# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name J.P.Coyle A.Kurek P.J.Pallister E.R.Sirianni G.P.A.Yap S.T.Barry _publ_contact_author_name 'Glenn P. A. Yap' _publ_contact_author_email gpyap@UDel.Edu data_seab057 _database_code_depnum_ccdc_archive 'CCDC 893889' #TrackingRef '- compound_1_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H38 Cu2 N4' _chemical_formula_weight 461.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 10.202(2) _cell_length_b 9.535(2) _cell_length_c 11.980(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.648(3) _cell_angle_gamma 90.00 _cell_volume 1110.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 956 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.98 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 1.926 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4590 _exptl_absorpt_correction_T_max 0.7293 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; Data collection is performed with four batch runs at \f = 0.00 \% (600 frames), at \f = 90.00 \% (600 frames), at \f = 180 \% (600 frames) and at \f = 270 \% (600 frames). Frame width = 0.30 \& in \w. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. ; _diffrn_ambient_temperature 200(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 AXS APEX diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 1 _diffrn_reflns_number 14501 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.32 _reflns_number_total 2757 _reflns_number_gt 2490 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2001)' _computing_publication_material 'SHELXTL (Sheldrick, 2001)' _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^)+(0.0545P)^2^+0.2574P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2757 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0860 _refine_ls_wR_factor_gt 0.0830 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Cu Cu 0.878593(19) 0.02862(2) 0.489253(17) 0.02631(10) Uani 1 1 d . . . N1 N 1.04879(14) -0.18341(14) 0.41692(12) 0.0281(3) Uani 1 1 d . . . N2 N 0.81903(14) -0.13073(15) 0.39402(12) 0.0279(3) Uani 1 1 d . . . C1 C 1.13406(18) -0.28623(17) 0.37703(15) 0.0308(3) Uani 1 1 d . . . C2 C 1.0365(2) -0.4091(2) 0.3328(2) 0.0482(5) Uani 1 1 d . . . H2A H 1.0424 -0.4778 0.3961 0.058 Uiso 1 1 calc R . . H2B H 1.0570 -0.4572 0.2668 0.058 Uiso 1 1 calc R . . C3 C 0.8946(2) -0.3391(2) 0.29270(18) 0.0423(4) Uani 1 1 d . . . H3A H 0.8692 -0.3119 0.2091 0.051 Uiso 1 1 calc R . . H3B H 0.8227 -0.4018 0.3048 0.051 Uiso 1 1 calc R . . C4 C 0.91513(17) -0.21028(16) 0.37199(13) 0.0269(3) Uani 1 1 d . . . C5 C 1.1835(2) -0.2235(2) 0.28051(19) 0.0457(5) Uani 1 1 d . . . H5A H 1.1045 -0.2071 0.2110 0.068 Uiso 1 1 calc R . . H5B H 1.2475 -0.2886 0.2609 0.068 Uiso 1 1 calc R . . H5C H 1.2303 -0.1344 0.3073 0.068 Uiso 1 1 calc R . . C6 C 1.2593(2) -0.3285(2) 0.47933(18) 0.0480(5) Uani 1 1 d . . . H6A H 1.2285 -0.3639 0.5440 0.072 Uiso 1 1 calc R . . H6B H 1.3187 -0.2467 0.5058 0.072 Uiso 1 1 calc R . . H6C H 1.3108 -0.4020 0.4536 0.072 Uiso 1 1 calc R . . C8 C 0.66996(17) -0.16555(19) 0.35011(15) 0.0327(4) Uani 1 1 d . . . C9 C 0.6147(2) -0.1722(3) 0.21601(18) 0.0524(5) Uani 1 1 d . . . H9A H 0.6425 -0.0875 0.1826 0.079 Uiso 1 1 calc R . . H9B H 0.5141 -0.1782 0.1917 0.079 Uiso 1 1 calc R . . H9C H 0.6522 -0.2550 0.1881 0.079 Uiso 1 1 calc R . . C10 C 0.6367(2) -0.3016(2) 0.4036(2) 0.0520(5) Uani 1 1 d . . . H10A H 0.6809 -0.3003 0.4885 0.078 Uiso 1 1 calc R . . H10B H 0.6710 -0.3817 0.3694 0.078 Uiso 1 1 calc R . . H10C H 0.5369 -0.3100 0.3871 0.078 Uiso 1 1 calc R . . C11 C 0.5954(2) -0.0459(3) 0.3897(3) 0.0574(7) Uani 1 1 d . . . H11A H 0.6094 0.0413 0.3516 0.086 Uiso 1 1 calc R . . H11B H 0.6320 -0.0352 0.4749 0.086 Uiso 1 1 calc R . . H11C H 0.4969 -0.0669 0.3681 0.086 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 Cu 0.02519(14) 0.02513(14) 0.02687(14) -0.00677(7) 0.00527(9) 0.00078(7) N1 0.0304(7) 0.0241(6) 0.0294(6) -0.0071(5) 0.0082(5) 0.0018(5) N2 0.0264(7) 0.0277(7) 0.0276(6) -0.0061(5) 0.0053(5) -0.0025(5) C1 0.0360(9) 0.0257(8) 0.0326(8) -0.0051(6) 0.0134(7) 0.0038(7) C2 0.0538(12) 0.0340(10) 0.0609(13) -0.0182(9) 0.0235(10) -0.0027(9) C3 0.0465(11) 0.0352(10) 0.0440(10) -0.0190(8) 0.0121(8) -0.0067(8) C4 0.0336(8) 0.0238(7) 0.0232(7) -0.0034(6) 0.0084(6) -0.0019(6) C5 0.0543(12) 0.0431(11) 0.0479(11) 0.0056(9) 0.0279(10) 0.0122(9) C6 0.0551(12) 0.0448(11) 0.0407(10) -0.0011(9) 0.0096(9) 0.0197(10) C8 0.0282(8) 0.0345(9) 0.0334(8) -0.0050(7) 0.0061(7) -0.0051(7) C9 0.0459(11) 0.0659(15) 0.0361(10) -0.0001(10) -0.0017(9) -0.0072(11) C10 0.0490(12) 0.0548(13) 0.0561(13) 0.0054(10) 0.0218(10) -0.0130(10) C11 0.0294(10) 0.0552(14) 0.0851(19) -0.0265(12) 0.0135(11) -0.0021(9) _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 Cu N1 1.8671(14) 3_756 ? Cu N2 1.8867(14) . ? Cu Cu 2.4728(7) 3_756 ? N1 C4 1.330(2) . ? N1 C1 1.483(2) . ? N1 Cu 1.8670(14) 3_756 ? N2 C4 1.328(2) . ? N2 C8 1.488(2) . ? C1 C5 1.517(3) . ? C1 C2 1.525(3) . ? C1 C6 1.532(3) . ? C2 C3 1.533(3) . ? C3 C4 1.528(2) . ? C8 C11 1.524(3) . ? C8 C10 1.530(3) . ? C8 C9 1.534(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu N2 175.59(6) 3_756 . ? N1 Cu Cu 84.82(4) 3_756 3_756 ? N2 Cu Cu 90.80(4) . 3_756 ? C4 N1 C1 111.84(13) . . ? C4 N1 Cu 124.53(11) . 3_756 ? C1 N1 Cu 123.52(11) . 3_756 ? C4 N2 C8 122.64(14) . . ? C4 N2 Cu 117.28(11) . . ? C8 N2 Cu 120.04(11) . . ? N1 C1 C5 110.38(15) . . ? N1 C1 C2 103.60(14) . . ? C5 C1 C2 111.74(17) . . ? N1 C1 C6 110.16(14) . . ? C5 C1 C6 108.91(17) . . ? C2 C1 C6 111.98(17) . . ? C1 C2 C3 103.28(15) . . ? C4 C3 C2 102.50(15) . . ? N2 C4 N1 122.53(14) . . ? N2 C4 C3 127.75(15) . . ? N1 C4 C3 109.70(14) . . ? N2 C8 C11 106.02(15) . . ? N2 C8 C10 111.95(16) . . ? C11 C8 C10 108.03(18) . . ? N2 C8 C9 113.01(15) . . ? C11 C8 C9 107.28(19) . . ? C10 C8 C9 110.24(17) . . ? 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 N1 Cu N2 C4 6.7(9) 3_756 . . . ? Cu Cu N2 C4 -0.49(12) 3_756 . . . ? N1 Cu N2 C8 -175.3(7) 3_756 . . . ? Cu Cu N2 C8 177.51(12) 3_756 . . . ? C4 N1 C1 C5 101.58(18) . . . . ? Cu N1 C1 C5 -74.58(18) 3_756 . . . ? C4 N1 C1 C2 -18.2(2) . . . . ? Cu N1 C1 C2 165.66(13) 3_756 . . . ? C4 N1 C1 C6 -138.11(17) . . . . ? Cu N1 C1 C6 45.7(2) 3_756 . . . ? N1 C1 C2 C3 28.5(2) . . . . ? C5 C1 C2 C3 -90.35(19) . . . . ? C6 C1 C2 C3 147.16(17) . . . . ? C1 C2 C3 C4 -28.4(2) . . . . ? C8 N2 C4 N1 -176.00(15) . . . . ? Cu N2 C4 N1 1.9(2) . . . . ? C8 N2 C4 C3 5.8(3) . . . . ? Cu N2 C4 C3 -176.26(14) . . . . ? C1 N1 C4 N2 -178.92(14) . . . . ? Cu N1 C4 N2 -2.8(2) 3_756 . . . ? C1 N1 C4 C3 -0.4(2) . . . . ? Cu N1 C4 C3 175.70(12) 3_756 . . . ? C2 C3 C4 N2 -162.95(18) . . . . ? C2 C3 C4 N1 18.7(2) . . . . ? C4 N2 C8 C11 -177.58(18) . . . . ? Cu N2 C8 C11 4.5(2) . . . . ? C4 N2 C8 C10 64.9(2) . . . . ? Cu N2 C8 C10 -113.04(16) . . . . ? C4 N2 C8 C9 -60.3(2) . . . . ? Cu N2 C8 C9 121.77(16) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.712 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.079