# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name S.Mitra C.R.Choudhury 'M.S.El Fallah' A.Majumder J.Ribas ; G.Rosair ; _publ_contact_author_name 'Dr Samiran Mitra' _publ_contact_author_email 'SMITRA 2002@YAHOO.COM' data_complex_1 _database_code_depnum_ccdc_archive 'CCDC 238039' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H36 Cu3 N12 O6, 2(Cl O4), C H4 O' _chemical_formula_sum 'C33 H40 Cl2 Cu3 N12 O15' _chemical_formula_weight 1106.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 9.156(2) _cell_length_b 9.156(2) _cell_length_c 44.51(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3231(2) _cell_formula_units_Z 3 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 34 _cell_measurement_theta_min 5.17 _cell_measurement_theta_max 11.38 _exptl_crystal_description hexagonal_plate _exptl_crystal_colour violet _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1689.0 _exptl_absorpt_coefficient_mu 1.673 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.7718 _exptl_absorpt_correction_T_max 0.8581 _exptl_absorpt_process_details 'North et al., 1968' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1389 _diffrn_reflns_av_R_equivalents 0.0944 _diffrn_reflns_av_sigmaI/netI 0.1313 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 52 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1254 _reflns_number_gt 746 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; the MeOH solvent was only partially modelled as one C atom which has a symmetry equivalent 1.9 a A away. data quality was low as the sample was weakly diffracting and the psi scan absorption correction was applied in both ellipsoid and lamina modes but highly anisotropic atoms still appeared, O1 N1 C15 and C11. Their anisotropy was restrained by the Shelx ISOR command The highest peak in the difference map is 0.994 A from Cu1 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^)+(0.1960P)^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 1254 _refine_ls_number_parameters 100 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1664 _refine_ls_R_factor_gt 0.1037 _refine_ls_wR_factor_ref 0.3044 _refine_ls_wR_factor_gt 0.2539 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.013 _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 0.5000 1.0000 0.0000 0.0140(7) Uani 1 2 d S . . O1 O 0.2921(9) 0.7821(9) -0.00013(15) 0.0125(17) Uani 1 1 d U . . Cl1 Cl 1.0000 0.0000 0.13393(11) 0.0173(12) Uani 1 3 d S . . N1 N 0.5011(10) 0.9983(11) 0.0449(2) 0.0110(19) Uani 1 1 d U . . C11 C 0.3602(15) 0.9217(14) 0.0609(2) 0.019(2) Uani 1 1 d U . . H11 H 0.2565 0.8624 0.0503 0.022 Uiso 1 1 calc R . . C12 C 0.3541(15) 0.9224(14) 0.0915(3) 0.025(3) Uani 1 1 d . . . H12 H 0.2482 0.8683 0.1014 0.030 Uiso 1 1 calc R . . C13 C 0.5047(15) 1.0034(13) 0.1083(3) 0.024(3) Uani 1 1 d . . . N13 N 0.5076(13) 1.0109(13) 0.1384(2) 0.028(3) Uani 1 1 d . . . H13A H 0.6046 1.0633 0.1479 0.034 Uiso 1 1 calc R . . H13B H 0.4125 0.9635 0.1485 0.034 Uiso 1 1 calc R . . C14 C 0.6522(15) 1.0767(14) 0.0916(3) 0.026(3) Uani 1 1 d . . . H14 H 0.7582 1.1283 0.1015 0.031 Uiso 1 1 calc R . . C15 C 0.6460(14) 1.0753(13) 0.0605(2) 0.015(2) Uani 1 1 d U . . H15 H 0.7492 1.1316 0.0497 0.018 Uiso 1 1 calc R . . C20 C 0.3333 0.6667 0.0004(4) 0.013(4) Uani 1 3 d S . . O11A O 0.9322(10) 0.1022(10) 0.14493(18) 0.024(2) Uani 1 1 d . . . O12A O 1.0000 0.0000 0.1022(3) 0.026(3) Uani 1 3 d S . . C1S C 1.0000 0.0000 0.021(3) 0.36(13) Uani 1 3 d S . . 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 0.0060(10) 0.0049(10) 0.0312(13) 0.0006(8) -0.0012(8) 0.0027(8) O1 0.0125(19) 0.0122(19) 0.0140(19) 0.0003(10) -0.0002(10) 0.0071(12) Cl1 0.0140(15) 0.0140(15) 0.024(3) 0.000 0.000 0.0070(8) N1 0.011(2) 0.011(2) 0.012(2) -0.0005(10) 0.0006(10) 0.0055(13) C11 0.018(3) 0.018(3) 0.019(3) -0.0003(10) 0.0002(10) 0.0092(15) C12 0.014(6) 0.013(6) 0.050(8) -0.003(6) 0.006(6) 0.007(5) C13 0.024(7) 0.010(6) 0.038(7) -0.006(5) -0.004(6) 0.009(5) N13 0.027(6) 0.024(6) 0.032(6) -0.002(5) 0.003(5) 0.011(5) C14 0.010(6) 0.015(6) 0.052(9) -0.001(6) -0.004(6) 0.005(5) C15 0.015(3) 0.015(3) 0.016(3) -0.0003(10) 0.0000(10) 0.0079(15) C20 0.008(6) 0.008(6) 0.023(10) 0.000 0.000 0.004(3) O11A 0.026(5) 0.018(4) 0.029(4) -0.007(4) -0.003(4) 0.011(4) O12A 0.027(5) 0.027(5) 0.024(8) 0.000 0.000 0.013(3) C1S 0.20(6) 0.20(6) 0.7(4) 0.000 0.000 0.10(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.951(7) 10_675 ? Cu1 O1 1.951(7) . ? Cu1 N1 1.997(9) 10_675 ? Cu1 N1 1.998(9) . ? O1 C20 1.288(7) . ? O1 Cu1 1.951(7) 10_675 ? Cl1 O12A 1.414(14) . ? Cl1 O11A 1.443(8) . ? Cl1 O11A 1.443(8) 3_765 ? Cl1 O11A 1.443(8) 2_645 ? N1 C11 1.326(14) . ? N1 C15 1.343(13) . ? N1 Cu1 1.998(9) 10_675 ? C11 C12 1.363(17) . ? C11 H11 0.9500 . ? C12 C13 1.412(17) . ? C12 H12 0.9500 . ? C13 N13 1.338(17) . ? C13 C14 1.387(17) . ? N13 H13A 0.8800 . ? N13 H13B 0.8800 . ? C14 C15 1.385(16) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C20 O1 1.288(7) 2_665 ? C20 O1 1.288(7) 3_565 ? C1S C1S 1.9(3) 10_755 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 180.0 10_675 . ? O1 Cu1 N1 90.1(3) 10_675 10_675 ? O1 Cu1 N1 89.9(3) . 10_675 ? O1 Cu1 N1 89.9(3) 10_675 . ? O1 Cu1 N1 90.1(3) . . ? N1 Cu1 N1 180.000(1) 10_675 . ? C20 O1 Cu1 107.6(4) . 10_675 ? C20 O1 Cu1 107.6(4) . . ? Cu1 O1 Cu1 0.0 10_675 . ? O12A Cl1 O11A 109.8(4) . . ? O12A Cl1 O11A 109.8(4) . 3_765 ? O11A Cl1 O11A 109.1(4) . 3_765 ? O12A Cl1 O11A 109.8(4) . 2_645 ? O11A Cl1 O11A 109.1(4) . 2_645 ? O11A Cl1 O11A 109.1(4) 3_765 2_645 ? C11 N1 C15 116.4(10) . . ? C11 N1 Cu1 122.3(7) . 10_675 ? C15 N1 Cu1 121.4(7) . 10_675 ? C11 N1 Cu1 122.3(7) . . ? C15 N1 Cu1 121.4(7) . . ? Cu1 N1 Cu1 0.0 10_675 . ? N1 C11 C12 124.4(11) . . ? N1 C11 H11 117.8 . . ? C12 C11 H11 117.8 . . ? C11 C12 C13 120.2(11) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? N13 C13 C14 121.6(11) . . ? N13 C13 C12 123.2(11) . . ? C14 C13 C12 115.2(12) . . ? C13 N13 H13A 120.0 . . ? C13 N13 H13B 120.0 . . ? H13A N13 H13B 120.0 . . ? C15 C14 C13 120.6(11) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? N1 C15 C14 123.1(10) . . ? N1 C15 H15 118.4 . . ? C14 C15 H15 118.4 . . ? O1 C20 O1 119.97(7) . 2_665 ? O1 C20 O1 119.97(7) . 3_565 ? O1 C20 O1 119.97(7) 2_665 3_565 ? 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 Cu1 O1 C20 91.7(10) 10_675 . . . ? N1 Cu1 O1 C20 -88.3(10) . . . . ? O1 Cu1 N1 C11 150.1(9) 10_675 . . . ? O1 Cu1 N1 C11 -29.9(9) . . . . ? O1 Cu1 N1 C15 -29.9(8) 10_675 . . . ? O1 Cu1 N1 C15 150.1(8) . . . . ? C15 N1 C11 C12 2.6(16) . . . . ? Cu1 N1 C11 C12 -177.4(9) 10_675 . . . ? Cu1 N1 C11 C12 -177.4(9) . . . . ? N1 C11 C12 C13 -2.3(18) . . . . ? C11 C12 C13 N13 179.0(10) . . . . ? C11 C12 C13 C14 -0.7(16) . . . . ? N13 C13 C14 C15 -176.4(10) . . . . ? C12 C13 C14 C15 3.2(16) . . . . ? C11 N1 C15 C14 0.1(15) . . . . ? Cu1 N1 C15 C14 -179.8(8) 10_675 . . . ? Cu1 N1 C15 C14 -179.8(8) . . . . ? C13 C14 C15 N1 -3.1(17) . . . . ? Cu1 O1 C20 O1 -178.8(12) 10_675 . . 2_665 ? Cu1 O1 C20 O1 -178.8(12) . . . 2_665 ? Cu1 O1 C20 O1 -2.2(19) 10_675 . . 3_565 ? Cu1 O1 C20 O1 -2.2(19) . . . 3_565 ? 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 N13 H13A O11A 0.88 2.28 3.025(14) 142.6 13_665 N13 H13B O11A 0.88 2.83 3.394(13) 123.7 3_675 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.680 _refine_diff_density_min -1.319 _refine_diff_density_rms 0.260