Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name C.Aakeroy _publ_contact_author_address ; Department of Chemistry Kansas State University Manhattan Kansas 66506-3701 UNITED STATES OF AMERICA ; _publ_contact_author_email AAKEROY@KSU.EDU _publ_section_title ; Directed Supramolecular Assembly of Cu(II)-based Paddlewheels Into Infinite 1-D Chains Using Structurally Bifunctional Ligands ; loop_ _publ_author_name 'C. Aakeroy' 'John Desper' 'Nate Schultheiss' data_7 _database_code_depnum_ccdc_archive 'CCDC 278015' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(2-amino-4-(3-pyridyl)-6-methylpyrimidine) mu-(OAc)4dicopper(II) ; _chemical_name_common ;bis(2-amino-4-(3-pyridyl)-6-methylpyrimidine) mu- (OAc)4dicopper(ii) ; _chemical_melting_point ? _chemical_formula_moiety ; (C10 H10 N4)2 Cu2 (C2 H3 O2)4 ; _chemical_formula_sum 'C28 H32 Cu2 N8 O8' _chemical_formula_weight 735.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0282(5) _cell_length_b 10.6399(7) _cell_length_c 18.9041(13) _cell_angle_alpha 90.00 _cell_angle_beta 99.3600(10) _cell_angle_gamma 90.00 _cell_volume 1593.27(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9401 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 30.0 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 1.396 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.825 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17891 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4630 _reflns_number_gt 4270 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+1.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4630 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0767 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.462311(19) 0.439494(15) 0.055368(8) 0.01102(6) Uani 1 1 d . . . N11 N 0.09429(15) 0.53063(11) 0.41833(6) 0.0155(2) Uani 1 1 d . . . C12 C 0.14818(17) 0.40981(13) 0.42452(7) 0.0153(2) Uani 1 1 d . . . N12 N 0.13080(18) 0.34958(13) 0.48548(7) 0.0208(3) Uani 1 1 d . . . H12A H 0.074(3) 0.387(2) 0.5130(11) 0.025 Uiso 1 1 d . . . H12B H 0.171(3) 0.274(2) 0.4920(11) 0.025 Uiso 1 1 d . . . N13 N 0.21770(15) 0.34481(11) 0.37516(6) 0.0148(2) Uani 1 1 d . . . C14 C 0.23682(16) 0.40786(13) 0.31574(7) 0.0132(2) Uani 1 1 d . . . C15 C 0.19181(18) 0.53398(13) 0.30590(7) 0.0154(2) Uani 1 1 d . . . H15 H 0.2098 0.5785 0.2642 0.019 Uiso 1 1 calc R . . C16 C 0.11936(17) 0.59216(13) 0.35964(7) 0.0145(2) Uani 1 1 d . . . C17 C 0.07116(19) 0.72802(13) 0.35467(8) 0.0199(3) Uani 1 1 d . . . H17A H -0.0361 0.7396 0.3722 0.030 Uiso 1 1 calc R . . H17B H 0.0588 0.7555 0.3046 0.030 Uiso 1 1 calc R . . H17C H 0.1592 0.7780 0.3839 0.030 Uiso 1 1 calc R . . N21 N 0.40246(14) 0.33167(11) 0.14568(6) 0.0137(2) Uani 1 1 d . . . C22 C 0.34705(17) 0.39363(13) 0.19912(7) 0.0138(2) Uani 1 1 d . . . H22 H 0.3352 0.4823 0.1954 0.017 Uiso 1 1 calc R . . C23 C 0.30597(16) 0.33480(13) 0.25988(7) 0.0132(2) Uani 1 1 d . . . C24 C 0.32661(18) 0.20462(13) 0.26517(7) 0.0162(2) Uani 1 1 d . . . H24 H 0.3030 0.1609 0.3062 0.019 Uiso 1 1 calc R . . C25 C 0.38205(18) 0.14001(13) 0.20962(7) 0.0176(3) Uani 1 1 d . . . H25 H 0.3950 0.0513 0.2119 0.021 Uiso 1 1 calc R . . C26 C 0.41840(18) 0.20641(13) 0.15067(7) 0.0162(2) Uani 1 1 d . . . H26 H 0.4557 0.1616 0.1127 0.019 Uiso 1 1 calc R . . C31 C 0.59961(16) 0.29669(13) -0.05024(7) 0.0139(2) Uani 1 1 d . . . O31 O 0.54690(13) 0.29206(10) 0.00921(5) 0.0174(2) Uani 1 1 d . . . O32 O 0.60947(12) 0.39504(9) -0.08686(5) 0.01516(19) Uani 1 1 d . . . C32 C 0.65970(19) 0.17496(14) -0.07849(8) 0.0197(3) Uani 1 1 d . . . H32 H 0.6737 0.1860 -0.1287 0.030 Uiso 1 1 calc R . . H32B H 0.5763 0.1088 -0.0753 0.030 Uiso 1 1 calc R . . H32C H 0.7680 0.1511 -0.0499 0.030 Uiso 1 1 calc R . . C41 C 0.79690(17) 0.53896(12) 0.06778(7) 0.0131(2) Uani 1 1 d . . . O41 O 0.69467(12) 0.48116(10) 0.10012(5) 0.01548(19) Uani 1 1 d . . . O42 O 0.76215(12) 0.58161(9) 0.00431(5) 0.01482(19) Uani 1 1 d . . . C42 C 0.97405(18) 0.55786(14) 0.10690(8) 0.0186(3) Uani 1 1 d . . . H42 H 0.9854 0.5189 0.1544 0.028 Uiso 1 1 calc R . . H42B H 0.9978 0.6480 0.1122 0.028 Uiso 1 1 calc R . . H42C H 1.0542 0.5189 0.0796 0.028 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 0.01235(9) 0.01183(9) 0.00924(8) -0.00010(5) 0.00289(6) -0.00039(5) N11 0.0179(5) 0.0144(5) 0.0148(5) -0.0007(4) 0.0041(4) 0.0017(4) C12 0.0175(6) 0.0155(6) 0.0133(6) -0.0002(5) 0.0042(5) 0.0021(5) N12 0.0327(7) 0.0173(6) 0.0152(6) 0.0034(5) 0.0119(5) 0.0090(5) N13 0.0187(5) 0.0149(5) 0.0117(5) 0.0009(4) 0.0051(4) 0.0020(4) C14 0.0137(5) 0.0152(6) 0.0108(5) -0.0004(5) 0.0025(4) -0.0003(5) C15 0.0183(6) 0.0148(6) 0.0136(6) 0.0018(5) 0.0036(5) 0.0004(5) C16 0.0147(6) 0.0137(6) 0.0144(6) -0.0006(5) 0.0006(5) 0.0002(5) C17 0.0231(7) 0.0131(6) 0.0233(7) 0.0006(5) 0.0038(6) 0.0022(5) N21 0.0148(5) 0.0153(5) 0.0113(5) 0.0002(4) 0.0030(4) 0.0005(4) C22 0.0155(6) 0.0140(6) 0.0120(6) 0.0002(5) 0.0026(4) -0.0002(5) C23 0.0145(6) 0.0149(6) 0.0102(5) 0.0000(4) 0.0028(4) 0.0005(4) C24 0.0204(6) 0.0160(6) 0.0130(6) 0.0030(5) 0.0051(5) 0.0026(5) C25 0.0241(7) 0.0143(6) 0.0154(6) 0.0025(5) 0.0060(5) 0.0045(5) C26 0.0195(6) 0.0170(6) 0.0129(6) 0.0012(5) 0.0048(5) 0.0022(5) C31 0.0127(5) 0.0152(6) 0.0132(5) -0.0028(5) 0.0005(4) 0.0003(4) O31 0.0225(5) 0.0153(4) 0.0151(4) -0.0003(4) 0.0058(4) 0.0025(4) O32 0.0174(4) 0.0149(4) 0.0139(4) -0.0016(4) 0.0047(4) 0.0007(4) C32 0.0222(7) 0.0169(6) 0.0201(6) -0.0045(5) 0.0040(5) 0.0041(5) C41 0.0133(5) 0.0116(5) 0.0143(6) -0.0028(4) 0.0021(5) 0.0011(4) O41 0.0141(4) 0.0179(5) 0.0143(4) 0.0012(4) 0.0019(3) -0.0006(4) O42 0.0142(4) 0.0173(5) 0.0130(4) -0.0011(4) 0.0024(3) -0.0024(3) C42 0.0133(6) 0.0216(7) 0.0201(7) -0.0018(5) 0.0000(5) -0.0011(5) _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 O31 1.9688(10) . ? Cu1 O41 1.9694(10) . ? Cu1 O32 1.9742(10) 3_665 ? Cu1 O42 1.9771(10) 3_665 ? Cu1 N21 2.1745(11) . ? Cu1 Cu1 2.6112(3) 3_665 ? N11 C16 1.3313(18) . ? N11 C12 1.3553(18) . ? C12 N12 1.3454(18) . ? C12 N13 1.3528(17) . ? N12 H12A 0.85(2) . ? N12 H12B 0.87(2) . ? N13 C14 1.3385(17) . ? C14 C15 1.3942(19) . ? C14 C23 1.4893(18) . ? C15 C16 1.3949(18) . ? C15 H15 0.9500 . ? C16 C17 1.4955(19) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N21 C26 1.3408(18) . ? N21 C22 1.3414(16) . ? C22 C23 1.3939(17) . ? C22 H22 0.9500 . ? C23 C24 1.3967(19) . ? C24 C25 1.3876(18) . ? C24 H24 0.9500 . ? C25 C26 1.3900(18) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 O32 1.2642(17) . ? C31 O31 1.2646(16) . ? C31 C32 1.5098(19) . ? O32 Cu1 1.9742(10) 3_665 ? C32 H32 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C41 O41 1.2605(16) . ? C41 O42 1.2706(17) . ? C41 C42 1.5060(19) . ? O42 Cu1 1.9771(10) 3_665 ? C42 H42 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? 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 O31 Cu1 O41 89.94(4) . . ? O31 Cu1 O32 169.36(4) . 3_665 ? O41 Cu1 O32 88.41(4) . 3_665 ? O31 Cu1 O42 90.27(4) . 3_665 ? O41 Cu1 O42 169.22(4) . 3_665 ? O32 Cu1 O42 89.40(4) 3_665 3_665 ? O31 Cu1 N21 93.66(4) . . ? O41 Cu1 N21 95.53(4) . . ? O32 Cu1 N21 96.96(4) 3_665 . ? O42 Cu1 N21 95.21(4) 3_665 . ? O31 Cu1 Cu1 84.03(3) . 3_665 ? O41 Cu1 Cu1 84.64(3) . 3_665 ? O32 Cu1 Cu1 85.36(3) 3_665 3_665 ? O42 Cu1 Cu1 84.67(3) 3_665 3_665 ? N21 Cu1 Cu1 177.68(3) . 3_665 ? C16 N11 C12 116.68(12) . . ? N12 C12 N13 117.34(13) . . ? N12 C12 N11 116.72(12) . . ? N13 C12 N11 125.94(12) . . ? C12 N12 H12A 116.4(14) . . ? C12 N12 H12B 118.3(14) . . ? H12A N12 H12B 125(2) . . ? C14 N13 C12 116.05(12) . . ? N13 C14 C15 122.12(12) . . ? N13 C14 C23 116.12(12) . . ? C15 C14 C23 121.75(12) . . ? C14 C15 C16 117.37(12) . . ? C14 C15 H15 121.3 . . ? C16 C15 H15 121.3 . . ? N11 C16 C15 121.74(13) . . ? N11 C16 C17 117.07(12) . . ? C15 C16 C17 121.16(13) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C26 N21 C22 118.36(12) . . ? C26 N21 Cu1 123.29(9) . . ? C22 N21 Cu1 118.35(9) . . ? N21 C22 C23 123.50(13) . . ? N21 C22 H22 118.3 . . ? C23 C22 H22 118.3 . . ? C22 C23 C24 117.59(12) . . ? C22 C23 C14 121.01(12) . . ? C24 C23 C14 121.37(12) . . ? C25 C24 C23 119.08(12) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 119.34(13) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? N21 C26 C25 122.11(12) . . ? N21 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? O32 C31 O31 125.36(13) . . ? O32 C31 C32 117.67(12) . . ? O31 C31 C32 116.95(12) . . ? C31 O31 Cu1 123.52(9) . . ? C31 O32 Cu1 121.72(8) . 3_665 ? C31 C32 H32 109.5 . . ? C31 C32 H32B 109.5 . . ? H32 C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32 C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O41 C41 O42 124.89(13) . . ? O41 C41 C42 117.67(12) . . ? O42 C41 C42 117.44(12) . . ? C41 O41 Cu1 123.19(9) . . ? C41 O42 Cu1 122.55(9) . 3_665 ? C41 C42 H42 109.5 . . ? C41 C42 H42B 109.5 . . ? H42 C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42 C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? 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 C16 N11 C12 N12 176.69(13) . . . . ? C16 N11 C12 N13 -3.2(2) . . . . ? N12 C12 N13 C14 -178.60(13) . . . . ? N11 C12 N13 C14 1.3(2) . . . . ? C12 N13 C14 C15 1.6(2) . . . . ? C12 N13 C14 C23 -177.28(12) . . . . ? N13 C14 C15 C16 -2.3(2) . . . . ? C23 C14 C15 C16 176.47(12) . . . . ? C12 N11 C16 C15 2.3(2) . . . . ? C12 N11 C16 C17 -175.92(12) . . . . ? C14 C15 C16 N11 0.3(2) . . . . ? C14 C15 C16 C17 178.40(13) . . . . ? O31 Cu1 N21 C26 -4.38(11) . . . . ? O41 Cu1 N21 C26 -94.67(11) . . . . ? O32 Cu1 N21 C26 176.26(11) 3_665 . . . ? O42 Cu1 N21 C26 86.22(11) 3_665 . . . ? Cu1 Cu1 N21 C26 -0.7(9) 3_665 . . . ? O31 Cu1 N21 C22 175.51(10) . . . . ? O41 Cu1 N21 C22 85.22(10) . . . . ? O32 Cu1 N21 C22 -3.85(10) 3_665 . . . ? O42 Cu1 N21 C22 -93.88(10) 3_665 . . . ? Cu1 Cu1 N21 C22 179(100) 3_665 . . . ? C26 N21 C22 C23 0.4(2) . . . . ? Cu1 N21 C22 C23 -179.52(10) . . . . ? N21 C22 C23 C24 1.0(2) . . . . ? N21 C22 C23 C14 -176.88(12) . . . . ? N13 C14 C23 C22 -173.49(12) . . . . ? C15 C14 C23 C22 7.7(2) . . . . ? N13 C14 C23 C24 8.73(19) . . . . ? C15 C14 C23 C24 -170.12(13) . . . . ? C22 C23 C24 C25 -1.7(2) . . . . ? C14 C23 C24 C25 176.18(13) . . . . ? C23 C24 C25 C26 1.1(2) . . . . ? C22 N21 C26 C25 -1.0(2) . . . . ? Cu1 N21 C26 C25 178.85(10) . . . . ? C24 C25 C26 N21 0.3(2) . . . . ? O32 C31 O31 Cu1 1.92(19) . . . . ? C32 C31 O31 Cu1 -179.77(9) . . . . ? O41 Cu1 O31 C31 -86.09(11) . . . . ? O32 Cu1 O31 C31 -5.1(3) 3_665 . . . ? O42 Cu1 O31 C31 83.14(11) 3_665 . . . ? N21 Cu1 O31 C31 178.38(11) . . . . ? Cu1 Cu1 O31 C31 -1.47(10) 3_665 . . . ? O31 C31 O32 Cu1 -0.98(19) . . . 3_665 ? C32 C31 O32 Cu1 -179.28(9) . . . 3_665 ? O42 C41 O41 Cu1 2.96(19) . . . . ? C42 C41 O41 Cu1 -176.38(9) . . . . ? O31 Cu1 O41 C41 81.45(11) . . . . ? O32 Cu1 O41 C41 -88.04(11) 3_665 . . . ? O42 Cu1 O41 C41 -9.6(3) 3_665 . . . ? N21 Cu1 O41 C41 175.12(11) . . . . ? Cu1 Cu1 O41 C41 -2.55(10) 3_665 . . . ? O41 C41 O42 Cu1 -1.11(19) . . . 3_665 ? C42 C41 O42 Cu1 178.23(9) . . . 3_665 ? 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 N12 H12A N11 0.85(2) 2.20(2) 3.0440(17) 174(2) 3_566 N12 H12B O42 0.87(2) 2.11(2) 2.9752(16) 171.3(19) 2_645 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.553 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.077 #END data_8 _database_code_depnum_ccdc_archive 'CCDC 278016' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(2-amino-4-(3-pyridyl)-6-methoxypyrimidine) mu-(OAc)4 dicopper(II) ; _chemical_name_common ;bis(2-amino-4-(3-pyridyl)-6-methoxypyrimidine) mu-(OAc)4 dicopper(ii) ; _chemical_melting_point ? _chemical_formula_moiety ; (C10 H10 N4 O)2 Cu2 (C2 H3 O2)4 ; _chemical_formula_sum 'C28 H32 Cu2 N8 O10' _chemical_formula_weight 767.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2800(6) _cell_length_b 9.3983(6) _cell_length_c 11.2233(7) _cell_angle_alpha 71.144(4) _cell_angle_beta 81.585(4) _cell_angle_gamma 79.240(4) _cell_volume 808.49(9) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2733 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 28.10 _exptl_crystal_description needle _exptl_crystal_colour aqua _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 394 _exptl_absorpt_coefficient_mu 1.383 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.781 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6060 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 28.24 _reflns_number_total 3638 _reflns_number_gt 3063 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3638 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.300 _refine_ls_restrained_S_all 1.300 _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 0.56055(4) 0.50763(3) 0.09840(2) 0.01528(11) Uani 1 1 d . . . N11 N 0.6667(3) 0.0940(2) 0.55428(19) 0.0214(5) Uani 1 1 d . . . C12 C 0.6944(3) -0.0456(3) 0.6363(2) 0.0208(5) Uani 1 1 d . . . N12 N 0.6286(3) -0.1563(3) 0.6162(2) 0.0261(5) Uani 1 1 d . . . H12A H 0.548(4) -0.132(3) 0.557(3) 0.031 Uiso 1 1 d . . . H12B H 0.632(4) -0.244(4) 0.681(3) 0.031 Uiso 1 1 d . . . N13 N 0.7824(3) -0.0885(2) 0.73718(19) 0.0238(5) Uani 1 1 d . . . C14 C 0.8459(4) 0.0201(3) 0.7553(2) 0.0262(6) Uani 1 1 d . . . C15 C 0.8290(4) 0.1699(3) 0.6755(3) 0.0295(6) Uani 1 1 d . . . H15 H 0.8780 0.2460 0.6898 0.035 Uiso 1 1 calc R . . C16 C 0.7379(3) 0.2003(3) 0.5758(2) 0.0217(5) Uani 1 1 d . . . O17 O 0.9320(3) -0.0100(2) 0.85484(19) 0.0338(5) Uani 1 1 d . . . C17 C 0.9573(4) -0.1656(3) 0.9357(3) 0.0347(7) Uani 1 1 d . . . H17A H 0.9954 -0.1688 1.0153 0.052 Uiso 1 1 calc R . . H17B H 1.0405 -0.2264 0.8933 0.052 Uiso 1 1 calc R . . H17C H 0.8531 -0.2070 0.9533 0.052 Uiso 1 1 calc R . . N21 N 0.6504(2) 0.5021(2) 0.27220(18) 0.0166(4) Uani 1 1 d . . . C22 C 0.6792(3) 0.3682(3) 0.3611(2) 0.0190(5) Uani 1 1 d . . . H22 H 0.6755 0.2785 0.3405 0.023 Uiso 1 1 calc R . . C23 C 0.7141(3) 0.3535(3) 0.4820(2) 0.0194(5) Uani 1 1 d . . . C24 C 0.7250(3) 0.4857(3) 0.5090(2) 0.0247(6) Uani 1 1 d . . . H24 H 0.7496 0.4812 0.5904 0.030 Uiso 1 1 calc R . . C25 C 0.6993(3) 0.6237(3) 0.4154(2) 0.0256(6) Uani 1 1 d . . . H25 H 0.7090 0.7152 0.4309 0.031 Uiso 1 1 calc R . . C26 C 0.6598(3) 0.6272(3) 0.2999(2) 0.0199(5) Uani 1 1 d . . . H26 H 0.6383 0.7229 0.2372 0.024 Uiso 1 1 calc R . . C31 C 0.4275(3) 0.7868(3) -0.0670(2) 0.0198(5) Uani 1 1 d . . . O31 O 0.4972(2) 0.72877(19) 0.03295(17) 0.0255(4) Uani 1 1 d . . . O32 O 0.3939(2) 0.71411(19) -0.13449(17) 0.0251(4) Uani 1 1 d . . . C32 C 0.3775(4) 0.9563(3) -0.1109(3) 0.0288(6) Uani 1 1 d . . . H32A H 0.4687 1.0062 -0.1051 0.043 Uiso 1 1 calc R . . H32B H 0.2804 0.9847 -0.0574 0.043 Uiso 1 1 calc R . . H32C H 0.3508 0.9886 -0.1988 0.043 Uiso 1 1 calc R . . C41 C 0.2196(3) 0.4812(3) 0.1244(2) 0.0176(5) Uani 1 1 d . . . O41 O 0.3360(2) 0.4866(2) 0.18251(16) 0.0240(4) Uani 1 1 d . . . O42 O 0.2337(2) 0.4786(2) 0.01228(16) 0.0237(4) Uani 1 1 d . . . C42 C 0.0522(3) 0.4766(3) 0.1950(2) 0.0265(6) Uani 1 1 d . . . H42A H -0.0290 0.4812 0.1380 0.040 Uiso 1 1 calc R . . H42B H 0.0227 0.5637 0.2280 0.040 Uiso 1 1 calc R . . H42C H 0.0529 0.3821 0.2655 0.040 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 0.01692(17) 0.01542(16) 0.01401(16) -0.00417(11) -0.00356(11) -0.00255(11) N11 0.0270(12) 0.0208(11) 0.0174(10) -0.0044(8) -0.0061(9) -0.0057(9) C12 0.0244(14) 0.0224(12) 0.0165(12) -0.0052(9) -0.0037(10) -0.0058(10) N12 0.0362(14) 0.0215(11) 0.0218(11) -0.0009(9) -0.0124(10) -0.0100(10) N13 0.0301(13) 0.0224(11) 0.0192(11) -0.0031(8) -0.0091(9) -0.0057(9) C14 0.0309(15) 0.0276(14) 0.0217(13) -0.0062(11) -0.0099(11) -0.0049(12) C15 0.0399(17) 0.0232(13) 0.0302(15) -0.0072(11) -0.0159(13) -0.0083(12) C16 0.0271(14) 0.0214(12) 0.0176(12) -0.0049(10) -0.0056(10) -0.0047(11) O17 0.0505(14) 0.0247(10) 0.0287(10) -0.0006(8) -0.0263(9) -0.0077(9) C17 0.051(2) 0.0218(14) 0.0308(15) 0.0002(11) -0.0254(14) -0.0029(13) N21 0.0159(10) 0.0176(10) 0.0147(9) -0.0032(7) -0.0029(8) -0.0005(8) C22 0.0188(12) 0.0203(12) 0.0201(12) -0.0077(9) -0.0038(10) -0.0043(10) C23 0.0184(12) 0.0219(12) 0.0186(12) -0.0051(9) -0.0060(9) -0.0032(10) C24 0.0290(15) 0.0255(13) 0.0223(13) -0.0091(10) -0.0076(11) -0.0029(11) C25 0.0334(16) 0.0204(13) 0.0273(14) -0.0118(10) -0.0068(11) -0.0030(11) C26 0.0219(13) 0.0174(12) 0.0200(12) -0.0054(9) -0.0037(10) -0.0013(10) C31 0.0199(13) 0.0160(11) 0.0223(12) -0.0059(9) 0.0001(10) -0.0016(10) O31 0.0344(11) 0.0178(9) 0.0256(10) -0.0059(7) -0.0123(8) -0.0011(8) O32 0.0359(11) 0.0168(9) 0.0239(9) -0.0058(7) -0.0094(8) -0.0029(8) C32 0.0343(16) 0.0160(12) 0.0341(15) -0.0051(11) -0.0077(12) 0.0002(11) C41 0.0170(12) 0.0147(11) 0.0200(12) -0.0029(9) -0.0042(9) -0.0018(9) O41 0.0189(9) 0.0360(11) 0.0195(9) -0.0099(8) -0.0023(7) -0.0073(8) O42 0.0193(9) 0.0353(10) 0.0189(9) -0.0090(7) -0.0029(7) -0.0077(8) C42 0.0182(13) 0.0368(15) 0.0259(14) -0.0115(11) -0.0015(11) -0.0044(11) _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 O42 1.9548(17) 2_665 ? Cu1 O31 1.9629(17) . ? Cu1 O32 1.9633(17) 2_665 ? Cu1 O41 1.9722(18) . ? Cu1 N21 2.169(2) . ? Cu1 Cu1 2.6099(6) 2_665 ? N11 C12 1.338(3) . ? N11 C16 1.350(3) . ? C12 N13 1.346(3) . ? C12 N12 1.353(3) . ? N12 H12A 0.95(3) . ? N12 H12B 0.91(3) . ? N13 C14 1.313(3) . ? C14 O17 1.337(3) . ? C14 C15 1.397(4) . ? C15 C16 1.365(4) . ? C15 H15 0.9500 . ? C16 C23 1.482(3) . ? O17 C17 1.445(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N21 C26 1.328(3) . ? N21 C22 1.334(3) . ? C22 C23 1.387(3) . ? C22 H22 0.9500 . ? C23 C24 1.392(4) . ? C24 C25 1.384(3) . ? C24 H24 0.9500 . ? C25 C26 1.372(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 O31 1.251(3) . ? C31 O32 1.259(3) . ? C31 C32 1.503(3) . ? O32 Cu1 1.9634(17) 2_665 ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C41 O42 1.254(3) . ? C41 O41 1.258(3) . ? C41 C42 1.494(3) . ? O42 Cu1 1.9548(17) 2_665 ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? 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 O42 Cu1 O31 90.24(8) 2_665 . ? O42 Cu1 O32 88.48(8) 2_665 2_665 ? O31 Cu1 O32 168.83(7) . 2_665 ? O42 Cu1 O41 168.75(7) 2_665 . ? O31 Cu1 O41 90.34(8) . . ? O32 Cu1 O41 88.78(8) 2_665 . ? O42 Cu1 N21 99.61(7) 2_665 . ? O31 Cu1 N21 97.34(8) . . ? O32 Cu1 N21 93.81(7) 2_665 . ? O41 Cu1 N21 91.46(7) . . ? O42 Cu1 Cu1 83.88(5) 2_665 2_665 ? O31 Cu1 Cu1 86.61(5) . 2_665 ? O32 Cu1 Cu1 82.22(5) 2_665 2_665 ? O41 Cu1 Cu1 84.94(5) . 2_665 ? N21 Cu1 Cu1 174.68(5) . 2_665 ? C12 N11 C16 115.3(2) . . ? N11 C12 N13 126.8(2) . . ? N11 C12 N12 117.2(2) . . ? N13 C12 N12 116.1(2) . . ? C12 N12 H12A 120.9(18) . . ? C12 N12 H12B 115(2) . . ? H12A N12 H12B 119(3) . . ? C14 N13 C12 115.4(2) . . ? N13 C14 O17 120.0(2) . . ? N13 C14 C15 123.6(2) . . ? O17 C14 C15 116.4(2) . . ? C16 C15 C14 115.9(2) . . ? C16 C15 H15 122.0 . . ? C14 C15 H15 122.0 . . ? N11 C16 C15 123.0(2) . . ? N11 C16 C23 115.6(2) . . ? C15 C16 C23 121.5(2) . . ? C14 O17 C17 117.4(2) . . ? O17 C17 H17A 109.5 . . ? O17 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O17 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C26 N21 C22 118.4(2) . . ? C26 N21 Cu1 122.73(16) . . ? C22 N21 Cu1 118.42(16) . . ? N21 C22 C23 123.3(2) . . ? N21 C22 H22 118.4 . . ? C23 C22 H22 118.4 . . ? C22 C23 C24 117.6(2) . . ? C22 C23 C16 119.4(2) . . ? C24 C23 C16 123.1(2) . . ? C25 C24 C23 118.8(2) . . ? C25 C24 H24 120.6 . . ? C23 C24 H24 120.6 . . ? C26 C25 C24 119.4(2) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? N21 C26 C25 122.5(2) . . ? N21 C26 H26 118.7 . . ? C25 C26 H26 118.7 . . ? O31 C31 O32 125.2(2) . . ? O31 C31 C32 118.3(2) . . ? O32 C31 C32 116.5(2) . . ? C31 O31 Cu1 120.54(17) . . ? C31 O32 Cu1 125.46(16) . 2_665 ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O42 C41 O41 125.0(2) . . ? O42 C41 C42 117.8(2) . . ? O41 C41 C42 117.2(2) . . ? C41 O41 Cu1 121.88(16) . . ? C41 O42 Cu1 124.15(16) . 2_665 ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? 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 C16 N11 C12 N13 1.2(4) . . . . ? C16 N11 C12 N12 -178.4(2) . . . . ? N11 C12 N13 C14 0.3(4) . . . . ? N12 C12 N13 C14 179.8(3) . . . . ? C12 N13 C14 O17 178.3(3) . . . . ? C12 N13 C14 C15 -1.5(4) . . . . ? N13 C14 C15 C16 1.2(5) . . . . ? O17 C14 C15 C16 -178.6(3) . . . . ? C12 N11 C16 C15 -1.4(4) . . . . ? C12 N11 C16 C23 177.3(2) . . . . ? C14 C15 C16 N11 0.3(4) . . . . ? C14 C15 C16 C23 -178.3(3) . . . . ? N13 C14 O17 C17 2.8(4) . . . . ? C15 C14 O17 C17 -177.4(3) . . . . ? O42 Cu1 N21 C26 87.0(2) 2_665 . . . ? O31 Cu1 N21 C26 -4.5(2) . . . . ? O32 Cu1 N21 C26 176.06(19) 2_665 . . . ? O41 Cu1 N21 C26 -95.1(2) . . . . ? Cu1 Cu1 N21 C26 -142.3(5) 2_665 . . . ? O42 Cu1 N21 C22 -100.98(18) 2_665 . . . ? O31 Cu1 N21 C22 167.53(18) . . . . ? O32 Cu1 N21 C22 -11.87(18) 2_665 . . . ? O41 Cu1 N21 C22 77.00(18) . . . . ? Cu1 Cu1 N21 C22 29.8(7) 2_665 . . . ? C26 N21 C22 C23 1.8(4) . . . . ? Cu1 N21 C22 C23 -170.62(19) . . . . ? N21 C22 C23 C24 -2.3(4) . . . . ? N21 C22 C23 C16 177.6(2) . . . . ? N11 C16 C23 C22 -23.4(4) . . . . ? C15 C16 C23 C22 155.4(3) . . . . ? N11 C16 C23 C24 156.6(3) . . . . ? C15 C16 C23 C24 -24.7(4) . . . . ? C22 C23 C24 C25 0.5(4) . . . . ? C16 C23 C24 C25 -179.4(2) . . . . ? C23 C24 C25 C26 1.7(4) . . . . ? C22 N21 C26 C25 0.6(4) . . . . ? Cu1 N21 C26 C25 172.7(2) . . . . ? C24 C25 C26 N21 -2.3(4) . . . . ? O32 C31 O31 Cu1 -1.0(4) . . . . ? C32 C31 O31 Cu1 178.34(17) . . . . ? O42 Cu1 O31 C31 84.4(2) 2_665 . . . ? O32 Cu1 O31 C31 1.1(5) 2_665 . . . ? O41 Cu1 O31 C31 -84.3(2) . . . . ? N21 Cu1 O31 C31 -175.86(19) . . . . ? Cu1 Cu1 O31 C31 0.56(19) 2_665 . . . ? O31 C31 O32 Cu1 0.9(4) . . . 2_665 ? C32 C31 O32 Cu1 -178.45(17) . . . 2_665 ? O42 C41 O41 Cu1 4.7(3) . . . . ? C42 C41 O41 Cu1 -175.61(17) . . . . ? O42 Cu1 O41 C41 -9.6(5) 2_665 . . . ? O31 Cu1 O41 C41 83.30(19) . . . . ? O32 Cu1 O41 C41 -85.57(19) 2_665 . . . ? N21 Cu1 O41 C41 -179.35(19) . . . . ? Cu1 Cu1 O41 C41 -3.27(18) 2_665 . . . ? O41 C41 O42 Cu1 -3.1(4) . . . 2_665 ? C42 C41 O42 Cu1 177.26(17) . . . 2_665 ? 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 N12 H12A N11 0.95(3) 2.24(3) 3.177(3) 171(2) 2_656 N12 H12B O41 0.91(3) 2.29(3) 3.185(3) 170(3) 2_656 _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.912 _refine_diff_density_max 0.371 _refine_diff_density_min -0.707 _refine_diff_density_rms 0.100 #END data_9 _database_code_depnum_ccdc_archive 'CCDC 278017' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [2-amino-4-(3-pyridyl)-6-methoxypyridine]2, [2-fluorobenzoate]4 Cu2 ; _chemical_name_common ;(2-amino-4-(3-pyridyl)-6-methoxypyridine)2, (2- fluorobenzoate)4 Cu2 ; _chemical_melting_point ? _chemical_formula_moiety ; (C10 H10 N4 O1)2 (C7 H4 O2 F)4 Cu2 ; _chemical_formula_sum 'C48 H36 Cu2 F4 N8 O10' _chemical_formula_weight 1087.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1310(9) _cell_length_b 10.5499(8) _cell_length_c 12.2936(9) _cell_angle_alpha 64.853(5) _cell_angle_beta 86.149(5) _cell_angle_gamma 67.896(4) _cell_volume 1095.24(15) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3287 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.70 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 554 _exptl_absorpt_coefficient_mu 1.061 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7872 _diffrn_reflns_av_R_equivalents 0.0785 _diffrn_reflns_av_sigmaI/netI 0.0850 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.85 _reflns_number_total 4793 _reflns_number_gt 3808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4793 _refine_ls_number_parameters 335 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1635 _refine_ls_wR_factor_gt 0.1523 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.045 _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 0.57241(4) 0.54519(5) 0.40872(3) 0.01658(15) Uani 1 1 d . . . N11 N 0.6790(3) 0.6331(3) 0.2541(3) 0.0197(6) Uani 1 1 d . . . C12 C 0.7045(4) 0.5758(4) 0.1741(3) 0.0204(7) Uani 1 1 d . . . H12 H 0.6917 0.4840 0.1944 0.025 Uiso 1 1 calc R . . C13 C 0.7490(4) 0.6428(4) 0.0619(3) 0.0240(8) Uani 1 1 d . . . C14 C 0.7713(5) 0.7730(5) 0.0339(4) 0.0310(9) Uani 1 1 d . . . H14 H 0.8022 0.8216 -0.0417 0.037 Uiso 1 1 calc R . . C15 C 0.7478(5) 0.8328(5) 0.1177(4) 0.0351(9) Uani 1 1 d . . . H15 H 0.7635 0.9224 0.1008 0.042 Uiso 1 1 calc R . . C16 C 0.7014(4) 0.7601(5) 0.2259(4) 0.0289(8) Uani 1 1 d . . . H16 H 0.6846 0.8018 0.2828 0.035 Uiso 1 1 calc R . . N21 N 0.7923(3) 0.4406(4) -0.1761(3) 0.0242(7) Uani 1 1 d . . . C22 C 0.7004(4) 0.4349(4) -0.0905(3) 0.0226(7) Uani 1 1 d . . . N22 N 0.6166(4) 0.3592(4) -0.0823(3) 0.0293(7) Uani 1 1 d . . . H22A H 0.5556 0.3519 -0.0277 0.035 Uiso 1 1 calc R . . H22B H 0.6227 0.3168 -0.1315 0.035 Uiso 1 1 calc R . . N23 N 0.6854(3) 0.4963(4) -0.0129(3) 0.0228(6) Uani 1 1 d . . . C24 C 0.7692(4) 0.5738(4) -0.0237(3) 0.0224(7) Uani 1 1 d . . . C25 C 0.8642(4) 0.5896(5) -0.1085(3) 0.0266(8) Uani 1 1 d . . . H25 H 0.9223 0.6449 -0.1156 0.032 Uiso 1 1 calc R . . C26 C 0.8704(4) 0.5193(5) -0.1842(3) 0.0264(8) Uani 1 1 d . . . C27 C 0.9616(5) 0.4783(6) -0.3532(4) 0.0381(11) Uani 1 1 d . . . H27A H 0.8641 0.5183 -0.3922 0.057 Uiso 1 1 calc R . . H27B H 0.9971 0.3673 -0.3112 0.057 Uiso 1 1 calc R . . H27C H 1.0245 0.5083 -0.4146 0.057 Uiso 1 1 calc R . . O27 O 0.9601(3) 0.5377(4) -0.2680(3) 0.0332(7) Uani 1 1 d . . . C31 C 0.4354(4) 0.2319(4) 0.3736(3) 0.0208(7) Uani 1 1 d D . . C32A C 0.3457(4) 0.1533(5) 0.4227(4) 0.0296(9) Uani 0.786(7) 1 d PD A 1 F32 F 0.2737(4) 0.1641(4) 0.5133(3) 0.0408(10) Uani 0.786(7) 1 d PD A 1 C32B C 0.3457(4) 0.1533(5) 0.4227(4) 0.0296(9) Uani 0.214(7) 1 d P A 2 H32 H 0.2960 0.1642 0.4885 0.036 Uiso 0.214(7) 1 calc PR A 2 C33 C 0.3271(5) 0.0605(5) 0.3786(4) 0.0365(10) Uani 1 1 d D . . H33 H 0.2645 0.0093 0.4135 0.044 Uiso 1 1 calc R A 1 C34 C 0.3983(5) 0.0417(5) 0.2848(4) 0.0372(11) Uani 1 1 d . A . H34 H 0.3878 -0.0248 0.2559 0.045 Uiso 1 1 calc R . . C35 C 0.4869(5) 0.1212(5) 0.2317(4) 0.0341(10) Uani 1 1 d D . . H35 H 0.5357 0.1108 0.1653 0.041 Uiso 1 1 calc R A 1 C36A C 0.5027(4) 0.2147(4) 0.2766(3) 0.0245(8) Uani 0.786(7) 1 d PD A 1 H36 H 0.5621 0.2692 0.2395 0.029 Uiso 0.786(7) 1 calc PR A 1 C36B C 0.5027(4) 0.2147(4) 0.2766(3) 0.0245(8) Uani 0.214(7) 1 d P A 2 F36 F 0.5829(10) 0.2805(12) 0.2217(9) 0.026(3) Uiso 0.214(7) 1 d PD A 2 C37 C 0.4592(4) 0.3312(4) 0.4205(3) 0.0189(7) Uani 1 1 d . A . O37 O 0.4067(3) 0.3315(3) 0.5167(2) 0.0241(6) Uani 1 1 d . . . O38 O 0.5315(3) 0.4065(3) 0.3623(2) 0.0250(6) Uani 1 1 d . . . C41 C 0.8651(4) 0.1497(4) 0.6858(3) 0.0243(8) Uani 1 1 d D . . C42A C 0.8874(4) 0.0681(5) 0.8097(4) 0.0281(8) Uani 0.641(8) 1 d PD B 1 F42 F 0.7870(4) 0.0981(4) 0.8789(3) 0.0384(12) Uani 0.641(8) 1 d PD B 1 C42B C 0.8874(4) 0.0681(5) 0.8097(4) 0.0281(8) Uani 0.359(8) 1 d P B 2 H42 H 0.8147 0.0992 0.8565 0.034 Uiso 0.359(8) 1 calc PR B 2 C43 C 1.0110(5) -0.0569(5) 0.8685(4) 0.0383(10) Uani 1 1 d D . . H43 H 1.0226 -0.1090 0.9542 0.046 Uiso 1 1 calc R B 1 C44 C 1.1166(5) -0.1059(6) 0.8041(4) 0.0449(12) Uani 1 1 d . B . H44 H 1.2010 -0.1933 0.8445 0.054 Uiso 1 1 calc R . . C45 C 1.1000(5) -0.0279(6) 0.6800(5) 0.0511(13) Uani 1 1 d D . . H45 H 1.1730 -0.0607 0.6340 0.061 Uiso 1 1 calc R B 1 C46A C 0.9760(5) 0.0988(5) 0.6229(4) 0.0391(10) Uani 0.641(8) 1 d PD B 1 H46 H 0.9663 0.1531 0.5373 0.047 Uiso 0.641(8) 1 calc PR B 1 C46B C 0.9760(5) 0.0988(5) 0.6229(4) 0.0391(10) Uani 0.359(8) 1 d P B 2 F46 F 0.9600(10) 0.1450(11) 0.5061(8) 0.059(3) Uiso 0.359(8) 1 d PD B 2 C47 C 0.7310(4) 0.2839(4) 0.6199(3) 0.0200(7) Uani 1 1 d . A . O47 O 0.6195(3) 0.2955(3) 0.6725(2) 0.0237(5) Uani 1 1 d . . . O48 O 0.7398(3) 0.3734(3) 0.5153(2) 0.0265(6) 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 0.0184(2) 0.0180(2) 0.0138(2) -0.00685(17) 0.00355(15) -0.00788(17) N11 0.0189(14) 0.0211(15) 0.0180(14) -0.0084(12) 0.0040(11) -0.0070(12) C12 0.0205(17) 0.0198(18) 0.0209(17) -0.0085(15) 0.0033(13) -0.0080(14) C13 0.0214(17) 0.029(2) 0.0189(17) -0.0092(16) 0.0029(13) -0.0090(15) C14 0.041(2) 0.035(2) 0.0206(18) -0.0123(18) 0.0131(16) -0.0208(19) C15 0.046(3) 0.033(2) 0.035(2) -0.0152(19) 0.0149(19) -0.026(2) C16 0.035(2) 0.033(2) 0.028(2) -0.0191(18) 0.0125(16) -0.0178(18) N21 0.0212(15) 0.0278(17) 0.0232(16) -0.0140(14) 0.0034(12) -0.0059(13) C22 0.0211(17) 0.0232(19) 0.0178(17) -0.0065(15) 0.0014(13) -0.0052(15) N22 0.0338(18) 0.0356(19) 0.0257(17) -0.0151(15) 0.0065(14) -0.0192(16) N23 0.0247(15) 0.0244(17) 0.0173(14) -0.0073(13) 0.0035(12) -0.0095(13) C24 0.0188(16) 0.0261(19) 0.0179(17) -0.0072(15) 0.0012(13) -0.0065(15) C25 0.0244(18) 0.033(2) 0.0238(19) -0.0122(17) 0.0061(14) -0.0133(17) C26 0.0184(17) 0.037(2) 0.0215(18) -0.0114(17) 0.0043(14) -0.0098(16) C27 0.032(2) 0.062(3) 0.033(2) -0.034(2) 0.0109(17) -0.016(2) O27 0.0283(15) 0.052(2) 0.0273(15) -0.0239(15) 0.0122(11) -0.0179(14) C31 0.0255(18) 0.0159(17) 0.0188(17) -0.0050(14) -0.0009(13) -0.0081(14) C32A 0.036(2) 0.031(2) 0.0232(19) -0.0083(17) -0.0002(16) -0.0180(18) F32 0.058(2) 0.052(2) 0.0344(18) -0.0223(17) 0.0198(15) -0.0410(19) C32B 0.036(2) 0.031(2) 0.0232(19) -0.0083(17) -0.0002(16) -0.0180(18) C33 0.048(3) 0.030(2) 0.035(2) -0.0088(19) -0.0039(19) -0.024(2) C34 0.052(3) 0.023(2) 0.040(2) -0.0167(19) -0.012(2) -0.0115(19) C35 0.039(2) 0.031(2) 0.034(2) -0.022(2) -0.0018(18) -0.0068(19) C36A 0.0239(18) 0.0186(18) 0.0268(19) -0.0105(16) -0.0009(15) -0.0023(15) C36B 0.0239(18) 0.0186(18) 0.0268(19) -0.0105(16) -0.0009(15) -0.0023(15) C37 0.0190(16) 0.0149(16) 0.0192(16) -0.0062(14) -0.0022(13) -0.0037(13) O37 0.0328(14) 0.0278(14) 0.0210(13) -0.0131(11) 0.0081(10) -0.0191(12) O38 0.0340(14) 0.0268(14) 0.0245(13) -0.0150(12) 0.0097(11) -0.0188(12) C41 0.0237(18) 0.0248(19) 0.0261(19) -0.0113(16) 0.0032(14) -0.0107(16) C42A 0.0255(19) 0.031(2) 0.0255(19) -0.0098(17) 0.0039(15) -0.0112(17) F42 0.048(3) 0.030(2) 0.022(2) -0.0077(17) 0.0064(16) -0.0032(18) C42B 0.0255(19) 0.031(2) 0.0255(19) -0.0098(17) 0.0039(15) -0.0112(17) C43 0.034(2) 0.040(3) 0.028(2) -0.0002(19) 0.0010(17) -0.017(2) C44 0.024(2) 0.035(3) 0.045(3) 0.003(2) -0.0034(19) -0.0019(19) C45 0.032(2) 0.050(3) 0.039(3) -0.009(2) 0.007(2) 0.004(2) C46A 0.033(2) 0.039(3) 0.026(2) -0.0074(19) 0.0050(17) -0.003(2) C46B 0.033(2) 0.039(3) 0.026(2) -0.0074(19) 0.0050(17) -0.003(2) C47 0.0199(16) 0.0190(17) 0.0219(17) -0.0102(15) 0.0001(13) -0.0062(14) O47 0.0185(12) 0.0254(14) 0.0211(13) -0.0057(11) 0.0021(10) -0.0072(11) O48 0.0233(13) 0.0238(14) 0.0200(13) -0.0028(11) 0.0027(10) -0.0039(11) _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 O37 1.956(2) 2_666 ? Cu1 O38 1.959(2) . ? Cu1 O48 1.961(3) . ? Cu1 O47 1.994(3) 2_666 ? Cu1 N11 2.149(3) . ? Cu1 Cu1 2.6252(8) 2_666 ? N11 C12 1.324(4) . ? N11 C16 1.338(5) . ? C12 C13 1.390(5) . ? C12 H12 0.9500 . ? C13 C14 1.370(6) . ? C13 C24 1.480(5) . ? C14 C15 1.387(6) . ? C14 H14 0.9500 . ? C15 C16 1.378(6) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N21 C26 1.318(5) . ? N21 C22 1.355(5) . ? C22 N23 1.336(5) . ? C22 N22 1.341(5) . ? N22 H22A 0.8800 . ? N22 H22B 0.8800 . ? N23 C24 1.349(5) . ? C24 C25 1.371(5) . ? C25 C26 1.401(5) . ? C25 H25 0.9500 . ? C26 O27 1.328(5) . ? C27 O27 1.428(4) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C31 C36A 1.378(5) . ? C31 C32A 1.395(5) . ? C31 C37 1.486(4) . ? C32A F32 1.312(5) . ? C32A C33 1.375(5) . ? C33 C34 1.365(7) . ? C33 H33 0.9500 . ? C34 C35 1.400(6) . ? C34 H34 0.9500 . ? C35 C36A 1.377(5) . ? C35 H35 0.9500 . ? C36A H36 0.9500 . ? C37 O38 1.250(4) . ? C37 O37 1.265(4) . ? O37 Cu1 1.956(2) 2_666 ? C41 C42A 1.378(5) . ? C41 C46A 1.390(6) . ? C41 C47 1.494(5) . ? C42A F42 1.315(5) . ? C42A C43 1.377(6) . ? C43 C44 1.363(7) . ? C43 H43 0.9500 . ? C44 C45 1.377(7) . ? C44 H44 0.9500 . ? C45 C46A 1.384(6) . ? C45 H45 0.9500 . ? C46A H46 0.9500 . ? C47 O48 1.252(4) . ? C47 O47 1.254(4) . ? O47 Cu1 1.994(3) 2_666 ? 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 O37 Cu1 O38 168.45(10) 2_666 . ? O37 Cu1 O48 89.56(11) 2_666 . ? O38 Cu1 O48 88.92(11) . . ? O37 Cu1 O47 89.84(11) 2_666 2_666 ? O38 Cu1 O47 89.39(11) . 2_666 ? O48 Cu1 O47 168.57(10) . 2_666 ? O37 Cu1 N11 94.85(11) 2_666 . ? O38 Cu1 N11 96.70(11) . . ? O48 Cu1 N11 98.53(11) . . ? O47 Cu1 N11 92.89(11) 2_666 . ? O37 Cu1 Cu1 84.14(8) 2_666 2_666 ? O38 Cu1 Cu1 84.32(8) . 2_666 ? O48 Cu1 Cu1 85.10(8) . 2_666 ? O47 Cu1 Cu1 83.49(8) 2_666 2_666 ? N11 Cu1 Cu1 176.24(8) . 2_666 ? C12 N11 C16 117.7(3) . . ? C12 N11 Cu1 120.1(2) . . ? C16 N11 Cu1 121.4(2) . . ? N11 C12 C13 123.5(3) . . ? N11 C12 H12 118.2 . . ? C13 C12 H12 118.2 . . ? C14 C13 C12 118.3(3) . . ? C14 C13 C24 122.1(3) . . ? C12 C13 C24 119.7(3) . . ? C13 C14 C15 118.9(4) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 118.8(4) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? N11 C16 C15 122.7(3) . . ? N11 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? C26 N21 C22 115.4(3) . . ? N23 C22 N22 116.7(3) . . ? N23 C22 N21 126.5(3) . . ? N22 C22 N21 116.8(3) . . ? C22 N22 H22A 120.0 . . ? C22 N22 H22B 120.0 . . ? H22A N22 H22B 120.0 . . ? C22 N23 C24 115.8(3) . . ? N23 C24 C25 122.8(3) . . ? N23 C24 C13 114.8(3) . . ? C25 C24 C13 122.4(3) . . ? C24 C25 C26 115.9(3) . . ? C24 C25 H25 122.0 . . ? C26 C25 H25 122.0 . . ? N21 C26 O27 120.6(3) . . ? N21 C26 C25 123.6(3) . . ? O27 C26 C25 115.8(3) . . ? O27 C27 H27A 109.5 . . ? O27 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O27 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 O27 C27 117.7(3) . . ? C36A C31 C32A 116.7(3) . . ? C36A C31 C37 120.2(3) . . ? C32A C31 C37 123.1(3) . . ? F32 C32A C33 116.1(4) . . ? F32 C32A C31 121.9(3) . . ? C33 C32A C31 121.9(4) . . ? C34 C33 C32A 120.2(4) . . ? C34 C33 H33 119.9 . . ? C32A C33 H33 119.9 . . ? C33 C34 C35 119.4(3) . . ? C33 C34 H34 120.3 . . ? C35 C34 H34 120.3 . . ? C36A C35 C34 119.3(4) . . ? C36A C35 H35 120.4 . . ? C34 C35 H35 120.4 . . ? C35 C36A C31 122.4(4) . . ? C35 C36A H36 118.8 . . ? C31 C36A H36 118.8 . . ? O38 C37 O37 125.1(3) . . ? O38 C37 C31 117.2(3) . . ? O37 C37 C31 117.7(3) . . ? C37 O37 Cu1 123.2(2) . 2_666 ? C37 O38 Cu1 123.2(2) . . ? C42A C41 C46A 115.8(4) . . ? C42A C41 C47 123.6(3) . . ? C46A C41 C47 120.6(4) . . ? F42 C42A C43 115.5(4) . . ? F42 C42A C41 121.7(4) . . ? C43 C42A C41 122.6(4) . . ? C44 C43 C42A 120.2(4) . . ? C44 C43 H43 119.9 . . ? C42A C43 H43 119.9 . . ? C43 C44 C45 119.5(4) . . ? C43 C44 H44 120.3 . . ? C45 C44 H44 120.3 . . ? C44 C45 C46A 119.3(5) . . ? C44 C45 H45 120.3 . . ? C46A C45 H45 120.3 . . ? C45 C46A C41 122.5(4) . . ? C45 C46A H46 118.7 . . ? C41 C46A H46 118.7 . . ? O48 C47 O47 125.8(3) . . ? O48 C47 C41 116.6(3) . . ? O47 C47 C41 117.6(3) . . ? C47 O47 Cu1 122.8(2) . 2_666 ? C47 O48 Cu1 122.7(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 O37 Cu1 N11 C12 174.9(3) 2_666 . . . ? O38 Cu1 N11 C12 -5.3(3) . . . . ? O48 Cu1 N11 C12 84.6(3) . . . . ? O47 Cu1 N11 C12 -95.0(3) 2_666 . . . ? Cu1 Cu1 N11 C12 -110.7(12) 2_666 . . . ? O37 Cu1 N11 C16 -15.5(3) 2_666 . . . ? O38 Cu1 N11 C16 164.3(3) . . . . ? O48 Cu1 N11 C16 -105.7(3) . . . . ? O47 Cu1 N11 C16 74.6(3) 2_666 . . . ? Cu1 Cu1 N11 C16 58.9(13) 2_666 . . . ? C16 N11 C12 C13 -1.9(5) . . . . ? Cu1 N11 C12 C13 168.1(3) . . . . ? N11 C12 C13 C14 1.7(6) . . . . ? N11 C12 C13 C24 -177.5(3) . . . . ? C12 C13 C14 C15 -0.4(6) . . . . ? C24 C13 C14 C15 178.9(4) . . . . ? C13 C14 C15 C16 -0.7(7) . . . . ? C12 N11 C16 C15 0.7(6) . . . . ? Cu1 N11 C16 C15 -169.1(3) . . . . ? C14 C15 C16 N11 0.6(7) . . . . ? C26 N21 C22 N23 -2.2(6) . . . . ? C26 N21 C22 N22 178.2(3) . . . . ? N22 C22 N23 C24 -179.1(3) . . . . ? N21 C22 N23 C24 1.4(5) . . . . ? C22 N23 C24 C25 0.0(5) . . . . ? C22 N23 C24 C13 179.1(3) . . . . ? C14 C13 C24 N23 -150.5(4) . . . . ? C12 C13 C24 N23 28.8(5) . . . . ? C14 C13 C24 C25 28.6(6) . . . . ? C12 C13 C24 C25 -152.2(4) . . . . ? N23 C24 C25 C26 -0.3(6) . . . . ? C13 C24 C25 C26 -179.3(3) . . . . ? C22 N21 C26 O27 -177.3(3) . . . . ? C22 N21 C26 C25 1.8(5) . . . . ? C24 C25 C26 N21 -0.6(6) . . . . ? C24 C25 C26 O27 178.5(3) . . . . ? N21 C26 O27 C27 4.0(6) . . . . ? C25 C26 O27 C27 -175.1(4) . . . . ? C36A C31 C32A F32 -178.4(4) . . . . ? C37 C31 C32A F32 1.2(6) . . . . ? C36A C31 C32A C33 1.3(6) . . . . ? C37 C31 C32A C33 -179.1(4) . . . . ? F32 C32A C33 C34 -179.7(4) . . . . ? C31 C32A C33 C34 0.6(6) . . . . ? C32A C33 C34 C35 -1.9(7) . . . . ? C33 C34 C35 C36A 1.3(6) . . . . ? C34 C35 C36A C31 0.8(6) . . . . ? C32A C31 C36A C35 -2.0(6) . . . . ? C37 C31 C36A C35 178.4(3) . . . . ? C36A C31 C37 O38 6.0(5) . . . . ? C32A C31 C37 O38 -173.6(3) . . . . ? C36A C31 C37 O37 -173.1(3) . . . . ? C32A C31 C37 O37 7.3(5) . . . . ? O38 C37 O37 Cu1 1.0(5) . . . 2_666 ? C31 C37 O37 Cu1 180.0(2) . . . 2_666 ? O37 C37 O38 Cu1 -1.8(5) . . . . ? C31 C37 O38 Cu1 179.3(2) . . . . ? O37 Cu1 O38 C37 4.0(7) 2_666 . . . ? O48 Cu1 O38 C37 86.5(3) . . . . ? O47 Cu1 O38 C37 -82.2(3) 2_666 . . . ? N11 Cu1 O38 C37 -175.1(3) . . . . ? Cu1 Cu1 O38 C37 1.3(3) 2_666 . . . ? C46A C41 C42A F42 -175.2(4) . . . . ? C47 C41 C42A F42 4.1(6) . . . . ? C46A C41 C42A C43 -0.4(6) . . . . ? C47 C41 C42A C43 178.9(4) . . . . ? F42 C42A C43 C44 174.1(4) . . . . ? C41 C42A C43 C44 -0.9(7) . . . . ? C42A C43 C44 C45 1.2(8) . . . . ? C43 C44 C45 C46A -0.2(8) . . . . ? C44 C45 C46A C41 -1.2(8) . . . . ? C42A C41 C46A C45 1.5(7) . . . . ? C47 C41 C46A C45 -177.9(4) . . . . ? C42A C41 C47 O48 159.2(4) . . . . ? C46A C41 C47 O48 -21.5(5) . . . . ? C42A C41 C47 O47 -22.3(5) . . . . ? C46A C41 C47 O47 157.0(4) . . . . ? O48 C47 O47 Cu1 5.1(5) . . . 2_666 ? C41 C47 O47 Cu1 -173.3(2) . . . 2_666 ? O47 C47 O48 Cu1 -4.3(5) . . . . ? C41 C47 O48 Cu1 174.1(2) . . . . ? O37 Cu1 O48 C47 85.6(3) 2_666 . . . ? O38 Cu1 O48 C47 -82.9(3) . . . . ? O47 Cu1 O48 C47 -1.4(7) 2_666 . . . ? N11 Cu1 O48 C47 -179.5(3) . . . . ? Cu1 Cu1 O48 C47 1.5(3) 2_666 . . . ? 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 N22 H22A N23 0.88 2.52 3.253(5) 141.2 2_665 _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.736 _refine_diff_density_min -0.759 _refine_diff_density_rms 0.135 #END data_10 _database_code_depnum_ccdc_archive 'CCDC 278018' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-amino-4-(3-pyridyl)-6-methylpyridine)2, (2FPhCOO)4 Cu2 ; _chemical_name_common '(2-amino-4-(3-pyridyl)-6-methylpyridine)2, (2FPhCOO)4 Cu2' _chemical_melting_point ? _chemical_formula_moiety ; (C10 H10 N4)2 Cu2 (C7 H4 O2 F)4 ; _chemical_formula_sum 'C48 H36 Cu2 F4 N8 O8' _chemical_formula_weight 1055.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 21.3553(18) _cell_length_b 17.9389(15) _cell_length_c 11.4887(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.742(5) _cell_angle_gamma 90.00 _cell_volume 4400.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3621 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.15 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2152 _exptl_absorpt_coefficient_mu 1.050 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31431 _diffrn_reflns_av_R_equivalents 0.0734 _diffrn_reflns_av_sigmaI/netI 0.0863 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.30 _reflns_number_total 9998 _reflns_number_gt 6283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9998 _refine_ls_number_parameters 658 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0965 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1240 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 0.946974(18) 0.51457(2) 0.05290(3) 0.01866(11) Uani 1 1 d . . . Cu2 Cu 0.493014(18) 0.47724(2) 0.39103(3) 0.02130(11) Uani 1 1 d . . . N11 N 0.86503(13) 0.54993(15) 0.1437(2) 0.0227(6) Uani 1 1 d . . . C12 C 0.85840(16) 0.53121(18) 0.2538(3) 0.0243(8) Uani 1 1 d . . . H12 H 0.8899 0.5010 0.2891 0.029 Uiso 1 1 calc R . . C13 C 0.80818(16) 0.55300(19) 0.3212(3) 0.0245(7) Uani 1 1 d . . . C14 C 0.76341(18) 0.5981(2) 0.2707(3) 0.0322(8) Uani 1 1 d . . . H14 H 0.7284 0.6144 0.3140 0.039 Uiso 1 1 calc R . . C15 C 0.77024(18) 0.6195(2) 0.1558(3) 0.0342(9) Uani 1 1 d . . . H15 H 0.7401 0.6510 0.1194 0.041 Uiso 1 1 calc R . . C16 C 0.82108(17) 0.5947(2) 0.0948(3) 0.0297(8) Uani 1 1 d . . . H16 H 0.8255 0.6094 0.0159 0.036 Uiso 1 1 calc R . . N21 N 0.78949(13) 0.48320(16) 0.6684(2) 0.0260(6) Uani 1 1 d . . . C22 C 0.74771(16) 0.52493(18) 0.6109(3) 0.0238(7) Uani 1 1 d . . . N22 N 0.69682(15) 0.54719(18) 0.6715(3) 0.0305(7) Uani 1 1 d . . . H22A H 0.6951(17) 0.528(2) 0.747(3) 0.037 Uiso 1 1 d . . . H22B H 0.6608(18) 0.563(2) 0.628(3) 0.037 Uiso 1 1 d . . . N23 N 0.75156(14) 0.54784(16) 0.4997(2) 0.0270(7) Uani 1 1 d . . . C24 C 0.80277(16) 0.52686(19) 0.4436(3) 0.0245(7) Uani 1 1 d . . . C25 C 0.84767(17) 0.4822(2) 0.4954(3) 0.0302(8) Uani 1 1 d . . . H25 H 0.8835 0.4664 0.4539 0.036 Uiso 1 1 calc R . . C26 C 0.83880(17) 0.4615(2) 0.6095(3) 0.0268(8) Uani 1 1 d . . . C27 C 0.88412(18) 0.4110(2) 0.6702(3) 0.0398(10) Uani 1 1 d . . . H27A H 0.8700 0.4017 0.7497 0.060 Uiso 1 1 calc R . . H27B H 0.9256 0.4345 0.6727 0.060 Uiso 1 1 calc R . . H27C H 0.8866 0.3636 0.6280 0.060 Uiso 1 1 calc R . . C31 C 0.93441(16) 0.60379(19) -0.2868(3) 0.0260(8) Uani 1 1 d . . . C32A C 0.8828(2) 0.6487(2) -0.2818(4) 0.0495(11) Uani 0.516(6) 1 d P A 1 F32 F 0.8476(3) 0.6575(3) -0.1941(4) 0.078(2) Uani 0.516(6) 1 d P A 1 C32B C 0.8828(2) 0.6487(2) -0.2818(4) 0.0495(11) Uani 0.484(6) 1 d P A 2 H32 H 0.8604 0.6515 -0.2110 0.059 Uiso 0.484(6) 1 calc PR A 2 C33 C 0.8620(3) 0.6901(3) -0.3760(5) 0.0713(15) Uani 1 1 d . . . H33 H 0.8257 0.7204 -0.3704 0.086 Uiso 1 1 calc R A 1 C34 C 0.8947(3) 0.6868(3) -0.4776(4) 0.0725(17) Uani 1 1 d . A . H34 H 0.8816 0.7158 -0.5427 0.087 Uiso 1 1 calc R . . C35 C 0.9456(2) 0.6422(3) -0.4855(3) 0.0556(13) Uani 1 1 d . . . H35 H 0.9679 0.6394 -0.5564 0.067 Uiso 1 1 calc R A 1 C36A C 0.96480(19) 0.6013(2) -0.3908(3) 0.0394(10) Uani 0.516(6) 1 d P A 1 H36 H 1.0005 0.5700 -0.3977 0.047 Uiso 0.516(6) 1 calc PR A 1 C36B C 0.96480(19) 0.6013(2) -0.3908(3) 0.0394(10) Uani 0.484(6) 1 d P A 2 F36 F 1.0105(2) 0.5585(3) -0.4119(3) 0.0566(19) Uani 0.484(6) 1 d P A 2 C37 C 0.95713(16) 0.56127(18) -0.1821(3) 0.0218(7) Uani 1 1 d . A . O37 O 0.92109(11) 0.55649(14) -0.09766(18) 0.0298(6) Uani 1 1 d . . . O38 O 1.01113(11) 0.53405(13) -0.18603(17) 0.0254(5) Uani 1 1 d . . . C41 C 1.07178(17) 0.69641(18) 0.1080(3) 0.0247(8) Uani 1 1 d . . . C42A C 1.04634(18) 0.7337(2) 0.2026(3) 0.0300(8) Uani 0.889(6) 1 d P B 1 F42 F 0.99547(12) 0.71000(13) 0.25345(19) 0.0415(9) Uani 0.889(6) 1 d P B 1 C42B C 1.04634(18) 0.7337(2) 0.2026(3) 0.0300(8) Uani 0.111(6) 1 d P B 2 H42 H 1.0083 0.7162 0.2346 0.036 Uiso 0.111(6) 1 calc PR B 2 C43 C 1.0752(2) 0.7954(2) 0.2509(3) 0.0389(10) Uani 1 1 d . . . H43 H 1.0576 0.8196 0.3163 0.047 Uiso 1 1 calc R B 1 C44 C 1.1298(2) 0.8216(2) 0.2035(4) 0.0439(11) Uani 1 1 d . B . H44 H 1.1502 0.8636 0.2369 0.053 Uiso 1 1 calc R . . C45 C 1.1549(2) 0.7871(2) 0.1080(3) 0.0414(10) Uani 1 1 d . . . H45 H 1.1921 0.8058 0.0742 0.050 Uiso 1 1 calc R B 1 C46A C 1.12573(18) 0.72543(19) 0.0621(3) 0.0310(8) Uani 0.889(6) 1 d P B 1 H46 H 1.1434 0.7019 -0.0039 0.037 Uiso 0.889(6) 1 calc PR B 1 C46B C 1.12573(18) 0.72543(19) 0.0621(3) 0.0310(8) Uani 0.111(6) 1 d P B 2 F46 F 1.1515(10) 0.7027(11) -0.0167(17) 0.045(7) Uiso 0.111(6) 1 d P B 2 C47 C 1.04471(16) 0.62494(18) 0.0630(2) 0.0211(7) Uani 1 1 d . A . O47 O 0.99037(11) 0.60840(13) 0.0892(2) 0.0313(6) Uani 1 1 d . . . O48 O 1.08021(10) 0.58516(12) 0.00105(18) 0.0237(5) Uani 1 1 d . . . N51 N 0.47945(12) 0.44069(15) 0.2144(2) 0.0229(6) Uani 1 1 d . . . C52 C 0.43259(15) 0.47230(19) 0.1553(3) 0.0238(7) Uani 1 1 d . . . H52 H 0.4100 0.5111 0.1922 0.029 Uiso 1 1 calc R . . C53 C 0.41478(16) 0.4523(2) 0.0438(3) 0.0249(8) Uani 1 1 d . . . C54 C 0.44954(17) 0.3977(2) -0.0107(3) 0.0374(9) Uani 1 1 d . . . H54 H 0.4400 0.3836 -0.0886 0.045 Uiso 1 1 calc R . . C55 C 0.49798(18) 0.3642(2) 0.0491(3) 0.0415(10) Uani 1 1 d . . . H55 H 0.5222 0.3264 0.0132 0.050 Uiso 1 1 calc R . . C56 C 0.51127(16) 0.3861(2) 0.1628(3) 0.0301(8) Uani 1 1 d . . . H56 H 0.5439 0.3616 0.2049 0.036 Uiso 1 1 calc R . . N61 N 0.25898(13) 0.56240(16) -0.1019(2) 0.0266(7) Uani 1 1 d . . . C62 C 0.26428(16) 0.54029(18) 0.0104(2) 0.0218(7) Uani 1 1 d . . . N62 N 0.21558(15) 0.55722(19) 0.0784(2) 0.0291(7) Uani 1 1 d . . . H62A H 0.2176(18) 0.545(2) 0.139(3) 0.035 Uiso 1 1 d . . . H62B H 0.1835(18) 0.572(2) 0.044(3) 0.035 Uiso 1 1 d . . . N63 N 0.31347(13) 0.50686(15) 0.0602(2) 0.0216(6) Uani 1 1 d . . . C64 C 0.36032(15) 0.49008(19) -0.0112(3) 0.0238(7) Uani 1 1 d . . . C65 C 0.35862(17) 0.5072(2) -0.1283(3) 0.0295(8) Uani 1 1 d . . . H65 H 0.3912 0.4924 -0.1787 0.035 Uiso 1 1 calc R . . C66 C 0.30753(17) 0.5466(2) -0.1687(3) 0.0288(8) Uani 1 1 d . . . C67 C 0.30561(18) 0.5764(2) -0.2908(3) 0.0391(10) Uani 1 1 d . . . H67A H 0.3438 0.5617 -0.3311 0.059 Uiso 1 1 calc R . . H67B H 0.3027 0.6309 -0.2887 0.059 Uiso 1 1 calc R . . H67C H 0.2690 0.5561 -0.3322 0.059 Uiso 1 1 calc R . . C71 C 0.60720(17) 0.67135(19) 0.3981(3) 0.0277(8) Uani 1 1 d . . . C72 C 0.5865(2) 0.7127(2) 0.3037(3) 0.0405(10) Uani 1 1 d . . . F72 F 0.53169(13) 0.69420(14) 0.25125(19) 0.0560(7) Uani 1 1 d . . . C73 C 0.6186(3) 0.7746(2) 0.2633(4) 0.0564(13) Uani 1 1 d . . . H73 H 0.6029 0.8025 0.1989 0.068 Uiso 1 1 calc R . . C74 C 0.6728(3) 0.7942(2) 0.3179(4) 0.0568(13) Uani 1 1 d . . . H74 H 0.6966 0.8349 0.2894 0.068 Uiso 1 1 calc R . . C75 C 0.6930(2) 0.7563(2) 0.4121(4) 0.0503(12) Uani 1 1 d . . . H75 H 0.7306 0.7713 0.4506 0.060 Uiso 1 1 calc R . . C76 C 0.66018(18) 0.6959(2) 0.4536(3) 0.0363(9) Uani 1 1 d . . . H76 H 0.6746 0.6710 0.5219 0.044 Uiso 1 1 calc R . . C77 C 0.57310(16) 0.60369(19) 0.4377(3) 0.0249(8) Uani 1 1 d . . . O77 O 0.55271(11) 0.55932(13) 0.36258(19) 0.0297(6) Uani 1 1 d . . . O78 O 0.56804(11) 0.59543(13) 0.54636(18) 0.0282(6) Uani 1 1 d . . . C81 C 0.36813(16) 0.65454(19) 0.4446(3) 0.0248(7) Uani 1 1 d . . . C82 C 0.36130(17) 0.7176(2) 0.5112(3) 0.0297(8) Uani 1 1 d . . . F82 F 0.40004(12) 0.73029(12) 0.60350(18) 0.0493(6) Uani 1 1 d . . . C83 C 0.31736(19) 0.7713(2) 0.4874(3) 0.0400(10) Uani 1 1 d . . . H83 H 0.3143 0.8145 0.5350 0.048 Uiso 1 1 calc R . . C84 C 0.27754(19) 0.7614(2) 0.3929(3) 0.0413(10) Uani 1 1 d . . . H84 H 0.2464 0.7976 0.3754 0.050 Uiso 1 1 calc R . . C85 C 0.28300(18) 0.6994(2) 0.3244(3) 0.0387(9) Uani 1 1 d . . . H85 H 0.2556 0.6926 0.2594 0.046 Uiso 1 1 calc R . . C86 C 0.32802(17) 0.6472(2) 0.3495(3) 0.0336(9) Uani 1 1 d . . . H86 H 0.3318 0.6049 0.3004 0.040 Uiso 1 1 calc R . . C87 C 0.41588(16) 0.59565(19) 0.4689(3) 0.0247(7) Uani 1 1 d . . . O87 O 0.42746(11) 0.55215(13) 0.38605(19) 0.0312(6) Uani 1 1 d . . . O88 O 0.44089(11) 0.59269(13) 0.56795(18) 0.0278(5) 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 0.0188(2) 0.0223(2) 0.01503(17) 0.00047(16) 0.00347(15) 0.00021(17) Cu2 0.0209(2) 0.0255(2) 0.01750(18) -0.00133(16) 0.00168(15) 0.00488(18) N11 0.0208(15) 0.0286(16) 0.0187(12) -0.0015(12) 0.0031(11) 0.0009(13) C12 0.0270(19) 0.028(2) 0.0183(14) 0.0048(14) 0.0031(13) 0.0028(15) C13 0.0254(19) 0.0270(19) 0.0211(15) -0.0004(14) 0.0041(14) 0.0009(15) C14 0.037(2) 0.032(2) 0.0281(17) 0.0026(16) 0.0085(16) 0.0090(18) C15 0.040(2) 0.034(2) 0.0287(18) 0.0056(16) 0.0043(17) 0.0109(18) C16 0.034(2) 0.030(2) 0.0247(16) 0.0080(15) 0.0066(15) 0.0003(17) N21 0.0296(17) 0.0285(16) 0.0199(13) -0.0010(12) 0.0023(12) 0.0031(14) C22 0.030(2) 0.0226(18) 0.0191(14) 0.0000(14) 0.0042(14) -0.0024(16) N22 0.0304(18) 0.0386(19) 0.0228(14) 0.0040(13) 0.0078(13) 0.0075(15) N23 0.0306(17) 0.0282(16) 0.0223(13) 0.0011(12) 0.0057(12) 0.0031(14) C24 0.0245(19) 0.029(2) 0.0204(15) -0.0015(14) 0.0046(14) -0.0013(16) C25 0.029(2) 0.039(2) 0.0237(16) 0.0020(16) 0.0074(15) 0.0085(18) C26 0.029(2) 0.033(2) 0.0185(15) -0.0019(14) 0.0012(14) 0.0008(16) C27 0.039(2) 0.054(3) 0.0266(18) 0.0084(18) 0.0036(16) 0.017(2) C31 0.028(2) 0.027(2) 0.0231(16) 0.0063(14) -0.0048(14) -0.0043(16) C32A 0.058(3) 0.048(3) 0.042(2) 0.008(2) -0.003(2) 0.013(2) F32 0.098(5) 0.098(5) 0.040(3) 0.011(3) 0.009(3) 0.068(4) C32B 0.058(3) 0.048(3) 0.042(2) 0.008(2) -0.003(2) 0.013(2) C33 0.082(4) 0.058(3) 0.073(3) 0.023(3) -0.019(3) 0.022(3) C34 0.087(4) 0.070(4) 0.059(3) 0.042(3) -0.029(3) -0.013(3) C35 0.061(3) 0.077(4) 0.029(2) 0.024(2) -0.008(2) -0.027(3) C36A 0.034(2) 0.057(3) 0.0270(18) 0.0119(18) -0.0008(17) -0.013(2) C36B 0.034(2) 0.057(3) 0.0270(18) 0.0119(18) -0.0008(17) -0.013(2) F36 0.045(3) 0.103(5) 0.021(2) 0.013(2) 0.010(2) 0.029(3) C37 0.0258(19) 0.0207(18) 0.0188(15) 0.0007(13) -0.0008(14) -0.0045(15) O37 0.0260(13) 0.0436(15) 0.0201(11) 0.0113(11) 0.0041(10) 0.0065(12) O38 0.0252(13) 0.0353(15) 0.0157(10) 0.0038(10) 0.0008(9) 0.0016(11) C41 0.035(2) 0.0198(18) 0.0194(15) -0.0004(13) -0.0046(14) 0.0049(15) C42A 0.036(2) 0.027(2) 0.0272(17) -0.0015(15) -0.0055(16) 0.0101(17) F42 0.0463(17) 0.0439(17) 0.0345(13) -0.0108(11) 0.0135(12) -0.0001(13) C42B 0.036(2) 0.027(2) 0.0272(17) -0.0015(15) -0.0055(16) 0.0101(17) C43 0.059(3) 0.028(2) 0.0289(18) -0.0091(16) -0.0142(19) 0.018(2) C44 0.056(3) 0.022(2) 0.054(2) -0.0033(19) -0.021(2) -0.003(2) C45 0.044(3) 0.031(2) 0.049(2) 0.0027(19) -0.008(2) -0.0079(19) C46A 0.035(2) 0.023(2) 0.0347(19) 0.0002(16) -0.0037(17) -0.0026(17) C46B 0.035(2) 0.023(2) 0.0347(19) 0.0002(16) -0.0037(17) -0.0026(17) C47 0.027(2) 0.0195(17) 0.0167(14) 0.0044(13) -0.0034(14) 0.0020(15) O47 0.0257(14) 0.0268(14) 0.0418(14) -0.0088(11) 0.0094(11) -0.0035(11) O48 0.0237(13) 0.0226(13) 0.0249(11) -0.0038(10) 0.0011(10) -0.0020(10) N51 0.0201(15) 0.0278(16) 0.0209(13) -0.0015(12) 0.0024(11) 0.0018(13) C52 0.0211(18) 0.029(2) 0.0214(15) -0.0024(14) 0.0046(13) 0.0018(15) C53 0.0193(18) 0.033(2) 0.0225(15) -0.0056(14) 0.0061(13) -0.0016(15) C54 0.032(2) 0.054(3) 0.0267(18) -0.0137(17) -0.0017(16) 0.0076(19) C55 0.033(2) 0.054(3) 0.037(2) -0.0200(19) 0.0004(17) 0.013(2) C56 0.0229(19) 0.036(2) 0.0311(18) -0.0037(16) 0.0008(15) 0.0058(16) N61 0.0252(16) 0.0368(18) 0.0180(12) 0.0011(12) 0.0000(12) -0.0037(14) C62 0.0221(18) 0.0273(19) 0.0160(14) 0.0010(13) 0.0014(13) -0.0037(14) N62 0.0240(17) 0.046(2) 0.0172(13) 0.0056(14) 0.0033(13) 0.0072(15) N63 0.0193(15) 0.0299(16) 0.0156(12) -0.0016(11) 0.0020(11) 0.0000(12) C64 0.0198(18) 0.030(2) 0.0212(15) -0.0043(14) 0.0018(13) -0.0019(15) C65 0.025(2) 0.047(2) 0.0165(15) -0.0034(15) 0.0082(14) -0.0026(17) C66 0.030(2) 0.038(2) 0.0186(15) 0.0008(15) 0.0026(15) -0.0068(17) C67 0.039(2) 0.056(3) 0.0224(17) 0.0064(17) 0.0035(16) -0.006(2) C71 0.037(2) 0.0211(19) 0.0251(16) -0.0033(14) 0.0094(15) 0.0060(16) C72 0.064(3) 0.033(2) 0.0246(18) -0.0017(16) 0.0112(19) 0.009(2) F72 0.0764(19) 0.0543(16) 0.0372(12) 0.0074(11) -0.0071(13) 0.0138(14) C73 0.098(4) 0.034(3) 0.038(2) 0.011(2) 0.027(3) 0.011(3) C74 0.086(4) 0.031(3) 0.053(3) 0.000(2) 0.029(3) -0.015(3) C75 0.060(3) 0.040(3) 0.052(3) -0.007(2) 0.017(2) -0.010(2) C76 0.043(2) 0.029(2) 0.0368(19) -0.0020(17) 0.0086(18) -0.0031(18) C77 0.0224(19) 0.0269(19) 0.0254(16) 0.0012(14) 0.0046(14) 0.0072(15) O77 0.0384(15) 0.0276(14) 0.0233(11) -0.0023(10) 0.0090(11) -0.0032(12) O78 0.0304(14) 0.0348(14) 0.0195(11) 0.0037(10) 0.0037(10) -0.0043(11) C81 0.0211(18) 0.0228(18) 0.0306(17) 0.0052(14) 0.0074(14) 0.0051(15) C82 0.031(2) 0.029(2) 0.0285(17) 0.0035(15) 0.0036(16) 0.0062(17) F82 0.0671(17) 0.0370(14) 0.0435(13) -0.0098(10) -0.0123(12) 0.0135(12) C83 0.048(3) 0.030(2) 0.042(2) 0.0004(18) 0.0108(19) 0.0135(19) C84 0.034(2) 0.039(2) 0.050(2) 0.013(2) 0.0069(19) 0.0169(19) C85 0.032(2) 0.038(2) 0.045(2) 0.0039(19) -0.0045(18) 0.0089(18) C86 0.036(2) 0.030(2) 0.0348(19) 0.0025(16) -0.0017(17) 0.0031(17) C87 0.0221(19) 0.0237(19) 0.0284(17) 0.0001(15) 0.0023(14) 0.0002(15) O87 0.0319(15) 0.0349(15) 0.0266(12) -0.0056(11) -0.0024(11) 0.0186(12) O88 0.0284(14) 0.0295(14) 0.0257(11) -0.0005(10) -0.0011(10) 0.0090(11) _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 O37 1.959(2) . ? Cu1 O47 1.964(2) . ? Cu1 O38 1.966(2) 3_765 ? Cu1 O48 1.978(2) 3_765 ? Cu1 N11 2.145(3) . ? Cu1 Cu1 2.6364(8) 3_765 ? Cu2 O87 1.941(2) . ? Cu2 O88 1.942(2) 3_666 ? Cu2 O77 1.978(2) . ? Cu2 O78 1.985(2) 3_666 ? Cu2 N51 2.149(2) . ? Cu2 Cu2 2.6467(7) 3_666 ? N11 C12 1.318(4) . ? N11 C16 1.352(4) . ? C12 C13 1.387(4) . ? C12 H12 0.9500 . ? C13 C14 1.376(5) . ? C13 C24 1.489(4) . ? C14 C15 1.384(4) . ? C14 H14 0.9500 . ? C15 C16 1.373(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N21 C26 1.318(4) . ? N21 C22 1.333(4) . ? C22 N23 1.346(4) . ? C22 N22 1.358(4) . ? N22 H22A 0.93(4) . ? N22 H22B 0.95(4) . ? N23 C24 1.331(4) . ? C24 C25 1.378(5) . ? C25 C26 1.379(4) . ? C25 H25 0.9500 . ? C26 C27 1.491(5) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C31 C36A 1.368(5) . ? C31 C32A 1.368(5) . ? C31 C37 1.500(4) . ? C32A F32 1.274(6) . ? C32A C33 1.381(6) . ? C33 C34 1.369(7) . ? C33 H33 0.9500 . ? C34 C35 1.353(7) . ? C34 H34 0.9500 . ? C35 C36A 1.371(5) . ? C35 H35 0.9500 . ? C36A H36 0.9500 . ? C37 O37 1.249(4) . ? C37 O38 1.254(4) . ? O38 Cu1 1.966(2) 3_765 ? C41 C46A 1.376(5) . ? C41 C42A 1.392(5) . ? C41 C47 1.496(4) . ? C42A F42 1.311(4) . ? C42A C43 1.381(5) . ? C43 C44 1.375(6) . ? C43 H43 0.9500 . ? C44 C45 1.374(6) . ? C44 H44 0.9500 . ? C45 C46A 1.372(5) . ? C45 H45 0.9500 . ? C46A H46 0.9500 . ? C47 O47 1.239(4) . ? C47 O48 1.267(4) . ? O48 Cu1 1.978(2) 3_765 ? N51 C52 1.329(4) . ? N51 C56 1.334(4) . ? C52 C53 1.379(4) . ? C52 H52 0.9500 . ? C53 C54 1.383(5) . ? C53 C64 1.481(5) . ? C54 C55 1.373(5) . ? C54 H54 0.9500 . ? C55 C56 1.390(5) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? N61 C66 1.328(4) . ? N61 C62 1.353(4) . ? C62 N63 1.332(4) . ? C62 N62 1.343(4) . ? N62 H62A 0.73(4) . ? N62 H62B 0.83(4) . ? N63 C64 1.336(4) . ? C64 C65 1.379(4) . ? C65 C66 1.376(5) . ? C65 H65 0.9500 . ? C66 C67 1.501(4) . ? C67 H67A 0.9800 . ? C67 H67B 0.9800 . ? C67 H67C 0.9800 . ? C71 C76 1.365(5) . ? C71 C72 1.382(5) . ? C71 C77 1.490(5) . ? C72 F72 1.352(5) . ? C72 C73 1.386(6) . ? C73 C74 1.356(7) . ? C73 H73 0.9500 . ? C74 C75 1.345(6) . ? C74 H74 0.9500 . ? C75 C76 1.379(5) . ? C75 H75 0.9500 . ? C76 H76 0.9500 . ? C77 O77 1.248(4) . ? C77 O78 1.263(4) . ? O78 Cu2 1.985(2) 3_666 ? C81 C82 1.375(5) . ? C81 C86 1.386(5) . ? C81 C87 1.492(4) . ? C82 F82 1.356(4) . ? C82 C83 1.369(5) . ? C83 C84 1.383(5) . ? C83 H83 0.9500 . ? C84 C85 1.368(5) . ? C84 H84 0.9500 . ? C85 C86 1.370(5) . ? C85 H85 0.9500 . ? C86 H86 0.9500 . ? C87 O88 1.252(4) . ? C87 O87 1.258(4) . ? O88 Cu2 1.942(2) 3_666 ? 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 O37 Cu1 O47 89.18(10) . . ? O37 Cu1 O38 167.83(9) . 3_765 ? O47 Cu1 O38 90.36(10) . 3_765 ? O37 Cu1 O48 89.55(9) . 3_765 ? O47 Cu1 O48 167.86(9) . 3_765 ? O38 Cu1 O48 88.35(9) 3_765 3_765 ? O37 Cu1 N11 95.36(10) . . ? O47 Cu1 N11 91.66(10) . . ? O38 Cu1 N11 96.81(10) 3_765 . ? O48 Cu1 N11 100.48(10) 3_765 . ? O37 Cu1 Cu1 84.45(7) . 3_765 ? O47 Cu1 Cu1 82.07(7) . 3_765 ? O38 Cu1 Cu1 83.44(7) 3_765 3_765 ? O48 Cu1 Cu1 85.79(7) 3_765 3_765 ? N11 Cu1 Cu1 173.73(8) . 3_765 ? O87 Cu2 O88 167.48(9) . 3_666 ? O87 Cu2 O77 86.90(11) . . ? O88 Cu2 O77 93.04(10) 3_666 . ? O87 Cu2 O78 89.34(10) . 3_666 ? O88 Cu2 O78 88.08(10) 3_666 3_666 ? O77 Cu2 O78 167.59(9) . 3_666 ? O87 Cu2 N51 95.45(10) . . ? O88 Cu2 N51 96.94(10) 3_666 . ? O77 Cu2 N51 98.65(10) . . ? O78 Cu2 N51 93.48(10) 3_666 . ? O87 Cu2 Cu2 83.50(7) . 3_666 ? O88 Cu2 Cu2 84.09(7) 3_666 3_666 ? O77 Cu2 Cu2 82.05(6) . 3_666 ? O78 Cu2 Cu2 85.78(6) 3_666 3_666 ? N51 Cu2 Cu2 178.71(8) . 3_666 ? C12 N11 C16 117.9(3) . . ? C12 N11 Cu1 119.3(2) . . ? C16 N11 Cu1 122.7(2) . . ? N11 C12 C13 123.9(3) . . ? N11 C12 H12 118.1 . . ? C13 C12 H12 118.1 . . ? C14 C13 C12 118.0(3) . . ? C14 C13 C24 121.5(3) . . ? C12 C13 C24 120.6(3) . . ? C13 C14 C15 119.0(3) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 119.4(3) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? N11 C16 C15 122.0(3) . . ? N11 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C26 N21 C22 116.5(3) . . ? N21 C22 N23 126.4(3) . . ? N21 C22 N22 116.5(3) . . ? N23 C22 N22 117.1(3) . . ? C22 N22 H22A 114(2) . . ? C22 N22 H22B 118(2) . . ? H22A N22 H22B 123(3) . . ? C24 N23 C22 115.7(3) . . ? N23 C24 C25 121.8(3) . . ? N23 C24 C13 116.3(3) . . ? C25 C24 C13 121.9(3) . . ? C24 C25 C26 117.7(3) . . ? C24 C25 H25 121.2 . . ? C26 C25 H25 121.2 . . ? N21 C26 C25 121.9(3) . . ? N21 C26 C27 117.2(3) . . ? C25 C26 C27 120.8(3) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C36A C31 C32A 116.6(3) . . ? C36A C31 C37 122.1(3) . . ? C32A C31 C37 121.2(3) . . ? F32 C32A C31 126.2(4) . . ? F32 C32A C33 111.5(5) . . ? C31 C32A C33 122.3(4) . . ? C34 C33 C32A 118.8(5) . . ? C34 C33 H33 120.6 . . ? C32A C33 H33 120.6 . . ? C35 C34 C33 120.2(4) . . ? C35 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C34 C35 C36A 119.7(4) . . ? C34 C35 H35 120.2 . . ? C36A C35 H35 120.2 . . ? C31 C36A C35 122.3(4) . . ? C31 C36A H36 118.8 . . ? C35 C36A H36 118.8 . . ? O37 C37 O38 125.3(3) . . ? O37 C37 C31 117.5(3) . . ? O38 C37 C31 117.2(3) . . ? C37 O37 Cu1 122.8(2) . . ? C37 O38 Cu1 123.64(19) . 3_765 ? C46A C41 C42A 117.1(3) . . ? C46A C41 C47 120.9(3) . . ? C42A C41 C47 121.9(3) . . ? F42 C42A C43 116.7(3) . . ? F42 C42A C41 121.8(3) . . ? C43 C42A C41 121.5(4) . . ? C44 C43 C42A 119.4(4) . . ? C44 C43 H43 120.3 . . ? C42A C43 H43 120.3 . . ? C45 C44 C43 120.3(4) . . ? C45 C44 H44 119.8 . . ? C43 C44 H44 119.8 . . ? C46A C45 C44 119.3(4) . . ? C46A C45 H45 120.3 . . ? C44 C45 H45 120.3 . . ? C45 C46A C41 122.4(4) . . ? C45 C46A H46 118.8 . . ? C41 C46A H46 118.8 . . ? O47 C47 O48 124.8(3) . . ? O47 C47 C41 118.7(3) . . ? O48 C47 C41 116.5(3) . . ? C47 O47 Cu1 126.5(2) . . ? C47 O48 Cu1 120.7(2) . 3_765 ? C52 N51 C56 118.1(3) . . ? C52 N51 Cu2 116.3(2) . . ? C56 N51 Cu2 125.4(2) . . ? N51 C52 C53 124.1(3) . . ? N51 C52 H52 118.0 . . ? C53 C52 H52 118.0 . . ? C52 C53 C54 117.5(3) . . ? C52 C53 C64 118.9(3) . . ? C54 C53 C64 123.6(3) . . ? C55 C54 C53 119.3(3) . . ? C55 C54 H54 120.4 . . ? C53 C54 H54 120.4 . . ? C54 C55 C56 119.3(3) . . ? C54 C55 H55 120.3 . . ? C56 C55 H55 120.3 . . ? N51 C56 C55 121.7(3) . . ? N51 C56 H56 119.1 . . ? C55 C56 H56 119.1 . . ? C66 N61 C62 115.6(3) . . ? N63 C62 N62 117.7(3) . . ? N63 C62 N61 126.7(3) . . ? N62 C62 N61 115.6(3) . . ? C62 N62 H62A 117(3) . . ? C62 N62 H62B 116(2) . . ? H62A N62 H62B 126(4) . . ? C62 N63 C64 115.5(3) . . ? N63 C64 C65 122.6(3) . . ? N63 C64 C53 115.5(3) . . ? C65 C64 C53 121.9(3) . . ? C66 C65 C64 117.0(3) . . ? C66 C65 H65 121.5 . . ? C64 C65 H65 121.5 . . ? N61 C66 C65 122.4(3) . . ? N61 C66 C67 116.9(3) . . ? C65 C66 C67 120.7(3) . . ? C66 C67 H67A 109.5 . . ? C66 C67 H67B 109.5 . . ? H67A C67 H67B 109.5 . . ? C66 C67 H67C 109.5 . . ? H67A C67 H67C 109.5 . . ? H67B C67 H67C 109.5 . . ? C76 C71 C72 116.6(4) . . ? C76 C71 C77 121.7(3) . . ? C72 C71 C77 121.7(3) . . ? F72 C72 C71 118.9(4) . . ? F72 C72 C73 118.4(4) . . ? C71 C72 C73 122.6(4) . . ? C74 C73 C72 118.3(4) . . ? C74 C73 H73 120.8 . . ? C72 C73 H73 120.8 . . ? C75 C74 C73 120.3(4) . . ? C75 C74 H74 119.8 . . ? C73 C74 H74 119.8 . . ? C74 C75 C76 121.0(4) . . ? C74 C75 H75 119.5 . . ? C76 C75 H75 119.5 . . ? C71 C76 C75 120.9(4) . . ? C71 C76 H76 119.5 . . ? C75 C76 H76 119.5 . . ? O77 C77 O78 125.1(3) . . ? O77 C77 C71 118.4(3) . . ? O78 C77 C71 116.5(3) . . ? C77 O77 Cu2 125.5(2) . . ? C77 O78 Cu2 120.0(2) . 3_666 ? C82 C81 C86 116.6(3) . . ? C82 C81 C87 123.8(3) . . ? C86 C81 C87 119.6(3) . . ? F82 C82 C83 116.6(3) . . ? F82 C82 C81 120.3(3) . . ? C83 C82 C81 123.1(3) . . ? C82 C83 C84 118.6(4) . . ? C82 C83 H83 120.7 . . ? C84 C83 H83 120.7 . . ? C85 C84 C83 120.1(4) . . ? C85 C84 H84 120.0 . . ? C83 C84 H84 120.0 . . ? C84 C85 C86 119.9(4) . . ? C84 C85 H85 120.0 . . ? C86 C85 H85 120.0 . . ? C85 C86 C81 121.8(4) . . ? C85 C86 H86 119.1 . . ? C81 C86 H86 119.1 . . ? O88 C87 O87 125.2(3) . . ? O88 C87 C81 118.8(3) . . ? O87 C87 C81 116.0(3) . . ? C87 O87 Cu2 123.8(2) . . ? C87 O88 Cu2 123.2(2) . 3_666 ? 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 O37 Cu1 N11 C12 177.0(3) . . . . ? O47 Cu1 N11 C12 -93.7(3) . . . . ? O38 Cu1 N11 C12 -3.2(3) 3_765 . . . ? O48 Cu1 N11 C12 86.4(3) 3_765 . . . ? Cu1 Cu1 N11 C12 -95.0(7) 3_765 . . . ? O37 Cu1 N11 C16 -7.1(3) . . . . ? O47 Cu1 N11 C16 82.3(3) . . . . ? O38 Cu1 N11 C16 172.8(3) 3_765 . . . ? O48 Cu1 N11 C16 -97.6(3) 3_765 . . . ? Cu1 Cu1 N11 C16 81.0(7) 3_765 . . . ? C16 N11 C12 C13 1.9(5) . . . . ? Cu1 N11 C12 C13 178.1(3) . . . . ? N11 C12 C13 C14 -1.5(5) . . . . ? N11 C12 C13 C24 177.4(3) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C24 C13 C14 C15 -178.7(3) . . . . ? C13 C14 C15 C16 0.5(6) . . . . ? C12 N11 C16 C15 -1.0(5) . . . . ? Cu1 N11 C16 C15 -177.1(3) . . . . ? C14 C15 C16 N11 -0.1(6) . . . . ? C26 N21 C22 N23 -1.2(5) . . . . ? C26 N21 C22 N22 179.8(3) . . . . ? N21 C22 N23 C24 -0.8(5) . . . . ? N22 C22 N23 C24 178.2(3) . . . . ? C22 N23 C24 C25 2.3(5) . . . . ? C22 N23 C24 C13 -178.9(3) . . . . ? C14 C13 C24 N23 1.9(5) . . . . ? C12 C13 C24 N23 -177.0(3) . . . . ? C14 C13 C24 C25 -179.3(3) . . . . ? C12 C13 C24 C25 1.8(5) . . . . ? N23 C24 C25 C26 -1.9(5) . . . . ? C13 C24 C25 C26 179.4(3) . . . . ? C22 N21 C26 C25 1.6(5) . . . . ? C22 N21 C26 C27 -176.4(3) . . . . ? C24 C25 C26 N21 -0.2(5) . . . . ? C24 C25 C26 C27 177.8(3) . . . . ? C36A C31 C32A F32 178.6(5) . . . . ? C37 C31 C32A F32 -3.0(7) . . . . ? C36A C31 C32A C33 -0.4(6) . . . . ? C37 C31 C32A C33 178.0(4) . . . . ? F32 C32A C33 C34 -179.9(6) . . . . ? C31 C32A C33 C34 -0.8(8) . . . . ? C32A C33 C34 C35 1.4(8) . . . . ? C33 C34 C35 C36A -0.9(8) . . . . ? C32A C31 C36A C35 0.9(6) . . . . ? C37 C31 C36A C35 -177.5(4) . . . . ? C34 C35 C36A C31 -0.3(7) . . . . ? C36A C31 C37 O37 -168.0(3) . . . . ? C32A C31 C37 O37 13.7(5) . . . . ? C36A C31 C37 O38 12.8(5) . . . . ? C32A C31 C37 O38 -165.6(3) . . . . ? O38 C37 O37 Cu1 7.4(5) . . . . ? C31 C37 O37 Cu1 -171.8(2) . . . . ? O47 Cu1 O37 C37 77.6(3) . . . . ? O38 Cu1 O37 C37 -10.3(6) 3_765 . . . ? O48 Cu1 O37 C37 -90.3(3) 3_765 . . . ? N11 Cu1 O37 C37 169.2(3) . . . . ? Cu1 Cu1 O37 C37 -4.5(3) 3_765 . . . ? O37 C37 O38 Cu1 -5.7(5) . . . 3_765 ? C31 C37 O38 Cu1 173.5(2) . . . 3_765 ? C46A C41 C42A F42 -179.2(3) . . . . ? C47 C41 C42A F42 -3.5(5) . . . . ? C46A C41 C42A C43 -2.3(5) . . . . ? C47 C41 C42A C43 173.4(3) . . . . ? F42 C42A C43 C44 178.1(3) . . . . ? C41 C42A C43 C44 1.1(5) . . . . ? C42A C43 C44 C45 0.8(6) . . . . ? C43 C44 C45 C46A -1.4(6) . . . . ? C44 C45 C46A C41 0.1(6) . . . . ? C42A C41 C46A C45 1.7(5) . . . . ? C47 C41 C46A C45 -174.0(3) . . . . ? C46A C41 C47 O47 -165.6(3) . . . . ? C42A C41 C47 O47 18.8(5) . . . . ? C46A C41 C47 O48 15.1(4) . . . . ? C42A C41 C47 O48 -160.4(3) . . . . ? O48 C47 O47 Cu1 4.8(4) . . . . ? C41 C47 O47 Cu1 -174.3(2) . . . . ? O37 Cu1 O47 C47 -86.9(3) . . . . ? O38 Cu1 O47 C47 80.9(3) 3_765 . . . ? O48 Cu1 O47 C47 -2.9(6) 3_765 . . . ? N11 Cu1 O47 C47 177.8(3) . . . . ? Cu1 Cu1 O47 C47 -2.4(2) 3_765 . . . ? O47 C47 O48 Cu1 -4.4(4) . . . 3_765 ? C41 C47 O48 Cu1 174.76(18) . . . 3_765 ? O87 Cu2 N51 C52 -3.2(3) . . . . ? O88 Cu2 N51 C52 174.9(2) 3_666 . . . ? O77 Cu2 N51 C52 -90.9(2) . . . . ? O78 Cu2 N51 C52 86.4(2) 3_666 . . . ? Cu2 Cu2 N51 C52 32(4) 3_666 . . . ? O87 Cu2 N51 C56 -178.6(3) . . . . ? O88 Cu2 N51 C56 -0.4(3) 3_666 . . . ? O77 Cu2 N51 C56 93.7(3) . . . . ? O78 Cu2 N51 C56 -88.9(3) 3_666 . . . ? Cu2 Cu2 N51 C56 -144(3) 3_666 . . . ? C56 N51 C52 C53 -0.1(5) . . . . ? Cu2 N51 C52 C53 -175.8(3) . . . . ? N51 C52 C53 C54 -2.4(5) . . . . ? N51 C52 C53 C64 177.9(3) . . . . ? C52 C53 C54 C55 2.5(6) . . . . ? C64 C53 C54 C55 -177.8(4) . . . . ? C53 C54 C55 C56 -0.4(6) . . . . ? C52 N51 C56 C55 2.4(5) . . . . ? Cu2 N51 C56 C55 177.7(3) . . . . ? C54 C55 C56 N51 -2.2(6) . . . . ? C66 N61 C62 N63 2.2(5) . . . . ? C66 N61 C62 N62 179.1(3) . . . . ? N62 C62 N63 C64 179.0(3) . . . . ? N61 C62 N63 C64 -4.2(5) . . . . ? C62 N63 C64 C65 1.0(5) . . . . ? C62 N63 C64 C53 -179.5(3) . . . . ? C52 C53 C64 N63 -36.2(5) . . . . ? C54 C53 C64 N63 144.2(4) . . . . ? C52 C53 C64 C65 143.3(3) . . . . ? C54 C53 C64 C65 -36.4(5) . . . . ? N63 C64 C65 C66 3.6(5) . . . . ? C53 C64 C65 C66 -175.8(3) . . . . ? C62 N61 C66 C65 3.1(5) . . . . ? C62 N61 C66 C67 -174.6(3) . . . . ? C64 C65 C66 N61 -5.8(5) . . . . ? C64 C65 C66 C67 171.9(3) . . . . ? C76 C71 C72 F72 -174.9(3) . . . . ? C77 C71 C72 F72 4.7(5) . . . . ? C76 C71 C72 C73 2.4(5) . . . . ? C77 C71 C72 C73 -178.1(3) . . . . ? F72 C72 C73 C74 178.4(4) . . . . ? C71 C72 C73 C74 1.0(6) . . . . ? C72 C73 C74 C75 -3.0(7) . . . . ? C73 C74 C75 C76 1.5(7) . . . . ? C72 C71 C76 C75 -4.0(5) . . . . ? C77 C71 C76 C75 176.5(3) . . . . ? C74 C75 C76 C71 2.2(6) . . . . ? C76 C71 C77 O77 -138.3(3) . . . . ? C72 C71 C77 O77 42.2(5) . . . . ? C76 C71 C77 O78 40.6(5) . . . . ? C72 C71 C77 O78 -138.9(3) . . . . ? O78 C77 O77 Cu2 13.5(5) . . . . ? C71 C77 O77 Cu2 -167.7(2) . . . . ? O87 Cu2 O77 C77 79.8(3) . . . . ? O88 Cu2 O77 C77 -87.7(3) 3_666 . . . ? O78 Cu2 O77 C77 7.2(6) 3_666 . . . ? N51 Cu2 O77 C77 174.8(3) . . . . ? Cu2 Cu2 O77 C77 -4.1(3) 3_666 . . . ? O77 C77 O78 Cu2 -16.1(5) . . . 3_666 ? C71 C77 O78 Cu2 165.0(2) . . . 3_666 ? C86 C81 C82 F82 -177.8(3) . . . . ? C87 C81 C82 F82 1.6(5) . . . . ? C86 C81 C82 C83 0.4(5) . . . . ? C87 C81 C82 C83 179.8(3) . . . . ? F82 C82 C83 C84 178.9(3) . . . . ? C81 C82 C83 C84 0.6(6) . . . . ? C82 C83 C84 C85 -0.8(6) . . . . ? C83 C84 C85 C86 -0.1(6) . . . . ? C84 C85 C86 C81 1.2(6) . . . . ? C82 C81 C86 C85 -1.3(5) . . . . ? C87 C81 C86 C85 179.3(3) . . . . ? C82 C81 C87 O88 18.1(5) . . . . ? C86 C81 C87 O88 -162.5(3) . . . . ? C82 C81 C87 O87 -162.2(3) . . . . ? C86 C81 C87 O87 17.2(5) . . . . ? O88 C87 O87 Cu2 -6.3(5) . . . . ? C81 C87 O87 Cu2 174.0(2) . . . . ? O88 Cu2 O87 C87 12.1(7) 3_666 . . . ? O77 Cu2 O87 C87 -77.9(3) . . . . ? O78 Cu2 O87 C87 90.2(3) 3_666 . . . ? N51 Cu2 O87 C87 -176.3(3) . . . . ? Cu2 Cu2 O87 C87 4.4(3) 3_666 . . . ? O87 C87 O88 Cu2 3.9(5) . . . 3_666 ? C81 C87 O88 Cu2 -176.4(2) . . . 3_666 ? 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 N22 H22A N63 0.93(4) 2.31(4) 3.241(4) 174(3) 3_666 N22 H22B O78 0.95(4) 2.26(4) 3.206(4) 173(3) . N62 H62A N21 0.73(4) 2.27(4) 3.001(4) 171(4) 3_666 N62 H62B O48 0.83(4) 2.27(4) 3.055(4) 159(3) 1_455 _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.913 _refine_diff_density_max 0.486 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.086 #END data_11 _database_code_depnum_ccdc_archive 'CCDC 278019' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(2-NH2-4-pyrimidyl)-2-(3-methoxy-5-pyridyl)ethyne (AcO)4Cu2 (EtO).6 (CH3CN).8 ; _chemical_name_common ;1-(2-NH2-4-pyrimidyl)-2-(3-methoxy-5-pyridyl)ethyne (AcO)4Cu2 (EtO).6 (CH3CN).8 ; _chemical_melting_point ? _chemical_formula_moiety ; (C34 H36 Cu2 N8 O10) (C2 H5 O)0.6 (C2 H3 N)0.8 ; _chemical_formula_sum 'C36.80 H41.40 Cu2 N8.80 O10.60' _chemical_formula_weight 903.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6304(13) _cell_length_b 11.3870(19) _cell_length_c 12.341(2) _cell_angle_alpha 76.216(3) _cell_angle_beta 84.191(3) _cell_angle_gamma 79.459(3) _cell_volume 1021.9(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4343 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 29.95 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_max 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 467 _exptl_absorpt_coefficient_mu 1.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.796 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9372 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 30.04 _reflns_number_total 5732 _reflns_number_gt 4969 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.6500P] 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_number_reflns 5732 _refine_ls_number_parameters 274 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1284 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.062 _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 0.57737(4) 0.42082(2) 0.08504(2) 0.02393(10) Uani 1 1 d . . . O1S O 0.8707(17) 0.3959(12) 0.4651(12) 0.0982(18) Uiso 0.30 1 d PD A 1 C1S C 0.738(3) 0.4966(18) 0.4811(14) 0.0982(18) Uiso 0.30 1 d PD A 1 H1A H 0.7917 0.5525 0.5135 0.118 Uiso 0.30 1 calc PR A 1 H1B H 0.6416 0.4664 0.5343 0.118 Uiso 0.30 1 calc PR A 1 C2S C 0.662(2) 0.5654(17) 0.3711(16) 0.0982(18) Uiso 0.30 1 d PD A 1 H2A H 0.7392 0.5405 0.3094 0.147 Uiso 0.30 1 calc PR A 1 H2B H 0.6542 0.6537 0.3642 0.147 Uiso 0.30 1 calc PR A 1 H2C H 0.5420 0.5468 0.3684 0.147 Uiso 0.30 1 calc PR A 1 N1S N 0.8841(15) 0.4762(12) 0.4989(11) 0.0982(18) Uiso 0.40 1 d PD B 2 C3S C 0.7577(18) 0.4964(16) 0.4466(13) 0.0982(18) Uiso 0.40 1 d PD B 2 C4S C 0.5967(17) 0.5456(15) 0.3843(13) 0.0982(18) Uiso 0.40 1 d PD B 2 H4A H 0.6058 0.5112 0.3180 0.147 Uiso 0.40 1 calc PR B 2 H4B H 0.5848 0.6350 0.3614 0.147 Uiso 0.40 1 calc PR B 2 H4C H 0.4917 0.5233 0.4321 0.147 Uiso 0.40 1 calc PR B 2 N11 N 0.0126(3) 0.06769(18) 0.84422(16) 0.0252(4) Uani 1 1 d . . . C12 C 0.1820(3) 0.0057(2) 0.84733(18) 0.0240(4) Uani 1 1 d . . . N12 N 0.2273(3) -0.07590(19) 0.94238(17) 0.0293(4) Uani 1 1 d . . . H12A H 0.323(5) -0.120(3) 0.939(3) 0.035 Uiso 1 1 d . . . H12B H 0.164(5) -0.075(3) 0.989(3) 0.035 Uiso 1 1 d . . . N13 N 0.3105(3) 0.01993(17) 0.76410(15) 0.0239(4) Uani 1 1 d . . . C14 C 0.2613(3) 0.1033(2) 0.67100(18) 0.0244(4) Uani 1 1 d . . . C15 C 0.0892(3) 0.1689(2) 0.65767(19) 0.0268(4) Uani 1 1 d . . . H15 H 0.0568 0.2258 0.5901 0.032 Uiso 1 1 calc R . . C16 C -0.0331(3) 0.1464(2) 0.74906(19) 0.0271(4) Uani 1 1 d . . . C17 C 0.3980(3) 0.1264(2) 0.58356(18) 0.0257(4) Uani 1 1 d . . . C18 C -0.2241(4) 0.2100(3) 0.7444(2) 0.0369(6) Uani 1 1 d . . . H18A H -0.3024 0.1502 0.7461 0.055 Uiso 1 1 calc R . . H18B H -0.2381 0.2736 0.6752 0.055 Uiso 1 1 calc R . . H18C H -0.2562 0.2477 0.8088 0.055 Uiso 1 1 calc R . . N21 N 0.6908(3) 0.29463(16) 0.23288(15) 0.0235(4) Uani 1 1 d . . . C22 C 0.8633(3) 0.24423(19) 0.23606(18) 0.0233(4) Uani 1 1 d . . . H22 H 0.9411 0.2651 0.1719 0.028 Uiso 1 1 calc R . . C23 C 0.9325(3) 0.16167(19) 0.33096(18) 0.0234(4) Uani 1 1 d . . . O23 O 1.1056(2) 0.10742(16) 0.33939(14) 0.0300(4) Uani 1 1 d . . . C24 C 0.8169(3) 0.1298(2) 0.42464(18) 0.0248(4) Uani 1 1 d . . . H24 H 0.8601 0.0738 0.4903 0.030 Uiso 1 1 calc R . . C25 C 0.6382(3) 0.18170(19) 0.41961(17) 0.0227(4) Uani 1 1 d . . . C26 C 0.5802(3) 0.26499(19) 0.32190(18) 0.0240(4) Uani 1 1 d . . . H26 H 0.4580 0.3016 0.3190 0.029 Uiso 1 1 calc R . . C27 C 0.5101(3) 0.1506(2) 0.51052(18) 0.0247(4) Uani 1 1 d . . . C28 C 1.2257(3) 0.1351(2) 0.2426(2) 0.0328(5) Uani 1 1 d . . . H28A H 1.3455 0.0895 0.2589 0.049 Uiso 1 1 calc R . . H28B H 1.2297 0.2232 0.2233 0.049 Uiso 1 1 calc R . . H28C H 1.1836 0.1115 0.1797 0.049 Uiso 1 1 calc R . . C31 C 0.2105(4) 0.5292(2) 0.1150(2) 0.0325(5) Uani 1 1 d . . . O31 O 0.3404(3) 0.45626(18) 0.15916(15) 0.0404(5) Uani 1 1 d . . . O32 O 0.2097(3) 0.59271(18) 0.01643(17) 0.0402(5) Uani 1 1 d . . . C32 C 0.0456(5) 0.5402(3) 0.1886(3) 0.0541(8) Uani 1 1 d . . . H32A H 0.0694 0.4908 0.2639 0.081 Uiso 1 1 calc R . . H32B H -0.0482 0.5108 0.1588 0.081 Uiso 1 1 calc R . . H32C H 0.0064 0.6262 0.1919 0.081 Uiso 1 1 calc R . . C41 C 0.6021(4) 0.6758(2) 0.0554(2) 0.0328(5) Uani 1 1 d . . . O41 O 0.6395(4) 0.56954(18) 0.11536(19) 0.0539(7) Uani 1 1 d . . . O42 O 0.5127(2) 0.70389(14) -0.02881(14) 0.0288(3) Uani 1 1 d . . . C42 C 0.6751(5) 0.7770(3) 0.0860(3) 0.0529(9) Uani 1 1 d . . . H42A H 0.6039 0.8562 0.0536 0.079 Uiso 1 1 calc R . . H42B H 0.7995 0.7758 0.0568 0.079 Uiso 1 1 calc R . . H42C H 0.6692 0.7649 0.1676 0.079 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 0.03290(17) 0.01657(13) 0.01945(14) 0.00260(9) -0.00732(10) -0.00229(10) N11 0.0256(9) 0.0260(9) 0.0221(8) -0.0033(7) -0.0008(7) -0.0027(7) C12 0.0276(11) 0.0225(9) 0.0206(9) -0.0038(7) -0.0014(8) -0.0023(8) N12 0.0307(11) 0.0275(9) 0.0212(9) 0.0017(7) 0.0039(8) 0.0046(8) N13 0.0279(9) 0.0211(8) 0.0199(8) -0.0028(6) -0.0002(7) -0.0003(7) C14 0.0305(11) 0.0216(9) 0.0197(9) -0.0037(7) -0.0014(8) -0.0024(8) C15 0.0295(11) 0.0262(10) 0.0212(9) -0.0008(8) -0.0047(8) 0.0001(8) C16 0.0272(11) 0.0265(10) 0.0262(10) -0.0049(8) -0.0046(8) -0.0008(8) C17 0.0304(11) 0.0226(9) 0.0215(9) -0.0014(7) -0.0045(8) -0.0010(8) C18 0.0280(12) 0.0437(14) 0.0326(12) -0.0030(11) -0.0043(10) 0.0047(10) N21 0.0300(10) 0.0196(8) 0.0179(8) 0.0023(6) -0.0048(7) -0.0031(7) C22 0.0265(11) 0.0199(9) 0.0210(9) 0.0025(7) -0.0043(8) -0.0050(8) C23 0.0240(10) 0.0214(9) 0.0225(9) 0.0005(7) -0.0048(8) -0.0032(8) O23 0.0241(8) 0.0321(8) 0.0273(8) 0.0054(6) -0.0039(6) -0.0025(6) C24 0.0289(11) 0.0232(9) 0.0189(9) 0.0027(7) -0.0058(8) -0.0030(8) C25 0.0281(11) 0.0201(9) 0.0179(9) -0.0007(7) -0.0025(8) -0.0034(8) C26 0.0267(11) 0.0211(9) 0.0210(9) 0.0009(7) -0.0056(8) -0.0010(8) C27 0.0287(11) 0.0228(9) 0.0197(9) -0.0012(7) -0.0041(8) -0.0002(8) C28 0.0252(11) 0.0336(12) 0.0344(12) 0.0020(10) -0.0004(9) -0.0053(9) C31 0.0374(13) 0.0220(10) 0.0343(12) -0.0014(9) 0.0014(10) -0.0034(9) O31 0.0483(12) 0.0368(10) 0.0233(8) 0.0016(7) 0.0012(8) 0.0127(8) O32 0.0301(9) 0.0390(10) 0.0388(10) 0.0144(8) -0.0020(8) -0.0036(8) C32 0.0430(17) 0.0458(17) 0.062(2) 0.0011(15) 0.0035(15) 0.0000(13) C41 0.0426(14) 0.0216(10) 0.0347(12) -0.0037(9) -0.0107(10) -0.0052(9) O41 0.0922(18) 0.0247(9) 0.0486(12) 0.0050(8) -0.0434(12) -0.0158(10) O42 0.0346(9) 0.0187(7) 0.0316(8) -0.0016(6) -0.0065(7) -0.0031(6) C42 0.076(2) 0.0299(13) 0.0592(19) -0.0100(13) -0.0296(17) -0.0123(14) _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 O32 1.955(2) 2_665 ? Cu1 O31 1.960(2) . ? Cu1 O41 1.9657(19) . ? Cu1 O42 1.9732(16) 2_665 ? Cu1 N21 2.1813(18) . ? Cu1 Cu1 2.6401(6) 2_665 ? O1S C1S 1.420(10) . ? C1S C2S 1.512(10) . ? C1S H1A 0.9900 . ? C1S H1B 0.9900 . ? C2S H2A 0.9800 . ? C2S H2B 0.9800 . ? C2S H2C 0.9800 . ? N1S C3S 1.172(4) . ? C3S C4S 1.466(4) . ? C4S H4A 0.9800 . ? C4S H4B 0.9800 . ? C4S H4C 0.9800 . ? N11 C16 1.331(3) . ? N11 C12 1.354(3) . ? C12 N12 1.343(3) . ? C12 N13 1.348(3) . ? N12 H12A 0.81(4) . ? N12 H12B 0.71(3) . ? N13 C14 1.341(3) . ? C14 C15 1.391(3) . ? C14 C17 1.435(3) . ? C15 C16 1.395(3) . ? C15 H15 0.9500 . ? C16 C18 1.504(3) . ? C17 C27 1.197(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? N21 C26 1.331(3) . ? N21 C22 1.337(3) . ? C22 C23 1.398(3) . ? C22 H22 0.9500 . ? C23 O23 1.354(3) . ? C23 C24 1.399(3) . ? O23 C28 1.439(3) . ? C24 C25 1.385(3) . ? C24 H24 0.9500 . ? C25 C26 1.400(3) . ? C25 C27 1.433(3) . ? C26 H26 0.9500 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C31 O31 1.250(3) . ? C31 O32 1.258(3) . ? C31 C32 1.480(4) . ? O32 Cu1 1.955(2) 2_665 ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C41 O42 1.246(3) . ? C41 O41 1.258(3) . ? C41 C42 1.506(4) . ? O42 Cu1 1.9732(16) 2_665 ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? 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 O32 Cu1 O31 168.08(8) 2_665 . ? O32 Cu1 O41 89.80(11) 2_665 . ? O31 Cu1 O41 89.65(11) . . ? O32 Cu1 O42 90.15(8) 2_665 2_665 ? O31 Cu1 O42 87.91(9) . 2_665 ? O41 Cu1 O42 167.87(7) . 2_665 ? O32 Cu1 N21 97.50(8) 2_665 . ? O31 Cu1 N21 94.40(8) . . ? O41 Cu1 N21 96.27(8) . . ? O42 Cu1 N21 95.75(7) 2_665 . ? O32 Cu1 Cu1 86.17(6) 2_665 2_665 ? O31 Cu1 Cu1 81.95(6) . 2_665 ? O41 Cu1 Cu1 82.61(6) . 2_665 ? O42 Cu1 Cu1 85.29(5) 2_665 2_665 ? N21 Cu1 Cu1 176.17(5) . 2_665 ? O1S C1S C2S 110.4(9) . . ? O1S C1S H1A 109.6 . . ? C2S C1S H1A 109.6 . . ? O1S C1S H1B 109.6 . . ? C2S C1S H1B 109.6 . . ? H1A C1S H1B 108.1 . . ? C1S C2S H2A 109.5 . . ? C1S C2S H2B 109.5 . . ? H2A C2S H2B 109.5 . . ? C1S C2S H2C 109.5 . . ? H2A C2S H2C 109.5 . . ? H2B C2S H2C 109.5 . . ? N1S C3S C4S 169.0(17) . . ? C3S C4S H4A 109.5 . . ? C3S C4S H4B 109.5 . . ? H4A C4S H4B 109.5 . . ? C3S C4S H4C 109.5 . . ? H4A C4S H4C 109.5 . . ? H4B C4S H4C 109.5 . . ? C16 N11 C12 117.11(19) . . ? N12 C12 N13 116.9(2) . . ? N12 C12 N11 117.2(2) . . ? N13 C12 N11 125.8(2) . . ? C12 N12 H12A 115(2) . . ? C12 N12 H12B 116(3) . . ? H12A N12 H12B 128(4) . . ? C14 N13 C12 115.3(2) . . ? N13 C14 C15 123.5(2) . . ? N13 C14 C17 116.7(2) . . ? C15 C14 C17 119.8(2) . . ? C14 C15 C16 116.3(2) . . ? C14 C15 H15 121.9 . . ? C16 C15 H15 121.9 . . ? N11 C16 C15 121.9(2) . . ? N11 C16 C18 116.7(2) . . ? C15 C16 C18 121.4(2) . . ? C27 C17 C14 177.3(2) . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C26 N21 C22 119.52(19) . . ? C26 N21 Cu1 117.59(15) . . ? C22 N21 Cu1 122.86(14) . . ? N21 C22 C23 121.9(2) . . ? N21 C22 H22 119.0 . . ? C23 C22 H22 119.0 . . ? O23 C23 C22 124.8(2) . . ? O23 C23 C24 116.40(19) . . ? C22 C23 C24 118.8(2) . . ? C23 O23 C28 117.41(18) . . ? C25 C24 C23 118.57(19) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C24 C25 C26 119.0(2) . . ? C24 C25 C27 121.99(19) . . ? C26 C25 C27 119.0(2) . . ? N21 C26 C25 122.2(2) . . ? N21 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? C17 C27 C25 177.5(2) . . ? O23 C28 H28A 109.5 . . ? O23 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O23 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O31 C31 O32 126.1(2) . . ? O31 C31 C32 115.1(2) . . ? O32 C31 C32 118.8(3) . . ? C31 O31 Cu1 125.35(17) . . ? C31 O32 Cu1 120.43(18) . 2_665 ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O42 C41 O41 125.4(2) . . ? O42 C41 C42 117.1(2) . . ? O41 C41 C42 117.4(2) . . ? C41 O41 Cu1 124.95(17) . . ? C41 O42 Cu1 121.68(15) . 2_665 ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? 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 C16 N11 C12 N12 -178.5(2) . . . . ? C16 N11 C12 N13 2.7(3) . . . . ? N12 C12 N13 C14 -179.1(2) . . . . ? N11 C12 N13 C14 -0.3(3) . . . . ? C12 N13 C14 C15 -2.0(3) . . . . ? C12 N13 C14 C17 176.09(19) . . . . ? N13 C14 C15 C16 1.8(3) . . . . ? C17 C14 C15 C16 -176.2(2) . . . . ? C12 N11 C16 C15 -2.8(3) . . . . ? C12 N11 C16 C18 176.9(2) . . . . ? C14 C15 C16 N11 0.8(3) . . . . ? C14 C15 C16 C18 -179.0(2) . . . . ? N13 C14 C17 C27 -128(5) . . . . ? C15 C14 C17 C27 50(5) . . . . ? O32 Cu1 N21 C26 -172.28(16) 2_665 . . . ? O31 Cu1 N21 C26 6.97(17) . . . . ? O41 Cu1 N21 C26 97.10(18) . . . . ? O42 Cu1 N21 C26 -81.37(17) 2_665 . . . ? Cu1 Cu1 N21 C26 24.3(9) 2_665 . . . ? O32 Cu1 N21 C22 5.78(18) 2_665 . . . ? O31 Cu1 N21 C22 -174.97(17) . . . . ? O41 Cu1 N21 C22 -84.85(19) . . . . ? O42 Cu1 N21 C22 96.69(17) 2_665 . . . ? Cu1 Cu1 N21 C22 -157.7(7) 2_665 . . . ? C26 N21 C22 C23 -0.7(3) . . . . ? Cu1 N21 C22 C23 -178.70(16) . . . . ? N21 C22 C23 O23 179.9(2) . . . . ? N21 C22 C23 C24 0.9(3) . . . . ? C22 C23 O23 C28 -1.3(3) . . . . ? C24 C23 O23 C28 177.7(2) . . . . ? O23 C23 C24 C25 -179.19(19) . . . . ? C22 C23 C24 C25 -0.1(3) . . . . ? C23 C24 C25 C26 -0.8(3) . . . . ? C23 C24 C25 C27 177.8(2) . . . . ? C22 N21 C26 C25 -0.3(3) . . . . ? Cu1 N21 C26 C25 177.82(16) . . . . ? C24 C25 C26 N21 1.1(3) . . . . ? C27 C25 C26 N21 -177.6(2) . . . . ? C14 C17 C27 C25 -73(9) . . . . ? C24 C25 C27 C17 -160(5) . . . . ? C26 C25 C27 C17 18(6) . . . . ? O32 C31 O31 Cu1 -0.5(4) . . . . ? C32 C31 O31 Cu1 -179.9(2) . . . . ? O32 Cu1 O31 C31 -5.4(6) 2_665 . . . ? O41 Cu1 O31 C31 82.0(2) . . . . ? O42 Cu1 O31 C31 -86.2(2) 2_665 . . . ? N21 Cu1 O31 C31 178.2(2) . . . . ? Cu1 Cu1 O31 C31 -0.6(2) 2_665 . . . ? O31 C31 O32 Cu1 1.9(4) . . . 2_665 ? C32 C31 O32 Cu1 -178.8(2) . . . 2_665 ? O42 C41 O41 Cu1 3.7(5) . . . . ? C42 C41 O41 Cu1 -174.6(2) . . . . ? O32 Cu1 O41 C41 83.8(3) 2_665 . . . ? O31 Cu1 O41 C41 -84.3(3) . . . . ? O42 Cu1 O41 C41 -6.0(7) 2_665 . . . ? N21 Cu1 O41 C41 -178.7(3) . . . . ? Cu1 Cu1 O41 C41 -2.4(3) 2_665 . . . ? O41 C41 O42 Cu1 -2.6(4) . . . 2_665 ? C42 C41 O42 Cu1 175.7(2) . . . 2_665 ? 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 N12 H12A O42 0.81(4) 2.22(4) 2.982(3) 156(3) 1_546 N12 H12B N11 0.71(3) 2.36(4) 3.062(3) 172(3) 2_557 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 1.138 _refine_diff_density_min -0.763 _refine_diff_density_rms 0.101 #END data_12 _database_code_depnum_ccdc_archive 'CCDC 278020' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(2-NH2-5-pyridyl)-2-(3-pyridyl)-ethyne, (2FPhCOO)4Cu2 ; _chemical_name_common '1-(2-NH2-5-pyridyl)-2-(3-pyridyl)-ethyne, (2FPhCOO)4Cu2' _chemical_melting_point ? _chemical_formula_moiety ; (C12 H9 N3) Cu2 (C7 H4 O2 F)4 ; _chemical_formula_sum 'C40 H25 Cu2 F4 N3 O8' _chemical_formula_weight 878.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.3471(9) _cell_length_b 15.5850(15) _cell_length_c 12.9025(11) _cell_angle_alpha 90.00 _cell_angle_beta 104.714(7) _cell_angle_gamma 90.00 _cell_volume 1817.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2305 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 26.25 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.250 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12614 _diffrn_reflns_av_R_equivalents 0.1368 _diffrn_reflns_av_sigmaI/netI 0.1396 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4188 _reflns_number_gt 2321 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0650P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0081(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4188 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1457 _refine_ls_wR_factor_gt 0.1275 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.894 _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 0.63109(5) 0.47848(4) 0.56134(4) 0.02735(19) Uani 1 1 d . . . N11 N 0.8450(3) 0.4505(2) 0.6676(3) 0.0302(8) Uani 1 1 d . . . C12A C 0.9683(5) 0.4448(3) 0.6343(3) 0.0351(10) Uani 0.50 1 d P A 1 N12 N 0.9662(8) 0.4180(6) 0.5365(6) 0.045(2) Uani 0.50 1 d P A 1 H12A H 0.8819 0.4034 0.4918 0.054 Uiso 0.50 1 calc PR A 1 H12B H 1.0491 0.4147 0.5162 0.054 Uiso 0.50 1 calc PR A 1 C12B C 0.9683(5) 0.4448(3) 0.6343(3) 0.0351(10) Uani 0.50 1 d P A 2 H12 H 0.9610 0.4312 0.5613 0.042 Uiso 0.50 1 calc PR A 2 C13 C 1.1059(5) 0.4579(3) 0.7021(4) 0.0450(13) Uani 1 1 d . . . H13 H 1.1916 0.4566 0.6754 0.054 Uiso 1 1 calc R A 1 C14 C 1.1181(5) 0.4728(3) 0.8081(4) 0.0466(12) Uani 1 1 d . A . H14 H 1.2124 0.4819 0.8560 0.056 Uiso 1 1 calc R . . C15 C 0.9932(5) 0.4746(3) 0.8446(3) 0.0354(10) Uani 1 1 d . . . C16 C 0.8591(4) 0.4644(3) 0.7715(3) 0.0339(11) Uani 1 1 d . A . H16 H 0.7719 0.4674 0.7964 0.041 Uiso 1 1 calc R . . C21 C 0.9987(5) 0.4915(3) 0.9550(4) 0.0455(12) Uani 1 1 d . . . C31 C 0.3196(5) 0.3064(3) 0.6238(4) 0.0353(11) Uani 1 1 d . . . C32A C 0.3744(6) 0.2938(3) 0.7343(4) 0.0467(13) Uani 0.571(5) 1 d P B 1 F32 F 0.4786(6) 0.3371(4) 0.7890(4) 0.0633(12) Uani 0.571(5) 1 d P B 1 C32B C 0.3744(6) 0.2938(3) 0.7343(4) 0.0467(13) Uani 0.429(5) 1 d P B 2 H32 H 0.4605 0.3238 0.7716 0.056 Uiso 0.429(5) 1 calc PR B 2 C33 C 0.3065(7) 0.2392(4) 0.7893(5) 0.0685(18) Uani 1 1 d . . . H33 H 0.3442 0.2328 0.8645 0.082 Uiso 1 1 calc R B 1 C34 C 0.1872(8) 0.1947(4) 0.7382(6) 0.077(2) Uani 1 1 d . B . H34 H 0.1417 0.1565 0.7776 0.092 Uiso 1 1 calc R . . C35 C 0.1293(6) 0.2031(4) 0.6299(6) 0.0683(18) Uani 1 1 d . . . H35 H 0.0455 0.1704 0.5940 0.082 Uiso 1 1 calc R B 1 C36A C 0.1955(6) 0.2604(3) 0.5735(5) 0.0532(14) Uani 0.571(5) 1 d P B 1 H36 H 0.1542 0.2679 0.4988 0.064 Uiso 0.571(5) 1 calc PR B 1 C36B C 0.1955(6) 0.2604(3) 0.5735(5) 0.0532(14) Uani 0.429(5) 1 d P B 2 F36 F 0.1377(8) 0.2638(5) 0.4785(5) 0.0633(12) Uani 0.429(5) 1 d P B 2 C37 C 0.3860(5) 0.3721(3) 0.5681(3) 0.0307(10) Uani 1 1 d . A . O37 O 0.5235(3) 0.3813(2) 0.5987(2) 0.0393(8) Uani 1 1 d . . . O38 O 0.3009(3) 0.4162(2) 0.4969(2) 0.0375(8) Uani 1 1 d . . . C41 C 0.5984(5) 0.3819(3) 0.2503(3) 0.0359(11) Uani 1 1 d . . . C42A C 0.7120(6) 0.3241(3) 0.2581(5) 0.0506(13) Uani 0.772(5) 1 d P C 1 F42 F 0.7905(4) 0.2957(3) 0.3488(3) 0.0665(12) Uani 0.772(5) 1 d P C 1 C42B C 0.7120(6) 0.3241(3) 0.2581(5) 0.0506(13) Uani 0.228(5) 1 d P C 2 H42 H 0.7701 0.3079 0.3270 0.061 Uiso 0.228(5) 1 calc PR C 2 C43 C 0.7436(6) 0.2890(4) 0.1674(5) 0.0624(16) Uani 1 1 d . . . H43 H 0.8210 0.2482 0.1741 0.075 Uiso 1 1 calc R C 1 C44 C 0.6623(7) 0.3138(4) 0.0689(5) 0.071(2) Uani 1 1 d . C . H44 H 0.6833 0.2902 0.0065 0.085 Uiso 1 1 calc R . . C45 C 0.5512(7) 0.3721(4) 0.0585(4) 0.0698(19) Uani 1 1 d . . . H45 H 0.4969 0.3898 -0.0108 0.084 Uiso 1 1 calc R C 1 C46A C 0.5174(6) 0.4053(4) 0.1473(4) 0.0500(14) Uani 0.772(5) 1 d P C 1 H46 H 0.4379 0.4448 0.1391 0.060 Uiso 0.772(5) 1 calc PR C 1 C46B C 0.5174(6) 0.4053(4) 0.1473(4) 0.0500(14) Uani 0.228(5) 1 d P C 2 F46 F 0.4233(16) 0.4583(10) 0.1261(11) 0.0665(12) Uani 0.228(5) 1 d P C 2 C47 C 0.5625(5) 0.4210(3) 0.3464(3) 0.0324(10) Uani 1 1 d . A . O47 O 0.6585(3) 0.4183(2) 0.4341(2) 0.0391(8) Uani 1 1 d . . . O48 O 0.4381(3) 0.4554(2) 0.3319(2) 0.0401(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0283(3) 0.0391(3) 0.0148(3) -0.0019(2) 0.00563(18) -0.0003(2) N11 0.0285(17) 0.041(2) 0.0212(19) 0.0005(16) 0.0061(15) 0.0010(14) C12A 0.037(2) 0.042(3) 0.028(2) 0.000(2) 0.013(2) -0.0002(19) N12 0.037(4) 0.074(6) 0.024(4) -0.001(4) 0.007(3) 0.001(4) C12B 0.037(2) 0.042(3) 0.028(2) 0.000(2) 0.013(2) -0.0002(19) C13 0.028(2) 0.057(4) 0.052(3) -0.009(3) 0.014(2) 0.004(2) C14 0.027(2) 0.056(3) 0.048(3) -0.005(3) -0.006(2) 0.001(2) C15 0.042(2) 0.040(3) 0.020(2) -0.001(2) -0.0002(18) 0.005(2) C16 0.027(2) 0.055(3) 0.019(2) -0.001(2) 0.0036(17) 0.0003(19) C21 0.045(2) 0.058(3) 0.026(2) 0.003(2) -0.005(2) 0.003(2) C31 0.045(2) 0.030(3) 0.037(3) -0.003(2) 0.021(2) 0.0018(19) C32A 0.069(3) 0.042(3) 0.040(3) 0.010(3) 0.032(3) 0.011(3) F32 0.073(3) 0.085(3) 0.031(2) -0.001(2) 0.014(2) -0.018(3) C32B 0.069(3) 0.042(3) 0.040(3) 0.010(3) 0.032(3) 0.011(3) C33 0.094(5) 0.060(4) 0.068(4) 0.023(3) 0.052(4) 0.016(4) C34 0.103(5) 0.051(4) 0.103(6) 0.021(4) 0.076(5) 0.012(4) C35 0.067(4) 0.042(4) 0.108(6) -0.015(4) 0.046(4) -0.015(3) C36A 0.060(3) 0.042(3) 0.066(4) -0.013(3) 0.033(3) -0.006(3) C36B 0.060(3) 0.042(3) 0.066(4) -0.013(3) 0.033(3) -0.006(3) F36 0.073(3) 0.085(3) 0.031(2) -0.001(2) 0.014(2) -0.018(3) C37 0.040(2) 0.033(3) 0.022(2) -0.006(2) 0.0132(19) 0.0021(19) O37 0.0360(16) 0.041(2) 0.041(2) 0.0089(16) 0.0108(14) 0.0016(14) O38 0.0384(16) 0.049(2) 0.0260(17) 0.0046(15) 0.0089(14) -0.0059(14) C41 0.043(2) 0.043(3) 0.027(2) -0.010(2) 0.018(2) -0.009(2) C42A 0.065(3) 0.047(3) 0.048(3) -0.009(3) 0.029(3) -0.004(3) F42 0.077(3) 0.080(3) 0.048(3) -0.002(2) 0.025(2) 0.027(2) C42B 0.065(3) 0.047(3) 0.048(3) -0.009(3) 0.029(3) -0.004(3) C43 0.069(4) 0.063(4) 0.071(4) -0.023(3) 0.048(3) -0.009(3) C44 0.092(5) 0.085(5) 0.052(4) -0.038(4) 0.048(4) -0.031(4) C45 0.086(4) 0.100(5) 0.029(3) -0.024(3) 0.026(3) -0.025(4) C46A 0.062(3) 0.064(4) 0.029(3) -0.017(3) 0.020(2) -0.020(3) C46B 0.062(3) 0.064(4) 0.029(3) -0.017(3) 0.020(2) -0.020(3) F46 0.077(3) 0.080(3) 0.048(3) -0.002(2) 0.025(2) 0.027(2) C47 0.041(2) 0.033(3) 0.026(2) -0.004(2) 0.015(2) -0.0080(19) O47 0.0372(16) 0.058(2) 0.0239(17) -0.0109(15) 0.0102(14) 0.0036(14) O48 0.0400(17) 0.056(2) 0.0235(17) -0.0084(15) 0.0075(13) 0.0078(14) _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 O37 1.945(3) . ? Cu1 O48 1.957(3) 3_666 ? Cu1 O47 1.963(3) . ? Cu1 O38 1.977(3) 3_666 ? Cu1 N11 2.162(3) . ? Cu1 Cu1 2.6439(10) 3_666 ? N11 C12A 1.331(5) . ? N11 C16 1.332(5) . ? C12A N12 1.325(8) . ? C12A C13 1.375(6) . ? N12 H12A 0.8800 . ? N12 H12B 0.8800 . ? C13 C14 1.363(6) . ? C13 H13 0.9500 . ? C14 C15 1.365(6) . ? C14 H14 0.9500 . ? C15 C16 1.373(6) . ? C15 C21 1.437(6) . ? C16 H16 0.9500 . ? C21 C21 1.185(9) 3_767 ? C31 C36A 1.377(7) . ? C31 C32A 1.401(7) . ? C31 C37 1.475(6) . ? C32A F32 1.247(7) . ? C32A C33 1.364(7) . ? C33 C34 1.336(9) . ? C33 H33 0.9500 . ? C34 C35 1.370(9) . ? C34 H34 0.9500 . ? C35 C36A 1.392(7) . ? C35 H35 0.9500 . ? C36A H36 0.9500 . ? C37 O37 1.253(5) . ? C37 O38 1.256(5) . ? O38 Cu1 1.976(3) 3_666 ? C41 C42A 1.376(7) . ? C41 C46A 1.401(7) . ? C41 C47 1.494(5) . ? C42A F42 1.291(6) . ? C42A C43 1.390(7) . ? C43 C44 1.361(8) . ? C43 H43 0.9500 . ? C44 C45 1.361(9) . ? C44 H44 0.9500 . ? C45 C46A 1.364(6) . ? C45 H45 0.9500 . ? C46A H46 0.9500 . ? C47 O48 1.251(5) . ? C47 O47 1.254(5) . ? O48 Cu1 1.957(3) 3_666 ? 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 O37 Cu1 O48 87.21(13) . 3_666 ? O37 Cu1 O47 91.16(13) . . ? O48 Cu1 O47 167.63(12) 3_666 . ? O37 Cu1 O38 167.79(12) . 3_666 ? O48 Cu1 O38 91.51(13) 3_666 3_666 ? O47 Cu1 O38 87.50(13) . 3_666 ? O37 Cu1 N11 98.00(13) . . ? O48 Cu1 N11 94.45(12) 3_666 . ? O47 Cu1 N11 97.92(12) . . ? O38 Cu1 N11 94.21(13) 3_666 . ? O37 Cu1 Cu1 83.51(9) . 3_666 ? O48 Cu1 Cu1 82.31(9) 3_666 3_666 ? O47 Cu1 Cu1 85.33(9) . 3_666 ? O38 Cu1 Cu1 84.28(9) 3_666 3_666 ? N11 Cu1 Cu1 176.37(10) . 3_666 ? C12A N11 C16 117.6(4) . . ? C12A N11 Cu1 123.1(3) . . ? C16 N11 Cu1 116.4(3) . . ? N12 C12A N11 121.6(5) . . ? N12 C12A C13 116.0(5) . . ? N11 C12A C13 122.1(4) . . ? C12A N12 H12A 120.0 . . ? C12A N12 H12B 120.0 . . ? H12A N12 H12B 120.0 . . ? C14 C13 C12A 119.4(4) . . ? C14 C13 H13 120.3 . . ? C12A C13 H13 120.3 . . ? C13 C14 C15 119.2(4) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C14 C15 C16 118.2(4) . . ? C14 C15 C21 121.8(4) . . ? C16 C15 C21 119.9(4) . . ? N11 C16 C15 123.3(4) . . ? N11 C16 H16 118.3 . . ? C15 C16 H16 118.3 . . ? C21 C21 C15 177.6(8) 3_767 . ? C36A C31 C32A 116.9(5) . . ? C36A C31 C37 122.7(4) . . ? C32A C31 C37 120.1(4) . . ? F32 C32A C33 116.3(6) . . ? F32 C32A C31 122.1(5) . . ? C33 C32A C31 121.2(6) . . ? C34 C33 C32A 120.5(6) . . ? C34 C33 H33 119.8 . . ? C32A C33 H33 119.8 . . ? C33 C34 C35 121.2(6) . . ? C33 C34 H34 119.4 . . ? C35 C34 H34 119.4 . . ? C34 C35 C36A 118.8(6) . . ? C34 C35 H35 120.6 . . ? C36A C35 H35 120.6 . . ? C31 C36A C35 121.4(6) . . ? C31 C36A H36 119.3 . . ? C35 C36A H36 119.3 . . ? O37 C37 O38 125.1(4) . . ? O37 C37 C31 116.8(4) . . ? O38 C37 C31 118.0(4) . . ? C37 O37 Cu1 124.4(3) . . ? C37 O38 Cu1 121.8(3) . 3_666 ? C42A C41 C46A 117.4(4) . . ? C42A C41 C47 122.5(4) . . ? C46A C41 C47 120.0(4) . . ? F42 C42A C41 122.7(5) . . ? F42 C42A C43 115.8(5) . . ? C41 C42A C43 121.4(6) . . ? C44 C43 C42A 119.1(6) . . ? C44 C43 H43 120.5 . . ? C42A C43 H43 120.5 . . ? C45 C44 C43 120.9(5) . . ? C45 C44 H44 119.6 . . ? C43 C44 H44 119.6 . . ? C44 C45 C46A 120.2(6) . . ? C44 C45 H45 119.9 . . ? C46A C45 H45 119.9 . . ? C45 C46A C41 120.9(6) . . ? C45 C46A H46 119.5 . . ? C41 C46A H46 119.5 . . ? O48 C47 O47 125.1(4) . . ? O48 C47 C41 116.6(4) . . ? O47 C47 C41 118.4(4) . . ? C47 O47 Cu1 121.5(3) . . ? C47 O48 Cu1 125.5(3) . 3_666 ? 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 O37 Cu1 N11 C12A 126.7(4) . . . . ? O48 Cu1 N11 C12A -145.5(4) 3_666 . . . ? O47 Cu1 N11 C12A 34.4(4) . . . . ? O38 Cu1 N11 C12A -53.6(4) 3_666 . . . ? Cu1 Cu1 N11 C12A -119.0(14) 3_666 . . . ? O37 Cu1 N11 C16 -73.0(3) . . . . ? O48 Cu1 N11 C16 14.8(3) 3_666 . . . ? O47 Cu1 N11 C16 -165.3(3) . . . . ? O38 Cu1 N11 C16 106.7(3) 3_666 . . . ? Cu1 Cu1 N11 C16 41.4(17) 3_666 . . . ? C16 N11 C12A N12 169.3(6) . . . . ? Cu1 N11 C12A N12 -30.6(7) . . . . ? C16 N11 C12A C13 -4.1(7) . . . . ? Cu1 N11 C12A C13 156.0(4) . . . . ? N12 C12A C13 C14 -170.1(6) . . . . ? N11 C12A C13 C14 3.5(8) . . . . ? C12A C13 C14 C15 -0.1(8) . . . . ? C13 C14 C15 C16 -2.5(8) . . . . ? C13 C14 C15 C21 -178.8(5) . . . . ? C12A N11 C16 C15 1.3(7) . . . . ? Cu1 N11 C16 C15 -160.1(4) . . . . ? C14 C15 C16 N11 2.0(7) . . . . ? C21 C15 C16 N11 178.4(5) . . . . ? C14 C15 C21 C21 106(17) . . . 3_767 ? C16 C15 C21 C21 -70(17) . . . 3_767 ? C36A C31 C32A F32 -174.1(5) . . . . ? C37 C31 C32A F32 0.5(7) . . . . ? C36A C31 C32A C33 -0.8(7) . . . . ? C37 C31 C32A C33 173.8(4) . . . . ? F32 C32A C33 C34 175.3(6) . . . . ? C31 C32A C33 C34 1.6(8) . . . . ? C32A C33 C34 C35 -0.6(9) . . . . ? C33 C34 C35 C36A -1.2(9) . . . . ? C32A C31 C36A C35 -1.0(7) . . . . ? C37 C31 C36A C35 -175.4(4) . . . . ? C34 C35 C36A C31 1.9(8) . . . . ? C36A C31 C37 O37 -148.1(4) . . . . ? C32A C31 C37 O37 37.6(6) . . . . ? C36A C31 C37 O38 34.2(6) . . . . ? C32A C31 C37 O38 -140.0(4) . . . . ? O38 C37 O37 Cu1 11.6(6) . . . . ? C31 C37 O37 Cu1 -165.9(3) . . . . ? O48 Cu1 O37 C37 76.9(3) 3_666 . . . ? O47 Cu1 O37 C37 -90.8(3) . . . . ? O38 Cu1 O37 C37 -7.3(8) 3_666 . . . ? N11 Cu1 O37 C37 171.0(3) . . . . ? Cu1 Cu1 O37 C37 -5.7(3) 3_666 . . . ? O37 C37 O38 Cu1 -10.8(6) . . . 3_666 ? C31 C37 O38 Cu1 166.6(3) . . . 3_666 ? C46A C41 C42A F42 -177.4(5) . . . . ? C47 C41 C42A F42 4.1(8) . . . . ? C46A C41 C42A C43 -1.2(7) . . . . ? C47 C41 C42A C43 -179.7(4) . . . . ? F42 C42A C43 C44 177.9(5) . . . . ? C41 C42A C43 C44 1.4(8) . . . . ? C42A C43 C44 C45 -0.1(9) . . . . ? C43 C44 C45 C46A -1.5(9) . . . . ? C44 C45 C46A C41 1.7(8) . . . . ? C42A C41 C46A C45 -0.4(7) . . . . ? C47 C41 C46A C45 178.1(5) . . . . ? C42A C41 C47 O48 -163.2(4) . . . . ? C46A C41 C47 O48 18.4(6) . . . . ? C42A C41 C47 O47 17.9(6) . . . . ? C46A C41 C47 O47 -160.5(4) . . . . ? O48 C47 O47 Cu1 -5.6(6) . . . . ? C41 C47 O47 Cu1 173.2(3) . . . . ? O37 Cu1 O47 C47 86.2(3) . . . . ? O48 Cu1 O47 C47 4.0(9) 3_666 . . . ? O38 Cu1 O47 C47 -81.7(3) 3_666 . . . ? N11 Cu1 O47 C47 -175.6(3) . . . . ? Cu1 Cu1 O47 C47 2.8(3) 3_666 . . . ? O47 C47 O48 Cu1 5.4(6) . . . 3_666 ? C41 C47 O48 Cu1 -173.4(3) . . . 3_666 ? 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 N12 H12B O38 0.88 2.43 3.295(8) 168.3 1_655 _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.703 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.121 #END data_13 _database_code_depnum_ccdc_archive 'CCDC 278021' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(2-NH2-5-pyridyl)-2-(3-pyridyl)-ethyne, (CH3COO)4Cu2 ; _chemical_name_common '1-(2-NH2-5-pyridyl)-2-(3-pyridyl)-ethyne, (CH3COO)4Cu2' _chemical_melting_point ? _chemical_formula_moiety ; (C12 H9 N3) Cu2 (C2 H3 O2)4 ; _chemical_formula_sum 'C20 H21 Cu2 N3 O8' _chemical_formula_weight 558.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1368(11) _cell_length_b 8.3062(11) _cell_length_c 8.7490(12) _cell_angle_alpha 86.244(3) _cell_angle_beta 80.480(3) _cell_angle_gamma 80.539(3) _cell_volume 574.79(13) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5375 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 30.00 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 1.900 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11035 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 30.08 _reflns_number_total 11035 _reflns_number_gt 9049 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11035 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1398 _refine_ls_wR_factor_gt 0.1354 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 0.42437(3) 0.45217(2) 0.13812(2) 0.01427(7) Uani 1 1 d . . . N11 N 0.29139(18) 0.38308(17) 0.36650(16) 0.0157(3) Uani 1 1 d . . . C12 C 0.2173(2) 0.2496(2) 0.37313(19) 0.0165(3) Uani 1 1 d . B . H12 H 0.2407 0.1833 0.2853 0.020 Uiso 1 1 calc R . . C13 C 0.1082(2) 0.2032(2) 0.5015(2) 0.0200(4) Uani 1 1 d . . . C14 C 0.0727(2) 0.3030(3) 0.6295(2) 0.0254(4) Uani 1 1 d . B . H14 H -0.0045 0.2779 0.7183 0.031 Uiso 1 1 calc R . . C15 C 0.1510(3) 0.4368(3) 0.6243(2) 0.0285(4) Uani 1 1 d . . . H15 H 0.1312 0.5038 0.7115 0.034 Uiso 1 1 calc R A 1 C16A C 0.2595(2) 0.4755(2) 0.4920(2) 0.0205(4) Uani 0.50 1 d P B 1 N16 N 0.3229(4) 0.6068(4) 0.5035(3) 0.0193(6) Uani 0.50 1 d P B 1 H16A H 0.3928 0.6416 0.4253 0.023 Uiso 0.50 1 calc PR B 1 H16B H 0.2961 0.6610 0.5895 0.023 Uiso 0.50 1 calc PR B 1 C16B C 0.2595(2) 0.4755(2) 0.4920(2) 0.0205(4) Uani 0.50 1 d P B 2 H16 H 0.3124 0.5696 0.4900 0.025 Uiso 0.50 1 calc PR B 2 C21 C 0.0324(2) 0.0599(2) 0.4998(2) 0.0269(4) Uani 1 1 d . . . C31 C 0.7765(2) 0.3332(2) 0.0546(2) 0.0171(3) Uani 1 1 d . B . O31 O 0.64950(16) 0.33078(15) 0.15945(14) 0.0198(3) Uani 1 1 d . . . O32 O 0.77700(17) 0.41370(17) -0.07237(15) 0.0248(3) Uani 1 1 d . . . C32 C 0.9408(2) 0.2308(2) 0.0824(2) 0.0238(4) Uani 1 1 d . . . H32A H 0.9270 0.1805 0.1873 0.036 Uiso 1 1 calc R B . H32B H 1.0288 0.3003 0.0716 0.036 Uiso 1 1 calc R . . H32C H 0.9733 0.1452 0.0064 0.036 Uiso 1 1 calc R . . C41 C 0.5659(2) 0.7507(2) 0.1153(2) 0.0176(3) Uani 1 1 d . B . O41 O 0.48989(18) 0.65158(16) 0.20408(15) 0.0242(3) Uani 1 1 d . . . O42 O 0.61706(17) 0.73278(16) -0.02751(15) 0.0217(3) Uani 1 1 d . . . C42 C 0.5945(3) 0.9030(2) 0.1839(2) 0.0242(4) Uani 1 1 d . . . H42A H 0.5762 0.8900 0.2973 0.036 Uiso 1 1 calc R B . H42B H 0.5154 0.9963 0.1519 0.036 Uiso 1 1 calc R . . H42C H 0.7104 0.9221 0.1474 0.036 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 0.01186(12) 0.01420(11) 0.01600(11) 0.00131(7) 0.00123(7) -0.00401(7) N11 0.0132(7) 0.0168(7) 0.0169(7) 0.0023(5) -0.0007(5) -0.0044(5) C12 0.0142(8) 0.0173(8) 0.0172(7) 0.0005(6) 0.0006(6) -0.0043(6) C13 0.0129(8) 0.0233(9) 0.0229(8) 0.0083(7) -0.0015(6) -0.0054(7) C14 0.0168(9) 0.0406(11) 0.0162(8) 0.0042(7) 0.0006(7) -0.0020(8) C15 0.0256(11) 0.0381(11) 0.0207(9) -0.0118(8) -0.0067(7) 0.0054(8) C16A 0.0175(9) 0.0184(8) 0.0268(9) -0.0020(7) -0.0082(7) -0.0017(7) N16 0.0204(16) 0.0206(15) 0.0178(13) -0.0006(11) 0.0012(11) -0.0100(12) C16B 0.0175(9) 0.0184(8) 0.0268(9) -0.0020(7) -0.0082(7) -0.0017(7) C21 0.0186(10) 0.0294(10) 0.0323(10) 0.0138(8) -0.0040(7) -0.0086(7) C31 0.0155(9) 0.0153(8) 0.0208(8) -0.0042(6) -0.0019(6) -0.0028(6) O31 0.0146(6) 0.0221(6) 0.0212(6) 0.0035(5) -0.0006(5) -0.0026(5) O32 0.0153(7) 0.0296(7) 0.0242(6) 0.0072(5) 0.0034(5) 0.0022(5) C32 0.0170(9) 0.0265(10) 0.0263(9) -0.0015(7) -0.0037(7) 0.0019(7) C41 0.0147(8) 0.0150(8) 0.0234(8) 0.0000(6) -0.0049(6) -0.0012(6) O41 0.0341(8) 0.0188(6) 0.0201(6) -0.0021(5) 0.0015(5) -0.0099(6) O42 0.0222(7) 0.0216(6) 0.0219(6) -0.0016(5) 0.0012(5) -0.0097(5) C42 0.0272(10) 0.0165(8) 0.0302(9) -0.0039(7) -0.0072(8) -0.0032(7) _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 O41 1.9692(14) . ? Cu1 O42 1.9706(13) 2_665 ? Cu1 O32 1.9709(13) 2_665 ? Cu1 O31 1.9719(13) . ? Cu1 N11 2.1981(14) . ? Cu1 Cu1 2.6595(5) 2_665 ? N11 C12 1.340(2) . ? N11 C16A 1.347(2) . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 C14 1.400(3) . ? C13 C21 1.430(3) . ? C14 C15 1.364(3) . ? C14 H14 0.9500 . ? C15 C16A 1.389(3) . ? C15 H15 0.9500 . ? C16A N16 1.297(3) . ? N16 H16A 0.8800 . ? N16 H16B 0.8800 . ? C21 C21 1.200(4) 2_556 ? C31 O32 1.258(2) . ? C31 O31 1.265(2) . ? C31 C32 1.509(2) . ? O32 Cu1 1.9709(13) 2_665 ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C41 O42 1.260(2) . ? C41 O41 1.261(2) . ? C41 C42 1.502(3) . ? O42 Cu1 1.9706(13) 2_665 ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? 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 O41 Cu1 O42 167.58(5) . 2_665 ? O41 Cu1 O32 89.06(6) . 2_665 ? O42 Cu1 O32 89.54(6) 2_665 2_665 ? O41 Cu1 O31 90.03(6) . . ? O42 Cu1 O31 88.73(6) 2_665 . ? O32 Cu1 O31 167.78(5) 2_665 . ? O41 Cu1 N11 95.98(6) . . ? O42 Cu1 N11 96.43(5) 2_665 . ? O32 Cu1 N11 94.38(5) 2_665 . ? O31 Cu1 N11 97.84(5) . . ? O41 Cu1 Cu1 82.83(4) . 2_665 ? O42 Cu1 Cu1 84.75(4) 2_665 2_665 ? O32 Cu1 Cu1 83.41(4) 2_665 2_665 ? O31 Cu1 Cu1 84.39(4) . 2_665 ? N11 Cu1 Cu1 177.49(4) . 2_665 ? C12 N11 C16A 118.05(15) . . ? C12 N11 Cu1 116.23(11) . . ? C16A N11 Cu1 125.03(12) . . ? N11 C12 C13 123.44(17) . . ? N11 C12 H12 118.3 . . ? C13 C12 H12 118.3 . . ? C12 C13 C14 117.82(17) . . ? C12 C13 C21 120.39(18) . . ? C14 C13 C21 121.77(17) . . ? C15 C14 C13 118.81(17) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C16A 120.21(18) . . ? C14 C15 H15 119.9 . . ? C16A C15 H15 119.9 . . ? N16 C16A N11 125.1(2) . . ? N16 C16A C15 113.2(2) . . ? N11 C16A C15 121.62(17) . . ? C16A N16 H16A 120.0 . . ? C16A N16 H16B 120.0 . . ? H16A N16 H16B 120.0 . . ? C21 C21 C13 179.2(3) 2_556 . ? O32 C31 O31 125.22(16) . . ? O32 C31 C32 116.93(15) . . ? O31 C31 C32 117.85(15) . . ? C31 O31 Cu1 122.80(11) . . ? C31 O32 Cu1 124.15(12) . 2_665 ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O42 C41 O41 124.74(17) . . ? O42 C41 C42 117.61(16) . . ? O41 C41 C42 117.64(16) . . ? C41 O41 Cu1 124.99(12) . . ? C41 O42 Cu1 122.63(12) . 2_665 ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? 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 O41 Cu1 N11 C12 177.47(12) . . . . ? O42 Cu1 N11 C12 -2.07(13) 2_665 . . . ? O32 Cu1 N11 C12 87.95(12) 2_665 . . . ? O31 Cu1 N11 C12 -91.68(12) . . . . ? Cu1 Cu1 N11 C12 115.9(9) 2_665 . . . ? O41 Cu1 N11 C16A 7.20(14) . . . . ? O42 Cu1 N11 C16A -172.34(14) 2_665 . . . ? O32 Cu1 N11 C16A -82.32(14) 2_665 . . . ? O31 Cu1 N11 C16A 98.05(14) . . . . ? Cu1 Cu1 N11 C16A -54.4(10) 2_665 . . . ? C16A N11 C12 C13 0.8(2) . . . . ? Cu1 N11 C12 C13 -170.17(13) . . . . ? N11 C12 C13 C14 0.9(3) . . . . ? N11 C12 C13 C21 179.38(16) . . . . ? C12 C13 C14 C15 -2.3(3) . . . . ? C21 C13 C14 C15 179.21(17) . . . . ? C13 C14 C15 C16A 2.1(3) . . . . ? C12 N11 C16A N16 179.3(2) . . . . ? Cu1 N11 C16A N16 -10.6(3) . . . . ? C12 N11 C16A C15 -1.1(3) . . . . ? Cu1 N11 C16A C15 169.04(13) . . . . ? C14 C15 C16A N16 179.3(2) . . . . ? C14 C15 C16A N11 -0.4(3) . . . . ? C12 C13 C21 C21 -176(100) . . . 2_556 ? C14 C13 C21 C21 2(20) . . . 2_556 ? O32 C31 O31 Cu1 1.5(3) . . . . ? C32 C31 O31 Cu1 -178.03(12) . . . . ? O41 Cu1 O31 C31 -82.92(14) . . . . ? O42 Cu1 O31 C31 84.72(14) 2_665 . . . ? O32 Cu1 O31 C31 2.8(3) 2_665 . . . ? N11 Cu1 O31 C31 -178.97(13) . . . . ? Cu1 Cu1 O31 C31 -0.13(13) 2_665 . . . ? O31 C31 O32 Cu1 -2.4(3) . . . 2_665 ? C32 C31 O32 Cu1 177.13(12) . . . 2_665 ? O42 C41 O41 Cu1 -3.1(3) . . . . ? C42 C41 O41 Cu1 175.58(12) . . . . ? O42 Cu1 O41 C41 1.6(3) 2_665 . . . ? O32 Cu1 O41 C41 -82.02(15) 2_665 . . . ? O31 Cu1 O41 C41 85.79(15) . . . . ? N11 Cu1 O41 C41 -176.32(15) . . . . ? Cu1 Cu1 O41 C41 1.45(14) 2_665 . . . ? O41 C41 O42 Cu1 3.0(3) . . . 2_665 ? C42 C41 O42 Cu1 -175.68(11) . . . 2_665 ? 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 N16 H16B O31 0.88 2.32 3.078(3) 144.5 2_666 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 30.08 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.186 _refine_diff_density_min -0.576 _refine_diff_density_rms 0.101 #END