# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Piersandro Pallavicini' 'Franck Denat' 'Yuri Diaz-Fernandez' 'Luca Pasotti' 'Yoann Rousselin' 'Nicolas Sok' _publ_contact_author_name 'Piersandro Pallavicini' _publ_contact_author_email PSP@UNIPV.IT _publ_section_title ; The Cu(II) complex of a C-lipophilized 13aneN4 macrocycle with a further protonable amine as micellar anion receptor ; # Attachment '07pavia01.cif' data_07pavia01 _database_code_depnum_ccdc_archive 'CCDC 727679' # start Validation Reply Form _vrf_PLAT029_07pavia01 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.89 RESPONSE: Due to one small crystal dimension, the intensities were too low to get data completeness. ; # end Validation Reply Form #Added by publCIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H25 Cu N5, 2(C F3 O3 S), C2 H3 N' _chemical_formula_sum 'C14 H28 Cu F6 N6 O6 S2' _chemical_formula_weight 618.08 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' Cu Cu 0.3201 1.2651 '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' 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _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 9.3423(4) _cell_length_b 11.7120(6) _cell_length_c 22.8011(13) _cell_angle_alpha 90.00 _cell_angle_beta 101.232(2) _cell_angle_gamma 90.00 _cell_volume 2447.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 63368 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description Plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1268 _exptl_absorpt_coefficient_mu 1.151 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7810 _diffrn_reflns_av_R_equivalents 0.0676 _diffrn_reflns_av_sigmaI/netI 0.0837 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 27.76 _reflns_number_total 5027 _reflns_number_gt 3490 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia,1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1409P)^2^+4.1846P] 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 5027 _refine_ls_number_parameters 334 _refine_ls_number_restraints 2 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1287 _refine_ls_R_factor_gt 0.0908 _refine_ls_wR_factor_ref 0.2462 _refine_ls_wR_factor_gt 0.2175 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 C1 C -0.2964(7) -0.2877(5) -0.1765(3) 0.0295(14) Uani 1 1 d . . . H6A H -0.3793 -0.2649 -0.1578 0.035 Uiso 1 1 calc R . . H6B H -0.2049 -0.2623 -0.1501 0.035 Uiso 1 1 calc R . . C2 C -0.2949(7) -0.4167(5) -0.1837(3) 0.0308(14) Uani 1 1 d . . . H7A H -0.2823 -0.4544 -0.1442 0.037 Uiso 1 1 calc R . . H7B H -0.3878 -0.4431 -0.2086 0.037 Uiso 1 1 calc R . . C3 C -0.1754(7) -0.5643(5) -0.2359(3) 0.0329(15) Uani 1 1 d . . . H8 H -0.2409 -0.6101 -0.2152 0.039 Uiso 1 1 calc R . . C4 C -0.2421(8) -0.5625(5) -0.3025(3) 0.0334(15) Uani 1 1 d . . . H9A H -0.2281 -0.6374 -0.3207 0.040 Uiso 1 1 calc R . . H9B H -0.3482 -0.5471 -0.3084 0.040 Uiso 1 1 calc R . . C5 C -0.2422(7) -0.4491(5) -0.3953(3) 0.0309(14) Uani 1 1 d . . . H1A H -0.3476 -0.4670 -0.4011 0.037 Uiso 1 1 calc R . . H1B H -0.1983 -0.4974 -0.4227 0.037 Uiso 1 1 calc R . . C6 C -0.2200(7) -0.3227(5) -0.4078(3) 0.0304(14) Uani 1 1 d . . . H2A H -0.1152 -0.3073 -0.4065 0.037 Uiso 1 1 calc R . . H2B H -0.2749 -0.3024 -0.4480 0.037 Uiso 1 1 calc R . . C7 C -0.4344(7) -0.2406(5) -0.3750(3) 0.0304(14) Uani 1 1 d . . . H3A H -0.4804 -0.3169 -0.3756 0.037 Uiso 1 1 calc R . . H3B H -0.4662 -0.2057 -0.4150 0.037 Uiso 1 1 calc R . . C8 C -0.4842(7) -0.1668(5) -0.3284(3) 0.0309(14) Uani 1 1 d . . . H4A H -0.5883 -0.1472 -0.3425 0.037 Uiso 1 1 calc R . . H4B H -0.4279 -0.0947 -0.3244 0.037 Uiso 1 1 calc R . . C9 C -0.4665(7) -0.2226(5) -0.2672(3) 0.0292(14) Uani 1 1 d . . . H5A H -0.5203 -0.1772 -0.2420 0.035 Uiso 1 1 calc R . . H5B H -0.5105 -0.2998 -0.2719 0.035 Uiso 1 1 calc R . . C10 C -0.0237(7) -0.6168(5) -0.2213(3) 0.0311(14) Uani 1 1 d . . . H10A H 0.0416 -0.5739 -0.2427 0.037 Uiso 1 1 calc R . . H10B H 0.0150 -0.6087 -0.1779 0.037 Uiso 1 1 calc R . . C11 C 0.3753(9) -0.3281(7) -0.0635(4) 0.0479(19) Uani 1 1 d . . . C12 C 0.2165(8) -0.4727(6) -0.4284(4) 0.0437(18) Uani 1 1 d . . . C13 C 0.0507(12) -0.6706(8) 0.0172(5) 0.070(3) Uani 1 1 d . . . H13A H 0.1366 -0.6220 0.0295 0.106 Uiso 1 1 calc R . . H13B H 0.0820 -0.7490 0.0114 0.106 Uiso 1 1 calc R . . H13C H -0.0087 -0.6696 0.0482 0.106 Uiso 1 1 calc R . . C14 C -0.0356(10) -0.6278(7) -0.0388(4) 0.055(2) Uani 1 1 d . . . Cu Cu -0.19015(7) -0.32879(5) -0.28228(3) 0.0226(3) Uani 1 1 d . . . F1 F 0.3202(6) -0.3360(5) -0.0145(2) 0.0680(15) Uani 1 1 d . . . F2 F 0.5059(5) -0.3767(5) -0.0521(3) 0.0748(16) Uani 1 1 d . . . F3 F 0.3936(7) -0.2185(4) -0.0744(3) 0.0807(18) Uani 1 1 d . . . F4 F 0.2310(6) -0.5814(4) -0.4439(2) 0.0684(15) Uani 1 1 d . . . F5 F 0.3142(6) -0.4121(4) -0.4509(2) 0.0649(15) Uani 1 1 d . . . F6 F 0.0840(6) -0.4371(5) -0.4552(3) 0.0720(15) Uani 1 1 d . . . N1 N -0.3107(6) -0.2326(4) -0.2363(3) 0.0269(11) Uani 1 1 d . . . H1F H -0.266(8) -0.167(6) -0.230(3) 0.040 Uiso 1 1 d . . . N2 N -0.1715(6) -0.4443(4) -0.2128(3) 0.0284(12) Uani 1 1 d . . . H1G H -0.089(9) -0.437(6) -0.187(4) 0.043 Uiso 1 1 d . . . N3 N -0.1690(6) -0.4708(4) -0.3316(2) 0.0265(11) Uani 1 1 d . . . H1D H -0.066(8) -0.487(6) -0.329(3) 0.040 Uiso 1 1 d . . . N4 N -0.2719(6) -0.2536(4) -0.3623(2) 0.0271(11) Uani 1 1 d D . . H1E H -0.233(7) -0.187(3) -0.363(4) 0.041 Uiso 1 1 d D . . N5 N -0.0209(6) -0.7396(4) -0.2377(3) 0.0302(12) Uani 1 1 d D . . H1H H -0.079(9) -0.770(7) -0.215(4) 0.045 Uiso 1 1 d . . . H2I H -0.071(7) -0.751(7) -0.2730(16) 0.045 Uiso 1 1 d D . . N6 N -0.1032(10) -0.5962(7) -0.0832(4) 0.071(2) Uani 1 1 d . . . O1 O 0.2461(6) -0.5129(4) -0.1055(3) 0.0525(14) Uani 1 1 d . . . O2 O 0.1181(5) -0.3344(4) -0.1341(2) 0.0427(12) Uani 1 1 d . . . O3 O 0.3283(6) -0.3820(5) -0.1753(3) 0.0512(14) Uani 1 1 d . . . O4 O 0.1382(5) -0.5330(4) -0.3328(2) 0.0357(11) Uani 1 1 d . . . O5 O 0.3950(5) -0.4925(4) -0.3258(2) 0.0360(11) Uani 1 1 d . . . O6 O 0.2188(5) -0.3369(4) -0.3411(2) 0.0407(12) Uani 1 1 d . . . S1 S 0.25351(18) -0.39777(14) -0.12757(8) 0.0337(4) Uani 1 1 d . . . S2 S 0.24683(17) -0.45665(13) -0.34797(8) 0.0290(4) 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 C1 0.035(3) 0.027(3) 0.030(4) 0.002(3) 0.016(3) 0.002(3) C2 0.032(3) 0.027(3) 0.037(4) 0.003(3) 0.016(3) -0.002(3) C3 0.042(4) 0.016(3) 0.043(4) 0.000(3) 0.015(3) -0.002(2) C4 0.046(4) 0.018(3) 0.039(4) 0.000(3) 0.015(3) 0.001(3) C5 0.037(4) 0.026(3) 0.032(4) -0.004(3) 0.013(3) 0.000(3) C6 0.039(4) 0.025(3) 0.029(3) 0.000(3) 0.013(3) 0.003(3) C7 0.032(3) 0.024(3) 0.036(4) 0.000(3) 0.008(3) 0.005(3) C8 0.031(3) 0.024(3) 0.039(4) 0.002(3) 0.010(3) 0.005(2) C9 0.036(3) 0.018(3) 0.040(4) -0.002(3) 0.020(3) 0.000(2) C10 0.033(3) 0.023(3) 0.039(4) -0.001(3) 0.011(3) -0.002(3) C11 0.048(5) 0.046(5) 0.046(5) 0.003(4) -0.001(4) -0.004(3) C12 0.050(5) 0.041(4) 0.040(5) -0.003(3) 0.009(3) -0.018(3) C13 0.093(7) 0.064(6) 0.058(6) -0.004(5) 0.024(5) 0.028(5) C14 0.071(6) 0.042(5) 0.057(6) -0.003(4) 0.023(5) 0.004(4) Cu 0.0272(4) 0.0124(4) 0.0313(5) -0.0011(3) 0.0131(3) 0.0003(3) F1 0.083(4) 0.083(4) 0.037(3) -0.013(2) 0.008(2) -0.011(3) F2 0.052(3) 0.080(4) 0.086(4) 0.014(3) -0.004(3) 0.001(3) F3 0.101(5) 0.040(3) 0.089(4) -0.002(3) -0.010(3) -0.024(3) F4 0.105(4) 0.054(3) 0.054(3) -0.025(2) 0.036(3) -0.020(3) F5 0.087(4) 0.072(3) 0.041(3) 0.004(2) 0.025(3) -0.040(3) F6 0.065(3) 0.084(4) 0.058(3) 0.002(3) -0.012(3) -0.012(3) N1 0.032(3) 0.017(2) 0.036(3) -0.005(2) 0.014(2) 0.001(2) N2 0.031(3) 0.020(2) 0.036(3) -0.002(2) 0.010(2) -0.001(2) N3 0.030(3) 0.020(2) 0.035(3) -0.002(2) 0.017(2) 0.003(2) N4 0.033(3) 0.017(2) 0.034(3) 0.001(2) 0.013(2) 0.001(2) N5 0.031(3) 0.021(3) 0.040(4) -0.002(2) 0.012(2) 0.004(2) N6 0.091(6) 0.063(5) 0.062(6) 0.012(4) 0.024(5) 0.024(4) O1 0.067(4) 0.027(3) 0.066(4) -0.006(2) 0.020(3) -0.006(2) O2 0.041(3) 0.044(3) 0.046(3) 0.001(2) 0.013(2) 0.010(2) O3 0.059(3) 0.057(3) 0.043(3) -0.001(3) 0.023(3) 0.008(3) O4 0.033(2) 0.028(2) 0.051(3) 0.006(2) 0.019(2) -0.0018(18) O5 0.032(2) 0.033(2) 0.047(3) 0.001(2) 0.017(2) 0.0007(19) O6 0.044(3) 0.030(3) 0.050(3) 0.003(2) 0.013(2) 0.005(2) S1 0.0396(9) 0.0248(8) 0.0374(10) -0.0050(7) 0.0093(7) 0.0016(7) S2 0.0302(8) 0.0226(8) 0.0366(9) 0.0017(6) 0.0125(7) 0.0010(6) _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 C1 N1 1.490(8) . ? C1 C2 1.520(8) . ? C1 H6A 0.9900 . ? C1 H6B 0.9900 . ? C2 N2 1.474(8) . ? C2 H7A 0.9900 . ? C2 H7B 0.9900 . ? C3 N2 1.499(7) . ? C3 C10 1.521(9) . ? C3 C4 1.525(10) . ? C3 H8 1.0000 . ? C4 N3 1.496(8) . ? C4 H9A 0.9900 . ? C4 H9B 0.9900 . ? C5 N3 1.501(9) . ? C5 C6 1.529(8) . ? C5 H1A 0.9900 . ? C5 H1B 0.9900 . ? C6 N4 1.470(8) . ? C6 H2A 0.9900 . ? C6 H2B 0.9900 . ? C7 N4 1.497(8) . ? C7 C8 1.512(9) . ? C7 H3A 0.9900 . ? C7 H3B 0.9900 . ? C8 C9 1.520(9) . ? C8 H4A 0.9900 . ? C8 H4B 0.9900 . ? C9 N1 1.493(9) . ? C9 H5A 0.9900 . ? C9 H5B 0.9900 . ? C10 N5 1.487(8) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 F1 1.319(10) . ? C11 F2 1.325(9) . ? C11 F3 1.326(9) . ? C11 S1 1.857(8) . ? C12 F5 1.335(8) . ? C12 F4 1.336(9) . ? C12 F6 1.336(9) . ? C12 S2 1.811(8) . ? C13 C14 1.459(13) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N6 1.145(12) . ? Cu N1 2.025(5) . ? Cu N4 2.035(5) . ? Cu N3 2.039(5) . ? Cu N2 2.065(6) . ? Cu N5 2.199(5) 2_554 ? N1 H1F 0.87(8) . ? N2 H1G 0.88(8) . ? N3 H1D 0.98(7) . ? N4 H1E 0.86(2) . ? N5 Cu 2.199(5) 2_544 ? N5 H1H 0.89(8) . ? N5 H2I 0.86(2) . ? O1 S1 1.446(5) . ? O2 S1 1.449(5) . ? O3 S1 1.415(5) . ? O4 S2 1.444(4) . ? O5 S2 1.440(5) . ? O6 S2 1.441(5) . ? 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 C1 C2 109.4(5) . . ? N1 C1 H6A 109.8 . . ? C2 C1 H6A 109.8 . . ? N1 C1 H6B 109.8 . . ? C2 C1 H6B 109.8 . . ? H6A C1 H6B 108.2 . . ? N2 C2 C1 107.0(5) . . ? N2 C2 H7A 110.3 . . ? C1 C2 H7A 110.3 . . ? N2 C2 H7B 110.3 . . ? C1 C2 H7B 110.3 . . ? H7A C2 H7B 108.6 . . ? N2 C3 C10 110.1(5) . . ? N2 C3 C4 108.3(5) . . ? C10 C3 C4 114.0(6) . . ? N2 C3 H8 108.1 . . ? C10 C3 H8 108.1 . . ? C4 C3 H8 108.1 . . ? N3 C4 C3 108.6(5) . . ? N3 C4 H9A 110.0 . . ? C3 C4 H9A 110.0 . . ? N3 C4 H9B 110.0 . . ? C3 C4 H9B 110.0 . . ? H9A C4 H9B 108.4 . . ? N3 C5 C6 106.9(5) . . ? N3 C5 H1A 110.3 . . ? C6 C5 H1A 110.3 . . ? N3 C5 H1B 110.3 . . ? C6 C5 H1B 110.3 . . ? H1A C5 H1B 108.6 . . ? N4 C6 C5 109.0(5) . . ? N4 C6 H2A 109.9 . . ? C5 C6 H2A 109.9 . . ? N4 C6 H2B 109.9 . . ? C5 C6 H2B 109.9 . . ? H2A C6 H2B 108.3 . . ? N4 C7 C8 111.1(5) . . ? N4 C7 H3A 109.4 . . ? C8 C7 H3A 109.4 . . ? N4 C7 H3B 109.4 . . ? C8 C7 H3B 109.4 . . ? H3A C7 H3B 108.0 . . ? C7 C8 C9 113.9(5) . . ? C7 C8 H4A 108.8 . . ? C9 C8 H4A 108.8 . . ? C7 C8 H4B 108.8 . . ? C9 C8 H4B 108.8 . . ? H4A C8 H4B 107.7 . . ? N1 C9 C8 112.9(5) . . ? N1 C9 H5A 109.0 . . ? C8 C9 H5A 109.0 . . ? N1 C9 H5B 109.0 . . ? C8 C9 H5B 109.0 . . ? H5A C9 H5B 107.8 . . ? N5 C10 C3 113.4(5) . . ? N5 C10 H10A 108.9 . . ? C3 C10 H10A 108.9 . . ? N5 C10 H10B 108.9 . . ? C3 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? F1 C11 F2 107.5(7) . . ? F1 C11 F3 108.2(7) . . ? F2 C11 F3 107.7(7) . . ? F1 C11 S1 110.8(5) . . ? F2 C11 S1 111.4(6) . . ? F3 C11 S1 111.0(6) . . ? F5 C12 F4 107.0(6) . . ? F5 C12 F6 107.5(7) . . ? F4 C12 F6 108.0(6) . . ? F5 C12 S2 110.5(5) . . ? F4 C12 S2 111.3(5) . . ? F6 C12 S2 112.3(6) . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N6 C14 C13 178.7(10) . . ? N1 Cu N4 94.2(2) . . ? N1 Cu N3 149.7(2) . . ? N4 Cu N3 85.3(2) . . ? N1 Cu N2 86.5(2) . . ? N4 Cu N2 158.7(2) . . ? N3 Cu N2 83.5(2) . . ? N1 Cu N5 101.2(2) . 2_554 ? N4 Cu N5 98.3(2) . 2_554 ? N3 Cu N5 108.8(2) . 2_554 ? N2 Cu N5 102.4(2) . 2_554 ? C1 N1 C9 111.8(5) . . ? C1 N1 Cu 105.9(4) . . ? C9 N1 Cu 112.8(4) . . ? C1 N1 H1F 105(5) . . ? C9 N1 H1F 114(5) . . ? Cu N1 H1F 107(5) . . ? C2 N2 C3 113.4(5) . . ? C2 N2 Cu 104.2(4) . . ? C3 N2 Cu 110.6(4) . . ? C2 N2 H1G 109(5) . . ? C3 N2 H1G 107(5) . . ? Cu N2 H1G 113(5) . . ? C4 N3 C5 112.9(5) . . ? C4 N3 Cu 103.8(4) . . ? C5 N3 Cu 108.7(3) . . ? C4 N3 H1D 111(4) . . ? C5 N3 H1D 111(4) . . ? Cu N3 H1D 109(4) . . ? C6 N4 C7 112.3(5) . . ? C6 N4 Cu 106.0(4) . . ? C7 N4 Cu 114.1(4) . . ? C6 N4 H1E 107(5) . . ? C7 N4 H1E 109(5) . . ? Cu N4 H1E 109(5) . . ? C10 N5 Cu 117.8(4) . 2_544 ? C10 N5 H1H 101(5) . . ? Cu N5 H1H 108(5) 2_544 . ? C10 N5 H2I 111(5) . . ? Cu N5 H2I 115(5) 2_544 . ? H1H N5 H2I 101(7) . . ? O3 S1 O1 117.0(3) . . ? O3 S1 O2 113.9(3) . . ? O1 S1 O2 114.4(3) . . ? O3 S1 C11 103.3(4) . . ? O1 S1 C11 101.5(4) . . ? O2 S1 C11 104.2(4) . . ? O5 S2 O6 115.3(3) . . ? O5 S2 O4 114.1(3) . . ? O6 S2 O4 115.2(3) . . ? O5 S2 C12 106.0(3) . . ? O6 S2 C12 102.4(3) . . ? O4 S2 C12 101.6(3) . . ? 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 C1 C2 N2 58.2(7) . . . . ? N2 C3 C4 N3 48.3(7) . . . . ? C10 C3 C4 N3 -74.7(6) . . . . ? N3 C5 C6 N4 -53.9(7) . . . . ? N4 C7 C8 C9 -69.9(7) . . . . ? C7 C8 C9 N1 70.9(7) . . . . ? N2 C3 C10 N5 174.5(5) . . . . ? C4 C3 C10 N5 -63.5(7) . . . . ? C2 C1 N1 C9 85.5(6) . . . . ? C2 C1 N1 Cu -37.7(6) . . . . ? C8 C9 N1 C1 -179.9(5) . . . . ? C8 C9 N1 Cu -60.7(6) . . . . ? N4 Cu N1 C1 167.8(4) . . . . ? N3 Cu N1 C1 79.9(6) . . . . ? N2 Cu N1 C1 9.1(4) . . . . ? N5 Cu N1 C1 -92.8(4) 2_554 . . . ? N4 Cu N1 C9 45.2(4) . . . . ? N3 Cu N1 C9 -42.7(7) . . . . ? N2 Cu N1 C9 -113.5(4) . . . . ? N5 Cu N1 C9 144.6(4) 2_554 . . . ? C1 C2 N2 C3 -166.6(5) . . . . ? C1 C2 N2 Cu -46.3(6) . . . . ? C10 C3 N2 C2 -137.0(6) . . . . ? C4 C3 N2 C2 97.7(6) . . . . ? C10 C3 N2 Cu 106.4(5) . . . . ? C4 C3 N2 Cu -18.9(6) . . . . ? N1 Cu N2 C2 21.0(4) . . . . ? N4 Cu N2 C2 -71.8(7) . . . . ? N3 Cu N2 C2 -130.4(4) . . . . ? N5 Cu N2 C2 121.7(4) 2_554 . . . ? N1 Cu N2 C3 143.1(4) . . . . ? N4 Cu N2 C3 50.4(7) . . . . ? N3 Cu N2 C3 -8.2(4) . . . . ? N5 Cu N2 C3 -116.1(4) 2_554 . . . ? C3 C4 N3 C5 -170.9(5) . . . . ? C3 C4 N3 Cu -53.4(5) . . . . ? C6 C5 N3 C4 148.9(5) . . . . ? C6 C5 N3 Cu 34.3(5) . . . . ? N1 Cu N3 C4 -38.2(7) . . . . ? N4 Cu N3 C4 -128.6(4) . . . . ? N2 Cu N3 C4 33.3(4) . . . . ? N5 Cu N3 C4 134.2(4) 2_554 . . . ? N1 Cu N3 C5 82.2(5) . . . . ? N4 Cu N3 C5 -8.2(4) . . . . ? N2 Cu N3 C5 153.7(4) . . . . ? N5 Cu N3 C5 -105.4(4) 2_554 . . . ? C5 C6 N4 C7 -79.5(6) . . . . ? C5 C6 N4 Cu 45.7(6) . . . . ? C8 C7 N4 C6 -178.6(5) . . . . ? C8 C7 N4 Cu 60.7(6) . . . . ? N1 Cu N4 C6 -170.3(4) . . . . ? N3 Cu N4 C6 -20.7(4) . . . . ? N2 Cu N4 C6 -78.9(7) . . . . ? N5 Cu N4 C6 87.7(4) 2_554 . . . ? N1 Cu N4 C7 -46.1(4) . . . . ? N3 Cu N4 C7 103.5(4) . . . . ? N2 Cu N4 C7 45.2(7) . . . . ? N5 Cu N4 C7 -148.1(4) 2_554 . . . ? C3 C10 N5 Cu -178.8(4) . . . 2_544 ? F1 C11 S1 O3 -179.7(5) . . . . ? F2 C11 S1 O3 -60.2(6) . . . . ? F3 C11 S1 O3 59.9(7) . . . . ? F1 C11 S1 O1 -58.2(6) . . . . ? F2 C11 S1 O1 61.4(6) . . . . ? F3 C11 S1 O1 -178.5(6) . . . . ? F1 C11 S1 O2 61.0(6) . . . . ? F2 C11 S1 O2 -179.4(5) . . . . ? F3 C11 S1 O2 -59.3(7) . . . . ? F5 C12 S2 O5 -57.1(6) . . . . ? F4 C12 S2 O5 61.7(6) . . . . ? F6 C12 S2 O5 -177.1(5) . . . . ? F5 C12 S2 O6 64.2(6) . . . . ? F4 C12 S2 O6 -177.1(5) . . . . ? F6 C12 S2 O6 -55.9(6) . . . . ? F5 C12 S2 O4 -176.5(5) . . . . ? F4 C12 S2 O4 -57.8(6) . . . . ? F6 C12 S2 O4 63.5(6) . . . . ? 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 N1 H1F O4 0.87(8) 2.29(8) 3.091(7) 152(7) 2_554 N2 H1G O2 0.88(8) 2.39(8) 3.210(8) 155(7) . N3 H1D O4 0.98(7) 2.00(7) 2.966(7) 173(7) . N4 H1E O1 0.86(2) 2.16(4) 2.935(7) 150(7) 2_554 N5 H1H O6 0.89(8) 2.15(8) 3.041(8) 178(7) 2_544 N5 H2I O2 0.86(2) 2.29(4) 3.092(8) 155(7) 2_544 _diffrn_measured_fraction_theta_max 0.870 _diffrn_reflns_theta_full 27.76 _diffrn_measured_fraction_theta_full 0.870 _refine_diff_density_max 1.821 _refine_diff_density_min -1.260 _refine_diff_density_rms 0.180