# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_publication_text _journal_name_full 'Dalton Trans.' #TrackingRef '- 1+2-crystaldata.CIF' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Christoph Janiak' _publ_contact_author_address ; Albertstr. 21 Freiburg D-79104 ; _publ_contact_author_email monfared@znu.ac.ir loop_ _publ_author_name _publ_author_address 'Hassan Hosseini Monfared' ; Departament of Chemistry Faculty of Sciences Zanjan University 45195-313 Zanjan Iran ; 'Morteza Vahedpour' ; Departament of Chemistry Faculty of Sciences Zanjan University 45195-313 Zanjan Iran ; 'Mahdi Mahdavi Yeganeh' ; Departament of Chemistry Faculty of Sciences Zanjan University 45195-313 Zanjan Iran ; 'Massomeh Ghorbanloo' ; Departament of Chemistry Faculty of Sciences Zanjan University 45195-313 Zanjan Iran ; 'Peter Mayer' ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus D) D-81377 M\"unchen Germany ; ; C.Janiak ; ; Institut f\u"r Anorganische und Analytische Chemie Universit\"at Freiburg Albertstr. 21 D-79104 Freiburg Germany ; _publ_section_title ; Concentration dependent tautomerism in green [Cu(HL^1^)(L^2^)] and brown [Cu(L^1^)(HL^2^)] with H2L^1^ = (E)-N'-(2-hydroxy-3-methoxybenzylidene)benzoylhydrazone and HL^2^ = pyridine-4-carboxylic acid ; #============================================================================== data_mn262a #?# MeasurementCode _database_code_depnum_ccdc_archive 'CCDC 720068' #TrackingRef '- 1+2-crystaldata.CIF' _audit_update_record 10-Feb-09 _chemical_name_common ? _chemical_compound_source ? _exptl_crystal_description platelet #?# e.g.: needle, platelet; _exptl_crystal_colour green _exptl_crystal_size_max 0.22 #?# in millimeters _exptl_crystal_size_mid 0.14 #?# in millimeters _exptl_crystal_size_min 0.04 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_author_name 'Mayer, P.' #?# X-ray operator _audit_creation_date 17-JUl-08 #?# style: 18-Aug-1998 _diffrn_ambient_temperature 200(2) #?# in K _diffrn_source_type 'FR 591 generator' _diffrn_source_power 3.025 #?# in kW _diffrn_source_voltage 55.00 #?# in kV _diffrn_source_current 55.00 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'MONTEL, graded multilayered X-ray optics' _diffrn_radiation_collimation 0.20 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD; rotation images; thick slices, phi/omega-scan' _diffrn_detector_area_resol_mean 9 _diffrn_special_details ? _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_UB_11 -0.0299929 _diffrn_orient_matrix_UB_12 -0.0000400 _diffrn_orient_matrix_UB_13 0.0698739 _diffrn_orient_matrix_UB_21 0.1355242 _diffrn_orient_matrix_UB_22 -0.0006570 _diffrn_orient_matrix_UB_23 0.0236057 _diffrn_orient_matrix_UB_31 0.0020746 _diffrn_orient_matrix_UB_32 0.0423369 _diffrn_orient_matrix_UB_33 0.0004324 loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _cell_length_a 13.6380(3) _cell_length_b 23.6172(5) _cell_length_c 7.24590(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.1919(12) _cell_angle_gamma 90.00 _cell_volume 2320.23(8) _cell_measurement_temperature 200(2) #?# in K _cell_measurement_reflns_used 47556 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 26.373 _cell_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.001000 0 0 -1 0.035000 5 -4 -1 0.108000 -5 2 1 0.111000 0 -1 0 0.064000 0 1 0 0.081000 -1 16 0 0.082000 _exptl_absorpt_coefficient_mu 0.991 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_reflns_number 17032 #xl _diffrn_reflns_av_R_equivalents 0.0420 #xl _diffrn_reflns_av_sigmaI/netI 0.0346 #xl _diffrn_reflns_limit_h_min -16 #xl _diffrn_reflns_limit_h_max 17 #xl _diffrn_reflns_limit_k_min -29 #xl _diffrn_reflns_limit_k_max 29 #xl _diffrn_reflns_limit_l_min -9 #xl _diffrn_reflns_limit_l_max 9 #xl _diffrn_reflns_theta_min 3.18 #xl _diffrn_reflns_theta_max 26.37 #xl _diffrn_measured_fraction_theta_max 0.998 #xl _diffrn_reflns_theta_full 26.37 #xl _diffrn_measured_fraction_theta_full 0.998 #xl _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' 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' _reflns_number_total 4735 #xl _reflns_number_gt 3757 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+1.2333P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 4735 #xl _refine_ls_number_parameters 325 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0511 #xl _refine_ls_R_factor_gt 0.0351 #xl _refine_ls_wR_factor_ref 0.0935 #xl _refine_ls_wR_factor_gt 0.0862 #xl _refine_ls_goodness_of_fit_ref 1.049 #xl _refine_ls_restrained_S_all 1.049 #xl _refine_ls_shift/su_max 0.001 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.398 #xl _refine_diff_density_min -0.505 #xl _refine_diff_density_rms 0.067 #xl _refine_special_details ; C-H: constr O-H and N-H: refall ; _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement 'SHELXL-97 (G. M. Sheldrick. University of G\"ottingen, 97-2 version)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.952577(19) 0.109099(11) 0.67780(4) 0.02802(10) Uani 1 1 d . . . O1 O 1.06324(11) 0.06880(6) 0.8232(2) 0.0330(4) Uani 1 1 d . . . O2 O 0.83604(11) 0.13840(6) 0.5482(2) 0.0330(4) Uani 1 1 d . . . O3 O 0.69364(13) 0.19958(8) 0.3925(3) 0.0468(4) Uani 1 1 d . . . O4 O 1.19604(13) 0.36427(8) 0.8546(3) 0.0508(5) Uani 1 1 d . . . O5 O 1.04755(11) 0.39007(6) 0.9252(2) 0.0313(4) Uani 1 1 d . . . O6 O 1.3757(3) 0.20094(15) 0.8617(4) 0.1051(12) Uani 1 1 d . . . H86 H 1.373(2) 0.2303(14) 0.835(4) 0.046(10) Uiso 1 1 d . . . O7 O 1.35686(18) 0.30828(12) 0.7317(4) 0.0631(6) Uani 1 1 d . . . H72 H 1.361(3) 0.3048(19) 0.633(6) 0.092(17) Uiso 1 1 d . . . H73 H 1.305(3) 0.3276(18) 0.757(5) 0.095(14) Uiso 1 1 d . . . N1 N 0.97316(14) -0.00713(8) 0.7205(3) 0.0282(4) Uani 1 1 d . . . H71 H 0.9653(19) -0.0429(13) 0.682(4) 0.044(8) Uiso 1 1 d . . . N2 N 0.90469(13) 0.03230(7) 0.6472(2) 0.0266(4) Uani 1 1 d . . . N3 N 1.00043(13) 0.18510(7) 0.7677(2) 0.0276(4) Uani 1 1 d . . . C1 C 1.05511(16) 0.01569(9) 0.8099(3) 0.0279(5) Uani 1 1 d . . . C2 C 1.13435(17) -0.02162(10) 0.8924(3) 0.0312(5) Uani 1 1 d . . . C3 C 1.22446(18) 0.00288(11) 0.9526(3) 0.0401(6) Uani 1 1 d . . . H3 H 1.2332 0.0426 0.9419 0.048 Uiso 1 1 calc R . . C4 C 1.3019(2) -0.03073(13) 1.0285(4) 0.0495(7) Uani 1 1 d . . . H4 H 1.3638 -0.0139 1.0686 0.059 Uiso 1 1 calc R . . C5 C 1.2897(2) -0.08802(13) 1.0461(4) 0.0495(7) Uani 1 1 d . . . H5 H 1.3431 -0.1107 1.0988 0.059 Uiso 1 1 calc R . . C6 C 1.1999(2) -0.11274(11) 0.9872(4) 0.0436(6) Uani 1 1 d . . . H6 H 1.1918 -0.1525 0.9993 0.052 Uiso 1 1 calc R . . C7 C 1.12214(19) -0.08010(10) 0.9111(3) 0.0361(5) Uani 1 1 d . . . H7 H 1.0604 -0.0972 0.8714 0.043 Uiso 1 1 calc R . . C8 C 0.81739(16) 0.01493(9) 0.5843(3) 0.0295(5) Uani 1 1 d . . . H8 H 0.8039 -0.0245 0.5881 0.035 Uiso 1 1 calc R . . C9 C 0.74035(16) 0.05193(10) 0.5096(3) 0.0300(5) Uani 1 1 d . . . C10 C 0.75432(16) 0.11090(10) 0.4947(3) 0.0291(5) Uani 1 1 d . . . C11 C 0.67217(17) 0.14350(10) 0.4133(3) 0.0339(5) Uani 1 1 d . . . C12 C 0.58185(18) 0.11865(12) 0.3621(3) 0.0412(6) Uani 1 1 d . . . H12 H 0.5278 0.1413 0.3120 0.049 Uiso 1 1 calc R . . C13 C 0.56942(19) 0.06052(12) 0.3835(4) 0.0457(6) Uani 1 1 d . . . H13 H 0.5068 0.0437 0.3495 0.055 Uiso 1 1 calc R . . C14 C 0.64703(17) 0.02781(11) 0.4530(3) 0.0393(6) Uani 1 1 d . . . H14 H 0.6383 -0.0119 0.4636 0.047 Uiso 1 1 calc R . . C15 C 0.6199(2) 0.23329(14) 0.2898(5) 0.0626(8) Uani 1 1 d . . . H15A H 0.6006 0.2155 0.1691 0.094 Uiso 1 1 calc R . . H15B H 0.6463 0.2712 0.2709 0.094 Uiso 1 1 calc R . . H15C H 0.5622 0.2363 0.3589 0.094 Uiso 1 1 calc R . . C16 C 1.09590(17) 0.19410(9) 0.8241(3) 0.0327(5) Uani 1 1 d . . . H16 H 1.1392 0.1625 0.8380 0.039 Uiso 1 1 calc R . . C17 C 1.13400(17) 0.24756(9) 0.8631(3) 0.0318(5) Uani 1 1 d . . . H17 H 1.2025 0.2525 0.8993 0.038 Uiso 1 1 calc R . . C18 C 1.07117(16) 0.29402(9) 0.8490(3) 0.0272(5) Uani 1 1 d . . . C19 C 0.97148(16) 0.28398(9) 0.7998(3) 0.0304(5) Uani 1 1 d . . . H19 H 0.9257 0.3144 0.7960 0.036 Uiso 1 1 calc R . . C20 C 0.93917(16) 0.22992(9) 0.7567(3) 0.0297(5) Uani 1 1 d . . . H20 H 0.8712 0.2240 0.7178 0.036 Uiso 1 1 calc R . . C21 C 1.10975(17) 0.35381(9) 0.8794(3) 0.0309(5) Uani 1 1 d . . . C22 C 1.4095(4) 0.1627(2) 0.7354(6) 0.0930(13) Uani 1 1 d . . . H22A H 1.4704 0.1777 0.6902 0.112 Uiso 1 1 calc R . . H22B H 1.3591 0.1584 0.6273 0.112 Uiso 1 1 calc R . . C23 C 1.4296(4) 0.10831(19) 0.8219(8) 0.1122(17) Uani 1 1 d . . . H23A H 1.4857 0.1117 0.9179 0.168 Uiso 1 1 calc R . . H23B H 1.4454 0.0809 0.7280 0.168 Uiso 1 1 calc R . . H23C H 1.3714 0.0955 0.8784 0.168 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 0.03327(17) 0.01670(15) 0.03346(16) -0.00084(11) 0.00077(11) -0.00201(11) O1 0.0390(9) 0.0203(8) 0.0387(9) 0.0008(7) -0.0007(7) -0.0010(7) O2 0.0321(8) 0.0235(8) 0.0424(9) 0.0001(7) -0.0007(7) -0.0041(7) O3 0.0423(10) 0.0353(10) 0.0602(12) 0.0079(9) -0.0057(8) 0.0058(8) O4 0.0378(10) 0.0304(10) 0.0869(14) -0.0090(10) 0.0181(9) -0.0064(8) O5 0.0384(9) 0.0173(8) 0.0395(9) -0.0007(6) 0.0097(7) 0.0009(6) O6 0.146(3) 0.091(2) 0.089(2) 0.0317(19) 0.064(2) 0.053(2) O7 0.0506(13) 0.0779(17) 0.0631(16) -0.0020(13) 0.0160(11) 0.0097(11) N1 0.0350(11) 0.0181(9) 0.0321(10) -0.0003(8) 0.0066(8) 0.0024(8) N2 0.0333(10) 0.0180(9) 0.0295(9) -0.0004(8) 0.0082(7) 0.0012(8) N3 0.0336(10) 0.0190(9) 0.0303(9) -0.0006(7) 0.0035(8) -0.0005(8) C1 0.0353(12) 0.0235(11) 0.0262(11) 0.0010(9) 0.0087(9) 0.0011(9) C2 0.0380(13) 0.0304(12) 0.0265(11) 0.0024(9) 0.0095(9) 0.0057(10) C3 0.0363(13) 0.0403(15) 0.0440(14) 0.0081(12) 0.0056(11) -0.0007(11) C4 0.0364(14) 0.0615(19) 0.0503(16) 0.0121(14) 0.0039(11) 0.0039(13) C5 0.0480(16) 0.0569(18) 0.0441(15) 0.0104(14) 0.0079(12) 0.0219(14) C6 0.0585(17) 0.0354(14) 0.0370(13) 0.0020(11) 0.0048(12) 0.0140(12) C7 0.0473(14) 0.0275(13) 0.0338(12) -0.0001(10) 0.0061(10) 0.0047(10) C8 0.0353(12) 0.0224(11) 0.0320(11) -0.0020(9) 0.0094(9) -0.0045(9) C9 0.0321(12) 0.0292(12) 0.0297(11) -0.0036(9) 0.0075(9) -0.0044(9) C10 0.0321(12) 0.0308(12) 0.0252(11) -0.0030(9) 0.0062(9) -0.0024(10) C11 0.0338(12) 0.0351(13) 0.0334(12) -0.0001(10) 0.0057(10) 0.0009(10) C12 0.0305(12) 0.0533(17) 0.0392(13) -0.0007(12) 0.0005(10) 0.0031(11) C13 0.0299(13) 0.0552(18) 0.0518(15) -0.0047(13) 0.0031(11) -0.0091(12) C14 0.0346(13) 0.0385(14) 0.0451(14) -0.0040(12) 0.0064(10) -0.0112(11) C15 0.0592(19) 0.0522(19) 0.072(2) 0.0178(16) -0.0121(15) 0.0137(15) C16 0.0374(13) 0.0209(11) 0.0388(13) -0.0022(10) -0.0001(10) 0.0052(9) C17 0.0302(12) 0.0252(12) 0.0394(12) -0.0033(10) 0.0006(9) -0.0015(9) C18 0.0351(12) 0.0204(11) 0.0266(11) -0.0017(9) 0.0063(9) -0.0017(9) C19 0.0341(12) 0.0212(11) 0.0355(12) -0.0013(9) 0.0026(9) 0.0022(9) C20 0.0291(11) 0.0246(12) 0.0350(12) -0.0007(9) 0.0013(9) 0.0002(9) C21 0.0365(13) 0.0216(11) 0.0348(12) -0.0012(9) 0.0045(10) -0.0024(9) C22 0.109(3) 0.102(4) 0.068(2) -0.010(2) 0.011(2) 0.009(3) C23 0.124(4) 0.078(3) 0.140(4) -0.026(3) 0.038(3) -0.011(3) 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 1.8881(15) . ? Cu1 N2 1.9325(18) . ? Cu1 O1 1.9878(15) . ? Cu1 N3 1.9951(18) . ? Cu1 O5 2.3539(15) 4_565 ? O1 C1 1.262(3) . ? O2 C10 1.312(3) . ? O3 C11 1.368(3) . ? O3 C15 1.428(3) . ? O4 C21 1.234(3) . ? O5 C21 1.274(3) . ? O5 Cu1 2.3539(15) 4_566 ? O6 C22 1.399(5) . ? O6 H86 0.72(3) . ? O7 H72 0.73(4) . ? O7 H73 0.88(4) . ? N1 C1 1.343(3) . ? N1 N2 1.383(3) . ? N1 H71 0.89(3) . ? N2 C8 1.295(3) . ? N3 C16 1.339(3) . ? N3 C20 1.346(3) . ? C1 C2 1.471(3) . ? C2 C3 1.386(3) . ? C2 C7 1.399(3) . ? C3 C4 1.386(4) . ? C3 H3 0.9500 . ? C4 C5 1.371(4) . ? C4 H4 0.9500 . ? C5 C6 1.383(4) . ? C5 H5 0.9500 . ? C6 C7 1.377(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.428(3) . ? C8 H8 0.9500 . ? C9 C10 1.411(3) . ? C9 C14 1.414(3) . ? C10 C11 1.433(3) . ? C11 C12 1.379(3) . ? C12 C13 1.394(4) . ? C12 H12 0.9500 . ? C13 C14 1.362(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.383(3) . ? C16 H16 0.9500 . ? C17 C18 1.389(3) . ? C17 H17 0.9500 . ? C18 C19 1.388(3) . ? C18 C21 1.515(3) . ? C19 C20 1.376(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C22 C23 1.443(6) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? 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 N2 91.78(7) . . ? O2 Cu1 O1 171.67(6) . . ? N2 Cu1 O1 80.75(7) . . ? O2 Cu1 N3 93.49(7) . . ? N2 Cu1 N3 167.56(7) . . ? O1 Cu1 N3 93.14(7) . . ? O2 Cu1 O5 96.56(6) . 4_565 ? N2 Cu1 O5 97.24(6) . 4_565 ? O1 Cu1 O5 88.07(6) . 4_565 ? N3 Cu1 O5 93.34(6) . 4_565 ? C1 O1 Cu1 112.32(14) . . ? C10 O2 Cu1 127.46(14) . . ? C11 O3 C15 116.7(2) . . ? C21 O5 Cu1 130.21(14) . 4_566 ? C22 O6 H86 117(3) . . ? H72 O7 H73 114(4) . . ? C1 N1 N2 114.03(18) . . ? C1 N1 H71 126.6(17) . . ? N2 N1 H71 117.6(17) . . ? C8 N2 N1 118.61(18) . . ? C8 N2 Cu1 128.63(15) . . ? N1 N2 Cu1 112.46(14) . . ? C16 N3 C20 118.05(19) . . ? C16 N3 Cu1 121.04(14) . . ? C20 N3 Cu1 120.62(15) . . ? O1 C1 N1 119.8(2) . . ? O1 C1 C2 120.6(2) . . ? N1 C1 C2 119.5(2) . . ? C3 C2 C7 119.5(2) . . ? C3 C2 C1 117.8(2) . . ? C7 C2 C1 122.7(2) . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.5(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.4(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C2 119.8(2) . . ? C6 C7 H7 120.1 . . ? C2 C7 H7 120.1 . . ? N2 C8 C9 123.4(2) . . ? N2 C8 H8 118.3 . . ? C9 C8 H8 118.3 . . ? C10 C9 C14 120.0(2) . . ? C10 C9 C8 122.2(2) . . ? C14 C9 C8 117.8(2) . . ? O2 C10 C9 125.7(2) . . ? O2 C10 C11 117.2(2) . . ? C9 C10 C11 117.1(2) . . ? O3 C11 C12 125.3(2) . . ? O3 C11 C10 113.5(2) . . ? C12 C11 C10 121.2(2) . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 120.0(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C9 121.2(2) . . ? C13 C14 H14 119.4 . . ? C9 C14 H14 119.4 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 C17 122.6(2) . . ? N3 C16 H16 118.7 . . ? C17 C16 H16 118.7 . . ? C16 C17 C18 119.4(2) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C19 C18 C17 117.6(2) . . ? C19 C18 C21 120.8(2) . . ? C17 C18 C21 121.6(2) . . ? C20 C19 C18 119.8(2) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? N3 C20 C19 122.3(2) . . ? N3 C20 H20 118.8 . . ? C19 C20 H20 118.8 . . ? O4 C21 O5 125.1(2) . . ? O4 C21 C18 119.1(2) . . ? O5 C21 C18 115.71(19) . . ? O6 C22 C23 110.5(4) . . ? O6 C22 H22A 109.5 . . ? C23 C22 H22A 109.5 . . ? O6 C22 H22B 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 O1 C1 6.88(14) . . . . ? N3 Cu1 O1 C1 175.98(14) . . . . ? O5 Cu1 O1 C1 -90.78(14) 4_565 . . . ? N2 Cu1 O2 C10 9.17(18) . . . . ? N3 Cu1 O2 C10 -159.56(17) . . . . ? O5 Cu1 O2 C10 106.67(17) 4_565 . . . ? C1 N1 N2 C8 -169.32(18) . . . . ? C1 N1 N2 Cu1 4.9(2) . . . . ? O2 Cu1 N2 C8 -9.06(19) . . . . ? O1 Cu1 N2 C8 167.26(19) . . . . ? N3 Cu1 N2 C8 106.0(4) . . . . ? O5 Cu1 N2 C8 -105.90(18) 4_565 . . . ? O2 Cu1 N2 N1 177.48(13) . . . . ? O1 Cu1 N2 N1 -6.20(13) . . . . ? N3 Cu1 N2 N1 -67.5(4) . . . . ? O5 Cu1 N2 N1 80.63(13) 4_565 . . . ? O2 Cu1 N3 C16 -159.50(17) . . . . ? N2 Cu1 N3 C16 85.6(4) . . . . ? O1 Cu1 N3 C16 25.54(18) . . . . ? O5 Cu1 N3 C16 -62.71(17) 4_565 . . . ? O2 Cu1 N3 C20 14.23(17) . . . . ? N2 Cu1 N3 C20 -100.7(4) . . . . ? O1 Cu1 N3 C20 -160.74(16) . . . . ? O5 Cu1 N3 C20 111.02(16) 4_565 . . . ? Cu1 O1 C1 N1 -6.4(2) . . . . ? Cu1 O1 C1 C2 174.03(15) . . . . ? N2 N1 C1 O1 1.1(3) . . . . ? N2 N1 C1 C2 -179.27(17) . . . . ? O1 C1 C2 C3 -12.2(3) . . . . ? N1 C1 C2 C3 168.2(2) . . . . ? O1 C1 C2 C7 168.13(19) . . . . ? N1 C1 C2 C7 -11.5(3) . . . . ? C7 C2 C3 C4 0.8(3) . . . . ? C1 C2 C3 C4 -178.9(2) . . . . ? C2 C3 C4 C5 -0.6(4) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? C4 C5 C6 C7 -0.2(4) . . . . ? C5 C6 C7 C2 0.4(4) . . . . ? C3 C2 C7 C6 -0.7(3) . . . . ? C1 C2 C7 C6 179.0(2) . . . . ? N1 N2 C8 C9 178.54(19) . . . . ? Cu1 N2 C8 C9 5.4(3) . . . . ? N2 C8 C9 C10 1.4(3) . . . . ? N2 C8 C9 C14 -177.3(2) . . . . ? Cu1 O2 C10 C9 -6.1(3) . . . . ? Cu1 O2 C10 C11 174.26(15) . . . . ? C14 C9 C10 O2 177.6(2) . . . . ? C8 C9 C10 O2 -1.1(3) . . . . ? C14 C9 C10 C11 -2.8(3) . . . . ? C8 C9 C10 C11 178.55(19) . . . . ? C15 O3 C11 C12 -7.8(4) . . . . ? C15 O3 C11 C10 171.7(2) . . . . ? O2 C10 C11 O3 3.9(3) . . . . ? C9 C10 C11 O3 -175.84(19) . . . . ? O2 C10 C11 C12 -176.5(2) . . . . ? C9 C10 C11 C12 3.7(3) . . . . ? O3 C11 C12 C13 177.5(2) . . . . ? C10 C11 C12 C13 -2.0(4) . . . . ? C11 C12 C13 C14 -0.9(4) . . . . ? C12 C13 C14 C9 1.8(4) . . . . ? C10 C9 C14 C13 0.1(3) . . . . ? C8 C9 C14 C13 178.8(2) . . . . ? C20 N3 C16 C17 -2.9(3) . . . . ? Cu1 N3 C16 C17 170.95(17) . . . . ? N3 C16 C17 C18 1.9(3) . . . . ? C16 C17 C18 C19 1.5(3) . . . . ? C16 C17 C18 C21 -176.5(2) . . . . ? C17 C18 C19 C20 -3.8(3) . . . . ? C21 C18 C19 C20 174.2(2) . . . . ? C16 N3 C20 C19 0.5(3) . . . . ? Cu1 N3 C20 C19 -173.39(17) . . . . ? C18 C19 C20 N3 2.9(3) . . . . ? Cu1 O5 C21 O4 -124.5(2) 4_566 . . . ? Cu1 O5 C21 C18 57.4(3) 4_566 . . . ? C19 C18 C21 O4 -153.3(2) . . . . ? C17 C18 C21 O4 24.6(3) . . . . ? C19 C18 C21 O5 25.0(3) . . . . ? C17 C18 C21 O5 -157.1(2) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 _geom_hbond_publ_flag O6 H86 O7 0.72(3) 1.99(3) 2.707(4) 173(4) . ? O7 H72 O6 0.73(4) 2.00(4) 2.729(4) 177(5) 4_565 ? O7 H73 O4 0.88(4) 1.92(5) 2.788(3) 170(4) . ? N1 H71 O5 0.89(3) 1.76(3) 2.650(2) 172(2) 2_746 ? _geom_special_details ? _audit_block_code Cu_C15H13N2O3_C6H4NO2_H2O_EtOH_mn262_monfared _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C21 H17 Cu N3 O5, C2 H6 O, H2 O' _chemical_formula_sum 'C23 H25 Cu N3 O7' _chemical_formula_weight 519.007 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 4 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.48579 _exptl_crystal_F_000 1076 #===END data_mo188 #?# MeasurementCode _database_code_depnum_ccdc_archive 'CCDC 720069' #TrackingRef '- 1+2-crystaldata.CIF' _audit_update_record 10-Feb-09 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description rod #?# e.g.: needle, platelet; prismatic _exptl_crystal_colour brown _exptl_crystal_size_max 0.15 #?# in millimeters _exptl_crystal_size_mid 0.07 #?# in millimeters _exptl_crystal_size_min 0.04 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_author_name 'P. Mayer' #?# X-ray operator _audit_creation_date ; 'Wed Jul 16 13:45:55 2008' ; _diffrn_ambient_temperature 200(2) #?# in K _diffrn_source_type 'Spellman generator' _diffrn_source_power 2.00 #?# in kW _diffrn_source_voltage 50 #?# in kV _diffrn_source_current 40 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation '0.5 mm collimator' _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Oxford XCalibur' _diffrn_measurement_method omega-scans _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -55.00 -16.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -14.3889 154.0000 -175.0000 0.0000 0.0000 39 #__ type_ start__ end____ width___ exp.time_ 2 omega 36.00 86.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 14.5452 45.0000 120.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 3 omega 53.00 92.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 14.5452 -154.0000 -35.0000 0.0000 0.0000 39 #__ type_ start__ end____ width___ exp.time_ 4 omega -13.00 38.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 14.5452 45.0000 240.0000 0.0000 0.0000 51 #__ type_ start__ end____ width___ exp.time_ 5 omega -22.00 18.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 14.5452 -101.0000 0.0000 0.0000 0.0000 40 #__ type_ start__ end____ width___ exp.time_ 6 omega -6.00 40.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 14.5452 -45.0000 0.0000 0.0000 0.0000 46 ; _diffrn_detector_area_resol_mean 15.9809 _diffrn_special_details ? _diffrn_orient_matrix_type ? _diffrn_orient_matrix_UB_11 0.0399743915 _diffrn_orient_matrix_UB_12 -0.0424054062 _diffrn_orient_matrix_UB_13 -0.0020830196 _diffrn_orient_matrix_UB_21 -0.1048056778 _diffrn_orient_matrix_UB_22 -0.0113676346 _diffrn_orient_matrix_UB_23 0.0180627219 _diffrn_orient_matrix_UB_31 -0.0997207601 _diffrn_orient_matrix_UB_32 -0.0050755303 _diffrn_orient_matrix_UB_33 -0.0230339041 loop_ _reflns_scale_group_code _reflns_scale_meas_F ? ? _cell_length_a 4.7333(3) _cell_length_b 16.0520(10) _cell_length_c 24.2371(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.195(5) _cell_angle_gamma 90.00 _cell_volume 1836.58(18) _cell_measurement_temperature 200(2) #?# in K _cell_measurement_reflns_used 2118 _cell_measurement_theta_min 3.8043 _cell_measurement_theta_max 25.2466 _cell_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 14 -2 0.0490 -1 -28 -11 0.0250 0 -5 -14 0.0300 1 18 30 0.1583 9 -11 0 0.0753 -30 -17 -14 0.0898 0 4 -29 0.0462 9 15 17 0.0741 -9 -3 -19 0.0776 5 -14 -1 0.0621 -20 15 -1 0.0806 _exptl_absorpt_coefficient_mu 1.231 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7551 _exptl_absorpt_correction_T_max 0.9302 _exptl_absorpt_process_details ; Crystal faces optimized with XShape, rev. 1.02, STOE (Darmstadt, Germany) Absorption correction with XRed, rev 1.09, STOE (Darmstadt, Germany) ; _diffrn_reflns_number 7223 #xl _diffrn_reflns_av_R_equivalents 0.0525 #xl _diffrn_reflns_av_sigmaI/netI 0.1180 #xl _diffrn_reflns_limit_h_min -4 #xl _diffrn_reflns_limit_h_max 5 #xl _diffrn_reflns_limit_k_min -18 #xl _diffrn_reflns_limit_k_max 16 #xl _diffrn_reflns_limit_l_min -28 #xl _diffrn_reflns_limit_l_max 21 #xl _diffrn_reflns_theta_min 3.90 #xl _diffrn_reflns_theta_max 24.00 #xl _diffrn_measured_fraction_theta_max 0.961 #xl _diffrn_reflns_theta_full 24.00 #xl _diffrn_measured_fraction_theta_full 0.961 #xl _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' 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' _reflns_number_total 2784 #xl _reflns_number_gt 1573 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0301P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 2784 #xl _refine_ls_number_parameters 276 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0943 #xl _refine_ls_R_factor_gt 0.0404 #xl _refine_ls_wR_factor_ref 0.0773 #xl _refine_ls_wR_factor_gt 0.0675 #xl _refine_ls_goodness_of_fit_ref 0.871 #xl _refine_ls_restrained_S_all 0.871 #xl _refine_ls_shift/su_max 0.000 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.694 #xl _refine_diff_density_min -0.348 #xl _refine_diff_density_rms 0.074 #xl _refine_special_details ; O-bonded H: refall C-bonded H: constr ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement 'SHELXL-97 (G. M. Sheldrick. University of G\"ottingen, 97-2 version)' _computing_molecular_graphics ? 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 0.94731(12) 0.21511(3) 0.191832(18) 0.02947(19) Uani 1 1 d . . . O1 O 1.1962(6) 0.30562(16) 0.17718(9) 0.0332(8) Uani 1 1 d . . . O2 O 0.6632(6) 0.13579(16) 0.19968(9) 0.0323(8) Uani 1 1 d . . . O3 O 0.2920(7) 0.02829(17) 0.23069(10) 0.0390(8) Uani 1 1 d . . . O4 O 1.3626(8) 0.3067(2) 0.46663(11) 0.0689(13) Uani 1 1 d . . . O5 O 1.0213(6) 0.21632(19) 0.47972(11) 0.0387(9) Uani 1 1 d . . . H1 H 1.064(10) 0.231(3) 0.519(2) 0.097(19) Uiso 1 1 d . . . N1 N 1.0995(7) 0.2637(2) 0.08717(12) 0.0253(9) Uani 1 1 d . . . N2 N 0.9257(7) 0.2070(2) 0.11286(11) 0.0243(8) Uani 1 1 d . . . N3 N 1.0207(7) 0.2267(2) 0.27406(12) 0.0251(9) Uani 1 1 d . . . C1 C 1.2272(9) 0.3132(3) 0.12398(16) 0.0258(11) Uani 1 1 d . . . C2 C 1.4077(9) 0.3806(3) 0.10584(14) 0.0228(11) Uani 1 1 d . . . C3 C 1.4398(9) 0.4528(3) 0.13771(15) 0.0342(12) Uani 1 1 d . . . H3 H 1.3473 0.4571 0.1711 0.041 Uiso 1 1 calc R . . C4 C 1.6046(10) 0.5183(3) 0.12133(16) 0.0350(12) Uani 1 1 d . . . H4 H 1.6257 0.5670 0.1435 0.042 Uiso 1 1 calc R . . C5 C 1.7379(10) 0.5128(3) 0.07279(16) 0.0391(13) Uani 1 1 d . . . H5 H 1.8484 0.5580 0.0610 0.047 Uiso 1 1 calc R . . C6 C 1.7096(9) 0.4406(3) 0.04115(16) 0.0348(13) Uani 1 1 d . . . H6 H 1.8051 0.4360 0.0081 0.042 Uiso 1 1 calc R . . C7 C 1.5449(9) 0.3761(3) 0.05728(14) 0.0277(11) Uani 1 1 d . . . H7 H 1.5244 0.3277 0.0349 0.033 Uiso 1 1 calc R . . C8 C 0.7640(9) 0.1584(2) 0.08212(15) 0.0249(11) Uani 1 1 d . . . H8 H 0.7750 0.1616 0.0432 0.030 Uiso 1 1 calc R . . C9 C 0.5711(9) 0.1006(2) 0.10258(15) 0.0210(10) Uani 1 1 d . . . C10 C 0.5282(9) 0.0923(3) 0.15958(16) 0.0251(11) Uani 1 1 d . . . C11 C 0.3262(9) 0.0321(3) 0.17475(16) 0.0276(11) Uani 1 1 d . . . C12 C 0.1820(10) -0.0157(3) 0.13573(16) 0.0331(13) Uani 1 1 d . . . H12 H 0.0500 -0.0556 0.1470 0.040 Uiso 1 1 calc R . . C13 C 0.2235(10) -0.0073(3) 0.07958(16) 0.0351(13) Uani 1 1 d . . . H13 H 0.1233 -0.0416 0.0529 0.042 Uiso 1 1 calc R . . C14 C 0.4098(10) 0.0509(2) 0.06395(15) 0.0289(12) Uani 1 1 d . . . H14 H 0.4325 0.0584 0.0256 0.035 Uiso 1 1 calc R . . C15 C 0.0900(10) -0.0301(3) 0.24730(15) 0.0473(15) Uani 1 1 d . . . H15A H -0.0937 -0.0192 0.2273 0.071 Uiso 1 1 calc R . . H15B H 0.0716 -0.0248 0.2872 0.071 Uiso 1 1 calc R . . H15C H 0.1525 -0.0866 0.2389 0.071 Uiso 1 1 calc R . . C16 C 1.2188(9) 0.2795(3) 0.29552(14) 0.0282(11) Uani 1 1 d . . . H16 H 1.3282 0.3096 0.2709 0.034 Uiso 1 1 calc R . . C17 C 1.2716(9) 0.2922(3) 0.35185(14) 0.0287(11) Uani 1 1 d . . . H17 H 1.4120 0.3307 0.3655 0.034 Uiso 1 1 calc R . . C18 C 1.1164(10) 0.2478(2) 0.38751(14) 0.0243(11) Uani 1 1 d . . . C19 C 0.9111(9) 0.1939(3) 0.36609(15) 0.0299(12) Uani 1 1 d . . . H19 H 0.7976 0.1636 0.3899 0.036 Uiso 1 1 calc R . . C20 C 0.8727(9) 0.1844(2) 0.30936(15) 0.0295(12) Uani 1 1 d . . . H20 H 0.7340 0.1459 0.2949 0.035 Uiso 1 1 calc R . . C21 C 1.1750(11) 0.2607(3) 0.44970(17) 0.0347(13) 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 Cu 0.0360(4) 0.0384(4) 0.0143(3) 0.0019(3) 0.0035(2) -0.0042(4) O1 0.038(2) 0.052(2) 0.0102(14) -0.0030(13) 0.0041(13) -0.0096(17) O2 0.043(2) 0.0375(19) 0.0159(15) 0.0028(14) -0.0005(14) -0.0124(17) O3 0.041(2) 0.051(2) 0.0255(16) 0.0046(14) 0.0048(15) -0.0171(19) O4 0.104(4) 0.078(3) 0.0232(18) 0.0036(17) -0.0068(19) -0.049(3) O5 0.047(2) 0.056(2) 0.0138(16) -0.0022(16) 0.0060(15) -0.008(2) N1 0.028(2) 0.032(2) 0.0165(18) -0.0008(16) 0.0058(16) -0.0044(19) N2 0.028(2) 0.030(2) 0.0159(17) 0.0015(18) 0.0066(16) 0.002(2) N3 0.026(2) 0.028(2) 0.0209(19) 0.0043(17) 0.0050(17) 0.002(2) C1 0.024(3) 0.034(3) 0.019(2) 0.004(2) 0.003(2) 0.003(2) C2 0.020(3) 0.035(3) 0.013(2) 0.003(2) 0.0005(19) 0.002(2) C3 0.025(3) 0.056(3) 0.023(2) -0.003(2) 0.006(2) -0.002(3) C4 0.036(4) 0.034(3) 0.035(3) -0.004(2) 0.007(2) -0.006(3) C5 0.035(4) 0.048(3) 0.035(3) 0.007(3) 0.004(2) -0.005(3) C6 0.035(4) 0.051(3) 0.019(2) 0.002(2) 0.010(2) -0.003(3) C7 0.032(3) 0.035(3) 0.017(2) 0.000(2) 0.003(2) 0.000(3) C8 0.034(3) 0.025(3) 0.016(2) 0.001(2) 0.005(2) 0.002(2) C9 0.022(3) 0.021(2) 0.020(2) 0.002(2) 0.001(2) 0.000(2) C10 0.018(3) 0.030(3) 0.027(2) -0.002(2) -0.001(2) 0.002(2) C11 0.022(3) 0.041(3) 0.020(2) 0.005(2) 0.003(2) -0.004(3) C12 0.040(4) 0.029(3) 0.030(3) 0.004(2) 0.000(2) -0.008(2) C13 0.043(4) 0.030(3) 0.032(3) -0.010(2) -0.004(2) -0.008(3) C14 0.043(4) 0.024(3) 0.018(2) -0.004(2) -0.004(2) -0.001(3) C15 0.045(4) 0.065(4) 0.033(3) 0.008(2) 0.013(3) -0.027(3) C16 0.034(3) 0.032(3) 0.019(2) 0.008(2) 0.007(2) 0.000(3) C17 0.036(3) 0.028(3) 0.022(2) 0.001(2) -0.002(2) -0.006(3) C18 0.037(3) 0.022(3) 0.014(2) -0.0006(19) 0.004(2) 0.008(2) C19 0.035(3) 0.040(3) 0.016(2) 0.007(2) 0.006(2) -0.005(3) C20 0.032(3) 0.032(3) 0.024(2) 0.001(2) -0.001(2) -0.002(2) C21 0.036(4) 0.044(3) 0.023(3) 0.001(2) -0.006(2) 0.003(3) 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 1.871(3) . ? Cu N2 1.914(3) . ? Cu O1 1.920(3) . ? Cu N3 2.006(3) . ? O1 C1 1.314(4) . ? O2 C10 1.323(4) . ? O3 C11 1.379(4) . ? O3 C15 1.418(5) . ? O4 C21 1.204(5) . ? O5 C21 1.282(5) . ? O5 H1 0.98(5) . ? N1 C1 1.310(4) . ? N1 N2 1.402(4) . ? N2 C8 1.291(4) . ? N3 C20 1.331(5) . ? N3 C16 1.340(5) . ? C1 C2 1.466(5) . ? C2 C7 1.387(5) . ? C2 C3 1.395(5) . ? C3 C4 1.385(6) . ? C3 H3 0.9500 . ? C4 C5 1.378(5) . ? C4 H4 0.9500 . ? C5 C6 1.391(5) . ? C5 H5 0.9500 . ? C6 C7 1.370(5) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.416(5) . ? C8 H8 0.9500 . ? C9 C14 1.412(5) . ? C9 C10 1.417(5) . ? C10 C11 1.426(5) . ? C11 C12 1.361(5) . ? C12 C13 1.395(5) . ? C12 H12 0.9500 . ? C13 C14 1.357(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.385(5) . ? C16 H16 0.9500 . ? C17 C18 1.374(5) . ? C17 H17 0.9500 . ? C18 C19 1.374(5) . ? C18 C21 1.527(5) . ? C19 C20 1.382(5) . ? C19 H19 0.9500 . ? C20 H20 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 Cu N2 93.96(13) . . ? O2 Cu O1 171.40(11) . . ? N2 Cu O1 81.67(13) . . ? O2 Cu N3 92.04(13) . . ? N2 Cu N3 172.95(16) . . ? O1 Cu N3 92.84(12) . . ? C1 O1 Cu 111.5(2) . . ? C10 O2 Cu 126.6(2) . . ? C11 O3 C15 116.0(3) . . ? C21 O5 H1 109(3) . . ? C1 N1 N2 110.4(3) . . ? C8 N2 N1 118.6(3) . . ? C8 N2 Cu 127.2(3) . . ? N1 N2 Cu 114.2(2) . . ? C20 N3 C16 117.3(3) . . ? C20 N3 Cu 122.0(3) . . ? C16 N3 Cu 120.6(3) . . ? N1 C1 O1 122.2(4) . . ? N1 C1 C2 119.6(3) . . ? O1 C1 C2 118.2(4) . . ? C7 C2 C3 118.3(4) . . ? C7 C2 C1 122.4(4) . . ? C3 C2 C1 119.3(4) . . ? C4 C3 C2 120.9(4) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 119.9(4) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.5(4) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 120.4(4) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C2 121.0(4) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? N2 C8 C9 124.3(4) . . ? N2 C8 H8 117.8 . . ? C9 C8 H8 117.8 . . ? C14 C9 C8 118.0(4) . . ? C14 C9 C10 118.9(4) . . ? C8 C9 C10 123.0(4) . . ? O2 C10 C9 124.8(4) . . ? O2 C10 C11 117.7(3) . . ? C9 C10 C11 117.5(4) . . ? C12 C11 O3 124.7(4) . . ? C12 C11 C10 120.9(4) . . ? O3 C11 C10 114.4(4) . . ? C11 C12 C13 121.6(4) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C14 C13 C12 118.6(4) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C9 122.3(4) . . ? C13 C14 H14 118.8 . . ? C9 C14 H14 118.8 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 C17 123.1(4) . . ? N3 C16 H16 118.4 . . ? C17 C16 H16 118.4 . . ? C18 C17 C16 118.5(4) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C17 C18 C19 119.0(4) . . ? C17 C18 C21 118.9(4) . . ? C19 C18 C21 122.1(4) . . ? C18 C19 C20 118.9(4) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? N3 C20 C19 123.1(4) . . ? N3 C20 H20 118.4 . . ? C19 C20 H20 118.4 . . ? O4 C21 O5 125.6(4) . . ? O4 C21 C18 119.7(5) . . ? O5 C21 C18 114.5(4) . . ? 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 Cu O1 C1 -1.6(3) . . . . ? N3 Cu O1 C1 173.9(3) . . . . ? N2 Cu O2 C10 2.9(3) . . . . ? N3 Cu O2 C10 -173.4(3) . . . . ? C1 N1 N2 C8 173.8(3) . . . . ? C1 N1 N2 Cu -3.6(4) . . . . ? O2 Cu N2 C8 -1.6(3) . . . . ? O1 Cu N2 C8 -174.2(3) . . . . ? O2 Cu N2 N1 175.5(3) . . . . ? O1 Cu N2 N1 2.9(3) . . . . ? O2 Cu N3 C20 -1.4(3) . . . . ? O1 Cu N3 C20 171.5(3) . . . . ? O2 Cu N3 C16 -179.8(3) . . . . ? O1 Cu N3 C16 -6.9(3) . . . . ? N2 N1 C1 O1 2.4(5) . . . . ? N2 N1 C1 C2 -176.6(3) . . . . ? Cu O1 C1 N1 0.0(5) . . . . ? Cu O1 C1 C2 179.0(3) . . . . ? N1 C1 C2 C7 -27.2(6) . . . . ? O1 C1 C2 C7 153.8(4) . . . . ? N1 C1 C2 C3 151.5(4) . . . . ? O1 C1 C2 C3 -27.5(6) . . . . ? C7 C2 C3 C4 -0.1(6) . . . . ? C1 C2 C3 C4 -178.8(4) . . . . ? C2 C3 C4 C5 0.4(7) . . . . ? C3 C4 C5 C6 -1.2(7) . . . . ? C4 C5 C6 C7 1.6(6) . . . . ? C5 C6 C7 C2 -1.3(7) . . . . ? C3 C2 C7 C6 0.5(6) . . . . ? C1 C2 C7 C6 179.2(4) . . . . ? N1 N2 C8 C9 -177.6(4) . . . . ? Cu N2 C8 C9 -0.6(6) . . . . ? N2 C8 C9 C14 -179.4(4) . . . . ? N2 C8 C9 C10 2.4(6) . . . . ? Cu O2 C10 C9 -2.1(5) . . . . ? Cu O2 C10 C11 177.3(3) . . . . ? C14 C9 C10 O2 -179.2(4) . . . . ? C8 C9 C10 O2 -0.9(6) . . . . ? C14 C9 C10 C11 1.3(6) . . . . ? C8 C9 C10 C11 179.6(4) . . . . ? C15 O3 C11 C12 -0.1(6) . . . . ? C15 O3 C11 C10 179.2(4) . . . . ? O2 C10 C11 C12 -179.2(4) . . . . ? C9 C10 C11 C12 0.3(6) . . . . ? O2 C10 C11 O3 1.5(6) . . . . ? C9 C10 C11 O3 -179.0(3) . . . . ? O3 C11 C12 C13 178.7(4) . . . . ? C10 C11 C12 C13 -0.6(7) . . . . ? C11 C12 C13 C14 -0.9(7) . . . . ? C12 C13 C14 C9 2.7(7) . . . . ? C8 C9 C14 C13 178.8(4) . . . . ? C10 C9 C14 C13 -2.9(6) . . . . ? C20 N3 C16 C17 -0.8(6) . . . . ? Cu N3 C16 C17 177.6(3) . . . . ? N3 C16 C17 C18 0.9(6) . . . . ? C16 C17 C18 C19 -1.3(6) . . . . ? C16 C17 C18 C21 179.4(4) . . . . ? C17 C18 C19 C20 1.7(6) . . . . ? C21 C18 C19 C20 -179.1(4) . . . . ? C16 N3 C20 C19 1.2(6) . . . . ? Cu N3 C20 C19 -177.2(3) . . . . ? C18 C19 C20 N3 -1.7(6) . . . . ? C17 C18 C21 O4 -2.9(7) . . . . ? C19 C18 C21 O4 177.8(4) . . . . ? C17 C18 C21 O5 -179.6(4) . . . . ? C19 C18 C21 O5 1.1(6) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 _geom_hbond_publ_flag O5 H1 N1 0.98(5) 1.66(5) 2.623(4) 168(4) 4_566 ? O5 H1 N2 0.98(5) 2.62(5) 3.514(4) 152(4) 4_566 ? _geom_special_details ? _audit_block_code Cu_C15H12N2O3_C6H5NO2_mo188_monfared _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C21 H17 Cu N3 O5' _chemical_formula_sum 'C21 H17 Cu N3 O5' _chemical_formula_weight 454.923 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 4 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.64529 _exptl_crystal_F_000 932 #===END