# 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 _publ_contact_author_name 'Thorsten Glaser' _publ_contact_author_address ; Department of Chemistry Lehrstuhl Anorganische Chemie I Universitaet Bielefeld Universitaetsstr. 25 Bielefeld 33615 GERMANY ; _publ_contact_author_email THORSTEN.GLASER@UNI-BIELEFELD.DE _publ_section_title ; Direct influence of hydrogen-bonding on the reduction potential of a CuII center ; loop_ _publ_author_name 'Thorsten Glaser' 'Roland Frohlich' 'Stefan Grimme' 'Olga M Kataeva' 'Ioannis Liratzis' 'Manuel Piacenza' # Attachment 'B517340J_revised.cif' #========================================================================== data_noabs _database_code_depnum_ccdc_archive 'CCDC 273718' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H20 Cu N2 O4' _chemical_formula_weight 475.97 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 monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.210(2) _cell_length_b 10.2458(11) _cell_length_c 17.7739(19) _cell_angle_alpha 90.00 _cell_angle_beta 100.842(2) _cell_angle_gamma 90.00 _cell_volume 3972.4(7) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1960 _exptl_absorpt_coefficient_mu 1.138 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS APEX' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18963 _diffrn_reflns_av_R_equivalents 0.0723 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4547 _reflns_number_gt 3271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker AXS, 2000)' _computing_cell_refinement 'SMART (Bruker AXS, 2000)' _computing_data_reduction 'SAINT (Bruker AXS, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 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^)+(0.0182P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4547 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0674 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.914 _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 Cu Cu 0.496939(11) 0.69016(2) 0.049972(14) 0.02637(9) Uani 1 1 d . . . N1 N 0.42980(8) 0.77819(17) -0.01818(10) 0.0269(4) Uani 1 1 d . . . N2 N 0.45286(8) 0.53500(17) 0.07303(10) 0.0305(4) Uani 1 1 d . . . O1 O 0.55774(6) 0.78881(13) 0.01122(8) 0.0277(3) Uani 1 1 d . . . O3 O 0.56367(7) 0.65209(13) 0.13290(8) 0.0301(4) Uani 1 1 d . . . C1 C 0.49449(10) 0.9223(2) -0.07972(12) 0.0266(5) Uani 1 1 d . . . C2 C 0.55145(10) 0.87578(19) -0.04366(12) 0.0237(5) Uani 1 1 d . . . C3 C 0.60642(10) 0.92389(19) -0.06708(12) 0.0251(5) Uani 1 1 d . . . C4 C 0.66538(10) 0.8790(2) -0.03375(13) 0.0291(5) Uani 1 1 d . . . C5 C 0.71625(11) 0.9225(2) -0.06028(15) 0.0361(6) Uani 1 1 d . . . C6 C 0.71017(13) 1.0112(2) -0.11973(15) 0.0395(6) Uani 1 1 d . . . C7 C 0.65418(13) 1.0589(2) -0.15206(15) 0.0372(6) Uani 1 1 d . . . C8 C 0.60107(10) 1.0186(2) -0.12664(12) 0.0293(5) Uani 1 1 d . . . C9 C 0.54242(12) 1.0671(2) -0.15849(14) 0.0355(6) Uani 1 1 d . . . C10 C 0.49146(12) 1.0215(2) -0.13654(13) 0.0333(6) Uani 1 1 d . . . C11 C 0.43826(10) 0.8716(2) -0.06338(13) 0.0286(5) Uani 1 1 d . . . C12 C 0.36432(11) 0.7451(3) -0.02045(16) 0.0374(6) Uani 1 1 d . . . C13 C 0.35417(12) 0.6459(3) 0.03894(16) 0.0409(6) Uani 1 1 d . . . C14 C 0.38811(11) 0.5198(3) 0.03592(16) 0.0377(6) Uani 1 1 d . . . C15 C 0.47695(11) 0.4433(2) 0.11818(13) 0.0316(5) Uani 1 1 d . . . C16 C 0.53731(10) 0.4359(2) 0.16328(12) 0.0278(5) Uani 1 1 d . . . C17 C 0.57750(9) 0.5435(2) 0.17102(11) 0.0247(5) Uani 1 1 d . . . C18 C 0.63543(10) 0.5342(2) 0.22294(11) 0.0257(5) Uani 1 1 d . . . C19 C 0.67703(10) 0.6409(2) 0.23533(12) 0.0263(5) Uani 1 1 d . . . C20 C 0.73135(11) 0.6305(2) 0.28628(14) 0.0332(6) Uani 1 1 d . . . C21 C 0.74708(12) 0.5157(2) 0.32546(14) 0.0390(6) Uani 1 1 d . . . C22 C 0.70856(12) 0.4099(2) 0.31474(14) 0.0367(6) Uani 1 1 d . . . C23 C 0.65261(10) 0.4163(2) 0.26380(12) 0.0295(5) Uani 1 1 d . . . C24 C 0.61115(12) 0.3091(2) 0.25162(13) 0.0347(6) Uani 1 1 d . . . C25 C 0.55647(11) 0.3201(2) 0.20473(13) 0.0320(5) Uani 1 1 d . . . H5 H 0.7498(9) 0.887(2) -0.0386(12) 0.023(6) Uiso 1 1 d . . . H6 H 0.7430(10) 1.035(2) -0.1399(12) 0.038(7) Uiso 1 1 d . . . H7 H 0.6509(10) 1.111(2) -0.1874(13) 0.036(7) Uiso 1 1 d . . . H9 H 0.5403(10) 1.128(2) -0.1934(13) 0.039(7) Uiso 1 1 d . . . H10 H 0.4541(9) 1.0521(18) -0.1555(11) 0.021(6) Uiso 1 1 d . . . H11 H 0.4050(9) 0.9151(19) -0.0926(12) 0.027(6) Uiso 1 1 d . . . H12A H 0.3486(10) 0.707(2) -0.0726(13) 0.039(7) Uiso 1 1 d . . . H12B H 0.3437(10) 0.825(2) -0.0121(13) 0.047(7) Uiso 1 1 d . . . H13A H 0.3673(11) 0.684(2) 0.0939(15) 0.055(7) Uiso 1 1 d . . . H13B H 0.3122(11) 0.631(2) 0.0337(12) 0.039(7) Uiso 1 1 d . . . H14A H 0.3695(10) 0.454(2) 0.0642(13) 0.039(7) Uiso 1 1 d . . . H14B H 0.3847(11) 0.506(2) -0.0228(14) 0.051(7) Uiso 1 1 d . . . H15 H 0.4521(9) 0.369(2) 0.1247(12) 0.030(6) Uiso 1 1 d . . . H20 H 0.7548(10) 0.6978(19) 0.2923(12) 0.027(6) Uiso 1 1 d . . . H21 H 0.7830(11) 0.508(2) 0.3605(12) 0.039(7) Uiso 1 1 d . . . H22 H 0.7196(10) 0.339(2) 0.3425(13) 0.035(7) Uiso 1 1 d . . . H24 H 0.6223(10) 0.235(2) 0.2760(13) 0.040(7) Uiso 1 1 d . . . H25 H 0.5314(9) 0.2548(19) 0.1965(11) 0.021(6) Uiso 1 1 d . . . O2 O 0.67394(8) 0.79245(16) 0.02455(10) 0.0389(4) Uani 1 1 d . . . O4 O 0.66354(8) 0.75552(15) 0.19762(10) 0.0329(4) Uani 1 1 d . . . H2A H 0.6422(10) 0.779(2) 0.0382(12) 0.028(7) Uiso 1 1 d . . . H4A H 0.6332(11) 0.743(2) 0.1663(14) 0.031(7) Uiso 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 Cu 0.02255(14) 0.02856(15) 0.02765(15) 0.00077(13) 0.00385(11) -0.00361(12) N1 0.0216(10) 0.0317(11) 0.0264(10) -0.0046(8) 0.0024(8) -0.0019(8) N2 0.0278(11) 0.0331(11) 0.0315(11) -0.0006(9) 0.0078(9) -0.0078(9) O1 0.0230(8) 0.0280(8) 0.0320(8) 0.0068(7) 0.0048(7) -0.0006(6) O3 0.0318(8) 0.0248(8) 0.0316(9) 0.0055(7) 0.0004(7) -0.0057(7) C1 0.0317(13) 0.0257(12) 0.0212(11) -0.0044(9) 0.0018(10) 0.0001(10) C2 0.0282(12) 0.0203(11) 0.0219(11) -0.0061(9) 0.0025(9) -0.0010(9) C3 0.0331(13) 0.0201(11) 0.0231(11) -0.0048(9) 0.0081(10) -0.0024(9) C4 0.0316(13) 0.0213(11) 0.0355(13) -0.0017(10) 0.0091(11) 0.0007(10) C5 0.0304(14) 0.0288(13) 0.0509(16) -0.0024(12) 0.0123(13) 0.0003(11) C6 0.0413(16) 0.0339(14) 0.0493(16) -0.0061(12) 0.0241(14) -0.0094(12) C7 0.0542(18) 0.0284(14) 0.0320(14) 0.0011(12) 0.0162(13) -0.0078(12) C8 0.0385(14) 0.0260(12) 0.0230(12) -0.0058(10) 0.0050(10) -0.0014(10) C9 0.0481(16) 0.0301(14) 0.0261(13) 0.0042(11) 0.0009(12) -0.0028(12) C10 0.0378(15) 0.0324(14) 0.0257(13) -0.0014(11) -0.0044(11) 0.0025(12) C11 0.0252(13) 0.0328(13) 0.0243(12) -0.0057(10) -0.0043(10) 0.0060(10) C12 0.0221(13) 0.0431(15) 0.0453(16) -0.0052(13) 0.0018(11) 0.0008(11) C13 0.0244(14) 0.0495(16) 0.0503(17) -0.0109(14) 0.0108(12) -0.0088(12) C14 0.0313(14) 0.0410(15) 0.0405(16) -0.0036(13) 0.0060(12) -0.0127(12) C15 0.0384(14) 0.0305(13) 0.0304(13) -0.0077(11) 0.0178(11) -0.0114(11) C16 0.0354(13) 0.0255(12) 0.0249(12) -0.0030(10) 0.0117(10) -0.0040(10) C17 0.0299(12) 0.0240(12) 0.0218(11) -0.0024(9) 0.0088(9) -0.0003(9) C18 0.0323(13) 0.0247(11) 0.0227(11) -0.0022(9) 0.0121(10) 0.0042(10) C19 0.0294(12) 0.0247(11) 0.0257(12) -0.0025(10) 0.0077(10) 0.0035(10) C20 0.0299(13) 0.0345(14) 0.0345(14) -0.0043(11) 0.0045(11) -0.0020(12) C21 0.0334(15) 0.0461(16) 0.0349(14) 0.0007(12) 0.0001(12) 0.0103(13) C22 0.0427(15) 0.0333(14) 0.0344(14) 0.0051(12) 0.0082(12) 0.0153(12) C23 0.0375(13) 0.0257(12) 0.0281(12) -0.0009(10) 0.0132(11) 0.0077(10) C24 0.0532(16) 0.0238(12) 0.0298(13) 0.0035(12) 0.0144(12) 0.0081(13) C25 0.0447(15) 0.0230(12) 0.0318(13) -0.0072(11) 0.0165(12) -0.0082(12) O2 0.0246(9) 0.0379(10) 0.0553(11) 0.0168(8) 0.0100(8) 0.0028(8) O4 0.0333(10) 0.0282(9) 0.0335(10) 0.0014(7) -0.0028(8) -0.0055(7) _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 Cu O1 1.9155(14) . ? Cu O3 1.9233(15) . ? Cu N2 1.9506(17) . ? Cu N1 1.9556(18) . ? N1 C11 1.286(3) . ? N1 C12 1.486(3) . ? N2 C15 1.285(3) . ? N2 C14 1.473(3) . ? O1 C2 1.309(2) . ? O3 C17 1.309(2) . ? C1 C2 1.390(3) . ? C1 C10 1.426(3) . ? C1 C11 1.432(3) . ? C2 C3 1.449(3) . ? C3 C4 1.409(3) . ? C3 C8 1.424(3) . ? C4 O2 1.350(3) . ? C4 C5 1.378(3) . ? C5 C6 1.381(3) . ? C5 H5 0.854(19) . ? C6 C7 1.359(4) . ? C6 H6 0.91(2) . ? C7 C8 1.403(3) . ? C7 H7 0.82(2) . ? C8 C9 1.410(3) . ? C9 C10 1.348(3) . ? C9 H9 0.88(2) . ? C10 H10 0.893(19) . ? C11 H11 0.93(2) . ? C12 C13 1.513(4) . ? C12 H12A 1.01(2) . ? C12 H12B 0.97(2) . ? C13 C14 1.501(3) . ? C13 H13A 1.04(3) . ? C13 H13B 0.93(2) . ? C14 H14A 0.98(2) . ? C14 H14B 1.04(2) . ? C15 C16 1.429(3) . ? C15 H15 0.96(2) . ? C16 C17 1.409(3) . ? C16 C25 1.419(3) . ? C17 C18 1.439(3) . ? C18 C19 1.421(3) . ? C18 C23 1.424(3) . ? C19 O4 1.357(2) . ? C19 C20 1.370(3) . ? C20 C21 1.378(3) . ? C20 H20 0.86(2) . ? C21 C22 1.372(3) . ? C21 H21 0.92(2) . ? C22 C23 1.395(3) . ? C22 H22 0.88(2) . ? C23 C24 1.423(3) . ? C24 C25 1.342(3) . ? C24 H24 0.88(2) . ? C25 H25 0.865(19) . ? O2 H2A 0.80(2) . ? O4 H4A 0.80(2) . ? 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 Cu O3 83.62(6) . . ? O1 Cu N2 157.10(7) . . ? O3 Cu N2 91.06(7) . . ? O1 Cu N1 92.34(7) . . ? O3 Cu N1 162.94(6) . . ? N2 Cu N1 98.72(8) . . ? C11 N1 C12 114.19(19) . . ? C11 N1 Cu 123.11(15) . . ? C12 N1 Cu 122.68(15) . . ? C15 N2 C14 117.34(19) . . ? C15 N2 Cu 124.10(16) . . ? C14 N2 Cu 118.56(15) . . ? C2 O1 Cu 130.05(13) . . ? C17 O3 Cu 129.88(13) . . ? C2 C1 C10 119.2(2) . . ? C2 C1 C11 122.3(2) . . ? C10 C1 C11 118.4(2) . . ? O1 C2 C1 122.48(19) . . ? O1 C2 C3 117.92(19) . . ? C1 C2 C3 119.60(19) . . ? C4 C3 C8 118.43(19) . . ? C4 C3 C2 122.33(19) . . ? C8 C3 C2 119.2(2) . . ? O2 C4 C5 118.0(2) . . ? O2 C4 C3 121.52(19) . . ? C5 C4 C3 120.5(2) . . ? C4 C5 C6 120.4(2) . . ? C4 C5 H5 114.0(14) . . ? C6 C5 H5 125.5(14) . . ? C7 C6 C5 120.7(2) . . ? C7 C6 H6 118.3(14) . . ? C5 C6 H6 120.9(15) . . ? C6 C7 C8 121.1(2) . . ? C6 C7 H7 120.2(16) . . ? C8 C7 H7 118.7(16) . . ? C7 C8 C9 122.4(2) . . ? C7 C8 C3 118.8(2) . . ? C9 C8 C3 118.7(2) . . ? C10 C9 C8 121.6(2) . . ? C10 C9 H9 121.0(15) . . ? C8 C9 H9 117.4(15) . . ? C9 C10 C1 121.5(2) . . ? C9 C10 H10 122.8(13) . . ? C1 C10 H10 115.8(13) . . ? N1 C11 C1 129.2(2) . . ? N1 C11 H11 120.7(12) . . ? C1 C11 H11 110.1(12) . . ? N1 C12 C13 114.1(2) . . ? N1 C12 H12A 106.4(13) . . ? C13 C12 H12A 107.9(12) . . ? N1 C12 H12B 107.0(13) . . ? C13 C12 H12B 109.1(14) . . ? H12A C12 H12B 112.5(19) . . ? C14 C13 C12 114.3(2) . . ? C14 C13 H13A 107.8(13) . . ? C12 C13 H13A 110.3(13) . . ? C14 C13 H13B 110.9(14) . . ? C12 C13 H13B 108.5(14) . . ? H13A C13 H13B 104.7(19) . . ? N2 C14 C13 110.35(19) . . ? N2 C14 H14A 108.3(13) . . ? C13 C14 H14A 108.0(13) . . ? N2 C14 H14B 110.1(13) . . ? C13 C14 H14B 101.9(13) . . ? H14A C14 H14B 117.8(18) . . ? N2 C15 C16 128.8(2) . . ? N2 C15 H15 118.4(13) . . ? C16 C15 H15 112.9(13) . . ? C17 C16 C25 118.8(2) . . ? C17 C16 C15 121.5(2) . . ? C25 C16 C15 119.6(2) . . ? O3 C17 C16 122.15(19) . . ? O3 C17 C18 118.88(18) . . ? C16 C17 C18 118.97(19) . . ? C19 C18 C23 118.0(2) . . ? C19 C18 C17 121.69(19) . . ? C23 C18 C17 120.32(19) . . ? O4 C19 C20 118.6(2) . . ? O4 C19 C18 120.80(19) . . ? C20 C19 C18 120.6(2) . . ? C19 C20 C21 120.6(2) . . ? C19 C20 H20 117.3(14) . . ? C21 C20 H20 122.1(14) . . ? C22 C21 C20 120.8(2) . . ? C22 C21 H21 117.8(14) . . ? C20 C21 H21 121.4(14) . . ? C21 C22 C23 120.6(2) . . ? C21 C22 H22 117.9(15) . . ? C23 C22 H22 121.4(15) . . ? C22 C23 C24 122.3(2) . . ? C22 C23 C18 119.4(2) . . ? C24 C23 C18 118.3(2) . . ? C25 C24 C23 120.9(2) . . ? C25 C24 H24 120.9(15) . . ? C23 C24 H24 118.2(15) . . ? C24 C25 C16 122.7(2) . . ? C24 C25 H25 121.2(14) . . ? C16 C25 H25 116.0(14) . . ? C4 O2 H2A 109.9(16) . . ? C19 O4 H4A 106.6(16) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.594 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.057 #========================================================================== data_han2709 _database_code_depnum_ccdc_archive 'CCDC 273719' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H20 Cu N2 O2' _chemical_formula_weight 443.97 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 monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.060(1) _cell_length_b 10.158(1) _cell_length_c 17.598(1) _cell_angle_alpha 90.00 _cell_angle_beta 100.97(1) _cell_angle_gamma 90.00 _cell_volume 3871.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1832 _exptl_absorpt_coefficient_mu 1.154 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6554 _exptl_absorpt_correction_T_max 0.9340 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995 & 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15324 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 27.90 _reflns_number_total 4601 _reflns_number_gt 3542 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 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^)+(0.0390P)^2^+4.0965P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4601 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0938 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Cu Cu 0.506228(12) 0.69076(3) 0.056463(14) 0.02784(10) Uani 1 1 d . . . O1 O 0.57217(7) 0.65744(15) 0.14238(9) 0.0338(4) Uani 1 1 d . . . O2 O 0.56718(7) 0.78716(15) 0.01579(9) 0.0314(4) Uani 1 1 d . . . N1 N 0.46134(8) 0.53340(18) 0.07872(10) 0.0302(4) Uani 1 1 d . . . N2 N 0.43740(8) 0.77524(18) -0.01448(10) 0.0283(4) Uani 1 1 d . . . C1 C 0.54653(10) 0.4372(2) 0.17122(12) 0.0281(5) Uani 1 1 d . . . C2 C 0.58597(10) 0.5473(2) 0.17884(11) 0.0275(5) Uani 1 1 d . . . C3 C 0.64542(10) 0.5375(2) 0.23094(11) 0.0264(5) Uani 1 1 d . . . C4 C 0.68692(11) 0.6436(2) 0.24017(12) 0.0310(5) Uani 1 1 d . . . H4 H 0.6762 0.7222 0.2115 0.037 Uiso 1 1 calc R . . C5 C 0.74265(11) 0.6353(3) 0.29004(13) 0.0368(5) Uani 1 1 d . . . H5 H 0.7701 0.7082 0.2961 0.044 Uiso 1 1 calc R . . C6 C 0.75916(11) 0.5197(3) 0.33209(14) 0.0390(6) Uani 1 1 d . . . H6 H 0.7977 0.5145 0.3668 0.047 Uiso 1 1 calc R . . C7 C 0.71999(11) 0.4141(2) 0.32337(13) 0.0360(5) Uani 1 1 d . . . H7 H 0.7319 0.3360 0.3521 0.043 Uiso 1 1 calc R . . C8 C 0.66235(10) 0.4189(2) 0.27258(12) 0.0291(5) Uani 1 1 d . . . C9 C 0.62113(11) 0.3094(2) 0.26202(13) 0.0328(5) Uani 1 1 d . . . H9 H 0.6325 0.2294 0.2889 0.039 Uiso 1 1 calc R . . C10 C 0.56593(11) 0.3197(2) 0.21366(12) 0.0318(5) Uani 1 1 d . . . H10 H 0.5389 0.2460 0.2076 0.038 Uiso 1 1 calc R . . C11 C 0.48602(11) 0.4405(2) 0.12486(12) 0.0313(5) Uani 1 1 d . . . H11 H 0.4608 0.3657 0.1282 0.038 Uiso 1 1 calc R . . C12 C 0.39639(10) 0.5159(2) 0.04110(14) 0.0342(5) Uani 1 1 d . . . H12A H 0.3774 0.4458 0.0680 0.041 Uiso 1 1 calc R . . H12B H 0.3941 0.4885 -0.0134 0.041 Uiso 1 1 calc R . . C13 C 0.36128(11) 0.6433(2) 0.04355(14) 0.0362(5) Uani 1 1 d . . . H13A H 0.3166 0.6234 0.0368 0.043 Uiso 1 1 calc R . . H13B H 0.3743 0.6843 0.0951 0.043 Uiso 1 1 calc R . . C14 C 0.37126(10) 0.7403(3) -0.01786(14) 0.0358(5) Uani 1 1 d . . . H14A H 0.3544 0.7026 -0.0694 0.043 Uiso 1 1 calc R . . H14B H 0.3478 0.8217 -0.0122 0.043 Uiso 1 1 calc R . . C15 C 0.44570(10) 0.8682(2) -0.06204(12) 0.0302(5) Uani 1 1 d . . . H15 H 0.4092 0.9082 -0.0899 0.036 Uiso 1 1 calc R . . C16 C 0.50253(10) 0.9184(2) -0.07802(12) 0.0282(5) Uani 1 1 d . . . C17 C 0.56016(10) 0.8723(2) -0.03977(11) 0.0259(5) Uani 1 1 d . . . C18 C 0.61488(10) 0.9222(2) -0.06387(12) 0.0281(5) Uani 1 1 d . . . C19 C 0.67387(10) 0.8773(2) -0.02808(14) 0.0331(5) Uani 1 1 d . . . H19 H 0.6777 0.8153 0.0130 0.040 Uiso 1 1 calc R . . C20 C 0.72572(11) 0.9222(2) -0.05183(15) 0.0406(6) Uani 1 1 d . . . H20 H 0.7652 0.8918 -0.0268 0.049 Uiso 1 1 calc R . . C21 C 0.72099(13) 1.0125(3) -0.11280(16) 0.0452(6) Uani 1 1 d . . . H21 H 0.7571 1.0420 -0.1297 0.054 Uiso 1 1 calc R . . C22 C 0.66415(12) 1.0580(2) -0.14799(14) 0.0402(6) Uani 1 1 d . . . H22 H 0.6614 1.1195 -0.1892 0.048 Uiso 1 1 calc R . . C23 C 0.60981(11) 1.0161(2) -0.12463(12) 0.0321(5) Uani 1 1 d . . . C24 C 0.55057(12) 1.0648(2) -0.15887(13) 0.0376(6) Uani 1 1 d . . . H24 H 0.5469 1.1308 -0.1977 0.045 Uiso 1 1 calc R . . C25 C 0.49932(11) 1.0174(2) -0.13642(12) 0.0352(5) Uani 1 1 d . . . H25 H 0.4601 1.0510 -0.1602 0.042 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 Cu 0.02745(16) 0.02577(16) 0.02899(15) 0.00435(11) 0.00203(11) -0.00358(11) O1 0.0356(9) 0.0270(8) 0.0345(8) 0.0085(7) -0.0043(7) -0.0065(7) O2 0.0279(8) 0.0291(9) 0.0361(8) 0.0101(6) 0.0030(7) -0.0024(6) N1 0.0295(10) 0.0289(10) 0.0312(9) 0.0003(8) 0.0036(8) -0.0053(8) N2 0.0249(10) 0.0287(10) 0.0305(9) -0.0018(8) 0.0035(8) -0.0022(8) C1 0.0343(12) 0.0263(12) 0.0244(10) -0.0002(9) 0.0072(9) -0.0047(9) C2 0.0339(12) 0.0265(12) 0.0223(10) -0.0003(8) 0.0063(9) -0.0010(9) C3 0.0309(12) 0.0253(11) 0.0239(10) -0.0002(8) 0.0077(9) 0.0007(9) C4 0.0362(13) 0.0282(12) 0.0289(11) -0.0010(9) 0.0069(10) -0.0009(10) C5 0.0355(13) 0.0375(14) 0.0365(12) -0.0025(10) 0.0049(10) -0.0056(11) C6 0.0338(13) 0.0438(15) 0.0362(12) -0.0007(11) -0.0016(10) 0.0014(11) C7 0.0381(13) 0.0330(13) 0.0360(12) 0.0041(10) 0.0045(10) 0.0076(11) C8 0.0351(13) 0.0271(12) 0.0261(10) -0.0013(9) 0.0082(9) 0.0030(10) C9 0.0437(14) 0.0231(12) 0.0324(11) 0.0034(9) 0.0093(10) 0.0020(10) C10 0.0419(14) 0.0239(12) 0.0306(11) -0.0004(9) 0.0094(10) -0.0065(10) C11 0.0394(13) 0.0267(12) 0.0288(11) -0.0026(9) 0.0089(10) -0.0088(10) C12 0.0300(12) 0.0316(13) 0.0399(12) -0.0018(10) 0.0042(10) -0.0071(10) C13 0.0268(12) 0.0392(14) 0.0437(13) -0.0036(11) 0.0096(10) -0.0059(10) C14 0.0262(12) 0.0359(14) 0.0440(13) 0.0004(11) 0.0034(10) -0.0012(10) C15 0.0294(12) 0.0288(12) 0.0298(11) -0.0019(9) -0.0012(9) 0.0028(10) C16 0.0314(12) 0.0256(12) 0.0260(10) -0.0003(9) 0.0016(9) -0.0018(9) C17 0.0307(12) 0.0227(11) 0.0237(10) -0.0025(8) 0.0042(9) -0.0025(9) C18 0.0350(12) 0.0218(11) 0.0283(10) -0.0059(8) 0.0076(9) -0.0048(9) C19 0.0314(12) 0.0256(12) 0.0426(13) -0.0023(10) 0.0080(10) -0.0013(10) C20 0.0319(13) 0.0319(14) 0.0590(16) -0.0062(12) 0.0111(11) -0.0016(10) C21 0.0438(15) 0.0411(16) 0.0569(16) -0.0105(13) 0.0253(13) -0.0126(12) C22 0.0557(17) 0.0332(14) 0.0358(12) -0.0015(10) 0.0186(12) -0.0120(12) C23 0.0419(14) 0.0292(12) 0.0262(11) -0.0051(9) 0.0092(10) -0.0068(10) C24 0.0506(15) 0.0346(14) 0.0255(11) 0.0064(10) 0.0021(10) -0.0079(11) C25 0.0387(13) 0.0363(14) 0.0270(11) 0.0047(10) -0.0027(10) 0.0007(11) _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 Cu O2 1.9092(15) . ? Cu O1 1.9182(15) . ? Cu N1 1.9588(18) . ? Cu N2 1.9695(18) . ? O1 C2 1.297(3) . ? O2 C17 1.292(3) . ? N1 C11 1.296(3) . ? N1 C12 1.470(3) . ? N2 C15 1.298(3) . ? N2 C14 1.492(3) . ? C1 C2 1.407(3) . ? C1 C11 1.426(3) . ? C1 C10 1.430(3) . ? C2 C3 1.454(3) . ? C3 C4 1.403(3) . ? C3 C8 1.423(3) . ? C4 C5 1.371(3) . ? C5 C6 1.399(3) . ? C6 C7 1.367(3) . ? C7 C8 1.409(3) . ? C8 C9 1.427(3) . ? C9 C10 1.350(3) . ? C12 C13 1.513(3) . ? C13 C14 1.510(3) . ? C15 C16 1.430(3) . ? C16 C17 1.401(3) . ? C16 C25 1.430(3) . ? C17 C18 1.445(3) . ? C18 C19 1.409(3) . ? C18 C23 1.421(3) . ? C19 C20 1.368(3) . ? C20 C21 1.400(4) . ? C21 C22 1.369(4) . ? C22 C23 1.405(3) . ? C23 C24 1.420(3) . ? C24 C25 1.355(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 O2 Cu O1 84.46(7) . . ? O2 Cu N1 155.84(8) . . ? O1 Cu N1 91.99(7) . . ? O2 Cu N2 92.97(7) . . ? O1 Cu N2 162.56(7) . . ? N1 Cu N2 97.14(8) . . ? C2 O1 Cu 127.85(14) . . ? C17 O2 Cu 129.44(14) . . ? C11 N1 C12 116.83(19) . . ? C11 N1 Cu 123.48(16) . . ? C12 N1 Cu 119.68(14) . . ? C15 N2 C14 113.84(18) . . ? C15 N2 Cu 122.65(15) . . ? C14 N2 Cu 123.50(15) . . ? C2 C1 C11 122.1(2) . . ? C2 C1 C10 119.7(2) . . ? C11 C1 C10 118.2(2) . . ? O1 C2 C1 123.7(2) . . ? O1 C2 C3 117.99(19) . . ? C1 C2 C3 118.27(19) . . ? C4 C3 C8 119.3(2) . . ? C4 C3 C2 120.7(2) . . ? C8 C3 C2 120.0(2) . . ? C5 C4 C3 120.8(2) . . ? C4 C5 C6 120.1(2) . . ? C7 C6 C5 120.3(2) . . ? C6 C7 C8 121.2(2) . . ? C7 C8 C3 118.2(2) . . ? C7 C8 C9 122.1(2) . . ? C3 C8 C9 119.7(2) . . ? C10 C9 C8 119.8(2) . . ? C9 C10 C1 122.6(2) . . ? N1 C11 C1 127.7(2) . . ? N1 C12 C13 110.11(18) . . ? C14 C13 C12 113.1(2) . . ? N2 C14 C13 113.66(19) . . ? N2 C15 C16 128.5(2) . . ? C17 C16 C25 119.8(2) . . ? C17 C16 C15 122.4(2) . . ? C25 C16 C15 117.8(2) . . ? O2 C17 C16 123.7(2) . . ? O2 C17 C18 118.04(19) . . ? C16 C17 C18 118.28(19) . . ? C19 C18 C23 119.1(2) . . ? C19 C18 C17 120.5(2) . . ? C23 C18 C17 120.4(2) . . ? C20 C19 C18 120.7(2) . . ? C19 C20 C21 120.5(2) . . ? C22 C21 C20 119.8(2) . . ? C21 C22 C23 121.6(2) . . ? C22 C23 C24 122.5(2) . . ? C22 C23 C18 118.3(2) . . ? C24 C23 C18 119.2(2) . . ? C25 C24 C23 120.3(2) . . ? C24 C25 C16 122.0(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.366 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.065 #====================================================================== _eof