# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_frit11 _database_code_depnum_ccdc_archive 'CCDC 902412' #TrackingRef '14118_web_deposit_cif_file_0_JosephM.Fritsch_1348167072.CF3 tBu H Zn OR submit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H39 Cl2 F3 N2 O2 Zn' _chemical_formula_weight 676.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 9.9750(10) _cell_length_b 20.603(2) _cell_length_c 15.6453(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.171(4) _cell_angle_gamma 90.00 _cell_volume 3202.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 7257 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 25.42 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.983 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.688 _exptl_absorpt_correction_T_max 0.836 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 14450 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.42 _reflns_number_total 5860 _reflns_number_gt 5094 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0450P)^2^+5.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5860 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.48608(3) 0.163419(14) 0.108496(18) 0.01312(11) Uani 1 1 d . . . Cl1 Cl 0.11112(17) -0.03053(6) -0.33841(8) 0.0792(4) Uani 1 1 d . . . Cl2 Cl 0.34949(14) 0.02862(6) -0.39938(7) 0.0696(4) Uani 1 1 d . . . F1 F -0.01395(15) 0.11593(9) 0.12279(11) 0.0284(4) Uani 1 1 d . . . F2 F 0.05744(15) 0.10439(8) -0.00083(10) 0.0222(4) Uani 1 1 d . . . F3 F 0.05568(16) 0.02245(8) 0.08609(10) 0.0236(4) Uani 1 1 d . . . O2 O 0.55567(18) 0.24803(9) 0.10319(11) 0.0156(4) Uani 1 1 d . . . O1 O 0.46226(18) 0.14617(9) 0.23046(11) 0.0165(4) Uani 1 1 d . . . N1 N 0.3289(2) 0.10231(10) 0.07191(13) 0.0131(4) Uani 1 1 d . . . N2 N 0.5578(2) 0.12569(10) 0.00180(14) 0.0145(5) Uani 1 1 d . . . C1 C 0.6731(3) 0.13985(14) -0.02931(18) 0.0182(6) Uani 1 1 d . . . H1A H 0.7312 0.1704 0.0005 0.022 Uiso 1 1 calc R . . C2 C 0.7134(3) 0.11174(14) -0.10438(18) 0.0200(6) Uani 1 1 d . . . H2A H 0.7967 0.1233 -0.1253 0.024 Uiso 1 1 calc R . . C3 C 0.6300(3) 0.06730(13) -0.14681(17) 0.0178(6) Uani 1 1 d . . . H3A H 0.6559 0.0472 -0.1974 0.021 Uiso 1 1 calc R . . C4 C 0.5054(3) 0.05110(13) -0.11584(16) 0.0144(5) Uani 1 1 d . . . C5 C 0.4156(3) 0.00515(13) -0.15645(16) 0.0161(5) Uani 1 1 d . . . H5A H 0.4355 -0.0153 -0.2083 0.019 Uiso 1 1 calc R . . C6 C 0.3003(3) -0.00931(13) -0.12018(17) 0.0172(6) Uani 1 1 d . . . H6A H 0.2408 -0.0408 -0.1469 0.021 Uiso 1 1 calc R . . C7 C 0.2662(3) 0.02100(13) -0.04418(16) 0.0151(5) Uani 1 1 d . . . H7A H 0.1862 0.0083 -0.0200 0.018 Uiso 1 1 calc R . . C8 C 0.3465(2) 0.06878(12) -0.00405(16) 0.0123(5) Uani 1 1 d . . . C9 C 0.2237(2) 0.10391(12) 0.11883(16) 0.0137(5) Uani 1 1 d . . . C10 C 0.2299(3) 0.12258(13) 0.20425(16) 0.0152(5) Uani 1 1 d . . . H10A H 0.1471 0.1239 0.2298 0.018 Uiso 1 1 calc R . . C11 C 0.3471(3) 0.13985(13) 0.25732(16) 0.0142(5) Uani 1 1 d . . . C12 C 0.0808(3) 0.08665(14) 0.08093(17) 0.0183(6) Uani 1 1 d . . . C13 C 0.3396(3) 0.15402(14) 0.35282(17) 0.0199(6) Uani 1 1 d . . . C14 C 0.2073(4) 0.1365(2) 0.3874(2) 0.0446(10) Uani 1 1 d . . . H14A H 0.1905 0.0899 0.3795 0.067 Uiso 1 1 calc R . . H14B H 0.1342 0.1612 0.3564 0.067 Uiso 1 1 calc R . . H14C H 0.2116 0.1471 0.4486 0.067 Uiso 1 1 calc R . . C15 C 0.3580(6) 0.2288(2) 0.3617(3) 0.0598(13) Uani 1 1 d . . . H15A H 0.3607 0.2410 0.4224 0.090 Uiso 1 1 calc R . . H15B H 0.2824 0.2508 0.3294 0.090 Uiso 1 1 calc R . . H15C H 0.4424 0.2417 0.3389 0.090 Uiso 1 1 calc R . . C16 C 0.4552(4) 0.1220(3) 0.4040(2) 0.0669(16) Uani 1 1 d . . . H16A H 0.4482 0.0748 0.3969 0.100 Uiso 1 1 calc R . . H16B H 0.4531 0.1331 0.4648 0.100 Uiso 1 1 calc R . . H16C H 0.5400 0.1371 0.3838 0.100 Uiso 1 1 calc R . . C17 C 0.5533(3) 0.29400(12) 0.16392(16) 0.0133(5) Uani 1 1 d . . . C18 C 0.6644(3) 0.30078(13) 0.22709(17) 0.0163(5) Uani 1 1 d . . . C19 C 0.6555(3) 0.34632(14) 0.29219(18) 0.0199(6) Uani 1 1 d . . . H19A H 0.7271 0.3497 0.3363 0.024 Uiso 1 1 calc R . . C20 C 0.5453(3) 0.38664(14) 0.29430(17) 0.0201(6) Uani 1 1 d . . . H20A H 0.5403 0.4165 0.3401 0.024 Uiso 1 1 calc R . . C21 C 0.4425(3) 0.38312(13) 0.22915(17) 0.0182(6) Uani 1 1 d . . . H21A H 0.3689 0.4124 0.2297 0.022 Uiso 1 1 calc R . . C22 C 0.4430(3) 0.33830(13) 0.16307(17) 0.0155(5) Uani 1 1 d . . . C23 C 0.7952(3) 0.26172(14) 0.22145(19) 0.0202(6) Uani 1 1 d . . . C24 C 0.7727(3) 0.18843(14) 0.23211(19) 0.0217(6) Uani 1 1 d . . . H24A H 0.7190 0.1810 0.2807 0.033 Uiso 1 1 calc R . . H24B H 0.8599 0.1666 0.2428 0.033 Uiso 1 1 calc R . . H24C H 0.7248 0.1710 0.1796 0.033 Uiso 1 1 calc R . . C25 C 0.8518(3) 0.27590(15) 0.1349(2) 0.0270(7) Uani 1 1 d . . . H25A H 0.8796 0.3215 0.1332 0.041 Uiso 1 1 calc R . . H25B H 0.7821 0.2674 0.0880 0.041 Uiso 1 1 calc R . . H25C H 0.9296 0.2478 0.1286 0.041 Uiso 1 1 calc R . . C26 C 0.9050(3) 0.28150(17) 0.2920(2) 0.0336(8) Uani 1 1 d . . . H26A H 0.8757 0.2705 0.3483 0.050 Uiso 1 1 calc R . . H26B H 0.9208 0.3284 0.2890 0.050 Uiso 1 1 calc R . . H26C H 0.9885 0.2582 0.2836 0.050 Uiso 1 1 calc R . . C27 C 0.3292(3) 0.33835(14) 0.08932(18) 0.0206(6) Uani 1 1 d . . . C28 C 0.3883(4) 0.34644(19) 0.0030(2) 0.0384(9) Uani 1 1 d . . . H28A H 0.4525 0.3113 -0.0045 0.058 Uiso 1 1 calc R . . H28B H 0.4346 0.3883 0.0018 0.058 Uiso 1 1 calc R . . H28C H 0.3156 0.3448 -0.0435 0.058 Uiso 1 1 calc R . . C29 C 0.2453(3) 0.27613(16) 0.0885(2) 0.0308(7) Uani 1 1 d . . . H29A H 0.2994 0.2395 0.0712 0.046 Uiso 1 1 calc R . . H29B H 0.1654 0.2809 0.0477 0.046 Uiso 1 1 calc R . . H29C H 0.2174 0.2682 0.1461 0.046 Uiso 1 1 calc R . . C30 C 0.2315(4) 0.39529(17) 0.0978(2) 0.0421(9) Uani 1 1 d . . . H30A H 0.1648 0.3960 0.0479 0.063 Uiso 1 1 calc R . . H30B H 0.2820 0.4362 0.1008 0.063 Uiso 1 1 calc R . . H30C H 0.1857 0.3899 0.1502 0.063 Uiso 1 1 calc R . . C31 C 0.4714(2) 0.08253(12) -0.04030(16) 0.0127(5) Uani 1 1 d . . . C32 C 0.1840(5) 0.0394(2) -0.3769(3) 0.0639(13) Uani 1 1 d . . . H32A H 0.1301 0.0538 -0.4297 0.077 Uiso 1 1 calc R . . H32B H 0.1806 0.0744 -0.3336 0.077 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01277(16) 0.01384(18) 0.01317(17) -0.00349(12) 0.00334(11) -0.00324(11) Cl1 0.1357(12) 0.0362(6) 0.0669(8) -0.0233(5) 0.0166(8) -0.0272(7) Cl2 0.0967(9) 0.0625(7) 0.0554(7) 0.0162(5) 0.0384(6) 0.0442(7) F1 0.0128(8) 0.0436(11) 0.0293(9) -0.0175(8) 0.0042(7) 0.0014(7) F2 0.0183(8) 0.0285(9) 0.0187(8) -0.0022(7) -0.0042(6) 0.0039(7) F3 0.0214(8) 0.0254(9) 0.0241(9) -0.0049(7) 0.0036(7) -0.0121(7) O2 0.0189(9) 0.0125(9) 0.0159(9) -0.0046(7) 0.0050(7) -0.0043(7) O1 0.0147(9) 0.0212(10) 0.0139(9) -0.0010(8) 0.0030(7) -0.0021(7) N1 0.0137(10) 0.0139(11) 0.0118(10) -0.0025(9) 0.0009(8) -0.0018(8) N2 0.0167(11) 0.0119(11) 0.0153(11) -0.0001(9) 0.0038(9) -0.0006(9) C1 0.0170(13) 0.0161(14) 0.0221(14) 0.0005(11) 0.0055(11) -0.0035(11) C2 0.0191(13) 0.0194(15) 0.0228(14) 0.0023(11) 0.0095(11) 0.0000(11) C3 0.0227(14) 0.0185(14) 0.0130(13) 0.0014(11) 0.0067(10) 0.0054(11) C4 0.0194(13) 0.0119(13) 0.0122(12) 0.0032(10) 0.0025(10) 0.0041(10) C5 0.0209(13) 0.0153(14) 0.0115(12) -0.0019(10) -0.0012(10) 0.0041(11) C6 0.0186(13) 0.0154(14) 0.0163(13) -0.0036(11) -0.0053(10) 0.0014(11) C7 0.0140(12) 0.0160(14) 0.0149(13) 0.0006(10) -0.0003(10) 0.0013(10) C8 0.0143(12) 0.0105(12) 0.0119(12) 0.0013(10) -0.0003(10) 0.0032(10) C9 0.0126(12) 0.0121(13) 0.0164(13) 0.0001(10) 0.0015(10) -0.0016(10) C10 0.0146(12) 0.0177(14) 0.0139(13) -0.0003(10) 0.0045(10) -0.0011(10) C11 0.0173(13) 0.0110(13) 0.0147(13) 0.0009(10) 0.0035(10) 0.0009(10) C12 0.0156(13) 0.0216(15) 0.0179(14) -0.0051(11) 0.0029(10) -0.0008(11) C13 0.0194(14) 0.0282(16) 0.0121(13) -0.0007(11) 0.0024(11) 0.0009(11) C14 0.039(2) 0.074(3) 0.0218(17) -0.0051(17) 0.0094(15) -0.0094(19) C15 0.109(4) 0.041(2) 0.033(2) -0.0161(18) 0.028(2) -0.014(2) C16 0.046(2) 0.136(5) 0.0183(18) 0.004(2) 0.0016(16) 0.042(3) C17 0.0174(13) 0.0112(13) 0.0120(12) -0.0003(10) 0.0057(10) -0.0037(10) C18 0.0153(13) 0.0141(14) 0.0200(14) -0.0014(11) 0.0039(10) -0.0015(10) C19 0.0196(14) 0.0205(15) 0.0185(14) -0.0048(11) -0.0037(11) -0.0008(11) C20 0.0249(14) 0.0198(15) 0.0158(13) -0.0076(11) 0.0031(11) 0.0008(11) C21 0.0173(13) 0.0173(14) 0.0208(14) -0.0007(11) 0.0056(11) 0.0030(11) C22 0.0172(13) 0.0158(14) 0.0137(13) 0.0014(10) 0.0022(10) -0.0021(10) C23 0.0155(13) 0.0154(14) 0.0294(15) -0.0066(12) 0.0010(11) 0.0004(11) C24 0.0168(13) 0.0178(15) 0.0307(16) 0.0008(12) 0.0035(11) 0.0030(11) C25 0.0215(15) 0.0204(15) 0.0412(18) -0.0031(14) 0.0139(13) -0.0048(12) C26 0.0180(15) 0.0308(18) 0.050(2) -0.0142(16) -0.0084(14) 0.0040(13) C27 0.0219(14) 0.0200(15) 0.0190(14) 0.0008(11) -0.0034(11) 0.0027(11) C28 0.043(2) 0.053(2) 0.0179(16) 0.0103(15) -0.0041(14) -0.0036(17) C29 0.0218(15) 0.0263(17) 0.0417(19) 0.0034(14) -0.0118(13) -0.0019(12) C30 0.043(2) 0.034(2) 0.044(2) -0.0081(16) -0.0247(17) 0.0161(16) C31 0.0148(12) 0.0116(13) 0.0114(12) 0.0025(10) 0.0007(10) 0.0021(10) C32 0.083(3) 0.043(3) 0.071(3) 0.018(2) 0.033(3) 0.025(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.8809(18) . ? Zn1 O1 1.9763(18) . ? Zn1 N2 2.029(2) . ? Zn1 N1 2.052(2) . ? Cl1 C32 1.746(5) . ? Cl2 C32 1.733(5) . ? F1 C12 1.340(3) . ? F2 C12 1.331(3) . ? F3 C12 1.350(3) . ? O2 C17 1.343(3) . ? O1 C11 1.265(3) . ? N1 C9 1.334(3) . ? N1 C8 1.399(3) . ? N2 C1 1.321(3) . ? N2 C31 1.366(3) . ? C1 C2 1.400(4) . ? C1 H1A 0.9500 . ? C2 C3 1.368(4) . ? C2 H2A 0.9500 . ? C3 C4 1.414(4) . ? C3 H3A 0.9500 . ? C4 C31 1.415(4) . ? C4 C5 1.414(4) . ? C5 C6 1.361(4) . ? C5 H5A 0.9500 . ? C6 C7 1.411(4) . ? C6 H6A 0.9500 . ? C7 C8 1.383(4) . ? C7 H7A 0.9500 . ? C8 C31 1.443(4) . ? C9 C10 1.387(4) . ? C9 C12 1.535(3) . ? C10 C11 1.417(4) . ? C10 H10A 0.9500 . ? C11 C13 1.531(4) . ? C13 C16 1.497(4) . ? C13 C14 1.513(4) . ? C13 C15 1.556(5) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.424(4) . ? C17 C22 1.428(4) . ? C18 C19 1.393(4) . ? C18 C23 1.542(4) . ? C19 C20 1.380(4) . ? C19 H19A 0.9500 . ? C20 C21 1.382(4) . ? C20 H20A 0.9500 . ? C21 C22 1.387(4) . ? C21 H21A 0.9500 . ? C22 C27 1.544(4) . ? C23 C26 1.538(4) . ? C23 C24 1.538(4) . ? C23 C25 1.541(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.530(4) . ? C27 C29 1.530(4) . ? C27 C30 1.538(4) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 O1 106.63(8) . . ? O2 Zn1 N2 99.19(8) . . ? O1 Zn1 N2 143.84(8) . . ? O2 Zn1 N1 146.32(8) . . ? O1 Zn1 N1 90.21(8) . . ? N2 Zn1 N1 81.54(9) . . ? C17 O2 Zn1 126.30(16) . . ? C11 O1 Zn1 122.07(16) . . ? C9 N1 C8 130.1(2) . . ? C9 N1 Zn1 116.78(17) . . ? C8 N1 Zn1 112.86(16) . . ? C1 N2 C31 119.9(2) . . ? C1 N2 Zn1 126.99(19) . . ? C31 N2 Zn1 113.09(17) . . ? N2 C1 C2 122.9(3) . . ? N2 C1 H1A 118.6 . . ? C2 C1 H1A 118.6 . . ? C3 C2 C1 118.4(3) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C2 C3 C4 120.4(2) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C31 C4 C3 117.5(2) . . ? C31 C4 C5 119.4(2) . . ? C3 C4 C5 123.0(2) . . ? C6 C5 C4 119.0(2) . . ? C6 C5 H5A 120.5 . . ? C4 C5 H5A 120.5 . . ? C5 C6 C7 122.1(2) . . ? C5 C6 H6A 119.0 . . ? C7 C6 H6A 119.0 . . ? C8 C7 C6 121.6(2) . . ? C8 C7 H7A 119.2 . . ? C6 C7 H7A 119.2 . . ? C7 C8 N1 128.7(2) . . ? C7 C8 C31 116.5(2) . . ? N1 C8 C31 114.6(2) . . ? N1 C9 C10 124.6(2) . . ? N1 C9 C12 122.0(2) . . ? C10 C9 C12 113.3(2) . . ? C9 C10 C11 126.7(2) . . ? C9 C10 H10A 116.7 . . ? C11 C10 H10A 116.7 . . ? O1 C11 C10 123.9(2) . . ? O1 C11 C13 115.5(2) . . ? C10 C11 C13 120.6(2) . . ? F2 C12 F1 106.0(2) . . ? F2 C12 F3 108.0(2) . . ? F1 C12 F3 105.6(2) . . ? F2 C12 C9 112.6(2) . . ? F1 C12 C9 112.2(2) . . ? F3 C12 C9 112.0(2) . . ? C16 C13 C14 111.0(3) . . ? C16 C13 C11 109.6(2) . . ? C14 C13 C11 115.1(2) . . ? C16 C13 C15 108.0(4) . . ? C14 C13 C15 107.7(3) . . ? C11 C13 C15 105.1(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 C18 119.8(2) . . ? O2 C17 C22 120.5(2) . . ? C18 C17 C22 119.6(2) . . ? C19 C18 C17 118.4(2) . . ? C19 C18 C23 120.2(2) . . ? C17 C18 C23 121.3(2) . . ? C20 C19 C18 121.8(2) . . ? C20 C19 H19A 119.1 . . ? C18 C19 H19A 119.1 . . ? C19 C20 C21 119.4(3) . . ? C19 C20 H20A 120.3 . . ? C21 C20 H20A 120.3 . . ? C20 C21 C22 122.2(3) . . ? C20 C21 H21A 118.9 . . ? C22 C21 H21A 118.9 . . ? C21 C22 C17 118.3(2) . . ? C21 C22 C27 120.3(2) . . ? C17 C22 C27 121.4(2) . . ? C26 C23 C24 106.5(2) . . ? C26 C23 C25 106.7(2) . . ? C24 C23 C25 110.5(2) . . ? C26 C23 C18 111.8(2) . . ? C24 C23 C18 111.9(2) . . ? C25 C23 C18 109.3(2) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C29 109.7(3) . . ? C28 C27 C22 110.1(2) . . ? C29 C27 C22 111.7(2) . . ? C28 C27 C30 106.9(3) . . ? C29 C27 C30 106.8(3) . . ? C22 C27 C30 111.4(2) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N2 C31 C4 120.8(2) . . ? N2 C31 C8 117.9(2) . . ? C4 C31 C8 121.2(2) . . ? Cl2 C32 Cl1 113.4(2) . . ? Cl2 C32 H32A 108.9 . . ? Cl1 C32 H32A 108.9 . . ? Cl2 C32 H32B 108.9 . . ? Cl1 C32 H32B 108.9 . . ? H32A C32 H32B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.366 _refine_diff_density_min -1.060 _refine_diff_density_rms 0.076 data_pep111s _database_code_depnum_ccdc_archive 'CCDC 902413' #TrackingRef '14119_web_deposit_cif_file_1_JosephM.Fritsch_1348167072.pep111s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H36 F3 N3 O Si2 Zn' _chemical_formula_sum 'C24 H36 F3 N3 O Si2 Zn' _chemical_formula_weight 561.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.3993(18) _cell_length_b 14.898(3) _cell_length_c 19.859(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.070(2) _cell_angle_gamma 90.00 _cell_volume 2776.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8296 _cell_measurement_theta_min 3.86 _cell_measurement_theta_max 29.92 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 1.012 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8465 _exptl_absorpt_correction_T_max 0.9511 _exptl_absorpt_process_details 'Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 38050 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 30.56 _reflns_number_total 8233 _reflns_number_gt 6194 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+1.1752P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8233 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0820 _refine_ls_wR_factor_gt 0.0735 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.05279(2) 0.631129(13) 0.148145(9) 0.01494(5) Uani 1 1 d . . . Si1 Si 0.30492(5) 0.64411(4) 0.25054(2) 0.02091(11) Uani 1 1 d . . . Si2 Si 0.01023(5) 0.66285(3) 0.30300(2) 0.01847(10) Uani 1 1 d . . . O1 O -0.09630(12) 0.72300(8) 0.12176(6) 0.0172(2) Uani 1 1 d . . . N1 N 0.15769(14) 0.66387(10) 0.06407(7) 0.0160(3) Uani 1 1 d . . . N2 N 0.05778(14) 0.50664(9) 0.10440(7) 0.0160(3) Uani 1 1 d . . . N3 N 0.12295(15) 0.63965(10) 0.24030(7) 0.0171(3) Uani 1 1 d . . . C1 C -0.05762(17) 0.79885(11) 0.10025(8) 0.0160(3) Uani 1 1 d . . . C2 C 0.07725(18) 0.81600(12) 0.07419(8) 0.0188(3) Uani 1 1 d . . . H2 H 0.1050 0.8771 0.0705 0.023 Uiso 1 1 calc R . . C3 C 0.17297(17) 0.75135(11) 0.05341(8) 0.0169(3) Uani 1 1 d . . . C4 C 0.20900(17) 0.58839(12) 0.03064(8) 0.0169(3) Uani 1 1 d . . . C5 C 0.15126(17) 0.50470(11) 0.05313(8) 0.0159(3) Uani 1 1 d . . . C6 C 0.00069(18) 0.43112(12) 0.12605(8) 0.0188(3) Uani 1 1 d . . . C7 C 0.0325(2) 0.34726(12) 0.09754(9) 0.0226(4) Uani 1 1 d . . . H7 H -0.0101 0.2940 0.1134 0.027 Uiso 1 1 calc R . . C8 C 0.1252(2) 0.34341(12) 0.04689(9) 0.0223(4) Uani 1 1 d . . . H8 H 0.1472 0.2871 0.0275 0.027 Uiso 1 1 calc R . . C9 C 0.18862(18) 0.42236(12) 0.02309(8) 0.0186(3) Uani 1 1 d . . . C10 C 0.28578(19) 0.42210(13) -0.02882(9) 0.0227(4) Uani 1 1 d . . . H10 H 0.3136 0.3671 -0.0485 0.027 Uiso 1 1 calc R . . C11 C 0.33899(19) 0.50125(13) -0.05028(9) 0.0255(4) Uani 1 1 d . . . H11 H 0.4041 0.5009 -0.0852 0.031 Uiso 1 1 calc R . . C12 C 0.30007(19) 0.58380(13) -0.02202(9) 0.0226(4) Uani 1 1 d . . . H12 H 0.3372 0.6378 -0.0395 0.027 Uiso 1 1 calc R . . C13 C 0.3729(2) 0.61737(14) 0.33902(9) 0.0267(4) Uani 1 1 d . . . H13A H 0.3321 0.6597 0.3704 0.040 Uiso 1 1 calc R . . H13B H 0.4770 0.6224 0.3423 0.040 Uiso 1 1 calc R . . H13C H 0.3452 0.5561 0.3505 0.040 Uiso 1 1 calc R . . C14 C 0.3923(2) 0.56151(17) 0.19463(10) 0.0373(5) Uani 1 1 d . . . H14A H 0.3513 0.5018 0.2009 0.056 Uiso 1 1 calc R . . H14B H 0.4948 0.5597 0.2064 0.056 Uiso 1 1 calc R . . H14C H 0.3763 0.5799 0.1474 0.056 Uiso 1 1 calc R . . C15 C 0.3758(2) 0.75782(16) 0.22938(10) 0.0337(5) Uani 1 1 d . . . H15A H 0.3490 0.7721 0.1822 0.051 Uiso 1 1 calc R . . H15B H 0.4798 0.7578 0.2361 0.051 Uiso 1 1 calc R . . H15C H 0.3355 0.8030 0.2588 0.051 Uiso 1 1 calc R . . C16 C -0.18139(19) 0.66131(13) 0.27150(9) 0.0252(4) Uani 1 1 d . . . H16A H -0.1955 0.7038 0.2341 0.038 Uiso 1 1 calc R . . H16B H -0.2417 0.6786 0.3081 0.038 Uiso 1 1 calc R . . H16C H -0.2071 0.6008 0.2559 0.038 Uiso 1 1 calc R . . C17 C 0.0448(2) 0.77693(13) 0.34117(10) 0.0299(4) Uani 1 1 d . . . H17A H 0.1437 0.7803 0.3593 0.045 Uiso 1 1 calc R . . H17B H -0.0197 0.7868 0.3776 0.045 Uiso 1 1 calc R . . H17C H 0.0284 0.8231 0.3065 0.045 Uiso 1 1 calc R . . C18 C 0.0252(2) 0.57749(14) 0.37285(9) 0.0300(4) Uani 1 1 d . . . H18A H 0.0312 0.5172 0.3535 0.045 Uiso 1 1 calc R . . H18B H -0.0589 0.5813 0.3999 0.045 Uiso 1 1 calc R . . H18C H 0.1111 0.5895 0.4016 0.045 Uiso 1 1 calc R . . C19 C -0.16548(18) 0.87560(12) 0.10451(9) 0.0202(3) Uani 1 1 d . . . C20 C -0.1472(2) 0.91285(14) 0.17687(10) 0.0342(5) Uani 1 1 d . . . H20A H -0.2136 0.9628 0.1822 0.051 Uiso 1 1 calc R . . H20B H -0.0493 0.9341 0.1854 0.051 Uiso 1 1 calc R . . H20C H -0.1672 0.8653 0.2091 0.051 Uiso 1 1 calc R . . C21 C -0.1414(2) 0.95215(14) 0.05458(11) 0.0326(5) Uani 1 1 d . . . H21A H -0.1394 0.9277 0.0088 0.049 Uiso 1 1 calc R . . H21B H -0.0505 0.9818 0.0666 0.049 Uiso 1 1 calc R . . H21C H -0.2191 0.9958 0.0564 0.049 Uiso 1 1 calc R . . C22 C -0.3145(2) 0.83863(15) 0.09140(14) 0.0397(6) Uani 1 1 d . . . H22A H -0.3236 0.8132 0.0459 0.060 Uiso 1 1 calc R . . H22B H -0.3841 0.8871 0.0954 0.060 Uiso 1 1 calc R . . H22C H -0.3322 0.7917 0.1245 0.060 Uiso 1 1 calc R . . C23 C 0.29716(19) 0.79002(12) 0.01622(9) 0.0233(4) Uani 1 1 d . . . F24 F 0.32246(12) 0.87614(7) 0.03148(7) 0.0351(3) Uani 1 1 d . . . F25 F 0.27269(12) 0.78637(8) -0.05129(5) 0.0319(3) Uani 1 1 d . . . F26 F 0.41930(11) 0.74628(8) 0.03138(6) 0.0285(3) Uani 1 1 d . . . C27 C -0.0979(2) 0.43809(13) 0.18288(9) 0.0246(4) Uani 1 1 d . . . H27A H -0.0428 0.4528 0.2247 0.037 Uiso 1 1 calc R . . H27B H -0.1468 0.3807 0.1882 0.037 Uiso 1 1 calc R . . H27C H -0.1683 0.4853 0.1728 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01610(9) 0.01505(10) 0.01393(9) -0.00105(7) 0.00309(7) 0.00042(7) Si1 0.0171(2) 0.0292(3) 0.0163(2) -0.00342(19) 0.00094(18) 0.0020(2) Si2 0.0207(2) 0.0194(2) 0.0158(2) -0.00117(18) 0.00621(18) -0.00134(19) O1 0.0167(6) 0.0162(6) 0.0187(6) -0.0005(5) 0.0022(5) 0.0003(5) N1 0.0164(7) 0.0164(7) 0.0156(6) -0.0011(5) 0.0034(5) 0.0011(5) N2 0.0163(6) 0.0171(7) 0.0143(6) -0.0012(5) -0.0007(5) 0.0015(5) N3 0.0177(7) 0.0195(7) 0.0144(6) -0.0013(5) 0.0024(5) -0.0007(6) C1 0.0169(8) 0.0174(8) 0.0137(7) -0.0036(6) -0.0002(6) -0.0007(6) C2 0.0190(8) 0.0166(8) 0.0210(8) -0.0005(7) 0.0024(7) -0.0017(7) C3 0.0159(7) 0.0190(8) 0.0158(7) 0.0005(6) 0.0019(6) -0.0016(6) C4 0.0163(7) 0.0199(9) 0.0145(7) -0.0016(6) -0.0011(6) 0.0032(6) C5 0.0142(7) 0.0199(8) 0.0132(7) -0.0015(6) -0.0029(6) 0.0034(6) C6 0.0203(8) 0.0184(9) 0.0174(7) 0.0006(6) -0.0030(7) -0.0005(7) C7 0.0277(9) 0.0148(8) 0.0248(9) -0.0004(7) -0.0025(7) -0.0009(7) C8 0.0262(9) 0.0183(9) 0.0216(8) -0.0051(7) -0.0062(7) 0.0053(7) C9 0.0175(8) 0.0209(9) 0.0167(7) -0.0038(7) -0.0047(6) 0.0043(7) C10 0.0205(8) 0.0267(10) 0.0206(8) -0.0083(7) -0.0003(7) 0.0079(7) C11 0.0214(9) 0.0337(11) 0.0218(8) -0.0065(8) 0.0048(7) 0.0061(8) C12 0.0218(8) 0.0254(10) 0.0211(8) -0.0015(7) 0.0055(7) 0.0006(7) C13 0.0262(9) 0.0315(11) 0.0218(8) -0.0013(8) -0.0038(7) 0.0023(8) C14 0.0251(10) 0.0579(15) 0.0283(10) -0.0151(10) -0.0031(8) 0.0147(10) C15 0.0265(10) 0.0481(13) 0.0264(10) 0.0039(9) -0.0001(8) -0.0117(9) C16 0.0230(9) 0.0285(10) 0.0247(9) -0.0003(8) 0.0087(7) -0.0016(7) C17 0.0322(10) 0.0271(10) 0.0313(10) -0.0103(8) 0.0115(8) -0.0043(8) C18 0.0329(10) 0.0345(11) 0.0235(9) 0.0060(8) 0.0088(8) -0.0012(9) C19 0.0194(8) 0.0169(8) 0.0244(8) -0.0018(7) 0.0042(7) 0.0027(7) C20 0.0457(12) 0.0278(11) 0.0299(10) -0.0047(8) 0.0090(9) 0.0076(9) C21 0.0326(11) 0.0301(11) 0.0354(11) 0.0065(9) 0.0045(9) 0.0091(9) C22 0.0194(9) 0.0252(11) 0.0745(17) -0.0045(11) 0.0017(10) 0.0040(8) C23 0.0216(9) 0.0214(9) 0.0274(9) 0.0010(7) 0.0073(7) -0.0010(7) F24 0.0304(6) 0.0218(6) 0.0548(8) -0.0019(5) 0.0182(6) -0.0072(5) F25 0.0318(6) 0.0408(7) 0.0243(5) 0.0091(5) 0.0118(5) 0.0025(5) F26 0.0157(5) 0.0325(6) 0.0378(6) -0.0016(5) 0.0052(5) -0.0007(4) C27 0.0298(10) 0.0204(9) 0.0241(9) 0.0015(7) 0.0070(8) -0.0031(7) _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 N3 1.9160(14) . ? Zn1 O1 2.0083(12) . ? Zn1 N1 2.0430(13) . ? Zn1 N2 2.0495(14) . ? Si1 N3 1.7129(15) . ? Si1 C14 1.876(2) . ? Si1 C15 1.876(2) . ? Si1 C13 1.8801(19) . ? Si2 N3 1.7127(14) . ? Si2 C16 1.875(2) . ? Si2 C18 1.8817(19) . ? Si2 C17 1.882(2) . ? O1 C1 1.268(2) . ? N1 C3 1.329(2) . ? N1 C4 1.404(2) . ? N2 C6 1.328(2) . ? N2 C5 1.3804(19) . ? C1 C2 1.418(2) . ? C1 C19 1.533(2) . ? C2 C3 1.395(2) . ? C2 H2 0.9500 . ? C3 C23 1.527(2) . ? C4 C12 1.388(2) . ? C4 C5 1.440(2) . ? C5 C9 1.416(2) . ? C6 C7 1.410(2) . ? C6 C27 1.501(2) . ? C7 C8 1.367(3) . ? C7 H7 0.9500 . ? C8 C9 1.411(3) . ? C8 H8 0.9500 . ? C9 C10 1.413(2) . ? C10 C11 1.358(3) . ? C10 H10 0.9500 . ? C11 C12 1.408(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C22 1.514(3) . ? C19 C21 1.536(3) . ? C19 C20 1.541(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 F24 1.337(2) . ? C23 F26 1.340(2) . ? C23 F25 1.349(2) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 N3 Zn1 O1 113.81(5) . . ? N3 Zn1 N1 127.47(6) . . ? O1 Zn1 N1 89.12(5) . . ? N3 Zn1 N2 116.76(6) . . ? O1 Zn1 N2 122.52(5) . . ? N1 Zn1 N2 81.18(5) . . ? N3 Si1 C14 111.73(9) . . ? N3 Si1 C15 111.88(9) . . ? C14 Si1 C15 106.73(11) . . ? N3 Si1 C13 112.96(8) . . ? C14 Si1 C13 106.05(9) . . ? C15 Si1 C13 107.07(9) . . ? N3 Si2 C16 112.06(8) . . ? N3 Si2 C18 112.02(8) . . ? C16 Si2 C18 105.68(9) . . ? N3 Si2 C17 112.02(8) . . ? C16 Si2 C17 106.70(9) . . ? C18 Si2 C17 107.99(10) . . ? C1 O1 Zn1 119.11(10) . . ? C3 N1 C4 131.83(14) . . ? C3 N1 Zn1 115.17(10) . . ? C4 N1 Zn1 112.84(11) . . ? C6 N2 C5 120.36(14) . . ? C6 N2 Zn1 127.63(11) . . ? C5 N2 Zn1 111.19(11) . . ? Si2 N3 Si1 123.96(9) . . ? Si2 N3 Zn1 120.87(8) . . ? Si1 N3 Zn1 113.97(7) . . ? O1 C1 C2 124.17(15) . . ? O1 C1 C19 116.32(14) . . ? C2 C1 C19 119.50(15) . . ? C3 C2 C1 125.93(16) . . ? C3 C2 H2 117.0 . . ? C1 C2 H2 117.0 . . ? N1 C3 C2 123.55(15) . . ? N1 C3 C23 122.60(15) . . ? C2 C3 C23 113.85(15) . . ? C12 C4 N1 129.56(16) . . ? C12 C4 C5 116.66(15) . . ? N1 C4 C5 113.70(14) . . ? N2 C5 C9 120.71(15) . . ? N2 C5 C4 118.42(14) . . ? C9 C5 C4 120.87(14) . . ? N2 C6 C7 121.50(15) . . ? N2 C6 C27 117.46(15) . . ? C7 C6 C27 121.04(15) . . ? C8 C7 C6 119.33(16) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 120.58(16) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C10 122.88(16) . . ? C8 C9 C5 117.52(15) . . ? C10 C9 C5 119.60(16) . . ? C11 C10 C9 119.32(16) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 121.68(16) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C4 C12 C11 121.81(17) . . ? C4 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? Si1 C13 H13A 109.5 . . ? Si1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? Si1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? Si1 C14 H14A 109.5 . . ? Si1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? Si1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? Si1 C15 H15A 109.5 . . ? Si1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Si1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? Si2 C16 H16A 109.5 . . ? Si2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Si2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Si2 C17 H17A 109.5 . . ? Si2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Si2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? Si2 C18 H18A 109.5 . . ? Si2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? Si2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C22 C19 C1 109.11(15) . . ? C22 C19 C21 109.00(17) . . ? C1 C19 C21 113.42(14) . . ? C22 C19 C20 110.30(16) . . ? C1 C19 C20 106.20(15) . . ? C21 C19 C20 108.76(16) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? F24 C23 F26 106.01(15) . . ? F24 C23 F25 106.42(15) . . ? F26 C23 F25 107.58(14) . . ? F24 C23 C3 112.56(14) . . ? F26 C23 C3 112.07(15) . . ? F25 C23 C3 111.80(15) . . ? C6 C27 H27A 109.5 . . ? C6 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C6 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 29.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.585 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.068 data_frit06 _database_code_depnum_ccdc_archive 'CCDC 902414' #TrackingRef '14120_web_deposit_cif_file_2_JosephM.Fritsch_1348167072.frit06 submit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H39 F3 N2 O2 Zn' _chemical_formula_weight 606.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 8.9795(15) _cell_length_b 18.148(3) _cell_length_c 18.590(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3029.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2820 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 24.43 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 0.860 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7948 _exptl_absorpt_correction_T_max 0.9190 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 14142 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_sigmaI/netI 0.0830 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.37 _reflns_number_total 5451 _reflns_number_gt 4793 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0580P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.005(14) _refine_ls_number_reflns 5451 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1144 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.41210(5) 0.38891(2) 0.22858(3) 0.02227(14) Uani 1 1 d . . . F1 F 0.3934(4) 0.36092(17) -0.04064(15) 0.0554(8) Uani 1 1 d . . . F2 F 0.2008(4) 0.29385(15) -0.01913(16) 0.0572(9) Uani 1 1 d . . . F3 F 0.1889(3) 0.41004(13) -0.00273(14) 0.0358(6) Uani 1 1 d . . . O2 O 0.5790(3) 0.40712(13) 0.28610(15) 0.0248(6) Uani 1 1 d . . . O1 O 0.3422(3) 0.28789(14) 0.23400(17) 0.0265(6) Uani 1 1 d . . . N2 N 0.2827(3) 0.48436(16) 0.2260(2) 0.0227(7) Uani 1 1 d . . . N1 N 0.3802(4) 0.39829(18) 0.12085(18) 0.0242(8) Uani 1 1 d . . . C1 C 0.2208(7) 0.1575(3) 0.2693(4) 0.0644(17) Uani 1 1 d . . . H1A H 0.2016 0.1054 0.2798 0.097 Uiso 1 1 calc R . . H1B H 0.1259 0.1840 0.2660 0.097 Uiso 1 1 calc R . . H1C H 0.2813 0.1789 0.3079 0.097 Uiso 1 1 calc R . . C2 C 0.4563(6) 0.1289(3) 0.2021(4) 0.069(2) Uani 1 1 d . . . H2A H 0.4466 0.0766 0.2145 0.103 Uiso 1 1 calc R . . H2B H 0.5164 0.1538 0.2387 0.103 Uiso 1 1 calc R . . H2C H 0.5050 0.1336 0.1551 0.103 Uiso 1 1 calc R . . C3 C 0.2129(7) 0.1215(3) 0.1412(4) 0.0634(17) Uani 1 1 d . . . H3A H 0.1990 0.0703 0.1567 0.095 Uiso 1 1 calc R . . H3B H 0.2671 0.1224 0.0954 0.095 Uiso 1 1 calc R . . H3C H 0.1154 0.1449 0.1349 0.095 Uiso 1 1 calc R . . C4 C 0.3030(5) 0.1638(2) 0.1989(3) 0.0324(11) Uani 1 1 d . . . C5 C 0.3264(4) 0.2460(2) 0.1805(3) 0.0296(11) Uani 1 1 d . . . C6 C 0.3243(5) 0.2686(2) 0.1079(2) 0.0303(10) Uani 1 1 d . . . H6A H 0.3152 0.2309 0.0728 0.036 Uiso 1 1 calc R . . C7 C 0.3341(4) 0.3411(2) 0.0822(2) 0.0276(10) Uani 1 1 d . . . C8 C 0.2778(6) 0.3517(3) 0.0048(3) 0.0356(11) Uani 1 1 d . . . C9 C 0.3685(4) 0.4743(2) 0.1039(2) 0.0257(10) Uani 1 1 d . . . C10 C 0.4174(5) 0.5083(2) 0.0420(2) 0.0279(9) Uani 1 1 d . . . H10A H 0.4670 0.4807 0.0058 0.033 Uiso 1 1 calc R . . C11 C 0.3930(5) 0.5851(2) 0.0328(3) 0.0338(11) Uani 1 1 d . . . H11A H 0.4280 0.6085 -0.0097 0.041 Uiso 1 1 calc R . . C12 C 0.3202(5) 0.6264(2) 0.0836(3) 0.0316(11) Uani 1 1 d . . . H12A H 0.2986 0.6768 0.0747 0.038 Uiso 1 1 calc R . . C13 C 0.2776(4) 0.5938(2) 0.1490(3) 0.0276(10) Uani 1 1 d . . . C14 C 0.2052(5) 0.6316(2) 0.2055(2) 0.0304(10) Uani 1 1 d . . . H14A H 0.1785 0.6819 0.1996 0.037 Uiso 1 1 calc R . . C15 C 0.1736(4) 0.5963(2) 0.2684(3) 0.0313(10) Uani 1 1 d . . . H15A H 0.1228 0.6217 0.3058 0.038 Uiso 1 1 calc R . . C16 C 0.2164(4) 0.5216(2) 0.2781(2) 0.0251(9) Uani 1 1 d . . . C17 C 0.3092(4) 0.5175(2) 0.1605(2) 0.0220(9) Uani 1 1 d . . . C18 C 0.1847(5) 0.4827(2) 0.3483(2) 0.0325(10) Uani 1 1 d . . . H18A H 0.2297 0.4335 0.3473 0.049 Uiso 1 1 calc R . . H18B H 0.0768 0.4781 0.3548 0.049 Uiso 1 1 calc R . . H18C H 0.2269 0.5111 0.3881 0.049 Uiso 1 1 calc R . . C19 C 0.7036(4) 0.37270(19) 0.3090(2) 0.0225(9) Uani 1 1 d . . . C20 C 0.7163(5) 0.3529(2) 0.3834(2) 0.0262(9) Uani 1 1 d . . . C21 C 0.8493(5) 0.3209(2) 0.4068(3) 0.0283(10) Uani 1 1 d . . . H21A H 0.8588 0.3075 0.4560 0.034 Uiso 1 1 calc R . . C22 C 0.9685(5) 0.3078(2) 0.3605(3) 0.0307(10) Uani 1 1 d . . . H22A H 1.0570 0.2853 0.3777 0.037 Uiso 1 1 calc R . . C23 C 0.9562(4) 0.3280(2) 0.2895(2) 0.0281(10) Uani 1 1 d . . . H23A H 1.0385 0.3201 0.2583 0.034 Uiso 1 1 calc R . . C24 C 0.8261(4) 0.3600(2) 0.2615(2) 0.0249(9) Uani 1 1 d . . . C25 C 0.5896(5) 0.3674(2) 0.4373(2) 0.0293(10) Uani 1 1 d . . . C26 C 0.4505(5) 0.3224(2) 0.4155(3) 0.0300(10) Uani 1 1 d . . . H26A H 0.4715 0.2697 0.4209 0.045 Uiso 1 1 calc R . . H26B H 0.4251 0.3330 0.3653 0.045 Uiso 1 1 calc R . . H26C H 0.3667 0.3359 0.4466 0.045 Uiso 1 1 calc R . . C27 C 0.6304(6) 0.3440(3) 0.5139(3) 0.0399(12) Uani 1 1 d . . . H27A H 0.6595 0.2919 0.5141 0.060 Uiso 1 1 calc R . . H27B H 0.5441 0.3509 0.5455 0.060 Uiso 1 1 calc R . . H27C H 0.7135 0.3741 0.5313 0.060 Uiso 1 1 calc R . . C28 C 0.5518(5) 0.4500(2) 0.4405(3) 0.0355(11) Uani 1 1 d . . . H28A H 0.4665 0.4576 0.4725 0.053 Uiso 1 1 calc R . . H28B H 0.5271 0.4677 0.3921 0.053 Uiso 1 1 calc R . . H28C H 0.6379 0.4774 0.4589 0.053 Uiso 1 1 calc R . . C29 C 0.8178(5) 0.3755(2) 0.1796(2) 0.0265(10) Uani 1 1 d . . . C30 C 0.7110(5) 0.3191(2) 0.1456(3) 0.0329(11) Uani 1 1 d . . . H30A H 0.6938 0.3320 0.0951 0.049 Uiso 1 1 calc R . . H30B H 0.6161 0.3196 0.1716 0.049 Uiso 1 1 calc R . . H30C H 0.7551 0.2698 0.1484 0.049 Uiso 1 1 calc R . . C31 C 0.9677(5) 0.3653(3) 0.1417(3) 0.0389(12) Uani 1 1 d . . . H31A H 1.0404 0.3999 0.1618 0.058 Uiso 1 1 calc R . . H31B H 0.9558 0.3748 0.0901 0.058 Uiso 1 1 calc R . . H31C H 1.0029 0.3148 0.1489 0.058 Uiso 1 1 calc R . . C32 C 0.7702(5) 0.4559(2) 0.1642(3) 0.0339(11) Uani 1 1 d . . . H32A H 0.8469 0.4897 0.1821 0.051 Uiso 1 1 calc R . . H32B H 0.6756 0.4662 0.1885 0.051 Uiso 1 1 calc R . . H32C H 0.7581 0.4628 0.1122 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0207(2) 0.0239(2) 0.0222(3) 0.0020(2) -0.0002(2) 0.00147(19) F1 0.070(2) 0.0654(18) 0.0309(16) -0.0001(14) 0.0174(18) 0.0159(17) F2 0.095(3) 0.0427(16) 0.0340(18) -0.0120(14) -0.0167(18) -0.0065(17) F3 0.0401(14) 0.0383(14) 0.0288(15) 0.0031(12) -0.0068(13) -0.0019(12) O2 0.0197(12) 0.0255(13) 0.0290(17) 0.0000(11) -0.0024(14) 0.0054(11) O1 0.0272(13) 0.0264(13) 0.0259(17) 0.0025(14) -0.0009(15) -0.0020(11) N2 0.0211(15) 0.0242(15) 0.0227(19) -0.0016(16) -0.0024(18) -0.0022(13) N1 0.0251(17) 0.0274(17) 0.0200(18) 0.0007(15) -0.0040(15) 0.0021(14) C1 0.087(4) 0.033(3) 0.073(4) 0.011(3) 0.026(4) -0.007(3) C2 0.035(3) 0.043(3) 0.129(6) 0.018(3) 0.010(3) 0.014(2) C3 0.057(3) 0.045(3) 0.089(5) 0.010(3) -0.015(4) -0.023(3) C4 0.028(2) 0.025(2) 0.044(3) 0.003(2) 0.002(2) 0.0006(18) C5 0.019(2) 0.028(2) 0.042(3) 0.001(2) 0.003(2) 0.0024(17) C6 0.036(2) 0.025(2) 0.031(3) -0.0095(19) 0.003(2) 0.0044(19) C7 0.023(2) 0.035(2) 0.025(3) -0.005(2) 0.005(2) 0.0070(18) C8 0.045(3) 0.038(2) 0.024(3) -0.006(2) 0.003(2) 0.002(2) C9 0.0211(19) 0.030(2) 0.026(3) 0.0048(19) -0.0047(19) -0.0009(16) C10 0.0235(18) 0.038(2) 0.022(2) 0.0041(18) -0.003(2) -0.003(2) C11 0.029(2) 0.038(2) 0.034(3) 0.016(2) -0.005(2) -0.008(2) C12 0.026(2) 0.026(2) 0.043(3) 0.008(2) -0.008(2) -0.0049(17) C13 0.0199(19) 0.030(2) 0.033(3) 0.0016(19) -0.008(2) -0.0014(17) C14 0.026(2) 0.029(2) 0.036(3) -0.0007(19) -0.005(2) 0.0042(17) C15 0.0209(18) 0.034(2) 0.039(3) -0.010(2) -0.001(2) 0.0050(16) C16 0.0161(16) 0.032(2) 0.027(2) -0.007(2) -0.001(2) -0.0015(16) C17 0.0150(17) 0.0250(19) 0.026(2) 0.0054(18) -0.0049(18) -0.0035(16) C18 0.030(2) 0.036(2) 0.031(3) -0.001(2) 0.005(2) -0.0004(19) C19 0.0222(18) 0.0195(19) 0.026(2) -0.0023(16) -0.0005(19) 0.0008(15) C20 0.026(2) 0.0240(19) 0.028(3) 0.0016(18) -0.005(2) -0.0048(18) C21 0.028(2) 0.025(2) 0.032(3) 0.0023(19) -0.009(2) -0.0042(17) C22 0.025(2) 0.027(2) 0.041(3) -0.002(2) -0.008(2) 0.0011(17) C23 0.0217(19) 0.0275(19) 0.035(3) -0.0029(19) 0.0007(19) -0.0007(16) C24 0.0232(18) 0.0216(17) 0.030(3) -0.0019(19) 0.003(2) -0.0033(16) C25 0.031(2) 0.033(2) 0.024(2) 0.0040(18) 0.004(2) 0.0001(19) C26 0.025(2) 0.036(2) 0.029(3) 0.004(2) 0.008(2) 0.0005(18) C27 0.044(3) 0.046(3) 0.029(3) 0.001(2) 0.007(2) 0.003(2) C28 0.035(3) 0.038(2) 0.034(3) -0.009(2) 0.003(2) 0.006(2) C29 0.024(2) 0.032(2) 0.023(2) -0.0057(19) 0.002(2) 0.0020(17) C30 0.029(2) 0.033(2) 0.037(3) -0.007(2) 0.001(2) 0.0015(19) C31 0.029(2) 0.052(3) 0.036(3) -0.001(2) 0.006(2) 0.001(2) C32 0.039(2) 0.033(2) 0.030(3) 0.005(2) 0.002(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.871(3) . ? Zn1 O1 1.940(3) . ? Zn1 N1 2.030(3) . ? Zn1 N2 2.087(3) . ? F1 C8 1.349(6) . ? F2 C8 1.334(5) . ? F3 C8 1.334(5) . ? O2 C19 1.350(5) . ? O1 C5 1.259(5) . ? N2 C16 1.322(5) . ? N2 C17 1.378(5) . ? N1 C7 1.328(5) . ? N1 C9 1.420(5) . ? C1 C4 1.507(7) . ? C2 C4 1.518(6) . ? C3 C4 1.548(7) . ? C4 C5 1.544(6) . ? C5 C6 1.412(6) . ? C6 C7 1.402(6) . ? C7 C8 1.537(6) . ? C9 C10 1.377(6) . ? C9 C17 1.417(6) . ? C10 C11 1.421(6) . ? C11 C12 1.372(6) . ? C12 C13 1.404(6) . ? C13 C14 1.413(6) . ? C13 C17 1.429(5) . ? C14 C15 1.364(6) . ? C15 C16 1.421(5) . ? C16 C18 1.511(6) . ? C19 C24 1.430(6) . ? C19 C20 1.432(6) . ? C20 C21 1.398(6) . ? C20 C25 1.538(6) . ? C21 C22 1.394(6) . ? C22 C23 1.374(6) . ? C23 C24 1.404(6) . ? C24 C29 1.550(6) . ? C25 C27 1.532(6) . ? C25 C28 1.539(6) . ? C25 C26 1.547(6) . ? C29 C31 1.531(6) . ? C29 C30 1.538(6) . ? C29 C32 1.548(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 O1 113.34(11) . . ? O2 Zn1 N1 131.46(12) . . ? O1 Zn1 N1 94.86(13) . . ? O2 Zn1 N2 108.23(12) . . ? O1 Zn1 N2 127.26(12) . . ? N1 Zn1 N2 80.17(14) . . ? C19 O2 Zn1 139.7(2) . . ? C5 O1 Zn1 124.5(3) . . ? C16 N2 C17 120.1(3) . . ? C16 N2 Zn1 131.2(3) . . ? C17 N2 Zn1 106.6(3) . . ? C7 N1 C9 128.0(4) . . ? C7 N1 Zn1 120.8(3) . . ? C9 N1 Zn1 108.2(3) . . ? C1 C4 C2 112.2(5) . . ? C1 C4 C5 109.5(4) . . ? C2 C4 C5 106.8(4) . . ? C1 C4 C3 107.9(4) . . ? C2 C4 C3 107.1(4) . . ? C5 C4 C3 113.4(4) . . ? O2 C5 C6 125.5(4) . . ? O2 C5 C4 115.1(4) . . ? C6 C5 C4 119.4(4) . . ? C7 C6 C5 126.7(4) . . ? N2 C7 C6 124.7(4) . . ? N2 C7 C8 120.7(4) . . ? C6 C7 C8 114.5(4) . . ? F2 C8 F3 106.2(4) . . ? F2 C8 F1 106.7(4) . . ? F3 C8 F1 107.2(4) . . ? F2 C8 C7 112.7(4) . . ? F3 C8 C7 113.2(4) . . ? F1 C8 C7 110.5(4) . . ? C10 C9 C17 119.6(4) . . ? C10 C9 N1 126.7(4) . . ? C17 C9 N1 113.5(4) . . ? C9 C10 C11 119.4(4) . . ? C12 C11 C10 121.7(4) . . ? C11 C12 C13 119.7(4) . . ? C12 C13 C14 124.3(4) . . ? C12 C13 C17 119.0(4) . . ? C14 C13 C17 116.7(4) . . ? C15 C14 C13 120.4(4) . . ? C14 C15 C16 120.0(4) . . ? N2 C16 C15 121.1(4) . . ? N2 C16 C18 118.6(4) . . ? C15 C16 C18 120.3(4) . . ? N2 C17 C9 118.7(3) . . ? N2 C17 C13 121.4(4) . . ? C9 C17 C13 119.9(4) . . ? O2 C19 C24 121.1(4) . . ? O2 C19 C20 119.1(4) . . ? C24 C19 C20 119.7(4) . . ? C21 C20 C19 118.2(4) . . ? C21 C20 C25 120.0(4) . . ? C19 C20 C25 121.8(4) . . ? C22 C21 C20 122.3(4) . . ? C23 C22 C21 119.1(4) . . ? C22 C23 C24 122.2(4) . . ? C23 C24 C19 118.6(4) . . ? C23 C24 C29 118.6(4) . . ? C19 C24 C29 122.7(4) . . ? C27 C25 C20 112.5(4) . . ? C27 C25 C28 106.7(4) . . ? C20 C25 C28 110.8(3) . . ? C27 C25 C26 106.8(4) . . ? C20 C25 C26 109.7(3) . . ? C28 C25 C26 110.3(4) . . ? C31 C29 C30 106.2(3) . . ? C31 C29 C32 105.7(4) . . ? C30 C29 C32 112.3(4) . . ? C31 C29 C24 112.8(4) . . ? C30 C29 C24 108.3(3) . . ? C32 C29 C24 111.5(3) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.716 _refine_diff_density_min -0.686 _refine_diff_density_rms 0.075 data_frit01 _database_code_depnum_ccdc_archive 'CCDC 902415' #TrackingRef 'web_deposit_cif_file_3_JosephM.Fritsch_1348167072.CF3PhNQOH 051712.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H13 F3 N2 O' _chemical_formula_weight 342.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 31.3066(17) _cell_length_b 31.3066(17) _cell_length_c 8.0145(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6802.7(6) _cell_formula_units_Z 18 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6066 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 25.45 _exptl_crystal_description tablet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3168 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.793 _exptl_absorpt_correction_T_max 0.913 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 11490 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 25.45 _reflns_number_total 2801 _reflns_number_gt 2504 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0500P)^2^+5.9000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00018(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2801 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.67325(3) 0.27228(3) -0.03693(10) 0.0297(2) Uani 1 1 d . . . F2 F 0.74085(3) 0.31939(3) 0.09271(11) 0.0306(2) Uani 1 1 d . . . F3 F 0.67806(3) 0.26552(3) 0.23019(10) 0.0279(2) Uani 1 1 d . . . O1 O 0.76617(3) 0.17944(3) -0.01960(13) 0.0271(2) Uani 1 1 d . . . N2 N 0.66662(4) 0.10697(4) 0.27646(13) 0.0212(3) Uani 1 1 d . . . N1 N 0.69003(4) 0.18812(4) 0.09914(14) 0.0208(2) Uani 1 1 d . . . C1 C 0.86876(5) 0.30026(5) -0.13427(16) 0.0221(3) Uani 1 1 d . . . H1B H 0.8582 0.3212 -0.0870 0.027 Uiso 1 1 calc R . . C2 C 0.91475(5) 0.32076(5) -0.20983(17) 0.0230(3) Uani 1 1 d . . . H2B H 0.9355 0.3556 -0.2138 0.028 Uiso 1 1 calc R . . C3 C 0.93042(5) 0.29036(5) -0.27954(16) 0.0236(3) Uani 1 1 d . . . H3A H 0.9617 0.3044 -0.3322 0.028 Uiso 1 1 calc R . . C4 C 0.90026(5) 0.23941(5) -0.27223(17) 0.0254(3) Uani 1 1 d . . . H4A H 0.9110 0.2186 -0.3195 0.030 Uiso 1 1 calc R . . C5 C 0.85449(5) 0.21903(5) -0.19600(16) 0.0226(3) Uani 1 1 d . . . H5A H 0.8342 0.1842 -0.1906 0.027 Uiso 1 1 calc R . . C6 C 0.83790(5) 0.24912(5) -0.12697(15) 0.0203(3) Uani 1 1 d . . . C7 C 0.78778(5) 0.22455(5) -0.04768(16) 0.0210(3) Uani 1 1 d . . . C8 C 0.76578(5) 0.25439(5) -0.00765(16) 0.0213(3) Uani 1 1 d . . . H8A H 0.7846 0.2888 -0.0287 0.026 Uiso 1 1 calc R . . C9 C 0.71975(4) 0.23620(5) 0.05834(15) 0.0197(3) Uani 1 1 d . . . C10 C 0.70260(5) 0.27326(5) 0.08728(16) 0.0228(3) Uani 1 1 d . . . C11 C 0.64077(5) 0.16035(4) 0.15353(16) 0.0197(3) Uani 1 1 d . . . C12 C 0.60365(5) 0.17017(5) 0.11683(17) 0.0224(3) Uani 1 1 d . . . H12A H 0.6107 0.1984 0.0520 0.027 Uiso 1 1 calc R . . C13 C 0.55515(5) 0.13881(5) 0.17439(17) 0.0255(3) Uani 1 1 d . . . H13A H 0.5304 0.1472 0.1524 0.031 Uiso 1 1 calc R . . C14 C 0.54299(5) 0.09669(5) 0.26097(17) 0.0247(3) Uani 1 1 d . . . H14A H 0.5101 0.0759 0.2982 0.030 Uiso 1 1 calc R . . C15 C 0.57976(5) 0.08420(5) 0.29493(16) 0.0216(3) Uani 1 1 d . . . C16 C 0.56976(5) 0.04016(5) 0.37799(16) 0.0253(3) Uani 1 1 d . . . H16A H 0.5371 0.0173 0.4126 0.030 Uiso 1 1 calc R . . C17 C 0.60708(5) 0.03074(5) 0.40799(16) 0.0253(3) Uani 1 1 d . . . H17A H 0.6008 0.0013 0.4629 0.030 Uiso 1 1 calc R . . C18 C 0.65517(5) 0.06558(5) 0.35596(16) 0.0237(3) Uani 1 1 d . . . H18A H 0.6810 0.0589 0.3795 0.028 Uiso 1 1 calc R . . C19 C 0.62923(5) 0.11632(5) 0.24427(15) 0.0194(3) Uani 1 1 d . . . H2 H 0.7040(6) 0.1716(6) 0.095(2) 0.031(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0283(4) 0.0304(4) 0.0352(5) 0.0079(3) 0.0009(3) 0.0184(4) F2 0.0250(4) 0.0162(4) 0.0474(5) -0.0011(3) 0.0072(4) 0.0080(3) F3 0.0261(4) 0.0254(4) 0.0302(4) -0.0045(3) 0.0067(3) 0.0114(3) O1 0.0231(5) 0.0187(5) 0.0389(6) 0.0028(4) 0.0061(4) 0.0101(4) N2 0.0217(6) 0.0200(5) 0.0225(6) -0.0014(4) -0.0018(4) 0.0108(5) N1 0.0181(5) 0.0181(5) 0.0276(6) 0.0020(4) 0.0029(4) 0.0101(5) C1 0.0217(6) 0.0218(6) 0.0231(7) -0.0011(5) -0.0009(5) 0.0111(5) C2 0.0194(6) 0.0204(6) 0.0246(7) 0.0011(5) -0.0028(5) 0.0064(5) C3 0.0173(6) 0.0284(7) 0.0235(6) 0.0025(5) 0.0002(5) 0.0103(5) C4 0.0241(7) 0.0275(7) 0.0278(7) 0.0000(6) 0.0018(5) 0.0154(6) C5 0.0216(6) 0.0192(6) 0.0258(7) 0.0005(5) -0.0002(5) 0.0092(5) C6 0.0191(6) 0.0227(6) 0.0195(6) 0.0008(5) -0.0020(5) 0.0106(5) C7 0.0205(6) 0.0198(6) 0.0212(6) 0.0007(5) -0.0004(5) 0.0089(5) C8 0.0204(6) 0.0174(6) 0.0239(7) 0.0017(5) 0.0018(5) 0.0077(5) C9 0.0211(6) 0.0198(6) 0.0184(6) -0.0006(5) -0.0019(5) 0.0106(5) C10 0.0217(6) 0.0188(6) 0.0270(7) 0.0011(5) 0.0032(5) 0.0095(5) C11 0.0191(6) 0.0176(6) 0.0203(6) -0.0029(5) 0.0001(5) 0.0078(5) C12 0.0228(7) 0.0199(6) 0.0250(7) -0.0020(5) -0.0010(5) 0.0111(5) C13 0.0207(7) 0.0267(7) 0.0315(7) -0.0054(6) -0.0022(5) 0.0136(6) C14 0.0178(6) 0.0235(7) 0.0288(7) -0.0043(5) 0.0024(5) 0.0074(5) C15 0.0214(6) 0.0202(6) 0.0201(6) -0.0036(5) 0.0004(5) 0.0080(5) C16 0.0252(7) 0.0208(7) 0.0232(7) -0.0010(5) 0.0042(5) 0.0065(6) C17 0.0325(7) 0.0204(6) 0.0212(6) 0.0019(5) 0.0010(6) 0.0118(6) C18 0.0274(7) 0.0242(7) 0.0219(6) -0.0002(5) -0.0022(5) 0.0149(6) C19 0.0198(6) 0.0189(6) 0.0184(6) -0.0036(5) -0.0006(5) 0.0088(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C10 1.3445(16) . ? F2 C10 1.3387(15) . ? F3 C10 1.3320(15) . ? O1 C7 1.2437(15) . ? N2 C18 1.3223(17) . ? N2 C19 1.3661(16) . ? N1 C9 1.3556(16) . ? N1 C11 1.4083(16) . ? C1 C2 1.3884(18) . ? C1 C6 1.3977(18) . ? C2 C3 1.3875(19) . ? C3 C4 1.3903(19) . ? C4 C5 1.3854(18) . ? C5 C6 1.3976(18) . ? C6 C7 1.5001(18) . ? C7 C8 1.4469(18) . ? C8 C9 1.3637(17) . ? C9 C10 1.5204(17) . ? C11 C12 1.3744(18) . ? C11 C19 1.4357(18) . ? C12 C13 1.4111(19) . ? C13 C14 1.3650(19) . ? C14 C15 1.4152(19) . ? C15 C16 1.4177(19) . ? C15 C19 1.4202(18) . ? C16 C17 1.362(2) . ? C17 C18 1.4099(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 C18 N2 C19 117.35(11) . . ? C9 N1 C11 133.77(11) . . ? C2 C1 C6 120.72(12) . . ? C3 C2 C1 119.95(12) . . ? C2 C3 C4 119.98(12) . . ? C5 C4 C3 119.98(12) . . ? C4 C5 C6 120.77(12) . . ? C5 C6 C1 118.59(12) . . ? C5 C6 C7 117.90(11) . . ? C1 C6 C7 123.50(11) . . ? O1 C7 C8 121.91(11) . . ? O1 C7 C6 119.65(11) . . ? C8 C7 C6 118.44(11) . . ? C9 C8 C7 124.13(12) . . ? N1 C9 C8 123.53(12) . . ? N1 C9 C10 120.15(11) . . ? C8 C9 C10 116.31(11) . . ? F3 C10 F2 106.97(10) . . ? F3 C10 F1 107.89(10) . . ? F2 C10 F1 106.33(10) . . ? F3 C10 C9 112.57(10) . . ? F2 C10 C9 111.18(10) . . ? F1 C10 C9 111.57(10) . . ? C12 C11 N1 125.67(12) . . ? C12 C11 C19 119.20(11) . . ? N1 C11 C19 114.95(11) . . ? C11 C12 C13 120.70(12) . . ? C14 C13 C12 121.44(12) . . ? C13 C14 C15 119.49(12) . . ? C14 C15 C16 122.99(12) . . ? C14 C15 C19 119.92(12) . . ? C16 C15 C19 117.09(12) . . ? C17 C16 C15 119.82(12) . . ? C16 C17 C18 118.68(12) . . ? N2 C18 C17 124.21(12) . . ? N2 C19 C15 122.83(11) . . ? N2 C19 C11 118.04(11) . . ? C15 C19 C11 119.13(11) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.253 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.040 data_frit12 _database_code_depnum_ccdc_archive 'CCDC 902416' #TrackingRef 'web_deposit_cif_file_4_JosephM.Fritsch_1348167072.frit12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 F3 N2 O' _chemical_formula_weight 280.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x+1/2, -y+1/2, z' '-x, -y, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' 'x-1/2, y-1/2, -z' _cell_length_a 7.1874(11) _cell_length_b 14.651(2) _cell_length_c 23.702(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2495.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1755 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 25.34 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.837 _exptl_absorpt_correction_T_max 0.911 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 8371 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.58 _reflns_number_total 2309 _reflns_number_gt 1619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0700P)^2^+0.7000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2309 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1426 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.3986(3) 0.98927(11) 0.26080(7) 0.0724(8) Uani 1 1 d . . . F2 F 0.2632(3) 0.86962(15) 0.23011(7) 0.0811(8) Uani 1 1 d . . . F3 F 0.5547(3) 0.88243(12) 0.22375(7) 0.0558(5) Uani 1 1 d . . . O1 O 0.3800(2) 0.90161(10) 0.35707(7) 0.0306(4) Uani 1 1 d . . . N1 N 0.4818(3) 0.75268(13) 0.41560(7) 0.0247(5) Uani 1 1 d . . . H1 H 0.4594 0.8117 0.4144 0.030 Uiso 1 1 calc R . . N2 N 0.5625(3) 0.85929(12) 0.50545(8) 0.0264(5) Uani 1 1 d . . . C1 C 0.4103(4) 0.89974(17) 0.25793(10) 0.0343(6) Uani 1 1 d . . . C2 C 0.4305(4) 0.85430(16) 0.31596(10) 0.0271(6) Uani 1 1 d . . . C3 C 0.5023(3) 0.76539(15) 0.31680(10) 0.0274(6) Uani 1 1 d . . . H3 H 0.5395 0.7387 0.2820 0.033 Uiso 1 1 calc R . . C4 C 0.5221(3) 0.71407(16) 0.36587(10) 0.0260(5) Uani 1 1 d . . . C5 C 0.4699(3) 0.71253(15) 0.46989(10) 0.0237(5) Uani 1 1 d . . . C6 C 0.5113(3) 0.77102(15) 0.51654(9) 0.0240(5) Uani 1 1 d . . . C7 C 0.4913(3) 0.73566(15) 0.57192(9) 0.0265(6) Uani 1 1 d . . . C8 C 0.5289(4) 0.79622(16) 0.61711(10) 0.0298(6) Uani 1 1 d . . . H8 H 0.5187 0.7756 0.6550 0.036 Uiso 1 1 calc R . . C9 C 0.5796(4) 0.88397(16) 0.60626(10) 0.0313(6) Uani 1 1 d . . . H9 H 0.6058 0.9251 0.6362 0.038 Uiso 1 1 calc R . . C10 C 0.4060(3) 0.62550(14) 0.47875(10) 0.0245(5) Uani 1 1 d . . . H10 H 0.3736 0.5881 0.4475 0.029 Uiso 1 1 calc R . . C11 C 0.3883(3) 0.59133(15) 0.53418(10) 0.0263(6) Uani 1 1 d . . . H11 H 0.3454 0.5307 0.5399 0.032 Uiso 1 1 calc R . . C12 C 0.4318(4) 0.64425(15) 0.57955(10) 0.0282(6) Uani 1 1 d . . . H12 H 0.4223 0.6197 0.6165 0.034 Uiso 1 1 calc R . . C13 C 0.5926(4) 0.91251(15) 0.54955(10) 0.0288(6) Uani 1 1 d . . . H13 H 0.6252 0.9743 0.5426 0.035 Uiso 1 1 calc R . . C14 C 0.5940(4) 0.61808(15) 0.36247(10) 0.0306(6) Uani 1 1 d . . . H14A H 0.6753 0.6060 0.3948 0.046 Uiso 1 1 calc R . . H14B H 0.6645 0.6102 0.3274 0.046 Uiso 1 1 calc R . . H14C H 0.4891 0.5754 0.3630 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.146(2) 0.0344(9) 0.0369(9) 0.0098(7) 0.0080(11) 0.0200(11) F2 0.0708(15) 0.1202(17) 0.0522(11) 0.0409(11) -0.0325(11) -0.0409(13) F3 0.0661(14) 0.0650(12) 0.0363(9) 0.0134(8) 0.0136(9) 0.0104(10) O1 0.0371(11) 0.0243(9) 0.0303(9) -0.0006(7) 0.0019(8) 0.0006(8) N1 0.0285(12) 0.0186(9) 0.0269(10) 0.0010(8) -0.0001(9) -0.0005(9) N2 0.0271(12) 0.0213(10) 0.0309(11) -0.0001(8) -0.0020(9) -0.0011(9) C1 0.0433(17) 0.0305(13) 0.0291(13) 0.0004(10) -0.0003(13) 0.0001(12) C2 0.0262(14) 0.0284(12) 0.0265(12) 0.0019(10) 0.0001(10) -0.0050(11) C3 0.0292(14) 0.0263(13) 0.0267(12) -0.0033(10) 0.0021(11) -0.0002(11) C4 0.0201(13) 0.0258(12) 0.0322(13) -0.0027(10) -0.0009(11) -0.0027(10) C5 0.0205(12) 0.0230(11) 0.0277(12) 0.0011(9) -0.0012(10) 0.0018(10) C6 0.0213(13) 0.0238(12) 0.0268(12) 0.0013(9) -0.0006(10) 0.0011(9) C7 0.0274(14) 0.0254(12) 0.0267(12) 0.0013(9) -0.0005(11) 0.0030(10) C8 0.0352(16) 0.0274(13) 0.0267(13) -0.0004(10) -0.0017(11) 0.0019(11) C9 0.0340(16) 0.0285(13) 0.0315(13) -0.0041(10) -0.0054(12) 0.0013(11) C10 0.0235(13) 0.0214(11) 0.0285(12) -0.0026(9) 0.0004(10) 0.0008(10) C11 0.0276(14) 0.0210(11) 0.0302(13) 0.0033(9) 0.0013(11) 0.0013(10) C12 0.0310(15) 0.0247(12) 0.0288(13) 0.0038(10) 0.0004(11) 0.0034(11) C13 0.0306(15) 0.0215(11) 0.0343(13) -0.0028(10) -0.0016(11) -0.0035(10) C14 0.0330(15) 0.0252(12) 0.0335(13) -0.0005(10) 0.0064(12) 0.0001(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.316(3) . ? F2 C1 1.322(3) . ? F3 C1 1.341(3) . ? O1 C2 1.250(3) . ? N1 C4 1.339(3) . ? N1 C5 1.417(3) . ? N1 H1 0.8800 . ? N2 C13 1.322(3) . ? N2 C6 1.370(3) . ? C1 C2 1.535(3) . ? C2 C3 1.401(3) . ? C3 C4 1.392(3) . ? C3 H3 0.9500 . ? C4 C14 1.500(3) . ? C5 C10 1.371(3) . ? C5 C6 1.430(3) . ? C6 C7 1.418(3) . ? C7 C8 1.417(3) . ? C7 C12 1.417(3) . ? C8 C9 1.361(3) . ? C8 H8 0.9500 . ? C9 C13 1.411(3) . ? C9 H9 0.9500 . ? C10 C11 1.412(3) . ? C10 H10 0.9500 . ? C11 C12 1.362(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C4 N1 C5 129.56(19) . . ? C4 N1 H1 115.2 . . ? C5 N1 H1 115.2 . . ? C13 N2 C6 116.67(19) . . ? F1 C1 F2 107.9(2) . . ? F1 C1 F3 105.6(2) . . ? F2 C1 F3 104.7(2) . . ? F1 C1 C2 113.1(2) . . ? F2 C1 C2 112.2(2) . . ? F3 C1 C2 112.7(2) . . ? O1 C2 C3 127.7(2) . . ? O1 C2 C1 115.5(2) . . ? C3 C2 C1 116.8(2) . . ? C4 C3 C2 123.5(2) . . ? C4 C3 H3 118.3 . . ? C2 C3 H3 118.3 . . ? N1 C4 C3 119.0(2) . . ? N1 C4 C14 121.2(2) . . ? C3 C4 C14 119.8(2) . . ? C10 C5 N1 123.0(2) . . ? C10 C5 C6 120.6(2) . . ? N1 C5 C6 116.14(19) . . ? N2 C6 C7 123.3(2) . . ? N2 C6 C5 118.23(19) . . ? C7 C6 C5 118.4(2) . . ? C8 C7 C12 123.6(2) . . ? C8 C7 C6 116.8(2) . . ? C12 C7 C6 119.6(2) . . ? C9 C8 C7 120.0(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C13 118.5(2) . . ? C8 C9 H9 120.7 . . ? C13 C9 H9 120.7 . . ? C5 C10 C11 120.2(2) . . ? C5 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 120.8(2) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C7 120.4(2) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? N2 C13 C9 124.6(2) . . ? N2 C13 H13 117.7 . . ? C9 C13 H13 117.7 . . ? C4 C14 H14A 109.5 . . ? C4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.262 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.051 data_frit03 _database_code_depnum_ccdc_archive 'CCDC 902417' #TrackingRef '14121_web_deposit_cif_file_5_JosephM.Fritsch_1348167072.CF3CH3NMeQOZnOR 051712 submit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H33 F3 N2 O2 Zn' _chemical_formula_weight 563.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0828(5) _cell_length_b 10.7266(6) _cell_length_c 12.2102(6) _cell_angle_alpha 90.098(3) _cell_angle_beta 99.192(3) _cell_angle_gamma 96.636(2) _cell_volume 1294.62(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9951 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 25.51 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 1.000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7338 _exptl_absorpt_correction_T_max 0.9066 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 16914 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 25.53 _reflns_number_total 4775 _reflns_number_gt 4507 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.5032P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4775 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0246 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0605 _refine_ls_wR_factor_gt 0.0596 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.449820(16) 0.113817(15) 0.247862(13) 0.01339(6) Uani 1 1 d . . . F1 F 0.39844(10) -0.26811(9) 0.09354(9) 0.0287(2) Uani 1 1 d . . . F2 F 0.59097(11) -0.25867(9) 0.04036(9) 0.0333(2) Uani 1 1 d . . . F3 F 0.57537(10) -0.29124(9) 0.21133(8) 0.0287(2) Uani 1 1 d . . . O2 O 0.26777(10) 0.13051(9) 0.19357(8) 0.0146(2) Uani 1 1 d . . . O1 O 0.47703(11) -0.06039(9) 0.22323(9) 0.0182(2) Uani 1 1 d . . . N1 N 0.61811(12) 0.18330(11) 0.18689(10) 0.0145(3) Uani 1 1 d . . . N2 N 0.54148(12) 0.22938(11) 0.38092(10) 0.0147(3) Uani 1 1 d . . . C1 C 0.17421(14) 0.16705(13) 0.24957(11) 0.0130(3) Uani 1 1 d . . . C2 C 0.09068(15) 0.07686(13) 0.30146(11) 0.0140(3) Uani 1 1 d . . . C3 C 0.00962(15) 0.12175(14) 0.37224(12) 0.0163(3) Uani 1 1 d . . . H3 H -0.0433 0.0631 0.4106 0.020 Uiso 1 1 calc R . . C4 C 0.00405(15) 0.24828(15) 0.38807(12) 0.0175(3) Uani 1 1 d . . . H4 H -0.0453 0.2764 0.4416 0.021 Uiso 1 1 calc R . . C5 C 0.07112(15) 0.33381(14) 0.32510(12) 0.0156(3) Uani 1 1 d . . . H5 H 0.0619 0.4205 0.3322 0.019 Uiso 1 1 calc R . . C6 C 0.15202(14) 0.29571(13) 0.25137(12) 0.0133(3) Uani 1 1 d . . . C7 C 0.20524(15) 0.38909(14) 0.16799(12) 0.0156(3) Uani 1 1 d . . . C8 C 0.36033(15) 0.41165(14) 0.18421(13) 0.0175(3) Uani 1 1 d . . . H8A H 0.3960 0.3341 0.1666 0.026 Uiso 1 1 calc R . . H8B H 0.3955 0.4371 0.2615 0.026 Uiso 1 1 calc R . . H8C H 0.3885 0.4781 0.1349 0.026 Uiso 1 1 calc R . . C9 C 0.15383(16) 0.51757(14) 0.17581(14) 0.0208(3) Uani 1 1 d . . . H9A H 0.1838 0.5718 0.1178 0.031 Uiso 1 1 calc R . . H9B H 0.1901 0.5563 0.2488 0.031 Uiso 1 1 calc R . . H9C H 0.0548 0.5066 0.1658 0.031 Uiso 1 1 calc R . . C10 C 0.15102(16) 0.33678(15) 0.05001(12) 0.0196(3) Uani 1 1 d . . . H10A H 0.0522 0.3332 0.0359 0.029 Uiso 1 1 calc R . . H10B H 0.1769 0.2522 0.0428 0.029 Uiso 1 1 calc R . . H10C H 0.1894 0.3916 -0.0040 0.029 Uiso 1 1 calc R . . C11 C 0.08534(15) -0.06590(14) 0.28226(12) 0.0163(3) Uani 1 1 d . . . C12 C 0.09110(18) -0.09964(15) 0.16052(13) 0.0228(3) Uani 1 1 d . . . H12A H 0.0797 -0.1911 0.1505 0.034 Uiso 1 1 calc R . . H12B H 0.1788 -0.0650 0.1418 0.034 Uiso 1 1 calc R . . H12C H 0.0185 -0.0642 0.1118 0.034 Uiso 1 1 calc R . . C13 C -0.04816(16) -0.13530(15) 0.30818(14) 0.0218(3) Uani 1 1 d . . . H13A H -0.1247 -0.0996 0.2648 0.033 Uiso 1 1 calc R . . H13B H -0.0517 -0.1259 0.3875 0.033 Uiso 1 1 calc R . . H13C H -0.0531 -0.2246 0.2887 0.033 Uiso 1 1 calc R . . C14 C 0.20175(16) -0.11931(14) 0.35722(13) 0.0204(3) Uani 1 1 d . . . H14A H 0.1990 -0.0984 0.4349 0.031 Uiso 1 1 calc R . . H14B H 0.2883 -0.0829 0.3375 0.031 Uiso 1 1 calc R . . H14C H 0.1923 -0.2107 0.3471 0.031 Uiso 1 1 calc R . . C15 C 0.68809(15) 0.11716(14) 0.13161(11) 0.0145(3) Uani 1 1 d . . . C16 C 0.82313(15) 0.16582(15) 0.10171(13) 0.0179(3) Uani 1 1 d . . . H16A H 0.8098 0.2166 0.0350 0.027 Uiso 1 1 calc R . . H16B H 0.8717 0.0950 0.0873 0.027 Uiso 1 1 calc R . . H16C H 0.8761 0.2177 0.1632 0.027 Uiso 1 1 calc R . . C17 C 0.64054(15) -0.01118(14) 0.10104(12) 0.0162(3) Uani 1 1 d . . . H17 H 0.6755 -0.0469 0.0420 0.019 Uiso 1 1 calc R . . C18 C 0.54930(15) -0.08607(14) 0.14991(12) 0.0148(3) Uani 1 1 d . . . C19 C 0.52949(16) -0.22615(15) 0.12261(13) 0.0187(3) Uani 1 1 d . . . C20 C 0.66874(14) 0.30134(14) 0.23744(12) 0.0154(3) Uani 1 1 d . . . C21 C 0.73955(15) 0.40019(14) 0.19210(13) 0.0182(3) Uani 1 1 d . . . H21 H 0.7562 0.3933 0.1180 0.022 Uiso 1 1 calc R . . C22 C 0.78745(16) 0.51113(15) 0.25410(14) 0.0213(3) Uani 1 1 d . . . H22 H 0.8352 0.5786 0.2209 0.026 Uiso 1 1 calc R . . C23 C 0.76679(15) 0.52409(14) 0.36125(14) 0.0201(3) Uani 1 1 d . . . H23 H 0.8061 0.5971 0.4040 0.024 Uiso 1 1 calc R . . C24 C 0.68649(15) 0.42803(14) 0.40801(13) 0.0175(3) Uani 1 1 d . . . C25 C 0.63318(14) 0.31887(14) 0.34471(12) 0.0148(3) Uani 1 1 d . . . C26 C 0.50608(15) 0.24324(14) 0.48018(12) 0.0170(3) Uani 1 1 d . . . C27 C 0.56526(16) 0.34516(15) 0.55149(13) 0.0201(3) Uani 1 1 d . . . H27 H 0.5442 0.3499 0.6244 0.024 Uiso 1 1 calc R . . C28 C 0.65274(16) 0.43699(15) 0.51574(13) 0.0198(3) Uani 1 1 d . . . H28 H 0.6909 0.5068 0.5630 0.024 Uiso 1 1 calc R . . C29 C 0.39868(17) 0.14996(15) 0.51352(13) 0.0217(3) Uani 1 1 d . . . H29A H 0.3102 0.1800 0.4923 0.033 Uiso 1 1 calc R . . H29B H 0.4162 0.1394 0.5940 0.033 Uiso 1 1 calc R . . H29C H 0.3991 0.0692 0.4760 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01183(10) 0.01427(10) 0.01481(10) -0.00068(6) 0.00374(7) 0.00241(6) F1 0.0207(5) 0.0203(5) 0.0426(6) -0.0033(4) 0.0002(4) -0.0018(4) F2 0.0460(6) 0.0237(5) 0.0351(6) -0.0106(4) 0.0247(5) -0.0001(4) F3 0.0397(6) 0.0195(5) 0.0271(5) 0.0040(4) -0.0002(4) 0.0125(4) O2 0.0127(5) 0.0168(5) 0.0151(5) -0.0012(4) 0.0041(4) 0.0032(4) O1 0.0198(6) 0.0162(5) 0.0214(5) 0.0015(4) 0.0101(5) 0.0050(4) N1 0.0133(6) 0.0164(6) 0.0138(6) 0.0009(5) 0.0025(5) 0.0019(5) N2 0.0129(6) 0.0166(6) 0.0148(6) 0.0002(5) 0.0003(5) 0.0047(5) C1 0.0113(7) 0.0171(7) 0.0102(6) -0.0013(5) -0.0006(5) 0.0028(6) C2 0.0139(7) 0.0158(7) 0.0118(7) 0.0003(5) -0.0007(6) 0.0030(6) C3 0.0169(8) 0.0193(7) 0.0127(7) 0.0022(6) 0.0031(6) 0.0013(6) C4 0.0167(8) 0.0236(8) 0.0137(7) -0.0012(6) 0.0050(6) 0.0058(6) C5 0.0148(7) 0.0150(7) 0.0168(7) -0.0020(6) -0.0002(6) 0.0040(6) C6 0.0097(7) 0.0158(7) 0.0133(7) 0.0003(5) -0.0012(6) 0.0008(6) C7 0.0143(7) 0.0147(7) 0.0182(7) 0.0019(6) 0.0032(6) 0.0022(6) C8 0.0145(8) 0.0154(7) 0.0226(8) 0.0013(6) 0.0037(6) 0.0009(6) C9 0.0173(8) 0.0176(8) 0.0286(8) 0.0059(6) 0.0055(7) 0.0048(6) C10 0.0179(8) 0.0236(8) 0.0165(7) 0.0040(6) 0.0019(6) 0.0001(6) C11 0.0188(8) 0.0145(7) 0.0160(7) 0.0001(6) 0.0038(6) 0.0017(6) C12 0.0340(10) 0.0154(7) 0.0189(8) -0.0032(6) 0.0062(7) 0.0003(7) C13 0.0222(8) 0.0184(8) 0.0239(8) -0.0009(6) 0.0043(7) -0.0019(6) C14 0.0220(8) 0.0155(7) 0.0240(8) 0.0028(6) 0.0040(7) 0.0031(6) C15 0.0127(7) 0.0201(7) 0.0105(6) 0.0019(6) -0.0006(6) 0.0041(6) C16 0.0141(8) 0.0218(8) 0.0184(7) -0.0013(6) 0.0045(6) 0.0021(6) C17 0.0157(7) 0.0203(8) 0.0131(7) -0.0013(6) 0.0025(6) 0.0046(6) C18 0.0137(7) 0.0176(7) 0.0129(7) -0.0005(6) -0.0008(6) 0.0057(6) C19 0.0181(8) 0.0213(8) 0.0179(7) 0.0007(6) 0.0045(6) 0.0050(6) C20 0.0100(7) 0.0173(7) 0.0188(7) -0.0004(6) 0.0000(6) 0.0040(6) C21 0.0143(7) 0.0197(8) 0.0215(8) 0.0019(6) 0.0040(6) 0.0044(6) C22 0.0158(8) 0.0171(8) 0.0317(9) 0.0027(6) 0.0053(7) 0.0024(6) C23 0.0144(8) 0.0150(7) 0.0299(8) -0.0038(6) 0.0002(7) 0.0022(6) C24 0.0129(7) 0.0179(7) 0.0216(8) -0.0008(6) -0.0012(6) 0.0064(6) C25 0.0110(7) 0.0158(7) 0.0177(7) 0.0011(6) -0.0003(6) 0.0055(6) C26 0.0160(8) 0.0198(8) 0.0160(7) 0.0008(6) 0.0007(6) 0.0075(6) C27 0.0213(8) 0.0242(8) 0.0151(7) -0.0023(6) 0.0001(6) 0.0077(7) C28 0.0179(8) 0.0202(8) 0.0204(8) -0.0049(6) -0.0030(6) 0.0064(6) C29 0.0245(9) 0.0253(8) 0.0156(7) -0.0015(6) 0.0049(7) 0.0016(7) _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 O2 1.8784(10) . ? Zn1 O1 1.9495(10) . ? Zn1 N1 2.0254(12) . ? Zn1 N2 2.0686(12) . ? F1 C19 1.3367(18) . ? F2 C19 1.3275(17) . ? F3 C19 1.3387(18) . ? O2 C1 1.3423(17) . ? O1 C18 1.2893(17) . ? N1 C15 1.3126(19) . ? N1 C20 1.4115(19) . ? N2 C26 1.3297(19) . ? N2 C25 1.3780(19) . ? C1 C6 1.424(2) . ? C1 C2 1.425(2) . ? C2 C3 1.401(2) . ? C2 C11 1.542(2) . ? C3 C4 1.379(2) . ? C4 C5 1.384(2) . ? C5 C6 1.398(2) . ? C6 C7 1.5432(19) . ? C7 C8 1.535(2) . ? C7 C9 1.535(2) . ? C7 C10 1.537(2) . ? C11 C14 1.535(2) . ? C11 C13 1.540(2) . ? C11 C12 1.541(2) . ? C15 C17 1.433(2) . ? C15 C16 1.502(2) . ? C17 C18 1.362(2) . ? C18 C19 1.522(2) . ? C20 C21 1.376(2) . ? C20 C25 1.430(2) . ? C21 C22 1.404(2) . ? C22 C23 1.367(2) . ? C23 C24 1.414(2) . ? C24 C25 1.406(2) . ? C24 C28 1.416(2) . ? C26 C27 1.410(2) . ? C26 C29 1.494(2) . ? C27 C28 1.365(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 O1 107.51(4) . . ? O2 Zn1 N1 129.15(5) . . ? O1 Zn1 N1 93.61(5) . . ? O2 Zn1 N2 116.48(4) . . ? O1 Zn1 N2 126.74(5) . . ? N1 Zn1 N2 81.37(5) . . ? C1 O2 Zn1 127.99(9) . . ? C18 O1 Zn1 119.07(9) . . ? C15 N1 C20 123.71(12) . . ? C15 N1 Zn1 124.77(10) . . ? C20 N1 Zn1 109.46(9) . . ? C26 N2 C25 119.62(13) . . ? C26 N2 Zn1 130.04(10) . . ? C25 N2 Zn1 108.71(9) . . ? O2 C1 C6 119.93(12) . . ? O2 C1 C2 120.45(13) . . ? C6 C1 C2 119.50(12) . . ? C3 C2 C1 117.62(13) . . ? C3 C2 C11 119.34(13) . . ? C1 C2 C11 123.04(12) . . ? C4 C3 C2 122.16(14) . . ? C3 C4 C5 119.23(13) . . ? C4 C5 C6 121.57(14) . . ? C5 C6 C1 118.18(13) . . ? C5 C6 C7 120.25(13) . . ? C1 C6 C7 121.38(12) . . ? C8 C7 C9 107.29(12) . . ? C8 C7 C10 109.33(12) . . ? C9 C7 C10 106.78(12) . . ? C8 C7 C6 112.89(12) . . ? C9 C7 C6 112.05(12) . . ? C10 C7 C6 108.31(12) . . ? C14 C11 C13 107.55(12) . . ? C14 C11 C12 108.81(13) . . ? C13 C11 C12 106.02(13) . . ? C14 C11 C2 111.23(12) . . ? C13 C11 C2 110.92(12) . . ? C12 C11 C2 112.07(12) . . ? N1 C15 C17 120.40(13) . . ? N1 C15 C16 123.71(13) . . ? C17 C15 C16 115.81(13) . . ? C18 C17 C15 125.22(13) . . ? O1 C18 C17 130.79(14) . . ? O1 C18 C19 110.74(12) . . ? C17 C18 C19 118.37(13) . . ? F2 C19 F1 106.51(13) . . ? F2 C19 F3 107.11(12) . . ? F1 C19 F3 106.52(12) . . ? F2 C19 C18 114.34(12) . . ? F1 C19 C18 111.20(12) . . ? F3 C19 C18 110.74(12) . . ? C21 C20 N1 127.15(14) . . ? C21 C20 C25 118.43(14) . . ? N1 C20 C25 114.30(12) . . ? C20 C21 C22 120.70(14) . . ? C23 C22 C21 121.34(14) . . ? C22 C23 C24 119.47(14) . . ? C25 C24 C23 119.40(14) . . ? C25 C24 C28 117.28(14) . . ? C23 C24 C28 123.29(14) . . ? N2 C25 C24 121.70(13) . . ? N2 C25 C20 118.21(13) . . ? C24 C25 C20 120.02(13) . . ? N2 C26 C27 121.19(14) . . ? N2 C26 C29 118.35(14) . . ? C27 C26 C29 120.44(13) . . ? C28 C27 C26 119.99(14) . . ? C27 C28 C24 119.85(14) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.298 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.045