# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name D.Ray G.Aromi P.K.Nanda _publ_contact_author_name 'Debashis Ray' _publ_contact_author_email dray@chem.iitkgp.ernet.in data_drpn0017 _database_code_depnum_ccdc_archive 'CCDC 292303' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C60 H98 Cl Cu4 N11 O22' _chemical_formula_weight 1614.52 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 C2/m 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 14.7689(4) _cell_length_b 18.0119(8) _cell_length_c 13.5174(9) _cell_angle_alpha 90.00 _cell_angle_beta 103.600(2) _cell_angle_gamma 90.00 _cell_volume 3495.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Green _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 1.320 _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 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 cad4 _diffrn_measurement_method /W-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 25 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5955 _diffrn_reflns_av_R_equivalents 0.1559 _diffrn_reflns_av_sigmaI/netI 0.1418 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3079 _reflns_number_gt 1620 _reflns_threshold_expression >2sigma(I) _computing_data_collection cad4 _computing_cell_refinement cad4 _computing_data_reduction cad4 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1232P)^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 3079 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1459 _refine_ls_R_factor_gt 0.0810 _refine_ls_wR_factor_ref 0.2343 _refine_ls_wR_factor_gt 0.1915 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 Cu1 Cu 0.18554(6) 0.41237(5) 0.10904(6) 0.0553(4) Uani 1 1 d . . . O1 O 0.2618(5) 0.5000 0.0910(4) 0.0497(15) Uani 1 2 d S . . O2 O 0.1662(4) 0.3905(3) -0.0303(4) 0.0694(15) Uani 1 1 d . . . O3A O 0.2485(12) 0.5000 0.8689(11) 0.058(4) Uiso 0.50 2 d SP . . O3B O 0.2078(15) 0.5000 0.8506(14) 0.079(6) Uiso 0.50 2 d SP . . O4A O 0.2870(19) 0.6352(16) 0.6003(17) 0.176(9) Uiso 0.50 1 d P . . O4B O 0.2196(18) 0.6360(15) 0.5920(16) 0.161(8) Uiso 0.50 1 d P . . O5 O 0.0279(17) 0.5354(15) 0.5417(16) 0.199(11) Uiso 0.50 1 d P . . O6A O 0.461(2) 0.677(2) 0.509(3) 0.243(16) Uiso 0.50 1 d P . . O6B O 0.409(2) 0.6697(19) 0.545(2) 0.194(10) Uiso 0.50 1 d P . . O7A O 0.129(3) 0.262(3) 0.503(3) 0.30(2) Uiso 0.50 1 d P . . O7B O 0.090(3) 0.324(3) 0.496(3) 0.32(2) Uiso 0.50 1 d P . . N1 N 0.1679(4) 0.3098(3) 0.1456(5) 0.0569(15) Uani 1 1 d . . . N2 N 0.2067(4) 0.4361(3) 0.2627(4) 0.0535(14) Uani 1 1 d . . . N3 N 0.0591(7) 0.5000 0.0711(8) 0.071(2) Uani 1 2 d S . . N4 N 0.0000 0.5000 0.0000 0.054(3) Uani 1 4 d S . . C1 C 0.1322(5) 0.3284(4) -0.0763(6) 0.0591(19) Uani 1 1 d . . . C2 C 0.1080(6) 0.3297(5) -0.1804(6) 0.068(2) Uani 1 1 d . . . H2 H 0.1116 0.3744 -0.2138 0.082 Uiso 1 1 calc R . . C3 C 0.0786(5) 0.2671(5) -0.2375(6) 0.067(2) Uani 1 1 d . . . H3 H 0.0626 0.2700 -0.3082 0.081 Uiso 1 1 calc R . . C4 C 0.0730(6) 0.2009(6) -0.1906(7) 0.082(3) Uani 1 1 d . . . H4 H 0.0538 0.1583 -0.2287 0.098 Uiso 1 1 calc R . . C5 C 0.0961(6) 0.1981(5) -0.0862(7) 0.075(2) Uani 1 1 d . . . H5 H 0.0905 0.1532 -0.0542 0.090 Uiso 1 1 calc R . . C6 C 0.1285(5) 0.2618(4) -0.0246(5) 0.0527(17) Uani 1 1 d . . . C7 C 0.1480(5) 0.2521(4) 0.0857(6) 0.0589(18) Uani 1 1 d . . . C8 C 0.1471(6) 0.1766(4) 0.1282(7) 0.075(2) Uani 1 1 d . . . H8A H 0.2032 0.1510 0.1245 0.112 Uiso 1 1 calc R . . H8B H 0.0942 0.1498 0.0897 0.112 Uiso 1 1 calc R . . H8C H 0.1431 0.1799 0.1979 0.112 Uiso 1 1 calc R . . C9 C 0.1843(6) 0.3010(5) 0.2546(6) 0.068(2) Uani 1 1 d . . . H9A H 0.2167 0.2546 0.2748 0.082 Uiso 1 1 calc R . . H9B H 0.1252 0.2993 0.2741 0.082 Uiso 1 1 calc R . . C10 C 0.2417(6) 0.3646(4) 0.3084(6) 0.0613(19) Uani 1 1 d . . . H10A H 0.2399 0.3643 0.3797 0.074 Uiso 1 1 calc R . . H10B H 0.3060 0.3583 0.3045 0.074 Uiso 1 1 calc R . . C11 C 0.2703(7) 0.5000 0.3036(7) 0.055(2) Uani 1 2 d S . . C12 C 0.2998(11) 0.5000 0.4208(10) 0.086(4) Uani 1 2 d S . . H12A H 0.3352 0.4560 0.4438 0.128 Uiso 0.50 1 calc PR . . H12B H 0.2453 0.5009 0.4480 0.128 Uiso 1 2 calc SR . . H12C H 0.3372 0.5430 0.4437 0.128 Uiso 0.50 1 calc PR . . C13 C 0.3561(7) 0.5000 0.2588(8) 0.057(3) Uani 1 2 d S . . C14 C 0.4473(8) 0.5000 0.3224(8) 0.066(3) Uani 1 2 d S . . H14 H 0.4554 0.5000 0.3927 0.079 Uiso 1 2 calc SR . . C15 C 0.5233(9) 0.5000 0.2813(12) 0.077(3) Uani 1 2 d S . . H15 H 0.5826 0.5000 0.3242 0.092 Uiso 1 2 calc SR . . C16 C 0.5139(9) 0.5000 0.1791(11) 0.073(3) Uani 1 2 d S . . H16 H 0.5665 0.5000 0.1525 0.088 Uiso 1 2 calc SR . . C17 C 0.4239(8) 0.5000 0.1130(9) 0.066(3) Uani 1 2 d S . . H17 H 0.4170 0.5000 0.0428 0.079 Uiso 1 2 calc SR . . C18 C 0.3457(6) 0.5000 0.1543(7) 0.046(2) Uani 1 2 d S . . C19 C 0.1157(6) 0.4579(5) 0.2886(6) 0.066(2) Uani 1 1 d . . . H19A H 0.0629 0.4388 0.2381 0.079 Uiso 1 1 calc R . . H19B H 0.1128 0.4388 0.3549 0.079 Uiso 1 1 calc R . . Cl1 Cl 0.1961(4) 0.5000 0.6895(4) 0.0760(16) Uani 0.50 2 d SP . . 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 0.0720(6) 0.0329(5) 0.0626(6) 0.0005(4) 0.0193(4) -0.0064(4) O1 0.066(4) 0.032(3) 0.055(3) 0.000 0.023(3) 0.000 O2 0.108(4) 0.038(3) 0.067(3) -0.010(2) 0.030(3) -0.008(3) N1 0.065(4) 0.035(3) 0.076(4) 0.007(3) 0.027(3) 0.003(3) N2 0.063(3) 0.039(3) 0.061(3) 0.000(3) 0.020(3) -0.008(3) N3 0.066(6) 0.053(6) 0.091(7) 0.000 0.012(5) 0.000 N4 0.047(7) 0.051(8) 0.060(7) 0.000 0.001(6) 0.000 C1 0.064(5) 0.041(4) 0.077(5) -0.011(3) 0.025(4) 0.003(4) C2 0.081(5) 0.056(5) 0.071(5) -0.007(4) 0.023(4) 0.005(4) C3 0.069(5) 0.069(6) 0.067(4) -0.027(4) 0.024(4) -0.011(4) C4 0.086(6) 0.074(7) 0.093(6) -0.033(5) 0.036(5) -0.027(5) C5 0.071(5) 0.057(5) 0.107(7) -0.010(5) 0.043(5) -0.010(4) C6 0.052(4) 0.034(4) 0.077(4) -0.008(3) 0.025(3) -0.005(3) C7 0.051(4) 0.038(4) 0.094(5) -0.009(4) 0.031(4) -0.003(3) C8 0.088(6) 0.034(4) 0.106(6) 0.010(4) 0.030(5) -0.006(4) C9 0.080(5) 0.053(5) 0.076(5) 0.018(4) 0.025(4) 0.000(4) C10 0.073(5) 0.046(5) 0.069(4) 0.007(4) 0.025(4) -0.006(4) C11 0.072(7) 0.035(5) 0.059(6) 0.000 0.017(5) 0.000 C12 0.118(11) 0.058(8) 0.086(8) 0.000 0.034(7) 0.000 C13 0.056(6) 0.039(6) 0.080(7) 0.000 0.022(5) 0.000 C14 0.070(7) 0.057(8) 0.062(6) 0.000 -0.003(6) 0.000 C15 0.060(7) 0.049(7) 0.114(10) 0.000 0.006(7) 0.000 C16 0.065(7) 0.053(7) 0.113(10) 0.000 0.042(7) 0.000 C17 0.083(8) 0.033(6) 0.086(7) 0.000 0.029(6) 0.000 C18 0.048(6) 0.029(5) 0.062(6) 0.000 0.011(5) 0.000 C19 0.078(5) 0.058(5) 0.070(4) -0.002(4) 0.033(4) -0.004(4) Cl1 0.073(4) 0.065(4) 0.076(3) 0.000 -0.010(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.880(5) . ? Cu1 N1 1.945(6) . ? Cu1 O1 1.987(4) . ? Cu1 N2 2.072(6) . ? Cu1 N3 2.406(8) . ? O1 C18 1.330(11) . ? O1 Cu1 1.987(4) 6_565 ? O2 C1 1.321(9) . ? O3A O3B 0.59(2) . ? O3B Cl1 2.144(19) . ? O4A O4B 0.98(3) . ? O5 O5 1.23(4) 2_556 ? O5 O5 1.28(5) 6_565 ? O5 O5 1.77(5) 5_566 ? O6A O6B 1.01(3) . ? O6A O6A 1.23(7) 2_656 ? O7A O7B 1.24(7) . ? N1 C7 1.309(9) . ? N1 C9 1.445(9) . ? N2 C10 1.469(10) . ? N2 C11 1.506(9) . ? N2 C19 1.519(9) . ? N3 N4 1.136(11) . ? N3 Cu1 2.406(8) 6_565 ? N4 N3 1.136(11) 5_565 ? C1 C2 1.369(10) . ? C1 C6 1.396(10) . ? C2 C3 1.377(11) . ? C3 C4 1.362(13) . ? C4 C5 1.374(12) . ? C5 C6 1.432(11) . ? C6 C7 1.461(10) . ? C7 C8 1.478(10) . ? C9 C10 1.506(11) . ? C11 N2 1.506(9) 6_565 ? C11 C13 1.527(14) . ? C11 C12 1.541(16) . ? C13 C18 1.386(14) . ? C13 C14 1.417(15) . ? C14 C15 1.365(18) . ? C15 C16 1.355(17) . ? C16 C17 1.418(18) . ? C17 C18 1.395(14) . ? C19 C19 1.516(17) 6_565 ? 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 O2 Cu1 N1 93.3(2) . . ? O2 Cu1 O1 90.0(2) . . ? N1 Cu1 O1 154.0(3) . . ? O2 Cu1 N2 179.8(2) . . ? N1 Cu1 N2 86.5(2) . . ? O1 Cu1 N2 90.2(2) . . ? O2 Cu1 N3 89.8(3) . . ? N1 Cu1 N3 122.2(3) . . ? O1 Cu1 N3 83.5(2) . . ? N2 Cu1 N3 90.3(3) . . ? C18 O1 Cu1 113.0(3) . . ? C18 O1 Cu1 113.0(3) . 6_565 ? Cu1 O1 Cu1 105.2(3) . 6_565 ? C1 O2 Cu1 126.9(5) . . ? O3A O3B Cl1 105(3) . . ? O5 O5 O5 90.000(2) 2_556 6_565 ? O5 O5 O5 46.0(15) 2_556 5_566 ? O5 O5 O5 44.0(15) 6_565 5_566 ? O6B O6A O6A 161(6) . 2_656 ? C7 N1 C9 120.2(7) . . ? C7 N1 Cu1 128.4(5) . . ? C9 N1 Cu1 111.3(5) . . ? C10 N2 C11 112.9(6) . . ? C10 N2 C19 111.9(6) . . ? C11 N2 C19 103.1(6) . . ? C10 N2 Cu1 101.3(4) . . ? C11 N2 Cu1 117.4(5) . . ? C19 N2 Cu1 110.6(4) . . ? N4 N3 Cu1 125.7(4) . 6_565 ? N4 N3 Cu1 125.7(4) . . ? Cu1 N3 Cu1 82.0(3) 6_565 . ? N3 N4 N3 180 . 5_565 ? O2 C1 C2 116.6(7) . . ? O2 C1 C6 123.2(7) . . ? C2 C1 C6 119.9(7) . . ? C1 C2 C3 122.2(8) . . ? C4 C3 C2 120.1(8) . . ? C3 C4 C5 118.9(8) . . ? C4 C5 C6 122.5(9) . . ? C1 C6 C5 116.4(7) . . ? C1 C6 C7 126.3(7) . . ? C5 C6 C7 117.1(7) . . ? N1 C7 C6 119.9(7) . . ? N1 C7 C8 120.8(7) . . ? C6 C7 C8 119.3(7) . . ? N1 C9 C10 110.4(6) . . ? N2 C10 C9 111.2(6) . . ? N2 C11 N2 99.7(8) . 6_565 ? N2 C11 C13 111.0(6) . . ? N2 C11 C13 111.0(6) 6_565 . ? N2 C11 C12 112.2(6) . . ? N2 C11 C12 112.2(6) 6_565 . ? C13 C11 C12 110.3(9) . . ? C18 C13 C14 118.7(9) . . ? C18 C13 C11 120.1(9) . . ? C14 C13 C11 121.2(10) . . ? C15 C14 C13 120.6(11) . . ? C16 C15 C14 121.2(11) . . ? C15 C16 C17 119.9(11) . . ? C18 C17 C16 119.3(10) . . ? O1 C18 C13 121.2(8) . . ? O1 C18 C17 118.5(9) . . ? C13 C18 C17 120.3(9) . . ? C19 C19 N2 105.0(4) 6_565 . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.899 _refine_diff_density_min -0.980 _refine_diff_density_rms 0.118