# Electronic Supplementary Material (ESI) for Chemical Communications # 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_liu20120512j #TrackingRef 'liu20120512j.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H16 F6 N2 S2' _chemical_formula_weight 474.48 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.8128(10) _cell_length_b 8.4517(3) _cell_length_c 24.4912(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.059(5) _cell_angle_gamma 90.00 _cell_volume 4376.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3832 _cell_measurement_theta_min 2.5901 _cell_measurement_theta_max 28.3328 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9939 _exptl_absorpt_correction_T_max 0.9970 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13611 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3862 _reflns_number_gt 2711 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0822P)^2^+6.9734P] 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 3862 _refine_ls_number_parameters 334 _refine_ls_number_restraints 1344 _refine_ls_R_factor_all 0.0865 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1840 _refine_ls_wR_factor_gt 0.1610 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.142 _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 S1 S 0.34953(6) -0.21687(16) 0.10111(6) 0.0904(4) Uani 1 1 d U . . S2 S 0.06137(8) 0.33937(19) -0.08805(6) 0.1093(6) Uani 1 1 d U A . F1 F 0.1715(15) 0.445(2) 0.0777(7) 0.082(3) Uani 0.22(2) 1 d PU A 1 F2 F 0.14074(14) 0.3139(4) 0.15341(14) 0.1075(9) Uani 1 1 d U A . F3 F 0.25476(18) 0.5144(4) 0.12359(17) 0.1049(15) Uani 0.792(7) 1 d PU A 1 F4 F 0.2382(2) 0.4959(5) 0.20450(17) 0.0937(14) Uani 0.778(7) 1 d PU A 1 F5 F 0.3300(7) 0.2573(14) 0.2260(5) 0.101(3) Uani 0.368(16) 1 d PU B 1 F6 F 0.3449(2) 0.3172(7) 0.1790(4) 0.0934(19) Uani 0.668(12) 1 d PU B 1 F1' F 0.1404(5) 0.4229(7) 0.0780(2) 0.092(2) Uani 0.78(2) 1 d PU A 2 F3' F 0.2537(7) 0.5425(18) 0.1769(8) 0.092(3) Uani 0.208(7) 1 d PU A 2 F4' F 0.2305(6) 0.3502(17) 0.2242(5) 0.092(3) Uani 0.222(7) 1 d PU A 2 F5' F 0.2950(5) 0.2314(7) 0.23361(18) 0.090(2) Uani 0.632(16) 1 d PU B 2 F6' F 0.3274(5) 0.3647(13) 0.1439(7) 0.090(3) Uani 0.332(12) 1 d PU B 2 N1 N 0.11891(13) 0.1353(4) 0.00940(12) 0.0553(7) Uani 1 1 d U A . N2 N -0.0125(2) 0.2068(8) -0.1785(2) 0.1254(15) Uani 1 1 d U A . C1 C 0.36700(19) -0.1980(6) 0.1756(2) 0.0795(11) Uani 1 1 d U . . C2 C 0.33577(19) -0.0740(5) 0.18552(19) 0.0730(10) Uani 1 1 d U . . H2 H 0.3395 -0.0429 0.2231 0.088 Uiso 1 1 calc R . . C3 C 0.29590(17) 0.0069(5) 0.13304(16) 0.0609(8) Uani 1 1 d U . . C4 C 0.29899(18) -0.0577(5) 0.08331(18) 0.0667(9) Uani 1 1 d U . . C5 C 0.25805(17) 0.1460(4) 0.13437(15) 0.0579(8) Uani 1 1 d U A . C6 C 0.2890(2) 0.2795(5) 0.17565(19) 0.0741(10) Uani 1 1 d U . . C7 C 0.2399(2) 0.4085(6) 0.1608(2) 0.0789(11) Uani 1 1 d U A . C8 C 0.17876(19) 0.3329(5) 0.12265(16) 0.0652(9) Uani 1 1 d U . . C9 C 0.19669(17) 0.1757(4) 0.10517(14) 0.0557(8) Uani 1 1 d U A . C10 C 0.14794(16) 0.0718(4) 0.06266(15) 0.0539(8) Uani 1 1 d U . . C11 C 0.13299(17) -0.0775(5) 0.07798(16) 0.0591(8) Uani 1 1 d U A . C12 C 0.08729(17) -0.1603(5) 0.03345(17) 0.0643(9) Uani 1 1 d U . . H12 H 0.0766 -0.2612 0.0418 0.077 Uiso 1 1 calc R A . C13 C 0.05685(16) -0.1015(5) -0.02235(17) 0.0605(9) Uani 1 1 d U A . C14 C 0.07392(16) 0.0515(5) -0.03253(15) 0.0578(8) Uani 1 1 d U . . C15 C 0.04417(18) 0.1421(5) -0.08797(16) 0.0679(9) Uani 1 1 d U A . C16 C 0.00586(19) 0.0897(6) -0.13724(16) 0.0741(11) Uani 1 1 d U . . H16 H -0.0078 -0.0147 -0.1441 0.089 Uiso 1 1 calc R A . C17 C 0.0127(3) 0.3500(8) -0.1596(2) 0.1137(17) Uani 1 1 d U . . H17 H 0.0044 0.4413 -0.1825 0.136 Uiso 1 1 calc R A . C18 C 0.4095(2) -0.3145(7) 0.2194(3) 0.118(2) Uani 1 1 d U . . H18A H 0.4344 -0.2598 0.2549 0.177 Uiso 1 1 calc R . . H18B H 0.4370 -0.3642 0.2030 0.177 Uiso 1 1 calc R . . H18C H 0.3841 -0.3935 0.2282 0.177 Uiso 1 1 calc R . . C19 C 0.2690(2) -0.0025(6) 0.02064(18) 0.0907(14) Uani 1 1 d U . . H19A H 0.2324 -0.0658 0.0002 0.136 Uiso 1 1 calc R . . H19B H 0.2988 -0.0129 0.0017 0.136 Uiso 1 1 calc R . . H19C H 0.2568 0.1063 0.0199 0.136 Uiso 1 1 calc R . . C20 C 0.1617(2) -0.1436(6) 0.13939(18) 0.0807(12) Uani 1 1 d U . . H20A H 0.1376 -0.2335 0.1429 0.121 Uiso 1 1 calc R A . H20B H 0.1614 -0.0640 0.1672 0.121 Uiso 1 1 calc R . . H20C H 0.2045 -0.1754 0.1473 0.121 Uiso 1 1 calc R . . C21 C 0.00615(19) -0.1983(5) -0.0680(2) 0.0795(12) Uani 1 1 d U . . H21A H 0.0035 -0.3006 -0.0520 0.119 Uiso 1 1 calc R A . H21B H 0.0166 -0.2105 -0.1023 0.119 Uiso 1 1 calc R . . H21C H -0.0338 -0.1452 -0.0787 0.119 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 S1 0.0666(7) 0.0883(8) 0.1214(10) -0.0307(7) 0.0410(7) 0.0006(6) S2 0.1193(11) 0.1070(10) 0.0727(8) 0.0211(7) 0.0030(7) -0.0229(9) F1 0.084(6) 0.073(5) 0.074(5) 0.001(4) 0.014(5) 0.001(5) F2 0.0979(18) 0.112(2) 0.136(2) -0.0459(17) 0.0707(17) -0.0127(16) F3 0.108(3) 0.097(2) 0.098(3) 0.015(2) 0.025(2) -0.027(2) F4 0.103(3) 0.094(3) 0.075(2) -0.040(2) 0.0232(19) 0.002(2) F5 0.088(5) 0.106(5) 0.074(4) -0.026(4) -0.010(4) -0.004(4) F6 0.061(2) 0.090(3) 0.110(4) -0.023(3) 0.010(3) -0.015(2) F1' 0.085(4) 0.071(2) 0.088(2) -0.0093(18) -0.002(2) 0.018(2) F3' 0.084(5) 0.081(5) 0.094(6) -0.025(5) 0.015(5) -0.001(5) F4' 0.091(5) 0.106(5) 0.069(5) -0.019(4) 0.020(4) 0.007(5) F5' 0.118(5) 0.093(3) 0.045(2) -0.0105(19) 0.012(2) -0.001(3) F6' 0.078(4) 0.090(5) 0.095(5) -0.016(4) 0.024(4) -0.011(4) N1 0.0504(14) 0.0673(16) 0.0472(14) -0.0048(13) 0.0173(12) -0.0045(13) N2 0.104(3) 0.162(4) 0.091(3) 0.005(3) 0.016(2) -0.015(3) C1 0.053(2) 0.080(2) 0.097(3) -0.008(2) 0.017(2) 0.0015(19) C2 0.0568(19) 0.081(2) 0.075(2) -0.0080(19) 0.0181(17) 0.0007(18) C3 0.0504(17) 0.0689(19) 0.0629(18) -0.0094(16) 0.0206(15) -0.0034(15) C4 0.0550(18) 0.075(2) 0.072(2) -0.0167(18) 0.0257(16) -0.0068(17) C5 0.0568(17) 0.0666(18) 0.0497(16) -0.0082(15) 0.0194(14) -0.0029(15) C6 0.066(2) 0.077(2) 0.067(2) -0.0153(18) 0.0115(18) -0.0010(19) C7 0.077(2) 0.075(2) 0.077(2) -0.023(2) 0.020(2) -0.004(2) C8 0.0672(19) 0.069(2) 0.0574(18) -0.0060(17) 0.0207(16) 0.0033(17) C9 0.0570(17) 0.0644(18) 0.0474(15) -0.0043(14) 0.0215(14) -0.0008(15) C10 0.0498(16) 0.0602(18) 0.0524(16) -0.0050(15) 0.0201(14) 0.0007(14) C11 0.0531(17) 0.0629(19) 0.0624(18) 0.0001(16) 0.0230(15) 0.0026(15) C12 0.0539(18) 0.060(2) 0.078(2) -0.0037(18) 0.0232(17) -0.0016(16) C13 0.0444(17) 0.068(2) 0.069(2) -0.0140(17) 0.0219(16) -0.0019(16) C14 0.0463(16) 0.075(2) 0.0532(17) -0.0089(16) 0.0207(14) -0.0033(16) C15 0.0571(18) 0.093(2) 0.0544(18) -0.0017(18) 0.0216(16) -0.0061(18) C16 0.067(2) 0.095(3) 0.0447(18) -0.0008(19) 0.0032(17) -0.017(2) C17 0.114(3) 0.132(4) 0.073(3) 0.028(3) 0.010(3) -0.013(3) C18 0.069(3) 0.097(4) 0.157(5) 0.009(4) 0.006(3) 0.019(3) C19 0.091(3) 0.115(4) 0.070(3) -0.025(3) 0.035(2) -0.006(3) C20 0.077(3) 0.081(3) 0.077(3) 0.021(2) 0.020(2) 0.000(2) C21 0.058(2) 0.083(3) 0.091(3) -0.026(2) 0.021(2) -0.013(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 S1 C4 1.718(4) . ? S1 C1 1.723(5) . ? S2 C17 1.688(5) . ? S2 C15 1.713(5) . ? F1 C8 1.413(17) . ? F2 C8 1.355(5) . ? F3 C7 1.406(6) . ? F4 C7 1.313(5) . ? F5 C6 1.251(9) . ? F6 C6 1.287(6) . ? F1' C8 1.349(6) . ? F3' C7 1.202(15) . ? F4' C7 1.717(14) . ? F5' C6 1.433(7) . ? F6' C6 1.551(13) . ? N1 C10 1.334(4) . ? N1 C14 1.348(4) . ? N2 C17 1.345(8) . ? N2 C16 1.364(7) . ? C1 C2 1.339(6) . ? C1 C18 1.509(7) . ? C2 C3 1.438(6) . ? C3 C4 1.360(5) . ? C3 C5 1.467(5) . ? C4 C19 1.501(6) . ? C5 C9 1.335(5) . ? C5 C6 1.502(5) . ? C6 C7 1.507(6) . ? C7 C8 1.498(6) . ? C8 C9 1.499(5) . ? C9 C10 1.491(5) . ? C10 C11 1.395(5) . ? C11 C12 1.383(5) . ? C11 C20 1.505(5) . ? C12 C13 1.372(5) . ? C13 C14 1.400(5) . ? C13 C21 1.512(5) . ? C14 C15 1.483(5) . ? C15 C16 1.274(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 S1 C1 93.6(2) . . ? C17 S2 C15 89.5(3) . . ? C10 N1 C14 119.4(3) . . ? C17 N2 C16 115.2(5) . . ? C2 C1 C18 128.6(5) . . ? C2 C1 S1 109.7(4) . . ? C18 C1 S1 121.6(4) . . ? C1 C2 C3 114.3(4) . . ? C4 C3 C2 112.4(4) . . ? C4 C3 C5 124.8(4) . . ? C2 C3 C5 122.8(3) . . ? C3 C4 C19 129.4(4) . . ? C3 C4 S1 110.0(3) . . ? C19 C4 S1 120.5(3) . . ? C9 C5 C3 130.3(3) . . ? C9 C5 C6 110.7(3) . . ? C3 C5 C6 119.0(3) . . ? F5 C6 F6 67.5(11) . . ? F5 C6 F5' 39.0(7) . . ? F6 C6 F5' 106.4(7) . . ? F5 C6 C5 122.6(6) . . ? F6 C6 C5 115.7(4) . . ? F5' C6 C5 107.4(4) . . ? F5 C6 C7 124.1(7) . . ? F6 C6 C7 117.8(5) . . ? F5' C6 C7 103.3(5) . . ? C5 C6 C7 105.1(3) . . ? F5 C6 F6' 102.1(12) . . ? F6 C6 F6' 35.3(4) . . ? F5' C6 F6' 140.1(7) . . ? C5 C6 F6' 102.8(5) . . ? C7 C6 F6' 93.0(6) . . ? F3' C7 F4 44.4(9) . . ? F3' C7 F3 61.0(10) . . ? F4 C7 F3 104.9(4) . . ? F3' C7 C8 132.4(8) . . ? F4 C7 C8 116.3(4) . . ? F3 C7 C8 105.2(4) . . ? F3' C7 C6 121.5(8) . . ? F4 C7 C6 117.1(4) . . ? F3 C7 C6 106.1(4) . . ? C8 C7 C6 106.0(4) . . ? F3' C7 F4' 94.5(11) . . ? F4 C7 F4' 51.2(5) . . ? F3 C7 F4' 155.5(6) . . ? C8 C7 F4' 92.2(5) . . ? C6 C7 F4' 84.7(5) . . ? F1' C8 F2 99.3(6) . . ? F1' C8 F1 30.8(9) . . ? F2 C8 F1 126.8(13) . . ? F1' C8 C7 115.6(5) . . ? F2 C8 C7 110.1(3) . . ? F1 C8 C7 90.6(12) . . ? F1' C8 C9 115.6(3) . . ? F2 C8 C9 110.8(3) . . ? F1 C8 C9 109.6(8) . . ? C7 C8 C9 105.4(3) . . ? C5 C9 C10 128.4(3) . . ? C5 C9 C8 110.9(3) . . ? C10 C9 C8 120.6(3) . . ? N1 C10 C11 123.0(3) . . ? N1 C10 C9 114.4(3) . . ? C11 C10 C9 122.6(3) . . ? C12 C11 C10 115.7(3) . . ? C12 C11 C20 121.1(4) . . ? C10 C11 C20 123.1(4) . . ? C13 C12 C11 123.5(4) . . ? C12 C13 C14 116.2(3) . . ? C12 C13 C21 120.1(4) . . ? C14 C13 C21 123.7(4) . . ? N1 C14 C13 122.2(3) . . ? N1 C14 C15 112.5(3) . . ? C13 C14 C15 125.3(3) . . ? C16 C15 C14 127.1(4) . . ? C16 C15 S2 114.4(4) . . ? C14 C15 S2 118.5(3) . . ? C15 C16 N2 111.1(5) . . ? N2 C17 S2 109.8(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.392 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 899297' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 F6 N S2' _chemical_formula_weight 473.49 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 8.8943(10) _cell_length_b 11.9170(14) _cell_length_c 12.0266(14) _cell_angle_alpha 66.6080(10) _cell_angle_beta 68.4160(10) _cell_angle_gamma 78.7220(10) _cell_volume 1086.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4641 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.305 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8826 _exptl_absorpt_correction_T_max 0.9008 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8409 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4017 _reflns_number_gt 3305 _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^)+(0.1021P)^2^+0.9558P] 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 SHELXL _refine_ls_extinction_coef 0.035(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4017 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.2049 _refine_ls_wR_factor_gt 0.1895 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 S1 S 0.46583(11) 1.09314(9) 0.11098(9) 0.0692(3) Uani 1 1 d . A 1 C2 C 0.6344(4) 0.9966(3) 0.1257(3) 0.0546(7) Uani 1 1 d . A 1 C3 C 0.6068(4) 0.9201(3) 0.2498(3) 0.0519(7) Uani 1 1 d . A 1 C4 C 0.4483(4) 0.9407(3) 0.3317(3) 0.0596(8) Uani 1 1 d . A 1 H4 H 0.4120 0.8965 0.4192 0.072 Uiso 1 1 calc R A 1 C5 C 0.3571(4) 1.0295(3) 0.2709(4) 0.0622(8) Uani 1 1 d . A 1 C1 C 0.7844(4) 1.0100(4) 0.0125(4) 0.0713(9) Uani 1 1 d . A 1 H1A H 0.8427 1.0762 -0.0003 0.107 Uiso 1 1 calc R A 1 H1B H 0.7553 1.0268 -0.0622 0.107 Uiso 1 1 calc R A 1 H1C H 0.8514 0.9354 0.0273 0.107 Uiso 1 1 calc R A 1 C6 C 0.1844(4) 1.0718(4) 0.3243(5) 0.0838(12) Uani 1 1 d . A 1 H6A H 0.1364 1.0145 0.4085 0.126 Uiso 1 1 calc R A 1 H6B H 0.1251 1.0770 0.2697 0.126 Uiso 1 1 calc R A 1 H6C H 0.1812 1.1510 0.3287 0.126 Uiso 1 1 calc R A 1 C7 C 0.7273(4) 0.8283(3) 0.2963(3) 0.0512(7) Uani 1 1 d . A 1 C11 C 0.8026(4) 0.7335(3) 0.2608(3) 0.0539(7) Uani 1 1 d . A 1 C8 C 0.7858(4) 0.8366(3) 0.3946(3) 0.0635(8) Uani 1 1 d . A 1 C10 C 0.9216(5) 0.6663(3) 0.3305(4) 0.0712(10) Uani 1 1 d . A 1 C9 C 0.9016(7) 0.7278(5) 0.4229(5) 0.1015(17) Uani 1 1 d . A 1 C16 C 0.9049(4) 0.6598(3) -0.0249(3) 0.0558(7) Uani 1 1 d . A 1 C12 C 0.7783(4) 0.6903(3) 0.1685(3) 0.0538(7) Uani 1 1 d . A 1 C13 C 0.6343(4) 0.6455(3) 0.1886(3) 0.0637(8) Uani 1 1 d . A 1 C14 C 0.6334(5) 0.6083(3) 0.0935(4) 0.0714(10) Uani 1 1 d . A 1 H14 H 0.5391 0.5778 0.1028 0.086 Uiso 1 1 calc R A 1 C15 C 0.7655(5) 0.6139(3) -0.0147(3) 0.0661(9) Uani 1 1 d . A 1 C17 C 0.4881(5) 0.6356(5) 0.3055(5) 0.0932(13) Uani 1 1 d . A 1 H17A H 0.4300 0.7140 0.2952 0.140 Uiso 1 1 calc R A 1 H17B H 0.5221 0.6095 0.3794 0.140 Uiso 1 1 calc R A 1 H17C H 0.4188 0.5769 0.3163 0.140 Uiso 1 1 calc R A 1 C18 C 0.7522(7) 0.5711(5) -0.1129(5) 0.1038(16) Uani 1 1 d . A 1 H18A H 0.8159 0.4956 -0.1100 0.156 Uiso 1 1 calc R A 1 H18B H 0.7912 0.6319 -0.1966 0.156 Uiso 1 1 calc R A 1 H18C H 0.6410 0.5584 -0.0945 0.156 Uiso 1 1 calc R A 1 C19 C 1.0568(5) 0.6758(3) -0.1321(3) 0.0635(9) Uani 1 1 d . A 1 C20 C 1.1105(6) 0.6467(3) -0.2415(4) 0.0806(11) Uani 1 1 d . A 1 H20 H 1.0491 0.6078 -0.2621 0.097 Uiso 1 1 calc R A 1 C21 C 1.2694(7) 0.6828(5) -0.3181(4) 0.1052(17) Uani 1 1 d . A 1 H21 H 1.3237 0.6696 -0.3946 0.126 Uiso 1 1 calc R A 1 C22 C 1.3339(8) 0.7377(5) -0.2704(5) 0.1162(19) Uani 1 1 d . A 1 H22 H 1.4372 0.7670 -0.3097 0.139 Uiso 1 1 calc R A 1 S2 S 1.20506(17) 0.74747(13) -0.12939(12) 0.1021(5) Uani 1 1 d . A 1 F2 F 0.8624(5) 0.9380(3) 0.3516(4) 0.1359(14) Uani 1 1 d . A 1 F4 F 1.0051(5) 0.7234(4) 0.4672(5) 0.128(2) Uani 0.735(7) 1 d P A 1 F1 F 0.6683(4) 0.8414(4) 0.4987(3) 0.1481(16) Uani 1 1 d . . . F6 F 1.0730(4) 0.6694(5) 0.2550(3) 0.1546(17) Uani 1 1 d . . . F5 F 0.8946(6) 0.5491(3) 0.3910(4) 0.1522(16) Uani 1 1 d . . . F3 F 0.8099(10) 0.6482(4) 0.5427(4) 0.235(4) Uani 1 1 d . . . N1 N 0.9097(3) 0.6961(2) 0.0663(2) 0.0534(6) Uani 1 1 d . . . F4' F 1.0674(10) 0.8097(7) 0.3285(8) 0.072(3) Uiso 0.265(7) 1 d P A 2 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 S1 0.0690(6) 0.0719(6) 0.0698(6) -0.0234(4) -0.0342(5) 0.0085(4) C2 0.0560(17) 0.0583(17) 0.0571(18) -0.0239(14) -0.0220(14) -0.0050(13) C3 0.0535(16) 0.0541(16) 0.0549(17) -0.0248(13) -0.0202(13) -0.0008(12) C4 0.0586(18) 0.0637(19) 0.0565(18) -0.0271(15) -0.0147(14) 0.0012(14) C5 0.0546(17) 0.067(2) 0.076(2) -0.0367(17) -0.0242(16) 0.0028(14) C1 0.065(2) 0.081(2) 0.063(2) -0.0236(18) -0.0151(16) -0.0092(17) C6 0.058(2) 0.099(3) 0.106(3) -0.056(3) -0.028(2) 0.0139(19) C7 0.0532(16) 0.0559(16) 0.0477(15) -0.0219(13) -0.0176(13) -0.0002(13) C11 0.0583(17) 0.0586(17) 0.0490(16) -0.0217(13) -0.0216(13) 0.0018(13) C8 0.067(2) 0.078(2) 0.0599(19) -0.0379(17) -0.0244(16) 0.0037(16) C10 0.083(2) 0.071(2) 0.076(2) -0.0377(19) -0.045(2) 0.0238(18) C9 0.150(4) 0.100(3) 0.094(3) -0.055(3) -0.088(3) 0.048(3) C16 0.082(2) 0.0413(14) 0.0520(17) -0.0183(12) -0.0294(15) 0.0000(14) C12 0.0645(18) 0.0478(15) 0.0558(17) -0.0215(13) -0.0266(15) 0.0030(13) C13 0.067(2) 0.0606(19) 0.069(2) -0.0254(16) -0.0261(17) -0.0033(15) C14 0.082(2) 0.064(2) 0.084(3) -0.0263(18) -0.039(2) -0.0137(17) C15 0.093(2) 0.0538(18) 0.065(2) -0.0210(15) -0.0386(19) -0.0081(16) C17 0.073(2) 0.110(3) 0.100(3) -0.049(3) -0.010(2) -0.023(2) C18 0.146(4) 0.112(4) 0.086(3) -0.044(3) -0.046(3) -0.043(3) C19 0.093(2) 0.0469(16) 0.0502(17) -0.0173(13) -0.0235(17) -0.0013(15) C20 0.117(3) 0.064(2) 0.063(2) -0.0304(18) -0.029(2) 0.007(2) C21 0.146(5) 0.086(3) 0.055(2) -0.028(2) -0.002(3) 0.000(3) C22 0.127(4) 0.109(4) 0.079(3) -0.035(3) 0.021(3) -0.039(3) S2 0.1123(9) 0.1129(9) 0.0795(7) -0.0484(7) 0.0092(6) -0.0520(8) F2 0.202(3) 0.0869(18) 0.177(3) -0.0277(19) -0.137(3) -0.027(2) F4 0.134(4) 0.156(4) 0.197(5) -0.131(4) -0.138(4) 0.081(3) F1 0.0923(19) 0.297(5) 0.0886(19) -0.118(3) -0.0339(15) 0.032(2) F6 0.0773(17) 0.297(5) 0.119(2) -0.114(3) -0.0555(17) 0.061(2) F5 0.259(5) 0.0680(16) 0.188(3) -0.0310(19) -0.173(4) 0.031(2) F3 0.440(10) 0.144(4) 0.092(3) -0.041(2) -0.104(4) 0.077(5) N1 0.0641(15) 0.0498(13) 0.0539(14) -0.0235(11) -0.0239(12) 0.0007(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 S1 C2 1.721(3) . ? S1 C5 1.723(4) . ? C2 C3 1.362(4) . ? C2 C1 1.494(5) . ? C3 C4 1.433(4) . ? C3 C7 1.467(4) . ? C4 C5 1.341(5) . ? C4 H4 0.9300 . ? C5 C6 1.502(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C11 1.336(4) . ? C7 C8 1.499(4) . ? C11 C12 1.489(4) . ? C11 C10 1.501(4) . ? C8 F1 1.317(4) . ? C8 F2 1.326(5) . ? C8 C9 1.497(5) . ? C10 F6 1.316(5) . ? C10 F5 1.316(5) . ? C10 C9 1.502(5) . ? C9 F4 1.206(5) . ? C9 F3 1.412(8) . ? C16 N1 1.346(4) . ? C16 C15 1.396(5) . ? C16 C19 1.466(5) . ? C12 N1 1.337(4) . ? C12 C13 1.387(5) . ? C13 C14 1.383(5) . ? C13 C17 1.505(5) . ? C14 C15 1.384(5) . ? C14 H14 0.9300 . ? C15 C18 1.508(5) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.383(5) . ? C19 S2 1.721(4) . ? C20 C21 1.413(7) . ? C20 H20 0.9300 . ? C21 C22 1.331(8) . ? C21 H21 0.9300 . ? C22 S2 1.697(5) . ? C22 H22 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C5 93.38(15) . . ? C3 C2 C1 130.0(3) . . ? C3 C2 S1 109.8(2) . . ? C1 C2 S1 120.1(2) . . ? C2 C3 C4 112.8(3) . . ? C2 C3 C7 124.0(3) . . ? C4 C3 C7 123.2(3) . . ? C5 C4 C3 113.9(3) . . ? C5 C4 H4 123.0 . . ? C3 C4 H4 123.0 . . ? C4 C5 C6 128.6(4) . . ? C4 C5 S1 110.0(3) . . ? C6 C5 S1 121.4(3) . . ? C11 C7 C3 129.2(3) . . ? C11 C7 C8 110.7(3) . . ? C3 C7 C8 120.1(3) . . ? C7 C11 C12 128.4(3) . . ? C7 C11 C10 111.0(3) . . ? C12 C11 C10 120.6(3) . . ? F1 C8 F2 104.2(4) . . ? F1 C8 C9 112.1(4) . . ? F2 C8 C9 109.2(4) . . ? F1 C8 C7 113.6(3) . . ? F2 C8 C7 111.9(3) . . ? C9 C8 C7 105.9(3) . . ? F6 C10 F5 105.1(4) . . ? F6 C10 C11 113.7(3) . . ? F5 C10 C11 111.9(3) . . ? F6 C10 C9 109.8(4) . . ? F5 C10 C9 111.0(4) . . ? C11 C10 C9 105.5(3) . . ? F4 C9 F3 89.9(5) . . ? F4 C9 C8 123.2(4) . . ? F3 C9 C8 102.9(5) . . ? F4 C9 C10 123.4(4) . . ? F3 C9 C10 104.7(5) . . ? C8 C9 C10 106.5(3) . . ? N1 C16 C15 121.4(3) . . ? N1 C16 C19 113.0(3) . . ? C15 C16 C19 125.6(3) . . ? N1 C12 C13 123.4(3) . . ? N1 C12 C11 113.6(3) . . ? C13 C12 C11 123.0(3) . . ? C14 C13 C12 115.3(3) . . ? C14 C13 C17 121.4(3) . . ? C12 C13 C17 123.3(3) . . ? C13 C14 C15 123.4(3) . . ? C13 C14 H14 118.3 . . ? C15 C14 H14 118.3 . . ? C14 C15 C16 116.5(3) . . ? C14 C15 C18 119.3(4) . . ? C16 C15 C18 124.1(4) . . ? C20 C19 C16 133.6(4) . . ? C20 C19 S2 109.7(3) . . ? C16 C19 S2 116.7(2) . . ? C19 C20 C21 112.2(4) . . ? C19 C20 H20 123.9 . . ? C21 C20 H20 123.9 . . ? C22 C21 C20 113.7(4) . . ? C22 C21 H21 123.1 . . ? C20 C21 H21 123.1 . . ? C21 C22 S2 111.9(4) . . ? C21 C22 H22 124.1 . . ? S2 C22 H22 124.1 . . ? C22 S2 C19 92.6(3) . . ? C12 N1 C16 119.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 S1 C2 C3 -0.8(2) . . . . ? C5 S1 C2 C1 -177.5(3) . . . . ? C1 C2 C3 C4 176.4(3) . . . . ? S1 C2 C3 C4 0.1(3) . . . . ? C1 C2 C3 C7 -2.1(5) . . . . ? S1 C2 C3 C7 -178.3(2) . . . . ? C2 C3 C4 C5 0.9(4) . . . . ? C7 C3 C4 C5 179.3(3) . . . . ? C3 C4 C5 C6 177.0(3) . . . . ? C3 C4 C5 S1 -1.5(4) . . . . ? C2 S1 C5 C4 1.3(3) . . . . ? C2 S1 C5 C6 -177.3(3) . . . . ? C2 C3 C7 C11 -59.8(5) . . . . ? C4 C3 C7 C11 121.9(4) . . . . ? C2 C3 C7 C8 118.0(4) . . . . ? C4 C3 C7 C8 -60.3(4) . . . . ? C3 C7 C11 C12 -3.7(6) . . . . ? C8 C7 C11 C12 178.4(3) . . . . ? C3 C7 C11 C10 177.8(3) . . . . ? C8 C7 C11 C10 -0.2(4) . . . . ? C11 C7 C8 F1 -127.2(4) . . . . ? C3 C7 C8 F1 54.7(5) . . . . ? C11 C7 C8 F2 115.2(4) . . . . ? C3 C7 C8 F2 -63.0(4) . . . . ? C11 C7 C8 C9 -3.7(4) . . . . ? C3 C7 C8 C9 178.1(4) . . . . ? C7 C11 C10 F6 -116.4(4) . . . . ? C12 C11 C10 F6 65.0(5) . . . . ? C7 C11 C10 F5 124.8(4) . . . . ? C12 C11 C10 F5 -53.9(5) . . . . ? C7 C11 C10 C9 4.0(5) . . . . ? C12 C11 C10 C9 -174.7(4) . . . . ? F1 C8 C9 F4 -78.0(7) . . . . ? F2 C8 C9 F4 36.9(7) . . . . ? C7 C8 C9 F4 157.6(6) . . . . ? F1 C8 C9 F3 20.5(5) . . . . ? F2 C8 C9 F3 135.4(4) . . . . ? C7 C8 C9 F3 -103.9(4) . . . . ? F1 C8 C9 C10 130.4(4) . . . . ? F2 C8 C9 C10 -114.7(4) . . . . ? C7 C8 C9 C10 6.0(5) . . . . ? F6 C10 C9 F4 -34.7(8) . . . . ? F5 C10 C9 F4 81.0(8) . . . . ? C11 C10 C9 F4 -157.6(6) . . . . ? F6 C10 C9 F3 -134.6(5) . . . . ? F5 C10 C9 F3 -18.9(6) . . . . ? C11 C10 C9 F3 102.5(4) . . . . ? F6 C10 C9 C8 116.8(4) . . . . ? F5 C10 C9 C8 -127.4(4) . . . . ? C11 C10 C9 C8 -6.0(5) . . . . ? C7 C11 C12 N1 117.3(4) . . . . ? C10 C11 C12 N1 -64.2(4) . . . . ? C7 C11 C12 C13 -64.3(5) . . . . ? C10 C11 C12 C13 114.1(4) . . . . ? N1 C12 C13 C14 -1.2(5) . . . . ? C11 C12 C13 C14 -179.4(3) . . . . ? N1 C12 C13 C17 178.1(3) . . . . ? C11 C12 C13 C17 -0.1(5) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? C17 C13 C14 C15 -179.0(4) . . . . ? C13 C14 C15 C16 0.2(5) . . . . ? C13 C14 C15 C18 -180.0(4) . . . . ? N1 C16 C15 C14 0.2(5) . . . . ? C19 C16 C15 C14 -178.8(3) . . . . ? N1 C16 C15 C18 -179.7(4) . . . . ? C19 C16 C15 C18 1.3(6) . . . . ? N1 C16 C19 C20 176.2(4) . . . . ? C15 C16 C19 C20 -4.8(6) . . . . ? N1 C16 C19 S2 -4.9(4) . . . . ? C15 C16 C19 S2 174.1(3) . . . . ? C16 C19 C20 C21 179.3(4) . . . . ? S2 C19 C20 C21 0.3(4) . . . . ? C19 C20 C21 C22 -0.4(6) . . . . ? C20 C21 C22 S2 0.3(6) . . . . ? C21 C22 S2 C19 -0.1(5) . . . . ? C20 C19 S2 C22 -0.1(3) . . . . ? C16 C19 S2 C22 -179.3(3) . . . . ? C13 C12 N1 C16 1.6(5) . . . . ? C11 C12 N1 C16 179.9(2) . . . . ? C15 C16 N1 C12 -1.0(4) . . . . ? C19 C16 N1 C12 178.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.651 _refine_diff_density_min -0.708 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 879873' ####################################################################### # # 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_liu20120513c #TrackingRef 'liu20120513c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H19 F6 N S' _chemical_formula_weight 467.46 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 9.2019(14) _cell_length_b 11.350(2) _cell_length_c 12.040(2) _cell_angle_alpha 92.035(16) _cell_angle_beta 105.450(16) _cell_angle_gamma 111.628(16) _cell_volume 1114.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1400 _cell_measurement_theta_min 2.8223 _cell_measurement_theta_max 28.5514 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9959 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7167 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3925 _reflns_number_gt 2889 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.3598P] 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 3925 _refine_ls_number_parameters 313 _refine_ls_number_restraints 1140 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1710 _refine_ls_wR_factor_gt 0.1543 _refine_ls_goodness_of_fit_ref 1.193 _refine_ls_restrained_S_all 1.390 _refine_ls_shift/su_max 0.009 _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 S1 S 0.50812(13) 0.93470(10) 0.21231(11) 0.0791(4) Uani 1 1 d U . . N1 N 0.7772(3) 0.5701(2) 0.3279(2) 0.0457(6) Uani 1 1 d U B . F1 F 1.0378(3) 0.6169(3) 0.1734(2) 0.1028(9) Uani 1 1 d U B . F2 F 0.7881(4) 0.4943(2) 0.0831(2) 0.1013(9) Uani 1 1 d U B . F3 F 0.930(3) 0.636(2) -0.0747(15) 0.077(3) Uani 0.25(2) 1 d PU A 1 F4 F 1.0551(4) 0.7640(3) 0.0215(3) 0.1162(10) Uani 1 1 d U . . F5 F 0.6406(4) 0.6773(3) -0.0833(2) 0.1105(9) Uani 1 1 d U B . F6 F 0.817(2) 0.8470(11) -0.0630(8) 0.083(2) Uani 0.60(3) 1 d PU B 1 F3' F 0.8501(15) 0.5881(8) -0.0932(5) 0.0916(18) Uani 0.75(2) 1 d PU A 2 F6' F 0.888(3) 0.8761(12) -0.0289(16) 0.081(3) Uani 0.40(3) 1 d PU B 2 C1 C 0.6497(5) 1.0403(4) 0.1573(4) 0.0662(9) Uani 1 1 d U . . C2 C 0.7395(4) 0.9834(3) 0.1235(3) 0.0593(8) Uani 1 1 d U . . H2 H 0.8217 1.0248 0.0903 0.071 Uiso 1 1 calc R . . C3 C 0.6964(4) 0.8531(3) 0.1437(3) 0.0528(7) Uani 1 1 d U . . C4 C 0.5708(4) 0.8121(3) 0.1910(3) 0.0596(8) Uani 1 1 d U . . C5 C 0.7762(4) 0.7701(3) 0.1139(3) 0.0492(7) Uani 1 1 d U B . C6 C 0.7913(5) 0.7518(4) -0.0057(3) 0.0667(9) Uani 1 1 d U . . C7 C 0.9000(5) 0.6780(4) 0.0034(3) 0.0666(9) Uani 1 1 d U A . C8 C 0.8936(5) 0.6189(4) 0.1138(3) 0.0598(8) Uani 1 1 d U . . C9 C 0.8367(4) 0.6973(3) 0.1809(3) 0.0469(7) Uani 1 1 d U B . C10 C 0.8551(4) 0.6882(3) 0.3064(3) 0.0451(7) Uani 1 1 d U . . C11 C 0.9521(4) 0.7933(3) 0.3936(3) 0.0509(7) Uani 1 1 d U B . C12 C 0.9624(4) 0.7689(3) 0.5072(3) 0.0588(8) Uani 1 1 d U . . H12 H 1.0265 0.8360 0.5682 0.071 Uiso 1 1 calc R B . C13 C 0.8816(4) 0.6499(3) 0.5331(3) 0.0530(8) Uani 1 1 d U B . C14 C 0.7875(4) 0.5504(3) 0.4388(3) 0.0459(7) Uani 1 1 d U . . C15 C 0.6885(4) 0.4166(3) 0.4509(3) 0.0498(7) Uani 1 1 d U B . C16 C 0.5307(5) 0.3551(4) 0.3756(4) 0.0706(10) Uani 1 1 d U . . H16 H 0.4897 0.3976 0.3186 0.085 Uiso 1 1 calc R B . C17 C 0.4341(5) 0.2323(4) 0.3840(4) 0.0854(12) Uani 1 1 d U B . H17 H 0.3278 0.1925 0.3339 0.103 Uiso 1 1 calc R . . C18 C 0.4955(5) 0.1682(4) 0.4672(4) 0.0799(11) Uani 1 1 d U . . H18 H 0.4305 0.0852 0.4736 0.096 Uiso 1 1 calc R B . C19 C 0.6511(5) 0.2265(4) 0.5396(4) 0.0725(10) Uani 1 1 d U B . H19 H 0.6930 0.1825 0.5946 0.087 Uiso 1 1 calc R . . C20 C 0.7477(4) 0.3506(4) 0.5324(3) 0.0615(9) Uani 1 1 d U . . H20 H 0.8537 0.3898 0.5830 0.074 Uiso 1 1 calc R B . C21 C 0.8941(6) 0.6328(4) 0.6590(3) 0.0790(12) Uani 1 1 d U . . H21A H 0.9751 0.5981 0.6886 0.119 Uiso 1 1 calc R B . H21B H 0.7899 0.5752 0.6638 0.119 Uiso 1 1 calc R . . H21C H 0.9254 0.7144 0.7044 0.119 Uiso 1 1 calc R . . C22 C 1.0431(5) 0.9242(3) 0.3685(4) 0.0710(10) Uani 1 1 d U . . H22A H 0.9673 0.9632 0.3380 0.107 Uiso 1 1 calc R B . H22B H 1.0975 0.9170 0.3122 0.107 Uiso 1 1 calc R . . H22C H 1.1229 0.9761 0.4391 0.107 Uiso 1 1 calc R . . C23 C 0.4831(5) 0.6826(4) 0.2195(5) 0.0809(12) Uani 1 1 d U . . H23A H 0.4986 0.6189 0.1748 0.121 Uiso 1 1 calc R . . H23B H 0.3682 0.6649 0.2007 0.121 Uiso 1 1 calc R . . H23C H 0.5262 0.6811 0.3011 0.121 Uiso 1 1 calc R . . C24 C 0.6576(6) 1.1750(4) 0.1486(5) 0.0876(13) Uani 1 1 d U . . H24A H 0.7400 1.2194 0.1129 0.131 Uiso 1 1 calc R . . H24B H 0.6847 1.2197 0.2252 0.131 Uiso 1 1 calc R . . H24C H 0.5531 1.1714 0.1022 0.131 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 S1 0.0785(7) 0.0726(7) 0.1137(9) 0.0270(6) 0.0507(6) 0.0438(6) N1 0.0551(13) 0.0499(14) 0.0385(13) 0.0145(11) 0.0183(10) 0.0240(11) F1 0.1209(19) 0.166(2) 0.0757(16) 0.0316(16) 0.0376(14) 0.1096(18) F2 0.176(2) 0.0585(14) 0.0876(17) 0.0155(12) 0.0693(17) 0.0452(15) F3 0.113(6) 0.103(6) 0.050(5) 0.017(4) 0.050(4) 0.064(4) F4 0.1021(19) 0.135(2) 0.142(3) 0.066(2) 0.0731(18) 0.0511(17) F5 0.119(2) 0.156(2) 0.0578(15) 0.0022(15) 0.0045(14) 0.0718(19) F6 0.129(5) 0.086(4) 0.060(3) 0.043(3) 0.039(3) 0.059(3) F3' 0.146(5) 0.084(3) 0.055(2) 0.006(2) 0.036(3) 0.052(3) F6' 0.110(6) 0.077(4) 0.073(5) 0.039(4) 0.057(4) 0.034(4) C1 0.068(2) 0.061(2) 0.078(2) 0.0225(17) 0.0224(17) 0.0335(17) C2 0.0640(18) 0.0591(18) 0.068(2) 0.0269(16) 0.0272(15) 0.0324(15) C3 0.0590(17) 0.0562(17) 0.0549(17) 0.0211(14) 0.0223(14) 0.0309(14) C4 0.0591(18) 0.0601(18) 0.071(2) 0.0192(16) 0.0277(15) 0.0292(15) C5 0.0591(16) 0.0538(16) 0.0464(16) 0.0197(13) 0.0249(13) 0.0277(13) C6 0.088(2) 0.074(2) 0.0516(18) 0.0263(16) 0.0279(16) 0.0413(17) C7 0.089(2) 0.075(2) 0.056(2) 0.0203(17) 0.0402(17) 0.0410(19) C8 0.078(2) 0.0671(19) 0.0518(18) 0.0180(15) 0.0274(15) 0.0410(16) C9 0.0565(15) 0.0488(15) 0.0447(15) 0.0156(12) 0.0243(12) 0.0240(12) C10 0.0538(15) 0.0494(15) 0.0435(15) 0.0154(12) 0.0211(12) 0.0277(12) C11 0.0588(17) 0.0496(16) 0.0494(17) 0.0098(13) 0.0178(13) 0.0257(13) C12 0.071(2) 0.0584(19) 0.0445(18) 0.0000(15) 0.0097(15) 0.0285(16) C13 0.0628(18) 0.0621(18) 0.0392(16) 0.0103(14) 0.0160(14) 0.0295(15) C14 0.0495(15) 0.0560(16) 0.0425(16) 0.0163(13) 0.0191(12) 0.0276(13) C15 0.0553(16) 0.0607(17) 0.0447(16) 0.0201(14) 0.0239(13) 0.0280(14) C16 0.067(2) 0.069(2) 0.066(2) 0.0284(17) 0.0142(17) 0.0181(17) C17 0.071(2) 0.072(2) 0.090(3) 0.027(2) 0.010(2) 0.0111(19) C18 0.080(2) 0.066(2) 0.094(3) 0.033(2) 0.035(2) 0.0202(19) C19 0.073(2) 0.072(2) 0.084(2) 0.0379(19) 0.0307(19) 0.0332(18) C20 0.0580(18) 0.0667(19) 0.066(2) 0.0258(16) 0.0212(15) 0.0288(15) C21 0.110(3) 0.085(3) 0.039(2) 0.0098(18) 0.017(2) 0.038(2) C22 0.081(2) 0.0479(19) 0.072(2) 0.0075(17) 0.0148(19) 0.0176(18) C23 0.072(2) 0.069(2) 0.117(3) 0.030(2) 0.048(2) 0.0287(19) C24 0.096(3) 0.063(2) 0.119(4) 0.026(2) 0.034(3) 0.047(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 S1 C1 1.714(4) . ? S1 C4 1.726(4) . ? N1 C10 1.339(4) . ? N1 C14 1.346(4) . ? F1 C8 1.339(4) . ? F2 C8 1.356(4) . ? F3 C7 1.178(14) . ? F4 C7 1.353(5) . ? F5 C6 1.379(5) . ? F6 C6 1.286(8) . ? F3' C7 1.375(7) . ? F6' C6 1.449(12) . ? C1 C2 1.349(5) . ? C1 C24 1.512(5) . ? C2 C3 1.430(5) . ? C3 C4 1.360(5) . ? C3 C5 1.477(4) . ? C4 C23 1.496(5) . ? C5 C9 1.339(4) . ? C5 C6 1.497(5) . ? C6 C7 1.510(5) . ? C7 C8 1.515(5) . ? C8 C9 1.495(5) . ? C9 C10 1.486(4) . ? C10 C11 1.397(5) . ? C11 C12 1.390(5) . ? C11 C22 1.500(5) . ? C12 C13 1.374(5) . ? C13 C14 1.406(5) . ? C13 C21 1.514(5) . ? C14 C15 1.492(4) . ? C15 C20 1.374(5) . ? C15 C16 1.387(5) . ? C16 C17 1.374(5) . ? C17 C18 1.380(6) . ? C18 C19 1.358(6) . ? C19 C20 1.382(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C4 93.15(17) . . ? C10 N1 C14 119.2(3) . . ? C2 C1 C24 129.0(4) . . ? C2 C1 S1 110.4(3) . . ? C24 C1 S1 120.6(3) . . ? C1 C2 C3 113.6(3) . . ? C4 C3 C2 112.9(3) . . ? C4 C3 C5 123.2(3) . . ? C2 C3 C5 124.0(3) . . ? C3 C4 C23 130.1(3) . . ? C3 C4 S1 110.0(3) . . ? C23 C4 S1 119.8(3) . . ? C9 C5 C3 128.4(3) . . ? C9 C5 C6 109.8(3) . . ? C3 C5 C6 121.7(3) . . ? F6 C6 F5 94.9(8) . . ? F6 C6 F6' 25.7(5) . . ? F5 C6 F6' 120.5(9) . . ? F6 C6 C5 118.9(5) . . ? F5 C6 C5 110.4(3) . . ? F6' C6 C5 107.5(7) . . ? F6 C6 C7 118.2(6) . . ? F5 C6 C7 107.7(3) . . ? F6' C6 C7 103.9(7) . . ? C5 C6 C7 105.7(3) . . ? F3 C7 F4 80.8(14) . . ? F3 C7 F3' 30.8(10) . . ? F4 C7 F3' 111.6(6) . . ? F3 C7 C6 126.1(8) . . ? F4 C7 C6 107.6(3) . . ? F3' C7 C6 112.5(5) . . ? F3 C7 C8 124.1(9) . . ? F4 C7 C8 107.6(3) . . ? F3' C7 C8 112.7(4) . . ? C6 C7 C8 104.3(3) . . ? F1 C8 F2 105.5(3) . . ? F1 C8 C9 113.0(3) . . ? F2 C8 C9 113.1(3) . . ? F1 C8 C7 112.6(3) . . ? F2 C8 C7 108.1(3) . . ? C9 C8 C7 104.7(3) . . ? C5 C9 C10 129.2(3) . . ? C5 C9 C8 111.3(3) . . ? C10 C9 C8 119.5(3) . . ? N1 C10 C11 123.5(3) . . ? N1 C10 C9 114.1(3) . . ? C11 C10 C9 122.3(3) . . ? C12 C11 C10 115.7(3) . . ? C12 C11 C22 121.3(3) . . ? C10 C11 C22 123.0(3) . . ? C13 C12 C11 122.7(3) . . ? C12 C13 C14 117.1(3) . . ? C12 C13 C21 119.3(3) . . ? C14 C13 C21 123.6(3) . . ? N1 C14 C13 121.8(3) . . ? N1 C14 C15 114.1(3) . . ? C13 C14 C15 124.1(3) . . ? C20 C15 C16 118.5(3) . . ? C20 C15 C14 122.8(3) . . ? C16 C15 C14 118.7(3) . . ? C17 C16 C15 120.9(4) . . ? C16 C17 C18 119.7(4) . . ? C19 C18 C17 119.9(4) . . ? C18 C19 C20 120.5(4) . . ? C15 C20 C19 120.5(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.455 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 899298' ####################################################################### # # 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_exp_1274 #TrackingRef 'exp_1274.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H13 F6 N S' _chemical_formula_weight 377.34 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' S S 0.1246 0.1234 '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/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.9922(12) _cell_length_b 8.6729(5) _cell_length_c 16.3046(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.157(8) _cell_angle_gamma 90.00 _cell_volume 1691.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2008 _cell_measurement_theta_min 2.6563 _cell_measurement_theta_max 28.1581 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.252 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9514 _exptl_absorpt_correction_T_max 0.9704 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9695 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2986 _reflns_number_gt 1964 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.9672P] 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 2986 _refine_ls_number_parameters 285 _refine_ls_number_restraints 1292 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1474 _refine_ls_wR_factor_gt 0.1204 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 0.977 _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 S1 S 0.50453(7) 0.71258(9) 0.58565(5) 0.0664(3) Uani 1 1 d U A . N1 N 0.6757(2) 0.4491(3) 0.90167(14) 0.0646(7) Uani 1 1 d U . . F1 F 0.4644(7) 0.1384(5) 0.8820(4) 0.093(2) Uani 0.436(7) 1 d PU A 1 F2 F 0.6423(8) 0.1247(7) 0.8757(5) 0.092(2) Uani 0.436(7) 1 d PU A 1 F3 F 0.4700(7) -0.0564(6) 0.7649(4) 0.085(2) Uani 0.436(7) 1 d PU A 1 F4 F 0.6284(5) 0.0195(9) 0.7298(3) 0.104(2) Uani 0.488(8) 1 d PU A 1 F5 F 0.5069(9) 0.1531(6) 0.6173(3) 0.092(2) Uani 0.488(8) 1 d PU A 1 F6 F 0.4034(8) 0.1426(8) 0.6495(5) 0.085(2) Uani 0.488(8) 1 d PU A 1 F1' F 0.5492(6) 0.1411(4) 0.9094(2) 0.0829(15) Uani 0.564(7) 1 d PU A 2 F2' F 0.6873(4) 0.1440(6) 0.8325(4) 0.0933(17) Uani 0.564(7) 1 d PU A 2 F3' F 0.4124(4) 0.0344(7) 0.7978(3) 0.108(2) Uani 0.564(7) 1 d PU A 2 F4' F 0.5628(8) -0.0630(6) 0.7584(3) 0.101(2) Uani 0.512(8) 1 d PU A 2 F5' F 0.3622(6) 0.1603(9) 0.6855(5) 0.092(2) Uani 0.512(8) 1 d PU A 2 F6' F 0.5807(7) 0.1400(6) 0.6426(4) 0.0913(18) Uani 0.512(8) 1 d PU A 2 C1 C 0.7084(3) 0.5575(4) 0.95496(19) 0.0783(10) Uani 1 1 d U . . H1 H 0.7790 0.5491 0.9823 0.094 Uiso 1 1 calc R . . C2 C 0.6432(3) 0.6825(4) 0.9720(2) 0.0779(10) Uani 1 1 d U . . H2 H 0.6693 0.7573 1.0095 0.094 Uiso 1 1 calc R . . C3 C 0.5389(3) 0.6941(3) 0.93244(18) 0.0690(9) Uani 1 1 d U . . H3 H 0.4933 0.7771 0.9435 0.083 Uiso 1 1 calc R . . C4 C 0.5007(2) 0.5825(3) 0.87576(16) 0.0529(7) Uani 1 1 d U . . C5 C 0.5742(2) 0.4624(3) 0.86222(15) 0.0486(6) Uani 1 1 d U . . C6 C 0.5469(2) 0.3342(3) 0.80387(15) 0.0479(6) Uani 1 1 d U A . C7 C 0.5646(3) 0.1700(3) 0.83244(19) 0.0692(8) Uani 1 1 d U . . C8 C 0.5206(3) 0.0708(4) 0.7631(2) 0.0770(10) Uani 1 1 d U A . C9 C 0.4877(3) 0.1755(3) 0.69347(19) 0.0685(9) Uani 1 1 d U . . C10 C 0.5076(2) 0.3372(3) 0.72512(15) 0.0479(6) Uani 1 1 d U A . C11 C 0.4860(2) 0.4682(3) 0.66911(15) 0.0475(6) Uani 1 1 d U . . C12 C 0.5592(2) 0.5869(3) 0.65927(15) 0.0510(7) Uani 1 1 d U A . C13 C 0.3832(2) 0.6081(3) 0.56784(16) 0.0589(8) Uani 1 1 d U . . C14 C 0.3862(2) 0.4818(3) 0.61627(16) 0.0563(7) Uani 1 1 d U A . H14 H 0.3285 0.4100 0.6153 0.068 Uiso 1 1 calc R . . C15 C 0.2930(3) 0.6578(4) 0.5042(2) 0.0838(11) Uani 1 1 d U A . H15A H 0.3193 0.6463 0.4503 0.126 Uiso 1 1 calc R . . H15B H 0.2744 0.7639 0.5131 0.126 Uiso 1 1 calc R . . H15C H 0.2279 0.5950 0.5087 0.126 Uiso 1 1 calc R . . C16 C 0.6737(2) 0.6144(4) 0.69996(19) 0.0686(9) Uani 1 1 d U . . H16A H 0.6688 0.6863 0.7443 0.103 Uiso 1 1 calc R A . H16B H 0.7213 0.6557 0.6605 0.103 Uiso 1 1 calc R . . H16C H 0.7041 0.5187 0.7211 0.103 Uiso 1 1 calc R . . C17 C 0.3850(3) 0.5945(4) 0.8346(2) 0.0740(9) Uani 1 1 d U . . H17A H 0.3876 0.6498 0.7838 0.111 Uiso 1 1 calc R . . H17B H 0.3376 0.6483 0.8700 0.111 Uiso 1 1 calc R . . H17C H 0.3557 0.4929 0.8237 0.111 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 S1 0.0814(6) 0.0567(5) 0.0604(5) 0.0109(4) 0.0012(4) 0.0056(4) N1 0.0683(16) 0.0594(14) 0.0620(15) -0.0076(12) -0.0227(12) 0.0007(12) F1 0.139(5) 0.064(3) 0.080(4) 0.004(3) 0.035(4) -0.013(3) F2 0.127(6) 0.058(3) 0.083(5) 0.007(3) -0.054(4) 0.012(4) F3 0.130(5) 0.043(3) 0.079(3) 0.011(2) -0.011(4) -0.016(3) F4 0.113(4) 0.101(4) 0.097(3) -0.020(3) 0.000(3) 0.032(3) F5 0.159(6) 0.057(2) 0.061(3) -0.012(2) 0.006(4) -0.006(4) F6 0.108(6) 0.063(3) 0.076(4) -0.008(3) -0.039(4) -0.020(4) F1' 0.131(5) 0.059(2) 0.057(2) 0.0075(16) -0.003(3) 0.009(3) F2' 0.088(3) 0.070(3) 0.118(4) -0.005(3) -0.017(3) 0.035(2) F3' 0.114(4) 0.109(4) 0.098(3) 0.022(3) -0.013(3) -0.040(3) F4' 0.163(6) 0.046(3) 0.089(3) -0.015(2) -0.019(4) 0.025(4) F5' 0.093(4) 0.070(3) 0.107(5) 0.010(3) -0.032(3) -0.029(3) F6' 0.128(5) 0.068(3) 0.082(4) -0.021(2) 0.029(3) 0.008(3) C1 0.084(2) 0.075(2) 0.071(2) -0.0061(18) -0.0275(18) -0.0107(19) C2 0.109(3) 0.0610(19) 0.0614(19) -0.0120(16) -0.0125(19) -0.0148(19) C3 0.100(2) 0.0493(16) 0.0574(18) -0.0091(14) 0.0057(17) 0.0069(17) C4 0.0644(18) 0.0485(15) 0.0456(15) -0.0013(13) 0.0027(13) 0.0030(13) C5 0.0585(16) 0.0449(14) 0.0408(14) 0.0008(11) -0.0069(12) -0.0019(13) C6 0.0512(15) 0.0440(14) 0.0473(14) -0.0017(12) -0.0057(12) 0.0045(12) C7 0.100(2) 0.0534(17) 0.0524(17) -0.0022(14) -0.0079(18) 0.0141(17) C8 0.100(3) 0.0459(18) 0.081(2) -0.0039(16) -0.022(2) 0.0008(18) C9 0.099(2) 0.0524(16) 0.0518(17) -0.0047(14) -0.0093(17) -0.0124(17) C10 0.0521(15) 0.0429(14) 0.0473(15) -0.0046(12) -0.0054(12) -0.0020(12) C11 0.0549(16) 0.0447(14) 0.0415(14) -0.0023(11) -0.0069(12) -0.0002(12) C12 0.0592(17) 0.0498(15) 0.0432(14) -0.0001(12) -0.0010(12) 0.0049(13) C13 0.0630(18) 0.0672(18) 0.0454(15) -0.0014(14) -0.0041(13) 0.0160(15) C14 0.0608(18) 0.0594(16) 0.0465(15) -0.0033(13) -0.0106(13) 0.0002(14) C15 0.092(3) 0.094(2) 0.0620(19) 0.0068(18) -0.0195(18) 0.027(2) C16 0.0613(19) 0.0676(19) 0.076(2) 0.0054(16) -0.0036(16) -0.0123(16) C17 0.069(2) 0.074(2) 0.078(2) -0.0116(17) 0.0008(17) 0.0172(17) _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 S1 C12 1.716(3) . ? S1 C13 1.720(3) . ? N1 C1 1.321(4) . ? N1 C5 1.340(3) . ? F1 C7 1.521(7) . ? F2 C7 1.193(6) . ? F3 C8 1.260(6) . ? F4 C8 1.505(7) . ? F5 C9 1.294(6) . ? F6 C9 1.230(7) . ? F1' C7 1.306(5) . ? F2' C7 1.488(6) . ? F3' C8 1.487(6) . ? F4' C8 1.270(6) . ? F5' C9 1.507(9) . ? F6' C9 1.470(7) . ? C1 C2 1.378(5) . ? C2 C3 1.368(5) . ? C3 C4 1.393(4) . ? C4 C5 1.393(4) . ? C4 C17 1.500(4) . ? C5 C6 1.485(3) . ? C6 C10 1.336(3) . ? C6 C7 1.508(4) . ? C7 C8 1.488(4) . ? C8 C9 1.485(4) . ? C9 C10 1.507(4) . ? C10 C11 1.469(3) . ? C11 C12 1.371(4) . ? C11 C14 1.428(3) . ? C12 C16 1.499(4) . ? C13 C14 1.350(4) . ? C13 C15 1.506(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 S1 C13 93.41(14) . . ? C1 N1 C5 118.1(3) . . ? N1 C1 C2 123.2(3) . . ? C3 C2 C1 118.4(3) . . ? C2 C3 C4 120.5(3) . . ? C3 C4 C5 116.3(3) . . ? C3 C4 C17 119.9(3) . . ? C5 C4 C17 123.8(2) . . ? N1 C5 C4 123.5(2) . . ? N1 C5 C6 113.2(2) . . ? C4 C5 C6 123.3(2) . . ? C10 C6 C5 130.4(2) . . ? C10 C6 C7 110.3(2) . . ? C5 C6 C7 119.3(2) . . ? F2 C7 F1' 61.8(4) . . ? F2 C7 C8 118.5(4) . . ? F1' C7 C8 123.5(4) . . ? F2 C7 F2' 38.8(4) . . ? F1' C7 F2' 100.3(4) . . ? C8 C7 F2' 102.0(3) . . ? F2 C7 C6 125.5(4) . . ? F1' C7 C6 116.8(3) . . ? C8 C7 C6 106.1(2) . . ? F2' C7 C6 105.1(3) . . ? F2 C7 F1 103.9(5) . . ? F1' C7 F1 44.2(3) . . ? C8 C7 F1 92.8(4) . . ? F2' C7 F1 142.4(4) . . ? C6 C7 F1 103.6(3) . . ? F3 C8 F4' 52.9(5) . . ? F3 C8 C9 116.8(4) . . ? F4' C8 C9 126.8(4) . . ? F3 C8 F3' 51.0(4) . . ? F4' C8 F3' 101.0(6) . . ? C9 C8 F3' 103.3(3) . . ? F3 C8 C7 129.3(4) . . ? F4' C8 C7 116.9(4) . . ? C9 C8 C7 106.7(3) . . ? F3' C8 C7 96.0(4) . . ? F3 C8 F4 100.3(6) . . ? F4' C8 F4 49.6(4) . . ? C9 C8 F4 95.3(4) . . ? F3' C8 F4 150.6(5) . . ? C7 C8 F4 100.2(4) . . ? F6 C9 F5 66.6(7) . . ? F6 C9 F6' 104.4(7) . . ? F5 C9 F6' 39.8(3) . . ? F6 C9 C8 117.7(5) . . ? F5 C9 C8 125.8(4) . . ? F6' C9 C8 97.6(4) . . ? F6 C9 F5' 32.4(4) . . ? F5 C9 F5' 98.7(7) . . ? F6' C9 F5' 136.7(6) . . ? C8 C9 F5' 102.8(4) . . ? F6 C9 C10 121.2(4) . . ? F5 C9 C10 115.7(3) . . ? F6' C9 C10 106.3(3) . . ? C8 C9 C10 106.3(2) . . ? F5' C9 C10 104.1(4) . . ? C6 C10 C11 130.3(2) . . ? C6 C10 C9 110.3(2) . . ? C11 C10 C9 119.4(2) . . ? C12 C11 C14 112.6(2) . . ? C12 C11 C10 124.6(2) . . ? C14 C11 C10 122.8(2) . . ? C11 C12 C16 129.9(2) . . ? C11 C12 S1 110.06(19) . . ? C16 C12 S1 120.0(2) . . ? C14 C13 C15 128.5(3) . . ? C14 C13 S1 110.1(2) . . ? C15 C13 S1 121.4(2) . . ? C13 C14 C11 113.9(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.188 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 918115'