data_sb0769a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Cu N7 O8' _chemical_formula_weight 501.93 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5396(8) _cell_length_b 9.7085(8) _cell_length_c 12.6295(12) _cell_angle_alpha 74.927(2) _cell_angle_beta 76.612(2) _cell_angle_gamma 87.388(2) _cell_volume 1098.61(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'green' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 1.051 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.7573 _exptl_absorpt_correction_T_max 0.8842 _exptl_absorpt_process_details 'sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II' _diffrn_measurement_method 'Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13046 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3830 _reflns_number_gt 3169 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction 'SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material 'Shelxl-97' _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^)+(0.0367P)^2^+0.4328P] 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 3830 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0822 _refine_ls_wR_factor_gt 0.0776 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 Cu1 Cu 0.66463(3) 0.59578(3) -0.39721(3) 0.03287(11) Uani 1 1 d . . . N1 N 0.7220(2) 0.5056(2) -0.25333(17) 0.0342(5) Uani 1 1 d . . . C2 C 0.8058(3) 0.3916(3) -0.2439(2) 0.0453(7) Uani 1 1 d . . . H2 H 0.8393 0.3545 -0.3059 0.054 Uiso 1 1 calc R . . C3 C 0.8434(4) 0.3285(4) -0.1445(3) 0.0627(9) Uani 1 1 d . . . H3 H 0.9002 0.2476 -0.1386 0.075 Uiso 1 1 calc R . . C4 C 0.7974(4) 0.3844(3) -0.0535(3) 0.0599(9) Uani 1 1 d . . . H4 H 0.8234 0.3420 0.0140 0.072 Uiso 1 1 calc R . . C5 C 0.7122(3) 0.5042(3) -0.0626(2) 0.0400(6) Uani 1 1 d . . . C6 C 0.6750(3) 0.5603(3) -0.1649(2) 0.0360(6) Uani 1 1 d . . . H6 H 0.6152 0.6390 -0.1723 0.043 Uiso 1 1 calc R . . N7 N 0.6650(3) 0.5606(2) 0.02986(18) 0.0466(6) Uani 1 1 d . . . H7 H 0.6703 0.5067 0.0946 0.056 Uiso 1 1 calc R . . C8 C 0.6099(3) 0.6967(3) 0.0271(2) 0.0413(6) Uani 1 1 d . . . O9 O 0.5977(3) 0.7817(2) -0.05925(17) 0.0676(7) Uani 1 1 d . . . N10 N 0.5721(2) 0.7230(2) 0.12939(18) 0.0423(6) Uani 1 1 d . . . H10 H 0.5823 0.6566 0.1872 0.051 Uiso 1 1 calc R . . C11 C 0.5151(3) 0.8583(3) 0.1460(2) 0.0417(7) Uani 1 1 d . . . H11A H 0.4410 0.8410 0.2153 0.050 Uiso 1 1 calc R . . H11B H 0.4702 0.9042 0.0846 0.050 Uiso 1 1 calc R . . C12 C 0.6291(3) 0.9588(3) 0.1521(2) 0.0467(7) Uani 1 1 d . . . H12A H 0.7002 0.9812 0.0811 0.056 Uiso 1 1 calc R . . H12B H 0.5842 1.0471 0.1633 0.056 Uiso 1 1 calc R . . C13 C 0.7031(3) 0.8949(3) 0.2459(3) 0.0496(7) Uani 1 1 d . . . H13A H 0.6309 0.8573 0.3145 0.059 Uiso 1 1 calc R . . H13B H 0.7614 0.8159 0.2280 0.059 Uiso 1 1 calc R . . N14 N 0.7945(2) 0.9977(2) 0.2652(2) 0.0496(6) Uani 1 1 d . . . H14 H 0.7724 1.0864 0.2495 0.060 Uiso 1 1 calc R . . C15 C 0.9112(3) 0.9594(3) 0.3064(2) 0.0360(6) Uani 1 1 d . . . O16 O 0.95753(19) 0.83782(19) 0.32313(17) 0.0461(5) Uani 1 1 d . . . N17 N 0.9756(2) 1.0687(2) 0.3289(2) 0.0457(6) Uani 1 1 d . . . H17 H 0.9309 1.1484 0.3216 0.055 Uiso 1 1 calc R . . C18 C 1.1054(3) 1.0650(3) 0.3624(2) 0.0336(6) Uani 1 1 d . . . C19 C 1.1891(3) 0.9461(3) 0.3880(2) 0.0443(7) Uani 1 1 d . . . H19 H 1.1599 0.8569 0.3858 0.053 Uiso 1 1 calc R . . C20 C 1.3173(3) 0.9634(3) 0.4170(2) 0.0452(7) Uani 1 1 d . . . H20 H 1.3748 0.8848 0.4352 0.054 Uiso 1 1 calc R . . C21 C 1.3600(3) 1.0941(3) 0.4191(2) 0.0398(6) Uani 1 1 d . . . H21 H 1.4477 1.1036 0.4370 0.048 Uiso 1 1 calc R . . N22 N 1.2790(2) 1.2098(2) 0.39612(17) 0.0334(5) Uani 1 1 d . . . C23 C 1.1543(3) 1.1936(3) 0.3695(2) 0.0360(6) Uani 1 1 d . . . H23 H 1.0971 1.2733 0.3548 0.043 Uiso 1 1 calc R . . O24 O 0.59893(18) 0.40774(17) -0.40483(14) 0.0367(4) Uani 1 1 d . . . O25 O 0.53513(19) 0.67390(17) -0.50057(15) 0.0363(4) Uani 1 1 d . . . C26 C 0.4814(3) 0.5766(2) -0.5275(2) 0.0315(6) Uani 1 1 d . . . O27 O 0.8582(3) 0.5808(3) -0.5275(2) 0.0536(6) Uani 1 1 d . . . N28 N 0.2417(3) 0.6127(3) 0.7068(2) 0.0566(7) Uani 1 1 d . . . O29 O 0.2938(3) 0.4944(3) 0.7110(2) 0.0817(8) Uani 1 1 d . . . O30 O 0.2694(4) 0.6830(3) 0.7665(2) 0.1130(12) Uani 1 1 d . . . O31 O 0.1619(3) 0.6583(3) 0.6412(2) 0.0763(7) Uani 1 1 d . . . H27B H 0.882(4) 0.651(4) -0.571(3) 0.068(14) Uiso 1 1 d . . . H27A H 0.853(4) 0.521(4) -0.553(3) 0.078(15) 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 Cu1 0.0428(2) 0.02494(18) 0.03948(19) -0.01167(13) -0.02267(14) 0.00142(13) N1 0.0406(12) 0.0302(12) 0.0391(12) -0.0118(10) -0.0203(10) 0.0027(9) C2 0.0590(18) 0.0391(16) 0.0473(17) -0.0190(14) -0.0246(14) 0.0149(14) C3 0.087(2) 0.057(2) 0.058(2) -0.0266(17) -0.0377(18) 0.0393(18) C4 0.087(2) 0.054(2) 0.0496(18) -0.0177(15) -0.0383(17) 0.0316(18) C5 0.0496(16) 0.0365(15) 0.0405(15) -0.0140(12) -0.0198(13) 0.0060(13) C6 0.0416(15) 0.0308(14) 0.0414(15) -0.0120(12) -0.0190(12) 0.0053(11) N7 0.0708(17) 0.0402(14) 0.0337(12) -0.0108(11) -0.0224(12) 0.0122(12) C8 0.0492(16) 0.0394(16) 0.0417(16) -0.0140(13) -0.0198(13) 0.0044(13) O9 0.122(2) 0.0470(13) 0.0400(12) -0.0127(10) -0.0335(12) 0.0304(13) N10 0.0610(15) 0.0366(13) 0.0358(12) -0.0118(10) -0.0211(11) 0.0011(11) C11 0.0468(16) 0.0413(16) 0.0476(16) -0.0209(13) -0.0224(13) 0.0082(13) C12 0.0543(18) 0.0381(16) 0.0566(18) -0.0163(14) -0.0254(15) -0.0001(13) C13 0.0513(17) 0.0415(17) 0.0654(19) -0.0149(15) -0.0296(15) -0.0059(14) N14 0.0523(14) 0.0306(13) 0.0802(18) -0.0190(12) -0.0380(13) 0.0015(11) C15 0.0364(14) 0.0324(15) 0.0443(15) -0.0149(12) -0.0136(12) -0.0003(12) O16 0.0444(11) 0.0293(10) 0.0746(14) -0.0205(10) -0.0256(10) 0.0028(8) N17 0.0442(13) 0.0265(12) 0.0810(18) -0.0229(12) -0.0344(13) 0.0080(10) C18 0.0360(14) 0.0301(14) 0.0422(15) -0.0153(12) -0.0170(12) 0.0021(11) C19 0.0513(17) 0.0253(14) 0.0671(19) -0.0204(14) -0.0263(15) 0.0054(12) C20 0.0524(17) 0.0277(14) 0.0672(19) -0.0187(14) -0.0315(15) 0.0131(12) C21 0.0416(15) 0.0348(15) 0.0537(17) -0.0180(13) -0.0257(13) 0.0083(12) N22 0.0394(12) 0.0268(11) 0.0414(12) -0.0129(10) -0.0198(10) 0.0044(9) C23 0.0404(15) 0.0277(14) 0.0478(16) -0.0148(12) -0.0212(12) 0.0071(11) O24 0.0487(11) 0.0255(9) 0.0452(10) -0.0091(8) -0.0292(9) 0.0026(8) O25 0.0499(11) 0.0219(9) 0.0471(10) -0.0101(8) -0.0294(9) 0.0003(8) C26 0.0380(14) 0.0263(14) 0.0349(13) -0.0102(11) -0.0154(11) 0.0036(11) O27 0.0588(14) 0.0411(15) 0.0603(15) -0.0170(14) -0.0080(11) 0.0024(12) N28 0.0822(19) 0.0460(16) 0.0449(15) -0.0143(13) -0.0217(14) 0.0193(14) O29 0.113(2) 0.0574(16) 0.0812(18) -0.0189(13) -0.0419(16) 0.0454(15) O30 0.221(4) 0.0657(18) 0.0824(19) -0.0341(16) -0.081(2) 0.024(2) O31 0.0920(18) 0.0692(16) 0.0797(17) -0.0224(14) -0.0470(15) 0.0414(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 Cu1 O25 1.9879(16) . ? Cu1 N1 1.989(2) . ? Cu1 O24 1.9897(16) . ? Cu1 N22 1.9908(19) 2_775 ? Cu1 O27 2.198(2) . ? N1 C2 1.331(3) . ? N1 C6 1.336(3) . ? C2 C3 1.368(4) . ? C2 H2 0.9300 . ? C3 C4 1.369(4) . ? C3 H3 0.9300 . ? C4 C5 1.384(4) . ? C4 H4 0.9300 . ? C5 C6 1.386(3) . ? C5 N7 1.390(3) . ? C6 H6 0.9300 . ? N7 C8 1.394(3) . ? N7 H7 0.8600 . ? C8 O9 1.211(3) . ? C8 N10 1.346(3) . ? N10 C11 1.446(3) . ? N10 H10 0.8600 . ? C11 C12 1.521(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.500(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N14 1.457(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? N14 C15 1.333(3) . ? N14 H14 0.8600 . ? C15 O16 1.224(3) . ? C15 N17 1.372(3) . ? N17 C18 1.395(3) . ? N17 H17 0.8600 . ? C18 C23 1.383(3) . ? C18 C19 1.385(3) . ? C19 C20 1.384(4) . ? C19 H19 0.9300 . ? C20 C21 1.359(4) . ? C20 H20 0.9300 . ? C21 N22 1.341(3) . ? C21 H21 0.9300 . ? N22 C23 1.335(3) . ? N22 Cu1 1.9908(19) 2_775 ? C23 H23 0.9300 . ? O24 C26 1.251(3) 2_664 ? O25 C26 1.250(3) . ? C26 O24 1.251(3) 2_664 ? C26 C26 1.533(5) 2_664 ? O27 H27B 0.76(4) . ? O27 H27A 0.74(4) . ? N28 O30 1.217(3) . ? N28 O29 1.224(3) . ? N28 O31 1.238(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 O25 Cu1 N1 158.27(8) . . ? O25 Cu1 O24 83.99(6) . . ? N1 Cu1 O24 90.81(7) . . ? O25 Cu1 N22 92.07(7) . 2_775 ? N1 Cu1 N22 92.78(8) . 2_775 ? O24 Cu1 N22 176.05(7) . 2_775 ? O25 Cu1 O27 97.02(9) . . ? N1 Cu1 O27 103.96(9) . . ? O24 Cu1 O27 88.69(10) . . ? N22 Cu1 O27 92.05(10) 2_775 . ? C2 N1 C6 119.7(2) . . ? C2 N1 Cu1 121.00(17) . . ? C6 N1 Cu1 119.27(17) . . ? N1 C2 C3 120.9(3) . . ? N1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 117.2(2) . . ? C4 C5 N7 119.8(2) . . ? C6 C5 N7 123.0(2) . . ? N1 C6 C5 122.4(2) . . ? N1 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? C5 N7 C8 125.9(2) . . ? C5 N7 H7 117.0 . . ? C8 N7 H7 117.0 . . ? O9 C8 N10 124.0(3) . . ? O9 C8 N7 122.8(2) . . ? N10 C8 N7 113.3(2) . . ? C8 N10 C11 122.6(2) . . ? C8 N10 H10 118.7 . . ? C11 N10 H10 118.7 . . ? N10 C11 C12 113.3(2) . . ? N10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? N10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 111.9(2) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? N14 C13 C12 112.6(2) . . ? N14 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? N14 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C15 N14 C13 122.4(2) . . ? C15 N14 H14 118.8 . . ? C13 N14 H14 118.8 . . ? O16 C15 N14 123.6(2) . . ? O16 C15 N17 122.5(2) . . ? N14 C15 N17 114.0(2) . . ? C15 N17 C18 127.2(2) . . ? C15 N17 H17 116.4 . . ? C18 N17 H17 116.4 . . ? C23 C18 C19 117.7(2) . . ? C23 C18 N17 116.1(2) . . ? C19 C18 N17 126.2(2) . . ? C20 C19 C18 118.2(2) . . ? C20 C19 H19 120.9 . . ? C18 C19 H19 120.9 . . ? C21 C20 C19 120.7(2) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? N22 C21 C20 121.7(2) . . ? N22 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? C23 N22 C21 117.9(2) . . ? C23 N22 Cu1 118.27(16) . 2_775 ? C21 N22 Cu1 123.78(16) . 2_775 ? N22 C23 C18 123.7(2) . . ? N22 C23 H23 118.1 . . ? C18 C23 H23 118.1 . . ? C26 O24 Cu1 110.89(15) 2_664 . ? C26 O25 Cu1 111.28(15) . . ? O25 C26 O24 126.4(2) . 2_664 ? O25 C26 C26 116.6(2) . 2_664 ? O24 C26 C26 117.1(2) 2_664 2_664 ? Cu1 O27 H27B 114(3) . . ? Cu1 O27 H27A 112(3) . . ? H27B O27 H27A 113(4) . . ? O30 N28 O29 119.6(3) . . ? O30 N28 O31 121.5(3) . . ? O29 N28 O31 118.9(3) . . ? 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 N7 H7 O30 0.86 2.34 3.170(3) 161.3 2_666 N7 H7 O29 0.86 2.55 3.289(3) 144.2 2_666 N10 H10 O29 0.86 2.18 2.982(3) 154.3 2_666 N14 H14 O30 0.86 2.22 3.071(4) 170.3 2_676 N17 H17 O31 0.86 2.15 2.977(3) 159.9 2_676 O27 H27B O16 0.76(4) 2.00(4) 2.761(4) 175(4) 1_554 O27 H27A O31 0.74(4) 2.32(4) 3.064(4) 177(4) 2_665 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.328 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.051