# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 186/1603 data_sz015m _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H24 Mn2 N16' _chemical_formula_weight 646.47 _chemical_melting_point ? _chemical_compound_source ? 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' '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 'P 1 21/n 1' 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 7.8380(2) _cell_length_b 19.8698(5) _cell_length_c 9.5558(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.9320(10) _cell_angle_gamma 90.00 _cell_volume 1380.51(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5441 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 33.16 _exptl_crystal_description slab _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method ? _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.963 _exptl_absorpt_correction_type 'empirical using SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.831 _exptl_absorpt_correction_T_max 0.962 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8896 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3170 _reflns_number_observed 2497 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1994)' _computing_structure_solution 'SHELXTL (Sheldrick, 1996)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1996)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1996)' _computing_publication_material ; SHELXTL (Sheldrick, 1996) PARST (Nardelli, 1995) ; _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating observed R-factor etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.3325P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3169 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_obs 0.0348 _refine_ls_wR_factor_all 0.0823 _refine_ls_wR_factor_obs 0.0735 _refine_ls_goodness_of_fit_all 1.075 _refine_ls_goodness_of_fit_obs 1.094 _refine_ls_restrained_S_all 1.076 _refine_ls_restrained_S_obs 1.094 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Mn1 Mn 0.06039(4) 0.03401(2) 0.35397(3) 0.02440(10) Uani 1 d . . N1 N -0.2230(2) 0.07652(9) 0.2438(2) 0.0293(4) Uani 1 d . . N2 N 0.0869(2) 0.14666(9) 0.3185(2) 0.0279(4) Uani 1 d . . N3 N 0.0353(3) 0.06143(10) 0.5833(2) 0.0329(4) Uani 1 d . . N4 N -0.0185(3) 0.11608(10) 0.5971(2) 0.0347(4) Uani 1 d . . N5 N -0.0680(4) 0.16901(13) 0.6095(3) 0.0710(8) Uani 1 d . . N6 N 0.0412(3) -0.00395(13) 0.1298(2) 0.0506(6) Uani 1 d . . N7 N 0.0000 0.0000 0.0000 0.0303(6) Uani 1 d S . N8 N 0.3537(3) 0.02218(13) 0.4527(3) 0.0542(6) Uani 1 d . . N9 N 0.5000 0.0000 0.5000 0.0294(6) Uani 1 d S . C1 C -0.3748(3) 0.03823(13) 0.2025(3) 0.0369(5) Uani 1 d . . C2 C -0.5483(3) 0.06321(14) 0.1269(3) 0.0399(6) Uani 1 d . . C3 C -0.5721(3) 0.13049(13) 0.0901(3) 0.0351(5) Uani 1 d . . C4 C -0.4157(3) 0.17105(12) 0.1358(3) 0.0327(5) Uani 1 d . . C5 C -0.2436(3) 0.14257(11) 0.2116(2) 0.0269(4) Uani 1 d . . C6 C -0.0700(3) 0.18262(11) 0.2589(2) 0.0268(4) Uani 1 d . . C7 C -0.0675(3) 0.25186(12) 0.2425(3) 0.0347(5) Uani 1 d . . C8 C 0.0973(3) 0.28686(12) 0.2865(3) 0.0370(5) Uani 1 d . . C9 C 0.2573(3) 0.24908(13) 0.3467(3) 0.0404(6) Uani 1 d . . C10 C 0.2468(3) 0.18048(13) 0.3621(3) 0.0358(5) Uani 1 d . . C11 C -0.7592(4) 0.1598(2) 0.0016(4) 0.0497(7) Uani 1 d . . C12 C 0.1016(6) 0.3618(2) 0.2702(5) 0.0570(8) Uani 1 d . . H1 H -0.3550(35) -0.0080(15) 0.2321(28) 0.045(7) Uiso 1 d . . H2 H -0.6541(40) 0.0345(13) 0.0971(30) 0.051(8) Uiso 1 d . . H4 H -0.4303(34) 0.2189(15) 0.1144(29) 0.047(7) Uiso 1 d . . H7 H -0.1760(31) 0.2723(12) 0.2009(25) 0.031(6) Uiso 1 d . . H9 H 0.3672(41) 0.2712(16) 0.3725(32) 0.062(9) Uiso 1 d . . H10 H 0.3553(33) 0.1550(13) 0.3994(27) 0.039(7) Uiso 1 d . . H11A H -0.8013(48) 0.1424(19) -0.0956(45) 0.092(13) Uiso 1 d . . H11B H -0.7607(48) 0.2080(21) -0.0101(41) 0.093(13) Uiso 1 d . . H11C H -0.8443(52) 0.1437(20) 0.0313(44) 0.099(13) Uiso 1 d . . H12A H -0.0182(58) 0.3800(21) 0.2233(46) 0.103(14) Uiso 1 d . . H12B H 0.1661(57) 0.3809(23) 0.3560(50) 0.111(16) Uiso 1 d . . H12C H 0.1447(52) 0.3707(21) 0.2014(44) 0.100(14) Uiso 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 Mn1 0.0221(2) 0.0248(2) 0.0261(2) 0.00299(13) 0.00888(12) 0.00253(13) N1 0.0260(9) 0.0254(10) 0.0338(9) 0.0042(7) 0.0080(7) -0.0025(7) N2 0.0241(9) 0.0278(10) 0.0296(9) 0.0039(7) 0.0076(7) -0.0011(7) N3 0.0424(11) 0.0248(10) 0.0348(10) 0.0038(8) 0.0180(8) 0.0046(8) N4 0.0479(11) 0.0279(11) 0.0336(10) -0.0014(8) 0.0215(9) -0.0022(9) N5 0.121(2) 0.0311(14) 0.081(2) -0.0016(12) 0.061(2) 0.0142(14) N6 0.0557(14) 0.067(2) 0.0311(12) -0.0082(10) 0.0184(10) -0.0077(12) N7 0.0242(12) 0.034(2) 0.0363(15) -0.0084(12) 0.0155(11) -0.0059(11) N8 0.0279(12) 0.068(2) 0.0611(15) 0.0057(12) 0.0098(10) 0.0122(10) N9 0.0215(13) 0.035(2) 0.0305(13) -0.0037(11) 0.0076(10) 0.0002(11) C1 0.0303(11) 0.0297(13) 0.0464(13) 0.0077(11) 0.0093(10) -0.0038(10) C2 0.0267(12) 0.0443(15) 0.0457(14) 0.0038(11) 0.0100(10) -0.0090(10) C3 0.0249(11) 0.0454(15) 0.0329(11) 0.0018(10) 0.0084(9) 0.0026(10) C4 0.0273(11) 0.0298(13) 0.0369(12) 0.0046(10) 0.0075(9) 0.0021(9) C5 0.0246(10) 0.0278(11) 0.0262(10) 0.0038(8) 0.0072(8) 0.0006(8) C6 0.0288(10) 0.0270(11) 0.0242(10) 0.0030(8) 0.0093(8) -0.0018(9) C7 0.0365(13) 0.0286(12) 0.0375(12) 0.0043(10) 0.0120(10) 0.0015(10) C8 0.0471(14) 0.0284(13) 0.0364(12) -0.0005(10) 0.0167(10) -0.0080(10) C9 0.0340(13) 0.0407(15) 0.0435(13) 0.0001(11) 0.0112(11) -0.0145(11) C10 0.0262(11) 0.0385(14) 0.0380(12) 0.0037(10) 0.0067(9) -0.0052(10) C11 0.0252(13) 0.060(2) 0.055(2) 0.0090(15) 0.0051(12) 0.0062(12) C12 0.071(2) 0.031(2) 0.070(2) 0.0032(15) 0.027(2) -0.0130(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 Mn1 N8 2.147(2) . ? Mn1 N3 2.203(2) 3_556 ? Mn1 N6 2.223(2) . ? Mn1 N1 2.238(2) . ? Mn1 N2 2.285(2) . ? Mn1 N3 2.336(2) . ? N1 C1 1.341(3) . ? N1 C5 1.344(3) . ? N2 C10 1.344(3) . ? N2 C6 1.351(3) . ? N3 N4 1.190(3) . ? N3 Mn1 2.203(2) 3_556 ? N4 N5 1.143(3) . ? N6 N7 1.162(2) . ? N7 N6 1.162(2) 3 ? N8 N9 1.152(2) . ? N9 N8 1.152(2) 3_656 ? C1 C2 1.372(3) . ? C2 C3 1.377(4) . ? C3 C4 1.394(3) . ? C3 C11 1.509(3) . ? C4 C5 1.391(3) . ? C5 C6 1.493(3) . ? C6 C7 1.386(3) . ? C7 C8 1.386(3) . ? C8 C9 1.389(4) . ? C8 C12 1.498(4) . ? C9 C10 1.377(4) . ? 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 N8 Mn1 N3 101.76(8) . 3_556 ? N8 Mn1 N6 93.58(9) . . ? N3 Mn1 N6 93.61(8) 3_556 . ? N8 Mn1 N1 163.67(8) . . ? N3 Mn1 N1 94.23(7) 3_556 . ? N6 Mn1 N1 88.65(8) . . ? N8 Mn1 N2 91.76(8) . . ? N3 Mn1 N2 160.49(7) 3_556 . ? N6 Mn1 N2 99.59(8) . . ? N1 Mn1 N2 71.93(6) . . ? N8 Mn1 N3 93.71(8) . . ? N3 Mn1 N3 77.82(8) 3_556 . ? N6 Mn1 N3 169.73(8) . . ? N1 Mn1 N3 86.38(7) . . ? N2 Mn1 N3 87.41(7) . . ? C1 N1 C5 118.0(2) . . ? C1 N1 Mn1 122.7(2) . . ? C5 N1 Mn1 119.29(13) . . ? C10 N2 C6 117.6(2) . . ? C10 N2 Mn1 124.7(2) . . ? C6 N2 Mn1 117.50(13) . . ? N4 N3 Mn1 125.7(2) . 3_556 ? N4 N3 Mn1 118.33(15) . . ? Mn1 N3 Mn1 102.18(8) 3_556 . ? N5 N4 N3 178.9(3) . . ? N7 N6 Mn1 153.9(2) . . ? N6 N7 N6 180.0 . 3 ? N9 N8 Mn1 163.8(2) . . ? N8 N9 N8 180.0 3_656 . ? N1 C1 C2 123.0(2) . . ? C1 C2 C3 119.9(2) . . ? C2 C3 C4 117.5(2) . . ? C2 C3 C11 121.9(2) . . ? C4 C3 C11 120.6(2) . . ? C5 C4 C3 119.8(2) . . ? N1 C5 C4 121.8(2) . . ? N1 C5 C6 115.7(2) . . ? C4 C5 C6 122.5(2) . . ? N2 C6 C7 121.6(2) . . ? N2 C6 C5 115.4(2) . . ? C7 C6 C5 123.0(2) . . ? C6 C7 C8 121.0(2) . . ? C7 C8 C9 116.7(2) . . ? C7 C8 C12 121.4(3) . . ? C9 C8 C12 121.9(2) . . ? C10 C9 C8 119.9(2) . . ? N2 C10 C9 123.3(2) . . ? 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 N8 Mn1 N1 C1 174.6(3) . . . . ? N3 Mn1 N1 C1 -17.0(2) 3_556 . . . ? N6 Mn1 N1 C1 76.5(2) . . . . ? N2 Mn1 N1 C1 177.0(2) . . . . ? N3 Mn1 N1 C1 -94.5(2) . . . . ? N8 Mn1 N1 C5 -2.6(4) . . . . ? N3 Mn1 N1 C5 165.7(2) 3_556 . . . ? N6 Mn1 N1 C5 -100.8(2) . . . . ? N2 Mn1 N1 C5 -0.24(14) . . . . ? N3 Mn1 N1 C5 88.2(2) . . . . ? N8 Mn1 N2 C10 -2.7(2) . . . . ? N3 Mn1 N2 C10 131.5(2) 3_556 . . . ? N6 Mn1 N2 C10 -96.6(2) . . . . ? N1 Mn1 N2 C10 178.0(2) . . . . ? N3 Mn1 N2 C10 91.0(2) . . . . ? N8 Mn1 N2 C6 -177.8(2) . . . . ? N3 Mn1 N2 C6 -43.6(3) 3_556 . . . ? N6 Mn1 N2 C6 88.2(2) . . . . ? N1 Mn1 N2 C6 2.84(14) . . . . ? N3 Mn1 N2 C6 -84.20(15) . . . . ? N8 Mn1 N3 N4 116.1(2) . . . . ? N3 Mn1 N3 N4 -142.7(2) 3_556 . . . ? N6 Mn1 N3 N4 -108.8(5) . . . . ? N1 Mn1 N3 N4 -47.6(2) . . . . ? N2 Mn1 N3 N4 24.5(2) . . . . ? N8 Mn1 N3 Mn1 -101.24(9) . . . 3_556 ? N3 Mn1 N3 Mn1 0.0 3_556 . . 3_556 ? N6 Mn1 N3 Mn1 33.9(5) . . . 3_556 ? N1 Mn1 N3 Mn1 95.12(8) . . . 3_556 ? N2 Mn1 N3 Mn1 167.17(7) . . . 3_556 ? Mn1 N3 N4 N5 177.0(1000) 3_556 . . . ? Mn1 N3 N4 N5 -49.9(131) . . . . ? N8 Mn1 N6 N7 -123.9(4) . . . . ? N3 Mn1 N6 N7 134.0(4) 3_556 . . . ? N1 Mn1 N6 N7 39.9(4) . . . . ? N2 Mn1 N6 N7 -31.6(4) . . . . ? N3 Mn1 N6 N7 100.9(6) . . . . ? Mn1 N6 N7 N6 -142.4(123) . . . 3 ? N3 Mn1 N8 N9 28.2(7) 3_556 . . . ? N6 Mn1 N8 N9 -66.3(7) . . . . ? N1 Mn1 N8 N9 -163.7(5) . . . . ? N2 Mn1 N8 N9 -166.0(6) . . . . ? N3 Mn1 N8 N9 106.5(6) . . . . ? Mn1 N8 N9 N8 16.0(1000) . . . 3_656 ? C5 N1 C1 C2 1.3(3) . . . . ? Mn1 N1 C1 C2 -176.0(2) . . . . ? N1 C1 C2 C3 0.0(4) . . . . ? C1 C2 C3 C4 -1.5(4) . . . . ? C1 C2 C3 C11 177.5(3) . . . . ? C2 C3 C4 C5 1.8(3) . . . . ? C11 C3 C4 C5 -177.2(2) . . . . ? C1 N1 C5 C4 -0.9(3) . . . . ? Mn1 N1 C5 C4 176.4(2) . . . . ? C1 N1 C5 C6 -179.5(2) . . . . ? Mn1 N1 C5 C6 -2.1(2) . . . . ? C3 C4 C5 N1 -0.6(3) . . . . ? C3 C4 C5 C6 177.8(2) . . . . ? C10 N2 C6 C7 0.2(3) . . . . ? Mn1 N2 C6 C7 175.7(2) . . . . ? C10 N2 C6 C5 179.7(2) . . . . ? Mn1 N2 C6 C5 -4.8(2) . . . . ? N1 C5 C6 N2 4.6(3) . . . . ? C4 C5 C6 N2 -174.0(2) . . . . ? N1 C5 C6 C7 -176.0(2) . . . . ? C4 C5 C6 C7 5.5(3) . . . . ? N2 C6 C7 C8 0.2(3) . . . . ? C5 C6 C7 C8 -179.2(2) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C6 C7 C8 C12 -179.6(3) . . . . ? C7 C8 C9 C10 -0.9(4) . . . . ? C12 C8 C9 C10 178.9(3) . . . . ? C6 N2 C10 C9 -1.0(3) . . . . ? Mn1 N2 C10 C9 -176.1(2) . . . . ? C8 C9 C10 N2 1.4(4) . . . . ? _refine_diff_density_max 0.287 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.058 #============================================================================ #END OF CIF data_sz012m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cu N8' _chemical_formula_weight 331.84 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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9610(6) _cell_length_b 9.3920(6) _cell_length_c 10.7626(8) _cell_angle_alpha 113.4390(10) _cell_angle_beta 101.2280(10) _cell_angle_gamma 101.9820(10) _cell_volume 686.89(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3295 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 28.30 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 338 _exptl_absorpt_coefficient_mu 1.596 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5822 _exptl_absorpt_correction_T_max 0.6460 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4892 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3352 _reflns_number_gt 2755 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996a)' _computing_cell_refinement 'SAINT (Siemens, 1996b)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PARST (Nardelli, 1995)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+0.0268P] 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 3352 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 -0.29254(5) 0.00051(4) 0.09009(3) 0.03338(14) Uani 1 1 d . . . N1 N -0.1590(3) 0.1206(3) 0.3023(3) 0.0345(5) Uani 1 1 d . . . N2 N -0.4218(3) -0.1515(3) 0.1564(2) 0.0283(4) Uani 1 1 d . . . N3 N -0.1502(4) 0.1743(4) 0.0563(3) 0.0519(7) Uani 1 1 d . . . N4 N -0.0412(4) 0.1636(3) 0.0049(3) 0.0447(6) Uani 1 1 d . . . N5 N 0.0764(6) 0.1640(5) -0.0456(6) 0.0903(14) Uani 1 1 d . . . N6 N -0.4494(4) -0.1359(3) -0.1109(3) 0.0447(6) Uani 1 1 d . . . N7 N -0.3995(4) -0.1314(3) -0.2078(3) 0.0426(6) Uani 1 1 d . . . N8 N -0.3610(6) -0.1313(5) -0.3043(3) 0.0734(10) Uani 1 1 d . . . C1 C -0.0187(5) 0.2592(4) 0.3688(4) 0.0507(8) Uani 1 1 d . . . H1A H 0.0272 0.3039 0.3145 0.061 Uiso 1 1 calc R . . C2 C 0.0598(5) 0.3377(4) 0.5141(4) 0.0530(9) Uani 1 1 d . . . H2A H 0.1573 0.4334 0.5561 0.064 Uiso 1 1 calc R . . C3 C -0.0049(4) 0.2754(4) 0.5978(3) 0.0425(7) Uani 1 1 d . . . C4 C -0.1481(4) 0.1287(4) 0.5282(3) 0.0373(6) Uani 1 1 d . . . H4A H -0.1946 0.0810 0.5804 0.045 Uiso 1 1 calc R . . C5 C -0.2202(4) 0.0550(3) 0.3822(3) 0.0300(5) Uani 1 1 d . . . C6 C -0.3674(3) -0.1041(3) 0.2973(3) 0.0277(5) Uani 1 1 d . . . C7 C -0.4371(4) -0.1993(3) 0.3570(3) 0.0348(6) Uani 1 1 d . . . H7A H -0.3984 -0.1617 0.4550 0.042 Uiso 1 1 calc R . . C8 C -0.5666(4) -0.3531(3) 0.2682(3) 0.0361(6) Uani 1 1 d . . . C9 C -0.6232(4) -0.3981(4) 0.1245(3) 0.0392(7) Uani 1 1 d . . . H9A H -0.7111 -0.4982 0.0624 0.047 Uiso 1 1 calc R . . C10 C -0.5505(4) -0.2961(3) 0.0723(3) 0.0359(6) Uani 1 1 d . . . H10A H -0.5922 -0.3286 -0.0248 0.043 Uiso 1 1 calc R . . C11 C 0.0731(6) 0.3624(5) 0.7575(4) 0.0618(10) Uani 1 1 d . . . H11A H 0.0950 0.4778 0.7908 0.093 Uiso 1 1 calc R . . H11B H 0.1846 0.3426 0.7852 0.093 Uiso 1 1 calc R . . H11C H -0.0106 0.3224 0.7985 0.093 Uiso 1 1 calc R . . C12 C -0.6368(5) -0.4636(4) 0.3281(4) 0.0551(9) Uani 1 1 d . . . H12A H -0.6532 -0.4001 0.4173 0.083 Uiso 1 1 calc R . . H12B H -0.5520 -0.5191 0.3426 0.083 Uiso 1 1 calc R . . H12C H -0.7504 -0.5427 0.2627 0.083 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 0.0429(2) 0.0351(2) 0.02337(19) 0.01666(15) 0.01256(14) 0.00600(14) N1 0.0361(12) 0.0340(12) 0.0276(11) 0.0144(9) 0.0068(9) 0.0021(9) N2 0.0346(11) 0.0292(11) 0.0199(10) 0.0118(8) 0.0082(8) 0.0067(9) N3 0.071(2) 0.0464(16) 0.0528(17) 0.0320(14) 0.0293(15) 0.0177(14) N4 0.0479(15) 0.0428(15) 0.0541(17) 0.0331(13) 0.0166(13) 0.0122(12) N5 0.089(3) 0.096(3) 0.145(4) 0.082(3) 0.082(3) 0.048(2) N6 0.0604(17) 0.0483(15) 0.0243(12) 0.0171(11) 0.0164(11) 0.0107(13) N7 0.0611(17) 0.0477(15) 0.0255(12) 0.0185(11) 0.0163(11) 0.0232(13) N8 0.104(3) 0.103(3) 0.0372(17) 0.0394(18) 0.0402(18) 0.046(2) C1 0.0467(18) 0.0453(18) 0.0478(19) 0.0222(15) 0.0083(15) -0.0053(14) C2 0.0457(18) 0.0386(17) 0.050(2) 0.0144(15) -0.0034(15) -0.0059(14) C3 0.0436(16) 0.0363(15) 0.0322(15) 0.0081(12) -0.0025(12) 0.0116(13) C4 0.0471(16) 0.0353(14) 0.0263(14) 0.0137(11) 0.0076(12) 0.0110(12) C5 0.0342(13) 0.0276(13) 0.0263(13) 0.0120(10) 0.0082(10) 0.0079(10) C6 0.0351(13) 0.0275(12) 0.0205(12) 0.0118(10) 0.0081(10) 0.0088(10) C7 0.0485(16) 0.0347(14) 0.0231(13) 0.0159(11) 0.0132(11) 0.0092(12) C8 0.0418(15) 0.0321(14) 0.0372(15) 0.0196(12) 0.0140(12) 0.0076(12) C9 0.0430(16) 0.0302(14) 0.0326(15) 0.0113(12) 0.0064(12) 0.0000(12) C10 0.0432(15) 0.0344(14) 0.0213(13) 0.0109(11) 0.0044(11) 0.0041(12) C11 0.069(2) 0.052(2) 0.0358(18) 0.0062(15) -0.0081(16) 0.0120(18) C12 0.070(2) 0.0455(19) 0.052(2) 0.0320(17) 0.0201(17) 0.0025(16) _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 N3 1.987(3) . ? Cu1 N6 1.990(3) . ? Cu1 N2 2.023(2) . ? Cu1 N1 2.031(2) . ? N1 C1 1.340(4) . ? N1 C5 1.348(4) . ? N2 C10 1.341(3) . ? N2 C6 1.346(3) . ? N3 N4 1.117(4) . ? N4 N5 1.171(5) . ? N6 N7 1.199(4) . ? N7 N8 1.139(4) . ? C1 C2 1.375(5) . ? C2 C3 1.376(5) . ? C3 C4 1.397(4) . ? C3 C11 1.505(4) . ? C4 C5 1.377(4) . ? C5 C6 1.487(4) . ? C6 C7 1.381(4) . ? C7 C8 1.401(4) . ? C8 C9 1.380(4) . ? C8 C12 1.495(4) . ? C9 C10 1.376(4) . ? 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 N3 Cu1 N6 95.62(12) . . ? N3 Cu1 N2 171.23(11) . . ? N6 Cu1 N2 92.82(10) . . ? N3 Cu1 N1 92.25(11) . . ? N6 Cu1 N1 171.81(10) . . ? N2 Cu1 N1 79.22(9) . . ? C1 N1 C5 117.9(3) . . ? C1 N1 Cu1 125.8(2) . . ? C5 N1 Cu1 116.30(18) . . ? C10 N2 C6 118.0(2) . . ? C10 N2 Cu1 125.77(18) . . ? C6 N2 Cu1 116.21(17) . . ? N4 N3 Cu1 125.1(3) . . ? N3 N4 N5 175.3(4) . . ? N7 N6 Cu1 121.3(2) . . ? N8 N7 N6 176.5(4) . . ? N1 C1 C2 122.5(3) . . ? C1 C2 C3 120.4(3) . . ? C2 C3 C4 117.2(3) . . ? C2 C3 C11 121.5(3) . . ? C4 C3 C11 121.3(3) . . ? C5 C4 C3 119.8(3) . . ? N1 C5 C4 122.2(3) . . ? N1 C5 C6 113.6(2) . . ? C4 C5 C6 124.2(3) . . ? N2 C6 C7 122.6(2) . . ? N2 C6 C5 114.5(2) . . ? C7 C6 C5 122.9(2) . . ? C6 C7 C8 119.3(2) . . ? C9 C8 C7 117.2(3) . . ? C9 C8 C12 122.0(3) . . ? C7 C8 C12 120.8(3) . . ? C10 C9 C8 120.5(3) . . ? N2 C10 C9 122.4(2) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.579 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.084