# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name Y.B.Xie _publ_contact_author_email xieyabo@126.comxieyabo@126.com loop_ _publ_author_name Q.Gao Y.Song Y.B.Xie data_1 _database_code_depnum_ccdc_archive 'CCDC 713145' #TrackingRef '- Complex 1.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cl0 Cu3 N14 O8' _chemical_formula_weight 670.98 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.5724(15) _cell_length_b 8.922(2) _cell_length_c 10.621(4) _cell_angle_alpha 108.461(5) _cell_angle_beta 94.233(5) _cell_angle_gamma 110.179(3) _cell_volume 542.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.053 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 333 _exptl_absorpt_coefficient_mu 2.989 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4675 _exptl_absorpt_correction_T_max 0.5340 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2772 _diffrn_reflns_av_R_equivalents 0.0103 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1890 _reflns_number_gt 1761 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0368P)^2^+0.1980P] 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 1890 _refine_ls_number_parameters 177 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0243 _refine_ls_R_factor_gt 0.0224 _refine_ls_wR_factor_ref 0.0620 _refine_ls_wR_factor_gt 0.0611 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.5000 0.5000 0.02598(12) Uani 1 2 d S . . Cu2 Cu 0.42494(4) 0.80625(3) 0.45366(2) 0.02466(11) Uani 1 1 d . . . O4 O 0.7671(3) 0.7800(2) 0.50225(17) 0.0332(4) Uani 1 1 d D . . N1 N 0.2947(3) 0.6246(2) 0.52664(19) 0.0261(4) Uani 1 1 d . . . N2 N 0.2230(3) 0.6548(2) 0.6306(2) 0.0298(4) Uani 1 1 d . . . N3 N 0.1525(4) 0.6810(3) 0.7260(3) 0.0485(6) Uani 1 1 d . . . N4 N 0.4702(4) 1.0053(2) 0.61955(19) 0.0305(4) Uani 1 1 d . . . N5 N 0.5480(3) 1.0280(2) 0.7347(2) 0.0281(4) Uani 1 1 d . . . N6 N 0.6157(4) 1.0512(3) 0.8437(2) 0.0433(6) Uani 1 1 d . . . N7 N 0.1055(3) 0.2010(2) -0.19123(18) 0.0299(4) Uani 1 1 d . . . C1 C 0.3501(4) 0.4897(3) 0.2309(2) 0.0241(5) Uani 1 1 d . . . C2 C 0.2701(4) 0.3885(3) 0.0810(2) 0.0230(4) Uani 1 1 d . . . C3 C 0.2247(4) 0.4651(3) -0.0058(2) 0.0252(5) Uani 1 1 d . . . H3 H 0.2496 0.5811 0.0277 0.030 Uiso 1 1 calc R . . C4 C 0.1426(4) 0.3698(3) -0.1417(2) 0.0287(5) Uani 1 1 d . . . H4 H 0.1122 0.4217 -0.2000 0.034 Uiso 1 1 calc R . . C5 C 0.1574(4) 0.1261(3) -0.1092(2) 0.0337(5) Uani 1 1 d . . . H5 H 0.1377 0.0113 -0.1452 0.040 Uiso 1 1 calc R . . C6 C 0.2391(4) 0.2168(3) 0.0268(2) 0.0303(5) Uani 1 1 d . . . H6 H 0.2737 0.1636 0.0828 0.036 Uiso 1 1 calc R . . O1 O 0.3517(3) 0.6388(2) 0.26975(15) 0.0327(4) Uani 1 1 d . . . O2 O 0.4084(3) 0.4185(2) 0.30224(15) 0.0319(4) Uani 1 1 d . . . O3 O 0.0165(3) 0.1116(2) -0.32056(16) 0.0441(5) Uani 1 1 d . . . H4B H 0.833(5) 0.866(3) 0.575(2) 0.064(10) Uiso 1 1 d D . . H4C H 0.821(5) 0.798(4) 0.436(2) 0.054(10) Uiso 1 1 d 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 0.0377(2) 0.0245(2) 0.0174(2) 0.00537(16) 0.00141(16) 0.01693(18) Cu2 0.03625(18) 0.01544(16) 0.01824(16) 0.00375(11) 0.00134(12) 0.00839(12) O4 0.0360(10) 0.0280(9) 0.0255(9) 0.0068(8) 0.0036(8) 0.0039(8) N1 0.0332(10) 0.0216(9) 0.0242(10) 0.0084(8) 0.0063(8) 0.0115(8) N2 0.0319(11) 0.0222(10) 0.0330(12) 0.0102(8) 0.0041(9) 0.0084(8) N3 0.0553(15) 0.0520(15) 0.0429(14) 0.0186(12) 0.0251(12) 0.0223(12) N4 0.0482(12) 0.0206(10) 0.0192(10) 0.0057(8) 0.0002(9) 0.0122(9) N5 0.0363(11) 0.0206(10) 0.0285(12) 0.0083(8) 0.0081(9) 0.0128(8) N6 0.0569(15) 0.0478(14) 0.0256(12) 0.0158(10) 0.0025(11) 0.0198(12) N7 0.0269(10) 0.0319(11) 0.0178(9) 0.0020(8) 0.0050(8) 0.0027(8) C1 0.0244(11) 0.0225(11) 0.0199(11) 0.0039(9) 0.0013(9) 0.0067(9) C2 0.0220(10) 0.0228(11) 0.0197(11) 0.0039(9) 0.0030(9) 0.0071(9) C3 0.0247(11) 0.0235(11) 0.0241(11) 0.0061(9) 0.0033(9) 0.0083(9) C4 0.0290(12) 0.0333(13) 0.0224(11) 0.0105(10) 0.0026(9) 0.0107(10) C5 0.0411(14) 0.0221(12) 0.0298(13) 0.0023(10) 0.0086(11) 0.0091(10) C6 0.0384(13) 0.0247(12) 0.0270(12) 0.0082(10) 0.0046(10) 0.0129(10) O1 0.0528(11) 0.0187(8) 0.0199(8) 0.0030(6) -0.0017(7) 0.0116(7) O2 0.0467(10) 0.0305(9) 0.0197(8) 0.0048(7) -0.0002(7) 0.0217(8) O3 0.0492(11) 0.0412(10) 0.0146(8) -0.0015(7) 0.0025(8) -0.0028(9) _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 1.9614(17) . ? Cu1 O2 1.9614(17) 2_666 ? Cu1 N1 2.0072(19) 2_666 ? Cu1 N1 2.0072(19) . ? Cu2 O1 1.9483(17) . ? Cu2 N1 1.9740(18) . ? Cu2 N4 1.981(2) . ? Cu2 N4 2.0035(19) 2_676 ? Cu2 O4 2.376(2) . ? Cu2 Cu2 3.0403(9) 2_676 ? O4 H4B 0.848(10) . ? O4 H4C 0.843(10) . ? N1 N2 1.220(3) . ? N2 N3 1.137(3) . ? N4 N5 1.216(3) . ? N4 Cu2 2.0035(19) 2_676 ? N5 N6 1.136(3) . ? N7 O3 1.316(2) . ? N7 C5 1.343(3) . ? N7 C4 1.353(3) . ? C1 O2 1.246(3) . ? C1 O1 1.258(3) . ? C1 C2 1.505(3) . ? C2 C3 1.380(3) . ? C2 C6 1.389(3) . ? C3 C4 1.375(3) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 C6 1.370(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? 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 O2 180 . 2_666 ? O2 Cu1 N1 88.70(7) . 2_666 ? O2 Cu1 N1 91.30(7) 2_666 2_666 ? O2 Cu1 N1 91.30(7) . . ? O2 Cu1 N1 88.70(7) 2_666 . ? N1 Cu1 N1 180.00(11) 2_666 . ? O1 Cu2 N1 91.83(8) . . ? O1 Cu2 N4 166.47(7) . . ? N1 Cu2 N4 97.56(8) . . ? O1 Cu2 N4 89.21(7) . 2_676 ? N1 Cu2 N4 174.41(8) . 2_676 ? N4 Cu2 N4 80.53(9) . 2_676 ? O1 Cu2 O4 92.21(7) . . ? N1 Cu2 O4 86.72(7) . . ? N4 Cu2 O4 98.00(8) . . ? N4 Cu2 O4 98.73(8) 2_676 . ? O1 Cu2 Cu2 128.63(5) . 2_676 ? N1 Cu2 Cu2 137.86(6) . 2_676 ? N4 Cu2 Cu2 40.54(5) . 2_676 ? N4 Cu2 Cu2 39.99(6) 2_676 2_676 ? O4 Cu2 Cu2 101.00(4) . 2_676 ? Cu2 O4 H4B 102(2) . . ? Cu2 O4 H4C 99(2) . . ? H4B O4 H4C 110(3) . . ? N2 N1 Cu2 120.86(15) . . ? N2 N1 Cu1 120.98(15) . . ? Cu2 N1 Cu1 102.92(9) . . ? N3 N2 N1 178.7(3) . . ? N5 N4 Cu2 126.69(16) . . ? N5 N4 Cu2 120.51(16) . 2_676 ? Cu2 N4 Cu2 99.47(9) . 2_676 ? N6 N5 N4 177.8(2) . . ? O3 N7 C5 120.7(2) . . ? O3 N7 C4 118.9(2) . . ? C5 N7 C4 120.4(2) . . ? O2 C1 O1 127.3(2) . . ? O2 C1 C2 117.28(19) . . ? O1 C1 C2 115.41(19) . . ? C3 C2 C6 118.5(2) . . ? C3 C2 C1 120.3(2) . . ? C6 C2 C1 121.2(2) . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? N7 C4 C3 120.4(2) . . ? N7 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? N7 C5 C6 120.7(2) . . ? N7 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C2 119.9(2) . . ? C5 C6 H6 120.1 . . ? C2 C6 H6 120.1 . . ? C1 O1 Cu2 128.86(15) . . ? C1 O2 Cu1 129.39(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu2 N1 N2 -153.85(19) . . . . ? N4 Cu2 N1 N2 16.4(2) . . . . ? N4 Cu2 N1 N2 -53.2(8) 2_676 . . . ? O4 Cu2 N1 N2 114.04(18) . . . . ? Cu2 Cu2 N1 N2 11.2(2) 2_676 . . . ? O1 Cu2 N1 Cu1 67.38(9) . . . . ? N4 Cu2 N1 Cu1 -122.39(9) . . . . ? N4 Cu2 N1 Cu1 168.0(7) 2_676 . . . ? O4 Cu2 N1 Cu1 -24.74(8) . . . . ? Cu2 Cu2 N1 Cu1 -127.53(6) 2_676 . . . ? O2 Cu1 N1 N2 154.76(18) . . . . ? O2 Cu1 N1 N2 -25.24(18) 2_666 . . . ? N1 Cu1 N1 N2 70(31) 2_666 . . . ? O2 Cu1 N1 Cu2 -66.52(9) . . . . ? O2 Cu1 N1 Cu2 113.48(9) 2_666 . . . ? N1 Cu1 N1 Cu2 -152(31) 2_666 . . . ? Cu2 N1 N2 N3 113(11) . . . . ? Cu1 N1 N2 N3 -116(11) . . . . ? O1 Cu2 N4 N5 178.9(3) . . . . ? N1 Cu2 N4 N5 45.3(2) . . . . ? N4 Cu2 N4 N5 -140.0(3) 2_676 . . . ? O4 Cu2 N4 N5 -42.4(2) . . . . ? Cu2 Cu2 N4 N5 -140.0(3) 2_676 . . . ? O1 Cu2 N4 Cu2 -41.1(4) . . . 2_676 ? N1 Cu2 N4 Cu2 -174.69(9) . . . 2_676 ? N4 Cu2 N4 Cu2 0.0 2_676 . . 2_676 ? O4 Cu2 N4 Cu2 97.58(8) . . . 2_676 ? Cu2 N4 N5 N6 -139(6) . . . . ? Cu2 N4 N5 N6 89(6) 2_676 . . . ? O2 C1 C2 C3 -173.3(2) . . . . ? O1 C1 C2 C3 6.1(3) . . . . ? O2 C1 C2 C6 7.1(3) . . . . ? O1 C1 C2 C6 -173.5(2) . . . . ? C6 C2 C3 C4 2.5(3) . . . . ? C1 C2 C3 C4 -177.16(19) . . . . ? O3 N7 C4 C3 176.6(2) . . . . ? C5 N7 C4 C3 -2.9(3) . . . . ? C2 C3 C4 N7 0.1(3) . . . . ? O3 N7 C5 C6 -176.5(2) . . . . ? C4 N7 C5 C6 3.0(4) . . . . ? N7 C5 C6 C2 -0.4(4) . . . . ? C3 C2 C6 C5 -2.3(4) . . . . ? C1 C2 C6 C5 177.3(2) . . . . ? O2 C1 O1 Cu2 -4.6(4) . . . . ? C2 C1 O1 Cu2 176.00(14) . . . . ? N1 Cu2 O1 C1 -34.8(2) . . . . ? N4 Cu2 O1 C1 -168.9(3) . . . . ? N4 Cu2 O1 C1 150.6(2) 2_676 . . . ? O4 Cu2 O1 C1 51.9(2) . . . . ? Cu2 Cu2 O1 C1 157.92(17) 2_676 . . . ? O1 C1 O2 Cu1 5.6(4) . . . . ? C2 C1 O2 Cu1 -175.01(14) . . . . ? O2 Cu1 O2 C1 175(100) 2_666 . . . ? N1 Cu1 O2 C1 -147.4(2) 2_666 . . . ? N1 Cu1 O2 C1 32.6(2) . . . . ? 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 O4 H4B O3 0.848(10) 1.982(18) 2.767(2) 153(3) 1_666 O4 H4C O3 0.843(10) 1.878(13) 2.706(2) 167(3) 2_665 O4 H4C N7 0.843(10) 2.685(13) 3.508(3) 166(3) 2_665 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.309 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.085 # Attachment '- Complex 2.txt' data_2 _database_code_depnum_ccdc_archive 'CCDC 713146' #TrackingRef '- Complex 2.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Cu3 N14 O6' _chemical_formula_weight 634.94 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2676(11) _cell_length_b 10.446(2) _cell_length_c 10.739(2) _cell_angle_alpha 116.41(3) _cell_angle_beta 103.82(3) _cell_angle_gamma 92.64(3) _cell_volume 506.00(18) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.084 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 313 _exptl_absorpt_coefficient_mu 3.192 _exptl_absorpt_correction_type Multi-scan _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5370 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2307 _reflns_number_gt 2044 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0324P)^2^+0.3113P] 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 2307 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0748 _refine_ls_wR_factor_gt 0.0728 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.160 _refine_ls_shift/su_max 0.001 _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 0.51295(6) 0.19675(3) 0.59269(3) 0.02362(11) Uani 1 1 d . . . Cu2 Cu 0.0000 0.0000 0.5000 0.02339(12) Uani 1 2 d S . . N1 N 0.7112(4) 0.4844(2) 0.7018(2) 0.0235(4) Uani 1 1 d . . . N2 N 0.1624(4) 0.1340(2) 0.4434(2) 0.0245(4) Uani 1 1 d . . . N3 N 0.0536(4) 0.2182(3) 0.4083(3) 0.0318(5) Uani 1 1 d . . . N4 N -0.0435(6) 0.2965(4) 0.3740(4) 0.0631(10) Uani 1 1 d . . . N5 N 0.3741(4) 0.0292(2) 0.6177(2) 0.0215(4) Uani 1 1 d . . . N6 N 0.4241(4) 0.0340(2) 0.7366(2) 0.0293(5) Uani 1 1 d . . . N7 N 0.4729(7) 0.0350(4) 0.8456(3) 0.0587(8) Uani 1 1 d . . . C1 C 0.5959(6) 0.6030(3) 0.7336(3) 0.0337(6) Uani 1 1 d . . . H1A H 0.4404 0.6006 0.6690 0.040 Uiso 1 1 calc R . . C2 C 0.7091(7) 0.7276(3) 0.8621(4) 0.0417(7) Uani 1 1 d . . . H2A H 0.6282 0.8092 0.8855 0.050 Uiso 1 1 calc R . . C3 C 0.9419(7) 0.7314(3) 0.9559(3) 0.0437(8) Uani 1 1 d . . . H3A H 1.0189 0.8152 1.0432 0.052 Uiso 1 1 calc R . . C4 C 1.0607(6) 0.6095(3) 0.9194(3) 0.0331(6) Uani 1 1 d . . . H4A H 1.2215 0.6123 0.9807 0.040 Uiso 1 1 calc R . . C5 C 0.9407(5) 0.4831(3) 0.7919(3) 0.0245(5) Uani 1 1 d . . . C6 C 1.0508(5) 0.3435(3) 0.7565(3) 0.0238(5) Uani 1 1 d . . . O1 O 0.5925(4) 0.3670(2) 0.5731(2) 0.0304(4) Uani 1 1 d . . . O2 O 0.8834(3) 0.22455(19) 0.7006(2) 0.0262(4) Uani 1 1 d . . . O3 O 1.2942(4) 0.3532(2) 0.7880(2) 0.0347(5) 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 0.01652(16) 0.02348(17) 0.03019(19) 0.01466(14) 0.00214(12) 0.00011(12) Cu2 0.0149(2) 0.0265(2) 0.0316(2) 0.01813(19) 0.00272(17) 0.00178(16) N1 0.0232(11) 0.0233(10) 0.0264(11) 0.0129(9) 0.0090(9) 0.0024(8) N2 0.0160(10) 0.0262(11) 0.0319(12) 0.0161(9) 0.0031(8) 0.0022(8) N3 0.0220(11) 0.0421(14) 0.0449(14) 0.0310(12) 0.0115(10) 0.0069(10) N4 0.0447(17) 0.084(2) 0.110(3) 0.080(2) 0.0340(18) 0.0328(17) N5 0.0158(10) 0.0234(10) 0.0253(11) 0.0124(9) 0.0043(8) 0.0032(8) N6 0.0271(12) 0.0279(12) 0.0308(13) 0.0142(10) 0.0042(10) 0.0032(9) N7 0.074(2) 0.065(2) 0.0352(16) 0.0276(15) 0.0058(15) 0.0057(16) C1 0.0303(14) 0.0358(15) 0.0440(17) 0.0257(13) 0.0114(12) 0.0108(12) C2 0.0507(19) 0.0304(15) 0.0497(18) 0.0183(14) 0.0232(16) 0.0190(14) C3 0.056(2) 0.0261(15) 0.0370(16) 0.0067(13) 0.0104(15) 0.0038(14) C4 0.0329(15) 0.0294(14) 0.0303(14) 0.0117(12) 0.0035(12) 0.0013(11) C5 0.0225(12) 0.0250(12) 0.0271(13) 0.0134(10) 0.0074(10) 0.0011(10) C6 0.0209(12) 0.0247(12) 0.0226(12) 0.0085(10) 0.0064(10) 0.0032(10) O1 0.0322(10) 0.0277(10) 0.0270(9) 0.0147(8) -0.0010(8) -0.0043(8) O2 0.0187(8) 0.0218(9) 0.0344(10) 0.0114(8) 0.0049(7) 0.0031(7) O3 0.0186(9) 0.0313(10) 0.0438(11) 0.0101(9) 0.0064(8) 0.0032(8) _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 1.9204(18) . ? Cu1 O2 1.9500(19) . ? Cu1 N2 1.987(2) . ? Cu1 N5 2.016(2) . ? Cu1 Cu2 2.9832(13) . ? Cu2 N2 1.989(2) . ? Cu2 N2 1.989(2) 2_556 ? Cu2 N5 1.996(2) . ? Cu2 N5 1.996(2) 2_556 ? Cu2 Cu1 2.9832(13) 2_556 ? N1 C1 1.346(3) . ? N1 O1 1.347(3) . ? N1 C5 1.361(3) . ? N2 N3 1.217(3) . ? N3 N4 1.133(3) . ? N5 N6 1.217(3) . ? N6 N7 1.133(3) . ? C1 C2 1.375(4) . ? C1 H1A 0.9300 . ? C2 C3 1.375(5) . ? C2 H2A 0.9300 . ? C3 C4 1.384(4) . ? C3 H3A 0.9300 . ? C4 C5 1.385(4) . ? C4 H4A 0.9300 . ? C5 C6 1.516(4) . ? C6 O3 1.232(3) . ? C6 O2 1.290(3) . ? 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 O2 89.74(8) . . ? O1 Cu1 N2 92.45(9) . . ? O2 Cu1 N2 166.27(8) . . ? O1 Cu1 N5 170.74(8) . . ? O2 Cu1 N5 97.49(8) . . ? N2 Cu1 N5 81.91(9) . . ? O1 Cu1 Cu2 130.99(6) . . ? O2 Cu1 Cu2 139.17(6) . . ? N2 Cu1 Cu2 41.42(7) . . ? N5 Cu1 Cu2 41.72(6) . . ? N2 Cu2 N2 180.00(8) . 2_556 ? N2 Cu2 N5 82.36(9) . . ? N2 Cu2 N5 97.64(9) 2_556 . ? N2 Cu2 N5 97.64(9) . 2_556 ? N2 Cu2 N5 82.36(9) 2_556 2_556 ? N5 Cu2 N5 180.0 . 2_556 ? N2 Cu2 Cu1 138.63(6) . 2_556 ? N2 Cu2 Cu1 41.37(6) 2_556 2_556 ? N5 Cu2 Cu1 137.77(6) . 2_556 ? N5 Cu2 Cu1 42.23(6) 2_556 2_556 ? N2 Cu2 Cu1 41.37(6) . . ? N2 Cu2 Cu1 138.63(6) 2_556 . ? N5 Cu2 Cu1 42.23(6) . . ? N5 Cu2 Cu1 137.77(6) 2_556 . ? Cu1 Cu2 Cu1 180.0 2_556 . ? C1 N1 O1 116.6(2) . . ? C1 N1 C5 122.3(2) . . ? O1 N1 C5 121.0(2) . . ? N3 N2 Cu1 121.81(19) . . ? N3 N2 Cu2 126.46(18) . . ? Cu1 N2 Cu2 97.22(10) . . ? N4 N3 N2 178.4(3) . . ? N6 N5 Cu2 121.19(17) . . ? N6 N5 Cu1 121.42(17) . . ? Cu2 N5 Cu1 96.05(9) . . ? N7 N6 N5 178.2(3) . . ? N1 C1 C2 119.8(3) . . ? N1 C1 H1A 120.1 . . ? C2 C1 H1A 120.1 . . ? C3 C2 C1 119.9(3) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C2 C3 C4 119.5(3) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C3 C4 C5 120.2(3) . . ? C3 C4 H4A 119.9 . . ? C5 C4 H4A 119.9 . . ? N1 C5 C4 118.4(2) . . ? N1 C5 C6 120.1(2) . . ? C4 C5 C6 121.4(2) . . ? O3 C6 O2 125.1(2) . . ? O3 C6 C5 117.3(2) . . ? O2 C6 C5 117.6(2) . . ? N1 O1 Cu1 112.58(14) . . ? C6 O2 Cu1 124.14(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 Cu2 N2 25.92(12) . . . . ? O2 Cu1 Cu2 N2 -159.08(13) . . . . ? N5 Cu1 Cu2 N2 -162.13(13) . . . . ? O1 Cu1 Cu2 N2 -154.08(12) . . . 2_556 ? O2 Cu1 Cu2 N2 20.92(13) . . . 2_556 ? N2 Cu1 Cu2 N2 180.0 . . . 2_556 ? N5 Cu1 Cu2 N2 17.87(13) . . . 2_556 ? O1 Cu1 Cu2 N5 -171.95(12) . . . . ? O2 Cu1 Cu2 N5 3.05(11) . . . . ? N2 Cu1 Cu2 N5 162.13(13) . . . . ? O1 Cu1 Cu2 N5 8.05(12) . . . 2_556 ? O2 Cu1 Cu2 N5 -176.95(11) . . . 2_556 ? N2 Cu1 Cu2 N5 -17.87(13) . . . 2_556 ? N5 Cu1 Cu2 N5 180.0 . . . 2_556 ? O1 Cu1 Cu2 Cu1 -113(100) . . . 2_556 ? O2 Cu1 Cu2 Cu1 62(100) . . . 2_556 ? N2 Cu1 Cu2 Cu1 -139(100) . . . 2_556 ? N5 Cu1 Cu2 Cu1 59(100) . . . 2_556 ? O1 Cu1 N2 N3 -19.1(2) . . . . ? O2 Cu1 N2 N3 -118.1(3) . . . . ? N5 Cu1 N2 N3 153.5(2) . . . . ? Cu2 Cu1 N2 N3 141.6(3) . . . . ? O1 Cu1 N2 Cu2 -160.72(9) . . . . ? O2 Cu1 N2 Cu2 100.3(3) . . . . ? N5 Cu1 N2 Cu2 11.90(8) . . . . ? N2 Cu2 N2 N3 -116(100) 2_556 . . . ? N5 Cu2 N2 N3 -151.0(3) . . . . ? N5 Cu2 N2 N3 29.0(3) 2_556 . . . ? Cu1 Cu2 N2 N3 41.0(3) 2_556 . . . ? Cu1 Cu2 N2 N3 -139.0(3) . . . . ? N2 Cu2 N2 Cu1 23(100) 2_556 . . . ? N5 Cu2 N2 Cu1 -12.01(8) . . . . ? N5 Cu2 N2 Cu1 167.99(8) 2_556 . . . ? Cu1 Cu2 N2 Cu1 180.0 2_556 . . . ? Cu1 N2 N3 N4 73(13) . . . . ? Cu2 N2 N3 N4 -157(13) . . . . ? N2 Cu2 N5 N6 144.4(2) . . . . ? N2 Cu2 N5 N6 -35.6(2) 2_556 . . . ? N5 Cu2 N5 N6 96(100) 2_556 . . . ? Cu1 Cu2 N5 N6 -47.4(2) 2_556 . . . ? Cu1 Cu2 N5 N6 132.6(2) . . . . ? N2 Cu2 N5 Cu1 11.81(8) . . . . ? N2 Cu2 N5 Cu1 -168.19(8) 2_556 . . . ? N5 Cu2 N5 Cu1 -36(100) 2_556 . . . ? Cu1 Cu2 N5 Cu1 180.0 2_556 . . . ? O1 Cu1 N5 N6 -91.4(5) . . . . ? O2 Cu1 N5 N6 49.6(2) . . . . ? N2 Cu1 N5 N6 -144.3(2) . . . . ? Cu2 Cu1 N5 N6 -132.5(2) . . . . ? O1 Cu1 N5 Cu2 41.0(5) . . . . ? O2 Cu1 N5 Cu2 -177.99(7) . . . . ? N2 Cu1 N5 Cu2 -11.83(8) . . . . ? Cu2 N5 N6 N7 111(10) . . . . ? Cu1 N5 N6 N7 -128(10) . . . . ? O1 N1 C1 C2 -178.9(3) . . . . ? C5 N1 C1 C2 -0.9(4) . . . . ? N1 C1 C2 C3 1.3(5) . . . . ? C1 C2 C3 C4 0.3(5) . . . . ? C2 C3 C4 C5 -2.3(5) . . . . ? C1 N1 C5 C4 -1.1(4) . . . . ? O1 N1 C5 C4 176.8(2) . . . . ? C1 N1 C5 C6 175.3(2) . . . . ? O1 N1 C5 C6 -6.8(3) . . . . ? C3 C4 C5 N1 2.7(4) . . . . ? C3 C4 C5 C6 -173.6(3) . . . . ? N1 C5 C6 O3 144.5(2) . . . . ? C4 C5 C6 O3 -39.2(4) . . . . ? N1 C5 C6 O2 -38.0(3) . . . . ? C4 C5 C6 O2 138.3(3) . . . . ? C1 N1 O1 Cu1 -125.5(2) . . . . ? C5 N1 O1 Cu1 56.5(3) . . . . ? O2 Cu1 O1 N1 -53.96(16) . . . . ? N2 Cu1 O1 N1 139.60(17) . . . . ? N5 Cu1 O1 N1 87.4(5) . . . . ? Cu2 Cu1 O1 N1 122.78(14) . . . . ? O3 C6 O2 Cu1 -158.4(2) . . . . ? C5 C6 O2 Cu1 24.3(3) . . . . ? O1 Cu1 O2 C6 15.5(2) . . . . ? N2 Cu1 O2 C6 114.8(4) . . . . ? N5 Cu1 O2 C6 -158.7(2) . . . . ? Cu2 Cu1 O2 C6 -160.73(16) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.322 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.077