 1 d . . . C7 C 0.3334(9) 0.1467(7) 0.4892(6) 0.0355(17) Uani 1 1 d . . . H7 H 0.3813 0.1717 0.5655 0.043 Uiso 1 1 calc R . . N2 N 0.3282(9) 0.2265(6) 0.4078(6) 0.0358(18) Uani 1 1 d . . . C8 C 0.3805(12) 0.3577(7) 0.4378(7) 0.052(2) Uani 1 1 d . . . H8A H 0.5045 0.3600 0.4799 0.063 Uiso 1 1 calc R . . H8B H 0.2913 0.3948 0.4896 0.063 Uiso 1 1 calc R . . C9 C 0.3805(12) 0.4302(6) 0.3255(6) 0.068(2) Uani 1 1 d . . . H9A H 0.3581 0.5201 0.3412 0.081 Uiso 1 1 calc R . . H9B H 0.5024 0.4225 0.2928 0.081 Uiso 1 1 calc R . . N3 N 0.2417(14) 0.3841(4) 0.2427(8) 0.0484(14) Uani 1 1 d . . . H3X H 0.135(9) 0.399(6) 0.283(6) 0.058 Uiso 1 1 d . . . C10 C 0.2444(10) 0.4258(6) 0.1199(6) 0.0502(18) Uani 1 1 d . . . H10A H 0.3701 0.4195 0.0924 0.060 Uiso 1 1 calc R . . H10B H 0.2010 0.5136 0.1109 0.060 Uiso 1 1 calc R . . C11 C 0.1157(11) 0.3377(8) 0.0536(7) 0.0431(19) Uani 1 1 d . . . H11A H -0.0132 0.3540 0.0718 0.052 Uiso 1 1 calc R . . H11B H 0.1249 0.3469 -0.0323 0.052 Uiso 1 1 calc R . . N4 N 0.1740(10) 0.2117(5) 0.0931(6) 0.0370(18) Uani 1 1 d . . . C12 C 0.1780(10) 0.1227(7) 0.0156(6) 0.0346(18) Uani 1 1 d . . . H12 H 0.1344 0.1414 -0.0632 0.042 Uiso 1 1 calc R . . C13 C 0.2442(9) -0.0031(7) 0.0407(6) 0.0314(16) Uani 1 1 d . . . C14 C 0.2721(10) -0.0795(8) -0.0561(6) 0.0403(18) Uani 1 1 d . . . H14 H 0.2380 -0.0492 -0.1331 0.048 Uiso 1 1 calc R . . C15 C 0.3463(11) -0.1953(8) -0.0432(8) 0.047(2) Uani 1 1 d . . . H15 H 0.3578 -0.2478 -0.1098 0.056 Uiso 1 1 calc R . . C16 C 0.4053(10) -0.2361(8) 0.0686(7) 0.0386(18) Uani 1 1 d . . . H16 H 0.4645 -0.3153 0.0788 0.046 Uiso 1 1 calc R . . C17 C 0.3778(9) -0.1612(7) 0.1669(6) 0.0318(16) Uani 1 1 d . . . H17 H 0.4216 -0.1903 0.2427 0.038 Uiso 1 1 calc R . . C18 C 0.2881(9) -0.0446(6) 0.1576(6) 0.0305(17) Uani 1 1 d . . . B1 B 0.3171(10) 0.4386(6) 0.7537(7) 0.047(2) Uani 1 1 d . . . F11 F 0.4730(6) 0.3831(4) 0.7122(4) 0.0691(12) Uani 1 1 d . . . F12 F 0.3679(7) 0.5072(4) 0.8531(4) 0.0685(13) Uani 1 1 d . . . F13 F 0.1941(6) 0.3469(4) 0.7789(4) 0.0691(12) Uani 1 1 d . . . F14 F 0.2370(6) 0.5173(4) 0.6673(4) 0.0716(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 Ni1 0.0554(4) 0.0209(3) 0.0360(4) 0.0002(5) 0.0087(3) 0.0015(5) N1 0.036(2) 0.0233(18) 0.026(2) -0.001(3) 0.0031(17) -0.002(3) C1 0.029(4) 0.024(4) 0.038(4) 0.001(3) 0.009(3) 0.000(3) C2 0.033(4) 0.030(4) 0.042(4) -0.003(3) 0.015(3) 0.006(3) C3 0.046(5) 0.022(4) 0.065(6) 0.013(4) 0.025(4) 0.002(3) C4 0.046(5) 0.045(4) 0.039(4) 0.018(3) 0.019(3) 0.015(4) C5 0.039(4) 0.045(4) 0.031(4) 0.006(3) 0.005(3) 0.008(3) C6 0.034(4) 0.032(4) 0.029(4) -0.003(3) 0.005(3) 0.008(3) C7 0.033(4) 0.037(4) 0.037(4) -0.011(3) -0.001(3) -0.002(3) N2 0.045(5) 0.025(4) 0.038(4) -0.006(3) 0.007(3) 0.002(3) C8 0.070(6) 0.026(4) 0.062(6) -0.019(4) 0.012(4) -0.006(4) C9 0.095(6) 0.038(4) 0.068(5) -0.014(4) -0.006(5) -0.028(4) N3 0.063(4) 0.033(2) 0.051(4) -0.002(4) 0.013(3) 0.007(4) C10 0.070(5) 0.024(3) 0.060(4) 0.022(3) 0.031(4) 0.009(3) C11 0.048(5) 0.031(4) 0.052(5) 0.007(3) 0.010(4) 0.007(3) N4 0.043(5) 0.030(4) 0.038(4) 0.011(3) 0.009(3) 0.006(2) C12 0.040(4) 0.032(4) 0.032(4) 0.000(3) 0.010(3) -0.006(3) C13 0.028(4) 0.028(3) 0.039(4) -0.007(3) 0.005(3) -0.004(3) C14 0.040(4) 0.045(4) 0.037(4) -0.006(3) 0.011(3) -0.004(3) C15 0.047(5) 0.046(5) 0.050(5) -0.022(4) 0.018(4) -0.005(3) C16 0.040(4) 0.025(3) 0.052(5) -0.006(3) 0.011(3) -0.001(3) C17 0.040(4) 0.022(3) 0.034(4) -0.005(3) 0.007(3) -0.003(3) C18 0.031(4) 0.027(4) 0.034(4) -0.003(3) 0.005(3) -0.011(3) B1 0.069(6) 0.032(4) 0.041(4) 0.009(4) 0.018(5) -0.001(3) F11 0.082(3) 0.059(2) 0.070(3) 0.017(2) 0.030(2) 0.022(2) F12 0.097(3) 0.046(2) 0.063(3) -0.015(2) 0.007(3) -0.006(2) F13 0.087(4) 0.053(2) 0.067(3) 0.003(2) -0.001(2) -0.023(2) F14 0.090(3) 0.067(3) 0.060(3) 0.025(2) 0.023(2) 0.025(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N4 1.830(7) . y Ni1 N2 1.861(7) . y Ni1 N1 1.869(3) . y Ni1 N3 1.924(4) . y N1 C18 1.404(8) . ? N1 C1 1.408(8) . ? C1 C6 1.409(9) . ? C1 C2 1.433(10) . ? C2 C3 1.357(10) . ? C2 H2 0.9500 . ? C3 C4 1.357(11) . ? C3 H3 0.9500 . ? C4 C5 1.394(10) . ? C4 H4 0.9500 . ? C5 C6 1.423(9) . ? C5 H5 0.9500 . ? C6 C7 1.426(10) . ? C7 N2 1.255(9) . ? C7 H7 0.9500 . ? N2 C8 1.482(10) . ? C8 C9 1.493(10) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N3 1.417(11) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N3 C10 1.467(10) . ? N3 H3X 0.94(7) . ? C10 C11 1.490(10) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N4 1.467(9) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N4 C12 1.297(9) . ? C12 C13 1.444(10) . ? C12 H12 0.9500 . ? C13 C14 1.396(10) . ? C13 C18 1.416(9) . ? C14 C15 1.349(11) . ? C14 H14 0.9500 . ? C15 C16 1.383(10) . ? C15 H15 0.9500 . ? C16 C17 1.400(10) . ? C16 H16 0.9500 . ? C17 C18 1.403(9) . ? C17 H17 0.9500 . ? B1 F13 1.368(7) . ? B1 F12 1.374(9) . ? B1 F14 1.388(8) . ? B1 F11 1.392(8) . ? 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 N4 Ni1 N2 169.83(19) . . y N4 Ni1 N1 95.3(3) . . y N2 Ni1 N1 94.9(3) . . y N4 Ni1 N3 84.6(3) . . y N2 Ni1 N3 85.2(3) . . y N1 Ni1 N3 179.3(4) . . y C18 N1 C1 117.6(4) . . ? C18 N1 Ni1 121.5(5) . . ? C1 N1 Ni1 121.0(5) . . ? N1 C1 C6 121.3(6) . . ? N1 C1 C2 121.6(6) . . ? C6 C1 C2 117.1(7) . . ? C3 C2 C1 120.9(7) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C4 C3 C2 123.2(7) . . ? C4 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? C3 C4 C5 118.1(7) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? C4 C5 C6 121.4(7) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 119.2(7) . . ? C1 C6 C7 124.3(7) . . ? C5 C6 C7 116.5(6) . . ? N2 C7 C6 123.4(7) . . ? N2 C7 H7 118.3 . . ? C6 C7 H7 118.3 . . ? C7 N2 C8 118.3(7) . . ? C7 N2 Ni1 128.0(6) . . ? C8 N2 Ni1 113.6(5) . . ? N2 C8 C9 107.8(6) . . ? N2 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? N2 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.5 . . ? N3 C9 C8 110.3(7) . . ? N3 C9 H9A 109.6 . . ? C8 C9 H9A 109.6 . . ? N3 C9 H9B 109.6 . . ? C8 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C9 N3 C10 118.1(7) . . ? C9 N3 Ni1 107.4(5) . . ? C10 N3 Ni1 109.8(5) . . ? C9 N3 H3X 101(4) . . ? C10 N3 H3X 119(4) . . ? Ni1 N3 H3X 100(4) . . ? N3 C10 C11 103.9(6) . . ? N3 C10 H10A 111.0 . . ? C11 C10 H10A 111.0 . . ? N3 C10 H10B 111.0 . . ? C11 C10 H10B 111.0 . . ? H10A C10 H10B 109.0 . . ? N4 C11 C10 105.3(6) . . ? N4 C11 H11A 110.7 . . ? C10 C11 H11A 110.7 . . ? N4 C11 H11B 110.7 . . ? C10 C11 H11B 110.7 . . ? H11A C11 H11B 108.8 . . ? C12 N4 C11 118.8(7) . . ? C12 N4 Ni1 127.4(5) . . ? C11 N4 Ni1 113.6(5) . . ? N4 C12 C13 124.5(7) . . ? N4 C12 H12 117.7 . . ? C13 C12 H12 117.7 . . ? C14 C13 C18 121.5(7) . . ? C14 C13 C12 116.7(7) . . ? C18 C13 C12 121.7(7) . . ? C15 C14 C13 121.8(7) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C14 C15 C16 118.8(7) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C15 C16 C17 120.2(7) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 122.5(7) . . ? C16 C17 H17 118.8 . . ? C18 C17 H17 118.8 . . ? C17 C18 N1 122.3(6) . . ? C17 C18 C13 114.8(6) . . ? N1 C18 C13 122.8(6) . . ? F13 B1 F12 110.4(6) . . ? F13 B1 F14 109.4(6) . . ? F12 B1 F14 109.6(5) . . ? F13 B1 F11 109.2(6) . . ? F12 B1 F11 109.2(6) . . ? F14 B1 F11 109.0(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Ni1 N1 C18 28.2(6) . . . . ? N2 Ni1 N1 C18 -151.4(5) . . . . ? N3 Ni1 N1 C18 110(33) . . . . ? N4 Ni1 N1 C1 -151.7(6) . . . . ? N2 Ni1 N1 C1 28.7(6) . . . . ? N3 Ni1 N1 C1 -70(33) . . . . ? C18 N1 C1 C6 152.0(6) . . . . ? Ni1 N1 C1 C6 -28.1(9) . . . . ? C18 N1 C1 C2 -29.7(10) . . . . ? Ni1 N1 C1 C2 150.2(6) . . . . ? N1 C1 C2 C3 177.3(6) . . . . ? C6 C1 C2 C3 -4.4(10) . . . . ? C1 C2 C3 C4 1.5(11) . . . . ? C2 C3 C4 C5 1.3(12) . . . . ? C3 C4 C5 C6 -0.9(11) . . . . ? N1 C1 C6 C5 -177.1(6) . . . . ? C2 C1 C6 C5 4.6(10) . . . . ? N1 C1 C6 C7 5.7(11) . . . . ? C2 C1 C6 C7 -172.7(6) . . . . ? C4 C5 C6 C1 -2.1(10) . . . . ? C4 C5 C6 C7 175.4(7) . . . . ? C1 C6 C7 N2 11.0(12) . . . . ? C5 C6 C7 N2 -166.3(7) . . . . ? C6 C7 N2 C8 174.4(6) . . . . ? C6 C7 N2 Ni1 -2.3(11) . . . . ? N4 Ni1 N2 C7 167.1(18) . . . . ? N1 Ni1 N2 C7 -14.8(7) . . . . ? N3 Ni1 N2 C7 164.5(7) . . . . ? N4 Ni1 N2 C8 -10(3) . . . . ? N1 Ni1 N2 C8 168.3(6) . . . . ? N3 Ni1 N2 C8 -12.3(6) . . . . ? C7 N2 C8 C9 174.6(7) . . . . ? Ni1 N2 C8 C9 -8.2(8) . . . . ? N2 C8 C9 N3 33.6(9) . . . . ? C8 C9 N3 C10 -167.8(7) . . . . ? C8 C9 N3 Ni1 -43.1(9) . . . . ? N4 Ni1 N3 C9 -148.5(7) . . . . ? N2 Ni1 N3 C9 31.1(7) . . . . ? N1 Ni1 N3 C9 130(32) . . . . ? N4 Ni1 N3 C10 -18.9(7) . . . . ? N2 Ni1 N3 C10 160.6(7) . . . . ? N1 Ni1 N3 C10 -101(33) . . . . ? C9 N3 C10 C11 166.1(7) . . . . ? Ni1 N3 C10 C11 42.7(8) . . . . ? N3 C10 C11 N4 -49.6(7) . . . . ? C10 C11 N4 C12 -138.5(8) . . . . ? C10 C11 N4 Ni1 37.2(7) . . . . ? N2 Ni1 N4 C12 161.9(18) . . . . ? N1 Ni1 N4 C12 -16.2(8) . . . . ? N3 Ni1 N4 C12 164.4(7) . . . . ? N2 Ni1 N4 C11 -13(3) . . . . ? N1 Ni1 N4 C11 168.5(6) . . . . ? N3 Ni1 N4 C11 -10.8(6) . . . . ? C11 N4 C12 C13 175.6(7) . . . . ? Ni1 N4 C12 C13 0.6(12) . . . . ? N4 C12 C13 C14 -167.9(7) . . . . ? N4 C12 C13 C18 8.7(11) . . . . ? C18 C13 C14 C15 -1.6(11) . . . . ? C12 C13 C14 C15 175.1(7) . . . . ? C13 C14 C15 C16 -3.6(12) . . . . ? C14 C15 C16 C17 3.8(12) . . . . ? C15 C16 C17 C18 1.2(11) . . . . ? C16 C17 C18 N1 177.8(6) . . . . ? C16 C17 C18 C13 -6.1(10) . . . . ? C1 N1 C18 C17 -31.4(10) . . . . ? Ni1 N1 C18 C17 148.7(6) . . . . ? C1 N1 C18 C13 152.8(6) . . . . ? Ni1 N1 C18 C13 -27.1(9) . . . . ? C14 C13 C18 C17 6.3(10) . . . . ? C12 C13 C18 C17 -170.3(6) . . . . ? C14 C13 C18 N1 -177.7(6) . . . . ? C12 C13 C18 N1 5.8(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3X F12 0.94(7) 2.38(7) 3.287(11) 163(5) 2_464 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.370 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.064 # Attachment 'rs36.cif' data_rs36 _database_code_depnum_ccdc_archive 'CCDC 804222' #TrackingRef 'rs36.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 B Cu F4 N4' _chemical_formula_weight 441.72 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.058(3) _cell_length_b 7.4261(18) _cell_length_c 19.403(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.651(15) _cell_angle_gamma 90.00 _cell_volume 1731.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 2897 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 23.82 _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 1.314 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6939 _exptl_absorpt_correction_T_max 0.9021 _exptl_absorpt_process_details twinabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(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 Kappa Apex II area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4205 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4318 _reflns_number_gt 3632 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Twinned so used cellnow and twinabs to process the data. Domain 1 is related to domain 2 by a 180 degree rotation about the a-axis. Solved using component 1 data; final refinement against both components, using cell that is a weighted average of the 2 components (the two cells are not significantly different at the 95% Confidence level). There are lots more reflections than expected (cifcheck alert) as a result of the twinning - only partial overlap of the lattices (only 1 in 4 reflections is more or less exactly overlapped). [Cu(II)(macrocycle-H)](BF4). No solvent. No disorder. All non-H ANIS. All H calc and ride. ; _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^)+(0.0910P)^2^+6.6220P] 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 4318 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0767 _refine_ls_wR_factor_ref 0.2081 _refine_ls_wR_factor_gt 0.1954 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.180 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.57773(7) 0.83411(13) 0.78288(4) 0.0244(3) Uani 1 1 d . . . N1 N 0.7244(4) 0.8206(8) 0.7498(3) 0.0197(12) Uani 1 1 d . . . C1 C 0.8156(5) 0.8384(9) 0.7979(3) 0.0154(13) Uani 1 1 d . . . C2 C 0.9170(5) 0.9143(9) 0.7792(3) 0.0202(14) Uani 1 1 d . . . H2 H 0.9226 0.9482 0.7324 0.024 Uiso 1 1 calc R . . C3 C 1.0081(5) 0.9411(9) 0.8263(3) 0.0225(14) Uani 1 1 d . . . H3 H 1.0738 0.9935 0.8112 0.027 Uiso 1 1 calc R . . C4 C 1.0048(6) 0.8923(9) 0.8957(4) 0.0253(15) Uani 1 1 d . . . H4 H 1.0675 0.9085 0.9280 0.030 Uiso 1 1 calc R . . C5 C 0.9078(5) 0.8202(9) 0.9154(3) 0.0205(14) Uani 1 1 d . . . H5 H 0.9040 0.7883 0.9626 0.025 Uiso 1 1 calc R . . C6 C 0.8135(5) 0.7911(9) 0.8692(3) 0.0189(14) Uani 1 1 d . . . C7 C 0.7174(5) 0.7232(9) 0.9005(3) 0.0190(14) Uani 1 1 d . . . H7 H 0.7288 0.6741 0.9457 0.023 Uiso 1 1 calc R . . N2 N 0.6177(4) 0.7243(7) 0.8717(3) 0.0194(12) Uani 1 1 d . . . C8 C 0.5221(6) 0.6738(11) 0.9103(3) 0.0269(15) Uani 1 1 d . . . H8A H 0.5161 0.7568 0.9498 0.032 Uiso 1 1 calc R . . H8B H 0.5318 0.5498 0.9286 0.032 Uiso 1 1 calc R . . C9 C 0.4165(6) 0.6853(11) 0.8603(4) 0.0305(17) Uani 1 1 d . . . H9A H 0.4110 0.5781 0.8299 0.037 Uiso 1 1 calc R . . H9B H 0.3496 0.6896 0.8867 0.037 Uiso 1 1 calc R . . N3 N 0.4236(5) 0.8515(8) 0.8181(3) 0.0235(12) Uani 1 1 d . . . H3X H 0.4196 0.9524 0.8462 0.028 Uiso 1 1 calc R . . C10 C 0.3419(6) 0.8665(10) 0.7585(4) 0.0277(17) Uani 1 1 d . . . H10A H 0.2714 0.9173 0.7728 0.033 Uiso 1 1 calc R . . H10B H 0.3262 0.7462 0.7379 0.033 Uiso 1 1 calc R . . C11 C 0.3905(5) 0.9890(10) 0.7064(4) 0.0262(16) Uani 1 1 d . . . H11A H 0.3454 0.9843 0.6615 0.031 Uiso 1 1 calc R . . H11B H 0.3928 1.1150 0.7232 0.031 Uiso 1 1 calc R . . N4 N 0.5040(4) 0.9211(8) 0.6993(3) 0.0206(12) Uani 1 1 d . . . C12 C 0.5422(6) 0.9028(9) 0.6395(3) 0.0208(14) Uani 1 1 d . . . H12 H 0.4953 0.9380 0.6001 0.025 Uiso 1 1 calc R . . C13 C 0.6499(5) 0.8336(9) 0.6280(3) 0.0183(13) Uani 1 1 d . . . C14 C 0.6655(6) 0.8006(10) 0.5579(3) 0.0265(16) Uani 1 1 d . . . H14 H 0.6078 0.8324 0.5239 0.032 Uiso 1 1 calc R . . C15 C 0.7611(6) 0.7241(9) 0.5368(3) 0.0238(15) Uani 1 1 d . . . H15 H 0.7695 0.7012 0.4893 0.029 Uiso 1 1 calc R . . C16 C 0.8449(6) 0.6819(10) 0.5879(3) 0.0234(14) Uani 1 1 d . . . H16 H 0.9118 0.6297 0.5745 0.028 Uiso 1 1 calc R . . C17 C 0.8343(5) 0.7129(9) 0.6566(3) 0.0213(15) Uani 1 1 d . . . H17 H 0.8937 0.6795 0.6893 0.026 Uiso 1 1 calc R . . C18 C 0.7377(5) 0.7931(8) 0.6809(3) 0.0174(14) Uani 1 1 d . . . B1 B 0.3188(6) 1.2178(10) 0.9058(4) 0.0201(16) Uani 1 1 d . . . F1 F 0.3671(4) 1.2482(6) 0.8437(2) 0.0370(11) Uani 1 1 d . . . F2 F 0.3826(4) 1.0931(6) 0.9454(2) 0.0371(11) Uani 1 1 d . . . F3 F 0.2162(4) 1.1473(10) 0.8916(3) 0.082(2) Uani 1 1 d . . . F4 F 0.3167(6) 1.3776(6) 0.9407(2) 0.0656(18) 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 Cu1 0.0165(4) 0.0365(5) 0.0209(4) -0.0030(4) 0.0053(3) -0.0020(4) N1 0.016(3) 0.025(3) 0.018(3) -0.006(2) 0.004(2) 0.003(3) C1 0.014(3) 0.012(3) 0.021(3) 0.005(3) 0.005(2) 0.006(3) C2 0.021(3) 0.017(3) 0.024(3) 0.002(3) 0.009(3) -0.004(3) C3 0.014(3) 0.027(4) 0.027(3) 0.001(3) 0.004(3) -0.002(3) C4 0.022(4) 0.022(4) 0.031(4) 0.003(3) 0.000(3) 0.003(3) C5 0.027(3) 0.012(3) 0.023(3) 0.004(3) 0.003(3) -0.004(3) C6 0.018(3) 0.017(3) 0.023(3) 0.000(2) 0.007(3) 0.005(3) C7 0.024(4) 0.013(3) 0.020(3) 0.001(2) 0.002(3) 0.005(3) N2 0.020(3) 0.017(3) 0.023(3) -0.004(2) 0.011(2) -0.005(2) C8 0.025(3) 0.037(4) 0.021(3) -0.001(3) 0.012(3) -0.006(3) C9 0.018(3) 0.032(4) 0.043(4) -0.003(4) 0.009(3) -0.004(3) N3 0.026(3) 0.017(3) 0.028(3) 0.000(2) 0.008(2) -0.004(3) C10 0.020(3) 0.030(4) 0.034(4) -0.012(3) 0.003(3) 0.004(3) C11 0.016(3) 0.023(4) 0.039(4) -0.007(3) 0.002(3) 0.000(3) N4 0.015(3) 0.021(3) 0.026(3) -0.010(2) 0.003(2) -0.001(2) C12 0.022(3) 0.019(3) 0.022(3) -0.006(3) 0.002(3) -0.001(3) C13 0.022(3) 0.018(3) 0.016(3) 0.002(3) 0.007(2) -0.001(3) C14 0.026(4) 0.033(4) 0.022(3) 0.004(3) 0.005(3) 0.000(3) C15 0.035(4) 0.018(4) 0.019(3) 0.000(3) 0.007(3) -0.001(3) C16 0.024(3) 0.022(4) 0.026(3) 0.002(3) 0.013(3) 0.000(3) C17 0.021(3) 0.015(4) 0.028(3) 0.004(3) 0.005(3) 0.007(3) C18 0.020(3) 0.012(3) 0.021(3) -0.002(3) 0.009(3) -0.001(3) B1 0.019(4) 0.010(4) 0.031(4) 0.006(3) 0.003(3) 0.001(3) F1 0.046(3) 0.043(3) 0.023(2) -0.0008(19) 0.0096(19) -0.001(2) F2 0.031(2) 0.041(3) 0.039(2) 0.011(2) 0.0012(19) 0.011(2) F3 0.039(3) 0.120(6) 0.081(4) 0.054(4) -0.029(3) -0.048(4) F4 0.145(6) 0.023(3) 0.034(3) 0.002(2) 0.038(3) 0.009(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 N4 1.898(6) . y Cu1 N1 1.932(5) . y Cu1 N2 1.932(6) . y Cu1 N3 2.036(6) . y N1 C18 1.376(8) . ? N1 C1 1.389(8) . ? C1 C2 1.420(9) . ? C1 C6 1.429(9) . ? C2 C3 1.385(9) . ? C2 H2 0.9500 . ? C3 C4 1.399(9) . ? C3 H3 0.9500 . ? C4 C5 1.368(9) . ? C4 H4 0.9500 . ? C5 C6 1.407(9) . ? C5 H5 0.9500 . ? C6 C7 1.442(9) . ? C7 N2 1.284(8) . ? C7 H7 0.9500 . ? N2 C8 1.473(8) . ? C8 C9 1.540(10) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N3 1.488(10) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N3 C10 1.462(9) . ? N3 H3X 0.9300 . ? C10 C11 1.512(10) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N4 1.476(8) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N4 C12 1.290(8) . ? C12 C13 1.430(9) . ? C12 H12 0.9500 . ? C13 C14 1.410(9) . ? C13 C18 1.445(9) . ? C14 C15 1.376(10) . ? C14 H14 0.9500 . ? C15 C16 1.393(10) . ? C15 H15 0.9500 . ? C16 C17 1.370(9) . ? C16 H16 0.9500 . ? C17 C18 1.421(9) . ? C17 H17 0.9500 . ? B1 F3 1.350(9) . ? B1 F4 1.367(9) . ? B1 F2 1.394(8) . ? B1 F1 1.399(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N1 96.4(2) . . y N4 Cu1 N2 166.2(2) . . y N1 Cu1 N2 96.1(2) . . y N4 Cu1 N3 83.6(2) . . y N1 Cu1 N3 179.3(3) . . y N2 Cu1 N3 84.0(2) . . y C18 N1 C1 121.2(5) . . ? C18 N1 Cu1 120.9(4) . . ? C1 N1 Cu1 118.0(4) . . ? N1 C1 C2 121.2(5) . . ? N1 C1 C6 123.4(6) . . ? C2 C1 C6 115.4(6) . . ? C3 C2 C1 122.8(6) . . ? C3 C2 H2 118.6 . . ? C1 C2 H2 118.6 . . ? C2 C3 C4 121.0(6) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 117.5(6) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? C4 C5 C6 123.1(6) . . ? C4 C5 H5 118.4 . . ? C6 C5 H5 118.4 . . ? C5 C6 C1 120.2(6) . . ? C5 C6 C7 114.9(6) . . ? C1 C6 C7 124.9(6) . . ? N2 C7 C6 124.8(6) . . ? N2 C7 H7 117.6 . . ? C6 C7 H7 117.6 . . ? C7 N2 C8 121.4(6) . . ? C7 N2 Cu1 123.2(4) . . ? C8 N2 Cu1 114.4(4) . . ? N2 C8 C9 107.9(5) . . ? N2 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? N2 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? N3 C9 C8 108.1(6) . . ? N3 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? N3 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? C10 N3 C9 115.7(6) . . ? C10 N3 Cu1 108.3(4) . . ? C9 N3 Cu1 103.1(4) . . ? C10 N3 H3X 109.8 . . ? C9 N3 H3X 109.8 . . ? Cu1 N3 H3X 109.8 . . ? N3 C10 C11 107.6(6) . . ? N3 C10 H10A 110.2 . . ? C11 C10 H10A 110.2 . . ? N3 C10 H10B 110.2 . . ? C11 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? N4 C11 C10 105.6(6) . . ? N4 C11 H11A 110.6 . . ? C10 C11 H11A 110.6 . . ? N4 C11 H11B 110.6 . . ? C10 C11 H11B 110.6 . . ? H11A C11 H11B 108.7 . . ? C12 N4 C11 121.5(6) . . ? C12 N4 Cu1 123.8(5) . . ? C11 N4 Cu1 114.2(4) . . ? N4 C12 C13 124.9(6) . . ? N4 C12 H12 117.5 . . ? C13 C12 H12 117.5 . . ? C14 C13 C12 114.0(6) . . ? C14 C13 C18 120.0(6) . . ? C12 C13 C18 125.9(5) . . ? C15 C14 C13 122.7(7) . . ? C15 C14 H14 118.6 . . ? C13 C14 H14 118.6 . . ? C14 C15 C16 117.2(6) . . ? C14 C15 H15 121.4 . . ? C16 C15 H15 121.4 . . ? C17 C16 C15 122.4(6) . . ? C17 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? C16 C17 C18 122.4(6) . . ? C16 C17 H17 118.8 . . ? C18 C17 H17 118.8 . . ? N1 C18 C17 123.2(6) . . ? N1 C18 C13 121.5(6) . . ? C17 C18 C13 115.2(6) . . ? F3 B1 F4 112.6(7) . . ? F3 B1 F2 108.1(6) . . ? F4 B1 F2 109.6(6) . . ? F3 B1 F1 109.0(6) . . ? F4 B1 F1 108.2(6) . . ? F2 B1 F1 109.4(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Cu1 N1 C18 -27.9(6) . . . . ? N2 Cu1 N1 C18 146.3(5) . . . . ? N3 Cu1 N1 C18 -119(19) . . . . ? N4 Cu1 N1 C1 152.5(5) . . . . ? N2 Cu1 N1 C1 -33.3(5) . . . . ? N3 Cu1 N1 C1 62(19) . . . . ? C18 N1 C1 C2 30.8(9) . . . . ? Cu1 N1 C1 C2 -149.6(5) . . . . ? C18 N1 C1 C6 -152.3(6) . . . . ? Cu1 N1 C1 C6 27.3(8) . . . . ? N1 C1 C2 C3 177.2(6) . . . . ? C6 C1 C2 C3 0.1(9) . . . . ? C1 C2 C3 C4 0.6(11) . . . . ? C2 C3 C4 C5 -1.1(11) . . . . ? C3 C4 C5 C6 1.0(11) . . . . ? C4 C5 C6 C1 -0.4(10) . . . . ? C4 C5 C6 C7 -176.8(6) . . . . ? N1 C1 C6 C5 -177.2(6) . . . . ? C2 C1 C6 C5 -0.2(9) . . . . ? N1 C1 C6 C7 -1.2(10) . . . . ? C2 C1 C6 C7 175.8(6) . . . . ? C5 C6 C7 N2 164.0(6) . . . . ? C1 C6 C7 N2 -12.1(11) . . . . ? C6 C7 N2 C8 -172.1(6) . . . . ? C6 C7 N2 Cu1 -4.5(9) . . . . ? N4 Cu1 N2 C7 178.4(8) . . . . ? N1 Cu1 N2 C7 23.3(6) . . . . ? N3 Cu1 N2 C7 -155.9(6) . . . . ? N4 Cu1 N2 C8 -13.2(12) . . . . ? N1 Cu1 N2 C8 -168.3(5) . . . . ? N3 Cu1 N2 C8 12.4(5) . . . . ? C7 N2 C8 C9 -178.6(6) . . . . ? Cu1 N2 C8 C9 12.8(7) . . . . ? N2 C8 C9 N3 -42.3(8) . . . . ? C8 C9 N3 C10 168.2(6) . . . . ? C8 C9 N3 Cu1 50.1(6) . . . . ? N4 Cu1 N3 C10 16.2(5) . . . . ? N1 Cu1 N3 C10 107(19) . . . . ? N2 Cu1 N3 C10 -157.8(5) . . . . ? N4 Cu1 N3 C9 139.3(5) . . . . ? N1 Cu1 N3 C9 -130(19) . . . . ? N2 Cu1 N3 C9 -34.7(4) . . . . ? C9 N3 C10 C11 -155.0(6) . . . . ? Cu1 N3 C10 C11 -39.9(6) . . . . ? N3 C10 C11 N4 48.9(7) . . . . ? C10 C11 N4 C12 135.2(7) . . . . ? C10 C11 N4 Cu1 -36.6(6) . . . . ? N1 Cu1 N4 C12 21.3(6) . . . . ? N2 Cu1 N4 C12 -133.8(9) . . . . ? N3 Cu1 N4 C12 -159.4(6) . . . . ? N1 Cu1 N4 C11 -167.2(5) . . . . ? N2 Cu1 N4 C11 37.7(12) . . . . ? N3 Cu1 N4 C11 12.1(5) . . . . ? C11 N4 C12 C13 -178.2(6) . . . . ? Cu1 N4 C12 C13 -7.3(10) . . . . ? N4 C12 C13 C14 170.6(7) . . . . ? N4 C12 C13 C18 -7.8(11) . . . . ? C12 C13 C14 C15 -176.1(7) . . . . ? C18 C13 C14 C15 2.3(11) . . . . ? C13 C14 C15 C16 -1.0(11) . . . . ? C14 C15 C16 C17 0.4(11) . . . . ? C15 C16 C17 C18 -1.0(11) . . . . ? C1 N1 C18 C17 25.3(10) . . . . ? Cu1 N1 C18 C17 -154.3(5) . . . . ? C1 N1 C18 C13 -159.0(6) . . . . ? Cu1 N1 C18 C13 21.4(9) . . . . ? C16 C17 C18 N1 178.1(6) . . . . ? C16 C17 C18 C13 2.2(10) . . . . ? C14 C13 C18 N1 -178.8(6) . . . . ? C12 C13 C18 N1 -0.5(10) . . . . ? C14 C13 C18 C17 -2.8(9) . . . . ? C12 C13 C18 C17 175.5(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3X F1 0.93 2.29 3.073(8) 142.2 . N3 H3X F2 0.93 2.27 3.124(7) 153.1 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.015 _refine_diff_density_min -1.248 _refine_diff_density_rms 0.179 data_rs45 _database_code_depnum_ccdc_archive 'CCDC 804223' #TrackingRef '- rs45.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51 H53 B2 F8 N11 Zn2' _chemical_formula_weight 1124.40 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 10.3702(16) _cell_length_b 10.6201(18) _cell_length_c 12.6948(19) _cell_angle_alpha 96.434(8) _cell_angle_beta 98.583(8) _cell_angle_gamma 116.065(7) _cell_volume 1216.8(3) _cell_formula_units_Z 1 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 2408 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 20.37 _exptl_crystal_description 'triangular plate' _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 578 _exptl_absorpt_coefficient_mu 1.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8150 _exptl_absorpt_correction_T_max 0.9586 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(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 Kappa APEX II area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19349 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.1175 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 26.55 _reflns_number_total 9848 _reflns_number_gt 6991 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Refined as racemically twinned in P1; BASF = 0.38(1). Asymmetric unit contains 2 x [Zn (MC-H) (pyridine)] 2 x BF4 and 1 pyridine of solvation. No disorder. All H calc and ride. All non-H ANIS except for C2, C32 and C35 which are isotropic. Reflection 1 0 1 was omitted as it was behind the beamstop. ; _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^)+(0.1305P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(8) _refine_ls_number_reflns 9848 _refine_ls_number_parameters 650 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1156 _refine_ls_R_factor_gt 0.0819 _refine_ls_wR_factor_ref 0.2265 _refine_ls_wR_factor_gt 0.2008 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 Zn1 Zn 0.68794(8) 0.00137(8) 0.81263(7) 0.0213(3) Uani 1 1 d . . . N1 N 0.5415(7) 0.0712(6) 0.8469(5) 0.0149(14) Uani 1 1 d . . . C1 C 0.4670(8) 0.0390(7) 0.9309(6) 0.0113(16) Uani 1 1 d . . . C2 C 0.3867(8) 0.1091(8) 0.9615(6) 0.0140(16) Uiso 1 1 d . . . H2 H 0.3812 0.1780 0.9218 0.017 Uiso 1 1 calc R . . C3 C 0.3154(8) 0.0832(8) 1.0460(7) 0.0190(17) Uani 1 1 d . . . H3 H 0.2641 0.1349 1.0644 0.023 Uiso 1 1 calc R . . C4 C 0.3187(9) -0.0179(9) 1.1038(7) 0.0198(19) Uani 1 1 d . . . H4 H 0.2660 -0.0401 1.1600 0.024 Uiso 1 1 calc R . . C5 C 0.3992(10) -0.0861(9) 1.0791(7) 0.027(2) Uani 1 1 d . . . H5 H 0.4027 -0.1546 1.1201 0.032 Uiso 1 1 calc R . . C6 C 0.4774(8) -0.0586(8) 0.9950(6) 0.0143(16) Uani 1 1 d . . . C7 C 0.5640(8) -0.1330(8) 0.9916(6) 0.0167(17) Uani 1 1 d . . . H7 H 0.5520 -0.2008 1.0371 0.020 Uiso 1 1 calc R . . N2 N 0.6576(8) -0.1132(8) 0.9301(5) 0.0224(16) Uani 1 1 d . . . C8 C 0.7566(9) -0.1816(9) 0.9407(7) 0.026(2) Uani 1 1 d . . . H8A H 0.7511 -0.2240 1.0065 0.031 Uiso 1 1 calc R . . H8B H 0.7267 -0.2585 0.8765 0.031 Uiso 1 1 calc R . . C9 C 0.9098(9) -0.0676(9) 0.9487(7) 0.026(2) Uani 1 1 d . . . H9A H 0.9429 0.0042 1.0168 0.031 Uiso 1 1 calc R . . H9B H 0.9779 -0.1101 0.9496 0.031 Uiso 1 1 calc R . . N3 N 0.9103(7) 0.0018(8) 0.8531(6) 0.0269(18) Uani 1 1 d . . . H3X H 0.9216 -0.0502 0.7944 0.032 Uiso 1 1 calc R . . C10 C 1.0172(10) 0.1496(10) 0.8710(8) 0.035(2) Uani 1 1 d . . . H10A H 1.1158 0.1578 0.8701 0.042 Uiso 1 1 calc R . . H10B H 1.0217 0.2006 0.9428 0.042 Uiso 1 1 calc R . . C11 C 0.9723(9) 0.2155(10) 0.7815(8) 0.027(2) Uani 1 1 d . . . H11A H 1.0407 0.3191 0.7947 0.032 Uiso 1 1 calc R . . H11B H 0.9760 0.1700 0.7103 0.032 Uiso 1 1 calc R . . N4 N 0.8225(8) 0.1927(7) 0.7809(6) 0.0223(16) Uani 1 1 d . . . C12 C 0.7790(10) 0.2820(9) 0.7552(7) 0.027(2) Uani 1 1 d . . . H12 H 0.8514 0.3726 0.7480 0.032 Uiso 1 1 calc R . . C13 C 0.6259(11) 0.2562(10) 0.7359(7) 0.028(2) Uani 1 1 d . . . C14 C 0.5917(11) 0.3394(10) 0.6724(7) 0.033(2) Uani 1 1 d . . . H14 H 0.6687 0.4179 0.6539 0.039 Uiso 1 1 calc R . . C15 C 0.4477(11) 0.3109(10) 0.6355(7) 0.028(2) Uani 1 1 d . . . H15 H 0.4270 0.3702 0.5925 0.034 Uiso 1 1 calc R . . C16 C 0.3351(12) 0.1985(11) 0.6599(7) 0.030(2) Uani 1 1 d . . . H16 H 0.2363 0.1765 0.6301 0.037 Uiso 1 1 calc R . . C17 C 0.3637(10) 0.1150(9) 0.7286(6) 0.0235(19) Uani 1 1 d . . . H17 H 0.2841 0.0369 0.7451 0.028 Uiso 1 1 calc R . . C18 C 0.5095(9) 0.1460(8) 0.7734(6) 0.0172(17) Uani 1 1 d . . . N21 N 0.5795(7) -0.1495(7) 0.6695(6) 0.0184(16) Uani 1 1 d . . . C21 C 0.6486(10) -0.1953(9) 0.6042(7) 0.024(2) Uani 1 1 d . . . H21 H 0.7530 -0.1458 0.6174 0.029 Uiso 1 1 calc R . . C22 C 0.5712(10) -0.3134(10) 0.5175(7) 0.026(2) Uani 1 1 d . . . H22 H 0.6212 -0.3453 0.4730 0.031 Uiso 1 1 calc R . . C23 C 0.4208(9) -0.3808(8) 0.4998(6) 0.0201(18) Uani 1 1 d . . . H23 H 0.3637 -0.4618 0.4426 0.024 Uiso 1 1 calc R . . C24 C 0.3526(8) -0.3295(9) 0.5663(6) 0.0188(17) Uani 1 1 d . . . H24 H 0.2483 -0.3745 0.5545 0.023 Uiso 1 1 calc R . . C25 C 0.4343(8) -0.2167(8) 0.6469(7) 0.0167(17) Uani 1 1 d . . . H25 H 0.3850 -0.1827 0.6907 0.020 Uiso 1 1 calc R . . B1 B 0.9773(12) -0.2651(13) 0.6742(8) 0.029(2) Uani 1 1 d . . . F11 F 1.0026(5) -0.1270(5) 0.6715(4) 0.0284(12) Uani 1 1 d . . . F12 F 0.8741(6) -0.3566(6) 0.5798(4) 0.0363(14) Uani 1 1 d . . . F13 F 1.1039(6) -0.2785(6) 0.6868(5) 0.0378(13) Uani 1 1 d . . . F14 F 0.9097(7) -0.3066(7) 0.7628(5) 0.0420(15) Uani 1 1 d . . . Zn2 Zn 0.05519(10) 0.48814(11) 0.16031(8) 0.0363(3) Uani 1 1 d . . . N31 N 0.2277(7) 0.4642(7) 0.1176(5) 0.0147(14) Uani 1 1 d . . . C31 C 0.2789(8) 0.4919(8) 0.0243(6) 0.0155(17) Uani 1 1 d . . . C32 C 0.3856(8) 0.4493(8) -0.0075(6) 0.0149(15) Uiso 1 1 d . . . H32 H 0.4242 0.4047 0.0398 0.018 Uiso 1 1 calc R . . C33 C 0.4323(9) 0.4701(9) -0.1010(7) 0.022(2) Uani 1 1 d . . . H33 H 0.5000 0.4377 -0.1187 0.027 Uiso 1 1 calc R . . C34 C 0.3810(9) 0.5403(9) -0.1737(7) 0.0224(18) Uani 1 1 d . . . H34 H 0.4155 0.5576 -0.2385 0.027 Uiso 1 1 calc R . . C35 C 0.2789(9) 0.5825(9) -0.1463(7) 0.0205(18) Uiso 1 1 d . . . H35 H 0.2440 0.6297 -0.1934 0.025 Uiso 1 1 calc R . . C36 C 0.2262(9) 0.5577(8) -0.0522(7) 0.0164(17) Uani 1 1 d . . . C37 C 0.1001(9) 0.5841(9) -0.0453(7) 0.0209(18) Uani 1 1 d . . . H37 H 0.0749 0.6293 -0.0994 0.025 Uiso 1 1 calc R . . N32 N 0.0212(8) 0.5542(8) 0.0233(5) 0.0213(16) Uani 1 1 d . . . C38 C -0.1142(10) 0.5714(10) 0.0097(7) 0.0235(19) Uani 1 1 d . . . H38A H -0.1470 0.5745 -0.0669 0.028 Uiso 1 1 calc R . . H38B H -0.0953 0.6615 0.0564 0.028 Uiso 1 1 calc R . . C39 C -0.2299(10) 0.4459(10) 0.0416(7) 0.027(2) Uani 1 1 d . . . H39A H -0.3225 0.4535 0.0329 0.032 Uiso 1 1 calc R . . H39B H -0.2494 0.3564 -0.0064 0.032 Uiso 1 1 calc R . . N33 N -0.1798(7) 0.4413(8) 0.1574(6) 0.0229(16) Uani 1 1 d . . . H33X H -0.1831 0.5128 0.2048 0.027 Uiso 1 1 calc R . . C40 C -0.2555(8) 0.3024(9) 0.1878(7) 0.0214(19) Uani 1 1 d . . . H40A H -0.3622 0.2589 0.1551 0.026 Uiso 1 1 calc R . . H40B H -0.2427 0.3163 0.2679 0.026 Uiso 1 1 calc R . . C41 C -0.1962(8) 0.2021(9) 0.1500(7) 0.0201(17) Uani 1 1 d . . . H41A H -0.2320 0.1184 0.1854 0.024 Uiso 1 1 calc R . . H41B H -0.2316 0.1673 0.0703 0.024 Uiso 1 1 calc R . . N34 N -0.0353(8) 0.2781(7) 0.1779(6) 0.0234(17) Uani 1 1 d . . . C42 C 0.0429(10) 0.2227(10) 0.2124(6) 0.0217(19) Uani 1 1 d . . . H42 H -0.0064 0.1275 0.2237 0.026 Uiso 1 1 calc R . . C43 C 0.2041(10) 0.2922(9) 0.2368(7) 0.0207(19) Uani 1 1 d . . . C44 C 0.2710(9) 0.2349(8) 0.3097(6) 0.0184(17) Uani 1 1 d . . . H44 H 0.2107 0.1542 0.3368 0.022 Uiso 1 1 calc R . . C45 C 0.4222(10) 0.2947(11) 0.3419(7) 0.028(2) Uani 1 1 d . . . H45 H 0.4657 0.2528 0.3882 0.033 Uiso 1 1 calc R . . C46 C 0.5107(9) 0.4171(10) 0.3061(7) 0.026(2) Uani 1 1 d . . . H46 H 0.6145 0.4634 0.3323 0.031 Uiso 1 1 calc R . . C47 C 0.4461(9) 0.4708(9) 0.2322(6) 0.0188(17) Uani 1 1 d . . . H47 H 0.5077 0.5523 0.2065 0.023 Uiso 1 1 calc R . . C48 C 0.2941(9) 0.4093(9) 0.1941(6) 0.0180(17) Uani 1 1 d . . . N51 N 0.1508(9) 0.6598(8) 0.2951(6) 0.0278(19) Uani 1 1 d . . . C51 C 0.0914(11) 0.7066(13) 0.3616(10) 0.041(3) Uani 1 1 d . . . H51 H -0.0099 0.6480 0.3590 0.049 Uiso 1 1 calc R . . C52 C 0.1617(11) 0.8329(12) 0.4350(8) 0.032(2) Uani 1 1 d . . . H52 H 0.1113 0.8591 0.4828 0.039 Uiso 1 1 calc R . . C53 C 0.3050(7) 0.9201(7) 0.4383(5) 0.027(2) Uani 1 1 d . . . H53 H 0.3583 1.0093 0.4879 0.032 Uiso 1 1 calc R . . C54 C 0.3695(7) 0.8749(7) 0.3680(5) 0.029(2) Uani 1 1 d R . . H54 H 0.4694 0.9342 0.3668 0.034 Uiso 1 1 d R . . C55 C 0.2937(10) 0.7474(9) 0.3000(6) 0.026(2) Uani 1 1 d . . . H55 H 0.3428 0.7176 0.2532 0.031 Uiso 1 1 calc R . . B2 B -0.1901(13) 0.8095(11) 0.2593(10) 0.033(3) Uani 1 1 d . . . F21 F -0.2379(7) 0.6735(6) 0.2097(8) 0.079(3) Uani 1 1 d . . . F22 F -0.1652(9) 0.8197(10) 0.3681(5) 0.073(3) Uani 1 1 d . . . F23 F -0.0594(9) 0.8924(8) 0.2331(7) 0.075(2) Uani 1 1 d . . . F24 F -0.2945(10) 0.8537(9) 0.2319(6) 0.090(3) Uani 1 1 d . . . N61 N 0.8002(11) 0.3159(13) 0.4856(8) 0.055(3) Uani 1 1 d . . . C61 C 0.9538(12) 0.3793(12) 0.5159(10) 0.047(3) Uani 1 1 d . . . H61 H 1.0087 0.4792 0.5444 0.056 Uiso 1 1 calc R . . C62 C 1.0236(12) 0.3008(13) 0.5052(11) 0.045(3) Uani 1 1 d . . . H62 H 1.1282 0.3453 0.5214 0.054 Uiso 1 1 calc R . . C63 C 0.9466(13) 0.1607(13) 0.4720(10) 0.049(3) Uani 1 1 d . . . H63 H 0.9947 0.1031 0.4647 0.058 Uiso 1 1 calc R . . C64 C 0.7927(12) 0.0986(12) 0.4478(8) 0.036(2) Uani 1 1 d . . . H64 H 0.7378 -0.0027 0.4289 0.043 Uiso 1 1 calc R . . C65 C 0.7205(10) 0.1747(9) 0.4500(7) 0.0215(19) Uani 1 1 d . . . H65 H 0.6163 0.1308 0.4272 0.026 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 Zn1 0.0139(5) 0.0231(5) 0.0206(5) -0.0047(4) 0.0031(4) 0.0053(4) N1 0.021(4) 0.003(3) 0.019(3) 0.001(3) 0.005(3) 0.004(3) C1 0.011(4) 0.003(3) 0.013(4) -0.002(3) -0.002(3) 0.000(3) C3 0.015(4) 0.014(4) 0.024(4) 0.000(3) -0.002(3) 0.006(3) C4 0.021(4) 0.018(4) 0.023(4) -0.001(4) 0.015(3) 0.009(4) C5 0.036(5) 0.022(5) 0.027(5) 0.011(4) 0.010(4) 0.015(4) C6 0.017(4) 0.012(4) 0.013(4) 0.001(3) 0.007(3) 0.005(3) C7 0.020(4) 0.013(4) 0.016(4) -0.003(3) 0.002(3) 0.008(3) N2 0.023(4) 0.031(4) 0.015(3) -0.003(3) -0.004(3) 0.019(3) C8 0.018(4) 0.029(5) 0.033(5) -0.005(4) -0.001(4) 0.017(4) C9 0.014(4) 0.018(4) 0.034(5) -0.003(4) 0.003(4) 0.000(4) N3 0.018(4) 0.036(5) 0.027(4) -0.005(3) -0.002(3) 0.017(3) C10 0.021(4) 0.031(5) 0.032(5) -0.015(4) 0.000(4) 0.001(4) C11 0.016(4) 0.023(5) 0.031(5) -0.008(4) 0.001(4) 0.005(4) N4 0.030(4) 0.008(3) 0.021(4) 0.005(3) 0.009(3) 0.000(3) C12 0.026(5) 0.018(5) 0.034(5) 0.001(4) 0.017(4) 0.007(4) C13 0.045(6) 0.027(5) 0.018(4) 0.000(4) 0.009(4) 0.023(5) C14 0.055(7) 0.034(5) 0.017(4) 0.012(4) 0.018(4) 0.022(5) C15 0.066(7) 0.031(5) 0.018(4) 0.019(4) 0.023(4) 0.041(5) C16 0.045(6) 0.035(6) 0.017(4) -0.004(4) -0.001(4) 0.028(5) C17 0.039(5) 0.022(5) 0.016(4) 0.002(3) 0.014(4) 0.018(4) C18 0.025(4) 0.012(4) 0.018(4) 0.000(3) 0.006(3) 0.012(3) N21 0.017(4) 0.015(4) 0.028(4) 0.007(3) 0.006(3) 0.012(3) C21 0.016(4) 0.022(5) 0.024(5) -0.013(4) -0.005(3) 0.007(4) C22 0.027(5) 0.041(6) 0.008(4) -0.007(4) 0.004(3) 0.018(4) C23 0.024(4) 0.006(4) 0.019(4) -0.005(3) -0.008(3) 0.002(3) C24 0.010(4) 0.023(4) 0.023(4) 0.008(3) 0.000(3) 0.009(3) C25 0.017(4) 0.016(4) 0.027(4) 0.015(3) 0.011(3) 0.012(3) B1 0.029(6) 0.045(7) 0.020(5) 0.007(5) 0.007(4) 0.023(5) F11 0.034(3) 0.026(3) 0.029(3) 0.004(2) 0.001(2) 0.019(2) F12 0.048(3) 0.036(3) 0.026(3) -0.010(2) -0.007(2) 0.029(3) F13 0.037(3) 0.042(3) 0.041(3) 0.009(3) 0.004(2) 0.026(3) F14 0.052(4) 0.054(4) 0.034(3) 0.022(3) 0.020(3) 0.031(3) Zn2 0.0286(6) 0.0400(7) 0.0328(6) -0.0002(5) 0.0040(5) 0.0120(5) N31 0.013(3) 0.010(3) 0.022(3) 0.004(3) 0.002(3) 0.007(3) C31 0.013(4) 0.009(4) 0.018(4) -0.006(3) -0.002(3) 0.003(3) C33 0.012(4) 0.018(4) 0.035(5) -0.007(4) 0.003(3) 0.008(3) C34 0.030(5) 0.020(4) 0.021(4) 0.003(3) 0.009(4) 0.014(4) C36 0.026(4) 0.008(4) 0.020(4) 0.001(3) -0.001(3) 0.013(3) C37 0.019(4) 0.020(4) 0.025(4) 0.004(3) -0.001(3) 0.012(4) N32 0.026(4) 0.025(4) 0.013(3) -0.002(3) -0.001(3) 0.015(3) C38 0.033(5) 0.025(5) 0.028(5) 0.014(4) 0.012(4) 0.023(4) C39 0.029(5) 0.037(5) 0.022(4) 0.005(4) 0.004(4) 0.024(4) N33 0.020(4) 0.029(4) 0.021(4) 0.000(3) 0.000(3) 0.016(3) C40 0.006(4) 0.032(5) 0.020(4) 0.006(4) 0.001(3) 0.004(4) C41 0.012(4) 0.018(4) 0.029(4) 0.005(3) 0.001(3) 0.007(3) N34 0.017(4) 0.011(3) 0.034(4) -0.002(3) -0.004(3) 0.004(3) C42 0.044(6) 0.029(5) 0.002(3) 0.005(3) 0.007(4) 0.024(5) C43 0.028(5) 0.020(4) 0.019(4) -0.006(3) 0.001(4) 0.020(4) C44 0.037(5) 0.014(4) 0.013(4) 0.005(3) 0.012(3) 0.017(4) C45 0.023(5) 0.041(6) 0.024(5) -0.002(4) 0.002(4) 0.022(4) C46 0.023(4) 0.033(5) 0.025(4) -0.001(4) 0.003(4) 0.019(4) C47 0.022(4) 0.025(5) 0.015(4) 0.005(3) 0.003(3) 0.017(4) C48 0.026(4) 0.019(4) 0.012(4) -0.001(3) 0.008(3) 0.013(4) N51 0.045(5) 0.028(4) 0.009(3) -0.002(3) -0.012(3) 0.022(4) C51 0.011(4) 0.057(7) 0.055(7) 0.038(6) 0.003(5) 0.013(5) C52 0.034(6) 0.048(6) 0.027(5) 0.013(5) 0.007(4) 0.028(5) C53 0.040(5) 0.022(5) 0.016(4) -0.004(4) -0.003(4) 0.017(4) C54 0.037(5) 0.012(4) 0.026(5) 0.000(4) 0.009(4) 0.002(4) C55 0.044(6) 0.023(5) 0.010(4) 0.001(3) 0.005(4) 0.017(4) B2 0.038(7) 0.016(5) 0.042(7) -0.006(5) -0.003(5) 0.017(5) F21 0.034(3) 0.019(3) 0.184(9) -0.003(4) 0.039(4) 0.013(3) F22 0.085(6) 0.146(8) 0.036(4) 0.032(5) 0.013(4) 0.092(6) F23 0.086(6) 0.048(4) 0.083(5) 0.032(4) 0.026(4) 0.017(4) F24 0.137(8) 0.107(6) 0.051(4) -0.033(4) -0.045(5) 0.110(6) N61 0.043(6) 0.086(9) 0.049(6) 0.039(6) 0.015(5) 0.033(6) C61 0.031(6) 0.037(6) 0.048(7) 0.001(5) 0.013(5) -0.005(5) C62 0.015(5) 0.047(7) 0.079(9) 0.013(6) 0.019(5) 0.016(5) C63 0.036(6) 0.046(7) 0.043(6) -0.017(5) -0.002(5) 0.010(5) C64 0.036(6) 0.041(6) 0.029(5) -0.007(4) 0.008(4) 0.019(5) C65 0.014(4) 0.019(4) 0.025(5) -0.006(4) 0.003(3) 0.005(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 Zn1 N2 2.003(7) . y Zn1 N4 2.025(7) . y Zn1 N1 2.040(7) . y Zn1 N21 2.070(7) . y Zn1 N3 2.284(7) . y N1 C18 1.384(10) . ? N1 C1 1.395(10) . ? C1 C6 1.418(11) . ? C1 C2 1.406(11) . ? C2 C3 1.378(11) . ? C2 H2 0.9500 . ? C3 C4 1.377(12) . ? C3 H3 0.9500 . ? C4 C5 1.371(12) . ? C4 H4 0.9500 . ? C5 C6 1.415(11) . ? C5 H5 0.9500 . ? C6 C7 1.436(11) . ? C7 N2 1.295(11) . ? C7 H7 0.9500 . ? N2 C8 1.496(10) . ? C8 C9 1.494(11) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N3 1.488(12) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N3 C10 1.436(11) . ? N3 H3X 0.9300 . ? C10 C11 1.518(14) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N4 1.462(11) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N4 C12 1.269(12) . ? C12 C13 1.464(13) . ? C12 H12 0.9500 . ? C13 C14 1.381(13) . ? C13 C18 1.452(13) . ? C14 C15 1.379(14) . ? C14 H14 0.9500 . ? C15 C16 1.360(14) . ? C15 H15 0.9500 . ? C16 C17 1.401(13) . ? C16 H16 0.9500 . ? C17 C18 1.408(12) . ? C17 H17 0.9500 . ? N21 C25 1.319(10) . ? N21 C21 1.354(11) . ? C21 C22 1.404(11) . ? C21 H21 0.9500 . ? C22 C23 1.369(12) . ? C22 H22 0.9500 . ? C23 C24 1.386(11) . ? C23 H23 0.9500 . ? C24 C25 1.332(12) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? B1 F13 1.370(11) . ? B1 F11 1.377(13) . ? B1 F12 1.403(11) . ? B1 F14 1.422(12) . ? Zn2 N32 1.987(7) . y Zn2 N31 2.054(7) . y Zn2 N34 2.060(7) . y Zn2 N51 2.108(7) . y Zn2 N33 2.257(7) . y N31 C31 1.378(11) . ? N31 C48 1.428(10) . ? C31 C36 1.435(11) . ? C31 C32 1.458(11) . ? C32 C33 1.353(12) . ? C32 H32 0.9500 . ? C33 C34 1.431(13) . ? C33 H33 0.9500 . ? C34 C35 1.390(12) . ? C34 H34 0.9500 . ? C35 C36 1.390(12) . ? C35 H35 0.9500 . ? C36 C37 1.465(11) . ? C37 N32 1.255(11) . ? C37 H37 0.9500 . ? N32 C38 1.481(11) . ? C38 C39 1.496(12) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 N33 1.498(11) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? N33 C40 1.464(11) . ? N33 H33X 0.9300 . ? C40 C41 1.514(12) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 N34 1.462(10) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? N34 C42 1.251(11) . ? C42 C43 1.465(13) . ? C42 H42 0.9500 . ? C43 C48 1.412(12) . ? C43 C44 1.419(11) . ? C44 C45 1.380(12) . ? C44 H44 0.9500 . ? C45 C46 1.396(13) . ? C45 H45 0.9500 . ? C46 C47 1.386(11) . ? C46 H46 0.9500 . ? C47 C48 1.394(11) . ? C47 H47 0.9500 . ? N51 C51 1.292(14) . ? N51 C55 1.346(12) . ? C51 C52 1.363(16) . ? C51 H51 0.9500 . ? C52 C53 1.353(12) . ? C52 H52 0.9500 . ? C53 C54 1.3560 . ? C53 H53 0.9500 . ? C54 C55 1.341(10) . ? C54 H54 0.9500 . ? C55 H55 0.9500 . ? B2 F21 1.342(12) . ? B2 F22 1.350(14) . ? B2 F23 1.369(14) . ? B2 F24 1.372(13) . ? N61 C65 1.335(14) . ? N61 C61 1.398(15) . ? C61 C62 1.331(16) . ? C61 H61 0.9500 . ? C62 C63 1.321(16) . ? C62 H62 0.9500 . ? C63 C64 1.399(16) . ? C63 H63 0.9500 . ? C64 C65 1.322(14) . ? C64 H64 0.9500 . ? C65 H65 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 N2 Zn1 N4 142.3(3) . . y N2 Zn1 N1 92.7(3) . . y N4 Zn1 N1 91.8(3) . . y N2 Zn1 N21 104.6(3) . . y N4 Zn1 N21 110.3(3) . . y N1 Zn1 N21 104.9(3) . . y N2 Zn1 N3 79.3(3) . . y N4 Zn1 N3 79.1(3) . . y N1 Zn1 N3 151.6(3) . . y N21 Zn1 N3 103.5(3) . . y C18 N1 C1 120.3(7) . . ? C18 N1 Zn1 114.6(5) . . ? C1 N1 Zn1 124.9(5) . . ? N1 C1 C6 121.6(7) . . ? N1 C1 C2 121.9(7) . . ? C6 C1 C2 116.4(7) . . ? C3 C2 C1 123.5(7) . . ? C3 C2 H2 118.3 . . ? C1 C2 H2 118.3 . . ? C2 C3 C4 119.7(8) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 119.0(8) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 122.6(8) . . ? C4 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C1 C6 C5 118.7(8) . . ? C1 C6 C7 129.2(7) . . ? C5 C6 C7 112.1(7) . . ? N2 C7 C6 123.8(8) . . ? N2 C7 H7 118.1 . . ? C6 C7 H7 118.1 . . ? C7 N2 C8 120.6(7) . . ? C7 N2 Zn1 127.3(6) . . ? C8 N2 Zn1 112.1(6) . . ? C9 C8 N2 107.4(7) . . ? C9 C8 H8A 110.2 . . ? N2 C8 H8A 110.2 . . ? C9 C8 H8B 110.2 . . ? N2 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? N3 C9 C8 108.5(7) . . ? N3 C9 H9A 110.0 . . ? C8 C9 H9A 110.0 . . ? N3 C9 H9B 110.0 . . ? C8 C9 H9B 110.0 . . ? H9A C9 H9B 108.4 . . ? C10 N3 C9 115.5(7) . . ? C10 N3 Zn1 104.7(6) . . ? C9 N3 Zn1 106.7(5) . . ? C10 N3 H3X 109.9 . . ? C9 N3 H3X 109.9 . . ? Zn1 N3 H3X 109.9 . . ? N3 C10 C11 108.5(7) . . ? N3 C10 H10A 110.0 . . ? C11 C10 H10A 110.0 . . ? N3 C10 H10B 110.0 . . ? C11 C10 H10B 110.0 . . ? H10A C10 H10B 108.4 . . ? N4 C11 C10 108.3(8) . . ? N4 C11 H11A 110.0 . . ? C10 C11 H11A 110.0 . . ? N4 C11 H11B 110.0 . . ? C10 C11 H11B 110.0 . . ? H11A C11 H11B 108.4 . . ? C12 N4 C11 122.2(7) . . ? C12 N4 Zn1 123.3(6) . . ? C11 N4 Zn1 114.4(6) . . ? N4 C12 C13 125.0(8) . . ? N4 C12 H12 117.5 . . ? C13 C12 H12 117.5 . . ? C14 C13 C18 119.1(9) . . ? C14 C13 C12 116.1(9) . . ? C18 C13 C12 124.7(8) . . ? C13 C14 C15 121.2(9) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 120.7(8) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 120.6(9) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 120.5(9) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? N1 C18 C17 121.8(8) . . ? N1 C18 C13 120.9(7) . . ? C17 C18 C13 117.2(8) . . ? C25 N21 C21 117.6(7) . . ? C25 N21 Zn1 118.3(6) . . ? C21 N21 Zn1 123.6(5) . . ? N21 C21 C22 122.2(8) . . ? N21 C21 H21 118.9 . . ? C22 C21 H21 118.9 . . ? C23 C22 C21 117.3(8) . . ? C23 C22 H22 121.4 . . ? C21 C22 H22 121.4 . . ? C22 C23 C24 119.3(7) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C25 C24 C23 119.6(7) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? N21 C25 C24 123.9(8) . . ? N21 C25 H25 118.1 . . ? C24 C25 H25 118.1 . . ? F13 B1 F11 112.6(8) . . ? F13 B1 F12 111.5(8) . . ? F11 B1 F12 109.0(8) . . ? F13 B1 F14 109.3(8) . . ? F11 B1 F14 107.9(8) . . ? F12 B1 F14 106.2(8) . . ? N32 Zn2 N31 90.4(3) . . y N32 Zn2 N34 125.3(3) . . y N31 Zn2 N34 88.0(3) . . y N32 Zn2 N51 111.0(3) . . y N31 Zn2 N51 105.5(3) . . y N34 Zn2 N51 122.0(3) . . y N32 Zn2 N33 83.3(3) . . y N31 Zn2 N33 158.6(3) . . y N34 Zn2 N33 79.2(3) . . y N51 Zn2 N33 95.9(3) . . y C31 N31 C48 119.7(7) . . ? C31 N31 Zn2 126.6(5) . . ? C48 N31 Zn2 113.7(5) . . ? N31 C31 C36 123.0(7) . . ? N31 C31 C32 122.4(7) . . ? C36 C31 C32 114.5(7) . . ? C33 C32 C31 123.1(8) . . ? C33 C32 H32 118.4 . . ? C31 C32 H32 118.4 . . ? C32 C33 C34 120.7(8) . . ? C32 C33 H33 119.6 . . ? C34 C33 H33 119.6 . . ? C35 C34 C33 117.8(8) . . ? C35 C34 H34 121.1 . . ? C33 C34 H34 121.1 . . ? C36 C35 C34 122.1(8) . . ? C36 C35 H35 118.9 . . ? C34 C35 H35 118.9 . . ? C35 C36 C31 121.5(8) . . ? C35 C36 C37 115.2(7) . . ? C31 C36 C37 122.7(8) . . ? N32 C37 C36 128.0(8) . . ? N32 C37 H37 116.0 . . ? C36 C37 H37 116.0 . . ? C37 N32 C38 120.7(7) . . ? C37 N32 Zn2 128.2(6) . . ? C38 N32 Zn2 111.1(5) . . ? N32 C38 C39 107.5(7) . . ? N32 C38 H38A 110.2 . . ? C39 C38 H38A 110.2 . . ? N32 C38 H38B 110.2 . . ? C39 C38 H38B 110.2 . . ? H38A C38 H38B 108.5 . . ? N33 C39 C38 110.1(7) . . ? N33 C39 H39A 109.6 . . ? C38 C39 H39A 109.6 . . ? N33 C39 H39B 109.6 . . ? C38 C39 H39B 109.6 . . ? H39A C39 H39B 108.2 . . ? C40 N33 C39 115.4(7) . . ? C40 N33 Zn2 108.2(5) . . ? C39 N33 Zn2 100.5(5) . . ? C40 N33 H33X 110.8 . . ? C39 N33 H33X 110.8 . . ? Zn2 N33 H33X 110.8 . . ? N33 C40 C41 111.4(7) . . ? N33 C40 H40A 109.3 . . ? C41 C40 H40A 109.3 . . ? N33 C40 H40B 109.3 . . ? C41 C40 H40B 109.3 . . ? H40A C40 H40B 108.0 . . ? N34 C41 C40 109.3(6) . . ? N34 C41 H41A 109.8 . . ? C40 C41 H41A 109.8 . . ? N34 C41 H41B 109.8 . . ? C40 C41 H41B 109.8 . . ? H41A C41 H41B 108.3 . . ? C42 N34 C41 123.5(8) . . ? C42 N34 Zn2 121.9(6) . . ? C41 N34 Zn2 114.6(5) . . ? N34 C42 C43 125.4(8) . . ? N34 C42 H42 117.3 . . ? C43 C42 H42 117.3 . . ? C48 C43 C44 119.2(8) . . ? C48 C43 C42 125.1(8) . . ? C44 C43 C42 115.7(8) . . ? C45 C44 C43 121.0(8) . . ? C45 C44 H44 119.5 . . ? C43 C44 H44 119.5 . . ? C44 C45 C46 119.5(9) . . ? C44 C45 H45 120.2 . . ? C46 C45 H45 120.2 . . ? C47 C46 C45 119.6(8) . . ? C47 C46 H46 120.2 . . ? C45 C46 H46 120.2 . . ? C46 C47 C48 122.3(8) . . ? C46 C47 H47 118.8 . . ? C48 C47 H47 118.8 . . ? C47 C48 C43 118.0(7) . . ? C47 C48 N31 122.3(7) . . ? C43 C48 N31 119.6(7) . . ? C51 N51 C55 115.3(8) . . ? C51 N51 Zn2 130.8(7) . . ? C55 N51 Zn2 112.8(6) . . ? N51 C51 C52 125.5(10) . . ? N51 C51 H51 117.2 . . ? C52 C51 H51 117.2 . . ? C53 C52 C51 118.4(9) . . ? C53 C52 H52 120.8 . . ? C51 C52 H52 120.8 . . ? C52 C53 C54 117.3(5) . . ? C52 C53 H53 121.3 . . ? C54 C53 H53 121.3 . . ? C55 C54 C53 120.6(5) . . ? C55 C54 H54 119.7 . . ? C53 C54 H54 119.7 . . ? C54 C55 N51 122.8(8) . . ? C54 C55 H55 118.6 . . ? N51 C55 H55 118.6 . . ? F21 B2 F22 109.6(10) . . ? F21 B2 F23 108.1(10) . . ? F22 B2 F23 108.2(9) . . ? F21 B2 F24 110.9(9) . . ? F22 B2 F24 107.1(9) . . ? F23 B2 F24 112.8(10) . . ? C65 N61 C61 120.7(11) . . ? C62 C61 N61 120.5(11) . . ? C62 C61 H61 119.7 . . ? N61 C61 H61 119.7 . . ? C63 C62 C61 119.5(11) . . ? C63 C62 H62 120.2 . . ? C61 C62 H62 120.2 . . ? C62 C63 C64 118.9(12) . . ? C62 C63 H63 120.6 . . ? C64 C63 H63 120.6 . . ? C65 C64 C63 122.9(11) . . ? C65 C64 H64 118.6 . . ? C63 C64 H64 118.6 . . ? C64 C65 N61 117.2(9) . . ? C64 C65 H65 121.4 . . ? N61 C65 H65 121.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Zn1 N1 C18 -172.3(6) . . . . ? N4 Zn1 N1 C18 45.1(6) . . . . ? N21 Zn1 N1 C18 -66.4(6) . . . . ? N3 Zn1 N1 C18 115.4(7) . . . . ? N2 Zn1 N1 C1 2.4(6) . . . . ? N4 Zn1 N1 C1 -140.2(6) . . . . ? N21 Zn1 N1 C1 108.3(6) . . . . ? N3 Zn1 N1 C1 -69.9(8) . . . . ? C18 N1 C1 C6 168.4(7) . . . . ? Zn1 N1 C1 C6 -6.0(10) . . . . ? C18 N1 C1 C2 -16.3(11) . . . . ? Zn1 N1 C1 C2 169.3(5) . . . . ? N1 C1 C2 C3 -178.0(7) . . . . ? C6 C1 C2 C3 -2.5(11) . . . . ? C1 C2 C3 C4 -1.2(12) . . . . ? C2 C3 C4 C5 3.1(12) . . . . ? C3 C4 C5 C6 -1.1(13) . . . . ? N1 C1 C6 C5 179.8(7) . . . . ? C2 C1 C6 C5 4.3(10) . . . . ? N1 C1 C6 C7 3.1(12) . . . . ? C2 C1 C6 C7 -172.4(8) . . . . ? C4 C5 C6 C1 -2.7(12) . . . . ? C4 C5 C6 C7 174.6(8) . . . . ? C1 C6 C7 N2 4.8(13) . . . . ? C5 C6 C7 N2 -172.1(7) . . . . ? C6 C7 N2 C8 172.6(7) . . . . ? C6 C7 N2 Zn1 -8.7(11) . . . . ? N4 Zn1 N2 C7 101.4(8) . . . . ? N1 Zn1 N2 C7 4.9(7) . . . . ? N21 Zn1 N2 C7 -101.2(7) . . . . ? N3 Zn1 N2 C7 157.4(7) . . . . ? N4 Zn1 N2 C8 -79.8(7) . . . . ? N1 Zn1 N2 C8 -176.3(5) . . . . ? N21 Zn1 N2 C8 77.5(5) . . . . ? N3 Zn1 N2 C8 -23.8(5) . . . . ? C7 N2 C8 C9 -130.5(8) . . . . ? Zn1 N2 C8 C9 50.7(8) . . . . ? N2 C8 C9 N3 -54.9(9) . . . . ? C8 C9 N3 C10 149.8(7) . . . . ? C8 C9 N3 Zn1 33.9(8) . . . . ? N2 Zn1 N3 C10 -128.8(6) . . . . ? N4 Zn1 N3 C10 20.1(6) . . . . ? N1 Zn1 N3 C10 -53.3(9) . . . . ? N21 Zn1 N3 C10 128.6(6) . . . . ? N2 Zn1 N3 C9 -5.9(5) . . . . ? N4 Zn1 N3 C9 143.1(6) . . . . ? N1 Zn1 N3 C9 69.7(8) . . . . ? N21 Zn1 N3 C9 -108.5(5) . . . . ? C9 N3 C10 C11 -162.0(7) . . . . ? Zn1 N3 C10 C11 -44.9(8) . . . . ? N3 C10 C11 N4 55.9(9) . . . . ? C10 C11 N4 C12 147.2(8) . . . . ? C10 C11 N4 Zn1 -37.3(8) . . . . ? N2 Zn1 N4 C12 -118.6(7) . . . . ? N1 Zn1 N4 C12 -21.8(7) . . . . ? N21 Zn1 N4 C12 84.8(7) . . . . ? N3 Zn1 N4 C12 -174.7(8) . . . . ? N2 Zn1 N4 C11 66.0(8) . . . . ? N1 Zn1 N4 C11 162.8(6) . . . . ? N21 Zn1 N4 C11 -90.6(6) . . . . ? N3 Zn1 N4 C11 9.9(6) . . . . ? C11 N4 C12 C13 169.6(8) . . . . ? Zn1 N4 C12 C13 -5.4(12) . . . . ? N4 C12 C13 C14 -157.2(9) . . . . ? N4 C12 C13 C18 19.3(14) . . . . ? C18 C13 C14 C15 -6.4(13) . . . . ? C12 C13 C14 C15 170.3(8) . . . . ? C13 C14 C15 C16 -0.6(13) . . . . ? C14 C15 C16 C17 4.0(13) . . . . ? C15 C16 C17 C18 -0.1(13) . . . . ? C1 N1 C18 C17 -43.1(11) . . . . ? Zn1 N1 C18 C17 131.8(6) . . . . ? C1 N1 C18 C13 139.6(7) . . . . ? Zn1 N1 C18 C13 -45.5(9) . . . . ? C16 C17 C18 N1 175.9(7) . . . . ? C16 C17 C18 C13 -6.7(11) . . . . ? C14 C13 C18 N1 -172.7(8) . . . . ? C12 C13 C18 N1 10.8(12) . . . . ? C14 C13 C18 C17 9.9(11) . . . . ? C12 C13 C18 C17 -166.6(8) . . . . ? N2 Zn1 N21 C25 71.1(6) . . . . ? N4 Zn1 N21 C25 -123.4(6) . . . . ? N1 Zn1 N21 C25 -25.7(6) . . . . ? N3 Zn1 N21 C25 153.4(6) . . . . ? N2 Zn1 N21 C21 -100.8(7) . . . . ? N4 Zn1 N21 C21 64.7(7) . . . . ? N1 Zn1 N21 C21 162.4(7) . . . . ? N3 Zn1 N21 C21 -18.5(7) . . . . ? C25 N21 C21 C22 -2.5(13) . . . . ? Zn1 N21 C21 C22 169.5(7) . . . . ? N21 C21 C22 C23 1.0(14) . . . . ? C21 C22 C23 C24 0.6(13) . . . . ? C22 C23 C24 C25 -0.7(12) . . . . ? C21 N21 C25 C24 2.4(12) . . . . ? Zn1 N21 C25 C24 -169.9(6) . . . . ? C23 C24 C25 N21 -0.9(12) . . . . ? N32 Zn2 N31 C31 0.3(6) . . . . ? N34 Zn2 N31 C31 125.6(6) . . . . ? N51 Zn2 N31 C31 -111.7(6) . . . . ? N33 Zn2 N31 C31 72.8(10) . . . . ? N32 Zn2 N31 C48 -177.9(6) . . . . ? N34 Zn2 N31 C48 -52.6(6) . . . . ? N51 Zn2 N31 C48 70.2(6) . . . . ? N33 Zn2 N31 C48 -105.3(8) . . . . ? C48 N31 C31 C36 -174.9(7) . . . . ? Zn2 N31 C31 C36 7.1(10) . . . . ? C48 N31 C31 C32 8.5(10) . . . . ? Zn2 N31 C31 C32 -169.5(5) . . . . ? N31 C31 C32 C33 177.1(7) . . . . ? C36 C31 C32 C33 0.3(11) . . . . ? C31 C32 C33 C34 1.8(12) . . . . ? C32 C33 C34 C35 -1.8(12) . . . . ? C33 C34 C35 C36 -0.3(12) . . . . ? C34 C35 C36 C31 2.5(12) . . . . ? C34 C35 C36 C37 -169.1(8) . . . . ? N31 C31 C36 C35 -179.2(7) . . . . ? C32 C31 C36 C35 -2.4(11) . . . . ? N31 C31 C36 C37 -8.3(12) . . . . ? C32 C31 C36 C37 168.6(7) . . . . ? C35 C36 C37 N32 170.7(8) . . . . ? C31 C36 C37 N32 -0.8(13) . . . . ? C36 C37 N32 C38 -171.9(8) . . . . ? C36 C37 N32 Zn2 10.3(13) . . . . ? N31 Zn2 N32 C37 -8.8(8) . . . . ? N34 Zn2 N32 C37 -96.5(8) . . . . ? N51 Zn2 N32 C37 98.0(8) . . . . ? N33 Zn2 N32 C37 -168.2(8) . . . . ? N31 Zn2 N32 C38 173.3(6) . . . . ? N34 Zn2 N32 C38 85.5(6) . . . . ? N51 Zn2 N32 C38 -79.9(6) . . . . ? N33 Zn2 N32 C38 13.9(5) . . . . ? C37 N32 C38 C39 139.6(8) . . . . ? Zn2 N32 C38 C39 -42.3(8) . . . . ? N32 C38 C39 N33 59.8(9) . . . . ? C38 C39 N33 C40 -159.9(7) . . . . ? C38 C39 N33 Zn2 -43.8(7) . . . . ? N32 Zn2 N33 C40 137.5(5) . . . . ? N31 Zn2 N33 C40 63.7(9) . . . . ? N34 Zn2 N33 C40 9.6(5) . . . . ? N51 Zn2 N33 C40 -112.0(5) . . . . ? N32 Zn2 N33 C39 16.2(5) . . . . ? N31 Zn2 N33 C39 -57.6(10) . . . . ? N34 Zn2 N33 C39 -111.7(5) . . . . ? N51 Zn2 N33 C39 126.7(5) . . . . ? C39 N33 C40 C41 79.1(8) . . . . ? Zn2 N33 C40 C41 -32.4(7) . . . . ? N33 C40 C41 N34 46.6(9) . . . . ? C40 C41 N34 C42 140.2(8) . . . . ? C40 C41 N34 Zn2 -38.1(8) . . . . ? N32 Zn2 N34 C42 123.8(7) . . . . ? N31 Zn2 N34 C42 34.7(7) . . . . ? N51 Zn2 N34 C42 -72.3(8) . . . . ? N33 Zn2 N34 C42 -162.5(7) . . . . ? N32 Zn2 N34 C41 -57.9(7) . . . . ? N31 Zn2 N34 C41 -146.9(6) . . . . ? N51 Zn2 N34 C41 106.1(6) . . . . ? N33 Zn2 N34 C41 15.9(6) . . . . ? C41 N34 C42 C43 177.1(8) . . . . ? Zn2 N34 C42 C43 -4.6(12) . . . . ? N34 C42 C43 C48 -21.7(13) . . . . ? N34 C42 C43 C44 158.0(8) . . . . ? C48 C43 C44 C45 2.0(12) . . . . ? C42 C43 C44 C45 -177.7(7) . . . . ? C43 C44 C45 C46 2.9(13) . . . . ? C44 C45 C46 C47 -4.9(12) . . . . ? C45 C46 C47 C48 2.0(12) . . . . ? C46 C47 C48 C43 2.8(12) . . . . ? C46 C47 C48 N31 -179.7(7) . . . . ? C44 C43 C48 C47 -4.8(11) . . . . ? C42 C43 C48 C47 174.9(7) . . . . ? C44 C43 C48 N31 177.7(7) . . . . ? C42 C43 C48 N31 -2.6(12) . . . . ? C31 N31 C48 C47 49.4(10) . . . . ? Zn2 N31 C48 C47 -132.4(6) . . . . ? C31 N31 C48 C43 -133.3(7) . . . . ? Zn2 N31 C48 C43 45.0(8) . . . . ? N32 Zn2 N51 C51 93.7(9) . . . . ? N31 Zn2 N51 C51 -169.7(8) . . . . ? N34 Zn2 N51 C51 -72.3(9) . . . . ? N33 Zn2 N51 C51 8.6(9) . . . . ? N32 Zn2 N51 C55 -73.7(6) . . . . ? N31 Zn2 N51 C55 22.9(6) . . . . ? N34 Zn2 N51 C55 120.3(6) . . . . ? N33 Zn2 N51 C55 -158.8(6) . . . . ? C55 N51 C51 C52 -1.2(14) . . . . ? Zn2 N51 C51 C52 -168.4(7) . . . . ? N51 C51 C52 C53 1.7(15) . . . . ? C51 C52 C53 C54 -0.3(10) . . . . ? C52 C53 C54 C55 -1.4(6) . . . . ? C53 C54 C55 N51 1.9(10) . . . . ? C51 N51 C55 C54 -0.6(12) . . . . ? Zn2 N51 C55 C54 168.9(6) . . . . ? C65 N61 C61 C62 3.0(17) . . . . ? N61 C61 C62 C63 -4.1(19) . . . . ? C61 C62 C63 C64 0.6(19) . . . . ? C62 C63 C64 C65 4.4(18) . . . . ? C63 C64 C65 N61 -5.5(16) . . . . ? C61 N61 C65 C64 1.8(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3X F11 0.93 2.12 3.034(9) 165.6 . N33 H33X F21 0.93 2.02 2.817(9) 142.9 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.55 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.547 _refine_diff_density_min -1.125 _refine_diff_density_rms 0.136 # Attachment 'rs50_orth.cif' data_rs50_orth _database_code_depnum_ccdc_archive 'CCDC 804224' #TrackingRef 'rs50_orth.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 Fe N7 O2 S2' _chemical_formula_weight 524.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.894(8) _cell_length_b 13.097(12) _cell_length_c 19.980(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2327(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 2092 _cell_measurement_theta_min 2.5025 _cell_measurement_theta_max 21.584 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 0.861 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.5840 _exptl_absorpt_correction_T_max 0.9112 _exptl_absorpt_process_details 'SCALE (Bruker AXS Inc.)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19217 _diffrn_reflns_av_R_equivalents 0.1131 _diffrn_reflns_av_sigmaI/netI 0.0961 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.34 _reflns_number_total 4241 _reflns_number_gt 3377 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. [Fe(III) (macrocycle-H) (NCS)2].NO2Me Entire complex in asym unit. No disorder. All non-H ANIS. All H calc and ride. SHEL used to limit to 0.83A resolution data (2theta max 50.68deg). ; _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^)+(0.0465P)^2^+2.3194P] 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 0.00(3) _refine_ls_number_reflns 4241 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1484 _refine_ls_wR_factor_gt 0.1389 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.32677(10) 0.82818(7) 0.81046(4) 0.0309(2) Uani 1 1 d . . . N1 N 0.3111(6) 0.7485(4) 0.8870(2) 0.0268(11) Uani 1 1 d . . . N2 N 0.1978(6) 0.7450(4) 0.7567(2) 0.0310(12) Uani 1 1 d . . . N3 N 0.3380(7) 0.9161(4) 0.7307(3) 0.0482(16) Uani 1 1 d . . . H3A H 0.2692 0.9677 0.7399 0.058 Uiso 1 1 calc R . . N4 N 0.4630(5) 0.9254(4) 0.8482(2) 0.0294(12) Uani 1 1 d . . . N50 N 0.4990(6) 0.7520(4) 0.7780(2) 0.0323(13) Uani 1 1 d . . . C50 C 0.6172(8) 0.7252(5) 0.7606(3) 0.0357(16) Uani 1 1 d . . . S50 S 0.7815(2) 0.6800(2) 0.73624(9) 0.0609(6) Uani 1 1 d . . . N60 N 0.1559(6) 0.9101(4) 0.8396(3) 0.0361(13) Uani 1 1 d . . . C60 C 0.0531(7) 0.9518(5) 0.8599(3) 0.0349(16) Uani 1 1 d . . . S60 S -0.0923(2) 1.01471(16) 0.89083(8) 0.0456(5) Uani 1 1 d . . . C1 C 0.2859(7) 0.6426(5) 0.8833(3) 0.0294(14) Uani 1 1 d . . . C2 C 0.3418(9) 0.5759(5) 0.9330(3) 0.0380(16) Uani 1 1 d . . . H2 H 0.4026 0.6027 0.9679 0.046 Uiso 1 1 calc R . . C3 C 0.3107(9) 0.4743(5) 0.9321(3) 0.0428(17) Uani 1 1 d . . . H3 H 0.3490 0.4313 0.9664 0.051 Uiso 1 1 calc R . . C4 C 0.2220(8) 0.4325(6) 0.8806(3) 0.0433(18) Uani 1 1 d . . . H4 H 0.1967 0.3620 0.8813 0.052 Uiso 1 1 calc R . . C5 C 0.1721(8) 0.4933(5) 0.8297(3) 0.0355(14) Uani 1 1 d . . . H5 H 0.1132 0.4644 0.7948 0.043 Uiso 1 1 calc R . . C6 C 0.2072(6) 0.5988(5) 0.8282(3) 0.0273(13) Uani 1 1 d . . . C7 C 0.1580(7) 0.6529(4) 0.7695(3) 0.0291(13) Uani 1 1 d . . . H7 H 0.0933 0.6190 0.7390 0.035 Uiso 1 1 calc R . . C8 C 0.1545(8) 0.7944(6) 0.6931(3) 0.0496(18) Uani 1 1 d . . . H8A H 0.1406 0.7422 0.6578 0.059 Uiso 1 1 calc R . . H8B H 0.0586 0.8318 0.6988 0.059 Uiso 1 1 calc R . . C9 C 0.2736(9) 0.8651(6) 0.6740(3) 0.053(2) Uani 1 1 d . . . H9A H 0.3535 0.8270 0.6501 0.064 Uiso 1 1 calc R . . H9B H 0.2322 0.9166 0.6428 0.064 Uiso 1 1 calc R . . C10 C 0.4787(9) 0.9684(7) 0.7293(3) 0.059(2) Uani 1 1 d . . . H10A H 0.4671 1.0328 0.7039 0.071 Uiso 1 1 calc R . . H10B H 0.5535 0.9257 0.7056 0.071 Uiso 1 1 calc R . . C11 C 0.5363(7) 0.9923(5) 0.7981(3) 0.0353(15) Uani 1 1 d . . . H11A H 0.6465 0.9820 0.7995 0.042 Uiso 1 1 calc R . . H11B H 0.5152 1.0647 0.8089 0.042 Uiso 1 1 calc R . . C12 C 0.4844(7) 0.9394(5) 0.9105(3) 0.0310(14) Uani 1 1 d . . . H12 H 0.5559 0.9893 0.9239 0.037 Uiso 1 1 calc R . . C13 C 0.4052(7) 0.8831(5) 0.9620(3) 0.0311(14) Uani 1 1 d . . . C14 C 0.4143(8) 0.9222(5) 1.0275(3) 0.0376(16) Uani 1 1 d . . . H14 H 0.4756 0.9803 1.0356 0.045 Uiso 1 1 calc R . . C15 C 0.3370(9) 0.8789(5) 1.0805(3) 0.0398(16) Uani 1 1 d . . . H15 H 0.3482 0.9049 1.1246 0.048 Uiso 1 1 calc R . . C16 C 0.2424(8) 0.7964(6) 1.0678(3) 0.0457(19) Uani 1 1 d . . . H16 H 0.1837 0.7682 1.1029 0.055 Uiso 1 1 calc R . . C17 C 0.2340(8) 0.7559(5) 1.0045(3) 0.0380(16) Uani 1 1 d . . . H17 H 0.1684 0.6998 0.9970 0.046 Uiso 1 1 calc R . . C18 C 0.3185(7) 0.7937(4) 0.9502(3) 0.0305(14) Uani 1 1 d . . . C31 C 0.2301(8) 0.1480(6) 0.9538(4) 0.051(2) Uani 1 1 d . . . H31A H 0.1538 0.1973 0.9681 0.077 Uiso 1 1 calc R . . H31B H 0.2116 0.0822 0.9756 0.077 Uiso 1 1 calc R . . H31C H 0.2251 0.1395 0.9051 0.077 Uiso 1 1 calc R . . N31 N 0.3815(7) 0.1859(5) 0.9728(3) 0.0472(15) Uani 1 1 d . . . O31 O 0.4088(8) 0.1973(5) 1.0317(3) 0.088(2) Uani 1 1 d . . . O32 O 0.4741(7) 0.2024(5) 0.9294(3) 0.078(2) 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 Fe1 0.0259(4) 0.0339(5) 0.0329(4) 0.0043(4) -0.0026(4) -0.0034(4) N1 0.023(3) 0.030(3) 0.027(2) 0.002(2) 0.008(2) -0.001(2) N2 0.025(3) 0.038(3) 0.029(3) 0.001(2) -0.005(2) -0.004(2) N3 0.053(4) 0.045(3) 0.047(3) 0.013(3) -0.013(3) -0.023(3) N4 0.020(3) 0.034(3) 0.035(3) 0.002(2) -0.004(2) -0.006(2) N50 0.030(3) 0.040(3) 0.027(3) 0.003(2) -0.001(2) -0.006(3) C50 0.035(4) 0.049(4) 0.023(3) 0.005(3) -0.004(3) 0.000(3) S50 0.0384(11) 0.1000(18) 0.0444(10) 0.0071(12) 0.0055(8) 0.0200(12) N60 0.025(3) 0.030(3) 0.053(3) 0.003(2) -0.001(3) -0.004(3) C60 0.029(4) 0.039(4) 0.037(4) 0.013(3) -0.010(3) -0.010(3) S60 0.0323(9) 0.0634(13) 0.0411(9) 0.0084(9) 0.0032(8) 0.0061(9) C1 0.027(3) 0.028(3) 0.033(3) 0.002(3) 0.008(3) -0.007(3) C2 0.047(4) 0.036(4) 0.031(3) -0.003(3) -0.002(3) 0.000(4) C3 0.056(5) 0.033(4) 0.039(3) 0.004(3) 0.004(4) 0.008(4) C4 0.050(4) 0.037(4) 0.044(4) -0.003(3) 0.010(3) -0.006(3) C5 0.036(4) 0.039(4) 0.032(3) -0.006(3) 0.002(3) -0.001(3) C6 0.018(3) 0.030(3) 0.034(3) -0.001(2) 0.006(2) -0.001(2) C7 0.019(3) 0.035(4) 0.034(3) -0.008(3) 0.003(3) -0.003(3) C8 0.044(4) 0.061(5) 0.043(4) 0.008(4) -0.009(4) -0.004(4) C9 0.072(5) 0.063(5) 0.026(3) 0.009(3) -0.003(3) -0.022(4) C10 0.062(5) 0.082(6) 0.033(4) 0.023(4) 0.004(3) -0.041(5) C11 0.022(3) 0.040(4) 0.045(4) 0.009(3) 0.004(3) -0.005(3) C12 0.021(3) 0.026(3) 0.046(4) -0.001(3) -0.004(3) 0.000(3) C13 0.020(3) 0.035(4) 0.038(3) 0.000(3) 0.003(3) 0.000(3) C14 0.042(4) 0.030(3) 0.041(4) -0.008(3) -0.003(3) -0.007(3) C15 0.042(4) 0.044(4) 0.033(3) -0.007(3) 0.003(3) -0.003(4) C16 0.049(5) 0.049(5) 0.039(4) -0.007(3) 0.008(3) -0.007(4) C17 0.039(4) 0.039(4) 0.036(3) -0.004(3) 0.007(3) -0.009(3) C18 0.027(3) 0.029(3) 0.035(3) -0.002(2) -0.003(3) 0.002(3) C31 0.041(4) 0.059(5) 0.055(4) 0.003(4) 0.003(3) 0.007(4) N31 0.048(4) 0.037(3) 0.056(4) 0.004(3) -0.004(3) -0.002(3) O31 0.105(5) 0.106(6) 0.054(3) -0.008(4) -0.006(3) -0.055(5) O32 0.058(4) 0.098(6) 0.077(4) -0.014(4) 0.016(3) -0.023(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 N1 1.858(5) . Y Fe1 N4 1.912(5) . Y Fe1 N2 1.912(5) . Y Fe1 N50 1.939(6) . Y Fe1 N60 1.949(6) . Y Fe1 N3 1.969(5) . Y N1 C18 1.397(7) . ? N1 C1 1.407(8) . ? N2 C7 1.283(8) . ? N2 C8 1.476(8) . ? N3 C10 1.427(9) . ? N3 C9 1.434(8) . ? N3 H3A 0.9300 . ? N4 C12 1.273(7) . ? N4 C11 1.481(7) . ? N50 C50 1.162(8) . ? C50 S50 1.650(7) . ? N60 C60 1.139(8) . ? C60 S60 1.654(7) . ? C1 C2 1.414(8) . ? C1 C6 1.425(8) . ? C2 C3 1.359(9) . ? C2 H2 0.9500 . ? C3 C4 1.408(10) . ? C3 H3 0.9500 . ? C4 C5 1.366(9) . ? C4 H4 0.9500 . ? C5 C6 1.416(8) . ? C5 H5 0.9500 . ? C6 C7 1.438(8) . ? C7 H7 0.9500 . ? C8 C9 1.457(10) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.500(8) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.449(8) . ? C12 H12 0.9500 . ? C13 C14 1.409(8) . ? C13 C18 1.421(8) . ? C14 C15 1.384(9) . ? C14 H14 0.9500 . ? C15 C16 1.392(9) . ? C15 H15 0.9500 . ? C16 C17 1.374(9) . ? C16 H16 0.9500 . ? C17 C18 1.409(8) . ? C17 H17 0.9500 . ? C31 N31 1.484(9) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? N31 O31 1.211(7) . ? N31 O32 1.216(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N4 95.6(2) . . Y N1 Fe1 N2 95.6(2) . . Y N4 Fe1 N2 168.7(2) . . Y N1 Fe1 N50 92.6(2) . . Y N4 Fe1 N50 88.5(2) . . Y N2 Fe1 N50 89.6(2) . . Y N1 Fe1 N60 90.3(2) . . Y N4 Fe1 N60 90.6(2) . . Y N2 Fe1 N60 90.8(2) . . Y N50 Fe1 N60 177.1(2) . . Y N1 Fe1 N3 177.9(3) . . Y N4 Fe1 N3 84.1(2) . . Y N2 Fe1 N3 84.7(2) . . Y N50 Fe1 N3 89.5(3) . . Y N60 Fe1 N3 87.7(3) . . Y C18 N1 C1 118.3(5) . . ? C18 N1 Fe1 120.2(4) . . ? C1 N1 Fe1 121.5(4) . . ? C7 N2 C8 120.8(5) . . ? C7 N2 Fe1 126.0(4) . . ? C8 N2 Fe1 113.0(4) . . ? C10 N3 C9 124.0(6) . . ? C10 N3 Fe1 109.9(4) . . ? C9 N3 Fe1 110.3(4) . . ? C10 N3 H3A 103.4 . . ? C9 N3 H3A 103.4 . . ? Fe1 N3 H3A 103.4 . . ? C12 N4 C11 120.6(5) . . ? C12 N4 Fe1 125.2(4) . . ? C11 N4 Fe1 114.0(4) . . ? C50 N50 Fe1 166.0(6) . . ? N50 C50 S50 176.6(7) . . ? C60 N60 Fe1 174.6(5) . . ? N60 C60 S60 178.1(6) . . ? N1 C1 C2 121.1(5) . . ? N1 C1 C6 121.1(5) . . ? C2 C1 C6 117.8(5) . . ? C3 C2 C1 121.6(6) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 120.3(6) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 120.0(6) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.8(6) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 119.0(5) . . ? C5 C6 C7 115.5(5) . . ? C1 C6 C7 125.4(5) . . ? N2 C7 C6 122.9(6) . . ? N2 C7 H7 118.5 . . ? C6 C7 H7 118.5 . . ? C9 C8 N2 108.3(6) . . ? C9 C8 H8A 110.0 . . ? N2 C8 H8A 110.0 . . ? C9 C8 H8B 110.0 . . ? N2 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? N3 C9 C8 112.2(5) . . ? N3 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? N3 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? N3 C10 C11 112.5(5) . . ? N3 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? N3 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? N4 C11 C10 110.2(5) . . ? N4 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? N4 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? N4 C12 C13 123.3(6) . . ? N4 C12 H12 118.4 . . ? C13 C12 H12 118.4 . . ? C14 C13 C18 119.0(6) . . ? C14 C13 C12 116.6(6) . . ? C18 C13 C12 124.5(6) . . ? C15 C14 C13 122.2(6) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C14 C15 C16 118.6(6) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C17 C16 C15 120.0(6) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 122.9(6) . . ? C16 C17 H17 118.5 . . ? C18 C17 H17 118.5 . . ? N1 C18 C17 121.4(6) . . ? N1 C18 C13 121.6(5) . . ? C17 C18 C13 116.9(5) . . ? N31 C31 H31A 109.5 . . ? N31 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N31 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O31 N31 O32 122.4(7) . . ? O31 N31 C31 118.2(6) . . ? O32 N31 C31 119.4(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Fe1 N1 C18 33.5(5) . . . . ? N2 Fe1 N1 C18 -147.9(5) . . . . ? N50 Fe1 N1 C18 122.2(5) . . . . ? N60 Fe1 N1 C18 -57.1(5) . . . . ? N3 Fe1 N1 C18 -48(7) . . . . ? N4 Fe1 N1 C1 -149.0(5) . . . . ? N2 Fe1 N1 C1 29.6(5) . . . . ? N50 Fe1 N1 C1 -60.2(5) . . . . ? N60 Fe1 N1 C1 120.4(5) . . . . ? N3 Fe1 N1 C1 129(6) . . . . ? N1 Fe1 N2 C7 -16.5(5) . . . . ? N4 Fe1 N2 C7 156.3(10) . . . . ? N50 Fe1 N2 C7 76.0(5) . . . . ? N60 Fe1 N2 C7 -106.9(5) . . . . ? N3 Fe1 N2 C7 165.5(6) . . . . ? N1 Fe1 N2 C8 168.2(4) . . . . ? N4 Fe1 N2 C8 -19.0(14) . . . . ? N50 Fe1 N2 C8 -99.2(5) . . . . ? N60 Fe1 N2 C8 77.9(5) . . . . ? N3 Fe1 N2 C8 -9.7(5) . . . . ? N1 Fe1 N3 C10 109(6) . . . . ? N4 Fe1 N3 C10 27.1(5) . . . . ? N2 Fe1 N3 C10 -151.1(6) . . . . ? N50 Fe1 N3 C10 -61.5(6) . . . . ? N60 Fe1 N3 C10 117.9(6) . . . . ? N1 Fe1 N3 C9 -111(6) . . . . ? N4 Fe1 N3 C9 167.2(6) . . . . ? N2 Fe1 N3 C9 -11.0(6) . . . . ? N50 Fe1 N3 C9 78.6(6) . . . . ? N60 Fe1 N3 C9 -102.0(6) . . . . ? N1 Fe1 N4 C12 -18.9(5) . . . . ? N2 Fe1 N4 C12 168.3(10) . . . . ? N50 Fe1 N4 C12 -111.4(5) . . . . ? N60 Fe1 N4 C12 71.4(5) . . . . ? N3 Fe1 N4 C12 159.0(6) . . . . ? N1 Fe1 N4 C11 166.1(4) . . . . ? N2 Fe1 N4 C11 -6.7(14) . . . . ? N50 Fe1 N4 C11 73.6(4) . . . . ? N60 Fe1 N4 C11 -103.6(4) . . . . ? N3 Fe1 N4 C11 -16.0(4) . . . . ? N1 Fe1 N50 C50 -115(2) . . . . ? N4 Fe1 N50 C50 -19(2) . . . . ? N2 Fe1 N50 C50 150(2) . . . . ? N60 Fe1 N50 C50 53(5) . . . . ? N3 Fe1 N50 C50 65(2) . . . . ? Fe1 N50 C50 S50 165(8) . . . . ? N1 Fe1 N60 C60 -18(6) . . . . ? N4 Fe1 N60 C60 -114(6) . . . . ? N2 Fe1 N60 C60 77(6) . . . . ? N50 Fe1 N60 C60 174(5) . . . . ? N3 Fe1 N60 C60 162(6) . . . . ? Fe1 N60 C60 S60 106(19) . . . . ? C18 N1 C1 C2 -32.7(8) . . . . ? Fe1 N1 C1 C2 149.7(5) . . . . ? C18 N1 C1 C6 149.2(6) . . . . ? Fe1 N1 C1 C6 -28.4(7) . . . . ? N1 C1 C2 C3 176.0(6) . . . . ? C6 C1 C2 C3 -5.8(10) . . . . ? C1 C2 C3 C4 0.5(11) . . . . ? C2 C3 C4 C5 2.8(11) . . . . ? C3 C4 C5 C6 -0.7(11) . . . . ? C4 C5 C6 C1 -4.7(9) . . . . ? C4 C5 C6 C7 175.5(6) . . . . ? N1 C1 C6 C5 -174.1(5) . . . . ? C2 C1 C6 C5 7.7(9) . . . . ? N1 C1 C6 C7 5.8(9) . . . . ? C2 C1 C6 C7 -172.4(6) . . . . ? C8 N2 C7 C6 175.0(6) . . . . ? Fe1 N2 C7 C6 0.1(8) . . . . ? C5 C6 C7 N2 -170.7(6) . . . . ? C1 C6 C7 N2 9.5(9) . . . . ? C7 N2 C8 C9 -147.6(6) . . . . ? Fe1 N2 C8 C9 27.9(7) . . . . ? C10 N3 C9 C8 163.4(7) . . . . ? Fe1 N3 C9 C8 30.0(8) . . . . ? N2 C8 C9 N3 -37.4(9) . . . . ? C9 N3 C10 C11 -166.0(7) . . . . ? Fe1 N3 C10 C11 -32.5(9) . . . . ? C12 N4 C11 C10 -173.1(6) . . . . ? Fe1 N4 C11 C10 2.2(7) . . . . ? N3 C10 C11 N4 20.1(9) . . . . ? C11 N4 C12 C13 173.9(5) . . . . ? Fe1 N4 C12 C13 -0.8(9) . . . . ? N4 C12 C13 C14 -165.8(6) . . . . ? N4 C12 C13 C18 12.9(10) . . . . ? C18 C13 C14 C15 -2.5(10) . . . . ? C12 C13 C14 C15 176.3(6) . . . . ? C13 C14 C15 C16 -2.7(11) . . . . ? C14 C15 C16 C17 3.8(11) . . . . ? C15 C16 C17 C18 0.3(11) . . . . ? C1 N1 C18 C17 -31.9(9) . . . . ? Fe1 N1 C18 C17 145.7(5) . . . . ? C1 N1 C18 C13 151.4(6) . . . . ? Fe1 N1 C18 C13 -30.9(8) . . . . ? C16 C17 C18 N1 177.8(6) . . . . ? C16 C17 C18 C13 -5.4(10) . . . . ? C14 C13 C18 N1 -176.8(6) . . . . ? C12 C13 C18 N1 4.4(10) . . . . ? C14 C13 C18 C17 6.4(9) . . . . ? C12 C13 C18 C17 -172.4(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A S50 0.93 2.86 3.676(8) 147.6 3_656 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.974 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.084