# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Juan C. Noveron' _publ_contact_author_address ; Chemistry University of Texas at El Paso 500 W. University Ave. El Paso Texas 79968-0513 UNITED STATES OF AMERICA ; _publ_contact_author_email JCNOVERON@UTEP.EDU _publ_section_title ; A novel class of metal-directed supramolecular DNA-delivery systems ; loop_ _publ_author_name 'Juan Noveron' 'Renato J. Aguilera' 'Alejandro Arzola' 'Itzia Cruz-Campa' 'Jason G. Parsons' ; L.Santiago ; 'Armando Varela-Ramirez' data_Cu_complex_3 _database_code_depnum_ccdc_archive 'CCDC 638805' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H30 Cu N6,2(C F3 O3 S),H2 O' _chemical_formula_sum 'C14 H32 Cu F6 N6 O7 S2' _chemical_formula_weight 638.12 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' S S 0.1246 0.1234 '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 Trigonal _symmetry_space_group_name_H-M 'P31 2 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'x-y, -y, -z+2/3' '-x, -x+y, -z+1/3' 'y, x, -z' _cell_length_a 9.4428(2) _cell_length_b 9.4428(2) _cell_length_c 24.7664(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1912.47(8) _cell_formula_units_Z 3 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 2725 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 987 _exptl_absorpt_coefficient_mu 1.110 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7108 _exptl_absorpt_correction_T_max 0.8691 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; The program Denzo-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL-97 input file. ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD Diffractometer' _diffrn_measurement_method 'Phi and Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5097 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2922 _reflns_number_gt 2726 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX, Ortep3' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0304P)^2^+0.8643P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.024(14) _refine_ls_number_reflns 2922 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 -0.05751(4) -0.05751(4) 0.5000 0.01749(10) Uani 1 2 d S . . S1 S -0.45633(8) 0.33894(8) 0.41194(2) 0.02602(14) Uani 1 1 d . . . F1 F -0.4068(4) 0.2144(3) 0.32528(9) 0.0827(8) Uani 1 1 d . . . F2 F -0.2090(3) 0.4470(5) 0.34651(9) 0.1065(11) Uani 1 1 d . . . F3 F -0.4258(3) 0.4250(3) 0.31061(8) 0.0627(6) Uani 1 1 d . . . O1 O -0.6287(2) 0.2338(3) 0.40154(8) 0.0415(5) Uani 1 1 d . . . O2 O -0.3817(4) 0.2693(4) 0.44396(9) 0.0617(7) Uani 1 1 d . . . O3 O -0.4138(3) 0.5020(3) 0.42636(10) 0.0459(5) Uani 1 1 d . . . O4 O -0.8635(3) 0.0000 0.3333 0.0344(6) Uani 1 2 d S . . H4 H -0.774(4) 0.070(4) 0.3483(14) 0.046(10) Uiso 1 1 d . . . N1 N -0.1006(2) 0.0101(2) 0.41309(7) 0.0234(4) Uani 1 1 d . . . H1 H -0.0409 -0.0111 0.3877 0.028 Uiso 1 1 calc R . . N2 N -0.0076(3) 0.1806(2) 0.51182(9) 0.0242(4) Uani 1 1 d . . . H2 H 0.0728 0.2283 0.5382 0.029 Uiso 1 1 calc R . . N3 N -0.2960(2) -0.1125(3) 0.50835(9) 0.0247(4) Uani 1 1 d . . . H3 H -0.3567 -0.2172 0.5226 0.030 Uiso 1 1 calc R . . C1 C -0.0517(3) 0.1846(3) 0.41323(11) 0.0283(6) Uani 1 1 d . . . H1A H -0.1506 0.1954 0.4146 0.034 Uiso 1 1 calc R . . H1B H 0.0074 0.2360 0.3794 0.034 Uiso 1 1 calc R . . C2 C 0.0576(3) 0.2734(3) 0.46126(11) 0.0272(6) Uani 1 1 d . . . H2A H 0.1685 0.2903 0.4546 0.033 Uiso 1 1 calc R . . H2B H 0.0672 0.3822 0.4651 0.033 Uiso 1 1 calc R . . C3 C -0.1575(3) 0.1791(3) 0.53180(11) 0.0286(6) Uani 1 1 d . . . H3A H -0.2023 0.2177 0.5029 0.034 Uiso 1 1 calc R . . H3B H -0.1289 0.2545 0.5629 0.034 Uiso 1 1 calc R . . C4 C -0.2861(3) 0.0071(4) 0.54900(11) 0.0298(6) Uani 1 1 d . . . H4A H -0.2568 -0.0185 0.5846 0.036 Uiso 1 1 calc R . . H4B H -0.3938 0.0004 0.5524 0.036 Uiso 1 1 calc R . . C5 C -0.3727(3) -0.1048(3) 0.45661(10) 0.0287(6) Uani 1 1 d . . . H5A H -0.3812 -0.0045 0.4564 0.034 Uiso 1 1 calc R . . H5B H -0.4849 -0.1999 0.4546 0.034 Uiso 1 1 calc R . . C6 C -0.2770(3) -0.1043(3) 0.40688(10) 0.0288(6) Uani 1 1 d . . . H6A H -0.2955 -0.2160 0.4008 0.035 Uiso 1 1 calc R . . H6B H -0.3177 -0.0730 0.3748 0.035 Uiso 1 1 calc R . . C7 C -0.3676(4) 0.3612(4) 0.34504(12) 0.0442(7) 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 0.01697(14) 0.01697(14) 0.01991(17) 0.00062(8) -0.00062(8) 0.00953(16) S1 0.0253(3) 0.0254(3) 0.0277(3) 0.0020(3) -0.0008(2) 0.0129(2) F1 0.115(2) 0.107(2) 0.0641(13) -0.0202(13) 0.0110(14) 0.0836(19) F2 0.0300(10) 0.194(3) 0.0593(13) 0.0043(19) 0.0099(10) 0.0287(16) F3 0.0659(14) 0.0805(15) 0.0389(10) 0.0216(10) -0.0007(9) 0.0344(13) O1 0.0281(10) 0.0372(11) 0.0380(11) -0.0053(10) 0.0044(8) 0.0004(9) O2 0.0866(19) 0.0879(19) 0.0446(12) 0.0152(13) -0.0036(13) 0.0693(16) O3 0.0467(13) 0.0290(11) 0.0562(13) -0.0128(10) -0.0140(11) 0.0146(10) O4 0.0297(10) 0.0430(16) 0.0349(14) -0.0126(12) -0.0063(6) 0.0215(8) N1 0.0257(10) 0.0240(11) 0.0222(9) 0.0009(9) 0.0017(8) 0.0138(9) N2 0.0261(11) 0.0235(10) 0.0259(10) -0.0002(9) -0.0011(9) 0.0147(9) N3 0.0189(9) 0.0266(11) 0.0278(10) 0.0057(9) 0.0035(8) 0.0108(9) C1 0.0352(15) 0.0249(13) 0.0278(13) 0.0095(10) 0.0043(11) 0.0173(12) C2 0.0304(13) 0.0181(11) 0.0321(13) 0.0038(10) 0.0027(11) 0.0114(10) C3 0.0354(15) 0.0328(14) 0.0282(12) -0.0031(11) -0.0012(11) 0.0250(12) C4 0.0307(13) 0.0431(15) 0.0259(12) 0.0022(12) 0.0035(11) 0.0263(12) C5 0.0198(11) 0.0341(14) 0.0303(13) 0.0042(11) -0.0042(10) 0.0122(11) C6 0.0281(12) 0.0307(14) 0.0238(12) 0.0010(11) -0.0059(10) 0.0119(11) C7 0.0336(15) 0.067(2) 0.0363(14) 0.0042(14) 0.0014(12) 0.0286(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 2.053(2) 6_556 ? Cu1 N3 2.053(2) . ? Cu1 N2 2.075(2) . ? Cu1 N2 2.075(2) 6_556 ? Cu1 N1 2.3377(19) . ? Cu1 N1 2.3378(19) 6_556 ? S1 O2 1.422(2) . ? S1 O3 1.428(2) . ? S1 O1 1.444(2) . ? S1 C7 1.821(3) . ? F1 C7 1.336(4) . ? F2 C7 1.299(4) . ? F3 C7 1.312(4) . ? O4 H4 0.86(3) . ? N1 C6 1.471(3) . ? N1 C1 1.473(3) . ? N1 H1 0.9300 . ? N2 C2 1.475(3) . ? N2 C3 1.492(3) . ? N2 H2 0.9300 . ? N3 C4 1.481(3) . ? N3 C5 1.491(3) . ? N3 H3 0.9300 . ? C1 C2 1.523(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.524(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.526(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N3 95.10(12) 6_556 . ? N3 Cu1 N2 177.36(9) 6_556 . ? N3 Cu1 N2 83.45(8) . . ? N3 Cu1 N2 83.45(8) 6_556 6_556 ? N3 Cu1 N2 177.36(9) . 6_556 ? N2 Cu1 N2 98.08(12) . 6_556 ? N3 Cu1 N1 102.92(8) 6_556 . ? N3 Cu1 N1 80.98(8) . . ? N2 Cu1 N1 79.06(8) . . ? N2 Cu1 N1 97.18(8) 6_556 . ? N3 Cu1 N1 80.97(8) 6_556 6_556 ? N3 Cu1 N1 102.92(8) . 6_556 ? N2 Cu1 N1 97.18(8) . 6_556 ? N2 Cu1 N1 79.06(8) 6_556 6_556 ? N1 Cu1 N1 174.33(10) . 6_556 ? O2 S1 O3 114.96(16) . . ? O2 S1 O1 115.50(17) . . ? O3 S1 O1 113.47(14) . . ? O2 S1 C7 104.77(14) . . ? O3 S1 C7 103.75(16) . . ? O1 S1 C7 102.27(13) . . ? C6 N1 C1 115.4(2) . . ? C6 N1 Cu1 100.58(14) . . ? C1 N1 Cu1 107.66(14) . . ? C6 N1 H1 110.9 . . ? C1 N1 H1 110.9 . . ? Cu1 N1 H1 110.9 . . ? C2 N2 C3 113.6(2) . . ? C2 N2 Cu1 108.98(15) . . ? C3 N2 Cu1 109.61(15) . . ? C2 N2 H2 108.2 . . ? C3 N2 H2 108.2 . . ? Cu1 N2 H2 108.2 . . ? C4 N3 C5 113.2(2) . . ? C4 N3 Cu1 103.47(15) . . ? C5 N3 Cu1 113.51(15) . . ? C4 N3 H3 108.8 . . ? C5 N3 H3 108.8 . . ? Cu1 N3 H3 108.8 . . ? N1 C1 C2 111.41(19) . . ? N1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? N1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? N2 C2 C1 111.7(2) . . ? N2 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N2 C3 C4 110.5(2) . . ? N2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? N2 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? N3 C4 C3 109.6(2) . . ? N3 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? N3 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? N3 C5 C6 113.1(2) . . ? N3 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? N3 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? N1 C6 C5 111.6(2) . . ? N1 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N1 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? F2 C7 F3 110.4(3) . . ? F2 C7 F1 107.0(3) . . ? F3 C7 F1 106.0(3) . . ? F2 C7 S1 111.5(2) . . ? F3 C7 S1 111.7(2) . . ? F1 C7 S1 109.9(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 N3 Cu1 N1 C6 63.36(15) 6_556 . . . ? N3 Cu1 N1 C6 -29.84(15) . . . . ? N2 Cu1 N1 C6 -114.86(15) . . . . ? N2 Cu1 N1 C6 148.25(15) 6_556 . . . ? N1 Cu1 N1 C6 -163.65(14) 6_556 . . . ? N3 Cu1 N1 C1 -175.51(15) 6_556 . . . ? N3 Cu1 N1 C1 91.29(16) . . . . ? N2 Cu1 N1 C1 6.27(15) . . . . ? N2 Cu1 N1 C1 -90.62(16) 6_556 . . . ? N1 Cu1 N1 C1 -42.52(14) 6_556 . . . ? N3 Cu1 N2 C2 -168.9(19) 6_556 . . . ? N3 Cu1 N2 C2 -112.03(17) . . . . ? N2 Cu1 N2 C2 65.80(15) 6_556 . . . ? N1 Cu1 N2 C2 -30.00(16) . . . . ? N1 Cu1 N2 C2 145.71(16) 6_556 . . . ? N3 Cu1 N2 C3 -44(2) 6_556 . . . ? N3 Cu1 N2 C3 12.81(16) . . . . ? N2 Cu1 N2 C3 -169.4(2) 6_556 . . . ? N1 Cu1 N2 C3 94.84(17) . . . . ? N1 Cu1 N2 C3 -89.46(16) 6_556 . . . ? N3 Cu1 N3 C4 142.59(18) 6_556 . . . ? N2 Cu1 N3 C4 -35.19(15) . . . . ? N2 Cu1 N3 C4 -161(2) 6_556 . . . ? N1 Cu1 N3 C4 -115.10(16) . . . . ? N1 Cu1 N3 C4 60.70(16) 6_556 . . . ? N3 Cu1 N3 C5 -94.33(18) 6_556 . . . ? N2 Cu1 N3 C5 87.89(19) . . . . ? N2 Cu1 N3 C5 -38(2) 6_556 . . . ? N1 Cu1 N3 C5 7.98(17) . . . . ? N1 Cu1 N3 C5 -176.21(17) 6_556 . . . ? C6 N1 C1 C2 129.6(2) . . . . ? Cu1 N1 C1 C2 18.3(2) . . . . ? C3 N2 C2 C1 -71.3(3) . . . . ? Cu1 N2 C2 C1 51.1(2) . . . . ? N1 C1 C2 N2 -45.9(3) . . . . ? C2 N2 C3 C4 134.7(2) . . . . ? Cu1 N2 C3 C4 12.6(2) . . . . ? C5 N3 C4 C3 -71.4(2) . . . . ? Cu1 N3 C4 C3 51.9(2) . . . . ? N2 C3 C4 N3 -43.7(3) . . . . ? C4 N3 C5 C6 133.4(2) . . . . ? Cu1 N3 C5 C6 15.8(3) . . . . ? C1 N1 C6 C5 -68.9(3) . . . . ? Cu1 N1 C6 C5 46.6(2) . . . . ? N3 C5 C6 N1 -45.7(3) . . . . ? O2 S1 C7 F2 -55.9(3) . . . . ? O3 S1 C7 F2 65.0(3) . . . . ? O1 S1 C7 F2 -176.8(3) . . . . ? O2 S1 C7 F3 180.0(3) . . . . ? O3 S1 C7 F3 -59.1(3) . . . . ? O1 S1 C7 F3 59.1(3) . . . . ? O2 S1 C7 F1 62.6(3) . . . . ? O3 S1 C7 F1 -176.5(2) . . . . ? O1 S1 C7 F1 -58.2(2) . . . . ? 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 O4 H4 O1 0.86(3) 1.97(3) 2.784(2) 158(3) . N1 H1 O4 0.93 2.11 3.023(3) 166.3 1_655 N2 H2 O1 0.93 2.08 2.990(3) 167.3 6_566 N3 H3 O3 0.93 2.08 2.987(3) 163.2 6_456 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.387 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.059