# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jean-Francois Carpentier' _publ_contact_author_email JEAN-FRANCOIS.CARPENTIER@UNIV-RENNES1.FR _publ_section_title ; Zinc Complexes of Fluorous Alkoxide-Imino Ligands: Synthesis, Structure, and Use in Ring-Opening Polymerization of Lactide and ?-Butyrolactone ; _publ_requested_category FM loop_ _publ_author_name 'Jean-Francois Carpentier' 'Ekaterina Grunova' 'Thierry Roisnel' # Attachment 'complex1_GE209_100K_APEX_10mars08.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-03-10 at 18:00:59 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\progs\wingx\files\archive.dat # CIF files read : job struct data_1 _database_code_depnum_ccdc_archive 'CCDC 718597' _audit_creation_date 2008-03-10T18:00:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H20 F12 N2 O2 Zn1' _chemical_formula_sum 'C24 H20 F12 N2 O2 Zn' _chemical_formula_weight 661.79 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 10.9991(3) _cell_length_b 22.5468(7) _cell_length_c 11.4441(3) _cell_angle_alpha 90 _cell_angle_beta 113.6710(10) _cell_angle_gamma 90 _cell_volume 2599.29(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9343 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 27.37 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.057 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.683 _exptl_absorpt_correction_T_max 0.752 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_unetI/netI 0.0315 _diffrn_reflns_number 22271 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 5908 _reflns_number_gt 5217 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0260P)^2^+1.5149P] 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_number_reflns 5908 _refine_ls_number_parameters 372 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0666 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.374 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn -0.027896(17) 0.138903(8) 0.670057(17) 0.01193(6) Uani 1 d . . . O1 O -0.14337(11) 0.07324(5) 0.65089(10) 0.0157(2) Uani 1 d . . . N11 N -0.02986(12) 0.17256(6) 0.83574(13) 0.0133(3) Uani 1 d . . . C11 C -0.02921(16) 0.23649(7) 0.84791(15) 0.0141(3) Uani 1 d . . . C12 C -0.14705(17) 0.26757(8) 0.78511(17) 0.0193(4) Uani 1 d . . . H12 H -0.2275 0.2468 0.7396 0.023 Uiso 1 calc R . . C13 C -0.14619(18) 0.32904(8) 0.78947(18) 0.0222(4) Uani 1 d . . . H13 H -0.2263 0.3504 0.7467 0.027 Uiso 1 calc R . . C14 C -0.02873(18) 0.35963(8) 0.85610(18) 0.0216(4) Uani 1 d . . . H14 H -0.0287 0.4017 0.8591 0.026 Uiso 1 calc R . . C15 C 0.08835(18) 0.32837(8) 0.91821(17) 0.0221(4) Uani 1 d . . . H15 H 0.1686 0.3492 0.9639 0.027 Uiso 1 calc R . . C16 C 0.08921(17) 0.26667(8) 0.91416(16) 0.0184(4) Uani 1 d . . . H16 H 0.1696 0.2454 0.9561 0.022 Uiso 1 calc R . . C17 C -0.06392(15) 0.13904(7) 0.90816(15) 0.0143(3) Uani 1 d . . . C18 C -0.09564(18) 0.16053(8) 1.01686(17) 0.0211(4) Uani 1 d . . . H18A H -0.0784 0.2032 1.0285 0.032 Uiso 1 calc R . . H18B H -0.0399 0.1396 1.0951 0.032 Uiso 1 calc R . . H18C H -0.1894 0.1528 0.9979 0.032 Uiso 1 calc R . . C19 C -0.07038(16) 0.07260(7) 0.88582(15) 0.0156(3) Uani 1 d . . . H19A H -0.0961 0.0533 0.9502 0.019 Uiso 1 calc R . . H19B H 0.0196 0.0584 0.9 0.019 Uiso 1 calc R . . C20 C -0.16895(15) 0.05213(7) 0.75038(15) 0.0144(3) Uani 1 d . . . C21 C -0.31242(17) 0.07015(8) 0.72957(17) 0.0208(4) Uani 1 d . . . F21A F -0.40370(10) 0.04936(5) 0.62009(11) 0.0301(3) Uani 1 d . . . F21B F -0.34767(11) 0.05199(6) 0.82325(12) 0.0409(3) Uani 1 d . . . F21C F -0.32449(10) 0.12959(5) 0.72499(11) 0.0279(3) Uani 1 d . . . C22 C -0.15882(17) -0.01631(8) 0.74988(16) 0.0195(4) Uani 1 d . . . F22A F -0.03394(10) -0.03276(5) 0.77321(11) 0.0295(3) Uani 1 d . . . F22B F -0.23724(11) -0.04059(5) 0.63849(10) 0.0251(2) Uani 1 d . . . F22C F -0.18949(12) -0.04276(5) 0.84094(10) 0.0299(3) Uani 1 d . . . O2 O -0.07822(10) 0.19509(5) 0.53407(11) 0.0146(2) Uani 1 d . . . N31 N 0.15552(13) 0.11797(6) 0.67954(13) 0.0139(3) Uani 1 d . . . C31 C 0.20546(15) 0.05853(8) 0.71762(16) 0.0157(3) Uani 1 d . . . C32 C 0.17959(17) 0.01400(8) 0.62697(17) 0.0212(4) Uani 1 d . . . H32 H 0.1313 0.0227 0.5391 0.025 Uiso 1 calc R . . C33 C 0.22461(19) -0.04326(9) 0.66526(19) 0.0279(4) Uani 1 d . . . H33 H 0.2075 -0.0737 0.6034 0.033 Uiso 1 calc R . . C34 C 0.29444(19) -0.05605(9) 0.7935(2) 0.0289(4) Uani 1 d . . . H34 H 0.3253 -0.0952 0.8194 0.035 Uiso 1 calc R . . C35 C 0.31930(18) -0.01161(9) 0.88404(18) 0.0266(4) Uani 1 d . . . H35 H 0.3674 -0.0205 0.9718 0.032 Uiso 1 calc R . . C36 C 0.27398(17) 0.04608(8) 0.84683(16) 0.0202(4) Uani 1 d . . . H36 H 0.2897 0.0764 0.9088 0.024 Uiso 1 calc R . . C37 C 0.21533(15) 0.15379(8) 0.63265(15) 0.0147(3) Uani 1 d . . . C38 C 0.34091(16) 0.13987(8) 0.61685(17) 0.0210(4) Uani 1 d . . . H38A H 0.3709 0.0999 0.6493 0.031 Uiso 1 calc R . . H38B H 0.4094 0.1688 0.6646 0.031 Uiso 1 calc R . . H38C H 0.3247 0.1418 0.5262 0.031 Uiso 1 calc R . . C39 C 0.16075(15) 0.21607(8) 0.59616(16) 0.0159(3) Uani 1 d . . . H39A H 0.2171 0.237 0.5602 0.019 Uiso 1 calc R . . H39B H 0.1698 0.2372 0.675 0.019 Uiso 1 calc R . . C40 C 0.01356(15) 0.22117(7) 0.49879(15) 0.0130(3) Uani 1 d . . . C41 C -0.00006(16) 0.19461(8) 0.36897(16) 0.0186(4) Uani 1 d . . . F41A F -0.12474(10) 0.19682(5) 0.28056(9) 0.0259(2) Uani 1 d . . . F41B F 0.07600(12) 0.22213(6) 0.31810(11) 0.0380(3) Uani 1 d . . . F41C F 0.03567(11) 0.13752(5) 0.38186(10) 0.0302(3) Uani 1 d . . . C42 C -0.01758(16) 0.28860(8) 0.48211(16) 0.0167(3) Uani 1 d . . . F42A F -0.00717(11) 0.31266(5) 0.59226(10) 0.0266(2) Uani 1 d . . . F42B F -0.14158(9) 0.29960(4) 0.39665(10) 0.0215(2) Uani 1 d . . . F42C F 0.06409(10) 0.31986(5) 0.44321(11) 0.0281(3) Uani 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 0.01306(9) 0.01130(10) 0.01285(10) 0.00000(7) 0.00668(7) 0.00046(7) O1 0.0193(6) 0.0162(6) 0.0128(6) -0.0009(5) 0.0077(5) -0.0044(5) N11 0.0125(6) 0.0135(7) 0.0134(7) -0.0017(5) 0.0046(5) 0.0014(5) C11 0.0193(8) 0.0124(8) 0.0138(8) -0.0017(6) 0.0099(6) 0.0011(6) C12 0.0165(8) 0.0182(9) 0.0225(9) -0.0028(7) 0.0070(7) 0.0007(7) C13 0.0224(9) 0.0173(9) 0.0276(10) -0.0003(7) 0.0109(8) 0.0053(7) C14 0.0319(10) 0.0124(9) 0.0262(10) -0.0018(7) 0.0176(8) -0.0003(7) C15 0.0221(9) 0.0212(10) 0.0243(9) -0.0060(7) 0.0106(7) -0.0078(7) C16 0.0168(8) 0.0199(9) 0.0191(9) -0.0012(7) 0.0078(7) 0.0007(7) C17 0.0125(7) 0.0161(9) 0.0116(8) -0.0004(6) 0.0019(6) 0.0021(6) C18 0.0307(9) 0.0177(9) 0.0184(9) -0.0016(7) 0.0136(7) 0.0008(8) C19 0.0181(8) 0.0139(8) 0.0137(8) 0.0013(6) 0.0054(6) 0.0020(6) C20 0.0148(7) 0.0143(9) 0.0148(8) -0.0005(6) 0.0064(6) -0.0013(6) C21 0.0184(8) 0.0257(10) 0.0195(9) 0.0021(7) 0.0089(7) -0.0007(7) F21A 0.0167(5) 0.0323(7) 0.0328(6) -0.0039(5) 0.0012(5) -0.0050(4) F21B 0.0303(6) 0.0637(9) 0.0404(7) 0.0183(6) 0.0263(6) 0.0082(6) F21C 0.0185(5) 0.0238(6) 0.0378(7) -0.0030(5) 0.0075(5) 0.0062(4) C22 0.0236(9) 0.0169(9) 0.0166(8) -0.0008(7) 0.0067(7) -0.0042(7) F22A 0.0278(6) 0.0165(6) 0.0407(7) -0.0035(5) 0.0101(5) 0.0052(4) F22B 0.0338(6) 0.0182(6) 0.0205(5) -0.0055(4) 0.0081(5) -0.0087(5) F22C 0.0491(7) 0.0180(6) 0.0232(6) 0.0029(4) 0.0151(5) -0.0109(5) O2 0.0124(5) 0.0150(6) 0.0164(6) 0.0035(5) 0.0058(4) -0.0002(4) N31 0.0127(6) 0.0160(7) 0.0118(7) 0.0002(5) 0.0037(5) 0.0025(5) C31 0.0119(7) 0.0180(9) 0.0181(8) 0.0023(7) 0.0069(6) 0.0033(6) C32 0.0229(9) 0.0214(10) 0.0183(9) 0.0003(7) 0.0073(7) 0.0048(7) C33 0.0317(10) 0.0212(10) 0.0315(11) -0.0042(8) 0.0134(9) 0.0060(8) C34 0.0299(10) 0.0184(10) 0.0380(11) 0.0086(8) 0.0133(9) 0.0092(8) C35 0.0245(9) 0.0292(11) 0.0219(9) 0.0109(8) 0.0049(8) 0.0042(8) C36 0.0211(8) 0.0231(10) 0.0156(8) 0.0003(7) 0.0065(7) 0.0008(7) C37 0.0127(7) 0.0193(9) 0.0093(7) -0.0013(6) 0.0015(6) -0.0001(6) C38 0.0147(8) 0.0272(10) 0.0234(9) 0.0036(8) 0.0101(7) 0.0026(7) C39 0.0130(7) 0.0170(9) 0.0162(8) 0.0003(7) 0.0042(6) -0.0028(6) C40 0.0133(7) 0.0132(8) 0.0124(8) 0.0000(6) 0.0050(6) -0.0004(6) C41 0.0172(8) 0.0217(10) 0.0156(8) 0.0003(7) 0.0054(7) 0.0034(7) F41A 0.0224(5) 0.0320(6) 0.0146(5) -0.0048(4) -0.0019(4) 0.0079(5) F41B 0.0441(7) 0.0533(8) 0.0299(6) -0.0086(6) 0.0287(6) -0.0134(6) F41C 0.0383(6) 0.0231(6) 0.0205(6) -0.0063(4) 0.0028(5) 0.0138(5) C42 0.0166(8) 0.0174(9) 0.0153(8) 0.0012(7) 0.0054(6) -0.0010(7) F42A 0.0398(6) 0.0176(6) 0.0197(5) -0.0043(4) 0.0091(5) 0.0043(5) F42B 0.0185(5) 0.0179(5) 0.0232(5) 0.0042(4) 0.0032(4) 0.0042(4) F42C 0.0264(5) 0.0202(6) 0.0402(7) 0.0104(5) 0.0161(5) -0.0027(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.9051(11) . ? Zn1 O2 1.9083(11) . ? Zn1 N31 2.0319(13) . ? Zn1 N11 2.0505(13) . ? O1 C20 1.3636(19) . ? N11 C17 1.284(2) . ? N11 C11 1.448(2) . ? C11 C12 1.393(2) . ? C11 C16 1.393(2) . ? C12 C13 1.387(3) . ? C12 H12 0.95 . ? C13 C14 1.391(3) . ? C13 H13 0.95 . ? C14 C15 1.388(3) . ? C14 H14 0.95 . ? C15 C16 1.392(3) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 C18 1.501(2) . ? C17 C19 1.516(2) . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 C20 1.563(2) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 C22 1.547(2) . ? C20 C21 1.553(2) . ? C21 F21A 1.337(2) . ? C21 F21B 1.342(2) . ? C21 F21C 1.346(2) . ? C22 F22B 1.336(2) . ? C22 F22A 1.342(2) . ? C22 F22C 1.356(2) . ? O2 C40 1.3620(19) . ? N31 C37 1.287(2) . ? N31 C31 1.448(2) . ? C31 C32 1.389(2) . ? C31 C36 1.392(2) . ? C32 C33 1.389(3) . ? C32 H32 0.95 . ? C33 C34 1.386(3) . ? C33 H33 0.95 . ? C34 C35 1.388(3) . ? C34 H34 0.95 . ? C35 C36 1.397(3) . ? C35 H35 0.95 . ? C36 H36 0.95 . ? C37 C38 1.497(2) . ? C37 C39 1.518(2) . ? C38 H38A 0.98 . ? C38 H38B 0.98 . ? C38 H38C 0.98 . ? C39 C40 1.558(2) . ? C39 H39A 0.99 . ? C39 H39B 0.99 . ? C40 C41 1.552(2) . ? C40 C42 1.553(2) . ? C41 F41C 1.337(2) . ? C41 F41A 1.3389(19) . ? C41 F41B 1.347(2) . ? C42 F42A 1.334(2) . ? C42 F42B 1.3443(18) . ? C42 F42C 1.3502(19) . ? 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 O2 117.41(5) . . ? O1 Zn1 N31 115.30(5) . . ? O2 Zn1 N31 98.89(5) . . ? O1 Zn1 N11 98.05(5) . . ? O2 Zn1 N11 113.65(5) . . ? N31 Zn1 N11 114.55(5) . . ? C20 O1 Zn1 121.78(10) . . ? C17 N11 C11 121.04(14) . . ? C17 N11 Zn1 119.55(11) . . ? C11 N11 Zn1 117.13(10) . . ? C12 C11 C16 120.52(16) . . ? C12 C11 N11 118.93(14) . . ? C16 C11 N11 120.40(14) . . ? C13 C12 C11 119.53(16) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.44(17) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 119.71(17) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.52(16) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 119.27(16) . . ? C15 C16 H16 120.4 . . ? C11 C16 H16 120.4 . . ? N11 C17 C18 124.76(15) . . ? N11 C17 C19 118.61(14) . . ? C18 C17 C19 116.62(14) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 C20 115.21(13) . . ? C17 C19 H19A 108.5 . . ? C20 C19 H19A 108.5 . . ? C17 C19 H19B 108.5 . . ? C20 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? O1 C20 C22 107.80(13) . . ? O1 C20 C21 108.56(13) . . ? C22 C20 C21 109.31(14) . . ? O1 C20 C19 115.57(13) . . ? C22 C20 C19 106.02(13) . . ? C21 C20 C19 109.43(13) . . ? F21A C21 F21B 107.01(14) . . ? F21A C21 F21C 106.71(14) . . ? F21B C21 F21C 106.22(15) . . ? F21A C21 C20 112.74(14) . . ? F21B C21 C20 113.54(14) . . ? F21C C21 C20 110.18(14) . . ? F22B C22 F22A 107.07(14) . . ? F22B C22 F22C 106.78(13) . . ? F22A C22 F22C 106.04(14) . . ? F22B C22 C20 113.09(14) . . ? F22A C22 C20 110.14(13) . . ? F22C C22 C20 113.29(14) . . ? C40 O2 Zn1 121.43(9) . . ? C37 N31 C31 120.72(14) . . ? C37 N31 Zn1 119.65(11) . . ? C31 N31 Zn1 118.67(10) . . ? C32 C31 C36 120.59(16) . . ? C32 C31 N31 120.35(15) . . ? C36 C31 N31 118.98(15) . . ? C31 C32 C33 119.74(17) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? C34 C33 C32 120.21(18) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C33 C34 C35 119.97(18) . . ? C33 C34 H34 120 . . ? C35 C34 H34 120 . . ? C34 C35 C36 120.37(17) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C31 C36 C35 119.09(17) . . ? C31 C36 H36 120.5 . . ? C35 C36 H36 120.5 . . ? N31 C37 C38 124.74(15) . . ? N31 C37 C39 118.89(14) . . ? C38 C37 C39 116.29(14) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C37 C39 C40 116.59(13) . . ? C37 C39 H39A 108.1 . . ? C40 C39 H39A 108.1 . . ? C37 C39 H39B 108.1 . . ? C40 C39 H39B 108.1 . . ? H39A C39 H39B 107.3 . . ? O2 C40 C41 108.60(13) . . ? O2 C40 C42 107.81(13) . . ? C41 C40 C42 109.16(13) . . ? O2 C40 C39 115.92(13) . . ? C41 C40 C39 109.23(13) . . ? C42 C40 C39 105.94(13) . . ? F41C C41 F41A 106.61(14) . . ? F41C C41 F41B 106.57(14) . . ? F41A C41 F41B 106.36(14) . . ? F41C C41 C40 110.78(14) . . ? F41A C41 C40 112.63(13) . . ? F41B C41 C40 113.44(14) . . ? F42A C42 F42B 106.83(13) . . ? F42A C42 F42C 106.45(14) . . ? F42B C42 F42C 106.19(13) . . ? F42A C42 C40 110.53(13) . . ? F42B C42 C40 112.29(13) . . ? F42C C42 C40 114.11(13) . . ? 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 Zn1 O1 C20 -140.32(11) . . . . ? N31 Zn1 O1 C20 103.74(12) . . . . ? N11 Zn1 O1 C20 -18.33(12) . . . . ? O1 Zn1 N11 C17 20.61(12) . . . . ? O2 Zn1 N11 C17 145.32(11) . . . . ? N31 Zn1 N11 C17 -102.01(12) . . . . ? O1 Zn1 N11 C11 -142.40(11) . . . . ? O2 Zn1 N11 C11 -17.69(12) . . . . ? N31 Zn1 N11 C11 94.98(11) . . . . ? C17 N11 C11 C12 -84.47(19) . . . . ? Zn1 N11 C11 C12 78.27(16) . . . . ? C17 N11 C11 C16 99.88(18) . . . . ? Zn1 N11 C11 C16 -97.38(15) . . . . ? C16 C11 C12 C13 -0.4(3) . . . . ? N11 C11 C12 C13 -176.04(15) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? C12 C13 C14 C15 0.2(3) . . . . ? C13 C14 C15 C16 0.1(3) . . . . ? C14 C15 C16 C11 -0.6(3) . . . . ? C12 C11 C16 C15 0.7(2) . . . . ? N11 C11 C16 C15 176.31(15) . . . . ? C11 N11 C17 C18 -4.9(2) . . . . ? Zn1 N11 C17 C18 -167.24(12) . . . . ? C11 N11 C17 C19 176.48(14) . . . . ? Zn1 N11 C17 C19 14.15(19) . . . . ? N11 C17 C19 C20 -59.4(2) . . . . ? C18 C17 C19 C20 121.88(16) . . . . ? Zn1 O1 C20 C22 -134.64(11) . . . . ? Zn1 O1 C20 C21 107.05(13) . . . . ? Zn1 O1 C20 C19 -16.29(18) . . . . ? C17 C19 C20 O1 60.71(19) . . . . ? C17 C19 C20 C22 -179.94(13) . . . . ? C17 C19 C20 C21 -62.16(18) . . . . ? O1 C20 C21 F21A 58.71(18) . . . . ? C22 C20 C21 F21A -58.64(18) . . . . ? C19 C20 C21 F21A -174.35(14) . . . . ? O1 C20 C21 F21B -179.38(14) . . . . ? C22 C20 C21 F21B 63.27(19) . . . . ? C19 C20 C21 F21B -52.43(19) . . . . ? O1 C20 C21 F21C -60.38(17) . . . . ? C22 C20 C21 F21C -177.73(13) . . . . ? C19 C20 C21 F21C 66.57(17) . . . . ? O1 C20 C22 F22B -54.95(18) . . . . ? C21 C20 C22 F22B 62.87(18) . . . . ? C19 C20 C22 F22B -179.27(13) . . . . ? O1 C20 C22 F22A 64.80(17) . . . . ? C21 C20 C22 F22A -177.37(13) . . . . ? C19 C20 C22 F22A -59.51(17) . . . . ? O1 C20 C22 F22C -176.63(13) . . . . ? C21 C20 C22 F22C -58.80(18) . . . . ? C19 C20 C22 F22C 59.06(17) . . . . ? O1 Zn1 O2 C40 -142.44(11) . . . . ? N31 Zn1 O2 C40 -17.81(12) . . . . ? N11 Zn1 O2 C40 104.02(12) . . . . ? O1 Zn1 N31 C37 146.74(12) . . . . ? O2 Zn1 N31 C37 20.63(13) . . . . ? N11 Zn1 N31 C37 -100.55(13) . . . . ? O1 Zn1 N31 C31 -22.10(13) . . . . ? O2 Zn1 N31 C31 -148.20(11) . . . . ? N11 Zn1 N31 C31 90.62(12) . . . . ? C37 N31 C31 C32 -79.9(2) . . . . ? Zn1 N31 C31 C32 88.82(17) . . . . ? C37 N31 C31 C36 103.26(19) . . . . ? Zn1 N31 C31 C36 -88.03(16) . . . . ? C36 C31 C32 C33 -1.2(3) . . . . ? N31 C31 C32 C33 -178.01(16) . . . . ? C31 C32 C33 C34 0.4(3) . . . . ? C32 C33 C34 C35 0.1(3) . . . . ? C33 C34 C35 C36 0.2(3) . . . . ? C32 C31 C36 C35 1.5(3) . . . . ? N31 C31 C36 C35 178.37(15) . . . . ? C34 C35 C36 C31 -1.0(3) . . . . ? C31 N31 C37 C38 -2.3(2) . . . . ? Zn1 N31 C37 C38 -170.87(12) . . . . ? C31 N31 C37 C39 -178.96(14) . . . . ? Zn1 N31 C37 C39 12.4(2) . . . . ? N31 C37 C39 C40 -56.7(2) . . . . ? C38 C37 C39 C40 126.36(15) . . . . ? Zn1 O2 C40 C41 107.49(12) . . . . ? Zn1 O2 C40 C42 -134.36(11) . . . . ? Zn1 O2 C40 C39 -15.88(18) . . . . ? C37 C39 C40 O2 58.68(19) . . . . ? C37 C39 C40 C41 -64.36(18) . . . . ? C37 C39 C40 C42 178.18(14) . . . . ? O2 C40 C41 F41C -67.33(17) . . . . ? C42 C40 C41 F41C 175.38(13) . . . . ? C39 C40 C41 F41C 59.96(17) . . . . ? O2 C40 C41 F41A 51.98(18) . . . . ? C42 C40 C41 F41A -65.32(17) . . . . ? C39 C40 C41 F41A 179.27(14) . . . . ? O2 C40 C41 F41B 172.86(13) . . . . ? C42 C40 C41 F41B 55.57(18) . . . . ? C39 C40 C41 F41B -59.84(18) . . . . ? O2 C40 C42 F42A 61.96(16) . . . . ? C41 C40 C42 F42A 179.75(13) . . . . ? C39 C40 C42 F42A -62.74(16) . . . . ? O2 C40 C42 F42B -57.22(17) . . . . ? C41 C40 C42 F42B 60.57(17) . . . . ? C39 C40 C42 F42B 178.08(13) . . . . ? O2 C40 C42 F42C -178.12(13) . . . . ? C41 C40 C42 F42C -60.33(17) . . . . ? C39 C40 C42 F42C 57.18(17) . . . . ? # Attachment 'complex3_GE224_2_100K_APEX_31mars08_archive.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-03-31 at 18:52:11 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\progs\wingx\files\archive.dat # CIF files read : job struct data_3 _database_code_depnum_ccdc_archive 'CCDC 718598' _audit_creation_date 2008-03-31T18:52:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H36 F12 N2 O2 Zn1' _chemical_formula_sum 'C34 H36 F12 N2 O2 Zn' _chemical_formula_weight 798.02 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 11.3204(5) _cell_length_b 13.5253(5) _cell_length_c 22.0649(9) _cell_angle_alpha 90 _cell_angle_beta 90.378(2) _cell_angle_gamma 90 _cell_volume 3378.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6108 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.49 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.22 _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.828 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.732 _exptl_absorpt_correction_T_max 0.833 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_unetI/netI 0.0338 _diffrn_reflns_number 36716 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 7744 _reflns_number_gt 6520 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0310P)^2^+1.2264P] 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_number_reflns 7744 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0714 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.419 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.514163(15) 0.181120(12) 0.121227(8) 0.01205(5) Uani 1 d . . . O1 O 0.47028(9) 0.05922(7) 0.15926(5) 0.0162(2) Uani 1 d . . . C2 C 0.50906(13) -0.02893(11) 0.13731(7) 0.0137(3) Uani 1 d . . . C3 C 0.40071(14) -0.09597(11) 0.12466(7) 0.0175(3) Uani 1 d . . . F3A F 0.42974(9) -0.18818(7) 0.10842(5) 0.0257(2) Uani 1 d . . . F3B F 0.32844(8) -0.10332(7) 0.17203(5) 0.0271(2) Uani 1 d . . . F3C F 0.33521(8) -0.05851(7) 0.07892(5) 0.0266(2) Uani 1 d . . . C4 C 0.58870(14) -0.07883(11) 0.18521(7) 0.0191(3) Uani 1 d . . . F4A F 0.67539(8) -0.01741(7) 0.20321(4) 0.0250(2) Uani 1 d . . . F4B F 0.64240(9) -0.16084(7) 0.16468(5) 0.0278(2) Uani 1 d . . . F4C F 0.52969(9) -0.10474(8) 0.23512(4) 0.0298(2) Uani 1 d . . . C5 C 0.57692(13) -0.02064(11) 0.07647(7) 0.0138(3) Uani 1 d . . . H5A H 0.5985 -0.088 0.0629 0.017 Uiso 1 calc R . . H5B H 0.5231 0.0078 0.0455 0.017 Uiso 1 calc R . . C6 C 0.68807(13) 0.04182(11) 0.07926(7) 0.0133(3) Uani 1 d . . . C7 C 0.80310(13) -0.01044(11) 0.07135(7) 0.0145(3) Uani 1 d . . . C8 C 0.81854(14) -0.07536(11) 0.02286(7) 0.0163(3) Uani 1 d . . . H8 H 0.7549 -0.0887 -0.0042 0.02 Uiso 1 calc R . . C9 C 0.92795(14) -0.12044(11) 0.01445(7) 0.0180(3) Uani 1 d . . . H9 H 0.9395 -0.1629 -0.0193 0.022 Uiso 1 calc R . . C10 C 1.01964(14) -0.10389(11) 0.05476(8) 0.0187(3) Uani 1 d . . . H10 H 1.0941 -0.1345 0.0484 0.022 Uiso 1 calc R . . C11 C 1.00346(14) -0.04260(11) 0.10456(8) 0.0181(3) Uani 1 d . . . H11 H 1.0659 -0.0328 0.1329 0.022 Uiso 1 calc R . . C12 C 0.89585(13) 0.00414(11) 0.11275(7) 0.0164(3) Uani 1 d . . . H12 H 0.8849 0.0464 0.1467 0.02 Uiso 1 calc R . . N13 N 0.67616(11) 0.13600(9) 0.08608(6) 0.0133(3) Uani 1 d . . . C14 C 0.77784(13) 0.20372(11) 0.07617(7) 0.0137(3) Uani 1 d . . . H14 H 0.849 0.1629 0.0666 0.016 Uiso 1 calc R . . C15 C 0.74942(13) 0.26884(11) 0.02137(7) 0.0154(3) Uani 1 d . . . H15A H 0.6757 0.306 0.029 0.018 Uiso 1 calc R . . H15B H 0.7365 0.2266 -0.0147 0.018 Uiso 1 calc R . . C16 C 0.85013(14) 0.34182(11) 0.00883(7) 0.0171(3) Uani 1 d . . . H16A H 0.9205 0.3048 -0.0049 0.021 Uiso 1 calc R . . H16B H 0.826 0.3872 -0.0242 0.021 Uiso 1 calc R . . C17 C 0.88241(15) 0.40212(11) 0.06509(8) 0.0200(3) Uani 1 d . . . H17A H 0.9525 0.4433 0.0564 0.024 Uiso 1 calc R . . H17B H 0.8162 0.4469 0.0751 0.024 Uiso 1 calc R . . C18 C 0.90886(14) 0.33564(12) 0.11926(7) 0.0192(3) Uani 1 d . . . H18A H 0.9244 0.377 0.1555 0.023 Uiso 1 calc R . . H18B H 0.9807 0.2962 0.1111 0.023 Uiso 1 calc R . . C19 C 0.80509(13) 0.26583(12) 0.13196(7) 0.0166(3) Uani 1 d . . . H19A H 0.8252 0.222 0.1665 0.02 Uiso 1 calc R . . H19B H 0.7346 0.3049 0.1431 0.02 Uiso 1 calc R . . O21 O 0.40948(10) 0.23138(8) 0.06012(5) 0.0175(2) Uani 1 d . . . C22 C 0.38294(13) 0.32929(11) 0.05756(7) 0.0141(3) Uani 1 d . . . C23 C 0.38552(14) 0.36147(12) -0.00961(8) 0.0185(3) Uani 1 d . . . F23A F 0.49684(8) 0.36265(7) -0.03034(4) 0.0231(2) Uani 1 d . . . F23B F 0.32433(9) 0.30107(7) -0.04583(4) 0.0267(2) Uani 1 d . . . F23C F 0.34226(9) 0.45336(7) -0.01865(4) 0.0253(2) Uani 1 d . . . C24 C 0.25619(14) 0.34686(12) 0.08216(8) 0.0195(3) Uani 1 d . . . F24A F 0.17243(9) 0.31177(8) 0.04510(5) 0.0315(3) Uani 1 d . . . F24B F 0.23075(8) 0.44286(7) 0.09126(5) 0.0293(2) Uani 1 d . . . F24C F 0.24266(9) 0.30220(8) 0.13588(5) 0.0295(2) Uani 1 d . . . C25 C 0.46993(13) 0.39884(11) 0.09271(7) 0.0137(3) Uani 1 d . . . H25A H 0.5501 0.3899 0.0759 0.016 Uiso 1 calc R . . H25B H 0.4462 0.4682 0.0851 0.016 Uiso 1 calc R . . C26 C 0.47590(12) 0.38238(11) 0.16053(7) 0.0124(3) Uani 1 d . . . C27 C 0.45666(13) 0.47270(11) 0.19847(7) 0.0147(3) Uani 1 d . . . C28 C 0.35734(14) 0.48401(12) 0.23489(7) 0.0181(3) Uani 1 d . . . H28 H 0.3 0.4329 0.2369 0.022 Uiso 1 calc R . . C29 C 0.34234(15) 0.57028(12) 0.26831(8) 0.0236(4) Uani 1 d . . . H29 H 0.2749 0.5779 0.2933 0.028 Uiso 1 calc R . . C30 C 0.42561(17) 0.64507(12) 0.26518(8) 0.0259(4) Uani 1 d . . . H30 H 0.4153 0.7038 0.2881 0.031 Uiso 1 calc R . . C31 C 0.52382(17) 0.63448(12) 0.22874(8) 0.0274(4) Uani 1 d . . . H31 H 0.5808 0.6859 0.2268 0.033 Uiso 1 calc R . . C32 C 0.53915(15) 0.54884(12) 0.19504(8) 0.0218(4) Uani 1 d . . . H32 H 0.606 0.5422 0.1696 0.026 Uiso 1 calc R . . N33 N 0.50269(11) 0.29659(9) 0.18150(6) 0.0127(3) Uani 1 d . . . C34 C 0.50787(13) 0.27816(11) 0.24804(7) 0.0137(3) Uani 1 d . . . H34 H 0.5057 0.3429 0.2699 0.016 Uiso 1 calc R . . C35 C 0.39940(14) 0.21699(11) 0.26564(7) 0.0165(3) Uani 1 d . . . H35A H 0.3268 0.2553 0.2568 0.02 Uiso 1 calc R . . H35B H 0.3969 0.1558 0.241 0.02 Uiso 1 calc R . . C36 C 0.40275(15) 0.18984(12) 0.33307(7) 0.0205(3) Uani 1 d . . . H36A H 0.3961 0.2507 0.3577 0.025 Uiso 1 calc R . . H36B H 0.3346 0.1468 0.3426 0.025 Uiso 1 calc R . . C37 C 0.51737(16) 0.13620(13) 0.34932(8) 0.0250(4) Uani 1 d . . . H37A H 0.5196 0.1231 0.3935 0.03 Uiso 1 calc R . . H37B H 0.5198 0.0718 0.328 0.03 Uiso 1 calc R . . C38 C 0.62481(15) 0.19740(13) 0.33174(7) 0.0216(4) Uani 1 d . . . H38A H 0.6976 0.1594 0.3408 0.026 Uiso 1 calc R . . H38B H 0.6267 0.2587 0.3562 0.026 Uiso 1 calc R . . C39 C 0.62220(14) 0.22434(12) 0.26425(7) 0.0164(3) Uani 1 d . . . H39A H 0.6905 0.2672 0.2548 0.02 Uiso 1 calc R . . H39B H 0.6287 0.1634 0.2396 0.02 Uiso 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 0.01345(9) 0.00994(9) 0.01276(10) 0.00010(6) 0.00075(7) 0.00082(6) O1 0.0221(6) 0.0102(5) 0.0163(6) 0.0000(4) 0.0059(5) 0.0006(4) C2 0.0164(7) 0.0109(7) 0.0138(8) 0.0005(6) 0.0015(6) 0.0002(6) C3 0.0182(8) 0.0155(8) 0.0188(9) -0.0010(6) 0.0032(7) -0.0009(6) F3A 0.0267(5) 0.0138(5) 0.0366(6) -0.0082(4) 0.0027(5) -0.0035(4) F3B 0.0263(5) 0.0266(5) 0.0285(6) -0.0014(4) 0.0128(4) -0.0079(4) F3C 0.0193(5) 0.0310(6) 0.0293(6) 0.0048(4) -0.0070(4) -0.0032(4) C4 0.0254(8) 0.0152(8) 0.0167(8) 0.0022(6) -0.0006(7) -0.0004(6) F4A 0.0275(5) 0.0258(5) 0.0216(5) 0.0016(4) -0.0098(4) -0.0044(4) F4B 0.0339(6) 0.0179(5) 0.0315(6) 0.0007(4) -0.0072(5) 0.0107(4) F4C 0.0401(6) 0.0324(6) 0.0168(5) 0.0112(4) 0.0014(5) -0.0031(5) C5 0.0169(7) 0.0129(7) 0.0117(8) -0.0015(6) 0.0004(6) -0.0004(6) C6 0.0152(7) 0.0159(7) 0.0089(7) -0.0008(6) -0.0001(6) 0.0004(6) C7 0.0159(7) 0.0124(7) 0.0152(8) 0.0019(6) 0.0030(6) 0.0002(6) C8 0.0179(8) 0.0139(7) 0.0172(8) 0.0006(6) 0.0015(6) 0.0002(6) C9 0.0218(8) 0.0148(8) 0.0175(8) -0.0012(6) 0.0051(7) 0.0011(6) C10 0.0161(8) 0.0150(8) 0.0251(9) 0.0033(6) 0.0042(7) 0.0036(6) C11 0.0175(8) 0.0168(8) 0.0200(9) 0.0039(6) -0.0017(6) 0.0016(6) C12 0.0194(8) 0.0144(8) 0.0154(8) -0.0003(6) 0.0008(6) 0.0001(6) N13 0.0136(6) 0.0140(6) 0.0124(7) 0.0001(5) 0.0012(5) -0.0010(5) C14 0.0125(7) 0.0134(7) 0.0153(8) 0.0006(6) 0.0019(6) 0.0008(5) C15 0.0153(7) 0.0163(8) 0.0145(8) -0.0007(6) -0.0003(6) 0.0023(6) C16 0.0206(8) 0.0146(8) 0.0163(8) 0.0025(6) 0.0018(6) 0.0006(6) C17 0.0230(8) 0.0133(8) 0.0237(9) 0.0001(6) 0.0020(7) -0.0017(6) C18 0.0213(8) 0.0203(8) 0.0160(8) -0.0029(6) -0.0003(7) -0.0051(6) C19 0.0165(8) 0.0194(8) 0.0140(8) 0.0010(6) 0.0006(6) 0.0001(6) O21 0.0220(6) 0.0109(5) 0.0196(6) 0.0001(4) -0.0057(5) 0.0008(4) C22 0.0144(7) 0.0125(7) 0.0152(8) 0.0008(6) -0.0011(6) 0.0005(6) C23 0.0195(8) 0.0167(8) 0.0194(9) 0.0019(6) -0.0026(7) 0.0002(6) F23A 0.0212(5) 0.0318(5) 0.0163(5) 0.0024(4) 0.0026(4) 0.0025(4) F23B 0.0337(6) 0.0286(5) 0.0177(5) 0.0004(4) -0.0100(4) -0.0061(4) F23C 0.0300(5) 0.0205(5) 0.0253(6) 0.0089(4) -0.0019(4) 0.0061(4) C24 0.0177(8) 0.0203(8) 0.0206(9) 0.0018(6) -0.0016(7) -0.0008(6) F24A 0.0162(5) 0.0439(7) 0.0343(6) -0.0045(5) -0.0051(4) -0.0056(4) F24B 0.0235(5) 0.0243(5) 0.0402(6) -0.0026(4) 0.0066(5) 0.0073(4) F24C 0.0201(5) 0.0414(6) 0.0269(6) 0.0114(5) 0.0055(4) -0.0024(4) C25 0.0152(7) 0.0123(7) 0.0136(8) 0.0012(6) 0.0011(6) 0.0002(6) C26 0.0089(6) 0.0134(7) 0.0150(8) -0.0005(6) 0.0009(6) -0.0021(5) C27 0.0187(7) 0.0115(7) 0.0141(8) 0.0013(6) -0.0015(6) 0.0017(6) C28 0.0187(8) 0.0165(8) 0.0190(8) -0.0002(6) 0.0000(6) 0.0032(6) C29 0.0265(9) 0.0246(9) 0.0197(9) -0.0010(7) -0.0012(7) 0.0126(7) C30 0.0413(11) 0.0147(8) 0.0217(9) -0.0044(7) -0.0064(8) 0.0088(7) C31 0.0407(11) 0.0145(8) 0.0270(10) -0.0019(7) -0.0021(8) -0.0057(7) C32 0.0262(9) 0.0179(8) 0.0213(9) -0.0013(6) 0.0030(7) -0.0034(7) N33 0.0114(6) 0.0137(6) 0.0130(7) -0.0002(5) 0.0008(5) -0.0004(5) C34 0.0183(7) 0.0124(7) 0.0106(7) 0.0005(6) 0.0006(6) 0.0009(6) C35 0.0173(7) 0.0165(8) 0.0159(8) -0.0007(6) 0.0020(6) -0.0014(6) C36 0.0254(9) 0.0200(8) 0.0160(8) 0.0006(6) 0.0058(7) -0.0038(7) C37 0.0375(10) 0.0205(9) 0.0170(9) 0.0057(7) 0.0032(8) 0.0039(7) C38 0.0243(9) 0.0261(9) 0.0143(8) 0.0013(7) -0.0017(7) 0.0068(7) C39 0.0184(8) 0.0178(8) 0.0131(8) -0.0005(6) 0.0003(6) 0.0023(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O21 1.9141(11) . ? Zn1 O1 1.9171(10) . ? Zn1 N33 2.0559(12) . ? Zn1 N13 2.0870(12) . ? O1 C2 1.3608(17) . ? C2 C4 1.540(2) . ? C2 C3 1.549(2) . ? C2 C5 1.5552(19) . ? C3 F3B 1.3352(17) . ? C3 F3A 1.3392(17) . ? C3 F3C 1.3473(19) . ? C4 F4C 1.3385(18) . ? C4 F4A 1.3438(19) . ? C4 F4B 1.3449(18) . ? C5 C6 1.517(2) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 N13 1.2898(19) . ? C6 C7 1.493(2) . ? C7 C8 1.396(2) . ? C7 C12 1.401(2) . ? C8 C9 1.394(2) . ? C8 H8 0.95 . ? C9 C10 1.381(2) . ? C9 H9 0.95 . ? C10 C11 1.390(2) . ? C10 H10 0.95 . ? C11 C12 1.385(2) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? N13 C14 1.4882(18) . ? C14 C19 1.520(2) . ? C14 C15 1.529(2) . ? C14 H14 1 . ? C15 C16 1.535(2) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17 1.528(2) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.524(2) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 C19 1.534(2) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? O21 C22 1.3590(17) . ? C22 C23 1.545(2) . ? C22 C24 1.556(2) . ? C22 C25 1.564(2) . ? C23 F23B 1.3337(19) . ? C23 F23A 1.3436(18) . ? C23 F23C 1.3502(18) . ? C24 F24A 1.3351(19) . ? C24 F24C 1.3401(19) . ? C24 F24B 1.3454(19) . ? C25 C26 1.514(2) . ? C25 H25A 0.99 . ? C25 H25B 0.99 . ? C26 N33 1.2847(19) . ? C26 C27 1.498(2) . ? C27 C32 1.393(2) . ? C27 C28 1.395(2) . ? C28 C29 1.391(2) . ? C28 H28 0.95 . ? C29 C30 1.385(3) . ? C29 H29 0.95 . ? C30 C31 1.384(3) . ? C30 H30 0.95 . ? C31 C32 1.388(2) . ? C31 H31 0.95 . ? C32 H32 0.95 . ? N33 C34 1.4900(19) . ? C34 C39 1.525(2) . ? C34 C35 1.533(2) . ? C34 H34 1 . ? C35 C36 1.533(2) . ? C35 H35A 0.99 . ? C35 H35B 0.99 . ? C36 C37 1.527(2) . ? C36 H36A 0.99 . ? C36 H36B 0.99 . ? C37 C38 1.524(2) . ? C37 H37A 0.99 . ? C37 H37B 0.99 . ? C38 C39 1.533(2) . ? C38 H38A 0.99 . ? C38 H38B 0.99 . ? C39 H39A 0.99 . ? C39 H39B 0.99 . ? 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 O21 Zn1 O1 116.93(5) . . ? O21 Zn1 N33 98.31(5) . . ? O1 Zn1 N33 110.64(5) . . ? O21 Zn1 N13 112.56(5) . . ? O1 Zn1 N13 98.17(5) . . ? N33 Zn1 N13 121.46(5) . . ? C2 O1 Zn1 120.83(9) . . ? O1 C2 C4 109.17(13) . . ? O1 C2 C3 108.66(12) . . ? C4 C2 C3 109.05(12) . . ? O1 C2 C5 113.98(12) . . ? C4 C2 C5 109.49(12) . . ? C3 C2 C5 106.36(12) . . ? F3B C3 F3A 107.03(12) . . ? F3B C3 F3C 106.10(12) . . ? F3A C3 F3C 106.53(13) . . ? F3B C3 C2 113.02(13) . . ? F3A C3 C2 113.45(12) . . ? F3C C3 C2 110.25(12) . . ? F4C C4 F4A 106.63(13) . . ? F4C C4 F4B 106.88(12) . . ? F4A C4 F4B 106.18(13) . . ? F4C C4 C2 112.72(13) . . ? F4A C4 C2 110.79(12) . . ? F4B C4 C2 113.21(13) . . ? C6 C5 C2 114.80(12) . . ? C6 C5 H5A 108.6 . . ? C2 C5 H5A 108.6 . . ? C6 C5 H5B 108.6 . . ? C2 C5 H5B 108.6 . . ? H5A C5 H5B 107.5 . . ? N13 C6 C7 124.97(13) . . ? N13 C6 C5 117.88(13) . . ? C7 C6 C5 117.10(12) . . ? C8 C7 C12 119.41(14) . . ? C8 C7 C6 120.08(14) . . ? C12 C7 C6 120.50(13) . . ? C9 C8 C7 119.54(15) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C10 C9 C8 120.54(15) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 120.25(14) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 119.73(15) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C7 120.43(15) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? C6 N13 C14 120.60(12) . . ? C6 N13 Zn1 115.14(10) . . ? C14 N13 Zn1 123.85(9) . . ? N13 C14 C19 111.96(12) . . ? N13 C14 C15 108.17(12) . . ? C19 C14 C15 111.26(12) . . ? N13 C14 H14 108.4 . . ? C19 C14 H14 108.4 . . ? C15 C14 H14 108.4 . . ? C14 C15 C16 111.14(13) . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108 . . ? C17 C16 C15 111.77(13) . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C16 111.54(13) . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 108 . . ? C17 C18 C19 111.08(14) . . ? C17 C18 H18A 109.4 . . ? C19 C18 H18A 109.4 . . ? C17 C18 H18B 109.4 . . ? C19 C18 H18B 109.4 . . ? H18A C18 H18B 108 . . ? C14 C19 C18 110.10(12) . . ? C14 C19 H19A 109.6 . . ? C18 C19 H19A 109.6 . . ? C14 C19 H19B 109.6 . . ? C18 C19 H19B 109.6 . . ? H19A C19 H19B 108.2 . . ? C22 O21 Zn1 120.72(10) . . ? O21 C22 C23 107.98(12) . . ? O21 C22 C24 109.78(12) . . ? C23 C22 C24 108.35(13) . . ? O21 C22 C25 115.30(13) . . ? C23 C22 C25 106.88(12) . . ? C24 C22 C25 108.33(12) . . ? F23B C23 F23A 106.73(13) . . ? F23B C23 F23C 106.78(13) . . ? F23A C23 F23C 106.18(12) . . ? F23B C23 C22 112.92(13) . . ? F23A C23 C22 110.71(13) . . ? F23C C23 C22 113.07(13) . . ? F24A C24 F24C 107.26(13) . . ? F24A C24 F24B 106.42(13) . . ? F24C C24 F24B 106.09(13) . . ? F24A C24 C22 112.65(13) . . ? F24C C24 C22 110.54(13) . . ? F24B C24 C22 113.47(13) . . ? C26 C25 C22 115.18(12) . . ? C26 C25 H25A 108.5 . . ? C22 C25 H25A 108.5 . . ? C26 C25 H25B 108.5 . . ? C22 C25 H25B 108.5 . . ? H25A C25 H25B 107.5 . . ? N33 C26 C27 124.76(14) . . ? N33 C26 C25 119.85(13) . . ? C27 C26 C25 115.27(12) . . ? C32 C27 C28 119.58(14) . . ? C32 C27 C26 118.21(13) . . ? C28 C27 C26 122.17(13) . . ? C29 C28 C27 119.94(15) . . ? C29 C28 H28 120 . . ? C27 C28 H28 120 . . ? C30 C29 C28 120.05(15) . . ? C30 C29 H29 120 . . ? C28 C29 H29 120 . . ? C31 C30 C29 120.21(16) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C30 C31 C32 120.09(16) . . ? C30 C31 H31 120 . . ? C32 C31 H31 120 . . ? C31 C32 C27 120.12(15) . . ? C31 C32 H32 119.9 . . ? C27 C32 H32 119.9 . . ? C26 N33 C34 120.91(12) . . ? C26 N33 Zn1 117.96(10) . . ? C34 N33 Zn1 120.53(9) . . ? N33 C34 C39 109.80(12) . . ? N33 C34 C35 108.28(12) . . ? C39 C34 C35 111.28(12) . . ? N33 C34 H34 109.1 . . ? C39 C34 H34 109.1 . . ? C35 C34 H34 109.1 . . ? C36 C35 C34 111.13(13) . . ? C36 C35 H35A 109.4 . . ? C34 C35 H35A 109.4 . . ? C36 C35 H35B 109.4 . . ? C34 C35 H35B 109.4 . . ? H35A C35 H35B 108 . . ? C37 C36 C35 110.94(13) . . ? C37 C36 H36A 109.5 . . ? C35 C36 H36A 109.5 . . ? C37 C36 H36B 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 108 . . ? C38 C37 C36 111.13(13) . . ? C38 C37 H37A 109.4 . . ? C36 C37 H37A 109.4 . . ? C38 C37 H37B 109.4 . . ? C36 C37 H37B 109.4 . . ? H37A C37 H37B 108 . . ? C37 C38 C39 111.49(14) . . ? C37 C38 H38A 109.3 . . ? C39 C38 H38A 109.3 . . ? C37 C38 H38B 109.3 . . ? C39 C38 H38B 109.3 . . ? H38A C38 H38B 108 . . ? C34 C39 C38 110.61(12) . . ? C34 C39 H39A 109.5 . . ? C38 C39 H39A 109.5 . . ? C34 C39 H39B 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 108.1 . . ? 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 O21 Zn1 O1 C2 92.10(12) . . . . ? N33 Zn1 O1 C2 -156.53(11) . . . . ? N13 Zn1 O1 C2 -28.40(12) . . . . ? Zn1 O1 C2 C4 116.09(11) . . . . ? Zn1 O1 C2 C3 -125.09(11) . . . . ? Zn1 O1 C2 C5 -6.69(17) . . . . ? O1 C2 C3 F3B -51.79(17) . . . . ? C4 C2 C3 F3B 67.11(16) . . . . ? C5 C2 C3 F3B -174.90(12) . . . . ? O1 C2 C3 F3A -173.87(12) . . . . ? C4 C2 C3 F3A -54.97(17) . . . . ? C5 C2 C3 F3A 63.02(16) . . . . ? O1 C2 C3 F3C 66.75(15) . . . . ? C4 C2 C3 F3C -174.35(12) . . . . ? C5 C2 C3 F3C -56.36(15) . . . . ? O1 C2 C4 F4C 66.01(16) . . . . ? C3 C2 C4 F4C -52.57(16) . . . . ? C5 C2 C4 F4C -168.57(12) . . . . ? O1 C2 C4 F4A -53.38(16) . . . . ? C3 C2 C4 F4A -171.96(12) . . . . ? C5 C2 C4 F4A 72.04(15) . . . . ? O1 C2 C4 F4B -172.53(12) . . . . ? C3 C2 C4 F4B 68.89(16) . . . . ? C5 C2 C4 F4B -47.11(16) . . . . ? O1 C2 C5 C6 60.89(17) . . . . ? C4 C2 C5 C6 -61.71(16) . . . . ? C3 C2 C5 C6 -179.40(12) . . . . ? C2 C5 C6 N13 -69.71(18) . . . . ? C2 C5 C6 C7 112.69(15) . . . . ? N13 C6 C7 C8 -128.05(16) . . . . ? C5 C6 C7 C8 49.36(19) . . . . ? N13 C6 C7 C12 52.7(2) . . . . ? C5 C6 C7 C12 -129.87(15) . . . . ? C12 C7 C8 C9 -3.5(2) . . . . ? C6 C7 C8 C9 177.24(13) . . . . ? C7 C8 C9 C10 2.1(2) . . . . ? C8 C9 C10 C11 0.6(2) . . . . ? C9 C10 C11 C12 -1.8(2) . . . . ? C10 C11 C12 C7 0.4(2) . . . . ? C8 C7 C12 C11 2.3(2) . . . . ? C6 C7 C12 C11 -178.47(14) . . . . ? C7 C6 N13 C14 10.5(2) . . . . ? C5 C6 N13 C14 -166.94(13) . . . . ? C7 C6 N13 Zn1 -162.54(12) . . . . ? C5 C6 N13 Zn1 20.07(17) . . . . ? O21 Zn1 N13 C6 -101.75(11) . . . . ? O1 Zn1 N13 C6 21.96(12) . . . . ? N33 Zn1 N13 C6 142.31(11) . . . . ? O21 Zn1 N13 C14 85.52(12) . . . . ? O1 Zn1 N13 C14 -150.77(11) . . . . ? N33 Zn1 N13 C14 -30.42(13) . . . . ? C6 N13 C14 C19 -122.51(15) . . . . ? Zn1 N13 C14 C19 49.84(16) . . . . ? C6 N13 C14 C15 114.54(15) . . . . ? Zn1 N13 C14 C15 -73.11(14) . . . . ? N13 C14 C15 C16 179.29(12) . . . . ? C19 C14 C15 C16 55.91(16) . . . . ? C14 C15 C16 C17 -53.37(17) . . . . ? C15 C16 C17 C18 53.43(18) . . . . ? C16 C17 C18 C19 -55.51(17) . . . . ? N13 C14 C19 C18 -178.99(12) . . . . ? C15 C14 C19 C18 -57.80(17) . . . . ? C17 C18 C19 C14 57.53(17) . . . . ? O1 Zn1 O21 C22 137.71(10) . . . . ? N33 Zn1 O21 C22 19.44(11) . . . . ? N13 Zn1 O21 C22 -109.73(11) . . . . ? Zn1 O21 C22 C23 137.47(10) . . . . ? Zn1 O21 C22 C24 -104.59(12) . . . . ? Zn1 O21 C22 C25 18.06(16) . . . . ? O21 C22 C23 F23B 48.69(17) . . . . ? C24 C22 C23 F23B -70.17(16) . . . . ? C25 C22 C23 F23B 173.29(12) . . . . ? O21 C22 C23 F23A -70.92(15) . . . . ? C24 C22 C23 F23A 170.23(12) . . . . ? C25 C22 C23 F23A 53.69(15) . . . . ? O21 C22 C23 F23C 170.08(12) . . . . ? C24 C22 C23 F23C 51.22(17) . . . . ? C25 C22 C23 F23C -65.32(16) . . . . ? O21 C22 C24 F24A -70.11(17) . . . . ? C23 C22 C24 F24A 47.59(17) . . . . ? C25 C22 C24 F24A 163.20(13) . . . . ? O21 C22 C24 F24C 49.86(17) . . . . ? C23 C22 C24 F24C 167.56(13) . . . . ? C25 C22 C24 F24C -76.83(16) . . . . ? O21 C22 C24 F24B 168.89(13) . . . . ? C23 C22 C24 F24B -73.41(17) . . . . ? C25 C22 C24 F24B 42.20(18) . . . . ? O21 C22 C25 C26 -62.76(17) . . . . ? C23 C22 C25 C26 177.23(12) . . . . ? C24 C22 C25 C26 60.67(16) . . . . ? C22 C25 C26 N33 56.78(18) . . . . ? C22 C25 C26 C27 -127.02(13) . . . . ? N33 C26 C27 C32 111.15(17) . . . . ? C25 C26 C27 C32 -64.84(19) . . . . ? N33 C26 C27 C28 -71.3(2) . . . . ? C25 C26 C27 C28 112.68(16) . . . . ? C32 C27 C28 C29 -1.1(2) . . . . ? C26 C27 C28 C29 -178.63(14) . . . . ? C27 C28 C29 C30 0.3(2) . . . . ? C28 C29 C30 C31 0.2(3) . . . . ? C29 C30 C31 C32 0.1(3) . . . . ? C30 C31 C32 C27 -0.9(3) . . . . ? C28 C27 C32 C31 1.4(2) . . . . ? C26 C27 C32 C31 179.04(15) . . . . ? C27 C26 N33 C34 4.9(2) . . . . ? C25 C26 N33 C34 -179.32(12) . . . . ? C27 C26 N33 Zn1 176.04(11) . . . . ? C25 C26 N33 Zn1 -8.13(17) . . . . ? O21 Zn1 N33 C26 -25.96(11) . . . . ? O1 Zn1 N33 C26 -148.92(10) . . . . ? N13 Zn1 N33 C26 96.98(11) . . . . ? O21 Zn1 N33 C34 145.26(10) . . . . ? O1 Zn1 N33 C34 22.30(11) . . . . ? N13 Zn1 N33 C34 -91.80(11) . . . . ? C26 N33 C34 C39 -131.92(14) . . . . ? Zn1 N33 C34 C39 57.12(14) . . . . ? C26 N33 C34 C35 106.40(15) . . . . ? Zn1 N33 C34 C35 -64.56(14) . . . . ? N33 C34 C35 C36 176.58(12) . . . . ? C39 C34 C35 C36 55.81(17) . . . . ? C34 C35 C36 C37 -55.48(17) . . . . ? C35 C36 C37 C38 55.65(18) . . . . ? C36 C37 C38 C39 -56.11(18) . . . . ? N33 C34 C39 C38 -175.53(12) . . . . ? C35 C34 C39 C38 -55.67(17) . . . . ? C37 C38 C39 C34 55.96(18) . . . . ? # Attachment 'complex5_GE231_octa_100K_APEX_09avril08_archive.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-04-09 at 14:27:09 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\progs\wingx\files\archive.dat # CIF files read : job struct data_5 _database_code_depnum_ccdc_archive 'CCDC 718599' _audit_creation_date 2008-04-09T14:27:09-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C40 H38 F12 N2 O2 Zn2' _chemical_formula_sum 'C40 H38 F12 N2 O2 Zn2' _chemical_formula_weight 937.46 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 9.7992(4) _cell_length_b 9.9849(4) _cell_length_c 20.4153(10) _cell_angle_alpha 90 _cell_angle_beta 100.386(2) _cell_angle_gamma 90 _cell_volume 1964.79(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7918 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.43 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.35 _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.515 _exptl_absorpt_correction_T_max 0.631 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_unetI/netI 0.032 _diffrn_reflns_number 20701 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4471 _reflns_number_gt 3782 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0290P)^2^+0.9596P] 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_number_reflns 4471 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.029 _refine_ls_wR_factor_ref 0.07 _refine_ls_wR_factor_gt 0.0671 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.514 _refine_diff_density_min -0.642 _refine_diff_density_rms 0.066 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.37524(2) 0.088687(19) 0.469974(10) 0.01253(7) Uani 1 d . . . C1 C 0.24171(19) 0.22620(18) 0.48812(10) 0.0201(4) Uani 1 d . . . H1A H 0.1567 0.1806 0.4963 0.024 Uiso 1 calc R . . H1B H 0.2824 0.2743 0.5294 0.024 Uiso 1 calc R . . C2 C 0.2005(2) 0.32949(19) 0.43226(10) 0.0243(4) Uani 1 d . . . H2A H 0.2826 0.3809 0.4262 0.036 Uiso 1 calc R . . H2B H 0.1305 0.3904 0.4442 0.036 Uiso 1 calc R . . H2C H 0.1623 0.2831 0.3907 0.036 Uiso 1 calc R . . N11 N 0.41002(15) 0.04275(14) 0.37360(7) 0.0141(3) Uani 1 d . . . C12 C 0.32981(19) -0.06765(17) 0.33517(9) 0.0173(4) Uani 1 d . . . H12A H 0.3006 -0.1333 0.3663 0.021 Uiso 1 calc R . . H12B H 0.389 -0.1146 0.308 0.021 Uiso 1 calc R . . C13 C 0.20297(18) -0.01038(17) 0.29018(9) 0.0160(4) Uani 1 d . . . C14 C 0.20139(19) 0.00199(18) 0.22194(9) 0.0197(4) Uani 1 d . . . H14 H 0.28 -0.0247 0.2039 0.024 Uiso 1 calc R . . C15 C 0.0845(2) 0.0535(2) 0.18010(10) 0.0234(4) Uani 1 d . . . H15 H 0.0838 0.0618 0.1337 0.028 Uiso 1 calc R . . C16 C -0.0304(2) 0.09250(19) 0.20610(11) 0.0247(4) Uani 1 d . . . H16 H -0.1098 0.1274 0.1775 0.03 Uiso 1 calc R . . C17 C -0.0297(2) 0.08064(19) 0.27380(11) 0.0252(4) Uani 1 d . . . H17 H -0.1087 0.1071 0.2916 0.03 Uiso 1 calc R . . C19 C 0.50255(17) 0.10931(16) 0.34990(8) 0.0127(3) Uani 1 d . . . C18 C 0.08689(19) 0.02987(19) 0.31597(10) 0.0206(4) Uani 1 d . . . H18 H 0.0872 0.0227 0.3624 0.025 Uiso 1 calc R . . C20 C 0.54273(18) 0.08829(17) 0.28321(9) 0.0150(4) Uani 1 d . . . C21 C 0.52524(18) 0.19570(19) 0.23823(9) 0.0187(4) Uani 1 d . . . H21 H 0.4947 0.28 0.2516 0.022 Uiso 1 calc R . . C22 C 0.5525(2) 0.1792(2) 0.17401(10) 0.0259(4) Uani 1 d . . . H22 H 0.539 0.2518 0.1434 0.031 Uiso 1 calc R . . C23 C 0.5993(2) 0.0573(2) 0.15480(10) 0.0289(5) Uani 1 d . . . H23 H 0.616 0.0456 0.1107 0.035 Uiso 1 calc R . . C24 C 0.6220(2) -0.0480(2) 0.19979(11) 0.0276(5) Uani 1 d . . . H24 H 0.6565 -0.1308 0.1867 0.033 Uiso 1 calc R . . C25 C 0.59447(19) -0.03331(19) 0.26404(10) 0.0208(4) Uani 1 d . . . H25 H 0.6108 -0.1056 0.2947 0.025 Uiso 1 calc R . . C26 C 0.56764(17) 0.22795(16) 0.39080(8) 0.0131(3) Uani 1 d . . . H26A H 0.4928 0.2893 0.3986 0.016 Uiso 1 calc R . . H26B H 0.6269 0.2774 0.3646 0.016 Uiso 1 calc R . . O31 O 0.59095(12) 0.10240(11) 0.49608(6) 0.0119(2) Uani 1 d . . . C32 C 0.65688(17) 0.18917(17) 0.45939(8) 0.0126(3) Uani 1 d . . . C33 C 0.79597(18) 0.12911(19) 0.44857(9) 0.0177(4) Uani 1 d . . . F33A F 0.87653(10) 0.09062(11) 0.50577(5) 0.0211(2) Uani 1 d . . . F33B F 0.87150(11) 0.21468(12) 0.41872(6) 0.0295(3) Uani 1 d . . . F33C F 0.77393(11) 0.01999(11) 0.40937(5) 0.0225(2) Uani 1 d . . . C34 C 0.68471(19) 0.32267(18) 0.49851(9) 0.0185(4) Uani 1 d . . . F34A F 0.56615(12) 0.36966(11) 0.51370(5) 0.0232(3) Uani 1 d . . . F34B F 0.77420(11) 0.30837(11) 0.55630(5) 0.0238(3) Uani 1 d . . . F34C F 0.73541(14) 0.41888(11) 0.46365(6) 0.0320(3) Uani 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 0.01242(11) 0.01260(11) 0.01291(11) 0.00181(8) 0.00315(7) 0.00049(8) C1 0.0180(9) 0.0183(9) 0.0248(10) 0.0003(8) 0.0062(7) 0.0044(7) C2 0.0245(10) 0.0172(9) 0.0288(11) 0.0001(8) -0.0016(8) 0.0035(8) N11 0.0154(7) 0.0135(7) 0.0123(7) 0.0011(6) -0.0002(6) -0.0005(6) C12 0.0209(9) 0.0156(8) 0.0151(9) -0.0003(7) 0.0025(7) -0.0054(7) C13 0.0177(9) 0.0152(8) 0.0146(9) -0.0025(7) 0.0014(7) -0.0064(7) C14 0.0190(9) 0.0249(10) 0.0159(9) -0.0024(8) 0.0055(7) -0.0066(8) C15 0.0278(10) 0.0271(10) 0.0137(9) 0.0025(8) -0.0003(8) -0.0082(8) C16 0.0215(10) 0.0219(10) 0.0275(11) -0.0006(8) -0.0042(8) -0.0019(8) C17 0.0192(9) 0.0268(10) 0.0304(12) -0.0106(9) 0.0063(8) -0.0018(8) C19 0.0151(8) 0.0127(8) 0.0093(8) 0.0008(6) -0.0004(6) 0.0033(7) C18 0.0234(10) 0.0237(9) 0.0155(9) -0.0055(8) 0.0052(7) -0.0052(8) C20 0.0137(8) 0.0191(9) 0.0118(8) -0.0036(7) 0.0017(7) -0.0012(7) C21 0.0183(9) 0.0238(9) 0.0138(9) 0.0015(8) 0.0025(7) 0.0012(8) C22 0.0252(10) 0.0391(12) 0.0130(9) 0.0026(9) 0.0022(8) -0.0014(9) C23 0.0237(10) 0.0490(13) 0.0154(10) -0.0109(9) 0.0075(8) -0.0080(9) C24 0.0228(10) 0.0322(11) 0.0298(12) -0.0172(9) 0.0100(8) -0.0031(9) C25 0.0210(9) 0.0190(9) 0.0227(10) -0.0043(8) 0.0049(8) -0.0023(8) C26 0.0157(8) 0.0124(8) 0.0111(8) 0.0013(7) 0.0022(6) -0.0013(7) O31 0.0121(6) 0.0134(6) 0.0109(6) 0.0027(5) 0.0041(5) -0.0016(5) C32 0.0145(8) 0.0144(8) 0.0090(8) 0.0008(7) 0.0023(6) -0.0027(7) C33 0.0170(9) 0.0220(9) 0.0149(9) 0.0050(7) 0.0047(7) -0.0018(7) F33A 0.0148(5) 0.0274(6) 0.0199(6) 0.0066(5) -0.0002(4) 0.0003(4) F33B 0.0189(6) 0.0379(7) 0.0345(7) 0.0170(6) 0.0121(5) -0.0017(5) F33C 0.0226(6) 0.0275(6) 0.0183(6) -0.0030(5) 0.0060(4) 0.0077(5) C34 0.0253(10) 0.0184(9) 0.0116(9) 0.0010(7) 0.0025(7) -0.0053(8) F34A 0.0316(6) 0.0192(5) 0.0183(6) -0.0056(4) 0.0031(5) 0.0039(5) F34B 0.0276(6) 0.0275(6) 0.0137(5) -0.0030(5) -0.0032(4) -0.0081(5) F34C 0.0565(8) 0.0216(6) 0.0191(6) 0.0003(5) 0.0102(6) -0.0212(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 1.9772(18) . ? Zn1 O31 2.0366(11) 3_656 ? Zn1 O31 2.0892(12) . ? Zn1 N11 2.1070(15) . ? Zn1 Zn1 3.0883(4) 3_656 ? C1 C2 1.537(3) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 H2A 0.98 . ? C2 H2B 0.98 . ? C2 H2C 0.98 . ? N11 C19 1.287(2) . ? N11 C12 1.492(2) . ? C12 C13 1.518(2) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 C14 1.396(3) . ? C13 C18 1.396(3) . ? C14 C15 1.398(3) . ? C14 H14 0.95 . ? C15 C16 1.384(3) . ? C15 H15 0.95 . ? C16 C17 1.386(3) . ? C16 H16 0.95 . ? C17 C18 1.396(3) . ? C17 H17 0.95 . ? C19 C20 1.499(2) . ? C19 C26 1.522(2) . ? C18 H18 0.95 . ? C20 C25 1.399(3) . ? C20 C21 1.402(3) . ? C21 C22 1.394(3) . ? C21 H21 0.95 . ? C22 C23 1.382(3) . ? C22 H22 0.95 . ? C23 C24 1.387(3) . ? C23 H23 0.95 . ? C24 C25 1.394(3) . ? C24 H24 0.95 . ? C25 H25 0.95 . ? C26 C32 1.560(2) . ? C26 H26A 0.99 . ? C26 H26B 0.99 . ? O31 C32 1.380(2) . ? O31 Zn1 2.0366(11) 3_656 ? C32 C33 1.541(3) . ? C32 C34 1.553(2) . ? C33 F33A 1.342(2) . ? C33 F33C 1.346(2) . ? C33 F33B 1.346(2) . ? C34 F34A 1.340(2) . ? C34 F34C 1.343(2) . ? C34 F34B 1.345(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 C1 Zn1 O31 131.25(7) . 3_656 ? C1 Zn1 O31 125.45(6) . . ? O31 Zn1 O31 83.08(5) 3_656 . ? C1 Zn1 N11 123.37(7) . . ? O31 Zn1 N11 94.02(5) 3_656 . ? O31 Zn1 N11 85.75(5) . . ? C1 Zn1 Zn1 145.81(6) . 3_656 ? O31 Zn1 Zn1 42.19(3) 3_656 3_656 ? O31 Zn1 Zn1 40.89(3) . 3_656 ? N11 Zn1 Zn1 89.77(4) . 3_656 ? C2 C1 Zn1 114.91(14) . . ? C2 C1 H1A 108.5 . . ? Zn1 C1 H1A 108.5 . . ? C2 C1 H1B 108.5 . . ? Zn1 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C19 N11 C12 121.60(15) . . ? C19 N11 Zn1 118.83(12) . . ? C12 N11 Zn1 119.55(11) . . ? N11 C12 C13 109.65(14) . . ? N11 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? N11 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C14 C13 C18 119.20(17) . . ? C14 C13 C12 119.86(17) . . ? C18 C13 C12 120.94(17) . . ? C13 C14 C15 120.18(19) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 120.19(18) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 119.99(18) . . ? C15 C16 H16 120 . . ? C17 C16 H16 120 . . ? C16 C17 C18 120.19(19) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? N11 C19 C20 125.98(15) . . ? N11 C19 C26 116.73(16) . . ? C20 C19 C26 117.05(15) . . ? C13 C18 C17 120.24(18) . . ? C13 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C25 C20 C21 119.24(18) . . ? C25 C20 C19 122.93(16) . . ? C21 C20 C19 117.82(16) . . ? C22 C21 C20 120.25(18) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C23 C22 C21 120.04(19) . . ? C23 C22 H22 120 . . ? C21 C22 H22 120 . . ? C22 C23 C24 120.07(19) . . ? C22 C23 H23 120 . . ? C24 C23 H23 120 . . ? C23 C24 C25 120.55(19) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C24 C25 C20 119.75(19) . . ? C24 C25 H25 120.1 . . ? C20 C25 H25 120.1 . . ? C19 C26 C32 114.27(13) . . ? C19 C26 H26A 108.7 . . ? C32 C26 H26A 108.7 . . ? C19 C26 H26B 108.7 . . ? C32 C26 H26B 108.7 . . ? H26A C26 H26B 107.6 . . ? C32 O31 Zn1 135.22(11) . 3_656 ? C32 O31 Zn1 117.00(9) . . ? Zn1 O31 Zn1 96.92(5) 3_656 . ? O31 C32 C33 110.25(14) . . ? O31 C32 C34 108.42(14) . . ? C33 C32 C34 109.27(14) . . ? O31 C32 C26 113.68(13) . . ? C33 C32 C26 109.57(14) . . ? C34 C32 C26 105.47(13) . . ? F33A C33 F33C 106.96(14) . . ? F33A C33 F33B 106.88(14) . . ? F33C C33 F33B 106.67(15) . . ? F33A C33 C32 112.54(15) . . ? F33C C33 C32 110.43(14) . . ? F33B C33 C32 112.99(15) . . ? F34A C34 F34C 106.93(15) . . ? F34A C34 F34B 106.83(15) . . ? F34C C34 F34B 107.21(14) . . ? F34A C34 C32 109.90(14) . . ? F34C C34 C32 112.89(15) . . ? F34B C34 C32 112.73(14) . . ? 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 O31 Zn1 C1 C2 -153.18(11) 3_656 . . . ? O31 Zn1 C1 C2 91.49(14) . . . . ? N11 Zn1 C1 C2 -19.61(17) . . . . ? Zn1 Zn1 C1 C2 144.39(10) 3_656 . . . ? C1 Zn1 N11 C19 88.55(14) . . . . ? O31 Zn1 N11 C19 -124.55(12) 3_656 . . . ? O31 Zn1 N11 C19 -41.80(12) . . . . ? Zn1 Zn1 N11 C19 -82.54(12) 3_656 . . . ? C1 Zn1 N11 C12 -92.88(14) . . . . ? O31 Zn1 N11 C12 54.02(12) 3_656 . . . ? O31 Zn1 N11 C12 136.76(12) . . . . ? Zn1 Zn1 N11 C12 96.03(11) 3_656 . . . ? C19 N11 C12 C13 -87.0(2) . . . . ? Zn1 N11 C12 C13 94.53(15) . . . . ? N11 C12 C13 C14 104.31(19) . . . . ? N11 C12 C13 C18 -76.0(2) . . . . ? C18 C13 C14 C15 -0.3(3) . . . . ? C12 C13 C14 C15 179.42(16) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? C14 C15 C16 C17 0.1(3) . . . . ? C15 C16 C17 C18 0.2(3) . . . . ? C12 N11 C19 C20 0.1(2) . . . . ? Zn1 N11 C19 C20 178.68(12) . . . . ? C12 N11 C19 C26 174.36(14) . . . . ? Zn1 N11 C19 C26 -7.11(19) . . . . ? C14 C13 C18 C17 0.6(3) . . . . ? C12 C13 C18 C17 -179.12(16) . . . . ? C16 C17 C18 C13 -0.6(3) . . . . ? N11 C19 C20 C25 -59.3(2) . . . . ? C26 C19 C20 C25 126.53(17) . . . . ? N11 C19 C20 C21 119.81(19) . . . . ? C26 C19 C20 C21 -54.4(2) . . . . ? C25 C20 C21 C22 3.2(3) . . . . ? C19 C20 C21 C22 -175.91(16) . . . . ? C20 C21 C22 C23 -1.1(3) . . . . ? C21 C22 C23 C24 -1.4(3) . . . . ? C22 C23 C24 C25 1.7(3) . . . . ? C23 C24 C25 C20 0.4(3) . . . . ? C21 C20 C25 C24 -2.9(3) . . . . ? C19 C20 C25 C24 176.21(17) . . . . ? N11 C19 C26 C32 66.0(2) . . . . ? C20 C19 C26 C32 -119.29(16) . . . . ? C1 Zn1 O31 C32 -73.41(14) . . . . ? O31 Zn1 O31 C32 149.79(13) 3_656 . . . ? N11 Zn1 O31 C32 55.22(11) . . . . ? Zn1 Zn1 O31 C32 149.79(13) 3_656 . . . ? C1 Zn1 O31 Zn1 136.80(8) . . . 3_656 ? O31 Zn1 O31 Zn1 0 3_656 . . 3_656 ? N11 Zn1 O31 Zn1 -94.58(6) . . . 3_656 ? Zn1 O31 C32 C33 -7.4(2) 3_656 . . . ? Zn1 O31 C32 C33 -142.27(11) . . . . ? Zn1 O31 C32 C34 -127.00(13) 3_656 . . . ? Zn1 O31 C32 C34 98.15(13) . . . . ? Zn1 O31 C32 C26 116.06(14) 3_656 . . . ? Zn1 O31 C32 C26 -18.78(18) . . . . ? C19 C26 C32 O31 -49.1(2) . . . . ? C19 C26 C32 C33 74.79(18) . . . . ? C19 C26 C32 C34 -167.70(15) . . . . ? O31 C32 C33 F33A -52.69(19) . . . . ? C34 C32 C33 F33A 66.37(18) . . . . ? C26 C32 C33 F33A -178.53(13) . . . . ? O31 C32 C33 F33C 66.75(17) . . . . ? C34 C32 C33 F33C -174.18(13) . . . . ? C26 C32 C33 F33C -59.08(18) . . . . ? O31 C32 C33 F33B -173.87(14) . . . . ? C34 C32 C33 F33B -54.80(19) . . . . ? C26 C32 C33 F33B 60.29(18) . . . . ? O31 C32 C34 F34A -54.06(17) . . . . ? C33 C32 C34 F34A -174.26(14) . . . . ? C26 C32 C34 F34A 68.03(17) . . . . ? O31 C32 C34 F34C -173.33(14) . . . . ? C33 C32 C34 F34C 66.47(19) . . . . ? C26 C32 C34 F34C -51.24(19) . . . . ? O31 C32 C34 F34B 64.99(19) . . . . ? C33 C32 C34 F34B -55.21(19) . . . . ? C26 C32 C34 F34B -172.92(15) . . . . ? # Attachment 'complex7_GE80_100K_APEX_06nov07_archive.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-11-07 at 10:07:45 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\progs\wingx\files\archive.dat # CIF files read : job struct data_7 _database_code_depnum_ccdc_archive 'CCDC 718600' _audit_creation_date 2007-11-07T10:07:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C40 H52 F12 N4 O2 Zn2' _chemical_formula_sum 'C40 H52 F12 N4 O2 Zn2' _chemical_formula_weight 979.6 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 12.3834(16) _cell_length_b 12.9413(15) _cell_length_c 14.1336(17) _cell_angle_alpha 90 _cell_angle_beta 109.417(4) _cell_angle_gamma 90 _cell_volume 2136.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5864 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 27.33 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.762 _exptl_absorpt_correction_T_max 0.953 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_unetI/netI 0.0452 _diffrn_reflns_number 17922 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4889 _reflns_number_gt 3754 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0441P)^2^+1.0412P] 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_number_reflns 4889 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.035 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0837 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.624 _refine_diff_density_min -0.769 _refine_diff_density_rms 0.079 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.61848(2) 0.031180(19) 0.57641(2) 0.01620(9) Uani 1 d . . . C1 C 0.7791(2) -0.0057(2) 0.5954(2) 0.0275(6) Uani 1 d . . . H1A H 0.7793 -0.0766 0.5691 0.033 Uiso 1 calc R . . H1B H 0.8063 0.041 0.5525 0.033 Uiso 1 calc R . . C2 C 0.8670(2) -0.0024(2) 0.7001(2) 0.0372(7) Uani 1 d . . . H2A H 0.8724 0.0681 0.7265 0.056 Uiso 1 calc R . . H2B H 0.9417 -0.0239 0.6974 0.056 Uiso 1 calc R . . H2C H 0.8434 -0.0493 0.7441 0.056 Uiso 1 calc R . . O3 O 0.48611(13) -0.06355(12) 0.56961(12) 0.0169(3) Uani 1 d . . . C4 C 0.4720(2) -0.15783(17) 0.60917(18) 0.0199(5) Uani 1 d . . . C5 C 0.5873(2) -0.2149(2) 0.6497(2) 0.0320(6) Uani 1 d . . . F5A F 0.57751(16) -0.30824(14) 0.68645(17) 0.0641(6) Uani 1 d . . . F5B F 0.66568(14) -0.16260(14) 0.72165(12) 0.0400(4) Uani 1 d . . . F5C F 0.63095(13) -0.23038(12) 0.57569(12) 0.0346(4) Uani 1 d . . . C6 C 0.4230(2) -0.13981(19) 0.69534(19) 0.0261(5) Uani 1 d . . . F6A F 0.32391(13) -0.08878(13) 0.66100(12) 0.0355(4) Uani 1 d . . . F6B F 0.40100(17) -0.22850(12) 0.73495(12) 0.0442(5) Uani 1 d . . . F6C F 0.49216(13) -0.08489(11) 0.77047(11) 0.0311(4) Uani 1 d . . . C7 C 0.3840(2) -0.22787(17) 0.53182(18) 0.0219(5) Uani 1 d . . . H7A H 0.3766 -0.2932 0.5656 0.026 Uiso 1 calc R . . H7B H 0.3085 -0.1931 0.5112 0.026 Uiso 1 calc R . . C8 C 0.4122(2) -0.25409(18) 0.43861(19) 0.0227(5) Uani 1 d . . . C9 C 0.4331(3) -0.36631(19) 0.4239(2) 0.0332(6) Uani 1 d . . . H9A H 0.3598 -0.4009 0.3908 0.05 Uiso 1 calc R . . H9B H 0.4711 -0.3986 0.4892 0.05 Uiso 1 calc R . . H9C H 0.4819 -0.3726 0.382 0.05 Uiso 1 calc R . . N10 N 0.41338(17) -0.17991(14) 0.37879(15) 0.0196(4) Uani 1 d . . . C11 C 0.4371(2) -0.20210(18) 0.28490(18) 0.0218(5) Uani 1 d . . . H11 H 0.415 -0.2752 0.2647 0.026 Uiso 1 calc R . . C12 C 0.3672(2) -0.13062(18) 0.20172(18) 0.0210(5) Uani 1 d . . . H12A H 0.3828 -0.0579 0.2237 0.025 Uiso 1 calc R . . H12B H 0.2846 -0.1441 0.1874 0.025 Uiso 1 calc R . . C13 C 0.3975(2) -0.14766(19) 0.10703(19) 0.0233(5) Uani 1 d . . . H13A H 0.3761 -0.2188 0.0821 0.028 Uiso 1 calc R . . H13B H 0.3534 -0.0989 0.0544 0.028 Uiso 1 calc R . . C14 C 0.5647(2) -0.1886(2) 0.30180(19) 0.0253(5) Uani 1 d . . . H14A H 0.5893 -0.1183 0.3276 0.03 Uiso 1 calc R . . H14B H 0.6094 -0.2392 0.3522 0.03 Uiso 1 calc R . . C15 C 0.5871(2) -0.2051(2) 0.20317(19) 0.0285(6) Uani 1 d . . . H15A H 0.6697 -0.1957 0.214 0.034 Uiso 1 calc R . . H15B H 0.5661 -0.2767 0.1794 0.034 Uiso 1 calc R . . N16 N 0.52050(17) -0.13203(15) 0.12694(15) 0.0218(4) Uani 1 d . . . C17 C 0.5481(2) -0.1413(2) 0.03469(19) 0.0250(5) Uani 1 d . . . H17A H 0.4891 -0.1045 -0.0198 0.03 Uiso 1 calc R . . H17B H 0.5455 -0.2152 0.0158 0.03 Uiso 1 calc R . . C18 C 0.6645(2) -0.09813(19) 0.04394(18) 0.0234(5) Uani 1 d . . . C19 C 0.7201(2) -0.0274(2) 0.11829(19) 0.0290(6) Uani 1 d . . . H19 H 0.6867 -0.0086 0.1674 0.035 Uiso 1 calc R . . C20 C 0.8236(2) 0.0158(3) 0.1218(2) 0.0379(7) Uani 1 d . . . H20 H 0.861 0.0637 0.1732 0.045 Uiso 1 calc R . . C21 C 0.8725(2) -0.0109(3) 0.0500(2) 0.0414(7) Uani 1 d . . . H21 H 0.943 0.0194 0.0517 0.05 Uiso 1 calc R . . C22 C 0.8190(2) -0.0810(2) -0.0236(2) 0.0351(7) Uani 1 d . . . H22 H 0.8527 -0.0993 -0.0726 0.042 Uiso 1 calc R . . C23 C 0.7159(2) -0.1252(2) -0.02669(19) 0.0272(6) Uani 1 d . . . H23 H 0.68 -0.1744 -0.0773 0.033 Uiso 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 0.01167(13) 0.01835(14) 0.02115(15) 0.00101(11) 0.00890(10) 0.00087(10) C1 0.0156(12) 0.0287(12) 0.0406(16) -0.0006(11) 0.0128(11) 0.0031(10) C2 0.0185(13) 0.0434(15) 0.0451(18) 0.0108(13) 0.0044(12) -0.0006(12) O3 0.0156(8) 0.0184(7) 0.0196(8) 0.0035(6) 0.0096(7) -0.0014(6) C4 0.0200(12) 0.0203(11) 0.0231(13) 0.0055(9) 0.0123(10) 0.0000(9) C5 0.0295(14) 0.0295(13) 0.0424(17) 0.0174(12) 0.0192(13) 0.0027(11) F5A 0.0447(11) 0.0462(11) 0.1049(18) 0.0534(11) 0.0293(12) 0.0129(9) F5B 0.0246(8) 0.0638(11) 0.0299(9) 0.0131(8) 0.0068(7) 0.0032(8) F5C 0.0266(8) 0.0307(8) 0.0522(10) 0.0024(7) 0.0208(8) 0.0097(6) C6 0.0318(14) 0.0276(12) 0.0234(14) 0.0020(10) 0.0152(11) -0.0091(11) F6A 0.0244(8) 0.0565(10) 0.0333(9) -0.0106(8) 0.0200(7) -0.0033(7) F6B 0.0736(13) 0.0367(9) 0.0356(10) -0.0010(7) 0.0361(9) -0.0239(9) F6C 0.0369(9) 0.0338(8) 0.0243(8) -0.0023(6) 0.0127(7) -0.0114(7) C7 0.0262(13) 0.0189(11) 0.0289(14) 0.0000(9) 0.0200(11) -0.0047(9) C8 0.0226(12) 0.0204(11) 0.0312(14) 0.0004(10) 0.0170(11) -0.0018(10) C9 0.0504(18) 0.0210(12) 0.0414(17) 0.0028(11) 0.0329(15) 0.0006(12) N10 0.0184(10) 0.0200(9) 0.0252(11) 0.0009(8) 0.0137(9) 0.0005(8) C11 0.0277(13) 0.0190(11) 0.0262(13) 0.0000(9) 0.0188(11) 0.0020(10) C12 0.0169(11) 0.0243(11) 0.0252(13) -0.0010(10) 0.0114(10) -0.0013(9) C13 0.0209(12) 0.0271(12) 0.0244(13) -0.0008(10) 0.0108(10) -0.0018(10) C14 0.0228(13) 0.0345(13) 0.0246(13) 0.0081(11) 0.0158(11) 0.0095(11) C15 0.0291(14) 0.0352(14) 0.0289(14) 0.0063(11) 0.0199(12) 0.0113(11) N16 0.0190(10) 0.0292(10) 0.0211(11) 0.0031(8) 0.0119(9) 0.0053(8) C17 0.0270(13) 0.0312(13) 0.0211(13) -0.0002(10) 0.0138(11) 0.0012(10) C18 0.0206(12) 0.0349(13) 0.0167(12) 0.0055(10) 0.0089(10) 0.0079(10) C19 0.0232(13) 0.0470(16) 0.0200(13) -0.0005(12) 0.0112(10) 0.0032(12) C20 0.0216(14) 0.063(2) 0.0279(15) -0.0076(14) 0.0075(12) -0.0029(13) C21 0.0185(13) 0.074(2) 0.0357(17) -0.0012(15) 0.0147(12) -0.0042(14) C22 0.0262(14) 0.0566(18) 0.0281(15) 0.0042(13) 0.0164(12) 0.0109(13) C23 0.0285(14) 0.0366(14) 0.0200(13) 0.0043(11) 0.0131(11) 0.0101(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 1.976(2) . ? Zn1 O3 2.0234(15) . ? Zn1 O3 2.0821(16) 3_656 ? Zn1 N10 2.1042(19) 3_656 ? Zn1 Zn1 3.1165(6) 3_656 ? C1 C2 1.519(4) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 H2A 0.98 . ? C2 H2B 0.98 . ? C2 H2C 0.98 . ? O3 C4 1.377(3) . ? O3 Zn1 2.0821(16) 3_656 ? C4 C5 1.539(3) . ? C4 C6 1.548(3) . ? C4 C7 1.553(3) . ? C5 F5B 1.333(3) . ? C5 F5A 1.337(3) . ? C5 F5C 1.343(3) . ? C6 F6C 1.327(3) . ? C6 F6A 1.335(3) . ? C6 F6B 1.344(3) . ? C7 C8 1.510(3) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 N10 1.282(3) . ? C8 C9 1.502(3) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? N10 C11 1.479(3) . ? N10 Zn1 2.1042(19) 3_656 ? C11 C12 1.520(3) . ? C11 C14 1.528(3) . ? C11 H11 1 . ? C12 C13 1.521(3) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 N16 1.469(3) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.524(3) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 N16 1.465(3) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? N16 C17 1.459(3) . ? C17 C18 1.510(3) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 C19 1.391(4) . ? C18 C23 1.396(3) . ? C19 C20 1.384(4) . ? C19 H19 0.95 . ? C20 C21 1.387(4) . ? C20 H20 0.95 . ? C21 C22 1.373(4) . ? C21 H21 0.95 . ? C22 C23 1.386(4) . ? C22 H22 0.95 . ? C23 H23 0.95 . ? 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 C1 Zn1 O3 128.57(9) . . ? C1 Zn1 O3 116.72(9) . 3_656 ? O3 Zn1 O3 81.24(6) . 3_656 ? C1 Zn1 N10 117.47(9) . 3_656 ? O3 Zn1 N10 109.78(7) . 3_656 ? O3 Zn1 N10 89.84(7) 3_656 3_656 ? C1 Zn1 Zn1 134.84(8) . 3_656 ? O3 Zn1 Zn1 41.32(4) . 3_656 ? O3 Zn1 Zn1 39.92(4) 3_656 3_656 ? N10 Zn1 Zn1 102.59(6) 3_656 3_656 ? C2 C1 Zn1 119.21(19) . . ? C2 C1 H1A 107.5 . . ? Zn1 C1 H1A 107.5 . . ? C2 C1 H1B 107.5 . . ? Zn1 C1 H1B 107.5 . . ? H1A C1 H1B 107 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 O3 Zn1 136.70(14) . . ? C4 O3 Zn1 117.35(14) . 3_656 ? Zn1 O3 Zn1 98.76(6) . 3_656 ? O3 C4 C5 110.38(19) . . ? O3 C4 C6 108.77(19) . . ? C5 C4 C6 109.7(2) . . ? O3 C4 C7 112.66(19) . . ? C5 C4 C7 109.2(2) . . ? C6 C4 C7 105.99(18) . . ? F5B C5 F5A 107.4(2) . . ? F5B C5 F5C 106.9(2) . . ? F5A C5 F5C 106.2(2) . . ? F5B C5 C4 113.0(2) . . ? F5A C5 C4 112.7(2) . . ? F5C C5 C4 110.2(2) . . ? F6C C6 F6A 107.3(2) . . ? F6C C6 F6B 106.9(2) . . ? F6A C6 F6B 106.6(2) . . ? F6C C6 C4 113.1(2) . . ? F6A C6 C4 110.0(2) . . ? F6B C6 C4 112.7(2) . . ? C8 C7 C4 115.73(19) . . ? C8 C7 H7A 108.3 . . ? C4 C7 H7A 108.3 . . ? C8 C7 H7B 108.3 . . ? C4 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? N10 C8 C9 126.3(2) . . ? N10 C8 C7 117.6(2) . . ? C9 C8 C7 116.0(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 N10 C11 119.67(19) . . ? C8 N10 Zn1 116.24(16) . 3_656 ? C11 N10 Zn1 124.09(14) . 3_656 ? N10 C11 C12 110.13(18) . . ? N10 C11 C14 109.9(2) . . ? C12 C11 C14 110.16(19) . . ? N10 C11 H11 108.9 . . ? C12 C11 H11 108.9 . . ? C14 C11 H11 108.9 . . ? C11 C12 C13 110.44(19) . . ? C11 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? C11 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? N16 C13 C12 110.8(2) . . ? N16 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? N16 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C15 C14 C11 109.5(2) . . ? C15 C14 H14A 109.8 . . ? C11 C14 H14A 109.8 . . ? C15 C14 H14B 109.8 . . ? C11 C14 H14B 109.8 . . ? H14A C14 H14B 108.2 . . ? N16 C15 C14 110.7(2) . . ? N16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? N16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C17 N16 C15 111.23(19) . . ? C17 N16 C13 110.7(2) . . ? C15 N16 C13 110.30(19) . . ? N16 C17 C18 113.1(2) . . ? N16 C17 H17A 109 . . ? C18 C17 H17A 109 . . ? N16 C17 H17B 109 . . ? C18 C17 H17B 109 . . ? H17A C17 H17B 107.8 . . ? C19 C18 C23 118.5(2) . . ? C19 C18 C17 121.8(2) . . ? C23 C18 C17 119.6(2) . . ? C20 C19 C18 120.9(2) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 119.8(3) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 120.0(3) . . ? C22 C21 H21 120 . . ? C20 C21 H21 120 . . ? C21 C22 C23 120.3(2) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C18 120.5(3) . . ? C22 C23 H23 119.7 . . ? C18 C23 H23 119.7 . . ? 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 O3 Zn1 C1 C2 -95.5(2) . . . . ? O3 Zn1 C1 C2 163.95(18) 3_656 . . . ? N10 Zn1 C1 C2 59.0(2) 3_656 . . . ? Zn1 Zn1 C1 C2 -151.31(16) 3_656 . . . ? C1 Zn1 O3 C4 30.0(2) . . . . ? O3 Zn1 O3 C4 147.3(2) 3_656 . . . ? N10 Zn1 O3 C4 -126.1(2) 3_656 . . . ? Zn1 Zn1 O3 C4 147.3(2) 3_656 . . . ? C1 Zn1 O3 Zn1 -117.32(11) . . . 3_656 ? O3 Zn1 O3 Zn1 0 3_656 . . 3_656 ? N10 Zn1 O3 Zn1 86.65(8) 3_656 . . 3_656 ? Zn1 O3 C4 C5 -16.1(3) . . . . ? Zn1 O3 C4 C5 126.90(18) 3_656 . . . ? Zn1 O3 C4 C6 104.3(2) . . . . ? Zn1 O3 C4 C6 -112.69(18) 3_656 . . . ? Zn1 O3 C4 C7 -138.51(17) . . . . ? Zn1 O3 C4 C7 4.5(2) 3_656 . . . ? O3 C4 C5 F5B 59.8(3) . . . . ? C6 C4 C5 F5B -60.1(3) . . . . ? C7 C4 C5 F5B -175.86(19) . . . . ? O3 C4 C5 F5A -178.2(2) . . . . ? C6 C4 C5 F5A 61.9(3) . . . . ? C7 C4 C5 F5A -53.9(3) . . . . ? O3 C4 C5 F5C -59.8(3) . . . . ? C6 C4 C5 F5C -179.63(19) . . . . ? C7 C4 C5 F5C 64.6(2) . . . . ? O3 C4 C6 F6C -61.8(3) . . . . ? C5 C4 C6 F6C 59.0(3) . . . . ? C7 C4 C6 F6C 176.8(2) . . . . ? O3 C4 C6 F6A 58.1(3) . . . . ? C5 C4 C6 F6A 178.93(19) . . . . ? C7 C4 C6 F6A -63.3(2) . . . . ? O3 C4 C6 F6B 176.8(2) . . . . ? C5 C4 C6 F6B -62.4(3) . . . . ? C7 C4 C6 F6B 55.4(3) . . . . ? O3 C4 C7 C8 59.7(3) . . . . ? C5 C4 C7 C8 -63.4(3) . . . . ? C6 C4 C7 C8 178.5(2) . . . . ? C4 C7 C8 N10 -65.4(3) . . . . ? C4 C7 C8 C9 116.3(3) . . . . ? C9 C8 N10 C11 0.0(4) . . . . ? C7 C8 N10 C11 -178.1(2) . . . . ? C9 C8 N10 Zn1 -179.6(2) . . . 3_656 ? C7 C8 N10 Zn1 2.3(3) . . . 3_656 ? C8 N10 C11 C12 144.9(2) . . . . ? Zn1 N10 C11 C12 -35.6(3) 3_656 . . . ? C8 N10 C11 C14 -93.6(3) . . . . ? Zn1 N10 C11 C14 86.0(2) 3_656 . . . ? N10 C11 C12 C13 175.94(19) . . . . ? C14 C11 C12 C13 54.5(3) . . . . ? C11 C12 C13 N16 -57.1(3) . . . . ? N10 C11 C14 C15 -176.54(18) . . . . ? C12 C11 C14 C15 -55.0(3) . . . . ? C11 C14 C15 N16 58.6(3) . . . . ? C14 C15 N16 C17 175.4(2) . . . . ? C14 C15 N16 C13 -61.4(3) . . . . ? C12 C13 N16 C17 -176.06(19) . . . . ? C12 C13 N16 C15 60.4(3) . . . . ? C15 N16 C17 C18 -72.7(3) . . . . ? C13 N16 C17 C18 164.3(2) . . . . ? N16 C17 C18 C19 -20.4(3) . . . . ? N16 C17 C18 C23 162.9(2) . . . . ? C23 C18 C19 C20 0.6(4) . . . . ? C17 C18 C19 C20 -176.1(3) . . . . ? C18 C19 C20 C21 0.4(5) . . . . ? C19 C20 C21 C22 -0.8(5) . . . . ? C20 C21 C22 C23 0.1(5) . . . . ? C21 C22 C23 C18 0.9(4) . . . . ? C19 C18 C23 C22 -1.2(4) . . . . ? C17 C18 C23 C22 175.6(2) . . . . ? # Attachment 'complex8_GE292_100K_APEX_30juin08_archive.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-06-30 at 18:33:47 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\progs\wingx\files\archive.dat # CIF files read : job struct data_8 _database_code_depnum_ccdc_archive 'CCDC 718601' _audit_creation_date 2008-06-30T18:33:47-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C42 H42 F12 N2 O4 Zn2' _chemical_formula_sum 'C42 H42 F12 N2 O4 Zn2' _chemical_formula_weight 997.52 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0679(8) _cell_length_b 10.4866(10) _cell_length_c 11.6709(11) _cell_angle_alpha 93.584(3) _cell_angle_beta 95.307(3) _cell_angle_gamma 108.236(3) _cell_volume 1044.63(17) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4308 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.25 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.246 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.512 _exptl_absorpt_correction_T_max 0.732 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_unetI/netI 0.0436 _diffrn_reflns_number 11342 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 4769 _reflns_number_gt 4074 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0272P)^2^+0.2129P] 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_number_reflns 4769 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.031 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0688 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.503 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.069 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.44167(2) 0.05459(2) 0.901410(18) 0.01254(7) Uani 1 d . . . O1 O 0.44164(14) 0.07095(13) 1.06863(11) 0.0140(3) Uani 1 d . . . C2 C 0.4416(2) 0.1881(2) 1.13918(17) 0.0177(4) Uani 1 d . . . H2 H 0.5298 0.2675 1.1228 0.021 Uiso 1 calc R . . C3 C 0.2881(3) 0.2137(2) 1.10663(19) 0.0311(5) Uani 1 d . . . H3A H 0.2797 0.2307 1.0251 0.047 Uiso 1 calc R . . H3B H 0.2846 0.2924 1.1548 0.047 Uiso 1 calc R . . H3C H 0.201 0.1345 1.119 0.047 Uiso 1 calc R . . C4 C 0.4646(3) 0.1653(2) 1.26532(17) 0.0265(5) Uani 1 d . . . H4A H 0.3759 0.0905 1.2829 0.04 Uiso 1 calc R . . H4B H 0.4714 0.2473 1.3135 0.04 Uiso 1 calc R . . H4C H 0.5614 0.1433 1.2813 0.04 Uiso 1 calc R . . N5 N 0.58450(16) 0.21221(15) 0.82689(13) 0.0128(3) Uani 1 d . . . C6 C 0.7543(2) 0.23600(19) 0.85237(16) 0.0147(4) Uani 1 d . . . H6A H 0.8116 0.2958 0.7975 0.018 Uiso 1 calc R . . H6B H 0.7762 0.1494 0.8437 0.018 Uiso 1 calc R . . C7 C 0.80757(19) 0.30113(19) 0.97486(16) 0.0135(4) Uani 1 d . . . C8 C 0.8004(2) 0.4300(2) 1.00411(18) 0.0201(4) Uani 1 d . . . H8 H 0.7594 0.4751 0.9475 0.024 Uiso 1 calc R . . C9 C 0.8525(2) 0.4923(2) 1.11466(19) 0.0240(5) Uani 1 d . . . H9 H 0.8478 0.5803 1.1336 0.029 Uiso 1 calc R . . C10 C 0.9120(2) 0.4268(2) 1.19869(18) 0.0252(5) Uani 1 d . . . H10 H 0.9489 0.4702 1.2745 0.03 Uiso 1 calc R . . C11 C 0.9170(2) 0.2981(2) 1.17098(18) 0.0229(4) Uani 1 d . . . H11 H 0.956 0.2525 1.2282 0.027 Uiso 1 calc R . . C12 C 0.8651(2) 0.2355(2) 1.05933(17) 0.0174(4) Uani 1 d . . . H12 H 0.869 0.1472 1.0407 0.021 Uiso 1 calc R . . C13 C 0.5271(2) 0.26686(18) 0.74667(16) 0.0128(4) Uani 1 d . . . C14 C 0.6180(2) 0.35069(19) 0.66162(15) 0.0138(4) Uani 1 d . . . C15 C 0.6999(2) 0.2963(2) 0.58689(17) 0.0181(4) Uani 1 d . . . H15 H 0.6991 0.2057 0.5899 0.022 Uiso 1 calc R . . C16 C 0.7825(2) 0.3760(2) 0.50816(17) 0.0215(4) Uani 1 d . . . H16 H 0.8368 0.3392 0.4564 0.026 Uiso 1 calc R . . C17 C 0.7859(2) 0.5083(2) 0.50485(18) 0.0244(5) Uani 1 d . . . H17 H 0.8438 0.5625 0.4516 0.029 Uiso 1 calc R . . C18 C 0.7046(2) 0.5625(2) 0.5792(2) 0.0258(5) Uani 1 d . . . H18 H 0.708 0.6538 0.5777 0.031 Uiso 1 calc R . . C19 C 0.6188(2) 0.4821(2) 0.65567(18) 0.0199(4) Uani 1 d . . . H19 H 0.5599 0.5178 0.7044 0.024 Uiso 1 calc R . . C20 C 0.3550(2) 0.25288(18) 0.74112(16) 0.0137(4) Uani 1 d . . . H20A H 0.3297 0.3061 0.6796 0.016 Uiso 1 calc R . . H20B H 0.3365 0.2929 0.8153 0.016 Uiso 1 calc R . . C21 C 0.2397(2) 0.10497(19) 0.71725(16) 0.0133(4) Uani 1 d . . . C22 C 0.2444(2) 0.0513(2) 0.59159(17) 0.0173(4) Uani 1 d . . . F23 F 0.38870(13) 0.04837(12) 0.57766(10) 0.0244(3) Uani 1 d . . . F24 F 0.20866(14) 0.12825(13) 0.51253(10) 0.0274(3) Uani 1 d . . . F25 F 0.14762(13) -0.07407(12) 0.56306(10) 0.0240(3) Uani 1 d . . . C26 C 0.0748(2) 0.1150(2) 0.72980(17) 0.0179(4) Uani 1 d . . . F27 F 0.03698(13) 0.20608(13) 0.66597(11) 0.0262(3) Uani 1 d . . . F28 F -0.03861(12) -0.00272(12) 0.70200(10) 0.0246(3) Uani 1 d . . . F29 F 0.06713(12) 0.15427(12) 0.84066(10) 0.0224(3) Uani 1 d . . . O30 O 0.26399(14) 0.01591(13) 0.78966(11) 0.0154(3) Uani 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 0.01354(11) 0.01504(12) 0.01011(11) 0.00320(8) 0.00132(8) 0.00574(8) O1 0.0177(6) 0.0157(7) 0.0110(6) 0.0006(5) 0.0027(5) 0.0085(5) C2 0.0232(10) 0.0160(10) 0.0151(10) -0.0017(8) 0.0014(8) 0.0088(8) C3 0.0399(13) 0.0379(14) 0.0227(12) -0.0076(10) -0.0033(10) 0.0268(11) C4 0.0386(12) 0.0312(13) 0.0143(10) -0.0051(9) -0.0029(9) 0.0207(10) N5 0.0113(7) 0.0127(8) 0.0135(8) 0.0004(6) -0.0002(6) 0.0033(6) C6 0.0115(8) 0.0187(10) 0.0148(10) 0.0029(8) 0.0013(7) 0.0058(7) C7 0.0081(8) 0.0162(10) 0.0146(9) 0.0021(8) 0.0019(7) 0.0013(7) C8 0.0159(9) 0.0198(11) 0.0251(11) 0.0048(9) 0.0027(8) 0.0058(8) C9 0.0207(10) 0.0192(11) 0.0291(12) -0.0049(9) 0.0073(9) 0.0025(8) C10 0.0229(10) 0.0278(12) 0.0165(10) -0.0055(9) 0.0039(8) -0.0028(9) C11 0.0227(10) 0.0267(12) 0.0148(10) 0.0054(9) -0.0013(8) 0.0020(9) C12 0.0169(9) 0.0160(10) 0.0185(10) 0.0027(8) 0.0023(8) 0.0039(8) C13 0.0138(8) 0.0114(9) 0.0122(9) -0.0017(7) 0.0006(7) 0.0033(7) C14 0.0136(9) 0.0166(10) 0.0102(9) 0.0029(7) -0.0012(7) 0.0041(7) C15 0.0188(9) 0.0182(10) 0.0170(10) 0.0019(8) 0.0024(8) 0.0054(8) C16 0.0197(10) 0.0303(12) 0.0144(10) 0.0027(9) 0.0051(8) 0.0066(9) C17 0.0212(10) 0.0318(12) 0.0193(11) 0.0122(9) 0.0054(8) 0.0048(9) C18 0.0281(11) 0.0203(11) 0.0302(12) 0.0119(9) 0.0057(9) 0.0073(9) C19 0.0215(10) 0.0194(11) 0.0202(11) 0.0051(8) 0.0048(8) 0.0073(8) C20 0.0141(9) 0.0144(10) 0.0132(9) 0.0021(7) -0.0003(7) 0.0054(7) C21 0.0130(8) 0.0152(10) 0.0107(9) 0.0006(7) -0.0007(7) 0.0039(7) C22 0.0169(9) 0.0183(10) 0.0156(10) 0.0016(8) -0.0003(8) 0.0050(8) F23 0.0190(6) 0.0311(7) 0.0227(7) -0.0054(5) 0.0050(5) 0.0082(5) F24 0.0401(7) 0.0318(7) 0.0123(6) 0.0057(5) -0.0014(5) 0.0148(6) F25 0.0240(6) 0.0199(6) 0.0225(6) -0.0071(5) -0.0006(5) 0.0017(5) C26 0.0155(9) 0.0205(11) 0.0169(10) 0.0014(8) -0.0006(8) 0.0056(8) F27 0.0202(6) 0.0336(7) 0.0300(7) 0.0095(6) 0.0000(5) 0.0156(5) F28 0.0136(5) 0.0264(7) 0.0275(7) -0.0027(5) 0.0003(5) -0.0007(5) F29 0.0166(6) 0.0324(7) 0.0178(6) -0.0028(5) 0.0042(5) 0.0077(5) O30 0.0148(6) 0.0145(7) 0.0151(7) 0.0047(5) -0.0017(5) 0.0027(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O30 1.8967(13) . ? Zn1 O1 1.9485(13) . ? Zn1 O1 1.9586(13) 2_657 ? Zn1 N5 2.0529(15) . ? Zn1 Zn1 2.8919(5) 2_657 ? O1 C2 1.436(2) . ? O1 Zn1 1.9586(13) 2_657 ? C2 C4 1.512(3) . ? C2 C3 1.517(3) . ? C2 H2 1 . ? C3 H3A 0.98 . ? C3 H3B 0.98 . ? C3 H3C 0.98 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? N5 C13 1.280(2) . ? N5 C6 1.479(2) . ? C6 C7 1.512(3) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C12 1.390(3) . ? C7 C8 1.396(3) . ? C8 C9 1.380(3) . ? C8 H8 0.95 . ? C9 C10 1.394(3) . ? C9 H9 0.95 . ? C10 C11 1.383(3) . ? C10 H10 0.95 . ? C11 C12 1.392(3) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 C14 1.498(2) . ? C13 C20 1.516(2) . ? C14 C19 1.382(3) . ? C14 C15 1.400(2) . ? C15 C16 1.391(3) . ? C15 H15 0.95 . ? C16 C17 1.382(3) . ? C16 H16 0.95 . ? C17 C18 1.391(3) . ? C17 H17 0.95 . ? C18 C19 1.387(3) . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C20 C21 1.566(2) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 O30 1.352(2) . ? C21 C22 1.547(3) . ? C21 C26 1.551(2) . ? C22 F25 1.334(2) . ? C22 F23 1.343(2) . ? C22 F24 1.345(2) . ? C26 F28 1.334(2) . ? C26 F29 1.348(2) . ? C26 F27 1.353(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 O30 Zn1 O1 126.03(5) . . ? O30 Zn1 O1 123.96(6) . 2_657 ? O1 Zn1 O1 84.51(5) . 2_657 ? O30 Zn1 N5 97.17(6) . . ? O1 Zn1 N5 118.52(6) . . ? O1 Zn1 N5 107.18(5) 2_657 . ? O30 Zn1 Zn1 140.77(4) . 2_657 ? O1 Zn1 Zn1 42.39(4) . 2_657 ? O1 Zn1 Zn1 42.12(4) 2_657 2_657 ? N5 Zn1 Zn1 121.45(4) . 2_657 ? C2 O1 Zn1 126.38(12) . . ? C2 O1 Zn1 129.19(12) . 2_657 ? Zn1 O1 Zn1 95.49(5) . 2_657 ? O1 C2 C4 109.40(16) . . ? O1 C2 C3 108.02(16) . . ? C4 C2 C3 112.26(16) . . ? O1 C2 H2 109 . . ? C4 C2 H2 109 . . ? C3 C2 H2 109 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C13 N5 C6 122.62(15) . . ? C13 N5 Zn1 120.20(12) . . ? C6 N5 Zn1 115.80(11) . . ? N5 C6 C7 108.79(14) . . ? N5 C6 H6A 109.9 . . ? C7 C6 H6A 109.9 . . ? N5 C6 H6B 109.9 . . ? C7 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? C12 C7 C8 119.01(18) . . ? C12 C7 C6 121.24(17) . . ? C8 C7 C6 119.75(18) . . ? C9 C8 C7 120.5(2) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.3(2) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 119.6(2) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.1(2) . . ? C10 C11 H11 120 . . ? C12 C11 H11 120 . . ? C7 C12 C11 120.52(19) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? N5 C13 C14 125.35(16) . . ? N5 C13 C20 117.64(15) . . ? C14 C13 C20 116.91(16) . . ? C19 C14 C15 119.80(17) . . ? C19 C14 C13 119.64(16) . . ? C15 C14 C13 120.55(17) . . ? C16 C15 C14 119.40(18) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C17 C16 C15 120.39(18) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 120.19(18) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C19 C18 C17 119.5(2) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C14 C19 C18 120.63(18) . . ? C14 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C13 C20 C21 115.31(15) . . ? C13 C20 H20A 108.4 . . ? C21 C20 H20A 108.4 . . ? C13 C20 H20B 108.4 . . ? C21 C20 H20B 108.4 . . ? H20A C20 H20B 107.5 . . ? O30 C21 C22 109.04(15) . . ? O30 C21 C26 107.50(14) . . ? C22 C21 C26 109.25(15) . . ? O30 C21 C20 116.29(15) . . ? C22 C21 C20 108.81(14) . . ? C26 C21 C20 105.74(14) . . ? F25 C22 F23 106.59(15) . . ? F25 C22 F24 107.01(16) . . ? F23 C22 F24 106.71(15) . . ? F25 C22 C21 112.94(15) . . ? F23 C22 C21 110.04(15) . . ? F24 C22 C21 113.16(16) . . ? F28 C26 F29 106.87(15) . . ? F28 C26 F27 107.04(15) . . ? F29 C26 F27 106.01(15) . . ? F28 C26 C21 112.73(15) . . ? F29 C26 C21 109.55(15) . . ? F27 C26 C21 114.18(15) . . ? C21 O30 Zn1 123.71(11) . . ? 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 O30 Zn1 O1 C2 -82.17(15) . . . . ? O1 Zn1 O1 C2 149.23(16) 2_657 . . . ? N5 Zn1 O1 C2 42.64(15) . . . . ? Zn1 Zn1 O1 C2 149.23(16) 2_657 . . . ? O30 Zn1 O1 Zn1 128.61(6) . . . 2_657 ? O1 Zn1 O1 Zn1 0 2_657 . . 2_657 ? N5 Zn1 O1 Zn1 -106.59(6) . . . 2_657 ? Zn1 O1 C2 C4 -172.08(12) . . . . ? Zn1 O1 C2 C4 -33.2(2) 2_657 . . . ? Zn1 O1 C2 C3 65.45(19) . . . . ? Zn1 O1 C2 C3 -155.62(13) 2_657 . . . ? O30 Zn1 N5 C13 13.70(15) . . . . ? O1 Zn1 N5 C13 -124.29(14) . . . . ? O1 Zn1 N5 C13 142.61(14) 2_657 . . . ? Zn1 Zn1 N5 C13 -173.52(12) 2_657 . . . ? O30 Zn1 N5 C6 -153.30(12) . . . . ? O1 Zn1 N5 C6 68.72(13) . . . . ? O1 Zn1 N5 C6 -24.38(13) 2_657 . . . ? Zn1 Zn1 N5 C6 19.48(14) 2_657 . . . ? C13 N5 C6 C7 118.55(19) . . . . ? Zn1 N5 C6 C7 -74.80(16) . . . . ? N5 C6 C7 C12 115.44(18) . . . . ? N5 C6 C7 C8 -65.1(2) . . . . ? C12 C7 C8 C9 1.2(3) . . . . ? C6 C7 C8 C9 -178.23(16) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C8 C9 C10 C11 -0.7(3) . . . . ? C9 C10 C11 C12 0.9(3) . . . . ? C8 C7 C12 C11 -1.0(3) . . . . ? C6 C7 C12 C11 178.49(16) . . . . ? C10 C11 C12 C7 -0.1(3) . . . . ? C6 N5 C13 C14 5.7(3) . . . . ? Zn1 N5 C13 C14 -160.35(13) . . . . ? C6 N5 C13 C20 -170.48(16) . . . . ? Zn1 N5 C13 C20 23.4(2) . . . . ? N5 C13 C14 C19 -121.1(2) . . . . ? C20 C13 C14 C19 55.1(2) . . . . ? N5 C13 C14 C15 60.0(3) . . . . ? C20 C13 C14 C15 -123.81(19) . . . . ? C19 C14 C15 C16 0.6(3) . . . . ? C13 C14 C15 C16 179.53(18) . . . . ? C14 C15 C16 C17 1.0(3) . . . . ? C15 C16 C17 C18 -1.0(3) . . . . ? C16 C17 C18 C19 -0.8(3) . . . . ? C15 C14 C19 C18 -2.4(3) . . . . ? C13 C14 C19 C18 178.70(19) . . . . ? C17 C18 C19 C14 2.5(3) . . . . ? N5 C13 C20 C21 -62.9(2) . . . . ? C14 C13 C20 C21 120.59(17) . . . . ? C13 C20 C21 O30 54.3(2) . . . . ? C13 C20 C21 C22 -69.2(2) . . . . ? C13 C20 C21 C26 173.54(15) . . . . ? O30 C21 C22 F25 53.1(2) . . . . ? C26 C21 C22 F25 -64.1(2) . . . . ? C20 C21 C22 F25 -179.10(15) . . . . ? O30 C21 C22 F23 -65.84(19) . . . . ? C26 C21 C22 F23 176.93(15) . . . . ? C20 C21 C22 F23 61.93(19) . . . . ? O30 C21 C22 F24 174.89(14) . . . . ? C26 C21 C22 F24 57.7(2) . . . . ? C20 C21 C22 F24 -57.34(19) . . . . ? O30 C21 C26 F28 -60.6(2) . . . . ? C22 C21 C26 F28 57.6(2) . . . . ? C20 C21 C26 F28 174.58(15) . . . . ? O30 C21 C26 F29 58.29(19) . . . . ? C22 C21 C26 F29 176.49(15) . . . . ? C20 C21 C26 F29 -66.56(18) . . . . ? O30 C21 C26 F27 176.99(15) . . . . ? C22 C21 C26 F27 -64.8(2) . . . . ? C20 C21 C26 F27 52.1(2) . . . . ? C22 C21 O30 Zn1 114.76(14) . . . . ? C26 C21 O30 Zn1 -126.91(13) . . . . ? C20 C21 O30 Zn1 -8.7(2) . . . . ? O1 Zn1 O30 C21 112.65(13) . . . . ? O1 Zn1 O30 C21 -137.04(12) 2_657 . . . ? N5 Zn1 O30 C21 -20.70(14) . . . . ? Zn1 Zn1 O30 C21 169.06(10) 2_657 . . . ?