Electronic Supplementary Material for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Matthias Wagner' _publ_contact_author_address ; Inst. fuer Anorganische Chemie Goethe-Universitaet Frankfurt Max-von Laue-Strasse 7 Frankfurt 60438 GERMANY ; _publ_contact_author_email MATTHIAS.WAGNER@CHEMIE.UNI-FRANKFURT.DE _publ_section_title ; Hydroquinone-Bridged Dinuclear CuII Complexes and Single-Crystalline CuII Coordination Polymers ; loop_ _publ_author_name 'Matthias Wagner' 'Jan W. Bats' 'Tonia Kretz' 'Michael Lang' 'Hans-Wolfram Lerner' 'Serena Losi' 'Bernd Wolf' ; P.Zanello ; # Attachment 'compound3.cif' data_lerner25 _database_code_depnum_ccdc_archive 'CCDC 613043' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H54 Cu2 N6 O4, 2 (C F3 S O3)' _chemical_formula_sum 'C32 H54 Cu2 F6 N6 O10 S2' _chemical_formula_weight 988.01 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7780(7) _cell_length_b 8.9085(8) _cell_length_c 15.9926(14) _cell_angle_alpha 102.564(5) _cell_angle_beta 96.494(5) _cell_angle_gamma 96.263(6) _cell_volume 1064.40(16) _cell_formula_units_Z 1 _cell_measurement_temperature 224(2) _cell_measurement_reflns_used 307 _cell_measurement_theta_min 3 _cell_measurement_theta_max 26 _exptl_crystal_description plate _exptl_crystal_colour deep_red _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 1.182 _exptl_absorpt_correction_type 'empirical, SADABS (Sheldrick, 2000)' _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 224(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type SIEMENS_SMART_CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 161 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1200 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 13846 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0916 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 30.87 _reflns_number_total 5625 _reflns_number_gt 3067 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.05P)^2^+0.5P] 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 5625 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1315 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.1352 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Cu Cu 0.42792(6) 0.20006(5) 0.16703(3) 0.04064(17) Uani 1 1 d . . . O2 O 0.3078(4) -0.0131(3) 0.12201(16) 0.0570(8) Uani 1 1 d . . . N2 N 0.4923(4) 0.1586(3) 0.28877(17) 0.0374(7) Uani 1 1 d . . . O1 O 0.4097(4) 0.2302(3) 0.05381(15) 0.0548(7) Uani 1 1 d . . . N1 N 0.5126(4) 0.4139(3) 0.21991(17) 0.0396(7) Uani 1 1 d . . . N3 N 0.1428(4) -0.2021(3) 0.01877(18) 0.0451(8) Uani 1 1 d . . . C2 C 0.5195(5) 0.5056(4) 0.0886(2) 0.0379(8) Uani 1 1 d . . . C4 C 0.5439(5) 0.5227(4) 0.1810(2) 0.0429(9) Uani 1 1 d . . . H4 H 0.5864 0.6224 0.2156 0.052 Uiso 1 1 calc R . . C3 C 0.4539(5) 0.3623(4) 0.0299(2) 0.0416(9) Uani 1 1 d . . . C1 C 0.5629(5) 0.6374(4) 0.0574(2) 0.0448(9) Uani 1 1 d . . . H1 H 0.6060 0.7312 0.0977 0.054 Uiso 1 1 calc R . . C13 C 0.2462(5) -0.0724(4) 0.0450(2) 0.0504(10) Uani 1 1 d . . . H13 H 0.2772 -0.0190 0.0031 0.060 Uiso 1 1 calc R . . C5 C 0.5456(6) 0.4450(4) 0.3144(2) 0.0493(10) Uani 1 1 d . . . H5A H 0.4378 0.4631 0.3391 0.059 Uiso 1 1 calc R . . H5B H 0.6330 0.5370 0.3377 0.059 Uiso 1 1 calc R . . C7 C 0.3302(6) 0.1245(6) 0.3305(3) 0.0612(12) Uani 1 1 d . . . H7 H 0.3035 0.0101 0.3192 0.073 Uiso 1 1 calc R . . C10 C 0.5896(5) 0.0181(4) 0.2765(2) 0.0440(9) Uani 1 1 d . . . H10A H 0.5016 -0.0735 0.2493 0.053 Uiso 1 1 calc R . . C11 C 0.7189(5) 0.0280(5) 0.2144(3) 0.0552(11) Uani 1 1 d . . . H11A H 0.6606 0.0457 0.1612 0.083 Uiso 1 1 calc R . . H11B H 0.7683 -0.0685 0.2018 0.083 Uiso 1 1 calc R . . H11C H 0.8116 0.1131 0.2400 0.083 Uiso 1 1 calc R . . C6 C 0.6121(5) 0.3027(4) 0.3363(2) 0.0454(9) Uani 1 1 d . . . H6A H 0.7295 0.2964 0.3204 0.054 Uiso 1 1 calc R . . H6B H 0.6194 0.3111 0.3988 0.054 Uiso 1 1 calc R . . C12 C 0.6751(6) -0.0120(5) 0.3611(3) 0.0699(13) Uani 1 1 d . . . H12A H 0.7337 -0.1033 0.3486 0.105 Uiso 1 1 calc R . . H12B H 0.5861 -0.0289 0.3973 0.105 Uiso 1 1 calc R . . H12C H 0.7595 0.0770 0.3912 0.105 Uiso 1 1 calc R . . C15 C 0.0958(8) -0.2948(6) 0.0787(3) 0.0935(19) Uani 1 1 d . . . H15A H 0.1481 -0.2412 0.1370 0.140 Uiso 1 1 calc R . . H15B H 0.1381 -0.3943 0.0634 0.140 Uiso 1 1 calc R . . H15C H -0.0303 -0.3112 0.0758 0.140 Uiso 1 1 calc R . . C8 C 0.1763(6) 0.1789(8) 0.2904(4) 0.104(2) Uani 1 1 d . . . H8A H 0.1618 0.1394 0.2281 0.156 Uiso 1 1 calc R . . H8B H 0.1927 0.2915 0.3039 0.156 Uiso 1 1 calc R . . H8C H 0.0731 0.1417 0.3127 0.156 Uiso 1 1 calc R . . C9 C 0.3527(7) 0.1856(7) 0.4288(3) 0.0933(18) Uani 1 1 d . . . H9A H 0.2447 0.1574 0.4501 0.140 Uiso 1 1 calc R . . H9B H 0.3816 0.2978 0.4430 0.140 Uiso 1 1 calc R . . H9C H 0.4460 0.1404 0.4556 0.140 Uiso 1 1 calc R . . C14 C 0.0791(6) -0.2712(5) -0.0719(3) 0.0734(15) Uani 1 1 d . . . H14A H 0.1180 -0.2011 -0.1067 0.110 Uiso 1 1 calc R . . H14B H -0.0475 -0.2898 -0.0802 0.110 Uiso 1 1 calc R . . H14C H 0.1244 -0.3688 -0.0892 0.110 Uiso 1 1 calc R . . S S 0.05569(16) 0.62742(14) 0.28997(7) 0.0601(3) Uani 1 1 d . . . F3 F 0.1916(5) 0.5869(5) 0.43894(19) 0.1251(14) Uani 1 1 d . . . F2 F -0.0614(5) 0.6535(6) 0.4370(2) 0.1540(18) Uani 1 1 d . . . C16 C 0.0849(8) 0.6703(7) 0.4064(3) 0.0796(15) Uani 1 1 d . . . O3 O -0.0563(5) 0.7312(5) 0.2684(2) 0.1133(15) Uani 1 1 d . . . O5 O -0.0229(7) 0.4730(5) 0.2674(3) 0.1388(18) Uani 1 1 d . . . O4 O 0.2265(5) 0.6507(6) 0.2710(2) 0.1191(16) Uani 1 1 d . . . F1 F 0.1511(8) 0.8125(6) 0.4395(3) 0.202(3) 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 Cu 0.0507(3) 0.0358(3) 0.0315(2) 0.01208(18) -0.00798(19) -0.00531(19) O2 0.080(2) 0.0453(15) 0.0353(15) 0.0162(12) -0.0175(13) -0.0235(14) N2 0.0393(17) 0.0416(17) 0.0310(15) 0.0132(13) -0.0018(13) 0.0008(13) O1 0.090(2) 0.0334(14) 0.0329(14) 0.0110(11) -0.0096(13) -0.0155(13) N1 0.0530(19) 0.0355(16) 0.0293(15) 0.0089(13) -0.0014(14) 0.0065(14) N3 0.0523(19) 0.0417(17) 0.0355(17) 0.0127(14) -0.0056(14) -0.0142(14) C2 0.050(2) 0.0304(18) 0.0303(18) 0.0083(14) -0.0019(16) -0.0015(16) C4 0.062(3) 0.0271(18) 0.036(2) 0.0040(15) -0.0037(17) 0.0047(17) C3 0.056(2) 0.0301(18) 0.035(2) 0.0108(15) -0.0045(17) -0.0041(16) C1 0.066(3) 0.0277(18) 0.0323(19) 0.0028(14) -0.0100(18) -0.0022(17) C13 0.065(3) 0.044(2) 0.038(2) 0.0162(18) -0.0055(19) -0.0118(19) C5 0.077(3) 0.043(2) 0.0254(18) 0.0069(16) -0.0008(18) 0.009(2) C7 0.053(3) 0.086(3) 0.053(3) 0.029(2) 0.012(2) 0.014(2) C10 0.054(2) 0.037(2) 0.039(2) 0.0131(16) -0.0064(18) 0.0029(17) C11 0.058(3) 0.051(2) 0.047(2) -0.0008(19) -0.004(2) 0.004(2) C6 0.057(3) 0.042(2) 0.0334(19) 0.0089(16) -0.0059(18) 0.0022(18) C12 0.093(4) 0.071(3) 0.049(3) 0.021(2) -0.008(2) 0.034(3) C15 0.133(5) 0.081(3) 0.049(3) 0.027(2) -0.013(3) -0.058(3) C8 0.054(3) 0.149(6) 0.104(5) 0.022(4) 0.007(3) 0.017(3) C9 0.079(4) 0.157(6) 0.058(3) 0.040(3) 0.027(3) 0.030(4) C14 0.099(4) 0.065(3) 0.040(2) 0.011(2) -0.013(2) -0.035(3) S 0.0694(8) 0.0765(8) 0.0393(6) 0.0154(5) 0.0090(5) 0.0254(6) F3 0.141(3) 0.198(4) 0.0540(18) 0.050(2) 0.0035(18) 0.068(3) F2 0.116(3) 0.298(6) 0.058(2) 0.039(3) 0.038(2) 0.053(3) C16 0.081(4) 0.106(4) 0.045(3) 0.008(3) -0.001(3) 0.010(3) O3 0.122(3) 0.169(4) 0.081(3) 0.053(3) 0.026(2) 0.096(3) O5 0.227(6) 0.092(3) 0.071(3) -0.010(2) -0.005(3) -0.007(3) O4 0.077(3) 0.228(5) 0.094(3) 0.090(3) 0.039(2) 0.069(3) F1 0.306(7) 0.140(4) 0.103(3) -0.040(3) -0.027(4) -0.024(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 Cu O1 1.880(2) . ? Cu N1 1.917(3) . ? Cu O2 1.965(2) . ? Cu N2 2.076(3) . ? O2 C13 1.246(4) . ? N2 C6 1.499(4) . ? N2 C10 1.521(4) . ? N2 C7 1.524(5) . ? O1 C3 1.336(4) . ? N1 C4 1.277(4) . ? N1 C5 1.464(4) . ? N3 C13 1.292(4) . ? N3 C15 1.446(5) . ? N3 C14 1.452(5) . ? C2 C1 1.396(5) . ? C2 C3 1.414(4) . ? C2 C4 1.441(5) . ? C3 C1 1.387(5) 2_665 ? C1 C3 1.387(5) 2_665 ? C5 C6 1.514(5) . ? C7 C8 1.472(6) . ? C7 C9 1.531(6) . ? C10 C11 1.501(5) . ? C10 C12 1.529(5) . ? S O5 1.395(4) . ? S O4 1.400(4) . ? S O3 1.407(3) . ? S C16 1.801(5) . ? F3 C16 1.310(6) . ? F2 C16 1.294(6) . ? C16 F1 1.286(7) . ? 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 O1 Cu N1 94.03(11) . . ? O1 Cu O2 89.77(10) . . ? N1 Cu O2 170.78(13) . . ? O1 Cu N2 169.88(12) . . ? N1 Cu N2 86.20(11) . . ? O2 Cu N2 91.55(10) . . ? C13 O2 Cu 125.6(2) . . ? C6 N2 C10 110.9(3) . . ? C6 N2 C7 114.5(3) . . ? C10 N2 C7 109.3(3) . . ? C6 N2 Cu 103.20(19) . . ? C10 N2 Cu 106.9(2) . . ? C7 N2 Cu 111.7(2) . . ? C3 O1 Cu 127.2(2) . . ? C4 N1 C5 120.5(3) . . ? C4 N1 Cu 126.7(2) . . ? C5 N1 Cu 112.8(2) . . ? C13 N3 C15 121.0(3) . . ? C13 N3 C14 123.2(3) . . ? C15 N3 C14 115.6(3) . . ? C1 C2 C3 119.8(3) . . ? C1 C2 C4 117.6(3) . . ? C3 C2 C4 122.6(3) . . ? N1 C4 C2 125.4(3) . . ? O1 C3 C1 119.6(3) . 2_665 ? O1 C3 C2 124.0(3) . . ? C1 C3 C2 116.4(3) 2_665 . ? C3 C1 C2 123.8(3) 2_665 . ? O2 C13 N3 124.6(3) . . ? N1 C5 C6 106.4(3) . . ? C8 C7 N2 112.2(4) . . ? C8 C7 C9 109.6(4) . . ? N2 C7 C9 114.8(4) . . ? C11 C10 N2 111.0(3) . . ? C11 C10 C12 111.5(3) . . ? N2 C10 C12 113.9(3) . . ? N2 C6 C5 110.4(3) . . ? O5 S O4 114.7(3) . . ? O5 S O3 113.2(3) . . ? O4 S O3 116.4(3) . . ? O5 S C16 102.7(3) . . ? O4 S C16 103.2(3) . . ? O3 S C16 104.3(3) . . ? F1 C16 F2 105.0(5) . . ? F1 C16 F3 105.5(5) . . ? F2 C16 F3 108.6(5) . . ? F1 C16 S 111.6(4) . . ? F2 C16 S 112.5(4) . . ? F3 C16 S 113.1(4) . . ? 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 O1 Cu O2 C13 -3.8(3) . . . . ? N1 Cu O2 C13 110.6(7) . . . . ? N2 Cu O2 C13 -173.8(3) . . . . ? O1 Cu N2 C6 74.9(6) . . . . ? N1 Cu N2 C6 -16.7(2) . . . . ? O2 Cu N2 C6 172.3(2) . . . . ? O1 Cu N2 C10 -42.1(7) . . . . ? N1 Cu N2 C10 -133.7(2) . . . . ? O2 Cu N2 C10 55.3(2) . . . . ? O1 Cu N2 C7 -161.6(5) . . . . ? N1 Cu N2 C7 106.8(3) . . . . ? O2 Cu N2 C7 -64.2(3) . . . . ? N1 Cu O1 C3 2.5(3) . . . . ? O2 Cu O1 C3 174.1(3) . . . . ? N2 Cu O1 C3 -88.4(7) . . . . ? O1 Cu N1 C4 -2.0(3) . . . . ? O2 Cu N1 C4 -116.1(7) . . . . ? N2 Cu N1 C4 167.9(3) . . . . ? O1 Cu N1 C5 179.6(3) . . . . ? O2 Cu N1 C5 65.6(8) . . . . ? N2 Cu N1 C5 -10.5(2) . . . . ? C5 N1 C4 C2 178.9(3) . . . . ? Cu N1 C4 C2 0.7(6) . . . . ? C1 C2 C4 N1 -179.2(4) . . . . ? C3 C2 C4 N1 1.0(6) . . . . ? Cu O1 C3 C1 177.8(3) . . . 2_665 ? Cu O1 C3 C2 -1.7(6) . . . . ? C1 C2 C3 O1 179.7(4) . . . . ? C4 C2 C3 O1 -0.4(6) . . . . ? C1 C2 C3 C1 0.2(6) . . . 2_665 ? C4 C2 C3 C1 180.0(3) . . . 2_665 ? C3 C2 C1 C3 -0.2(7) . . . 2_665 ? C4 C2 C1 C3 180.0(4) . . . 2_665 ? Cu O2 C13 N3 -167.7(3) . . . . ? C15 N3 C13 O2 -3.0(7) . . . . ? C14 N3 C13 O2 -177.4(4) . . . . ? C4 N1 C5 C6 -143.4(3) . . . . ? Cu N1 C5 C6 35.1(4) . . . . ? C6 N2 C7 C8 97.6(4) . . . . ? C10 N2 C7 C8 -137.3(4) . . . . ? Cu N2 C7 C8 -19.2(5) . . . . ? C6 N2 C7 C9 -28.3(5) . . . . ? C10 N2 C7 C9 96.7(4) . . . . ? Cu N2 C7 C9 -145.2(3) . . . . ? C6 N2 C10 C11 -68.7(4) . . . . ? C7 N2 C10 C11 164.1(3) . . . . ? Cu N2 C10 C11 43.1(3) . . . . ? C6 N2 C10 C12 58.1(4) . . . . ? C7 N2 C10 C12 -69.1(4) . . . . ? Cu N2 C10 C12 169.8(3) . . . . ? C10 N2 C6 C5 154.6(3) . . . . ? C7 N2 C6 C5 -81.1(4) . . . . ? Cu N2 C6 C5 40.5(3) . . . . ? N1 C5 C6 N2 -50.7(4) . . . . ? O5 S C16 F1 -177.5(5) . . . . ? O4 S C16 F1 62.9(6) . . . . ? O3 S C16 F1 -59.2(5) . . . . ? O5 S C16 F2 -59.8(5) . . . . ? O4 S C16 F2 -179.4(5) . . . . ? O3 S C16 F2 58.5(5) . . . . ? O5 S C16 F3 63.7(5) . . . . ? O4 S C16 F3 -55.8(5) . . . . ? O3 S C16 F3 -177.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.840 _diffrn_reflns_theta_full 30.87 _diffrn_measured_fraction_theta_full 0.840 _refine_diff_density_max 0.586 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.072 # Attachment 'compound4.cif' data_lerner24 _database_code_depnum_ccdc_archive 'CCDC 613044' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H48 Cu2 F6 N8 O12 S2' _chemical_formula_weight 1090.02 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0083(12) _cell_length_b 12.3677(14) _cell_length_c 13.1673(19) _cell_angle_alpha 63.661(14) _cell_angle_beta 88.820(13) _cell_angle_gamma 77.488(11) _cell_volume 1136.7(3) _cell_formula_units_Z 1 _cell_measurement_temperature 155(2) _cell_measurement_reflns_used 146 _cell_measurement_theta_min 3 _cell_measurement_theta_max 23 _exptl_crystal_description rod _exptl_crystal_colour red_brown _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 1.119 _exptl_absorpt_correction_type 'numerical, SHELXTL (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.649 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 155(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type SIEMENS_SMART_CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 237 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1200 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 19872 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 32.64 _reflns_number_total 7375 _reflns_number_gt 5438 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (siemens, 1995)' _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.03P)^2^+0.5P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7375 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.0877 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.240 _refine_ls_shift/su_mean 0.002 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 0.01901(3) 0.38972(2) -0.039281(19) 0.01651(7) Uani 1 1 d . . . O2 O 0.16054(16) 0.27562(12) 0.10795(11) 0.0205(3) Uani 1 1 d . . . N2 N 0.20817(19) 0.31998(15) -0.11887(14) 0.0201(3) Uani 1 1 d . . . C13 C 0.3998(2) 0.1323(2) 0.28984(18) 0.0265(4) Uani 1 1 d . . . H13A H 0.4132 0.1158 0.2235 0.040 Uiso 1 1 calc R . . H13B H 0.4477 0.0560 0.3588 0.040 Uiso 1 1 calc R . . H13C H 0.4605 0.1962 0.2814 0.040 Uiso 1 1 calc R . . N3 N 0.2175(2) 0.17541(15) 0.29839(13) 0.0201(3) Uani 1 1 d . . . C12 C 0.1131(2) 0.24497(17) 0.20627(16) 0.0194(4) Uani 1 1 d . . . H12 H -0.0041 0.2735 0.2144 0.023 Uiso 1 1 calc R . . C14 C 0.1584(3) 0.1403(2) 0.41221(17) 0.0265(4) Uani 1 1 d . . . H14A H 0.0342 0.1736 0.4059 0.040 Uiso 1 1 calc R . . H14B H 0.2173 0.1741 0.4519 0.040 Uiso 1 1 calc R . . H14C H 0.1840 0.0497 0.4551 0.040 Uiso 1 1 calc R . . C11 C 0.3655(3) 0.2648(2) -0.06400(19) 0.0306(5) Uani 1 1 d . . . H11 H 0.3877 0.2677 0.0052 0.037 Uiso 1 1 calc R . . C7 C 0.1811(2) 0.31912(17) -0.21978(16) 0.0195(4) Uani 1 1 d . . . C9 C 0.4663(3) 0.1991(2) -0.2028(2) 0.0369(5) Uani 1 1 d . . . H9 H 0.5528 0.1554 -0.2302 0.044 Uiso 1 1 calc R . . C8 C 0.3085(3) 0.2586(2) -0.26219(18) 0.0266(4) Uani 1 1 d . . . H8 H 0.2861 0.2585 -0.3327 0.032 Uiso 1 1 calc R . . C6 C 0.0121(3) 0.3878(2) -0.28805(17) 0.0261(4) Uani 1 1 d . . . H6A H -0.0721 0.3357 -0.2573 0.031 Uiso 1 1 calc R . . H6B H 0.0253 0.4015 -0.3675 0.031 Uiso 1 1 calc R . . C10 C 0.4967(3) 0.2040(3) -0.1028(2) 0.0426(6) Uani 1 1 d . . . H10 H 0.6061 0.1662 -0.0611 0.051 Uiso 1 1 calc R . . S S -0.62913(6) 0.76292(5) -0.48813(4) 0.02394(11) Uani 1 1 d . . . F1 F -0.6540(2) 0.61820(15) -0.58118(14) 0.0510(4) Uani 1 1 d . . . F2 F -0.6661(2) 0.53572(14) -0.39947(15) 0.0631(5) Uani 1 1 d . . . O4 O -0.7066(2) 0.77241(17) -0.39204(14) 0.0390(4) Uani 1 1 d . . . F3 F -0.88287(18) 0.67153(17) -0.50938(14) 0.0517(4) Uani 1 1 d . . . O6 O -0.44635(19) 0.71593(17) -0.47216(14) 0.0396(4) Uani 1 1 d . . . O5 O -0.6925(2) 0.86622(15) -0.59618(15) 0.0441(4) Uani 1 1 d . . . C18 C -0.7103(3) 0.6406(2) -0.4954(2) 0.0337(5) Uani 1 1 d . . . O3 O -0.1207(2) 0.20906(15) -0.00255(14) 0.0361(4) Uani 1 1 d . . . N4 N -0.0813(2) 0.05159(17) 0.17672(15) 0.0290(4) Uani 1 1 d . . . C17 C -0.1321(3) 0.0036(2) 0.2929(2) 0.0384(5) Uani 1 1 d . . . H17A H -0.2115 0.0701 0.3025 0.058 Uiso 1 1 calc R . . H17B H -0.0300 -0.0276 0.3464 0.058 Uiso 1 1 calc R . . H17C H -0.1888 -0.0641 0.3076 0.058 Uiso 1 1 calc R . . C16 C 0.0596(4) -0.0265(3) 0.1522(2) 0.0617(9) Uani 1 1 d . . . H16A H 0.0167 -0.0872 0.1378 0.093 Uiso 1 1 calc R . . H16B H 0.1463 -0.0700 0.2174 0.093 Uiso 1 1 calc R . . H16C H 0.1113 0.0249 0.0849 0.093 Uiso 1 1 calc R . . C15 C -0.1567(3) 0.1626(2) 0.0966(2) 0.0291(5) Uani 1 1 d . . . H15 H -0.2469 0.2107 0.1175 0.035 Uiso 1 1 calc R . . O1 O -0.14664(15) 0.44598(12) 0.04564(10) 0.0167(3) Uani 1 1 d . . . N1 N -0.13279(19) 0.49153(14) -0.18019(12) 0.0168(3) Uani 1 1 d . . . C2 C -0.3164(2) 0.47048(16) 0.02228(15) 0.0144(3) Uani 1 1 d . . . C5 C -0.0589(2) 0.51259(19) -0.28826(16) 0.0232(4) Uani 1 1 d . . . H5A H 0.0341 0.5567 -0.2979 0.028 Uiso 1 1 calc R . . H5B H -0.1483 0.5645 -0.3523 0.028 Uiso 1 1 calc R . . C3 C -0.3947(2) 0.51308(16) -0.08797(15) 0.0146(3) Uani 1 1 d . . . C4 C -0.2966(2) 0.52901(17) -0.18504(15) 0.0170(3) Uani 1 1 d . . . H4 H -0.3579 0.5704 -0.2581 0.020 Uiso 1 1 calc R . . C1 C -0.4257(2) 0.45690(16) 0.10892(15) 0.0158(3) Uani 1 1 d . . . H1 H -0.3772 0.4264 0.1845 0.019 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 0.01060(10) 0.02384(13) 0.01529(11) -0.01004(9) 0.00128(8) -0.00159(8) O2 0.0151(6) 0.0253(7) 0.0189(7) -0.0094(6) 0.0004(5) -0.0015(5) N2 0.0141(7) 0.0270(9) 0.0223(8) -0.0138(7) 0.0035(6) -0.0049(6) C13 0.0177(9) 0.0282(11) 0.0243(10) -0.0059(9) -0.0027(8) -0.0001(8) N3 0.0158(7) 0.0225(8) 0.0197(8) -0.0077(7) -0.0004(6) -0.0037(6) C12 0.0143(8) 0.0209(9) 0.0234(10) -0.0105(8) 0.0004(7) -0.0033(7) C14 0.0288(11) 0.0289(11) 0.0192(10) -0.0091(9) 0.0029(8) -0.0055(9) C11 0.0167(9) 0.0490(14) 0.0301(11) -0.0237(11) 0.0012(8) -0.0022(9) C7 0.0185(9) 0.0224(10) 0.0204(9) -0.0116(8) 0.0044(7) -0.0058(8) C9 0.0243(11) 0.0484(15) 0.0401(13) -0.0274(12) 0.0073(10) 0.0035(10) C8 0.0250(10) 0.0330(11) 0.0272(11) -0.0194(9) 0.0073(8) -0.0045(9) C6 0.0209(9) 0.0389(12) 0.0222(10) -0.0188(9) 0.0006(8) -0.0032(9) C10 0.0178(10) 0.0675(18) 0.0438(14) -0.0345(14) -0.0021(10) 0.0093(11) S 0.0231(2) 0.0270(3) 0.0228(2) -0.0126(2) -0.00024(19) -0.0046(2) F1 0.0550(9) 0.0692(10) 0.0650(10) -0.0556(9) 0.0305(8) -0.0306(8) F2 0.0781(12) 0.0301(8) 0.0692(12) -0.0102(8) 0.0322(10) -0.0188(8) O4 0.0347(9) 0.0587(11) 0.0362(9) -0.0341(9) 0.0036(7) -0.0069(8) F3 0.0327(8) 0.0918(12) 0.0627(10) -0.0555(10) 0.0192(7) -0.0324(8) O6 0.0219(8) 0.0581(11) 0.0435(10) -0.0273(9) 0.0002(7) -0.0080(8) O5 0.0569(12) 0.0276(9) 0.0351(9) -0.0062(7) -0.0025(8) -0.0021(8) C18 0.0344(12) 0.0395(13) 0.0375(13) -0.0243(11) 0.0152(10) -0.0145(10) O3 0.0396(9) 0.0347(9) 0.0330(9) -0.0119(7) -0.0014(7) -0.0134(7) N4 0.0272(9) 0.0300(10) 0.0291(10) -0.0153(8) -0.0016(7) -0.0007(8) C17 0.0425(14) 0.0365(13) 0.0351(13) -0.0141(11) 0.0052(11) -0.0114(11) C16 0.064(2) 0.0609(19) 0.0405(16) -0.0256(15) -0.0069(14) 0.0309(15) C15 0.0235(10) 0.0264(11) 0.0404(13) -0.0167(10) 0.0004(9) -0.0074(9) O1 0.0078(5) 0.0258(7) 0.0171(6) -0.0110(6) 0.0003(5) -0.0021(5) N1 0.0132(7) 0.0220(8) 0.0143(7) -0.0073(6) 0.0032(6) -0.0045(6) C2 0.0108(8) 0.0166(9) 0.0154(8) -0.0071(7) -0.0002(6) -0.0022(7) C5 0.0179(9) 0.0313(11) 0.0155(9) -0.0078(8) 0.0062(7) -0.0026(8) C3 0.0109(8) 0.0179(9) 0.0144(8) -0.0067(7) 0.0015(6) -0.0034(7) C4 0.0137(8) 0.0203(9) 0.0150(8) -0.0064(7) 0.0007(6) -0.0035(7) C1 0.0115(8) 0.0200(9) 0.0140(8) -0.0066(7) 0.0002(6) -0.0023(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 Cu O1 1.9297(12) . ? Cu N1 1.9653(16) . ? Cu O2 2.0010(14) . ? Cu N2 2.0754(15) . ? Cu O1 2.4344(13) 2_565 ? Cu O3 2.5652(16) . ? O2 C12 1.253(2) . ? N2 C11 1.342(3) . ? N2 C7 1.356(2) . ? C13 N3 1.462(2) . ? N3 C12 1.310(2) . ? N3 C14 1.463(2) . ? C11 C10 1.382(3) . ? C7 C8 1.389(3) . ? C7 C6 1.495(3) . ? C9 C8 1.370(3) . ? C9 C10 1.374(3) . ? C6 C5 1.523(3) . ? S O5 1.4317(18) . ? S O6 1.4353(16) . ? S O4 1.4379(16) . ? S C18 1.810(2) . ? F1 C18 1.326(2) . ? F2 C18 1.330(3) . ? F3 C18 1.345(3) . ? O3 C15 1.228(3) . ? N4 C15 1.320(3) . ? N4 C16 1.449(3) . ? N4 C17 1.459(3) . ? O1 C2 1.338(2) . ? O1 Cu 2.4344(13) 2_565 ? N1 C4 1.286(2) . ? N1 C5 1.465(2) . ? C2 C1 1.396(2) . ? C2 C3 1.412(2) . ? C3 C1 1.406(2) 2_465 ? C3 C4 1.447(2) . ? C1 C3 1.406(2) 2_465 ? 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 O1 Cu N1 90.85(6) . . ? O1 Cu O2 88.07(5) . . ? N1 Cu O2 175.04(6) . . ? O1 Cu N2 175.61(6) . . ? N1 Cu N2 93.51(6) . . ? O2 Cu N2 87.55(6) . . ? O1 Cu O1 83.37(5) . 2_565 ? N1 Cu O1 96.50(6) . 2_565 ? O2 Cu O1 88.19(5) . 2_565 ? N2 Cu O1 96.57(5) . 2_565 ? O1 Cu O3 90.63(5) . . ? N1 Cu O3 89.17(6) . . ? O2 Cu O3 86.00(5) . . ? N2 Cu O3 88.99(6) . . ? O1 Cu O3 171.78(5) 2_565 . ? C12 O2 Cu 127.18(12) . . ? C11 N2 C7 117.32(16) . . ? C11 N2 Cu 118.20(13) . . ? C7 N2 Cu 124.34(13) . . ? C12 N3 C13 120.26(16) . . ? C12 N3 C14 121.92(16) . . ? C13 N3 C14 117.81(16) . . ? O2 C12 N3 123.07(17) . . ? N2 C11 C10 123.5(2) . . ? N2 C7 C8 121.37(18) . . ? N2 C7 C6 119.11(16) . . ? C8 C7 C6 119.50(17) . . ? C8 C9 C10 118.56(19) . . ? C9 C8 C7 120.32(19) . . ? C7 C6 C5 113.83(16) . . ? C9 C10 C11 118.8(2) . . ? O5 S O6 115.19(11) . . ? O5 S O4 115.05(11) . . ? O6 S O4 115.08(10) . . ? O5 S C18 102.45(11) . . ? O6 S C18 103.64(11) . . ? O4 S C18 102.84(10) . . ? F1 C18 F2 108.40(19) . . ? F1 C18 F3 107.63(19) . . ? F2 C18 F3 106.77(18) . . ? F1 C18 S 112.27(15) . . ? F2 C18 S 111.13(17) . . ? F3 C18 S 110.42(16) . . ? C15 O3 Cu 109.80(13) . . ? C15 N4 C16 120.5(2) . . ? C15 N4 C17 122.19(19) . . ? C16 N4 C17 117.3(2) . . ? O3 C15 N4 125.8(2) . . ? C2 O1 Cu 123.12(10) . . ? C2 O1 Cu 118.85(10) . 2_565 ? Cu O1 Cu 96.63(5) . 2_565 ? C4 N1 C5 116.53(16) . . ? C4 N1 Cu 125.06(12) . . ? C5 N1 Cu 117.86(12) . . ? O1 C2 C1 119.87(15) . . ? O1 C2 C3 123.41(15) . . ? C1 C2 C3 116.70(15) . . ? N1 C5 C6 108.90(16) . . ? C1 C3 C2 121.15(15) 2_465 . ? C1 C3 C4 116.40(16) 2_465 . ? C2 C3 C4 122.45(15) . . ? N1 C4 C3 125.13(17) . . ? C2 C1 C3 122.12(16) . 2_465 ? 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 O1 Cu O2 C12 15.27(15) . . . . ? N1 Cu O2 C12 -62.2(7) . . . . ? N2 Cu O2 C12 -164.65(15) . . . . ? O1 Cu O2 C12 98.69(15) 2_565 . . . ? O3 Cu O2 C12 -75.49(15) . . . . ? O1 Cu N2 C11 -21.8(8) . . . . ? N1 Cu N2 C11 164.14(16) . . . . ? O2 Cu N2 C11 -20.72(16) . . . . ? O1 Cu N2 C11 67.18(16) 2_565 . . . ? O3 Cu N2 C11 -106.76(16) . . . . ? O1 Cu N2 C7 153.8(7) . . . . ? N1 Cu N2 C7 -20.34(16) . . . . ? O2 Cu N2 C7 154.81(15) . . . . ? O1 Cu N2 C7 -117.30(15) 2_565 . . . ? O3 Cu N2 C7 68.77(15) . . . . ? Cu O2 C12 N3 -175.70(13) . . . . ? C13 N3 C12 O2 1.7(3) . . . . ? C14 N3 C12 O2 -179.57(17) . . . . ? C7 N2 C11 C10 -2.6(3) . . . . ? Cu N2 C11 C10 173.2(2) . . . . ? C11 N2 C7 C8 2.9(3) . . . . ? Cu N2 C7 C8 -172.63(14) . . . . ? C11 N2 C7 C6 -175.35(18) . . . . ? Cu N2 C7 C6 9.1(2) . . . . ? C10 C9 C8 C7 -1.9(4) . . . . ? N2 C7 C8 C9 -0.7(3) . . . . ? C6 C7 C8 C9 177.6(2) . . . . ? N2 C7 C6 C5 40.2(2) . . . . ? C8 C7 C6 C5 -138.13(18) . . . . ? C8 C9 C10 C11 2.3(4) . . . . ? N2 C11 C10 C9 0.0(4) . . . . ? O5 S C18 F1 59.6(2) . . . . ? O6 S C18 F1 -60.5(2) . . . . ? O4 S C18 F1 179.32(18) . . . . ? O5 S C18 F2 -178.76(15) . . . . ? O6 S C18 F2 61.10(17) . . . . ? O4 S C18 F2 -59.09(17) . . . . ? O5 S C18 F3 -60.47(18) . . . . ? O6 S C18 F3 179.39(15) . . . . ? O4 S C18 F3 59.20(18) . . . . ? O1 Cu O3 C15 -42.33(15) . . . . ? N1 Cu O3 C15 -133.17(15) . . . . ? O2 Cu O3 C15 45.69(15) . . . . ? N2 Cu O3 C15 133.30(16) . . . . ? O1 Cu O3 C15 0.6(4) 2_565 . . . ? Cu O3 C15 N4 -110.6(2) . . . . ? C16 N4 C15 O3 1.3(4) . . . . ? C17 N4 C15 O3 179.8(2) . . . . ? N1 Cu O1 C2 34.54(13) . . . . ? O2 Cu O1 C2 -140.61(13) . . . . ? N2 Cu O1 C2 -139.6(7) . . . . ? O1 Cu O1 C2 130.99(15) 2_565 . . . ? O3 Cu O1 C2 -54.64(13) . . . . ? N1 Cu O1 Cu -96.44(6) . . . 2_565 ? O2 Cu O1 Cu 88.40(5) . . . 2_565 ? N2 Cu O1 Cu 89.4(8) . . . 2_565 ? O1 Cu O1 Cu 0.0 2_565 . . 2_565 ? O3 Cu O1 Cu 174.38(5) . . . 2_565 ? O1 Cu N1 C4 -23.44(15) . . . . ? O2 Cu N1 C4 53.9(7) . . . . ? N2 Cu N1 C4 156.11(15) . . . . ? O1 Cu N1 C4 -106.86(15) 2_565 . . . ? O3 Cu N1 C4 67.17(15) . . . . ? O1 Cu N1 C5 165.42(13) . . . . ? O2 Cu N1 C5 -117.2(6) . . . . ? N2 Cu N1 C5 -15.03(14) . . . . ? O1 Cu N1 C5 82.00(13) 2_565 . . . ? O3 Cu N1 C5 -103.97(14) . . . . ? Cu O1 C2 C1 151.61(13) . . . . ? Cu O1 C2 C1 -87.27(17) 2_565 . . . ? Cu O1 C2 C3 -29.9(2) . . . . ? Cu O1 C2 C3 91.21(17) 2_565 . . . ? C4 N1 C5 C6 -112.68(19) . . . . ? Cu N1 C5 C6 59.22(18) . . . . ? C7 C6 C5 N1 -77.6(2) . . . . ? O1 C2 C3 C1 -176.94(16) . . . 2_465 ? C1 C2 C3 C1 1.6(3) . . . 2_465 ? O1 C2 C3 C4 2.7(3) . . . . ? C1 C2 C3 C4 -178.80(16) . . . . ? C5 N1 C4 C3 177.66(17) . . . . ? Cu N1 C4 C3 6.4(3) . . . . ? C1 C3 C4 N1 -170.44(17) 2_465 . . . ? C2 C3 C4 N1 9.9(3) . . . . ? O1 C2 C1 C3 176.98(16) . . . 2_465 ? C3 C2 C1 C3 -1.6(3) . . . 2_465 ? _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 32.64 _diffrn_measured_fraction_theta_full 0.886 _refine_diff_density_max 0.451 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.078 # Attachment 'compound5.cif' data_lerner22 _database_code_depnum_ccdc_archive 'CCDC 613045' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H48 B2 Cu2 F8 N8 O6' _chemical_formula_weight 965.50 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' B B 0.0013 0.0007 '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' O O 0.0106 0.0060 '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 7.8730(9) _cell_length_b 11.3337(17) _cell_length_c 12.3291(15) _cell_angle_alpha 110.619(5) _cell_angle_beta 96.191(6) _cell_angle_gamma 96.164(5) _cell_volume 1011.1(2) _cell_formula_units_Z 1 _cell_measurement_temperature 157(2) _cell_measurement_reflns_used 255 _cell_measurement_theta_min 3 _cell_measurement_theta_max 26 _exptl_crystal_description rod _exptl_crystal_colour dark_brown _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.143 _exptl_absorpt_correction_type 'empirical, SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.801 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 157(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type SIEMENS_SMART_CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 88 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1200 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 8967 _diffrn_reflns_av_R_equivalents 0.1008 _diffrn_reflns_av_sigmaI/netI 0.2272 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 29.10 _reflns_number_total 4481 _reflns_number_gt 2107 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.04P)^2^] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4481 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1953 _refine_ls_R_factor_gt 0.0804 _refine_ls_wR_factor_ref 0.1390 _refine_ls_wR_factor_gt 0.1101 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _refine_ls_shift/su_max 0.002 _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 -0.00114(9) 0.12294(8) -0.04902(7) 0.0211(2) Uani 1 1 d . . . O3 O -0.1430(4) 0.0630(3) 0.0442(3) 0.0195(10) Uani 1 1 d . . . O2 O 0.1642(4) 0.2227(4) 0.0998(3) 0.0220(10) Uani 1 1 d . . . N3 N -0.1753(6) 0.0437(4) -0.1915(4) 0.0205(12) Uani 1 1 d . . . N4 N 0.1791(6) 0.1842(4) -0.1381(4) 0.0203(12) Uani 1 1 d . . . N2 N 0.2462(6) 0.3096(5) 0.2957(4) 0.0258(13) Uani 1 1 d . . . C9 C 0.4479(8) 0.2565(6) -0.2418(6) 0.0373(18) Uani 1 1 d . . . H9 H 0.5407 0.2805 -0.2768 0.045 Uiso 1 1 calc R . . C4 C -0.3330(7) 0.0004(5) -0.1917(5) 0.0205(14) Uani 1 1 d . . . H4 H -0.4060 -0.0342 -0.2657 0.025 Uiso 1 1 calc R . . N1 N -0.0881(6) 0.4652(5) 0.1896(4) 0.0298(13) Uani 1 1 d . . . C2 C -0.4111(7) -0.0013(5) -0.0914(5) 0.0151(13) Uani 1 1 d . . . O1 O -0.1460(5) 0.3205(4) 0.0015(4) 0.0406(12) Uani 1 1 d . . . C1 C -0.3173(7) 0.0359(5) 0.0214(5) 0.0162(13) Uani 1 1 d . . . C11 C 0.3017(8) 0.2848(6) -0.0777(6) 0.0346(18) Uani 1 1 d . . . H11 H 0.2958 0.3320 0.0021 0.042 Uiso 1 1 calc R . . C15 C 0.1333(7) 0.2463(6) 0.2017(5) 0.0247(15) Uani 1 1 d . . . H15 H 0.0207 0.2165 0.2116 0.030 Uiso 1 1 calc R . . C3 C -0.5910(7) -0.0365(5) -0.1112(5) 0.0185(14) Uani 1 1 d . . . H3 H -0.6519 -0.0616 -0.1886 0.022 Uiso 1 1 calc R . . C5 C -0.1314(7) 0.0412(6) -0.3054(5) 0.0265(16) Uani 1 1 d . . . H5A H -0.1377 0.1258 -0.3108 0.032 Uiso 1 1 calc R . . H5B H -0.2172 -0.0226 -0.3694 0.032 Uiso 1 1 calc R . . C7 C 0.1870(7) 0.1196(5) -0.2518(5) 0.0218(14) Uani 1 1 d . . . C8 C 0.3211(7) 0.1544(6) -0.3047(5) 0.0280(16) Uani 1 1 d . . . H8 H 0.3251 0.1072 -0.3849 0.034 Uiso 1 1 calc R . . C17 C 0.2098(8) 0.3345(6) 0.4152(5) 0.0362(18) Uani 1 1 d . . . H17A H 0.0924 0.2934 0.4119 0.054 Uiso 1 1 calc R . . H17B H 0.2196 0.4268 0.4573 0.054 Uiso 1 1 calc R . . H17C H 0.2931 0.3001 0.4562 0.054 Uiso 1 1 calc R . . C16 C 0.4203(7) 0.3595(6) 0.2858(5) 0.0302(16) Uani 1 1 d . . . H16A H 0.4380 0.3247 0.2037 0.045 Uiso 1 1 calc R . . H16B H 0.5056 0.3346 0.3342 0.045 Uiso 1 1 calc R . . H16C H 0.4342 0.4528 0.3127 0.045 Uiso 1 1 calc R . . C6 C 0.0481(7) 0.0083(6) -0.3215(5) 0.0263(15) Uani 1 1 d . . . H6A H 0.0643 -0.0643 -0.2965 0.032 Uiso 1 1 calc R . . H6B H 0.0592 -0.0186 -0.4057 0.032 Uiso 1 1 calc R . . C14 C -0.1345(8) 0.5082(7) 0.3060(6) 0.045(2) Uani 1 1 d . . . H14A H -0.1810 0.5883 0.3211 0.068 Uiso 1 1 calc R . . H14B H -0.0317 0.5220 0.3640 0.068 Uiso 1 1 calc R . . H14C H -0.2223 0.4433 0.3117 0.068 Uiso 1 1 calc R . . C12 C -0.1763(8) 0.3619(6) 0.1031(6) 0.0369(18) Uani 1 1 d . . . H12 H -0.2705 0.3164 0.1213 0.044 Uiso 1 1 calc R . . C13 C 0.0617(8) 0.5381(6) 0.1700(6) 0.044(2) Uani 1 1 d . . . H13A H 0.1063 0.4844 0.1012 0.065 Uiso 1 1 calc R . . H13B H 0.1519 0.5656 0.2391 0.065 Uiso 1 1 calc R . . H13C H 0.0277 0.6131 0.1567 0.065 Uiso 1 1 calc R . . C10 C 0.4357(8) 0.3220(6) -0.1275(6) 0.0375(18) Uani 1 1 d . . . H10 H 0.5202 0.3938 -0.0818 0.045 Uiso 1 1 calc R . . F1 F -0.2418(5) -0.7452(4) 0.3872(3) 0.0538(12) Uani 1 1 d . . . F2 F -0.1425(5) -0.7743(4) 0.5527(3) 0.0538(12) Uani 1 1 d . . . B B -0.2858(11) -0.7542(8) 0.4907(7) 0.036(2) Uani 1 1 d . . . F3 F -0.3383(5) -0.6410(4) 0.5559(3) 0.0579(12) Uani 1 1 d . . . F4 F -0.4178(6) -0.8525(4) 0.4637(4) 0.0795(16) 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 0.0147(4) 0.0267(5) 0.0200(5) 0.0078(3) 0.0030(3) -0.0022(3) O3 0.011(2) 0.029(3) 0.017(2) 0.008(2) 0.0024(17) -0.0006(18) O2 0.017(2) 0.032(3) 0.013(2) 0.006(2) 0.0028(19) -0.0029(19) N3 0.017(3) 0.022(3) 0.025(3) 0.010(2) 0.010(2) 0.004(2) N4 0.021(3) 0.023(3) 0.013(3) 0.003(2) 0.005(2) -0.002(2) N2 0.019(3) 0.035(3) 0.020(3) 0.008(3) 0.000(2) -0.002(2) C9 0.033(4) 0.049(5) 0.034(4) 0.020(4) 0.015(3) -0.002(4) C4 0.025(3) 0.018(3) 0.019(3) 0.007(3) -0.001(3) 0.006(3) N1 0.024(3) 0.035(3) 0.023(3) 0.002(3) 0.007(2) -0.001(3) C2 0.011(3) 0.019(3) 0.018(3) 0.008(3) 0.007(3) 0.005(2) O1 0.048(3) 0.038(3) 0.036(3) 0.012(3) 0.008(2) 0.009(2) C1 0.010(3) 0.015(3) 0.021(3) 0.006(3) -0.002(3) 0.000(2) C11 0.039(4) 0.038(4) 0.025(4) 0.013(3) 0.008(3) -0.006(3) C15 0.018(3) 0.025(4) 0.027(4) 0.006(3) 0.002(3) -0.001(3) C3 0.013(3) 0.021(3) 0.019(3) 0.005(3) -0.002(3) 0.003(3) C5 0.023(4) 0.034(4) 0.019(4) 0.007(3) 0.005(3) 0.000(3) C7 0.022(3) 0.024(4) 0.020(4) 0.009(3) 0.005(3) 0.002(3) C8 0.026(4) 0.034(4) 0.026(4) 0.011(3) 0.015(3) 0.007(3) C17 0.044(4) 0.040(4) 0.016(4) 0.004(3) 0.001(3) -0.004(3) C16 0.018(3) 0.033(4) 0.033(4) 0.006(3) 0.000(3) -0.001(3) C6 0.020(3) 0.037(4) 0.022(4) 0.008(3) 0.009(3) 0.003(3) C14 0.041(4) 0.055(5) 0.038(5) 0.014(4) 0.012(4) 0.007(4) C12 0.034(4) 0.033(4) 0.045(5) 0.016(4) 0.007(4) 0.009(3) C13 0.049(5) 0.034(4) 0.045(5) 0.020(4) -0.001(4) -0.012(4) C10 0.038(4) 0.042(5) 0.032(4) 0.018(4) 0.007(3) -0.014(3) F1 0.054(3) 0.086(3) 0.040(3) 0.038(2) 0.014(2) 0.028(2) F2 0.069(3) 0.054(3) 0.040(3) 0.022(2) -0.005(2) 0.013(2) B 0.048(5) 0.026(5) 0.034(5) 0.017(4) 0.000(4) -0.003(4) F3 0.067(3) 0.046(3) 0.051(3) 0.006(2) 0.010(2) 0.013(2) F4 0.080(3) 0.062(3) 0.073(3) 0.011(3) 0.008(3) -0.036(3) _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 O3 1.921(3) . ? Cu1 N3 1.969(5) . ? Cu1 O2 2.012(4) . ? Cu1 N4 2.089(4) . ? Cu1 O3 2.514(4) 2 ? Cu1 O1 2.534(5) . ? O3 C1 1.349(6) . ? O2 C15 1.246(6) . ? N3 C4 1.285(6) . ? N3 C5 1.474(6) . ? N4 C11 1.340(7) . ? N4 C7 1.345(7) . ? N2 C15 1.305(6) . ? N2 C16 1.461(6) . ? N2 C17 1.465(7) . ? C9 C10 1.362(8) . ? C9 C8 1.375(8) . ? C4 C2 1.445(7) . ? N1 C12 1.333(7) . ? N1 C14 1.445(7) . ? N1 C13 1.457(7) . ? C2 C1 1.399(7) . ? C2 C3 1.400(7) . ? O1 C12 1.233(7) . ? C1 C3 1.383(7) 2_455 ? C11 C10 1.376(7) . ? C3 C1 1.384(7) 2_455 ? C5 C6 1.516(7) . ? C7 C8 1.392(7) . ? C7 C6 1.504(7) . ? F1 B 1.392(8) . ? F2 B 1.378(9) . ? B F4 1.359(8) . ? B F3 1.386(9) . ? 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 O3 Cu1 N3 92.78(16) . . ? O3 Cu1 O2 87.64(15) . . ? N3 Cu1 O2 173.24(19) . . ? O3 Cu1 N4 172.93(18) . . ? N3 Cu1 N4 92.95(18) . . ? O2 Cu1 N4 87.16(16) . . ? O3 Cu1 O3 80.53(15) . 2 ? N3 Cu1 O3 102.02(16) . 2 ? O2 Cu1 O3 84.71(14) . 2 ? N4 Cu1 O3 94.22(16) . 2 ? O3 Cu1 O1 88.65(15) . . ? N3 Cu1 O1 88.42(17) . . ? O2 Cu1 O1 84.84(15) . . ? N4 Cu1 O1 95.65(17) . . ? O3 Cu1 O1 165.24(13) 2 . ? C1 O3 Cu1 124.7(3) . . ? C15 O2 Cu1 126.3(3) . . ? C4 N3 C5 115.9(5) . . ? C4 N3 Cu1 124.0(4) . . ? C5 N3 Cu1 119.9(3) . . ? C11 N4 C7 118.3(5) . . ? C11 N4 Cu1 119.0(4) . . ? C7 N4 Cu1 122.4(4) . . ? C15 N2 C16 120.4(5) . . ? C15 N2 C17 123.6(5) . . ? C16 N2 C17 116.1(5) . . ? C10 C9 C8 117.6(6) . . ? N3 C4 C2 126.9(5) . . ? C12 N1 C14 121.9(5) . . ? C12 N1 C13 120.6(5) . . ? C14 N1 C13 117.5(5) . . ? C1 C2 C3 120.5(5) . . ? C1 C2 C4 123.2(5) . . ? C3 C2 C4 116.2(5) . . ? C12 O1 Cu1 114.6(4) . . ? O3 C1 C3 119.4(5) . 2_455 ? O3 C1 C2 122.9(5) . . ? C3 C1 C2 117.5(5) 2_455 . ? N4 C11 C10 122.3(6) . . ? O2 C15 N2 124.0(5) . . ? C1 C3 C2 122.0(5) 2_455 . ? N3 C5 C6 111.8(5) . . ? N4 C7 C8 120.9(5) . . ? N4 C7 C6 119.0(5) . . ? C8 C7 C6 120.1(5) . . ? C9 C8 C7 120.5(6) . . ? C7 C6 C5 111.9(5) . . ? O1 C12 N1 125.6(6) . . ? C9 C10 C11 120.4(6) . . ? F4 B F2 110.8(6) . . ? F4 B F3 109.6(7) . . ? F2 B F3 110.0(6) . . ? F4 B F1 109.0(6) . . ? F2 B F1 108.7(6) . . ? F3 B F1 108.7(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 N3 Cu1 O3 C1 -25.7(4) . . . . ? O2 Cu1 O3 C1 147.5(4) . . . . ? N4 Cu1 O3 C1 -169.9(13) . . . . ? O3 Cu1 O3 C1 -127.5(4) 2 . . . ? O1 Cu1 O3 C1 62.6(4) . . . . ? O3 Cu1 O2 C15 -15.0(5) . . . . ? N3 Cu1 O2 C15 78.7(17) . . . . ? N4 Cu1 O2 C15 169.8(5) . . . . ? O3 Cu1 O2 C15 -95.7(5) 2 . . . ? O1 Cu1 O2 C15 73.9(5) . . . . ? O3 Cu1 N3 C4 13.5(5) . . . . ? O2 Cu1 N3 C4 -79.9(17) . . . . ? N4 Cu1 N3 C4 -170.6(5) . . . . ? O3 Cu1 N3 C4 94.4(5) 2 . . . ? O1 Cu1 N3 C4 -75.0(5) . . . . ? O3 Cu1 N3 C5 -171.6(4) . . . . ? O2 Cu1 N3 C5 95.0(16) . . . . ? N4 Cu1 N3 C5 4.3(4) . . . . ? O3 Cu1 N3 C5 -90.7(4) 2 . . . ? O1 Cu1 N3 C5 99.9(4) . . . . ? O3 Cu1 N4 C11 -60.6(17) . . . . ? N3 Cu1 N4 C11 155.3(5) . . . . ? O2 Cu1 N4 C11 -17.9(5) . . . . ? O3 Cu1 N4 C11 -102.4(5) 2 . . . ? O1 Cu1 N4 C11 66.6(5) . . . . ? O3 Cu1 N4 C7 113.1(14) . . . . ? N3 Cu1 N4 C7 -31.0(5) . . . . ? O2 Cu1 N4 C7 155.8(5) . . . . ? O3 Cu1 N4 C7 71.3(5) 2 . . . ? O1 Cu1 N4 C7 -119.7(5) . . . . ? C5 N3 C4 C2 -176.4(5) . . . . ? Cu1 N3 C4 C2 -1.3(8) . . . . ? N3 C4 C2 C1 -5.7(9) . . . . ? N3 C4 C2 C3 171.1(5) . . . . ? O3 Cu1 O1 C12 38.2(5) . . . . ? N3 Cu1 O1 C12 131.1(5) . . . . ? O2 Cu1 O1 C12 -49.5(4) . . . . ? N4 Cu1 O1 C12 -136.1(4) . . . . ? O3 Cu1 O1 C12 -4.4(8) 2 . . . ? Cu1 O3 C1 C3 -157.8(4) . . . 2_455 ? Cu1 O3 C1 C2 26.4(7) . . . . ? C3 C2 C1 O3 175.7(5) . . . . ? C4 C2 C1 O3 -7.6(8) . . . . ? C3 C2 C1 C3 -0.1(9) . . . 2_455 ? C4 C2 C1 C3 176.5(5) . . . 2_455 ? C7 N4 C11 C10 -1.3(10) . . . . ? Cu1 N4 C11 C10 172.7(5) . . . . ? Cu1 O2 C15 N2 178.7(4) . . . . ? C16 N2 C15 O2 1.0(9) . . . . ? C17 N2 C15 O2 -178.6(6) . . . . ? C1 C2 C3 C1 0.1(9) . . . 2_455 ? C4 C2 C3 C1 -176.7(5) . . . 2_455 ? C4 N3 C5 C6 -142.5(5) . . . . ? Cu1 N3 C5 C6 42.1(6) . . . . ? C11 N4 C7 C8 1.4(9) . . . . ? Cu1 N4 C7 C8 -172.3(4) . . . . ? C11 N4 C7 C6 -178.6(5) . . . . ? Cu1 N4 C7 C6 7.6(8) . . . . ? C10 C9 C8 C7 -0.7(10) . . . . ? N4 C7 C8 C9 -0.5(9) . . . . ? C6 C7 C8 C9 179.6(6) . . . . ? N4 C7 C6 C5 48.4(7) . . . . ? C8 C7 C6 C5 -131.7(6) . . . . ? N3 C5 C6 C7 -76.3(6) . . . . ? Cu1 O1 C12 N1 104.8(7) . . . . ? C14 N1 C12 O1 179.0(6) . . . . ? C13 N1 C12 O1 -2.0(10) . . . . ? C8 C9 C10 C11 0.9(10) . . . . ? N4 C11 C10 C9 0.1(10) . . . . ? _diffrn_measured_fraction_theta_max 0.827 _diffrn_reflns_theta_full 29.10 _diffrn_measured_fraction_theta_full 0.827 _refine_diff_density_max 0.555 _refine_diff_density_min -0.674 _refine_diff_density_rms 0.119