# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_x _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H20 N2 O8' _chemical_formula_weight 464.42 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5171(4) _cell_length_b 18.7049(6) _cell_length_c 10.6498(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.156(4) _cell_angle_gamma 90.00 _cell_volume 2048.07(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14624 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.10 _reflns_number_total 4470 _reflns_number_gt 2916 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0200P)^2^+0.8000P] 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 4470 _refine_ls_number_parameters 337 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0924 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.000 _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 O1 O 0.24031(13) 0.60963(8) 0.58254(15) 0.0285(4) Uani 1 1 d D . . H1C H 0.196(4) 0.586(2) 0.621(4) 0.034 Uiso 0.50 1 d PD . . O2 O 0.27953(14) 0.50707(8) 0.48920(16) 0.0297(4) Uani 1 1 d D . . H2A H 0.232(4) 0.490(2) 0.534(4) 0.036 Uiso 0.50 1 d PD . . O3 O 0.57363(15) 0.50146(8) 0.18934(16) 0.0323(4) Uani 1 1 d D . . H3A H 0.610(4) 0.481(2) 0.138(4) 0.039 Uiso 0.50 1 d PD . . O4 O 0.63345(16) 0.60412(8) 0.11400(18) 0.0379(4) Uani 1 1 d D . . H4A H 0.681(4) 0.577(2) 0.084(5) 0.045 Uiso 0.50 1 d PD . . O5 O 0.90396(14) 0.46451(8) 0.28778(17) 0.0345(4) Uani 1 1 d D . . H5 H 0.858(4) 0.445(2) 0.331(4) 0.041 Uiso 0.50 1 d PD . . O6 O 0.87916(16) 0.56264(9) 0.39811(18) 0.0403(4) Uani 1 1 d D . . H6A H 0.827(4) 0.539(2) 0.429(5) 0.048 Uiso 0.50 1 d PD . . O7 O 1.31833(14) 0.56888(8) -0.02667(16) 0.0289(4) Uani 1 1 d D . . H7A H 1.356(4) 0.544(2) -0.070(4) 0.035 Uiso 0.50 1 d PD . . O8 O 1.22974(14) 0.46623(8) 0.02052(17) 0.0337(4) Uani 1 1 d D . . H8 H 1.279(4) 0.448(2) -0.020(4) 0.040 Uiso 0.50 1 d PD . . N1 N 1.12175(16) 0.75542(9) 0.21576(18) 0.0243(4) Uani 1 1 d D . . H1 H 1.1876(14) 0.7751(10) 0.187(2) 0.029 Uiso 1 1 d D . . N2 N 0.47014(16) 0.79568(9) 0.36885(19) 0.0270(4) Uani 1 1 d D . . H2 H 0.4301(18) 0.8189(10) 0.4203(17) 0.032 Uiso 1 1 d D . . C1 C 0.53235(18) 0.83745(11) 0.2844(2) 0.0268(5) Uani 1 1 d . . . H1A H 0.5186 0.8887 0.3006 0.032 Uiso 1 1 calc R . . H1B H 0.4881 0.8272 0.1947 0.032 Uiso 1 1 calc R . . C2 C 0.67681(18) 0.82503(10) 0.2969(2) 0.0224(5) Uani 1 1 d . . . C3 C 0.75409(19) 0.79663(10) 0.4067(2) 0.0237(5) Uani 1 1 d . . . H3 H 0.7168 0.7844 0.4777 0.028 Uiso 1 1 calc R . . C4 C 0.88529(19) 0.78607(10) 0.4135(2) 0.0246(5) Uani 1 1 d . . . H4 H 0.9371 0.7660 0.4892 0.029 Uiso 1 1 calc R . . C5 C 0.94301(18) 0.80408(10) 0.3125(2) 0.0229(5) Uani 1 1 d . . . C6 C 0.86588(19) 0.83322(10) 0.2023(2) 0.0253(5) Uani 1 1 d . . . H6 H 0.9037 0.8463 0.1321 0.030 Uiso 1 1 calc R . . C7 C 0.73417(19) 0.84317(11) 0.1946(2) 0.0263(5) Uani 1 1 d . . . H7 H 0.6821 0.8626 0.1185 0.032 Uiso 1 1 calc R . . C8 C 1.08732(18) 0.79212(11) 0.3238(2) 0.0248(5) Uani 1 1 d . . . H8A H 1.1316 0.8391 0.3341 0.030 Uiso 1 1 calc R . . H8B H 1.1209 0.7641 0.4026 0.030 Uiso 1 1 calc R . . C9 C 1.11069(18) 0.68170(10) 0.2046(2) 0.0214(5) Uani 1 1 d . . . C10 C 1.02888(18) 0.64264(10) 0.2666(2) 0.0223(5) Uani 1 1 d . . . H10 H 0.9819 0.6664 0.3213 0.027 Uiso 1 1 calc R . . C11 C 1.01564(18) 0.56928(10) 0.2488(2) 0.0215(5) Uani 1 1 d . . . C12 C 1.08386(17) 0.53260(11) 0.1707(2) 0.0221(5) Uani 1 1 d . . . H12 H 1.0742 0.4824 0.1589 0.026 Uiso 1 1 calc R . . C13 C 1.16662(18) 0.57139(10) 0.1104(2) 0.0211(5) Uani 1 1 d . . . C14 C 1.18030(18) 0.64462(10) 0.1269(2) 0.0212(5) Uani 1 1 d . . . H14 H 1.2377 0.6700 0.0850 0.025 Uiso 1 1 calc R . . C15 C 1.24315(18) 0.53333(11) 0.0291(2) 0.0223(5) Uani 1 1 d . . . C16 C 0.92752(19) 0.52943(11) 0.3163(2) 0.0243(5) Uani 1 1 d . . . C17 C 0.45821(17) 0.72268(10) 0.3602(2) 0.0211(4) Uani 1 1 d . . . C18 C 0.51773(18) 0.68299(10) 0.2767(2) 0.0222(5) Uani 1 1 d . . . H18 H 0.5647 0.7069 0.2222 0.027 Uiso 1 1 calc R . . C19 C 0.50849(18) 0.60905(10) 0.2732(2) 0.0205(5) Uani 1 1 d . . . C20 C 0.43734(17) 0.57238(10) 0.3491(2) 0.0212(4) Uani 1 1 d . . . H20 H 0.4313 0.5217 0.3462 0.025 Uiso 1 1 calc R . . C21 C 0.37533(17) 0.61180(10) 0.4294(2) 0.0196(4) Uani 1 1 d . . . C22 C 0.38640(17) 0.68549(10) 0.4360(2) 0.0211(5) Uani 1 1 d . . . H22 H 0.3447 0.7113 0.4928 0.025 Uiso 1 1 calc R . . C23 C 0.29343(18) 0.57378(11) 0.5064(2) 0.0226(5) Uani 1 1 d . . . C24 C 0.57618(18) 0.56941(10) 0.1860(2) 0.0230(5) 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 O1 0.0314(8) 0.0284(9) 0.0317(10) -0.0008(7) 0.0201(7) -0.0015(7) O2 0.0373(9) 0.0228(9) 0.0348(10) 0.0004(7) 0.0205(7) -0.0034(7) O3 0.0457(10) 0.0186(8) 0.0411(11) -0.0038(7) 0.0283(8) 0.0004(7) O4 0.0523(10) 0.0250(9) 0.0481(11) 0.0030(8) 0.0369(9) 0.0033(7) O5 0.0432(10) 0.0245(9) 0.0416(11) -0.0018(7) 0.0218(8) -0.0089(7) O6 0.0509(11) 0.0345(10) 0.0471(12) -0.0055(8) 0.0364(9) -0.0083(8) O7 0.0306(8) 0.0292(9) 0.0327(10) -0.0031(7) 0.0196(7) -0.0014(7) O8 0.0424(10) 0.0206(9) 0.0441(11) -0.0027(7) 0.0230(8) 0.0027(7) N1 0.0253(9) 0.0205(9) 0.0303(11) -0.0016(8) 0.0128(8) -0.0036(7) N2 0.0297(10) 0.0185(9) 0.0385(12) -0.0044(8) 0.0199(9) 0.0002(7) C1 0.0290(11) 0.0199(11) 0.0335(14) 0.0005(10) 0.0111(10) 0.0020(9) C2 0.0263(11) 0.0145(10) 0.0276(13) -0.0035(9) 0.0083(9) -0.0013(8) C3 0.0309(11) 0.0198(11) 0.0229(12) -0.0022(9) 0.0114(9) -0.0018(9) C4 0.0276(11) 0.0227(11) 0.0226(12) -0.0014(9) 0.0034(9) -0.0005(9) C5 0.0256(11) 0.0147(10) 0.0282(13) -0.0032(9) 0.0055(9) -0.0026(8) C6 0.0315(11) 0.0235(11) 0.0242(12) -0.0004(9) 0.0139(10) -0.0023(9) C7 0.0306(11) 0.0226(11) 0.0255(13) 0.0020(9) 0.0053(10) 0.0015(9) C8 0.0258(11) 0.0202(11) 0.0299(13) -0.0035(9) 0.0091(9) -0.0023(9) C9 0.0207(10) 0.0222(11) 0.0212(12) 0.0002(9) 0.0040(8) -0.0004(8) C10 0.0220(10) 0.0246(11) 0.0218(12) -0.0021(9) 0.0080(9) 0.0020(9) C11 0.0214(10) 0.0232(11) 0.0206(12) 0.0011(9) 0.0058(9) -0.0015(8) C12 0.0248(11) 0.0187(10) 0.0237(12) 0.0006(9) 0.0074(9) 0.0012(8) C13 0.0216(10) 0.0218(11) 0.0205(12) 0.0001(9) 0.0056(9) 0.0020(8) C14 0.0202(10) 0.0237(11) 0.0208(12) 0.0022(9) 0.0071(9) -0.0002(8) C15 0.0232(10) 0.0228(12) 0.0215(12) 0.0007(9) 0.0060(9) 0.0020(9) C16 0.0261(11) 0.0229(11) 0.0266(13) 0.0004(10) 0.0115(9) -0.0006(9) C17 0.0193(10) 0.0200(11) 0.0242(12) -0.0027(9) 0.0055(9) 0.0011(8) C18 0.0204(10) 0.0231(11) 0.0243(12) 0.0021(9) 0.0076(9) -0.0020(8) C19 0.0196(10) 0.0212(11) 0.0219(12) -0.0003(9) 0.0069(9) 0.0013(8) C20 0.0221(10) 0.0175(10) 0.0252(12) 0.0005(9) 0.0080(9) -0.0014(8) C21 0.0169(9) 0.0245(11) 0.0177(11) 0.0010(9) 0.0042(8) 0.0010(8) C22 0.0190(10) 0.0252(11) 0.0199(12) -0.0029(9) 0.0061(8) 0.0023(8) C23 0.0187(10) 0.0261(12) 0.0233(12) 0.0018(9) 0.0054(9) 0.0012(9) C24 0.0231(11) 0.0188(11) 0.0285(13) 0.0002(9) 0.0087(9) 0.0009(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 O1 C23 1.269(2) . ? O1 H1C 0.815(10) . ? O2 C23 1.265(2) . ? O2 H2A 0.823(10) . ? O3 C24 1.272(2) . ? O3 H3A 0.822(10) . ? O4 C24 1.252(2) . ? O4 H4A 0.820(10) . ? O5 C16 1.264(2) . ? O5 H5 0.821(7) . ? O6 C16 1.261(3) . ? O6 H6A 0.818(10) . ? O7 C15 1.272(2) . ? O7 H7A 0.819(10) . ? O8 C15 1.264(2) . ? O8 H8 0.819(10) . ? N1 C9 1.387(2) . ? N1 C8 1.449(3) . ? N1 H1 0.894(9) . ? N2 C17 1.373(2) . ? N2 C1 1.447(3) . ? N2 H2 0.874(9) . ? C1 C2 1.515(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.383(3) . ? C2 C7 1.393(3) . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? C4 C5 1.384(3) . ? C4 H4 0.9500 . ? C5 C6 1.390(3) . ? C5 C8 1.514(3) . ? C6 C7 1.383(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.396(3) . ? C9 C14 1.399(3) . ? C10 C11 1.388(3) . ? C10 H10 0.9500 . ? C11 C12 1.389(3) . ? C11 C16 1.487(3) . ? C12 C13 1.390(3) . ? C12 H12 0.9500 . ? C13 C14 1.385(3) . ? C13 C15 1.482(3) . ? C14 H14 0.9500 . ? C17 C22 1.401(3) . ? C17 C18 1.403(3) . ? C18 C19 1.386(3) . ? C18 H18 0.9500 . ? C19 C20 1.392(3) . ? C19 C24 1.482(3) . ? C20 C21 1.391(3) . ? C20 H20 0.9500 . ? C21 C22 1.384(3) . ? C21 C23 1.489(3) . ? C22 H22 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C23 O1 H1C 114(3) . . ? C23 O2 H2A 112(3) . . ? C24 O3 H3A 115(4) . . ? C24 O4 H4A 110(4) . . ? C16 O5 H5 114(4) . . ? C16 O6 H6A 114(4) . . ? C15 O7 H7A 113(3) . . ? C15 O8 H8 112(4) . . ? C9 N1 C8 120.56(18) . . ? C9 N1 H1 115.9(14) . . ? C8 N1 H1 114.8(14) . . ? C17 N2 C1 122.82(18) . . ? C17 N2 H2 119.2(14) . . ? C1 N2 H2 117.5(15) . . ? N2 C1 C2 116.06(17) . . ? N2 C1 H1A 108.3 . . ? C2 C1 H1A 108.3 . . ? N2 C1 H1B 108.3 . . ? C2 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C3 C2 C7 118.74(19) . . ? C3 C2 C1 122.19(19) . . ? C7 C2 C1 119.07(19) . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 121.5(2) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C4 C5 C6 118.59(19) . . ? C4 C5 C8 119.92(19) . . ? C6 C5 C8 121.49(19) . . ? C7 C6 C5 120.1(2) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C2 121.0(2) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? N1 C8 C5 114.88(17) . . ? N1 C8 H8A 108.5 . . ? C5 C8 H8A 108.5 . . ? N1 C8 H8B 108.5 . . ? C5 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? N1 C9 C10 121.92(18) . . ? N1 C9 C14 119.92(18) . . ? C10 C9 C14 118.14(18) . . ? C11 C10 C9 120.47(19) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 121.34(18) . . ? C10 C11 C16 118.98(18) . . ? C12 C11 C16 119.67(18) . . ? C11 C12 C13 118.16(18) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? C14 C13 C12 121.05(18) . . ? C14 C13 C15 119.66(18) . . ? C12 C13 C15 119.28(18) . . ? C13 C14 C9 120.83(18) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? O8 C15 O7 123.76(19) . . ? O8 C15 C13 116.96(18) . . ? O7 C15 C13 119.28(18) . . ? O6 C16 O5 123.53(19) . . ? O6 C16 C11 118.04(18) . . ? O5 C16 C11 118.42(19) . . ? N2 C17 C22 120.51(18) . . ? N2 C17 C18 121.51(18) . . ? C22 C17 C18 117.97(18) . . ? C19 C18 C17 120.46(19) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 121.27(18) . . ? C18 C19 C24 118.41(18) . . ? C20 C19 C24 120.32(18) . . ? C21 C20 C19 118.33(18) . . ? C21 C20 H20 120.8 . . ? C19 C20 H20 120.8 . . ? C22 C21 C20 120.91(18) . . ? C22 C21 C23 120.01(18) . . ? C20 C21 C23 119.06(18) . . ? C21 C22 C17 121.01(18) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? O2 C23 O1 124.11(19) . . ? O2 C23 C21 116.99(18) . . ? O1 C23 C21 118.88(18) . . ? O4 C24 O3 123.42(19) . . ? O4 C24 C19 118.74(18) . . ? O3 C24 C19 117.84(18) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.282 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 937202' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 Co N O9' _chemical_formula_weight 379.19 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.8521(19) _cell_length_b 17.5183(10) _cell_length_c 10.0543(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.024(7) _cell_angle_gamma 90.00 _cell_volume 3496.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 1.023 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8294 _exptl_absorpt_correction_T_max 0.8617 _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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11495 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.97 _reflns_number_total 3411 _reflns_number_gt 2573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+55.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3411 _refine_ls_number_parameters 247 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0989 _refine_ls_R_factor_gt 0.0776 _refine_ls_wR_factor_ref 0.1880 _refine_ls_wR_factor_gt 0.1738 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.074 _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 O4 O 0.3451(3) 0.4343(2) -0.0239(4) 0.0520(14) Uani 1 1 d . . . O3 O 0.2960(2) 0.4239(2) 0.1697(4) 0.0392(10) Uani 1 1 d . . . C12 C 0.3239(3) 0.3941(3) 0.0702(5) 0.0320(13) Uani 1 1 d . . . O6W O 0.0784(4) 0.2364(4) 0.5597(8) 0.037(2) Uani 0.50 1 d P . . O4W O 0.1700(3) 0.3021(3) 0.4125(6) 0.0615(15) Uani 1 1 d D . . C1 C 0.2702(3) 0.1371(3) 0.2582(5) 0.0308(13) Uani 1 1 d . . . C2 C 0.3050(3) 0.1848(3) 0.1563(5) 0.0250(11) Uani 1 1 d . . . C3 C 0.3011(3) 0.2642(3) 0.1632(5) 0.0275(12) Uani 1 1 d . . . H3A H 0.2787 0.2876 0.2336 0.033 Uiso 1 1 calc R . . C4 C 0.3308(3) 0.3082(3) 0.0641(5) 0.0270(12) Uani 1 1 d . . . C5 C 0.3642(3) 0.2732(3) -0.0409(5) 0.0277(12) Uani 1 1 d . . . H5A H 0.3840 0.3030 -0.1065 0.033 Uiso 1 1 calc R . . C6 C 0.3683(3) 0.1930(3) -0.0493(5) 0.0255(11) Uani 1 1 d . . . C7 C 0.3393(3) 0.1495(3) 0.0516(5) 0.0245(11) Uani 1 1 d . . . H7A H 0.3429 0.0966 0.0493 0.029 Uiso 1 1 calc R . . C8 C 0.4036(3) 0.0781(3) -0.1726(5) 0.0302(12) Uani 1 1 d . . . H8A H 0.4154 0.0660 -0.2638 0.036 Uiso 1 1 calc R . . H8B H 0.3592 0.0572 -0.1560 0.036 Uiso 1 1 calc R . . C9 C 0.4533(3) 0.0388(3) -0.0812(5) 0.0253(11) Uani 1 1 d . . . C10 C 0.4540(3) -0.0406(3) -0.0743(6) 0.0358(13) Uani 1 1 d . . . H10A H 0.4232 -0.0686 -0.1241 0.043 Uiso 1 1 calc R . . C11 C 0.4998(3) 0.0784(3) -0.0065(7) 0.0382(14) Uani 1 1 d . . . H11A H 0.5004 0.1315 -0.0101 0.046 Uiso 1 1 calc R . . Co1 Co 0.19997(5) 0.04369(4) 0.41722(7) 0.0361(3) Uani 1 1 d D . . N1 N 0.4001(2) 0.1602(3) -0.1594(4) 0.0318(11) Uani 1 1 d . . . H1A H 0.4176 0.1890 -0.2194 0.038 Uiso 1 1 calc R . . O1 O 0.2729(2) 0.0651(2) 0.2504(3) 0.0322(9) Uani 1 1 d . . . O2 O 0.2370(3) 0.1683(2) 0.3509(4) 0.0545(15) Uani 1 1 d . . . O2W O 0.2848(2) 0.0409(2) 0.5544(4) 0.0319(9) Uani 1 1 d D . . O3W O 0.1460(2) 0.1009(2) 0.5815(4) 0.0394(10) Uani 1 1 d D . . O1W O 0.1143(3) 0.0635(3) 0.2845(4) 0.0523(13) Uani 1 1 d D . . O5W O 0.0322(9) 0.198(2) 0.367(2) 0.223(16) Uani 0.50 1 d P . . H1WA H 0.0704(13) 0.072(6) 0.297(4) 0.11(4) Uiso 1 1 d D . . H3WA H 0.107(3) 0.126(5) 0.587(4) 0.09(3) Uiso 1 1 d D . . H2WB H 0.314(3) 0.075(2) 0.589(8) 0.10(4) Uiso 1 1 d D . . H3WB H 0.154(5) 0.108(9) 0.667(4) 0.20(7) Uiso 1 1 d D . . H2WA H 0.300(3) 0.008(3) 0.616(7) 0.09(3) Uiso 1 1 d D . . H1WB H 0.108(2) 0.069(7) 0.197(2) 0.13(4) Uiso 1 1 d D . . H4WB H 0.152(7) 0.328(6) 0.356(9) 0.156 Uiso 1 1 d D . . H4WA H 0.177(7) 0.317(7) 0.489(5) 0.156 Uiso 1 1 d 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 O4 0.111(4) 0.020(2) 0.025(2) 0.0060(17) -0.002(2) -0.003(2) O3 0.068(3) 0.0164(18) 0.033(2) -0.0004(17) 0.000(2) 0.0061(19) C12 0.054(4) 0.020(3) 0.022(3) 0.004(2) -0.016(3) 0.000(2) O6W 0.053(5) 0.025(4) 0.035(4) 0.003(3) -0.006(4) 0.013(4) O4W 0.055(3) 0.059(3) 0.070(4) -0.025(3) -0.016(3) 0.014(3) C1 0.057(4) 0.021(3) 0.015(2) 0.002(2) 0.003(2) 0.002(3) C2 0.044(3) 0.015(2) 0.016(2) 0.0018(19) -0.003(2) 0.001(2) C3 0.046(3) 0.016(2) 0.020(3) 0.002(2) -0.003(2) 0.005(2) C4 0.041(3) 0.016(2) 0.024(3) 0.003(2) -0.009(2) 0.001(2) C5 0.033(3) 0.022(3) 0.028(3) 0.012(2) -0.002(2) -0.002(2) C6 0.031(3) 0.022(3) 0.024(3) 0.006(2) -0.004(2) 0.005(2) C7 0.034(3) 0.017(2) 0.023(2) 0.005(2) -0.003(2) 0.001(2) C8 0.032(3) 0.034(3) 0.025(3) -0.001(2) 0.002(2) 0.007(2) C9 0.024(3) 0.026(3) 0.027(3) 0.000(2) 0.004(2) 0.004(2) C10 0.031(3) 0.029(3) 0.047(4) -0.005(3) -0.009(3) 0.000(2) C11 0.032(3) 0.022(3) 0.061(4) 0.001(3) -0.008(3) 0.003(2) Co1 0.0667(6) 0.0195(4) 0.0220(4) -0.0004(3) 0.0060(4) 0.0004(4) N1 0.042(3) 0.028(2) 0.026(2) 0.008(2) 0.011(2) 0.008(2) O1 0.065(3) 0.0148(17) 0.0166(18) 0.0002(14) 0.0061(17) -0.0001(17) O2 0.118(4) 0.020(2) 0.025(2) 0.0037(17) 0.030(2) 0.015(2) O2W 0.056(3) 0.0189(18) 0.0208(18) 0.0029(16) 0.0039(17) -0.0031(18) O3W 0.065(3) 0.028(2) 0.025(2) -0.0013(17) 0.002(2) 0.011(2) O1W 0.083(4) 0.044(3) 0.030(2) 0.004(2) -0.010(2) 0.018(3) O5W 0.067(10) 0.48(5) 0.124(15) 0.12(2) 0.041(10) 0.107(18) _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 O4 C12 1.253(7) . ? O4 Co1 2.372(5) 4 ? O3 C12 1.255(7) . ? O3 Co1 2.275(4) 4 ? C12 C4 1.513(7) . ? O4W H4WB 0.81(2) . ? O4W H4WA 0.82(2) . ? C1 O2 1.265(7) . ? C1 O1 1.265(6) . ? C1 C2 1.491(7) . ? C2 C3 1.396(7) . ? C2 C7 1.399(7) . ? C3 C4 1.391(8) . ? C3 H3A 0.9300 . ? C4 C5 1.389(8) . ? C5 C6 1.409(7) . ? C5 H5A 0.9300 . ? C6 C7 1.393(7) . ? C6 N1 1.398(7) . ? C7 H7A 0.9300 . ? C8 N1 1.446(7) . ? C8 C9 1.515(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C11 1.377(8) . ? C9 C10 1.392(8) . ? C10 C11 1.393(8) 5_655 ? C10 H10A 0.9300 . ? C11 C10 1.393(8) 5_655 ? C11 H11A 0.9300 . ? Co1 O2W 2.177(4) . ? Co1 O1W 2.189(5) . ? Co1 O3W 2.210(4) . ? Co1 O1 2.247(4) . ? Co1 O3 2.275(4) 4_545 ? Co1 O4 2.372(5) 4_545 ? Co1 O2 2.398(4) . ? N1 H1A 0.8600 . ? O2W H2WB 0.892(18) . ? O2W H2WA 0.900(18) . ? O3W H3WA 0.893(18) . ? O3W H3WB 0.881(18) . ? O1W H1WA 0.892(18) . ? O1W H1WB 0.889(18) . ? 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 C12 O4 Co1 89.1(4) . 4 ? C12 O3 Co1 93.5(3) . 4 ? O4 C12 O3 121.1(5) . . ? O4 C12 C4 119.8(5) . . ? O3 C12 C4 119.0(5) . . ? H4WB O4W H4WA 123(6) . . ? O2 C1 O1 119.9(5) . . ? O2 C1 C2 120.4(5) . . ? O1 C1 C2 119.8(5) . . ? C3 C2 C7 120.4(5) . . ? C3 C2 C1 119.9(5) . . ? C7 C2 C1 119.7(4) . . ? C4 C3 C2 119.5(5) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C5 C4 C3 120.2(5) . . ? C5 C4 C12 120.9(5) . . ? C3 C4 C12 118.9(5) . . ? C4 C5 C6 120.9(5) . . ? C4 C5 H5A 119.6 . . ? C6 C5 H5A 119.6 . . ? C7 C6 N1 122.6(5) . . ? C7 C6 C5 118.5(5) . . ? N1 C6 C5 118.9(5) . . ? C6 C7 C2 120.5(5) . . ? C6 C7 H7A 119.7 . . ? C2 C7 H7A 119.7 . . ? N1 C8 C9 115.4(5) . . ? N1 C8 H8A 108.4 . . ? C9 C8 H8A 108.4 . . ? N1 C8 H8B 108.4 . . ? C9 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C11 C9 C10 118.1(5) . . ? C11 C9 C8 122.5(5) . . ? C10 C9 C8 119.4(5) . . ? C9 C10 C11 120.7(5) . 5_655 ? C9 C10 H10A 119.7 . . ? C11 C10 H10A 119.7 5_655 . ? C9 C11 C10 121.3(5) . 5_655 ? C9 C11 H11A 119.4 . . ? C10 C11 H11A 119.4 5_655 . ? O2W Co1 O1W 172.08(17) . . ? O2W Co1 O3W 84.94(16) . . ? O1W Co1 O3W 90.38(18) . . ? O2W Co1 O1 88.76(15) . . ? O1W Co1 O1 91.11(18) . . ? O3W Co1 O1 142.66(15) . . ? O2W Co1 O3 101.27(16) . 4_545 ? O1W Co1 O3 86.52(17) . 4_545 ? O3W Co1 O3 136.24(17) . 4_545 ? O1 Co1 O3 81.08(14) . 4_545 ? O2W Co1 O4 89.26(16) . 4_545 ? O1W Co1 O4 96.3(2) . 4_545 ? O3W Co1 O4 81.07(16) . 4_545 ? O1 Co1 O4 135.70(15) . 4_545 ? O3 Co1 O4 56.04(15) 4_545 4_545 ? O2W Co1 O2 87.68(17) . . ? O1W Co1 O2 85.7(2) . . ? O3W Co1 O2 86.81(15) . . ? O1 Co1 O2 56.14(13) . . ? O3 Co1 O2 136.24(14) 4_545 . ? O4 Co1 O2 167.71(14) 4_545 . ? C6 N1 C8 120.2(4) . . ? C6 N1 H1A 119.9 . . ? C8 N1 H1A 119.9 . . ? C1 O1 Co1 95.3(3) . . ? C1 O2 Co1 88.4(3) . . ? Co1 O2W H2WB 137(3) . . ? Co1 O2W H2WA 135(3) . . ? H2WB O2W H2WA 87(3) . . ? Co1 O3W H3WA 134(2) . . ? Co1 O3W H3WB 135(3) . . ? H3WA O3W H3WB 91(3) . . ? Co1 O1W H1WA 135(3) . . ? Co1 O1W H1WB 136(3) . . ? H1WA O1W H1WB 89(3) . . ? 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 Co1 O4 C12 O3 -4.1(6) 4 . . . ? Co1 O4 C12 C4 175.2(5) 4 . . . ? Co1 O3 C12 O4 4.2(6) 4 . . . ? Co1 O3 C12 C4 -175.0(5) 4 . . . ? O2 C1 C2 C3 0.2(9) . . . . ? O1 C1 C2 C3 178.9(5) . . . . ? O2 C1 C2 C7 -177.6(6) . . . . ? O1 C1 C2 C7 1.1(8) . . . . ? C7 C2 C3 C4 0.9(8) . . . . ? C1 C2 C3 C4 -176.8(5) . . . . ? C2 C3 C4 C5 0.0(8) . . . . ? C2 C3 C4 C12 177.7(5) . . . . ? O4 C12 C4 C5 3.9(9) . . . . ? O3 C12 C4 C5 -176.8(5) . . . . ? O4 C12 C4 C3 -173.8(6) . . . . ? O3 C12 C4 C3 5.5(8) . . . . ? C3 C4 C5 C6 0.2(8) . . . . ? C12 C4 C5 C6 -177.4(5) . . . . ? C4 C5 C6 C7 -1.3(8) . . . . ? C4 C5 C6 N1 177.6(5) . . . . ? N1 C6 C7 C2 -176.6(5) . . . . ? C5 C6 C7 C2 2.2(8) . . . . ? C3 C2 C7 C6 -2.0(8) . . . . ? C1 C2 C7 C6 175.7(5) . . . . ? N1 C8 C9 C11 -10.3(8) . . . . ? N1 C8 C9 C10 171.6(5) . . . . ? C11 C9 C10 C11 0.3(10) . . . 5_655 ? C8 C9 C10 C11 178.5(6) . . . 5_655 ? C10 C9 C11 C10 -0.3(10) . . . 5_655 ? C8 C9 C11 C10 -178.4(6) . . . 5_655 ? C7 C6 N1 C8 0.4(8) . . . . ? C5 C6 N1 C8 -178.4(5) . . . . ? C9 C8 N1 C6 -74.1(7) . . . . ? O2 C1 O1 Co1 5.5(6) . . . . ? C2 C1 O1 Co1 -173.2(5) . . . . ? O2W Co1 O1 C1 -91.0(4) . . . . ? O1W Co1 O1 C1 81.0(4) . . . . ? O3W Co1 O1 C1 -11.1(5) . . . . ? O3 Co1 O1 C1 167.3(4) 4_545 . . . ? O4 Co1 O1 C1 -178.7(3) 4_545 . . . ? O2 Co1 O1 C1 -3.0(3) . . . . ? O1 C1 O2 Co1 -5.1(6) . . . . ? C2 C1 O2 Co1 173.6(5) . . . . ? O2W Co1 O2 C1 93.1(4) . . . . ? O1W Co1 O2 C1 -91.3(4) . . . . ? O3W Co1 O2 C1 178.1(4) . . . . ? O1 Co1 O2 C1 3.0(3) . . . . ? O3 Co1 O2 C1 -10.9(5) 4_545 . . . ? O4 Co1 O2 C1 168.8(8) 4_545 . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.610 _refine_diff_density_min -0.939 _refine_diff_density_rms 0.130 _database_code_depnum_ccdc_archive 'CCDC 937204' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 Mn N O9' _chemical_formula_weight 375.20 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.9019(15) _cell_length_b 17.4988(9) _cell_length_c 10.0418(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.003(5) _cell_angle_gamma 90.00 _cell_volume 3497.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.796 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8381 _exptl_absorpt_correction_T_max 0.8700 _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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10551 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3056 _reflns_number_gt 2339 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+45.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3056 _refine_ls_number_parameters 249 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.1718 _refine_ls_wR_factor_gt 0.1638 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 O4 O 0.2961(2) 0.4241(2) 0.8304(4) 0.0431(10) Uani 1 1 d . . . O3 O 0.3435(3) 0.4342(2) 1.0250(4) 0.0571(13) Uani 1 1 d . . . C12 C 0.3233(3) 0.3941(3) 0.9303(5) 0.0368(13) Uani 1 1 d . . . Mn1 Mn 0.20054(5) 0.04377(4) 0.58207(7) 0.0330(3) Uani 1 1 d D . . O3W O 0.2853(2) 0.0410(2) 0.4453(4) 0.0378(9) Uani 1 1 d D . . O1 O 0.2371(3) 0.1684(2) 0.6490(4) 0.0598(14) Uani 1 1 d . . . O2 O 0.2731(2) 0.06506(19) 0.7487(3) 0.0371(9) Uani 1 1 d . . . C4 C 0.3309(3) 0.3080(3) 0.9365(5) 0.0303(12) Uani 1 1 d . . . C1 C 0.2705(3) 0.1374(3) 0.7419(5) 0.0361(13) Uani 1 1 d . . . O2W O 0.1147(3) 0.0635(3) 0.7150(4) 0.0574(13) Uani 1 1 d D . . C6 C 0.3683(3) 0.1931(3) 1.0487(5) 0.0301(11) Uani 1 1 d . . . C3 C 0.3009(3) 0.2641(3) 0.8376(5) 0.0323(12) Uani 1 1 d . . . H3A H 0.2783 0.2876 0.7677 0.039 Uiso 1 1 calc R . . N1 N 0.4000(2) 0.1599(3) 1.1592(4) 0.0371(11) Uani 1 1 d . . . H1A H 0.4173 0.1887 1.2195 0.045 Uiso 1 1 calc R . . C5 C 0.3636(3) 0.2732(3) 1.0406(5) 0.0313(12) Uani 1 1 d . . . H5A H 0.3831 0.3031 1.1068 0.038 Uiso 1 1 calc R . . O1W O 0.1465(3) 0.1007(2) 0.4185(4) 0.0435(10) Uani 1 1 d D . . C2 C 0.3049(3) 0.1848(3) 0.8437(5) 0.0294(12) Uani 1 1 d . . . C9 C 0.4533(3) 0.0388(3) 1.0808(5) 0.0302(11) Uani 1 1 d . . . C7 C 0.3392(3) 0.1497(3) 0.9478(5) 0.0281(11) Uani 1 1 d . . . H7A H 0.3427 0.0967 0.9499 0.034 Uiso 1 1 calc R . . C11 C 0.4543(3) -0.0406(3) 1.0742(6) 0.0399(13) Uani 1 1 d . . . H11A H 0.4236 -0.0688 1.1238 0.048 Uiso 1 1 calc R . . C8 C 0.4039(3) 0.0781(3) 1.1726(5) 0.0337(12) Uani 1 1 d . . . H8A H 0.3596 0.0569 1.1566 0.040 Uiso 1 1 calc R . . H8B H 0.4160 0.0662 1.2638 0.040 Uiso 1 1 calc R . . O4W O 0.3299(3) 0.1973(3) 0.4116(6) 0.0679(15) Uani 1 1 d D . . C10 C 0.4992(3) 0.0782(3) 1.0060(6) 0.0433(14) Uani 1 1 d . . . H10A H 0.4994 0.1314 1.0089 0.052 Uiso 1 1 calc R . . O5W O 0.0789(4) 0.2365(4) 0.4398(8) 0.0418(19) Uani 0.50 1 d P . . O6W O 0.0346(8) 0.2059(18) 0.6351(19) 0.199(12) Uani 0.50 1 d P . . H1WB H 0.162(3) 0.089(3) 0.344(3) 0.043(18) Uiso 1 1 d D . . H3WA H 0.282(3) 0.013(3) 0.378(4) 0.06(2) Uiso 1 1 d D . . H1WA H 0.110(2) 0.123(4) 0.411(6) 0.07(3) Uiso 1 1 d D . . H2WA H 0.1243(17) 0.065(4) 0.7928(17) 0.08(3) Uiso 1 1 d D . . H3WB H 0.302(3) 0.082(2) 0.417(6) 0.07(2) Uiso 1 1 d D . . H4WB H 0.319(6) 0.242(3) 0.388(9) 0.14(5) Uiso 1 1 d D . . H4WA H 0.332(8) 0.200(3) 0.496(2) 0.24(9) Uiso 1 1 d D . . H2WB H 0.0868(19) 0.091(4) 0.683(4) 0.07(3) Uiso 1 1 d 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 O4 0.074(3) 0.0201(18) 0.035(2) 0.0009(16) -0.003(2) 0.0046(19) O3 0.120(4) 0.023(2) 0.029(2) -0.0062(17) -0.003(2) -0.003(2) C12 0.059(4) 0.025(3) 0.026(3) -0.004(2) 0.014(3) -0.002(3) Mn1 0.0632(6) 0.0161(4) 0.0196(4) 0.0007(3) -0.0082(3) 0.0002(4) O3W 0.064(3) 0.0227(19) 0.0265(19) -0.0037(17) -0.0084(18) -0.0034(19) O1 0.126(4) 0.023(2) 0.030(2) -0.0032(17) -0.033(2) 0.015(2) O2 0.070(3) 0.0188(18) 0.0230(18) -0.0012(14) -0.0098(18) -0.0006(17) C4 0.048(3) 0.017(2) 0.025(2) -0.002(2) 0.010(2) 0.000(2) C1 0.065(4) 0.023(3) 0.020(2) -0.001(2) -0.004(2) 0.007(3) O2W 0.089(4) 0.050(3) 0.033(2) -0.003(2) 0.000(2) 0.021(3) C6 0.035(3) 0.028(3) 0.027(3) -0.005(2) 0.003(2) 0.005(2) C3 0.054(4) 0.019(2) 0.023(2) 0.001(2) 0.002(2) 0.004(2) N1 0.050(3) 0.030(2) 0.031(2) -0.0089(19) -0.015(2) 0.010(2) C5 0.039(3) 0.024(3) 0.032(3) -0.011(2) 0.001(2) -0.001(2) O1W 0.070(3) 0.035(2) 0.026(2) 0.0007(17) -0.002(2) 0.014(2) C2 0.047(3) 0.018(2) 0.022(2) -0.002(2) 0.002(2) 0.003(2) C9 0.032(3) 0.030(3) 0.029(3) 0.001(2) -0.004(2) 0.003(2) C7 0.041(3) 0.018(2) 0.025(2) -0.0039(19) 0.002(2) 0.002(2) C11 0.036(3) 0.033(3) 0.051(3) 0.006(3) 0.008(3) 0.000(3) C8 0.037(3) 0.035(3) 0.028(3) 0.003(2) -0.006(2) 0.008(2) O4W 0.064(3) 0.060(3) 0.079(4) 0.027(3) 0.009(3) 0.015(3) C10 0.044(4) 0.023(3) 0.063(4) 0.000(3) 0.004(3) 0.003(2) O5W 0.056(5) 0.027(4) 0.042(4) -0.004(3) 0.005(4) 0.016(4) O6W 0.065(10) 0.40(4) 0.134(14) -0.078(19) -0.033(9) 0.053(15) _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 O4 C12 1.254(7) . ? O4 Mn1 2.271(4) 4_556 ? O3 C12 1.249(7) . ? O3 Mn1 2.367(4) 4_556 ? C12 C4 1.516(7) . ? Mn1 O3W 2.176(4) . ? Mn1 O2W 2.195(5) . ? Mn1 O1W 2.201(4) . ? Mn1 O2 2.241(4) . ? Mn1 O4 2.271(4) 4_546 ? Mn1 O3 2.367(4) 4_546 ? Mn1 O1 2.396(4) . ? O3W H3WA 0.84(2) . ? O3W H3WB 0.83(2) . ? O1 C1 1.268(6) . ? O2 C1 1.269(6) . ? C4 C5 1.374(8) . ? C4 C3 1.390(7) . ? C1 C2 1.483(7) . ? O2W H2WA 0.805(19) . ? O2W H2WB 0.800(19) . ? C6 C7 1.393(7) . ? C6 N1 1.402(7) . ? C6 C5 1.408(7) . ? C3 C2 1.392(7) . ? C3 H3A 0.9300 . ? N1 C8 1.440(7) . ? N1 H1A 0.8600 . ? C5 H5A 0.9300 . ? O1W H1WB 0.831(19) . ? O1W H1WA 0.83(2) . ? C2 C7 1.390(7) . ? C9 C10 1.371(8) . ? C9 C11 1.391(8) . ? C9 C8 1.513(7) . ? C7 H7A 0.9300 . ? C11 C10 1.392(8) 5_657 ? C11 H11A 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O4W H4WB 0.84(2) . ? O4W H4WA 0.85(2) . ? C10 C11 1.392(8) 5_657 ? C10 H10A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O4 Mn1 93.7(3) . 4_556 ? C12 O3 Mn1 89.4(3) . 4_556 ? O3 C12 O4 120.9(5) . . ? O3 C12 C4 119.6(5) . . ? O4 C12 C4 119.5(5) . . ? O3W Mn1 O2W 172.13(17) . . ? O3W Mn1 O1W 85.28(16) . . ? O2W Mn1 O1W 90.14(18) . . ? O3W Mn1 O2 88.60(15) . . ? O2W Mn1 O2 91.20(18) . . ? O1W Mn1 O2 142.80(15) . . ? O3W Mn1 O4 101.58(15) . 4_546 ? O2W Mn1 O4 86.15(17) . 4_546 ? O1W Mn1 O4 136.06(16) . 4_546 ? O2 Mn1 O4 81.10(14) . 4_546 ? O3W Mn1 O3 88.99(16) . 4_546 ? O2W Mn1 O3 96.64(19) . 4_546 ? O1W Mn1 O3 81.17(15) . 4_546 ? O2 Mn1 O3 135.45(14) . 4_546 ? O4 Mn1 O3 55.95(14) 4_546 4_546 ? O3W Mn1 O1 87.82(17) . . ? O2W Mn1 O1 85.54(19) . . ? O1W Mn1 O1 86.89(15) . . ? O2 Mn1 O1 56.19(13) . . ? O4 Mn1 O1 136.19(13) 4_546 . ? O3 Mn1 O1 167.85(13) 4_546 . ? Mn1 O3W H3WA 118(5) . . ? Mn1 O3W H3WB 120(5) . . ? H3WA O3W H3WB 105(4) . . ? C1 O1 Mn1 88.6(3) . . ? C1 O2 Mn1 95.7(3) . . ? C5 C4 C3 120.2(5) . . ? C5 C4 C12 121.3(5) . . ? C3 C4 C12 118.5(5) . . ? O1 C1 O2 119.2(5) . . ? O1 C1 C2 120.6(5) . . ? O2 C1 C2 120.2(5) . . ? Mn1 O2W H2WA 114(2) . . ? Mn1 O2W H2WB 113(2) . . ? H2WA O2W H2WB 122(4) . . ? C7 C6 N1 122.5(5) . . ? C7 C6 C5 118.2(5) . . ? N1 C6 C5 119.2(5) . . ? C4 C3 C2 119.6(5) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C6 N1 C8 120.7(4) . . ? C6 N1 H1A 119.7 . . ? C8 N1 H1A 119.7 . . ? C4 C5 C6 121.1(5) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? Mn1 O1W H1WB 112(4) . . ? Mn1 O1W H1WA 135(4) . . ? H1WB O1W H1WA 111(4) . . ? C7 C2 C3 120.1(5) . . ? C7 C2 C1 119.8(4) . . ? C3 C2 C1 120.0(5) . . ? C10 C9 C11 117.9(5) . . ? C10 C9 C8 122.6(5) . . ? C11 C9 C8 119.5(5) . . ? C2 C7 C6 120.7(5) . . ? C2 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? C9 C11 C10 120.6(5) . 5_657 ? C9 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 5_657 . ? N1 C8 C9 115.5(5) . . ? N1 C8 H8A 108.4 . . ? C9 C8 H8A 108.4 . . ? N1 C8 H8B 108.4 . . ? C9 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? H4WB O4W H4WA 104(5) . . ? C9 C10 C11 121.5(5) . 5_657 ? C9 C10 H10A 119.3 . . ? C11 C10 H10A 119.3 5_657 . ? 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 Mn1 O3 C12 O4 3.7(6) 4_556 . . . ? Mn1 O3 C12 C4 -175.6(5) 4_556 . . . ? Mn1 O4 C12 O3 -3.9(6) 4_556 . . . ? Mn1 O4 C12 C4 175.4(4) 4_556 . . . ? O3W Mn1 O1 C1 -92.7(4) . . . . ? O2W Mn1 O1 C1 91.5(4) . . . . ? O1W Mn1 O1 C1 -178.1(4) . . . . ? O2 Mn1 O1 C1 -2.9(3) . . . . ? O4 Mn1 O1 C1 11.8(5) 4_546 . . . ? O3 Mn1 O1 C1 -167.6(8) 4_546 . . . ? O3W Mn1 O2 C1 91.3(4) . . . . ? O2W Mn1 O2 C1 -80.9(4) . . . . ? O1W Mn1 O2 C1 10.9(5) . . . . ? O4 Mn1 O2 C1 -166.8(4) 4_546 . . . ? O3 Mn1 O2 C1 178.4(3) 4_546 . . . ? O1 Mn1 O2 C1 2.9(3) . . . . ? O3 C12 C4 C5 -4.3(8) . . . . ? O4 C12 C4 C5 176.4(5) . . . . ? O3 C12 C4 C3 172.4(5) . . . . ? O4 C12 C4 C3 -6.8(8) . . . . ? Mn1 O1 C1 O2 4.9(6) . . . . ? Mn1 O1 C1 C2 -173.5(5) . . . . ? Mn1 O2 C1 O1 -5.3(6) . . . . ? Mn1 O2 C1 C2 173.1(5) . . . . ? C5 C4 C3 C2 -0.7(8) . . . . ? C12 C4 C3 C2 -177.5(5) . . . . ? C7 C6 N1 C8 0.2(8) . . . . ? C5 C6 N1 C8 178.2(5) . . . . ? C3 C4 C5 C6 0.7(8) . . . . ? C12 C4 C5 C6 177.5(5) . . . . ? C7 C6 C5 C4 0.5(8) . . . . ? N1 C6 C5 C4 -177.6(5) . . . . ? C4 C3 C2 C7 -0.5(8) . . . . ? C4 C3 C2 C1 177.3(5) . . . . ? O1 C1 C2 C7 177.5(6) . . . . ? O2 C1 C2 C7 -0.9(8) . . . . ? O1 C1 C2 C3 -0.3(9) . . . . ? O2 C1 C2 C3 -178.7(5) . . . . ? C3 C2 C7 C6 1.7(8) . . . . ? C1 C2 C7 C6 -176.1(5) . . . . ? N1 C6 C7 C2 176.4(5) . . . . ? C5 C6 C7 C2 -1.7(8) . . . . ? C10 C9 C11 C10 0.1(10) . . . 5_657 ? C8 C9 C11 C10 -177.8(5) . . . 5_657 ? C6 N1 C8 C9 73.5(7) . . . . ? C10 C9 C8 N1 10.5(8) . . . . ? C11 C9 C8 N1 -171.7(5) . . . . ? C11 C9 C10 C11 -0.1(10) . . . 5_657 ? C8 C9 C10 C11 177.7(5) . . . 5_657 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.561 _refine_diff_density_min -0.686 _refine_diff_density_rms 0.116 _database_code_depnum_ccdc_archive 'CCDC 937205' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 Cd N O8' _chemical_formula_weight 414.66 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' Cd Cd -0.8075 1.2024 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.073(9) _cell_length_b 17.960(8) _cell_length_c 10.293(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.471(10) _cell_angle_gamma 90.00 _cell_volume 3699(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 1.213 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8113 _exptl_absorpt_correction_T_max 0.8583 _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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9460 _diffrn_reflns_av_R_equivalents 0.0917 _diffrn_reflns_av_sigmaI/netI 0.1013 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3621 _reflns_number_gt 2443 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+70.0954P] 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 3621 _refine_ls_number_parameters 223 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0795 _refine_ls_wR_factor_ref 0.1961 _refine_ls_wR_factor_gt 0.1821 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.059 _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 Cd1 Cd 0.29434(4) -0.04168(4) 0.09536(6) 0.0461(3) Uani 1 1 d D . . C1 C 0.3189(5) 0.1085(5) 0.0843(9) 0.047(2) Uani 1 1 d . . . C8 C 0.4056(6) 0.4103(6) -0.1625(10) 0.058(3) Uani 1 1 d . . . H8A H 0.3611 0.4293 -0.1519 0.070 Uiso 1 1 calc R . . H8B H 0.4147 0.4176 -0.2528 0.070 Uiso 1 1 calc R . . C10 C 0.4532(7) 0.5303(7) -0.0846(14) 0.079(4) Uani 1 1 d . . . H10A H 0.4223 0.5531 -0.1437 0.094 Uiso 1 1 calc R . . O1 O 0.2899(4) 0.0811(3) 0.1788(6) 0.0575(19) Uani 1 1 d . . . O1W O 0.2056(5) -0.0419(5) -0.0603(8) 0.082(3) Uani 1 1 d D . . H1WB H 0.186(4) -0.002(3) -0.060(8) 0.099 Uiso 1 1 d D . . H1WA H 0.2203(18) -0.048(7) -0.134(2) 0.124 Uiso 1 1 d D . . O2W O 0.3478(6) -0.1049(6) -0.0615(9) 0.102(4) Uani 1 1 d D . . H2WB H 0.340(6) -0.084(9) -0.134(8) 0.122 Uiso 1 1 d D . . H2WA H 0.3887(18) -0.106(11) -0.043(14) 0.122 Uiso 1 1 d D . . O2 O 0.3392(4) 0.0672(4) -0.0041(6) 0.0582(19) Uani 1 1 d . . . O3 O 0.2421(4) 0.3352(4) 0.3393(7) 0.069(2) Uani 1 1 d . . . O3W O 0.3846(4) -0.0609(5) 0.2494(7) 0.071(2) Uani 1 1 d D . . H3WB H 0.3688(15) -0.071(6) 0.320(3) 0.086 Uiso 1 1 d D . . H3WA H 0.406(3) -0.021(3) 0.255(8) 0.086 Uiso 1 1 d D . . O4 O 0.2825(4) 0.4333(4) 0.2458(6) 0.0520(17) Uani 1 1 d . . . O4W O 0.1692(8) 0.2069(9) 0.4185(14) 0.129(4) Uani 1 1 d D . . H4WB H 0.186(10) 0.230(10) 0.359(14) 0.154 Uiso 1 1 d D . . H4WA H 0.173(12) 0.234(11) 0.484(14) 0.154 Uiso 1 1 d D . . C14 C 0.5022(6) 0.4249(7) 0.0030(14) 0.075(4) Uani 1 1 d . . . H14A H 0.5065 0.3733 0.0066 0.090 Uiso 1 1 calc R . . C2 C 0.3290(4) 0.1924(5) 0.0770(8) 0.0347(18) Uani 1 1 d . . . C9 C 0.4552(5) 0.4544(5) -0.0771(9) 0.041(2) Uani 1 1 d . . . C3 C 0.3009(4) 0.2378(5) 0.1666(8) 0.0378(19) Uani 1 1 d . . . H3A H 0.2769 0.2171 0.2313 0.045 Uiso 1 1 calc R . . C5 C 0.3447(4) 0.3452(5) 0.0609(8) 0.039(2) Uani 1 1 d . . . H5A H 0.3506 0.3966 0.0577 0.047 Uiso 1 1 calc R . . C11 C 0.2757(5) 0.3637(5) 0.2532(8) 0.043(2) Uani 1 1 d . . . C4 C 0.3088(5) 0.3144(5) 0.1594(8) 0.038(2) Uani 1 1 d . . . C7 C 0.3646(4) 0.2229(5) -0.0216(8) 0.041(2) Uani 1 1 d . . . H7A H 0.3836 0.1917 -0.0806 0.049 Uiso 1 1 calc R . . C6 C 0.3719(4) 0.3003(5) -0.0324(8) 0.041(2) Uani 1 1 d . . . N1 N 0.4069(5) 0.3289(5) -0.1335(8) 0.059(2) Uani 1 1 d . . . H1A H 0.4292 0.2993 -0.1794 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0767(5) 0.0263(4) 0.0359(4) -0.0009(3) 0.0080(3) -0.0064(4) C1 0.069(6) 0.029(5) 0.043(5) -0.003(4) 0.003(5) -0.015(5) C8 0.070(7) 0.059(7) 0.046(5) 0.009(5) 0.011(5) -0.023(6) C10 0.080(8) 0.046(7) 0.105(10) 0.021(6) -0.021(8) -0.003(7) O1 0.093(5) 0.028(4) 0.055(4) 0.001(3) 0.023(4) -0.004(4) O1W 0.124(8) 0.056(5) 0.063(5) 0.014(4) -0.021(5) -0.018(5) O2W 0.179(11) 0.068(6) 0.063(5) -0.001(5) 0.042(6) 0.037(8) O2 0.100(6) 0.027(3) 0.049(4) -0.008(3) 0.017(4) -0.009(4) O3 0.113(6) 0.038(4) 0.061(4) -0.004(3) 0.044(4) 0.000(4) O3W 0.073(5) 0.084(6) 0.056(4) 0.019(4) 0.004(4) 0.004(5) O4 0.084(5) 0.029(3) 0.044(3) 0.001(3) 0.011(3) 0.004(4) O4W 0.116(9) 0.132(12) 0.139(12) 0.035(9) 0.013(9) -0.033(9) C14 0.071(8) 0.028(6) 0.125(11) -0.001(6) -0.009(8) -0.004(6) C2 0.042(5) 0.025(4) 0.035(4) 0.000(3) -0.006(4) -0.004(4) C9 0.044(5) 0.035(5) 0.045(5) 0.012(4) 0.004(4) -0.013(4) C3 0.048(5) 0.032(5) 0.034(4) 0.004(3) 0.003(4) -0.001(4) C5 0.049(5) 0.028(5) 0.039(4) 0.003(3) 0.000(4) -0.004(4) C11 0.064(6) 0.034(5) 0.031(4) 0.000(3) -0.001(4) 0.002(5) C4 0.051(5) 0.025(4) 0.038(4) -0.003(3) 0.003(4) -0.006(4) C7 0.045(5) 0.036(5) 0.042(5) -0.004(4) 0.006(4) -0.006(4) C6 0.042(5) 0.040(5) 0.041(4) -0.002(4) -0.001(4) -0.018(4) N1 0.079(6) 0.051(5) 0.052(5) -0.006(4) 0.027(4) -0.023(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 Cd1 O1W 2.301(9) . ? Cd1 O2W 2.306(8) . ? Cd1 O3W 2.338(8) . ? Cd1 O1 2.371(6) . ? Cd1 O4 2.376(6) 4_545 ? Cd1 O2 2.414(7) . ? Cd1 O3 2.440(7) 4_545 ? Cd1 C1 2.745(9) . ? C1 O2 1.265(11) . ? C1 O1 1.271(10) . ? C1 C2 1.523(12) . ? C8 N1 1.492(14) . ? C8 C9 1.502(14) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C9 1.365(15) . ? C10 C14 1.428(18) 5_665 ? C10 H10A 0.9300 . ? O1W H1WB 0.83(2) . ? O1W H1WA 0.84(2) . ? O2W H2WB 0.84(2) . ? O2W H2WA 0.83(2) . ? O3 C11 1.263(10) . ? O3 Cd1 2.440(7) 4 ? O3W H3WB 0.83(2) . ? O3W H3WA 0.83(2) . ? O4 C11 1.261(11) . ? O4 Cd1 2.376(6) 4 ? O4W H4WB 0.83(2) . ? O4W H4WA 0.83(2) . ? C14 C9 1.315(15) . ? C14 C10 1.428(18) 5_665 ? C14 H14A 0.9300 . ? C2 C3 1.384(11) . ? C2 C7 1.398(11) . ? C3 C4 1.388(12) . ? C3 H3A 0.9300 . ? C5 C6 1.397(12) . ? C5 C4 1.403(11) . ? C5 H5A 0.9300 . ? C11 C4 1.502(12) . ? C7 C6 1.403(13) . ? C7 H7A 0.9300 . ? C6 N1 1.397(11) . ? N1 H1A 0.8600 . ? 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 O1W Cd1 O2W 83.6(4) . . ? O1W Cd1 O3W 171.4(3) . . ? O2W Cd1 O3W 91.4(4) . . ? O1W Cd1 O1 101.8(3) . . ? O2W Cd1 O1 138.1(3) . . ? O3W Cd1 O1 86.6(3) . . ? O1W Cd1 O4 88.3(3) . 4_545 ? O2W Cd1 O4 138.7(3) . 4_545 ? O3W Cd1 O4 90.9(3) . 4_545 ? O1 Cd1 O4 83.2(2) . 4_545 ? O1W Cd1 O2 90.0(3) . . ? O2W Cd1 O2 83.8(3) . . ? O3W Cd1 O2 96.4(3) . . ? O1 Cd1 O2 55.0(2) . . ? O4 Cd1 O2 136.8(2) 4_545 . ? O1W Cd1 O3 87.6(3) . 4_545 ? O2W Cd1 O3 85.0(3) . 4_545 ? O3W Cd1 O3 85.0(3) . 4_545 ? O1 Cd1 O3 136.3(2) . 4_545 ? O4 Cd1 O3 54.2(2) 4_545 4_545 ? O2 Cd1 O3 168.8(2) . 4_545 ? O1W Cd1 C1 96.0(3) . . ? O2W Cd1 C1 111.1(3) . . ? O3W Cd1 C1 92.3(3) . . ? O1 Cd1 C1 27.5(2) . . ? O4 Cd1 C1 110.0(2) 4_545 . ? O2 Cd1 C1 27.4(2) . . ? O3 Cd1 C1 163.8(2) 4_545 . ? O2 C1 O1 121.1(8) . . ? O2 C1 C2 119.5(8) . . ? O1 C1 C2 119.4(8) . . ? O2 C1 Cd1 61.6(5) . . ? O1 C1 Cd1 59.6(5) . . ? C2 C1 Cd1 177.3(7) . . ? N1 C8 C9 113.6(9) . . ? N1 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? N1 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C9 C10 C14 121.0(12) . 5_665 ? C9 C10 H10A 119.5 . . ? C14 C10 H10A 119.5 5_665 . ? C1 O1 Cd1 92.9(5) . . ? Cd1 O1W H1WB 110(2) . . ? Cd1 O1W H1WA 109(2) . . ? H1WB O1W H1WA 109(5) . . ? Cd1 O2W H2WB 110(10) . . ? Cd1 O2W H2WA 111(10) . . ? H2WB O2W H2WA 110(5) . . ? C1 O2 Cd1 91.0(5) . . ? C11 O3 Cd1 90.8(5) . 4 ? Cd1 O3W H3WB 107(2) . . ? Cd1 O3W H3WA 107(2) . . ? H3WB O3W H3WA 111(5) . . ? C11 O4 Cd1 93.8(5) . 4 ? H4WB O4W H4WA 106(10) . . ? C9 C14 C10 121.8(11) . 5_665 ? C9 C14 H14A 119.1 . . ? C10 C14 H14A 119.1 5_665 . ? C3 C2 C7 120.7(8) . . ? C3 C2 C1 119.2(7) . . ? C7 C2 C1 120.1(8) . . ? C14 C9 C10 117.1(10) . . ? C14 C9 C8 124.4(10) . . ? C10 C9 C8 118.5(10) . . ? C2 C3 C4 119.6(7) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C6 C5 C4 121.3(8) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? O4 C11 O3 120.7(8) . . ? O4 C11 C4 119.3(8) . . ? O3 C11 C4 120.0(8) . . ? C3 C4 C5 119.8(8) . . ? C3 C4 C11 119.5(7) . . ? C5 C4 C11 120.7(8) . . ? C2 C7 C6 120.6(8) . . ? C2 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? C5 C6 N1 123.1(8) . . ? C5 C6 C7 118.0(8) . . ? N1 C6 C7 119.0(8) . . ? C6 N1 C8 120.5(8) . . ? C6 N1 H1A 119.8 . . ? C8 N1 H1A 119.8 . . ? 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 O1W Cd1 C1 O2 -78.4(7) . . . . ? O2W Cd1 C1 O2 7.1(8) . . . . ? O3W Cd1 C1 O2 99.5(6) . . . . ? O1 Cd1 C1 O2 177.5(11) . . . . ? O4 Cd1 C1 O2 -168.7(6) 4_545 . . . ? O3 Cd1 C1 O2 179.6(10) 4_545 . . . ? O1W Cd1 C1 O1 104.1(7) . . . . ? O2W Cd1 C1 O1 -170.4(7) . . . . ? O3W Cd1 C1 O1 -78.0(6) . . . . ? O4 Cd1 C1 O1 13.8(7) 4_545 . . . ? O2 Cd1 C1 O1 -177.5(11) . . . . ? O3 Cd1 C1 O1 2.1(15) 4_545 . . . ? O1W Cd1 C1 C2 35(13) . . . . ? O2W Cd1 C1 C2 121(13) . . . . ? O3W Cd1 C1 C2 -147(13) . . . . ? O1 Cd1 C1 C2 -69(13) . . . . ? O4 Cd1 C1 C2 -55(13) 4_545 . . . ? O2 Cd1 C1 C2 114(13) . . . . ? O3 Cd1 C1 C2 -67(13) 4_545 . . . ? O2 C1 O1 Cd1 -2.6(11) . . . . ? C2 C1 O1 Cd1 177.1(8) . . . . ? O1W Cd1 O1 C1 -80.2(7) . . . . ? O2W Cd1 O1 C1 13.4(9) . . . . ? O3W Cd1 O1 C1 101.7(6) . . . . ? O4 Cd1 O1 C1 -167.0(7) 4_545 . . . ? O2 Cd1 O1 C1 1.4(6) . . . . ? O3 Cd1 O1 C1 -179.2(6) 4_545 . . . ? O1 C1 O2 Cd1 2.5(11) . . . . ? C2 C1 O2 Cd1 -177.1(8) . . . . ? O1W Cd1 O2 C1 103.1(7) . . . . ? O2W Cd1 O2 C1 -173.4(7) . . . . ? O3W Cd1 O2 C1 -82.6(7) . . . . ? O1 Cd1 O2 C1 -1.4(6) . . . . ? O4 Cd1 O2 C1 15.6(8) 4_545 . . . ? O3 Cd1 O2 C1 -179.4(14) 4_545 . . . ? O2 C1 C2 C3 173.7(9) . . . . ? O1 C1 C2 C3 -6.0(14) . . . . ? Cd1 C1 C2 C3 61(13) . . . . ? O2 C1 C2 C7 -4.5(14) . . . . ? O1 C1 C2 C7 175.9(9) . . . . ? Cd1 C1 C2 C7 -117(12) . . . . ? C10 C14 C9 C10 4(2) 5_665 . . . ? C10 C14 C9 C8 -178.2(11) 5_665 . . . ? C14 C10 C9 C14 -4(2) 5_665 . . . ? C14 C10 C9 C8 178.1(11) 5_665 . . . ? N1 C8 C9 C14 9.4(14) . . . . ? N1 C8 C9 C10 -172.5(10) . . . . ? C7 C2 C3 C4 -0.7(13) . . . . ? C1 C2 C3 C4 -178.9(9) . . . . ? Cd1 O4 C11 O3 -7.3(10) 4 . . . ? Cd1 O4 C11 C4 173.5(8) 4 . . . ? Cd1 O3 C11 O4 7.1(10) 4 . . . ? Cd1 O3 C11 C4 -173.7(8) 4 . . . ? C2 C3 C4 C5 0.4(14) . . . . ? C2 C3 C4 C11 177.3(8) . . . . ? C6 C5 C4 C3 1.2(14) . . . . ? C6 C5 C4 C11 -175.6(9) . . . . ? O4 C11 C4 C3 -179.4(9) . . . . ? O3 C11 C4 C3 1.4(14) . . . . ? O4 C11 C4 C5 -2.6(14) . . . . ? O3 C11 C4 C5 178.2(9) . . . . ? C3 C2 C7 C6 -0.7(14) . . . . ? C1 C2 C7 C6 177.5(8) . . . . ? C4 C5 C6 N1 178.7(9) . . . . ? C4 C5 C6 C7 -2.5(14) . . . . ? C2 C7 C6 C5 2.3(14) . . . . ? C2 C7 C6 N1 -178.9(8) . . . . ? C5 C6 N1 C8 -12.0(15) . . . . ? C7 C6 N1 C8 169.2(9) . . . . ? C9 C8 N1 C6 83.0(12) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.016 _refine_diff_density_min -1.394 _refine_diff_density_rms 0.162 _database_code_depnum_ccdc_archive 'CCDC 937206' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H32 N6 O11 Zn2' _chemical_formula_weight 951.50 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.733(15) _cell_length_b 10.217(6) _cell_length_c 14.405(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.450(9) _cell_angle_gamma 90.00 _cell_volume 4078(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1944 _exptl_absorpt_coefficient_mu 1.248 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7539 _exptl_absorpt_correction_T_max 0.8546 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12160 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0631 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 28.03 _reflns_number_total 4858 _reflns_number_gt 3463 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0861P)^2^+1.9051P] 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 4858 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1624 _refine_ls_wR_factor_gt 0.1482 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 Zn1 Zn 0.592554(13) 0.80307(4) 0.60391(3) 0.04437(16) Uani 1 1 d . . . O1 O 0.59850(9) 0.2831(3) 0.98263(17) 0.0550(6) Uani 1 1 d . . . O4 O 0.63935(8) 0.7100(2) 0.68860(18) 0.0508(6) Uani 1 1 d . . . N2 N 0.59856(9) 1.0031(3) 0.61608(18) 0.0467(7) Uani 1 1 d . . . N3 N 0.51985(10) 0.8536(3) 0.62034(19) 0.0481(7) Uani 1 1 d . . . C6 C 0.69571(10) 0.4780(3) 0.7300(2) 0.0367(6) Uani 1 1 d . . . H6 H 0.7072 0.5261 0.6808 0.044 Uiso 1 1 calc R . . C5 C 0.64840(10) 0.4998(3) 0.75907(19) 0.0360(6) Uani 1 1 d . . . C2 C 0.70708(11) 0.3151(3) 0.8502(2) 0.0393(7) Uani 1 1 d . . . H2 H 0.7266 0.2546 0.8822 0.047 Uiso 1 1 calc R . . O3 O 0.57378(8) 0.5898(3) 0.69560(19) 0.0580(7) Uani 1 1 d . . . C1 C 0.72564(10) 0.3841(3) 0.7749(2) 0.0365(6) Uani 1 1 d . . . N1 N 0.77266(10) 0.3620(3) 0.7501(2) 0.0487(7) Uani 1 1 d . . . C3 C 0.65995(12) 0.3357(3) 0.8778(2) 0.0411(7) Uani 1 1 d . . . C7 C 0.61796(11) 0.6044(3) 0.7116(2) 0.0397(7) Uani 1 1 d . . . C4 C 0.63014(11) 0.4278(3) 0.8314(2) 0.0403(7) Uani 1 1 d . . . H4 H 0.5986 0.4405 0.8488 0.048 Uiso 1 1 calc R . . C10 C 0.76921(12) 0.3234(3) 0.5771(2) 0.0475(8) Uani 1 1 d . . . C18 C 0.51226(11) 0.9845(4) 0.6231(2) 0.0474(8) Uani 1 1 d . . . C17 C 0.55609(12) 1.0689(4) 0.6203(2) 0.0476(8) Uani 1 1 d . . . C12 C 0.77133(15) 0.1858(4) 0.5750(3) 0.0566(10) Uani 1 1 d . . . H12 H 0.7856 0.1414 0.6254 0.068 Uiso 1 1 calc R . . C9 C 0.79065(11) 0.3995(4) 0.6602(2) 0.0523(8) Uani 1 1 d . . . H9A H 0.8254 0.3881 0.6624 0.063 Uiso 1 1 calc R . . H9B H 0.7841 0.4919 0.6504 0.063 Uiso 1 1 calc R . . C13 C 0.63962(13) 1.0728(4) 0.6121(3) 0.0609(10) Uani 1 1 d . . . H13 H 0.6688 1.0281 0.6104 0.073 Uiso 1 1 calc R . . C16 C 0.55424(17) 1.2036(4) 0.6202(3) 0.0712(13) Uani 1 1 d . . . H16 H 0.5249 1.2467 0.6247 0.085 Uiso 1 1 calc R . . C11 C 0.74736(14) 0.3855(4) 0.5005(3) 0.0568(9) Uani 1 1 d . . . H11 H 0.7452 0.4764 0.4997 0.068 Uiso 1 1 calc R . . C19 C 0.46540(13) 1.0368(5) 0.6260(3) 0.0639(11) Uani 1 1 d . . . H19 H 0.4605 1.1268 0.6272 0.077 Uiso 1 1 calc R . . C21 C 0.43497(15) 0.8186(5) 0.6253(4) 0.0785(15) Uani 1 1 d . . . H21 H 0.4092 0.7603 0.6258 0.094 Uiso 1 1 calc R . . C14 C 0.64027(18) 1.2086(4) 0.6103(4) 0.0787(15) Uani 1 1 d . . . H14 H 0.6692 1.2539 0.6071 0.094 Uiso 1 1 calc R . . C22 C 0.48231(14) 0.7728(5) 0.6229(3) 0.0650(11) Uani 1 1 d . . . H22 H 0.4878 0.6830 0.6232 0.078 Uiso 1 1 calc R . . C20 C 0.42706(14) 0.9514(6) 0.6269(3) 0.0796(15) Uani 1 1 d . . . H20 H 0.3957 0.9836 0.6286 0.096 Uiso 1 1 calc R . . O2 O 0.66868(12) 0.1769(3) 0.9995(2) 0.0825(10) Uani 1 1 d . . . C8 C 0.64234(13) 0.2582(4) 0.9583(2) 0.0504(8) Uani 1 1 d . . . OW1 O 0.5000 0.4169(5) 0.7500 0.113(2) Uani 1 2 d S . . C15 C 0.59708(18) 1.2748(5) 0.6133(4) 0.0888(17) Uani 1 1 d . . . H15 H 0.5964 1.3657 0.6108 0.107 Uiso 1 1 calc R . . OW2 O 0.5249(9) 0.475(3) 0.961(2) 0.635(18) Uiso 1 1 d . . . H1 H 0.7897(17) 0.298(4) 0.777(3) 0.068(13) 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 Zn1 0.0362(2) 0.0515(3) 0.0459(2) 0.00028(15) 0.00647(15) 0.01268(16) O1 0.0402(12) 0.0724(17) 0.0531(14) 0.0109(12) 0.0099(10) -0.0093(12) O4 0.0393(12) 0.0442(13) 0.0680(16) 0.0104(11) -0.0082(11) -0.0038(10) N2 0.0392(15) 0.0535(17) 0.0476(15) -0.0076(12) 0.0042(11) 0.0135(13) N3 0.0383(15) 0.0607(18) 0.0460(15) 0.0094(13) 0.0108(11) 0.0077(14) C6 0.0283(14) 0.0424(16) 0.0396(15) 0.0016(12) 0.0054(11) -0.0018(12) C5 0.0298(14) 0.0389(15) 0.0395(15) -0.0030(12) 0.0029(11) -0.0009(12) C2 0.0367(16) 0.0362(16) 0.0453(17) 0.0028(12) 0.0040(12) 0.0039(13) O3 0.0276(11) 0.0592(16) 0.0869(18) 0.0099(13) -0.0005(11) 0.0044(11) C1 0.0285(14) 0.0408(16) 0.0403(15) -0.0050(12) 0.0042(11) 0.0005(12) N1 0.0316(14) 0.0623(19) 0.0529(16) 0.0110(14) 0.0089(11) 0.0109(14) C3 0.0413(16) 0.0396(16) 0.0430(17) -0.0012(12) 0.0095(13) -0.0020(14) C7 0.0361(16) 0.0418(17) 0.0413(16) -0.0035(13) 0.0023(12) 0.0043(14) C4 0.0309(15) 0.0449(17) 0.0457(17) -0.0024(13) 0.0090(12) 0.0003(13) C10 0.0355(16) 0.056(2) 0.0530(19) 0.0162(15) 0.0201(14) 0.0081(14) C18 0.0408(17) 0.071(2) 0.0312(15) 0.0009(14) 0.0105(12) 0.0176(16) C17 0.0416(18) 0.061(2) 0.0401(17) -0.0124(14) 0.0025(13) 0.0162(16) C12 0.058(2) 0.057(2) 0.054(2) 0.0196(17) 0.0103(17) 0.0142(18) C9 0.0299(16) 0.063(2) 0.065(2) 0.0078(17) 0.0168(14) 0.0024(16) C13 0.0399(19) 0.067(3) 0.076(3) -0.0204(19) 0.0009(17) 0.0032(18) C16 0.057(2) 0.063(3) 0.093(3) -0.031(2) -0.004(2) 0.018(2) C11 0.060(2) 0.049(2) 0.063(2) 0.0170(17) 0.0191(17) 0.0143(18) C19 0.044(2) 0.084(3) 0.064(2) 0.019(2) 0.0174(17) 0.024(2) C21 0.040(2) 0.106(4) 0.091(3) 0.040(3) 0.017(2) -0.005(2) C14 0.060(3) 0.062(3) 0.113(4) -0.034(2) -0.006(3) -0.004(2) C22 0.046(2) 0.077(3) 0.073(3) 0.022(2) 0.0163(18) 0.001(2) C20 0.038(2) 0.117(4) 0.086(3) 0.042(3) 0.0222(19) 0.018(2) O2 0.086(2) 0.073(2) 0.092(2) 0.0403(16) 0.0430(18) 0.0276(17) C8 0.053(2) 0.0445(19) 0.055(2) 0.0055(15) 0.0183(16) -0.0054(17) OW1 0.067(3) 0.074(3) 0.203(6) 0.000 0.056(3) 0.000 C15 0.082(4) 0.052(3) 0.131(5) -0.038(3) -0.008(3) 0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.970(3) 6_565 ? Zn1 O4 1.985(2) . ? Zn1 N2 2.058(3) . ? Zn1 N3 2.104(3) . ? O1 C8 1.305(4) . ? O1 Zn1 1.970(3) 6_566 ? O4 C7 1.282(4) . ? N2 C13 1.347(5) . ? N2 C17 1.360(4) . ? N3 C22 1.331(5) . ? N3 C18 1.354(5) . ? C6 C1 1.408(4) . ? C6 C5 1.412(4) . ? C6 H6 0.9300 . ? C5 C4 1.388(4) . ? C5 C7 1.508(4) . ? C2 C3 1.399(5) . ? C2 C1 1.410(4) . ? C2 H2 0.9300 . ? O3 C7 1.246(4) . ? C1 N1 1.385(4) . ? N1 C9 1.458(4) . ? N1 H1 0.89(4) . ? C3 C4 1.403(4) . ? C3 C8 1.502(5) . ? C4 H4 0.9300 . ? C10 C11 1.389(5) . ? C10 C12 1.407(5) . ? C10 C9 1.527(5) . ? C18 C19 1.407(5) . ? C18 C17 1.493(5) . ? C17 C16 1.377(5) . ? C12 C11 1.391(6) 7_656 ? C12 H12 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C13 C14 1.387(6) . ? C13 H13 0.9300 . ? C16 C15 1.400(7) . ? C16 H16 0.9300 . ? C11 C12 1.391(6) 7_656 ? C11 H11 0.9300 . ? C19 C20 1.376(6) . ? C19 H19 0.9300 . ? C21 C20 1.375(7) . ? C21 C22 1.395(6) . ? C21 H21 0.9300 . ? C14 C15 1.378(7) . ? C14 H14 0.9300 . ? C22 H22 0.9300 . ? C20 H20 0.9300 . ? O2 C8 1.241(5) . ? C15 H15 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O4 104.69(11) 6_565 . ? O1 Zn1 N2 120.67(11) 6_565 . ? O4 Zn1 N2 112.04(10) . . ? O1 Zn1 N3 109.05(11) 6_565 . ? O4 Zn1 N3 130.75(11) . . ? N2 Zn1 N3 79.68(11) . . ? C8 O1 Zn1 105.4(2) . 6_566 ? C7 O4 Zn1 105.35(19) . . ? C13 N2 C17 118.4(3) . . ? C13 N2 Zn1 126.0(2) . . ? C17 N2 Zn1 115.3(2) . . ? C22 N3 C18 119.3(3) . . ? C22 N3 Zn1 127.3(3) . . ? C18 N3 Zn1 113.4(2) . . ? C1 C6 C5 120.6(3) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C4 C5 C6 120.8(3) . . ? C4 C5 C7 120.0(3) . . ? C6 C5 C7 119.1(3) . . ? C3 C2 C1 121.3(3) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? N1 C1 C6 122.4(3) . . ? N1 C1 C2 119.7(3) . . ? C6 C1 C2 117.8(3) . . ? C1 N1 C9 123.2(3) . . ? C1 N1 H1 120(3) . . ? C9 N1 H1 113(3) . . ? C2 C3 C4 120.3(3) . . ? C2 C3 C8 118.6(3) . . ? C4 C3 C8 121.1(3) . . ? O3 C7 O4 121.0(3) . . ? O3 C7 C5 121.8(3) . . ? O4 C7 C5 117.2(3) . . ? C5 C4 C3 119.1(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C11 C10 C12 117.1(4) . . ? C11 C10 C9 122.1(3) . . ? C12 C10 C9 120.7(3) . . ? N3 C18 C19 121.4(4) . . ? N3 C18 C17 116.2(3) . . ? C19 C18 C17 122.4(4) . . ? N2 C17 C16 121.8(4) . . ? N2 C17 C18 115.0(3) . . ? C16 C17 C18 123.2(3) . . ? C11 C12 C10 121.7(3) 7_656 . ? C11 C12 H12 119.1 7_656 . ? C10 C12 H12 119.1 . . ? N1 C9 C10 115.2(3) . . ? N1 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? N1 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? N2 C13 C14 122.8(4) . . ? N2 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C17 C16 C15 119.2(4) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C10 C11 C12 121.1(3) . 7_656 ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 7_656 . ? C20 C19 C18 118.3(4) . . ? C20 C19 H19 120.8 . . ? C18 C19 H19 120.8 . . ? C20 C21 C22 118.8(4) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? C15 C14 C13 118.6(5) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? N3 C22 C21 122.1(4) . . ? N3 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C21 C20 C19 120.1(4) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? O2 C8 O1 122.5(3) . . ? O2 C8 C3 121.2(3) . . ? O1 C8 C3 116.2(3) . . ? C14 C15 C16 119.2(5) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.016 _refine_diff_density_min -0.818 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 937207' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H42 Cd2 N6 O13' _chemical_formula_weight 1087.59 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' Cd Cd -0.8075 1.2024 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 10.235(5) _cell_length_b 9.554(5) _cell_length_c 24.242(9) _cell_angle_alpha 90.00 _cell_angle_beta 112.620(16) _cell_angle_gamma 90.00 _cell_volume 2188.2(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4073 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 27.49 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 1.045 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8343 _exptl_absorpt_correction_T_max 0.8849 _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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11638 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4275 _reflns_number_gt 3504 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+4.1576P] 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 4275 _refine_ls_number_parameters 304 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1027 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.015 _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 Cd1 Cd 0.07318(3) 0.83781(3) 0.181712(13) 0.03018(11) Uani 1 1 d . . . O1 O 0.1841(4) 0.6598(3) 0.1483(2) 0.0633(11) Uani 1 1 d . . . O2 O 0.3152(3) 0.8457(3) 0.18299(16) 0.0524(9) Uani 1 1 d . . . O3 O 0.8380(3) 0.8254(3) 0.21421(13) 0.0408(7) Uani 1 1 d . . . O4 O 0.8894(3) 0.6789(3) 0.15449(18) 0.0587(10) Uani 1 1 d . . . N1 N -0.0486(4) 0.9575(4) 0.09004(17) 0.0481(10) Uani 1 1 d . . . N2 N 0.0935(4) 1.0800(4) 0.19677(16) 0.0415(9) Uani 1 1 d . . . N3 N 0.4766(4) 0.3349(4) 0.0760(2) 0.0642(14) Uani 1 1 d . . . H3B H 0.3939 0.2976 0.0646 0.077 Uiso 1 1 d R . . C1 C -0.1187(6) 0.8920(8) 0.0378(3) 0.0685(16) Uani 1 1 d . . . H1A H -0.1221 0.7947 0.0370 0.082 Uiso 1 1 calc R . . C2 C -0.1872(6) 0.9673(10) -0.0159(2) 0.078(2) Uani 1 1 d . . . H2A H -0.2340 0.9203 -0.0517 0.094 Uiso 1 1 calc R . . C3 C -0.1835(7) 1.1094(10) -0.0142(3) 0.083(2) Uani 1 1 d . . . H3A H -0.2291 1.1608 -0.0489 0.100 Uiso 1 1 calc R . . C4 C -0.1125(6) 1.1765(7) 0.0388(2) 0.0682(16) Uani 1 1 d . . . H4A H -0.1092 1.2738 0.0401 0.082 Uiso 1 1 calc R . . C5 C -0.0446(5) 1.0987(5) 0.0910(2) 0.0458(11) Uani 1 1 d . . . C6 C 0.0347(5) 1.1666(5) 0.1486(2) 0.0471(11) Uani 1 1 d . . . C7 C 0.0557(9) 1.3129(6) 0.1559(3) 0.089(2) Uani 1 1 d . . . H7A H 0.0162 1.3723 0.1233 0.107 Uiso 1 1 calc R . . C8 C 0.1336(12) 1.3666(7) 0.2107(4) 0.130(4) Uani 1 1 d . . . H8A H 0.1481 1.4627 0.2156 0.156 Uiso 1 1 calc R . . C9 C 0.1894(11) 1.2800(7) 0.2574(3) 0.123(4) Uani 1 1 d . . . H9A H 0.2412 1.3159 0.2952 0.147 Uiso 1 1 calc R . . C10 C 0.1696(7) 1.1360(5) 0.2492(2) 0.0699(18) Uani 1 1 d . . . H10A H 0.2117 1.0771 0.2818 0.084 Uiso 1 1 calc R . . C11 C 0.3000(4) 0.7244(4) 0.16214(19) 0.0357(9) Uani 1 1 d . . . C12 C 0.4206(4) 0.6547(4) 0.15166(18) 0.0325(8) Uani 1 1 d . . . C13 C 0.5555(4) 0.7160(4) 0.17287(16) 0.0283(8) Uani 1 1 d . . . H13A H 0.5727 0.7982 0.1951 0.034 Uiso 1 1 calc R . . C14 C 0.6638(4) 0.6523(4) 0.16028(16) 0.0268(8) Uani 1 1 d . . . C15 C 0.6387(4) 0.5288(4) 0.12759(18) 0.0337(9) Uani 1 1 d . . . H15A H 0.7113 0.4889 0.1188 0.040 Uiso 1 1 calc R . . C16 C 0.5058(4) 0.4629(4) 0.1076(2) 0.0440(11) Uani 1 1 d . . . C17 C 0.3971(4) 0.5289(4) 0.1199(2) 0.0459(11) Uani 1 1 d . . . H17A H 0.3078 0.4880 0.1066 0.055 Uiso 1 1 calc R . . C18 C 0.5898(5) 0.2667(5) 0.0627(2) 0.0516(13) Uani 1 1 d . . . H18A H 0.6705 0.2507 0.0996 0.062 Uiso 1 1 calc R . . H18B H 0.6196 0.3282 0.0379 0.062 Uiso 1 1 calc R . . C19 C 0.5408(4) 0.1280(4) 0.0305(2) 0.0381(10) Uani 1 1 d . . . C20 C 0.4706(5) 0.1245(4) -0.0311(2) 0.0452(11) Uani 1 1 d . . . H20A H 0.4502 0.2079 -0.0525 0.054 Uiso 1 1 calc R . . C21 C 0.5699(5) 0.0027(5) 0.06164(19) 0.0424(10) Uani 1 1 d . . . H21A H 0.6165 0.0031 0.1030 0.051 Uiso 1 1 calc R . . C22 C 0.8064(4) 0.7221(4) 0.17813(18) 0.0325(9) Uani 1 1 d . . . O1W O -0.0230(11) 0.4683(10) 0.9716(4) 0.103(3) Uani 0.50 1 d P . . O2W O 0.2116(11) 0.4483(7) 0.9712(3) 0.145(3) Uani 1 1 d D . . H2WB H 0.256(12) 0.386(9) 0.998(3) 0.175 Uiso 1 1 d D . . H2WA H 0.201(11) 0.404(9) 0.938(2) 0.175 Uiso 1 1 d D . . O3W O 0.4308(9) 0.1338(7) 0.1796(4) 0.169(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 Cd1 0.02667(17) 0.02522(16) 0.04096(19) -0.00428(12) 0.01556(13) -0.00144(11) O1 0.0427(19) 0.0405(18) 0.124(3) -0.0103(19) 0.051(2) -0.0018(15) O2 0.0402(18) 0.052(2) 0.068(2) -0.0214(16) 0.0233(16) 0.0074(15) O3 0.0405(17) 0.0315(15) 0.0458(17) -0.0121(13) 0.0113(14) -0.0099(13) O4 0.0434(19) 0.0447(18) 0.104(3) -0.0290(18) 0.047(2) -0.0147(15) N1 0.037(2) 0.066(3) 0.038(2) -0.0060(18) 0.0105(17) 0.0002(18) N2 0.054(2) 0.0277(18) 0.042(2) 0.0038(15) 0.0185(18) 0.0005(16) N3 0.036(2) 0.042(2) 0.114(4) -0.048(2) 0.029(2) -0.0108(18) C1 0.049(3) 0.099(4) 0.058(4) -0.023(3) 0.021(3) -0.011(3) C2 0.038(3) 0.159(7) 0.032(3) -0.013(4) 0.007(2) -0.009(4) C3 0.061(4) 0.135(7) 0.053(4) 0.022(4) 0.022(3) 0.017(4) C4 0.062(3) 0.094(4) 0.053(3) 0.027(3) 0.026(3) 0.020(3) C5 0.042(3) 0.055(3) 0.047(3) 0.015(2) 0.025(2) 0.016(2) C6 0.058(3) 0.037(2) 0.051(3) 0.014(2) 0.026(2) 0.013(2) C7 0.143(7) 0.040(3) 0.083(5) 0.026(3) 0.041(4) 0.015(4) C8 0.246(12) 0.036(3) 0.085(5) -0.006(3) 0.039(6) -0.033(5) C9 0.211(10) 0.047(4) 0.081(5) -0.013(4) 0.022(6) -0.049(5) C10 0.108(5) 0.037(3) 0.047(3) -0.003(2) 0.009(3) -0.020(3) C11 0.034(2) 0.035(2) 0.043(2) 0.0049(18) 0.0192(19) 0.0073(17) C12 0.032(2) 0.0273(19) 0.042(2) -0.0009(16) 0.0181(18) 0.0027(16) C13 0.031(2) 0.0215(17) 0.033(2) -0.0035(15) 0.0139(17) -0.0003(15) C14 0.0265(19) 0.0234(18) 0.0303(19) -0.0003(15) 0.0107(15) -0.0015(15) C15 0.031(2) 0.0233(18) 0.050(2) -0.0070(17) 0.0187(18) 0.0036(15) C16 0.032(2) 0.029(2) 0.071(3) -0.017(2) 0.021(2) -0.0026(17) C17 0.029(2) 0.035(2) 0.076(3) -0.019(2) 0.023(2) -0.0082(18) C18 0.042(3) 0.038(2) 0.074(3) -0.029(2) 0.021(2) -0.005(2) C19 0.032(2) 0.029(2) 0.051(3) -0.0159(18) 0.015(2) -0.0019(17) C20 0.055(3) 0.029(2) 0.049(3) 0.0006(18) 0.016(2) 0.005(2) C21 0.046(3) 0.041(2) 0.035(2) -0.0065(19) 0.0108(19) -0.001(2) C22 0.030(2) 0.0237(18) 0.044(2) -0.0013(17) 0.0149(18) -0.0021(16) O1W 0.110(8) 0.085(7) 0.103(7) -0.010(6) 0.027(7) -0.006(6) O2W 0.230(9) 0.103(5) 0.129(5) -0.023(4) 0.098(6) -0.010(5) O3W 0.183(7) 0.121(5) 0.250(9) -0.034(5) 0.136(7) -0.065(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 Cd1 O4 2.308(3) 1_455 ? Cd1 O3 2.333(3) 2_655 ? Cd1 N2 2.339(4) . ? Cd1 O1 2.355(3) . ? Cd1 N1 2.381(4) . ? Cd1 O2 2.466(3) . ? O1 C11 1.263(5) . ? O2 C11 1.250(5) . ? O3 C22 1.275(5) . ? O3 Cd1 2.333(3) 2_655 ? O4 C22 1.262(5) . ? O4 Cd1 2.308(3) 1_655 ? N1 C1 1.346(6) . ? N1 C5 1.350(6) . ? N2 C10 1.321(6) . ? N2 C6 1.367(6) . ? N3 C16 1.413(5) . ? N3 C18 1.469(6) . ? N3 H3B 0.8598 . ? C1 C2 1.415(9) . ? C1 H1A 0.9300 . ? C2 C3 1.359(10) . ? C2 H2A 0.9300 . ? C3 C4 1.367(9) . ? C3 H3A 0.9300 . ? C4 C5 1.401(7) . ? C4 H4A 0.9300 . ? C5 C6 1.469(7) . ? C6 C7 1.415(7) . ? C7 C8 1.359(11) . ? C7 H7A 0.9300 . ? C8 C9 1.341(10) . ? C8 H8A 0.9300 . ? C9 C10 1.394(8) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.508(5) . ? C12 C17 1.397(6) . ? C12 C13 1.403(5) . ? C13 C14 1.397(5) . ? C13 H13A 0.9300 . ? C14 C15 1.389(5) . ? C14 C22 1.509(5) . ? C15 C16 1.405(6) . ? C15 H15A 0.9300 . ? C16 C17 1.407(6) . ? C17 H17A 0.9300 . ? C18 C19 1.521(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C21 1.385(6) . ? C19 C20 1.388(6) . ? C20 C21 1.400(6) 3_655 ? C20 H20A 0.9300 . ? C21 C20 1.400(6) 3_655 ? C21 H21A 0.9300 . ? O1W O1W 1.409(19) 3_567 ? O2W H2WB 0.87(2) . ? O2W H2WA 0.87(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 O4 Cd1 O3 102.22(13) 1_455 2_655 ? O4 Cd1 N2 135.16(12) 1_455 . ? O3 Cd1 N2 84.67(11) 2_655 . ? O4 Cd1 O1 82.78(12) 1_455 . ? O3 Cd1 O1 107.23(13) 2_655 . ? N2 Cd1 O1 137.96(12) . . ? O4 Cd1 N1 88.41(14) 1_455 . ? O3 Cd1 N1 151.67(12) 2_655 . ? N2 Cd1 N1 69.75(13) . . ? O1 Cd1 N1 100.07(14) . . ? O4 Cd1 O2 136.72(10) 1_455 . ? O3 Cd1 O2 90.93(12) 2_655 . ? N2 Cd1 O2 86.53(12) . . ? O1 Cd1 O2 53.96(11) . . ? N1 Cd1 O2 99.20(13) . . ? C11 O1 Cd1 94.8(3) . . ? C11 O2 Cd1 89.9(3) . . ? C22 O3 Cd1 132.2(3) . 2_655 ? C22 O4 Cd1 105.8(2) . 1_655 ? C1 N1 C5 118.9(5) . . ? C1 N1 Cd1 123.6(4) . . ? C5 N1 Cd1 117.5(3) . . ? C10 N2 C6 118.6(4) . . ? C10 N2 Cd1 122.3(3) . . ? C6 N2 Cd1 118.8(3) . . ? C16 N3 C18 118.9(4) . . ? C16 N3 H3B 120.6 . . ? C18 N3 H3B 120.5 . . ? N1 C1 C2 121.7(6) . . ? N1 C1 H1A 119.2 . . ? C2 C1 H1A 119.2 . . ? C3 C2 C1 118.8(6) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C2 C3 C4 119.7(6) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C3 C4 C5 120.0(6) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? N1 C5 C4 120.9(5) . . ? N1 C5 C6 117.4(4) . . ? C4 C5 C6 121.7(5) . . ? N2 C6 C7 119.7(5) . . ? N2 C6 C5 116.4(4) . . ? C7 C6 C5 123.8(5) . . ? C8 C7 C6 119.9(6) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? C9 C8 C7 119.5(6) . . ? C9 C8 H8A 120.3 . . ? C7 C8 H8A 120.3 . . ? C8 C9 C10 119.8(7) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? N2 C10 C9 122.5(6) . . ? N2 C10 H10A 118.8 . . ? C9 C10 H10A 118.8 . . ? O2 C11 O1 121.3(4) . . ? O2 C11 C12 119.7(4) . . ? O1 C11 C12 119.0(4) . . ? C17 C12 C13 119.8(4) . . ? C17 C12 C11 119.6(4) . . ? C13 C12 C11 120.5(3) . . ? C14 C13 C12 119.3(3) . . ? C14 C13 H13A 120.3 . . ? C12 C13 H13A 120.3 . . ? C15 C14 C13 120.4(3) . . ? C15 C14 C22 119.0(3) . . ? C13 C14 C22 120.4(3) . . ? C14 C15 C16 121.3(4) . . ? C14 C15 H15A 119.4 . . ? C16 C15 H15A 119.4 . . ? C15 C16 C17 117.8(4) . . ? C15 C16 N3 123.3(4) . . ? C17 C16 N3 118.9(4) . . ? C12 C17 C16 121.3(4) . . ? C12 C17 H17A 119.4 . . ? C16 C17 H17A 119.4 . . ? N3 C18 C19 111.5(4) . . ? N3 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? N3 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C21 C19 C20 118.6(4) . . ? C21 C19 C18 121.0(4) . . ? C20 C19 C18 120.3(4) . . ? C19 C20 C21 121.0(4) . 3_655 ? C19 C20 H20A 119.5 . . ? C21 C20 H20A 119.5 3_655 . ? C19 C21 C20 120.3(4) . 3_655 ? C19 C21 H21A 119.8 . . ? C20 C21 H21A 119.8 3_655 . ? O4 C22 O3 121.8(4) . . ? O4 C22 C14 118.1(3) . . ? O3 C22 C14 120.0(3) . . ? H2WB O2W H2WA 101(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 O4 Cd1 O1 C11 -177.1(3) 1_455 . . . ? O3 Cd1 O1 C11 -76.5(3) 2_655 . . . ? N2 Cd1 O1 C11 25.0(4) . . . . ? N1 Cd1 O1 C11 95.8(3) . . . . ? O2 Cd1 O1 C11 1.7(3) . . . . ? O4 Cd1 O2 C11 0.0(4) 1_455 . . . ? O3 Cd1 O2 C11 109.1(3) 2_655 . . . ? N2 Cd1 O2 C11 -166.3(3) . . . . ? O1 Cd1 O2 C11 -1.7(3) . . . . ? N1 Cd1 O2 C11 -97.5(3) . . . . ? O4 Cd1 N1 C1 -39.7(4) 1_455 . . . ? O3 Cd1 N1 C1 -153.0(3) 2_655 . . . ? N2 Cd1 N1 C1 -179.7(4) . . . . ? O1 Cd1 N1 C1 42.7(4) . . . . ? O2 Cd1 N1 C1 97.4(4) . . . . ? O4 Cd1 N1 C5 141.3(3) 1_455 . . . ? O3 Cd1 N1 C5 28.0(5) 2_655 . . . ? N2 Cd1 N1 C5 1.2(3) . . . . ? O1 Cd1 N1 C5 -136.4(3) . . . . ? O2 Cd1 N1 C5 -81.6(3) . . . . ? O4 Cd1 N2 C10 117.7(5) 1_455 . . . ? O3 Cd1 N2 C10 15.7(5) 2_655 . . . ? O1 Cd1 N2 C10 -94.2(5) . . . . ? N1 Cd1 N2 C10 -176.7(5) . . . . ? O2 Cd1 N2 C10 -75.5(5) . . . . ? O4 Cd1 N2 C6 -68.2(4) 1_455 . . . ? O3 Cd1 N2 C6 -170.1(4) 2_655 . . . ? O1 Cd1 N2 C6 79.9(4) . . . . ? N1 Cd1 N2 C6 -2.5(3) . . . . ? O2 Cd1 N2 C6 98.6(4) . . . . ? C5 N1 C1 C2 0.3(7) . . . . ? Cd1 N1 C1 C2 -178.7(4) . . . . ? N1 C1 C2 C3 -0.9(9) . . . . ? C1 C2 C3 C4 0.9(10) . . . . ? C2 C3 C4 C5 -0.3(9) . . . . ? C1 N1 C5 C4 0.3(7) . . . . ? Cd1 N1 C5 C4 179.3(4) . . . . ? C1 N1 C5 C6 -179.0(4) . . . . ? Cd1 N1 C5 C6 0.1(6) . . . . ? C3 C4 C5 N1 -0.3(8) . . . . ? C3 C4 C5 C6 179.0(5) . . . . ? C10 N2 C6 C7 -0.5(8) . . . . ? Cd1 N2 C6 C7 -174.8(5) . . . . ? C10 N2 C6 C5 177.9(5) . . . . ? Cd1 N2 C6 C5 3.5(6) . . . . ? N1 C5 C6 N2 -2.3(6) . . . . ? C4 C5 C6 N2 178.4(4) . . . . ? N1 C5 C6 C7 175.9(6) . . . . ? C4 C5 C6 C7 -3.3(8) . . . . ? N2 C6 C7 C8 -0.2(12) . . . . ? C5 C6 C7 C8 -178.4(8) . . . . ? C6 C7 C8 C9 -0.3(16) . . . . ? C7 C8 C9 C10 1.4(17) . . . . ? C6 N2 C10 C9 1.6(10) . . . . ? Cd1 N2 C10 C9 175.8(7) . . . . ? C8 C9 C10 N2 -2.1(15) . . . . ? Cd1 O2 C11 O1 3.0(5) . . . . ? Cd1 O2 C11 C12 -178.6(3) . . . . ? Cd1 O1 C11 O2 -3.2(5) . . . . ? Cd1 O1 C11 C12 178.4(3) . . . . ? O2 C11 C12 C17 -170.0(4) . . . . ? O1 C11 C12 C17 8.4(6) . . . . ? O2 C11 C12 C13 9.2(6) . . . . ? O1 C11 C12 C13 -172.4(4) . . . . ? C17 C12 C13 C14 1.9(6) . . . . ? C11 C12 C13 C14 -177.2(3) . . . . ? C12 C13 C14 C15 -0.6(6) . . . . ? C12 C13 C14 C22 174.9(3) . . . . ? C13 C14 C15 C16 -1.5(6) . . . . ? C22 C14 C15 C16 -177.1(4) . . . . ? C14 C15 C16 C17 2.2(7) . . . . ? C14 C15 C16 N3 -177.8(4) . . . . ? C18 N3 C16 C15 -0.6(8) . . . . ? C18 N3 C16 C17 179.4(5) . . . . ? C13 C12 C17 C16 -1.2(7) . . . . ? C11 C12 C17 C16 178.0(4) . . . . ? C15 C16 C17 C12 -0.9(7) . . . . ? N3 C16 C17 C12 179.1(5) . . . . ? C16 N3 C18 C19 177.9(5) . . . . ? N3 C18 C19 C21 -97.0(5) . . . . ? N3 C18 C19 C20 85.5(6) . . . . ? C21 C19 C20 C21 -0.2(8) . . . 3_655 ? C18 C19 C20 C21 177.3(4) . . . 3_655 ? C20 C19 C21 C20 0.2(7) . . . 3_655 ? C18 C19 C21 C20 -177.3(4) . . . 3_655 ? Cd1 O4 C22 O3 -6.7(5) 1_655 . . . ? Cd1 O4 C22 C14 170.4(3) 1_655 . . . ? Cd1 O3 C22 O4 -99.4(5) 2_655 . . . ? Cd1 O3 C22 C14 83.6(4) 2_655 . . . ? C15 C14 C22 O4 11.6(6) . . . . ? C13 C14 C22 O4 -164.1(4) . . . . ? C15 C14 C22 O3 -171.3(4) . . . . ? C13 C14 C22 O3 13.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.293 _refine_diff_density_min -0.542 _refine_diff_density_rms 0.096 _database_code_depnum_ccdc_archive 'CCDC 937208' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 N3 O5 Zn' _chemical_formula_weight 493.77 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.937(8) _cell_length_b 10.472(3) _cell_length_c 14.340(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.467(7) _cell_angle_gamma 90.00 _cell_volume 4195(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1625 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 18.68 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2008 _exptl_absorpt_coefficient_mu 1.214 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7593 _exptl_absorpt_correction_T_max 0.8111 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11314 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4122 _reflns_number_gt 2434 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+5.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4122 _refine_ls_number_parameters 307 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1392 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 O3 O 0.11075(11) -0.2081(3) 0.4876(2) 0.0700(9) Uani 1 1 d . . . C20 C 0.15270(17) -0.2352(4) 0.4592(3) 0.0618(12) Uani 1 1 d . . . Zn1 Zn 0.103368(17) 0.29123(5) 0.10731(4) 0.0605(2) Uani 1 1 d . . . O1 O 0.14469(11) 0.1989(3) 0.1931(2) 0.0701(9) Uani 1 1 d . . . N2 N 0.10737(13) 0.4860(4) 0.1223(2) 0.0583(9) Uani 1 1 d . . . C14 C 0.15644(15) -0.0053(4) 0.2581(3) 0.0533(11) Uani 1 1 d . . . C18 C 0.23298(15) -0.1108(4) 0.2691(3) 0.0512(10) Uani 1 1 d . . . N3 N 0.27921(12) -0.1307(3) 0.2402(2) 0.0610(10) Uani 1 1 d . . . H3B H 0.2995 -0.1632 0.2788 0.073 Uiso 1 1 calc R . . C16 C 0.16960(15) -0.1623(4) 0.3769(3) 0.0530(10) Uani 1 1 d . . . C19 C 0.20272(14) -0.0216(4) 0.2271(3) 0.0534(10) Uani 1 1 d . . . H19A H 0.2138 0.0274 0.1777 0.064 Uiso 1 1 calc R . . O4 O 0.17818(14) -0.3128(4) 0.4993(3) 0.0977(12) Uani 1 1 d . . . C6 C 0.06421(18) 0.5410(5) 0.1252(3) 0.0659(13) Uani 1 1 d . . . N1 N 0.03116(14) 0.3333(5) 0.1221(3) 0.0805(13) Uani 1 1 d . . . C17 C 0.21579(15) -0.1793(4) 0.3459(3) 0.0522(10) Uani 1 1 d . . . H17A H 0.2358 -0.2370 0.3764 0.063 Uiso 1 1 calc R . . C15 C 0.13925(15) -0.0764(4) 0.3315(3) 0.0546(10) Uani 1 1 d . . . H15A H 0.1077 -0.0671 0.3506 0.065 Uiso 1 1 calc R . . C13 C 0.12476(17) 0.0938(4) 0.2133(3) 0.0612(12) Uani 1 1 d . . . O2 O 0.08257(12) 0.0717(3) 0.1964(3) 0.0935(12) Uani 1 1 d . . . C5 C 0.02382(18) 0.4622(6) 0.1246(3) 0.0733(16) Uani 1 1 d . . . C12 C 0.1457(2) 0.5598(5) 0.1222(3) 0.0736(13) Uani 1 1 d . . . H12A H 0.1756 0.5211 0.1197 0.088 Uiso 1 1 calc R . . C21 C 0.29486(16) -0.0992(5) 0.1475(3) 0.0679(12) Uani 1 1 d . . . H21A H 0.3292 -0.1115 0.1444 0.081 Uiso 1 1 calc R . . H21B H 0.2885 -0.0095 0.1362 0.081 Uiso 1 1 calc R . . C22 C 0.27148(15) -0.1763(4) 0.0712(3) 0.0581(11) Uani 1 1 d . . . C23 C 0.27520(18) -0.3078(5) 0.0696(3) 0.0700(13) Uani 1 1 d . . . H23A H 0.2924 -0.3486 0.1167 0.084 Uiso 1 1 calc R . . C24 C 0.24581(17) -0.1201(5) -0.0007(3) 0.0695(13) Uani 1 1 d . . . H24A H 0.2427 -0.0317 -0.0024 0.083 Uiso 1 1 calc R . . C7 C 0.0593(3) 0.6762(6) 0.1284(4) 0.095(2) Uani 1 1 d . . . C8 C 0.0120(4) 0.7257(10) 0.1291(6) 0.151(4) Uani 1 1 d . . . H8A H 0.0078 0.8138 0.1298 0.182 Uiso 1 1 calc R . . C11 C 0.1436(3) 0.6909(5) 0.1254(4) 0.102(2) Uani 1 1 d . . . H11A H 0.1715 0.7394 0.1253 0.123 Uiso 1 1 calc R . . C9 C -0.0258(3) 0.6524(10) 0.1289(5) 0.125(3) Uani 1 1 d . . . H9A H -0.0559 0.6907 0.1305 0.150 Uiso 1 1 calc R . . C2 C -0.0527(4) 0.2977(9) 0.1207(6) 0.147(4) Uani 1 1 d U . . H2A H -0.0784 0.2413 0.1173 0.177 Uiso 1 1 calc R . . C4 C -0.0232(2) 0.5141(9) 0.1263(3) 0.107(3) Uani 1 1 d . . . C10 C 0.1017(3) 0.7462(7) 0.1285(5) 0.123(3) Uani 1 1 d . . . H10A H 0.1001 0.8349 0.1310 0.148 Uiso 1 1 calc R . . C1 C -0.0049(2) 0.2531(8) 0.1208(5) 0.124(3) Uani 1 1 d . . . H1 H 0.0010 0.1657 0.1200 0.149 Uiso 1 1 calc R . . C3 C -0.0595(2) 0.4213(13) 0.1256(4) 0.154(5) Uani 1 1 d . . . H3A H -0.0909 0.4500 0.1288 0.185 Uiso 1 1 calc R . . O1W O 0.0471(3) 0.9910(8) 0.9843(7) 0.129(3) Uani 0.50 1 d P . . O2W O 0.0130(4) 0.9774(9) 0.2892(9) 0.154(4) Uani 0.50 1 d P . . 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 O3 0.0541(19) 0.078(2) 0.078(2) 0.0068(17) -0.0059(16) -0.0080(16) C20 0.057(3) 0.056(3) 0.073(3) -0.004(2) 0.000(2) -0.007(2) Zn1 0.0519(3) 0.0547(3) 0.0748(4) 0.0074(3) -0.0038(2) 0.0088(2) O1 0.069(2) 0.0437(17) 0.097(2) 0.0072(17) -0.0308(17) -0.0009(15) N2 0.063(2) 0.057(2) 0.055(2) -0.0003(17) -0.0001(18) 0.0201(19) C14 0.055(3) 0.039(2) 0.065(3) -0.005(2) -0.020(2) -0.0016(19) C18 0.058(3) 0.041(2) 0.055(2) -0.006(2) -0.012(2) 0.002(2) N3 0.055(2) 0.071(3) 0.057(2) 0.0050(19) -0.0083(17) 0.0075(19) C16 0.060(3) 0.039(2) 0.060(3) -0.003(2) -0.009(2) -0.005(2) C19 0.056(3) 0.046(2) 0.058(3) 0.000(2) -0.013(2) -0.001(2) O4 0.098(3) 0.079(3) 0.116(3) 0.045(2) 0.024(2) 0.022(2) C6 0.063(3) 0.092(4) 0.043(3) -0.004(2) -0.002(2) 0.034(3) N1 0.049(2) 0.123(4) 0.070(3) 0.028(3) 0.0001(19) -0.001(3) C17 0.059(3) 0.036(2) 0.061(3) 0.0007(19) -0.014(2) 0.0011(18) C15 0.051(2) 0.043(2) 0.070(3) -0.002(2) -0.008(2) -0.0061(19) C13 0.063(3) 0.047(3) 0.073(3) -0.002(2) -0.019(2) 0.001(2) O2 0.060(2) 0.079(2) 0.141(3) 0.023(2) -0.037(2) -0.0026(18) C5 0.065(3) 0.118(5) 0.037(2) 0.012(3) 0.001(2) 0.047(3) C12 0.086(4) 0.053(3) 0.081(3) -0.004(3) -0.008(3) 0.004(3) C21 0.059(3) 0.072(3) 0.073(3) 0.010(3) 0.003(2) 0.005(2) C22 0.063(3) 0.059(3) 0.052(3) 0.007(2) 0.003(2) 0.011(2) C23 0.085(3) 0.066(3) 0.059(3) 0.017(3) -0.008(2) 0.022(3) C24 0.088(3) 0.058(3) 0.063(3) 0.012(2) -0.002(3) 0.018(3) C7 0.118(5) 0.092(4) 0.074(4) -0.022(3) -0.026(3) 0.070(4) C8 0.166(8) 0.160(9) 0.128(6) -0.045(6) -0.041(6) 0.115(8) C11 0.128(6) 0.057(4) 0.121(5) -0.016(3) -0.035(4) 0.007(3) C9 0.105(6) 0.188(10) 0.081(4) -0.024(5) -0.021(4) 0.104(6) C2 0.146(4) 0.148(4) 0.147(4) 0.0015(10) 0.0015(10) -0.0016(10) C4 0.076(4) 0.203(8) 0.041(3) 0.009(4) 0.000(3) 0.061(5) C10 0.177(8) 0.064(4) 0.129(6) -0.037(4) -0.050(6) 0.021(5) C1 0.058(4) 0.186(7) 0.129(6) 0.056(5) -0.006(3) -0.012(4) C3 0.037(3) 0.371(16) 0.055(3) 0.009(6) 0.005(3) 0.003(6) O1W 0.131(7) 0.084(6) 0.172(9) 0.022(6) -0.008(6) -0.043(5) O2W 0.130(10) 0.114(7) 0.216(14) 0.013(7) -0.005(8) 0.013(6) _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 O3 C20 1.275(5) . ? O3 Zn1 1.938(3) 6_556 ? C20 O4 1.221(5) . ? C20 C16 1.486(6) . ? Zn1 O3 1.938(3) 6 ? Zn1 O1 1.938(3) . ? Zn1 N2 2.054(4) . ? Zn1 N1 2.077(4) . ? O1 C13 1.269(5) . ? N2 C12 1.320(6) . ? N2 C6 1.337(5) . ? C14 C15 1.378(6) . ? C14 C19 1.381(6) . ? C14 C13 1.505(5) . ? C18 N3 1.376(5) . ? C18 C19 1.393(5) . ? C18 C17 1.403(5) . ? N3 C21 1.440(5) . ? N3 H3B 0.8600 . ? C16 C17 1.380(6) . ? C16 C15 1.394(5) . ? C19 H19A 0.9300 . ? C6 C5 1.397(7) . ? C6 C7 1.424(8) . ? N1 C1 1.312(7) . ? N1 C5 1.366(7) . ? C17 H17A 0.9300 . ? C15 H15A 0.9300 . ? C13 O2 1.224(5) . ? C5 C4 1.423(7) . ? C12 C11 1.375(7) . ? C12 H12A 0.9300 . ? C21 C22 1.505(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.381(6) . ? C22 C24 1.383(6) . ? C23 C24 1.372(6) 7_545 ? C23 H23A 0.9300 . ? C24 C23 1.372(6) 7_545 ? C24 H24A 0.9300 . ? C7 C8 1.419(10) . ? C7 C10 1.393(9) . ? C8 C9 1.306(12) . ? C8 H8A 0.9300 . ? C11 C10 1.308(9) . ? C11 H11A 0.9300 . ? C9 C4 1.451(11) . ? C9 H9A 0.9300 . ? C2 C3 1.311(12) . ? C2 C1 1.415(10) . ? C2 H2A 0.9300 . ? C4 C3 1.403(11) . ? C10 H10A 0.9300 . ? C1 H1 0.9300 . ? C3 H3A 0.9300 . ? O2W O2W 1.33(2) 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 C20 O3 Zn1 106.7(3) . 6_556 ? O4 C20 O3 122.1(5) . . ? O4 C20 C16 121.9(4) . . ? O3 C20 C16 115.9(4) . . ? O3 Zn1 O1 105.73(14) 6 . ? O3 Zn1 N2 122.21(13) 6 . ? O1 Zn1 N2 113.40(13) . . ? O3 Zn1 N1 107.22(15) 6 . ? O1 Zn1 N1 127.96(15) . . ? N2 Zn1 N1 80.25(18) . . ? C13 O1 Zn1 108.5(3) . . ? C12 N2 C6 118.6(4) . . ? C12 N2 Zn1 128.7(3) . . ? C6 N2 Zn1 112.5(3) . . ? C15 C14 C19 120.8(4) . . ? C15 C14 C13 119.4(4) . . ? C19 C14 C13 119.8(4) . . ? N3 C18 C19 122.6(4) . . ? N3 C18 C17 119.2(4) . . ? C19 C18 C17 118.2(4) . . ? C18 N3 C21 122.4(3) . . ? C18 N3 H3B 118.8 . . ? C21 N3 H3B 118.8 . . ? C17 C16 C15 120.0(4) . . ? C17 C16 C20 119.5(4) . . ? C15 C16 C20 120.4(4) . . ? C18 C19 C14 120.7(4) . . ? C18 C19 H19A 119.7 . . ? C14 C19 H19A 119.7 . . ? N2 C6 C5 118.3(5) . . ? N2 C6 C7 121.1(5) . . ? C5 C6 C7 120.6(5) . . ? C1 N1 C5 121.2(5) . . ? C1 N1 Zn1 127.5(5) . . ? C5 N1 Zn1 111.0(3) . . ? C16 C17 C18 120.9(4) . . ? C16 C17 H17A 119.6 . . ? C18 C17 H17A 119.6 . . ? C14 C15 C16 119.4(4) . . ? C14 C15 H15A 120.3 . . ? C16 C15 H15A 120.3 . . ? O2 C13 O1 122.8(4) . . ? O2 C13 C14 121.1(4) . . ? O1 C13 C14 116.0(4) . . ? N1 C5 C6 117.5(4) . . ? N1 C5 C4 121.1(6) . . ? C6 C5 C4 121.4(6) . . ? N2 C12 C11 123.4(5) . . ? N2 C12 H12A 118.3 . . ? C11 C12 H12A 118.3 . . ? N3 C21 C22 114.5(4) . . ? N3 C21 H21A 108.6 . . ? C22 C21 H21A 108.6 . . ? N3 C21 H21B 108.6 . . ? C22 C21 H21B 108.6 . . ? H21A C21 H21B 107.6 . . ? C23 C22 C24 116.9(4) . . ? C23 C22 C21 121.0(4) . . ? C24 C22 C21 122.2(4) . . ? C24 C23 C22 121.9(4) 7_545 . ? C24 C23 H23A 119.0 7_545 . ? C22 C23 H23A 119.0 . . ? C23 C24 C22 121.2(4) 7_545 . ? C23 C24 H24A 119.4 7_545 . ? C22 C24 H24A 119.4 . . ? C6 C7 C8 117.0(8) . . ? C6 C7 C10 116.2(5) . . ? C8 C7 C10 126.9(8) . . ? C9 C8 C7 122.6(9) . . ? C9 C8 H8A 118.7 . . ? C7 C8 H8A 118.7 . . ? C10 C11 C12 118.7(7) . . ? C10 C11 H11A 120.6 . . ? C12 C11 H11A 120.6 . . ? C8 C9 C4 123.1(7) . . ? C8 C9 H9A 118.5 . . ? C4 C9 H9A 118.5 . . ? C3 C2 C1 117.5(9) . . ? C3 C2 H2A 121.2 . . ? C1 C2 H2A 121.2 . . ? C3 C4 C5 113.7(8) . . ? C3 C4 C9 131.0(7) . . ? C5 C4 C9 115.3(7) . . ? C11 C10 C7 121.9(6) . . ? C11 C10 H10A 119.0 . . ? C7 C10 H10A 119.0 . . ? N1 C1 C2 120.9(8) . . ? N1 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C2 C3 C4 125.5(8) . . ? C2 C3 H3A 117.3 . . ? C4 C3 H3A 117.3 . . ? 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 Zn1 O3 C20 O4 8.2(6) 6_556 . . . ? Zn1 O3 C20 C16 -169.2(3) 6_556 . . . ? O3 Zn1 O1 C13 -75.9(3) 6 . . . ? N2 Zn1 O1 C13 147.7(3) . . . . ? N1 Zn1 O1 C13 51.7(4) . . . . ? O3 Zn1 N2 C12 -75.6(4) 6 . . . ? O1 Zn1 N2 C12 52.8(4) . . . . ? N1 Zn1 N2 C12 -179.9(4) . . . . ? O3 Zn1 N2 C6 98.8(3) 6 . . . ? O1 Zn1 N2 C6 -132.8(3) . . . . ? N1 Zn1 N2 C6 -5.5(3) . . . . ? C19 C18 N3 C21 -23.1(6) . . . . ? C17 C18 N3 C21 159.1(4) . . . . ? O4 C20 C16 C17 -2.0(7) . . . . ? O3 C20 C16 C17 175.4(4) . . . . ? O4 C20 C16 C15 178.6(4) . . . . ? O3 C20 C16 C15 -4.0(6) . . . . ? N3 C18 C19 C14 179.6(4) . . . . ? C17 C18 C19 C14 -2.6(6) . . . . ? C15 C14 C19 C18 0.3(6) . . . . ? C13 C14 C19 C18 178.5(3) . . . . ? C12 N2 C6 C5 179.5(4) . . . . ? Zn1 N2 C6 C5 4.4(5) . . . . ? C12 N2 C6 C7 -0.2(6) . . . . ? Zn1 N2 C6 C7 -175.3(3) . . . . ? O3 Zn1 N1 C1 58.8(5) 6 . . . ? O1 Zn1 N1 C1 -68.2(5) . . . . ? N2 Zn1 N1 C1 179.6(5) . . . . ? O3 Zn1 N1 C5 -115.1(3) 6 . . . ? O1 Zn1 N1 C5 117.9(3) . . . . ? N2 Zn1 N1 C5 5.7(3) . . . . ? C15 C16 C17 C18 0.2(6) . . . . ? C20 C16 C17 C18 -179.2(4) . . . . ? N3 C18 C17 C16 -179.8(4) . . . . ? C19 C18 C17 C16 2.3(6) . . . . ? C19 C14 C15 C16 2.3(6) . . . . ? C13 C14 C15 C16 -175.9(4) . . . . ? C17 C16 C15 C14 -2.6(6) . . . . ? C20 C16 C15 C14 176.9(4) . . . . ? Zn1 O1 C13 O2 -14.2(6) . . . . ? Zn1 O1 C13 C14 164.4(3) . . . . ? C15 C14 C13 O2 -43.1(6) . . . . ? C19 C14 C13 O2 138.7(5) . . . . ? C15 C14 C13 O1 138.3(4) . . . . ? C19 C14 C13 O1 -39.9(6) . . . . ? C1 N1 C5 C6 -179.6(5) . . . . ? Zn1 N1 C5 C6 -5.3(5) . . . . ? C1 N1 C5 C4 0.2(7) . . . . ? Zn1 N1 C5 C4 174.5(3) . . . . ? N2 C6 C5 N1 0.7(6) . . . . ? C7 C6 C5 N1 -179.7(4) . . . . ? N2 C6 C5 C4 -179.1(4) . . . . ? C7 C6 C5 C4 0.5(7) . . . . ? C6 N2 C12 C11 0.4(7) . . . . ? Zn1 N2 C12 C11 174.6(4) . . . . ? C18 N3 C21 C22 -65.0(5) . . . . ? N3 C21 C22 C23 -58.9(6) . . . . ? N3 C21 C22 C24 121.7(5) . . . . ? C24 C22 C23 C24 -0.5(8) . . . 7_545 ? C21 C22 C23 C24 -180.0(4) . . . 7_545 ? C23 C22 C24 C23 0.5(8) . . . 7_545 ? C21 C22 C24 C23 180.0(4) . . . 7_545 ? N2 C6 C7 C8 178.6(5) . . . . ? C5 C6 C7 C8 -1.1(8) . . . . ? N2 C6 C7 C10 -0.2(7) . . . . ? C5 C6 C7 C10 -179.9(5) . . . . ? C6 C7 C8 C9 1.4(11) . . . . ? C10 C7 C8 C9 -180.0(8) . . . . ? N2 C12 C11 C10 -0.2(9) . . . . ? C7 C8 C9 C4 -1.1(13) . . . . ? N1 C5 C4 C3 0.3(6) . . . . ? C6 C5 C4 C3 -179.9(4) . . . . ? N1 C5 C4 C9 -180.0(5) . . . . ? C6 C5 C4 C9 -0.2(7) . . . . ? C8 C9 C4 C3 -179.9(7) . . . . ? C8 C9 C4 C5 0.5(10) . . . . ? C12 C11 C10 C7 -0.2(11) . . . . ? C6 C7 C10 C11 0.4(10) . . . . ? C8 C7 C10 C11 -178.2(7) . . . . ? C5 N1 C1 C2 0.9(10) . . . . ? Zn1 N1 C1 C2 -172.4(5) . . . . ? C3 C2 C1 N1 -2.6(12) . . . . ? C1 C2 C3 C4 3.3(13) . . . . ? C5 C4 C3 C2 -2.2(10) . . . . ? C9 C4 C3 C2 178.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.647 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 937209' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 Cu N3 O5' _chemical_formula_weight 491.95 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.746(4) _cell_length_b 15.840(5) _cell_length_c 15.859(6) _cell_angle_alpha 90.00 _cell_angle_beta 130.94(4) _cell_angle_gamma 90.00 _cell_volume 2039.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3304 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 26.80 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 1.116 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8160 _exptl_absorpt_correction_T_max 0.8505 _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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10989 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4005 _reflns_number_gt 3203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+1.6889P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4005 _refine_ls_number_parameters 298 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 Cu1 Cu 0.19903(4) 0.54797(2) 0.44676(3) 0.02740(12) Uani 1 1 d . . . O1 O 0.2454(2) 0.60871(12) 0.57365(16) 0.0346(5) Uani 1 1 d . . . O2 O 0.4380(2) 0.68045(13) 0.58832(16) 0.0366(5) Uani 1 1 d . . . O3 O 0.7523(3) 0.91115(14) 0.8843(2) 0.0514(6) Uani 1 1 d . . . O4 O 0.6579(2) 0.95058(11) 0.96891(16) 0.0322(5) Uani 1 1 d . . . O1W O -0.0302(2) 0.47566(13) 0.38944(18) 0.0424(5) Uani 1 1 d . . . H1WB H -0.0047 0.4352 0.4336 0.064 Uiso 1 1 d R . . H1WA H -0.1117 0.4835 0.3861 0.064 Uiso 1 1 d R . . N1 N 0.0421(3) 0.63957(14) 0.3380(2) 0.0303(5) Uani 1 1 d . . . N2 N 0.2105(3) 0.52767(13) 0.32309(19) 0.0283(5) Uani 1 1 d . . . N3 N 0.2857(3) 0.71091(14) 0.8926(2) 0.0345(6) Uani 1 1 d . . . H3A H 0.2726 0.7485 0.9253 0.041 Uiso 1 1 d R . . C1 C -0.0416(4) 0.69412(18) 0.3480(3) 0.0373(7) Uani 1 1 d . . . H1 H -0.0292 0.6919 0.4118 0.045 Uiso 1 1 calc R . . C2 C -0.1484(4) 0.7552(2) 0.2660(3) 0.0467(8) Uani 1 1 d . . . H2 H -0.2060 0.7918 0.2755 0.056 Uiso 1 1 calc R . . C3 C -0.1667(4) 0.7601(2) 0.1720(3) 0.0510(9) Uani 1 1 d . . . H3 H -0.2355 0.8006 0.1178 0.061 Uiso 1 1 calc R . . C4 C -0.0801(4) 0.7030(2) 0.1581(3) 0.0416(8) Uani 1 1 d . . . C5 C 0.0217(3) 0.64290(17) 0.2439(2) 0.0304(6) Uani 1 1 d . . . C6 C 0.1140(3) 0.58323(17) 0.2361(2) 0.0289(6) Uani 1 1 d . . . C7 C 0.1070(4) 0.58518(19) 0.1445(2) 0.0373(7) Uani 1 1 d . . . C8 C 0.0017(5) 0.6465(2) 0.0581(3) 0.0520(9) Uani 1 1 d . . . H8 H -0.0050 0.6480 -0.0033 0.062 Uiso 1 1 calc R . . C9 C -0.0883(5) 0.7023(2) 0.0641(3) 0.0565(10) Uani 1 1 d . . . H9 H -0.1564 0.7406 0.0063 0.068 Uiso 1 1 calc R . . C10 C 0.2064(4) 0.5268(2) 0.1449(3) 0.0427(8) Uani 1 1 d . . . H10 H 0.2060 0.5256 0.0861 0.051 Uiso 1 1 calc R . . C11 C 0.3039(4) 0.4719(2) 0.2327(3) 0.0409(8) Uani 1 1 d . . . H11 H 0.3698 0.4332 0.2335 0.049 Uiso 1 1 calc R . . C12 C 0.3040(4) 0.47412(18) 0.3210(2) 0.0334(7) Uani 1 1 d . . . H12 H 0.3717 0.4369 0.3803 0.040 Uiso 1 1 calc R . . C13 C 0.3591(3) 0.66548(16) 0.6187(2) 0.0268(6) Uani 1 1 d . . . C14 C 0.3966(3) 0.71500(16) 0.7152(2) 0.0259(6) Uani 1 1 d . . . C15 C 0.3258(3) 0.68906(17) 0.7594(2) 0.0294(6) Uani 1 1 d . . . H15 H 0.2578 0.6418 0.7302 0.035 Uiso 1 1 calc R . . C16 C 0.3565(3) 0.73375(16) 0.8478(2) 0.0272(6) Uani 1 1 d . . . C17 C 0.2313(4) 0.62412(18) 0.8844(3) 0.0388(7) Uani 1 1 d . . . H17A H 0.1497 0.6088 0.8062 0.047 Uiso 1 1 calc R . . H17B H 0.1783 0.6220 0.9157 0.047 Uiso 1 1 calc R . . C18 C 0.3696(4) 0.55948(18) 0.9439(3) 0.0360(7) Uani 1 1 d . . . C19 C 0.5152(5) 0.5732(2) 1.0514(3) 0.0702(13) Uani 1 1 d . . . H19 H 0.5284 0.6228 1.0880 0.084 Uiso 1 1 calc R . . C20 C 0.3575(5) 0.4854(2) 0.8941(3) 0.0653(12) Uani 1 1 d . . . H20 H 0.2612 0.4742 0.8216 0.078 Uiso 1 1 calc R . . C21 C 0.6571(3) 0.90379(17) 0.9027(2) 0.0290(6) Uani 1 1 d D . . C22 C 0.5346(3) 0.83078(16) 0.8480(2) 0.0258(6) Uani 1 1 d D . . C23 C 0.4587(3) 0.80574(16) 0.8891(2) 0.0279(6) Uani 1 1 d . . . H23 H 0.4760 0.8374 0.9454 0.033 Uiso 1 1 calc R . . C24 C 0.5033(3) 0.78471(16) 0.7604(2) 0.0269(6) Uani 1 1 d . . . H24 H 0.5532 0.8003 0.7321 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0317(2) 0.02451(18) 0.0272(2) 0.00083(13) 0.01980(17) 0.00129(14) O1 0.0446(12) 0.0322(10) 0.0325(11) -0.0088(9) 0.0277(10) -0.0101(9) O2 0.0436(12) 0.0431(12) 0.0354(12) -0.0042(9) 0.0312(11) -0.0043(10) O3 0.0540(14) 0.0507(13) 0.0764(17) -0.0313(12) 0.0544(14) -0.0239(11) O4 0.0365(11) 0.0314(10) 0.0319(11) -0.0101(8) 0.0237(10) -0.0080(9) O1W 0.0367(12) 0.0457(12) 0.0485(13) -0.0044(10) 0.0295(11) -0.0096(10) N1 0.0303(13) 0.0273(12) 0.0344(13) -0.0012(10) 0.0218(12) -0.0020(10) N2 0.0285(12) 0.0258(11) 0.0297(13) 0.0013(9) 0.0187(11) -0.0004(9) N3 0.0481(15) 0.0302(12) 0.0452(15) -0.0006(11) 0.0392(14) 0.0006(11) C1 0.0373(17) 0.0362(16) 0.0459(19) -0.0007(14) 0.0306(16) 0.0004(13) C2 0.0391(18) 0.0428(18) 0.058(2) 0.0050(16) 0.0319(18) 0.0127(15) C3 0.044(2) 0.049(2) 0.044(2) 0.0113(16) 0.0216(17) 0.0208(16) C4 0.0365(17) 0.0426(17) 0.0330(17) 0.0061(14) 0.0172(15) 0.0091(14) C5 0.0273(15) 0.0313(14) 0.0264(15) 0.0008(11) 0.0148(13) -0.0005(11) C6 0.0260(14) 0.0295(14) 0.0237(14) -0.0005(11) 0.0130(13) -0.0017(11) C7 0.0385(17) 0.0384(16) 0.0272(16) -0.0009(13) 0.0182(15) 0.0008(13) C8 0.065(2) 0.057(2) 0.0311(18) 0.0096(15) 0.0304(18) 0.0121(18) C9 0.062(2) 0.059(2) 0.0356(19) 0.0193(17) 0.0267(19) 0.0239(19) C10 0.053(2) 0.0471(18) 0.0347(18) -0.0026(14) 0.0313(17) 0.0001(15) C11 0.0450(19) 0.0391(17) 0.0432(19) -0.0015(14) 0.0310(17) 0.0072(14) C12 0.0351(16) 0.0304(14) 0.0340(16) 0.0019(12) 0.0223(15) 0.0031(12) C13 0.0326(15) 0.0249(13) 0.0239(14) 0.0009(11) 0.0189(13) 0.0036(11) C14 0.0281(14) 0.0262(13) 0.0247(14) -0.0011(11) 0.0178(13) 0.0010(11) C15 0.0349(16) 0.0248(13) 0.0321(16) -0.0037(11) 0.0235(14) -0.0046(11) C16 0.0288(14) 0.0284(14) 0.0279(14) 0.0035(11) 0.0201(13) 0.0044(11) C17 0.0450(18) 0.0386(16) 0.0489(19) 0.0019(14) 0.0378(17) -0.0040(14) C18 0.0416(17) 0.0340(16) 0.0386(17) 0.0011(13) 0.0290(16) -0.0049(13) C19 0.076(3) 0.047(2) 0.046(2) -0.0162(17) 0.022(2) 0.0143(19) C20 0.059(2) 0.047(2) 0.042(2) -0.0131(17) 0.0119(19) 0.0038(18) C21 0.0273(15) 0.0287(14) 0.0283(15) -0.0027(12) 0.0171(13) -0.0003(11) C22 0.0248(14) 0.0248(13) 0.0263(14) -0.0004(11) 0.0160(13) 0.0003(11) C23 0.0304(15) 0.0277(14) 0.0271(15) -0.0011(11) 0.0194(13) 0.0033(11) C24 0.0281(14) 0.0284(14) 0.0282(15) 0.0013(11) 0.0202(13) 0.0004(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.9590(19) 2_646 ? Cu1 O1 1.977(2) . ? Cu1 N1 2.028(2) . ? Cu1 N2 2.070(2) . ? Cu1 O1W 2.296(2) . ? O1 C13 1.291(3) . ? O2 C13 1.242(3) . ? O3 C21 1.240(3) . ? O4 C21 1.280(3) . ? O4 Cu1 1.9590(19) 2_656 ? O1W H1WB 0.8517 . ? O1W H1WA 0.8511 . ? N1 C1 1.330(4) . ? N1 C5 1.360(4) . ? N2 C12 1.331(4) . ? N2 C6 1.370(3) . ? N3 C16 1.386(3) . ? N3 C17 1.466(4) . ? N3 H3A 0.8601 . ? C1 C2 1.410(4) . ? C1 H1 0.9300 . ? C2 C3 1.371(5) . ? C2 H2 0.9300 . ? C3 C4 1.414(5) . ? C3 H3 0.9300 . ? C4 C5 1.416(4) . ? C4 C9 1.435(5) . ? C5 C6 1.432(4) . ? C6 C7 1.406(4) . ? C7 C10 1.409(4) . ? C7 C8 1.438(4) . ? C8 C9 1.358(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.372(4) . ? C10 H10 0.9300 . ? C11 C12 1.401(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.521(4) . ? C14 C15 1.392(4) . ? C14 C24 1.404(4) . ? C15 C16 1.404(4) . ? C15 H15 0.9300 . ? C16 C23 1.412(4) . ? C17 C18 1.520(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C20 1.372(4) . ? C18 C19 1.380(5) . ? C19 C20 1.390(5) 3_667 ? C19 H19 0.9300 . ? C20 C19 1.390(5) 3_667 ? C20 H20 0.9300 . ? C21 C22 1.525(4) . ? C22 C23 1.394(4) . ? C22 C24 1.402(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu1 O1 97.28(9) 2_646 . ? O4 Cu1 N1 170.89(9) 2_646 . ? O1 Cu1 N1 91.84(10) . . ? O4 Cu1 N2 90.98(9) 2_646 . ? O1 Cu1 N2 155.28(9) . . ? N1 Cu1 N2 80.67(10) . . ? O4 Cu1 O1W 92.06(9) 2_646 . ? O1 Cu1 O1W 97.78(9) . . ? N1 Cu1 O1W 86.65(10) . . ? N2 Cu1 O1W 105.19(9) . . ? C13 O1 Cu1 114.72(17) . . ? C21 O4 Cu1 126.60(18) . 2_656 ? Cu1 O1W H1WB 111.5 . . ? Cu1 O1W H1WA 138.2 . . ? H1WB O1W H1WA 85.6 . . ? C1 N1 C5 118.1(3) . . ? C1 N1 Cu1 127.9(2) . . ? C5 N1 Cu1 114.04(18) . . ? C12 N2 C6 118.1(3) . . ? C12 N2 Cu1 129.6(2) . . ? C6 N2 Cu1 112.20(18) . . ? C16 N3 C17 121.4(2) . . ? C16 N3 H3A 119.3 . . ? C17 N3 H3A 119.3 . . ? N1 C1 C2 122.7(3) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 119.5(3) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 119.5(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 116.9(3) . . ? C3 C4 C9 124.7(3) . . ? C5 C4 C9 118.4(3) . . ? N1 C5 C4 123.3(3) . . ? N1 C5 C6 116.5(2) . . ? C4 C5 C6 120.2(3) . . ? N2 C6 C7 123.1(3) . . ? N2 C6 C5 116.6(3) . . ? C7 C6 C5 120.2(3) . . ? C6 C7 C10 117.0(3) . . ? C6 C7 C8 118.3(3) . . ? C10 C7 C8 124.7(3) . . ? C9 C8 C7 121.7(3) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C4 121.0(3) . . ? C8 C9 H9 119.5 . . ? C4 C9 H9 119.5 . . ? C11 C10 C7 119.6(3) . . ? C11 C10 H10 120.2 . . ? C7 C10 H10 120.2 . . ? C10 C11 C12 119.9(3) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? N2 C12 C11 122.3(3) . . ? N2 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? O2 C13 O1 123.9(3) . . ? O2 C13 C14 119.6(2) . . ? O1 C13 C14 116.5(2) . . ? C15 C14 C24 120.5(2) . . ? C15 C14 C13 118.9(2) . . ? C24 C14 C13 120.6(2) . . ? C14 C15 C16 120.4(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? N3 C16 C15 122.1(3) . . ? N3 C16 C23 119.7(2) . . ? C15 C16 C23 118.2(3) . . ? N3 C17 C18 114.0(2) . . ? N3 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? N3 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C20 C18 C19 116.7(3) . . ? C20 C18 C17 122.2(3) . . ? C19 C18 C17 121.1(3) . . ? C18 C19 C20 121.3(3) . 3_667 ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 3_667 . ? C18 C20 C19 122.0(3) . 3_667 ? C18 C20 H20 119.0 . . ? C19 C20 H20 119.0 3_667 . ? O3 C21 O4 125.1(3) . . ? O3 C21 C22 118.4(2) . . ? O4 C21 C22 116.4(2) . . ? C23 C22 C24 118.8(2) . . ? C23 C22 C21 120.1(2) . . ? C24 C22 C21 121.0(2) . . ? C22 C23 C16 121.9(3) . . ? C22 C23 H23 119.0 . . ? C16 C23 H23 119.0 . . ? C22 C24 C14 120.0(2) . . ? C22 C24 H24 120.0 . . ? C14 C24 H24 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Cu1 O1 C13 95.31(19) 2_646 . . . ? N1 Cu1 O1 C13 -84.73(19) . . . . ? N2 Cu1 O1 C13 -13.3(3) . . . . ? O1W Cu1 O1 C13 -171.60(18) . . . . ? O4 Cu1 N1 C1 155.4(5) 2_646 . . . ? O1 Cu1 N1 C1 -24.4(2) . . . . ? N2 Cu1 N1 C1 179.3(2) . . . . ? O1W Cu1 N1 C1 73.3(2) . . . . ? O4 Cu1 N1 C5 -23.7(6) 2_646 . . . ? O1 Cu1 N1 C5 156.47(19) . . . . ? N2 Cu1 N1 C5 0.15(18) . . . . ? O1W Cu1 N1 C5 -105.84(19) . . . . ? O4 Cu1 N2 C12 -8.2(2) 2_646 . . . ? O1 Cu1 N2 C12 101.7(3) . . . . ? N1 Cu1 N2 C12 175.5(2) . . . . ? O1W Cu1 N2 C12 -100.6(2) . . . . ? O4 Cu1 N2 C6 176.90(18) 2_646 . . . ? O1 Cu1 N2 C6 -73.2(3) . . . . ? N1 Cu1 N2 C6 0.58(18) . . . . ? O1W Cu1 N2 C6 84.50(19) . . . . ? C5 N1 C1 C2 -0.6(4) . . . . ? Cu1 N1 C1 C2 -179.7(2) . . . . ? N1 C1 C2 C3 -0.8(5) . . . . ? C1 C2 C3 C4 1.0(5) . . . . ? C2 C3 C4 C5 0.3(5) . . . . ? C2 C3 C4 C9 -179.6(3) . . . . ? C1 N1 C5 C4 2.0(4) . . . . ? Cu1 N1 C5 C4 -178.8(2) . . . . ? C1 N1 C5 C6 179.9(2) . . . . ? Cu1 N1 C5 C6 -0.9(3) . . . . ? C3 C4 C5 N1 -1.8(4) . . . . ? C9 C4 C5 N1 178.1(3) . . . . ? C3 C4 C5 C6 -179.7(3) . . . . ? C9 C4 C5 C6 0.2(4) . . . . ? C12 N2 C6 C7 1.2(4) . . . . ? Cu1 N2 C6 C7 176.7(2) . . . . ? C12 N2 C6 C5 -176.8(2) . . . . ? Cu1 N2 C6 C5 -1.2(3) . . . . ? N1 C5 C6 N2 1.4(4) . . . . ? C4 C5 C6 N2 179.5(3) . . . . ? N1 C5 C6 C7 -176.6(2) . . . . ? C4 C5 C6 C7 1.4(4) . . . . ? N2 C6 C7 C10 -0.5(4) . . . . ? C5 C6 C7 C10 177.4(3) . . . . ? N2 C6 C7 C8 -179.8(3) . . . . ? C5 C6 C7 C8 -1.9(4) . . . . ? C6 C7 C8 C9 0.8(5) . . . . ? C10 C7 C8 C9 -178.5(3) . . . . ? C7 C8 C9 C4 0.9(6) . . . . ? C3 C4 C9 C8 178.5(4) . . . . ? C5 C4 C9 C8 -1.3(5) . . . . ? C6 C7 C10 C11 -0.1(5) . . . . ? C8 C7 C10 C11 179.2(3) . . . . ? C7 C10 C11 C12 0.0(5) . . . . ? C6 N2 C12 C11 -1.3(4) . . . . ? Cu1 N2 C12 C11 -176.0(2) . . . . ? C10 C11 C12 N2 0.8(5) . . . . ? Cu1 O1 C13 O2 -1.9(3) . . . . ? Cu1 O1 C13 C14 178.85(17) . . . . ? O2 C13 C14 C15 -170.2(3) . . . . ? O1 C13 C14 C15 9.1(4) . . . . ? O2 C13 C14 C24 8.6(4) . . . . ? O1 C13 C14 C24 -172.2(2) . . . . ? C24 C14 C15 C16 1.8(4) . . . . ? C13 C14 C15 C16 -179.4(2) . . . . ? C17 N3 C16 C15 24.8(4) . . . . ? C17 N3 C16 C23 -157.4(3) . . . . ? C14 C15 C16 N3 178.6(3) . . . . ? C14 C15 C16 C23 0.8(4) . . . . ? C16 N3 C17 C18 62.6(4) . . . . ? N3 C17 C18 C20 -132.0(4) . . . . ? N3 C17 C18 C19 47.4(4) . . . . ? C20 C18 C19 C20 -0.2(7) . . . 3_667 ? C17 C18 C19 C20 -179.6(4) . . . 3_667 ? C19 C18 C20 C19 0.2(7) . . . 3_667 ? C17 C18 C20 C19 179.6(4) . . . 3_667 ? Cu1 O4 C21 O3 2.7(4) 2_656 . . . ? Cu1 O4 C21 C22 179.23(16) 2_656 . . . ? O3 C21 C22 C23 162.1(3) . . . . ? O4 C21 C22 C23 -14.7(4) . . . . ? O3 C21 C22 C24 -14.2(4) . . . . ? O4 C21 C22 C24 169.0(2) . . . . ? C24 C22 C23 C16 2.4(4) . . . . ? C21 C22 C23 C16 -174.0(2) . . . . ? N3 C16 C23 C22 179.2(2) . . . . ? C15 C16 C23 C22 -2.9(4) . . . . ? C23 C22 C24 C14 0.3(4) . . . . ? C21 C22 C24 C14 176.7(2) . . . . ? C15 C14 C24 C22 -2.4(4) . . . . ? C13 C14 C24 C22 178.9(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 N3 H3A O2 0.86 2.26 2.935(3) 136.0 4_576 N3 H3A N1 0.86 2.59 3.200(3) 129.0 4_576 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.499 _refine_diff_density_min -0.560 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 937210' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 N3 Ni O6' _chemical_formula_weight 481.10 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' Ni Ni 0.3393 1.1124 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.130(4) _cell_length_b 9.703(5) _cell_length_c 15.619(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.37(3) _cell_angle_gamma 90.00 _cell_volume 4193(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 1.518 _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1976 _exptl_absorpt_coefficient_mu 0.971 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8371 _exptl_absorpt_correction_T_max 0.8681 _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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11159 _diffrn_reflns_av_R_equivalents 0.0925 _diffrn_reflns_av_sigmaI/netI 0.1142 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4107 _reflns_number_gt 2172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+16.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4107 _refine_ls_number_parameters 304 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.1319 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1569 _refine_ls_wR_factor_gt 0.1327 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.042 _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 O3W O 0.0245(4) 0.4701(9) 0.9416(8) 0.094(4) Uani 0.50 1 d P . . O2W O 0.0214(4) 0.4293(11) 0.1934(8) 0.099(4) Uani 0.50 1 d PU . . O1W O 0.04589(14) 0.7712(5) 0.3396(3) 0.0492(12) Uani 1 1 d D . . C2 C 0.0619(2) 0.8258(7) 0.5686(4) 0.0534(18) Uani 1 1 d . . . H2A H 0.0627 0.7300 0.5681 0.064 Uiso 1 1 calc R . . C3 C 0.0416(3) 0.8899(9) 0.6330(5) 0.066(2) Uani 1 1 d . . . H3A H 0.0293 0.8388 0.6744 0.079 Uiso 1 1 calc R . . C4 C 0.0404(3) 1.0299(10) 0.6333(5) 0.070(2) Uani 1 1 d . . . H4A H 0.0271 1.0767 0.6753 0.084 Uiso 1 1 calc R . . C5 C 0.0590(2) 1.1014(8) 0.5715(5) 0.060(2) Uani 1 1 d . . . H5A H 0.0586 1.1972 0.5715 0.072 Uiso 1 1 calc R . . C6 C 0.0787(2) 1.0300(7) 0.5084(4) 0.0475(17) Uani 1 1 d . . . C7 C 0.0998(2) 1.0979(7) 0.4393(4) 0.0443(16) Uani 1 1 d . . . C8 C 0.1026(3) 1.2373(7) 0.4309(6) 0.072(2) Uani 1 1 d . . . H8A H 0.0904 1.2956 0.4690 0.087 Uiso 1 1 calc R . . C9 C 0.1236(3) 1.2900(8) 0.3653(6) 0.078(2) Uani 1 1 d . . . H9A H 0.1273 1.3848 0.3606 0.094 Uiso 1 1 calc R . . C10 C 0.1390(3) 1.2051(8) 0.3079(5) 0.068(2) Uani 1 1 d . . . H10A H 0.1514 1.2404 0.2611 0.082 Uiso 1 1 calc R . . C11 C 0.1361(2) 1.0654(7) 0.3196(4) 0.0532(18) Uani 1 1 d . . . H11A H 0.1482 1.0066 0.2817 0.064 Uiso 1 1 calc R . . C12 C 0.1293(2) 0.6516(6) 0.2585(4) 0.0370(15) Uani 1 1 d . . . C13 C 0.16212(19) 0.5532(6) 0.2232(4) 0.0331(14) Uani 1 1 d . . . C14 C 0.1475(2) 0.4951(6) 0.1419(4) 0.0370(14) Uani 1 1 d . . . H14A H 0.1179 0.5197 0.1087 0.044 Uiso 1 1 calc R . . C15 C 0.1764(2) 0.4008(6) 0.1094(4) 0.0324(13) Uani 1 1 d . . . C16 C 0.2201(2) 0.3629(6) 0.1588(4) 0.0358(14) Uani 1 1 d . . . H16A H 0.2394 0.2986 0.1371 0.043 Uiso 1 1 calc R . . C17 C 0.23563(19) 0.4202(5) 0.2412(4) 0.0312(13) Uani 1 1 d . . . C18 C 0.20594(19) 0.5154(6) 0.2730(4) 0.0345(14) Uani 1 1 d . . . H18A H 0.2157 0.5536 0.3279 0.041 Uiso 1 1 calc R . . C19 C 0.1583(2) 0.3322(6) 0.0253(4) 0.0358(14) Uani 1 1 d . . . C20 C 0.2959(2) 0.4105(7) 0.3787(4) 0.0448(16) Uani 1 1 d . . . H20A H 0.2910 0.5076 0.3888 0.054 Uiso 1 1 calc R . . H20B H 0.3304 0.3927 0.3935 0.054 Uiso 1 1 calc R . . C21 C 0.27043(19) 0.3266(6) 0.4399(4) 0.0366(15) Uani 1 1 d . . . C22 C 0.2579(2) 0.1907(7) 0.4247(4) 0.0448(15) Uani 1 1 d . . . H22A H 0.2630 0.1491 0.3734 0.054 Uiso 1 1 calc R . . C23 C 0.2623(2) 0.3858(6) 0.5157(4) 0.0454(16) Uani 1 1 d . . . H23A H 0.2703 0.4777 0.5272 0.055 Uiso 1 1 calc R . . N1 N 0.08009(18) 0.8922(6) 0.5080(3) 0.0444(13) Uani 1 1 d . . . N2 N 0.11650(17) 1.0111(5) 0.3831(3) 0.0435(13) Uani 1 1 d . . . N3 N 0.28009(16) 0.3821(5) 0.2870(3) 0.0410(13) Uani 1 1 d . . . H3 H 0.2995 0.3391 0.2597 0.049 Uiso 1 1 calc R . . Ni1 Ni 0.11295(3) 0.80781(8) 0.41214(5) 0.0365(2) Uani 1 1 d D . . O1 O 0.14750(13) 0.7317(4) 0.3177(2) 0.0402(10) Uani 1 1 d . . . O2 O 0.08549(15) 0.6474(5) 0.2257(3) 0.0594(13) Uani 1 1 d . . . O3 O 0.12064(14) 0.3804(4) -0.0227(3) 0.0405(10) Uani 1 1 d . . . O4 O 0.17662(14) 0.2220(4) 0.0062(2) 0.0423(10) Uani 1 1 d . . . H1WB H 0.0453(10) 0.739(6) 0.2880(15) 0.051 Uiso 1 1 d D . . H1WA H 0.0250(9) 0.729(5) 0.361(2) 0.051 Uiso 1 1 d 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 O3W 0.108(9) 0.042(6) 0.159(12) 0.016(6) 0.101(8) 0.022(6) O2W 0.062(6) 0.096(7) 0.134(8) -0.064(6) 0.005(5) -0.013(5) O1W 0.043(3) 0.062(3) 0.043(3) -0.006(2) 0.008(2) 0.005(2) C2 0.061(4) 0.054(5) 0.049(4) 0.001(4) 0.021(4) 0.008(4) C3 0.066(5) 0.089(7) 0.047(5) 0.004(4) 0.023(4) 0.015(4) C4 0.069(5) 0.087(7) 0.057(5) -0.005(5) 0.021(4) 0.025(5) C5 0.065(5) 0.052(5) 0.064(5) -0.009(4) 0.014(4) 0.017(4) C6 0.041(4) 0.056(5) 0.043(4) -0.009(4) -0.002(3) 0.007(3) C7 0.047(4) 0.037(4) 0.049(4) -0.001(3) 0.008(3) 0.004(3) C8 0.087(6) 0.036(4) 0.099(7) -0.003(4) 0.029(5) 0.009(4) C9 0.112(7) 0.039(5) 0.088(7) 0.018(5) 0.030(6) -0.002(5) C10 0.076(5) 0.055(5) 0.072(6) 0.007(5) 0.012(4) -0.006(4) C11 0.059(5) 0.055(5) 0.048(4) 0.009(4) 0.016(4) -0.002(4) C12 0.036(4) 0.042(4) 0.034(4) 0.003(3) 0.008(3) 0.002(3) C13 0.037(3) 0.031(3) 0.033(3) 0.005(3) 0.010(3) 0.006(3) C14 0.035(3) 0.036(4) 0.039(4) -0.001(3) 0.002(3) 0.001(3) C15 0.037(3) 0.030(3) 0.030(3) 0.000(3) 0.007(3) -0.004(3) C16 0.042(4) 0.032(3) 0.033(3) 0.001(3) 0.005(3) 0.004(3) C17 0.038(3) 0.028(3) 0.028(3) 0.006(3) 0.006(3) -0.003(3) C18 0.039(3) 0.038(4) 0.029(3) 0.001(3) 0.012(3) -0.005(3) C19 0.044(4) 0.030(4) 0.034(4) 0.000(3) 0.008(3) -0.002(3) C20 0.045(4) 0.050(4) 0.036(4) -0.001(3) -0.002(3) 0.003(3) C21 0.033(3) 0.045(4) 0.030(3) -0.003(3) 0.000(3) 0.003(3) C22 0.057(4) 0.044(4) 0.035(4) -0.012(3) 0.012(3) -0.001(3) C23 0.062(4) 0.035(4) 0.040(4) -0.010(3) 0.011(3) -0.001(3) N1 0.050(3) 0.044(4) 0.040(3) 0.000(3) 0.012(3) 0.004(3) N2 0.044(3) 0.043(3) 0.041(3) 0.003(3) 0.003(3) 0.002(3) N3 0.041(3) 0.051(3) 0.030(3) 0.003(2) 0.004(2) 0.010(2) Ni1 0.0424(5) 0.0360(5) 0.0315(4) 0.0008(4) 0.0077(3) 0.0043(4) O1 0.041(2) 0.043(3) 0.037(2) -0.012(2) 0.0105(19) -0.0038(19) O2 0.042(3) 0.072(3) 0.060(3) -0.028(3) -0.001(2) 0.011(2) O3 0.044(2) 0.040(3) 0.035(2) -0.002(2) 0.002(2) 0.002(2) O4 0.054(3) 0.035(3) 0.037(2) -0.0049(19) 0.003(2) 0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1W Ni1 2.049(4) . ? O1W H1WB 0.860(18) . ? O1W H1WA 0.829(18) . ? C2 N1 1.321(7) . ? C2 C3 1.390(9) . ? C2 H2A 0.9300 . ? C3 C4 1.359(10) . ? C3 H3A 0.9300 . ? C4 C5 1.367(10) . ? C4 H4A 0.9300 . ? C5 C6 1.398(9) . ? C5 H5A 0.9300 . ? C6 N1 1.338(8) . ? C6 C7 1.477(9) . ? C7 N2 1.359(7) . ? C7 C8 1.363(9) . ? C8 C9 1.371(10) . ? C8 H8A 0.9300 . ? C9 C10 1.346(10) . ? C9 H9A 0.9300 . ? C10 C11 1.373(9) . ? C10 H10A 0.9300 . ? C11 N2 1.327(7) . ? C11 H11A 0.9300 . ? C12 O1 1.246(6) . ? C12 O2 1.246(6) . ? C12 C13 1.500(7) . ? C13 C18 1.383(7) . ? C13 C14 1.384(7) . ? C14 C15 1.381(7) . ? C14 H14A 0.9300 . ? C15 C16 1.378(7) . ? C15 C19 1.479(7) . ? C16 C17 1.398(7) . ? C16 H16A 0.9300 . ? C17 N3 1.375(7) . ? C17 C18 1.395(7) . ? C18 H18A 0.9300 . ? C19 O4 1.247(6) . ? C19 O3 1.271(6) . ? C19 Ni1 2.405(6) 6_565 ? C20 N3 1.448(7) . ? C20 C21 1.529(8) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C23 1.371(8) . ? C21 C22 1.375(8) . ? C22 C23 1.389(8) 7_556 ? C22 H22A 0.9300 . ? C23 C22 1.389(8) 7_556 ? C23 H23A 0.9300 . ? N1 Ni1 2.066(5) . ? N2 Ni1 2.030(5) . ? N3 H3 0.8600 . ? Ni1 O1 2.045(4) . ? Ni1 O3 2.082(4) 6_566 ? Ni1 O4 2.122(4) 6_566 ? Ni1 C19 2.405(6) 6_566 ? O3 Ni1 2.082(4) 6_565 ? O4 Ni1 2.122(4) 6_565 ? 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 Ni1 O1W H1WB 116(2) . . ? Ni1 O1W H1WA 121(2) . . ? H1WB O1W H1WA 108(3) . . ? N1 C2 C3 124.3(7) . . ? N1 C2 H2A 117.9 . . ? C3 C2 H2A 117.9 . . ? C4 C3 C2 117.6(7) . . ? C4 C3 H3A 121.2 . . ? C2 C3 H3A 121.2 . . ? C3 C4 C5 119.5(7) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C4 C5 C6 119.8(7) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? N1 C6 C5 120.9(7) . . ? N1 C6 C7 115.2(6) . . ? C5 C6 C7 123.8(7) . . ? N2 C7 C8 121.4(6) . . ? N2 C7 C6 115.3(6) . . ? C8 C7 C6 123.4(7) . . ? C7 C8 C9 118.9(7) . . ? C7 C8 H8A 120.6 . . ? C9 C8 H8A 120.6 . . ? C10 C9 C8 120.2(7) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? C9 C10 C11 118.7(7) . . ? C9 C10 H10A 120.6 . . ? C11 C10 H10A 120.6 . . ? N2 C11 C10 122.4(7) . . ? N2 C11 H11A 118.8 . . ? C10 C11 H11A 118.8 . . ? O1 C12 O2 124.7(5) . . ? O1 C12 C13 118.1(5) . . ? O2 C12 C13 117.2(5) . . ? C18 C13 C14 119.7(5) . . ? C18 C13 C12 120.6(5) . . ? C14 C13 C12 119.7(5) . . ? C15 C14 C13 120.7(5) . . ? C15 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C16 C15 C14 119.8(5) . . ? C16 C15 C19 120.5(5) . . ? C14 C15 C19 119.5(5) . . ? C15 C16 C17 120.6(5) . . ? C15 C16 H16A 119.7 . . ? C17 C16 H16A 119.7 . . ? N3 C17 C18 122.7(5) . . ? N3 C17 C16 118.4(5) . . ? C18 C17 C16 118.9(5) . . ? C13 C18 C17 120.4(5) . . ? C13 C18 H18A 119.8 . . ? C17 C18 H18A 119.8 . . ? O4 C19 O3 120.7(5) . . ? O4 C19 C15 120.5(5) . . ? O3 C19 C15 118.5(5) . . ? O4 C19 Ni1 61.8(3) . 6_565 ? O3 C19 Ni1 59.9(3) . 6_565 ? C15 C19 Ni1 163.7(4) . 6_565 ? N3 C20 C21 114.9(5) . . ? N3 C20 H20A 108.5 . . ? C21 C20 H20A 108.5 . . ? N3 C20 H20B 108.5 . . ? C21 C20 H20B 108.5 . . ? H20A C20 H20B 107.5 . . ? C23 C21 C22 118.3(6) . . ? C23 C21 C20 119.1(6) . . ? C22 C21 C20 122.5(5) . . ? C21 C22 C23 121.3(6) . 7_556 ? C21 C22 H22A 119.4 . . ? C23 C22 H22A 119.4 7_556 . ? C21 C23 C22 120.5(6) . 7_556 ? C21 C23 H23A 119.8 . . ? C22 C23 H23A 119.8 7_556 . ? C2 N1 C6 117.9(6) . . ? C2 N1 Ni1 127.4(5) . . ? C6 N1 Ni1 114.6(4) . . ? C11 N2 C7 118.3(6) . . ? C11 N2 Ni1 126.6(5) . . ? C7 N2 Ni1 114.9(4) . . ? C17 N3 C20 123.6(5) . . ? C17 N3 H3 118.2 . . ? C20 N3 H3 118.2 . . ? N2 Ni1 O1 98.11(19) . . ? N2 Ni1 O1W 97.05(19) . . ? O1 Ni1 O1W 92.78(16) . . ? N2 Ni1 N1 79.8(2) . . ? O1 Ni1 N1 177.45(19) . . ? O1W Ni1 N1 88.96(18) . . ? N2 Ni1 O3 162.91(18) . 6_566 ? O1 Ni1 O3 90.84(16) . 6_566 ? O1W Ni1 O3 97.02(17) . 6_566 ? N1 Ni1 O3 90.79(19) . 6_566 ? N2 Ni1 O4 102.56(17) . 6_566 ? O1 Ni1 O4 89.91(15) . 6_566 ? O1W Ni1 O4 159.62(17) . 6_566 ? N1 Ni1 O4 89.10(18) . 6_566 ? O3 Ni1 O4 62.73(15) 6_566 6_566 ? N2 Ni1 C19 132.2(2) . 6_566 ? O1 Ni1 C19 93.93(18) . 6_566 ? O1W Ni1 C19 128.4(2) . 6_566 ? N1 Ni1 C19 86.4(2) . 6_566 ? O3 Ni1 C19 31.89(16) 6_566 6_566 ? O4 Ni1 C19 31.19(16) 6_566 6_566 ? C12 O1 Ni1 125.1(4) . . ? C19 O3 Ni1 88.2(3) . 6_565 ? C19 O4 Ni1 87.1(3) . 6_565 ? 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 N1 C2 C3 C4 0.2(11) . . . . ? C2 C3 C4 C5 -0.2(11) . . . . ? C3 C4 C5 C6 0.5(11) . . . . ? C4 C5 C6 N1 -0.7(10) . . . . ? C4 C5 C6 C7 -179.7(6) . . . . ? N1 C6 C7 N2 1.9(8) . . . . ? C5 C6 C7 N2 -179.1(6) . . . . ? N1 C6 C7 C8 -178.3(6) . . . . ? C5 C6 C7 C8 0.7(10) . . . . ? N2 C7 C8 C9 -1.4(11) . . . . ? C6 C7 C8 C9 178.9(7) . . . . ? C7 C8 C9 C10 3.3(13) . . . . ? C8 C9 C10 C11 -4.2(12) . . . . ? C9 C10 C11 N2 3.3(11) . . . . ? O1 C12 C13 C18 23.5(8) . . . . ? O2 C12 C13 C18 -156.9(6) . . . . ? O1 C12 C13 C14 -159.5(5) . . . . ? O2 C12 C13 C14 20.2(8) . . . . ? C18 C13 C14 C15 -0.7(9) . . . . ? C12 C13 C14 C15 -177.8(5) . . . . ? C13 C14 C15 C16 0.8(9) . . . . ? C13 C14 C15 C19 175.2(5) . . . . ? C14 C15 C16 C17 -0.7(8) . . . . ? C19 C15 C16 C17 -175.2(5) . . . . ? C15 C16 C17 N3 -178.2(5) . . . . ? C15 C16 C17 C18 0.7(8) . . . . ? C14 C13 C18 C17 0.7(8) . . . . ? C12 C13 C18 C17 177.7(5) . . . . ? N3 C17 C18 C13 178.1(5) . . . . ? C16 C17 C18 C13 -0.7(8) . . . . ? C16 C15 C19 O4 14.7(8) . . . . ? C14 C15 C19 O4 -159.8(5) . . . . ? C16 C15 C19 O3 -172.2(5) . . . . ? C14 C15 C19 O3 13.3(8) . . . . ? C16 C15 C19 Ni1 107.9(15) . . . 6_565 ? C14 C15 C19 Ni1 -66.5(17) . . . 6_565 ? N3 C20 C21 C23 -146.3(5) . . . . ? N3 C20 C21 C22 37.9(8) . . . . ? C23 C21 C22 C23 -0.4(10) . . . 7_556 ? C20 C21 C22 C23 175.5(5) . . . 7_556 ? C22 C21 C23 C22 0.4(10) . . . 7_556 ? C20 C21 C23 C22 -175.7(5) . . . 7_556 ? C3 C2 N1 C6 -0.4(10) . . . . ? C3 C2 N1 Ni1 177.8(5) . . . . ? C5 C6 N1 C2 0.7(9) . . . . ? C7 C6 N1 C2 179.7(6) . . . . ? C5 C6 N1 Ni1 -177.8(5) . . . . ? C7 C6 N1 Ni1 1.3(7) . . . . ? C10 C11 N2 C7 -1.4(9) . . . . ? C10 C11 N2 Ni1 -176.5(5) . . . . ? C8 C7 N2 C11 0.4(9) . . . . ? C6 C7 N2 C11 -179.8(6) . . . . ? C8 C7 N2 Ni1 176.1(5) . . . . ? C6 C7 N2 Ni1 -4.2(7) . . . . ? C18 C17 N3 C20 14.7(8) . . . . ? C16 C17 N3 C20 -166.6(5) . . . . ? C21 C20 N3 C17 70.6(7) . . . . ? C11 N2 Ni1 O1 0.5(5) . . . . ? C7 N2 Ni1 O1 -174.8(4) . . . . ? C11 N2 Ni1 O1W -93.4(5) . . . . ? C7 N2 Ni1 O1W 91.4(4) . . . . ? C11 N2 Ni1 N1 178.9(6) . . . . ? C7 N2 Ni1 N1 3.7(4) . . . . ? C11 N2 Ni1 O3 121.4(7) . . . 6_566 ? C7 N2 Ni1 O3 -53.8(8) . . . 6_566 ? C11 N2 Ni1 O4 92.2(5) . . . 6_566 ? C7 N2 Ni1 O4 -83.1(4) . . . 6_566 ? C11 N2 Ni1 C19 103.3(5) . . . 6_566 ? C7 N2 Ni1 C19 -71.9(5) . . . 6_566 ? C2 N1 Ni1 N2 179.0(6) . . . . ? C6 N1 Ni1 N2 -2.7(4) . . . . ? C2 N1 Ni1 O1 -145(4) . . . . ? C6 N1 Ni1 O1 33(4) . . . . ? C2 N1 Ni1 O1W 81.7(6) . . . . ? C6 N1 Ni1 O1W -100.0(4) . . . . ? C2 N1 Ni1 O3 -15.3(5) . . . 6_566 ? C6 N1 Ni1 O3 163.0(4) . . . 6_566 ? C2 N1 Ni1 O4 -78.0(5) . . . 6_566 ? C6 N1 Ni1 O4 100.3(4) . . . 6_566 ? C2 N1 Ni1 C19 -46.9(5) . . . 6_566 ? C6 N1 Ni1 C19 131.4(4) . . . 6_566 ? O2 C12 O1 Ni1 29.9(8) . . . . ? C13 C12 O1 Ni1 -150.4(4) . . . . ? N2 Ni1 O1 C12 -118.8(5) . . . . ? O1W Ni1 O1 C12 -21.2(5) . . . . ? N1 Ni1 O1 C12 -154(4) . . . . ? O3 Ni1 O1 C12 75.8(5) 6_566 . . . ? O4 Ni1 O1 C12 138.6(5) 6_566 . . . ? C19 Ni1 O1 C12 107.6(5) 6_566 . . . ? O4 C19 O3 Ni1 11.7(5) . . . 6_565 ? C15 C19 O3 Ni1 -161.4(5) . . . 6_565 ? O3 C19 O4 Ni1 -11.5(5) . . . 6_565 ? C15 C19 O4 Ni1 161.4(5) . . . 6_565 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.373 _refine_diff_density_min -0.608 _refine_diff_density_rms 0.094 _database_code_depnum_ccdc_archive 'CCDC 937211' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 N3 O5 Zn' _chemical_formula_weight 493.78 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.523(4) _cell_length_b 16.289(7) _cell_length_c 11.710(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.087(7) _cell_angle_gamma 90.00 _cell_volume 2006.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 _exptl_absorpt_coefficient_mu 1.269 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.808 _exptl_absorpt_correction_T_max 0.859 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10046 _diffrn_reflns_av_R_equivalents 0.1338 _diffrn_reflns_av_sigmaI/netI 0.1154 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3528 _reflns_number_gt 2400 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0491P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3528 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _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 Zn1 Zn 0.22557(4) 0.04312(3) 0.04764(4) 0.03111(19) Uani 1 1 d . . . N3 N 0.3788(3) 0.0357(2) 0.1712(3) 0.0326(8) Uani 1 1 d . . . C6 C 0.0760(4) 0.3060(2) -0.3967(3) 0.0315(10) Uani 1 1 d . . . H6 H 0.0409 0.3395 -0.4533 0.038 Uiso 1 1 calc R . . C7 C 0.1916(4) 0.3282(2) -0.3457(4) 0.0307(10) Uani 1 1 d . . . C9 C 0.1734(4) 0.2101(3) -0.2204(3) 0.0292(10) Uani 1 1 d . . . C12 C 0.2227(4) 0.1577(3) -0.1241(3) 0.0319(10) Uani 1 1 d . . . C10 C 0.0616(4) 0.1877(3) -0.2766(4) 0.0332(10) Uani 1 1 d . . . H10 H 0.0195 0.1403 -0.2543 0.040 Uiso 1 1 calc R . . C5 C 0.0114(4) 0.2347(3) -0.3653(4) 0.0312(10) Uani 1 1 d . . . N1 N -0.1008(4) 0.2146(2) -0.4220(4) 0.0411(10) Uani 1 1 d . . . C8 C 0.2405(4) 0.2796(2) -0.2560(3) 0.0297(10) Uani 1 1 d . . . H8 H 0.3172 0.2936 -0.2202 0.036 Uiso 1 1 calc R . . N2 N 0.1924(3) 0.1467(2) 0.1640(3) 0.0361(9) Uani 1 1 d . . . C16 C 0.2687(4) 0.2119(3) 0.3388(4) 0.0429(12) Uani 1 1 d . . . C21 C 0.3745(4) 0.0903(3) 0.2589(4) 0.0359(11) Uani 1 1 d . . . C2 C -0.0750(4) 0.0650(3) -0.4600(4) 0.0390(11) Uani 1 1 d . . . C17 C 0.2754(4) 0.1511(3) 0.2537(4) 0.0347(11) Uani 1 1 d . . . C15 C 0.1733(5) 0.2709(3) 0.3259(4) 0.0516(13) Uani 1 1 d . . . H15 H 0.1673 0.3135 0.3784 0.062 Uiso 1 1 calc R . . C4 C -0.1564(4) 0.1339(3) -0.4160(4) 0.0439(12) Uani 1 1 d . . . H4A H -0.2360 0.1343 -0.4592 0.053 Uiso 1 1 calc R . . H4B H -0.1761 0.1225 -0.3370 0.053 Uiso 1 1 calc R . . C20 C 0.4623(4) 0.0916(3) 0.3505(4) 0.0394(11) Uani 1 1 d . . . C14 C 0.0881(5) 0.2661(3) 0.2356(5) 0.0512(13) Uani 1 1 d . . . H14 H 0.0231 0.3045 0.2271 0.061 Uiso 1 1 calc R . . C19 C 0.4494(5) 0.1529(3) 0.4376(4) 0.0567(15) Uani 1 1 d . . . H19 H 0.5055 0.1528 0.5000 0.068 Uiso 1 1 calc R . . C18 C 0.3580(5) 0.2105(3) 0.4308(4) 0.0581(15) Uani 1 1 d . . . H18 H 0.3534 0.2502 0.4876 0.070 Uiso 1 1 calc R . . C13 C 0.1014(4) 0.2030(3) 0.1575(4) 0.0429(12) Uani 1 1 d . . . H2 H 0.0431 0.1999 0.0969 0.052 Uiso 1 1 calc R . . C3 C -0.0792(5) -0.0116(3) -0.4110(5) 0.0601(15) Uani 1 1 d . . . H3 H -0.1326 -0.0204 -0.3498 0.072 Uiso 1 1 calc R . . C1 C 0.0067(5) 0.0750(3) -0.5501(4) 0.0605(15) Uani 1 1 d . . . H1 H 0.0124 0.1261 -0.5851 0.073 Uiso 1 1 calc R . . O1 O 0.2092(3) 0.44300(18) -0.4675(2) 0.0404(8) Uani 1 1 d . . . OW O 0.0718(3) -0.0115(2) 0.1217(3) 0.0368(8) Uani 1 1 d . . . O3 O 0.3363(3) 0.16249(18) -0.0913(3) 0.0413(8) Uani 1 1 d . . . O4 O 0.1438(3) 0.10896(17) -0.0779(2) 0.0402(8) Uani 1 1 d . . . O2 O 0.3719(3) 0.4131(2) -0.3497(3) 0.0633(11) Uani 1 1 d . . . C11 C 0.2649(4) 0.4012(3) -0.3902(4) 0.0334(10) Uani 1 1 d . . . C22 C 0.5574(5) 0.0323(3) 0.3507(4) 0.0501(13) Uani 1 1 d . . . H22 H 0.6164 0.0300 0.4108 0.060 Uiso 1 1 calc R . . C24 C 0.4731(4) -0.0183(3) 0.1755(4) 0.0440(12) Uani 1 1 d . . . H24 H 0.4789 -0.0560 0.1162 0.053 Uiso 1 1 calc R . . C23 C 0.5640(5) -0.0221(3) 0.2635(5) 0.0530(14) Uani 1 1 d . . . H23 H 0.6282 -0.0613 0.2624 0.064 Uiso 1 1 calc R . . H13 H -0.116(4) 0.245(2) -0.484(4) 0.032(12) Uiso 1 1 d . . . HWB H 0.046(4) -0.046(3) 0.090(4) 0.033(16) Uiso 1 1 d . . . HWA H 0.008(6) 0.026(4) 0.130(5) 0.08(2) 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 Zn1 0.0320(3) 0.0320(3) 0.0294(3) 0.0006(2) 0.0021(2) 0.0017(2) N3 0.034(2) 0.036(2) 0.028(2) -0.0064(17) 0.0080(16) -0.0066(17) C6 0.037(2) 0.033(2) 0.024(2) 0.0026(19) -0.0008(19) 0.004(2) C7 0.031(2) 0.030(2) 0.031(2) 0.000(2) 0.001(2) 0.0017(19) C9 0.031(2) 0.033(2) 0.023(2) -0.0011(19) 0.0023(19) 0.0044(19) C12 0.042(3) 0.032(2) 0.022(2) -0.0045(19) 0.000(2) 0.002(2) C10 0.033(2) 0.030(2) 0.037(3) 0.001(2) 0.001(2) -0.0044(19) C5 0.028(2) 0.034(2) 0.031(2) -0.002(2) -0.001(2) 0.0023(19) N1 0.041(2) 0.036(2) 0.046(3) 0.003(2) -0.016(2) -0.0032(18) C8 0.029(2) 0.031(2) 0.028(2) -0.0018(19) 0.0008(19) -0.0022(19) N2 0.036(2) 0.037(2) 0.036(2) 0.0036(17) 0.0028(18) 0.0011(17) C16 0.045(3) 0.047(3) 0.037(3) -0.004(2) 0.004(2) -0.001(2) C21 0.037(3) 0.040(3) 0.031(3) 0.001(2) 0.009(2) -0.007(2) C2 0.038(3) 0.043(3) 0.036(3) -0.002(2) -0.004(2) -0.007(2) C17 0.033(2) 0.040(3) 0.031(3) 0.000(2) 0.009(2) -0.005(2) C15 0.056(3) 0.052(3) 0.047(3) -0.008(3) 0.012(3) 0.000(3) C4 0.034(2) 0.044(3) 0.054(3) -0.004(2) -0.004(2) -0.005(2) C20 0.042(3) 0.046(3) 0.031(3) -0.001(2) 0.000(2) 0.000(2) C14 0.050(3) 0.047(3) 0.057(3) -0.001(3) 0.009(3) 0.005(2) C19 0.060(3) 0.072(4) 0.038(3) -0.018(3) -0.012(3) 0.009(3) C18 0.063(4) 0.071(4) 0.041(3) -0.023(3) -0.003(3) 0.011(3) C13 0.039(3) 0.042(3) 0.048(3) 0.002(2) 0.003(2) -0.003(2) C3 0.080(4) 0.044(3) 0.057(3) 0.004(3) 0.038(3) -0.006(3) C1 0.082(4) 0.046(3) 0.054(3) 0.010(3) 0.023(3) 0.002(3) O1 0.0416(18) 0.0437(19) 0.0357(19) 0.0129(15) -0.0035(15) -0.0061(15) OW 0.0334(19) 0.039(2) 0.039(2) -0.0052(17) 0.0034(15) -0.0044(17) O3 0.0374(18) 0.0487(19) 0.0374(19) -0.0002(15) -0.0113(15) 0.0054(15) O4 0.0490(19) 0.0369(18) 0.0345(18) 0.0114(14) -0.0078(15) -0.0103(15) O2 0.0336(19) 0.065(2) 0.091(3) 0.036(2) -0.014(2) -0.0149(17) C11 0.033(3) 0.036(3) 0.031(3) 0.004(2) 0.005(2) -0.001(2) C22 0.042(3) 0.067(4) 0.041(3) 0.000(3) -0.004(2) 0.003(3) C24 0.039(3) 0.047(3) 0.046(3) -0.008(2) 0.005(2) 0.003(2) C23 0.051(3) 0.056(3) 0.052(3) -0.003(3) -0.007(3) 0.008(3) _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 Zn1 O4 2.001(3) . ? Zn1 O1 2.009(3) 2_544 ? Zn1 OW 2.053(3) . ? Zn1 N3 2.150(3) . ? Zn1 N2 2.200(4) . ? N3 C24 1.327(5) . ? N3 C21 1.360(5) . ? C6 C7 1.393(5) . ? C6 C5 1.398(6) . ? C6 H6 0.9300 . ? C7 C8 1.405(5) . ? C7 C11 1.516(6) . ? C9 C10 1.385(5) . ? C9 C8 1.402(6) . ? C9 C12 1.500(6) . ? C12 O3 1.251(5) . ? C12 O4 1.276(5) . ? C10 C5 1.387(6) . ? C10 H10 0.9300 . ? C5 N1 1.383(5) . ? N1 C4 1.441(6) . ? N1 H13 0.89(4) . ? C8 H8 0.9300 . ? N2 C13 1.329(5) . ? N2 C17 1.355(5) . ? C16 C15 1.397(6) . ? C16 C17 1.407(6) . ? C16 C18 1.416(6) . ? C21 C20 1.403(6) . ? C21 C17 1.439(6) . ? C2 C3 1.374(7) . ? C2 C1 1.383(7) . ? C2 C4 1.509(6) . ? C15 C14 1.375(6) . ? C15 H15 0.9300 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C20 C22 1.390(6) . ? C20 C19 1.436(7) . ? C14 C13 1.385(7) . ? C14 H14 0.9300 . ? C19 C18 1.345(7) . ? C19 H19 0.9300 . ? C18 H18 0.9300 . ? C13 H2 0.9300 . ? C3 C1 1.368(7) 3_554 ? C3 H3 0.9300 . ? C1 C3 1.368(7) 3_554 ? C1 H1 0.9300 . ? O1 C11 1.268(5) . ? O1 Zn1 2.009(3) 2_554 ? OW HWB 0.72(4) . ? OW HWA 0.91(6) . ? O2 C11 1.229(5) . ? C22 C23 1.355(7) . ? C22 H22 0.9300 . ? C24 C23 1.394(6) . ? C24 H24 0.9300 . ? C23 H23 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Zn1 O1 103.76(12) . 2_544 ? O4 Zn1 OW 102.19(13) . . ? O1 Zn1 OW 97.17(15) 2_544 . ? O4 Zn1 N3 146.22(12) . . ? O1 Zn1 N3 90.59(12) 2_544 . ? OW Zn1 N3 106.18(13) . . ? O4 Zn1 N2 88.46(13) . . ? O1 Zn1 N2 166.20(12) 2_544 . ? OW Zn1 N2 86.29(15) . . ? N3 Zn1 N2 75.62(13) . . ? C24 N3 C21 116.2(4) . . ? C24 N3 Zn1 127.8(3) . . ? C21 N3 Zn1 115.9(3) . . ? C7 C6 C5 121.9(4) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C7 C8 118.6(4) . . ? C6 C7 C11 120.2(4) . . ? C8 C7 C11 121.2(4) . . ? C10 C9 C8 120.0(4) . . ? C10 C9 C12 119.1(4) . . ? C8 C9 C12 120.9(4) . . ? O3 C12 O4 122.3(4) . . ? O3 C12 C9 120.7(4) . . ? O4 C12 C9 117.0(4) . . ? C9 C10 C5 121.2(4) . . ? C9 C10 H10 119.4 . . ? C5 C10 H10 119.4 . . ? N1 C5 C10 122.6(4) . . ? N1 C5 C6 119.1(4) . . ? C10 C5 C6 118.4(4) . . ? C5 N1 C4 122.5(4) . . ? C5 N1 H13 114(3) . . ? C4 N1 H13 118(3) . . ? C9 C8 C7 119.8(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C13 N2 C17 117.4(4) . . ? C13 N2 Zn1 128.1(3) . . ? C17 N2 Zn1 114.5(3) . . ? C15 C16 C17 117.0(4) . . ? C15 C16 C18 124.0(4) . . ? C17 C16 C18 119.1(4) . . ? N3 C21 C20 123.8(4) . . ? N3 C21 C17 117.0(4) . . ? C20 C21 C17 119.2(4) . . ? C3 C2 C1 116.8(5) . . ? C3 C2 C4 120.6(4) . . ? C1 C2 C4 122.6(4) . . ? N2 C17 C16 123.2(4) . . ? N2 C17 C21 116.8(4) . . ? C16 C17 C21 120.0(4) . . ? C14 C15 C16 120.0(5) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? N1 C4 C2 115.3(4) . . ? N1 C4 H4A 108.4 . . ? C2 C4 H4A 108.4 . . ? N1 C4 H4B 108.4 . . ? C2 C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? C22 C20 C21 117.1(4) . . ? C22 C20 C19 124.0(4) . . ? C21 C20 C19 119.0(4) . . ? C15 C14 C13 118.5(5) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C18 C19 C20 121.3(4) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? C19 C18 C16 121.4(5) . . ? C19 C18 H18 119.3 . . ? C16 C18 H18 119.3 . . ? N2 C13 C14 123.8(4) . . ? N2 C13 H2 118.1 . . ? C14 C13 H2 118.1 . . ? C1 C3 C2 121.6(5) 3_554 . ? C1 C3 H3 119.2 3_554 . ? C2 C3 H3 119.2 . . ? C3 C1 C2 121.6(5) 3_554 . ? C3 C1 H1 119.2 3_554 . ? C2 C1 H1 119.2 . . ? C11 O1 Zn1 127.7(3) . 2_554 ? Zn1 OW HWB 114(4) . . ? Zn1 OW HWA 110(4) . . ? HWB OW HWA 108(5) . . ? C12 O4 Zn1 111.8(3) . . ? O2 C11 O1 126.8(4) . . ? O2 C11 C7 117.4(4) . . ? O1 C11 C7 115.8(4) . . ? C23 C22 C20 120.0(5) . . ? C23 C22 H22 120.0 . . ? C20 C22 H22 120.0 . . ? N3 C24 C23 124.0(4) . . ? N3 C24 H24 118.0 . . ? C23 C24 H24 118.0 . . ? C22 C23 C24 118.9(5) . . ? C22 C23 H23 120.5 . . ? C24 C23 H23 120.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.955 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.102 _database_code_depnum_ccdc_archive 'CCDC 959347' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d:\3/4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H34 Cu N6 O8' _chemical_formula_weight 838.31 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 'Pn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 11.4050(8) _cell_length_b 11.1560(8) _cell_length_c 15.1930(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.2110(10) _cell_angle_gamma 90.00 _cell_volume 1927.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2762 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 23.00 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 866 _exptl_absorpt_coefficient_mu 0.631 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8948 _exptl_absorpt_correction_T_max 0.9281 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10457 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7069 _reflns_number_gt 5409 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0056P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.008(9) _refine_ls_number_reflns 7069 _refine_ls_number_parameters 534 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.0786 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 O1 O -0.2341(2) 1.0848(2) 0.72641(16) 0.0585(7) Uani 1 1 d . . . O2 O -0.2463(3) 1.1321(3) 0.58403(19) 0.0693(8) Uani 1 1 d . . . O3 O 0.0216(3) 0.9132(3) 0.38926(19) 0.0974(12) Uani 1 1 d . . . O4 O 0.1110(2) 0.7507(2) 0.44220(15) 0.0550(7) Uani 1 1 d . . . H4 H 0.1356 0.7488 0.3928 0.083 Uiso 1 1 calc R . . O5 O 0.9686(3) 0.6388(2) 1.0430(2) 0.0833(9) Uani 1 1 d . . . H5 H 1.0296 0.6242 1.0730 0.125 Uiso 1 1 calc R . . O6 O 0.9764(3) 0.4468(2) 1.01010(18) 0.0715(9) Uani 1 1 d . . . O7 O 0.6787(3) 0.2848(2) 0.78061(18) 0.0493(6) Uani 1 1 d . . . O8 O 0.6210(2) 0.4146(2) 0.67452(18) 0.0660(8) Uani 1 1 d . . . C1 C -0.2088(3) 1.0686(3) 0.6442(3) 0.0487(9) Uani 1 1 d . . . C2 C -0.1286(3) 0.9653(3) 0.6309(2) 0.0432(8) Uani 1 1 d . . . C3 C -0.0931(3) 0.8896(3) 0.6996(2) 0.0446(8) Uani 1 1 d . . . H3 H -0.1223 0.9016 0.7545 0.054 Uiso 1 1 calc R . . C4 C -0.0148(3) 0.7959(3) 0.6890(2) 0.0403(9) Uani 1 1 d . . . C5 C 0.0273(3) 0.7805(3) 0.6054(2) 0.0406(8) Uani 1 1 d . . . H5A H 0.0793 0.7183 0.5962 0.049 Uiso 1 1 calc R . . C6 C -0.0073(3) 0.8564(3) 0.5362(2) 0.0406(8) Uani 1 1 d . . . C7 C -0.0857(3) 0.9483(3) 0.5484(2) 0.0446(8) Uani 1 1 d . . . H7 H -0.1096 0.9987 0.5017 0.053 Uiso 1 1 calc R . . C8 C 0.0404(3) 0.8427(4) 0.4479(2) 0.0486(9) Uani 1 1 d . . . C9 C 0.1117(3) 0.6347(3) 0.7587(3) 0.0545(10) Uani 1 1 d . . . H9A H 0.0974 0.5836 0.7073 0.065 Uiso 1 1 calc R . . H9B H 0.1089 0.5845 0.8106 0.065 Uiso 1 1 calc R . . C10 C 0.2340(3) 0.6878(3) 0.7575(3) 0.0496(10) Uani 1 1 d . . . C11 C 0.3009(3) 0.6710(3) 0.6871(2) 0.0509(9) Uani 1 1 d . . . H11 H 0.2716 0.6253 0.6392 0.061 Uiso 1 1 calc R . . C12 C 0.4120(3) 0.7215(3) 0.6868(2) 0.0524(9) Uani 1 1 d . . . H12 H 0.4558 0.7098 0.6382 0.063 Uiso 1 1 calc R . . C13 C 0.4587(3) 0.7883(3) 0.7566(2) 0.0498(9) Uani 1 1 d . . . C14 C 0.3920(4) 0.8043(4) 0.8280(3) 0.0616(12) Uani 1 1 d . . . H14 H 0.4220 0.8496 0.8758 0.074 Uiso 1 1 calc R . . C15 C 0.2812(3) 0.7539(3) 0.8293(3) 0.0588(11) Uani 1 1 d . . . H15 H 0.2381 0.7643 0.8783 0.071 Uiso 1 1 calc R . . C16 C 0.5802(3) 0.8457(3) 0.7546(3) 0.0603(10) Uani 1 1 d . . . H16A H 0.6140 0.8212 0.7007 0.072 Uiso 1 1 calc R . . H16B H 0.5707 0.9320 0.7524 0.072 Uiso 1 1 calc R . . C17 C 0.7102(3) 0.7033(3) 0.8404(2) 0.0400(8) Uani 1 1 d . . . C18 C 0.7974(3) 0.6834(3) 0.9086(2) 0.0396(8) Uani 1 1 d . . . H18 H 0.8256 0.7473 0.9433 0.048 Uiso 1 1 calc R . . C19 C 0.8421(3) 0.5695(3) 0.9248(2) 0.0367(7) Uani 1 1 d . . . C20 C 0.7987(3) 0.4728(3) 0.8741(2) 0.0373(8) Uani 1 1 d . . . H20 H 0.8251 0.3955 0.8872 0.045 Uiso 1 1 calc R . . C21 C 0.7163(2) 0.4925(3) 0.80437(19) 0.0326(7) Uani 1 1 d . . . C22 C 0.6753(3) 0.6076(3) 0.7864(2) 0.0369(8) Uani 1 1 d . . . H22 H 0.6235 0.6209 0.7372 0.044 Uiso 1 1 calc R . . C23 C 0.6678(3) 0.3897(3) 0.7484(2) 0.0389(8) Uani 1 1 d . . . C24 C 0.9359(3) 0.5437(4) 0.9965(2) 0.0432(9) Uani 1 1 d . . . C25 C 0.1345(4) 0.3562(4) 0.6008(3) 0.0611(12) Uani 1 1 d . . . H25 H 0.2151 0.3462 0.5979 0.073 Uiso 1 1 calc R . . C26 C 0.0750(3) 0.4224(4) 0.5367(3) 0.0580(12) Uani 1 1 d . . . H26 H 0.1151 0.4568 0.4919 0.070 Uiso 1 1 calc R . . C27 C -0.0447(3) 0.4383(3) 0.5384(2) 0.0416(8) Uani 1 1 d . . . C28 C -0.0964(3) 0.3846(4) 0.6061(3) 0.0773(14) Uani 1 1 d . . . H28 H -0.1770 0.3923 0.6101 0.093 Uiso 1 1 calc R . . C29 C -0.0315(4) 0.3199(4) 0.6680(3) 0.0741(14) Uani 1 1 d . . . H29 H -0.0705 0.2845 0.7129 0.089 Uiso 1 1 calc R . . C30 C -0.1118(3) 0.5129(3) 0.4729(2) 0.0441(9) Uani 1 1 d . . . C31 C -0.2045(4) 0.5822(4) 0.4971(3) 0.0720(14) Uani 1 1 d . . . H31 H -0.2273 0.5791 0.5545 0.086 Uiso 1 1 calc R . . C32 C -0.2628(4) 0.6557(5) 0.4360(3) 0.0805(15) Uani 1 1 d . . . H32 H -0.3243 0.7021 0.4541 0.097 Uiso 1 1 calc R . . C33 C -0.1485(3) 0.5957(3) 0.3298(2) 0.0433(8) Uani 1 1 d . . . H33 H -0.1288 0.5982 0.2715 0.052 Uiso 1 1 calc R . . C34 C -0.0852(3) 0.5219(3) 0.3866(2) 0.0438(8) Uani 1 1 d . . . H34 H -0.0235 0.4773 0.3668 0.053 Uiso 1 1 calc R . . C35 C 0.3943(3) 0.1378(3) 0.6904(2) 0.0400(8) Uani 1 1 d . . . H35 H 0.4347 0.1864 0.7321 0.048 Uiso 1 1 calc R . . C36 C 0.4539(3) 0.0963(3) 0.6208(2) 0.0385(8) Uani 1 1 d . . . H36 H 0.5311 0.1197 0.6144 0.046 Uiso 1 1 calc R . . C37 C 0.3969(3) 0.0197(3) 0.5609(2) 0.0366(9) Uani 1 1 d . . . C38 C 0.2827(3) -0.0111(4) 0.5745(3) 0.0620(12) Uani 1 1 d . . . H38 H 0.2421 -0.0645 0.5363 0.074 Uiso 1 1 calc R . . C39 C 0.2291(4) 0.0365(4) 0.6437(3) 0.0629(12) Uani 1 1 d . . . H39 H 0.1516 0.0152 0.6511 0.075 Uiso 1 1 calc R . . C40 C 0.4557(3) -0.0291(3) 0.4850(2) 0.0377(9) Uani 1 1 d . . . C41 C 0.5440(3) 0.0317(3) 0.4464(2) 0.0521(10) Uani 1 1 d . . . H41 H 0.5673 0.1072 0.4671 0.062 Uiso 1 1 calc R . . C42 C 0.5978(3) -0.0194(3) 0.3771(2) 0.0534(10) Uani 1 1 d . . . H42 H 0.6561 0.0241 0.3516 0.064 Uiso 1 1 calc R . . C43 C 0.4854(3) -0.1837(3) 0.3828(3) 0.0554(11) Uani 1 1 d . . . H43 H 0.4639 -0.2591 0.3612 0.066 Uiso 1 1 calc R . . C44 C 0.4268(3) -0.1405(3) 0.4504(2) 0.0540(10) Uani 1 1 d . . . H44 H 0.3676 -0.1856 0.4733 0.065 Uiso 1 1 calc R . . Cu1 Cu 0.17845(3) 0.21983(3) 0.76897(3) 0.04304(11) Uani 1 1 d . . . N1 N 0.0183(3) 0.7228(3) 0.7590(2) 0.0575(8) Uani 1 1 d . . . H1A H -0.0186 0.7296 0.8060 0.069 Uiso 1 1 calc R . . N2 N 0.6622(3) 0.8165(2) 0.8281(2) 0.0568(8) Uani 1 1 d . . . H2 H 0.6820 0.8716 0.8659 0.068 Uiso 1 1 calc R . . N3 N 0.0827(3) 0.3043(3) 0.66821(19) 0.0460(8) Uani 1 1 d . . . N4 N -0.2365(3) 0.6643(3) 0.35231(19) 0.0467(8) Uani 1 1 d . . . N5 N 0.2829(3) 0.1125(3) 0.70153(19) 0.0439(7) Uani 1 1 d . . . N6 N 0.5705(2) -0.1276(3) 0.34486(18) 0.0410(7) 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 O1 0.0623(17) 0.0542(17) 0.0602(17) -0.0060(12) 0.0125(14) 0.0094(13) O2 0.0698(19) 0.068(2) 0.0691(19) 0.0005(15) -0.0028(15) 0.0257(17) O3 0.150(3) 0.098(3) 0.0448(18) 0.0166(17) 0.0169(19) 0.064(2) O4 0.0680(17) 0.0540(17) 0.0451(15) 0.0007(11) 0.0180(13) 0.0130(13) O5 0.094(2) 0.0569(18) 0.090(2) -0.0223(17) -0.0480(18) 0.0209(17) O6 0.082(2) 0.0555(19) 0.072(2) -0.0067(15) -0.0317(16) 0.0190(16) O7 0.0729(14) 0.0384(12) 0.0375(15) -0.0055(12) 0.0098(12) 0.0022(14) O8 0.0729(18) 0.0628(18) 0.0575(17) -0.0048(14) -0.0278(14) 0.0048(14) C1 0.040(2) 0.048(2) 0.059(3) -0.008(2) 0.0041(18) -0.0018(18) C2 0.0356(18) 0.038(2) 0.055(2) -0.0080(17) -0.0013(16) -0.0017(15) C3 0.0406(19) 0.048(2) 0.046(2) -0.0073(17) 0.0098(16) -0.0021(17) C4 0.0321(19) 0.047(2) 0.042(2) -0.0041(16) 0.0081(15) -0.0018(16) C5 0.0318(17) 0.043(2) 0.047(2) -0.0062(17) 0.0025(15) 0.0011(15) C6 0.0382(19) 0.041(2) 0.0418(19) -0.0074(16) 0.0008(15) -0.0007(16) C7 0.043(2) 0.048(2) 0.042(2) -0.0022(15) -0.0015(16) 0.0084(16) C8 0.051(2) 0.052(2) 0.042(2) -0.0021(18) -0.0022(18) 0.005(2) C9 0.060(2) 0.047(2) 0.058(2) 0.0141(19) 0.0097(19) 0.011(2) C10 0.053(2) 0.040(2) 0.056(2) 0.0100(18) 0.0061(19) 0.0128(18) C11 0.048(2) 0.056(2) 0.048(2) 0.0015(17) -0.0013(18) 0.0054(18) C12 0.047(2) 0.063(3) 0.046(2) 0.0057(19) -0.0002(17) 0.012(2) C13 0.049(2) 0.039(2) 0.061(2) 0.0140(18) -0.0006(18) 0.0176(18) C14 0.068(3) 0.050(3) 0.067(3) -0.015(2) 0.004(2) 0.010(2) C15 0.060(3) 0.058(3) 0.060(3) -0.005(2) 0.014(2) 0.016(2) C16 0.060(3) 0.043(2) 0.076(3) 0.017(2) -0.005(2) 0.0101(19) C17 0.0385(18) 0.034(2) 0.048(2) 0.0079(16) 0.0102(16) 0.0002(15) C18 0.0408(19) 0.038(2) 0.0402(19) 0.0000(15) 0.0063(16) -0.0017(15) C19 0.0367(18) 0.040(2) 0.0337(18) -0.0012(15) 0.0048(14) 0.0030(15) C20 0.0391(18) 0.0340(19) 0.0391(19) 0.0047(15) 0.0047(15) 0.0126(15) C21 0.0314(17) 0.0347(19) 0.0321(17) 0.0021(13) 0.0051(13) 0.0029(14) C22 0.0306(16) 0.0425(19) 0.037(2) 0.0066(15) -0.0015(15) 0.0027(16) C23 0.0340(18) 0.048(2) 0.035(2) -0.0026(15) 0.0065(16) 0.0012(17) C24 0.042(2) 0.045(2) 0.041(2) -0.0044(16) -0.0016(16) 0.0118(18) C25 0.050(2) 0.083(3) 0.052(2) 0.021(2) 0.017(2) 0.016(2) C26 0.050(2) 0.078(3) 0.047(3) 0.019(2) 0.017(2) 0.006(2) C27 0.0380(19) 0.050(2) 0.038(2) 0.0040(17) 0.0056(16) -0.0033(17) C28 0.039(2) 0.116(4) 0.077(3) 0.043(3) 0.010(2) 0.005(2) C29 0.050(2) 0.114(4) 0.059(3) 0.046(3) 0.010(2) -0.003(2) C30 0.041(2) 0.048(2) 0.043(2) 0.0024(17) 0.0017(16) -0.0035(17) C31 0.069(3) 0.111(4) 0.037(2) 0.025(2) 0.017(2) 0.036(3) C32 0.083(3) 0.114(4) 0.048(3) 0.019(3) 0.023(2) 0.050(3) C33 0.054(2) 0.044(2) 0.0323(18) 0.0019(16) 0.0100(16) -0.0014(18) C34 0.046(2) 0.041(2) 0.045(2) 0.0007(16) 0.0086(17) 0.0051(17) C35 0.0349(19) 0.045(2) 0.0394(19) -0.0106(16) -0.0033(15) 0.0041(16) C36 0.0318(17) 0.039(2) 0.045(2) 0.0003(16) 0.0006(15) 0.0023(15) C37 0.038(2) 0.040(2) 0.0325(19) -0.0037(15) 0.0076(16) -0.0005(16) C38 0.046(2) 0.074(3) 0.069(3) -0.037(2) 0.020(2) -0.016(2) C39 0.045(2) 0.068(3) 0.078(3) -0.031(2) 0.019(2) -0.018(2) C40 0.041(2) 0.033(2) 0.040(2) -0.0001(16) 0.0056(17) -0.0003(17) C41 0.067(3) 0.040(2) 0.052(2) -0.0111(18) 0.020(2) -0.0191(19) C42 0.056(2) 0.052(3) 0.056(2) -0.0041(19) 0.0251(19) -0.017(2) C43 0.052(2) 0.049(2) 0.069(3) -0.0239(19) 0.024(2) -0.0172(18) C44 0.051(2) 0.055(3) 0.059(2) -0.0137(19) 0.0239(19) -0.0184(19) Cu1 0.0453(2) 0.0499(2) 0.0349(2) -0.0023(2) 0.00932(15) -0.0003(3) N1 0.0567(19) 0.070(2) 0.0479(18) 0.0130(16) 0.0190(15) 0.0190(17) N2 0.058(2) 0.0327(18) 0.078(2) 0.0035(15) -0.0099(17) 0.0068(15) N3 0.0452(19) 0.054(2) 0.0393(17) 0.0082(14) 0.0069(14) -0.0028(15) N4 0.0465(18) 0.054(2) 0.0396(17) 0.0044(14) 0.0048(14) 0.0028(16) N5 0.0421(17) 0.0461(19) 0.0447(18) -0.0077(15) 0.0112(15) 0.0006(15) N6 0.0437(17) 0.0424(18) 0.0381(17) -0.0059(14) 0.0111(14) -0.0056(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 O1 C1 1.315(5) . ? O2 C1 1.210(5) . ? O3 C8 1.196(4) . ? O4 C8 1.311(4) . ? O4 H4 0.8200 . ? O5 C24 1.314(4) . ? O5 H5 0.8200 . ? O6 C24 1.188(4) . ? O7 C23 1.271(4) . ? O8 C23 1.239(4) . ? C1 C2 1.494(5) . ? C2 C3 1.380(5) . ? C2 C7 1.391(4) . ? C3 C4 1.392(5) . ? C3 H3 0.9300 . ? C4 N1 1.371(4) . ? C4 C5 1.401(5) . ? C5 C6 1.384(4) . ? C5 H5A 0.9300 . ? C6 C7 1.382(4) . ? C6 C8 1.492(5) . ? C7 H7 0.9300 . ? C9 N1 1.450(4) . ? C9 C10 1.516(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.372(5) . ? C10 C15 1.392(5) . ? C11 C12 1.387(5) . ? C11 H11 0.9300 . ? C12 C13 1.372(5) . ? C12 H12 0.9300 . ? C13 C14 1.380(5) . ? C13 C16 1.530(5) . ? C14 C15 1.385(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 N2 1.440(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N2 1.383(4) . ? C17 C22 1.387(4) . ? C17 C18 1.401(4) . ? C18 C19 1.385(4) . ? C18 H18 0.9300 . ? C19 C20 1.396(4) . ? C19 C24 1.497(5) . ? C20 C21 1.381(4) . ? C20 H20 0.9300 . ? C21 C22 1.387(4) . ? C21 C23 1.508(4) . ? C22 H22 0.9300 . ? C25 N3 1.350(4) . ? C25 C26 1.363(5) . ? C25 H25 0.9300 . ? C26 C27 1.379(5) . ? C26 H26 0.9300 . ? C27 C28 1.361(5) . ? C27 C30 1.470(4) . ? C28 C29 1.359(5) . ? C28 H28 0.9300 . ? C29 N3 1.314(5) . ? C29 H29 0.9300 . ? C30 C34 1.370(4) . ? C30 C31 1.381(5) . ? C31 C32 1.373(6) . ? C31 H31 0.9300 . ? C32 N4 1.331(5) . ? C32 H32 0.9300 . ? C33 N4 1.327(4) . ? C33 C34 1.361(4) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 N5 1.324(4) . ? C35 C36 1.379(4) . ? C35 H35 0.9300 . ? C36 C37 1.376(5) . ? C36 H36 0.9300 . ? C37 C38 1.378(5) . ? C37 C40 1.479(4) . ? C38 C39 1.363(5) . ? C38 H38 0.9300 . ? C39 N5 1.337(5) . ? C39 H39 0.9300 . ? C40 C44 1.379(5) . ? C40 C41 1.381(5) . ? C41 C42 1.380(5) . ? C41 H41 0.9300 . ? C42 N6 1.331(4) . ? C42 H42 0.9300 . ? C43 N6 1.322(4) . ? C43 C44 1.354(5) . ? C43 H43 0.9300 . ? C44 H44 0.9300 . ? Cu1 N4 2.008(3) 2_565 ? Cu1 N5 2.020(3) . ? Cu1 N6 2.028(3) 2_455 ? Cu1 N3 2.044(3) . ? N1 H1A 0.8600 . ? N2 H2 0.8600 . ? N4 Cu1 2.008(3) 2_464 ? N6 Cu1 2.028(3) 2_554 ? 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 C8 O4 H4 109.5 . . ? C24 O5 H5 109.5 . . ? O2 C1 O1 123.1(4) . . ? O2 C1 C2 122.4(4) . . ? O1 C1 C2 114.5(4) . . ? C3 C2 C7 119.7(3) . . ? C3 C2 C1 121.2(3) . . ? C7 C2 C1 119.1(3) . . ? C2 C3 C4 121.7(3) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? N1 C4 C3 120.0(3) . . ? N1 C4 C5 122.5(3) . . ? C3 C4 C5 117.6(3) . . ? C6 C5 C4 121.1(3) . . ? C6 C5 H5A 119.5 . . ? C4 C5 H5A 119.5 . . ? C7 C6 C5 120.2(3) . . ? C7 C6 C8 118.6(3) . . ? C5 C6 C8 121.2(3) . . ? C6 C7 C2 119.7(3) . . ? C6 C7 H7 120.1 . . ? C2 C7 H7 120.1 . . ? O3 C8 O4 122.9(4) . . ? O3 C8 C6 123.0(4) . . ? O4 C8 C6 113.9(3) . . ? N1 C9 C10 114.3(3) . . ? N1 C9 H9A 108.7 . . ? C10 C9 H9A 108.7 . . ? N1 C9 H9B 108.7 . . ? C10 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C11 C10 C15 118.5(4) . . ? C11 C10 C9 121.4(3) . . ? C15 C10 C9 120.1(3) . . ? C10 C11 C12 120.5(4) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 121.4(4) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 118.2(4) . . ? C12 C13 C16 120.8(3) . . ? C14 C13 C16 121.0(4) . . ? C13 C14 C15 121.0(4) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C14 C15 C10 120.3(4) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? N2 C16 C13 115.3(3) . . ? N2 C16 H16A 108.4 . . ? C13 C16 H16A 108.4 . . ? N2 C16 H16B 108.4 . . ? C13 C16 H16B 108.4 . . ? H16A C16 H16B 107.5 . . ? N2 C17 C22 122.0(3) . . ? N2 C17 C18 119.8(3) . . ? C22 C17 C18 118.2(3) . . ? C19 C18 C17 120.7(3) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 120.0(3) . . ? C18 C19 C24 122.7(3) . . ? C20 C19 C24 117.3(3) . . ? C21 C20 C19 119.6(3) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 119.9(3) . . ? C20 C21 C23 120.8(3) . . ? C22 C21 C23 119.2(3) . . ? C17 C22 C21 121.3(3) . . ? C17 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? O8 C23 O7 125.3(3) . . ? O8 C23 C21 117.2(3) . . ? O7 C23 C21 117.5(3) . . ? O6 C24 O5 123.4(3) . . ? O6 C24 C19 123.3(3) . . ? O5 C24 C19 113.3(3) . . ? N3 C25 C26 123.5(4) . . ? N3 C25 H25 118.2 . . ? C26 C25 H25 118.2 . . ? C25 C26 C27 119.8(4) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C28 C27 C26 116.3(3) . . ? C28 C27 C30 121.9(3) . . ? C26 C27 C30 121.8(3) . . ? C29 C28 C27 120.8(4) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? N3 C29 C28 124.2(4) . . ? N3 C29 H29 117.9 . . ? C28 C29 H29 117.9 . . ? C34 C30 C31 116.2(3) . . ? C34 C30 C27 123.3(3) . . ? C31 C30 C27 120.5(3) . . ? C32 C31 C30 119.7(4) . . ? C32 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? N4 C32 C31 123.9(4) . . ? N4 C32 H32 118.1 . . ? C31 C32 H32 118.1 . . ? N4 C33 C34 124.2(3) . . ? N4 C33 H33 117.9 . . ? C34 C33 H33 117.9 . . ? C33 C34 C30 120.4(3) . . ? C33 C34 H34 119.8 . . ? C30 C34 H34 119.8 . . ? N5 C35 C36 123.9(3) . . ? N5 C35 H35 118.0 . . ? C36 C35 H35 118.0 . . ? C37 C36 C35 118.7(3) . . ? C37 C36 H36 120.7 . . ? C35 C36 H36 120.7 . . ? C36 C37 C38 117.5(3) . . ? C36 C37 C40 121.7(3) . . ? C38 C37 C40 120.8(3) . . ? C39 C38 C37 120.1(4) . . ? C39 C38 H38 120.0 . . ? C37 C38 H38 120.0 . . ? N5 C39 C38 123.0(4) . . ? N5 C39 H39 118.5 . . ? C38 C39 H39 118.5 . . ? C44 C40 C41 116.3(3) . . ? C44 C40 C37 121.3(3) . . ? C41 C40 C37 122.4(3) . . ? C42 C41 C40 120.0(3) . . ? C42 C41 H41 120.0 . . ? C40 C41 H41 120.0 . . ? N6 C42 C41 123.4(3) . . ? N6 C42 H42 118.3 . . ? C41 C42 H42 118.3 . . ? N6 C43 C44 125.5(3) . . ? N6 C43 H43 117.2 . . ? C44 C43 H43 117.2 . . ? C43 C44 C40 119.5(3) . . ? C43 C44 H44 120.3 . . ? C40 C44 H44 120.3 . . ? N4 Cu1 N5 115.19(13) 2_565 . ? N4 Cu1 N6 104.68(12) 2_565 2_455 ? N5 Cu1 N6 113.12(10) . 2_455 ? N4 Cu1 N3 112.50(12) 2_565 . ? N5 Cu1 N3 101.28(12) . . ? N6 Cu1 N3 110.26(12) 2_455 . ? C4 N1 C9 124.2(3) . . ? C4 N1 H1A 117.9 . . ? C9 N1 H1A 117.9 . . ? C17 N2 C16 122.6(3) . . ? C17 N2 H2 118.7 . . ? C16 N2 H2 118.7 . . ? C29 N3 C25 115.4(3) . . ? C29 N3 Cu1 122.6(3) . . ? C25 N3 Cu1 121.8(3) . . ? C33 N4 C32 115.6(3) . . ? C33 N4 Cu1 123.3(2) . 2_464 ? C32 N4 Cu1 121.1(3) . 2_464 ? C35 N5 C39 116.7(3) . . ? C35 N5 Cu1 123.0(2) . . ? C39 N5 Cu1 116.7(2) . . ? C43 N6 C42 115.3(3) . . ? C43 N6 Cu1 120.2(2) . 2_554 ? C42 N6 Cu1 122.3(2) . 2_554 ? 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 C3 -175.8(3) . . . . ? O1 C1 C2 C3 4.7(5) . . . . ? O2 C1 C2 C7 6.7(5) . . . . ? O1 C1 C2 C7 -172.8(3) . . . . ? C7 C2 C3 C4 0.0(5) . . . . ? C1 C2 C3 C4 -177.4(3) . . . . ? C2 C3 C4 N1 180.0(3) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? N1 C4 C5 C6 -179.6(3) . . . . ? C3 C4 C5 C6 0.5(5) . . . . ? C4 C5 C6 C7 -0.8(5) . . . . ? C4 C5 C6 C8 178.0(3) . . . . ? C5 C6 C7 C2 0.8(5) . . . . ? C8 C6 C7 C2 -178.1(3) . . . . ? C3 C2 C7 C6 -0.4(5) . . . . ? C1 C2 C7 C6 177.1(3) . . . . ? C7 C6 C8 O3 6.4(6) . . . . ? C5 C6 C8 O3 -172.5(4) . . . . ? C7 C6 C8 O4 -178.0(3) . . . . ? C5 C6 C8 O4 3.2(5) . . . . ? N1 C9 C10 C11 -115.3(4) . . . . ? N1 C9 C10 C15 65.6(4) . . . . ? C15 C10 C11 C12 -1.6(5) . . . . ? C9 C10 C11 C12 179.2(3) . . . . ? C10 C11 C12 C13 0.7(5) . . . . ? C11 C12 C13 C14 0.0(5) . . . . ? C11 C12 C13 C16 -178.7(3) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C16 C13 C14 C15 179.0(3) . . . . ? C13 C14 C15 C10 -1.2(6) . . . . ? C11 C10 C15 C14 1.9(5) . . . . ? C9 C10 C15 C14 -178.9(3) . . . . ? C12 C13 C16 N2 -125.5(4) . . . . ? C14 C13 C16 N2 55.8(5) . . . . ? N2 C17 C18 C19 176.6(3) . . . . ? C22 C17 C18 C19 -3.9(4) . . . . ? C17 C18 C19 C20 -1.2(4) . . . . ? C17 C18 C19 C24 179.6(3) . . . . ? C18 C19 C20 C21 4.0(4) . . . . ? C24 C19 C20 C21 -176.8(3) . . . . ? C19 C20 C21 C22 -1.5(4) . . . . ? C19 C20 C21 C23 -179.9(3) . . . . ? N2 C17 C22 C21 -174.0(3) . . . . ? C18 C17 C22 C21 6.5(5) . . . . ? C20 C21 C22 C17 -3.9(4) . . . . ? C23 C21 C22 C17 174.6(3) . . . . ? C20 C21 C23 O8 -160.5(3) . . . . ? C22 C21 C23 O8 21.0(4) . . . . ? C20 C21 C23 O7 19.0(5) . . . . ? C22 C21 C23 O7 -159.5(3) . . . . ? C18 C19 C24 O6 -178.7(4) . . . . ? C20 C19 C24 O6 2.1(5) . . . . ? C18 C19 C24 O5 1.6(5) . . . . ? C20 C19 C24 O5 -177.6(3) . . . . ? N3 C25 C26 C27 -0.5(7) . . . . ? C25 C26 C27 C28 -0.2(6) . . . . ? C25 C26 C27 C30 177.5(4) . . . . ? C26 C27 C28 C29 0.3(7) . . . . ? C30 C27 C28 C29 -177.3(4) . . . . ? C27 C28 C29 N3 0.2(8) . . . . ? C28 C27 C30 C34 -148.2(4) . . . . ? C26 C27 C30 C34 34.2(6) . . . . ? C28 C27 C30 C31 34.1(6) . . . . ? C26 C27 C30 C31 -143.4(4) . . . . ? C34 C30 C31 C32 -0.8(7) . . . . ? C27 C30 C31 C32 177.0(4) . . . . ? C30 C31 C32 N4 0.7(8) . . . . ? N4 C33 C34 C30 1.3(5) . . . . ? C31 C30 C34 C33 -0.1(5) . . . . ? C27 C30 C34 C33 -177.8(3) . . . . ? N5 C35 C36 C37 -3.0(5) . . . . ? C35 C36 C37 C38 -0.1(5) . . . . ? C35 C36 C37 C40 -179.5(3) . . . . ? C36 C37 C38 C39 1.9(6) . . . . ? C40 C37 C38 C39 -178.7(4) . . . . ? C37 C38 C39 N5 -0.9(7) . . . . ? C36 C37 C40 C44 149.5(4) . . . . ? C38 C37 C40 C44 -29.9(5) . . . . ? C36 C37 C40 C41 -28.8(4) . . . . ? C38 C37 C40 C41 151.9(4) . . . . ? C44 C40 C41 C42 0.1(6) . . . . ? C37 C40 C41 C42 178.4(3) . . . . ? C40 C41 C42 N6 -1.1(6) . . . . ? N6 C43 C44 C40 -0.2(6) . . . . ? C41 C40 C44 C43 0.5(5) . . . . ? C37 C40 C44 C43 -177.8(3) . . . . ? C3 C4 N1 C9 -170.5(3) . . . . ? C5 C4 N1 C9 9.6(5) . . . . ? C10 C9 N1 C4 68.9(5) . . . . ? C22 C17 N2 C16 -5.3(5) . . . . ? C18 C17 N2 C16 174.2(3) . . . . ? C13 C16 N2 C17 69.7(4) . . . . ? C28 C29 N3 C25 -0.9(7) . . . . ? C28 C29 N3 Cu1 174.0(4) . . . . ? C26 C25 N3 C29 1.0(6) . . . . ? C26 C25 N3 Cu1 -173.9(3) . . . . ? N4 Cu1 N3 C29 -100.6(4) 2_565 . . . ? N5 Cu1 N3 C29 135.9(4) . . . . ? N6 Cu1 N3 C29 15.9(4) 2_455 . . . ? N4 Cu1 N3 C25 73.9(3) 2_565 . . . ? N5 Cu1 N3 C25 -49.6(3) . . . . ? N6 Cu1 N3 C25 -169.6(3) 2_455 . . . ? C34 C33 N4 C32 -1.4(6) . . . . ? C34 C33 N4 Cu1 176.0(3) . . . 2_464 ? C31 C32 N4 C33 0.4(7) . . . . ? C31 C32 N4 Cu1 -177.0(4) . . . 2_464 ? C36 C35 N5 C39 4.0(5) . . . . ? C36 C35 N5 Cu1 -154.1(3) . . . . ? C38 C39 N5 C35 -2.0(6) . . . . ? C38 C39 N5 Cu1 157.5(4) . . . . ? N4 Cu1 N5 C35 -20.1(3) 2_565 . . . ? N6 Cu1 N5 C35 -140.5(3) 2_455 . . . ? N3 Cu1 N5 C35 101.6(3) . . . . ? N4 Cu1 N5 C39 -178.3(3) 2_565 . . . ? N6 Cu1 N5 C39 61.4(3) 2_455 . . . ? N3 Cu1 N5 C39 -56.6(3) . . . . ? C44 C43 N6 C42 -0.7(6) . . . . ? C44 C43 N6 Cu1 163.1(3) . . . 2_554 ? C41 C42 N6 C43 1.3(6) . . . . ? C41 C42 N6 Cu1 -162.1(3) . . . 2_554 ? 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 O7 0.82 1.85 2.657(4) 169.0 2_464 O5 H5 O8 0.82 1.85 2.619(4) 156.0 2_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.327 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 959348'