# Electronic Supplementary Material (ESI) for RSC Advances # 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_bq6metf _audit_creation_date 2010-08-12T17:21:24-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H23 N5 O2, 2(C F3 O3 S), 3(H2 O)' _chemical_formula_sum 'C29 H29 F6 N5 O11 S2' _chemical_formula_weight 801.71 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _space_group_IT_number 2 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9610(8) _cell_length_b 11.9210(10) _cell_length_c 16.3160(17) _cell_angle_alpha 83.883(8) _cell_angle_beta 81.522(8) _cell_angle_gamma 87.348(7) _cell_volume 1713.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 4291 _cell_measurement_theta_min 3.7277 _cell_measurement_theta_max 67.998 _cell_measurement_wavelength 1.5418 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description lamina _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3017 _exptl_crystal_size_mid 0.2454 _exptl_crystal_size_min 0.0206 _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -2 -1 0.139 0 2 1 0.0926 1 0 1 0.151 -1 0 -1 0.1093 0 0 -1 0.0097 0 0 1 0.0109 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.307 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.611 _exptl_absorpt_correction_T_max 0.955 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 10.4685 _diffrn_orient_matrix_ub_11 0.1005162 _diffrn_orient_matrix_ub_12 -0.1071623 _diffrn_orient_matrix_ub_13 -0.0114998 _diffrn_orient_matrix_ub_21 0.0756102 _diffrn_orient_matrix_ub_22 0.0545112 _diffrn_orient_matrix_ub_23 -0.0849244 _diffrn_orient_matrix_ub_31 0.1200881 _diffrn_orient_matrix_ub_32 0.0495243 _diffrn_orient_matrix_ub_33 0.0431597 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_unetI/netI 0.0411 _diffrn_reflns_number 11533 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 68.11 _diffrn_reflns_theta_full 68.11 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 6243 _reflns_number_gt 4626 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0354P)^2^+3.4252P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6243 _refine_ls_number_parameters 504 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.077 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1344 _refine_ls_wR_factor_gt 0.1223 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.469 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.064 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7769(3) 0.5411(3) 0.02278(19) 0.0238(7) Uani 1 1 d . . . C2 C 0.7722(4) 0.5808(3) 0.1003(2) 0.0281(7) Uani 1 1 d . . . H2 H 0.8355 0.6396 0.1076 0.034 Uiso 1 1 calc R . . C3 C 0.6737(4) 0.5327(3) 0.1662(2) 0.0319(8) Uani 1 1 d . . . H3 H 0.668 0.5583 0.2198 0.038 Uiso 1 1 calc R . . C4 C 0.5835(4) 0.4474(3) 0.1537(2) 0.0284(7) Uani 1 1 d . . . H4 H 0.5142 0.4135 0.1982 0.034 Uiso 1 1 calc R . . C5 C 0.5964(3) 0.4120(3) 0.07423(18) 0.0231(6) Uani 1 1 d . . . C6 C 0.5000(3) 0.3178(3) 0.06000(19) 0.0242(7) Uani 1 1 d . . . C7 C 0.4595(3) 0.1898(3) -0.04348(19) 0.0240(7) Uani 1 1 d . . . C8 C 0.5129(4) 0.1601(3) -0.1245(2) 0.0300(7) Uani 1 1 d . . . H8 H 0.5864 0.2054 -0.1591 0.036 Uiso 1 1 calc R . . C9 C 0.4626(4) 0.0684(3) -0.1548(2) 0.0291(7) Uani 1 1 d . . . H9 H 0.5015 0.0501 -0.2093 0.035 Uiso 1 1 calc R . . C10 C 0.3531(3) 0.0017(3) -0.10458(19) 0.0251(7) Uani 1 1 d . . . C11 C 0.2943(3) 0.0314(3) -0.0245(2) 0.0256(7) Uani 1 1 d . . . C12 C 0.3488(3) 0.1267(3) 0.00527(19) 0.0257(7) Uani 1 1 d . . . H12 H 0.3088 0.1472 0.0591 0.031 Uiso 1 1 calc R . . C13 C 0.1847(4) -0.0363(3) 0.0252(2) 0.0303(7) Uani 1 1 d . . . H13 H 0.1448 -0.0178 0.0795 0.036 Uiso 1 1 calc R . . C14 C 0.1351(4) -0.1292(3) -0.0045(2) 0.0305(7) Uani 1 1 d . . . H14 H 0.0604 -0.175 0.0287 0.037 Uiso 1 1 calc R . . C15 C 0.1955(4) -0.1554(3) -0.0837(2) 0.0312(8) Uani 1 1 d . . . H15 H 0.1608 -0.2195 -0.1043 0.037 Uiso 1 1 calc R . . C16 C 0.8773(4) 0.5967(3) -0.0507(2) 0.0266(7) Uani 1 1 d . . . C17 C 0.9514(3) 0.5974(3) -0.20106(19) 0.0242(7) Uani 1 1 d . . . C18 C 0.9640(4) 0.7157(3) -0.2204(2) 0.0291(7) Uani 1 1 d . . . H18 H 0.9221 0.7648 -0.1801 0.035 Uiso 1 1 calc R . . C19 C 1.0353(4) 0.7604(3) -0.2958(2) 0.0296(7) Uani 1 1 d . . . H19 H 1.0448 0.8398 -0.3073 0.035 Uiso 1 1 calc R . . C20 C 1.0944(4) 0.6886(3) -0.3564(2) 0.0278(7) Uani 1 1 d . . . C21 C 1.0773(4) 0.5710(3) -0.3394(2) 0.0272(7) Uani 1 1 d . . . C22 C 1.0068(4) 0.5272(3) -0.2601(2) 0.0276(7) Uani 1 1 d . . . H22 H 0.9977 0.4479 -0.2476 0.033 Uiso 1 1 calc R . . C23 C 1.1343(4) 0.5007(3) -0.4013(2) 0.0381(8) Uani 1 1 d . . . H23 H 1.1249 0.4212 -0.3905 0.046 Uiso 1 1 calc R . . C24 C 1.2030(4) 0.5458(3) -0.4769(2) 0.0399(9) Uani 1 1 d . . . H24 H 1.239 0.4987 -0.5195 0.048 Uiso 1 1 calc R . . C25 C 1.2195(4) 0.6616(3) -0.4907(2) 0.0362(8) Uani 1 1 d . . . H25 H 1.2696 0.693 -0.5429 0.043 Uiso 1 1 calc R . . C26 C 0.3605(4) -0.1270(3) -0.2146(2) 0.0338(8) Uani 1 1 d . . . H26A H 0.3114 -0.1953 -0.2239 0.051 Uiso 1 1 calc R . . H26B H 0.4696 -0.1419 -0.218 0.051 Uiso 1 1 calc R . . H26C H 0.3406 -0.0659 -0.2571 0.051 Uiso 1 1 calc R . . C27 C 1.1947(5) 0.8521(3) -0.4517(2) 0.0420(9) Uani 1 1 d . . . H27A H 1.2586 0.8662 -0.5056 0.063 Uiso 1 1 calc R . . H27B H 1.2453 0.8775 -0.408 0.063 Uiso 1 1 calc R . . H27C H 1.098 0.8935 -0.4533 0.063 Uiso 1 1 calc R . . C28" C 0.6786(5) 0.8411(4) 0.5880(4) 0.0641(13) Uani 1 1 d . . . C29" C -0.0554(5) 0.1388(3) 0.6732(2) 0.0385(9) Uani 1 1 d . . . N1 N 0.6912(3) 0.4574(2) 0.00937(15) 0.0230(6) Uani 1 1 d . . . N2 N 0.5257(3) 0.2824(2) -0.01761(16) 0.0255(6) Uani 1 1 d . . . N3 N 0.3004(3) -0.0936(2) -0.13159(16) 0.0264(6) Uani 1 1 d . . . N4 N 0.8773(3) 0.5522(2) -0.12313(16) 0.0248(6) Uani 1 1 d . . . N5 N 1.1679(3) 0.7298(2) -0.43372(16) 0.0305(6) Uani 1 1 d . . . O1 O 0.4073(3) 0.2773(2) 0.11655(13) 0.0322(5) Uani 1 1 d . . . O2 O 0.9529(3) 0.6769(2) -0.04226(14) 0.0356(6) Uani 1 1 d . . . O1W O 0.5937(5) 0.6937(3) 0.3421(2) 0.0723(11) Uani 1 1 d . . . O3" O 0.5640(4) 0.6931(3) 0.51347(18) 0.0770(11) Uani 1 1 d . . . O2W O 0.6641(4) 0.4005(3) 0.69012(18) 0.0467(7) Uani 1 1 d . . . O4" O 0.6899(4) 0.6308(2) 0.6313(2) 0.0683(9) Uani 1 1 d . . . O3W O 0.7604(3) 0.3476(2) 0.83866(15) 0.0333(6) Uani 1 1 d . . . O5" O 0.4484(3) 0.7270(3) 0.65027(17) 0.0546(8) Uani 1 1 d . . . O6" O 0.2155(3) 0.1197(2) 0.70878(17) 0.0449(6) Uani 1 1 d . . . O7" O 0.0226(3) 0.0075(2) 0.79494(15) 0.0429(6) Uani 1 1 d . . . O8" O 0.0237(3) 0.2099(2) 0.80328(16) 0.0475(7) Uani 1 1 d . . . F1" F 0.8102(4) 0.8387(3) 0.5404(2) 0.1063(12) Uani 1 1 d . . . F2" F 0.7053(3) 0.8684(2) 0.6612(2) 0.0815(9) Uani 1 1 d . . . F3" F 0.5947(5) 0.9244(3) 0.5563(3) 0.146(2) Uani 1 1 d . . . F4" F -0.0320(3) 0.05823(19) 0.62221(14) 0.0559(6) Uani 1 1 d . . . F5" F -0.2003(3) 0.1403(2) 0.70492(16) 0.0559(6) Uani 1 1 d . . . F6" F -0.0281(3) 0.23696(19) 0.62729(15) 0.0594(7) Uani 1 1 d . . . S1" S 0.58404(10) 0.70884(8) 0.59630(5) 0.0367(2) Uani 1 1 d . . . S2" S 0.06547(10) 0.11671(7) 0.75437(5) 0.0326(2) Uani 1 1 d . . . H4N H 0.836(4) 0.497(3) -0.124(2) 0.039 Uiso 1 1 d . . . H2N H 0.589(4) 0.312(3) -0.050(2) 0.039 Uiso 1 1 d . . . H3D H 0.829(5) 0.304(4) 0.829(3) 0.049 Uiso 1 1 d . . . H1E H 0.535(5) 0.736(4) 0.377(3) 0.049 Uiso 1 1 d . . . H3E H 0.733(5) 0.367(4) 0.793(3) 0.049 Uiso 1 1 d . . . H2D H 0.653(5) 0.462(4) 0.679(3) 0.049 Uiso 1 1 d . . . H1D H 0.658(5) 0.752(4) 0.320(3) 0.049 Uiso 1 1 d . . . H2E H 0.584(5) 0.380(4) 0.680(3) 0.049 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 C1 0.0219(15) 0.0259(17) 0.0241(16) -0.0029(13) -0.0061(12) 0.0039(13) C2 0.0289(17) 0.0296(18) 0.0285(17) -0.0074(14) -0.0097(14) 0.0000(14) C3 0.0380(19) 0.038(2) 0.0212(16) -0.0089(14) -0.0080(14) 0.0041(16) C4 0.0280(17) 0.0324(18) 0.0243(16) -0.0017(13) -0.0041(13) 0.0024(14) C5 0.0231(15) 0.0251(16) 0.0209(15) -0.0004(12) -0.0053(12) 0.0039(12) C6 0.0225(16) 0.0256(16) 0.0248(16) -0.0005(13) -0.0072(13) 0.0035(13) C7 0.0225(16) 0.0235(16) 0.0275(16) -0.0020(13) -0.0090(13) -0.0015(13) C8 0.0315(18) 0.0331(19) 0.0257(17) -0.0007(14) -0.0054(14) -0.0063(14) C9 0.0323(18) 0.0307(18) 0.0250(16) -0.0037(14) -0.0045(14) -0.0030(14) C10 0.0242(16) 0.0231(16) 0.0294(17) -0.0015(13) -0.0100(13) 0.0015(13) C11 0.0211(15) 0.0261(17) 0.0295(17) 0.0014(13) -0.0069(13) 0.0010(13) C12 0.0231(16) 0.0295(17) 0.0246(16) -0.0034(13) -0.0042(13) 0.0009(13) C13 0.0277(17) 0.0343(19) 0.0287(17) -0.0031(14) -0.0037(14) 0.0004(14) C14 0.0291(17) 0.0301(18) 0.0318(18) 0.0022(14) -0.0066(14) -0.0020(14) C15 0.0308(18) 0.0242(17) 0.040(2) -0.0016(15) -0.0126(15) -0.0006(14) C16 0.0252(17) 0.0285(17) 0.0274(17) -0.0058(13) -0.0066(13) 0.0020(14) C17 0.0212(15) 0.0287(17) 0.0238(16) -0.0028(13) -0.0057(12) -0.0029(13) C18 0.0338(18) 0.0293(18) 0.0257(17) -0.0068(14) -0.0074(14) 0.0035(14) C19 0.0352(18) 0.0254(17) 0.0300(17) -0.0027(14) -0.0109(14) -0.0003(14) C20 0.0287(17) 0.0286(18) 0.0275(17) -0.0009(13) -0.0099(14) -0.0017(14) C21 0.0255(16) 0.0321(18) 0.0260(16) -0.0066(14) -0.0070(13) -0.0023(14) C22 0.0290(17) 0.0262(17) 0.0286(17) -0.0037(13) -0.0056(14) -0.0050(14) C23 0.048(2) 0.0306(19) 0.0353(19) -0.0088(15) -0.0011(16) -0.0007(16) C24 0.051(2) 0.039(2) 0.0290(19) -0.0120(16) -0.0001(16) 0.0032(17) C25 0.040(2) 0.043(2) 0.0245(17) -0.0011(15) -0.0039(15) 0.0008(16) C26 0.041(2) 0.0325(19) 0.0291(18) -0.0059(15) -0.0060(15) 0.0014(16) C27 0.053(2) 0.036(2) 0.035(2) 0.0046(16) -0.0062(17) -0.0043(18) C28" 0.050(3) 0.055(3) 0.084(4) 0.019(3) -0.017(3) -0.007(2) C29" 0.052(2) 0.0303(19) 0.0343(19) -0.0035(15) -0.0117(17) 0.0039(17) N1 0.0214(13) 0.0262(14) 0.0228(13) -0.0045(11) -0.0079(10) 0.0033(11) N2 0.0261(14) 0.0285(15) 0.0219(14) -0.0010(11) -0.0039(11) -0.0007(12) N3 0.0271(14) 0.0239(14) 0.0287(14) -0.0002(11) -0.0079(11) 0.0012(11) N4 0.0275(15) 0.0242(14) 0.0236(13) -0.0054(11) -0.0040(11) -0.0033(11) N5 0.0331(15) 0.0325(16) 0.0265(14) -0.0005(12) -0.0079(12) -0.0008(12) O1 0.0334(13) 0.0374(13) 0.0246(12) -0.0030(10) 0.0001(10) -0.0022(10) O2 0.0388(14) 0.0396(14) 0.0308(13) -0.0081(11) -0.0054(10) -0.0144(11) O1W 0.100(3) 0.077(3) 0.0440(19) 0.0002(17) -0.0161(18) -0.043(2) O3" 0.071(2) 0.128(3) 0.0350(16) -0.0214(18) -0.0047(15) -0.018(2) O2W 0.0542(18) 0.0461(17) 0.0391(15) -0.0013(13) -0.0072(13) 0.0021(15) O4" 0.074(2) 0.0414(17) 0.096(3) -0.0074(17) -0.0393(19) 0.0109(15) O3W 0.0409(15) 0.0302(14) 0.0286(13) -0.0078(11) -0.0004(11) -0.0042(11) O5" 0.0462(16) 0.071(2) 0.0484(17) -0.0249(15) -0.0004(13) -0.0032(15) O6" 0.0352(14) 0.0478(16) 0.0497(16) -0.0012(13) -0.0025(12) -0.0008(12) O7" 0.0539(16) 0.0355(14) 0.0347(14) 0.0073(11) -0.0017(12) 0.0065(12) O8" 0.0558(17) 0.0463(16) 0.0458(16) -0.0204(13) -0.0172(13) 0.0099(13) F1" 0.068(2) 0.149(3) 0.094(2) 0.018(2) 0.0086(18) -0.048(2) F2" 0.0641(18) 0.0693(19) 0.120(3) -0.0362(18) -0.0192(18) -0.0174(15) F3" 0.117(3) 0.065(2) 0.257(6) 0.074(3) -0.092(3) -0.025(2) F4" 0.0809(17) 0.0498(14) 0.0433(13) -0.0212(11) -0.0218(12) 0.0104(12) F5" 0.0400(13) 0.0636(16) 0.0676(16) -0.0147(13) -0.0153(12) 0.0049(11) F6" 0.0802(18) 0.0418(14) 0.0575(15) 0.0147(11) -0.0289(13) -0.0007(12) S1" 0.0409(5) 0.0387(5) 0.0314(5) -0.0080(4) -0.0050(4) -0.0002(4) S2" 0.0375(5) 0.0317(5) 0.0289(4) -0.0040(3) -0.0071(4) 0.0052(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.342(4) . ? C1 C2 1.391(4) . ? C1 C16 1.501(4) . ? C2 C3 1.378(5) . ? C2 H2 0.95 . ? C3 C4 1.378(5) . ? C3 H3 0.95 . ? C4 C5 1.393(4) . ? C4 H4 0.95 . ? C5 N1 1.337(4) . ? C5 C6 1.506(4) . ? C6 O1 1.221(4) . ? C6 N2 1.361(4) . ? C7 C12 1.375(4) . ? C7 N2 1.409(4) . ? C7 C8 1.414(4) . ? C8 C9 1.366(5) . ? C8 H8 0.95 . ? C9 C10 1.401(5) . ? C9 H9 0.95 . ? C10 N3 1.388(4) . ? C10 C11 1.410(4) . ? C11 C13 1.405(5) . ? C11 C12 1.416(4) . ? C12 H12 0.95 . ? C13 C14 1.372(5) . ? C13 H13 0.95 . ? C14 C15 1.387(5) . ? C14 H14 0.95 . ? C15 N3 1.327(4) . ? C15 H15 0.95 . ? C16 O2 1.229(4) . ? C16 N4 1.346(4) . ? C17 C22 1.366(4) . ? C17 N4 1.409(4) . ? C17 C18 1.418(4) . ? C18 C19 1.367(5) . ? C18 H18 0.95 . ? C19 C20 1.405(4) . ? C19 H19 0.95 . ? C20 N5 1.386(4) . ? C20 C21 1.411(5) . ? C21 C23 1.405(5) . ? C21 C22 1.411(5) . ? C22 H22 0.95 . ? C23 C24 1.362(5) . ? C23 H23 0.95 . ? C24 C25 1.386(5) . ? C24 H24 0.95 . ? C25 N5 1.318(4) . ? C25 H25 0.95 . ? C26 N3 1.470(4) . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? C27 N5 1.479(4) . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? C28" F1" 1.314(6) . ? C28" F3" 1.325(5) . ? C28" F2" 1.328(6) . ? C28" S1" 1.807(5) . ? C29" F5" 1.325(4) . ? C29" F4" 1.326(4) . ? C29" F6" 1.333(4) . ? C29" S2" 1.822(4) . ? N2 H2N 0.79(4) . ? N4 H4N 0.77(4) . ? O1W H1E 0.90(4) . ? O1W H1D 0.93(4) . ? O3" S1" 1.422(3) . ? O2W H2D 0.75(4) . ? O2W H2E 0.81(4) . ? O4" S1" 1.434(3) . ? O3W H3D 0.80(4) . ? O3W H3E 0.82(4) . ? O5" S1" 1.414(3) . ? O6" S2" 1.438(3) . ? O7" S2" 1.439(3) . ? O8" S2" 1.440(3) . ? 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 N1 C1 C2 123.1(3) . . ? N1 C1 C16 117.7(3) . . ? C2 C1 C16 119.2(3) . . ? C3 C2 C1 118.5(3) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C4 C3 C2 119.5(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 118.3(3) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N1 C5 C4 123.3(3) . . ? N1 C5 C6 117.9(3) . . ? C4 C5 C6 118.8(3) . . ? O1 C6 N2 124.2(3) . . ? O1 C6 C5 120.1(3) . . ? N2 C6 C5 115.7(3) . . ? C12 C7 N2 124.1(3) . . ? C12 C7 C8 118.8(3) . . ? N2 C7 C8 117.1(3) . . ? C9 C8 C7 122.3(3) . . ? C9 C8 H8 118.8 . . ? C7 C8 H8 118.8 . . ? C8 C9 C10 119.3(3) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? N3 C10 C9 121.6(3) . . ? N3 C10 C11 118.7(3) . . ? C9 C10 C11 119.6(3) . . ? C13 C11 C10 119.0(3) . . ? C13 C11 C12 121.2(3) . . ? C10 C11 C12 119.8(3) . . ? C7 C12 C11 120.1(3) . . ? C7 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C11 120.2(3) . . ? C14 C13 H13 119.9 . . ? C11 C13 H13 119.9 . . ? C13 C14 C15 119.0(3) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? N3 C15 C14 122.1(3) . . ? N3 C15 H15 119 . . ? C14 C15 H15 119 . . ? O2 C16 N4 124.3(3) . . ? O2 C16 C1 120.1(3) . . ? N4 C16 C1 115.6(3) . . ? C22 C17 N4 119.9(3) . . ? C22 C17 C18 119.3(3) . . ? N4 C17 C18 120.7(3) . . ? C19 C18 C17 121.2(3) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 C20 119.8(3) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? N5 C20 C19 121.9(3) . . ? N5 C20 C21 118.3(3) . . ? C19 C20 C21 119.8(3) . . ? C23 C21 C20 119.0(3) . . ? C23 C21 C22 122.0(3) . . ? C20 C21 C22 119.1(3) . . ? C17 C22 C21 120.9(3) . . ? C17 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C24 C23 C21 120.4(3) . . ? C24 C23 H23 119.8 . . ? C21 C23 H23 119.8 . . ? C23 C24 C25 118.9(3) . . ? C23 C24 H24 120.6 . . ? C25 C24 H24 120.6 . . ? N5 C25 C24 122.2(3) . . ? N5 C25 H25 118.9 . . ? C24 C25 H25 118.9 . . ? N3 C26 H26A 109.5 . . ? N3 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N3 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N5 C27 H27A 109.5 . . ? N5 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N5 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? F1" C28" F3" 108.1(5) . . ? F1" C28" F2" 106.2(4) . . ? F3" C28" F2" 107.1(5) . . ? F1" C28" S1" 112.1(4) . . ? F3" C28" S1" 110.4(3) . . ? F2" C28" S1" 112.7(3) . . ? F5" C29" F4" 108.0(3) . . ? F5" C29" F6" 107.4(3) . . ? F4" C29" F6" 107.4(3) . . ? F5" C29" S2" 111.7(3) . . ? F4" C29" S2" 111.3(2) . . ? F6" C29" S2" 110.8(3) . . ? C5 N1 C1 117.4(3) . . ? C6 N2 C7 126.0(3) . . ? C6 N2 H2N 118(3) . . ? C7 N2 H2N 116(3) . . ? C15 N3 C10 121.0(3) . . ? C15 N3 C26 119.1(3) . . ? C10 N3 C26 119.9(3) . . ? C16 N4 C17 125.1(3) . . ? C16 N4 H4N 120(3) . . ? C17 N4 H4N 115(3) . . ? C25 N5 C20 121.3(3) . . ? C25 N5 C27 119.2(3) . . ? C20 N5 C27 119.5(3) . . ? H1E O1W H1D 95(4) . . ? H2D O2W H2E 99(5) . . ? H3D O3W H3E 105(4) . . ? O5" S1" O3" 114.48(19) . . ? O5" S1" O4" 114.5(2) . . ? O3" S1" O4" 114.6(2) . . ? O5" S1" C28" 103.8(2) . . ? O3" S1" C28" 105.3(2) . . ? O4" S1" C28" 102.2(2) . . ? O6" S2" O7" 114.53(16) . . ? O6" S2" O8" 114.99(17) . . ? O7" S2" O8" 115.32(17) . . ? O6" S2" C29" 103.64(17) . . ? O7" S2" C29" 102.56(17) . . ? O8" S2" C29" 103.41(16) . . ? 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 N1 C1 C2 C3 -0.8(5) . . . . ? C16 C1 C2 C3 176.7(3) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? C3 C4 C5 N1 -0.6(5) . . . . ? C3 C4 C5 C6 179.2(3) . . . . ? N1 C5 C6 O1 -176.8(3) . . . . ? C4 C5 C6 O1 3.4(4) . . . . ? N1 C5 C6 N2 4.0(4) . . . . ? C4 C5 C6 N2 -175.7(3) . . . . ? C12 C7 C8 C9 -2.6(5) . . . . ? N2 C7 C8 C9 176.7(3) . . . . ? C7 C8 C9 C10 0.7(5) . . . . ? C8 C9 C10 N3 -178.6(3) . . . . ? C8 C9 C10 C11 1.3(5) . . . . ? N3 C10 C11 C13 0.0(4) . . . . ? C9 C10 C11 C13 -179.9(3) . . . . ? N3 C10 C11 C12 178.5(3) . . . . ? C9 C10 C11 C12 -1.5(4) . . . . ? N2 C7 C12 C11 -176.8(3) . . . . ? C8 C7 C12 C11 2.4(4) . . . . ? C13 C11 C12 C7 178.0(3) . . . . ? C10 C11 C12 C7 -0.4(4) . . . . ? C10 C11 C13 C14 -0.6(5) . . . . ? C12 C11 C13 C14 -179.1(3) . . . . ? C11 C13 C14 C15 0.5(5) . . . . ? C13 C14 C15 N3 0.2(5) . . . . ? N1 C1 C16 O2 176.8(3) . . . . ? C2 C1 C16 O2 -0.8(4) . . . . ? N1 C1 C16 N4 -3.5(4) . . . . ? C2 C1 C16 N4 178.9(3) . . . . ? C22 C17 C18 C19 -2.4(5) . . . . ? N4 C17 C18 C19 -179.8(3) . . . . ? C17 C18 C19 C20 1.5(5) . . . . ? C18 C19 C20 N5 -179.8(3) . . . . ? C18 C19 C20 C21 1.1(5) . . . . ? N5 C20 C21 C23 -0.4(5) . . . . ? C19 C20 C21 C23 178.7(3) . . . . ? N5 C20 C21 C22 178.1(3) . . . . ? C19 C20 C21 C22 -2.8(5) . . . . ? N4 C17 C22 C21 178.1(3) . . . . ? C18 C17 C22 C21 0.6(5) . . . . ? C23 C21 C22 C17 -179.6(3) . . . . ? C20 C21 C22 C17 2.0(5) . . . . ? C20 C21 C23 C24 -0.9(5) . . . . ? C22 C21 C23 C24 -179.4(3) . . . . ? C21 C23 C24 C25 1.9(6) . . . . ? C23 C24 C25 N5 -1.5(6) . . . . ? C4 C5 N1 C1 0.0(4) . . . . ? C6 C5 N1 C1 -179.8(2) . . . . ? C2 C1 N1 C5 0.7(4) . . . . ? C16 C1 N1 C5 -176.8(3) . . . . ? O1 C6 N2 C7 -5.0(5) . . . . ? C5 C6 N2 C7 174.1(3) . . . . ? C12 C7 N2 C6 5.5(5) . . . . ? C8 C7 N2 C6 -173.7(3) . . . . ? C14 C15 N3 C10 -0.9(5) . . . . ? C14 C15 N3 C26 179.4(3) . . . . ? C9 C10 N3 C15 -179.4(3) . . . . ? C11 C10 N3 C15 0.7(4) . . . . ? C9 C10 N3 C26 0.4(4) . . . . ? C11 C10 N3 C26 -179.6(3) . . . . ? O2 C16 N4 C17 -6.7(5) . . . . ? C1 C16 N4 C17 173.6(3) . . . . ? C22 C17 N4 C16 148.8(3) . . . . ? C18 C17 N4 C16 -33.7(5) . . . . ? C24 C25 N5 C20 0.2(5) . . . . ? C24 C25 N5 C27 177.7(3) . . . . ? C19 C20 N5 C25 -178.3(3) . . . . ? C21 C20 N5 C25 0.8(5) . . . . ? C19 C20 N5 C27 4.2(5) . . . . ? C21 C20 N5 C27 -176.7(3) . . . . ? F1" C28" S1" O5" 178.9(3) . . . . ? F3" C28" S1" O5" -60.5(5) . . . . ? F2" C28" S1" O5" 59.2(4) . . . . ? F1" C28" S1" O3" -60.5(4) . . . . ? F3" C28" S1" O3" 60.1(5) . . . . ? F2" C28" S1" O3" 179.8(3) . . . . ? F1" C28" S1" O4" 59.6(4) . . . . ? F3" C28" S1" O4" -179.9(4) . . . . ? F2" C28" S1" O4" -60.2(4) . . . . ? F5" C29" S2" O6" -178.9(2) . . . . ? F4" C29" S2" O6" 60.3(3) . . . . ? F6" C29" S2" O6" -59.2(3) . . . . ? F5" C29" S2" O7" 61.6(3) . . . . ? F4" C29" S2" O7" -59.2(3) . . . . ? F6" C29" S2" O7" -178.6(3) . . . . ? F5" C29" S2" O8" -58.6(3) . . . . ? F4" C29" S2" O8" -179.4(3) . . . . ? F6" C29" S2" O8" 61.1(3) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 941790' ####################################################################### # # 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_bqsmetf _audit_creation_date 2013-05-28T18:45:09-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C29 H25 F6 N5 O9 S2' _chemical_formula_sum 'C29 H25 F6 N5 O9 S2' _chemical_formula_weight 765.66 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' _space_group_IT_number 14 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.2140(5) _cell_length_b 13.4000(3) _cell_length_c 14.3990(4) _cell_angle_alpha 90 _cell_angle_beta 103.862(3) _cell_angle_gamma 90 _cell_volume 3224.65(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5594 _cell_measurement_theta_min 3.6003 _cell_measurement_theta_max 67.9966 _cell_measurement_wavelength 1.5418 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5275 _exptl_crystal_size_mid 0.4003 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.14 0 0 1 0.1607 0 0 -1 0.1607 -1 0 0 0.14 0 -1 0 0.2646 1 2 0 0.1918 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.376 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.41 _exptl_absorpt_correction_T_max 0.6 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 10.4685 _diffrn_orient_matrix_ub_11 0.0888963 _diffrn_orient_matrix_ub_12 0.0027888 _diffrn_orient_matrix_ub_13 -0.0026001 _diffrn_orient_matrix_ub_21 0.024304 _diffrn_orient_matrix_ub_22 -0.0106582 _diffrn_orient_matrix_ub_23 0.1097335 _diffrn_orient_matrix_ub_31 -0.0001015 _diffrn_orient_matrix_ub_32 -0.1144249 _diffrn_orient_matrix_ub_33 -0.0103178 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_unetI/netI 0.023 _diffrn_reflns_number 11934 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.23 _diffrn_reflns_theta_max 68.11 _diffrn_reflns_theta_full 68.11 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 5876 _reflns_number_gt 4432 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0998P)^2^+1.6931P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5876 _refine_ls_number_parameters 468 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.172 _refine_ls_wR_factor_gt 0.1582 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.785 _refine_diff_density_min -0.58 _refine_diff_density_rms 0.064 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.09242(15) 0.38634(15) 0.14873(19) 0.0680(7) Uani 1 1 d . . . O2 O -0.12250(12) 0.83551(17) 0.07284(17) 0.0606(6) Uani 1 1 d . . . N1 N 0.01163(13) 0.63060(16) 0.11860(15) 0.0405(5) Uani 1 1 d . . . N2 N 0.15369(15) 0.53756(17) 0.18069(19) 0.0475(6) Uani 1 1 d D . . N3 N 0.43921(16) 0.5714(2) 0.2149(2) 0.0647(7) Uani 1 1 d . . . N4 N 0.01363(13) 0.83177(16) 0.11725(17) 0.0433(5) Uani 1 1 d D . . N5 N 0.20083(15) 1.09796(17) 0.11894(17) 0.0462(6) Uani 1 1 d . . . C1 C -0.05894(16) 0.6773(2) 0.09508(19) 0.0427(6) Uani 1 1 d . . . C2 C -0.13161(19) 0.6269(3) 0.0721(2) 0.0553(8) Uani 1 1 d . . . H2A H -0.1796 0.662 0.0567 0.066 Uiso 1 1 calc R . . C3 C -0.1313(2) 0.5247(3) 0.0726(2) 0.0605(9) Uani 1 1 d . . . H3 H -0.1791 0.4893 0.0567 0.073 Uiso 1 1 calc R . . C4 C -0.0594(2) 0.4751(2) 0.0970(2) 0.0550(8) Uani 1 1 d . . . H4A H -0.0578 0.4057 0.0979 0.066 Uiso 1 1 calc R . . C5 C 0.01112(18) 0.5305(2) 0.1202(2) 0.0442(6) Uani 1 1 d . . . C6 C 0.08950(19) 0.4774(2) 0.1509(2) 0.0476(7) Uani 1 1 d . . . C7 C 0.23216(18) 0.5032(2) 0.2202(2) 0.0450(6) Uani 1 1 d . . . C8 C 0.2468(2) 0.4256(2) 0.2837(2) 0.0590(8) Uani 1 1 d . . . H8 H 0.2043 0.3925 0.2997 0.071 Uiso 1 1 calc R . . C9 C 0.3254(3) 0.3962(3) 0.3246(3) 0.0722(10) Uani 1 1 d . . . H9 H 0.3342 0.3435 0.368 0.087 Uiso 1 1 calc R . . C10 C 0.3890(2) 0.4412(3) 0.3034(3) 0.0696(10) Uani 1 1 d . . . H10 H 0.4406 0.4194 0.3311 0.083 Uiso 1 1 calc R . . C11 C 0.37603(19) 0.5219(2) 0.2387(2) 0.0545(8) Uani 1 1 d . . . C12 C 0.29708(18) 0.5535(2) 0.1950(2) 0.0446(6) Uani 1 1 d . . . C13 C 0.28654(19) 0.6325(2) 0.1293(2) 0.0496(7) Uani 1 1 d . . . H13 H 0.2352 0.6531 0.0985 0.06 Uiso 1 1 calc R . . C14 C 0.3519(2) 0.6793(3) 0.1105(3) 0.0632(9) Uani 1 1 d . . . H14 H 0.3452 0.7326 0.0679 0.076 Uiso 1 1 calc R . . C15 C 0.4272(2) 0.6471(3) 0.1549(3) 0.0695(10) Uani 1 1 d . . . H15 H 0.4712 0.6797 0.1423 0.083 Uiso 1 1 calc R . . C16 C -0.05969(16) 0.7889(2) 0.09409(19) 0.0432(6) Uani 1 1 d . . . C17 C 0.02938(16) 0.93508(19) 0.12337(17) 0.0371(6) Uani 1 1 d . . . C18 C -0.02306(18) 1.0035(2) 0.1443(2) 0.0458(6) Uani 1 1 d . . . H18 H -0.0733 0.9832 0.1503 0.055 Uiso 1 1 calc R . . C19 C -0.00103(19) 1.1042(2) 0.1566(2) 0.0496(7) Uani 1 1 d . . . H19 H -0.038 1.1501 0.1687 0.06 Uiso 1 1 calc R . . C20 C 0.07223(19) 1.1370(2) 0.1515(2) 0.0477(7) Uani 1 1 d . . . H20 H 0.0867 1.2034 0.1638 0.057 Uiso 1 1 calc R . . C21 C 0.12611(16) 1.06827(19) 0.12715(18) 0.0394(6) Uani 1 1 d . . . C22 C 0.10381(15) 0.96742(18) 0.10747(17) 0.0359(5) Uani 1 1 d . . . C23 C 0.15401(17) 0.9056(2) 0.0682(2) 0.0430(6) Uani 1 1 d . . . H23 H 0.1392 0.84 0.0518 0.052 Uiso 1 1 calc R . . C24 C 0.22415(19) 0.9420(2) 0.0542(2) 0.0519(7) Uani 1 1 d . . . H24 H 0.2564 0.9024 0.0258 0.062 Uiso 1 1 calc R . . C25 C 0.24714(19) 1.0384(2) 0.0824(2) 0.0523(7) Uani 1 1 d . . . H25 H 0.2963 1.0618 0.0755 0.063 Uiso 1 1 calc R . . C26 C 0.5228(2) 0.5371(4) 0.2550(4) 0.0993(15) Uani 1 1 d . . . H26A H 0.5594 0.5836 0.2378 0.149 Uiso 1 1 calc R . . H26B H 0.5301 0.4725 0.2295 0.149 Uiso 1 1 calc R . . H26C H 0.5327 0.5331 0.3234 0.149 Uiso 1 1 calc R . . C27 C 0.2303(2) 1.1994(3) 0.1513(3) 0.0695(10) Uani 1 1 d . . . H27A H 0.2829 1.2086 0.1412 0.104 Uiso 1 1 calc R . . H27B H 0.2322 1.2066 0.2182 0.104 Uiso 1 1 calc R . . H27C H 0.1947 1.2485 0.1156 0.104 Uiso 1 1 calc R . . S1" S 0.21887(5) 0.75956(5) 0.33895(5) 0.0468(2) Uani 1 1 d . . . F1" F 0.24173(16) 0.94543(15) 0.29516(17) 0.0813(6) Uani 1 1 d . . . F2" F 0.32603(14) 0.84438(19) 0.26120(18) 0.0899(7) Uani 1 1 d . . . F3" F 0.33540(16) 0.8865(2) 0.40604(17) 0.0988(8) Uani 1 1 d . . . O3" O 0.18094(15) 0.79277(18) 0.41098(19) 0.0691(7) Uani 1 1 d . . . O4" O 0.27470(15) 0.67917(17) 0.36890(17) 0.0664(6) Uani 1 1 d . . . O5" O 0.16957(14) 0.74877(16) 0.24457(18) 0.0635(6) Uani 1 1 d . . . C28" C 0.2843(2) 0.8631(3) 0.3251(2) 0.0589(8) Uani 1 1 d . . . S2" S 0.44280(7) 0.26114(8) 0.05978(9) 0.0802(3) Uani 1 1 d . . . F4" F 0.4356(3) 0.4469(2) 0.0148(4) 0.1673(17) Uani 1 1 d . . . F5" F 0.3311(2) 0.3938(3) 0.0450(3) 0.1364(13) Uani 1 1 d . . . F6" F 0.3579(3) 0.3558(3) -0.0852(2) 0.1473(14) Uani 1 1 d . . . O6" O 0.4965(3) 0.2442(3) 0.0003(4) 0.1386(17) Uani 1 1 d . . . O7" O 0.3841(2) 0.1862(3) 0.0487(3) 0.1131(12) Uani 1 1 d . . . O8" O 0.4758(3) 0.2923(4) 0.1557(3) 0.1393(15) Uani 1 1 d . . . C29" C 0.3900(3) 0.3660(4) 0.0069(3) 0.0824(12) Uani 1 1 d . . . O1W O 0.4158(3) 0.5716(4) 0.5235(3) 0.1451(16) Uani 1 1 d . . . H1E H 0.4568 0.5999 0.5123 0.218 Uiso 1 1 d R . . H1D H 0.3802 0.5652 0.4715 0.218 Uiso 1 1 d R . . H2F H 0.142(4) 0.6051(19) 0.172(5) 0.174 Uiso 1 1 d D . . H4F H 0.058(3) 0.792(4) 0.130(5) 0.174 Uiso 1 1 d 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 O1 0.0808(16) 0.0308(11) 0.0935(18) -0.0076(11) 0.0232(14) -0.0063(10) O2 0.0418(11) 0.0578(13) 0.0762(15) 0.0051(11) 0.0025(10) 0.0035(10) N1 0.0471(13) 0.0368(11) 0.0394(11) -0.0008(9) 0.0141(10) -0.0089(10) N2 0.0526(14) 0.0304(11) 0.0623(15) -0.0021(10) 0.0194(12) 0.0003(10) N3 0.0495(15) 0.0731(19) 0.0700(18) -0.0141(16) 0.0114(13) -0.0042(14) N4 0.0406(12) 0.0332(11) 0.0547(13) 0.0046(10) 0.0088(10) -0.0002(9) N5 0.0517(14) 0.0347(12) 0.0519(14) 0.0029(10) 0.0119(11) -0.0050(10) C1 0.0440(15) 0.0446(15) 0.0399(14) 0.0034(11) 0.0107(11) -0.0081(12) C2 0.0462(16) 0.0625(19) 0.0564(18) 0.0050(15) 0.0107(14) -0.0132(14) C3 0.0556(19) 0.061(2) 0.063(2) 0.0011(16) 0.0107(15) -0.0279(16) C4 0.068(2) 0.0422(16) 0.0560(18) -0.0036(13) 0.0167(15) -0.0213(15) C5 0.0550(16) 0.0381(14) 0.0436(14) -0.0047(11) 0.0198(12) -0.0127(12) C6 0.0641(19) 0.0317(14) 0.0519(16) -0.0051(12) 0.0234(14) -0.0084(13) C7 0.0582(17) 0.0319(13) 0.0475(15) -0.0048(11) 0.0175(13) 0.0009(12) C8 0.076(2) 0.0417(16) 0.0616(19) 0.0037(14) 0.0212(17) -0.0020(15) C9 0.090(3) 0.0509(19) 0.068(2) 0.0142(17) 0.006(2) 0.0107(19) C10 0.066(2) 0.062(2) 0.072(2) 0.0046(18) 0.0004(18) 0.0102(18) C11 0.0577(18) 0.0510(17) 0.0533(17) -0.0109(14) 0.0103(14) 0.0047(15) C12 0.0546(16) 0.0388(14) 0.0423(14) -0.0075(11) 0.0150(12) 0.0028(12) C13 0.0573(17) 0.0445(16) 0.0495(16) -0.0009(13) 0.0174(13) 0.0007(13) C14 0.075(2) 0.058(2) 0.063(2) 0.0019(16) 0.0293(18) -0.0050(17) C15 0.065(2) 0.073(2) 0.077(2) -0.009(2) 0.0299(19) -0.0154(19) C16 0.0423(15) 0.0465(15) 0.0404(14) 0.0033(12) 0.0089(11) -0.0033(12) C17 0.0432(14) 0.0343(13) 0.0323(12) 0.0039(10) 0.0061(10) 0.0004(11) C18 0.0481(16) 0.0472(16) 0.0443(15) 0.0017(12) 0.0153(12) 0.0037(13) C19 0.0611(18) 0.0437(15) 0.0469(15) -0.0016(12) 0.0187(14) 0.0145(14) C20 0.0678(19) 0.0294(13) 0.0466(15) -0.0009(11) 0.0150(14) 0.0045(13) C21 0.0490(15) 0.0318(13) 0.0363(13) 0.0039(10) 0.0081(11) -0.0001(11) C22 0.0424(14) 0.0307(12) 0.0328(12) 0.0033(10) 0.0054(10) 0.0034(10) C23 0.0477(15) 0.0332(13) 0.0478(15) 0.0017(11) 0.0110(12) 0.0027(11) C24 0.0522(17) 0.0444(16) 0.0635(18) -0.0014(14) 0.0224(14) 0.0049(13) C25 0.0473(16) 0.0492(17) 0.0621(19) 0.0065(14) 0.0164(14) -0.0030(13) C26 0.052(2) 0.116(4) 0.123(4) -0.007(3) 0.007(2) 0.003(2) C27 0.070(2) 0.0440(18) 0.094(3) -0.0073(17) 0.0172(19) -0.0170(16) S1" 0.0594(4) 0.0333(3) 0.0476(4) -0.0042(3) 0.0129(3) 0.0020(3) F1" 0.1139(18) 0.0493(11) 0.0791(14) 0.0078(10) 0.0199(13) 0.0004(11) F2" 0.0861(16) 0.1052(19) 0.0901(16) -0.0049(14) 0.0440(13) -0.0147(14) F3" 0.1042(18) 0.1069(18) 0.0670(13) 0.0004(13) -0.0154(12) -0.0469(15) O3" 0.0764(16) 0.0570(14) 0.0829(17) -0.0057(12) 0.0366(13) 0.0027(12) O4" 0.0808(16) 0.0521(13) 0.0639(14) 0.0054(11) 0.0128(12) 0.0228(12) O5" 0.0603(13) 0.0464(12) 0.0743(15) -0.0035(10) -0.0029(11) -0.0036(10) C28" 0.066(2) 0.059(2) 0.0487(17) -0.0056(15) 0.0073(15) -0.0075(16) S2" 0.0781(7) 0.0760(7) 0.0931(8) -0.0066(5) 0.0332(6) -0.0142(5) F4" 0.162(3) 0.0730(19) 0.256(5) 0.013(2) 0.028(3) -0.033(2) F5" 0.108(2) 0.157(3) 0.143(3) -0.041(2) 0.028(2) 0.032(2) F6" 0.214(4) 0.120(3) 0.097(2) -0.0008(19) 0.018(2) 0.025(3) O6" 0.143(3) 0.111(3) 0.202(5) 0.024(3) 0.120(3) 0.031(3) O7" 0.131(3) 0.100(2) 0.117(3) -0.006(2) 0.047(2) -0.053(2) O8" 0.143(3) 0.144(3) 0.106(3) -0.026(3) -0.020(2) 0.004(3) C29" 0.074(3) 0.091(3) 0.083(3) -0.022(2) 0.020(2) -0.005(2) O1W 0.123(3) 0.182(4) 0.129(3) -0.028(3) 0.027(3) -0.033(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.223(3) . ? O2 C16 1.223(3) . ? N1 C1 1.336(4) . ? N1 C5 1.342(3) . ? N2 C6 1.352(4) . ? N2 C7 1.412(4) . ? N2 H2F 0.93(2) . ? N3 C15 1.316(5) . ? N3 C11 1.385(4) . ? N3 C26 1.488(5) . ? N4 C16 1.354(4) . ? N4 C17 1.409(3) . ? N4 H4F 0.91(2) . ? N5 C25 1.323(4) . ? N5 C21 1.378(4) . ? N5 C27 1.486(4) . ? C1 C2 1.390(4) . ? C1 C16 1.496(4) . ? C2 C3 1.370(5) . ? C2 H2A 0.93 . ? C3 C4 1.374(5) . ? C3 H3 0.93 . ? C4 C5 1.393(4) . ? C4 H4A 0.93 . ? C5 C6 1.495(4) . ? C7 C8 1.367(4) . ? C7 C12 1.425(4) . ? C8 C9 1.398(5) . ? C8 H8 0.93 . ? C9 C10 1.347(6) . ? C9 H9 0.93 . ? C10 C11 1.410(5) . ? C10 H10 0.93 . ? C11 C12 1.419(4) . ? C12 C13 1.402(4) . ? C13 C14 1.370(5) . ? C13 H13 0.93 . ? C14 C15 1.371(5) . ? C14 H14 0.93 . ? C15 H15 0.93 . ? C17 C18 1.370(4) . ? C17 C22 1.422(4) . ? C18 C19 1.401(4) . ? C18 H18 0.93 . ? C19 C20 1.354(4) . ? C19 H19 0.93 . ? C20 C21 1.409(4) . ? C20 H20 0.93 . ? C21 C22 1.415(4) . ? C22 C23 1.409(4) . ? C23 C24 1.361(4) . ? C23 H23 0.93 . ? C24 C25 1.383(4) . ? C24 H24 0.93 . ? C25 H25 0.93 . ? C26 H26A 0.96 . ? C26 H26B 0.96 . ? C26 H26C 0.96 . ? C27 H27A 0.96 . ? C27 H27B 0.96 . ? C27 H27C 0.96 . ? S1" O3" 1.423(2) . ? S1" O5" 1.427(2) . ? S1" O4" 1.439(2) . ? S1" C28" 1.828(4) . ? F1" C28" 1.338(4) . ? F2" C28" 1.319(4) . ? F3" C28" 1.319(4) . ? S2" O7" 1.406(3) . ? S2" O6" 1.421(4) . ? S2" O8" 1.424(4) . ? S2" C29" 1.746(5) . ? F4" C29" 1.327(5) . ? F5" C29" 1.318(5) . ? F6" C29" 1.316(5) . ? O1W H1E 0.8499 . ? O1W H1D 0.8501 . ? 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 N1 C5 117.6(2) . . ? C6 N2 C7 124.3(2) . . ? C6 N2 H2F 114(4) . . ? C7 N2 H2F 121(4) . . ? C15 N3 C11 121.5(3) . . ? C15 N3 C26 118.5(4) . . ? C11 N3 C26 120.0(4) . . ? C16 N4 C17 125.9(2) . . ? C16 N4 H4F 119(5) . . ? C17 N4 H4F 115(5) . . ? C25 N5 C21 121.6(2) . . ? C25 N5 C27 118.9(3) . . ? C21 N5 C27 119.5(3) . . ? N1 C1 C2 123.0(3) . . ? N1 C1 C16 118.4(2) . . ? C2 C1 C16 118.6(3) . . ? C3 C2 C1 118.8(3) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C2 C3 C4 119.1(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 118.9(3) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? N1 C5 C4 122.5(3) . . ? N1 C5 C6 118.1(2) . . ? C4 C5 C6 119.4(3) . . ? O1 C6 N2 124.6(3) . . ? O1 C6 C5 120.4(3) . . ? N2 C6 C5 115.0(2) . . ? C8 C7 N2 121.5(3) . . ? C8 C7 C12 120.0(3) . . ? N2 C7 C12 118.4(2) . . ? C7 C8 C9 120.1(3) . . ? C7 C8 H8 120 . . ? C9 C8 H8 120 . . ? C10 C9 C8 122.4(3) . . ? C10 C9 H9 118.8 . . ? C8 C9 H9 118.8 . . ? C9 C10 C11 119.0(3) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? N3 C11 C10 121.4(3) . . ? N3 C11 C12 118.2(3) . . ? C10 C11 C12 120.3(3) . . ? C13 C12 C11 118.7(3) . . ? C13 C12 C7 123.1(3) . . ? C11 C12 C7 118.2(3) . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13 120 . . ? C12 C13 H13 120 . . ? C13 C14 C15 119.5(3) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? N3 C15 C14 122.1(3) . . ? N3 C15 H15 118.9 . . ? C14 C15 H15 118.9 . . ? O2 C16 N4 124.1(3) . . ? O2 C16 C1 121.2(3) . . ? N4 C16 C1 114.6(2) . . ? C18 C17 N4 123.0(2) . . ? C18 C17 C22 119.9(2) . . ? N4 C17 C22 117.2(2) . . ? C17 C18 C19 120.0(3) . . ? C17 C18 H18 120 . . ? C19 C18 H18 120 . . ? C20 C19 C18 122.2(3) . . ? C20 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? C19 C20 C21 118.6(3) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? N5 C21 C20 121.1(2) . . ? N5 C21 C22 118.2(2) . . ? C20 C21 C22 120.7(3) . . ? C23 C22 C21 118.6(2) . . ? C23 C22 C17 123.3(2) . . ? C21 C22 C17 118.1(2) . . ? C24 C23 C22 120.0(3) . . ? C24 C23 H23 120 . . ? C22 C23 H23 120 . . ? C23 C24 C25 119.5(3) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? N5 C25 C24 121.5(3) . . ? N5 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? N3 C26 H26A 109.5 . . ? N3 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N3 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N5 C27 H27A 109.5 . . ? N5 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N5 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O3" S1" O5" 116.99(16) . . ? O3" S1" O4" 113.94(15) . . ? O5" S1" O4" 114.31(14) . . ? O3" S1" C28" 104.17(15) . . ? O5" S1" C28" 102.39(14) . . ? O4" S1" C28" 102.47(16) . . ? F3" C28" F2" 107.6(3) . . ? F3" C28" F1" 106.6(3) . . ? F2" C28" F1" 106.2(3) . . ? F3" C28" S1" 112.5(2) . . ? F2" C28" S1" 112.6(2) . . ? F1" C28" S1" 110.9(2) . . ? O7" S2" O6" 111.7(3) . . ? O7" S2" O8" 115.4(3) . . ? O6" S2" O8" 117.7(3) . . ? O7" S2" C29" 104.0(2) . . ? O6" S2" C29" 102.2(2) . . ? O8" S2" C29" 103.4(2) . . ? F6" C29" F5" 105.6(4) . . ? F6" C29" F4" 105.6(5) . . ? F5" C29" F4" 103.4(4) . . ? F6" C29" S2" 113.9(3) . . ? F5" C29" S2" 114.7(4) . . ? F4" C29" S2" 112.6(3) . . ? H1E O1W H1D 109.5 . . ? 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 N1 C1 C2 -0.3(4) . . . . ? C5 N1 C1 C16 179.3(2) . . . . ? N1 C1 C2 C3 -0.6(5) . . . . ? C16 C1 C2 C3 179.8(3) . . . . ? C1 C2 C3 C4 0.8(5) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C1 N1 C5 C4 1.1(4) . . . . ? C1 N1 C5 C6 -177.1(2) . . . . ? C3 C4 C5 N1 -0.8(4) . . . . ? C3 C4 C5 C6 177.3(3) . . . . ? C7 N2 C6 O1 -5.0(5) . . . . ? C7 N2 C6 C5 174.5(3) . . . . ? N1 C5 C6 O1 -176.2(3) . . . . ? C4 C5 C6 O1 5.6(4) . . . . ? N1 C5 C6 N2 4.3(4) . . . . ? C4 C5 C6 N2 -173.9(3) . . . . ? C6 N2 C7 C8 -41.2(4) . . . . ? C6 N2 C7 C12 141.0(3) . . . . ? N2 C7 C8 C9 -177.3(3) . . . . ? C12 C7 C8 C9 0.5(5) . . . . ? C7 C8 C9 C10 -0.4(6) . . . . ? C8 C9 C10 C11 0.9(6) . . . . ? C15 N3 C11 C10 -179.6(3) . . . . ? C26 N3 C11 C10 2.5(5) . . . . ? C15 N3 C11 C12 1.2(5) . . . . ? C26 N3 C11 C12 -176.6(3) . . . . ? C9 C10 C11 N3 179.5(3) . . . . ? C9 C10 C11 C12 -1.4(5) . . . . ? N3 C11 C12 C13 0.6(4) . . . . ? C10 C11 C12 C13 -178.5(3) . . . . ? N3 C11 C12 C7 -179.4(3) . . . . ? C10 C11 C12 C7 1.4(4) . . . . ? C8 C7 C12 C13 178.9(3) . . . . ? N2 C7 C12 C13 -3.2(4) . . . . ? C8 C7 C12 C11 -1.0(4) . . . . ? N2 C7 C12 C11 176.8(2) . . . . ? C11 C12 C13 C14 -1.8(4) . . . . ? C7 C12 C13 C14 178.2(3) . . . . ? C12 C13 C14 C15 1.2(5) . . . . ? C11 N3 C15 C14 -1.9(5) . . . . ? C26 N3 C15 C14 176.0(4) . . . . ? C13 C14 C15 N3 0.7(6) . . . . ? C17 N4 C16 O2 2.0(4) . . . . ? C17 N4 C16 C1 -178.7(2) . . . . ? N1 C1 C16 O2 179.8(3) . . . . ? C2 C1 C16 O2 -0.6(4) . . . . ? N1 C1 C16 N4 0.4(4) . . . . ? C2 C1 C16 N4 -180.0(3) . . . . ? C16 N4 C17 C18 27.0(4) . . . . ? C16 N4 C17 C22 -153.5(3) . . . . ? N4 C17 C18 C19 175.0(3) . . . . ? C22 C17 C18 C19 -4.5(4) . . . . ? C17 C18 C19 C20 -2.1(4) . . . . ? C18 C19 C20 C21 4.0(4) . . . . ? C25 N5 C21 C20 -169.7(3) . . . . ? C27 N5 C21 C20 10.0(4) . . . . ? C25 N5 C21 C22 8.4(4) . . . . ? C27 N5 C21 C22 -172.0(3) . . . . ? C19 C20 C21 N5 178.6(3) . . . . ? C19 C20 C21 C22 0.7(4) . . . . ? N5 C21 C22 C23 -8.5(4) . . . . ? C20 C21 C22 C23 169.5(3) . . . . ? N5 C21 C22 C17 175.1(2) . . . . ? C20 C21 C22 C17 -6.9(4) . . . . ? C18 C17 C22 C23 -167.5(3) . . . . ? N4 C17 C22 C23 13.0(4) . . . . ? C18 C17 C22 C21 8.8(4) . . . . ? N4 C17 C22 C21 -170.7(2) . . . . ? C21 C22 C23 C24 3.1(4) . . . . ? C17 C22 C23 C24 179.4(3) . . . . ? C22 C23 C24 C25 2.7(4) . . . . ? C21 N5 C25 C24 -2.6(4) . . . . ? C27 N5 C25 C24 177.7(3) . . . . ? C23 C24 C25 N5 -3.1(5) . . . . ? O3" S1" C28" F3" 57.1(3) . . . . ? O5" S1" C28" F3" 179.4(3) . . . . ? O4" S1" C28" F3" -61.9(3) . . . . ? O3" S1" C28" F2" 178.9(2) . . . . ? O5" S1" C28" F2" -58.8(3) . . . . ? O4" S1" C28" F2" 59.9(3) . . . . ? O3" S1" C28" F1" -62.2(3) . . . . ? O5" S1" C28" F1" 60.1(3) . . . . ? O4" S1" C28" F1" 178.8(2) . . . . ? O7" S2" C29" F6" -62.9(4) . . . . ? O6" S2" C29" F6" 53.5(5) . . . . ? O8" S2" C29" F6" 176.2(4) . . . . ? O7" S2" C29" F5" 58.9(4) . . . . ? O6" S2" C29" F5" 175.3(4) . . . . ? O8" S2" C29" F5" -62.0(4) . . . . ? O7" S2" C29" F4" 176.9(4) . . . . ? O6" S2" C29" F4" -66.8(5) . . . . ? O8" S2" C29" F4" 56.0(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4F N1 0.91(2) 2.30(7) 2.696(3) 106(5) . N4 H4F O5" 0.91(2) 2.29(5) 3.073(3) 144(6) . N2 H2F O5" 0.93(2) 2.18(5) 2.968(3) 142(6) . # END of CIF _database_code_depnum_ccdc_archive 'CCDC 941791' ####################################################################### # # 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_mq3metf _audit_creation_date 2010-04-12T14:20:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H15 F3 N2 O4 S1' _chemical_formula_sum 'C18 H15 F3 N2 O4 S' _chemical_formula_weight 412.38 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' _space_group_IT_number 14 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.4540(3) _cell_length_b 15.1350(5) _cell_length_c 14.5480(5) _cell_angle_alpha 90 _cell_angle_beta 104.356(3) _cell_angle_gamma 90 _cell_volume 1803.31(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6907 _cell_measurement_theta_min 4.2829 _cell_measurement_theta_max 67.9991 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -10 0 0.2158 1 -1 -9 0.3588 -1 -4 9 0.1923 -5 0 0 0.0138 5 0 0 0.0138 -1 0 9 0.2542 0 10 0 0.2158 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.141 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.867 _exptl_absorpt_correction_T_max 0.987 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 10.4685 _diffrn_orient_matrix_ub_11 0.1878379 _diffrn_orient_matrix_ub_12 0.0044231 _diffrn_orient_matrix_ub_13 0.0255798 _diffrn_orient_matrix_ub_21 -0.0079055 _diffrn_orient_matrix_ub_22 0.1009461 _diffrn_orient_matrix_ub_23 0.012056 _diffrn_orient_matrix_ub_31 0.0035567 _diffrn_orient_matrix_ub_32 -0.0125546 _diffrn_orient_matrix_ub_33 0.1055751 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_unetI/netI 0.014 _diffrn_reflns_number 11644 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.29 _diffrn_reflns_theta_max 68.11 _diffrn_reflns_theta_full 68.11 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3285 _reflns_number_gt 2783 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0897P)^2^+0.8096P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3285 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1501 _refine_ls_wR_factor_gt 0.1416 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.458 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.4686(3) 0.32041(17) 0.35635(18) 0.0537(6) Uani 1 1 d . . . H1 H -0.4462 0.3806 0.3609 0.064 Uiso 1 1 calc R . . C2 C -0.6246(3) 0.29229(19) 0.3142(2) 0.0604(7) Uani 1 1 d . . . H2 H -0.7063 0.3334 0.2905 0.072 Uiso 1 1 calc R . . C3 C -0.6596(3) 0.20364(19) 0.30718(19) 0.0582(6) Uani 1 1 d . . . H3 H -0.7651 0.1844 0.2796 0.07 Uiso 1 1 calc R . . C4 C -0.5374(3) 0.14367(19) 0.3412(2) 0.0654(7) Uani 1 1 d . . . H4 H -0.5606 0.0835 0.3359 0.078 Uiso 1 1 calc R . . C5 C -0.3804(3) 0.17136(16) 0.3833(2) 0.0552(6) Uani 1 1 d . . . H5 H -0.2986 0.13 0.4058 0.066 Uiso 1 1 calc R . . C6 C -0.3448(3) 0.26087(14) 0.39195(15) 0.0411(5) Uani 1 1 d . . . C7 C 0.1083(3) 0.25610(14) 0.49745(16) 0.0430(5) Uani 1 1 d . . . C8 C 0.2088(3) 0.18139(14) 0.52050(17) 0.0449(5) Uani 1 1 d . . . H8 H 0.1628 0.1257 0.5059 0.054 Uiso 1 1 calc R . . C9 C 0.4424(3) 0.26782(14) 0.58546(15) 0.0419(5) Uani 1 1 d . . . C10 C 0.6090(3) 0.27414(18) 0.62925(17) 0.0524(6) Uani 1 1 d . . . H10 H 0.6722 0.2234 0.6439 0.063 Uiso 1 1 calc R . . C11 C 0.6777(3) 0.3552(2) 0.6502(2) 0.0657(7) Uani 1 1 d . . . H11 H 0.7884 0.3596 0.6794 0.079 Uiso 1 1 calc R . . C12 C 0.5840(4) 0.4319(2) 0.6282(2) 0.0704(8) Uani 1 1 d . . . H12 H 0.6334 0.4868 0.6426 0.084 Uiso 1 1 calc R . . C13 C 0.4216(3) 0.42742(17) 0.5861(2) 0.0586(6) Uani 1 1 d . . . H13 H 0.3608 0.479 0.572 0.07 Uiso 1 1 calc R . . C14 C 0.3450(3) 0.34439(15) 0.56375(16) 0.0436(5) Uani 1 1 d . . . C15 C 0.1782(3) 0.33792(14) 0.52056(17) 0.0453(5) Uani 1 1 d . . . H15 H 0.1146 0.3887 0.5075 0.054 Uiso 1 1 calc R . . N1 N -0.0539(2) 0.23906(13) 0.45226(17) 0.0523(5) Uani 1 1 d . . . C17 C -0.1805(3) 0.29763(14) 0.43879(15) 0.0415(5) Uani 1 1 d . . . C18 C 0.4586(3) 0.10375(16) 0.5856(2) 0.0582(6) Uani 1 1 d . . . H18A H 0.4951 0.098 0.6532 0.087 Uiso 1 1 calc R . . H18B H 0.5513 0.1047 0.5586 0.087 Uiso 1 1 calc R . . H18C H 0.3898 0.0546 0.5602 0.087 Uiso 1 1 calc R . . C19" C -0.0639(3) 0.04814(17) 0.75537(19) 0.0540(6) Uani 1 1 d . . . N2 N 0.3654(2) 0.18700(12) 0.56193(13) 0.0429(4) Uani 1 1 d . . . O1" O -0.1273(3) 0.04763(19) 0.57365(16) 0.1004(9) Uani 1 1 d . . . O1 O -0.1614(2) 0.37456(11) 0.46254(14) 0.0569(5) Uani 1 1 d . . . O2" O 0.1561(3) 0.04762(17) 0.66261(17) 0.0879(7) Uani 1 1 d . . . O3" O -0.0048(3) -0.08133(13) 0.65650(15) 0.0740(6) Uani 1 1 d . . . S1" S -0.00521(7) 0.01310(4) 0.64904(4) 0.0507(2) Uani 1 1 d . . . F1" F 0.0377(3) 0.02119(16) 0.83243(13) 0.0958(7) Uani 1 1 d . . . F2" F -0.2112(2) 0.02414(18) 0.75546(17) 0.1057(8) Uani 1 1 d . . . F3" F -0.0628(3) 0.13587(13) 0.76125(17) 0.1049(7) Uani 1 1 d . . . H1N H -0.068(7) 0.187(4) 0.439(4) 0.157 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 C1 0.0457(12) 0.0452(13) 0.0665(16) -0.0031(11) 0.0072(11) 0.0056(10) C2 0.0435(12) 0.0636(16) 0.0697(16) 0.0023(13) 0.0056(11) 0.0100(12) C3 0.0397(12) 0.0717(17) 0.0593(15) 0.0026(13) 0.0052(10) -0.0080(12) C4 0.0547(15) 0.0485(14) 0.086(2) 0.0060(13) 0.0036(13) -0.0133(12) C5 0.0454(12) 0.0426(13) 0.0721(16) 0.0092(11) 0.0041(11) 0.0003(10) C6 0.0394(11) 0.0426(11) 0.0418(11) 0.0011(9) 0.0107(9) 0.0003(9) C7 0.0394(11) 0.0376(11) 0.0490(12) 0.0003(9) 0.0052(9) 0.0003(9) C8 0.0431(11) 0.0368(11) 0.0530(13) -0.0010(9) 0.0084(10) -0.0012(9) C9 0.0427(11) 0.0439(12) 0.0394(11) 0.0026(9) 0.0112(9) -0.0008(9) C10 0.0418(12) 0.0599(15) 0.0528(13) 0.0021(11) 0.0064(10) 0.0010(11) C11 0.0441(13) 0.0739(18) 0.0727(18) -0.0037(14) 0.0026(12) -0.0090(12) C12 0.0570(16) 0.0564(16) 0.090(2) -0.0102(14) 0.0037(14) -0.0170(13) C13 0.0534(14) 0.0419(13) 0.0753(17) -0.0028(12) 0.0060(12) -0.0046(11) C14 0.0425(11) 0.0424(12) 0.0445(11) 0.0004(9) 0.0080(9) -0.0017(9) C15 0.0432(11) 0.0368(11) 0.0533(13) 0.0010(9) 0.0068(10) 0.0024(9) N1 0.0381(10) 0.0355(10) 0.0757(14) -0.0046(9) -0.0004(9) 0.0011(8) C17 0.0414(11) 0.0388(11) 0.0443(11) 0.0007(9) 0.0106(9) 0.0003(9) C18 0.0489(13) 0.0441(13) 0.0780(18) 0.0055(12) 0.0092(12) 0.0130(11) C19" 0.0428(12) 0.0560(14) 0.0589(15) -0.0116(11) 0.0044(11) 0.0038(11) N2 0.0411(9) 0.0385(10) 0.0476(10) 0.0033(8) 0.0084(8) 0.0047(7) O1" 0.113(2) 0.115(2) 0.0606(13) 0.0019(13) -0.0040(13) 0.0407(16) O1 0.0451(9) 0.0405(9) 0.0826(12) -0.0106(8) 0.0111(8) 0.0007(7) O2" 0.0812(15) 0.1007(17) 0.0910(16) -0.0221(13) 0.0388(13) -0.0337(13) O3" 0.0942(15) 0.0491(11) 0.0798(14) -0.0146(9) 0.0239(12) -0.0012(10) S1" 0.0522(4) 0.0472(4) 0.0505(4) -0.0063(2) 0.0085(3) -0.0045(2) F1" 0.0904(14) 0.1347(19) 0.0553(10) -0.0090(10) 0.0048(9) 0.0403(12) F2" 0.0599(11) 0.156(2) 0.1096(16) -0.0437(14) 0.0362(11) -0.0258(12) F3" 0.143(2) 0.0633(11) 0.1123(16) -0.0280(11) 0.0392(14) 0.0133(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.376(3) . ? C1 C6 1.381(3) . ? C1 H1 0.93 . ? C2 C3 1.372(4) . ? C2 H2 0.93 . ? C3 C4 1.372(4) . ? C3 H3 0.93 . ? C4 C5 1.382(4) . ? C4 H4 0.93 . ? C5 C6 1.387(3) . ? C5 H5 0.93 . ? C6 C17 1.495(3) . ? C7 C15 1.377(3) . ? C7 N1 1.390(3) . ? C7 C8 1.404(3) . ? C8 N2 1.314(3) . ? C8 H8 0.93 . ? C9 N2 1.388(3) . ? C9 C10 1.398(3) . ? C9 C14 1.411(3) . ? C10 C11 1.359(4) . ? C10 H10 0.93 . ? C11 C12 1.398(4) . ? C11 H11 0.93 . ? C12 C13 1.359(4) . ? C12 H12 0.93 . ? C13 C14 1.414(3) . ? C13 H13 0.93 . ? C14 C15 1.398(3) . ? C15 H15 0.93 . ? N1 C17 1.366(3) . ? N1 H1N 0.82(6) . ? C17 O1 1.214(3) . ? C18 N2 1.481(3) . ? C18 H18A 0.96 . ? C18 H18B 0.96 . ? C18 H18C 0.96 . ? C19" F2" 1.297(3) . ? C19" F1" 1.298(3) . ? C19" F3" 1.330(3) . ? C19" S1" 1.817(3) . ? O1" S1" 1.407(2) . ? O2" S1" 1.428(2) . ? O3" S1" 1.433(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 C2 C1 C6 121.2(2) . . ? C2 C1 H1 119.4 . . ? C6 C1 H1 119.4 . . ? C3 C2 C1 120.0(2) . . ? C3 C2 H2 120 . . ? C1 C2 H2 120 . . ? C4 C3 C2 119.4(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 120.9(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120 . . ? C6 C5 H5 120 . . ? C1 C6 C5 118.5(2) . . ? C1 C6 C17 117.4(2) . . ? C5 C6 C17 124.1(2) . . ? C15 C7 N1 126.5(2) . . ? C15 C7 C8 117.9(2) . . ? N1 C7 C8 115.53(19) . . ? N2 C8 C7 122.6(2) . . ? N2 C8 H8 118.7 . . ? C7 C8 H8 118.7 . . ? N2 C9 C10 122.1(2) . . ? N2 C9 C14 117.17(19) . . ? C10 C9 C14 120.8(2) . . ? C11 C10 C9 119.4(2) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 120.8(2) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C13 C12 C11 120.9(3) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 120.1(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C9 120.7(2) . . ? C15 C14 C13 121.3(2) . . ? C9 C14 C13 118.0(2) . . ? C7 C15 C14 119.8(2) . . ? C7 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 N1 C7 126.41(19) . . ? C17 N1 H1N 122(4) . . ? C7 N1 H1N 111(4) . . ? O1 C17 N1 122.5(2) . . ? O1 C17 C6 122.0(2) . . ? N1 C17 C6 115.50(19) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? F2" C19" F1" 110.0(3) . . ? F2" C19" F3" 105.7(2) . . ? F1" C19" F3" 105.4(2) . . ? F2" C19" S1" 112.58(18) . . ? F1" C19" S1" 112.42(18) . . ? F3" C19" S1" 110.3(2) . . ? C8 N2 C9 121.84(18) . . ? C8 N2 C18 117.97(19) . . ? C9 N2 C18 120.17(19) . . ? O1" S1" O2" 117.57(19) . . ? O1" S1" O3" 114.63(16) . . ? O2" S1" O3" 111.74(15) . . ? O1" S1" C19" 104.63(14) . . ? O2" S1" C19" 103.22(12) . . ? O3" S1" C19" 102.86(12) . . ? 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 C6 C1 C2 C3 0.1(4) . . . . ? C1 C2 C3 C4 -0.9(4) . . . . ? C2 C3 C4 C5 0.7(4) . . . . ? C3 C4 C5 C6 0.3(5) . . . . ? C2 C1 C6 C5 0.8(4) . . . . ? C2 C1 C6 C17 -178.4(2) . . . . ? C4 C5 C6 C1 -1.0(4) . . . . ? C4 C5 C6 C17 178.1(2) . . . . ? C15 C7 C8 N2 -0.7(4) . . . . ? N1 C7 C8 N2 178.9(2) . . . . ? N2 C9 C10 C11 179.7(2) . . . . ? C14 C9 C10 C11 -0.6(4) . . . . ? C9 C10 C11 C12 -0.2(4) . . . . ? C10 C11 C12 C13 0.5(5) . . . . ? C11 C12 C13 C14 -0.1(5) . . . . ? N2 C9 C14 C15 0.1(3) . . . . ? C10 C9 C14 C15 -179.5(2) . . . . ? N2 C9 C14 C13 -179.2(2) . . . . ? C10 C9 C14 C13 1.1(3) . . . . ? C12 C13 C14 C15 179.9(3) . . . . ? C12 C13 C14 C9 -0.7(4) . . . . ? N1 C7 C15 C14 -178.2(2) . . . . ? C8 C7 C15 C14 1.4(3) . . . . ? C9 C14 C15 C7 -1.1(3) . . . . ? C13 C14 C15 C7 178.3(2) . . . . ? C15 C7 N1 C17 -13.6(4) . . . . ? C8 C7 N1 C17 166.9(2) . . . . ? C7 N1 C17 O1 3.3(4) . . . . ? C7 N1 C17 C6 -177.2(2) . . . . ? C1 C6 C17 O1 14.7(3) . . . . ? C5 C6 C17 O1 -164.4(2) . . . . ? C1 C6 C17 N1 -164.8(2) . . . . ? C5 C6 C17 N1 16.1(3) . . . . ? C7 C8 N2 C9 -0.2(3) . . . . ? C7 C8 N2 C18 178.2(2) . . . . ? C10 C9 N2 C8 -179.8(2) . . . . ? C14 C9 N2 C8 0.5(3) . . . . ? C10 C9 N2 C18 1.8(3) . . . . ? C14 C9 N2 C18 -177.9(2) . . . . ? F2" C19" S1" O1" 55.1(3) . . . . ? F1" C19" S1" O1" 180.0(2) . . . . ? F3" C19" S1" O1" -62.7(2) . . . . ? F2" C19" S1" O2" 178.7(2) . . . . ? F1" C19" S1" O2" -56.5(3) . . . . ? F3" C19" S1" O2" 60.8(2) . . . . ? F2" C19" S1" O3" -65.0(2) . . . . ? F1" C19" S1" O3" 59.9(2) . . . . ? F3" C19" S1" O3" 177.18(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3" 0.82(6) 2.30(6) 2.973(3) 141(5) 3_556 # END of CIF _database_code_depnum_ccdc_archive 'CCDC 941792' ####################################################################### # # 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_anaquinm _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 N2 O, I' _chemical_formula_sum 'C17 H15 I N2 O' _chemical_formula_weight 390.21 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' I I -0.4742 1.8119 '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 8.2858(12) _cell_length_b 8.3312(12) _cell_length_c 11.5680(17) _cell_angle_alpha 86.458(2) _cell_angle_beta 77.472(2) _cell_angle_gamma 81.506(2) _cell_volume 770.62(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3027 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 23.74 _exptl_crystal_description rhombohedral _exptl_crystal_colour orange _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 2.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.64 _exptl_absorpt_correction_T_max 0.73 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7487 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2709 _reflns_number_gt 2383 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _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^)+(0.0410P)^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 2709 _refine_ls_number_parameters 194 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0722 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 I1 I 0.36612(3) 0.32680(3) 0.162619(19) 0.05196(12) Uani 1 1 d . . . N1 N 1.1733(3) -0.1812(3) 0.1186(2) 0.0440(7) Uani 1 1 d . . . N2 N 0.6010(3) 0.1651(4) 0.3881(3) 0.0451(7) Uani 1 1 d D . . H2' H 0.517(3) 0.187(5) 0.354(3) 0.068 Uiso 1 1 d D . . O1 O 0.6847(3) 0.1761(4) 0.5600(2) 0.0773(9) Uani 1 1 d . . . C1 C 1.1604(5) -0.2692(4) 0.0312(3) 0.0501(9) Uani 1 1 d . . . H1 H 1.2558 -0.3305 -0.0105 0.060 Uiso 1 1 calc R . . C2 C 1.0095(5) -0.2737(5) -0.0006(3) 0.0525(9) Uani 1 1 d . . . H2 H 1.0044 -0.3355 -0.0637 0.063 Uiso 1 1 calc R . . C3 C 0.8682(5) -0.1863(4) 0.0615(3) 0.0485(9) Uani 1 1 d . . . H3 H 0.7661 -0.1885 0.0409 0.058 Uiso 1 1 calc R . . C4 C 0.8772(4) -0.0932(4) 0.1566(3) 0.0398(8) Uani 1 1 d . . . C5 C 0.7333(4) -0.0051(4) 0.2264(3) 0.0423(8) Uani 1 1 d . . . H5 H 0.6292 -0.0056 0.2086 0.051 Uiso 1 1 calc R . . C6 C 0.7474(4) 0.0809(4) 0.3200(3) 0.0404(8) Uani 1 1 d . . . C7 C 0.9055(4) 0.0865(4) 0.3444(3) 0.0487(9) Uani 1 1 d . . . H7 H 0.9144 0.1483 0.4064 0.058 Uiso 1 1 calc R . . C8 C 1.0461(4) 0.0027(4) 0.2787(3) 0.0468(8) Uani 1 1 d . . . H8 H 1.1498 0.0076 0.2960 0.056 Uiso 1 1 calc R . . C9 C 1.0337(4) -0.0900(4) 0.1859(3) 0.0390(7) Uani 1 1 d . . . C10 C 0.5769(5) 0.2090(4) 0.5024(3) 0.0486(9) Uani 1 1 d . . . C11 C 0.4082(4) 0.2971(4) 0.5550(3) 0.0430(8) Uani 1 1 d . . . C12 C 0.2633(5) 0.2735(5) 0.5218(3) 0.0518(9) Uani 1 1 d . . . H12 H 0.2684 0.2039 0.4609 0.062 Uiso 1 1 calc R . . C13 C 0.1108(5) 0.3526(5) 0.5785(4) 0.0580(10) Uani 1 1 d . . . H13 H 0.0134 0.3344 0.5568 0.070 Uiso 1 1 calc R . . C14 C 0.1029(5) 0.4584(5) 0.6673(4) 0.0633(12) Uani 1 1 d . . . H14 H 0.0006 0.5129 0.7050 0.076 Uiso 1 1 calc R . . C15 C 0.2470(5) 0.4827(5) 0.6997(4) 0.0618(11) Uani 1 1 d . . . H15 H 0.2412 0.5542 0.7596 0.074 Uiso 1 1 calc R . . C16 C 0.4007(5) 0.4032(5) 0.6454(3) 0.0514(9) Uani 1 1 d . . . H16 H 0.4973 0.4201 0.6687 0.062 Uiso 1 1 calc R . . C17 C 1.3387(4) -0.1794(5) 0.1473(4) 0.0620(11) Uani 1 1 d . . . H17A H 1.4207 -0.2535 0.0977 0.093 Uiso 1 1 calc R . . H17B H 1.3340 -0.2119 0.2289 0.093 Uiso 1 1 calc R . . H17C H 1.3687 -0.0718 0.1338 0.093 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 I1 0.04625(17) 0.0641(2) 0.04601(16) -0.00901(12) -0.01338(11) -0.00048(12) N1 0.0459(17) 0.0439(17) 0.0407(16) -0.0046(13) -0.0091(13) 0.0001(13) N2 0.0384(17) 0.0530(18) 0.0423(16) -0.0105(13) -0.0102(13) 0.0053(14) O1 0.0584(18) 0.121(3) 0.0476(16) -0.0213(16) -0.0222(14) 0.0272(17) C1 0.058(2) 0.045(2) 0.043(2) -0.0054(17) -0.0072(17) 0.0020(17) C2 0.058(2) 0.057(2) 0.044(2) -0.0131(18) -0.0143(18) -0.0036(19) C3 0.047(2) 0.056(2) 0.045(2) -0.0083(17) -0.0142(17) -0.0059(17) C4 0.049(2) 0.0359(19) 0.0349(18) -0.0015(14) -0.0103(15) -0.0054(15) C5 0.0398(19) 0.046(2) 0.0417(19) -0.0037(16) -0.0111(15) -0.0023(15) C6 0.0413(19) 0.038(2) 0.0403(18) -0.0029(15) -0.0085(15) 0.0008(15) C7 0.044(2) 0.052(2) 0.051(2) -0.0128(17) -0.0123(17) -0.0034(17) C8 0.0376(19) 0.054(2) 0.050(2) -0.0086(17) -0.0135(16) -0.0040(16) C9 0.0390(18) 0.0378(19) 0.0391(18) -0.0004(15) -0.0084(15) -0.0019(15) C10 0.052(2) 0.050(2) 0.0416(19) -0.0072(17) -0.0113(17) 0.0048(17) C11 0.048(2) 0.039(2) 0.0373(18) -0.0002(15) -0.0051(16) 0.0022(16) C12 0.056(2) 0.056(2) 0.041(2) -0.0016(17) -0.0111(17) 0.0017(18) C13 0.044(2) 0.066(3) 0.059(2) 0.008(2) -0.0072(18) 0.0015(19) C14 0.057(3) 0.056(3) 0.060(3) 0.004(2) 0.010(2) 0.010(2) C15 0.075(3) 0.047(2) 0.052(2) -0.0104(19) 0.007(2) 0.002(2) C16 0.059(2) 0.049(2) 0.043(2) -0.0059(17) -0.0035(17) -0.0066(18) C17 0.044(2) 0.076(3) 0.064(3) -0.017(2) -0.0122(19) 0.006(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 N1 C1 1.316(4) . ? N1 C9 1.394(4) . ? N1 C17 1.481(4) . ? N2 C10 1.359(4) . ? N2 C6 1.409(4) . ? O1 C10 1.217(4) . ? C1 C2 1.384(5) . ? C2 C3 1.366(5) . ? C3 C4 1.405(5) . ? C4 C9 1.415(5) . ? C4 C5 1.418(5) . ? C5 C6 1.369(5) . ? C6 C7 1.407(5) . ? C7 C8 1.365(5) . ? C8 C9 1.390(5) . ? C10 C11 1.499(5) . ? C11 C12 1.381(5) . ? C11 C16 1.396(5) . ? C12 C13 1.381(5) . ? C13 C14 1.380(6) . ? C14 C15 1.372(6) . ? C15 C16 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 N1 C9 121.4(3) . . ? C1 N1 C17 119.7(3) . . ? C9 N1 C17 118.9(3) . . ? C10 N2 C6 126.8(3) . . ? N1 C1 C2 122.2(3) . . ? C3 C2 C1 119.3(3) . . ? C2 C3 C4 119.9(3) . . ? C3 C4 C9 119.3(3) . . ? C3 C4 C5 122.1(3) . . ? C9 C4 C5 118.6(3) . . ? C6 C5 C4 120.1(3) . . ? C5 C6 C7 119.9(3) . . ? C5 C6 N2 118.3(3) . . ? C7 C6 N2 121.7(3) . . ? C8 C7 C6 121.2(3) . . ? C7 C8 C9 119.7(3) . . ? C8 C9 N1 121.7(3) . . ? C8 C9 C4 120.4(3) . . ? N1 C9 C4 117.9(3) . . ? O1 C10 N2 122.1(3) . . ? O1 C10 C11 121.6(3) . . ? N2 C10 C11 116.3(3) . . ? C12 C11 C16 119.7(3) . . ? C12 C11 C10 123.6(3) . . ? C16 C11 C10 116.7(3) . . ? C11 C12 C13 120.5(4) . . ? C12 C13 C14 120.0(4) . . ? C15 C14 C13 119.6(4) . . ? C14 C15 C16 121.5(4) . . ? C15 C16 C11 118.8(4) . . ? 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 C9 N1 C1 C2 1.5(5) . . . . ? C17 N1 C1 C2 -179.1(3) . . . . ? N1 C1 C2 C3 -1.1(6) . . . . ? C1 C2 C3 C4 0.1(6) . . . . ? C2 C3 C4 C9 0.6(5) . . . . ? C2 C3 C4 C5 -177.8(4) . . . . ? C3 C4 C5 C6 178.4(3) . . . . ? C9 C4 C5 C6 0.0(5) . . . . ? C4 C5 C6 C7 2.2(5) . . . . ? C4 C5 C6 N2 -179.2(3) . . . . ? C10 N2 C6 C5 155.9(4) . . . . ? C10 N2 C6 C7 -25.5(5) . . . . ? C5 C6 C7 C8 -2.3(5) . . . . ? N2 C6 C7 C8 179.2(3) . . . . ? C6 C7 C8 C9 0.0(6) . . . . ? C7 C8 C9 N1 -178.2(3) . . . . ? C7 C8 C9 C4 2.3(5) . . . . ? C1 N1 C9 C8 179.7(3) . . . . ? C17 N1 C9 C8 0.2(5) . . . . ? C1 N1 C9 C4 -0.8(5) . . . . ? C17 N1 C9 C4 179.8(3) . . . . ? C3 C4 C9 C8 179.3(3) . . . . ? C5 C4 C9 C8 -2.3(5) . . . . ? C3 C4 C9 N1 -0.3(5) . . . . ? C5 C4 C9 N1 178.1(3) . . . . ? C6 N2 C10 O1 -0.9(6) . . . . ? C6 N2 C10 C11 -179.5(3) . . . . ? O1 C10 C11 C12 -148.3(4) . . . . ? N2 C10 C11 C12 30.3(5) . . . . ? O1 C10 C11 C16 29.1(5) . . . . ? N2 C10 C11 C16 -152.2(3) . . . . ? C16 C11 C12 C13 -0.9(5) . . . . ? C10 C11 C12 C13 176.5(3) . . . . ? C11 C12 C13 C14 1.3(6) . . . . ? C12 C13 C14 C15 -0.8(6) . . . . ? C13 C14 C15 C16 -0.1(6) . . . . ? C14 C15 C16 C11 0.5(6) . . . . ? C12 C11 C16 C15 -0.1(5) . . . . ? C10 C11 C16 C15 -177.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.645 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 941793' ####################################################################### # # 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_jul4neum _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 N2 O, C F3 O3 S' _chemical_formula_sum 'C18 H15 F3 N2 O4 S' _chemical_formula_weight 412.38 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' 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 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 9.3966(18) _cell_length_b 15.386(3) _cell_length_c 12.114(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.451(3) _cell_angle_gamma 90.00 _cell_volume 1750.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4842 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 27.72 _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.245 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.93 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16621 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3082 _reflns_number_gt 2788 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _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^)+(0.0645P)^2^+1.1069P] 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 3082 _refine_ls_number_parameters 257 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1526 _refine_ls_wR_factor_gt 0.1479 _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_restrained_S_all 1.190 _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 N1 N 0.9093(3) 0.20809(17) 0.3118(2) 0.0433(6) Uani 1 1 d . . . N2 N 0.4454(3) 0.26840(15) 0.4565(2) 0.0396(6) Uani 1 1 d D . . H2' H 0.412(3) 0.2215(12) 0.427(3) 0.059 Uiso 1 1 d D . . C1 C 0.8877(4) 0.1237(2) 0.3248(3) 0.0533(8) Uani 1 1 d . . . H1 H 0.9569 0.0849 0.3020 0.064 Uiso 1 1 calc R . . C2 C 0.7669(3) 0.0918(2) 0.3705(3) 0.0514(8) Uani 1 1 d . . . H2 H 0.7548 0.0322 0.3789 0.062 Uiso 1 1 calc R . . C3 C 0.6644(3) 0.14776(19) 0.4038(2) 0.0427(7) Uani 1 1 d . . . H3 H 0.5834 0.1265 0.4372 0.051 Uiso 1 1 calc R . . C4 C 0.6805(3) 0.23732(17) 0.3881(2) 0.0342(6) Uani 1 1 d . . . C5 C 0.5759(3) 0.29980(18) 0.4176(2) 0.0358(6) Uani 1 1 d . . . C6 C 0.6035(3) 0.38622(19) 0.4067(3) 0.0448(7) Uani 1 1 d . . . H6 H 0.5365 0.4270 0.4280 0.054 Uiso 1 1 calc R . . C7 C 0.7322(3) 0.4137(2) 0.3636(3) 0.0490(8) Uani 1 1 d . . . H7 H 0.7496 0.4730 0.3576 0.059 Uiso 1 1 calc R . . C8 C 0.8327(3) 0.3571(2) 0.3300(3) 0.0453(7) Uani 1 1 d . . . H8 H 0.9163 0.3772 0.2994 0.054 Uiso 1 1 calc R . . C9 C 0.8082(3) 0.26806(19) 0.3421(2) 0.0378(7) Uani 1 1 d . . . C10 C 0.3598(3) 0.31124(18) 0.5281(2) 0.0372(6) Uani 1 1 d . . . C11 C 0.2232(3) 0.26692(18) 0.5541(2) 0.0371(6) Uani 1 1 d . . . C12 C 0.2050(3) 0.17818(19) 0.5522(3) 0.0477(8) Uani 1 1 d . . . H12 H 0.2800 0.1423 0.5329 0.057 Uiso 1 1 calc R . . C13 C 0.0757(4) 0.1423(2) 0.5789(3) 0.0549(9) Uani 1 1 d . . . H13 H 0.0638 0.0823 0.5770 0.066 Uiso 1 1 calc R . . C14 C -0.0352(4) 0.1945(2) 0.6081(3) 0.0522(8) Uani 1 1 d . . . H14 H -0.1219 0.1700 0.6265 0.063 Uiso 1 1 calc R . . C15 C -0.0183(4) 0.2824(2) 0.6101(3) 0.0577(9) Uani 1 1 d . . . H15 H -0.0939 0.3179 0.6292 0.069 Uiso 1 1 calc R . . C16 C 0.1110(3) 0.3191(2) 0.5840(3) 0.0494(8) Uani 1 1 d . . . H16 H 0.1223 0.3791 0.5866 0.059 Uiso 1 1 calc R . . C17 C 1.0460(3) 0.2373(2) 0.2671(3) 0.0604(9) Uani 1 1 d . . . H17A H 1.1013 0.1876 0.2468 0.091 Uiso 1 1 calc R . . H17B H 1.0974 0.2703 0.3222 0.091 Uiso 1 1 calc R . . H17C H 1.0281 0.2729 0.2032 0.091 Uiso 1 1 calc R . . S1 S 0.32142(9) 0.01671(5) 0.32986(6) 0.0448(3) Uani 1 1 d . . . F1 F 0.2495(3) -0.09227(13) 0.17543(19) 0.0784(7) Uani 1 1 d . . . F2 F 0.4004(3) 0.00198(15) 0.12599(18) 0.0801(7) Uani 1 1 d . . . F3 F 0.1834(3) 0.03787(16) 0.1438(2) 0.0861(8) Uani 1 1 d . . . C18 C 0.2870(4) -0.0093(2) 0.1859(3) 0.0515(8) Uani 1 1 d . . . O1 O 0.3917(2) 0.38065(13) 0.56909(18) 0.0512(6) Uani 1 1 d . . . O2 O 0.4348(3) -0.03998(19) 0.3601(2) 0.0809(8) Uani 1 1 d . . . O3 O 0.1884(3) -0.00002(16) 0.3784(2) 0.0760(8) Uani 1 1 d . . . O4 O 0.3565(3) 0.10737(15) 0.32602(19) 0.0622(7) Uani 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 N1 0.0381(13) 0.0481(15) 0.0438(14) -0.0028(11) 0.0025(11) 0.0008(11) N2 0.0390(13) 0.0331(13) 0.0468(14) -0.0049(11) 0.0054(11) -0.0029(10) C1 0.0511(19) 0.050(2) 0.059(2) -0.0016(16) 0.0057(16) 0.0144(16) C2 0.0525(19) 0.0349(16) 0.067(2) 0.0050(15) 0.0093(16) 0.0054(14) C3 0.0420(16) 0.0390(16) 0.0474(17) 0.0012(13) 0.0039(13) -0.0011(13) C4 0.0373(15) 0.0325(14) 0.0325(14) -0.0024(11) -0.0025(12) -0.0004(12) C5 0.0371(15) 0.0360(15) 0.0343(15) -0.0029(12) 0.0004(12) -0.0033(12) C6 0.0487(17) 0.0344(16) 0.0516(18) -0.0058(13) 0.0055(14) 0.0006(13) C7 0.0553(19) 0.0343(16) 0.058(2) -0.0015(14) 0.0045(16) -0.0110(14) C8 0.0438(17) 0.0433(17) 0.0489(18) -0.0028(14) 0.0059(14) -0.0114(14) C9 0.0370(15) 0.0426(16) 0.0337(15) -0.0031(12) -0.0016(12) 0.0007(12) C10 0.0413(15) 0.0358(15) 0.0344(15) -0.0026(12) -0.0007(12) 0.0037(12) C11 0.0422(16) 0.0374(15) 0.0317(14) -0.0022(12) 0.0003(12) 0.0019(12) C12 0.0493(18) 0.0375(16) 0.0570(19) 0.0008(14) 0.0127(15) 0.0054(14) C13 0.058(2) 0.0378(17) 0.070(2) 0.0014(16) 0.0133(17) -0.0044(15) C14 0.0490(18) 0.0532(19) 0.055(2) -0.0021(15) 0.0139(15) -0.0081(15) C15 0.050(2) 0.055(2) 0.069(2) -0.0141(17) 0.0186(17) 0.0058(16) C16 0.0509(19) 0.0374(17) 0.061(2) -0.0098(14) 0.0136(16) 0.0006(14) C17 0.0418(18) 0.069(2) 0.071(2) -0.0065(18) 0.0100(17) -0.0046(16) S1 0.0501(5) 0.0413(4) 0.0434(4) -0.0024(3) 0.0064(3) -0.0072(3) F1 0.1011(18) 0.0505(12) 0.0827(15) -0.0216(11) -0.0150(13) -0.0055(11) F2 0.0947(17) 0.0842(16) 0.0627(14) -0.0023(11) 0.0303(13) 0.0072(13) F3 0.0952(18) 0.0778(16) 0.0833(16) -0.0064(12) -0.0374(14) 0.0320(13) C18 0.056(2) 0.0433(18) 0.055(2) -0.0050(15) -0.0024(17) 0.0078(15) O1 0.0566(13) 0.0424(12) 0.0549(13) -0.0168(10) 0.0095(11) -0.0090(10) O2 0.088(2) 0.084(2) 0.0698(18) 0.0060(15) -0.0190(15) 0.0176(16) O3 0.0830(19) 0.0613(16) 0.0856(19) -0.0108(14) 0.0414(16) -0.0209(14) O4 0.0768(17) 0.0516(14) 0.0587(15) -0.0122(11) 0.0107(12) -0.0244(12) _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 N1 C1 1.324(4) . ? N1 C9 1.381(4) . ? N1 C17 1.476(4) . ? N2 C10 1.367(4) . ? N2 C5 1.411(4) . ? C1 C2 1.367(5) . ? C2 C3 1.361(4) . ? C3 C4 1.400(4) . ? C4 C9 1.417(4) . ? C4 C5 1.426(4) . ? C5 C6 1.362(4) . ? C6 C7 1.395(4) . ? C7 C8 1.354(4) . ? C8 C9 1.398(4) . ? C10 O1 1.212(3) . ? C10 C11 1.494(4) . ? C11 C12 1.376(4) . ? C11 C16 1.381(4) . ? C12 C13 1.380(4) . ? C13 C14 1.369(5) . ? C14 C15 1.362(5) . ? C15 C16 1.383(5) . ? S1 O2 1.418(3) . ? S1 O3 1.418(3) . ? S1 O4 1.434(2) . ? S1 C18 1.811(3) . ? F1 C18 1.329(4) . ? F2 C18 1.316(4) . ? F3 C18 1.308(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 C1 N1 C9 121.0(3) . . ? C1 N1 C17 118.6(3) . . ? C9 N1 C17 120.4(3) . . ? C10 N2 C5 125.3(2) . . ? N1 C1 C2 122.1(3) . . ? C3 C2 C1 119.6(3) . . ? C2 C3 C4 120.2(3) . . ? C3 C4 C9 118.5(3) . . ? C3 C4 C5 123.5(3) . . ? C9 C4 C5 118.0(2) . . ? C6 C5 N2 122.4(3) . . ? C6 C5 C4 120.0(3) . . ? N2 C5 C4 117.6(2) . . ? C5 C6 C7 120.1(3) . . ? C8 C7 C6 122.4(3) . . ? C7 C8 C9 118.7(3) . . ? N1 C9 C8 120.7(3) . . ? N1 C9 C4 118.5(3) . . ? C8 C9 C4 120.8(3) . . ? O1 C10 N2 122.8(3) . . ? O1 C10 C11 121.4(3) . . ? N2 C10 C11 115.8(2) . . ? C12 C11 C16 119.0(3) . . ? C12 C11 C10 123.8(3) . . ? C16 C11 C10 117.1(3) . . ? C11 C12 C13 120.2(3) . . ? C14 C13 C12 120.4(3) . . ? C15 C14 C13 119.9(3) . . ? C14 C15 C16 120.3(3) . . ? C11 C16 C15 120.2(3) . . ? O2 S1 O3 116.46(18) . . ? O2 S1 O4 115.77(17) . . ? O3 S1 O4 113.32(15) . . ? O2 S1 C18 103.14(16) . . ? O3 S1 C18 102.78(17) . . ? O4 S1 C18 102.69(15) . . ? F3 C18 F2 108.5(3) . . ? F3 C18 F1 107.7(3) . . ? F2 C18 F1 106.9(3) . . ? F3 C18 S1 111.4(2) . . ? F2 C18 S1 112.0(2) . . ? F1 C18 S1 110.2(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 C9 N1 C1 C2 -1.5(5) . . . . ? C17 N1 C1 C2 176.8(3) . . . . ? N1 C1 C2 C3 0.3(5) . . . . ? C1 C2 C3 C4 2.0(5) . . . . ? C2 C3 C4 C9 -3.1(4) . . . . ? C2 C3 C4 C5 178.0(3) . . . . ? C10 N2 C5 C6 -29.1(4) . . . . ? C10 N2 C5 C4 151.6(3) . . . . ? C3 C4 C5 C6 175.5(3) . . . . ? C9 C4 C5 C6 -3.4(4) . . . . ? C3 C4 C5 N2 -5.1(4) . . . . ? C9 C4 C5 N2 175.9(2) . . . . ? N2 C5 C6 C7 -177.4(3) . . . . ? C4 C5 C6 C7 1.9(4) . . . . ? C5 C6 C7 C8 0.8(5) . . . . ? C6 C7 C8 C9 -2.0(5) . . . . ? C1 N1 C9 C8 178.9(3) . . . . ? C17 N1 C9 C8 0.7(4) . . . . ? C1 N1 C9 C4 0.3(4) . . . . ? C17 N1 C9 C4 -177.9(3) . . . . ? C7 C8 C9 N1 -178.2(3) . . . . ? C7 C8 C9 C4 0.3(4) . . . . ? C3 C4 C9 N1 1.9(4) . . . . ? C5 C4 C9 N1 -179.1(2) . . . . ? C3 C4 C9 C8 -176.7(3) . . . . ? C5 C4 C9 C8 2.3(4) . . . . ? C5 N2 C10 O1 -2.9(5) . . . . ? C5 N2 C10 C11 177.5(2) . . . . ? O1 C10 C11 C12 -151.0(3) . . . . ? N2 C10 C11 C12 28.6(4) . . . . ? O1 C10 C11 C16 27.4(4) . . . . ? N2 C10 C11 C16 -153.0(3) . . . . ? C16 C11 C12 C13 0.7(5) . . . . ? C10 C11 C12 C13 179.1(3) . . . . ? C11 C12 C13 C14 -0.4(5) . . . . ? C12 C13 C14 C15 0.4(5) . . . . ? C13 C14 C15 C16 -0.7(5) . . . . ? C12 C11 C16 C15 -0.9(5) . . . . ? C10 C11 C16 C15 -179.4(3) . . . . ? C14 C15 C16 C11 0.9(5) . . . . ? O2 S1 C18 F3 -180.0(3) . . . . ? O3 S1 C18 F3 58.5(3) . . . . ? O4 S1 C18 F3 -59.3(3) . . . . ? O2 S1 C18 F2 -58.3(3) . . . . ? O3 S1 C18 F2 -179.7(2) . . . . ? O4 S1 C18 F2 62.4(3) . . . . ? O2 S1 C18 F1 60.6(3) . . . . ? O3 S1 C18 F1 -60.9(3) . . . . ? O4 S1 C18 F1 -178.7(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.406 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 941794'