# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jonathan Steed' _publ_contact_author_email JON.STEED@DUR.AC.UK loop_ _publ_author_name J.Steed A.Goeta S.Handa J.Lipkowski D.Swierczynski data_2.CIF _database_code_depnum_ccdc_archive 'CCDC 622422' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common TACNCU3 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H50 Cl4 Cu2 N6 O4' _chemical_formula_weight 683.52 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' 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 13.7720(14) _cell_length_b 13.5920(14) _cell_length_c 8.5480(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.364(3) _cell_angle_gamma 90.00 _cell_volume 1568.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow-olive _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 1.729 _exptl_absorpt_correction_type Scalepack _exptl_absorpt_correction_T_min 0.7237 _exptl_absorpt_correction_T_max 0.8461 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2876 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2876 _reflns_number_gt 2558 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed interface to POVRay' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0665P)^2^+1.3816P] 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 SHELXL _refine_ls_extinction_coef 0.018(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2876 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1223 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.89066(3) 0.25219(2) 0.15701(4) 0.0401(2) Uani 1 1 d . . . Cl1 Cl 1.03225(7) 0.32244(6) 0.07155(12) 0.0673(3) Uani 1 1 d . . . O1 O 0.5791(3) 0.3772(4) -0.4632(4) 0.1289(16) Uani 1 1 d . . . N1 N 0.8222(2) 0.19622(18) -0.0752(3) 0.0468(6) Uani 1 1 d . . . C1 C 0.7947(3) 0.2878(3) -0.1672(4) 0.0575(8) Uani 1 1 d . . . H1A H 0.7535 0.2715 -0.2696 0.069 Uiso 1 1 calc R . . H1B H 0.8542 0.3195 -0.1871 0.069 Uiso 1 1 calc R . . Cl2 Cl 1.0000 0.10936(9) 0.2500 0.0608(3) Uani 1 2 d S . . O2 O 0.5000 0.5077(4) -0.2500 0.0858(12) Uani 1 2 d S . . N2 N 0.7929(2) 0.37358(18) 0.0880(3) 0.0502(6) Uani 1 1 d . . . C2 C 0.7397(3) 0.3581(2) -0.0801(4) 0.0577(8) Uani 1 1 d . . . H2A H 0.7323 0.4208 -0.1355 0.069 Uiso 1 1 calc R . . H2B H 0.6741 0.3323 -0.0801 0.069 Uiso 1 1 calc R . . Cl3 Cl 0.5414(3) 0.1641(4) -0.4226(5) 0.1443(14) Uani 0.50 1 d P . . O3 O 0.5000 -0.0417(6) -0.2500 0.160(3) Uani 1 2 d S . . N3 N 0.7652(2) 0.18790(18) 0.2265(3) 0.0468(6) Uani 1 1 d . . . C3 C 0.7250(3) 0.3654(2) 0.2015(4) 0.0574(8) Uani 1 1 d . . . H3A H 0.6705 0.4112 0.1708 0.069 Uiso 1 1 calc R . . H3B H 0.7601 0.3834 0.3074 0.069 Uiso 1 1 calc R . . C4 C 0.6842(3) 0.2622(2) 0.2060(5) 0.0547(8) Uani 1 1 d . . . H4A H 0.6491 0.2568 0.2936 0.066 Uiso 1 1 calc R . . H4B H 0.6374 0.2492 0.1075 0.066 Uiso 1 1 calc R . . C5 C 0.7413(3) 0.1045(2) 0.1134(4) 0.0547(8) Uani 1 1 d . . . H5A H 0.6787 0.0756 0.1248 0.066 Uiso 1 1 calc R . . H5B H 0.7921 0.0545 0.1390 0.066 Uiso 1 1 calc R . . C6 C 0.7346(3) 0.1376(2) -0.0569(4) 0.0536(8) Uani 1 1 d . . . H6A H 0.7293 0.0805 -0.1259 0.064 Uiso 1 1 calc R . . H6B H 0.6753 0.1770 -0.0897 0.064 Uiso 1 1 calc R . . C7 C 0.8913(3) 0.1373(3) -0.1494(4) 0.0651(9) Uani 1 1 d . . . H7A H 0.9095 0.0787 -0.0878 0.098 Uiso 1 1 calc R . . H7B H 0.9497 0.1753 -0.1526 0.098 Uiso 1 1 calc R . . H7C H 0.8597 0.1196 -0.2560 0.098 Uiso 1 1 calc R . . C8 C 0.8413(3) 0.4712(2) 0.1060(5) 0.0677(10) Uani 1 1 d . . . H8A H 0.7917 0.5217 0.0876 0.102 Uiso 1 1 calc R . . H8B H 0.8838 0.4776 0.0301 0.102 Uiso 1 1 calc R . . H8C H 0.8798 0.4776 0.2121 0.102 Uiso 1 1 calc R . . C9 C 0.7854(3) 0.1505(3) 0.3928(4) 0.0641(9) Uani 1 1 d . . . H9A H 0.7997 0.2048 0.4655 0.096 Uiso 1 1 calc R . . H9B H 0.8412 0.1068 0.4077 0.096 Uiso 1 1 calc R . . H9C H 0.7283 0.1158 0.4127 0.096 Uiso 1 1 calc R . . 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 0.0337(3) 0.0438(3) 0.0417(3) -0.00198(13) 0.00497(17) 0.00045(12) Cl1 0.0725(7) 0.0548(5) 0.0796(6) -0.0019(4) 0.0275(5) -0.0070(4) O1 0.111(3) 0.187(4) 0.081(2) -0.020(2) 0.001(2) 0.065(3) N1 0.0493(16) 0.0466(13) 0.0467(13) -0.0022(11) 0.0146(11) 0.0023(10) C1 0.067(2) 0.062(2) 0.0412(16) 0.0062(14) 0.0058(14) 0.0033(17) Cl2 0.0724(8) 0.0548(6) 0.0582(7) 0.000 0.0201(6) 0.000 O2 0.080(3) 0.108(3) 0.073(2) 0.000 0.025(2) 0.000 N2 0.0587(17) 0.0433(13) 0.0494(14) -0.0033(11) 0.0126(12) -0.0030(11) C2 0.067(2) 0.0520(18) 0.0500(17) 0.0077(14) 0.0018(15) 0.0079(15) Cl3 0.092(2) 0.184(4) 0.142(3) 0.028(3) -0.0140(19) -0.018(2) O3 0.108(5) 0.176(7) 0.217(8) 0.000 0.080(5) 0.000 N3 0.0490(16) 0.0486(13) 0.0437(13) 0.0009(10) 0.0112(10) 0.0042(11) C3 0.055(2) 0.0551(18) 0.067(2) -0.0061(15) 0.0225(16) 0.0096(14) C4 0.045(2) 0.064(2) 0.0588(19) 0.0015(15) 0.0191(15) 0.0076(14) C5 0.053(2) 0.0479(17) 0.0633(19) -0.0036(14) 0.0122(15) -0.0092(14) C6 0.049(2) 0.0529(18) 0.0569(18) -0.0123(14) 0.0043(14) -0.0064(14) C7 0.071(3) 0.068(2) 0.063(2) -0.0121(17) 0.0293(18) 0.0064(17) C8 0.086(3) 0.0466(18) 0.072(2) -0.0040(16) 0.0180(19) -0.0087(17) C9 0.080(3) 0.066(2) 0.0488(18) 0.0122(16) 0.0185(17) 0.0039(18) _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 N3 2.123(3) . ? Cu1 N2 2.138(3) . ? Cu1 N1 2.161(3) . ? Cu1 Cl1 2.4102(10) . ? Cu1 Cl2 2.4892(10) . ? Cu1 Cl1 2.5400(11) 2_755 ? Cl1 Cu1 2.5400(11) 2_755 ? N1 C7 1.480(4) . ? N1 C6 1.480(4) . ? N1 C1 1.482(4) . ? C1 C2 1.504(5) . ? Cl2 Cu1 2.4892(10) 2_755 ? N2 C3 1.479(4) . ? N2 C8 1.479(4) . ? N2 C2 1.494(4) . ? N3 C9 1.483(4) . ? N3 C5 1.484(4) . ? N3 C4 1.490(4) . ? C3 C4 1.515(5) . ? C5 C6 1.509(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N2 83.80(10) . . ? N3 Cu1 N1 83.11(10) . . ? N2 Cu1 N1 83.18(10) . . ? N3 Cu1 Cl1 178.42(7) . . ? N2 Cu1 Cl1 96.52(8) . . ? N1 Cu1 Cl1 95.38(7) . . ? N3 Cu1 Cl2 93.68(7) . . ? N2 Cu1 Cl2 176.87(7) . . ? N1 Cu1 Cl2 98.38(7) . . ? Cl1 Cu1 Cl2 86.05(3) . . ? N3 Cu1 Cl1 96.66(7) . 2_755 ? N2 Cu1 Cl1 95.11(7) . 2_755 ? N1 Cu1 Cl1 178.28(7) . 2_755 ? Cl1 Cu1 Cl1 84.86(4) . 2_755 ? Cl2 Cu1 Cl1 83.33(3) . 2_755 ? Cu1 Cl1 Cu1 77.98(3) . 2_755 ? C7 N1 C6 111.2(3) . . ? C7 N1 C1 110.2(3) . . ? C6 N1 C1 112.3(3) . . ? C7 N1 Cu1 112.5(2) . . ? C6 N1 Cu1 108.06(18) . . ? C1 N1 Cu1 102.21(19) . . ? N1 C1 C2 111.8(3) . . ? Cu1 Cl2 Cu1 77.50(4) 2_755 . ? C3 N2 C8 109.2(3) . . ? C3 N2 C2 111.5(3) . . ? C8 N2 C2 110.6(3) . . ? C3 N2 Cu1 101.91(19) . . ? C8 N2 Cu1 114.7(2) . . ? C2 N2 Cu1 108.65(19) . . ? N2 C2 C1 111.5(3) . . ? C9 N3 C5 109.8(3) . . ? C9 N3 C4 109.8(3) . . ? C5 N3 C4 112.1(3) . . ? C9 N3 Cu1 113.6(2) . . ? C5 N3 Cu1 102.73(18) . . ? C4 N3 Cu1 108.67(19) . . ? N2 C3 C4 111.8(3) . . ? N3 C4 C3 111.0(3) . . ? N3 C5 C6 111.4(3) . . ? N1 C6 C5 111.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 Cl1 Cu1 -123(3) . . . 2_755 ? N2 Cu1 Cl1 Cu1 135.50(7) . . . 2_755 ? N1 Cu1 Cl1 Cu1 -140.78(7) . . . 2_755 ? Cl2 Cu1 Cl1 Cu1 -42.72(2) . . . 2_755 ? Cl1 Cu1 Cl1 Cu1 40.93(3) 2_755 . . 2_755 ? N3 Cu1 N1 C7 -128.5(2) . . . . ? N2 Cu1 N1 C7 146.9(2) . . . . ? Cl1 Cu1 N1 C7 51.0(2) . . . . ? Cl2 Cu1 N1 C7 -35.8(2) . . . . ? Cl1 Cu1 N1 C7 149(2) 2_755 . . . ? N3 Cu1 N1 C6 -5.39(19) . . . . ? N2 Cu1 N1 C6 -89.9(2) . . . . ? Cl1 Cu1 N1 C6 174.12(18) . . . . ? Cl2 Cu1 N1 C6 87.33(19) . . . . ? Cl1 Cu1 N1 C6 -88(2) 2_755 . . . ? N3 Cu1 N1 C1 113.2(2) . . . . ? N2 Cu1 N1 C1 28.7(2) . . . . ? Cl1 Cu1 N1 C1 -67.25(19) . . . . ? Cl2 Cu1 N1 C1 -154.04(18) . . . . ? Cl1 Cu1 N1 C1 31(2) 2_755 . . . ? C7 N1 C1 C2 -169.7(3) . . . . ? C6 N1 C1 C2 65.8(4) . . . . ? Cu1 N1 C1 C2 -49.8(3) . . . . ? N3 Cu1 Cl2 Cu1 -137.66(7) . . . 2_755 ? N2 Cu1 Cl2 Cu1 -101.6(13) . . . 2_755 ? N1 Cu1 Cl2 Cu1 138.77(7) . . . 2_755 ? Cl1 Cu1 Cl2 Cu1 43.91(2) . . . 2_755 ? Cl1 Cu1 Cl2 Cu1 -41.37(2) 2_755 . . 2_755 ? N3 Cu1 N2 C3 29.4(2) . . . . ? N1 Cu1 N2 C3 113.2(2) . . . . ? Cl1 Cu1 N2 C3 -152.12(19) . . . . ? Cl2 Cu1 N2 C3 -6.8(15) . . . . ? Cl1 Cu1 N2 C3 -66.72(19) 2_755 . . . ? N3 Cu1 N2 C8 147.3(2) . . . . ? N1 Cu1 N2 C8 -129.0(2) . . . . ? Cl1 Cu1 N2 C8 -34.3(2) . . . . ? Cl2 Cu1 N2 C8 111.1(13) . . . . ? Cl1 Cu1 N2 C8 51.1(2) 2_755 . . . ? N3 Cu1 N2 C2 -88.4(2) . . . . ? N1 Cu1 N2 C2 -4.6(2) . . . . ? Cl1 Cu1 N2 C2 90.0(2) . . . . ? Cl2 Cu1 N2 C2 -124.6(13) . . . . ? Cl1 Cu1 N2 C2 175.4(2) 2_755 . . . ? C3 N2 C2 C1 -132.8(3) . . . . ? C8 N2 C2 C1 105.5(3) . . . . ? Cu1 N2 C2 C1 -21.2(3) . . . . ? N1 C1 C2 N2 50.1(4) . . . . ? N2 Cu1 N3 C9 -128.0(2) . . . . ? N1 Cu1 N3 C9 148.2(2) . . . . ? Cl1 Cu1 N3 C9 130(3) . . . . ? Cl2 Cu1 N3 C9 50.2(2) . . . . ? Cl1 Cu1 N3 C9 -33.5(2) 2_755 . . . ? N2 Cu1 N3 C5 113.49(19) . . . . ? N1 Cu1 N3 C5 29.65(19) . . . . ? Cl1 Cu1 N3 C5 12(3) . . . . ? Cl2 Cu1 N3 C5 -68.36(18) . . . . ? Cl1 Cu1 N3 C5 -152.06(18) 2_755 . . . ? N2 Cu1 N3 C4 -5.4(2) . . . . ? N1 Cu1 N3 C4 -89.3(2) . . . . ? Cl1 Cu1 N3 C4 -107(3) . . . . ? Cl2 Cu1 N3 C4 172.7(2) . . . . ? Cl1 Cu1 N3 C4 89.0(2) 2_755 . . . ? C8 N2 C3 C4 -171.9(3) . . . . ? C2 N2 C3 C4 65.6(4) . . . . ? Cu1 N2 C3 C4 -50.2(3) . . . . ? C9 N3 C4 C3 104.5(3) . . . . ? C5 N3 C4 C3 -133.2(3) . . . . ? Cu1 N3 C4 C3 -20.3(3) . . . . ? N2 C3 C4 N3 49.7(4) . . . . ? C9 N3 C5 C6 -171.9(3) . . . . ? C4 N3 C5 C6 65.7(3) . . . . ? Cu1 N3 C5 C6 -50.8(3) . . . . ? C7 N1 C6 C5 103.2(3) . . . . ? C1 N1 C6 C5 -132.8(3) . . . . ? Cu1 N1 C6 C5 -20.8(3) . . . . ? N3 C5 C6 N1 50.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.509 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.075 # Attachment '31.CIF' data_tacncu _database_code_depnum_ccdc_archive 'CCDC 622423' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C9.50 H22 Cl3 Cu N3' _chemical_formula_weight 348.19 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' 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 ORTHORHOMBIC _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y, -z-1/2' 'x-1/2, y-1/2, -z-1/2' _cell_length_a 13.7910(3) _cell_length_b 14.5310(2) _cell_length_c 15.0530(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3016.58(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 1.961 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi scans 2o frames DX=25mm' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33372 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2580 _reflns_number_gt 2397 _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 'RES2INS (Barbour, 1995)' _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 w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+3.8144P] 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 SHELXL _refine_ls_extinction_coef 0.0053(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2580 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.04249(2) 0.16340(2) 0.49108(2) 0.03320(18) Uani 1 d . . . Cl1 Cl -0.06294(6) 0.21605(6) 0.59848(5) 0.0521(3) Uani 1 d . . . Cl2 Cl -0.08229(6) 0.12998(8) 0.39971(6) 0.0688(3) Uani 1 d . . . Cl3 Cl 0.60305(9) 0.02822(9) 0.27327(9) 0.0865(4) Uani 1 d . . . N1 N 0.16105(18) 0.16990(18) 0.57837(17) 0.0420(6) Uani 1 d . . . N2 N 0.14702(18) 0.10893(17) 0.40316(16) 0.0411(6) Uani 1 d . . . N3 N 0.10074(18) 0.29775(17) 0.44339(19) 0.0476(6) Uani 1 d . . . C1 C 0.2450(3) 0.1239(4) 0.5371(3) 0.0756(12) Uani 1 d . . . H1A H 0.2915 0.1704 0.5190 0.091 Uiso 1 calc R . . H1B H 0.2762 0.0852 0.5811 0.091 Uiso 1 calc R . . C2 C 0.2209(3) 0.0691(3) 0.4621(3) 0.0741(12) Uani 1 d . . . H2A H 0.1979 0.0098 0.4829 0.089 Uiso 1 calc R . . H2B H 0.2794 0.0584 0.4278 0.089 Uiso 1 calc R . . C3 C 0.1877(3) 0.1859(3) 0.3503(3) 0.0705(11) Uani 1 d . . . H3A H 0.2544 0.1954 0.3687 0.085 Uiso 1 calc R . . H3B H 0.1888 0.1675 0.2884 0.085 Uiso 1 calc R . . C4 C 0.1372(4) 0.2732(3) 0.3567(3) 0.0798(13) Uani 1 d . . . H4A H 0.1809 0.3214 0.3371 0.096 Uiso 1 calc R . . H4B H 0.0830 0.2720 0.3157 0.096 Uiso 1 calc R . . C5 C 0.1765(4) 0.3237(3) 0.5075(3) 0.0745(13) Uani 1 d . . . H5A H 0.2391 0.3184 0.4784 0.089 Uiso 1 calc R . . H5B H 0.1676 0.3879 0.5232 0.089 Uiso 1 calc R . . C6 C 0.1790(4) 0.2698(3) 0.5886(3) 0.0755(12) Uani 1 d . . . H6A H 0.1309 0.2945 0.6292 0.091 Uiso 1 calc R . . H6B H 0.2420 0.2780 0.6161 0.091 Uiso 1 calc R . . C7 C 0.1418(3) 0.1295(3) 0.6663(2) 0.0688(11) Uani 1 d . . . H7A H 0.0881 0.1608 0.6935 0.083 Uiso 1 calc R . . H7B H 0.1982 0.1359 0.7031 0.083 Uiso 1 calc R . . H7C H 0.1264 0.0654 0.6597 0.083 Uiso 1 calc R . . C8 C 0.1134(3) 0.0342(3) 0.3442(3) 0.0762(12) Uani 1 d . . . H8A H 0.0711 0.0591 0.2996 0.091 Uiso 1 calc R . . H8B H 0.0790 -0.0109 0.3785 0.091 Uiso 1 calc R . . H8C H 0.1683 0.0058 0.3161 0.091 Uiso 1 calc R . . C9 C 0.0257(3) 0.3688(3) 0.4360(4) 0.0853(15) Uani 1 d . . . H9A H 0.0545 0.4252 0.4159 0.102 Uiso 1 calc R . . H9B H -0.0038 0.3783 0.4930 0.102 Uiso 1 calc R . . H9C H -0.0227 0.3493 0.3942 0.102 Uiso 1 calc R . . C1S C 0.5000 0.0950(4) 0.2500 0.0761(16) Uani 1 d S . . H1S1 H 0.4864 0.1344 0.3005 0.091 Uiso 0.50 calc PR . . H1S2 H 0.5136 0.1344 0.1995 0.091 Uiso 0.50 calc PR . . 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 0.0271(2) 0.0372(3) 0.0353(2) 0.00144(13) 0.00019(12) -0.00205(12) Cl1 0.0374(4) 0.0680(5) 0.0509(5) -0.0081(4) 0.0082(3) 0.0020(3) Cl2 0.0373(4) 0.1090(8) 0.0600(6) -0.0225(5) -0.0081(4) -0.0051(4) Cl3 0.0812(8) 0.0792(8) 0.0989(9) -0.0046(6) -0.0057(6) 0.0060(5) N1 0.0348(12) 0.0547(16) 0.0365(13) 0.0016(10) -0.0030(10) -0.0027(10) N2 0.0391(13) 0.0452(14) 0.0390(13) -0.0039(10) 0.0020(10) -0.0001(10) N3 0.0400(13) 0.0401(14) 0.0629(17) 0.0145(12) 0.0086(12) 0.0035(11) C1 0.050(2) 0.120(4) 0.058(2) -0.003(2) -0.0106(18) 0.036(2) C2 0.061(2) 0.091(3) 0.070(2) -0.013(2) -0.007(2) 0.040(2) C3 0.080(3) 0.072(2) 0.060(2) 0.0103(19) 0.033(2) 0.002(2) C4 0.098(3) 0.071(3) 0.071(3) 0.032(2) 0.030(2) 0.010(2) C5 0.074(3) 0.042(2) 0.107(4) -0.0024(19) -0.011(2) -0.0164(18) C6 0.081(3) 0.075(3) 0.070(3) -0.006(2) -0.019(2) -0.032(2) C7 0.059(2) 0.104(3) 0.0431(19) 0.017(2) -0.0087(16) -0.003(2) C8 0.067(2) 0.081(3) 0.081(3) -0.042(2) 0.011(2) -0.010(2) C9 0.066(3) 0.056(2) 0.134(4) 0.039(3) 0.021(3) 0.0179(19) C1S 0.087(4) 0.054(3) 0.087(4) 0.000 -0.013(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 N1 2.100(2) . ? Cu1 N2 2.111(2) . ? Cu1 N3 2.230(2) . ? Cu1 Cl2 2.2558(9) . ? Cu1 Cl1 2.3050(8) . ? Cl3 C1S 1.756(4) . ? N1 C7 1.472(4) . ? N1 C1 1.475(4) . ? N1 C6 1.481(5) . ? N2 C2 1.470(4) . ? N2 C8 1.478(4) . ? N2 C3 1.483(4) . ? N3 C4 1.443(5) . ? N3 C9 1.466(4) . ? N3 C5 1.471(5) . ? C1 C2 1.420(6) . ? C3 C4 1.450(6) . ? C5 C6 1.451(6) . ? C1S Cl3 1.756(4) 7_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 82.96(10) . . ? N1 Cu1 N3 83.20(10) . . ? N2 Cu1 N3 83.13(10) . . ? N1 Cu1 Cl2 170.15(8) . . ? N2 Cu1 Cl2 93.32(7) . . ? N3 Cu1 Cl2 105.49(8) . . ? N1 Cu1 Cl1 92.14(7) . . ? N2 Cu1 Cl1 174.24(7) . . ? N3 Cu1 Cl1 99.35(7) . . ? Cl2 Cu1 Cl1 91.03(3) . . ? C7 N1 C1 109.9(3) . . ? C7 N1 C6 109.1(3) . . ? C1 N1 C6 110.9(3) . . ? C7 N1 Cu1 113.8(2) . . ? C1 N1 Cu1 109.1(2) . . ? C6 N1 Cu1 103.9(2) . . ? C2 N2 C8 106.9(3) . . ? C2 N2 C3 111.0(3) . . ? C8 N2 C3 110.5(3) . . ? C2 N2 Cu1 104.0(2) . . ? C8 N2 Cu1 116.0(2) . . ? C3 N2 Cu1 108.2(2) . . ? C4 N3 C9 110.6(3) . . ? C4 N3 C5 114.1(3) . . ? C9 N3 C5 111.8(4) . . ? C4 N3 Cu1 101.5(2) . . ? C9 N3 Cu1 112.7(2) . . ? C5 N3 Cu1 105.6(2) . . ? C2 C1 N1 113.9(3) . . ? C1 C2 N2 114.9(3) . . ? C4 C3 N2 116.2(3) . . ? N3 C4 C3 116.4(3) . . ? C6 C5 N3 115.5(3) . . ? C5 C6 N1 115.9(3) . . ? Cl3 C1S Cl3 112.9(3) 7_656 . ? 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 N2 Cu1 N1 C7 -130.3(3) . . . . ? N3 Cu1 N1 C7 145.8(3) . . . . ? Cl2 Cu1 N1 C7 -62.0(5) . . . . ? Cl1 Cu1 N1 C7 46.7(3) . . . . ? N2 Cu1 N1 C1 -7.2(3) . . . . ? N3 Cu1 N1 C1 -91.0(3) . . . . ? Cl2 Cu1 N1 C1 61.2(5) . . . . ? Cl1 Cu1 N1 C1 169.8(3) . . . . ? N2 Cu1 N1 C6 111.2(2) . . . . ? N3 Cu1 N1 C6 27.3(2) . . . . ? Cl2 Cu1 N1 C6 179.5(4) . . . . ? Cl1 Cu1 N1 C6 -71.9(2) . . . . ? N1 Cu1 N2 C2 25.4(3) . . . . ? N3 Cu1 N2 C2 109.3(3) . . . . ? Cl2 Cu1 N2 C2 -145.5(2) . . . . ? Cl1 Cu1 N2 C2 -6.5(9) . . . . ? N1 Cu1 N2 C8 142.4(3) . . . . ? N3 Cu1 N2 C8 -133.6(3) . . . . ? Cl2 Cu1 N2 C8 -28.4(3) . . . . ? Cl1 Cu1 N2 C8 110.6(7) . . . . ? N1 Cu1 N2 C3 -92.7(2) . . . . ? N3 Cu1 N2 C3 -8.8(2) . . . . ? Cl2 Cu1 N2 C3 96.4(2) . . . . ? Cl1 Cu1 N2 C3 -124.6(7) . . . . ? N1 Cu1 N3 C4 109.8(3) . . . . ? N2 Cu1 N3 C4 26.1(2) . . . . ? Cl2 Cu1 N3 C4 -65.5(2) . . . . ? Cl1 Cu1 N3 C4 -159.2(2) . . . . ? N1 Cu1 N3 C9 -131.9(3) . . . . ? N2 Cu1 N3 C9 144.4(3) . . . . ? Cl2 Cu1 N3 C9 52.9(3) . . . . ? Cl1 Cu1 N3 C9 -40.8(3) . . . . ? N1 Cu1 N3 C5 -9.5(3) . . . . ? N2 Cu1 N3 C5 -93.2(3) . . . . ? Cl2 Cu1 N3 C5 175.2(2) . . . . ? Cl1 Cu1 N3 C5 81.5(2) . . . . ? C7 N1 C1 C2 111.2(4) . . . . ? C6 N1 C1 C2 -128.1(4) . . . . ? Cu1 N1 C1 C2 -14.3(5) . . . . ? N1 C1 C2 N2 39.6(6) . . . . ? C8 N2 C2 C1 -165.6(4) . . . . ? C3 N2 C2 C1 73.8(5) . . . . ? Cu1 N2 C2 C1 -42.4(5) . . . . ? C2 N2 C3 C4 -124.9(4) . . . . ? C8 N2 C3 C4 116.7(4) . . . . ? Cu1 N2 C3 C4 -11.3(5) . . . . ? C9 N3 C4 C3 -161.2(4) . . . . ? C5 N3 C4 C3 71.8(5) . . . . ? Cu1 N3 C4 C3 -41.3(5) . . . . ? N2 C3 C4 N3 38.8(6) . . . . ? C4 N3 C5 C6 -122.6(4) . . . . ? C9 N3 C5 C6 111.0(4) . . . . ? Cu1 N3 C5 C6 -12.0(5) . . . . ? N3 C5 C6 N1 39.5(6) . . . . ? C7 N1 C6 C5 -166.0(4) . . . . ? C1 N1 C6 C5 72.8(5) . . . . ? Cu1 N1 C6 C5 -44.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 0.531 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.061