# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_AZ12408627_AcOH _database_code_depnum_ccdc_archive 'CCDC 886319' #TrackingRef '11862_web_deposit_cif_file_0_AnneErtan_1339576411.AZ12408627AcOH.cif' #============================================================================== _audit_creation_method 'maXus and PLATON' _chemical_name_systematic ; (trans-4-{4-[({5-[(2,4,5-trifluorophenyl)amino]-1,3,4-oxadiazol-2-yl} carbonyl)amino]phenyl}cyclohexyl)acetic acid ; _chemical_name_common ;AZ12408627 acetic acid solvate, Analysis Report AZ SBBG: 2005-39-301, DGAT1 project ; _chemical_melting_point ? _chemical_formula_moiety 'C23 H21 F3 N4 O4, C2 H4 O2' _chemical_formula_structural ? _chemical_formula_sum 'C25 H25 F3 N4 O6' _chemical_formula_iupac ? _chemical_formula_weight 534.491 _chemical_compound_source 'Local laboratory at SBBG' _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_F_000 556 _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment mixed _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLUTON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.03646 _diffrn_orient_matrix_UB_12 -0.08959 _diffrn_orient_matrix_UB_13 0.01761 _diffrn_orient_matrix_UB_21 -0.18783 _diffrn_orient_matrix_UB_22 -0.00935 _diffrn_orient_matrix_UB_23 -0.00262 _diffrn_orient_matrix_UB_31 0.03370 _diffrn_orient_matrix_UB_32 -0.01062 _diffrn_orient_matrix_UB_33 -0.04477 _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _diffrn_radiation_type ' MoK\a' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 5.1885(5) _cell_length_b 11.4587(10) _cell_length_c 21.469(2) _cell_angle_alpha 75.373(5) _cell_angle_beta 86.058(5) _cell_angle_gamma 83.124(4) _cell_volume 1225.2(2) _diffrn_reflns_number 5552 _diffrn_reflns_theta_max 25.10 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_full 25.10 _cell_measurement_reflns_used 12354 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 25.108 _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.044 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' _exptl_absorpt_coefficient_mu 0.119 _reflns_number_total 3628 _reflns_number_gt 1988 _reflns_threshold_expression >2sigma(I) _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^)+(0.0718P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3628 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 0.922 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.269 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.051 #=============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS/PLATON 2003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags F32 F Uani -0.1067(6) 1.0270(3) 0.20129(13) 1.000 0.0707(11) . . F33 F Uani 0.4417(7) 1.1935(3) 0.02677(16) 1.000 0.1138(16) . . F34 F Uani 0.7530(7) 0.9834(3) 0.04842(14) 1.000 0.0992(14) . . O16 O Uani 0.4667(6) -0.4943(3) 0.77224(16) 1.000 0.0632(12) . . O17 O Uani 0.5727(7) -0.3995(3) 0.84348(17) 1.000 0.0756(16) . . O19 O Uani 0.2400(6) 0.4504(3) 0.41208(14) 1.000 0.0508(11) . . O24 O Uani 0.2762(5) 0.6489(3) 0.31394(13) 1.000 0.0439(11) . . N7 N Uani 0.6698(7) 0.4387(3) 0.43296(17) 1.000 0.0436(12) . . N21 N Uani 0.6950(7) 0.6464(3) 0.32579(18) 1.000 0.0499(16) . . N22 N Uani 0.6220(8) 0.7436(3) 0.27242(18) 1.000 0.0503(16) . . N25 N Uani 0.2007(7) 0.8118(4) 0.22887(18) 1.000 0.0531(16) . . C1 C Uani 0.9166(8) 0.2113(4) 0.5764(2) 1.000 0.0427(17) . . C2 C Uani 0.7585(8) 0.1180(4) 0.58383(19) 1.000 0.0411(17) . . C3 C Uani 0.5633(8) 0.1364(4) 0.5396(2) 1.000 0.0464(17) . . C4 C Uani 0.5294(8) 0.2409(4) 0.4910(2) 1.000 0.0452(17) . . C5 C Uani 0.6903(8) 0.3320(4) 0.48434(19) 1.000 0.0402(17) . . C6 C Uani 0.8845(8) 0.3155(4) 0.5274(2) 1.000 0.0429(17) . . C8 C Uani 0.8059(8) 0.0003(4) 0.6341(2) 1.000 0.0427(16) . . C9 C Uani 0.9226(8) -0.1010(4) 0.6029(2) 1.000 0.0490(17) . . C10 C Uani 0.9813(9) -0.2213(4) 0.6530(2) 1.000 0.0498(17) . . C11 C Uani 0.7437(8) -0.2600(4) 0.6959(2) 1.000 0.0454(17) . . C12 C Uani 0.6258(8) -0.1580(4) 0.7258(2) 1.000 0.0490(17) . . C13 C Uani 0.5665(8) -0.0395(4) 0.6761(2) 1.000 0.0479(17) . . C14 C Uani 0.8247(9) -0.3775(4) 0.7466(2) 1.000 0.0526(17) . . C15 C Uani 0.6063(9) -0.4282(4) 0.7893(3) 1.000 0.0527(17) . . C18 C Uani 0.4546(9) 0.4875(4) 0.4005(2) 1.000 0.0416(17) . . C20 C Uani 0.4898(9) 0.5957(4) 0.3472(2) 1.000 0.0415(17) . . C23 C Uani 0.3731(9) 0.7395(4) 0.2689(2) 1.000 0.0443(17) . . C26 C Uani 0.2648(9) 0.9077(5) 0.1769(2) 1.000 0.0495(19) . . C27 C Uani 0.4845(10) 0.8969(5) 0.1373(2) 1.000 0.060(2) . . C28 C Uani 0.5369(12) 0.9949(6) 0.0873(3) 1.000 0.070(2) . . C29 C Uani 0.3791(14) 1.1011(6) 0.0760(3) 1.000 0.077(3) . . C30 C Uani 0.1615(13) 1.1128(5) 0.1132(3) 1.000 0.072(3) . . C31 C Uani 0.1100(10) 1.0163(5) 0.1630(2) 1.000 0.055(2) . . O37 O Uani -0.1858(9) 0.4988(5) 0.0827(2) 1.000 0.1045(19) . . O38 O Uani -0.1178(7) 0.6147(4) 0.1469(2) 1.000 0.0864(17) . . C35 C Uani 0.1176(13) 0.6463(7) 0.0482(3) 1.000 0.114(3) . . C36 C Uani -0.0764(12) 0.5804(7) 0.0949(3) 1.000 0.081(3) . . H1 H Uiso 1.04834 0.20787 0.60629 1.000 0.0484 . . H3 H Uiso 0.45914 0.07103 0.54322 1.000 0.0523 . . H4 H Uiso 0.39779 0.25091 0.46019 1.000 0.0505 . . H6 H Uiso 0.99749 0.37755 0.52414 1.000 0.0478 . . H7 H Uiso 0.802(10) 0.474(4) 0.422(2) 1.000 0.0480 . . H8 H Uiso 0.93877 0.00218 0.66271 1.000 0.0482 . . H9A H Uiso 1.08838 -0.08627 0.58144 1.000 0.0528 . . H9B H Uiso 0.79390 -0.11355 0.57588 1.000 0.0528 . . H10A H Uiso 1.13346 -0.21741 0.67510 1.000 0.0549 . . H10B H Uiso 1.05242 -0.28243 0.63037 1.000 0.0549 . . H11 H Uiso 0.61175 -0.27957 0.67219 1.000 0.0508 . . H12A H Uiso 0.74513 -0.14498 0.75507 1.000 0.0533 . . H12B H Uiso 0.46633 -0.17968 0.74887 1.000 0.0533 . . H13A H Uiso 0.45217 -0.04909 0.64478 1.000 0.0524 . . H13B H Uiso 0.46517 0.02249 0.69265 1.000 0.0524 . . H14A H Uiso 0.87711 -0.43578 0.72174 1.000 0.0578 . . H14B H Uiso 0.96420 -0.35888 0.76573 1.000 0.0578 . . H17 H Uiso 0.439(9) -0.430(4) 0.865(2) 1.000 0.0811 . . H25 H Uiso 0.048(10) 0.816(5) 0.242(3) 1.000 0.0560 . . H27 H Uiso 0.58406 0.82971 0.14472 1.000 0.0652 . . H30 H Uiso 0.05103 1.18796 0.10361 1.000 0.0746 . . H35A H Uiso 0.18156 0.70647 0.06533 1.000 0.1065 . . H35B H Uiso 0.25976 0.58918 0.04053 1.000 0.1065 . . H35C H Uiso 0.03536 0.68488 0.00843 1.000 0.1065 . . H38 H Uiso -0.210(12) 0.589(5) 0.179(3) 1.000 0.0890 . . 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 F32 0.068(2) 0.071(2) 0.0670(18) -0.0093(15) -0.0025(16) 0.0002(15) F33 0.129(3) 0.116(3) 0.075(2) 0.032(2) -0.001(2) -0.050(2) F34 0.078(2) 0.153(3) 0.0617(19) -0.010(2) 0.0163(18) -0.039(2) O16 0.054(2) 0.071(2) 0.069(2) -0.0224(19) 0.0091(18) -0.0191(19) O17 0.083(3) 0.085(3) 0.063(2) -0.022(2) 0.018(2) -0.029(2) O19 0.0310(19) 0.056(2) 0.062(2) -0.0079(16) 0.0069(15) -0.0103(16) O24 0.0278(18) 0.052(2) 0.0485(18) -0.0054(16) 0.0036(15) -0.0086(16) N7 0.031(2) 0.045(2) 0.055(2) -0.011(2) 0.0047(19) -0.0108(18) N21 0.036(2) 0.055(3) 0.055(3) -0.007(2) 0.007(2) -0.009(2) N22 0.040(3) 0.051(3) 0.056(2) -0.004(2) 0.0001(19) -0.0105(19) N25 0.038(2) 0.062(3) 0.054(3) -0.003(2) 0.004(2) -0.012(2) C1 0.033(3) 0.049(3) 0.050(3) -0.019(3) 0.002(2) -0.007(2) C2 0.034(3) 0.044(3) 0.046(3) -0.015(2) 0.009(2) -0.005(2) C3 0.040(3) 0.043(3) 0.059(3) -0.015(3) 0.003(2) -0.013(2) C4 0.041(3) 0.042(3) 0.053(3) -0.011(3) 0.000(2) -0.009(2) C5 0.032(3) 0.045(3) 0.043(3) -0.012(2) 0.008(2) -0.005(2) C6 0.033(3) 0.046(3) 0.051(3) -0.012(3) 0.008(2) -0.015(2) C8 0.028(2) 0.049(3) 0.053(3) -0.014(2) -0.003(2) -0.008(2) C9 0.039(3) 0.051(3) 0.056(3) -0.013(3) 0.011(2) -0.009(2) C10 0.039(3) 0.049(3) 0.060(3) -0.015(3) 0.011(2) -0.003(2) C11 0.041(3) 0.044(3) 0.052(3) -0.011(2) 0.004(2) -0.013(2) C12 0.041(3) 0.053(3) 0.052(3) -0.012(3) 0.008(2) -0.009(2) C13 0.042(3) 0.047(3) 0.052(3) -0.013(2) 0.017(2) -0.003(2) C14 0.046(3) 0.049(3) 0.062(3) -0.010(3) 0.002(3) -0.012(2) C15 0.049(3) 0.050(3) 0.057(3) -0.012(3) 0.002(3) -0.002(3) C18 0.029(3) 0.048(3) 0.048(3) -0.014(2) 0.005(2) -0.004(2) C20 0.025(3) 0.049(3) 0.050(3) -0.013(3) 0.003(2) -0.003(2) C23 0.038(3) 0.047(3) 0.047(3) -0.011(3) 0.004(3) -0.005(3) C26 0.044(3) 0.062(4) 0.042(3) -0.006(3) 0.002(3) -0.020(3) C27 0.056(4) 0.073(4) 0.053(3) -0.012(3) -0.001(3) -0.018(3) C28 0.063(4) 0.098(5) 0.047(3) -0.006(4) 0.009(3) -0.035(4) C29 0.088(5) 0.085(5) 0.050(4) 0.014(4) -0.005(4) -0.039(4) C30 0.089(5) 0.064(4) 0.057(4) 0.005(3) -0.016(3) -0.015(3) C31 0.056(4) 0.065(4) 0.046(3) -0.014(3) 0.000(3) -0.011(3) O37 0.084(3) 0.143(4) 0.087(3) -0.024(3) 0.023(2) -0.038(3) O38 0.074(3) 0.088(3) 0.084(3) -0.001(2) 0.026(2) -0.016(2) C35 0.082(5) 0.134(6) 0.091(4) 0.029(4) 0.027(4) -0.015(4) C36 0.061(4) 0.102(5) 0.059(4) 0.011(4) 0.008(3) 0.000(4) #=============================================================================== # MOLECULAR GEOMETRY/PLATON 2003 _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F32 C31 1.359(6) . . yes F33 C29 1.347(7) . . yes F34 C28 1.365(7) . . yes O16 C15 1.241(6) . . yes O17 C15 1.282(7) . . yes O19 C18 1.226(6) . . yes O24 C20 1.355(5) . . yes O24 C23 1.348(5) . . yes O17 H17 0.87(5) . . no O37 C36 1.239(9) . . yes O38 C36 1.271(8) . . yes O38 H38 0.82(6) . . no N7 C5 1.424(6) . . yes N7 C18 1.344(6) . . yes N21 C20 1.276(6) . . yes N21 N22 1.418(5) . . yes N22 C23 1.306(6) . . yes N25 C26 1.407(6) . . yes N25 C23 1.339(6) . . yes N7 H7 0.83(5) . . no N25 H25 0.82(5) . . no C1 C2 1.395(6) . . no C1 C6 1.379(6) . . no C2 C8 1.505(6) . . no C2 C3 1.397(6) . . no C3 C4 1.377(6) . . no C4 C5 1.387(6) . . no C5 C6 1.378(6) . . no C8 C13 1.529(6) . . no C8 C9 1.527(6) . . no C9 C10 1.532(6) . . no C10 C11 1.527(6) . . no C11 C12 1.519(6) . . no C11 C14 1.537(6) . . no C12 C13 1.513(6) . . no C14 C15 1.486(7) . . no C18 C20 1.480(6) . . no C26 C31 1.374(8) . . no C26 C27 1.387(7) . . no C27 C28 1.383(8) . . no C28 C29 1.360(10) . . no C29 C30 1.351(10) . . no C30 C31 1.368(8) . . no C1 H1 0.9600 . . no C3 H3 0.9596 . . no C4 H4 0.9602 . . no C6 H6 0.9608 . . no C8 H8 0.9599 . . no C9 H9B 0.9599 . . no C9 H9A 0.9599 . . no C10 H10B 0.9738 . . no C10 H10A 0.9596 . . no C11 H11 0.9593 . . no C12 H12A 0.9609 . . no C12 H12B 0.9603 . . no C13 H13B 0.9589 . . no C13 H13A 0.9611 . . no C14 H14B 0.9274 . . no C14 H14A 0.9599 . . no C27 H27 0.8597 . . no C30 H30 0.9597 . . no C35 C36 1.500(9) . . no C35 H35A 0.9594 . . no C35 H35B 0.9600 . . no C35 H35C 0.9596 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 O24 C23 101.9(3) . . . yes C15 O17 H17 111(3) . . . no C36 O38 H38 131(4) . . . no C5 N7 C18 125.8(4) . . . yes N22 N21 C20 106.6(4) . . . yes N21 N22 C23 104.0(4) . . . yes C23 N25 C26 124.4(4) . . . yes C18 N7 H7 117(3) . . . no C5 N7 H7 117(3) . . . no C23 N25 H25 117(4) . . . no C26 N25 H25 115(4) . . . no C2 C1 C6 121.8(4) . . . no C1 C2 C8 121.9(4) . . . no C3 C2 C8 121.5(4) . . . no C1 C2 C3 116.5(4) . . . no C2 C3 C4 121.8(4) . . . no C3 C4 C5 120.6(4) . . . no C4 C5 C6 118.5(4) . . . no N7 C5 C4 122.4(4) . . . yes N7 C5 C6 119.1(4) . . . yes C1 C6 C5 120.8(4) . . . no C2 C8 C13 114.7(4) . . . no C2 C8 C9 110.5(3) . . . no C9 C8 C13 109.5(4) . . . no C8 C9 C10 111.9(3) . . . no C9 C10 C11 112.7(4) . . . no C10 C11 C12 110.0(4) . . . no C10 C11 C14 108.8(4) . . . no C12 C11 C14 112.7(3) . . . no C11 C12 C13 112.6(3) . . . no C8 C13 C12 112.4(4) . . . no C11 C14 C15 114.0(4) . . . no O17 C15 C14 116.3(4) . . . yes O16 C15 O17 123.1(5) . . . yes O16 C15 C14 120.6(5) . . . yes O19 C18 N7 125.6(4) . . . yes O19 C18 C20 119.7(4) . . . yes N7 C18 C20 114.8(4) . . . yes O24 C20 N21 113.5(4) . . . yes N21 C20 C18 129.9(4) . . . yes O24 C20 C18 116.6(4) . . . yes O24 C23 N22 113.9(4) . . . yes O24 C23 N25 115.7(4) . . . yes N22 C23 N25 130.4(4) . . . yes N25 C26 C27 121.8(5) . . . yes N25 C26 C31 121.1(4) . . . yes C27 C26 C31 117.1(4) . . . no C26 C27 C28 118.8(5) . . . no C27 C28 C29 121.8(6) . . . no F34 C28 C29 119.7(6) . . . yes F34 C28 C27 118.5(6) . . . yes C28 C29 C30 120.3(6) . . . no F33 C29 C28 119.0(6) . . . yes F33 C29 C30 120.7(6) . . . yes C29 C30 C31 118.0(6) . . . no C26 C31 C30 123.9(5) . . . no F32 C31 C26 117.3(4) . . . yes F32 C31 C30 118.8(5) . . . yes C6 C1 H1 116.47 . . . no C2 C1 H1 121.67 . . . no C4 C3 H3 121.27 . . . no C2 C3 H3 116.89 . . . no C3 C4 H4 120.64 . . . no C5 C4 H4 118.69 . . . no C1 C6 H6 119.03 . . . no C5 C6 H6 120.18 . . . no C9 C8 H8 101.94 . . . no C13 C8 H8 106.98 . . . no C2 C8 H8 112.41 . . . no C8 C9 H9A 113.05 . . . no C10 C9 H9A 103.45 . . . no C10 C9 H9B 106.71 . . . no C8 C9 H9B 107.25 . . . no H9A C9 H9B 114.40 . . . no C9 C10 H10B 108.17 . . . no C11 C10 H10A 115.77 . . . no C11 C10 H10B 111.78 . . . no H10A C10 H10B 98.52 . . . no C9 C10 H10A 108.89 . . . no C12 C11 H11 107.78 . . . no C14 C11 H11 105.55 . . . no C10 C11 H11 111.98 . . . no C11 C12 H12B 109.41 . . . no C13 C12 H12A 107.89 . . . no C13 C12 H12B 108.02 . . . no H12A C12 H12B 109.41 . . . no C11 C12 H12A 109.43 . . . no C8 C13 H13A 101.87 . . . no C8 C13 H13B 115.46 . . . no C12 C13 H13B 114.29 . . . no H13A C13 H13B 100.59 . . . no C12 C13 H13A 110.74 . . . no C11 C14 H14A 104.04 . . . no C11 C14 H14B 103.93 . . . no C15 C14 H14B 117.86 . . . no H14A C14 H14B 111.95 . . . no C15 C14 H14A 104.42 . . . no C28 C27 H27 122.13 . . . no C26 C27 H27 119.02 . . . no C29 C30 H30 118.76 . . . no C31 C30 H30 123.22 . . . no O37 C36 C35 121.5(6) . . . yes O38 C36 C35 115.0(6) . . . yes O37 C36 O38 123.5(6) . . . yes C36 C35 H35A 110.21 . . . no C36 C35 H35B 109.18 . . . no C36 C35 H35C 109.09 . . . no H35A C35 H35B 109.46 . . . no H35A C35 H35C 109.43 . . . no H35B C35 H35C 109.45 . . . no 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 C23 O24 C20 N21 0.0(5) . . . . no C23 O24 C20 C18 -178.2(4) . . . . no C20 O24 C23 N22 0.5(5) . . . . no C20 O24 C23 N25 -178.2(4) . . . . no C5 N7 C18 C20 -177.3(4) . . . . no C18 N7 C5 C4 25.8(7) . . . . no C5 N7 C18 O19 3.4(7) . . . . no C18 N7 C5 C6 -157.3(4) . . . . no C20 N21 N22 C23 0.7(5) . . . . no N22 N21 C20 O24 -0.4(5) . . . . no N22 N21 C20 C18 177.4(4) . . . . no N21 N22 C23 O24 -0.7(5) . . . . no N21 N22 C23 N25 177.8(5) . . . . no C26 N25 C23 N22 4.6(8) . . . . no C23 N25 C26 C27 40.9(7) . . . . no C23 N25 C26 C31 -139.5(5) . . . . no C26 N25 C23 O24 -176.9(4) . . . . no C6 C1 C2 C3 -0.9(6) . . . . no C6 C1 C2 C8 175.3(4) . . . . no C2 C1 C6 C5 1.1(7) . . . . no C1 C2 C8 C9 -105.7(5) . . . . no C3 C2 C8 C13 -54.1(6) . . . . no C1 C2 C8 C13 129.9(4) . . . . no C3 C2 C8 C9 70.3(5) . . . . no C8 C2 C3 C4 -175.9(4) . . . . no C1 C2 C3 C4 0.3(6) . . . . no C2 C3 C4 C5 0.1(7) . . . . no C3 C4 C5 N7 176.9(4) . . . . no C3 C4 C5 C6 0.0(7) . . . . no N7 C5 C6 C1 -177.6(4) . . . . no C4 C5 C6 C1 -0.6(7) . . . . no C2 C8 C13 C12 -179.8(4) . . . . no C9 C8 C13 C12 55.3(5) . . . . no C13 C8 C9 C10 -54.5(5) . . . . no C2 C8 C9 C10 178.2(4) . . . . no C8 C9 C10 C11 55.1(5) . . . . no C9 C10 C11 C12 -53.2(5) . . . . no C9 C10 C11 C14 -177.1(4) . . . . no C14 C11 C12 C13 175.3(4) . . . . no C12 C11 C14 C15 60.8(5) . . . . no C10 C11 C14 C15 -176.9(4) . . . . no C10 C11 C12 C13 53.7(5) . . . . no C11 C12 C13 C8 -56.1(5) . . . . no C11 C14 C15 O17 -95.5(5) . . . . no C11 C14 C15 O16 84.3(6) . . . . no N7 C18 C20 O24 -178.9(4) . . . . no N7 C18 C20 N21 3.3(7) . . . . no O19 C18 C20 O24 0.5(6) . . . . no O19 C18 C20 N21 -177.3(5) . . . . no N25 C26 C27 C28 -179.6(5) . . . . no C27 C26 C31 C30 -0.4(8) . . . . no N25 C26 C31 F32 -0.1(7) . . . . no N25 C26 C31 C30 -179.9(5) . . . . no C31 C26 C27 C28 0.8(7) . . . . no C27 C26 C31 F32 179.4(4) . . . . no C26 C27 C28 F34 -179.8(5) . . . . no C26 C27 C28 C29 0.0(9) . . . . no C27 C28 C29 C30 -1.2(10) . . . . no F34 C28 C29 C30 178.5(6) . . . . no C27 C28 C29 F33 179.6(5) . . . . no F34 C28 C29 F33 -0.7(9) . . . . no F33 C29 C30 C31 -179.2(5) . . . . no C28 C29 C30 C31 1.6(10) . . . . no C29 C30 C31 C26 -0.9(9) . . . . no C29 C30 C31 F32 179.3(5) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F32 N25 2.725(6) . . no F32 C27 3.286(6) . 1_455 no F32 C28 3.284(7) . 1_455 no F33 F34 2.688(5) . . no F33 C35 3.193(8) . 2_675 no F34 C31 3.299(6) . 1_655 no F34 C29 3.203(7) . 2_675 no F34 F33 2.688(5) . . no F34 C30 3.290(7) . 1_655 no F34 C28 3.311(7) . 2_675 no F32 H25 2.41(6) . . no F32 H13B 2.8254 . 2_566 no F32 H12B 2.7525 . 2_566 no F32 H12A 2.7772 . 2_666 no F33 H35C 2.7456 . 2_575 no F33 H35A 2.8114 . 2_675 no O16 N21 3.258(5) . 2_656 no O16 O24 3.015(5) . 2_656 no O16 O38 2.674(5) . 2_556 no O16 C36 3.387(7) . 2_556 no O16 C20 3.056(6) . 2_656 no O16 C23 3.156(6) . 2_656 no O17 O37 2.652(6) . 2_556 no O17 C12 3.267(6) . . no O17 C36 3.266(8) . 2_656 no O19 C5 3.411(5) . 1_455 no O19 C6 3.169(5) . 1_455 no O19 C4 2.885(5) . . no O19 O24 2.697(4) . . no O19 N7 2.975(5) . 1_455 no O19 C6 3.245(6) . 2_666 no O24 O16 3.015(5) . 2_656 no O24 N22 2.224(5) . . no O24 O19 2.697(4) . . no O24 C1 3.210(5) . 2_666 no O24 N21 3.011(5) . 1_455 no O37 C15 3.382(7) . 2_556 no O37 O17 2.652(6) . 2_556 no O38 C14 3.358(6) . 2_656 no O38 O16 2.674(5) . 2_556 no O38 C15 3.339(6) . 2_656 no O16 H14B 2.8628 . 1_455 no O16 H38 1.90(6) . 2_556 no O17 H12B 2.8306 . . no O19 H7 2.26(5) . 1_455 no O19 H6 2.7982 . 2_666 no O19 H6 2.6246 . 1_455 no O19 H4 2.3320 . . no O37 H17 1.79(5) . 2_556 no O38 H27 2.7394 . 1_455 no O38 H17 2.92(5) . 2_556 no N7 O19 2.975(5) . 1_655 no N7 N21 2.871(5) . . no N21 N7 2.871(5) . . no N21 O24 2.201(5) . . no N21 O16 3.258(5) . 2_656 no N21 O24 3.011(5) . 1_655 no N22 C27 3.069(6) . . no N22 O24 2.224(5) . . no N22 N25 3.210(6) . 1_655 no N25 N22 3.210(6) . 1_455 no N25 F32 2.725(6) . . no N7 H10B 2.7339 . 2_756 no N21 H7 2.51(4) . . no N22 H13B 2.9376 . 2_666 no N22 H27 2.6814 . . no N22 H25 2.44(5) . 1_655 no C1 C4 3.567(6) . 1_655 no C1 O24 3.210(5) . 2_666 no C1 C3 3.450(6) . 1_655 no C1 C20 3.502(6) . 2_666 no C3 C1 3.450(6) . 1_455 no C4 O19 2.885(5) . . no C4 C1 3.567(6) . 1_455 no C4 C6 3.439(6) . 1_455 no C5 C18 3.593(6) . 2_666 no C5 O19 3.411(5) . 1_655 no C6 C20 3.499(6) . 2_666 no C6 O19 3.169(5) . 1_655 no C6 C18 3.321(6) . 2_666 no C6 O19 3.245(6) . 2_666 no C6 C4 3.439(6) . 1_655 no C12 O17 3.267(6) . . no C14 O38 3.358(6) . 2_656 no C15 O38 3.339(6) . 2_656 no C15 C36 3.577(8) . 2_656 no C15 O37 3.382(7) . 2_556 no C18 C6 3.321(6) . 2_666 no C18 C5 3.593(6) . 2_666 no C20 C6 3.499(6) . 2_666 no C20 O16 3.056(6) . 2_656 no C20 C1 3.502(6) . 2_666 no C23 O16 3.156(6) . 2_656 no C27 N22 3.069(6) . . no C27 F32 3.286(6) . 1_655 no C28 F34 3.311(7) . 2_675 no C28 C31 3.547(8) . 1_655 no C28 F32 3.284(7) . 1_655 no C29 F34 3.203(7) . 2_675 no C30 F34 3.290(7) . 1_455 no C31 F34 3.299(6) . 1_455 no C31 C28 3.547(8) . 1_455 no C35 F33 3.193(8) . 2_675 no C36 O17 3.266(8) . 2_656 no C36 C15 3.577(8) . 2_656 no C36 O16 3.387(7) . 2_556 no C3 H1 3.0660 . 1_455 no C3 H13A 2.7640 . . no C3 H9B 2.9021 . . no C4 H9B 2.9967 . 2_656 no C5 H10B 2.8709 . 2_756 no C6 H4 3.0431 . 1_655 no C9 H3 3.0532 . . no C12 H10A 3.0570 . 1_455 no C13 H3 2.8771 . . no C15 H38 2.86(6) . 2_556 no C15 H12B 2.7810 . . no C18 H4 2.7320 . . no C23 H27 2.8021 . . no C30 H12A 3.0210 . 2_666 no C31 H12A 2.7550 . 2_666 no C36 H17 2.66(5) . 2_556 no H1 H8 2.4759 . . no H1 C3 3.0660 . 1_655 no H3 C9 3.0532 . . no H3 C13 2.8771 . . no H3 H9B 2.5535 . . no H3 H13A 2.2661 . . no H4 H9B 2.2721 . 2_656 no H4 O19 2.3320 . . no H4 C6 3.0431 . 1_455 no H4 C18 2.7320 . . no H6 H7 2.4232 . . no H6 O19 2.6246 . 1_655 no H6 O19 2.7982 . 2_666 no H7 H6 2.4232 . . no H7 N21 2.51(4) . . no H7 O19 2.26(5) . 1_655 no H8 H10A 2.5521 . . no H8 H12A 2.4955 . . no H8 H1 2.4759 . . no H9A H13A 2.5359 . 1_655 no H9B H3 2.5535 . . no H9B H13A 2.3989 . . no H9B C3 2.9021 . . no H9B H4 2.2721 . 2_656 no H9B C4 2.9967 . 2_656 no H10A C12 3.0570 . 1_655 no H10A H14B 2.3870 . . no H10A H12B 2.5648 . 1_655 no H10A H8 2.5521 . . no H10A H11 2.4993 . 1_655 no H10B H14A 2.4818 . . no H10B N7 2.7339 . 2_756 no H10B C5 2.8709 . 2_756 no H11 H10A 2.4993 . 1_455 no H12A H14B 2.5372 . . no H12A F32 2.7772 . 2_666 no H12A C30 3.0210 . 2_666 no H12A H8 2.4955 . . no H12A C31 2.7550 . 2_666 no H12B O17 2.8306 . . no H12B C15 2.7810 . . no H12B F32 2.7525 . 2_566 no H12B H10A 2.5648 . 1_455 no H13A H9A 2.5359 . 1_455 no H13A H9B 2.3989 . . no H13A H3 2.2661 . . no H13A C3 2.7640 . . no H13B N22 2.9376 . 2_666 no H13B F32 2.8254 . 2_566 no H14A H10B 2.4818 . . no H14B H12A 2.5372 . . no H14B O16 2.8628 . 1_655 no H14B H10A 2.3870 . . no H17 O37 1.79(5) . 2_556 no H17 C36 2.66(5) . 2_556 no H17 O38 2.92(5) . 2_556 no H25 F32 2.41(6) . . no H25 N22 2.44(5) . 1_455 no H27 C23 2.8021 . . no H27 N22 2.6814 . . no H27 O38 2.7394 . 1_655 no H30 H35C 2.5163 . 2_575 no H35A F33 2.8114 . 2_675 no H35C F33 2.7456 . 2_575 no H35C H30 2.5163 . 2_575 no H38 O16 1.90(6) . 2_556 no H38 C15 2.86(6) . 2_556 no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N7 H7 O19 0.83(5) 2.26(5) 2.975(5) 145(4) 1_655 yes N7 H7 N21 0.83(5) 2.51(4) 2.871(5) 107(4) . yes O17 H17 O37 0.87(5) 1.79(5) 2.652(6) 173(4) 2_556 yes N25 H25 F32 0.82(5) 2.41(6) 2.725(6) 104(5) . yes N25 H25 N22 0.82(5) 2.44(5) 3.210(6) 156(5) 1_455 yes O38 H38 O16 0.82(6) 1.90(6) 2.674(5) 155(6) 2_556 yes C4 H4 O19 0.9600 2.3300 2.885(5) 116.00 . yes data_AZ12934226 _database_code_depnum_ccdc_archive 'CCDC 886320' #TrackingRef '11863_web_deposit_cif_file_1_AnneErtan_1339576411.AZ12934226.cif' _audit_update_record ; 2012-06-13 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(6-fluoro-5-(5-(2,4,5- trifluorophenylamino)-1,3,4-oxadiazole-2- carboxamido)pyridin-2-yloxy)cyclo- hexanecarboxylic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H17 F4 N5 O5' _chemical_formula_sum 'C21 H17 F4 N5 O5' _chemical_formula_weight 495.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.7773(14) _cell_length_b 6.3200(3) _cell_length_c 23.2587(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.671(3) _cell_angle_gamma 90.00 _cell_volume 4301.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 6628 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 21.72 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2032 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details ' APEXII' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 55003 _diffrn_reflns_av_R_equivalents 0.0687 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4007 _reflns_number_gt 2557 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0823P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4007 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0924 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1372 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.33665(5) -0.9317(2) 1.00336(6) 0.0338(4) Uani 1 1 d . . . O1 O 0.23094(5) -0.3882(2) 0.93614(7) 0.0224(4) Uani 1 1 d . . . F2 F 0.33617(5) -1.4422(2) 0.85548(7) 0.0435(4) Uani 1 1 d . . . O3 O 0.02723(5) 0.6413(2) 0.88580(7) 0.0252(4) Uani 1 1 d . . . F4 F 0.09560(5) 0.0369(2) 0.96760(6) 0.0343(4) Uani 1 1 d . . . F3 F 0.27357(5) -1.2111(2) 0.78317(6) 0.0420(4) Uani 1 1 d . . . O2 O 0.18940(6) -0.0097(3) 0.95882(7) 0.0317(5) Uani 1 1 d . . . N5 N 0.06263(6) 0.3366(3) 0.92847(9) 0.0236(5) Uani 1 1 d . . . N2 N 0.21836(7) -0.5746(3) 0.85340(9) 0.0258(5) Uani 1 1 d . . . N1 N 0.27425(6) -0.6907(3) 0.93484(9) 0.0237(5) Uani 1 1 d . . . H1 H 0.2873 -0.6551 0.9696 0.028 Uiso 1 1 calc R . . N3 N 0.18953(7) -0.3973(3) 0.84763(9) 0.0254(5) Uani 1 1 d . . . N4 N 0.13935(7) -0.0393(3) 0.87216(9) 0.0245(5) Uani 1 1 d . . . H4 H 0.1324 -0.1160 0.8413 0.029 Uiso 1 1 calc R . . C7 C 0.24169(8) -0.5610(4) 0.90639(11) 0.0210(6) Uani 1 1 d . . . C1 C 0.28862(8) -0.8799(4) 0.91201(11) 0.0226(6) Uani 1 1 d . . . C2 C 0.32093(8) -1.0028(4) 0.94789(11) 0.0244(6) Uani 1 1 d . . . C19 C -0.05429(8) 0.8946(3) 0.86002(11) 0.0242(6) Uani 1 1 d . . . H19A H -0.0695 1.0306 0.8588 0.029 Uiso 1 1 calc R . . H19B H -0.0344 0.8970 0.8314 0.029 Uiso 1 1 calc R . . C17 C -0.06763(8) 0.5005(3) 0.85071(11) 0.0235(6) Uani 1 1 d . . . H17A H -0.0912 0.3928 0.8432 0.028 Uiso 1 1 calc R . . H17B H -0.0479 0.4837 0.8222 0.028 Uiso 1 1 calc R . . C13 C 0.05497(8) 0.4733(4) 0.88398(11) 0.0227(6) Uani 1 1 d . . . C21 C -0.11637(8) 0.7453(4) 0.78301(11) 0.0230(6) Uani 1 1 d . . . C6 C 0.27271(8) -0.9531(4) 0.85564(11) 0.0261(6) Uani 1 1 d . . . H6 H 0.2512 -0.8755 0.8300 0.031 Uiso 1 1 calc R . . C14 C 0.09010(8) 0.1773(4) 0.92308(10) 0.0227(6) Uani 1 1 d . . . C9 C 0.17534(8) -0.0998(4) 0.91246(11) 0.0232(6) Uani 1 1 d . . . C8 C 0.19749(8) -0.2951(4) 0.89620(10) 0.0209(6) Uani 1 1 d . . . C16 C -0.03975(8) 0.4713(4) 0.91212(10) 0.0250(6) Uani 1 1 d . . . H16A H -0.0601 0.4744 0.9403 0.030 Uiso 1 1 calc R . . H16B H -0.0249 0.3341 0.9148 0.030 Uiso 1 1 calc R . . C5 C 0.28898(9) -1.1403(4) 0.83811(11) 0.0275(6) Uani 1 1 d . . . C20 C -0.02552(8) 0.8609(4) 0.92102(11) 0.0255(6) Uani 1 1 d . . . H20A H -0.0017 0.9676 0.9283 0.031 Uiso 1 1 calc R . . H20B H -0.0447 0.8778 0.9501 0.031 Uiso 1 1 calc R . . C3 C 0.33738(8) -1.1905(4) 0.93047(12) 0.0286(6) Uani 1 1 d . . . H3 H 0.3589 -1.2692 0.9558 0.034 Uiso 1 1 calc R . . C10 C 0.11186(8) 0.1415(4) 0.87658(11) 0.0222(6) Uani 1 1 d . . . C4 C 0.32100(9) -1.2576(4) 0.87463(12) 0.0291(6) Uani 1 1 d . . . C18 C -0.08987(8) 0.7211(3) 0.84403(10) 0.0211(6) Uani 1 1 d . . . H18 H -0.1114 0.7303 0.8711 0.025 Uiso 1 1 calc R . . C12 C 0.07431(8) 0.4542(4) 0.83447(11) 0.0276(6) Uani 1 1 d . . . H12 H 0.0679 0.5522 0.8042 0.033 Uiso 1 1 calc R . . C11 C 0.10322(8) 0.2862(4) 0.83121(11) 0.0270(6) Uani 1 1 d . . . H11 H 0.1169 0.2701 0.7986 0.032 Uiso 1 1 calc R . . C15 C -0.00379(8) 0.6429(4) 0.92723(11) 0.0229(6) Uani 1 1 d . . . H15 H 0.0133 0.6226 0.9671 0.027 Uiso 1 1 calc R . . O4 O -0.10723(6) 0.8707(3) 0.74722(8) 0.0345(5) Uani 1 1 d . . . O5 O -0.15021(6) 0.6080(3) 0.77031(8) 0.0392(5) Uani 1 1 d . . . H5 H -0.1619 0.6186 0.7356 0.059 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0320(9) 0.0321(8) 0.0322(10) 0.0006(7) -0.0071(7) 0.0038(7) O1 0.0231(9) 0.0227(9) 0.0199(10) -0.0029(7) -0.0006(7) 0.0061(7) F2 0.0502(10) 0.0269(8) 0.0564(11) -0.0051(8) 0.0178(9) 0.0144(8) O3 0.0227(9) 0.0220(9) 0.0310(11) 0.0050(8) 0.0050(8) 0.0080(7) F4 0.0382(9) 0.0364(9) 0.0288(9) 0.0130(7) 0.0076(7) 0.0169(7) F3 0.0588(11) 0.0367(9) 0.0301(10) -0.0109(7) 0.0069(8) 0.0069(8) O2 0.0314(11) 0.0348(10) 0.0246(11) -0.0110(9) -0.0061(8) 0.0081(8) N5 0.0208(11) 0.0246(11) 0.0238(12) 0.0026(10) -0.0002(9) 0.0064(9) N2 0.0253(12) 0.0250(11) 0.0237(13) -0.0038(9) -0.0046(10) 0.0081(9) N1 0.0254(11) 0.0221(11) 0.0200(12) -0.0037(9) -0.0050(9) 0.0066(9) N3 0.0247(12) 0.0235(11) 0.0259(13) -0.0019(10) -0.0009(10) 0.0079(9) N4 0.0242(11) 0.0238(11) 0.0213(12) -0.0088(9) -0.0062(9) 0.0063(9) C7 0.0234(13) 0.0198(12) 0.0191(14) -0.0021(11) 0.0023(11) 0.0013(11) C1 0.0218(13) 0.0199(13) 0.0264(15) 0.0004(11) 0.0054(12) 0.0001(10) C2 0.0219(14) 0.0267(14) 0.0228(15) -0.0006(11) -0.0009(11) -0.0033(11) C19 0.0261(14) 0.0158(12) 0.0283(15) 0.0007(11) -0.0010(12) 0.0021(10) C17 0.0244(14) 0.0179(13) 0.0267(15) 0.0007(11) 0.0009(11) 0.0008(10) C13 0.0172(13) 0.0217(13) 0.0270(15) 0.0005(11) -0.0016(11) 0.0011(11) C21 0.0229(14) 0.0215(13) 0.0233(15) -0.0004(12) 0.0011(11) 0.0047(11) C6 0.0273(15) 0.0249(13) 0.0253(16) 0.0008(12) 0.0027(12) 0.0036(11) C14 0.0236(14) 0.0243(13) 0.0184(14) 0.0052(11) -0.0010(11) 0.0035(11) C9 0.0205(13) 0.0227(13) 0.0255(15) -0.0039(11) 0.0024(12) 0.0008(11) C8 0.0189(13) 0.0215(13) 0.0196(14) -0.0021(11) -0.0030(11) 0.0012(10) C16 0.0248(14) 0.0218(13) 0.0271(15) 0.0065(11) 0.0013(12) 0.0056(11) C5 0.0360(16) 0.0247(14) 0.0227(15) -0.0039(11) 0.0079(12) -0.0027(12) C20 0.0237(13) 0.0238(13) 0.0265(15) -0.0036(11) -0.0014(11) 0.0037(11) C3 0.0218(14) 0.0218(14) 0.0416(18) 0.0053(12) 0.0045(12) 0.0037(11) C10 0.0199(13) 0.0201(13) 0.0245(15) -0.0030(11) -0.0011(11) 0.0033(10) C4 0.0293(15) 0.0189(13) 0.0425(18) -0.0007(13) 0.0154(13) 0.0031(11) C18 0.0213(13) 0.0226(13) 0.0181(14) -0.0005(10) 0.0005(11) 0.0034(10) C12 0.0303(15) 0.0251(13) 0.0270(16) 0.0057(11) 0.0040(12) 0.0038(12) C11 0.0286(15) 0.0278(14) 0.0249(15) 0.0000(12) 0.0059(12) 0.0025(12) C15 0.0233(14) 0.0268(13) 0.0180(14) 0.0014(11) 0.0022(11) 0.0038(11) O4 0.0423(12) 0.0328(10) 0.0241(11) 0.0081(8) -0.0048(9) -0.0103(9) O5 0.0390(12) 0.0477(12) 0.0245(11) 0.0082(9) -0.0104(9) -0.0194(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.364(3) . ? O1 C7 1.363(3) . ? O1 C8 1.363(3) . ? F2 C4 1.356(3) . ? O3 C13 1.350(3) . ? O3 C15 1.453(3) . ? F4 C14 1.350(3) . ? F3 C5 1.352(3) . ? O2 C9 1.223(3) . ? N5 C14 1.318(3) . ? N5 C13 1.335(3) . ? N2 C7 1.301(3) . ? N2 N3 1.403(3) . ? N1 C7 1.346(3) . ? N1 C1 1.407(3) . ? N1 H1 0.8600 . ? N3 C8 1.285(3) . ? N4 C9 1.342(3) . ? N4 C10 1.421(3) . ? N4 H4 0.8600 . ? C1 C6 1.388(3) . ? C1 C2 1.389(3) . ? C2 C3 1.373(3) . ? C19 C18 1.522(3) . ? C19 C20 1.530(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C17 C16 1.525(3) . ? C17 C18 1.539(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C13 C12 1.385(4) . ? C21 O4 1.216(3) . ? C21 O5 1.321(3) . ? C21 C18 1.499(3) . ? C6 C5 1.369(3) . ? C6 H6 0.9300 . ? C14 C10 1.378(3) . ? C9 C8 1.481(3) . ? C16 C15 1.519(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C5 C4 1.371(4) . ? C20 C15 1.518(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C3 C4 1.368(4) . ? C3 H3 0.9300 . ? C10 C11 1.384(3) . ? C18 H18 0.9800 . ? C12 C11 1.378(3) . ? C12 H12 0.9300 . ? C11 H11 0.9300 . ? C15 H15 0.9800 . ? O5 H5 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 C8 102.16(17) . . ? C13 O3 C15 119.60(18) . . ? C14 N5 C13 116.2(2) . . ? C7 N2 N3 104.35(18) . . ? C7 N1 C1 125.0(2) . . ? C7 N1 H1 117.5 . . ? C1 N1 H1 117.5 . . ? C8 N3 N2 107.92(18) . . ? C9 N4 C10 125.1(2) . . ? C9 N4 H4 117.5 . . ? C10 N4 H4 117.5 . . ? N2 C7 N1 129.4(2) . . ? N2 C7 O1 113.6(2) . . ? N1 C7 O1 117.0(2) . . ? C6 C1 C2 117.3(2) . . ? C6 C1 N1 124.4(2) . . ? C2 C1 N1 118.3(2) . . ? F1 C2 C3 119.0(2) . . ? F1 C2 C1 117.5(2) . . ? C3 C2 C1 123.5(2) . . ? C18 C19 C20 111.78(19) . . ? C18 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? C18 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? C16 C17 C18 110.70(19) . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? N5 C13 O3 120.1(2) . . ? N5 C13 C12 123.4(2) . . ? O3 C13 C12 116.4(2) . . ? O4 C21 O5 122.2(2) . . ? O4 C21 C18 124.7(2) . . ? O5 C21 C18 113.0(2) . . ? C5 C6 C1 119.4(2) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? N5 C14 F4 114.7(2) . . ? N5 C14 C10 126.1(2) . . ? F4 C14 C10 119.1(2) . . ? O2 C9 N4 125.6(2) . . ? O2 C9 C8 121.1(2) . . ? N4 C9 C8 113.2(2) . . ? N3 C8 O1 112.00(19) . . ? N3 C8 C9 128.7(2) . . ? O1 C8 C9 119.3(2) . . ? C15 C16 C17 111.65(19) . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? F3 C5 C6 119.4(2) . . ? F3 C5 C4 118.8(2) . . ? C6 C5 C4 121.8(2) . . ? C15 C20 C19 111.73(19) . . ? C15 C20 H20A 109.3 . . ? C19 C20 H20A 109.3 . . ? C15 C20 H20B 109.3 . . ? C19 C20 H20B 109.3 . . ? H20A C20 H20B 107.9 . . ? C4 C3 C2 117.7(2) . . ? C4 C3 H3 121.2 . . ? C2 C3 H3 121.2 . . ? C14 C10 C11 116.2(2) . . ? C14 C10 N4 123.3(2) . . ? C11 C10 N4 120.3(2) . . ? F2 C4 C3 119.8(2) . . ? F2 C4 C5 119.9(2) . . ? C3 C4 C5 120.3(2) . . ? C21 C18 C19 112.22(19) . . ? C21 C18 C17 109.24(18) . . ? C19 C18 C17 111.15(19) . . ? C21 C18 H18 108.0 . . ? C19 C18 H18 108.0 . . ? C17 C18 H18 108.0 . . ? C11 C12 C13 118.2(2) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? C12 C11 C10 119.8(2) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? O3 C15 C20 104.79(19) . . ? O3 C15 C16 110.43(19) . . ? C20 C15 C16 110.87(19) . . ? O3 C15 H15 110.2 . . ? C20 C15 H15 110.2 . . ? C16 C15 H15 110.2 . . ? C21 O5 H5 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.411 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.168