Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address "Bertrand, H\'el\`ene" ;Institut Curie, Section Recherche Centre Universitaire Paris XI B\^at. 110, 91405 Orsay France ; 'De Cian, Anne' ;Laboratoire de Biophysique Mus\'eum National d?Histoire Naturelle 43 Rue Cuvier 75005 Paris France. ; "Guillot, R\'egis" ;Institut de Chimie Mol\'eculaire et des Mat\'eriaux d?Orsay Universit\'e Paris Sud XI B\^at. 420 91405 Orsay France ; 'Teulade-Fichou, Marie-Paule' ;Institut Curie, Section Recherche Centre Universitaire Paris XI B\^at. 110, 91405 Orsay France ; 'Monchaud, David' ;Institut Curie, Section Recherche Centre Universitaire Paris XI B\^at. 110, 91405 Orsay France ; _publ_contact_author_address ;Institut Curie, Section Recherche Centre Universitaire Paris XI B\^at. 110, 91405 Orsay France ; _publ_contact_author_email marie-paule.teulade-fichou@curie.fr _publ_contact_author_fax '+33 1 6907 5381' _publ_contact_author_phone '+33 1 6986 3086' _publ_contact_author_name 'Marie-Paule Teulade-Fichou' _publ_section_title ;The importance of the metal geometry in the recognition of G-quadruplex-DNA by metal-terpyridine complexes ; data_627GuillotICMMO _database_code_depnum_ccdc_archive 'CCDC 649829' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H17 Cu N5 O6' _chemical_formula_sum 'C22 H17 Cu N5 O6' _chemical_formula_weight 510.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0031 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' Cu Cu 0.3221 1.2697 '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 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc ' 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 12.996(2) _cell_length_b 9.9631(15) _cell_length_c 17.8565(18) _cell_angle_alpha 90.00 _cell_angle_beta 116.763(8) _cell_angle_gamma 90.00 _cell_volume 2064.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 5798 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 33.06 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.310 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044 _exptl_absorpt_coefficient_mu 1.112 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.90 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'kapa X8 APEX II Bruker ICMMO' _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 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 30472 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 34.90 _reflns_number_total 8376 _reflns_number_gt 7202 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0000P)^2^+26.2672P] 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 8376 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0733 _refine_ls_wR_factor_ref 0.2111 _refine_ls_wR_factor_gt 0.2070 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 Cu2 Cu 0.32899(6) 0.75877(7) 0.36642(4) 0.02148(16) Uani 1 1 d . . . O1 O 0.5388(4) 0.8618(5) 0.4668(3) 0.0264(8) Uani 1 1 d . . . O2 O 0.4130(4) 0.9009(5) 0.3378(2) 0.0235(8) Uani 1 1 d . . . O3 O 0.5675(4) 1.0223(5) 0.3964(3) 0.0327(10) Uani 1 1 d . . . N1 N 0.4067(4) 0.5885(5) 0.3577(2) 0.0176(8) Uani 1 1 d . . . N2 N 0.2894(4) 0.6369(5) 0.4335(3) 0.0211(9) Uani 1 1 d . . . N3 N 0.2430(4) 0.8857(5) 0.4049(4) 0.0254(10) Uani 1 1 d . . . N5 N 0.5091(4) 0.9291(5) 0.4024(3) 0.0189(8) Uani 1 1 d . . . C1 C 0.4692(5) 0.5734(6) 0.3142(3) 0.0248(11) Uani 1 1 d . . . H1 H 0.4781 0.6471 0.2856 0.030 Uiso 1 1 calc R . . C2 C 0.5201(6) 0.4530(7) 0.3106(4) 0.0293(12) Uani 1 1 d . . . H2 H 0.5633 0.4464 0.2811 0.035 Uiso 1 1 calc R . . C3 C 0.5053(5) 0.3433(6) 0.3517(3) 0.0259(11) Uani 1 1 d . . . H3 H 0.5388 0.2614 0.3503 0.031 Uiso 1 1 calc R . . C5 C 0.3930(4) 0.4798(6) 0.3970(3) 0.0189(9) Uani 1 1 d . . . C4 C 0.4396(5) 0.3556(6) 0.3954(3) 0.0244(11) Uani 1 1 d . . . H4 H 0.4275 0.2823 0.4227 0.029 Uiso 1 1 calc R . . C6 C 0.3241(4) 0.5083(6) 0.4419(3) 0.0202(9) Uani 1 1 d . . . C7 C 0.2951(4) 0.4197(5) 0.4893(3) 0.0189(9) Uani 1 1 d . . . H7 H 0.3181 0.3304 0.4943 0.023 Uiso 1 1 calc R . . C8 C 0.2312(4) 0.4654(6) 0.5296(4) 0.0205(9) Uani 1 1 d . . . C9 C 0.1986(5) 0.6020(6) 0.5202(4) 0.0266(12) Uani 1 1 d . . . H9 H 0.1561 0.6360 0.5461 0.032 Uiso 1 1 calc R . . C10 C 0.2309(4) 0.6849(6) 0.4717(4) 0.0256(12) Uani 1 1 d . . . C11 C 0.2016(4) 0.8294(6) 0.4557(4) 0.0265(12) Uani 1 1 d . . . C12 C 0.1386(5) 0.9015(6) 0.4857(6) 0.0364(16) Uani 1 1 d . . . H12 H 0.1133 0.8622 0.5217 0.044 Uiso 1 1 calc R . . C13 C 0.1132(6) 1.0343(7) 0.4614(6) 0.0368(16) Uani 1 1 d . . . H13 H 0.0707 1.0855 0.4812 0.044 Uiso 1 1 calc R . . C14 C 0.1518(5) 1.0902(7) 0.4072(5) 0.0355(15) Uani 1 1 d . . . H14 H 0.1329 1.1782 0.3886 0.043 Uiso 1 1 calc R . . C15 C 0.2188(5) 1.0137(6) 0.3812(5) 0.0281(12) Uani 1 1 d . . . H15 H 0.2472 1.0517 0.3474 0.034 Uiso 1 1 calc R . . C16 C 0.1995(4) 0.3759(6) 0.5826(4) 0.0209(9) Uani 1 1 d . . . C17 C 0.2548(6) 0.2547(8) 0.6120(5) 0.0391(17) Uani 1 1 d . . . H17 H 0.3131 0.2287 0.5985 0.047 Uiso 1 1 calc R . . C18 C 0.2248(6) 0.1705(7) 0.6617(5) 0.0357(15) Uani 1 1 d . . . H18 H 0.2626 0.0888 0.6798 0.043 Uiso 1 1 calc R . . C19 C 0.1402(5) 0.2062(6) 0.6846(3) 0.0244(11) Uani 1 1 d . . . C20 C 0.0859(5) 0.3298(6) 0.6560(4) 0.0256(11) Uani 1 1 d . . . H20 H 0.0293 0.3572 0.6710 0.031 Uiso 1 1 calc R . . C21 C 0.1143(5) 0.4117(6) 0.6063(4) 0.0228(10) Uani 1 1 d . . . H21 H 0.0759 0.4930 0.5880 0.027 Uiso 1 1 calc R . . C22 C 0.1082(7) 0.1162(7) 0.7389(4) 0.0358(15) Uani 1 1 d . . . H22A H 0.0479 0.1576 0.7478 0.054 Uiso 1 1 calc R . . H22B H 0.1744 0.1025 0.7919 0.054 Uiso 1 1 calc R . . H22C H 0.0819 0.0313 0.7114 0.054 Uiso 1 1 calc R . . O4 O 0.0639(4) 0.7655(5) 0.1214(2) 0.0295(9) Uani 1 1 d . . . O5A O 0.1651(6) 0.7532(10) 0.2560(5) 0.0233(15) Uani 0.50 1 d P . 1 N4A N 0.1650(8) 0.7468(9) 0.1852(6) 0.0168(15) Uani 0.50 1 d P . 1 O6A O 0.2558(7) 0.7268(10) 0.1810(5) 0.0258(17) Uani 0.50 1 d P . .1 N4B N 0.1227(9) 0.7488(10) 0.1979(6) 0.0203(17) Uani 0.50 1 d P . 2 O6B O 0.2292(7) 0.7750(11) 0.2241(5) 0.0285(19) Uani 0.50 1 d P . 2 O5B O 0.0886(8) 0.7092(9) 0.2480(5) 0.0285(18) Uani 0.50 1 d P . 2 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 Cu2 0.0161(3) 0.0207(3) 0.0261(3) 0.0031(3) 0.0080(2) 0.0021(2) O1 0.0262(19) 0.030(2) 0.0195(18) 0.0075(16) 0.0069(15) 0.0025(16) O2 0.0278(19) 0.039(2) 0.0129(14) 0.0065(15) 0.0140(14) 0.0021(17) O3 0.043(3) 0.028(2) 0.041(3) 0.0004(19) 0.030(2) -0.0065(19) N1 0.0206(18) 0.029(2) 0.0132(15) 0.0008(15) 0.0119(14) 0.0045(16) N2 0.0115(16) 0.0179(19) 0.031(2) 0.0012(17) 0.0064(16) 0.0021(14) N3 0.0140(18) 0.023(2) 0.040(3) 0.004(2) 0.0132(18) 0.0010(16) N5 0.0229(19) 0.024(2) 0.0188(18) 0.0011(16) 0.0170(16) 0.0040(16) C1 0.029(3) 0.031(3) 0.0105(19) -0.0001(19) 0.0057(18) 0.005(2) C2 0.034(3) 0.035(3) 0.017(2) -0.004(2) 0.010(2) 0.007(2) C3 0.037(3) 0.030(3) 0.012(2) -0.0013(19) 0.012(2) 0.009(2) C5 0.0162(19) 0.024(2) 0.0123(18) 0.0004(17) 0.0028(16) 0.0057(17) C4 0.030(3) 0.025(3) 0.015(2) 0.0002(19) 0.0069(19) 0.008(2) C6 0.0135(19) 0.021(2) 0.021(2) -0.0003(18) 0.0029(17) 0.0038(17) C7 0.0151(19) 0.020(2) 0.021(2) 0.0005(18) 0.0078(17) 0.0030(16) C8 0.0134(19) 0.021(2) 0.029(2) 0.0025(19) 0.0105(18) 0.0029(17) C9 0.017(2) 0.019(2) 0.050(4) 0.002(2) 0.021(2) 0.0022(18) C10 0.0110(19) 0.019(2) 0.049(4) 0.003(2) 0.015(2) 0.0015(17) C11 0.0122(19) 0.021(2) 0.050(4) 0.007(2) 0.018(2) 0.0037(17) C12 0.024(3) 0.022(3) 0.075(5) 0.009(3) 0.032(3) 0.007(2) C13 0.025(3) 0.024(3) 0.070(5) 0.006(3) 0.029(3) 0.006(2) C14 0.023(3) 0.023(3) 0.064(5) 0.009(3) 0.023(3) 0.003(2) C15 0.018(2) 0.019(2) 0.048(4) 0.001(2) 0.015(2) -0.0017(18) C16 0.016(2) 0.019(2) 0.025(2) 0.0019(19) 0.0074(18) 0.0012(17) C17 0.027(3) 0.037(3) 0.058(4) 0.029(3) 0.023(3) 0.016(3) C18 0.029(3) 0.032(3) 0.040(4) 0.018(3) 0.010(3) 0.010(2) C19 0.027(2) 0.026(3) 0.014(2) 0.0018(18) 0.0036(18) -0.007(2) C20 0.033(3) 0.026(3) 0.021(2) -0.003(2) 0.016(2) -0.001(2) C21 0.024(2) 0.023(2) 0.026(2) 0.000(2) 0.016(2) 0.0003(19) C22 0.051(4) 0.035(3) 0.021(3) 0.008(2) 0.016(3) -0.005(3) O4 0.030(2) 0.032(2) 0.0175(17) -0.0001(16) 0.0027(15) -0.0102(18) O5A 0.020(3) 0.037(4) 0.014(3) -0.008(3) 0.008(3) 0.003(3) N4A 0.015(4) 0.015(4) 0.019(4) -0.010(3) 0.006(3) 0.001(3) O6A 0.019(3) 0.038(5) 0.021(3) 0.000(3) 0.009(3) 0.004(3) N4B 0.023(4) 0.013(4) 0.024(5) 0.012(3) 0.009(4) -0.002(4) O6B 0.020(4) 0.046(6) 0.021(4) 0.006(4) 0.010(3) 0.002(4) O5B 0.039(5) 0.032(5) 0.025(4) 0.000(3) 0.024(4) -0.010(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu2 N2 1.931(5) . ? Cu2 O2 1.990(4) . ? Cu2 N3 2.003(5) . ? Cu2 N1 2.016(5) . ? Cu2 O5A 2.155(7) . ? Cu2 O6B 2.280(8) . ? O1 N5 1.234(6) . ? O2 N5 1.293(6) . ? O3 N5 1.234(6) . ? N1 C5 1.345(7) . ? N1 C1 1.362(7) . ? N2 C10 1.318(7) . ? N2 C6 1.344(7) . ? N3 C15 1.336(8) . ? N3 C11 1.367(8) . ? C1 C2 1.385(9) . ? C1 H1 0.9300 . ? C2 C3 1.377(9) . ? C2 H2 0.9300 . ? C3 C4 1.398(8) . ? C3 H3 0.9300 . ? C5 C4 1.383(8) . ? C5 C6 1.474(8) . ? C4 H4 0.9300 . ? C6 C7 1.388(8) . ? C7 C8 1.396(7) . ? C7 H7 0.9300 . ? C8 C9 1.412(8) . ? C8 C16 1.488(8) . ? C9 C10 1.392(8) . ? C9 H9 0.9300 . ? C10 C11 1.484(8) . ? C11 C12 1.367(8) . ? C12 C13 1.385(9) . ? C12 H12 0.9300 . ? C13 C14 1.392(10) . ? C13 H13 0.9300 . ? C14 C15 1.385(9) . ? C14 H14 0.9300 . ? C16 C17 1.382(8) . ? C16 C21 1.398(8) . ? C17 C18 1.398(9) . ? C17 H17 0.9300 . ? C18 C19 1.381(10) . ? C18 H18 0.9300 . ? C19 C20 1.396(9) . ? C19 C22 1.510(8) . ? C20 C21 1.373(8) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? O4 N4B 1.241(10) . ? O4 N4A 1.309(10) . ? O5A N4B 0.931(12) . ? O5A O5B 1.037(11) . ? O5A O6B 1.222(11) . ? O5A N4A 1.264(11) . ? N4A N4B 0.683(11) . ? N4A O6B 0.858(12) . ? N4A O6A 1.233(12) . ? N4A O5B 1.840(13) . ? O6A O6B 1.087(12) . ? N4B O5B 1.229(12) . ? N4B O6B 1.273(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu2 O2 159.53(18) . . ? N2 Cu2 N3 80.7(2) . . ? O2 Cu2 N3 95.42(19) . . ? N2 Cu2 N1 78.56(18) . . ? O2 Cu2 N1 103.10(18) . . ? N3 Cu2 N1 159.10(19) . . ? N2 Cu2 O5A 97.0(3) . . ? O2 Cu2 O5A 102.3(3) . . ? N3 Cu2 O5A 81.7(3) . . ? N1 Cu2 O5A 103.3(3) . . ? N2 Cu2 O6B 124.0(3) . . ? O2 Cu2 O6B 76.4(3) . . ? N3 Cu2 O6B 102.3(3) . . ? N1 Cu2 O6B 91.5(3) . . ? O5A Cu2 O6B 31.8(3) . . ? N5 O2 Cu2 110.3(3) . . ? C5 N1 C1 117.5(5) . . ? C5 N1 Cu2 116.7(3) . . ? C1 N1 Cu2 125.9(4) . . ? C10 N2 C6 122.1(5) . . ? C10 N2 Cu2 118.0(4) . . ? C6 N2 Cu2 119.9(4) . . ? C15 N3 C11 119.7(5) . . ? C15 N3 Cu2 125.6(4) . . ? C11 N3 Cu2 114.6(4) . . ? O3 N5 O1 122.9(5) . . ? O3 N5 O2 118.1(5) . . ? O1 N5 O2 119.0(5) . . ? N1 C1 C2 122.8(6) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 118.6(6) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 119.6(6) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? N1 C5 C4 123.2(5) . . ? N1 C5 C6 112.6(5) . . ? C4 C5 C6 124.2(5) . . ? C5 C4 C3 118.2(6) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N2 C6 C7 120.3(5) . . ? N2 C6 C5 112.2(5) . . ? C7 C6 C5 127.5(5) . . ? C6 C7 C8 119.7(5) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C8 C9 118.0(5) . . ? C7 C8 C16 122.1(5) . . ? C9 C8 C16 119.9(5) . . ? C10 C9 C8 119.1(5) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? N2 C10 C9 120.8(5) . . ? N2 C10 C11 114.2(5) . . ? C9 C10 C11 124.9(5) . . ? C12 C11 N3 121.9(6) . . ? C12 C11 C10 125.6(6) . . ? N3 C11 C10 112.5(5) . . ? C11 C12 C13 118.7(7) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C12 C13 C14 119.4(6) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 119.4(6) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? N3 C15 C14 120.9(6) . . ? C17 C16 C21 117.1(5) . . ? C17 C16 C8 121.3(5) . . ? C21 C16 C8 121.6(5) . . ? C16 C17 C18 121.3(6) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C19 C18 C17 121.3(6) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 C20 117.3(5) . . ? C18 C19 C22 121.5(6) . . ? C20 C19 C22 121.2(6) . . ? C21 C20 C19 121.4(6) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C20 C21 C16 121.6(6) . . ? C20 C21 H21 119.2 . . ? C16 C21 H21 119.2 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N4B O5A O5B 77.1(9) . . ? N4B O5A O6B 71.1(8) . . ? O5B O5A O6B 145.6(10) . . ? O5B O5A N4A 105.8(9) . . ? N4B O5A Cu2 150.1(9) . . ? O5B O5A Cu2 128.9(8) . . ? O6B O5A Cu2 79.8(6) . . ? N4A O5A Cu2 118.2(6) . . ? N4B N4A O6B 111.0(15) . . ? N4B N4A O6A 164.1(16) . . ? O6B N4A O6A 59.5(9) . . ? N4B N4A O5A 46.1(11) . . ? O6B N4A O5A 67.2(9) . . ? O6A N4A O5A 119.9(9) . . ? N4B N4A O4 69.1(11) . . ? O6B N4A O4 152.6(13) . . ? O6A N4A O4 125.6(9) . . ? O5A N4A O4 114.4(9) . . ? O6B N4A O5B 99.8(10) . . ? O6A N4A O5B 143.1(9) . . ? O4 N4A O5B 87.4(6) . . ? N4A N4B O5A 102.0(15) . . ? N4A N4B O5B 147.2(16) . . ? O5A N4B O5B 55.4(8) . . ? N4A N4B O4 80.0(12) . . ? O5A N4B O4 169.4(13) . . ? O5B N4B O4 126.9(10) . . ? O5A N4B O6B 65.2(8) . . ? O5B N4B O6B 119.2(10) . . ? O4 N4B O6B 113.9(9) . . ? N4A O6B Cu2 137.3(10) . . ? O6A O6B Cu2 123.7(7) . . ? O5A O6B Cu2 68.4(5) . . ? N4B O6B Cu2 111.9(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu2 O2 N5 11.3(7) . . . . ? N3 Cu2 O2 N5 89.2(4) . . . . ? N1 Cu2 O2 N5 -81.0(4) . . . . ? O5A Cu2 O2 N5 171.9(4) . . . . ? O6B Cu2 O2 N5 -169.4(4) . . . . ? N2 Cu2 N1 C5 1.6(4) . . . . ? O2 Cu2 N1 C5 160.8(4) . . . . ? N3 Cu2 N1 C5 8.9(8) . . . . ? O5A Cu2 N1 C5 -93.0(4) . . . . ? O6B Cu2 N1 C5 -122.8(4) . . . . ? N2 Cu2 N1 C1 -180.0(5) . . . . ? O2 Cu2 N1 C1 -20.9(5) . . . . ? N3 Cu2 N1 C1 -172.7(5) . . . . ? O5A Cu2 N1 C1 85.4(5) . . . . ? O6B Cu2 N1 C1 55.6(5) . . . . ? O2 Cu2 N2 C10 79.9(7) . . . . ? N3 Cu2 N2 C10 -0.6(4) . . . . ? N1 Cu2 N2 C10 176.8(5) . . . . ? O5A Cu2 N2 C10 -81.0(5) . . . . ? O6B Cu2 N2 C10 -99.2(5) . . . . ? O2 Cu2 N2 C6 -98.4(7) . . . . ? N3 Cu2 N2 C6 -178.9(4) . . . . ? N1 Cu2 N2 C6 -1.5(4) . . . . ? O5A Cu2 N2 C6 100.7(4) . . . . ? O6B Cu2 N2 C6 82.5(5) . . . . ? N2 Cu2 N3 C15 -175.9(5) . . . . ? O2 Cu2 N3 C15 24.3(5) . . . . ? N1 Cu2 N3 C15 176.8(5) . . . . ? O5A Cu2 N3 C15 -77.4(6) . . . . ? O6B Cu2 N3 C15 -52.9(6) . . . . ? N2 Cu2 N3 C11 0.1(4) . . . . ? O2 Cu2 N3 C11 -159.7(4) . . . . ? N1 Cu2 N3 C11 -7.2(8) . . . . ? O5A Cu2 N3 C11 98.6(5) . . . . ? O6B Cu2 N3 C11 123.1(5) . . . . ? Cu2 O2 N5 O3 -175.0(4) . . . . ? Cu2 O2 N5 O1 5.5(6) . . . . ? C5 N1 C1 C2 -1.4(8) . . . . ? Cu2 N1 C1 C2 -179.8(4) . . . . ? N1 C1 C2 C3 1.1(9) . . . . ? C1 C2 C3 C4 0.2(9) . . . . ? C1 N1 C5 C4 0.4(8) . . . . ? Cu2 N1 C5 C4 178.9(4) . . . . ? C1 N1 C5 C6 180.0(4) . . . . ? Cu2 N1 C5 C6 -1.5(5) . . . . ? N1 C5 C4 C3 0.8(8) . . . . ? C6 C5 C4 C3 -178.7(5) . . . . ? C2 C3 C4 C5 -1.1(8) . . . . ? C10 N2 C6 C7 2.4(8) . . . . ? Cu2 N2 C6 C7 -179.4(4) . . . . ? C10 N2 C6 C5 -177.1(5) . . . . ? Cu2 N2 C6 C5 1.2(6) . . . . ? N1 C5 C6 N2 0.3(6) . . . . ? C4 C5 C6 N2 179.9(5) . . . . ? N1 C5 C6 C7 -179.1(5) . . . . ? C4 C5 C6 C7 0.4(8) . . . . ? N2 C6 C7 C8 -1.1(8) . . . . ? C5 C6 C7 C8 178.3(5) . . . . ? C6 C7 C8 C9 -0.1(8) . . . . ? C6 C7 C8 C16 -178.8(5) . . . . ? C7 C8 C9 C10 0.1(9) . . . . ? C16 C8 C9 C10 178.8(5) . . . . ? C6 N2 C10 C9 -2.5(9) . . . . ? Cu2 N2 C10 C9 179.3(5) . . . . ? C6 N2 C10 C11 179.2(5) . . . . ? Cu2 N2 C10 C11 1.0(7) . . . . ? C8 C9 C10 N2 1.2(9) . . . . ? C8 C9 C10 C11 179.3(6) . . . . ? C15 N3 C11 C12 -2.1(10) . . . . ? Cu2 N3 C11 C12 -178.4(5) . . . . ? C15 N3 C11 C10 176.7(5) . . . . ? Cu2 N3 C11 C10 0.4(7) . . . . ? N2 C10 C11 C12 177.9(7) . . . . ? C9 C10 C11 C12 -0.4(11) . . . . ? N2 C10 C11 N3 -0.9(8) . . . . ? C9 C10 C11 N3 -179.1(6) . . . . ? N3 C11 C12 C13 2.1(11) . . . . ? C10 C11 C12 C13 -176.5(7) . . . . ? C11 C12 C13 C14 0.2(11) . . . . ? C12 C13 C14 C15 -2.5(11) . . . . ? C11 N3 C15 C14 -0.3(9) . . . . ? Cu2 N3 C15 C14 175.5(5) . . . . ? C13 C14 C15 N3 2.6(11) . . . . ? C7 C8 C16 C17 16.6(9) . . . . ? C9 C8 C16 C17 -162.0(6) . . . . ? C7 C8 C16 C21 -164.7(5) . . . . ? C9 C8 C16 C21 16.7(8) . . . . ? C21 C16 C17 C18 1.4(11) . . . . ? C8 C16 C17 C18 -179.9(7) . . . . ? C16 C17 C18 C19 -1.1(12) . . . . ? C17 C18 C19 C20 0.0(10) . . . . ? C17 C18 C19 C22 -179.5(7) . . . . ? C18 C19 C20 C21 0.9(9) . . . . ? C22 C19 C20 C21 -179.7(6) . . . . ? C19 C20 C21 C16 -0.6(9) . . . . ? C17 C16 C21 C20 -0.5(9) . . . . ? C8 C16 C21 C20 -179.3(5) . . . . ? N2 Cu2 O5A N4B -138(2) . . . . ? O2 Cu2 O5A N4B 49(2) . . . . ? N3 Cu2 O5A N4B 143(2) . . . . ? N1 Cu2 O5A N4B -58(2) . . . . ? O6B Cu2 O5A N4B 13.0(18) . . . . ? N2 Cu2 O5A O5B 8.0(11) . . . . ? O2 Cu2 O5A O5B -165.2(10) . . . . ? N3 Cu2 O5A O5B -71.5(10) . . . . ? N1 Cu2 O5A O5B 87.9(11) . . . . ? O6B Cu2 O5A O5B 158.6(15) . . . . ? N2 Cu2 O5A O6B -150.6(7) . . . . ? O2 Cu2 O5A O6B 36.2(7) . . . . ? N3 Cu2 O5A O6B 129.9(7) . . . . ? N1 Cu2 O5A O6B -70.7(7) . . . . ? N2 Cu2 O5A N4A -137.9(8) . . . . ? O2 Cu2 O5A N4A 48.8(9) . . . . ? N3 Cu2 O5A N4A 142.6(9) . . . . ? N1 Cu2 O5A N4A -58.1(9) . . . . ? O6B Cu2 O5A N4A 12.7(7) . . . . ? O5B O5A N4A N4B 26.6(16) . . . . ? O6B O5A N4A N4B -161(2) . . . . ? Cu2 O5A N4A N4B 179.6(16) . . . . ? N4B O5A N4A O6B 161(2) . . . . ? O5B O5A N4A O6B -172.5(13) . . . . ? Cu2 O5A N4A O6B -19.5(11) . . . . ? N4B O5A N4A O6A -171(2) . . . . ? O5B O5A N4A O6A -144.0(11) . . . . ? O6B O5A N4A O6A 28.6(11) . . . . ? Cu2 O5A N4A O6A 9.1(14) . . . . ? N4B O5A N4A O4 10.8(13) . . . . ? O5B O5A N4A O4 37.4(13) . . . . ? O6B O5A N4A O4 -150.1(14) . . . . ? Cu2 O5A N4A O4 -169.5(6) . . . . ? N4B O5A N4A O5B -26.6(16) . . . . ? O6B O5A N4A O5B 172.5(13) . . . . ? Cu2 O5A N4A O5B 153.1(14) . . . . ? N4B O4 N4A O6B -96(3) . . . . ? N4B O4 N4A O6A 173(2) . . . . ? N4B O4 N4A O5A -8.3(10) . . . . ? N4B O4 N4A O5B 10.9(11) . . . . ? N4B N4A O6A O6B -56(6) . . . . ? O5A N4A O6A O6B -30.8(11) . . . . ? O4 N4A O6A O6B 147.7(16) . . . . ? O5B N4A O6A O6B -62.9(14) . . . . ? O6B N4A N4B O5A -19(2) . . . . ? O6A N4A N4B O5A 31(6) . . . . ? O4 N4A N4B O5A -169.5(13) . . . . ? O5B N4A N4B O5A 42(2) . . . . ? O6B N4A N4B O5B -61(3) . . . . ? O6A N4A N4B O5B -11(8) . . . . ? O5A N4A N4B O5B -42(2) . . . . ? O4 N4A N4B O5B 148(3) . . . . ? O6B N4A N4B O4 150.6(14) . . . . ? O6A N4A N4B O4 -159(6) . . . . ? O5A N4A N4B O4 169.5(13) . . . . ? O5B N4A N4B O4 -148(3) . . . . ? O6A N4A N4B O6B 50(5) . . . . ? O5A N4A N4B O6B 19(2) . . . . ? O4 N4A N4B O6B -150.6(14) . . . . ? O5B N4A N4B O6B 61(3) . . . . ? O5B O5A N4B N4A -153.8(16) . . . . ? O6B O5A N4B N4A 12.9(14) . . . . ? Cu2 O5A N4B N4A -1(3) . . . . ? O6B O5A N4B O5B 166.7(11) . . . . ? N4A O5A N4B O5B 153.8(16) . . . . ? Cu2 O5A N4B O5B 153(2) . . . . ? O5B O5A N4B O4 106(7) . . . . ? O6B O5A N4B O4 -87(7) . . . . ? N4A O5A N4B O4 -100(7) . . . . ? Cu2 O5A N4B O4 -101(7) . . . . ? O5B O5A N4B O6B -166.7(11) . . . . ? N4A O5A N4B O6B -12.9(14) . . . . ? Cu2 O5A N4B O6B -13.6(19) . . . . ? N4A O4 N4B O5A 102(7) . . . . ? N4A O4 N4B O5B -159(2) . . . . ? N4A O4 N4B O6B 19.7(10) . . . . ? N4B N4A O6B O6A 165.9(17) . . . . ? O5A N4A O6B O6A 151.2(10) . . . . ? O4 N4A O6B O6A -109(3) . . . . ? O5B N4A O6B O6A 147.1(8) . . . . ? N4B N4A O6B O5A 14.6(16) . . . . ? O6A N4A O6B O5A -151.2(10) . . . . ? O4 N4A O6B O5A 99(3) . . . . ? O5B N4A O6B O5A -4.1(7) . . . . ? O6A N4A O6B N4B -165.9(17) . . . . ? O5A N4A O6B N4B -14.6(16) . . . . ? O4 N4A O6B N4B 85(3) . . . . ? O5B N4A O6B N4B -18.7(13) . . . . ? N4B N4A O6B Cu2 39(2) . . . . ? O6A N4A O6B Cu2 -127.0(16) . . . . ? O5A N4A O6B Cu2 24.2(13) . . . . ? O4 N4A O6B Cu2 124(2) . . . . ? O5B N4A O6B Cu2 20.1(16) . . . . ? N4A O6A O6B O5A 44.2(13) . . . . ? N4A O6A O6B N4B 7.3(9) . . . . ? N4A O6A O6B Cu2 139.4(14) . . . . ? N4B O5A O6B N4A -10.5(11) . . . . ? O5B O5A O6B N4A 13(2) . . . . ? Cu2 O5A O6B N4A 162.6(10) . . . . ? N4B O5A O6B O6A -56.1(17) . . . . ? O5B O5A O6B O6A -33(3) . . . . ? N4A O5A O6B O6A -45.6(14) . . . . ? Cu2 O5A O6B O6A 117.1(14) . . . . ? O5B O5A O6B N4B 23.3(18) . . . . ? N4A O5A O6B N4B 10.5(11) . . . . ? Cu2 O5A O6B N4B 173.2(10) . . . . ? N4B O5A O6B Cu2 -173.2(10) . . . . ? O5B O5A O6B Cu2 -150(2) . . . . ? N4A O5A O6B Cu2 -162.6(10) . . . . ? O5A N4B O6B N4A 160(2) . . . . ? O5B N4B O6B N4A 147(2) . . . . ? O4 N4B O6B N4A -31.9(16) . . . . ? N4A N4B O6B O6A -14.4(17) . . . . ? O5A N4B O6B O6A 145.2(13) . . . . ? O5B N4B O6B O6A 132.7(12) . . . . ? O4 N4B O6B O6A -46.4(13) . . . . ? N4A N4B O6B O5A -160(2) . . . . ? O5B N4B O6B O5A -12.5(10) . . . . ? O4 N4B O6B O5A 168.5(14) . . . . ? N4A N4B O6B Cu2 -152.8(18) . . . . ? O5A N4B O6B Cu2 6.9(10) . . . . ? O5B N4B O6B Cu2 -5.6(14) . . . . ? O4 N4B O6B Cu2 175.3(7) . . . . ? N2 Cu2 O6B N4A 11.2(17) . . . . ? O2 Cu2 O6B N4A -168.5(16) . . . . ? N3 Cu2 O6B N4A -75.8(16) . . . . ? N1 Cu2 O6B N4A 88.4(15) . . . . ? O5A Cu2 O6B N4A -24.8(13) . . . . ? N2 Cu2 O6B O6A -99.1(10) . . . . ? O2 Cu2 O6B O6A 81.2(10) . . . . ? N3 Cu2 O6B O6A 173.9(10) . . . . ? N1 Cu2 O6B O6A -21.9(10) . . . . ? O5A Cu2 O6B O6A -135.2(14) . . . . ? N2 Cu2 O6B O5A 36.1(8) . . . . ? O2 Cu2 O6B O5A -143.6(7) . . . . ? N3 Cu2 O6B O5A -50.9(7) . . . . ? N1 Cu2 O6B O5A 113.3(7) . . . . ? N2 Cu2 O6B N4B 31.0(9) . . . . ? O2 Cu2 O6B N4B -148.7(9) . . . . ? N3 Cu2 O6B N4B -56.0(8) . . . . ? N1 Cu2 O6B N4B 108.2(8) . . . . ? O5A Cu2 O6B N4B -5.1(7) . . . . ? O6B O5A O5B N4B -22.6(18) . . . . ? N4A O5A O5B N4B -14.0(9) . . . . ? Cu2 O5A O5B N4B -163.2(14) . . . . ? N4B O5A O5B N4A 14.0(9) . . . . ? O6B O5A O5B N4A -8.5(15) . . . . ? Cu2 O5A O5B N4A -149.1(14) . . . . ? N4A N4B O5B O5A 53(3) . . . . ? O4 N4B O5B O5A -167.3(16) . . . . ? O6B N4B O5B O5A 13.8(11) . . . . ? O5A N4B O5B N4A -53(3) . . . . ? O4 N4B O5B N4A 140(4) . . . . ? O6B N4B O5B N4A -39(2) . . . . ? N4B N4A O5B O5A -117(3) . . . . ? O6B N4A O5B O5A 7.0(12) . . . . ? O6A N4A O5B O5A 58.1(16) . . . . ? O4 N4A O5B O5A -146.4(12) . . . . ? O6B N4A O5B N4B 124(3) . . . . ? O6A N4A O5B N4B 175(4) . . . . ? O5A N4A O5B N4B 117(3) . . . . ? O4 N4A O5B N4B -29(3) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.888 _refine_diff_density_min -0.769 _refine_diff_density_rms 0.181