# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_nesn132 _database_code_depnum_ccdc_archive 'CCDC 876009' #TrackingRef 'nesn132.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 F N O2' _chemical_formula_sum 'C16 H14 F N O2' _chemical_formula_weight 271.28 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5984(4) _cell_length_b 9.3308(7) _cell_length_c 14.7806(12) _cell_angle_alpha 90.00 _cell_angle_beta 100.934(4) _cell_angle_gamma 90.00 _cell_volume 1299.73(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6943 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .4 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6943 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2807 _reflns_number_gt 1896 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0449P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2807 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0723 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.0951 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.008 _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 0.62056(8) -0.17320(9) 0.22083(6) 0.0317(3) Uani 1 1 d . . . O1 O 0.69203(11) 0.52135(12) -0.06222(7) 0.0250(3) Uani 1 1 d . . . H1A H 0.762(2) 0.589(2) -0.0576(14) 0.064(7) Uiso 1 1 d . . . O2 O 1.09247(10) 0.27427(12) 0.03138(8) 0.0299(3) Uani 1 1 d . . . N1 N 0.85918(11) 0.33037(14) -0.02891(9) 0.0222(3) Uani 1 1 d . . . C1 C 0.62285(15) -0.05513(17) 0.16596(11) 0.0229(4) Uani 1 1 d . . . C2 C 0.68826(14) -0.06620(17) 0.09100(11) 0.0241(4) Uani 1 1 d . . . H2 H 0.7335 -0.1524 0.0783 0.029 Uiso 1 1 calc R . . C3 C 0.68562(14) 0.05314(17) 0.03482(11) 0.0230(4) Uani 1 1 d . . . H3 H 0.7299 0.0482 -0.0174 0.028 Uiso 1 1 calc R . . C4 C 0.61978(13) 0.17982(16) 0.05303(10) 0.0205(4) Uani 1 1 d . . . C5 C 0.60732(14) 0.30758(16) -0.01067(10) 0.0225(4) Uani 1 1 d . . . H5A H 0.5261 0.3663 -0.0001 0.027 Uiso 1 1 calc R . . H5B H 0.5842 0.2720 -0.0749 0.027 Uiso 1 1 calc R . . C6 C 0.73721(14) 0.40552(17) -0.00216(10) 0.0214(4) Uani 1 1 d . . . C7 C 0.97634(14) 0.32724(17) 0.03841(11) 0.0235(4) Uani 1 1 d . . . C8 C 0.93921(14) 0.40169(16) 0.11884(10) 0.0215(4) Uani 1 1 d . . . C9 C 0.80059(14) 0.45045(16) 0.09555(10) 0.0204(4) Uani 1 1 d . . . C10 C 0.74065(15) 0.52878(17) 0.15752(10) 0.0232(4) Uani 1 1 d . . . H10 H 0.6453 0.5614 0.1422 0.028 Uiso 1 1 calc R . . C11 C 0.82428(15) 0.55864(17) 0.24339(11) 0.0258(4) Uani 1 1 d . . . H11 H 0.7858 0.6139 0.2867 0.031 Uiso 1 1 calc R . . C12 C 0.96262(16) 0.50911(17) 0.26653(11) 0.0269(4) Uani 1 1 d . . . H12 H 1.0173 0.5302 0.3256 0.032 Uiso 1 1 calc R . . C13 C 1.02204(15) 0.42916(17) 0.20454(11) 0.0258(4) Uani 1 1 d . . . H13 H 1.1165 0.3943 0.2203 0.031 Uiso 1 1 calc R . . C14 C 0.85358(15) 0.27198(19) -0.12025(11) 0.0301(4) Uani 1 1 d . . . H14A H 0.9502 0.2614 -0.1319 0.045 Uiso 1 1 calc R . . H14B H 0.7997 0.3369 -0.1661 0.045 Uiso 1 1 calc R . . H14C H 0.8070 0.1781 -0.1246 0.045 Uiso 1 1 calc R . . C15 C 0.55745(15) 0.18548(17) 0.13074(11) 0.0251(4) Uani 1 1 d . . . H15 H 0.5133 0.2717 0.1447 0.030 Uiso 1 1 calc R . . C16 C 0.55858(15) 0.06791(17) 0.18795(11) 0.0252(4) Uani 1 1 d . . . H16 H 0.5161 0.0723 0.2409 0.030 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 0.0366(5) 0.0252(6) 0.0338(6) 0.0071(4) 0.0078(4) -0.0001(4) O1 0.0254(6) 0.0226(7) 0.0263(6) 0.0048(5) 0.0034(4) -0.0001(5) O2 0.0219(6) 0.0252(7) 0.0443(7) -0.0015(6) 0.0104(5) 0.0036(5) N1 0.0223(7) 0.0225(8) 0.0229(8) -0.0035(6) 0.0073(5) -0.0003(5) C1 0.0212(8) 0.0214(10) 0.0245(9) 0.0047(7) 0.0006(6) -0.0034(6) C2 0.0201(8) 0.0207(10) 0.0307(10) -0.0021(7) 0.0030(6) 0.0001(6) C3 0.0191(8) 0.0263(10) 0.0239(9) -0.0019(8) 0.0046(6) -0.0011(6) C4 0.0143(7) 0.0226(9) 0.0235(9) -0.0004(7) 0.0005(6) -0.0033(6) C5 0.0204(8) 0.0222(10) 0.0246(9) -0.0001(7) 0.0033(6) -0.0009(6) C6 0.0221(8) 0.0189(9) 0.0238(9) 0.0020(7) 0.0056(6) 0.0021(6) C7 0.0220(8) 0.0164(9) 0.0330(10) 0.0027(7) 0.0071(7) -0.0022(6) C8 0.0205(8) 0.0161(9) 0.0280(9) 0.0020(7) 0.0047(6) -0.0005(6) C9 0.0214(8) 0.0168(9) 0.0228(9) 0.0022(7) 0.0043(6) -0.0026(6) C10 0.0215(8) 0.0226(10) 0.0255(10) 0.0012(7) 0.0045(6) 0.0012(6) C11 0.0317(9) 0.0215(10) 0.0250(9) -0.0001(7) 0.0074(7) -0.0003(7) C12 0.0301(9) 0.0243(10) 0.0238(9) 0.0037(8) -0.0007(7) -0.0047(7) C13 0.0207(8) 0.0220(10) 0.0327(10) 0.0029(8) 0.0005(7) 0.0001(6) C14 0.0357(9) 0.0291(11) 0.0283(10) -0.0048(8) 0.0133(7) -0.0032(7) C15 0.0243(8) 0.0207(10) 0.0305(10) -0.0024(8) 0.0054(6) 0.0021(6) C16 0.0269(8) 0.0254(10) 0.0249(9) -0.0008(8) 0.0088(7) -0.0008(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 F1 C1 1.3706(17) . ? O1 C6 1.4136(18) . ? O1 H1A 0.91(2) . ? O2 C7 1.2416(17) . ? N1 C7 1.3531(19) . ? N1 C14 1.4474(19) . ? N1 C6 1.4813(18) . ? C1 C16 1.371(2) . ? C1 C2 1.377(2) . ? C2 C3 1.386(2) . ? C2 H2 0.9500 . ? C3 C4 1.390(2) . ? C3 H3 0.9500 . ? C4 C15 1.393(2) . ? C4 C5 1.510(2) . ? C5 C6 1.5316(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C9 1.516(2) . ? C7 C8 1.478(2) . ? C8 C9 1.3864(19) . ? C8 C13 1.386(2) . ? C9 C10 1.380(2) . ? C10 C11 1.395(2) . ? C10 H10 0.9500 . ? C11 C12 1.386(2) . ? C11 H11 0.9500 . ? C12 C13 1.386(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.384(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O1 H1A 110.4(13) . . ? C7 N1 C14 123.81(12) . . ? C7 N1 C6 113.74(12) . . ? C14 N1 C6 122.40(11) . . ? F1 C1 C16 118.31(14) . . ? F1 C1 C2 118.47(14) . . ? C16 C1 C2 123.21(15) . . ? C1 C2 C3 117.54(15) . . ? C1 C2 H2 121.2 . . ? C3 C2 H2 121.2 . . ? C2 C3 C4 121.60(14) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C4 C15 118.29(14) . . ? C3 C4 C5 122.39(14) . . ? C15 C4 C5 119.25(13) . . ? C4 C5 C6 116.93(11) . . ? C4 C5 H5A 108.1 . . ? C6 C5 H5A 108.1 . . ? C4 C5 H5B 108.1 . . ? C6 C5 H5B 108.1 . . ? H5A C5 H5B 107.3 . . ? O1 C6 N1 110.99(11) . . ? O1 C6 C9 114.00(13) . . ? N1 C6 C9 100.99(11) . . ? O1 C6 C5 104.87(11) . . ? N1 C6 C5 111.58(12) . . ? C9 C6 C5 114.62(12) . . ? O2 C7 N1 125.53(15) . . ? O2 C7 C8 127.72(13) . . ? N1 C7 C8 106.73(12) . . ? C9 C8 C13 121.57(14) . . ? C9 C8 C7 108.72(13) . . ? C13 C8 C7 129.66(13) . . ? C10 C9 C8 120.69(14) . . ? C10 C9 C6 129.52(13) . . ? C8 C9 C6 109.79(13) . . ? C9 C10 C11 117.99(13) . . ? C9 C10 H10 121.0 . . ? C11 C10 H10 121.0 . . ? C12 C11 C10 121.12(15) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 120.77(14) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C8 117.86(13) . . ? C12 C13 H13 121.1 . . ? C8 C13 H13 121.1 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C4 121.26(15) . . ? C16 C15 H15 119.4 . . ? C4 C15 H15 119.4 . . ? C1 C16 C15 118.07(14) . . ? C1 C16 H16 121.0 . . ? C15 C16 H16 121.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C1 C2 C3 178.08(12) . . . . ? C16 C1 C2 C3 -1.3(2) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? C2 C3 C4 C15 1.0(2) . . . . ? C2 C3 C4 C5 -175.86(12) . . . . ? C3 C4 C5 C6 -81.42(18) . . . . ? C15 C4 C5 C6 101.75(15) . . . . ? C7 N1 C6 O1 121.55(14) . . . . ? C14 N1 C6 O1 -55.84(18) . . . . ? C7 N1 C6 C9 0.34(16) . . . . ? C14 N1 C6 C9 -177.05(13) . . . . ? C7 N1 C6 C5 -121.88(14) . . . . ? C14 N1 C6 C5 60.73(18) . . . . ? C4 C5 C6 O1 -174.51(13) . . . . ? C4 C5 C6 N1 65.25(17) . . . . ? C4 C5 C6 C9 -48.74(18) . . . . ? C14 N1 C7 O2 -0.4(2) . . . . ? C6 N1 C7 O2 -177.77(14) . . . . ? C14 N1 C7 C8 178.04(14) . . . . ? C6 N1 C7 C8 0.68(17) . . . . ? O2 C7 C8 C9 176.86(15) . . . . ? N1 C7 C8 C9 -1.54(17) . . . . ? O2 C7 C8 C13 -0.6(3) . . . . ? N1 C7 C8 C13 -179.06(15) . . . . ? C13 C8 C9 C10 0.2(2) . . . . ? C7 C8 C9 C10 -177.58(14) . . . . ? C13 C8 C9 C6 179.55(14) . . . . ? C7 C8 C9 C6 1.80(17) . . . . ? O1 C6 C9 C10 58.9(2) . . . . ? N1 C6 C9 C10 177.99(15) . . . . ? C5 C6 C9 C10 -61.9(2) . . . . ? O1 C6 C9 C8 -120.39(14) . . . . ? N1 C6 C9 C8 -1.32(16) . . . . ? C5 C6 C9 C8 118.75(14) . . . . ? C8 C9 C10 C11 0.8(2) . . . . ? C6 C9 C10 C11 -178.43(14) . . . . ? C9 C10 C11 C12 -1.1(2) . . . . ? C10 C11 C12 C13 0.4(2) . . . . ? C11 C12 C13 C8 0.5(2) . . . . ? C9 C8 C13 C12 -0.9(2) . . . . ? C7 C8 C13 C12 176.39(15) . . . . ? C3 C4 C15 C16 -1.0(2) . . . . ? C5 C4 C15 C16 175.97(13) . . . . ? F1 C1 C16 C15 -178.08(12) . . . . ? C2 C1 C16 C15 1.3(2) . . . . ? C4 C15 C16 C1 -0.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.186 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.045 data_nesn142 _database_code_depnum_ccdc_archive 'CCDC 876010' #TrackingRef 'nesn142.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H14 F3 N O2' _chemical_formula_sum 'C17 H14 F3 N O2' _chemical_formula_weight 321.29 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.6286(10) _cell_length_b 8.6250(7) _cell_length_c 10.8601(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.661(4) _cell_angle_gamma 90.00 _cell_volume 1454.02(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7237 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .3 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7237 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3147 _reflns_number_gt 2218 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0466P)^2^+0.1155P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3147 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1025 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F -0.08109(7) -0.66569(14) 0.29684(12) 0.0624(4) Uani 1 1 d . . . F2 F -0.02385(7) -0.59778(18) 0.13464(10) 0.0670(4) Uani 1 1 d . . . F3 F -0.05391(6) -0.42867(12) 0.26509(10) 0.0435(3) Uani 1 1 d . . . O1 O 0.37727(7) -0.78059(14) 0.34988(9) 0.0265(3) Uani 1 1 d . . . H1A H 0.4029(13) -0.860(3) 0.3286(18) 0.051(7) Uiso 1 1 d . . . O2 O 0.52324(7) -0.96860(13) 0.70118(9) 0.0231(3) Uani 1 1 d . . . N1 N 0.45097(8) -0.81091(15) 0.55333(11) 0.0215(3) Uani 1 1 d . . . C1 C -0.02203(11) -0.5713(2) 0.25600(16) 0.0331(4) Uani 1 1 d . . . C2 C 0.06559(10) -0.59009(19) 0.32469(14) 0.0266(4) Uani 1 1 d . . . C3 C 0.13684(11) -0.5468(2) 0.26883(14) 0.0279(4) Uani 1 1 d . . . H3 H 0.1299 -0.5034 0.1879 0.034 Uiso 1 1 calc R . . C4 C 0.21841(11) -0.56679(19) 0.33125(15) 0.0265(4) Uani 1 1 d . . . H4 H 0.2673 -0.5361 0.2927 0.032 Uiso 1 1 calc R . . C5 C 0.23017(10) -0.63102(19) 0.44937(13) 0.0233(4) Uani 1 1 d . . . C6 C 0.31906(10) -0.65519(19) 0.51661(13) 0.0251(4) Uani 1 1 d . . . H6A H 0.3144 -0.6633 0.6065 0.030 Uiso 1 1 calc R . . H6B H 0.3544 -0.5626 0.5038 0.030 Uiso 1 1 calc R . . C7 C 0.36638(10) -0.79957(19) 0.47599(13) 0.0223(4) Uani 1 1 d . . . C8 C 0.45911(10) -0.93753(18) 0.62668(13) 0.0200(4) Uani 1 1 d . . . C9 C 0.37931(10) -1.02981(19) 0.59765(13) 0.0210(4) Uani 1 1 d . . . C10 C 0.32608(10) -0.95271(18) 0.50612(13) 0.0219(4) Uani 1 1 d . . . C11 C 0.24943(10) -1.0195(2) 0.45461(14) 0.0279(4) Uani 1 1 d . . . H11 H 0.2134 -0.9687 0.3905 0.033 Uiso 1 1 calc R . . C12 C 0.22681(11) -1.1633(2) 0.49962(15) 0.0303(4) Uani 1 1 d . . . H12 H 0.1745 -1.2110 0.4658 0.036 Uiso 1 1 calc R . . C13 C 0.27957(10) -1.2383(2) 0.59325(14) 0.0273(4) Uani 1 1 d . . . H13 H 0.2622 -1.3353 0.6236 0.033 Uiso 1 1 calc R . . C14 C 0.35719(10) -1.17322(19) 0.64273(14) 0.0241(4) Uani 1 1 d . . . H14 H 0.3940 -1.2250 0.7054 0.029 Uiso 1 1 calc R . . C15 C 0.51614(10) -0.69126(18) 0.55353(14) 0.0243(4) Uani 1 1 d . . . H15A H 0.5146 -0.6471 0.4702 0.036 Uiso 1 1 calc R . . H15B H 0.5731 -0.7363 0.5784 0.036 Uiso 1 1 calc R . . H15C H 0.5048 -0.6095 0.6121 0.036 Uiso 1 1 calc R . . C16 C 0.15747(11) -0.67074(19) 0.50478(14) 0.0286(4) Uani 1 1 d . . . H16 H 0.1641 -0.7119 0.5865 0.034 Uiso 1 1 calc R . . C17 C 0.07574(11) -0.6516(2) 0.44353(14) 0.0301(4) Uani 1 1 d . . . H17 H 0.0267 -0.6805 0.4825 0.036 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 0.0331(7) 0.0540(9) 0.0962(9) 0.0202(7) -0.0096(6) -0.0101(6) F2 0.0414(7) 0.1127(12) 0.0430(7) -0.0297(7) -0.0120(5) 0.0198(7) F3 0.0379(6) 0.0373(7) 0.0530(6) 0.0005(5) -0.0047(5) 0.0125(5) O1 0.0334(7) 0.0263(7) 0.0196(6) 0.0028(5) 0.0022(4) 0.0088(6) O2 0.0244(6) 0.0235(6) 0.0204(5) 0.0006(5) -0.0017(4) 0.0029(5) N1 0.0219(7) 0.0200(8) 0.0221(6) 0.0004(6) -0.0003(5) 0.0012(6) C1 0.0288(10) 0.0323(12) 0.0379(10) -0.0025(8) 0.0027(7) 0.0037(8) C2 0.0256(9) 0.0218(9) 0.0321(9) -0.0029(7) 0.0015(7) 0.0031(7) C3 0.0320(10) 0.0262(10) 0.0253(8) 0.0044(7) 0.0018(7) 0.0047(8) C4 0.0263(9) 0.0243(10) 0.0300(9) 0.0040(7) 0.0079(7) 0.0029(7) C5 0.0278(9) 0.0169(8) 0.0254(8) -0.0019(7) 0.0033(6) 0.0044(7) C6 0.0278(9) 0.0228(9) 0.0243(8) -0.0009(7) 0.0011(6) 0.0035(7) C7 0.0233(9) 0.0239(9) 0.0188(7) 0.0009(7) -0.0010(6) 0.0046(7) C8 0.0241(9) 0.0186(9) 0.0177(7) -0.0034(7) 0.0043(6) 0.0037(7) C9 0.0234(9) 0.0217(9) 0.0182(7) -0.0027(7) 0.0036(6) 0.0029(7) C10 0.0239(9) 0.0214(9) 0.0205(8) -0.0027(7) 0.0026(6) 0.0032(7) C11 0.0266(9) 0.0272(10) 0.0283(8) -0.0031(7) -0.0032(7) 0.0055(8) C12 0.0240(9) 0.0298(11) 0.0363(9) -0.0065(8) 0.0000(7) -0.0017(8) C13 0.0301(10) 0.0208(9) 0.0320(9) -0.0031(8) 0.0074(7) -0.0005(8) C14 0.0291(9) 0.0224(9) 0.0213(8) -0.0004(7) 0.0050(6) 0.0035(7) C15 0.0274(9) 0.0215(9) 0.0239(8) 0.0003(7) 0.0031(6) 0.0000(7) C16 0.0332(10) 0.0280(10) 0.0253(8) 0.0055(7) 0.0069(7) 0.0072(8) C17 0.0289(10) 0.0287(11) 0.0341(9) 0.0036(8) 0.0098(7) 0.0018(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.344(2) . ? F2 C1 1.335(2) . ? F3 C1 1.335(2) . ? O1 C7 1.4091(17) . ? O1 H1A 0.84(2) . ? O2 C8 1.2421(18) . ? N1 C8 1.3491(19) . ? N1 C15 1.4498(19) . ? N1 C7 1.4850(19) . ? C1 C2 1.490(2) . ? C2 C3 1.380(2) . ? C2 C17 1.388(2) . ? C3 C4 1.383(2) . ? C3 H3 0.9500 . ? C4 C5 1.390(2) . ? C4 H4 0.9500 . ? C5 C16 1.389(2) . ? C5 C6 1.507(2) . ? C6 C7 1.539(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C10 1.515(2) . ? C8 C9 1.482(2) . ? C9 C14 1.389(2) . ? C9 C10 1.389(2) . ? C10 C11 1.387(2) . ? C11 C12 1.394(2) . ? C11 H11 0.9500 . ? C12 C13 1.392(2) . ? C12 H12 0.9500 . ? C13 C14 1.387(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.380(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1A 106.8(14) . . ? C8 N1 C15 123.87(12) . . ? C8 N1 C7 113.84(12) . . ? C15 N1 C7 122.21(12) . . ? F2 C1 F3 105.38(14) . . ? F2 C1 F1 106.59(14) . . ? F3 C1 F1 104.90(14) . . ? F2 C1 C2 112.89(14) . . ? F3 C1 C2 113.09(14) . . ? F1 C1 C2 113.29(15) . . ? C3 C2 C17 120.10(15) . . ? C3 C2 C1 119.47(15) . . ? C17 C2 C1 120.43(15) . . ? C2 C3 C4 119.71(15) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 121.18(15) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C16 C5 C4 118.09(15) . . ? C16 C5 C6 120.69(14) . . ? C4 C5 C6 121.21(14) . . ? C5 C6 C7 114.82(13) . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? O1 C7 N1 110.94(12) . . ? O1 C7 C10 114.28(12) . . ? N1 C7 C10 100.69(12) . . ? O1 C7 C6 107.51(12) . . ? N1 C7 C6 108.49(12) . . ? C10 C7 C6 114.70(13) . . ? O2 C8 N1 124.96(14) . . ? O2 C8 C9 128.18(14) . . ? N1 C8 C9 106.84(13) . . ? C14 C9 C10 121.71(15) . . ? C14 C9 C8 129.87(14) . . ? C10 C9 C8 108.32(14) . . ? C11 C10 C9 120.47(15) . . ? C11 C10 C7 129.50(14) . . ? C9 C10 C7 110.02(13) . . ? C10 C11 C12 118.06(15) . . ? C10 C11 H11 121.0 . . ? C12 C11 H11 121.0 . . ? C13 C12 C11 121.13(16) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C14 C13 C12 120.81(16) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C9 117.79(15) . . ? C13 C14 H14 121.1 . . ? C9 C14 H14 121.1 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C5 121.32(14) . . ? C17 C16 H16 119.3 . . ? C5 C16 H16 119.3 . . ? C16 C17 C2 119.58(15) . . ? C16 C17 H17 120.2 . . ? C2 C17 H17 120.2 . . ? 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 F2 C1 C2 C3 35.5(2) . . . . ? F3 C1 C2 C3 -84.1(2) . . . . ? F1 C1 C2 C3 156.73(16) . . . . ? F2 C1 C2 C17 -144.06(17) . . . . ? F3 C1 C2 C17 96.40(19) . . . . ? F1 C1 C2 C17 -22.8(2) . . . . ? C17 C2 C3 C4 0.8(3) . . . . ? C1 C2 C3 C4 -178.74(15) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C16 -1.8(2) . . . . ? C3 C4 C5 C6 179.02(15) . . . . ? C16 C5 C6 C7 101.45(17) . . . . ? C4 C5 C6 C7 -79.39(19) . . . . ? C8 N1 C7 O1 -126.63(13) . . . . ? C15 N1 C7 O1 56.53(17) . . . . ? C8 N1 C7 C10 -5.29(15) . . . . ? C15 N1 C7 C10 177.88(12) . . . . ? C8 N1 C7 C6 115.48(14) . . . . ? C15 N1 C7 C6 -61.35(17) . . . . ? C5 C6 C7 O1 62.12(17) . . . . ? C5 C6 C7 N1 -177.84(12) . . . . ? C5 C6 C7 C10 -66.18(17) . . . . ? C15 N1 C8 O2 -1.3(2) . . . . ? C7 N1 C8 O2 -178.07(13) . . . . ? C15 N1 C8 C9 -179.77(12) . . . . ? C7 N1 C8 C9 3.45(16) . . . . ? O2 C8 C9 C14 -1.9(3) . . . . ? N1 C8 C9 C14 176.52(14) . . . . ? O2 C8 C9 C10 -178.26(15) . . . . ? N1 C8 C9 C10 0.15(16) . . . . ? C14 C9 C10 C11 -1.6(2) . . . . ? C8 C9 C10 C11 175.16(13) . . . . ? C14 C9 C10 C7 179.74(13) . . . . ? C8 C9 C10 C7 -3.54(16) . . . . ? O1 C7 C10 C11 -54.4(2) . . . . ? N1 C7 C10 C11 -173.38(15) . . . . ? C6 C7 C10 C11 70.4(2) . . . . ? O1 C7 C10 C9 124.12(14) . . . . ? N1 C7 C10 C9 5.16(15) . . . . ? C6 C7 C10 C9 -111.07(14) . . . . ? C9 C10 C11 C12 1.6(2) . . . . ? C7 C10 C11 C12 -179.97(14) . . . . ? C10 C11 C12 C13 -0.2(2) . . . . ? C11 C12 C13 C14 -1.3(2) . . . . ? C12 C13 C14 C9 1.4(2) . . . . ? C10 C9 C14 C13 0.0(2) . . . . ? C8 C9 C14 C13 -175.91(14) . . . . ? C4 C5 C16 C17 1.9(2) . . . . ? C6 C5 C16 C17 -178.91(15) . . . . ? C5 C16 C17 C2 -0.7(3) . . . . ? C3 C2 C17 C16 -0.7(3) . . . . ? C1 C2 C17 C16 178.83(15) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.229 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.045