data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year 2012 _journal_volume 41 _journal_page_first 9192 _publ_contact_author_address ? _publ_contact_author_email anne.duhme-klair@york.ac.uk _publ_contact_author_phone ? _publ_contact_author_name 'Anne-Kathrin Duhme-Klair' loop_ _publ_author_name 'Abeda Jamadar' A.-K.Duhme-Klair 'Kiranmayi Vemuri' 'Manjula Sritharan' 'Prasad Dandawate' 'Subhash Padhye' data_akd0903m _database_code_depnum_ccdc_archive 'CCDC 866682' #TrackingRef '- akd0903m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 N2 Na O5' _chemical_formula_sum 'C11 H15 N2 Na O5' _chemical_formula_weight 278.24 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 30.7555(9) _cell_length_b 30.7555(9) _cell_length_c 7.3013(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5981.0(6) _cell_formula_units_Z 18 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4444 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 28.15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2628 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.836 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details 'SADABS v2.10; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 20886 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3303 _reflns_number_gt 2741 _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. C-H hydrogens were placed using a riding model. O-H and N-H hydrogens were located by difference map after all other atoms werre located. The methyl hydrogens on the phenyl group were found to be disordered and were modelled in two positions 60 degrees apart with equal occupancy using AFIX 127. ; _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^)+(0.0715P)^2^+2.3390P] 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 3303 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1026 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 C1 C 0.91253(5) 0.18629(5) 0.84256(19) 0.0184(3) Uani 1 1 d . . . C2 C 0.86702(5) 0.13393(5) 0.87032(18) 0.0169(3) Uani 1 1 d . . . C3 C 0.76769(5) 0.15473(5) 0.98248(17) 0.0162(3) Uani 1 1 d . . . C4 C 0.76241(5) 0.20040(5) 1.00222(18) 0.0168(3) Uani 1 1 d . . . C5 C 0.80269(5) 0.24971(5) 0.99507(19) 0.0192(3) Uani 1 1 d . . . H5 H 0.8357 0.2557 0.9743 0.023 Uiso 1 1 calc R . . C6 C 0.79458(5) 0.28989(5) 1.01813(19) 0.0215(3) Uani 1 1 d . . . H6 H 0.8222 0.3232 1.0132 0.026 Uiso 1 1 calc R . . C7 C 0.74647(5) 0.28205(5) 1.0484(2) 0.0244(3) Uani 1 1 d . . . C8 C 0.70646(5) 0.23282(5) 1.0541(2) 0.0283(3) Uani 1 1 d . . . H8 H 0.6734 0.2268 1.0740 0.034 Uiso 1 1 calc R . . C9 C 0.71433(5) 0.19250(5) 1.0313(2) 0.0242(3) Uani 1 1 d . . . H9 H 0.6866 0.1592 1.0356 0.029 Uiso 1 1 calc R . . C10 C 0.87594(5) 0.09062(5) 0.8480(2) 0.0218(3) Uani 1 1 d . . . H10A H 0.8446 0.0592 0.8710 0.033 Uiso 1 1 calc R . . H10B H 0.9016 0.0939 0.9353 0.033 Uiso 1 1 calc R . . H10C H 0.8874 0.0904 0.7229 0.033 Uiso 1 1 calc R . . C11 C 0.73828(6) 0.32610(6) 1.0770(3) 0.0348(4) Uani 1 1 d . . . H11A H 0.7036 0.3139 1.1170 0.052 Uiso 0.50 1 calc PR . . H11B H 0.7444 0.3446 0.9618 0.052 Uiso 0.50 1 calc PR . . H11C H 0.7615 0.3484 1.1709 0.052 Uiso 0.50 1 calc PR . . H11D H 0.7694 0.3574 1.0495 0.052 Uiso 0.50 1 calc PR . . H11E H 0.7287 0.3266 1.2046 0.052 Uiso 0.50 1 calc PR . . H11F H 0.7115 0.3229 0.9956 0.052 Uiso 0.50 1 calc PR . . N1 N 0.82223(4) 0.12363(4) 0.91403(16) 0.0181(2) Uani 1 1 d . . . N2 N 0.81375(4) 0.16355(4) 0.93269(16) 0.0184(2) Uani 1 1 d . . . H2 H 0.8416(7) 0.1946(7) 0.918(2) 0.029(5) Uiso 1 1 d . . . Na1 Na 0.700684(18) 0.049964(19) 1.23753(7) 0.01704(15) Uani 1 1 d . . . O1 O 0.90780(3) 0.22448(3) 0.87389(13) 0.0192(2) Uani 1 1 d . . . O2 O 0.95150(4) 0.18731(4) 0.79270(17) 0.0315(3) Uani 1 1 d . . . O3 O 0.73182(3) 0.11232(3) 1.01019(13) 0.0192(2) Uani 1 1 d . . . O4 O 0.75051(4) 0.02671(4) 1.07492(14) 0.0189(2) Uani 1 1 d . . . H4A H 0.7732(8) 0.0509(9) 1.024(3) 0.049(6) Uiso 1 1 d . . . H4B H 0.7621(7) 0.0094(7) 1.123(3) 0.035(5) Uiso 1 1 d . . . O5 O 0.62960(4) -0.00844(4) 1.06118(15) 0.0195(2) Uani 1 1 d . . . H5A H 0.6118(8) -0.0075(8) 0.984(3) 0.046(6) Uiso 1 1 d . . . H5B H 0.6092(8) -0.0240(8) 1.142(3) 0.039(6) 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 C1 0.0167(6) 0.0153(6) 0.0206(6) -0.0023(5) -0.0011(5) 0.0060(5) C2 0.0178(6) 0.0141(6) 0.0177(6) -0.0010(5) 0.0000(5) 0.0071(5) C3 0.0156(6) 0.0165(6) 0.0154(6) -0.0004(5) -0.0014(4) 0.0072(5) C4 0.0160(6) 0.0148(6) 0.0188(6) -0.0001(5) -0.0013(5) 0.0070(5) C5 0.0148(6) 0.0177(6) 0.0239(7) -0.0008(5) -0.0015(5) 0.0071(5) C6 0.0195(6) 0.0142(6) 0.0275(7) -0.0011(5) -0.0037(5) 0.0060(5) C7 0.0239(7) 0.0203(7) 0.0322(8) -0.0028(6) -0.0038(6) 0.0134(6) C8 0.0171(7) 0.0231(7) 0.0469(9) -0.0018(6) -0.0003(6) 0.0116(6) C9 0.0170(6) 0.0176(6) 0.0357(8) -0.0001(5) 0.0005(5) 0.0070(5) C10 0.0212(7) 0.0159(6) 0.0283(7) -0.0007(5) 0.0031(5) 0.0091(5) C11 0.0320(8) 0.0236(8) 0.0545(11) -0.0039(7) -0.0021(7) 0.0182(7) N1 0.0182(5) 0.0134(5) 0.0223(6) -0.0002(4) 0.0008(4) 0.0076(4) N2 0.0149(5) 0.0126(5) 0.0267(6) 0.0007(4) 0.0023(4) 0.0061(4) Na1 0.0155(3) 0.0148(3) 0.0196(3) -0.00023(19) 0.00120(19) 0.0066(2) O1 0.0164(4) 0.0142(4) 0.0255(5) -0.0017(4) 0.0007(4) 0.0065(4) O2 0.0175(5) 0.0198(5) 0.0551(8) -0.0069(5) 0.0069(5) 0.0077(4) O3 0.0164(5) 0.0141(4) 0.0239(5) 0.0014(4) 0.0017(4) 0.0053(4) O4 0.0153(5) 0.0156(5) 0.0250(5) 0.0022(4) 0.0011(4) 0.0071(4) O5 0.0151(5) 0.0249(5) 0.0178(5) -0.0001(4) 0.0001(4) 0.0094(4) _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 C1 O2 1.2380(16) . ? C1 O1 1.2743(16) . ? C1 C2 1.5295(17) . ? C2 N1 1.2897(17) . ? C2 C10 1.4970(18) . ? C3 O3 1.2330(15) . ? C3 N2 1.3522(16) . ? C3 C4 1.4996(17) . ? C4 C9 1.3896(18) . ? C4 C5 1.3996(18) . ? C5 C6 1.3878(18) . ? C5 H5 0.9500 . ? C6 C7 1.393(2) . ? C6 H6 0.9500 . ? C7 C8 1.395(2) . ? C7 C11 1.511(2) . ? C8 C9 1.3872(19) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C11 H11D 0.9800 . ? C11 H11E 0.9800 . ? C11 H11F 0.9800 . ? N1 N2 1.3835(15) . ? N2 H2 0.916(18) . ? Na1 O4 2.3162(11) . ? Na1 O4 2.3459(11) 5_545 ? Na1 O3 2.3482(10) . ? Na1 O5 2.3952(11) . ? Na1 O1 2.4222(11) 13_657 ? Na1 O5 2.4232(11) 5_545 ? Na1 Na1 3.3864(6) 5_545 ? Na1 Na1 3.3864(6) 9_654 ? Na1 H5B 2.68(2) . ? O1 Na1 2.4223(11) 13_657 ? O4 Na1 2.3458(11) 9_654 ? O4 H4A 0.81(2) . ? O4 H4B 0.85(2) . ? O5 Na1 2.4233(11) 9_654 ? O5 H5A 0.79(2) . ? O5 H5B 0.82(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 O2 C1 O1 125.78(12) . . ? O2 C1 C2 115.49(11) . . ? O1 C1 C2 118.72(11) . . ? N1 C2 C10 117.19(11) . . ? N1 C2 C1 126.45(11) . . ? C10 C2 C1 116.35(11) . . ? O3 C3 N2 123.37(12) . . ? O3 C3 C4 121.08(11) . . ? N2 C3 C4 115.55(11) . . ? C9 C4 C5 118.90(12) . . ? C9 C4 C3 117.07(11) . . ? C5 C4 C3 124.03(11) . . ? C6 C5 C4 120.29(12) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 120.90(12) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C6 C7 C8 118.49(13) . . ? C6 C7 C11 120.36(13) . . ? C8 C7 C11 121.14(13) . . ? C9 C8 C7 120.88(13) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C4 120.53(13) . . ? C8 C9 H9 119.7 . . ? C4 C9 H9 119.7 . . ? C2 C10 H10A 109.5 . . ? C2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C11 H11D 109.5 . . ? H11A C11 H11D 141.1 . . ? H11B C11 H11D 56.3 . . ? H11C C11 H11D 56.3 . . ? C7 C11 H11E 109.5 . . ? H11A C11 H11E 56.3 . . ? H11B C11 H11E 141.1 . . ? H11C C11 H11E 56.3 . . ? H11D C11 H11E 109.5 . . ? C7 C11 H11F 109.5 . . ? H11A C11 H11F 56.3 . . ? H11B C11 H11F 56.3 . . ? H11C C11 H11F 141.1 . . ? H11D C11 H11F 109.5 . . ? H11E C11 H11F 109.5 . . ? C2 N1 N2 117.29(11) . . ? C3 N2 N1 119.46(11) . . ? C3 N2 H2 125.5(11) . . ? N1 N2 H2 114.8(11) . . ? O4 Na1 O4 169.16(4) . 5_545 ? O4 Na1 O3 80.05(4) . . ? O4 Na1 O3 108.51(4) 5_545 . ? O4 Na1 O5 89.40(4) . . ? O4 Na1 O5 83.40(4) 5_545 . ? O3 Na1 O5 94.53(4) . . ? O4 Na1 O1 102.61(4) . 13_657 ? O4 Na1 O1 84.23(4) 5_545 13_657 ? O3 Na1 O1 90.86(4) . 13_657 ? O5 Na1 O1 167.54(4) . 13_657 ? O4 Na1 O5 82.50(4) . 5_545 ? O4 Na1 O5 88.03(4) 5_545 5_545 ? O3 Na1 O5 160.98(4) . 5_545 ? O5 Na1 O5 77.694(16) . 5_545 ? O1 Na1 O5 100.34(4) 13_657 5_545 ? O4 Na1 Na1 127.44(3) . 5_545 ? O4 Na1 Na1 43.07(3) 5_545 5_545 ? O3 Na1 Na1 150.97(3) . 5_545 ? O5 Na1 Na1 78.49(3) . 5_545 ? O1 Na1 Na1 91.38(3) 13_657 5_545 ? O5 Na1 Na1 45.01(3) 5_545 5_545 ? O4 Na1 Na1 43.76(3) . 9_654 ? O4 Na1 Na1 128.23(3) 5_545 9_654 ? O3 Na1 Na1 87.67(3) . 9_654 ? O5 Na1 Na1 45.69(2) . 9_654 ? O1 Na1 Na1 146.02(3) 13_657 9_654 ? O5 Na1 Na1 74.43(3) 5_545 9_654 ? Na1 Na1 Na1 105.950(17) 5_545 9_654 ? O4 Na1 H5B 100.4(4) . . ? O4 Na1 H5B 70.8(4) 5_545 . ? O3 Na1 H5B 109.6(5) . . ? O5 Na1 H5B 17.4(5) . . ? O1 Na1 H5B 151.5(5) 13_657 . ? O5 Na1 H5B 66.2(4) 5_545 . ? Na1 Na1 H5B 61.1(5) 5_545 . ? Na1 Na1 H5B 57.5(4) 9_654 . ? C1 O1 Na1 115.29(8) . 13_657 ? C3 O3 Na1 139.79(9) . . ? Na1 O4 Na1 93.17(4) . 9_654 ? Na1 O4 H4A 110.5(16) . . ? Na1 O4 H4A 120.2(15) 9_654 . ? Na1 O4 H4B 122.3(13) . . ? Na1 O4 H4B 101.7(13) 9_654 . ? H4A O4 H4B 109(2) . . ? Na1 O5 Na1 89.30(3) . 9_654 ? Na1 O5 H5A 137.8(15) . . ? Na1 O5 H5A 105.2(16) 9_654 . ? Na1 O5 H5B 101.3(14) . . ? Na1 O5 H5B 126.5(14) 9_654 . ? H5A O5 H5B 101(2) . . ? 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 O2 C1 C2 N1 -176.85(14) . . . . ? O1 C1 C2 N1 4.0(2) . . . . ? O2 C1 C2 C10 4.47(18) . . . . ? O1 C1 C2 C10 -174.65(12) . . . . ? O3 C3 C4 C9 -7.45(19) . . . . ? N2 C3 C4 C9 172.40(13) . . . . ? O3 C3 C4 C5 171.82(12) . . . . ? N2 C3 C4 C5 -8.33(19) . . . . ? C9 C4 C5 C6 0.5(2) . . . . ? C3 C4 C5 C6 -178.77(12) . . . . ? C4 C5 C6 C7 -0.1(2) . . . . ? C5 C6 C7 C8 -0.3(2) . . . . ? C5 C6 C7 C11 178.78(14) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C11 C7 C8 C9 -178.73(16) . . . . ? C7 C8 C9 C4 0.0(2) . . . . ? C5 C4 C9 C8 -0.4(2) . . . . ? C3 C4 C9 C8 178.86(14) . . . . ? C10 C2 N1 N2 -179.27(12) . . . . ? C1 C2 N1 N2 2.1(2) . . . . ? O3 C3 N2 N1 -1.2(2) . . . . ? C4 C3 N2 N1 179.00(11) . . . . ? C2 N1 N2 C3 -178.49(12) . . . . ? O2 C1 O1 Na1 -55.45(18) . . . 13_657 ? C2 C1 O1 Na1 123.57(10) . . . 13_657 ? N2 C3 O3 Na1 78.48(18) . . . . ? C4 C3 O3 Na1 -101.68(15) . . . . ? O4 Na1 O3 C3 -89.47(13) . . . . ? O4 Na1 O3 C3 97.39(14) 5_545 . . . ? O5 Na1 O3 C3 -178.06(13) . . . . ? O1 Na1 O3 C3 13.18(14) 13_657 . . . ? O5 Na1 O3 C3 -113.27(17) 5_545 . . . ? Na1 Na1 O3 C3 107.58(13) 5_545 . . . ? Na1 Na1 O3 C3 -132.86(13) 9_654 . . . ? O4 Na1 O4 Na1 45.9(3) 5_545 . . 9_654 ? O3 Na1 O4 Na1 -97.09(4) . . . 9_654 ? O5 Na1 O4 Na1 -2.38(4) . . . 9_654 ? O1 Na1 O4 Na1 174.27(4) 13_657 . . 9_654 ? O5 Na1 O4 Na1 75.29(4) 5_545 . . 9_654 ? Na1 Na1 O4 Na1 72.59(5) 5_545 . . 9_654 ? O4 Na1 O5 Na1 2.30(4) . . . 9_654 ? O4 Na1 O5 Na1 -169.58(4) 5_545 . . 9_654 ? O3 Na1 O5 Na1 82.27(4) . . . 9_654 ? O1 Na1 O5 Na1 -162.35(18) 13_657 . . 9_654 ? O5 Na1 O5 Na1 -80.16(4) 5_545 . . 9_654 ? Na1 Na1 O5 Na1 -126.21(3) 5_545 . . 9_654 ? 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 N2 H2 O1 0.916(18) 1.795(18) 2.5772(14) 141.7(16) . O4 H4A N1 0.81(2) 2.13(2) 2.9249(15) 165(2) . O4 H4B O2 0.85(2) 1.91(2) 2.7268(15) 159.1(19) 12_547 O5 H5A O1 0.79(2) 2.08(2) 2.8674(14) 171(2) 17_556 O5 H5B O3 0.82(2) 2.08(2) 2.8756(14) 164.7(19) 5_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.470 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.114 # Attachment '9539_web_deposit_cif_file_1_Anne-KathrinDuhme-Klair_1329126975.akd0921m.cif' data_akd0921m _database_code_depnum_ccdc_archive 'CCDC 866683' #TrackingRef '9539_web_deposit_cif_file_1_Anne-KathrinDuhme-Klair_1329126975.akd0921m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H15 Cu N3 O7' _chemical_formula_sum 'C12 H15 Cu N3 O7' _chemical_formula_weight 376.81 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 _symmetry_space_group_name_Hall '-P 2yn' 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 7.8471(4) _cell_length_b 17.0584(8) _cell_length_c 11.0122(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.9220(10) _cell_angle_gamma 90.00 _cell_volume 1470.63(12) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 8498 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 28.29 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 1.527 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.823 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_process_details 'SADABS v2.10; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 15054 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3660 _reflns_number_gt 3371 _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, 1997)' _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. The O-H hydrogens of the methanols were located by difference map after all other atoms had been located ; _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^)+(0.0410P)^2^+0.6751P] 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 3660 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0709 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.002 _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 C1 C 0.35284(17) 0.01322(8) 0.89079(12) 0.0163(3) Uani 1 1 d . . . C2 C 0.43624(17) 0.08800(8) 0.85108(12) 0.0164(3) Uani 1 1 d . . . C3 C 0.29034(17) 0.27155(8) 0.90897(12) 0.0168(3) Uani 1 1 d . . . C4 C 0.31818(18) 0.35746(8) 0.89598(13) 0.0167(3) Uani 1 1 d . . . C5 C 0.20893(19) 0.40998(8) 0.95014(13) 0.0199(3) Uani 1 1 d . . . H5 H 0.1184 0.3906 0.9947 0.024 Uiso 1 1 calc R . . C6 C 0.2327(2) 0.49004(9) 0.93877(14) 0.0219(3) Uani 1 1 d . . . H6 H 0.1604 0.5261 0.9762 0.026 Uiso 1 1 calc R . . C7 C 0.36446(19) 0.51645(8) 0.87151(13) 0.0197(3) Uani 1 1 d . . . C8 C 0.47479(19) 0.46600(8) 0.81703(13) 0.0201(3) Uani 1 1 d . . . H8 H 0.5641 0.4857 0.7716 0.024 Uiso 1 1 calc R . . C9 C 0.45138(18) 0.38596(8) 0.83065(13) 0.0192(3) Uani 1 1 d . . . H9 H 0.5266 0.3503 0.7952 0.023 Uiso 1 1 calc R . . C10 C 0.59249(19) 0.08738(9) 0.78155(14) 0.0224(3) Uani 1 1 d . . . H10A H 0.6017 0.1373 0.7384 0.034 Uiso 1 1 calc R . . H10B H 0.5852 0.0443 0.7226 0.034 Uiso 1 1 calc R . . H10C H 0.6934 0.0801 0.8379 0.034 Uiso 1 1 calc R . . C11 C 0.3532(2) 0.19557(10) 1.22131(17) 0.0309(4) Uani 1 1 d . . . H11A H 0.4427 0.2167 1.1727 0.046 Uiso 1 1 calc R . . H11B H 0.4020 0.1833 1.3034 0.046 Uiso 1 1 calc R . . H11C H 0.2623 0.2346 1.2263 0.046 Uiso 1 1 calc R . . C12 C -0.17991(19) 0.18828(8) 1.04551(15) 0.0217(3) Uani 1 1 d . . . H12A H -0.1137 0.2245 1.0993 0.032 Uiso 1 1 calc R . . H12B H -0.2800 0.1701 1.0860 0.032 Uiso 1 1 calc R . . H12C H -0.2173 0.2153 0.9698 0.032 Uiso 1 1 calc R . . Cu1 Cu 0.15665(2) 0.133837(9) 0.972900(15) 0.01611(7) Uani 1 1 d . . . N1 N 0.35625(15) 0.14902(7) 0.88525(11) 0.0161(2) Uani 1 1 d . . . N2 N 0.40519(15) 0.22452(7) 0.86227(11) 0.0174(2) Uani 1 1 d . . . N3 N 0.38795(18) 0.60154(7) 0.85687(12) 0.0243(3) Uani 1 1 d . . . O1 O 0.21185(13) 0.02092(6) 0.94460(9) 0.0180(2) Uani 1 1 d . . . O2 O 0.41965(13) -0.05053(6) 0.87142(10) 0.0210(2) Uani 1 1 d . . . O3 O 0.15919(12) 0.24909(6) 0.96372(9) 0.0197(2) Uani 1 1 d . . . O4 O 0.28421(14) 0.12576(6) 1.16507(10) 0.0200(2) Uani 1 1 d . . . H4 H 0.354(3) 0.1000(13) 1.1588(18) 0.024(5) Uiso 1 1 d . . . O5 O -0.07505(14) 0.12206(6) 1.01819(11) 0.0221(2) Uani 1 1 d . . . H5A H -0.110(3) 0.0833(15) 1.031(2) 0.038(6) Uiso 1 1 d . . . O6 O 0.29554(19) 0.64567(7) 0.91038(13) 0.0356(3) Uani 1 1 d . . . O7 O 0.49767(17) 0.62383(7) 0.78999(13) 0.0336(3) 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 C1 0.0152(6) 0.0152(6) 0.0185(6) -0.0008(5) -0.0001(5) -0.0001(5) C2 0.0149(6) 0.0157(6) 0.0186(6) 0.0002(5) 0.0012(5) 0.0001(5) C3 0.0166(6) 0.0143(6) 0.0195(6) 0.0018(5) 0.0020(5) 0.0005(5) C4 0.0172(6) 0.0142(6) 0.0186(6) 0.0010(5) 0.0012(5) 0.0010(5) C5 0.0202(7) 0.0179(7) 0.0221(6) 0.0008(5) 0.0046(5) 0.0014(5) C6 0.0248(7) 0.0166(7) 0.0244(7) -0.0018(5) 0.0019(6) 0.0041(5) C7 0.0237(7) 0.0126(6) 0.0220(7) 0.0010(5) -0.0042(5) -0.0008(5) C8 0.0204(7) 0.0172(6) 0.0227(7) 0.0011(5) 0.0022(5) -0.0027(5) C9 0.0188(6) 0.0162(6) 0.0228(7) 0.0000(5) 0.0035(5) 0.0008(5) C10 0.0192(7) 0.0196(7) 0.0295(7) -0.0028(6) 0.0094(6) -0.0004(5) C11 0.0254(8) 0.0246(8) 0.0421(9) -0.0127(7) -0.0022(7) 0.0010(6) C12 0.0187(7) 0.0143(7) 0.0327(8) -0.0002(5) 0.0066(6) 0.0026(5) Cu1 0.01443(10) 0.01167(10) 0.02286(11) 0.00058(6) 0.00576(7) 0.00048(5) N1 0.0159(5) 0.0132(5) 0.0193(5) 0.0010(4) 0.0023(4) -0.0006(4) N2 0.0180(6) 0.0125(5) 0.0221(6) 0.0015(4) 0.0043(4) -0.0004(4) N3 0.0281(7) 0.0146(6) 0.0289(7) 0.0001(5) -0.0069(5) -0.0008(5) O1 0.0165(5) 0.0136(4) 0.0245(5) -0.0005(4) 0.0051(4) 0.0001(4) O2 0.0193(5) 0.0143(5) 0.0297(5) -0.0021(4) 0.0033(4) 0.0024(4) O3 0.0183(5) 0.0132(5) 0.0286(5) 0.0023(4) 0.0078(4) 0.0009(4) O4 0.0176(5) 0.0175(5) 0.0252(5) -0.0037(4) 0.0035(4) 0.0022(4) O5 0.0165(5) 0.0127(5) 0.0382(6) -0.0001(4) 0.0103(4) 0.0002(4) O6 0.0467(8) 0.0166(5) 0.0434(7) -0.0034(5) 0.0033(6) 0.0066(5) O7 0.0321(7) 0.0188(5) 0.0498(8) 0.0048(5) 0.0027(6) -0.0072(5) _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 C1 O2 1.2322(17) . ? C1 O1 1.2970(17) . ? C1 C2 1.5119(19) . ? C2 N1 1.2852(18) . ? C2 C10 1.4893(19) . ? C3 O3 1.2862(17) . ? C3 N2 1.3355(18) . ? C3 C4 1.4902(19) . ? C4 C9 1.396(2) . ? C4 C5 1.4011(19) . ? C5 C6 1.385(2) . ? C5 H5 0.9500 . ? C6 C7 1.387(2) . ? C6 H6 0.9500 . ? C7 C8 1.386(2) . ? C7 N3 1.4734(18) . ? C8 C9 1.387(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O4 1.4315(18) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O5 1.4413(17) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? Cu1 N1 1.9128(12) . ? Cu1 O5 1.9285(11) . ? Cu1 O3 1.9688(11) . ? Cu1 O1 2.0033(10) . ? Cu1 O4 2.2824(11) . ? N1 N2 1.3724(16) . ? N3 O6 1.2240(19) . ? N3 O7 1.2308(19) . ? O4 H4 0.71(2) . ? O5 H5A 0.73(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 C1 O1 123.70(13) . . ? O2 C1 C2 119.79(12) . . ? O1 C1 C2 116.51(12) . . ? N1 C2 C10 126.30(13) . . ? N1 C2 C1 111.65(12) . . ? C10 C2 C1 122.05(12) . . ? O3 C3 N2 125.75(13) . . ? O3 C3 C4 117.72(12) . . ? N2 C3 C4 116.53(12) . . ? C9 C4 C5 119.88(13) . . ? C9 C4 C3 120.78(12) . . ? C5 C4 C3 119.34(13) . . ? C6 C5 C4 120.10(13) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 118.59(13) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C8 C7 C6 122.66(13) . . ? C8 C7 N3 118.54(14) . . ? C6 C7 N3 118.80(13) . . ? C7 C8 C9 118.24(13) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? C8 C9 C4 120.51(13) . . ? C8 C9 H9 119.7 . . ? C4 C9 H9 119.7 . . ? C2 C10 H10A 109.5 . . ? C2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 C11 H11A 109.5 . . ? O4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O5 C12 H12A 109.5 . . ? O5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 Cu1 O5 164.51(5) . . ? N1 Cu1 O3 80.06(5) . . ? O5 Cu1 O3 97.49(4) . . ? N1 Cu1 O1 81.87(5) . . ? O5 Cu1 O1 99.08(4) . . ? O3 Cu1 O1 161.64(4) . . ? N1 Cu1 O4 98.84(5) . . ? O5 Cu1 O4 96.62(5) . . ? O3 Cu1 O4 95.89(4) . . ? O1 Cu1 O4 90.02(4) . . ? C2 N1 N2 123.90(12) . . ? C2 N1 Cu1 118.12(10) . . ? N2 N1 Cu1 117.98(9) . . ? C3 N2 N1 106.74(11) . . ? O6 N3 O7 124.04(14) . . ? O6 N3 C7 118.07(14) . . ? O7 N3 C7 117.89(13) . . ? C1 O1 Cu1 111.64(8) . . ? C3 O3 Cu1 109.43(9) . . ? C11 O4 Cu1 118.68(10) . . ? C11 O4 H4 106.6(17) . . ? Cu1 O4 H4 103.8(16) . . ? C12 O5 Cu1 122.28(9) . . ? C12 O5 H5A 115.8(19) . . ? Cu1 O5 H5A 121.3(19) . . ? 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 O2 C1 C2 N1 -175.75(12) . . . . ? O1 C1 C2 N1 4.17(18) . . . . ? O2 C1 C2 C10 4.0(2) . . . . ? O1 C1 C2 C10 -176.12(13) . . . . ? O3 C3 C4 C9 -175.75(13) . . . . ? N2 C3 C4 C9 4.3(2) . . . . ? O3 C3 C4 C5 4.2(2) . . . . ? N2 C3 C4 C5 -175.72(13) . . . . ? C9 C4 C5 C6 0.1(2) . . . . ? C3 C4 C5 C6 -179.87(13) . . . . ? C4 C5 C6 C7 1.0(2) . . . . ? C5 C6 C7 C8 -1.1(2) . . . . ? C5 C6 C7 N3 178.66(13) . . . . ? C6 C7 C8 C9 0.1(2) . . . . ? N3 C7 C8 C9 -179.66(13) . . . . ? C7 C8 C9 C4 1.0(2) . . . . ? C5 C4 C9 C8 -1.1(2) . . . . ? C3 C4 C9 C8 178.84(13) . . . . ? C10 C2 N1 N2 -0.3(2) . . . . ? C1 C2 N1 N2 179.43(12) . . . . ? C10 C2 N1 Cu1 179.53(11) . . . . ? C1 C2 N1 Cu1 -0.78(15) . . . . ? O5 Cu1 N1 C2 -96.14(19) . . . . ? O3 Cu1 N1 C2 -178.28(11) . . . . ? O1 Cu1 N1 C2 -1.51(10) . . . . ? O4 Cu1 N1 C2 87.24(11) . . . . ? O5 Cu1 N1 N2 83.7(2) . . . . ? O3 Cu1 N1 N2 1.53(9) . . . . ? O1 Cu1 N1 N2 178.30(10) . . . . ? O4 Cu1 N1 N2 -92.95(10) . . . . ? O3 C3 N2 N1 -0.52(19) . . . . ? C4 C3 N2 N1 179.43(11) . . . . ? C2 N1 N2 C3 178.74(13) . . . . ? Cu1 N1 N2 C3 -1.05(14) . . . . ? C8 C7 N3 O6 -176.35(14) . . . . ? C6 C7 N3 O6 3.9(2) . . . . ? C8 C7 N3 O7 4.8(2) . . . . ? C6 C7 N3 O7 -175.02(14) . . . . ? O2 C1 O1 Cu1 174.67(11) . . . . ? C2 C1 O1 Cu1 -5.24(15) . . . . ? N1 Cu1 O1 C1 3.77(9) . . . . ? O5 Cu1 O1 C1 168.12(9) . . . . ? O3 Cu1 O1 C1 13.91(19) . . . . ? O4 Cu1 O1 C1 -95.16(9) . . . . ? N2 C3 O3 Cu1 1.71(17) . . . . ? C4 C3 O3 Cu1 -178.24(10) . . . . ? N1 Cu1 O3 C3 -1.60(9) . . . . ? O5 Cu1 O3 C3 -166.12(9) . . . . ? O1 Cu1 O3 C3 -11.80(19) . . . . ? O4 Cu1 O3 C3 96.38(9) . . . . ? N1 Cu1 O4 C11 72.08(11) . . . . ? O5 Cu1 O4 C11 -107.01(11) . . . . ? O3 Cu1 O4 C11 -8.74(11) . . . . ? O1 Cu1 O4 C11 153.85(11) . . . . ? N1 Cu1 O5 C12 -85.8(2) . . . . ? O3 Cu1 O5 C12 -6.00(12) . . . . ? O1 Cu1 O5 C12 -178.05(11) . . . . ? O4 Cu1 O5 C12 90.86(12) . . . . ? 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 O4 H4 O2 0.71(2) 2.02(2) 2.7085(15) 166(2) 3_657 O5 H5A O1 0.73(3) 1.97(3) 2.7072(15) 176(2) 3_557 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.454 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.065 # Attachment '9540_web_deposit_cif_file_2_Anne-KathrinDuhme-Klair_1329126975.akd0924m.cif' data_akd0924m _database_code_depnum_ccdc_archive 'CCDC 866684' #TrackingRef '9540_web_deposit_cif_file_2_Anne-KathrinDuhme-Klair_1329126975.akd0924m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 Cu N2 O5' _chemical_formula_sum 'C11 H14 Cu N2 O5' _chemical_formula_weight 317.78 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3879(9) _cell_length_b 11.4695(13) _cell_length_c 15.3898(18) _cell_angle_alpha 93.602(2) _cell_angle_beta 102.437(2) _cell_angle_gamma 103.124(2) _cell_volume 1231.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4970 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 28.33 _exptl_crystal_description blocks _exptl_crystal_colour green _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.714 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 1.792 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.619 _exptl_absorpt_correction_T_max 0.882 _exptl_absorpt_process_details 'SADABS v2.10; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 10913 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 28.33 _reflns_number_total 5970 _reflns_number_gt 4986 _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. H4a-O4 and H4b-O4 restrained to be equal. H9a-O9 and H9b-O9 restrained to be equal. ; _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^)+(0.0607P)^2^+0.9052P] 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 5970 _refine_ls_number_parameters 371 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.046 _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 C1 C 1.1424(3) 0.6724(2) 0.69288(16) 0.0179(4) Uani 1 1 d . . . C2 C 1.1268(3) 0.6011(2) 0.77154(15) 0.0162(4) Uani 1 1 d . . . C3 C 0.8514(3) 0.3155(2) 0.75929(15) 0.0166(4) Uani 1 1 d . . . C4 C 0.7998(3) 0.2127(2) 0.81052(16) 0.0170(4) Uani 1 1 d . . . C5 C 0.8789(3) 0.2223(2) 0.90237(16) 0.0206(5) Uani 1 1 d . . . H5 H 0.9634 0.2958 0.9324 0.025 Uiso 1 1 calc R . . C6 C 0.8353(3) 0.1254(2) 0.95007(16) 0.0215(5) Uani 1 1 d . . . H6 H 0.8907 0.1330 1.0125 0.026 Uiso 1 1 calc R . . C7 C 0.7098(3) 0.0159(2) 0.90690(17) 0.0200(5) Uani 1 1 d . . . C8 C 0.6304(3) 0.0076(2) 0.81564(16) 0.0188(4) Uani 1 1 d . . . H8 H 0.5445 -0.0655 0.7857 0.023 Uiso 1 1 calc R . . C9 C 0.6741(3) 0.1044(2) 0.76726(16) 0.0179(4) Uani 1 1 d . . . H9 H 0.6186 0.0970 0.7048 0.021 Uiso 1 1 calc R . . C10 C 1.2317(3) 0.6512(2) 0.86443(16) 0.0223(5) Uani 1 1 d . . . H10A H 1.3649 0.6458 0.8735 0.033 Uiso 1 1 calc R . . H10B H 1.1714 0.6051 0.9066 0.033 Uiso 1 1 calc R . . H10C H 1.2283 0.7358 0.8746 0.033 Uiso 1 1 calc R . . C11 C 0.6627(4) -0.0895(2) 0.95888(18) 0.0264(5) Uani 1 1 d . . . H11A H 0.6628 -0.1638 0.9238 0.040 Uiso 1 1 calc R . . H11B H 0.5360 -0.0959 0.9709 0.040 Uiso 1 1 calc R . . H11C H 0.7586 -0.0773 1.0158 0.040 Uiso 1 1 calc R . . Cu1 Cu 0.88526(4) 0.45370(2) 0.624500(18) 0.01800(9) Uani 1 1 d . . . N1 N 1.0171(3) 0.49451(17) 0.74685(13) 0.0162(4) Uani 1 1 d . . . N2 N 0.9841(3) 0.41027(17) 0.80480(13) 0.0177(4) Uani 1 1 d . . . O1 O 1.0345(3) 0.61882(15) 0.61689(11) 0.0223(4) Uani 1 1 d . . . O2 O 1.2539(2) 0.77221(15) 0.70421(11) 0.0205(3) Uani 1 1 d . . . O3 O 0.7686(2) 0.30741(15) 0.67474(11) 0.0188(3) Uani 1 1 d . . . O4 O 0.7002(3) 0.46111(18) 0.51411(14) 0.0317(5) Uani 1 1 d D . . H4A H 0.640(5) 0.414(3) 0.481(2) 0.038 Uiso 1 1 d D . . H4B H 0.647(5) 0.489(3) 0.536(2) 0.038 Uiso 1 1 d D . . O5 O 1.0473(3) 0.35392(17) 0.55471(13) 0.0253(4) Uani 1 1 d . . . H5A H 0.993(4) 0.340(3) 0.497(2) 0.030 Uiso 1 1 d . . . H5B H 1.045(5) 0.291(3) 0.571(2) 0.030 Uiso 1 1 d . . . C12 C 0.0388(3) -0.0472(2) 0.38135(15) 0.0171(4) Uani 1 1 d . . . C13 C 0.0239(3) 0.0301(2) 0.30499(15) 0.0168(4) Uani 1 1 d . . . C14 C 0.3240(3) 0.3042(2) 0.30539(15) 0.0167(4) Uani 1 1 d . . . C15 C 0.3788(3) 0.4032(2) 0.25136(16) 0.0179(4) Uani 1 1 d . . . C16 C 0.2897(3) 0.3949(2) 0.16059(16) 0.0200(5) Uani 1 1 d . . . H16 H 0.1892 0.3264 0.1337 0.024 Uiso 1 1 calc R . . C17 C 0.3461(3) 0.4856(2) 0.10930(17) 0.0215(5) Uani 1 1 d . . . H17 H 0.2841 0.4785 0.0477 0.026 Uiso 1 1 calc R . . C18 C 0.4946(3) 0.5880(2) 0.14800(17) 0.0190(4) Uani 1 1 d . . . C19 C 0.5793(3) 0.5966(2) 0.23829(16) 0.0209(5) Uani 1 1 d . . . H19 H 0.6777 0.6659 0.2657 0.025 Uiso 1 1 calc R . . C20 C 0.5236(3) 0.5061(2) 0.28979(17) 0.0211(5) Uani 1 1 d . . . H20 H 0.5843 0.5141 0.3517 0.025 Uiso 1 1 calc R . . C21 C -0.1230(3) -0.0086(2) 0.21914(16) 0.0211(5) Uani 1 1 d . . . H21A H -0.1485 0.0627 0.1917 0.032 Uiso 1 1 calc R . . H21B H -0.2412 -0.0568 0.2307 0.032 Uiso 1 1 calc R . . H21C H -0.0762 -0.0571 0.1784 0.032 Uiso 1 1 calc R . . C22 C 0.5611(4) 0.6859(2) 0.09318(18) 0.0245(5) Uani 1 1 d . . . H22A H 0.5222 0.7585 0.1107 0.037 Uiso 1 1 calc R . . H22B H 0.5036 0.6588 0.0295 0.037 Uiso 1 1 calc R . . H22C H 0.7007 0.7044 0.1036 0.037 Uiso 1 1 calc R . . Cu2 Cu 0.33621(4) 0.15566(2) 0.436586(19) 0.01845(9) Uani 1 1 d . . . N3 N 0.1572(3) 0.12863(17) 0.32338(13) 0.0161(4) Uani 1 1 d . . . N4 N 0.1794(3) 0.21244(17) 0.26431(13) 0.0178(4) Uani 1 1 d . . . O6 O 0.1797(2) -0.00586(15) 0.44918(11) 0.0211(3) Uani 1 1 d . . . O7 O -0.0832(2) -0.14422(15) 0.37379(12) 0.0208(3) Uani 1 1 d . . . O8 O 0.4173(2) 0.31107(15) 0.38785(11) 0.0207(3) Uani 1 1 d . . . O9 O 0.5991(3) 0.1119(2) 0.42532(15) 0.0380(6) Uani 1 1 d D . . H9A H 0.671(5) 0.095(3) 0.461(2) 0.046 Uiso 1 1 d D . . H9B H 0.650(5) 0.152(3) 0.398(2) 0.046 Uiso 1 1 d D . . O10 O 0.4173(3) 0.2078(2) 0.56653(13) 0.0301(5) Uani 1 1 d . . . H10D H 0.514(5) 0.227(3) 0.599(2) 0.036 Uiso 1 1 d . . . H10E H 0.349(5) 0.192(3) 0.588(2) 0.036 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 C1 0.0197(10) 0.0152(11) 0.0203(11) 0.0056(9) 0.0082(8) 0.0029(8) C2 0.0173(10) 0.0134(10) 0.0180(11) 0.0034(8) 0.0063(8) 0.0014(8) C3 0.0157(10) 0.0157(10) 0.0188(11) 0.0022(8) 0.0066(8) 0.0024(8) C4 0.0149(9) 0.0144(10) 0.0213(11) 0.0038(9) 0.0067(8) -0.0001(8) C5 0.0218(11) 0.0168(11) 0.0211(12) 0.0023(9) 0.0066(9) -0.0010(9) C6 0.0238(11) 0.0201(11) 0.0191(11) 0.0037(9) 0.0064(9) 0.0006(9) C7 0.0201(10) 0.0142(11) 0.0269(12) 0.0081(9) 0.0095(9) 0.0014(8) C8 0.0159(10) 0.0129(10) 0.0259(12) 0.0022(9) 0.0059(9) -0.0009(8) C9 0.0180(10) 0.0159(11) 0.0190(11) 0.0026(9) 0.0050(8) 0.0018(8) C10 0.0231(11) 0.0204(12) 0.0197(11) 0.0026(9) 0.0046(9) -0.0016(9) C11 0.0290(12) 0.0185(12) 0.0301(13) 0.0102(10) 0.0086(10) -0.0009(10) Cu1 0.02099(15) 0.01417(15) 0.01545(15) 0.00339(11) 0.00331(11) -0.00198(11) N1 0.0183(9) 0.0136(9) 0.0161(9) 0.0043(7) 0.0051(7) 0.0007(7) N2 0.0197(9) 0.0137(9) 0.0188(9) 0.0056(7) 0.0062(7) -0.0003(7) O1 0.0304(9) 0.0155(8) 0.0169(8) 0.0041(6) 0.0047(7) -0.0026(7) O2 0.0229(8) 0.0152(8) 0.0222(9) 0.0048(7) 0.0086(7) -0.0016(6) O3 0.0190(7) 0.0155(8) 0.0183(8) 0.0031(6) 0.0038(6) -0.0028(6) O4 0.0357(11) 0.0209(10) 0.0280(11) 0.0031(8) -0.0083(8) 0.0005(8) O5 0.0364(10) 0.0173(9) 0.0224(9) 0.0068(7) 0.0072(8) 0.0059(7) C12 0.0184(10) 0.0153(10) 0.0198(11) 0.0050(9) 0.0080(8) 0.0046(8) C13 0.0178(10) 0.0138(10) 0.0195(11) 0.0027(8) 0.0063(8) 0.0035(8) C14 0.0164(10) 0.0136(10) 0.0205(11) 0.0029(8) 0.0064(8) 0.0023(8) C15 0.0173(10) 0.0133(10) 0.0233(11) 0.0036(9) 0.0073(8) 0.0016(8) C16 0.0204(11) 0.0146(11) 0.0236(12) 0.0039(9) 0.0053(9) 0.0008(8) C17 0.0233(11) 0.0183(11) 0.0209(11) 0.0059(9) 0.0032(9) 0.0020(9) C18 0.0196(10) 0.0129(10) 0.0261(12) 0.0066(9) 0.0087(9) 0.0031(8) C19 0.0229(11) 0.0135(11) 0.0237(12) 0.0024(9) 0.0075(9) -0.0026(8) C20 0.0239(11) 0.0160(11) 0.0210(11) 0.0033(9) 0.0064(9) -0.0013(9) C21 0.0206(11) 0.0156(11) 0.0225(12) 0.0016(9) 0.0002(9) -0.0001(8) C22 0.0272(12) 0.0185(12) 0.0267(13) 0.0084(10) 0.0096(10) -0.0008(9) Cu2 0.01689(14) 0.01667(15) 0.01791(15) 0.00539(11) 0.00218(11) -0.00274(10) N3 0.0172(8) 0.0134(9) 0.0173(9) 0.0042(7) 0.0048(7) 0.0015(7) N4 0.0192(9) 0.0126(9) 0.0200(10) 0.0058(7) 0.0042(7) -0.0002(7) O6 0.0200(8) 0.0189(8) 0.0216(8) 0.0080(7) 0.0032(6) -0.0009(6) O7 0.0213(8) 0.0143(8) 0.0253(9) 0.0060(7) 0.0065(7) -0.0010(6) O8 0.0196(8) 0.0181(8) 0.0195(8) 0.0032(7) 0.0030(6) -0.0041(6) O9 0.0252(10) 0.0599(15) 0.0405(12) 0.0371(11) 0.0166(9) 0.0168(9) O10 0.0196(9) 0.0436(12) 0.0187(9) 0.0020(8) 0.0059(7) -0.0102(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.226(3) . ? C1 O1 1.291(3) . ? C1 C2 1.513(3) . ? C2 N1 1.286(3) . ? C2 C10 1.480(3) . ? C3 O3 1.301(3) . ? C3 N2 1.326(3) . ? C3 C4 1.483(3) . ? C4 C5 1.395(3) . ? C4 C9 1.397(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.407(3) . ? C6 H6 0.9500 . ? C7 C8 1.389(3) . ? C7 C11 1.508(3) . ? C8 C9 1.392(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? Cu1 N1 1.8988(19) . ? Cu1 O4 1.958(2) . ? Cu1 O3 1.9873(16) . ? Cu1 O1 1.9877(16) . ? Cu1 O5 2.218(2) . ? N1 N2 1.372(2) . ? O4 H4A 0.71(2) . ? O4 H4B 0.69(2) . ? O5 H5A 0.88(3) . ? O5 H5B 0.77(3) . ? C12 O7 1.244(3) . ? C12 O6 1.282(3) . ? C12 C13 1.516(3) . ? C13 N3 1.289(3) . ? C13 C21 1.487(3) . ? C14 O8 1.295(3) . ? C14 N4 1.328(3) . ? C14 C15 1.483(3) . ? C15 C20 1.397(3) . ? C15 C16 1.397(3) . ? C16 C17 1.388(3) . ? C16 H16 0.9500 . ? C17 C18 1.409(3) . ? C17 H17 0.9500 . ? C18 C19 1.383(3) . ? C18 C22 1.504(3) . ? C19 C20 1.388(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? Cu2 N3 1.9065(19) . ? Cu2 O10 1.971(2) . ? Cu2 O8 1.9939(16) . ? Cu2 O6 1.9940(16) . ? Cu2 O9 2.152(2) . ? N3 N4 1.371(2) . ? O9 H9A 0.75(3) . ? O9 H9B 0.74(3) . ? O10 H10D 0.75(4) . ? O10 H10E 0.65(4) . ? 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 C1 O1 125.2(2) . . ? O2 C1 C2 119.9(2) . . ? O1 C1 C2 114.82(19) . . ? N1 C2 C10 125.9(2) . . ? N1 C2 C1 111.9(2) . . ? C10 C2 C1 122.2(2) . . ? O3 C3 N2 124.6(2) . . ? O3 C3 C4 119.51(19) . . ? N2 C3 C4 115.9(2) . . ? C5 C4 C9 119.2(2) . . ? C5 C4 C3 120.3(2) . . ? C9 C4 C3 120.5(2) . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.6(2) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 118.5(2) . . ? C8 C7 C11 121.0(2) . . ? C6 C7 C11 120.6(2) . . ? C7 C8 C9 121.2(2) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C8 C9 C4 120.0(2) . . ? C8 C9 H9 120.0 . . ? C4 C9 H9 120.0 . . ? C2 C10 H10A 109.5 . . ? C2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 Cu1 O4 156.67(9) . . ? N1 Cu1 O3 79.98(7) . . ? O4 Cu1 O3 105.71(8) . . ? N1 Cu1 O1 81.46(7) . . ? O4 Cu1 O1 90.13(8) . . ? O3 Cu1 O1 161.11(7) . . ? N1 Cu1 O5 108.83(8) . . ? O4 Cu1 O5 93.73(9) . . ? O3 Cu1 O5 92.16(7) . . ? O1 Cu1 O5 97.10(7) . . ? C2 N1 N2 123.5(2) . . ? C2 N1 Cu1 118.26(15) . . ? N2 N1 Cu1 118.14(14) . . ? C3 N2 N1 107.91(18) . . ? C1 O1 Cu1 113.35(14) . . ? C3 O3 Cu1 109.13(13) . . ? Cu1 O4 H4A 131(3) . . ? Cu1 O4 H4B 94(3) . . ? H4A O4 H4B 111(4) . . ? Cu1 O5 H5A 109(2) . . ? Cu1 O5 H5B 112(2) . . ? H5A O5 H5B 105(3) . . ? O7 C12 O6 125.3(2) . . ? O7 C12 C13 118.6(2) . . ? O6 C12 C13 116.03(19) . . ? N3 C13 C21 125.7(2) . . ? N3 C13 C12 111.5(2) . . ? C21 C13 C12 122.79(19) . . ? O8 C14 N4 124.1(2) . . ? O8 C14 C15 119.46(19) . . ? N4 C14 C15 116.4(2) . . ? C20 C15 C16 118.5(2) . . ? C20 C15 C14 120.6(2) . . ? C16 C15 C14 120.9(2) . . ? C17 C16 C15 120.8(2) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 120.5(2) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 118.3(2) . . ? C19 C18 C22 120.4(2) . . ? C17 C18 C22 121.3(2) . . ? C18 C19 C20 121.4(2) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? C19 C20 C15 120.5(2) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? C13 C21 H21A 109.5 . . ? C13 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C13 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 H22A 109.5 . . ? C18 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C18 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N3 Cu2 O10 152.75(9) . . ? N3 Cu2 O8 78.91(7) . . ? O10 Cu2 O8 101.09(8) . . ? N3 Cu2 O6 81.66(7) . . ? O10 Cu2 O6 94.46(8) . . ? O8 Cu2 O6 160.22(7) . . ? N3 Cu2 O9 111.51(9) . . ? O10 Cu2 O9 95.72(9) . . ? O8 Cu2 O9 89.83(8) . . ? O6 Cu2 O9 100.79(8) . . ? C13 N3 N4 123.07(19) . . ? C13 N3 Cu2 118.10(15) . . ? N4 N3 Cu2 118.80(14) . . ? C14 N4 N3 107.53(18) . . ? C12 O6 Cu2 112.68(14) . . ? C14 O8 Cu2 109.88(14) . . ? Cu2 O9 H9A 127(3) . . ? Cu2 O9 H9B 112(3) . . ? H9A O9 H9B 109(4) . . ? Cu2 O10 H10D 133(3) . . ? Cu2 O10 H10E 114(3) . . ? H10D O10 H10E 111(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 O2 C1 C2 N1 -174.1(2) . . . . ? O1 C1 C2 N1 4.8(3) . . . . ? O2 C1 C2 C10 4.7(3) . . . . ? O1 C1 C2 C10 -176.4(2) . . . . ? O3 C3 C4 C5 -176.3(2) . . . . ? N2 C3 C4 C5 4.5(3) . . . . ? O3 C3 C4 C9 4.8(3) . . . . ? N2 C3 C4 C9 -174.4(2) . . . . ? C9 C4 C5 C6 0.7(4) . . . . ? C3 C4 C5 C6 -178.2(2) . . . . ? C4 C5 C6 C7 -0.3(4) . . . . ? C5 C6 C7 C8 -0.3(4) . . . . ? C5 C6 C7 C11 179.9(2) . . . . ? C6 C7 C8 C9 0.5(4) . . . . ? C11 C7 C8 C9 -179.7(2) . . . . ? C7 C8 C9 C4 -0.2(3) . . . . ? C5 C4 C9 C8 -0.4(3) . . . . ? C3 C4 C9 C8 178.4(2) . . . . ? C10 C2 N1 N2 -1.0(4) . . . . ? C1 C2 N1 N2 177.69(19) . . . . ? C10 C2 N1 Cu1 176.26(18) . . . . ? C1 C2 N1 Cu1 -5.0(3) . . . . ? O4 Cu1 N1 C2 -66.8(3) . . . . ? O3 Cu1 N1 C2 -173.34(19) . . . . ? O1 Cu1 N1 C2 3.15(18) . . . . ? O5 Cu1 N1 C2 97.79(18) . . . . ? O4 Cu1 N1 N2 110.6(2) . . . . ? O3 Cu1 N1 N2 4.08(16) . . . . ? O1 Cu1 N1 N2 -179.42(17) . . . . ? O5 Cu1 N1 N2 -84.78(16) . . . . ? O3 C3 N2 N1 -0.7(3) . . . . ? C4 C3 N2 N1 178.46(18) . . . . ? C2 N1 N2 C3 174.1(2) . . . . ? Cu1 N1 N2 C3 -3.2(2) . . . . ? O2 C1 O1 Cu1 176.44(19) . . . . ? C2 C1 O1 Cu1 -2.4(2) . . . . ? N1 Cu1 O1 C1 -0.14(16) . . . . ? O4 Cu1 O1 C1 158.02(17) . . . . ? O3 Cu1 O1 C1 10.6(3) . . . . ? O5 Cu1 O1 C1 -108.21(17) . . . . ? N2 C3 O3 Cu1 3.8(3) . . . . ? C4 C3 O3 Cu1 -175.32(16) . . . . ? N1 Cu1 O3 C3 -3.95(15) . . . . ? O4 Cu1 O3 C3 -160.73(15) . . . . ? O1 Cu1 O3 C3 -14.7(3) . . . . ? O5 Cu1 O3 C3 104.79(15) . . . . ? O7 C12 C13 N3 178.5(2) . . . . ? O6 C12 C13 N3 -1.8(3) . . . . ? O7 C12 C13 C21 -3.9(3) . . . . ? O6 C12 C13 C21 175.8(2) . . . . ? O8 C14 C15 C20 -3.1(3) . . . . ? N4 C14 C15 C20 177.1(2) . . . . ? O8 C14 C15 C16 175.7(2) . . . . ? N4 C14 C15 C16 -4.1(3) . . . . ? C20 C15 C16 C17 1.3(4) . . . . ? C14 C15 C16 C17 -177.5(2) . . . . ? C15 C16 C17 C18 -0.1(4) . . . . ? C16 C17 C18 C19 -1.3(4) . . . . ? C16 C17 C18 C22 178.6(2) . . . . ? C17 C18 C19 C20 1.4(4) . . . . ? C22 C18 C19 C20 -178.4(2) . . . . ? C18 C19 C20 C15 -0.2(4) . . . . ? C16 C15 C20 C19 -1.2(4) . . . . ? C14 C15 C20 C19 177.7(2) . . . . ? C21 C13 N3 N4 0.3(4) . . . . ? C12 C13 N3 N4 177.85(19) . . . . ? C21 C13 N3 Cu2 -177.44(18) . . . . ? C12 C13 N3 Cu2 0.1(3) . . . . ? O10 Cu2 N3 C13 -82.6(3) . . . . ? O8 Cu2 N3 C13 -175.28(19) . . . . ? O6 Cu2 N3 C13 0.97(17) . . . . ? O9 Cu2 N3 C13 99.34(18) . . . . ? O10 Cu2 N3 N4 99.6(2) . . . . ? O8 Cu2 N3 N4 6.84(16) . . . . ? O6 Cu2 N3 N4 -176.91(17) . . . . ? O9 Cu2 N3 N4 -78.54(18) . . . . ? O8 C14 N4 N3 -2.7(3) . . . . ? C15 C14 N4 N3 177.11(18) . . . . ? C13 N3 N4 C14 177.6(2) . . . . ? Cu2 N3 N4 C14 -4.6(2) . . . . ? O7 C12 O6 Cu2 -177.81(19) . . . . ? C13 C12 O6 Cu2 2.5(2) . . . . ? N3 Cu2 O6 C12 -1.95(16) . . . . ? O10 Cu2 O6 C12 150.90(17) . . . . ? O8 Cu2 O6 C12 9.0(3) . . . . ? O9 Cu2 O6 C12 -112.40(16) . . . . ? N4 C14 O8 Cu2 7.9(3) . . . . ? C15 C14 O8 Cu2 -171.83(16) . . . . ? N3 Cu2 O8 C14 -7.36(15) . . . . ? O10 Cu2 O8 C14 -159.59(15) . . . . ? O6 Cu2 O8 C14 -18.4(3) . . . . ? O9 Cu2 O8 C14 104.62(16) . . . . ? 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 O4 H4A O8 0.71(2) 2.01(3) 2.702(3) 164(4) . O4 H4B O4 0.69(2) 2.72(3) 3.230(5) 134(4) 2_666 O5 H5A O1 0.88(3) 1.83(3) 2.634(3) 152(3) 2_766 O5 H5B O7 0.77(3) 1.98(4) 2.750(2) 170(3) 2_656 O9 H9A O6 0.75(3) 2.05(3) 2.778(3) 165(4) 2_656 O9 H9B O2 0.74(3) 2.03(3) 2.744(2) 164(4) 2_766 O10 H10D O3 0.75(4) 1.97(4) 2.714(3) 169(4) . O10 H10E O7 0.65(4) 2.14(4) 2.777(3) 166(4) 2_556 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.982 _refine_diff_density_min -0.728 _refine_diff_density_rms 0.107 # Attachment '9541_web_deposit_cif_file_3_Anne-KathrinDuhme-Klair_1329126975.akdk1102.cif' data_akdk1102 _database_code_depnum_ccdc_archive 'CCDC 866685' #TrackingRef '9541_web_deposit_cif_file_3_Anne-KathrinDuhme-Klair_1329126975.akdk1102.cif' _audit_creation_date 2011-04-15 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H17 Cu N3 O7' _chemical_formula_sum 'C13 H17 Cu N3 O7' _chemical_formula_weight 390.84 _chemical_melting_point ? _chemical_oxdiff_formula 'C11 H13 Cu N3 O7' _chemical_oxdiff_usercomment "Abeda's CuNP3Me4NO2" 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.159(3) _cell_length_b 14.1559(7) _cell_length_c 11.895(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.11(3) _cell_angle_gamma 90.00 _cell_volume 1561.3(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6396 _cell_measurement_temperature 110.0 _cell_measurement_theta_max 32.0397 _cell_measurement_theta_min 2.8749 _exptl_absorpt_coefficient_mu 1.441 _exptl_absorpt_correction_T_max 0.945 _exptl_absorpt_correction_T_min 0.823 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour green _exptl_crystal_colour_primary green _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 804 _exptl_crystal_size_max 0.1963 _exptl_crystal_size_mid 0.0833 _exptl_crystal_size_min 0.042 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_unetI/netI 0.0295 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 13154 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 32.11 _diffrn_reflns_theta_min 2.88 _diffrn_ambient_temperature 110.0 _diffrn_detector_area_resol_mean 16.1450 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.894 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -15.00 19.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -25.1672 37.0000 60.0000 34 #__ type_ start__ end____ width___ exp.time_ 2 omega -78.00 -8.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -25.1672 -54.0000 80.0000 70 #__ type_ start__ end____ width___ exp.time_ 3 omega 41.00 81.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 26.4172 172.0000 -99.0000 40 #__ type_ start__ end____ width___ exp.time_ 4 omega -39.00 -13.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -17.6138 37.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega 17.00 44.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -17.6138 37.0000 60.0000 27 #__ type_ start__ end____ width___ exp.time_ 6 omega 0.00 72.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 18.8638 37.0000 -60.0000 72 #__ type_ start__ end____ width___ exp.time_ 7 omega -80.00 -54.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -24.9830 -77.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega -42.00 -14.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -24.9830 -77.0000 -90.0000 28 #__ type_ start__ end____ width___ exp.time_ 9 omega 16.00 46.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 26.3892 54.0000 99.0000 30 #__ type_ start__ end____ width___ exp.time_ 10 omega 69.00 95.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 26.3892 37.0000 -150.0000 26 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0438579000 _diffrn_orient_matrix_UB_12 -0.0289578000 _diffrn_orient_matrix_UB_13 0.0499013000 _diffrn_orient_matrix_UB_21 -0.0619902000 _diffrn_orient_matrix_UB_22 -0.0152242000 _diffrn_orient_matrix_UB_23 0.0082675000 _diffrn_orient_matrix_UB_31 -0.0087729000 _diffrn_orient_matrix_UB_32 -0.0380374000 _diffrn_orient_matrix_UB_33 -0.0413794000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4257 _reflns_number_total 4881 _reflns_odcompleteness_completeness 99.12 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.01 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.466 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.071 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 4881 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0300 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0256P)^2^+1.0972P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.0723 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C1 C 1.04704(16) 0.28370(10) 1.02814(13) 0.0133(3) Uani 1 1 d . . . C2 C 1.03007(16) 0.21400(10) 0.92605(13) 0.0130(3) Uani 1 1 d . . . C3 C 1.05189(19) 0.11098(10) 0.95014(14) 0.0177(3) Uani 1 1 d . . . H3A H 1.1537 0.0986 1.0021 0.027 Uiso 1 1 calc R . . H3B H 1.0240 0.0772 0.8719 0.027 Uiso 1 1 calc R . . H3C H 0.9924 0.0892 0.9923 0.027 Uiso 1 1 calc R . . C4 C 0.93576(16) 0.27537(10) 0.62599(13) 0.0135(3) Uani 1 1 d . . . C5 C 0.89460(16) 0.24274(10) 0.49687(13) 0.0134(3) Uani 1 1 d . . . C6 C 0.86613(16) 0.14780(11) 0.46498(14) 0.0142(3) Uani 1 1 d . . . H6 H 0.8734 0.1035 0.5273 0.017 Uiso 1 1 calc R . . C7 C 0.82735(16) 0.11545(10) 0.34467(14) 0.0140(3) Uani 1 1 d . . . C8 C 0.81895(17) 0.18504(11) 0.25761(13) 0.0149(3) Uani 1 1 d . . . C9 C 0.84337(18) 0.28026(11) 0.28607(14) 0.0185(3) Uani 1 1 d . . . H9 H 0.8340 0.3250 0.2237 0.022 Uiso 1 1 calc R . . C10 C 0.88149(18) 0.30929(11) 0.40642(14) 0.0174(3) Uani 1 1 d . . . H10 H 0.8986 0.3743 0.4273 0.021 Uiso 1 1 calc R . . C11 C 0.79355(19) 0.01257(11) 0.31623(15) 0.0201(3) Uani 1 1 d . . . H11A H 0.8725 -0.0177 0.3025 0.030 Uiso 1 1 calc R . . H11B H 0.7039 0.0063 0.2420 0.030 Uiso 1 1 calc R . . H11C H 0.7822 -0.0180 0.3857 0.030 Uiso 1 1 calc R . . C12 C 0.6798(2) 0.42182(14) 0.86053(17) 0.0255(4) Uani 1 1 d . . . H12A H 0.5862 0.4528 0.8178 0.038 Uiso 1 1 calc R . . H12B H 0.7487 0.4670 0.9164 0.038 Uiso 1 1 calc R . . H12C H 0.6691 0.3680 0.9079 0.038 Uiso 1 1 calc R . . C13 C 0.8606(2) 0.56869(12) 0.69515(15) 0.0235(4) Uani 1 1 d . . . H13A H 0.8684 0.5378 0.6244 0.035 Uiso 1 1 calc R . . H13B H 0.8811 0.6363 0.6942 0.035 Uiso 1 1 calc R . . H13C H 0.7627 0.5603 0.6904 0.035 Uiso 1 1 calc R . . Cu1 Cu 0.96446(2) 0.389151(12) 0.815406(16) 0.01154(6) Uani 1 1 d . . . N1 N 0.99310(14) 0.25536(9) 0.82162(11) 0.0129(2) Uani 1 1 d . . . N2 N 0.96538(14) 0.20911(9) 0.71222(11) 0.0140(2) Uani 1 1 d . . . N3 N 0.78483(15) 0.15960(10) 0.12861(12) 0.0184(3) Uani 1 1 d . . . O1 O 1.02961(12) 0.37242(7) 0.99707(9) 0.0144(2) Uani 1 1 d . . . O2 O 1.07326(13) 0.25454(8) 1.13249(10) 0.0193(2) Uani 1 1 d . . . O3 O 0.93868(13) 0.36528(7) 0.64429(10) 0.0160(2) Uani 1 1 d . . . O4 O 0.72764(15) 0.21963(9) 0.04917(11) 0.0269(3) Uani 1 1 d . . . O5 O 0.81782(16) 0.08054(9) 0.10687(11) 0.0283(3) Uani 1 1 d . . . O6 O 0.73103(13) 0.38966(9) 0.77307(12) 0.0206(2) Uani 1 1 d . . . H6A H 0.690(3) 0.3515(17) 0.736(2) 0.028(6) Uiso 1 1 d . . . O7 O 0.96341(12) 0.52682(8) 0.80817(10) 0.0141(2) Uani 1 1 d . . . H7 H 0.968(2) 0.5546(17) 0.865(2) 0.032(6) 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 C1 0.0146(6) 0.0124(6) 0.0122(6) -0.0005(5) 0.0046(5) 0.0025(5) C2 0.0146(6) 0.0111(6) 0.0126(6) -0.0012(5) 0.0047(5) 0.0012(5) C3 0.0258(8) 0.0105(6) 0.0153(7) -0.0005(5) 0.0067(6) 0.0030(6) C4 0.0148(6) 0.0132(6) 0.0126(6) -0.0019(5) 0.0058(5) 0.0002(5) C5 0.0147(6) 0.0138(6) 0.0113(6) -0.0022(5) 0.0049(5) 0.0009(5) C6 0.0144(6) 0.0144(7) 0.0144(6) -0.0016(5) 0.0064(5) -0.0001(5) C7 0.0126(6) 0.0146(7) 0.0156(7) -0.0039(5) 0.0065(5) 0.0000(5) C8 0.0155(7) 0.0175(7) 0.0102(6) -0.0028(5) 0.0038(5) 0.0025(6) C9 0.0266(8) 0.0150(7) 0.0131(7) 0.0010(5) 0.0072(6) 0.0046(6) C10 0.0247(8) 0.0128(7) 0.0140(7) -0.0011(5) 0.0072(6) 0.0020(6) C11 0.0260(8) 0.0161(7) 0.0209(8) -0.0052(6) 0.0124(7) -0.0052(6) C12 0.0215(8) 0.0326(9) 0.0256(9) -0.0057(7) 0.0127(7) -0.0003(7) C13 0.0327(9) 0.0149(7) 0.0137(7) 0.0023(6) 0.0000(7) -0.0007(7) Cu1 0.01664(9) 0.00839(9) 0.00909(9) -0.00100(6) 0.00473(7) 0.00110(7) N1 0.0162(6) 0.0111(5) 0.0113(5) -0.0020(4) 0.0056(5) 0.0011(5) N2 0.0184(6) 0.0122(6) 0.0111(5) -0.0028(4) 0.0056(5) 0.0017(5) N3 0.0198(6) 0.0205(7) 0.0133(6) -0.0029(5) 0.0052(5) 0.0020(5) O1 0.0209(5) 0.0100(5) 0.0104(5) -0.0006(4) 0.0045(4) 0.0023(4) O2 0.0308(6) 0.0140(5) 0.0120(5) 0.0011(4) 0.0077(5) 0.0042(5) O3 0.0259(6) 0.0107(5) 0.0114(5) -0.0014(4) 0.0078(4) 0.0006(4) O4 0.0351(7) 0.0265(6) 0.0128(5) 0.0013(5) 0.0032(5) 0.0066(5) O5 0.0450(8) 0.0215(6) 0.0194(6) -0.0049(5) 0.0141(6) 0.0071(6) O6 0.0175(5) 0.0238(6) 0.0212(6) -0.0109(5) 0.0087(5) -0.0065(5) O7 0.0206(5) 0.0102(5) 0.0098(5) -0.0014(4) 0.0044(4) 0.0004(4) _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 C1 C2 1.519(2) . ? C1 O1 1.3008(17) . ? C1 O2 1.2296(18) . ? C2 C3 1.485(2) . ? C2 N1 1.2829(19) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.491(2) . ? C4 N2 1.3305(19) . ? C4 O3 1.2896(18) . ? C5 C6 1.394(2) . ? C5 C10 1.395(2) . ? C6 H6 0.9500 . ? C6 C7 1.397(2) . ? C7 C8 1.406(2) . ? C7 C11 1.503(2) . ? C8 C9 1.387(2) . ? C8 N3 1.4730(19) . ? C9 H9 0.9500 . ? C9 C10 1.384(2) . ? C10 H10 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C12 O6 1.415(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13 O7 1.450(2) . ? Cu1 N1 1.9130(13) . ? Cu1 O1 1.9988(12) . ? Cu1 O3 1.9725(11) . ? Cu1 O6 2.2138(14) . ? Cu1 O7 1.9506(11) . ? N1 N2 1.3791(16) . ? N3 O4 1.2264(18) . ? N3 O5 1.2257(18) . ? O6 H6A 0.71(2) . ? O7 H7 0.77(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 C1 C2 116.24(12) . . ? O2 C1 C2 119.74(13) . . ? O2 C1 O1 124.00(13) . . ? C3 C2 C1 121.62(13) . . ? N1 C2 C1 111.74(13) . . ? N1 C2 C3 126.63(13) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3B 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 C5 117.12(13) . . ? O3 C4 C5 117.19(13) . . ? O3 C4 N2 125.69(13) . . ? C6 C5 C4 121.24(13) . . ? C6 C5 C10 119.82(13) . . ? C10 C5 C4 118.92(13) . . ? C5 C6 H6 118.8 . . ? C5 C6 C7 122.34(14) . . ? C7 C6 H6 118.8 . . ? C6 C7 C8 115.57(13) . . ? C6 C7 C11 119.41(14) . . ? C8 C7 C11 124.99(13) . . ? C7 C8 N3 120.90(13) . . ? C9 C8 C7 123.35(14) . . ? C9 C8 N3 115.75(13) . . ? C8 C9 H9 120.4 . . ? C10 C9 C8 119.18(14) . . ? C10 C9 H9 120.4 . . ? C5 C10 H10 120.1 . . ? C9 C10 C5 119.70(14) . . ? C9 C10 H10 120.1 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O6 C12 H12A 109.5 . . ? O6 C12 H12B 109.5 . . ? O6 C12 H12C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O7 C13 H13A 109.5 . . ? O7 C13 H13B 109.5 . . ? O7 C13 H13C 109.5 . . ? N1 Cu1 O1 82.12(5) . . ? N1 Cu1 O3 79.88(5) . . ? N1 Cu1 O6 98.27(5) . . ? N1 Cu1 O7 171.44(5) . . ? O1 Cu1 O6 95.58(6) . . ? O3 Cu1 O1 160.24(5) . . ? O3 Cu1 O6 95.02(6) . . ? O7 Cu1 O1 99.18(4) . . ? O7 Cu1 O3 97.44(4) . . ? O7 Cu1 O6 90.04(5) . . ? C2 N1 Cu1 117.97(10) . . ? C2 N1 N2 124.27(13) . . ? N2 N1 Cu1 117.67(9) . . ? C4 N2 N1 106.71(12) . . ? O4 N3 C8 117.97(13) . . ? O5 N3 C8 118.35(13) . . ? O5 N3 O4 123.66(14) . . ? C1 O1 Cu1 111.60(9) . . ? C4 O3 Cu1 109.11(9) . . ? C12 O6 Cu1 121.01(11) . . ? C12 O6 H6A 113.2(19) . . ? Cu1 O6 H6A 116.3(19) . . ? C13 O7 Cu1 115.98(9) . . ? C13 O7 H7 111.8(18) . . ? Cu1 O7 H7 118.3(17) . . ? 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 C1 C2 N1 Cu1 -1.20(17) . . . . ? C1 C2 N1 N2 -177.71(12) . . . . ? C2 C1 O1 Cu1 5.88(16) . . . . ? C2 N1 N2 C4 -177.82(14) . . . . ? C3 C2 N1 Cu1 177.37(12) . . . . ? C3 C2 N1 N2 0.9(2) . . . . ? C4 C5 C6 C7 179.99(14) . . . . ? C4 C5 C10 C9 180.00(14) . . . . ? C5 C4 N2 N1 -177.08(12) . . . . ? C5 C4 O3 Cu1 170.86(10) . . . . ? C5 C6 C7 C8 0.0(2) . . . . ? C5 C6 C7 C11 -178.02(14) . . . . ? C6 C5 C10 C9 -1.4(2) . . . . ? C6 C7 C8 C9 -1.6(2) . . . . ? C6 C7 C8 N3 177.54(13) . . . . ? C7 C8 C9 C10 1.6(2) . . . . ? C7 C8 N3 O4 153.63(15) . . . . ? C7 C8 N3 O5 -27.9(2) . . . . ? C8 C9 C10 C5 -0.1(2) . . . . ? C9 C8 N3 O4 -27.2(2) . . . . ? C9 C8 N3 O5 151.30(16) . . . . ? C10 C5 C6 C7 1.4(2) . . . . ? C11 C7 C8 C9 176.35(15) . . . . ? C11 C7 C8 N3 -4.5(2) . . . . ? Cu1 N1 N2 C4 5.66(15) . . . . ? N1 Cu1 O1 C1 -5.08(10) . . . . ? N1 Cu1 O3 C4 8.29(10) . . . . ? N1 Cu1 O6 C12 111.56(13) . . . . ? N1 Cu1 O7 C13 110.9(3) . . . . ? N2 C4 C5 C6 9.9(2) . . . . ? N2 C4 C5 C10 -171.53(14) . . . . ? N2 C4 O3 Cu1 -8.68(19) . . . . ? N3 C8 C9 C10 -177.54(14) . . . . ? O1 C1 C2 C3 177.99(14) . . . . ? O1 C1 C2 N1 -3.35(19) . . . . ? O1 Cu1 N1 C2 3.42(11) . . . . ? O1 Cu1 N1 N2 -179.84(11) . . . . ? O1 Cu1 O3 C4 33.0(2) . . . . ? O1 Cu1 O6 C12 28.74(13) . . . . ? O1 Cu1 O7 C13 -150.96(11) . . . . ? O2 C1 C2 C3 -3.2(2) . . . . ? O2 C1 C2 N1 175.41(14) . . . . ? O2 C1 O1 Cu1 -172.82(13) . . . . ? O3 C4 C5 C6 -169.67(14) . . . . ? O3 C4 C5 C10 8.9(2) . . . . ? O3 C4 N2 N1 2.5(2) . . . . ? O3 Cu1 N1 C2 175.23(12) . . . . ? O3 Cu1 N1 N2 -8.03(10) . . . . ? O3 Cu1 O1 C1 -29.60(19) . . . . ? O3 Cu1 O6 C12 -167.96(13) . . . . ? O3 Cu1 O7 C13 39.76(12) . . . . ? O6 Cu1 N1 C2 -91.11(12) . . . . ? O6 Cu1 N1 N2 85.63(11) . . . . ? O6 Cu1 O1 C1 92.53(10) . . . . ? O6 Cu1 O3 C4 -89.24(10) . . . . ? O6 Cu1 O7 C13 -55.31(12) . . . . ? O7 Cu1 N1 C2 102.8(3) . . . . ? O7 Cu1 N1 N2 -80.5(4) . . . . ? O7 Cu1 O1 C1 -176.53(10) . . . . ? O7 Cu1 O3 C4 -179.93(10) . . . . ? O7 Cu1 O6 C12 -70.49(13) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 -1 -1 0.0655 0.0015 -0.9991 -1.0032 -0.0210 0.0067 0.0795 -1 2 -1 0.0811 -0.9997 2.0042 -1.0038 -0.1522 0.0233 -0.0258 1 1 -1 0.0362 0.9999 1.0018 -0.9999 -0.0350 -0.0855 -0.0055 -1 -1 0 0.0546 -0.9990 -1.0000 -0.0027 -0.0150 0.0771 0.0469 1 1 0 0.0546 0.9990 1.0000 0.0027 0.0150 -0.0771 -0.0469 1 -2 1 0.0811 0.9997 -2.0042 1.0038 0.1522 -0.0233 0.0258 1 0 -1 0.0210 1.0005 0.0010 -1.0004 -0.0060 -0.0704 0.0326 0 0 -1 0.0762 0.0010 0.0018 -1.0026 -0.0500 -0.0084 0.0414 0 -1 0 0.0377 0.0006 -1.0008 -0.0005 0.0290 0.0151 0.0381 0 1 0 0.0456 -0.0006 1.0008 0.0005 -0.0290 -0.0151 -0.0381 0 1 1 0.0785 -0.0015 0.9991 1.0032 0.0210 -0.0067 -0.0795 -1 0 1 0.0210 -1.0005 -0.0010 1.0004 0.0060 0.0704 -0.0326 -1 -1 1 0.0362 -0.9999 -1.0018 0.9999 0.0350 0.0855 0.0055 data_akd1019 _database_code_depnum_ccdc_archive 'CCDC 866686' #TrackingRef '- akd1019.cif' _audit_creation_date 2012-04-12 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H8 N4 O3, H2 O' _chemical_formula_sum 'C8 H10 N4 O4' _chemical_formula_weight 226.20 _chemical_melting_point ? _chemical_oxdiff_formula 'Zn C16 N4 O6 H14' _chemical_oxdiff_usercomment "Abeda's ZnNPPZH" 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 8.1680(5) _cell_length_b 8.2337(6) _cell_length_c 8.5815(6) _cell_angle_alpha 109.642(7) _cell_angle_beta 99.708(5) _cell_angle_gamma 110.471(6) _cell_volume 481.70(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2099 _cell_measurement_temperature 110.0 _cell_measurement_theta_max 27.4951 _cell_measurement_theta_min 2.9158 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83413 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 236 _exptl_crystal_size_max 0.2073 _exptl_crystal_size_mid 0.1309 _exptl_crystal_size_min 0.0521 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_unetI/netI 0.0333 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4178 _diffrn_reflns_theta_full 27.56 _diffrn_reflns_theta_max 27.56 _diffrn_reflns_theta_min 2.92 _diffrn_ambient_temperature 110.0 _diffrn_detector_area_resol_mean 16.1450 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -90.00 10.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -20.1392 -77.0000 -180.0000 100 #__ type_ start__ end____ width___ exp.time_ 2 omega 9.00 42.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 21.3892 37.0000 -180.0000 33 #__ type_ start__ end____ width___ exp.time_ 3 omega -3.00 81.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 21.3892 67.0000 16.0000 84 #__ type_ start__ end____ width___ exp.time_ 4 omega 3.00 72.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 21.3892 37.0000 0.0000 69 #__ type_ start__ end____ width___ exp.time_ 5 omega 1.00 53.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 21.3892 67.0000 117.0000 52 #__ type_ start__ end____ width___ exp.time_ 6 omega -50.00 30.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 21.3892 -37.0000 -150.0000 80 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0159580000 _diffrn_orient_matrix_UB_12 -0.0965596000 _diffrn_orient_matrix_UB_13 -0.0454602000 _diffrn_orient_matrix_UB_21 0.0488717000 _diffrn_orient_matrix_UB_22 0.0261419000 _diffrn_orient_matrix_UB_23 -0.0552773000 _diffrn_orient_matrix_UB_31 0.0834210000 _diffrn_orient_matrix_UB_32 0.0185324000 _diffrn_orient_matrix_UB_33 0.0590366000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1800 _reflns_number_total 2229 _reflns_odcompleteness_completeness 99.87 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 27.50 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.296 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.050 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 2229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0413 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.1269P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1059 _refine_ls_wR_factor_ref 0.1137 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C1 C 0.6371(2) 0.7923(2) 0.4977(2) 0.0197(3) Uani 1 1 d . . . H1 H 0.542(2) 0.817(2) 0.545(2) 0.024 Uiso 1 1 d . . . C2 C 0.6879(2) 0.8588(2) 0.37578(19) 0.0185(3) Uani 1 1 d . . . H2 H 0.6289 0.9270 0.3393 0.022 Uiso 1 1 calc R . . C3 C 0.89215(19) 0.73071(19) 0.36405(18) 0.0139(3) Uani 1 1 d . . . C4 C 0.8419(2) 0.6629(2) 0.48488(19) 0.0179(3) Uani 1 1 d . . . H4 H 0.8991 0.5923 0.5194 0.022 Uiso 1 1 calc R . . C5 C 1.03847(19) 0.6933(2) 0.29525(19) 0.0153(3) Uani 1 1 d . . . C6 C 1.23692(18) 0.7854(2) -0.01378(18) 0.0138(3) Uani 1 1 d . . . C7 C 1.38043(19) 0.7471(2) -0.09007(18) 0.0142(3) Uani 1 1 d . . . C8 C 1.1545(2) 0.9001(2) -0.0706(2) 0.0194(3) Uani 1 1 d . . . H8A H 1.2048 0.9315 -0.1581 0.029 Uiso 1 1 calc R . . H8B H 1.1844 1.0188 0.0307 0.029 Uiso 1 1 calc R . . H8C H 1.0200 0.8253 -0.1216 0.029 Uiso 1 1 calc R . . N1 N 0.71462(17) 0.69473(18) 0.55384(17) 0.0200(3) Uani 1 1 d . . . N2 N 0.81647(16) 0.83011(17) 0.30835(16) 0.0156(3) Uani 1 1 d . . . N3 N 1.07105(16) 0.75231(17) 0.16847(16) 0.0146(3) Uani 1 1 d . . . H3 H 0.999(3) 0.792(3) 0.131(3) 0.033(5) Uiso 1 1 d . . . N4 N 1.20074(16) 0.71751(17) 0.09734(15) 0.0140(3) Uani 1 1 d . . . O1 O 1.12305(16) 0.61811(17) 0.35253(15) 0.0256(3) Uani 1 1 d . . . O2 O 1.44366(14) 0.64361(15) -0.03334(14) 0.0187(3) Uani 1 1 d . . . H2A H 1.533(3) 0.623(3) -0.081(3) 0.045(6) Uiso 1 1 d . . . O3 O 1.42837(14) 0.80838(15) -0.19353(14) 0.0200(3) Uani 1 1 d . . . O4 O 0.69860(15) 0.59945(16) 0.84459(15) 0.0188(3) Uani 1 1 d . . . H4A H 0.690(3) 0.604(3) 0.748(3) 0.041(6) Uiso 1 1 d . . . H4B H 0.713(3) 0.499(3) 0.835(3) 0.051(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 C1 0.0187(7) 0.0235(8) 0.0197(7) 0.0095(6) 0.0098(6) 0.0104(6) C2 0.0192(7) 0.0216(8) 0.0200(7) 0.0111(6) 0.0073(6) 0.0121(6) C3 0.0160(7) 0.0135(7) 0.0138(7) 0.0069(5) 0.0056(5) 0.0067(6) C4 0.0224(7) 0.0200(7) 0.0196(7) 0.0126(6) 0.0113(6) 0.0122(6) C5 0.0192(7) 0.0154(7) 0.0177(7) 0.0103(6) 0.0088(6) 0.0100(6) C6 0.0126(6) 0.0133(7) 0.0162(7) 0.0076(5) 0.0046(5) 0.0053(5) C7 0.0143(6) 0.0137(7) 0.0150(7) 0.0068(5) 0.0047(5) 0.0060(5) C8 0.0185(7) 0.0244(8) 0.0286(8) 0.0201(7) 0.0127(6) 0.0130(6) N1 0.0231(7) 0.0218(7) 0.0202(7) 0.0119(5) 0.0117(5) 0.0104(5) N2 0.0185(6) 0.0166(6) 0.0154(6) 0.0087(5) 0.0070(5) 0.0092(5) N3 0.0164(6) 0.0184(6) 0.0188(6) 0.0122(5) 0.0097(5) 0.0121(5) N4 0.0142(6) 0.0153(6) 0.0162(6) 0.0082(5) 0.0074(5) 0.0079(5) O1 0.0349(7) 0.0388(7) 0.0314(6) 0.0276(6) 0.0216(5) 0.0295(6) O2 0.0215(5) 0.0247(6) 0.0260(6) 0.0180(5) 0.0156(4) 0.0168(5) O3 0.0230(6) 0.0254(6) 0.0222(6) 0.0164(5) 0.0138(4) 0.0132(5) O4 0.0244(6) 0.0210(6) 0.0234(6) 0.0146(5) 0.0143(5) 0.0152(5) _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 C1 H1 0.984(18) . ? C1 C2 1.392(2) . ? C1 N1 1.339(2) . ? C2 H2 0.9500 . ? C2 N2 1.3339(19) . ? C3 C4 1.389(2) . ? C3 C5 1.498(2) . ? C3 N2 1.3408(18) . ? C4 H4 0.9500 . ? C4 N1 1.3392(19) . ? C5 N3 1.3615(18) . ? C5 O1 1.2209(17) . ? C6 C7 1.510(2) . ? C6 C8 1.4923(19) . ? C6 N4 1.2831(18) . ? C7 O2 1.3163(17) . ? C7 O3 1.2150(17) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? N3 H3 0.83(2) . ? N3 N4 1.3746(16) . ? O2 H2A 0.94(2) . ? O4 H4A 0.83(2) . ? O4 H4B 0.85(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 C2 C1 H1 120.0(10) . . ? N1 C1 H1 118.3(11) . . ? N1 C1 C2 121.69(14) . . ? C1 C2 H2 118.8 . . ? N2 C2 C1 122.38(14) . . ? N2 C2 H2 118.8 . . ? C4 C3 C5 118.56(13) . . ? N2 C3 C4 122.57(13) . . ? N2 C3 C5 118.87(12) . . ? C3 C4 H4 119.3 . . ? N1 C4 C3 121.47(14) . . ? N1 C4 H4 119.3 . . ? N3 C5 C3 115.10(12) . . ? O1 C5 C3 121.55(13) . . ? O1 C5 N3 123.34(13) . . ? C8 C6 C7 117.80(12) . . ? N4 C6 C7 115.74(12) . . ? N4 C6 C8 126.45(13) . . ? O2 C7 C6 113.30(12) . . ? O3 C7 C6 121.32(13) . . ? O3 C7 O2 125.38(13) . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 N1 C4 116.32(13) . . ? C2 N2 C3 115.55(13) . . ? C5 N3 H3 116.2(14) . . ? C5 N3 N4 117.70(12) . . ? N4 N3 H3 125.4(14) . . ? C6 N4 N3 116.29(12) . . ? C7 O2 H2A 111.9(13) . . ? H4A O4 H4B 107(2) . . ? 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 O2 H2A O4 0.94(2) 1.63(2) 2.5642(14) 176(2) 1_654 O4 H4A N1 0.83(2) 2.06(2) 2.8656(17) 164(2) . 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 C1 C2 N2 C3 0.8(2) . . . . ? C2 C1 N1 C4 -0.7(2) . . . . ? C3 C4 N1 C1 1.1(2) . . . . ? C3 C5 N3 N4 -178.45(11) . . . . ? C4 C3 C5 N3 175.61(12) . . . . ? C4 C3 C5 O1 -5.6(2) . . . . ? C4 C3 N2 C2 -0.5(2) . . . . ? C5 C3 C4 N1 178.71(13) . . . . ? C5 C3 N2 C2 -179.68(13) . . . . ? C5 N3 N4 C6 -175.75(12) . . . . ? C7 C6 N4 N3 179.65(11) . . . . ? C8 C6 C7 O2 -179.43(12) . . . . ? C8 C6 C7 O3 0.4(2) . . . . ? C8 C6 N4 N3 1.0(2) . . . . ? N1 C1 C2 N2 -0.2(2) . . . . ? N2 C3 C4 N1 -0.5(2) . . . . ? N2 C3 C5 N3 -5.2(2) . . . . ? N2 C3 C5 O1 173.62(13) . . . . ? N4 C6 C7 O2 1.81(19) . . . . ? N4 C6 C7 O3 -178.34(13) . . . . ? O1 C5 N3 N4 2.8(2) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -1 0 0 0.0716 -1.0000 0.0000 -0.0000 0.0160 -0.0488 -0.0836 1 0 0 0.0716 1.0000 -0.0000 0.0000 -0.0160 0.0488 0.0836 0 0 1 0.0228 -0.0000 -0.0000 1.0000 -0.0454 -0.0554 0.0591 0 0 -1 0.0293 0.0000 0.0000 -1.0000 0.0454 0.0554 -0.0591 0 -1 0 0.0695 -0.0000 -1.0000 -0.0000 0.0969 -0.0261 -0.0186 0 1 0 0.0473 0.0000 1.0000 0.0000 -0.0969 0.0261 0.0186 1 -2 1 0.0689 1.0000 -2.0000 1.0000 0.1323 -0.0589 0.1054 0 -2 1 0.0639 0.0000 -2.0000 1.0000 0.1483 -0.1077 0.0219