# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 loop_ _publ_author_name _publ_author_address V.Amendola 'Dipartimento di Chimica Generale, University of Pavia, Italy' G.Bergamaschi 'Dipartimento di Chimica Generale, University of Pavia, Italy' M.Boiocchi 'Centro Grandi Strumenti, Univerity of Pavia, Italy' L.Fabbrizzi 'Dipartimento di Chimica Generale, University of Pavia, Italy' N.Fusco 'Dipartimento di Chimica Generale, University of Pavia, Italy' #TrackingRef '- CHEM_SCI_[LH3]_[LHBr]_[LHAg].cif' _publ_contact_author ; Prof Luigi Fabbrizzi Dipartimento di Chimica Generale University of Pavia via Taramelli 12, I-27100 Pavia, ITALY ; _publ_contact_author_email luigi.fabbrizzi@unipv.it _publ_section_title ; The solution stability of copper(I) and silver(I) complexes with N-heterocyclic carbenes ; _publ_contact_author_name 'Prof Luigi Fabbrizzi' data_[LH3]_Br _database_code_depnum_ccdc_archive 'CCDC 824174' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 12,14,16,52,54,56-Hexamethyl-1,5(1,3,5)-tribenzena- 3,7,10(1,3)-tri-benzimidazoliabicyclo(3.3.3)undecaphane tribromide 7.7hydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C45 H45 N6, 7.70 (H2 O), 3 (Br)' _chemical_formula_sum 'C45 H60.40 Br3 N6 O7.70' _chemical_formula_weight 1048.38 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m' _symmetry_space_group_name_Hall '-C 2y' _symmetry_Int_Tables_number 12 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 21.808(2) _cell_length_b 17.0480(18) _cell_length_c 15.9333(17) _cell_angle_alpha 90.00 _cell_angle_beta 120.487(2) _cell_angle_gamma 90.00 _cell_volume 5104.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4342 _cell_measurement_theta_min 2 _cell_measurement_theta_max 20 _exptl_crystal_description 'platy prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2156 _exptl_absorpt_coefficient_mu 2.424 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Axs Smart-Apex CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_decay_% 0 _diffrn_reflns_number 20614 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4666 _reflns_number_gt 3442 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker-Axs Inc)' _computing_cell_refinement 'SAINT (Bruker-Axs Inc)' _computing_data_reduction 'SAINT (Bruker-Axs Inc)' _computing_structure_solution 'SIR-97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (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^ > 2\s(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. The Br counterions and water solvent molecules are placed on partly populated atom sites; some of them are mutually exclusive. Positions for H atoms bonded to oxygens placed at the partly populated O4W, O5W and O6W atom sites are not located. ; _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^)+(0.1556P)^2^+3.8700P] 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 4666 _refine_ls_number_parameters 327 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_gt 0.0716 _refine_ls_wR_factor_ref 0.2331 _refine_ls_wR_factor_gt 0.2118 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.2632(2) 0.14812(18) 0.1716(3) 0.0418(8) Uani 1 1 d . . . C2 C 0.2251(2) 0.14655(19) 0.0694(3) 0.0447(9) Uani 1 1 d . . . C3 C 0.2631(2) 0.14752(19) 0.0196(3) 0.0420(8) Uani 1 1 d . . . C4 C 0.3374(2) 0.14603(19) 0.0706(3) 0.0446(9) Uani 1 1 d . . . C5 C 0.3747(2) 0.14802(19) 0.1731(3) 0.0420(8) Uani 1 1 d . . . C6 C 0.3377(2) 0.14837(19) 0.2243(3) 0.0428(9) Uani 1 1 d . . . C7 C 0.2233(2) 0.1462(2) 0.2260(3) 0.0484(9) Uani 1 1 d . . . H7A H 0.2502 0.1743 0.2870 0.058 Uiso 1 1 calc R . . H7B H 0.1777 0.1721 0.1877 0.058 Uiso 1 1 calc R . . C8 C 0.1455(2) 0.1389(3) 0.0145(3) 0.0611(11) Uani 1 1 d . . . H8A H 0.1305 0.1149 0.0556 0.092 Uiso 1 1 calc R . . H8B H 0.1309 0.1068 -0.0422 0.092 Uiso 1 1 calc R . . H8C H 0.1244 0.1899 -0.0052 0.092 Uiso 1 1 calc R . . C9 C 0.2223(2) 0.1453(2) -0.0916(3) 0.0501(10) Uani 1 1 d . . . H9A H 0.1776 0.1731 -0.1164 0.060 Uiso 1 1 calc R . . H9B H 0.2498 0.1716 -0.1157 0.060 Uiso 1 1 calc R . . C10 C 0.3773(3) 0.1371(3) 0.0164(3) 0.0630(12) Uani 1 1 d . . . H10A H 0.3450 0.1204 -0.0491 0.095 Uiso 1 1 calc R . . H10B H 0.4143 0.0988 0.0487 0.095 Uiso 1 1 calc R . . H10C H 0.3980 0.1866 0.0154 0.095 Uiso 1 1 calc R . . C11 C 0.4547(2) 0.1459(2) 0.2295(3) 0.0496(9) Uani 1 1 d . . . H11A H 0.4729 0.1682 0.1904 0.060 Uiso 1 1 calc R . . H11B H 0.4723 0.1773 0.2880 0.060 Uiso 1 1 calc R . . C12 C 0.3781(2) 0.1439(3) 0.3343(3) 0.0609(11) Uani 1 1 d . . . H12A H 0.4229 0.1184 0.3565 0.091 Uiso 1 1 calc R . . H12B H 0.3507 0.1146 0.3555 0.091 Uiso 1 1 calc R . . H12C H 0.3861 0.1959 0.3609 0.091 Uiso 1 1 calc R . . C13 C 0.17992(19) 0.0410(2) 0.2983(3) 0.0453(8) Uani 1 1 d . . . C14 C 0.1521(2) 0.0843(3) 0.3446(3) 0.0590(11) Uani 1 1 d . . . H14 H 0.1522 0.1389 0.3449 0.071 Uiso 1 1 calc R . . C15 C 0.1243(3) 0.0408(3) 0.3902(4) 0.0736(13) Uani 1 1 d . . . H15 H 0.1047 0.0670 0.4223 0.088 Uiso 1 1 calc R . . C16 C 0.2296(3) 0.0000 0.2163(4) 0.0478(13) Uani 1 2 d S . . H16 H 0.2517 0.0000 0.1794 0.057 Uiso 1 2 calc SR . . C17 C 0.1688(2) 0.0406(2) -0.2240(3) 0.0470(9) Uani 1 1 d . . . C18 C 0.1315(2) 0.0841(3) -0.3097(3) 0.0606(11) Uani 1 1 d . . . H18 H 0.1312 0.1386 -0.3099 0.073 Uiso 1 1 calc R . . C19 C 0.0954(3) 0.0411(3) -0.3933(3) 0.0748(14) Uani 1 1 d . . . H19 H 0.0700 0.0674 -0.4524 0.090 Uiso 1 1 calc R . . C20 C 0.2297(3) 0.0000 -0.0733(4) 0.0481(13) Uani 1 2 d S . . H20 H 0.2567 0.0000 -0.0056 0.058 Uiso 1 2 calc SR . . C21 C 0.5490(2) 0.0410(3) 0.3229(3) 0.0585(10) Uani 1 1 d . . . C22 C 0.6101(3) 0.0842(4) 0.3814(4) 0.0881(17) Uani 1 1 d . . . H22 H 0.6106 0.1387 0.3823 0.106 Uiso 1 1 calc R . . C23 C 0.6702(3) 0.0396(4) 0.4384(6) 0.128(3) Uani 1 1 d . . . H23 H 0.7128 0.0655 0.4787 0.154 Uiso 1 1 calc R . . C24 C 0.4420(3) 0.0000 0.2171(4) 0.0481(13) Uani 1 2 d S . . H24 H 0.3943 0.0000 0.1685 0.058 Uiso 1 2 calc SR . . N1 N 0.21184(17) 0.06411(18) 0.2458(2) 0.0453(7) Uani 1 1 d . . . N2 N 0.20828(16) 0.06392(17) -0.1271(2) 0.0427(7) Uani 1 1 d . . . N3 N 0.48066(17) 0.06398(18) 0.2564(2) 0.0484(8) Uani 1 1 d . . . Br1 Br 0.54609(5) 0.25675(6) 0.12103(7) 0.0670(3) Uani 0.50 1 d P . . Br2 Br 0.54491(5) 0.27900(6) 0.44847(7) 0.0670(3) Uani 0.50 1 d P . . Br3 Br 0.28981(8) 0.26773(8) 0.45057(10) 0.0809(5) Uani 0.4255(18) 1 d P S 1 Br4 Br 0.5764(4) 0.0000 0.1344(4) 0.0596(18) Uani 0.149(4) 2 d SP S 2 O1W O 0.1919(4) 0.3393(3) 0.2372(3) 0.1285(19) Uani 1 1 d D . . H1WA H 0.1454 0.3284 0.2280 0.154 Uiso 1 1 d RD . . H1WB H 0.2304 0.3390 0.3037 0.154 Uiso 1 1 d RD . . O2W O 0.4691(2) 0.3408(2) 0.2284(3) 0.0863(11) Uani 1 1 d D . . H2WA H 0.498(3) 0.327(4) 0.200(4) 0.104 Uiso 1 1 d D . . H2WB H 0.491(3) 0.341(4) 0.2983(9) 0.104 Uiso 1 1 d D . . O3W O 0.4539(3) 0.5000 0.1675(5) 0.0925(16) Uani 1 2 d SD . . H3W H 0.469(3) 0.457(3) 0.213(4) 0.111 Uiso 1 1 d D . . O4W O 0.5394(5) 0.5365(6) 0.0911(8) 0.119(3) Uani 0.50 1 d P B -1 O5W O 0.6706(5) 0.0000 0.1840(7) 0.114(2) Uani 0.851(4) 2 d SP S 1 O6W O 0.5371(8) -0.0339(10) 0.1044(10) 0.123(5) Uani 0.4245(18) 1 d P S 1 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 0.054(2) 0.0242(16) 0.048(2) -0.0020(14) 0.0264(18) -0.0008(14) C2 0.054(2) 0.0233(16) 0.048(2) -0.0004(14) 0.0195(18) 0.0024(14) C3 0.056(2) 0.0242(16) 0.0397(18) -0.0005(13) 0.0203(17) -0.0013(14) C4 0.061(2) 0.0244(16) 0.051(2) -0.0023(14) 0.0296(19) -0.0063(15) C5 0.050(2) 0.0276(17) 0.046(2) -0.0018(14) 0.0223(18) -0.0030(14) C6 0.054(2) 0.0279(17) 0.0422(19) -0.0048(14) 0.0212(18) -0.0042(15) C7 0.062(2) 0.0321(18) 0.057(2) -0.0039(16) 0.034(2) 0.0033(17) C8 0.048(2) 0.062(3) 0.059(2) -0.002(2) 0.017(2) 0.0070(19) C9 0.071(3) 0.0269(18) 0.043(2) 0.0007(15) 0.0226(19) 0.0001(17) C10 0.077(3) 0.062(3) 0.061(3) -0.005(2) 0.043(2) -0.013(2) C11 0.058(2) 0.0346(19) 0.056(2) -0.0041(16) 0.028(2) -0.0092(16) C12 0.064(3) 0.070(3) 0.044(2) -0.0038(19) 0.024(2) -0.002(2) C13 0.043(2) 0.050(2) 0.0438(19) -0.0004(16) 0.0225(17) -0.0008(16) C14 0.062(3) 0.063(3) 0.060(2) -0.007(2) 0.036(2) 0.003(2) C15 0.080(3) 0.086(3) 0.080(3) -0.004(3) 0.058(3) 0.005(3) C16 0.059(3) 0.040(3) 0.058(3) 0.000 0.039(3) 0.000 C17 0.061(2) 0.0418(19) 0.0369(18) -0.0002(15) 0.0238(18) 0.0010(17) C18 0.076(3) 0.052(2) 0.046(2) 0.0071(18) 0.026(2) 0.004(2) C19 0.095(4) 0.070(3) 0.037(2) 0.008(2) 0.017(2) 0.002(3) C20 0.063(3) 0.032(3) 0.039(3) 0.000 0.018(3) 0.000 C21 0.042(2) 0.060(2) 0.066(2) -0.002(2) 0.021(2) -0.0033(18) C22 0.052(3) 0.080(4) 0.102(4) -0.011(3) 0.017(3) -0.012(3) C23 0.052(3) 0.109(5) 0.148(6) -0.014(4) -0.004(4) -0.008(3) C24 0.043(3) 0.040(3) 0.054(3) 0.000 0.019(3) 0.000 N1 0.0528(18) 0.0378(16) 0.0484(16) -0.0021(13) 0.0281(15) 0.0004(14) N2 0.0547(18) 0.0325(15) 0.0346(15) 0.0033(12) 0.0181(14) 0.0018(13) N3 0.0437(18) 0.0413(17) 0.0561(19) 0.0000(14) 0.0223(16) -0.0032(14) Br1 0.0523(6) 0.0848(7) 0.0733(6) -0.0064(5) 0.0387(5) -0.0164(4) Br2 0.0766(7) 0.0554(6) 0.0593(6) -0.0042(4) 0.0273(5) -0.0074(4) Br3 0.0892(10) 0.0756(9) 0.0784(9) -0.0193(6) 0.0427(7) -0.0056(6) Br4 0.079(4) 0.054(3) 0.052(3) 0.000 0.037(3) 0.000 O1W 0.221(6) 0.077(3) 0.089(3) 0.010(2) 0.080(4) 0.028(3) O2W 0.087(3) 0.073(2) 0.081(2) 0.005(2) 0.030(2) -0.001(2) O3W 0.096(4) 0.071(4) 0.096(4) 0.000 0.038(3) 0.000 O4W 0.096(6) 0.133(9) 0.128(7) -0.006(6) 0.056(6) -0.002(5) O5W 0.112(6) 0.096(5) 0.136(6) 0.000 0.064(5) 0.000 O6W 0.129(10) 0.158(15) 0.119(9) 0.033(9) 0.089(9) 0.048(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.401(5) . ? C1 C2 1.404(5) . ? C1 C7 1.508(5) . ? C2 C3 1.408(5) . ? C2 C8 1.500(6) . ? C3 C4 1.397(6) . ? C3 C9 1.527(5) . ? C4 C5 1.407(5) . ? C4 C10 1.513(6) . ? C5 C6 1.408(5) . ? C5 C11 1.504(6) . ? C6 C12 1.513(5) . ? C7 N1 1.483(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N2 1.471(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N3 1.486(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.381(6) . ? C13 N1 1.389(5) . ? C13 C13 1.399(8) 6 ? C14 C15 1.377(7) . ? C14 H14 0.9300 . ? C15 C15 1.391(11) 6 ? C15 H15 0.9300 . ? C16 N1 1.323(4) . ? C16 N1 1.323(4) 6 ? C16 H16 0.9300 . ? C17 C17 1.385(8) 6 ? C17 N2 1.391(5) . ? C17 C18 1.395(6) . ? C18 C19 1.366(6) . ? C18 H18 0.9300 . ? C19 C19 1.402(10) 6 ? C19 H19 0.9300 . ? C20 N2 1.317(4) 6 ? C20 N2 1.317(4) . ? C20 H20 0.9300 . ? C21 N3 1.377(5) . ? C21 C22 1.388(7) . ? C21 C21 1.396(9) 6 ? C22 C23 1.383(8) . ? C22 H22 0.9300 . ? C23 C23 1.351(14) 6 ? C23 H23 0.9300 . ? C24 N3 1.325(4) 6 ? C24 N3 1.325(4) . ? C24 H24 0.9300 . ? Br4 O6W 0.939(17) . ? Br4 O6W 0.939(17) 6 ? Br4 O5W 1.787(11) . ? O1W H1WA 0.9664 . ? O1W H1WB 0.9621 . ? O2W H2WA 0.97(7) . ? O2W H2WB 0.97(7) . ? O3W H3W 0.96(5) . ? O4W O4W 1.25(2) 6_565 ? O6W O6W 1.15(4) 6 ? 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 C6 C1 C2 121.3(3) . . ? C6 C1 C7 119.2(3) . . ? C2 C1 C7 119.5(3) . . ? C1 C2 C3 118.8(3) . . ? C1 C2 C8 120.5(4) . . ? C3 C2 C8 120.6(3) . . ? C4 C3 C2 120.8(3) . . ? C4 C3 C9 119.7(3) . . ? C2 C3 C9 119.4(3) . . ? C3 C4 C5 119.5(3) . . ? C3 C4 C10 120.2(3) . . ? C5 C4 C10 120.2(4) . . ? C4 C5 C6 120.5(3) . . ? C4 C5 C11 120.4(3) . . ? C6 C5 C11 119.0(3) . . ? C1 C6 C5 119.0(3) . . ? C1 C6 C12 120.6(3) . . ? C5 C6 C12 120.3(3) . . ? N1 C7 C1 110.6(3) . . ? N1 C7 H7A 109.5 . . ? C1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C3 110.7(3) . . ? N2 C9 H9A 109.5 . . ? C3 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C5 110.6(3) . . ? N3 C11 H11A 109.5 . . ? C5 C11 H11A 109.5 . . ? N3 C11 H11B 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 N1 131.3(4) . . ? C14 C13 C13 122.3(3) . 6 ? N1 C13 C13 106.4(2) . 6 ? C15 C14 C13 115.1(4) . . ? C15 C14 H14 122.4 . . ? C13 C14 H14 122.4 . . ? C14 C15 C15 122.6(3) . 6 ? C14 C15 H15 118.7 . . ? C15 C15 H15 118.7 6 . ? N1 C16 N1 111.4(5) . 6 ? N1 C16 H16 124.3 . . ? N1 C16 H16 124.3 6 . ? C17 C17 N2 106.6(2) 6 . ? C17 C17 C18 122.1(2) 6 . ? N2 C17 C18 131.3(4) . . ? C19 C18 C17 115.5(4) . . ? C19 C18 H18 122.2 . . ? C17 C18 H18 122.2 . . ? C18 C19 C19 122.4(3) . 6 ? C18 C19 H19 118.8 . . ? C19 C19 H19 118.8 6 . ? N2 C20 N2 111.7(4) 6 . ? N2 C20 H20 124.2 6 . ? N2 C20 H20 124.2 . . ? N3 C21 C22 131.4(5) . . ? N3 C21 C21 106.6(2) . 6 ? C22 C21 C21 122.0(3) . 6 ? C23 C22 C21 114.6(6) . . ? C23 C22 H22 122.7 . . ? C21 C22 H22 122.7 . . ? C23 C23 C22 123.3(4) 6 . ? C23 C23 H23 118.3 6 . ? C22 C23 H23 118.3 . . ? N3 C24 N3 110.8(5) 6 . ? N3 C24 H24 124.6 6 . ? N3 C24 H24 124.6 . . ? C16 N1 C13 107.9(3) . . ? C16 N1 C7 126.3(3) . . ? C13 N1 C7 125.8(3) . . ? C20 N2 C17 107.6(3) . . ? C20 N2 C9 126.5(3) . . ? C17 N2 C9 125.9(3) . . ? C24 N3 C21 108.0(3) . . ? C24 N3 C11 125.4(3) . . ? C21 N3 C11 126.5(3) . . ? O6W Br4 O6W 75.9(18) . 6 ? O6W Br4 O5W 140.6(9) . . ? O6W Br4 O5W 140.6(9) 6 . ? H1WA O1W H1WB 115.4 . . ? H2WA O2W H2WB 118(6) . . ? Br4 O6W O6W 52.1(9) . 6 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.995 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.107 #===END data_[CuLH]_ClO4 _database_code_depnum_ccdc_archive 'CCDC 824175' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (12,14,16,52,54,56-Hexamethyl-1,5(1,3,5)-tribenzena- 3,7,10(1,3)-tri-benzimidazoliabicyclo(3.3.3)undecaphane -32,72- diylidene)-cooper(i) bis(perchlorate) ; _chemical_melting_point ? _chemical_formula_moiety '2(C45 H43 Cu N6), 4 (CL O4)' _chemical_formula_sum 'C90 H86 Cl4 Cu2 N12 O16' _chemical_formula_weight 1860.60 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' Cl Cl 0.1484 0.1585 '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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.0018(14) _cell_length_b 25.6183(12) _cell_length_c 21.9405(12) _cell_angle_alpha 90.00 _cell_angle_beta 97.7970(10) _cell_angle_gamma 90.00 _cell_volume 8354.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6836 _cell_measurement_theta_min 2 _cell_measurement_theta_max 24 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3856 _exptl_absorpt_coefficient_mu 0.714 _exptl_absorpt_correction_T_min 0.762 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Axs Smart-Apex CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_decay_% 0 _diffrn_reflns_number 79425 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 25.07 _reflns_number_total 14809 _reflns_number_gt 10539 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker-Axs Inc)' _computing_cell_refinement 'SAINT (Bruker-Axs Inc)' _computing_data_reduction 'SAINT (Bruker-Axs Inc)' _computing_structure_solution 'SIR-97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (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^ > 2\s(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. The Cu atoms are disordered over two alternative positions with very different occupancies: 0.93(1) vs. 0.07(1). A different geometrical arrangement for the cage is probably present in the unit cell having Cu species in the secondary position. However, these unit cells are only 7% of those forming the crystal and the features of the cage in this minority portion of the crystal cannot be characterized through X-ray diffraction analysis. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1562P)^2^+7.0833P] 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 14809 _refine_ls_number_parameters 1136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0989 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.2482 _refine_ls_wR_factor_gt 0.2214 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.001 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 0.28302(4) 0.00250(2) 0.30855(3) 0.0524(2) Uani 0.9287(17) 1 d P A 1 Cu2 Cu 0.72379(4) -0.24433(2) 0.23937(3) 0.0519(2) Uani 0.9287(17) 1 d P A 1 C1 C 0.3640(3) 0.05499(17) 0.3559(2) 0.0542(11) Uani 1 1 d . A 1 C2 C 0.4177(3) 0.13017(18) 0.4023(2) 0.0592(12) Uani 1 1 d . A 1 C3 C 0.4308(4) 0.1818(2) 0.4230(2) 0.0713(14) Uani 1 1 d . A 1 H3 H 0.3859 0.2069 0.4156 0.086 Uiso 1 1 calc R A 1 C4 C 0.5135(5) 0.1930(2) 0.4547(2) 0.0815(18) Uani 1 1 d . A 1 H4 H 0.5251 0.2269 0.4688 0.098 Uiso 1 1 calc R A 1 C5 C 0.5806(4) 0.1558(2) 0.4666(2) 0.0809(17) Uani 1 1 d . A 1 H5 H 0.6355 0.1654 0.4887 0.097 Uiso 1 1 calc R A 1 C6 C 0.5680(4) 0.1042(2) 0.4463(2) 0.0704(14) Uani 1 1 d . A 1 H6 H 0.6126 0.0789 0.4545 0.084 Uiso 1 1 calc R A 1 C7 C 0.4849(3) 0.09330(18) 0.4133(2) 0.0569(11) Uani 1 1 d . A 1 C8 C 0.2612(4) 0.1344(2) 0.3475(3) 0.0737(15) Uani 1 1 d . A 1 H8A H 0.2739 0.1713 0.3441 0.088 Uiso 1 1 calc R A 1 H8B H 0.2206 0.1300 0.3779 0.088 Uiso 1 1 calc R A 1 C9 C 0.2176(3) 0.11360(18) 0.2857(3) 0.0625(13) Uani 1 1 d . A 1 C10 C 0.2559(3) 0.12530(18) 0.2331(3) 0.0659(13) Uani 1 1 d . A 1 C11 C 0.2232(3) 0.10004(19) 0.1771(3) 0.0639(13) Uani 1 1 d . A 1 C12 C 0.1580(3) 0.0618(2) 0.1756(3) 0.0662(13) Uani 1 1 d . A 1 C13 C 0.1203(3) 0.05052(18) 0.2293(3) 0.0610(12) Uani 1 1 d . A 1 C14 C 0.1478(3) 0.07796(19) 0.2840(3) 0.0651(13) Uani 1 1 d . A 1 C15 C 0.0602(3) 0.0037(2) 0.2308(3) 0.0704(14) Uani 1 1 d . A 1 H15A H 0.0254 0.0071 0.2648 0.085 Uiso 1 1 calc R A 1 H15B H 0.0186 0.0021 0.1930 0.085 Uiso 1 1 calc R A 1 C16 C 0.2007(3) -0.05039(18) 0.2628(2) 0.0595(12) Uani 1 1 d . A 1 C17 C 0.0754(3) -0.0915(2) 0.2156(2) 0.0648(13) Uani 1 1 d . A 1 C18 C -0.0107(4) -0.1036(2) 0.1876(3) 0.0775(16) Uani 1 1 d . A 1 H18 H -0.0573 -0.0794 0.1824 0.093 Uiso 1 1 calc R A 1 C19 C -0.0211(5) -0.1554(3) 0.1677(3) 0.091(2) Uani 1 1 d . A 1 H19 H -0.0769 -0.1659 0.1478 0.109 Uiso 1 1 calc R A 1 C20 C 0.0460(5) -0.1910(3) 0.1760(3) 0.090(2) Uani 1 1 d . A 1 H20 H 0.0347 -0.2247 0.1612 0.109 Uiso 1 1 calc R A 1 C21 C 0.1290(4) -0.1793(2) 0.2049(3) 0.0799(17) Uani 1 1 d . A 1 H21 H 0.1743 -0.2043 0.2111 0.096 Uiso 1 1 calc R A 1 C22 C 0.1431(3) -0.12807(18) 0.2250(2) 0.0601(12) Uani 1 1 d . A 1 C23 C 0.3053(3) -0.13024(18) 0.2675(3) 0.0667(13) Uani 1 1 d . A 1 H23A H 0.3100 -0.1557 0.2354 0.080 Uiso 1 1 calc R A 1 H23B H 0.3076 -0.1487 0.3063 0.080 Uiso 1 1 calc R A 1 C24 C 0.3822(3) -0.09289(16) 0.2708(2) 0.0533(11) Uani 1 1 d . A 1 C25 C 0.4110(3) -0.07520(17) 0.2171(2) 0.0556(11) Uani 1 1 d . A 1 C26 C 0.4785(3) -0.03733(17) 0.2201(2) 0.0538(11) Uani 1 1 d . A 1 C27 C 0.5124(3) -0.01434(17) 0.2765(2) 0.0546(11) Uani 1 1 d . A 1 C28 C 0.4792(3) -0.03167(17) 0.3298(2) 0.0532(11) Uani 1 1 d . A 1 C29 C 0.4185(3) -0.07262(17) 0.3281(2) 0.0545(11) Uani 1 1 d . A 1 C30 C 0.5021(4) -0.00039(18) 0.3881(2) 0.0640(13) Uani 1 1 d . A 1 H30A H 0.4894 -0.0209 0.4230 0.077 Uiso 1 1 calc R A 1 H30B H 0.5657 0.0080 0.3939 0.077 Uiso 1 1 calc R A 1 C31 C 0.5106(4) -0.0183(2) 0.1618(2) 0.0671(13) Uani 1 1 d . A 1 H31A H 0.5728 -0.0071 0.1707 0.081 Uiso 1 1 calc R A 1 H31B H 0.5079 -0.0468 0.1324 0.081 Uiso 1 1 calc R A 1 C32 C 0.3777(3) 0.0436(2) 0.1508(2) 0.0630(12) Uani 1 1 d . A 1 H32 H 0.3500 0.0299 0.1828 0.076 Uiso 1 1 calc R A 1 C33 C 0.4063(4) 0.0917(2) 0.0731(2) 0.0662(13) Uani 1 1 d . A 1 C34 C 0.4055(5) 0.1295(3) 0.0263(3) 0.090(2) Uani 1 1 d . A 1 H34 H 0.3605 0.1545 0.0185 0.108 Uiso 1 1 calc R A 1 C35 C 0.4763(5) 0.1266(3) -0.0066(3) 0.098(2) Uani 1 1 d . A 1 H35 H 0.4792 0.1505 -0.0382 0.118 Uiso 1 1 calc R A 1 C36 C 0.5449(5) 0.0893(3) 0.0047(2) 0.089(2) Uani 1 1 d . A 1 H36 H 0.5914 0.0895 -0.0193 0.107 Uiso 1 1 calc R A 1 C37 C 0.5452(4) 0.0527(2) 0.0501(2) 0.0719(15) Uani 1 1 d . A 1 H37 H 0.5903 0.0277 0.0577 0.086 Uiso 1 1 calc R A 1 C38 C 0.4739(3) 0.0554(2) 0.0840(2) 0.0608(12) Uani 1 1 d . A 1 C39 C 0.2636(4) 0.1133(2) 0.1194(3) 0.0767(15) Uani 1 1 d . A 1 H39A H 0.2201 0.1060 0.0836 0.092 Uiso 1 1 calc R A 1 H39B H 0.2774 0.1503 0.1193 0.092 Uiso 1 1 calc R A 1 C40 C 0.3363(4) 0.1624(2) 0.2357(3) 0.0876(18) Uani 1 1 d . A 1 H40A H 0.3154 0.1979 0.2354 0.131 Uiso 1 1 calc R A 1 H40B H 0.3669 0.1566 0.2006 0.131 Uiso 1 1 calc R A 1 H40C H 0.3769 0.1561 0.2726 0.131 Uiso 1 1 calc R A 1 C41 C 0.1039(5) 0.0671(3) 0.3413(3) 0.103(2) Uani 1 1 d . A 1 H41A H 0.1379 0.0410 0.3658 0.155 Uiso 1 1 calc R A 1 H41B H 0.0436 0.0547 0.3294 0.155 Uiso 1 1 calc R A 1 H41C H 0.1024 0.0986 0.3648 0.155 Uiso 1 1 calc R A 1 C42 C 0.1299(5) 0.0287(3) 0.1193(3) 0.0905(18) Uani 1 1 d . A 1 H42A H 0.0697 0.0377 0.1018 0.136 Uiso 1 1 calc R A 1 H42B H 0.1320 -0.0075 0.1306 0.136 Uiso 1 1 calc R A 1 H42C H 0.1701 0.0348 0.0895 0.136 Uiso 1 1 calc R A 1 C43 C 0.3670(4) -0.0954(2) 0.1553(3) 0.0851(17) Uani 1 1 d . A 1 H43A H 0.3983 -0.1260 0.1444 0.128 Uiso 1 1 calc R A 1 H43B H 0.3697 -0.0689 0.1246 0.128 Uiso 1 1 calc R A 1 H43C H 0.3054 -0.1040 0.1578 0.128 Uiso 1 1 calc R A 1 C44 C 0.5799(4) 0.0303(2) 0.2790(3) 0.0850(17) Uani 1 1 d . A 1 H44A H 0.5558 0.0605 0.2969 0.127 Uiso 1 1 calc R A 1 H44B H 0.5916 0.0385 0.2381 0.127 Uiso 1 1 calc R A 1 H44C H 0.6350 0.0201 0.3036 0.127 Uiso 1 1 calc R A 1 C45 C 0.3885(5) -0.0932(2) 0.3861(3) 0.0841(17) Uani 1 1 d . A 1 H45A H 0.4391 -0.0949 0.4179 0.126 Uiso 1 1 calc R A 1 H45B H 0.3635 -0.1275 0.3787 0.126 Uiso 1 1 calc R A 1 H45C H 0.3436 -0.0705 0.3988 0.126 Uiso 1 1 calc R A 1 N1 N 0.3455(3) 0.10569(15) 0.36670(18) 0.0577(9) Uani 1 1 d . A 1 N2 N 0.4495(3) 0.04777(15) 0.38473(17) 0.0569(9) Uani 1 1 d . A 1 N3 N 0.1131(3) -0.04425(15) 0.2380(2) 0.0606(10) Uani 1 1 d . A 1 N4 N 0.2184(3) -0.10190(15) 0.2543(2) 0.0604(10) Uani 1 1 d . A 1 N5 N 0.3463(3) 0.08318(16) 0.11557(19) 0.0648(11) Uani 1 1 d . A 1 N6 N 0.4545(3) 0.02591(15) 0.13433(18) 0.0592(10) Uani 1 1 d . A 1 C46 C 0.6473(3) -0.29098(18) 0.1818(2) 0.0560(11) Uani 1 1 d . A 1 C47 C 0.5384(4) -0.3167(2) 0.1048(2) 0.0644(13) Uani 1 1 d . A 1 C48 C 0.4618(4) -0.3198(3) 0.0604(2) 0.0799(16) Uani 1 1 d . A 1 H48 H 0.4182 -0.2938 0.0556 0.096 Uiso 1 1 calc R A 1 C49 C 0.4558(5) -0.3640(3) 0.0246(3) 0.095(2) Uani 1 1 d . A 1 H49 H 0.4062 -0.3682 -0.0054 0.114 Uiso 1 1 calc R A 1 C50 C 0.5213(5) -0.4026(3) 0.0317(3) 0.095(2) Uani 1 1 d . A 1 H50 H 0.5135 -0.4319 0.0066 0.114 Uiso 1 1 calc R A 1 C51 C 0.5972(4) -0.3993(2) 0.0742(3) 0.0804(16) Uani 1 1 d . A 1 H51 H 0.6412 -0.4252 0.0784 0.096 Uiso 1 1 calc R A 1 C52 C 0.6038(4) -0.3545(2) 0.1106(2) 0.0645(13) Uani 1 1 d . A 1 C53 C 0.5086(3) -0.2341(2) 0.1573(2) 0.0643(13) Uani 1 1 d . A 1 H53A H 0.4461 -0.2452 0.1518 0.077 Uiso 1 1 calc R A 1 H53B H 0.5157 -0.2080 0.1264 0.077 Uiso 1 1 calc R A 1 C54 C 0.5318(3) -0.21049(17) 0.2205(2) 0.0531(11) Uani 1 1 d . A 1 C55 C 0.4990(3) -0.23350(17) 0.2710(2) 0.0543(11) Uani 1 1 d . A 1 C56 C 0.5301(3) -0.21558(17) 0.3303(2) 0.0530(10) Uani 1 1 d . A 1 C57 C 0.5946(3) -0.17605(18) 0.3395(2) 0.0576(11) Uani 1 1 d . A 1 C58 C 0.6250(3) -0.15296(17) 0.2885(2) 0.0546(11) Uani 1 1 d . A 1 C59 C 0.5934(3) -0.16950(18) 0.2288(2) 0.0570(11) Uani 1 1 d . A 1 C60 C 0.7026(3) -0.11521(18) 0.2976(3) 0.0676(13) Uani 1 1 d . A 1 H60A H 0.6976 -0.0909 0.2635 0.081 Uiso 1 1 calc R A 1 H60B H 0.7001 -0.0954 0.3350 0.081 Uiso 1 1 calc R A 1 C61 C 0.8044(3) -0.19357(19) 0.2870(2) 0.0577(11) Uani 1 1 d . A 1 C62 C 0.8671(3) -0.11719(19) 0.3270(2) 0.0592(12) Uani 1 1 d . A 1 C63 C 0.8835(4) -0.0667(2) 0.3485(2) 0.0682(13) Uani 1 1 d . A 1 H63 H 0.8379 -0.0419 0.3471 0.082 Uiso 1 1 calc R A 1 C64 C 0.9713(4) -0.0553(2) 0.3723(3) 0.0779(16) Uani 1 1 d . A 1 H64 H 0.9849 -0.0221 0.3878 0.093 Uiso 1 1 calc R A 1 C65 C 1.0397(4) -0.0916(2) 0.3739(3) 0.0780(16) Uani 1 1 d . A 1 H65 H 1.0981 -0.0818 0.3894 0.094 Uiso 1 1 calc R A 1 C66 C 1.0236(3) -0.1422(2) 0.3531(2) 0.0679(13) Uani 1 1 d . A 1 H66 H 1.0694 -0.1668 0.3549 0.082 Uiso 1 1 calc R A 1 C67 C 0.9357(3) -0.15410(19) 0.3293(2) 0.0562(11) Uani 1 1 d . A 1 C68 C 0.9479(3) -0.24884(19) 0.3057(2) 0.0593(12) Uani 1 1 d . A 1 H68A H 0.9917 -0.2505 0.3425 0.071 Uiso 1 1 calc R A 1 H68B H 0.9803 -0.2490 0.2703 0.071 Uiso 1 1 calc R A 1 C69 C 0.8871(3) -0.29580(18) 0.3031(2) 0.0546(11) Uani 1 1 d . A 1 C70 C 0.8589(3) -0.31919(18) 0.2462(2) 0.0585(12) Uani 1 1 d . A 1 C71 C 0.7901(3) -0.35640(18) 0.2415(2) 0.0578(11) Uani 1 1 d . A 1 C72 C 0.7547(3) -0.37315(19) 0.2934(3) 0.0632(12) Uani 1 1 d . A 1 C73 C 0.7886(3) -0.35161(19) 0.3509(2) 0.0610(12) Uani 1 1 d . A 1 C74 C 0.8514(3) -0.31210(19) 0.3556(2) 0.0580(12) Uani 1 1 d . A 1 C75 C 0.7460(4) -0.3725(2) 0.1799(3) 0.0701(14) Uani 1 1 d . A 1 H75A H 0.7893 -0.3709 0.1509 0.084 Uiso 1 1 calc R A 1 H75B H 0.7255 -0.4083 0.1817 0.084 Uiso 1 1 calc R A 1 C76 C 0.7494(3) -0.3711(2) 0.4077(3) 0.0698(14) Uani 1 1 d . A 1 H76A H 0.7416 -0.4087 0.4052 0.084 Uiso 1 1 calc R A 1 H76B H 0.7910 -0.3633 0.4444 0.084 Uiso 1 1 calc R A 1 C77 C 0.6317(3) -0.30106(19) 0.3874(2) 0.0585(12) Uani 1 1 d . A 1 H77 H 0.6627 -0.2805 0.3624 0.070 Uiso 1 1 calc R A 1 C78 C 0.5283(3) -0.32836(18) 0.4415(2) 0.0538(11) Uani 1 1 d . A 1 C79 C 0.4530(3) -0.3343(2) 0.4708(2) 0.0608(12) Uani 1 1 d . A 1 H79 H 0.4060 -0.3103 0.4660 0.073 Uiso 1 1 calc R A 1 C80 C 0.4518(4) -0.3784(2) 0.5078(2) 0.0694(14) Uani 1 1 d . A 1 H80 H 0.4032 -0.3840 0.5292 0.083 Uiso 1 1 calc R A 1 C81 C 0.5218(4) -0.4140(2) 0.5134(3) 0.0741(15) Uani 1 1 d . A 1 H81 H 0.5184 -0.4430 0.5386 0.089 Uiso 1 1 calc R A 1 C82 C 0.5958(4) -0.4086(2) 0.4836(2) 0.0643(13) Uani 1 1 d . A 1 H82 H 0.6422 -0.4330 0.4877 0.077 Uiso 1 1 calc R A 1 C83 C 0.5977(3) -0.36487(19) 0.4471(2) 0.0563(11) Uani 1 1 d . A 1 C84 C 0.4974(3) -0.24203(19) 0.3842(2) 0.0629(12) Uani 1 1 d . A 1 H84A H 0.5009 -0.2179 0.4185 0.075 Uiso 1 1 calc R A 1 H84B H 0.4349 -0.2521 0.3734 0.075 Uiso 1 1 calc R A 1 C85 C 0.4356(4) -0.2800(2) 0.2618(3) 0.0766(15) Uani 1 1 d . A 1 H85A H 0.4054 -0.2840 0.2974 0.115 Uiso 1 1 calc R A 1 H85B H 0.4693 -0.3110 0.2560 0.115 Uiso 1 1 calc R A 1 H85C H 0.3919 -0.2742 0.2262 0.115 Uiso 1 1 calc R A 1 C86 C 0.6288(4) -0.1458(2) 0.1739(3) 0.0800(16) Uani 1 1 d . A 1 H86A H 0.5795 -0.1327 0.1456 0.120 Uiso 1 1 calc R A 1 H86B H 0.6604 -0.1719 0.1539 0.120 Uiso 1 1 calc R A 1 H86C H 0.6691 -0.1176 0.1873 0.120 Uiso 1 1 calc R A 1 C87 C 0.6347(4) -0.1605(3) 0.4041(3) 0.0812(16) Uani 1 1 d . A 1 H87A H 0.5967 -0.1350 0.4197 0.122 Uiso 1 1 calc R A 1 H87B H 0.6935 -0.1460 0.4032 0.122 Uiso 1 1 calc R A 1 H87C H 0.6392 -0.1907 0.4302 0.122 Uiso 1 1 calc R A 1 C88 C 0.6756(4) -0.4114(2) 0.2872(3) 0.0842(17) Uani 1 1 d . A 1 H88A H 0.6316 -0.4009 0.2535 0.126 Uiso 1 1 calc R A 1 H88B H 0.6489 -0.4114 0.3245 0.126 Uiso 1 1 calc R A 1 H88C H 0.6968 -0.4458 0.2796 0.126 Uiso 1 1 calc R A 1 C89 C 0.8789(4) -0.2824(3) 0.4158(2) 0.0821(16) Uani 1 1 d . A 1 H89A H 0.8458 -0.2957 0.4470 0.123 Uiso 1 1 calc R A 1 H89B H 0.8660 -0.2460 0.4095 0.123 Uiso 1 1 calc R A 1 H89C H 0.9422 -0.2870 0.4287 0.123 Uiso 1 1 calc R A 1 C90 C 0.8986(4) -0.3016(2) 0.1895(3) 0.0811(16) Uani 1 1 d . A 1 H90A H 0.8870 -0.3276 0.1579 0.122 Uiso 1 1 calc R A 1 H90B H 0.9624 -0.2970 0.1998 0.122 Uiso 1 1 calc R A 1 H90C H 0.8716 -0.2692 0.1750 0.122 Uiso 1 1 calc R A 1 N7 N 0.5662(3) -0.27899(15) 0.14905(17) 0.0587(10) Uani 1 1 d . A 1 N8 N 0.6693(3) -0.33872(14) 0.15852(18) 0.0577(9) Uani 1 1 d . A 1 N9 N 0.7890(3) -0.14252(15) 0.30187(19) 0.0588(10) Uani 1 1 d . A 1 N10 N 0.8954(2) -0.19992(15) 0.30615(18) 0.0552(9) Uani 1 1 d . A 1 N11 N 0.5523(2) -0.28911(15) 0.40288(17) 0.0542(9) Uani 1 1 d . A 1 N12 N 0.6617(3) -0.34593(15) 0.41194(18) 0.0577(10) Uani 1 1 d . A 1 Cu1B Cu 0.2916(7) -0.0003(3) 0.2063(5) 0.074(3) Uani 0.0713(17) 1 d P A 2 Cu2B Cu 0.7167(8) -0.2515(4) 0.3413(7) 0.098(4) Uani 0.0713(17) 1 d P A 2 Cl1 Cl 0.25309(11) 0.01828(7) 0.51295(7) 0.0867(5) Uani 1 1 d . . . O1 O 0.2434(6) 0.0718(3) 0.5056(5) 0.218(5) Uani 1 1 d . . . O2 O 0.2711(4) 0.0037(3) 0.5753(3) 0.163(3) Uani 1 1 d . . . O3 O 0.3400(6) 0.0132(4) 0.4917(3) 0.211(4) Uani 1 1 d . . . O4 O 0.1705(9) 0.0025(4) 0.4924(7) 0.358(11) Uani 1 1 d . . . Cl2 Cl 0.22786(11) -0.23421(6) 0.40756(11) 0.1082(7) Uani 1 1 d . . . O5 O 0.2227(5) -0.1820(2) 0.4194(5) 0.215(5) Uani 1 1 d . . . O6 O 0.1454(3) -0.25857(18) 0.3990(3) 0.1109(17) Uani 1 1 d . . . O7 O 0.2757(6) -0.2565(3) 0.4607(6) 0.232(5) Uani 1 1 d . . . O8 O 0.2815(5) -0.2490(4) 0.3629(5) 0.232(5) Uani 1 1 d . . . Cl3 Cl 0.76024(10) -0.28652(6) 0.56783(6) 0.0773(4) Uani 1 1 d . . . O9 O 0.7778(3) -0.26274(17) 0.6258(2) 0.0899(12) Uani 1 1 d . . . O10 O 0.7335(6) -0.2521(3) 0.5219(3) 0.193(4) Uani 1 1 d . . . O11 O 0.8388(4) -0.3114(2) 0.55469(19) 0.1112(17) Uani 1 1 d . . . O12 O 0.6927(6) -0.3231(5) 0.5716(3) 0.246(6) Uani 1 1 d . . . Cl4 Cl 0.72717(11) -0.53422(6) 0.41488(10) 0.0977(6) Uani 1 1 d . . . O13 O 0.6384(3) -0.5135(2) 0.3982(3) 0.1214(18) Uani 1 1 d . . . O14 O 0.7623(5) -0.5124(3) 0.4745(3) 0.160(3) Uani 1 1 d . . . O15 O 0.7206(4) -0.5889(2) 0.4149(4) 0.171(3) Uani 1 1 d . . . O16 O 0.7805(4) -0.5170(3) 0.3716(3) 0.147(2) 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 0.0519(4) 0.0415(3) 0.0632(4) -0.0049(3) 0.0051(3) -0.0017(2) Cu2 0.0503(4) 0.0468(3) 0.0567(4) -0.0017(3) 0.0003(3) 0.0009(2) C1 0.056(3) 0.050(3) 0.058(3) -0.004(2) 0.010(2) 0.000(2) C2 0.074(3) 0.053(3) 0.051(3) -0.008(2) 0.013(2) -0.011(2) C3 0.099(4) 0.059(3) 0.060(3) -0.015(2) 0.024(3) -0.012(3) C4 0.127(5) 0.065(3) 0.053(3) -0.013(3) 0.013(3) -0.033(3) C5 0.106(5) 0.085(4) 0.048(3) -0.005(3) -0.005(3) -0.035(4) C6 0.086(4) 0.071(3) 0.050(3) 0.006(2) -0.005(3) -0.018(3) C7 0.072(3) 0.054(3) 0.044(2) -0.001(2) 0.006(2) -0.011(2) C8 0.073(3) 0.053(3) 0.095(4) -0.020(3) 0.011(3) 0.012(2) C9 0.054(3) 0.043(2) 0.089(4) 0.000(2) 0.007(2) 0.013(2) C10 0.055(3) 0.045(3) 0.095(4) 0.009(3) 0.003(3) 0.008(2) C11 0.054(3) 0.056(3) 0.081(3) 0.020(2) 0.004(2) 0.009(2) C12 0.060(3) 0.059(3) 0.077(3) 0.013(2) -0.002(3) 0.010(2) C13 0.049(3) 0.051(3) 0.082(3) 0.005(2) 0.004(2) 0.004(2) C14 0.053(3) 0.052(3) 0.091(4) 0.001(3) 0.014(3) 0.009(2) C15 0.050(3) 0.071(3) 0.089(4) 0.003(3) 0.003(3) -0.005(2) C16 0.059(3) 0.048(3) 0.072(3) -0.002(2) 0.012(2) -0.007(2) C17 0.069(3) 0.071(3) 0.055(3) -0.003(2) 0.012(2) -0.025(3) C18 0.074(4) 0.090(4) 0.067(3) 0.004(3) 0.004(3) -0.029(3) C19 0.091(4) 0.108(5) 0.072(4) -0.010(3) 0.003(3) -0.053(4) C20 0.109(5) 0.083(4) 0.085(4) -0.027(3) 0.034(4) -0.047(4) C21 0.088(4) 0.067(3) 0.094(4) -0.021(3) 0.044(3) -0.032(3) C22 0.067(3) 0.053(3) 0.065(3) -0.005(2) 0.025(2) -0.018(2) C23 0.071(3) 0.041(2) 0.090(4) -0.006(2) 0.019(3) -0.005(2) C24 0.056(3) 0.035(2) 0.071(3) 0.000(2) 0.017(2) 0.0022(19) C25 0.065(3) 0.044(2) 0.059(3) -0.005(2) 0.010(2) 0.008(2) C26 0.056(3) 0.046(2) 0.062(3) 0.006(2) 0.015(2) 0.010(2) C27 0.049(2) 0.046(2) 0.070(3) 0.004(2) 0.009(2) 0.0032(19) C28 0.056(3) 0.045(2) 0.057(3) 0.0013(19) 0.000(2) 0.010(2) C29 0.063(3) 0.045(2) 0.058(3) 0.005(2) 0.015(2) 0.007(2) C30 0.064(3) 0.057(3) 0.066(3) -0.001(2) -0.009(2) 0.012(2) C31 0.069(3) 0.063(3) 0.074(3) 0.013(3) 0.026(3) 0.010(2) C32 0.065(3) 0.064(3) 0.062(3) 0.017(2) 0.018(2) 0.007(2) C33 0.066(3) 0.074(3) 0.055(3) 0.013(2) -0.003(2) -0.015(3) C34 0.097(4) 0.096(4) 0.070(4) 0.036(3) -0.015(3) -0.022(4) C35 0.100(5) 0.134(6) 0.055(3) 0.040(4) -0.006(3) -0.043(4) C36 0.093(4) 0.122(5) 0.051(3) 0.002(3) 0.009(3) -0.051(4) C37 0.069(3) 0.092(4) 0.055(3) 0.000(3) 0.011(2) -0.026(3) C38 0.064(3) 0.069(3) 0.048(3) 0.005(2) 0.003(2) -0.017(2) C39 0.071(3) 0.070(3) 0.086(4) 0.023(3) 0.003(3) 0.007(3) C40 0.082(4) 0.067(3) 0.112(5) 0.009(3) 0.006(3) -0.018(3) C41 0.100(5) 0.109(5) 0.108(5) -0.024(4) 0.043(4) -0.026(4) C42 0.100(5) 0.095(5) 0.073(4) 0.007(3) -0.002(3) -0.007(4) C43 0.102(5) 0.085(4) 0.069(4) -0.021(3) 0.012(3) -0.016(3) C44 0.073(4) 0.070(4) 0.110(5) -0.005(3) 0.006(3) -0.019(3) C45 0.106(5) 0.079(4) 0.073(4) 0.013(3) 0.032(3) 0.000(3) N1 0.061(2) 0.049(2) 0.063(2) -0.0081(18) 0.0095(19) 0.0023(18) N2 0.066(2) 0.052(2) 0.051(2) -0.0035(17) 0.0000(18) -0.0021(18) N3 0.054(2) 0.051(2) 0.076(3) 0.0031(19) 0.0023(19) -0.0068(18) N4 0.057(2) 0.045(2) 0.081(3) -0.0034(19) 0.015(2) -0.0108(17) N5 0.060(2) 0.068(3) 0.066(3) 0.021(2) 0.003(2) -0.001(2) N6 0.064(2) 0.057(2) 0.058(2) 0.0099(18) 0.0146(19) 0.0006(19) C46 0.058(3) 0.053(3) 0.056(3) -0.003(2) 0.004(2) 0.004(2) C47 0.072(3) 0.072(3) 0.048(3) -0.002(2) 0.003(2) -0.017(3) C48 0.081(4) 0.094(4) 0.059(3) 0.000(3) -0.008(3) -0.013(3) C49 0.111(5) 0.106(5) 0.061(3) -0.014(3) -0.010(3) -0.029(4) C50 0.120(6) 0.093(5) 0.071(4) -0.025(3) 0.009(4) -0.022(4) C51 0.100(4) 0.074(4) 0.068(3) -0.017(3) 0.014(3) -0.015(3) C52 0.072(3) 0.065(3) 0.058(3) -0.010(2) 0.014(2) -0.010(3) C53 0.059(3) 0.068(3) 0.061(3) 0.001(2) -0.009(2) 0.007(2) C54 0.052(3) 0.050(2) 0.055(3) 0.006(2) -0.002(2) 0.011(2) C55 0.045(2) 0.047(2) 0.069(3) 0.003(2) -0.002(2) 0.0077(19) C56 0.048(2) 0.051(2) 0.060(3) 0.006(2) 0.005(2) 0.008(2) C57 0.052(3) 0.052(3) 0.065(3) -0.003(2) -0.004(2) 0.009(2) C58 0.049(2) 0.043(2) 0.070(3) 0.004(2) -0.001(2) 0.0055(19) C59 0.054(3) 0.049(2) 0.066(3) 0.009(2) 0.003(2) 0.011(2) C60 0.065(3) 0.046(3) 0.090(4) 0.001(2) 0.003(3) 0.002(2) C61 0.054(3) 0.057(3) 0.062(3) 0.002(2) 0.006(2) 0.001(2) C62 0.059(3) 0.063(3) 0.055(3) 0.000(2) 0.006(2) -0.013(2) C63 0.073(3) 0.058(3) 0.075(3) -0.005(2) 0.018(3) -0.012(3) C64 0.083(4) 0.078(4) 0.074(4) -0.014(3) 0.017(3) -0.028(3) C65 0.069(4) 0.091(4) 0.073(3) -0.005(3) 0.008(3) -0.030(3) C66 0.052(3) 0.086(4) 0.066(3) -0.001(3) 0.006(2) -0.014(3) C67 0.053(3) 0.064(3) 0.052(3) 0.000(2) 0.010(2) -0.009(2) C68 0.042(2) 0.072(3) 0.063(3) 0.001(2) 0.006(2) 0.002(2) C69 0.049(2) 0.058(3) 0.056(3) 0.005(2) 0.004(2) 0.011(2) C70 0.062(3) 0.055(3) 0.061(3) 0.002(2) 0.017(2) 0.010(2) C71 0.064(3) 0.048(3) 0.062(3) 0.002(2) 0.010(2) 0.012(2) C72 0.059(3) 0.052(3) 0.080(3) 0.011(2) 0.015(2) 0.014(2) C73 0.053(3) 0.064(3) 0.068(3) 0.020(2) 0.014(2) 0.019(2) C74 0.048(3) 0.067(3) 0.059(3) 0.013(2) 0.007(2) 0.011(2) C75 0.074(3) 0.056(3) 0.081(4) -0.012(3) 0.015(3) 0.007(3) C76 0.059(3) 0.079(3) 0.075(3) 0.030(3) 0.019(2) 0.016(3) C77 0.057(3) 0.057(3) 0.063(3) 0.016(2) 0.014(2) 0.004(2) C78 0.054(3) 0.052(3) 0.055(3) 0.003(2) 0.005(2) -0.004(2) C79 0.053(3) 0.072(3) 0.058(3) -0.006(2) 0.009(2) -0.008(2) C80 0.065(3) 0.078(4) 0.068(3) 0.003(3) 0.018(3) -0.018(3) C81 0.080(4) 0.072(3) 0.070(3) 0.017(3) 0.012(3) -0.014(3) C82 0.069(3) 0.059(3) 0.064(3) 0.012(2) 0.006(2) 0.000(2) C83 0.051(3) 0.065(3) 0.052(3) 0.003(2) 0.003(2) -0.006(2) C84 0.058(3) 0.062(3) 0.070(3) 0.010(2) 0.016(2) 0.011(2) C85 0.069(3) 0.071(3) 0.086(4) 0.001(3) -0.001(3) -0.016(3) C86 0.096(4) 0.067(3) 0.078(4) 0.022(3) 0.013(3) 0.003(3) C87 0.080(4) 0.092(4) 0.067(3) -0.012(3) -0.004(3) -0.004(3) C88 0.082(4) 0.074(4) 0.098(4) 0.010(3) 0.019(3) -0.008(3) C89 0.084(4) 0.106(5) 0.055(3) 0.006(3) 0.005(3) -0.001(3) C90 0.092(4) 0.088(4) 0.067(3) -0.006(3) 0.025(3) -0.018(3) N7 0.065(2) 0.058(2) 0.051(2) -0.0021(18) 0.0010(18) 0.0016(19) N8 0.066(2) 0.049(2) 0.059(2) -0.0056(17) 0.0093(19) 0.0000(18) N9 0.052(2) 0.050(2) 0.073(3) -0.0019(18) 0.0023(19) -0.0027(17) N10 0.046(2) 0.056(2) 0.062(2) 0.0014(18) 0.0015(17) -0.0021(17) N11 0.049(2) 0.057(2) 0.058(2) 0.0076(17) 0.0104(17) 0.0049(17) N12 0.053(2) 0.060(2) 0.062(2) 0.0145(19) 0.0126(18) 0.0074(18) Cu1B 0.094(7) 0.058(5) 0.068(6) -0.001(4) 0.003(5) 0.010(5) Cu2B 0.089(8) 0.074(7) 0.126(10) 0.018(6) -0.010(7) -0.002(6) Cl1 0.0860(10) 0.0865(10) 0.0842(10) -0.0006(8) -0.0005(8) 0.0179(8) O1 0.194(8) 0.087(4) 0.358(14) -0.013(6) -0.018(8) 0.017(5) O2 0.083(3) 0.322(10) 0.084(3) 0.032(4) 0.012(3) 0.055(5) O3 0.229(8) 0.289(10) 0.131(5) 0.093(6) 0.087(6) 0.131(8) O4 0.343(14) 0.204(9) 0.435(18) 0.160(10) -0.283(14) -0.169(10) Cl2 0.0695(10) 0.0649(9) 0.181(2) -0.0041(11) -0.0167(11) -0.0024(7) O5 0.141(6) 0.083(4) 0.394(13) -0.044(6) -0.061(7) -0.004(4) O6 0.063(3) 0.088(3) 0.177(5) -0.010(3) -0.003(3) -0.012(2) O7 0.194(8) 0.170(7) 0.291(13) -0.004(7) -0.117(8) 0.023(6) O8 0.118(6) 0.316(12) 0.276(12) -0.100(9) 0.080(7) -0.016(6) Cl3 0.0740(9) 0.0975(11) 0.0603(8) -0.0006(7) 0.0089(6) 0.0060(8) O9 0.088(3) 0.098(3) 0.085(3) -0.028(2) 0.014(2) -0.003(2) O10 0.246(8) 0.237(8) 0.103(4) 0.068(5) 0.045(5) 0.161(7) O11 0.144(4) 0.126(4) 0.068(3) 0.010(2) 0.030(3) 0.067(3) O12 0.214(8) 0.393(14) 0.138(6) -0.107(7) 0.048(5) -0.204(9) Cl4 0.0791(10) 0.0697(9) 0.1516(17) 0.0140(10) 0.0424(11) -0.0024(8) O13 0.080(3) 0.104(4) 0.181(5) -0.024(4) 0.020(3) 0.016(3) O14 0.122(5) 0.222(8) 0.136(5) -0.008(5) 0.017(4) 0.032(5) O15 0.124(5) 0.074(3) 0.334(11) 0.033(5) 0.093(6) 0.009(3) O16 0.126(5) 0.144(5) 0.183(6) 0.009(4) 0.070(4) -0.025(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 2.005(5) . ? Cu1 C16 2.008(5) . ? Cu2 C61 1.976(5) . ? Cu2 C46 1.987(5) . ? C1 N1 1.356(6) . ? C1 N2 1.364(6) . ? C2 C7 1.379(7) . ? C2 N1 1.395(6) . ? C2 C3 1.404(7) . ? C3 C4 1.367(8) . ? C3 H3 0.9300 . ? C4 C5 1.385(9) . ? C4 H4 0.9300 . ? C5 C6 1.400(8) . ? C5 H5 0.9300 . ? C6 C7 1.383(7) . ? C6 H6 0.9300 . ? C7 N2 1.394(6) . ? C8 N1 1.474(6) . ? C8 C9 1.520(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.386(7) . ? C9 C10 1.390(7) . ? C10 C11 1.415(8) . ? C10 C40 1.531(7) . ? C11 C12 1.382(7) . ? C11 C39 1.515(8) . ? C12 C13 1.405(7) . ? C12 C42 1.511(8) . ? C13 C14 1.404(7) . ? C13 C15 1.502(7) . ? C14 C41 1.522(8) . ? C15 N3 1.460(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N3 1.362(6) . ? C16 N4 1.364(6) . ? C17 C22 1.377(7) . ? C17 C18 1.388(7) . ? C17 N3 1.397(6) . ? C18 C19 1.399(8) . ? C18 H18 0.9300 . ? C19 C20 1.352(9) . ? C19 H19 0.9300 . ? C20 C21 1.352(9) . ? C20 H20 0.9300 . ? C21 C22 1.392(7) . ? C21 H21 0.9300 . ? C22 N4 1.393(6) . ? C23 N4 1.486(6) . ? C23 C24 1.492(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.386(7) . ? C24 C29 1.400(7) . ? C25 C26 1.397(7) . ? C25 C43 1.517(7) . ? C26 C27 1.401(7) . ? C26 C31 1.508(7) . ? C27 C28 1.405(7) . ? C27 C44 1.524(7) . ? C28 C29 1.387(6) . ? C28 C30 1.508(7) . ? C29 C45 1.502(7) . ? C30 N2 1.461(6) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 N6 1.489(6) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 N5 1.324(6) . ? C32 N6 1.333(6) . ? C32 H32 0.9300 . ? C33 C38 1.374(7) . ? C33 N5 1.398(6) . ? C33 C34 1.412(7) . ? C34 C35 1.365(9) . ? C34 H34 0.9300 . ? C35 C36 1.401(10) . ? C35 H35 0.9300 . ? C36 C37 1.368(8) . ? C36 H36 0.9300 . ? C37 C38 1.385(7) . ? C37 H37 0.9300 . ? C38 N6 1.399(6) . ? C39 N5 1.473(7) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 N7 1.361(6) . ? C46 N8 1.383(6) . ? C47 C52 1.371(7) . ? C47 N7 1.393(6) . ? C47 C48 1.404(7) . ? C48 C49 1.375(9) . ? C48 H48 0.9300 . ? C49 C50 1.388(10) . ? C49 H49 0.9300 . ? C50 C51 1.372(9) . ? C50 H50 0.9300 . ? C51 C52 1.395(7) . ? C51 H51 0.9300 . ? C52 N8 1.399(6) . ? C53 N7 1.465(6) . ? C53 C54 1.509(7) . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C54 C59 1.394(7) . ? C54 C55 1.401(7) . ? C55 C56 1.400(7) . ? C55 C85 1.520(7) . ? C56 C57 1.396(7) . ? C56 C84 1.502(7) . ? C57 C58 1.397(7) . ? C57 C87 1.515(7) . ? C58 C59 1.397(7) . ? C58 C60 1.506(6) . ? C59 C86 1.508(7) . ? C60 N9 1.464(6) . ? C60 H60A 0.9700 . ? C60 H60B 0.9700 . ? C61 N9 1.375(6) . ? C61 N10 1.383(6) . ? C62 N9 1.387(6) . ? C62 C63 1.388(7) . ? C62 C67 1.393(7) . ? C63 C64 1.380(8) . ? C63 H63 0.9300 . ? C64 C65 1.381(8) . ? C64 H64 0.9300 . ? C65 C66 1.385(8) . ? C65 H65 0.9300 . ? C66 C67 1.384(6) . ? C66 H66 0.9300 . ? C67 N10 1.385(6) . ? C68 N10 1.481(6) . ? C68 C69 1.507(7) . ? C68 H68A 0.9700 . ? C68 H68B 0.9700 . ? C69 C74 1.397(6) . ? C69 C70 1.398(7) . ? C70 C71 1.399(7) . ? C70 C90 1.518(7) . ? C71 C72 1.388(7) . ? C71 C75 1.480(7) . ? C72 C73 1.409(7) . ? C72 C88 1.530(8) . ? C73 C74 1.377(7) . ? C73 C76 1.531(7) . ? C74 C89 1.532(7) . ? C75 N8 1.465(6) . ? C75 H75A 0.9700 . ? C75 H75B 0.9700 . ? C76 N12 1.481(6) . ? C76 H76A 0.9700 . ? C76 H76B 0.9700 . ? C77 N11 1.318(6) . ? C77 N12 1.322(6) . ? C77 H77 0.9300 . ? C78 C79 1.382(6) . ? C78 C83 1.393(7) . ? C78 N11 1.393(6) . ? C79 C80 1.394(7) . ? C79 H79 0.9300 . ? C80 C81 1.384(8) . ? C80 H80 0.9300 . ? C81 C82 1.371(7) . ? C81 H81 0.9300 . ? C82 C83 1.380(7) . ? C82 H82 0.9300 . ? C83 N12 1.397(6) . ? C84 N11 1.487(6) . ? C84 H84A 0.9700 . ? C84 H84B 0.9700 . ? C85 H85A 0.9600 . ? C85 H85B 0.9600 . ? C85 H85C 0.9600 . ? C86 H86A 0.9600 . ? C86 H86B 0.9600 . ? C86 H86C 0.9600 . ? C87 H87A 0.9600 . ? C87 H87B 0.9600 . ? C87 H87C 0.9600 . ? C88 H88A 0.9600 . ? C88 H88B 0.9600 . ? C88 H88C 0.9600 . ? C89 H89A 0.9600 . ? C89 H89B 0.9600 . ? C89 H89C 0.9600 . ? C90 H90A 0.9600 . ? C90 H90B 0.9600 . ? C90 H90C 0.9600 . ? Cl1 O4 1.324(9) . ? Cl1 O1 1.385(7) . ? Cl1 O2 1.409(6) . ? Cl1 O3 1.449(7) . ? Cl2 O5 1.367(6) . ? Cl2 O6 1.375(4) . ? Cl2 O8 1.401(8) . ? Cl2 O7 1.404(9) . ? Cl3 O10 1.357(6) . ? Cl3 O12 1.390(7) . ? Cl3 O9 1.402(4) . ? Cl3 O11 1.404(4) . ? Cl4 O16 1.394(6) . ? Cl4 O15 1.404(5) . ? Cl4 O13 1.434(5) . ? Cl4 O14 1.454(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 C1 Cu1 C16 178.76(19) . . ? C61 Cu2 C46 172.6(2) . . ? N1 C1 N2 104.5(4) . . ? N1 C1 Cu1 127.5(3) . . ? N2 C1 Cu1 128.0(3) . . ? C7 C2 N1 106.5(4) . . ? C7 C2 C3 121.4(5) . . ? N1 C2 C3 132.0(5) . . ? C4 C3 C2 116.1(6) . . ? C4 C3 H3 121.9 . . ? C2 C3 H3 121.9 . . ? C3 C4 C5 122.6(5) . . ? C3 C4 H4 118.7 . . ? C5 C4 H4 118.7 . . ? C4 C5 C6 121.7(5) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 115.5(6) . . ? C7 C6 H6 122.2 . . ? C5 C6 H6 122.2 . . ? C2 C7 C6 122.7(5) . . ? C2 C7 N2 105.6(4) . . ? C6 C7 N2 131.7(5) . . ? N1 C8 C9 109.3(4) . . ? N1 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? N1 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? C14 C9 C10 121.1(5) . . ? C14 C9 C8 119.1(5) . . ? C10 C9 C8 119.2(5) . . ? C9 C10 C11 119.2(5) . . ? C9 C10 C40 121.0(5) . . ? C11 C10 C40 119.7(5) . . ? C12 C11 C10 120.4(5) . . ? C12 C11 C39 120.1(5) . . ? C10 C11 C39 119.4(5) . . ? C11 C12 C13 119.3(5) . . ? C11 C12 C42 122.4(5) . . ? C13 C12 C42 118.2(5) . . ? C14 C13 C12 120.6(5) . . ? C14 C13 C15 119.2(5) . . ? C12 C13 C15 119.5(5) . . ? C9 C14 C13 119.0(5) . . ? C9 C14 C41 120.6(5) . . ? C13 C14 C41 120.3(5) . . ? N3 C15 C13 110.8(4) . . ? N3 C15 H15A 109.5 . . ? C13 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? N3 C16 N4 104.6(4) . . ? N3 C16 Cu1 128.1(3) . . ? N4 C16 Cu1 127.1(4) . . ? C22 C17 C18 122.5(5) . . ? C22 C17 N3 106.4(4) . . ? C18 C17 N3 131.1(5) . . ? C17 C18 C19 114.1(6) . . ? C17 C18 H18 123.0 . . ? C19 C18 H18 123.0 . . ? C20 C19 C18 123.2(6) . . ? C20 C19 H19 118.4 . . ? C18 C19 H19 118.4 . . ? C21 C20 C19 122.4(6) . . ? C21 C20 H20 118.8 . . ? C19 C20 H20 118.8 . . ? C20 C21 C22 116.7(6) . . ? C20 C21 H21 121.7 . . ? C22 C21 H21 121.7 . . ? C17 C22 C21 121.1(5) . . ? C17 C22 N4 106.1(4) . . ? C21 C22 N4 132.8(5) . . ? N4 C23 C24 110.4(4) . . ? N4 C23 H23A 109.6 . . ? C24 C23 H23A 109.6 . . ? N4 C23 H23B 109.6 . . ? C24 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? C25 C24 C29 120.9(4) . . ? C25 C24 C23 119.8(5) . . ? C29 C24 C23 119.0(4) . . ? C24 C25 C26 119.7(4) . . ? C24 C25 C43 120.1(5) . . ? C26 C25 C43 120.2(5) . . ? C25 C26 C27 120.5(4) . . ? C25 C26 C31 119.8(4) . . ? C27 C26 C31 119.6(4) . . ? C26 C27 C28 118.4(4) . . ? C26 C27 C44 120.5(5) . . ? C28 C27 C44 121.0(5) . . ? C29 C28 C27 121.5(4) . . ? C29 C28 C30 119.8(4) . . ? C27 C28 C30 118.2(4) . . ? C28 C29 C24 118.6(4) . . ? C28 C29 C45 121.0(5) . . ? C24 C29 C45 120.3(5) . . ? N2 C30 C28 110.3(4) . . ? N2 C30 H30A 109.6 . . ? C28 C30 H30A 109.6 . . ? N2 C30 H30B 109.6 . . ? C28 C30 H30B 109.6 . . ? H30A C30 H30B 108.1 . . ? N6 C31 C26 111.1(4) . . ? N6 C31 H31A 109.4 . . ? C26 C31 H31A 109.4 . . ? N6 C31 H31B 109.4 . . ? C26 C31 H31B 109.4 . . ? H31A C31 H31B 108.0 . . ? N5 C32 N6 110.7(4) . . ? N5 C32 H32 124.6 . . ? N6 C32 H32 124.6 . . ? C38 C33 N5 107.8(4) . . ? C38 C33 C34 121.7(5) . . ? N5 C33 C34 130.5(6) . . ? C35 C34 C33 114.6(6) . . ? C35 C34 H34 122.7 . . ? C33 C34 H34 122.7 . . ? C34 C35 C36 123.3(5) . . ? C34 C35 H35 118.3 . . ? C36 C35 H35 118.3 . . ? C37 C36 C35 121.8(6) . . ? C37 C36 H36 119.1 . . ? C35 C36 H36 119.1 . . ? C36 C37 C38 115.5(6) . . ? C36 C37 H37 122.2 . . ? C38 C37 H37 122.2 . . ? C33 C38 C37 123.1(5) . . ? C33 C38 N6 105.9(4) . . ? C37 C38 N6 131.0(5) . . ? N5 C39 C11 111.4(4) . . ? N5 C39 H39A 109.3 . . ? C11 C39 H39A 109.3 . . ? N5 C39 H39B 109.3 . . ? C11 C39 H39B 109.3 . . ? H39A C39 H39B 108.0 . . ? C10 C40 H40A 109.5 . . ? C10 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C10 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C14 C41 H41A 109.5 . . ? C14 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C14 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C12 C42 H42A 109.5 . . ? C12 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C12 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C25 C43 H43A 109.5 . . ? C25 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C25 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C27 C44 H44A 109.5 . . ? C27 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C27 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C29 C45 H45A 109.5 . . ? C29 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C29 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C1 N1 C2 111.5(4) . . ? C1 N1 C8 128.0(4) . . ? C2 N1 C8 120.4(4) . . ? C1 N2 C7 111.8(4) . . ? C1 N2 C30 127.2(4) . . ? C7 N2 C30 120.9(4) . . ? C16 N3 C17 111.3(4) . . ? C16 N3 C15 128.4(4) . . ? C17 N3 C15 120.3(4) . . ? C16 N4 C22 111.6(4) . . ? C16 N4 C23 128.9(4) . . ? C22 N4 C23 119.3(4) . . ? C32 N5 C33 107.3(4) . . ? C32 N5 C39 127.2(4) . . ? C33 N5 C39 125.4(4) . . ? C32 N6 C38 108.1(4) . . ? C32 N6 C31 127.6(4) . . ? C38 N6 C31 124.2(4) . . ? N7 C46 N8 104.2(4) . . ? N7 C46 Cu2 126.7(3) . . ? N8 C46 Cu2 128.4(3) . . ? C52 C47 N7 106.4(4) . . ? C52 C47 C48 122.2(5) . . ? N7 C47 C48 131.4(5) . . ? C49 C48 C47 115.3(6) . . ? C49 C48 H48 122.4 . . ? C47 C48 H48 122.4 . . ? C48 C49 C50 122.1(6) . . ? C48 C49 H49 119.0 . . ? C50 C49 H49 119.0 . . ? C51 C50 C49 122.9(6) . . ? C51 C50 H50 118.5 . . ? C49 C50 H50 118.5 . . ? C50 C51 C52 115.2(6) . . ? C50 C51 H51 122.4 . . ? C52 C51 H51 122.4 . . ? C47 C52 C51 122.3(5) . . ? C47 C52 N8 106.7(4) . . ? C51 C52 N8 131.0(5) . . ? N7 C53 C54 111.2(4) . . ? N7 C53 H53A 109.4 . . ? C54 C53 H53A 109.4 . . ? N7 C53 H53B 109.4 . . ? C54 C53 H53B 109.4 . . ? H53A C53 H53B 108.0 . . ? C59 C54 C55 120.8(4) . . ? C59 C54 C53 119.2(4) . . ? C55 C54 C53 119.6(4) . . ? C56 C55 C54 119.2(4) . . ? C56 C55 C85 120.3(4) . . ? C54 C55 C85 120.3(4) . . ? C57 C56 C55 120.6(4) . . ? C57 C56 C84 120.5(4) . . ? C55 C56 C84 118.8(4) . . ? C56 C57 C58 119.1(4) . . ? C56 C57 C87 120.3(5) . . ? C58 C57 C87 120.4(5) . . ? C57 C58 C59 121.1(4) . . ? C57 C58 C60 119.7(4) . . ? C59 C58 C60 118.6(5) . . ? C54 C59 C58 119.0(4) . . ? C54 C59 C86 119.9(5) . . ? C58 C59 C86 121.0(5) . . ? N9 C60 C58 111.3(4) . . ? N9 C60 H60A 109.4 . . ? C58 C60 H60A 109.4 . . ? N9 C60 H60B 109.4 . . ? C58 C60 H60B 109.4 . . ? H60A C60 H60B 108.0 . . ? N9 C61 N10 103.4(4) . . ? N9 C61 Cu2 129.9(3) . . ? N10 C61 Cu2 126.3(3) . . ? N9 C62 C63 132.2(5) . . ? N9 C62 C67 106.1(4) . . ? C63 C62 C67 121.7(5) . . ? C64 C63 C62 116.1(5) . . ? C64 C63 H63 121.9 . . ? C62 C63 H63 121.9 . . ? C63 C64 C65 122.4(5) . . ? C63 C64 H64 118.8 . . ? C65 C64 H64 118.8 . . ? C64 C65 C66 121.7(5) . . ? C64 C65 H65 119.2 . . ? C66 C65 H65 119.2 . . ? C67 C66 C65 116.5(5) . . ? C67 C66 H66 121.8 . . ? C65 C66 H66 121.8 . . ? C66 C67 N10 132.2(5) . . ? C66 C67 C62 121.6(5) . . ? N10 C67 C62 106.2(4) . . ? N10 C68 C69 110.9(4) . . ? N10 C68 H68A 109.5 . . ? C69 C68 H68A 109.5 . . ? N10 C68 H68B 109.5 . . ? C69 C68 H68B 109.5 . . ? H68A C68 H68B 108.1 . . ? C74 C69 C70 120.3(5) . . ? C74 C69 C68 120.4(4) . . ? C70 C69 C68 118.9(4) . . ? C69 C70 C71 119.2(4) . . ? C69 C70 C90 120.0(5) . . ? C71 C70 C90 120.6(5) . . ? C72 C71 C70 120.7(5) . . ? C72 C71 C75 119.3(5) . . ? C70 C71 C75 119.4(4) . . ? C71 C72 C73 118.8(5) . . ? C71 C72 C88 120.2(5) . . ? C73 C72 C88 120.8(5) . . ? C74 C73 C72 121.0(4) . . ? C74 C73 C76 120.9(5) . . ? C72 C73 C76 118.0(5) . . ? C73 C74 C69 119.6(5) . . ? C73 C74 C89 122.0(4) . . ? C69 C74 C89 118.3(5) . . ? N8 C75 C71 111.2(4) . . ? N8 C75 H75A 109.4 . . ? C71 C75 H75A 109.4 . . ? N8 C75 H75B 109.4 . . ? C71 C75 H75B 109.4 . . ? H75A C75 H75B 108.0 . . ? N12 C76 C73 110.6(4) . . ? N12 C76 H76A 109.5 . . ? C73 C76 H76A 109.5 . . ? N12 C76 H76B 109.5 . . ? C73 C76 H76B 109.5 . . ? H76A C76 H76B 108.1 . . ? N11 C77 N12 111.5(4) . . ? N11 C77 H77 124.3 . . ? N12 C77 H77 124.3 . . ? C79 C78 C83 122.3(4) . . ? C79 C78 N11 131.1(4) . . ? C83 C78 N11 106.6(4) . . ? C78 C79 C80 115.8(5) . . ? C78 C79 H79 122.1 . . ? C80 C79 H79 122.1 . . ? C81 C80 C79 121.2(5) . . ? C81 C80 H80 119.4 . . ? C79 C80 H80 119.4 . . ? C82 C81 C80 123.0(5) . . ? C82 C81 H81 118.5 . . ? C80 C81 H81 118.5 . . ? C81 C82 C83 116.2(5) . . ? C81 C82 H82 121.9 . . ? C83 C82 H82 121.9 . . ? C82 C83 C78 121.5(4) . . ? C82 C83 N12 132.2(5) . . ? C78 C83 N12 106.2(4) . . ? N11 C84 C56 110.7(4) . . ? N11 C84 H84A 109.5 . . ? C56 C84 H84A 109.5 . . ? N11 C84 H84B 109.5 . . ? C56 C84 H84B 109.5 . . ? H84A C84 H84B 108.1 . . ? C55 C85 H85A 109.5 . . ? C55 C85 H85B 109.5 . . ? H85A C85 H85B 109.5 . . ? C55 C85 H85C 109.5 . . ? H85A C85 H85C 109.5 . . ? H85B C85 H85C 109.5 . . ? C59 C86 H86A 109.5 . . ? C59 C86 H86B 109.5 . . ? H86A C86 H86B 109.5 . . ? C59 C86 H86C 109.5 . . ? H86A C86 H86C 109.5 . . ? H86B C86 H86C 109.5 . . ? C57 C87 H87A 109.5 . . ? C57 C87 H87B 109.5 . . ? H87A C87 H87B 109.5 . . ? C57 C87 H87C 109.5 . . ? H87A C87 H87C 109.5 . . ? H87B C87 H87C 109.5 . . ? C72 C88 H88A 109.5 . . ? C72 C88 H88B 109.5 . . ? H88A C88 H88B 109.5 . . ? C72 C88 H88C 109.5 . . ? H88A C88 H88C 109.5 . . ? H88B C88 H88C 109.5 . . ? C74 C89 H89A 109.5 . . ? C74 C89 H89B 109.5 . . ? H89A C89 H89B 109.5 . . ? C74 C89 H89C 109.5 . . ? H89A C89 H89C 109.5 . . ? H89B C89 H89C 109.5 . . ? C70 C90 H90A 109.5 . . ? C70 C90 H90B 109.5 . . ? H90A C90 H90B 109.5 . . ? C70 C90 H90C 109.5 . . ? H90A C90 H90C 109.5 . . ? H90B C90 H90C 109.5 . . ? C46 N7 C47 111.9(4) . . ? C46 N7 C53 127.7(4) . . ? C47 N7 C53 120.4(4) . . ? C46 N8 C52 110.8(4) . . ? C46 N8 C75 128.4(4) . . ? C52 N8 C75 120.8(4) . . ? C61 N9 C62 112.3(4) . . ? C61 N9 C60 128.0(4) . . ? C62 N9 C60 119.6(4) . . ? C61 N10 C67 112.0(4) . . ? C61 N10 C68 127.0(4) . . ? C67 N10 C68 120.9(4) . . ? C77 N11 C78 107.8(4) . . ? C77 N11 C84 127.2(4) . . ? C78 N11 C84 125.0(4) . . ? C77 N12 C83 107.8(4) . . ? C77 N12 C76 127.6(4) . . ? C83 N12 C76 124.5(4) . . ? O4 Cl1 O1 100.7(6) . . ? O4 Cl1 O2 107.3(7) . . ? O1 Cl1 O2 112.3(6) . . ? O4 Cl1 O3 134.8(9) . . ? O1 Cl1 O3 97.8(6) . . ? O2 Cl1 O3 103.1(4) . . ? O5 Cl2 O6 113.4(4) . . ? O5 Cl2 O8 116.8(7) . . ? O6 Cl2 O8 111.9(5) . . ? O5 Cl2 O7 106.0(6) . . ? O6 Cl2 O7 106.1(5) . . ? O8 Cl2 O7 101.1(7) . . ? O10 Cl3 O12 109.7(7) . . ? O10 Cl3 O9 113.0(4) . . ? O12 Cl3 O9 106.7(4) . . ? O10 Cl3 O11 108.4(4) . . ? O12 Cl3 O11 110.2(6) . . ? O9 Cl3 O11 108.9(3) . . ? O16 Cl4 O15 111.2(4) . . ? O16 Cl4 O13 108.0(4) . . ? O15 Cl4 O13 107.8(4) . . ? O16 Cl4 O14 108.7(4) . . ? O15 Cl4 O14 113.6(5) . . ? O13 Cl4 O14 107.3(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.288 _refine_diff_density_min -0.555 _refine_diff_density_rms 0.091 #===END data_[AgLH]_NO3 _database_code_depnum_ccdc_archive 'CCDC 824176' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C45 H43 Ag N6, 2(N O3), 5 (H2 O)' _chemical_formula_sum 'C45 H53 Ag N8 O11' _chemical_formula_weight 989.74 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' Ag Ag -0.8971 1.1015 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'I b m m' _symmetry_space_group_name_Hall '-I 2c 2c' _symmetry_Int_Tables_number 74 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, -z+1/2' '-x, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1' 'x+1/2, -y+1/2, -z+1' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, -z-1/2' '-x, y, z-1/2' 'x, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y+1/2, -z' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 15.243(7) _cell_length_b 17.179(8) _cell_length_c 17.400(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4556(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 15 _exptl_crystal_description PRISM _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2056 _exptl_absorpt_coefficient_mu 0.511 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.731 _exptl_absorpt_correction_T_max 0.776 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Enraf-Nonius CAD4' _diffrn_measurement_method 'omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 300 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4231 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2163 _reflns_number_gt 1503 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR-97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (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^ > 2\s(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. The O2W site is only half populated by oxygen of a water molecule. Positions for H atom forming water molecules are not located ; _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^)+(0.1820P)^2^+0.0000P] 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 2163 _refine_ls_number_parameters 170 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.1151 _refine_ls_R_factor_gt 0.0914 _refine_ls_wR_factor_ref 0.2719 _refine_ls_wR_factor_gt 0.2487 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.147 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 Ag1 Ag 0.35159(6) 1.0000 0.7500 0.0794(6) Uani 1 4 d S . . C1 C 0.3557(5) 0.8779(8) 0.7500 0.078(3) Uani 1 2 d S . . C2 C 0.3670(4) 0.7545(6) 0.7906(5) 0.088(2) Uani 1 1 d . . . C3 C 0.3772(6) 0.6858(6) 0.8318(7) 0.105(3) Uani 1 1 d . . . H3 H 0.3780 0.6856 0.8853 0.126 Uiso 1 1 calc R . . C4 C 0.3859(9) 0.6186(9) 0.7906(8) 0.152(5) Uani 1 1 d . . . H4 H 0.3920 0.5717 0.8167 0.183 Uiso 1 1 calc R . . C5 C 0.3574(4) 0.8543(6) 0.8934(4) 0.087(2) Uani 1 1 d . . . H5A H 0.3825 0.8139 0.9257 0.105 Uiso 1 1 calc R . . H5B H 0.2968 0.8617 0.9087 0.105 Uiso 1 1 calc R . . C6 C 0.4078(4) 0.9296(5) 0.9049(3) 0.080(2) Uani 1 1 d . . . C7 C 0.4987(4) 0.9295(5) 0.8984(3) 0.085(2) Uani 1 1 d . . . C8 C 0.5433(6) 1.0000 0.8987(5) 0.075(3) Uani 1 2 d S . . C9 C 0.6441(5) 1.0000 0.8932(6) 0.092(4) Uani 1 2 d S . . H9A H 0.6671 1.0457 0.9190 0.110 Uiso 0.50 1 calc PR . . H9B H 0.6671 0.9543 0.9190 0.110 Uiso 0.50 1 calc PR . . C10 C 0.7589(8) 1.0000 0.7883(7) 0.111(4) Uani 1 2 d SU . . C11 C 0.8342(9) 1.0000 0.8353(11) 0.133(5) Uani 1 2 d SU . . H11 H 0.8305 1.0000 0.8886 0.159 Uiso 1 2 calc SR . . C12 C 0.919(2) 1.0000 0.7947(18) 0.256(14) Uani 1 2 d SU . . H12 H 0.9717 1.0000 0.8220 0.307 Uiso 1 2 calc SR . . C13 C 0.6249(9) 1.0000 0.7500 0.090(5) Uani 1 4 d S . . H13 H 0.5638 1.0000 0.7500 0.108 Uiso 1 4 calc SR . . C14 C 0.5481(5) 0.8549(6) 0.8888(5) 0.107(3) Uani 1 1 d . . . H14A H 0.5280 0.8287 0.8434 0.160 Uiso 1 1 calc R . . H14B H 0.5383 0.8223 0.9328 0.160 Uiso 1 1 calc R . . H14C H 0.6096 0.8659 0.8841 0.160 Uiso 1 1 calc R . . C15 C 0.3611(6) 1.0000 0.9112(5) 0.075(3) Uani 1 2 d S . . C16 C 0.2634(6) 1.0000 0.9219(6) 0.095(3) Uani 1 2 d S . . H16A H 0.2501 1.0000 0.9759 0.143 Uiso 1 2 d SR . . H16B H 0.2389 0.9544 0.8985 0.143 Uiso 1 1 d R . . N1 N 0.3610(3) 0.8295(4) 0.8117(4) 0.0785(16) Uani 1 1 d . . . N2 N 0.6735(5) 1.0000 0.8129(5) 0.094(3) Uani 1 2 d S . . N3 N 0.5000 0.6211(17) 0.5000 0.294(10) Uani 1 2 d SDU . . O1 O 0.5669(12) 0.5823(9) 0.4976(11) 0.282(7) Uani 1 1 d DU . . O2 O 0.5000 0.6932(17) 0.5000 0.326(11) Uani 1 2 d SDU . . O1W O 0.7909(13) 0.8325(8) 0.9425(10) 0.275(8) Uani 1 1 d . . . O2W O 0.724(3) 0.818(2) 0.7500 0.264(18) Uani 0.50 2 d SPU . . 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 Ag1 0.0727(7) 0.1278(11) 0.0377(6) 0.000 0.000 0.000 C1 0.057(5) 0.128(9) 0.049(5) 0.000 0.000 0.004(5) C2 0.051(3) 0.135(7) 0.077(4) 0.016(5) 0.004(3) -0.008(4) C3 0.082(5) 0.109(7) 0.125(8) 0.010(6) 0.001(5) -0.016(5) C4 0.129(8) 0.157(10) 0.172(12) 0.038(9) -0.008(8) -0.040(8) C5 0.074(4) 0.141(7) 0.047(3) 0.013(4) 0.003(3) -0.003(4) C6 0.065(4) 0.143(7) 0.033(3) 0.002(3) -0.001(2) 0.003(4) C7 0.061(3) 0.157(7) 0.036(3) 0.007(3) -0.004(2) 0.010(4) C8 0.060(5) 0.130(8) 0.035(4) 0.000 -0.001(3) 0.000 C9 0.059(5) 0.171(11) 0.046(5) 0.000 -0.006(4) 0.000 C10 0.077(6) 0.168(9) 0.086(6) 0.000 -0.023(5) 0.000 C11 0.083(6) 0.195(10) 0.121(9) 0.000 -0.005(6) 0.000 C12 0.243(16) 0.274(16) 0.250(17) 0.000 -0.002(10) 0.000 C13 0.050(6) 0.175(16) 0.045(7) 0.000 0.000 0.000 C14 0.078(5) 0.164(8) 0.079(5) 0.003(5) -0.009(4) 0.015(5) C15 0.063(5) 0.134(9) 0.029(4) 0.000 0.002(3) 0.000 C16 0.062(5) 0.162(11) 0.061(5) 0.000 0.001(4) 0.000 N1 0.061(3) 0.116(5) 0.059(3) 0.004(3) -0.001(2) -0.007(3) N2 0.046(4) 0.192(10) 0.043(4) 0.000 -0.002(3) 0.000 N3 0.295(18) 0.306(18) 0.281(15) 0.000 0.047(17) 0.000 O1 0.282(16) 0.288(15) 0.276(15) 0.072(12) 0.039(15) 0.069(11) O2 0.337(13) 0.321(14) 0.320(13) 0.000 0.016(9) 0.000 O1W 0.299(17) 0.187(11) 0.34(2) -0.028(13) 0.013(16) 0.032(12) O2W 0.26(2) 0.27(2) 0.26(2) 0.000 0.000 0.000(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Ag1 C1 2.098(13) . ? Ag1 C1 2.098(13) 3_576 ? C1 N1 1.361(10) 10_557 ? C1 N1 1.361(10) . ? C2 N1 1.343(12) . ? C2 C3 1.389(13) . ? C2 C2 1.414(16) 10_557 ? C3 C4 1.365(16) . ? C3 H3 0.9300 . ? C4 C4 1.41(3) 10_557 ? C4 H4 0.9300 . ? C5 N1 1.486(9) . ? C5 C6 1.517(12) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.390(9) . ? C6 C15 1.407(8) . ? C7 C8 1.389(9) . ? C7 C14 1.494(12) . ? C8 C7 1.389(9) 12_575 ? C8 C9 1.540(12) . ? C9 N2 1.466(12) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C10 1.33(2) 10_557 ? C10 N2 1.370(14) . ? C10 C11 1.409(18) . ? C11 C12 1.48(3) . ? C11 H11 0.9300 . ? C12 C12 1.56(6) 10_557 ? C12 H12 0.9300 . ? C13 N2 1.322(10) . ? C13 N2 1.322(10) 10_557 ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C6 1.407(9) 12_575 ? C15 C16 1.501(12) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? N3 O1 1.22(2) 4_656 ? N3 O1 1.22(2) . ? N3 O2 1.24(4) . ? 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 C1 Ag1 C1 176.6(4) . 3_576 ? N1 C1 N1 104.2(11) 10_557 . ? N1 C1 Ag1 127.8(5) 10_557 . ? N1 C1 Ag1 127.8(5) . . ? N1 C2 C3 132.9(8) . . ? N1 C2 C2 105.9(4) . 10_557 ? C3 C2 C2 121.1(6) . 10_557 ? C4 C3 C2 117.3(11) . . ? C4 C3 H3 121.4 . . ? C2 C3 H3 121.4 . . ? C3 C4 C4 121.7(7) . 10_557 ? C3 C4 H4 119.2 . . ? C4 C4 H4 119.2 10_557 . ? N1 C5 C6 110.6(6) . . ? N1 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C7 C6 C15 120.8(8) . . ? C7 C6 C5 119.5(7) . . ? C15 C6 C5 119.2(6) . . ? C8 C7 C6 119.1(8) . . ? C8 C7 C14 120.1(6) . . ? C6 C7 C14 120.8(8) . . ? C7 C8 C7 121.4(8) . 12_575 ? C7 C8 C9 119.2(4) . . ? C7 C8 C9 119.2(4) 12_575 . ? N2 C9 C8 111.4(7) . . ? N2 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? N2 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C10 C10 N2 108.2(6) 10_557 . ? C10 C10 C11 125.5(9) 10_557 . ? N2 C10 C11 126.3(12) . . ? C10 C11 C12 116(2) . . ? C10 C11 H11 122.0 . . ? C12 C11 H11 122.0 . . ? C11 C12 C12 118.5(15) . 10_557 ? C11 C12 H12 120.7 . . ? C12 C12 H12 120.7 10_557 . ? N2 C13 N2 111.8(11) . 10_557 ? N2 C13 H13 124.1 . . ? N2 C13 H13 124.1 10_557 . ? C7 C14 H14A 109.5 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C6 C15 C6 118.5(8) 12_575 . ? C6 C15 C16 120.7(4) 12_575 . ? C6 C15 C16 120.7(4) . . ? C15 C16 H16A 109.4 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C2 N1 C1 112.0(7) . . ? C2 N1 C5 122.7(7) . . ? C1 N1 C5 125.3(8) . . ? C13 N2 C10 105.9(9) . . ? C13 N2 C9 128.1(8) . . ? C10 N2 C9 126.0(8) . . ? O1 N3 O1 114(3) 4_656 . ? O1 N3 O2 123.1(17) 4_656 . ? O1 N3 O2 123.1(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 -176.4(9) . . . . ? C2 C2 C3 C4 -0.9(11) 10_557 . . . ? C2 C3 C4 C4 0.9(11) . . . 10_557 ? N1 C5 C6 C7 -69.3(8) . . . . ? N1 C5 C6 C15 101.8(7) . . . . ? C15 C6 C7 C8 0.4(9) . . . . ? C5 C6 C7 C8 171.4(6) . . . . ? C15 C6 C7 C14 -177.7(7) . . . . ? C5 C6 C7 C14 -6.7(9) . . . . ? C6 C7 C8 C7 -5.8(12) . . . 12_575 ? C14 C7 C8 C7 172.3(6) . . . 12_575 ? C6 C7 C8 C9 178.8(7) . . . . ? C14 C7 C8 C9 -3.1(11) . . . . ? C7 C8 C9 N2 87.7(6) . . . . ? C7 C8 C9 N2 -87.7(6) 12_575 . . . ? C10 C10 C11 C12 0.000(6) 10_557 . . . ? N2 C10 C11 C12 180.000(6) . . . . ? C10 C11 C12 C12 0.000(11) . . . 10_557 ? C7 C6 C15 C6 4.7(11) . . . 12_575 ? C5 C6 C15 C6 -166.3(5) . . . 12_575 ? C7 C6 C15 C16 -177.1(7) . . . . ? C5 C6 C15 C16 11.9(10) . . . . ? C3 C2 N1 C1 177.0(8) . . . . ? C2 C2 N1 C1 1.0(6) 10_557 . . . ? C3 C2 N1 C5 -5.1(11) . . . . ? C2 C2 N1 C5 178.9(4) 10_557 . . . ? N1 C1 N1 C2 -1.6(9) 10_557 . . . ? Ag1 C1 N1 C2 -176.6(5) . . . . ? N1 C1 N1 C5 -179.4(4) 10_557 . . . ? Ag1 C1 N1 C5 5.5(10) . . . . ? C6 C5 N1 C2 143.0(6) . . . . ? C6 C5 N1 C1 -39.4(9) . . . . ? N2 C13 N2 C10 0.000(3) 10_557 . . . ? N2 C13 N2 C9 180.000(3) 10_557 . . . ? C10 C10 N2 C13 0.000(2) 10_557 . . . ? C11 C10 N2 C13 180.000(3) . . . . ? C10 C10 N2 C9 180.000(3) 10_557 . . . ? C11 C10 N2 C9 0.000(3) . . . . ? C8 C9 N2 C13 0.000(3) . . . . ? C8 C9 N2 C10 180.000(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.843 _refine_diff_density_min -0.785 _refine_diff_density_rms 0.146