# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'M. Zaworotko' _publ_contact_author_address ; Chair, Department of Chemistry University of South Florida 4202 East Fowler Avenue Tampa Florida 33620-5250 UNITED STATES OF AMERICA ; _publ_contact_author_email XTAL@USF.EDU _publ_section_title ; A Novel Metal-Organic Ternary Network Constructed from Vertex-Linked Polygons and Polyhedra (VLPP) ; loop_ _publ_author_name 'M. Zaworotko' 'Derek A. Beauchamp' 'Gregory McManus' 'Zhenqiang Wang.' # Attachment '1,2-new.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 658210' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H30 Cu2 N3 O15.50' _chemical_formula_weight 699.56 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 Orthorhombic _symmetry_space_group_name_H-M Ibam loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1, y+1, -z+1/2' 'x+1, -y+1, -z+1/2' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' 'x, -y, z+1/2' '-x, y, z+1/2' _cell_length_a 14.669(7) _cell_length_b 16.833(8) _cell_length_c 24.743(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6109(5) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2872 _exptl_absorpt_coefficient_mu 1.464 _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 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14695 _diffrn_reflns_av_R_equivalents 0.1695 _diffrn_reflns_av_sigmaI/netI 0.1576 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.11 _reflns_number_total 2787 _reflns_number_gt 1283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1031P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00107(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2787 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1534 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.1883 _refine_ls_wR_factor_gt 0.1612 _refine_ls_goodness_of_fit_ref 0.882 _refine_ls_restrained_S_all 0.882 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O13 O -0.3872(3) 0.2927(3) 0.2900(2) 0.0501(16) Uani 1 1 d . . . C19 C -0.3514(6) 0.3389(6) 0.3227(4) 0.060(3) Uani 1 1 d . . . O12 O -0.1170(4) 0.4739(3) 0.4452(2) 0.0559(17) Uani 1 1 d . . . Cu1 Cu 0.07280(8) 0.45242(8) 0.5000 0.0326(4) Uani 1 2 d S . . Cu2 Cu 0.0000 0.19400(9) 0.2500 0.0474(5) Uani 1 2 d S . . N11 N -0.0756(4) 0.1707(4) 0.3178(2) 0.0395(16) Uani 1 1 d . . . H11A H -0.1166 0.1326 0.3099 0.047 Uiso 1 1 calc R . . H11B H -0.0384 0.1515 0.3436 0.047 Uiso 1 1 calc R . . O11 O 0.0030(4) 0.3949(3) 0.4446(2) 0.0586(17) Uani 1 1 d . . . O14 O -0.3910(5) 0.3983(5) 0.3410(4) 0.154(4) Uani 1 1 d . . . C11 C -0.1221(5) 0.3591(5) 0.3910(3) 0.0362(19) Uani 1 1 d . . . C12 C -0.0794(5) 0.2908(5) 0.3725(3) 0.042(2) Uani 1 1 d . . . H12 H -0.0200 0.2802 0.3834 0.050 Uiso 1 1 calc R . . C13 C -0.1226(5) 0.2385(5) 0.3385(3) 0.039(2) Uani 1 1 d . . . C14 C -0.2118(5) 0.2526(5) 0.3232(3) 0.039(2) Uani 1 1 d . . . H14 H -0.2422 0.2162 0.3014 0.047 Uiso 1 1 calc R . . C15 C -0.2561(5) 0.3210(5) 0.3405(3) 0.044(2) Uani 1 1 d . . . C16 C -0.2113(5) 0.3744(5) 0.3751(3) 0.048(2) Uani 1 1 d . . . H16 H -0.2412 0.4197 0.3873 0.057 Uiso 1 1 calc R . . C18 C -0.0756(5) 0.4145(5) 0.4297(3) 0.042(2) Uani 1 1 d . . . N21 N 0.1865(7) 0.3739(6) 0.5000 0.049(3) Uani 1 2 d S . . C21 C 0.2716(10) 0.4019(11) 0.5000 0.112(6) Uani 1 2 d S . . H21 H 0.2802 0.4566 0.5000 0.134 Uiso 1 2 calc SR . . C22 C 0.3462(13) 0.3541(15) 0.5000 0.139(9) Uani 1 2 d S . . H22 H 0.4048 0.3752 0.5000 0.167 Uiso 1 2 calc SR . . C23 C 0.3315(14) 0.2715(16) 0.5000 0.112(8) Uani 1 2 d S . . H23 H 0.3811 0.2370 0.5000 0.135 Uiso 1 2 calc SR . . C24 C 0.2512(16) 0.2436(12) 0.5000 0.115(7) Uani 1 2 d S . . H24 H 0.2410 0.1890 0.5000 0.138 Uiso 1 2 calc SR . . C25 C 0.1777(11) 0.2977(11) 0.5000 0.086(5) Uani 1 2 d S . . H25 H 0.1189 0.2770 0.5000 0.103 Uiso 1 2 calc SR . . O31 O 0.0000 0.3313(6) 0.2500 0.110(4) Uani 1 2 d S . . H31A H 0.0471 0.3589 0.2667 0.132 Uiso 0.50 1 calc PR . . H31B H -0.0471 0.3589 0.2333 0.132 Uiso 0.50 1 calc PR . . O1S O 0.7928(6) 0.0374(4) 0.2998(3) 0.114(3) Uani 1 1 d . . . O2S O 0.0000 0.0000 0.2500 0.253(15) Uani 1 4 d S . . O3S O 0.1104(9) 0.4239(9) 0.3314(5) 0.266(9) Uani 1 1 d . . . O4S O 0.0661(9) 0.0595(10) 0.4444(5) 0.275(8) 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 O13 0.025(3) 0.079(4) 0.046(3) -0.011(3) -0.020(2) 0.002(3) C19 0.026(5) 0.062(6) 0.092(7) -0.025(6) -0.018(5) 0.014(5) O12 0.039(4) 0.056(4) 0.072(4) -0.027(3) -0.021(3) 0.008(3) Cu1 0.0183(7) 0.0479(9) 0.0315(7) 0.000 0.000 -0.0044(6) Cu2 0.0214(7) 0.0742(12) 0.0467(9) 0.000 -0.0116(6) 0.000 N11 0.026(3) 0.048(4) 0.045(4) -0.002(3) -0.017(3) 0.004(3) O11 0.036(3) 0.075(4) 0.065(4) -0.030(3) -0.027(3) 0.009(3) O14 0.059(5) 0.142(8) 0.259(11) -0.142(8) -0.086(6) 0.049(5) C11 0.024(4) 0.046(5) 0.038(4) 0.000(4) -0.003(3) -0.008(4) C12 0.023(4) 0.062(6) 0.041(4) 0.002(4) -0.008(4) -0.007(4) C13 0.024(5) 0.049(5) 0.044(5) -0.003(4) -0.007(3) 0.000(4) C14 0.025(4) 0.048(5) 0.044(5) -0.006(4) -0.007(4) 0.000(4) C15 0.029(5) 0.057(6) 0.046(5) -0.012(4) -0.012(4) 0.007(4) C16 0.027(5) 0.062(6) 0.054(5) -0.006(5) -0.007(4) 0.004(4) C18 0.026(5) 0.056(6) 0.043(5) -0.002(4) -0.008(4) -0.016(5) N21 0.047(7) 0.042(7) 0.057(6) 0.000 0.000 0.004(6) C21 0.022(9) 0.118(15) 0.196(19) 0.000 0.000 0.005(10) C22 0.043(11) 0.16(2) 0.21(2) 0.000 0.000 0.036(15) C23 0.068(14) 0.18(2) 0.085(12) 0.000 0.000 0.069(17) C24 0.121(18) 0.115(17) 0.108(14) 0.000 0.000 0.058(16) C25 0.065(11) 0.092(14) 0.101(12) 0.000 0.000 0.004(11) O31 0.132(10) 0.107(9) 0.090(8) 0.000 -0.011(7) 0.000 O1S 0.118(6) 0.079(5) 0.145(7) -0.001(5) 0.024(6) -0.043(5) O2S 0.17(2) 0.45(5) 0.14(2) 0.000 0.000 0.000 O3S 0.265(15) 0.306(17) 0.228(13) -0.157(12) 0.149(12) -0.183(13) O4S 0.210(14) 0.43(2) 0.184(12) -0.014(14) 0.062(11) -0.125(14) _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 O13 C19 1.239(9) . ? O13 Cu2 1.940(5) 13_455 ? C19 O14 1.242(10) . ? C19 C15 1.496(10) . ? O12 C18 1.230(9) . ? O12 Cu1 1.948(5) 9_566 ? Cu1 O12 1.948(5) 9_566 ? Cu1 O12 1.948(5) 2_565 ? Cu1 O11 1.965(5) . ? Cu1 O11 1.965(5) 10_556 ? Cu1 N21 2.128(10) . ? Cu1 Cu1 2.670(3) 9_566 ? Cu2 O13 1.940(5) 11_665 ? Cu2 O13 1.940(5) 13_455 ? Cu2 N11 2.048(6) . ? Cu2 N11 2.048(6) 7_445 ? Cu2 O31 2.311(11) . ? N11 C13 1.429(9) . ? N11 H11A 0.9000 . ? N11 H11B 0.9000 . ? O11 C18 1.255(9) . ? C11 C12 1.387(10) . ? C11 C16 1.391(9) . ? C11 C18 1.501(10) . ? C12 C13 1.373(10) . ? C12 H12 0.9300 . ? C13 C14 1.384(9) . ? C14 C15 1.391(10) . ? C14 H14 0.9300 . ? C15 C16 1.404(10) . ? C16 H16 0.9300 . ? N21 C25 1.288(17) . ? N21 C21 1.334(16) . ? C21 C22 1.36(2) . ? C21 H21 0.9300 . ? C22 C23 1.41(3) . ? C22 H22 0.9300 . ? C23 C24 1.27(2) . ? C23 H23 0.9300 . ? C24 C25 1.41(2) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? O31 H31A 0.9300 . ? O31 H31B 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 O13 Cu2 128.5(6) . 13_455 ? O13 C19 O14 123.1(8) . . ? O13 C19 C15 117.6(8) . . ? O14 C19 C15 119.4(8) . . ? C18 O12 Cu1 124.8(5) . 9_566 ? O12 Cu1 O12 88.2(4) 9_566 2_565 ? O12 Cu1 O11 166.4(2) 9_566 . ? O12 Cu1 O11 90.1(2) 2_565 . ? O12 Cu1 O11 90.1(2) 9_566 10_556 ? O12 Cu1 O11 166.4(2) 2_565 10_556 ? O11 Cu1 O11 88.4(4) . 10_556 ? O12 Cu1 N21 97.8(3) 9_566 . ? O12 Cu1 N21 97.8(3) 2_565 . ? O11 Cu1 N21 95.8(3) . . ? O11 Cu1 N21 95.8(3) 10_556 . ? O12 Cu1 Cu1 83.33(18) 9_566 9_566 ? O12 Cu1 Cu1 83.33(18) 2_565 9_566 ? O11 Cu1 Cu1 83.06(16) . 9_566 ? O11 Cu1 Cu1 83.06(16) 10_556 9_566 ? N21 Cu1 Cu1 178.5(3) . 9_566 ? O13 Cu2 O13 166.7(4) 11_665 13_455 ? O13 Cu2 N11 93.8(2) 11_665 . ? O13 Cu2 N11 88.8(2) 13_455 . ? O13 Cu2 N11 88.8(2) 11_665 7_445 ? O13 Cu2 N11 93.8(2) 13_455 7_445 ? N11 Cu2 N11 157.9(4) . 7_445 ? O13 Cu2 O31 83.37(18) 11_665 . ? O13 Cu2 O31 83.37(18) 13_455 . ? N11 Cu2 O31 101.06(18) . . ? N11 Cu2 O31 101.06(18) 7_445 . ? C13 N11 Cu2 113.7(5) . . ? C13 N11 H11A 108.8 . . ? Cu2 N11 H11A 108.8 . . ? C13 N11 H11B 108.8 . . ? Cu2 N11 H11B 108.8 . . ? H11A N11 H11B 107.7 . . ? C18 O11 Cu1 123.6(5) . . ? C12 C11 C16 119.0(7) . . ? C12 C11 C18 121.4(7) . . ? C16 C11 C18 119.6(7) . . ? C13 C12 C11 121.7(7) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 119.6(7) . . ? C12 C13 N11 120.7(7) . . ? C14 C13 N11 119.7(7) . . ? C13 C14 C15 120.0(7) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 120.0(7) . . ? C14 C15 C19 120.8(7) . . ? C16 C15 C19 119.2(7) . . ? C11 C16 C15 119.6(7) . . ? C11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? O12 C18 O11 125.1(7) . . ? O12 C18 C11 118.6(7) . . ? O11 C18 C11 116.2(8) . . ? C25 N21 C21 116.4(13) . . ? C25 N21 Cu1 122.7(10) . . ? C21 N21 Cu1 120.9(10) . . ? N21 C21 C22 123.1(17) . . ? N21 C21 H21 118.5 . . ? C22 C21 H21 118.5 . . ? C21 C22 C23 117.4(19) . . ? C21 C22 H22 121.3 . . ? C23 C22 H22 121.3 . . ? C24 C23 C22 121(2) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 118(2) . . ? C23 C24 H24 121.0 . . ? C25 C24 H24 121.0 . . ? N21 C25 C24 124.5(16) . . ? N21 C25 H25 117.8 . . ? C24 C25 H25 117.8 . . ? Cu2 O31 H31A 120.0 . . ? Cu2 O31 H31B 120.0 . . ? H31A O31 H31B 120.0 . . ? 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 Cu2 O13 C19 O14 11.0(15) 13_455 . . . ? Cu2 O13 C19 C15 -169.3(6) 13_455 . . . ? O13 Cu2 N11 C13 96.9(5) 11_665 . . . ? O13 Cu2 N11 C13 -70.1(5) 13_455 . . . ? N11 Cu2 N11 C13 -167.1(5) 7_445 . . . ? O31 Cu2 N11 C13 12.9(5) . . . . ? O12 Cu1 O11 C18 -2.6(15) 9_566 . . . ? O12 Cu1 O11 C18 -85.3(6) 2_565 . . . ? O11 Cu1 O11 C18 81.2(7) 10_556 . . . ? N21 Cu1 O11 C18 176.9(6) . . . . ? Cu1 Cu1 O11 C18 -2.0(6) 9_566 . . . ? C16 C11 C12 C13 0.7(11) . . . . ? C18 C11 C12 C13 177.8(7) . . . . ? C11 C12 C13 C14 -1.8(11) . . . . ? C11 C12 C13 N11 176.8(7) . . . . ? Cu2 N11 C13 C12 -84.5(7) . . . . ? Cu2 N11 C13 C14 94.1(7) . . . . ? C12 C13 C14 C15 2.6(11) . . . . ? N11 C13 C14 C15 -176.0(7) . . . . ? C13 C14 C15 C16 -2.3(12) . . . . ? C13 C14 C15 C19 177.6(8) . . . . ? O13 C19 C15 C14 -3.5(13) . . . . ? O14 C19 C15 C14 176.2(10) . . . . ? O13 C19 C15 C16 176.4(8) . . . . ? O14 C19 C15 C16 -3.9(14) . . . . ? C12 C11 C16 C15 -0.4(11) . . . . ? C18 C11 C16 C15 -177.6(7) . . . . ? C14 C15 C16 C11 1.2(12) . . . . ? C19 C15 C16 C11 -178.7(8) . . . . ? Cu1 O12 C18 O11 -4.0(12) 9_566 . . . ? Cu1 O12 C18 C11 174.3(5) 9_566 . . . ? Cu1 O11 C18 O12 4.2(12) . . . . ? Cu1 O11 C18 C11 -174.2(5) . . . . ? C12 C11 C18 O12 -179.4(7) . . . . ? C16 C11 C18 O12 -2.2(11) . . . . ? C12 C11 C18 O11 -0.9(11) . . . . ? C16 C11 C18 O11 176.3(7) . . . . ? O12 Cu1 N21 C25 135.41(18) 9_566 . . . ? O12 Cu1 N21 C25 -135.41(18) 2_565 . . . ? O11 Cu1 N21 C25 -44.47(18) . . . . ? O11 Cu1 N21 C25 44.47(18) 10_556 . . . ? Cu1 Cu1 N21 C25 0.0 9_566 . . . ? O12 Cu1 N21 C21 -44.59(18) 9_566 . . . ? O12 Cu1 N21 C21 44.59(18) 2_565 . . . ? O11 Cu1 N21 C21 135.53(18) . . . . ? O11 Cu1 N21 C21 -135.53(18) 10_556 . . . ? Cu1 Cu1 N21 C21 180.0 9_566 . . . ? C25 N21 C21 C22 0.0 . . . . ? Cu1 N21 C21 C22 180.0 . . . . ? N21 C21 C22 C23 0.0 . . . . ? C21 C22 C23 C24 0.0 . . . . ? C22 C23 C24 C25 0.0 . . . . ? C21 N21 C25 C24 0.0 . . . . ? Cu1 N21 C25 C24 180.0 . . . . ? C23 C24 C25 N21 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.11 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.995 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.126 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 658211' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Cu N2 O4' _chemical_formula_weight 335.80 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.7210(18) _cell_length_b 7.7387(11) _cell_length_c 14.005(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.106(2) _cell_angle_gamma 90.00 _cell_volume 1310.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 1.684 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.683 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Saint, 1995, Bruker Axs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6452 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.14 _reflns_number_total 2316 _reflns_number_gt 1776 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0498P)^2^+0.8462P] 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 2316 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1139 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O13 O -0.1401(2) 0.2768(3) 0.7015(2) 0.0290(7) Uani 1 1 d . . . O14 O 0.0205(2) 0.1685(3) 0.7787(2) 0.0357(8) Uani 1 1 d . . . C19 C -0.0458(3) 0.2942(5) 0.7650(3) 0.0223(9) Uani 1 1 d . . . O12 O 0.2672(2) 0.5118(3) 1.0680(2) 0.0307(7) Uani 1 1 d . . . C18 C 0.2006(3) 0.6401(5) 1.0516(3) 0.0228(9) Uani 1 1 d . . . Cu1 Cu -0.10334(4) 1.02491(6) 0.67992(4) 0.0269(2) Uani 1 1 d . . . N11 N -0.1348(3) 0.8981(4) 0.8095(2) 0.0231(8) Uani 1 1 d . . . H11A H -0.1250 0.9755 0.8595 0.028 Uiso 1 1 calc R . . H11B H -0.2055 0.8623 0.7915 0.028 Uiso 1 1 calc R . . O11 O 0.2116(2) 0.7690(4) 1.1055(2) 0.0356(8) Uani 1 1 d . . . C11 C -0.0156(3) 0.4582(5) 0.8216(3) 0.0206(9) Uani 1 1 d . . . C12 C 0.0794(3) 0.4733(5) 0.9043(3) 0.0228(9) Uani 1 1 d . . . H12 H 0.1279 0.3804 0.9231 0.027 Uiso 1 1 calc R . . C13 C 0.1018(3) 0.6261(5) 0.9586(3) 0.0193(9) Uani 1 1 d . . . C14 C 0.0297(3) 0.7655(5) 0.9284(3) 0.0215(9) Uani 1 1 d . . . H14 H 0.0447 0.8681 0.9647 0.026 Uiso 1 1 calc R . . C15 C -0.0636(3) 0.7539(5) 0.8453(3) 0.0197(9) Uani 1 1 d . . . C16 C -0.0867(3) 0.5989(5) 0.7925(3) 0.0209(9) Uani 1 1 d . . . H16 H -0.1501 0.5892 0.7374 0.025 Uiso 1 1 calc R . . N21 N -0.0005(3) 0.8744(4) 0.6337(3) 0.0290(8) Uani 1 1 d . . . C21 C 0.1012(4) 0.8416(6) 0.6947(3) 0.0409(12) Uani 1 1 d . . . H21 H 0.1221 0.8865 0.7595 0.049 Uiso 1 1 calc R . . C22 C 0.1763(4) 0.7440(7) 0.6656(4) 0.0475(14) Uani 1 1 d . . . H22 H 0.2462 0.7240 0.7107 0.057 Uiso 1 1 calc R . . C23 C 0.1486(4) 0.6748(6) 0.5691(4) 0.0365(11) Uani 1 1 d . . . C24 C 0.0424(4) 0.7117(6) 0.5077(3) 0.0365(11) Uani 1 1 d . . . H24 H 0.0188 0.6687 0.4425 0.044 Uiso 1 1 calc R . . C25 C -0.0281(4) 0.8100(6) 0.5411(3) 0.0336(11) Uani 1 1 d . . . H25 H -0.0983 0.8329 0.4974 0.040 Uiso 1 1 calc R . . C26 C 0.2269(4) 0.5667(7) 0.5344(4) 0.0522(14) Uani 1 1 d . . . H26A H 0.2036 0.4482 0.5297 0.078 Uiso 1 1 calc R . . H26B H 0.2999 0.5764 0.5815 0.078 Uiso 1 1 calc R . . H26C H 0.2276 0.6062 0.4696 0.078 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 O13 0.0245(17) 0.0226(15) 0.0325(16) -0.0071(12) -0.0016(14) 0.0043(12) O14 0.0264(17) 0.0246(16) 0.0427(18) -0.0099(13) -0.0089(15) 0.0088(13) C19 0.019(2) 0.020(2) 0.022(2) -0.0004(17) -0.0022(18) -0.0054(16) O12 0.0232(16) 0.0269(16) 0.0317(16) 0.0044(13) -0.0063(13) 0.0045(12) C18 0.021(2) 0.024(2) 0.020(2) 0.0067(17) 0.0026(18) -0.0044(17) Cu1 0.0226(3) 0.0224(3) 0.0279(3) -0.0059(2) -0.0037(2) 0.0010(2) N11 0.0190(18) 0.0188(17) 0.0246(18) -0.0020(14) -0.0031(15) 0.0017(14) O11 0.0342(19) 0.0305(17) 0.0288(16) -0.0063(14) -0.0094(14) -0.0026(14) C11 0.021(2) 0.0166(19) 0.022(2) -0.0022(16) 0.0046(18) -0.0005(16) C12 0.018(2) 0.019(2) 0.027(2) 0.0021(17) 0.0013(18) 0.0010(16) C13 0.018(2) 0.019(2) 0.018(2) 0.0009(16) 0.0009(17) -0.0028(16) C14 0.023(2) 0.018(2) 0.018(2) -0.0024(16) -0.0005(18) -0.0035(16) C15 0.018(2) 0.021(2) 0.018(2) 0.0021(16) 0.0025(17) 0.0004(16) C16 0.015(2) 0.025(2) 0.0167(19) -0.0008(17) -0.0041(17) -0.0002(16) N21 0.026(2) 0.0277(19) 0.032(2) -0.0038(16) 0.0063(17) 0.0013(15) C21 0.033(3) 0.050(3) 0.031(3) -0.010(2) -0.002(2) 0.006(2) C22 0.036(3) 0.060(3) 0.038(3) -0.005(2) -0.002(2) 0.013(2) C23 0.033(3) 0.032(3) 0.045(3) 0.000(2) 0.013(2) 0.002(2) C24 0.038(3) 0.039(3) 0.032(2) -0.008(2) 0.010(2) 0.000(2) C25 0.029(3) 0.036(3) 0.032(2) -0.005(2) 0.005(2) -0.0017(19) C26 0.040(3) 0.054(3) 0.057(3) -0.016(3) 0.008(3) 0.010(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 O13 C19 1.260(4) . ? O13 Cu1 2.049(3) 1_545 ? O14 C19 1.262(5) . ? O14 Cu1 2.067(3) 1_545 ? C19 C11 1.482(5) . ? C19 Cu1 2.400(4) 1_545 ? O12 C18 1.279(5) . ? O12 Cu1 1.909(3) 4_676 ? C18 O11 1.232(5) . ? C18 C13 1.506(5) . ? Cu1 O12 1.909(3) 4_575 ? Cu1 N21 2.004(4) . ? Cu1 O13 2.049(3) 1_565 ? Cu1 O14 2.067(3) 1_565 ? Cu1 N11 2.206(3) . ? Cu1 C19 2.400(4) 1_565 ? N11 C15 1.426(5) . ? N11 H11A 0.9000 . ? N11 H11B 0.9000 . ? C11 C16 1.393(5) . ? C11 C12 1.395(5) . ? C12 C13 1.387(5) . ? C12 H12 0.9300 . ? C13 C14 1.394(5) . ? C14 C15 1.383(5) . ? C14 H14 0.9300 . ? C15 C16 1.392(5) . ? C16 H16 0.9300 . ? N21 C25 1.329(5) . ? N21 C21 1.335(5) . ? C21 C22 1.375(7) . ? C21 H21 0.9300 . ? C22 C23 1.393(6) . ? C22 H22 0.9300 . ? C23 C24 1.387(6) . ? C23 C26 1.494(7) . ? C24 C25 1.365(6) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? 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 C19 O13 Cu1 89.7(2) . 1_545 ? C19 O14 Cu1 88.8(2) . 1_545 ? O13 C19 O14 117.9(3) . . ? O13 C19 C11 120.1(3) . . ? O14 C19 C11 122.0(3) . . ? O13 C19 Cu1 58.61(18) . 1_545 ? O14 C19 Cu1 59.5(2) . 1_545 ? C11 C19 Cu1 176.0(3) . 1_545 ? C18 O12 Cu1 128.1(3) . 4_676 ? O11 C18 O12 125.1(4) . . ? O11 C18 C13 119.6(3) . . ? O12 C18 C13 115.3(3) . . ? O12 Cu1 N21 97.53(13) 4_575 . ? O12 Cu1 O13 94.86(11) 4_575 1_565 ? N21 Cu1 O13 143.37(14) . 1_565 ? O12 Cu1 O14 155.86(11) 4_575 1_565 ? N21 Cu1 O14 95.19(13) . 1_565 ? O13 Cu1 O14 63.33(11) 1_565 1_565 ? O12 Cu1 N11 106.19(13) 4_575 . ? N21 Cu1 N11 108.11(13) . . ? O13 Cu1 N11 101.19(12) 1_565 . ? O14 Cu1 N11 89.09(12) 1_565 . ? O12 Cu1 C19 126.12(12) 4_575 1_565 ? N21 Cu1 C19 122.43(14) . 1_565 ? O13 Cu1 C19 31.66(11) 1_565 1_565 ? O14 Cu1 C19 31.72(12) 1_565 1_565 ? N11 Cu1 C19 94.77(13) . 1_565 ? C15 N11 Cu1 112.4(2) . . ? C15 N11 H11A 109.1 . . ? Cu1 N11 H11A 109.1 . . ? C15 N11 H11B 109.1 . . ? Cu1 N11 H11B 109.1 . . ? H11A N11 H11B 107.9 . . ? C16 C11 C12 119.6(3) . . ? C16 C11 C19 118.5(3) . . ? C12 C11 C19 121.9(3) . . ? C13 C12 C11 120.3(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 119.3(3) . . ? C12 C13 C18 120.7(3) . . ? C14 C13 C18 120.0(3) . . ? C15 C14 C13 121.2(3) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 119.1(3) . . ? C14 C15 N11 122.1(3) . . ? C16 C15 N11 118.8(3) . . ? C15 C16 C11 120.5(3) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C25 N21 C21 117.5(4) . . ? C25 N21 Cu1 122.1(3) . . ? C21 N21 Cu1 120.3(3) . . ? N21 C21 C22 122.7(4) . . ? N21 C21 H21 118.7 . . ? C22 C21 H21 118.7 . . ? C21 C22 C23 120.5(5) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 115.3(4) . . ? C24 C23 C26 122.2(4) . . ? C22 C23 C26 122.5(4) . . ? C25 C24 C23 121.3(4) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? N21 C25 C24 122.7(4) . . ? N21 C25 H25 118.6 . . ? C24 C25 H25 118.6 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 Cu1 O13 C19 O14 4.0(4) 1_545 . . . ? Cu1 O13 C19 C11 -175.7(3) 1_545 . . . ? Cu1 O14 C19 O13 -4.0(4) 1_545 . . . ? Cu1 O14 C19 C11 175.7(4) 1_545 . . . ? Cu1 O12 C18 O11 3.0(6) 4_676 . . . ? Cu1 O12 C18 C13 -176.6(2) 4_676 . . . ? O12 Cu1 N11 C15 113.7(2) 4_575 . . . ? N21 Cu1 N11 C15 9.9(3) . . . . ? O13 Cu1 N11 C15 -147.8(2) 1_565 . . . ? O14 Cu1 N11 C15 -85.2(2) 1_565 . . . ? C19 Cu1 N11 C15 -116.5(3) 1_565 . . . ? O13 C19 C11 C16 -9.3(6) . . . . ? O14 C19 C11 C16 171.1(4) . . . . ? Cu1 C19 C11 C16 -79(4) 1_545 . . . ? O13 C19 C11 C12 168.6(4) . . . . ? O14 C19 C11 C12 -11.1(6) . . . . ? Cu1 C19 C11 C12 99(4) 1_545 . . . ? C16 C11 C12 C13 1.3(6) . . . . ? C19 C11 C12 C13 -176.5(4) . . . . ? C11 C12 C13 C14 -1.4(6) . . . . ? C11 C12 C13 C18 176.4(4) . . . . ? O11 C18 C13 C12 -171.1(4) . . . . ? O12 C18 C13 C12 8.5(6) . . . . ? O11 C18 C13 C14 6.6(6) . . . . ? O12 C18 C13 C14 -173.8(4) . . . . ? C12 C13 C14 C15 0.1(6) . . . . ? C18 C13 C14 C15 -177.7(4) . . . . ? C13 C14 C15 C16 1.3(6) . . . . ? C13 C14 C15 N11 -176.1(4) . . . . ? Cu1 N11 C15 C14 99.8(4) . . . . ? Cu1 N11 C15 C16 -77.6(4) . . . . ? C14 C15 C16 C11 -1.3(6) . . . . ? N11 C15 C16 C11 176.1(4) . . . . ? C12 C11 C16 C15 0.0(6) . . . . ? C19 C11 C16 C15 177.9(4) . . . . ? O12 Cu1 N21 C25 10.7(4) 4_575 . . . ? O13 Cu1 N21 C25 -98.0(4) 1_565 . . . ? O14 Cu1 N21 C25 -148.7(3) 1_565 . . . ? N11 Cu1 N21 C25 120.5(3) . . . . ? C19 Cu1 N21 C25 -131.3(3) 1_565 . . . ? O12 Cu1 N21 C21 -172.2(3) 4_575 . . . ? O13 Cu1 N21 C21 79.1(4) 1_565 . . . ? O14 Cu1 N21 C21 28.4(4) 1_565 . . . ? N11 Cu1 N21 C21 -62.4(4) . . . . ? C19 Cu1 N21 C21 45.8(4) 1_565 . . . ? C25 N21 C21 C22 -0.6(7) . . . . ? Cu1 N21 C21 C22 -177.8(4) . . . . ? N21 C21 C22 C23 0.3(8) . . . . ? C21 C22 C23 C24 -0.1(7) . . . . ? C21 C22 C23 C26 -179.5(5) . . . . ? C22 C23 C24 C25 0.3(7) . . . . ? C26 C23 C24 C25 179.7(5) . . . . ? C21 N21 C25 C24 0.8(7) . . . . ? Cu1 N21 C25 C24 177.9(4) . . . . ? C23 C24 C25 N21 -0.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.493 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.091