# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- k1727k1774corrected2.cif' _publ_contact_author_name 'Dimitris P. Kessissoglou' _publ_contact_author_address ; Department of General and Inorganic Chemistry Faculty of Chemistry Aristotle University of Thessaloniki P.O. Box 135 GR 54124 Thessaloniki Greece ; _publ_contact_author_email kessisog@chem.auth.gr loop_ _publ_author_name _publ_author_address 'Alketa Tarushi' ; Department of General and Inorganic Chemistry Faculty of Chemistry Aristotle University of Thessaloniki P.O. Box 135 GR 54124 Thessaloniki Greece ; 'Eleni Polatoglou' ; Department of General and Inorganic Chemistry Faculty of Chemistry Aristotle University of Thessaloniki P.O. Box 135 GR 54124 Thessaloniki Greece ; 'Jakob Kljun' ; Faculty of Chemistry and Chemical Technology University of Ljubljana Askerceva 5, P. O. Box 537 1000 Ljubljana Slovenia ; 'Iztok Turel' ; Faculty of Chemistry and Chemical Technology University of Ljubljana Askerceva 5, P. O. Box 537 1000 Ljubljana Slovenia ; 'George Psomas' ; Department of General and Inorganic Chemistry Faculty of Chemistry Aristotle University of Thessaloniki P.O. Box 135 GR 54124 Thessaloniki Greece ; ; D.P.Kessissoglou ; ; Department of General and Inorganic Chemistry Faculty of Chemistry Aristotle University of Thessaloniki P.O. Box 135 GR 54124 Thessaloniki Greece ; _publ_section_title ; Interaction of Zn(II) with quinolone drugs: Structure and biological evaluation ; data_1 _database_code_depnum_ccdc_archive 'CCDC 823685' #TrackingRef '- k1727k1774corrected2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [(1,10-phenanthroline)di(5-amino-1-cyclopropyl-7-((3S,5R)-3,5- dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylato- \k^2^O,O)zinc(II)] bis methanol solvate ; _chemical_name_common ; ((1,10-phenanthroline)di(5-amino-1-cyclopropyl-7-((3S,5R)-3,5- dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3- carboxylato-kappa$2!O,O)zinc(ii)) bis methanol solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C50 H50 F4 N10 O6 Zn, 4(C H4 O)' _chemical_formula_sum 'C54 H66 F4 N10 O10 Zn' _chemical_formula_weight 1156.54 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' F F 0.0171 0.0103 '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 orthorhombic _symmetry_space_group_name_H-M 'P c c n' _symmetry_space_group_name_Hall '-P 2ab 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 14.774(5) _cell_length_b 15.850(5) _cell_length_c 23.734(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5558(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6952 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2424 _exptl_absorpt_coefficient_mu 0.522 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9258 _exptl_absorpt_correction_T_max 0.9545 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12083 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6355 _reflns_number_gt 4487 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinovski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinovski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0648P)^2^+6.7471P] 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 6355 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0848 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1457 _refine_ls_wR_factor_gt 0.1255 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.7500 0.2500 0.270323(17) 0.02342(13) Uani 1 2 d S . . C01 C 0.62103(19) 0.38126(17) 0.31893(11) 0.0254(6) Uani 1 1 d . . . C02 C 0.68738(19) 0.40030(17) 0.36539(11) 0.0245(6) Uani 1 1 d . . . C03 C 0.66250(19) 0.45968(17) 0.40421(11) 0.0263(6) Uani 1 1 d . . . H03 H 0.6051 0.4857 0.3994 0.032 Uiso 1 1 calc R . . C04 C 0.79250(19) 0.44074(16) 0.46125(11) 0.0241(6) Uani 1 1 d . . . C05 C 0.82675(18) 0.38183(16) 0.42067(11) 0.0232(5) Uani 1 1 d . . . C06 C 0.77763(18) 0.36672(16) 0.36893(11) 0.0234(6) Uani 1 1 d . . . C07 C 0.6863(2) 0.56119(18) 0.47868(13) 0.0313(6) Uani 1 1 d . . . H07 H 0.6530 0.5534 0.5150 0.038 Uiso 1 1 calc R . . C08 C 0.6613(3) 0.6364(2) 0.44455(17) 0.0565(11) Uani 1 1 d . . . H08A H 0.6130 0.6738 0.4592 0.068 Uiso 1 1 calc R . . H08B H 0.6631 0.6310 0.4030 0.068 Uiso 1 1 calc R . . C09 C 0.7495(3) 0.63430(19) 0.47568(15) 0.0455(8) Uani 1 1 d . . . H09A H 0.8056 0.6276 0.4533 0.055 Uiso 1 1 calc R . . H09B H 0.7555 0.6703 0.5096 0.055 Uiso 1 1 calc R . . C10 C 0.90787(18) 0.33647(17) 0.43399(11) 0.0251(6) Uani 1 1 d . . . C11 C 0.94803(18) 0.35114(18) 0.48577(11) 0.0256(6) Uani 1 1 d . . . C12 C 0.91333(19) 0.40342(17) 0.52771(11) 0.0262(6) Uani 1 1 d . . . C13 C 0.8349(2) 0.44864(17) 0.51303(11) 0.0266(6) Uani 1 1 d . . . C14 C 1.0005(2) 0.33823(18) 0.60598(12) 0.0301(6) Uani 1 1 d . . . H14A H 1.0655 0.3482 0.5983 0.036 Uiso 1 1 calc R . . H14B H 0.9831 0.2842 0.5881 0.036 Uiso 1 1 calc R . . C15 C 0.9848(2) 0.33319(19) 0.66949(12) 0.0306(6) Uani 1 1 d . . . H15 H 0.9198 0.3192 0.6766 0.037 Uiso 1 1 calc R . . C16 C 1.0438(2) 0.2651(2) 0.69550(14) 0.0400(8) Uani 1 1 d . . . H16A H 1.1076 0.2783 0.6886 0.060 Uiso 1 1 calc R . . H16B H 1.0291 0.2105 0.6785 0.060 Uiso 1 1 calc R . . H16C H 1.0327 0.2626 0.7362 0.060 Uiso 1 1 calc R . . C17 C 0.9642(2) 0.48822(18) 0.60962(12) 0.0303(6) Uani 1 1 d . . . H17A H 0.9246 0.5321 0.5930 0.036 Uiso 1 1 calc R . . H17B H 1.0279 0.5050 0.6033 0.036 Uiso 1 1 calc R . . C18 C 0.9459(2) 0.48120(18) 0.67237(12) 0.0301(6) Uani 1 1 d . . . H18 H 0.8814 0.4642 0.6784 0.036 Uiso 1 1 calc R . . C19 C 0.9631(2) 0.5653(2) 0.70179(13) 0.0402(8) Uani 1 1 d . . . H19A H 0.9557 0.5583 0.7426 0.060 Uiso 1 1 calc R . . H19B H 0.9198 0.6074 0.6881 0.060 Uiso 1 1 calc R . . H19C H 1.0249 0.5843 0.6937 0.060 Uiso 1 1 calc R . . C20 C 0.6431(2) 0.1151(2) 0.20020(18) 0.0467(9) Uani 1 1 d . . . H20 H 0.6279 0.0907 0.2355 0.056 Uiso 1 1 calc R . . C21 C 0.6081(3) 0.0791(3) 0.1509(2) 0.0647(13) Uani 1 1 d . . . H21 H 0.5678 0.0325 0.1533 0.078 Uiso 1 1 calc R . . C22 C 0.6312(3) 0.1101(3) 0.1003(2) 0.0651(13) Uani 1 1 d . . . H22 H 0.6082 0.0850 0.0669 0.078 Uiso 1 1 calc R . . C23 C 0.6899(3) 0.1804(2) 0.09707(14) 0.0489(10) Uani 1 1 d . . . C24 C 0.7207(2) 0.21380(19) 0.14844(12) 0.0312(6) Uani 1 1 d . . . C25 C 0.7210(3) 0.2173(3) 0.04550(14) 0.0683(16) Uani 1 1 d . . . H25 H 0.7003 0.1951 0.0106 0.082 Uiso 1 1 calc R . . O26 O 0.54450(13) 0.41653(13) 0.32182(8) 0.0313(5) Uani 1 1 d . . . O27 O 0.64275(14) 0.33202(12) 0.27947(8) 0.0303(4) Uani 1 1 d . . . O28 O 0.81444(13) 0.32430(13) 0.32982(8) 0.0299(4) Uani 1 1 d . . . N29 N 0.71258(16) 0.48430(14) 0.44867(9) 0.0257(5) Uani 1 1 d . . . N30 N 0.94730(17) 0.28148(16) 0.39764(10) 0.0316(6) Uani 1 1 d . . . H30A H 0.9978 0.2556 0.4071 0.038 Uiso 1 1 calc R . . H30B H 0.9224 0.2717 0.3646 0.038 Uiso 1 1 calc R . . N31 N 0.94669(17) 0.40688(15) 0.58215(10) 0.0306(5) Uani 1 1 d . . . N32 N 1.00550(16) 0.41577(16) 0.69530(10) 0.0303(5) Uani 1 1 d . . . H32 H 0.996(2) 0.411(2) 0.7356(14) 0.032(8) Uiso 1 1 d . . . N33 N 0.69676(15) 0.18211(15) 0.19917(10) 0.0294(5) Uani 1 1 d . . . F34 F 0.79312(12) 0.49220(10) 0.55499(7) 0.0321(4) Uani 1 1 d . . . F35 F 1.02811(11) 0.31031(11) 0.49466(7) 0.0340(4) Uani 1 1 d . . . C36 C 0.7534(3) 0.5749(3) 0.28679(18) 0.0588(10) Uani 1 1 d . . . H36A H 0.6911 0.5600 0.2969 0.088 Uiso 1 1 calc R . . H36B H 0.7724 0.5416 0.2541 0.088 Uiso 1 1 calc R . . H36C H 0.7565 0.6351 0.2776 0.088 Uiso 1 1 calc R . . O37 O 0.81102(17) 0.5577(2) 0.33241(11) 0.0603(8) Uani 1 1 d . . . H37 H 0.8650 0.5654 0.3226 0.090 Uiso 1 1 calc R . . C38 C 0.8469(4) 0.6531(4) 0.1262(2) 0.0928(18) Uani 1 1 d . . . H38A H 0.8314 0.6086 0.1531 0.139 Uiso 1 1 calc R . . H38B H 0.7966 0.6613 0.0999 0.139 Uiso 1 1 calc R . . H38C H 0.8585 0.7059 0.1465 0.139 Uiso 1 1 calc R . . O39 O 0.92575(19) 0.62942(17) 0.09577(11) 0.0538(7) Uani 1 1 d . . . H39 H 0.9668 0.6159 0.1185 0.081 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 Zn1 0.0273(2) 0.0238(2) 0.0192(2) 0.000 0.000 0.00205(19) C01 0.0282(14) 0.0226(13) 0.0255(13) 0.0029(11) -0.0015(11) 0.0004(11) C02 0.0262(13) 0.0225(13) 0.0247(13) 0.0007(11) -0.0012(11) -0.0002(11) C03 0.0265(14) 0.0267(14) 0.0257(14) 0.0025(11) -0.0003(11) 0.0012(11) C04 0.0256(14) 0.0207(13) 0.0261(13) -0.0013(10) 0.0020(11) -0.0029(11) C05 0.0249(13) 0.0214(13) 0.0234(13) -0.0008(10) 0.0001(11) -0.0008(11) C06 0.0277(14) 0.0192(13) 0.0232(13) -0.0013(10) 0.0001(10) -0.0027(10) C07 0.0349(16) 0.0270(14) 0.0321(15) -0.0069(12) 0.0004(13) 0.0056(12) C08 0.086(3) 0.0304(17) 0.053(2) -0.0068(16) -0.007(2) 0.0228(19) C09 0.060(2) 0.0255(15) 0.051(2) -0.0078(14) 0.0063(18) -0.0017(16) C10 0.0264(14) 0.0242(13) 0.0247(13) 0.0000(11) 0.0013(11) -0.0010(11) C11 0.0222(13) 0.0267(13) 0.0278(14) 0.0033(11) -0.0021(11) -0.0006(11) C12 0.0278(14) 0.0253(14) 0.0256(14) 0.0005(11) -0.0008(11) -0.0069(11) C13 0.0314(15) 0.0252(13) 0.0231(13) -0.0056(11) 0.0029(11) -0.0043(11) C14 0.0320(15) 0.0325(15) 0.0259(14) 0.0000(12) -0.0011(12) -0.0021(12) C15 0.0306(15) 0.0340(15) 0.0272(14) 0.0026(12) -0.0008(12) -0.0076(12) C16 0.0438(18) 0.0417(19) 0.0345(16) 0.0068(14) -0.0057(14) -0.0022(14) C17 0.0353(16) 0.0278(14) 0.0280(14) -0.0027(11) -0.0028(12) -0.0076(12) C18 0.0306(15) 0.0318(15) 0.0281(14) -0.0035(12) -0.0004(12) -0.0087(12) C19 0.0489(19) 0.0405(18) 0.0313(16) -0.0086(14) -0.0019(14) -0.0103(15) C20 0.0374(18) 0.0335(17) 0.069(2) -0.0163(17) 0.0121(17) -0.0055(14) C21 0.038(2) 0.051(2) 0.105(4) -0.043(3) -0.008(2) 0.0004(18) C22 0.051(2) 0.068(3) 0.076(3) -0.050(2) -0.026(2) 0.025(2) C23 0.051(2) 0.057(2) 0.0391(19) -0.0226(16) -0.0177(16) 0.0346(18) C24 0.0301(15) 0.0366(15) 0.0270(14) -0.0089(12) -0.0049(11) 0.0164(12) C25 0.093(4) 0.084(3) 0.0275(17) -0.0143(16) -0.0137(18) 0.065(3) O26 0.0271(10) 0.0369(11) 0.0299(10) -0.0004(9) -0.0019(8) 0.0070(9) O27 0.0329(11) 0.0300(10) 0.0281(10) -0.0040(8) -0.0080(8) 0.0058(9) O28 0.0288(10) 0.0352(11) 0.0255(10) -0.0086(8) -0.0042(8) 0.0067(9) N29 0.0296(12) 0.0232(11) 0.0243(12) -0.0040(9) 0.0007(9) 0.0021(10) N30 0.0323(13) 0.0358(13) 0.0266(12) -0.0084(10) -0.0064(10) 0.0107(11) N31 0.0394(14) 0.0285(12) 0.0240(12) -0.0025(10) -0.0072(10) 0.0000(11) N32 0.0309(13) 0.0373(13) 0.0227(12) -0.0002(10) -0.0007(10) -0.0087(11) N33 0.0239(12) 0.0288(12) 0.0355(13) -0.0065(10) 0.0041(10) 0.0008(10) F34 0.0345(9) 0.0356(9) 0.0262(8) -0.0093(7) 0.0015(7) 0.0013(8) F35 0.0286(9) 0.0441(10) 0.0292(9) -0.0030(7) -0.0052(7) 0.0076(8) C36 0.046(2) 0.067(3) 0.064(2) 0.019(2) -0.014(2) -0.012(2) O37 0.0360(13) 0.094(2) 0.0508(15) 0.0265(15) -0.0068(12) -0.0210(14) C38 0.075(3) 0.118(5) 0.085(4) -0.012(3) -0.027(3) 0.028(3) O39 0.0597(17) 0.0553(16) 0.0466(14) 0.0059(12) -0.0162(13) -0.0161(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O27 2.061(2) . ? Zn1 O27 2.061(2) 2_655 ? Zn1 O28 2.071(2) . ? Zn1 O28 2.0707(19) 2_655 ? Zn1 N33 2.151(2) . ? Zn1 N33 2.151(2) 2_655 ? C01 O27 1.261(3) . ? C01 O26 1.263(3) . ? C01 C02 1.506(4) . ? C02 C03 1.367(4) . ? C02 C06 1.438(4) . ? C03 N29 1.347(4) . ? C04 C13 1.385(4) . ? C04 N29 1.400(4) . ? C04 C05 1.434(4) . ? C05 C10 1.433(4) . ? C05 C06 1.446(4) . ? C06 O28 1.269(3) . ? C07 N29 1.464(3) . ? C07 C08 1.488(5) . ? C07 C09 1.490(5) . ? C08 C09 1.498(6) . ? C10 N30 1.358(4) . ? C10 C11 1.384(4) . ? C11 F35 1.365(3) . ? C11 C12 1.393(4) . ? C12 N31 1.384(4) . ? C12 C13 1.406(4) . ? C13 F34 1.360(3) . ? C14 N31 1.461(4) . ? C14 C15 1.527(4) . ? C15 N32 1.477(4) . ? C15 C16 1.519(4) . ? C17 N31 1.468(4) . ? C17 C18 1.518(4) . ? C18 N32 1.466(4) . ? C18 C19 1.527(4) . ? C20 N33 1.326(4) . ? C20 C21 1.400(6) . ? C21 C22 1.342(7) . ? C22 C23 1.415(6) . ? C23 C24 1.405(4) . ? C23 C25 1.432(6) . ? C24 N33 1.352(4) . ? C24 C24 1.437(7) 2_655 ? C25 C25 1.345(10) 2_655 ? C36 O37 1.404(4) . ? C38 O39 1.420(6) . ? 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 O27 Zn1 O27 167.90(11) . 2_655 ? O27 Zn1 O28 85.58(8) . . ? O27 Zn1 O28 86.18(8) 2_655 . ? O27 Zn1 O28 86.18(8) . 2_655 ? O27 Zn1 O28 85.58(8) 2_655 2_655 ? O28 Zn1 O28 94.00(12) . 2_655 ? O27 Zn1 N33 96.72(8) . . ? O27 Zn1 N33 92.77(9) 2_655 . ? O28 Zn1 N33 171.08(9) . . ? O28 Zn1 N33 94.75(9) 2_655 . ? O27 Zn1 N33 92.77(9) . 2_655 ? O27 Zn1 N33 96.72(8) 2_655 2_655 ? O28 Zn1 N33 94.75(9) . 2_655 ? O28 Zn1 N33 171.08(9) 2_655 2_655 ? N33 Zn1 N33 76.56(13) . 2_655 ? O27 C01 O26 122.8(3) . . ? O27 C01 C02 120.2(2) . . ? O26 C01 C02 117.0(2) . . ? C03 C02 C06 117.7(2) . . ? C03 C02 C01 117.1(2) . . ? C06 C02 C01 124.9(2) . . ? N29 C03 C02 125.4(3) . . ? C13 C04 N29 121.8(2) . . ? C13 C04 C05 119.7(3) . . ? N29 C04 C05 118.4(2) . . ? C10 C05 C04 118.3(2) . . ? C10 C05 C06 121.6(2) . . ? C04 C05 C06 120.1(2) . . ? O28 C06 C02 123.4(2) . . ? O28 C06 C05 119.6(2) . . ? C02 C06 C05 117.0(2) . . ? N29 C07 C08 117.9(3) . . ? N29 C07 C09 117.3(3) . . ? C08 C07 C09 60.4(3) . . ? C07 C08 C09 59.8(2) . . ? C07 C09 C08 59.7(2) . . ? N30 C10 C11 119.2(2) . . ? N30 C10 C05 122.7(2) . . ? C11 C10 C05 118.0(2) . . ? F35 C11 C10 115.4(2) . . ? F35 C11 C12 119.4(2) . . ? C10 C11 C12 125.2(3) . . ? N31 C12 C11 124.0(3) . . ? N31 C12 C13 120.3(3) . . ? C11 C12 C13 115.4(2) . . ? F34 C13 C04 119.3(3) . . ? F34 C13 C12 116.8(2) . . ? C04 C13 C12 123.1(3) . . ? N31 C14 C15 109.8(2) . . ? N32 C15 C16 110.0(2) . . ? N32 C15 C14 109.4(2) . . ? C16 C15 C14 110.6(3) . . ? N31 C17 C18 109.9(2) . . ? N32 C18 C17 108.0(2) . . ? N32 C18 C19 110.3(2) . . ? C17 C18 C19 110.8(2) . . ? N33 C20 C21 122.2(4) . . ? C22 C21 C20 120.3(4) . . ? C21 C22 C23 119.6(3) . . ? C24 C23 C22 116.6(4) . . ? C24 C23 C25 119.0(4) . . ? C22 C23 C25 124.4(4) . . ? N33 C24 C23 123.3(3) . . ? N33 C24 C24 117.01(16) . 2_655 ? C23 C24 C24 119.7(2) . 2_655 ? C25 C25 C23 121.3(2) 2_655 . ? C01 O27 Zn1 131.64(18) . . ? C06 O28 Zn1 127.10(18) . . ? C03 N29 C04 119.2(2) . . ? C03 N29 C07 118.5(2) . . ? C04 N29 C07 122.0(2) . . ? C12 N31 C14 121.7(2) . . ? C12 N31 C17 120.8(2) . . ? C14 N31 C17 112.7(2) . . ? C18 N32 C15 110.4(2) . . ? C20 N33 C24 118.1(3) . . ? C20 N33 Zn1 127.2(2) . . ? C24 N33 Zn1 114.69(19) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.384 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.069 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 823686' #TrackingRef '- k1727k1774corrected2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-[diaquadi((S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-3,7- dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylato-\k^2^O,O)zinc(II)] dihydrate ; _chemical_name_common ; trans-(diaquadi((S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1- yl)-7-oxo-3,7-dihydro-2H-(1,4)oxazino(2,3,4-ij)quinoline-6-carboxylato- kappa$2!O,O)zinc(ii)) dihydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C36 H42 F2 N6 O10 Zn, 2(H2 O)' _chemical_formula_sum 'C36 H46 F2 N6 O12 Zn' _chemical_formula_weight 858.16 _chemical_absolute_configuration rm 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' F F 0.0171 0.0103 '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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.970(5) _cell_length_b 9.739(5) _cell_length_c 17.920(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.158(5) _cell_angle_gamma 90.00 _cell_volume 1895.1(14) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4527 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.730 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8984 _exptl_absorpt_correction_T_max 0.9306 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8586 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.46 _reflns_number_total 8586 _reflns_number_gt 7368 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinovski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinovski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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. 9 restraints were used in the refinement of the structure, one due to the floating origin of the polar space group P21. 8 hydrogen-oxygen distances in the four water molecules were restrained using the DFIX command due to the instability of the unrestrained refinement. ; _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^)+(0.0677P)^2^+1.4311P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.013(10) _refine_ls_number_reflns 8586 _refine_ls_number_parameters 542 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.967 _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 0.25959(3) 0.82725(5) 0.50513(2) 0.01794(9) Uani 1 1 d . . . O1 O 0.1077(2) 1.2211(3) 0.47007(14) 0.0252(5) Uani 1 1 d . . . O2 O 0.1710(2) 1.0129(2) 0.50727(13) 0.0212(5) Uani 1 1 d . . . O3 O 0.2996(2) 0.8749(2) 0.39995(13) 0.0217(5) Uani 1 1 d . . . O4 O 0.3703(2) 0.4179(3) 0.51680(14) 0.0270(6) Uani 1 1 d . . . O5 O 0.3432(2) 0.6406(2) 0.49906(13) 0.0221(5) Uani 1 1 d . . . O6 O 0.2162(2) 0.7719(2) 0.60829(13) 0.0206(5) Uani 1 1 d . . . O7 O 0.4258(2) 0.9132(3) 0.55681(14) 0.0228(5) Uani 1 1 d D . . H7A H 0.416(4) 0.995(2) 0.567(2) 0.027 Uiso 1 1 d D . . H7B H 0.490(2) 0.911(5) 0.540(2) 0.027 Uiso 1 1 d D . . O8 O 0.0904(2) 0.7363(3) 0.45435(14) 0.0237(5) Uani 1 1 d D . . H8A H 0.028(3) 0.734(5) 0.475(2) 0.028 Uiso 1 1 d D . . H8B H 0.091(4) 0.653(2) 0.443(2) 0.028 Uiso 1 1 d D . . O9 O 0.4874(2) 1.2969(2) 0.19978(13) 0.0249(6) Uani 1 1 d . . . O10 O 0.0128(2) 0.3385(3) 0.79391(12) 0.0265(5) Uani 1 1 d . . . O11 O 0.5411(2) 0.6818(3) 0.41245(15) 0.0248(5) Uani 1 1 d D . . H11A H 0.576(4) 0.742(3) 0.440(2) 0.030 Uiso 1 1 d D . . H11B H 0.475(2) 0.675(5) 0.429(2) 0.030 Uiso 1 1 d D . . O12 O 0.0286(2) 0.4740(3) 0.41010(15) 0.0262(5) Uani 1 1 d D . . H12A H -0.035(3) 0.481(5) 0.430(2) 0.031 Uiso 1 1 d D . . H12B H 0.051(4) 0.394(2) 0.418(2) 0.031 Uiso 1 1 d D . . F13 F 0.52791(18) 0.8148(3) 0.18311(10) 0.0263(4) Uani 1 1 d . . . F14 F -0.03823(18) 0.8221(3) 0.81259(11) 0.0310(4) Uani 1 1 d . . . N15 N 0.3317(3) 1.2592(3) 0.31145(15) 0.0188(6) Uani 1 1 d . . . N16 N 0.5584(3) 1.0624(3) 0.12078(15) 0.0217(6) Uani 1 1 d . . . N17 N 0.6860(3) 1.0967(4) -0.00579(16) 0.0266(7) Uani 1 1 d . . . N18 N 0.1384(3) 0.3810(3) 0.67135(16) 0.0201(6) Uani 1 1 d . . . N19 N -0.0620(3) 0.5557(3) 0.87559(16) 0.0238(6) Uani 1 1 d . . . N20 N -0.1994(3) 0.5367(4) 0.99888(17) 0.0289(7) Uani 1 1 d . . . C21 C 0.1718(3) 1.1152(3) 0.46417(18) 0.0173(6) Uani 1 1 d . . . C22 C 0.2514(3) 1.1154(3) 0.40216(18) 0.0183(7) Uani 1 1 d . . . C23 C 0.2659(3) 1.2399(4) 0.36794(18) 0.0196(7) Uani 1 1 d . . . H23 H 0.2263 1.3176 0.3858 0.024 Uiso 1 1 calc R . . C24 C 0.3920(3) 1.1482(4) 0.28347(18) 0.0191(7) Uani 1 1 d . . . C25 C 0.3784(3) 1.0173(3) 0.31307(18) 0.0181(7) Uani 1 1 d . . . C26 C 0.3081(3) 0.9955(3) 0.37570(17) 0.0171(6) Uani 1 1 d . . . C27 C 0.4313(3) 0.9043(4) 0.28059(19) 0.0214(7) Uani 1 1 d . . . H27 H 0.4277 0.8149 0.3014 0.026 Uiso 1 1 calc R . . C28 C 0.4872(3) 0.9260(4) 0.21921(19) 0.0205(7) Uani 1 1 d . . . C29 C 0.5053(3) 1.0562(4) 0.18730(18) 0.0198(7) Uani 1 1 d . . . C30 C 0.4628(3) 1.1693(4) 0.22425(18) 0.0196(7) Uani 1 1 d . . . C31 C 0.4646(3) 1.4047(4) 0.25127(19) 0.0239(7) Uani 1 1 d . . . H31A H 0.4752 1.4953 0.2280 0.029 Uiso 1 1 calc R . . H31B H 0.5243 1.3978 0.2980 0.029 Uiso 1 1 calc R . . C32 C 0.3346(3) 1.3916(3) 0.26992(18) 0.0202(6) Uani 1 1 d . . . H32 H 0.2775 1.3832 0.2214 0.024 Uiso 1 1 calc R . . C33 C 0.2941(4) 1.5127(3) 0.3122(2) 0.0273(7) Uani 1 1 d . . . H33A H 0.2078 1.5009 0.3192 0.041 Uiso 1 1 calc R . . H33B H 0.3028 1.5968 0.2834 0.041 Uiso 1 1 calc R . . H33C H 0.3454 1.5194 0.3615 0.041 Uiso 1 1 calc R . . C34 C 0.5191(4) 1.1690(4) 0.06497(19) 0.0291(8) Uani 1 1 d . . . H34A H 0.5608 1.2569 0.0802 0.035 Uiso 1 1 calc R . . H34B H 0.4290 1.1833 0.0608 0.035 Uiso 1 1 calc R . . C35 C 0.5533(3) 1.1212(4) -0.01060(19) 0.0305(8) Uani 1 1 d . . . H35A H 0.5082 1.0355 -0.0262 0.037 Uiso 1 1 calc R . . H35B H 0.5280 1.1918 -0.0494 0.037 Uiso 1 1 calc R . . C36 C 0.7226(3) 0.9901(4) 0.05053(19) 0.0292(8) Uani 1 1 d . . . H36A H 0.8124 0.9740 0.0544 0.035 Uiso 1 1 calc R . . H36B H 0.6798 0.9032 0.0346 0.035 Uiso 1 1 calc R . . C37 C 0.6906(3) 1.0331(4) 0.12710(18) 0.0243(7) Uani 1 1 d . . . H37A H 0.7125 0.9585 0.1641 0.029 Uiso 1 1 calc R . . H37B H 0.7383 1.1159 0.1451 0.029 Uiso 1 1 calc R . . C38 C 0.7159(4) 1.0562(5) -0.0791(2) 0.0382(9) Uani 1 1 d . . . H38A H 0.8047 1.0399 -0.0754 0.057 Uiso 1 1 calc R . . H38B H 0.6919 1.1295 -0.1157 0.057 Uiso 1 1 calc R . . H38C H 0.6714 0.9718 -0.0956 0.057 Uiso 1 1 calc R . . C39 C 0.3240(3) 0.5289(4) 0.53223(18) 0.0192(7) Uani 1 1 d . . . C40 C 0.2404(3) 0.5289(4) 0.59205(17) 0.0182(7) Uani 1 1 d . . . C41 C 0.2082(3) 0.4023(4) 0.61638(18) 0.0205(7) Uani 1 1 d . . . H41 H 0.2373 0.3238 0.5927 0.025 Uiso 1 1 calc R . . C42 C 0.0951(3) 0.4916(4) 0.70850(18) 0.0200(7) Uani 1 1 d . . . C43 C 0.1216(3) 0.6254(4) 0.68650(18) 0.0183(7) Uani 1 1 d . . . C44 C 0.1952(3) 0.6496(4) 0.62565(17) 0.0182(7) Uani 1 1 d . . . C45 C 0.0761(3) 0.7375(4) 0.72288(19) 0.0221(7) Uani 1 1 d . . . H45 H 0.0896 0.8289 0.7074 0.026 Uiso 1 1 calc R . . C46 C 0.0112(3) 0.7121(4) 0.78163(19) 0.0217(7) Uani 1 1 d . . . C47 C -0.0100(3) 0.5810(4) 0.80968(19) 0.0226(7) Uani 1 1 d . . . C48 C 0.0305(3) 0.4710(4) 0.76960(18) 0.0224(7) Uani 1 1 d . . . C49 C -0.0009(4) 0.2419(4) 0.7322(2) 0.0296(8) Uani 1 1 d . . . H49A H -0.0732 0.2679 0.6953 0.036 Uiso 1 1 calc R . . H49B H -0.0161 0.1491 0.7515 0.036 Uiso 1 1 calc R . . C50 C 0.1120(3) 0.2384(4) 0.69339(19) 0.0235(7) Uani 1 1 d . . . H50 H 0.0927 0.1825 0.6464 0.028 Uiso 1 1 calc R . . C51 C 0.2237(4) 0.1754(4) 0.7412(2) 0.0332(8) Uani 1 1 d . . . H51A H 0.2359 0.2189 0.7910 0.050 Uiso 1 1 calc R . . H51B H 0.2968 0.1900 0.7165 0.050 Uiso 1 1 calc R . . H51C H 0.2103 0.0767 0.7468 0.050 Uiso 1 1 calc R . . C52 C -0.1827(3) 0.4886(4) 0.86620(19) 0.0287(8) Uani 1 1 d . . . H52A H -0.1845 0.4139 0.8286 0.034 Uiso 1 1 calc R . . H52B H -0.2474 0.5560 0.8474 0.034 Uiso 1 1 calc R . . C53 C -0.2081(3) 0.4300(4) 0.9409(2) 0.0306(8) Uani 1 1 d . . . H53A H -0.2916 0.3891 0.9346 0.037 Uiso 1 1 calc R . . H53B H -0.1480 0.3563 0.9571 0.037 Uiso 1 1 calc R . . C54 C -0.0766(4) 0.5970(5) 1.0081(2) 0.0355(9) Uani 1 1 d . . . H54A H -0.0145 0.5251 1.0238 0.043 Uiso 1 1 calc R . . H54B H -0.0700 0.6679 1.0480 0.043 Uiso 1 1 calc R . . C55 C -0.0513(4) 0.6616(4) 0.9345(2) 0.0350(9) Uani 1 1 d . . . H55A H -0.1112 0.7361 0.9196 0.042 Uiso 1 1 calc R . . H55B H 0.0326 0.7015 0.9410 0.042 Uiso 1 1 calc R . . C56 C -0.2260(4) 0.4819(5) 1.0709(2) 0.0403(10) Uani 1 1 d . . . H56A H -0.3058 0.4351 1.0633 0.060 Uiso 1 1 calc R . . H56B H -0.2284 0.5574 1.1068 0.060 Uiso 1 1 calc R . . H56C H -0.1615 0.4166 1.0907 0.060 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 Zn1 0.02057(17) 0.01514(15) 0.01940(17) 0.00236(15) 0.00733(12) 0.00062(16) O1 0.0284(12) 0.0184(12) 0.0320(13) 0.0055(10) 0.0151(11) 0.0062(10) O2 0.0254(12) 0.0175(13) 0.0228(11) 0.0050(10) 0.0102(10) 0.0013(10) O3 0.0296(12) 0.0143(12) 0.0225(11) 0.0029(9) 0.0080(10) 0.0003(9) O4 0.0310(13) 0.0190(13) 0.0344(13) 0.0042(11) 0.0164(11) 0.0053(11) O5 0.0246(12) 0.0177(12) 0.0263(12) 0.0046(10) 0.0116(10) 0.0035(10) O6 0.0284(12) 0.0152(12) 0.0198(11) 0.0023(9) 0.0083(10) 0.0007(9) O7 0.0177(11) 0.0212(13) 0.0305(13) -0.0036(11) 0.0069(10) -0.0032(11) O8 0.0232(12) 0.0240(13) 0.0251(12) -0.0012(11) 0.0073(10) -0.0005(11) O9 0.0316(12) 0.0208(15) 0.0249(11) 0.0024(9) 0.0128(10) -0.0043(10) O10 0.0354(12) 0.0230(12) 0.0229(10) 0.0004(12) 0.0104(9) -0.0073(13) O11 0.0238(12) 0.0193(12) 0.0322(14) -0.0025(11) 0.0067(11) -0.0005(10) O12 0.0256(12) 0.0201(13) 0.0356(14) 0.0038(11) 0.0134(11) 0.0008(11) F13 0.0340(9) 0.0215(12) 0.0256(9) -0.0030(9) 0.0121(8) 0.0055(10) F14 0.0379(10) 0.0279(11) 0.0308(9) 0.0022(11) 0.0171(8) 0.0081(12) N15 0.0210(13) 0.0162(14) 0.0197(13) 0.0036(11) 0.0043(11) -0.0016(11) N16 0.0200(13) 0.0301(16) 0.0157(12) 0.0043(11) 0.0056(11) 0.0036(12) N17 0.0245(14) 0.0391(19) 0.0174(14) -0.0020(12) 0.0076(12) -0.0024(13) N18 0.0238(14) 0.0175(14) 0.0186(13) 0.0012(10) 0.0016(11) -0.0019(11) N19 0.0221(14) 0.0333(17) 0.0178(13) -0.0037(12) 0.0086(11) -0.0098(12) N20 0.0252(15) 0.0371(18) 0.0268(15) 0.0024(13) 0.0115(13) 0.0006(14) C21 0.0162(14) 0.0156(17) 0.0201(15) 0.0021(13) 0.0025(12) -0.0020(12) C22 0.0190(14) 0.0195(17) 0.0161(14) 0.0004(12) 0.0015(12) -0.0001(13) C23 0.0203(15) 0.0185(16) 0.0206(15) -0.0017(13) 0.0046(13) 0.0031(13) C24 0.0194(15) 0.0187(17) 0.0185(15) -0.0006(13) 0.0007(13) 0.0002(13) C25 0.0185(15) 0.0186(17) 0.0168(14) 0.0001(12) 0.0012(12) -0.0011(13) C26 0.0194(15) 0.0155(16) 0.0167(14) -0.0006(12) 0.0036(12) -0.0004(13) C27 0.0209(15) 0.0222(18) 0.0211(15) 0.0009(14) 0.0025(13) 0.0019(14) C28 0.0206(15) 0.0210(17) 0.0193(15) -0.0023(13) 0.0007(13) 0.0053(13) C29 0.0166(15) 0.0281(19) 0.0157(14) 0.0002(13) 0.0059(12) 0.0021(13) C30 0.0185(15) 0.0216(18) 0.0191(15) 0.0020(14) 0.0037(13) -0.0022(13) C31 0.0306(17) 0.0182(17) 0.0243(17) 0.0020(14) 0.0083(14) -0.0072(14) C32 0.0259(16) 0.0141(15) 0.0209(15) 0.0012(12) 0.0047(13) -0.0002(13) C33 0.038(2) 0.0160(16) 0.0293(17) 0.0027(13) 0.0099(15) -0.0028(14) C34 0.0314(18) 0.037(2) 0.0212(16) 0.0115(15) 0.0104(14) 0.0038(16) C35 0.0282(18) 0.045(2) 0.0194(16) 0.0042(15) 0.0066(14) 0.0035(17) C36 0.0215(16) 0.041(2) 0.0259(17) -0.0025(16) 0.0056(14) 0.0031(15) C37 0.0180(15) 0.0355(19) 0.0196(15) -0.0003(14) 0.0031(13) 0.0003(14) C38 0.039(2) 0.053(3) 0.0246(18) -0.0056(17) 0.0124(17) -0.0016(19) C39 0.0180(15) 0.0184(18) 0.0213(15) 0.0007(13) 0.0036(13) 0.0037(13) C40 0.0190(15) 0.0194(17) 0.0165(14) 0.0011(12) 0.0039(13) 0.0024(13) C41 0.0205(15) 0.0212(17) 0.0195(15) 0.0002(13) 0.0018(13) 0.0001(13) C42 0.0214(15) 0.0217(17) 0.0169(14) 0.0013(13) 0.0021(12) -0.0020(14) C43 0.0167(14) 0.0227(17) 0.0157(14) 0.0027(13) 0.0028(12) 0.0000(13) C44 0.0171(14) 0.0202(18) 0.0174(15) 0.0041(13) 0.0028(12) -0.0009(13) C45 0.0232(16) 0.0214(18) 0.0223(15) 0.0049(14) 0.0057(14) 0.0002(14) C46 0.0224(16) 0.0220(19) 0.0218(16) -0.0015(13) 0.0065(14) 0.0021(14) C47 0.0194(16) 0.031(2) 0.0178(15) 0.0026(14) 0.0034(13) -0.0042(14) C48 0.0221(16) 0.0264(19) 0.0178(15) 0.0035(14) 0.0003(13) -0.0054(14) C49 0.0343(19) 0.029(2) 0.0264(17) -0.0007(15) 0.0076(16) -0.0104(16) C50 0.0282(18) 0.0210(17) 0.0206(16) 0.0011(13) 0.0007(14) -0.0089(14) C51 0.038(2) 0.0285(19) 0.0303(18) 0.0069(16) -0.0039(16) -0.0045(17) C52 0.0209(16) 0.043(2) 0.0229(16) 0.0023(15) 0.0043(13) -0.0091(15) C53 0.0248(16) 0.041(2) 0.0273(17) 0.0051(16) 0.0071(14) -0.0077(16) C54 0.035(2) 0.051(3) 0.0227(17) -0.0087(17) 0.0095(16) -0.0075(18) C55 0.044(2) 0.038(2) 0.0258(18) -0.0085(16) 0.0144(17) -0.0147(18) C56 0.044(2) 0.051(3) 0.0290(19) 0.0028(18) 0.0182(17) 0.002(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O6 2.046(2) . ? Zn1 O5 2.046(3) . ? Zn1 O3 2.048(2) . ? Zn1 O2 2.055(3) . ? Zn1 O7 2.099(2) . ? Zn1 O8 2.139(3) . ? O1 C21 1.260(4) . ? O2 C21 1.262(4) . ? O3 C26 1.260(4) . ? O4 C39 1.242(4) . ? O5 C39 1.272(4) . ? O6 C44 1.260(4) . ? O9 C30 1.358(4) . ? O9 C31 1.443(4) . ? O10 C48 1.384(5) . ? O10 C49 1.444(5) . ? F13 C28 1.369(4) . ? F14 C46 1.355(4) . ? N15 C23 1.337(4) . ? N15 C24 1.397(5) . ? N15 C32 1.491(4) . ? N16 C29 1.400(4) . ? N16 C34 1.464(4) . ? N16 C37 1.467(4) . ? N17 C38 1.453(5) . ? N17 C36 1.464(5) . ? N17 C35 1.465(5) . ? N18 C41 1.347(5) . ? N18 C42 1.386(5) . ? N18 C50 1.483(5) . ? N19 C47 1.404(4) . ? N19 C52 1.465(4) . ? N19 C55 1.468(5) . ? N20 C54 1.457(5) . ? N20 C53 1.462(5) . ? N20 C56 1.463(5) . ? C21 C22 1.508(5) . ? C22 C23 1.378(5) . ? C22 C26 1.435(5) . ? C24 C25 1.397(5) . ? C24 C30 1.416(5) . ? C25 C27 1.408(5) . ? C25 C26 1.464(5) . ? C27 C28 1.350(5) . ? C28 C29 1.417(5) . ? C29 C30 1.399(5) . ? C31 C32 1.515(5) . ? C32 C33 1.503(5) . ? C34 C35 1.529(5) . ? C36 C37 1.522(5) . ? C39 C40 1.506(4) . ? C40 C41 1.371(5) . ? C40 C44 1.440(5) . ? C42 C48 1.400(5) . ? C42 C43 1.404(5) . ? C43 C45 1.400(5) . ? C43 C44 1.465(5) . ? C45 C46 1.374(5) . ? C46 C47 1.403(5) . ? C47 C48 1.397(5) . ? C49 C50 1.504(5) . ? C50 C51 1.521(5) . ? C52 C53 1.518(5) . ? C54 C55 1.522(5) . ? 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 O6 Zn1 O5 88.70(10) . . ? O6 Zn1 O3 177.49(11) . . ? O5 Zn1 O3 89.77(10) . . ? O6 Zn1 O2 92.50(10) . . ? O5 Zn1 O2 177.69(10) . . ? O3 Zn1 O2 88.95(9) . . ? O6 Zn1 O7 90.31(10) . . ? O5 Zn1 O7 90.56(10) . . ? O3 Zn1 O7 91.70(10) . . ? O2 Zn1 O7 91.40(10) . . ? O6 Zn1 O8 88.63(10) . . ? O5 Zn1 O8 88.74(10) . . ? O3 Zn1 O8 89.34(10) . . ? O2 Zn1 O8 89.32(10) . . ? O7 Zn1 O8 178.75(12) . . ? C21 O2 Zn1 129.7(2) . . ? C26 O3 Zn1 124.4(2) . . ? C39 O5 Zn1 129.1(2) . . ? C44 O6 Zn1 123.1(2) . . ? C30 O9 C31 113.5(3) . . ? C48 O10 C49 111.7(3) . . ? C23 N15 C24 119.8(3) . . ? C23 N15 C32 123.5(3) . . ? C24 N15 C32 116.4(3) . . ? C29 N16 C34 119.6(3) . . ? C29 N16 C37 116.9(3) . . ? C34 N16 C37 112.5(3) . . ? C38 N17 C36 110.8(3) . . ? C38 N17 C35 110.0(3) . . ? C36 N17 C35 109.2(3) . . ? C41 N18 C42 120.1(3) . . ? C41 N18 C50 119.5(3) . . ? C42 N18 C50 120.5(3) . . ? C47 N19 C52 116.8(3) . . ? C47 N19 C55 118.7(3) . . ? C52 N19 C55 112.0(3) . . ? C54 N20 C53 109.5(3) . . ? C54 N20 C56 110.1(3) . . ? C53 N20 C56 111.5(3) . . ? O1 C21 O2 122.8(3) . . ? O1 C21 C22 116.7(3) . . ? O2 C21 C22 120.5(3) . . ? C23 C22 C26 119.1(3) . . ? C23 C22 C21 116.4(3) . . ? C26 C22 C21 124.5(3) . . ? N15 C23 C22 124.7(3) . . ? C25 C24 N15 119.2(3) . . ? C25 C24 C30 121.1(3) . . ? N15 C24 C30 119.6(3) . . ? C24 C25 C27 118.9(3) . . ? C24 C25 C26 121.3(3) . . ? C27 C25 C26 119.7(3) . . ? O3 C26 C22 126.0(3) . . ? O3 C26 C25 118.2(3) . . ? C22 C26 C25 115.8(3) . . ? C28 C27 C25 118.4(3) . . ? C27 C28 F13 118.5(3) . . ? C27 C28 C29 125.1(3) . . ? F13 C28 C29 116.3(3) . . ? C30 C29 N16 125.2(3) . . ? C30 C29 C28 116.0(3) . . ? N16 C29 C28 118.8(3) . . ? O9 C30 C29 118.2(3) . . ? O9 C30 C24 122.0(3) . . ? C29 C30 C24 119.7(3) . . ? O9 C31 C32 109.5(3) . . ? N15 C32 C33 113.5(3) . . ? N15 C32 C31 105.7(3) . . ? C33 C32 C31 113.6(3) . . ? N16 C34 C35 107.7(3) . . ? N17 C35 C34 111.4(3) . . ? N17 C36 C37 110.5(3) . . ? N16 C37 C36 109.6(3) . . ? O4 C39 O5 122.7(3) . . ? O4 C39 C40 117.9(3) . . ? O5 C39 C40 119.4(3) . . ? C41 C40 C44 118.8(3) . . ? C41 C40 C39 115.9(3) . . ? C44 C40 C39 125.3(3) . . ? N18 C41 C40 124.7(3) . . ? N18 C42 C48 120.7(3) . . ? N18 C42 C43 119.2(3) . . ? C48 C42 C43 120.1(3) . . ? C45 C43 C42 119.4(3) . . ? C45 C43 C44 119.5(3) . . ? C42 C43 C44 121.1(3) . . ? O6 C44 C40 125.6(3) . . ? O6 C44 C43 118.3(3) . . ? C40 C44 C43 116.0(3) . . ? C46 C45 C43 118.3(3) . . ? F14 C46 C45 116.9(3) . . ? F14 C46 C47 118.4(3) . . ? C45 C46 C47 124.7(3) . . ? C48 C47 C46 115.6(3) . . ? C48 C47 N19 119.6(3) . . ? C46 C47 N19 124.7(3) . . ? O10 C48 C47 118.9(3) . . ? O10 C48 C42 119.3(3) . . ? C47 C48 C42 121.7(3) . . ? O10 C49 C50 111.4(3) . . ? N18 C50 C49 107.9(3) . . ? N18 C50 C51 110.8(3) . . ? C49 C50 C51 113.5(3) . . ? N19 C52 C53 110.0(3) . . ? N20 C53 C52 111.0(3) . . ? N20 C54 C55 110.4(3) . . ? N19 C55 C54 109.1(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.372 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.105