# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2011 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Johnson, Andrew' _publ_contact_author_email chsalj@bath.ac.uk _publ_section_title ; Plasma Deposited Schiff-base Coordinated Zinc Compounds as Antimicrobials ; loop_ _publ_author_name A.Johnson T.Jenkins N.Poulter M.Donaldson G.Mulley L.Duque ; N.Waterfield ; A.Shard S.Spencer data_h08alj06 _database_code_depnum_ccdc_archive 'CCDC 771905' #TrackingRef 'h08alj06.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 N2 O2 Zn' _chemical_formula_weight 385.75 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' O O 0.0106 0.0060 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8230(5) _cell_length_b 10.3560(6) _cell_length_c 10.7400(6) _cell_angle_alpha 63.590(3) _cell_angle_beta 76.146(3) _cell_angle_gamma 70.354(2) _cell_volume 916.31(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4188 _cell_measurement_theta_min 3.95 _cell_measurement_theta_max 27.61 _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 1.355 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6867 _exptl_absorpt_correction_T_max 0.8764 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Kappa CCD Diffractometer' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11966 _diffrn_reflns_av_R_equivalents 0.0705 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _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 3.95 _diffrn_reflns_theta_max 27.61 _reflns_number_total 4188 _reflns_number_gt 3286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (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^)+(0.0740P)^2^+0.1790P] 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 4188 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1400 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 Zn1 Zn 1.13976(4) 0.05167(4) -0.00177(4) 0.03061(15) Uani 1 1 d . . . O1 O 1.2150(3) 0.1015(2) 0.1230(2) 0.0349(5) Uani 1 1 d . . . O2 O 0.9407(2) 0.0307(2) 0.1064(2) 0.0326(5) Uani 1 1 d . . . N1 N 1.1227(3) 0.2633(3) -0.1545(3) 0.0347(6) Uani 1 1 d . . . N2 N 0.6754(3) 0.1226(3) -0.0081(3) 0.0323(6) Uani 1 1 d . . . C1 C 1.2119(3) 0.2323(4) 0.1119(3) 0.0324(7) Uani 1 1 d . . . C2 C 1.2389(4) 0.2484(4) 0.2273(3) 0.0357(7) Uani 1 1 d . . . H2A H 1.2547 0.1635 0.3131 0.043 Uiso 1 1 calc R . . C3 C 1.2430(4) 0.3835(4) 0.2184(4) 0.0387(7) Uani 1 1 d . . . H3 H 1.2608 0.3903 0.2981 0.046 Uiso 1 1 calc R . . C4 C 1.2214(4) 0.5112(4) 0.0942(4) 0.0424(8) Uani 1 1 d . . . H4 H 1.2277 0.6035 0.0881 0.051 Uiso 1 1 calc R . . C5 C 1.1909(4) 0.5009(4) -0.0186(4) 0.0392(7) Uani 1 1 d . . . H5 H 1.1754 0.5876 -0.1031 0.047 Uiso 1 1 calc R . . C6 C 1.1819(4) 0.3651(4) -0.0128(3) 0.0337(7) Uani 1 1 d . . . C7 C 1.1420(4) 0.3703(4) -0.1356(3) 0.0361(7) Uani 1 1 d . . . H7 H 1.1281 0.4646 -0.2127 0.043 Uiso 1 1 calc R . . C8 C 1.0686(4) 0.3043(4) -0.2872(4) 0.0427(8) Uani 1 1 d . . . H8A H 1.0321 0.4144 -0.3320 0.051 Uiso 1 1 calc R . . H8B H 0.9860 0.2612 -0.2674 0.051 Uiso 1 1 calc R . . C9 C 1.1828(5) 0.2509(4) -0.3870(4) 0.0469(9) Uani 1 1 d . . . H9 H 1.1504 0.2515 -0.4639 0.056 Uiso 1 1 calc R . . C10 C 1.3224(5) 0.2036(5) -0.3782(4) 0.0574(11) Uani 1 1 d . . . H10A H 1.3600 0.2009 -0.3032 0.069 Uiso 1 1 calc R . . H10B H 1.3865 0.1718 -0.4469 0.069 Uiso 1 1 calc R . . C11 C 0.8617(4) 0.0899(3) 0.1976(3) 0.0310(6) Uani 1 1 d . . . C12 C 0.9262(4) 0.0855(4) 0.3036(3) 0.0355(7) Uani 1 1 d . . . H12 H 1.0275 0.0413 0.3093 0.043 Uiso 1 1 calc R . . C13 C 0.8453(4) 0.1439(4) 0.3992(4) 0.0407(8) Uani 1 1 d . . . H13 H 0.8917 0.1379 0.4704 0.049 Uiso 1 1 calc R . . C14 C 0.6970(4) 0.2115(4) 0.3938(4) 0.0457(8) Uani 1 1 d . . . H14 H 0.6422 0.2515 0.4604 0.055 Uiso 1 1 calc R . . C15 C 0.6308(4) 0.2195(4) 0.2896(4) 0.0399(8) Uani 1 1 d . . . H15 H 0.5297 0.2663 0.2845 0.048 Uiso 1 1 calc R . . C16 C 0.7108(4) 0.1593(4) 0.1903(3) 0.0333(7) Uani 1 1 d . . . C17 C 0.6309(4) 0.1822(4) 0.0820(3) 0.0330(7) Uani 1 1 d . . . H17 H 0.5358 0.2480 0.0769 0.040 Uiso 1 1 calc R . . C18 C 0.5762(4) 0.1753(4) -0.1159(4) 0.0382(7) Uani 1 1 d . . . H18A H 0.4830 0.2408 -0.0933 0.046 Uiso 1 1 calc R . . H18B H 0.5557 0.0887 -0.1172 0.046 Uiso 1 1 calc R . . C19 C 0.6462(4) 0.2603(4) -0.2568(4) 0.0421(8) Uani 1 1 d . . . H19 H 0.7344 0.2085 -0.2932 0.051 Uiso 1 1 calc R . . C20 C 0.5921(6) 0.4015(5) -0.3319(5) 0.0637(12) Uani 1 1 d . . . H20A H 0.5041 0.4560 -0.2980 0.076 Uiso 1 1 calc R . . H20B H 0.6408 0.4498 -0.4204 0.076 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 Zn1 0.0322(2) 0.0312(2) 0.0335(2) -0.01666(16) -0.00480(14) -0.00821(15) O1 0.0400(13) 0.0309(11) 0.0389(12) -0.0162(9) -0.0108(9) -0.0077(9) O2 0.0322(11) 0.0367(11) 0.0371(11) -0.0233(10) -0.0026(9) -0.0077(9) N1 0.0398(15) 0.0360(14) 0.0337(14) -0.0170(11) -0.0043(11) -0.0118(12) N2 0.0352(14) 0.0327(13) 0.0312(13) -0.0136(11) -0.0054(10) -0.0090(11) C1 0.0273(15) 0.0362(16) 0.0405(17) -0.0214(14) -0.0014(12) -0.0097(13) C2 0.0378(18) 0.0399(17) 0.0359(17) -0.0192(14) -0.0047(13) -0.0119(14) C3 0.0372(18) 0.0481(19) 0.0429(18) -0.0282(16) 0.0007(14) -0.0151(15) C4 0.042(2) 0.0411(18) 0.055(2) -0.0272(17) -0.0017(15) -0.0160(15) C5 0.045(2) 0.0322(16) 0.0405(18) -0.0146(14) -0.0065(14) -0.0088(14) C6 0.0352(17) 0.0351(16) 0.0347(16) -0.0164(13) -0.0019(12) -0.0117(13) C7 0.0364(18) 0.0317(15) 0.0378(17) -0.0120(13) -0.0024(13) -0.0097(13) C8 0.054(2) 0.0410(19) 0.0368(17) -0.0131(15) -0.0128(15) -0.0145(16) C9 0.065(3) 0.051(2) 0.0311(17) -0.0156(15) -0.0010(16) -0.0278(19) C10 0.067(3) 0.065(3) 0.041(2) -0.0229(19) 0.0115(18) -0.029(2) C11 0.0357(17) 0.0286(14) 0.0295(15) -0.0123(12) 0.0005(12) -0.0110(12) C12 0.0391(18) 0.0356(16) 0.0334(16) -0.0151(14) -0.0065(13) -0.0078(14) C13 0.047(2) 0.0460(19) 0.0333(16) -0.0196(15) -0.0091(14) -0.0084(15) C14 0.046(2) 0.058(2) 0.0396(18) -0.0299(17) -0.0015(15) -0.0086(17) C15 0.0356(18) 0.0465(19) 0.0386(17) -0.0246(15) -0.0005(13) -0.0042(14) C16 0.0378(17) 0.0341(16) 0.0315(15) -0.0159(13) -0.0035(12) -0.0098(13) C17 0.0287(16) 0.0369(16) 0.0365(16) -0.0172(13) -0.0041(12) -0.0085(13) C18 0.0328(17) 0.0436(18) 0.0450(18) -0.0241(15) -0.0095(14) -0.0054(14) C19 0.048(2) 0.048(2) 0.0392(18) -0.0210(16) -0.0127(15) -0.0117(16) C20 0.094(4) 0.050(2) 0.053(2) -0.015(2) -0.027(2) -0.019(2) _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 Zn1 O1 1.988(2) . ? Zn1 O2 2.048(2) . ? Zn1 N1 2.051(3) . ? Zn1 N2 2.070(3) 2_755 ? Zn1 O2 2.085(2) 2_755 ? O1 C1 1.297(4) . ? O2 C11 1.337(4) . ? O2 Zn1 2.085(2) 2_755 ? N1 C7 1.290(4) . ? N1 C8 1.472(4) . ? N2 C17 1.287(4) . ? N2 C18 1.486(4) . ? N2 Zn1 2.070(3) 2_755 ? C1 C2 1.416(4) . ? C1 C6 1.431(5) . ? C2 C3 1.373(5) . ? C2 H2A 0.9500 . ? C3 C4 1.396(5) . ? C3 H3 0.9500 . ? C4 C5 1.372(5) . ? C4 H4 0.9500 . ? C5 C6 1.411(5) . ? C5 H5 0.9500 . ? C6 C7 1.438(5) . ? C7 H7 0.9500 . ? C8 C9 1.499(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.303(6) . ? C9 H9 0.9500 . ? C10 H10A 0.9500 . ? C10 H10B 0.9500 . ? C11 C12 1.407(5) . ? C11 C16 1.417(5) . ? C12 C13 1.374(5) . ? C12 H12 0.9500 . ? C13 C14 1.391(5) . ? C13 H13 0.9500 . ? C14 C15 1.383(5) . ? C14 H14 0.9500 . ? C15 C16 1.416(5) . ? C15 H15 0.9500 . ? C16 C17 1.446(4) . ? C17 H17 0.9500 . ? C18 C19 1.504(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.306(6) . ? C19 H19 0.9500 . ? C20 H20A 0.9500 . ? C20 H20B 0.9500 . ? 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 Zn1 O2 99.58(9) . . ? O1 Zn1 N1 91.27(10) . . ? O2 Zn1 N1 110.49(10) . . ? O1 Zn1 N2 90.43(10) . 2_755 ? O2 Zn1 N2 125.62(10) . 2_755 ? N1 Zn1 N2 122.65(11) . 2_755 ? O1 Zn1 O2 171.31(9) . 2_755 ? O2 Zn1 O2 76.21(9) . 2_755 ? N1 Zn1 O2 97.33(10) . 2_755 ? N2 Zn1 O2 86.05(10) 2_755 2_755 ? C1 O1 Zn1 128.3(2) . . ? C11 O2 Zn1 129.0(2) . . ? C11 O2 Zn1 125.1(2) . 2_755 ? Zn1 O2 Zn1 103.79(9) . 2_755 ? C7 N1 C8 116.4(3) . . ? C7 N1 Zn1 123.2(2) . . ? C8 N1 Zn1 120.0(2) . . ? C17 N2 C18 115.6(3) . . ? C17 N2 Zn1 124.3(2) . 2_755 ? C18 N2 Zn1 119.7(2) . 2_755 ? O1 C1 C2 119.7(3) . . ? O1 C1 C6 123.4(3) . . ? C2 C1 C6 116.9(3) . . ? C3 C2 C1 121.7(3) . . ? C3 C2 H2A 119.2 . . ? C1 C2 H2A 119.2 . . ? C2 C3 C4 121.2(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 118.7(3) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 121.9(3) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C1 119.5(3) . . ? C5 C6 C7 116.6(3) . . ? C1 C6 C7 124.0(3) . . ? N1 C7 C6 128.2(3) . . ? N1 C7 H7 115.9 . . ? C6 C7 H7 115.9 . . ? N1 C8 C9 112.8(3) . . ? N1 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? N1 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 126.2(4) . . ? C10 C9 H9 116.9 . . ? C8 C9 H9 116.9 . . ? C9 C10 H10A 120.0 . . ? C9 C10 H10B 120.0 . . ? H10A C10 H10B 120.0 . . ? O2 C11 C12 120.9(3) . . ? O2 C11 C16 121.2(3) . . ? C12 C11 C16 118.0(3) . . ? C13 C12 C11 121.3(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 121.4(3) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C15 C14 C13 118.8(3) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C16 121.2(3) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C15 C16 C11 119.4(3) . . ? C15 C16 C17 115.9(3) . . ? C11 C16 C17 124.6(3) . . ? N2 C17 C16 126.6(3) . . ? N2 C17 H17 116.7 . . ? C16 C17 H17 116.7 . . ? N2 C18 C19 109.4(3) . . ? N2 C18 H18A 109.8 . . ? C19 C18 H18A 109.8 . . ? N2 C18 H18B 109.8 . . ? C19 C18 H18B 109.8 . . ? H18A C18 H18B 108.2 . . ? C20 C19 C18 123.5(4) . . ? C20 C19 H19 118.3 . . ? C18 C19 H19 118.3 . . ? C19 C20 H20A 120.0 . . ? C19 C20 H20B 120.0 . . ? H20A C20 H20B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.61 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.145 _refine_diff_density_min -0.661 _refine_diff_density_rms 0.117 # Attachment 'h08alj15.cif' data_h08alj15 _database_code_depnum_ccdc_archive 'CCDC 771906' #TrackingRef 'h08alj15.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Cu N2 O2' _chemical_formula_weight 383.92 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' 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.7130(2) _cell_length_b 7.35600(10) _cell_length_c 22.3240(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.8980(10) _cell_angle_gamma 90.00 _cell_volume 1714.85(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4117 _cell_measurement_theta_min 8.54 _cell_measurement_theta_max 28.28 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 796 _exptl_absorpt_coefficient_mu 1.289 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7826 _exptl_absorpt_correction_T_max 0.8503 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Kappa CCD Diffractometer' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 24844 _diffrn_reflns_av_R_equivalents 0.1017 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 8.54 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4117 _reflns_number_gt 3479 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (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^)+(0.0446P)^2^+0.6218P] 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 0.0031(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4117 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.828350(18) 0.26658(3) 0.383655(9) 0.01733(10) Uani 1 1 d . . . O1 O 0.80129(13) 0.2141(2) 0.29848(6) 0.0270(3) Uani 1 1 d . . . O2 O 0.84908(12) 0.30596(19) 0.46897(6) 0.0240(3) Uani 1 1 d . . . N1 N 0.65130(13) 0.37235(19) 0.37203(6) 0.0186(3) Uani 1 1 d . . . N2 N 1.00529(13) 0.16555(19) 0.39405(6) 0.0179(3) Uani 1 1 d . . . C1 C 0.71334(17) 0.2731(2) 0.25249(8) 0.0194(3) Uani 1 1 d . . . C2 C 0.72756(18) 0.2424(2) 0.19171(9) 0.0226(4) Uani 1 1 d . . . H2 H 0.8017 0.1813 0.1854 0.027 Uiso 1 1 calc R . . C3 C 0.63620(18) 0.2991(3) 0.14161(8) 0.0247(4) Uani 1 1 d . . . H3 H 0.6490 0.2783 0.1014 0.030 Uiso 1 1 calc R . . C4 C 0.52496(18) 0.3868(3) 0.14895(8) 0.0266(4) Uani 1 1 d . . . H4 H 0.4619 0.4244 0.1141 0.032 Uiso 1 1 calc R . . C5 C 0.50804(17) 0.4181(2) 0.20741(8) 0.0231(4) Uani 1 1 d . . . H5 H 0.4323 0.4773 0.2126 0.028 Uiso 1 1 calc R . . C6 C 0.60045(16) 0.3643(2) 0.25969(8) 0.0192(3) Uani 1 1 d . . . C7 C 0.57655(16) 0.4055(2) 0.31929(8) 0.0193(3) Uani 1 1 d . . . H7 H 0.4974 0.4632 0.3198 0.023 Uiso 1 1 calc R . . C8 C 0.60204(17) 0.4314(2) 0.42583(8) 0.0217(3) Uani 1 1 d . . . H8A H 0.5270 0.5118 0.4119 0.026 Uiso 1 1 calc R . . H8B H 0.6690 0.5022 0.4540 0.026 Uiso 1 1 calc R . . C9 C 0.5639(2) 0.2729(2) 0.45961(9) 0.0245(4) Uani 1 1 d . . . H9 H 0.6284 0.1886 0.4778 0.029 Uiso 1 1 calc R . . C10 C 0.4462(2) 0.2435(3) 0.46560(12) 0.0359(5) Uani 1 1 d . . . H10A H 0.3797 0.3256 0.4479 0.043 Uiso 1 1 calc R . . H10B H 0.4276 0.1402 0.4876 0.043 Uiso 1 1 calc R . . C21 C 0.95023(16) 0.2869(2) 0.51336(8) 0.0181(3) Uani 1 1 d . . . C22 C 0.94614(17) 0.3463(2) 0.57348(8) 0.0227(4) Uani 1 1 d . . . H22 H 0.8704 0.4020 0.5802 0.027 Uiso 1 1 calc R . . C23 C 1.04938(18) 0.3250(3) 0.62222(8) 0.0250(4) Uani 1 1 d . . . H23 H 1.0435 0.3662 0.6618 0.030 Uiso 1 1 calc R . . C24 C 1.16282(18) 0.2438(2) 0.61450(8) 0.0253(4) Uani 1 1 d . . . H24 H 1.2334 0.2285 0.6484 0.030 Uiso 1 1 calc R . . C25 C 1.16973(17) 0.1866(3) 0.55670(8) 0.0234(4) Uani 1 1 d . . . H25 H 1.2462 0.1306 0.5511 0.028 Uiso 1 1 calc R . . C26 C 1.06691(16) 0.2086(2) 0.50550(8) 0.0186(3) Uani 1 1 d . . . C27 C 1.08438(16) 0.1490(2) 0.44657(8) 0.0186(3) Uani 1 1 d . . . H27 H 1.1634 0.0906 0.4463 0.022 Uiso 1 1 calc R . . C28 C 1.05192(16) 0.0970(2) 0.34055(8) 0.0199(3) Uani 1 1 d . . . H28A H 0.9839 0.0232 0.3142 0.024 Uiso 1 1 calc R . . H28B H 1.1270 0.0173 0.3552 0.024 Uiso 1 1 calc R . . C29 C 1.08887(19) 0.2489(2) 0.30329(9) 0.0235(4) Uani 1 1 d . . . H29 H 1.0270 0.3401 0.2883 0.028 Uiso 1 1 calc R . . C30 C 1.2030(2) 0.2633(3) 0.29011(11) 0.0313(4) Uani 1 1 d . . . H30A H 1.2668 0.1741 0.3045 0.038 Uiso 1 1 calc R . . H30B H 1.2211 0.3627 0.2662 0.038 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 0.01541(13) 0.02307(14) 0.01367(13) 0.00080(7) 0.00356(8) 0.00243(7) O1 0.0224(6) 0.0427(8) 0.0155(6) 0.0000(5) 0.0033(5) 0.0114(6) O2 0.0186(6) 0.0364(7) 0.0170(6) -0.0005(5) 0.0037(5) 0.0043(5) N1 0.0192(7) 0.0194(7) 0.0181(7) -0.0002(5) 0.0062(5) 0.0011(5) N2 0.0191(7) 0.0183(7) 0.0173(7) 0.0010(5) 0.0061(5) 0.0008(5) C1 0.0180(8) 0.0221(8) 0.0174(8) 0.0016(6) 0.0026(6) -0.0020(6) C2 0.0209(9) 0.0280(9) 0.0195(8) -0.0012(6) 0.0057(7) -0.0031(7) C3 0.0289(9) 0.0277(9) 0.0171(8) 0.0008(7) 0.0044(7) -0.0084(7) C4 0.0278(9) 0.0266(9) 0.0212(9) 0.0044(7) -0.0035(7) -0.0032(7) C5 0.0222(8) 0.0221(8) 0.0230(9) 0.0014(6) 0.0007(7) 0.0005(7) C6 0.0208(8) 0.0173(8) 0.0193(8) 0.0016(6) 0.0042(6) -0.0014(6) C7 0.0159(7) 0.0199(8) 0.0222(8) -0.0006(6) 0.0045(6) 0.0013(6) C8 0.0214(8) 0.0249(9) 0.0205(8) -0.0015(6) 0.0086(7) 0.0059(7) C9 0.0265(9) 0.0277(9) 0.0210(9) -0.0033(7) 0.0092(7) -0.0004(7) C10 0.0308(11) 0.0425(12) 0.0387(12) -0.0049(9) 0.0171(9) -0.0058(8) C21 0.0188(8) 0.0204(8) 0.0148(8) 0.0021(6) 0.0029(6) -0.0024(6) C22 0.0265(9) 0.0241(9) 0.0184(8) 0.0000(6) 0.0071(7) -0.0001(7) C23 0.0325(10) 0.0243(9) 0.0174(8) -0.0012(6) 0.0041(7) -0.0052(7) C24 0.0240(9) 0.0302(10) 0.0182(9) 0.0026(7) -0.0026(7) -0.0066(7) C25 0.0195(8) 0.0266(9) 0.0239(9) 0.0023(7) 0.0042(7) -0.0017(7) C26 0.0192(8) 0.0194(8) 0.0173(8) 0.0013(6) 0.0040(6) -0.0019(6) C27 0.0161(7) 0.0183(8) 0.0222(8) 0.0015(6) 0.0057(6) -0.0004(6) C28 0.0210(8) 0.0222(8) 0.0183(8) 0.0002(6) 0.0083(6) 0.0039(6) C29 0.0272(9) 0.0243(9) 0.0206(9) 0.0007(6) 0.0087(7) 0.0040(7) C30 0.0311(11) 0.0316(10) 0.0346(11) -0.0015(8) 0.0147(9) -0.0024(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 O2 1.8899(13) . ? Cu1 O1 1.8980(13) . ? Cu1 N2 2.0007(14) . ? Cu1 N1 2.0126(14) . ? O1 C1 1.303(2) . ? O2 C21 1.302(2) . ? N1 C7 1.291(2) . ? N1 C8 1.481(2) . ? N2 C27 1.290(2) . ? N2 C28 1.482(2) . ? C1 C2 1.417(3) . ? C1 C6 1.423(2) . ? C2 C3 1.376(3) . ? C2 H2 0.9500 . ? C3 C4 1.397(3) . ? C3 H3 0.9500 . ? C4 C5 1.376(3) . ? C4 H4 0.9500 . ? C5 C6 1.408(2) . ? C5 H5 0.9500 . ? C6 C7 1.442(2) . ? C7 H7 0.9500 . ? C8 C9 1.494(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.316(3) . ? C9 H9 0.9500 . ? C10 H10A 0.9500 . ? C10 H10B 0.9500 . ? C21 C22 1.421(2) . ? C21 C26 1.422(2) . ? C22 C23 1.376(3) . ? C22 H22 0.9500 . ? C23 C24 1.399(3) . ? C23 H23 0.9500 . ? C24 C25 1.375(3) . ? C24 H24 0.9500 . ? C25 C26 1.409(2) . ? C25 H25 0.9500 . ? C26 C27 1.438(2) . ? C27 H27 0.9500 . ? C28 C29 1.498(2) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.325(3) . ? C29 H29 0.9500 . ? C30 H30A 0.9500 . ? C30 H30B 0.9500 . ? 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 O1 176.43(6) . . ? O2 Cu1 N2 92.57(6) . . ? O1 Cu1 N2 88.25(6) . . ? O2 Cu1 N1 88.05(5) . . ? O1 Cu1 N1 91.19(6) . . ? N2 Cu1 N1 178.78(6) . . ? C1 O1 Cu1 130.05(12) . . ? C21 O2 Cu1 129.86(11) . . ? C7 N1 C8 115.05(14) . . ? C7 N1 Cu1 124.44(12) . . ? C8 N1 Cu1 120.35(10) . . ? C27 N2 C28 115.41(14) . . ? C27 N2 Cu1 123.62(11) . . ? C28 N2 Cu1 120.93(10) . . ? O1 C1 C2 119.21(16) . . ? O1 C1 C6 123.45(16) . . ? C2 C1 C6 117.32(16) . . ? C3 C2 C1 121.39(18) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 121.02(17) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 119.00(16) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.46(17) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 119.79(16) . . ? C5 C6 C7 117.96(15) . . ? C1 C6 C7 122.25(15) . . ? N1 C7 C6 126.87(15) . . ? N1 C7 H7 116.6 . . ? C6 C7 H7 116.6 . . ? N1 C8 C9 111.56(14) . . ? N1 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N1 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C10 C9 C8 123.79(19) . . ? C10 C9 H9 118.1 . . ? C8 C9 H9 118.1 . . ? C9 C10 H10A 120.0 . . ? C9 C10 H10B 120.0 . . ? H10A C10 H10B 120.0 . . ? O2 C21 C22 119.32(15) . . ? O2 C21 C26 123.67(15) . . ? C22 C21 C26 117.01(15) . . ? C23 C22 C21 121.52(17) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C22 C23 C24 121.20(16) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.4 . . ? C25 C24 C23 118.46(16) . . ? C25 C24 H24 120.8 . . ? C23 C24 H24 120.8 . . ? C24 C25 C26 122.04(17) . . ? C24 C25 H25 119.0 . . ? C26 C25 H25 119.0 . . ? C25 C26 C21 119.73(16) . . ? C25 C26 C27 118.01(15) . . ? C21 C26 C27 122.27(15) . . ? N2 C27 C26 127.55(15) . . ? N2 C27 H27 116.2 . . ? C26 C27 H27 116.2 . . ? N2 C28 C29 111.84(14) . . ? N2 C28 H28A 109.2 . . ? C29 C28 H28A 109.2 . . ? N2 C28 H28B 109.2 . . ? C29 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? C30 C29 C28 123.66(18) . . ? C30 C29 H29 118.2 . . ? C28 C29 H29 118.2 . . ? C29 C30 H30A 120.0 . . ? C29 C30 H30B 120.0 . . ? H30A C30 H30B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.336 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.066