# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Peterson, Matthew' 'Stanton, Mary' 'Kelly, Ron' 'Staples, Richard' 'Cheng, Alan' _publ_contact_author_name 'Peterson, Matthew' _publ_contact_author_email petersom@amgen.com _publ_section_title ; Preparation, Solid State Characterization and Single Crystal Structure Analysis of N-(4-(6-(4-(trifluoromethyl)phenyl) pyrimidine-4-yloxy)benzo[d]thiazol-2-yl)acetamide Crystal Forms ; # Attachment 'ADA_1.cif' data_ADA_1 _database_code_depnum_ccdc_archive 'CCDC 791323' #TrackingRef 'ADA_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C20 H13 F3 N4 O2 S, 0.5(C6 H10 O4)' _chemical_formula_sum 'C46 H36 F6 N8 O8 S2' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour colourless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 1006.95 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.113(5) _cell_length_b 15.131(5) _cell_length_c 15.413(5) _cell_angle_alpha 108.414(5) _cell_angle_beta 94.125(5) _cell_angle_gamma 96.846(5) _cell_volume 1115.7(12) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 614 _cell_measurement_theta_min 5.02 _cell_measurement_theta_max 46.72 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 518 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9682 _exptl_absorpt_correction_T_max 0.9856 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 60 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83 to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Scaling and absorption corrections were performed by the SADABS program. The structures are solved by the direct method using the SIR-97 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V6.1. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 836.6 _diffrn_reflns_number 3898 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1194 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 25.31 _reflns_number_total 3898 _reflns_number_gt 1614 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.58, 2007)' _computing_cell_refinement 'APEX2 (BRUKER, V5-0, 2008)' _computing_data_reduction 'SAINT (BRUKER, V7.56A, 2008)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.1859P)^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 3898 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1998 _refine_ls_R_factor_gt 0.1070 _refine_ls_wR_factor_ref 0.3390 _refine_ls_wR_factor_gt 0.2886 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.7731(4) 0.48074(14) 0.57267(13) 0.1027(9) Uani 1 1 d . . . F1 F -1.2275(17) -0.0021(5) 0.7852(8) 0.247(5) Uani 1 1 d . . . F2 F -0.9327(17) -0.0710(5) 0.8204(12) 0.410(13) Uani 1 1 d . . . F3 F -1.1472(15) 0.0075(5) 0.9189(8) 0.204(4) Uani 1 1 d . . . O1 O 0.0752(10) 0.4610(4) 0.7713(4) 0.1105(19) Uani 1 1 d . . . O2 O 0.8355(11) 0.3444(4) 0.4133(3) 0.113(2) Uani 1 1 d . . . N1 N 0.3649(13) 0.3962(4) 0.6212(5) 0.095(2) Uani 1 1 d . . . N2 N 0.4858(14) 0.3056(4) 0.4803(5) 0.105(2) Uani 1 1 d . . . H2 H 0.3535 0.2612 0.4768 0.126 Uiso 1 1 calc R . . N3 N 0.2306(10) 0.4491(4) 0.9125(4) 0.0830(17) Uani 1 1 d . . . N4 N -0.0287(11) 0.3437(4) 0.9713(4) 0.0920(18) Uani 1 1 d . . . C1 C 0.3098(16) 0.5165(6) 0.7658(7) 0.103(3) Uani 1 1 d . . . C2 C 0.3949(15) 0.6046(5) 0.8304(6) 0.106(3) Uani 1 1 d . . . H2A H 0.3044 0.6280 0.8828 0.128 Uiso 1 1 calc R . . C3 C 0.6220(17) 0.6583(6) 0.8152(7) 0.109(3) Uani 1 1 d . . . H3A H 0.6904 0.7176 0.8600 0.131 Uiso 1 1 calc R . . C4 C 0.7451(17) 0.6277(6) 0.7384(7) 0.106(3) Uani 1 1 d . . . H4 H 0.8920 0.6666 0.7285 0.127 Uiso 1 1 calc R . . C5 C 0.6554(15) 0.5392(5) 0.6745(5) 0.100(3) Uani 1 1 d . . . C6 C 0.4328(16) 0.4832(6) 0.6894(6) 0.100(3) Uani 1 1 d . . . C7 C 0.5212(18) 0.3878(5) 0.5569(6) 0.102(3) Uani 1 1 d . . . C8 C 0.6421(17) 0.2901(5) 0.4115(6) 0.098(3) Uani 1 1 d . . . C9 C 0.5560(18) 0.1981(6) 0.3352(5) 0.122(3) Uani 1 1 d . . . H9A H 0.4937 0.2104 0.2791 0.182 Uiso 1 1 calc R . . H9B H 0.4119 0.1609 0.3529 0.182 Uiso 1 1 calc R . . H9C H 0.7063 0.1630 0.3238 0.182 Uiso 1 1 calc R . . C10 C 0.0483(14) 0.4252(5) 0.8413(6) 0.094(2) Uani 1 1 d . . . C11 C -0.1808(14) 0.3614(5) 0.8300(6) 0.095(2) Uani 1 1 d . . . H11 H -0.3119 0.3476 0.7787 0.114 Uiso 1 1 calc R . . C12 C -0.2090(14) 0.3190(5) 0.8970(6) 0.093(2) Uani 1 1 d . . . C13 C 0.1794(15) 0.4066(5) 0.9754(6) 0.099(2) Uani 1 1 d . . . H13 H 0.3059 0.4235 1.0284 0.119 Uiso 1 1 calc R . . C14 C -0.4292(14) 0.2417(5) 0.8872(7) 0.101(3) Uani 1 1 d . . . C15 C -0.4339(16) 0.1936(6) 0.9506(7) 0.111(3) Uani 1 1 d . . . H15 H -0.3005 0.2120 1.0017 0.133 Uiso 1 1 calc R . . C16 C -0.6318(19) 0.1194(6) 0.9393(9) 0.139(4) Uani 1 1 d . . . H16 H -0.6388 0.0886 0.9843 0.167 Uiso 1 1 calc R . . C17 C -0.820(2) 0.0894(7) 0.8633(11) 0.151(5) Uani 1 1 d . . . C18 C -0.8227(19) 0.1362(7) 0.8024(9) 0.148(5) Uani 1 1 d . . . H18 H -0.9586 0.1171 0.7521 0.178 Uiso 1 1 calc R . . C19 C -0.6246(15) 0.2140(6) 0.8127(7) 0.119(3) Uani 1 1 d . . . H19 H -0.6257 0.2467 0.7693 0.142 Uiso 1 1 calc R . . C20 C -1.004(3) -0.0013(12) 0.8493(17) 0.224(9) Uani 1 1 d . . . O3 O -0.0310(13) 0.2671(4) 0.6299(4) 0.131(2) Uani 1 1 d . . . H3 H 0.0709 0.3078 0.6170 0.197 Uiso 1 1 calc R . . O4 O 0.0423(12) 0.1735(4) 0.4941(4) 0.1054(19) Uani 1 1 d . . . C21 C -0.0752(18) 0.1881(6) 0.5590(7) 0.106(3) Uani 1 1 d . . . C22 C -0.3128(17) 0.1228(6) 0.5706(6) 0.120(3) Uani 1 1 d . . . H22A H -0.2745 0.1087 0.6283 0.144 Uiso 1 1 calc R . . H22B H -0.4694 0.1561 0.5767 0.144 Uiso 1 1 calc R . . C23 C -0.3796(15) 0.0316(5) 0.4920(5) 0.103(3) Uani 1 1 d . . . H23A H -0.2243 -0.0023 0.4855 0.124 Uiso 1 1 calc R . . H23B H -0.4208 0.0450 0.4341 0.124 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.1070(16) 0.0898(13) 0.0888(13) 0.0334(10) -0.0395(11) -0.0540(11) F1 0.160(7) 0.140(6) 0.338(13) -0.023(7) 0.011(7) -0.088(5) F2 0.161(8) 0.050(3) 0.90(3) -0.027(8) 0.194(13) -0.020(4) F3 0.097(5) 0.129(5) 0.380(13) 0.099(7) 0.002(6) -0.026(4) O1 0.082(4) 0.095(4) 0.132(4) 0.035(3) -0.036(3) -0.035(3) O2 0.111(4) 0.101(4) 0.106(4) 0.040(3) -0.032(3) -0.054(3) N1 0.098(5) 0.077(4) 0.089(4) 0.028(3) -0.044(4) -0.040(3) N2 0.113(5) 0.092(4) 0.089(4) 0.035(4) -0.038(4) -0.056(4) N3 0.056(3) 0.062(3) 0.111(4) 0.011(3) -0.019(3) -0.006(3) N4 0.066(4) 0.070(3) 0.122(5) 0.019(3) -0.003(3) -0.014(3) C1 0.082(5) 0.103(6) 0.102(6) 0.034(5) -0.035(5) -0.039(5) C2 0.080(5) 0.090(5) 0.127(6) 0.029(5) -0.034(5) -0.024(4) C3 0.106(7) 0.080(5) 0.109(6) 0.015(5) -0.045(5) -0.037(5) C4 0.099(6) 0.090(5) 0.111(6) 0.040(5) -0.043(5) -0.042(5) C5 0.097(5) 0.098(5) 0.082(5) 0.035(4) -0.049(4) -0.053(4) C6 0.088(5) 0.093(5) 0.100(6) 0.034(5) -0.034(5) -0.035(5) C7 0.108(6) 0.098(5) 0.076(5) 0.032(4) -0.044(5) -0.054(5) C8 0.105(6) 0.092(5) 0.085(5) 0.042(4) -0.026(5) -0.042(5) C9 0.126(7) 0.108(6) 0.095(5) 0.024(5) -0.045(5) -0.063(5) C10 0.070(5) 0.069(4) 0.118(6) 0.012(4) -0.023(4) -0.015(4) C11 0.068(5) 0.080(5) 0.112(6) 0.011(4) -0.014(4) -0.013(4) C12 0.064(5) 0.065(4) 0.128(6) 0.013(4) -0.010(4) -0.012(4) C13 0.083(5) 0.067(4) 0.128(6) 0.023(4) -0.018(5) -0.016(4) C14 0.051(4) 0.062(4) 0.155(8) -0.009(5) 0.000(5) 0.004(4) C15 0.087(6) 0.071(5) 0.154(8) 0.015(5) 0.013(5) -0.007(4) C16 0.099(7) 0.078(5) 0.215(11) 0.027(6) 0.014(7) -0.022(5) C17 0.081(7) 0.076(6) 0.254(15) 0.006(8) 0.018(8) -0.020(5) C18 0.066(6) 0.092(7) 0.218(13) -0.032(7) 0.009(7) -0.018(6) C19 0.064(5) 0.085(5) 0.166(8) -0.001(5) 0.002(5) -0.023(4) C20 0.081(9) 0.142(13) 0.36(2) -0.025(13) 0.047(12) -0.053(9) O3 0.139(5) 0.093(4) 0.118(4) 0.008(3) -0.006(4) -0.065(4) O4 0.109(4) 0.089(3) 0.098(4) 0.032(3) -0.023(3) -0.050(3) C21 0.104(7) 0.096(6) 0.102(6) 0.044(5) -0.028(5) -0.049(5) C22 0.100(6) 0.091(5) 0.136(7) 0.019(5) -0.011(5) -0.046(5) C23 0.095(6) 0.088(5) 0.110(5) 0.041(4) -0.026(4) -0.047(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C5 1.730(9) . ? S1 C7 1.733(7) . ? F1 C20 1.45(2) . ? F2 C20 1.123(17) . ? F3 C20 1.32(2) . ? O1 C10 1.359(9) . ? O1 C1 1.404(9) . ? O2 C8 1.201(8) . ? N1 C7 1.302(10) . ? N1 C6 1.387(10) . ? N2 C8 1.352(10) . ? N2 C7 1.401(11) . ? N3 C10 1.314(9) . ? N3 C13 1.346(9) . ? N4 C13 1.324(8) . ? N4 C12 1.340(9) . ? C1 C6 1.358(12) . ? C1 C2 1.386(11) . ? C2 C3 1.414(11) . ? C3 C4 1.357(12) . ? C4 C5 1.389(11) . ? C5 C6 1.413(10) . ? C8 C9 1.504(11) . ? C10 C11 1.389(9) . ? C11 C12 1.385(10) . ? C12 C14 1.485(10) . ? C14 C19 1.387(11) . ? C14 C15 1.390(12) . ? C15 C16 1.377(10) . ? C16 C17 1.379(16) . ? C17 C18 1.342(17) . ? C17 C20 1.515(16) . ? C18 C19 1.418(12) . ? O3 C21 1.323(11) . ? O4 C21 1.178(10) . ? C21 C22 1.531(10) . ? C22 C23 1.503(11) . ? C23 C23 1.549(12) 2_456 ? 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 C5 S1 C7 88.4(4) . . ? C10 O1 C1 122.1(6) . . ? C7 N1 C6 110.5(6) . . ? C8 N2 C7 124.1(6) . . ? C10 N3 C13 114.7(6) . . ? C13 N4 C12 117.4(7) . . ? C6 C1 C2 122.1(8) . . ? C6 C1 O1 116.3(7) . . ? C2 C1 O1 121.3(10) . . ? C1 C2 C3 117.2(9) . . ? C4 C3 C2 121.9(7) . . ? C3 C4 C5 119.7(8) . . ? C4 C5 C6 119.4(9) . . ? C4 C5 S1 130.3(7) . . ? C6 C5 S1 110.3(6) . . ? C1 C6 N1 126.6(7) . . ? C1 C6 C5 119.6(7) . . ? N1 C6 C5 113.8(9) . . ? N1 C7 N2 120.2(6) . . ? N1 C7 S1 117.0(6) . . ? N2 C7 S1 122.8(8) . . ? O2 C8 N2 122.4(7) . . ? O2 C8 C9 123.7(9) . . ? N2 C8 C9 113.9(7) . . ? N3 C10 O1 121.4(6) . . ? N3 C10 C11 123.8(9) . . ? O1 C10 C11 114.8(7) . . ? C12 C11 C10 116.8(7) . . ? N4 C12 C11 120.4(6) . . ? N4 C12 C14 117.7(8) . . ? C11 C12 C14 121.8(7) . . ? N4 C13 N3 126.8(7) . . ? C19 C14 C15 119.4(8) . . ? C19 C14 C12 120.5(10) . . ? C15 C14 C12 120.1(8) . . ? C16 C15 C14 120.1(9) . . ? C15 C16 C17 120.5(11) . . ? C18 C17 C16 120.3(9) . . ? C18 C17 C20 122.8(15) . . ? C16 C17 C20 116.7(16) . . ? C17 C18 C19 120.6(11) . . ? C14 C19 C18 119.0(11) . . ? F2 C20 F3 116(2) . . ? F2 C20 F1 106.0(17) . . ? F3 C20 F1 93.8(11) . . ? F2 C20 C17 120.0(13) . . ? F3 C20 C17 110.6(14) . . ? F1 C20 C17 105.9(18) . . ? O4 C21 O3 124.4(7) . . ? O4 C21 C22 125.4(8) . . ? O3 C21 C22 110.1(9) . . ? C23 C22 C21 113.6(8) . . ? C22 C23 C23 111.2(9) . 2_456 ? 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 C10 O1 C1 C6 120.4(8) . . . . ? C10 O1 C1 C2 -65.9(11) . . . . ? C6 C1 C2 C3 -1.8(12) . . . . ? O1 C1 C2 C3 -175.2(7) . . . . ? C1 C2 C3 C4 3.3(12) . . . . ? C2 C3 C4 C5 -3.2(13) . . . . ? C3 C4 C5 C6 1.5(12) . . . . ? C3 C4 C5 S1 -178.7(6) . . . . ? C7 S1 C5 C4 -179.5(8) . . . . ? C7 S1 C5 C6 0.4(6) . . . . ? C2 C1 C6 N1 179.5(7) . . . . ? O1 C1 C6 N1 -6.8(12) . . . . ? C2 C1 C6 C5 0.3(13) . . . . ? O1 C1 C6 C5 173.9(6) . . . . ? C7 N1 C6 C1 178.8(8) . . . . ? C7 N1 C6 C5 -1.9(9) . . . . ? C4 C5 C6 C1 0.0(11) . . . . ? S1 C5 C6 C1 -179.9(6) . . . . ? C4 C5 C6 N1 -179.4(7) . . . . ? S1 C5 C6 N1 0.8(8) . . . . ? C6 N1 C7 N2 -179.2(7) . . . . ? C6 N1 C7 S1 2.3(9) . . . . ? C8 N2 C7 N1 -178.5(7) . . . . ? C8 N2 C7 S1 0.0(11) . . . . ? C5 S1 C7 N1 -1.6(7) . . . . ? C5 S1 C7 N2 179.9(7) . . . . ? C7 N2 C8 O2 4.3(12) . . . . ? C7 N2 C8 C9 -177.5(7) . . . . ? C13 N3 C10 O1 -178.7(7) . . . . ? C13 N3 C10 C11 -0.1(11) . . . . ? C1 O1 C10 N3 7.3(12) . . . . ? C1 O1 C10 C11 -171.5(8) . . . . ? N3 C10 C11 C12 -2.4(12) . . . . ? O1 C10 C11 C12 176.3(7) . . . . ? C13 N4 C12 C11 -2.8(11) . . . . ? C13 N4 C12 C14 174.1(6) . . . . ? C10 C11 C12 N4 3.9(11) . . . . ? C10 C11 C12 C14 -172.9(7) . . . . ? C12 N4 C13 N3 0.1(12) . . . . ? C10 N3 C13 N4 1.3(11) . . . . ? N4 C12 C14 C19 178.8(7) . . . . ? C11 C12 C14 C19 -4.3(12) . . . . ? N4 C12 C14 C15 -4.2(11) . . . . ? C11 C12 C14 C15 172.6(8) . . . . ? C19 C14 C15 C16 -0.2(13) . . . . ? C12 C14 C15 C16 -177.2(7) . . . . ? C14 C15 C16 C17 2.9(15) . . . . ? C15 C16 C17 C18 -4.5(18) . . . . ? C15 C16 C17 C20 171.1(11) . . . . ? C16 C17 C18 C19 3.3(19) . . . . ? C20 C17 C18 C19 -171.9(11) . . . . ? C15 C14 C19 C18 -0.9(12) . . . . ? C12 C14 C19 C18 176.1(7) . . . . ? C17 C18 C19 C14 -0.7(15) . . . . ? C18 C17 C20 F2 98(3) . . . . ? C16 C17 C20 F2 -78(3) . . . . ? C18 C17 C20 F3 -122.4(18) . . . . ? C16 C17 C20 F3 62(2) . . . . ? C18 C17 C20 F1 -22(2) . . . . ? C16 C17 C20 F1 162.6(13) . . . . ? O4 C21 C22 C23 3.5(13) . . . . ? O3 C21 C22 C23 179.2(8) . . . . ? C21 C22 C23 C23 179.7(8) . . . 2_456 ? 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 N2 H2 O4 0.88 2.04 2.905(8) 169.0 . O3 H3 N1 0.84 1.87 2.682(8) 161.5 . _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 25.31 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.430 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.070 # Attachment 'FB_H2O.CIF' data_FB_H20 _database_code_depnum_ccdc_archive 'CCDC 791324' #TrackingRef 'FB_H2O.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H15 F3 N4 O3 S' _chemical_formula_weight 448.42 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.8813(11) _cell_length_b 10.601(2) _cell_length_c 18.823(4) _cell_angle_alpha 96.910(4) _cell_angle_beta 91.332(4) _cell_angle_gamma 98.650(4) _cell_volume 955.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 809 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 27.81 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an oxford low-temperature apparatus perating at 193 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 45 s, such that a hemisphere was collected. A total of 1271 frames wer e collected with a final resolution of 0.76 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V6.1. All H atoms were found by difference fouier methods and refined istropically. ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD' _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 6875 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.92 _reflns_number_total 4544 _reflns_number_gt 3550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.625, 2001)' _computing_data_reduction 'SAINT (BRUKER, V6.22, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 2000, V6.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.0647P)^2^+0.2500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4544 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.18600(10) 0.42576(4) 0.16982(3) 0.02330(14) Uani 1 1 d . . . O1 O 0.6777(3) 0.04864(13) 0.17581(8) 0.0276(3) Uani 1 1 d . . . O2 O -0.1906(3) 0.46347(14) 0.07590(8) 0.0335(3) Uani 1 1 d . . . F1 F -0.5415(4) -0.36745(15) 0.51692(9) 0.0622(5) Uani 1 1 d . . . F2 F -0.2217(4) -0.2385(2) 0.57987(9) 0.0696(5) Uani 1 1 d . . . F3 F -0.5574(3) -0.16780(16) 0.53285(9) 0.0584(5) Uani 1 1 d . . . N1 N 0.4386(4) -0.28625(16) 0.25711(10) 0.0282(4) Uani 1 1 d . . . N2 N 0.7024(3) -0.15933(16) 0.17888(9) 0.0261(4) Uani 1 1 d . . . N3 N 0.2849(3) 0.19633(15) 0.11980(9) 0.0234(3) Uani 1 1 d . . . N4 N -0.0421(4) 0.27196(17) 0.05044(10) 0.0257(4) Uani 1 1 d . . . H1 H -0.062(5) 0.211(2) 0.0192(14) 0.035(7) Uiso 1 1 d . . . C1 C -0.3846(5) -0.2530(2) 0.52075(13) 0.0367(5) Uani 1 1 d . . . C2 C -0.2192(4) -0.2367(2) 0.45573(12) 0.0299(5) Uani 1 1 d . . . C3 C -0.1664(5) -0.1176(2) 0.43143(13) 0.0359(5) Uani 1 1 d . . . H2 H -0.248(6) -0.050(3) 0.4506(15) 0.055(8) Uiso 1 1 d . . . C4 C 0.0072(5) -0.1007(2) 0.37551(13) 0.0337(5) Uani 1 1 d . . . H3 H 0.044(5) -0.018(3) 0.3626(15) 0.050(8) Uiso 1 1 d . . . C5 C 0.1289(4) -0.20117(19) 0.34226(11) 0.0253(4) Uani 1 1 d . . . C6 C 0.0658(5) -0.3210(2) 0.36587(13) 0.0342(5) Uani 1 1 d . . . H4 H 0.137(5) -0.386(3) 0.3436(15) 0.042(7) Uiso 1 1 d . . . C7 C -0.1055(5) -0.3387(2) 0.42221(13) 0.0352(5) Uani 1 1 d . . . H5 H -0.146(5) -0.418(3) 0.4362(14) 0.044(7) Uiso 1 1 d . . . C8 C 0.3253(4) -0.18310(18) 0.28370(11) 0.0240(4) Uani 1 1 d . . . C9 C 0.3951(4) -0.06549(19) 0.25821(12) 0.0268(4) Uani 1 1 d . . . H6 H 0.320(4) 0.008(2) 0.2765(12) 0.028(6) Uiso 1 1 d . . . C10 C 0.5881(4) -0.05944(18) 0.20559(11) 0.0238(4) Uani 1 1 d . . . C11 C 0.6176(4) -0.26870(19) 0.20624(12) 0.0282(4) Uani 1 1 d . . . H7 H 0.696(5) -0.342(2) 0.1883(13) 0.034(6) Uiso 1 1 d . . . C12 C 0.6326(4) 0.16642(18) 0.21213(11) 0.0238(4) Uani 1 1 d . . . C13 C 0.7818(4) 0.21603(19) 0.27479(11) 0.0273(4) Uani 1 1 d . . . H8 H 0.904(4) 0.164(2) 0.2943(11) 0.023(5) Uiso 1 1 d . . . C14 C 0.7496(4) 0.3369(2) 0.30916(12) 0.0284(4) Uani 1 1 d . . . H9 H 0.853(5) 0.372(2) 0.3498(14) 0.033(6) Uiso 1 1 d . . . C15 C 0.5721(4) 0.4091(2) 0.28070(11) 0.0260(4) Uani 1 1 d . . . H10 H 0.547(4) 0.492(2) 0.3037(12) 0.028(6) Uiso 1 1 d . . . C16 C 0.4244(4) 0.35765(18) 0.21724(10) 0.0218(4) Uani 1 1 d . . . C17 C 0.4472(4) 0.23533(17) 0.18164(10) 0.0222(4) Uani 1 1 d . . . C18 C 0.1389(4) 0.28579(18) 0.10818(11) 0.0228(4) Uani 1 1 d . . . C19 C -0.2014(4) 0.3631(2) 0.03590(11) 0.0274(4) Uani 1 1 d . . . C20 C -0.3788(5) 0.3294(2) -0.03097(14) 0.0347(5) Uani 1 1 d . . . H11 H -0.505(6) 0.380(3) -0.0310(16) 0.058(9) Uiso 1 1 d . . . H12 H -0.484(6) 0.242(3) -0.0348(15) 0.051(8) Uiso 1 1 d . . . H13 H -0.267(7) 0.333(3) -0.072(2) 0.076(10) Uiso 1 1 d . . . O1S O 0.0912(4) 0.91943(18) 0.06651(10) 0.0444(5) Uani 1 1 d . . . H1S H -0.022(6) 0.901(3) 0.0978(17) 0.052(9) Uiso 1 1 d . . . H2S H 0.146(6) 0.995(3) 0.0713(17) 0.057(9) 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 S1 0.0263(2) 0.0192(2) 0.0253(3) 0.00254(18) 0.00115(18) 0.00643(18) O1 0.0345(8) 0.0192(7) 0.0318(8) 0.0078(6) 0.0089(6) 0.0083(6) O2 0.0379(8) 0.0308(8) 0.0337(8) 0.0015(6) -0.0031(7) 0.0139(7) F1 0.0759(11) 0.0439(9) 0.0632(11) 0.0078(8) 0.0344(9) -0.0082(8) F2 0.0562(10) 0.1208(17) 0.0344(9) 0.0207(10) 0.0017(8) 0.0136(10) F3 0.0613(10) 0.0574(10) 0.0649(11) 0.0169(8) 0.0315(9) 0.0250(8) N1 0.0339(9) 0.0192(8) 0.0316(9) 0.0036(7) 0.0018(7) 0.0041(7) N2 0.0296(8) 0.0222(8) 0.0272(9) 0.0032(7) 0.0018(7) 0.0057(7) N3 0.0246(8) 0.0195(8) 0.0263(9) 0.0031(6) 0.0030(7) 0.0038(6) N4 0.0273(8) 0.0247(9) 0.0250(9) 0.0013(7) -0.0010(7) 0.0061(7) C1 0.0387(12) 0.0367(12) 0.0354(13) 0.0063(10) 0.0058(10) 0.0058(10) C2 0.0276(10) 0.0312(11) 0.0302(11) 0.0038(9) 0.0001(8) 0.0024(8) C3 0.0434(13) 0.0289(11) 0.0379(13) 0.0048(9) 0.0079(10) 0.0117(10) C4 0.0408(12) 0.0239(11) 0.0394(13) 0.0107(9) 0.0081(10) 0.0078(9) C5 0.0251(9) 0.0235(10) 0.0265(10) 0.0037(8) -0.0027(8) 0.0015(8) C6 0.0391(12) 0.0231(10) 0.0411(13) 0.0039(9) 0.0102(10) 0.0063(9) C7 0.0402(12) 0.0239(11) 0.0418(13) 0.0097(9) 0.0087(10) 0.0006(9) C8 0.0226(9) 0.0211(9) 0.0280(10) 0.0040(8) -0.0034(8) 0.0024(7) C9 0.0275(10) 0.0214(10) 0.0332(11) 0.0056(8) 0.0040(8) 0.0074(8) C10 0.0254(9) 0.0190(9) 0.0269(10) 0.0048(7) -0.0041(8) 0.0028(7) C11 0.0341(11) 0.0193(9) 0.0314(11) 0.0015(8) 0.0015(9) 0.0063(8) C12 0.0264(9) 0.0177(9) 0.0290(10) 0.0070(7) 0.0070(8) 0.0044(7) C13 0.0284(10) 0.0254(10) 0.0302(11) 0.0102(8) 0.0028(8) 0.0051(8) C14 0.0309(10) 0.0286(10) 0.0249(11) 0.0057(8) -0.0025(9) 0.0008(8) C15 0.0299(10) 0.0221(10) 0.0265(10) 0.0032(8) 0.0043(8) 0.0049(8) C16 0.0224(9) 0.0202(9) 0.0244(10) 0.0071(7) 0.0048(7) 0.0039(7) C17 0.0240(9) 0.0186(9) 0.0249(10) 0.0063(7) 0.0053(8) 0.0026(7) C18 0.0241(9) 0.0197(9) 0.0248(10) 0.0034(7) 0.0058(8) 0.0031(7) C19 0.0248(9) 0.0285(10) 0.0303(11) 0.0070(8) 0.0027(8) 0.0056(8) C20 0.0334(12) 0.0366(13) 0.0358(13) 0.0054(10) -0.0049(10) 0.0110(10) O1S 0.0598(12) 0.0288(9) 0.0406(10) -0.0055(8) 0.0192(9) -0.0004(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C16 1.7412(19) . ? S1 C18 1.753(2) . ? O1 C10 1.354(2) . ? O1 C12 1.400(2) . ? O2 C19 1.221(3) . ? F1 C1 1.327(3) . ? F2 C1 1.332(3) . ? F3 C1 1.330(3) . ? N1 C11 1.322(3) . ? N1 C8 1.347(3) . ? N2 C10 1.322(3) . ? N2 C11 1.338(3) . ? N3 C18 1.304(2) . ? N3 C17 1.377(3) . ? N4 C18 1.364(3) . ? N4 C19 1.376(3) . ? N4 H1 0.81(3) . ? C1 C2 1.495(3) . ? C2 C7 1.381(3) . ? C2 C3 1.384(3) . ? C3 C4 1.378(3) . ? C3 H2 0.92(3) . ? C4 C5 1.388(3) . ? C4 H3 0.93(3) . ? C5 C6 1.390(3) . ? C5 C8 1.489(3) . ? C6 C7 1.379(3) . ? C6 H4 0.88(3) . ? C7 H5 0.91(3) . ? C8 C9 1.387(3) . ? C9 C10 1.383(3) . ? C9 H6 0.94(2) . ? C11 H7 0.95(2) . ? C12 C13 1.376(3) . ? C12 C17 1.399(3) . ? C13 C14 1.397(3) . ? C13 H8 0.97(2) . ? C14 C15 1.378(3) . ? C14 H9 0.91(3) . ? C15 C16 1.389(3) . ? C15 H10 0.96(2) . ? C16 C17 1.407(3) . ? C19 C20 1.486(3) . ? C20 H11 0.88(3) . ? C20 H12 0.98(3) . ? C20 H13 0.95(4) . ? O1S H1S 0.84(3) . ? O1S H2S 0.80(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 C16 S1 C18 88.17(9) . . ? C10 O1 C12 117.90(15) . . ? C11 N1 C8 116.50(17) . . ? C10 N2 C11 115.21(17) . . ? C18 N3 C17 109.33(16) . . ? C18 N4 C19 124.04(18) . . ? C18 N4 H1 124.2(18) . . ? C19 N4 H1 111.6(18) . . ? F1 C1 F3 105.5(2) . . ? F1 C1 F2 107.4(2) . . ? F3 C1 F2 105.5(2) . . ? F1 C1 C2 112.9(2) . . ? F3 C1 C2 113.45(19) . . ? F2 C1 C2 111.54(19) . . ? C7 C2 C3 119.8(2) . . ? C7 C2 C1 119.98(19) . . ? C3 C2 C1 120.1(2) . . ? C4 C3 C2 119.7(2) . . ? C4 C3 H2 118.5(18) . . ? C2 C3 H2 121.8(18) . . ? C3 C4 C5 121.3(2) . . ? C3 C4 H3 116.7(17) . . ? C5 C4 H3 121.9(17) . . ? C4 C5 C6 118.1(2) . . ? C4 C5 C8 121.97(18) . . ? C6 C5 C8 119.96(19) . . ? C7 C6 C5 121.0(2) . . ? C7 C6 H4 120.8(17) . . ? C5 C6 H4 118.2(17) . . ? C6 C7 C2 120.1(2) . . ? C6 C7 H5 119.3(17) . . ? C2 C7 H5 120.6(17) . . ? N1 C8 C9 120.92(19) . . ? N1 C8 C5 116.86(17) . . ? C9 C8 C5 122.21(18) . . ? C10 C9 C8 116.86(18) . . ? C10 C9 H6 120.8(13) . . ? C8 C9 H6 122.3(13) . . ? N2 C10 O1 113.15(17) . . ? N2 C10 C9 123.21(17) . . ? O1 C10 C9 123.63(17) . . ? N1 C11 N2 127.29(19) . . ? N1 C11 H7 115.5(14) . . ? N2 C11 H7 117.2(14) . . ? C13 C12 C17 121.04(18) . . ? C13 C12 O1 119.82(17) . . ? C17 C12 O1 119.04(18) . . ? C12 C13 C14 120.15(19) . . ? C12 C13 H8 117.9(13) . . ? C14 C13 H8 121.9(13) . . ? C15 C14 C13 120.9(2) . . ? C15 C14 H9 118.5(15) . . ? C13 C14 H9 120.5(15) . . ? C14 C15 C16 118.06(19) . . ? C14 C15 H10 122.0(14) . . ? C16 C15 H10 119.9(14) . . ? C15 C16 C17 122.76(17) . . ? C15 C16 S1 128.09(15) . . ? C17 C16 S1 109.14(15) . . ? N3 C17 C12 126.73(18) . . ? N3 C17 C16 116.22(16) . . ? C12 C17 C16 117.05(18) . . ? N3 C18 N4 121.76(18) . . ? N3 C18 S1 117.14(15) . . ? N4 C18 S1 121.10(14) . . ? O2 C19 N4 120.8(2) . . ? O2 C19 C20 124.26(19) . . ? N4 C19 C20 114.96(19) . . ? C19 C20 H11 110(2) . . ? C19 C20 H12 112.5(16) . . ? H11 C20 H12 105(2) . . ? C19 C20 H13 110(2) . . ? H11 C20 H13 112(3) . . ? H12 C20 H13 107(3) . . ? H1S O1S H2S 111(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C1 C2 C7 -38.0(3) . . . . ? F3 C1 C2 C7 -158.0(2) . . . . ? F2 C1 C2 C7 83.0(3) . . . . ? F1 C1 C2 C3 145.7(2) . . . . ? F3 C1 C2 C3 25.7(3) . . . . ? F2 C1 C2 C3 -93.3(3) . . . . ? C7 C2 C3 C4 -2.2(4) . . . . ? C1 C2 C3 C4 174.1(2) . . . . ? C2 C3 C4 C5 0.7(4) . . . . ? C3 C4 C5 C6 1.5(3) . . . . ? C3 C4 C5 C8 -177.6(2) . . . . ? C4 C5 C6 C7 -2.1(3) . . . . ? C8 C5 C6 C7 177.0(2) . . . . ? C5 C6 C7 C2 0.5(4) . . . . ? C3 C2 C7 C6 1.6(4) . . . . ? C1 C2 C7 C6 -174.7(2) . . . . ? C11 N1 C8 C9 0.1(3) . . . . ? C11 N1 C8 C5 -178.54(18) . . . . ? C4 C5 C8 N1 177.66(19) . . . . ? C6 C5 C8 N1 -1.4(3) . . . . ? C4 C5 C8 C9 -1.0(3) . . . . ? C6 C5 C8 C9 -180.0(2) . . . . ? N1 C8 C9 C10 -1.0(3) . . . . ? C5 C8 C9 C10 177.56(18) . . . . ? C11 N2 C10 O1 -179.31(17) . . . . ? C11 N2 C10 C9 0.2(3) . . . . ? C12 O1 C10 N2 -162.86(17) . . . . ? C12 O1 C10 C9 17.6(3) . . . . ? C8 C9 C10 N2 0.9(3) . . . . ? C8 C9 C10 O1 -179.67(18) . . . . ? C8 N1 C11 N2 1.1(3) . . . . ? C10 N2 C11 N1 -1.3(3) . . . . ? C10 O1 C12 C13 71.1(2) . . . . ? C10 O1 C12 C17 -112.6(2) . . . . ? C17 C12 C13 C14 0.1(3) . . . . ? O1 C12 C13 C14 176.31(17) . . . . ? C12 C13 C14 C15 -0.9(3) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? C14 C15 C16 C17 0.6(3) . . . . ? C14 C15 C16 S1 179.49(15) . . . . ? C18 S1 C16 C15 -178.70(19) . . . . ? C18 S1 C16 C17 0.34(14) . . . . ? C18 N3 C17 C12 -179.96(18) . . . . ? C18 N3 C17 C16 -0.4(2) . . . . ? C13 C12 C17 N3 -179.47(18) . . . . ? O1 C12 C17 N3 4.3(3) . . . . ? C13 C12 C17 C16 1.0(3) . . . . ? O1 C12 C17 C16 -175.25(16) . . . . ? C15 C16 C17 N3 179.08(17) . . . . ? S1 C16 C17 N3 0.0(2) . . . . ? C15 C16 C17 C12 -1.4(3) . . . . ? S1 C16 C17 C12 179.54(14) . . . . ? C17 N3 C18 N4 -179.57(17) . . . . ? C17 N3 C18 S1 0.7(2) . . . . ? C19 N4 C18 N3 179.77(18) . . . . ? C19 N4 C18 S1 -0.5(3) . . . . ? C16 S1 C18 N3 -0.65(15) . . . . ? C16 S1 C18 N4 179.65(17) . . . . ? C18 N4 C19 O2 -1.0(3) . . . . ? C18 N4 C19 C20 178.42(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 N4 H1 O1S 0.81(3) 1.98(3) 2.788(3) 172(2) 2_565 O1S H1S N2 0.84(3) 2.15(3) 2.985(3) 176(3) 1_465 O1S H1S O1 0.84(3) 2.65(3) 3.245(2) 130(2) 1_465 O1S H2S N3 0.80(3) 2.22(3) 2.988(2) 162(3) 1_565 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.92 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.554 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.063 # Attachment 'GUA.cif' data_GUA _database_code_depnum_ccdc_archive 'CCDC 791325' #TrackingRef 'GUA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H13 F3 N4 O2 S, C5 H8 O4' _chemical_formula_sum 'C25 H21 F3 N4 O6 S' _chemical_formula_weight 562.52 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.62940(10) _cell_length_b 11.2970(3) _cell_length_c 24.1522(7) _cell_angle_alpha 89.900(2) _cell_angle_beta 86.2950(10) _cell_angle_gamma 81.042(2) _cell_volume 1245.06(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6128 _cell_measurement_theta_min 3.67 _cell_measurement_theta_max 67.01 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 1.806 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5240 _exptl_absorpt_correction_T_max 0.8932 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83 to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Scaling and absorption corrections were performed by the SADABS program. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V6.1. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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 836.6 _diffrn_reflns_number 14117 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0449 _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 -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 67.56 _reflns_number_total 4281 _reflns_number_gt 3420 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V5.007, 2006)' _computing_cell_refinement 'APEX2 (BRUKER, V2.1-0, 2006)' _computing_data_reduction 'SAINT (BRUKER, V7.34A, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (BRUKER, 2000, V6.14)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, v6.12, 2001,)' _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^)+(0.0337P)^2^+2.0011P] 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 4281 _refine_ls_number_parameters 368 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1256 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.66438(15) 0.58811(7) 0.04653(3) 0.02757(19) Uani 1 1 d . . . F1 F 1.1542(5) 1.4915(2) 0.41959(8) 0.0584(6) Uani 1 1 d . . . F2 F 1.2077(5) 1.3318(2) 0.46781(8) 0.0531(6) Uani 1 1 d . . . F3 F 0.7832(5) 1.4336(2) 0.46227(8) 0.0601(7) Uani 1 1 d . . . O1 O 1.1216(4) 0.88386(18) 0.14824(8) 0.0266(5) Uani 1 1 d . . . O2 O 0.3187(5) 0.4309(2) 0.09286(10) 0.0428(6) Uani 1 1 d . . . N1 N 0.7547(5) 0.7039(2) 0.13563(9) 0.0237(5) Uani 1 1 d . . . N2 N 0.4444(5) 0.5635(2) 0.15344(10) 0.0273(6) Uani 1 1 d . . . H2 H 0.4258 0.5876 0.1883 0.033 Uiso 1 1 calc R . . N3 N 0.7476(5) 1.0403(2) 0.13530(9) 0.0272(6) Uani 1 1 d . . . N4 N 0.6406(5) 1.1973(2) 0.20343(10) 0.0320(6) Uani 1 1 d . . . C1 C 0.6182(6) 0.6197(3) 0.11741(11) 0.0248(6) Uani 1 1 d . . . C2 C 0.9069(6) 0.7505(3) 0.09176(11) 0.0232(6) Uani 1 1 d . . . C3 C 0.8813(6) 0.7008(3) 0.03949(11) 0.0249(6) Uani 1 1 d . . . O3 O 0.6807(8) 0.7982(3) 0.23896(9) 0.0694(10) Uani 1 1 d . A . H3 H 0.7063 0.7615 0.2084 0.104 Uiso 1 1 calc R . . C4 C 1.0151(6) 0.7428(3) -0.00849(11) 0.0286(7) Uani 1 1 d . . . H4A H 0.9946 0.7093 -0.0438 0.034 Uiso 1 1 calc R . . C5 C 1.1775(7) 0.8340(3) -0.00333(12) 0.0315(7) Uani 1 1 d . . . H5 H 1.2672 0.8644 -0.0357 0.038 Uiso 1 1 calc R . . O4 O 0.4676(7) 0.6448(3) 0.26411(10) 0.0611(8) Uani 1 1 d . A . O5 O 0.5429(7) 0.9322(3) 0.43853(10) 0.0730(10) Uani 1 1 d . . . C6 C 1.2133(6) 0.8829(3) 0.04851(12) 0.0287(7) Uani 1 1 d . . . H6 H 1.3305 0.9442 0.0514 0.034 Uiso 1 1 calc R . . O6 O 0.2665(8) 0.8888(3) 0.50903(11) 0.0849(12) Uani 1 1 d . . . H6A H 0.3405 0.9429 0.5241 0.127 Uiso 1 1 calc R . . C7 C 1.0773(6) 0.8412(3) 0.09526(11) 0.0249(6) Uani 1 1 d . . . C8 C 0.2963(6) 0.4724(3) 0.13944(13) 0.0311(7) Uani 1 1 d . . . C9 C 0.1156(7) 0.4298(3) 0.18660(14) 0.0372(8) Uani 1 1 d . . . H9A H -0.0512 0.3985 0.1723 0.056 Uiso 1 1 calc R . . H9B H 0.0438 0.4966 0.2122 0.056 Uiso 1 1 calc R . . H9C H 0.2358 0.3661 0.2063 0.056 Uiso 1 1 calc R . . C10 C 0.9564(6) 0.9884(3) 0.16581(11) 0.0229(6) Uani 1 1 d . . . C11 C 1.0204(6) 1.0340(3) 0.21624(11) 0.0263(6) Uani 1 1 d . . . H11 H 1.1710 0.9934 0.2374 0.032 Uiso 1 1 calc R . . C12 C 0.8558(6) 1.1405(3) 0.23413(11) 0.0249(6) Uani 1 1 d . . . C13 C 0.6018(7) 1.1435(3) 0.15647(12) 0.0326(7) Uani 1 1 d . . . H13 H 0.4512 1.1832 0.1351 0.039 Uiso 1 1 calc R . . C14 C 0.9011(6) 1.2026(3) 0.28642(11) 0.0267(6) Uani 1 1 d . . . C15 C 0.7534(8) 1.3168(3) 0.29780(14) 0.0439(9) Uani 1 1 d . . . H15 H 0.6187 1.3540 0.2726 0.053 Uiso 1 1 calc R . . C16 C 0.7985(8) 1.3774(3) 0.34505(15) 0.0474(9) Uani 1 1 d . . . H17 H 0.6977 1.4564 0.3518 0.057 Uiso 1 1 calc R . . C17 C 0.9878(7) 1.3247(3) 0.38259(12) 0.0304(7) Uani 1 1 d . . . C18 C 1.1356(9) 1.2116(3) 0.37226(14) 0.0517(10) Uani 1 1 d . . . H18 H 1.2678 1.1745 0.3979 0.062 Uiso 1 1 calc R . . C19 C 1.0928(9) 1.1512(3) 0.32453(14) 0.0496(10) Uani 1 1 d . . . H19 H 1.1970 1.0727 0.3177 0.060 Uiso 1 1 calc R . . C20 C 1.0327(7) 1.3943(3) 0.43300(13) 0.0377(8) Uani 1 1 d . . . C21 C 0.5490(8) 0.7363(3) 0.27499(13) 0.0378(8) Uani 1 1 d . . . C22 C 0.4391(15) 0.8069(6) 0.3301(2) 0.0333(12) Uani 0.563(6) 1 d P A 1 H22A H 0.5688 0.8666 0.3368 0.040 Uiso 0.563(6) 1 calc PR A 1 H22B H 0.2387 0.8506 0.3264 0.040 Uiso 0.563(6) 1 calc PR A 1 C23 C 0.4373(19) 0.7236(7) 0.3784(3) 0.0390(16) Uani 0.563(6) 1 d P A 1 H23A H 0.3523 0.6532 0.3667 0.047 Uiso 0.563(6) 1 calc PR A 1 H23B H 0.6436 0.6945 0.3861 0.047 Uiso 0.563(6) 1 calc PR A 1 C22B C 0.587(2) 0.7645(8) 0.3344(3) 0.0333(12) Uani 0.437(6) 1 d P A 2 H22C H 0.6562 0.8427 0.3373 0.040 Uiso 0.437(6) 1 calc PR A 2 H22D H 0.7335 0.7020 0.3499 0.040 Uiso 0.437(6) 1 calc PR A 2 C23B C 0.287(2) 0.7688(8) 0.3671(3) 0.0298(18) Uani 0.437(6) 1 d P A 2 H23C H 0.1577 0.8420 0.3560 0.036 Uiso 0.437(6) 1 calc PR A 2 H23D H 0.1990 0.6993 0.3552 0.036 Uiso 0.437(6) 1 calc PR A 2 C24 C 0.2830(9) 0.7680(3) 0.43027(13) 0.0441(9) Uani 1 1 d . . . H24A H 0.2963 0.7005 0.4566 0.053 Uiso 1 1 calc R A 1 H24B H 0.0734 0.7908 0.4232 0.053 Uiso 1 1 calc R A 1 C25 C 0.3779(7) 0.8717(3) 0.45871(12) 0.0333(7) Uani 1 1 d . A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0280(4) 0.0303(5) 0.0254(4) -0.0079(3) -0.0078(3) -0.0050(3) F1 0.0968(18) 0.0491(14) 0.0387(11) -0.0136(10) -0.0010(11) -0.0421(13) F2 0.0716(14) 0.0596(15) 0.0319(10) -0.0101(10) -0.0171(10) -0.0167(11) F3 0.0556(13) 0.0893(19) 0.0361(11) -0.0357(11) 0.0072(9) -0.0169(12) O1 0.0323(11) 0.0239(12) 0.0236(10) -0.0062(8) -0.0065(8) -0.0020(8) O2 0.0487(14) 0.0418(15) 0.0431(14) -0.0060(11) -0.0133(11) -0.0187(11) N1 0.0218(12) 0.0259(14) 0.0231(12) -0.0028(10) -0.0046(9) -0.0019(10) N2 0.0248(12) 0.0297(15) 0.0281(12) -0.0044(11) -0.0039(10) -0.0058(10) N3 0.0306(13) 0.0292(15) 0.0221(12) -0.0043(11) -0.0034(10) -0.0049(11) N4 0.0351(14) 0.0336(16) 0.0261(13) -0.0070(11) -0.0063(10) 0.0003(11) C1 0.0211(14) 0.0263(17) 0.0273(14) -0.0024(12) -0.0067(11) -0.0020(12) C2 0.0203(13) 0.0270(17) 0.0209(13) -0.0019(12) -0.0051(10) 0.0015(11) C3 0.0219(14) 0.0275(18) 0.0247(14) -0.0064(12) -0.0076(11) 0.0011(12) O3 0.130(3) 0.070(2) 0.0234(12) -0.0124(13) 0.0157(14) -0.0709(19) C4 0.0344(16) 0.0299(19) 0.0204(14) -0.0058(13) -0.0058(12) 0.0008(13) C5 0.0362(17) 0.0331(19) 0.0236(14) 0.0023(13) 0.0012(12) -0.0018(13) O4 0.103(2) 0.0554(19) 0.0318(13) -0.0148(12) 0.0188(13) -0.0450(17) O5 0.108(2) 0.083(2) 0.0392(14) -0.0328(15) 0.0323(15) -0.067(2) C6 0.0316(16) 0.0278(18) 0.0271(15) -0.0005(13) -0.0046(12) -0.0047(13) O6 0.136(3) 0.101(3) 0.0341(14) -0.0318(16) 0.0347(16) -0.085(2) C7 0.0259(14) 0.0269(18) 0.0205(13) -0.0058(12) -0.0045(11) 0.0014(12) C8 0.0220(15) 0.0277(18) 0.0438(19) 0.0007(15) -0.0106(13) -0.0017(12) C9 0.0304(16) 0.0278(19) 0.055(2) 0.0037(15) -0.0084(14) -0.0055(13) C10 0.0260(14) 0.0243(17) 0.0197(13) -0.0015(12) 0.0008(11) -0.0089(12) C11 0.0321(15) 0.0258(17) 0.0222(14) 0.0001(12) -0.0054(11) -0.0068(12) C12 0.0291(15) 0.0257(17) 0.0210(13) -0.0011(12) 0.0005(11) -0.0090(12) C13 0.0341(16) 0.037(2) 0.0260(15) -0.0049(14) -0.0082(12) 0.0006(14) C14 0.0332(16) 0.0262(18) 0.0225(14) -0.0028(12) 0.0003(11) -0.0104(12) C15 0.049(2) 0.045(2) 0.0340(17) -0.0164(16) -0.0144(15) 0.0093(16) C16 0.055(2) 0.040(2) 0.0438(19) -0.0227(17) -0.0108(16) 0.0081(17) C17 0.0393(17) 0.0317(19) 0.0228(14) -0.0048(13) 0.0030(12) -0.0153(14) C18 0.084(3) 0.038(2) 0.0347(18) -0.0050(16) -0.0311(18) -0.0022(19) C19 0.080(3) 0.029(2) 0.0389(19) -0.0095(16) -0.0265(18) 0.0045(18) C20 0.048(2) 0.043(2) 0.0260(16) -0.0070(15) 0.0006(14) -0.0194(16) C21 0.051(2) 0.041(2) 0.0262(16) -0.0038(15) -0.0006(14) -0.0222(16) C22 0.039(4) 0.033(4) 0.028(2) -0.006(2) 0.001(3) -0.007(2) C23 0.053(5) 0.035(4) 0.030(3) -0.002(3) 0.003(3) -0.014(3) C22B 0.039(4) 0.033(4) 0.028(2) -0.006(2) 0.001(3) -0.007(2) C23B 0.033(4) 0.032(5) 0.025(4) -0.007(3) 0.001(3) -0.007(4) C24 0.066(2) 0.045(2) 0.0269(16) -0.0032(15) 0.0027(15) -0.0276(18) C25 0.0437(18) 0.034(2) 0.0217(14) -0.0007(13) 0.0007(13) -0.0067(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C3 1.741(3) . ? S1 C1 1.742(3) . ? F1 C20 1.340(4) . ? F2 C20 1.331(4) . ? F3 C20 1.329(4) . ? O1 C10 1.356(3) . ? O1 C7 1.407(3) . ? O2 C8 1.212(4) . ? N1 C1 1.312(4) . ? N1 C2 1.384(4) . ? N2 C1 1.369(4) . ? N2 C8 1.376(4) . ? N2 H2 0.8800 . ? N3 C10 1.317(4) . ? N3 C13 1.337(4) . ? N4 C13 1.323(4) . ? N4 C12 1.360(4) . ? C2 C7 1.392(4) . ? C2 C3 1.402(4) . ? C3 C4 1.396(4) . ? O3 C21 1.296(4) . ? O3 H3 0.8400 . ? C4 C5 1.377(4) . ? C4 H4A 0.9500 . ? C5 C6 1.399(4) . ? C5 H5 0.9500 . ? O4 C21 1.189(4) . ? O5 C25 1.184(4) . ? C6 C7 1.375(4) . ? C6 H6 0.9500 . ? O6 C25 1.292(4) . ? O6 H6A 0.8400 . ? C8 C9 1.493(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.390(4) . ? C11 C12 1.374(4) . ? C11 H11 0.9500 . ? C12 C14 1.488(4) . ? C13 H13 0.9500 . ? C14 C15 1.381(4) . ? C14 C19 1.384(4) . ? C15 C16 1.376(5) . ? C15 H15 0.9500 . ? C16 C17 1.372(5) . ? C16 H17 0.9500 . ? C17 C18 1.368(5) . ? C17 C20 1.494(4) . ? C18 C19 1.381(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C21 C22B 1.498(8) . ? C21 C22 1.567(7) . ? C22 C23 1.499(10) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.451(7) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C22B C23B 1.546(12) . ? C22B H22C 0.9900 . ? C22B H22D 0.9900 . ? C23B C24 1.525(8) . ? C23B H23C 0.9900 . ? C23B H23D 0.9900 . ? C24 C25 1.496(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 S1 C1 88.50(13) . . ? C10 O1 C7 117.5(2) . . ? C1 N1 C2 109.7(2) . . ? C1 N2 C8 125.2(3) . . ? C1 N2 H2 117.4 . . ? C8 N2 H2 117.4 . . ? C10 N3 C13 114.2(2) . . ? C13 N4 C12 116.0(3) . . ? N1 C1 N2 120.0(2) . . ? N1 C1 S1 116.7(2) . . ? N2 C1 S1 123.3(2) . . ? N1 C2 C7 126.0(2) . . ? N1 C2 C3 115.6(3) . . ? C7 C2 C3 118.5(3) . . ? C4 C3 C2 121.3(3) . . ? C4 C3 S1 129.2(2) . . ? C2 C3 S1 109.5(2) . . ? C21 O3 H3 109.5 . . ? C5 C4 C3 118.3(3) . . ? C5 C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? C4 C5 C6 121.5(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C7 C6 C5 119.4(3) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C25 O6 H6A 109.5 . . ? C6 C7 C2 121.0(3) . . ? C6 C7 O1 120.8(3) . . ? C2 C7 O1 118.1(2) . . ? O2 C8 N2 121.7(3) . . ? O2 C8 C9 124.3(3) . . ? N2 C8 C9 114.0(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 O1 119.5(2) . . ? N3 C10 C11 123.9(3) . . ? O1 C10 C11 116.6(2) . . ? C12 C11 C10 117.0(3) . . ? C12 C11 H11 121.5 . . ? C10 C11 H11 121.5 . . ? N4 C12 C11 120.7(3) . . ? N4 C12 C14 115.6(3) . . ? C11 C12 C14 123.6(3) . . ? N4 C13 N3 128.2(3) . . ? N4 C13 H13 115.9 . . ? N3 C13 H13 115.9 . . ? C15 C14 C19 117.6(3) . . ? C15 C14 C12 120.0(3) . . ? C19 C14 C12 122.4(3) . . ? C16 C15 C14 121.0(3) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C17 C16 C15 120.6(3) . . ? C17 C16 H17 119.7 . . ? C15 C16 H17 119.7 . . ? C18 C17 C16 119.4(3) . . ? C18 C17 C20 121.8(3) . . ? C16 C17 C20 118.8(3) . . ? C17 C18 C19 120.0(3) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 C14 121.4(3) . . ? C18 C19 H19 119.3 . . ? C14 C19 H19 119.3 . . ? F3 C20 F2 106.3(3) . . ? F3 C20 F1 106.3(3) . . ? F2 C20 F1 106.3(3) . . ? F3 C20 C17 112.6(3) . . ? F2 C20 C17 113.3(3) . . ? F1 C20 C17 111.5(3) . . ? O4 C21 O3 123.5(3) . . ? O4 C21 C22B 118.8(4) . . ? O3 C21 C22B 115.1(4) . . ? O4 C21 C22 121.5(4) . . ? O3 C21 C22 113.5(4) . . ? C22B C21 C22 29.5(3) . . ? C23 C22 C21 111.0(5) . . ? C23 C22 H22A 109.4 . . ? C21 C22 H22A 109.4 . . ? C23 C22 H22B 109.4 . . ? C21 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C24 C23 C22 118.7(7) . . ? C24 C23 H23A 107.6 . . ? C22 C23 H23A 107.6 . . ? C24 C23 H23B 107.6 . . ? C22 C23 H23B 107.6 . . ? H23A C23 H23B 107.1 . . ? C21 C22B C23B 108.1(7) . . ? C21 C22B H22C 110.1 . . ? C23B C22B H22C 110.1 . . ? C21 C22B H22D 110.1 . . ? C23B C22B H22D 110.1 . . ? H22C C22B H22D 108.4 . . ? C24 C23B C22B 117.6(7) . . ? C24 C23B H23C 107.9 . . ? C22B C23B H23C 107.9 . . ? C24 C23B H23D 107.9 . . ? C22B C23B H23D 107.9 . . ? H23C C23B H23D 107.2 . . ? C23 C24 C25 118.8(4) . . ? C23 C24 C23B 33.3(3) . . ? C25 C24 C23B 118.0(4) . . ? C23 C24 H24A 107.6 . . ? C25 C24 H24A 107.6 . . ? C23B C24 H24A 130.6 . . ? C23 C24 H24B 107.6 . . ? C25 C24 H24B 107.6 . . ? C23B C24 H24B 77.0 . . ? H24A C24 H24B 107.1 . . ? O5 C25 O6 121.9(3) . . ? O5 C25 C24 124.7(3) . . ? O6 C25 C24 113.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 N2 -177.7(2) . . . . ? C2 N1 C1 S1 0.8(3) . . . . ? C8 N2 C1 N1 -178.4(3) . . . . ? C8 N2 C1 S1 3.2(4) . . . . ? C3 S1 C1 N1 -1.5(2) . . . . ? C3 S1 C1 N2 177.0(2) . . . . ? C1 N1 C2 C7 -179.9(3) . . . . ? C1 N1 C2 C3 0.6(3) . . . . ? N1 C2 C3 C4 177.6(2) . . . . ? C7 C2 C3 C4 -1.9(4) . . . . ? N1 C2 C3 S1 -1.6(3) . . . . ? C7 C2 C3 S1 178.8(2) . . . . ? C1 S1 C3 C4 -177.6(3) . . . . ? C1 S1 C3 C2 1.6(2) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? S1 C3 C4 C5 179.9(2) . . . . ? C3 C4 C5 C6 1.0(4) . . . . ? C4 C5 C6 C7 -1.7(4) . . . . ? C5 C6 C7 C2 0.6(4) . . . . ? C5 C6 C7 O1 176.6(2) . . . . ? N1 C2 C7 C6 -178.3(3) . . . . ? C3 C2 C7 C6 1.2(4) . . . . ? N1 C2 C7 O1 5.6(4) . . . . ? C3 C2 C7 O1 -174.9(2) . . . . ? C10 O1 C7 C6 83.3(3) . . . . ? C10 O1 C7 C2 -100.6(3) . . . . ? C1 N2 C8 O2 2.8(4) . . . . ? C1 N2 C8 C9 -178.3(3) . . . . ? C13 N3 C10 O1 -179.3(2) . . . . ? C13 N3 C10 C11 1.1(4) . . . . ? C7 O1 C10 N3 5.5(4) . . . . ? C7 O1 C10 C11 -174.8(2) . . . . ? N3 C10 C11 C12 -0.9(4) . . . . ? O1 C10 C11 C12 179.4(2) . . . . ? C13 N4 C12 C11 0.3(4) . . . . ? C13 N4 C12 C14 179.1(3) . . . . ? C10 C11 C12 N4 0.1(4) . . . . ? C10 C11 C12 C14 -178.5(3) . . . . ? C12 N4 C13 N3 -0.1(5) . . . . ? C10 N3 C13 N4 -0.6(5) . . . . ? N4 C12 C14 C15 -7.4(4) . . . . ? C11 C12 C14 C15 171.4(3) . . . . ? N4 C12 C14 C19 174.0(3) . . . . ? C11 C12 C14 C19 -7.3(5) . . . . ? C19 C14 C15 C16 0.7(5) . . . . ? C12 C14 C15 C16 -178.0(3) . . . . ? C14 C15 C16 C17 -1.2(6) . . . . ? C15 C16 C17 C18 1.0(6) . . . . ? C15 C16 C17 C20 179.3(3) . . . . ? C16 C17 C18 C19 -0.3(6) . . . . ? C20 C17 C18 C19 -178.6(3) . . . . ? C17 C18 C19 C14 -0.2(6) . . . . ? C15 C14 C19 C18 0.0(6) . . . . ? C12 C14 C19 C18 178.7(3) . . . . ? C18 C17 C20 F3 -126.1(4) . . . . ? C16 C17 C20 F3 55.6(4) . . . . ? C18 C17 C20 F2 -5.3(5) . . . . ? C16 C17 C20 F2 176.4(3) . . . . ? C18 C17 C20 F1 114.6(4) . . . . ? C16 C17 C20 F1 -63.7(4) . . . . ? O4 C21 C22 C23 43.5(8) . . . . ? O3 C21 C22 C23 -150.1(5) . . . . ? C22B C21 C22 C23 -50.3(9) . . . . ? C21 C22 C23 C24 -166.5(5) . . . . ? O4 C21 C22B C23B -60.1(8) . . . . ? O3 C21 C22B C23B 137.5(6) . . . . ? C22 C21 C22B C23B 43.7(8) . . . . ? C21 C22B C23B C24 166.5(6) . . . . ? C22 C23 C24 C25 -60.3(8) . . . . ? C22 C23 C24 C23B 37.8(8) . . . . ? C22B C23B C24 C23 -36.9(8) . . . . ? C22B C23B C24 C25 63.7(9) . . . . ? C23 C24 C25 O5 11.3(7) . . . . ? C23B C24 C25 O5 -26.7(7) . . . . ? C23 C24 C25 O6 -167.2(5) . . . . ? C23B C24 C25 O6 154.7(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 N2 H2 O4 0.88 1.97 2.842(3) 168.6 . O3 H3 N1 0.84 1.86 2.696(3) 171.1 . O6 H6A O5 0.84 1.84 2.680(4) 172.9 2_676 _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.420 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.058 # Attachment 'GYA.cif' data_GYA _database_code_depnum_ccdc_archive 'CCDC 791326' #TrackingRef 'GYA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C20 H13 F3 N4 O2 S, C2 H4 O3' _chemical_formula_sum 'C22 H17 F3 N4 O5 S' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour colourless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 506.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_int_tables_number 4 _chemical_absolute_configuration ad _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.0502(2) _cell_length_b 5.6882(2) _cell_length_c 19.3565(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.058(2) _cell_angle_gamma 90.00 _cell_volume 1098.18(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2240 _cell_measurement_theta_min 10.60 _cell_measurement_theta_max 69.00 _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 1.942 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3837 _exptl_absorpt_correction_T_max 0.8776 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83 to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Scaling and absorption corrections were performed by the SADABS program. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V6.1. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_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 836.6 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13369 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 67.76 _reflns_number_total 3906 _reflns_number_gt 3619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V5.007, 2006)' _computing_cell_refinement 'APEX2 (BRUKER, V2.1-0, 2006)' _computing_data_reduction 'SAINT (BRUKER, V7.34A, 2006)' _computing_structure_solution 'BRUKER, SHELXS-90, V6.14)' _computing_structure_refinement 'BRUKER, SHELXL-01, V6.14)' _computing_molecular_graphics 'SHELXTL (BRUKER, 2000, V6.14)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, v6.12, 2001,)' _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^)+(0.0593P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.006(17) _refine_ls_number_reflns 3906 _refine_ls_number_parameters 319 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.86504(5) 0.31953(10) 0.94488(3) 0.02432(14) Uani 1 1 d . . . F1 F -0.3204(2) -0.1411(5) 0.51067(13) 0.0793(8) Uani 1 1 d . . . F2 F -0.3750(2) 0.2130(6) 0.50795(15) 0.0890(9) Uani 1 1 d . . . F3 F -0.2403(2) 0.0820(6) 0.43933(10) 0.0736(8) Uani 1 1 d . . . O1 O 0.46503(16) -0.0393(3) 0.80283(8) 0.0251(4) Uani 1 1 d . . . O2 O 1.02586(17) 0.6655(3) 0.90796(9) 0.0328(4) Uani 1 1 d . . . N1 N 0.68552(17) 0.3034(4) 0.83497(9) 0.0221(4) Uani 1 1 d . . . N2 N 0.8421(2) 0.6032(4) 0.83046(10) 0.0265(4) Uani 1 1 d . . . H2 H 0.7979 0.6502 0.7908 0.032 Uiso 1 1 calc R . . N3 N 0.35841(18) 0.3030(4) 0.83111(10) 0.0277(4) Uani 1 1 d . . . N4 N 0.1665(2) 0.4375(4) 0.75575(12) 0.0324(5) Uani 1 1 d . . . C1 C 0.7916(2) 0.4161(4) 0.86329(12) 0.0227(4) Uani 1 1 d . . . C2 C 0.6537(2) 0.1263(4) 0.87917(12) 0.0223(4) Uani 1 1 d . . . C3 C 0.7392(2) 0.1056(4) 0.94183(12) 0.0242(5) Uani 1 1 d . . . C4 C 0.7227(2) -0.0658(5) 0.99096(12) 0.0288(5) Uani 1 1 d . . . H4 H 0.7820 -0.0757 1.0330 0.035 Uiso 1 1 calc R . . C5 C 0.6175(3) -0.2215(4) 0.97704(13) 0.0300(5) Uani 1 1 d . . . H5A H 0.6043 -0.3407 1.0099 0.036 Uiso 1 1 calc R . . C6 C 0.5302(2) -0.2056(5) 0.91508(13) 0.0285(5) Uani 1 1 d . . . H6 H 0.4584 -0.3142 0.9061 0.034 Uiso 1 1 calc R . . C7 C 0.5479(2) -0.0337(4) 0.86713(12) 0.0230(5) Uani 1 1 d . . . C8 C 0.9568(2) 0.7223(4) 0.85499(13) 0.0257(5) Uani 1 1 d . . . C9 C 0.9892(3) 0.9242(5) 0.81003(14) 0.0312(5) Uani 1 1 d . . . H9A H 1.0382 1.0448 0.8390 0.047 Uiso 1 1 calc R . . H9B H 0.9059 0.9913 0.7866 0.047 Uiso 1 1 calc R . . H9C H 1.0447 0.8682 0.7751 0.047 Uiso 1 1 calc R . . C10 C 0.3668(2) 0.1238(4) 0.78878(12) 0.0229(5) Uani 1 1 d . . . C11 C 0.2573(3) 0.4527(5) 0.81094(14) 0.0317(5) Uani 1 1 d . . . H11 H 0.2505 0.5857 0.8400 0.038 Uiso 1 1 calc R . . C12 C 0.2783(2) 0.0875(4) 0.72859(13) 0.0246(5) Uani 1 1 d . . . H12 H 0.2881 -0.0419 0.6986 0.030 Uiso 1 1 calc R . . C13 C 0.1752(2) 0.2481(4) 0.71438(12) 0.0248(5) Uani 1 1 d . . . C14 C 0.0645(2) 0.2140(5) 0.65708(12) 0.0276(5) Uani 1 1 d . . . C15 C 0.0603(4) 0.0168(7) 0.6136(2) 0.0571(10) Uani 1 1 d . . . H15 H 0.1331 -0.0907 0.6181 0.069 Uiso 1 1 calc R . . C16 C -0.0485(4) -0.0230(7) 0.5642(2) 0.0605(10) Uani 1 1 d . . . H16 H -0.0499 -0.1580 0.5352 0.073 Uiso 1 1 calc R . . C17 C -0.1539(3) 0.1292(6) 0.55665(14) 0.0383(6) Uani 1 1 d . . . C18 C -0.1504(3) 0.3251(7) 0.59806(15) 0.0448(7) Uani 1 1 d . . . H18 H -0.2233 0.4325 0.5928 0.054 Uiso 1 1 calc R . . C19 C -0.0416(3) 0.3676(5) 0.64751(15) 0.0413(7) Uani 1 1 d . . . H19 H -0.0402 0.5054 0.6753 0.050 Uiso 1 1 calc R . . C20 C -0.2719(3) 0.0760(7) 0.50323(17) 0.0502(8) Uani 1 1 d . . . O3 O 0.60464(18) 0.3352(3) 0.69419(8) 0.0309(4) Uani 1 1 d . . . H3 H 0.6283 0.3453 0.7372 0.046 Uiso 1 1 calc R . . O4 O 0.70435(17) 0.7881(3) 0.70842(10) 0.0340(4) Uani 1 1 d . . . O5 O 0.51834(17) 0.9272(3) 0.64740(9) 0.0286(4) Uani 1 1 d . . . H5 H 0.5524 1.0582 0.6592 0.043 Uiso 1 1 calc R . . C21 C 0.5933(2) 0.7585(4) 0.67806(11) 0.0245(5) Uani 1 1 d . . . C22 C 0.5219(3) 0.5257(4) 0.67230(15) 0.0333(6) Uani 1 1 d . . . H22A H 0.4464 0.5309 0.7006 0.040 Uiso 1 1 calc R . . H22B H 0.4839 0.5004 0.6232 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0219(2) 0.0261(3) 0.0230(2) 0.0017(2) -0.00516(17) -0.0027(2) F1 0.0609(13) 0.0913(19) 0.0776(15) 0.0112(14) -0.0237(11) -0.0342(13) F2 0.0445(11) 0.126(2) 0.0866(17) -0.0271(17) -0.0305(12) 0.0236(13) F3 0.0539(12) 0.131(2) 0.0316(9) 0.0029(11) -0.0117(8) -0.0228(13) O1 0.0228(8) 0.0250(9) 0.0256(8) -0.0021(7) -0.0040(6) 0.0016(6) O2 0.0263(8) 0.0378(10) 0.0321(9) 0.0017(8) -0.0046(7) -0.0054(7) N1 0.0201(8) 0.0207(9) 0.0248(8) 0.0001(9) -0.0007(7) 0.0005(8) N2 0.0245(9) 0.0284(10) 0.0252(9) 0.0049(8) -0.0021(8) -0.0012(8) N3 0.0230(8) 0.0288(10) 0.0300(9) -0.0047(10) -0.0016(7) -0.0004(9) N4 0.0277(10) 0.0291(11) 0.0385(11) -0.0046(9) -0.0032(9) 0.0022(9) C1 0.0199(10) 0.0236(10) 0.0234(10) 0.0002(9) -0.0026(8) 0.0026(9) C2 0.0220(10) 0.0229(11) 0.0216(10) -0.0009(9) 0.0009(8) 0.0034(9) C3 0.0211(10) 0.0245(12) 0.0257(11) -0.0018(9) -0.0016(9) -0.0002(9) C4 0.0287(11) 0.0336(13) 0.0225(10) 0.0008(10) -0.0029(9) 0.0022(10) C5 0.0346(12) 0.0250(13) 0.0301(11) 0.0062(10) 0.0030(9) -0.0028(10) C6 0.0250(10) 0.0279(13) 0.0322(11) -0.0024(11) 0.0016(9) -0.0052(10) C7 0.0207(10) 0.0236(12) 0.0240(10) -0.0026(9) -0.0002(8) 0.0025(8) C8 0.0204(10) 0.0262(11) 0.0303(12) -0.0038(10) 0.0030(9) 0.0001(9) C9 0.0267(11) 0.0277(12) 0.0389(13) 0.0000(11) 0.0034(10) -0.0035(10) C10 0.0194(10) 0.0228(11) 0.0266(11) 0.0021(9) 0.0031(9) -0.0019(9) C11 0.0281(12) 0.0284(13) 0.0374(13) -0.0116(11) -0.0006(10) -0.0013(10) C12 0.0237(11) 0.0213(11) 0.0286(11) -0.0029(9) 0.0024(9) -0.0025(9) C13 0.0232(10) 0.0263(12) 0.0250(10) 0.0009(9) 0.0038(9) -0.0019(8) C14 0.0241(11) 0.0326(12) 0.0256(11) 0.0019(10) 0.0012(9) 0.0003(10) C15 0.0487(19) 0.055(2) 0.059(2) -0.0225(17) -0.0265(17) 0.0211(16) C16 0.054(2) 0.060(2) 0.059(2) -0.0255(18) -0.0255(17) 0.0148(17) C17 0.0315(13) 0.0526(17) 0.0291(13) 0.0025(12) -0.0031(11) -0.0008(12) C18 0.0293(12) 0.0615(18) 0.0410(14) -0.0057(16) -0.0054(11) 0.0195(14) C19 0.0335(14) 0.0470(19) 0.0412(14) -0.0077(13) -0.0039(11) 0.0092(12) C20 0.0355(15) 0.071(2) 0.0411(16) -0.0016(15) -0.0055(13) -0.0011(15) O3 0.0433(9) 0.0190(8) 0.0278(8) 0.0010(7) -0.0058(7) 0.0023(8) O4 0.0308(8) 0.0276(9) 0.0405(9) 0.0080(8) -0.0083(7) -0.0021(7) O5 0.0336(9) 0.0191(7) 0.0310(8) 0.0012(7) -0.0040(7) 0.0037(7) C21 0.0280(11) 0.0243(12) 0.0205(10) 0.0019(8) -0.0004(9) 0.0030(8) C22 0.0319(12) 0.0238(12) 0.0413(14) 0.0036(11) -0.0079(11) 0.0000(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.747(2) . ? S1 C3 1.751(2) . ? F1 C20 1.342(5) . ? F2 C20 1.308(4) . ? F3 C20 1.315(4) . ? O1 C10 1.357(3) . ? O1 C7 1.410(3) . ? O2 C8 1.210(3) . ? N1 C1 1.306(3) . ? N1 C2 1.385(3) . ? N2 C1 1.368(3) . ? N2 C8 1.370(3) . ? N2 H2 0.8800 . ? N3 C10 1.317(3) . ? N3 C11 1.346(3) . ? N4 C11 1.320(3) . ? N4 C13 1.351(3) . ? C2 C7 1.397(3) . ? C2 C3 1.403(3) . ? C3 C4 1.386(4) . ? C4 C5 1.380(4) . ? C4 H4 0.9500 . ? C5 C6 1.399(3) . ? C5 H5A 0.9500 . ? C6 C7 1.375(4) . ? C6 H6 0.9500 . ? C8 C9 1.500(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C12 1.392(3) . ? C11 H11 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 C14 1.484(3) . ? C14 C19 1.373(4) . ? C14 C15 1.400(4) . ? C15 C16 1.379(4) . ? C15 H15 0.9500 . ? C16 C17 1.362(5) . ? C16 H16 0.9500 . ? C17 C18 1.370(5) . ? C17 C20 1.505(4) . ? C18 C19 1.383(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? O3 C22 1.399(3) . ? O3 H3 0.8400 . ? O4 C21 1.207(3) . ? O5 C21 1.315(3) . ? O5 H5 0.8400 . ? C21 C22 1.504(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C3 88.00(11) . . ? C10 O1 C7 119.83(18) . . ? C1 N1 C2 109.68(19) . . ? C1 N2 C8 124.59(19) . . ? C1 N2 H2 117.7 . . ? C8 N2 H2 117.7 . . ? C10 N3 C11 114.40(19) . . ? C11 N4 C13 116.3(2) . . ? N1 C1 N2 121.1(2) . . ? N1 C1 S1 117.21(18) . . ? N2 C1 S1 121.65(17) . . ? N1 C2 C7 126.9(2) . . ? N1 C2 C3 115.6(2) . . ? C7 C2 C3 117.5(2) . . ? C4 C3 C2 122.7(2) . . ? C4 C3 S1 127.78(18) . . ? C2 C3 S1 109.51(18) . . ? C5 C4 C3 118.1(2) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C7 C6 C5 120.4(2) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C2 120.6(2) . . ? C6 C7 O1 117.9(2) . . ? C2 C7 O1 121.1(2) . . ? O2 C8 N2 122.1(2) . . ? O2 C8 C9 123.6(2) . . ? N2 C8 C9 114.2(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 O1 120.3(2) . . ? N3 C10 C12 123.5(2) . . ? O1 C10 C12 116.1(2) . . ? N4 C11 N3 128.0(2) . . ? N4 C11 H11 116.0 . . ? N3 C11 H11 116.0 . . ? C13 C12 C10 117.0(2) . . ? C13 C12 H12 121.5 . . ? C10 C12 H12 121.5 . . ? N4 C13 C12 120.7(2) . . ? N4 C13 C14 116.7(2) . . ? C12 C13 C14 122.4(2) . . ? C19 C14 C15 117.6(2) . . ? C19 C14 C13 121.1(2) . . ? C15 C14 C13 121.2(2) . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 120.7(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 119.3(3) . . ? C16 C17 C20 118.9(3) . . ? C18 C17 C20 121.8(3) . . ? C17 C18 C19 120.5(3) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C14 C19 C18 121.1(3) . . ? C14 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? F2 C20 F3 109.6(3) . . ? F2 C20 F1 103.9(3) . . ? F3 C20 F1 104.9(3) . . ? F2 C20 C17 113.3(3) . . ? F3 C20 C17 112.3(3) . . ? F1 C20 C17 112.2(3) . . ? C22 O3 H3 109.5 . . ? C21 O5 H5 109.5 . . ? O4 C21 O5 124.2(2) . . ? O4 C21 C22 124.2(2) . . ? O5 C21 C22 111.55(19) . . ? O3 C22 C21 113.5(2) . . ? O3 C22 H22A 108.9 . . ? C21 C22 H22A 108.9 . . ? O3 C22 H22B 108.9 . . ? C21 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? 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 C2 N1 C1 N2 -178.7(2) . . . . ? C2 N1 C1 S1 0.8(3) . . . . ? C8 N2 C1 N1 -176.4(2) . . . . ? C8 N2 C1 S1 4.2(3) . . . . ? C3 S1 C1 N1 -0.7(2) . . . . ? C3 S1 C1 N2 178.8(2) . . . . ? C1 N1 C2 C7 -179.3(2) . . . . ? C1 N1 C2 C3 -0.5(3) . . . . ? N1 C2 C3 C4 -178.6(2) . . . . ? C7 C2 C3 C4 0.3(3) . . . . ? N1 C2 C3 S1 0.0(3) . . . . ? C7 C2 C3 S1 178.98(17) . . . . ? C1 S1 C3 C4 178.9(2) . . . . ? C1 S1 C3 C2 0.31(18) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? S1 C3 C4 C5 -178.34(19) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C4 C5 C6 C7 -0.2(4) . . . . ? C5 C6 C7 C2 0.5(4) . . . . ? C5 C6 C7 O1 174.1(2) . . . . ? N1 C2 C7 C6 178.2(2) . . . . ? C3 C2 C7 C6 -0.6(3) . . . . ? N1 C2 C7 O1 4.8(4) . . . . ? C3 C2 C7 O1 -174.0(2) . . . . ? C10 O1 C7 C6 108.0(2) . . . . ? C10 O1 C7 C2 -78.4(3) . . . . ? C1 N2 C8 O2 2.1(4) . . . . ? C1 N2 C8 C9 -178.8(2) . . . . ? C11 N3 C10 O1 179.5(2) . . . . ? C11 N3 C10 C12 -1.0(3) . . . . ? C7 O1 C10 N3 8.0(3) . . . . ? C7 O1 C10 C12 -171.6(2) . . . . ? C13 N4 C11 N3 0.3(4) . . . . ? C10 N3 C11 N4 1.6(4) . . . . ? N3 C10 C12 C13 -1.3(4) . . . . ? O1 C10 C12 C13 178.2(2) . . . . ? C11 N4 C13 C12 -2.8(4) . . . . ? C11 N4 C13 C14 172.9(2) . . . . ? C10 C12 C13 N4 3.3(3) . . . . ? C10 C12 C13 C14 -172.2(2) . . . . ? N4 C13 C14 C19 -0.5(4) . . . . ? C12 C13 C14 C19 175.1(3) . . . . ? N4 C13 C14 C15 -176.6(3) . . . . ? C12 C13 C14 C15 -0.9(4) . . . . ? C19 C14 C15 C16 -1.5(6) . . . . ? C13 C14 C15 C16 174.6(4) . . . . ? C14 C15 C16 C17 0.2(7) . . . . ? C15 C16 C17 C18 0.8(6) . . . . ? C15 C16 C17 C20 -178.6(4) . . . . ? C16 C17 C18 C19 -0.5(5) . . . . ? C20 C17 C18 C19 179.0(3) . . . . ? C15 C14 C19 C18 1.9(5) . . . . ? C13 C14 C19 C18 -174.3(3) . . . . ? C17 C18 C19 C14 -0.9(5) . . . . ? C16 C17 C20 F2 170.0(4) . . . . ? C18 C17 C20 F2 -9.5(5) . . . . ? C16 C17 C20 F3 -65.1(5) . . . . ? C18 C17 C20 F3 115.4(4) . . . . ? C16 C17 C20 F1 52.7(5) . . . . ? C18 C17 C20 F1 -126.7(3) . . . . ? O4 C21 C22 O3 -11.2(4) . . . . ? O5 C21 C22 O3 170.4(2) . . . . ? 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 O3 H3 N1 0.84 1.92 2.752(2) 169.0 . O5 H5 O3 0.84 1.77 2.601(3) 170.5 1_565 N2 H2 O4 0.88 1.92 2.793(3) 173.6 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.501 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.052 # Attachment 'GYA_H2O.cif' data_GYA_H2O _database_code_depnum_ccdc_archive 'CCDC 791327' #TrackingRef 'GYA_H2O.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H15.50 F3 N4 O3.75 S' _chemical_melting_point ? _exptl_crystal_description chunk _exptl_crystal_colour colourless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 472.93 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 _chemical_absolute_configuration ? 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 30.9755(4) _cell_length_b 6.79220(10) _cell_length_c 41.2428(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.5970(10) _cell_angle_gamma 90.00 _cell_volume 8649.23(19) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9878 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 67.55 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3880 _exptl_absorpt_coefficient_mu 1.886 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6479 _exptl_absorpt_correction_T_max 0.7549 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83 to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Scaling and absorption corrections were performed by the SADABS program. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V6.1. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_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 836.6 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43333 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 68.00 _reflns_number_total 7597 _reflns_number_gt 6018 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V5.007, 2006)' _computing_cell_refinement 'APEX2 (BRUKER, V2.1-0, 2006)' _computing_data_reduction 'SAINT (BRUKER, V7.34A, 2006)' _computing_structure_solution 'BRUKER, SHELXS-90, V6.14)' _computing_structure_refinement 'BRUKER, SHELXL-01, V6.14)' _computing_molecular_graphics 'SHELXTL (BRUKER, 2000, V6.14)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, v6.12, 2001,)' _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^)+(0.0837P)^2^+35.5912P] 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 ref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7597 _refine_ls_number_parameters 623 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0698 _refine_ls_wR_factor_ref 0.1923 _refine_ls_wR_factor_gt 0.1821 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.005 _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 S1A S 0.70087(3) 1.15905(14) 0.16191(2) 0.0286(2) Uani 1 1 d . . . F1A F 1.00700(8) 0.7751(5) -0.00546(7) 0.0606(8) Uani 1 1 d . . . F2A F 0.97788(10) 0.6002(5) -0.04377(8) 0.0731(10) Uani 1 1 d . . . F3A F 0.97954(10) 0.9162(6) -0.04851(8) 0.0757(10) Uani 1 1 d . . . O1A O 0.76543(10) 1.1409(5) 0.21121(7) 0.0445(7) Uani 1 1 d . . . O2A O 0.71971(9) 1.1077(4) 0.04368(6) 0.0359(6) Uani 1 1 d . . . N1A N 0.78962(10) 1.1400(5) 0.16141(8) 0.0343(7) Uani 1 1 d . . . H1A H 0.8129 1.1407 0.1505 0.041 Uiso 1 1 calc R . . N2A N 0.74774(10) 1.1294(5) 0.11221(8) 0.0310(7) Uani 1 1 d . . . N3A N 0.73235(11) 0.7800(5) 0.05704(8) 0.0362(8) Uani 1 1 d . . . N4A N 0.79566(11) 0.6200(5) 0.04026(8) 0.0392(8) Uani 1 1 d . . . C1A C 0.74987(12) 1.1417(5) 0.14355(9) 0.0291(8) Uani 1 1 d . . . C2A C 0.67408(12) 1.1530(5) 0.12316(9) 0.0267(8) Uani 1 1 d . . . C3A C 0.70462(12) 1.1332(5) 0.10016(9) 0.0291(8) Uani 1 1 d . . . C4A C 0.68958(12) 1.1158(6) 0.06751(9) 0.0313(8) Uani 1 1 d . . . C5A C 0.64607(13) 1.1217(6) 0.05828(10) 0.0349(9) Uani 1 1 d . . . H5A H 0.6362 1.1092 0.0360 0.042 Uiso 1 1 calc R . . C6A C 0.61613(13) 1.1461(6) 0.08174(10) 0.0348(9) Uani 1 1 d . . . H6A H 0.5861 1.1522 0.0751 0.042 Uiso 1 1 calc R . . C7A C 0.62967(12) 1.1613(5) 0.11441(9) 0.0306(8) Uani 1 1 d . . . H7A H 0.6094 1.1768 0.1303 0.037 Uiso 1 1 calc R . . C8A C 0.79590(13) 1.1375(6) 0.19437(10) 0.0359(9) Uani 1 1 d . . . C9A C 0.84237(14) 1.1319(8) 0.20776(11) 0.0480(11) Uani 1 1 d . . . H9A1 H 0.8438 1.1366 0.2316 0.072 Uiso 1 1 calc R . . H9A2 H 0.8578 1.2454 0.1996 0.072 Uiso 1 1 calc R . . H9A3 H 0.8559 1.0101 0.2008 0.072 Uiso 1 1 calc R . . C10A C 0.75872(14) 0.6269(7) 0.05454(11) 0.0416(10) Uani 1 1 d . . . H10A H 0.7500 0.5076 0.0642 0.050 Uiso 1 1 calc R . . C11A C 0.74493(12) 0.9432(6) 0.04311(9) 0.0322(9) Uani 1 1 d . . . C12A C 0.78273(13) 0.9577(7) 0.02722(9) 0.0353(9) Uani 1 1 d . . . H12A H 0.7909 1.0767 0.0173 0.042 Uiso 1 1 calc R . . C13A C 0.80761(13) 0.7903(7) 0.02670(9) 0.0355(9) Uani 1 1 d . . . C14A C 0.85014(13) 0.7874(6) 0.01192(9) 0.0348(9) Uani 1 1 d . . . C15A C 0.88170(14) 0.6518(7) 0.02330(10) 0.0411(10) Uani 1 1 d . . . H15A H 0.8757 0.5604 0.0398 0.049 Uiso 1 1 calc R . . C16A C 0.92158(15) 0.6500(7) 0.01069(11) 0.0451(11) Uani 1 1 d . . . H16A H 0.9429 0.5573 0.0185 0.054 Uiso 1 1 calc R . . C17A C 0.93067(13) 0.7837(7) -0.01344(9) 0.0366(9) Uani 1 1 d . . . C18A C 0.89993(14) 0.9188(7) -0.02440(10) 0.0414(10) Uani 1 1 d . . . H18A H 0.9062 1.0112 -0.0406 0.050 Uiso 1 1 calc R . . C19A C 0.85973(13) 0.9208(7) -0.01187(10) 0.0414(10) Uani 1 1 d . . . H19A H 0.8386 1.0144 -0.0197 0.050 Uiso 1 1 calc R . . C20A C 0.97351(15) 0.7717(8) -0.02777(11) 0.0481(11) Uani 1 1 d . . . S1B S 0.76591(3) 1.15326(14) 0.34352(2) 0.0302(2) Uani 1 1 d . . . F1B F 0.95691(12) 0.5681(8) 0.09465(8) 0.1005(14) Uani 1 1 d . . . F2B F 1.00620(18) 0.7774(8) 0.10296(10) 0.1227(19) Uani 1 1 d . . . F3B F 1.01854(16) 0.4948(9) 0.11635(10) 0.138(2) Uani 1 1 d . . . O1B O 0.68889(10) 1.1375(5) 0.30651(7) 0.0491(8) Uani 1 1 d . . . O2B O 0.91230(8) 1.1188(4) 0.30323(6) 0.0322(6) Uani 1 1 d . . . N1B N 0.74763(10) 1.1272(5) 0.27734(8) 0.0332(7) Uani 1 1 d . . . H1B H 0.7565 1.1216 0.2576 0.040 Uiso 1 1 calc R . . N2B N 0.81957(10) 1.1211(4) 0.29786(7) 0.0286(7) Uani 1 1 d . . . N3B N 0.91464(10) 0.7783(5) 0.30824(8) 0.0300(7) Uani 1 1 d . . . N4B N 0.93698(10) 0.5852(5) 0.26428(8) 0.0330(7) Uani 1 1 d . . . C1B C 0.77880(12) 1.1317(5) 0.30302(9) 0.0290(8) Uani 1 1 d . . . C2B C 0.82133(12) 1.1521(5) 0.35518(9) 0.0292(8) Uani 1 1 d . . . C3B C 0.84425(12) 1.1324(5) 0.32727(9) 0.0277(8) Uani 1 1 d . . . C4B C 0.88927(12) 1.1282(5) 0.33124(9) 0.0296(8) Uani 1 1 d . . . C5B C 0.91073(13) 1.1479(6) 0.36139(10) 0.0342(9) Uani 1 1 d . . . H5B H 0.9415 1.1479 0.3638 0.041 Uiso 1 1 calc R . . C6B C 0.88677(14) 1.1682(6) 0.38871(10) 0.0357(9) Uani 1 1 d . . . H6B H 0.9017 1.1814 0.4096 0.043 Uiso 1 1 calc R . . C7B C 0.84220(14) 1.1696(6) 0.38595(9) 0.0332(9) Uani 1 1 d . . . H7B H 0.8263 1.1822 0.4046 0.040 Uiso 1 1 calc R . . C8B C 0.70401(13) 1.1306(6) 0.28008(10) 0.0387(10) Uani 1 1 d . . . C9B C 0.67699(14) 1.1246(8) 0.24842(11) 0.0480(11) Uani 1 1 d . . . H9B1 H 0.6470 1.0932 0.2524 0.072 Uiso 1 1 calc R . . H9B2 H 0.6883 1.0235 0.2344 0.072 Uiso 1 1 calc R . . H9B3 H 0.6780 1.2532 0.2377 0.072 Uiso 1 1 calc R . . C10B C 0.92463(13) 0.6109(6) 0.29411(9) 0.0331(9) Uani 1 1 d . . . H10B H 0.9227 0.4952 0.3069 0.040 Uiso 1 1 calc R . . C11B C 0.91861(11) 0.9373(5) 0.29028(9) 0.0258(8) Uani 1 1 d . . . C12B C 0.93036(11) 0.9328(6) 0.25857(9) 0.0287(8) Uani 1 1 d . . . H12B H 0.9324 1.0498 0.2462 0.034 Uiso 1 1 calc R . . C13B C 0.93897(11) 0.7505(6) 0.24587(9) 0.0285(8) Uani 1 1 d . . . C14B C 0.95014(12) 0.7236(6) 0.21204(9) 0.0321(9) Uani 1 1 d . . . C15B C 0.94152(14) 0.5447(7) 0.19614(11) 0.0417(10) Uani 1 1 d . . . H15B H 0.9278 0.4418 0.2070 0.050 Uiso 1 1 calc R . . C16B C 0.95276(15) 0.5157(8) 0.16471(11) 0.0478(11) Uani 1 1 d . . . H16B H 0.9466 0.3939 0.1540 0.057 Uiso 1 1 calc R . . C17B C 0.97321(14) 0.6669(8) 0.14892(10) 0.0443(11) Uani 1 1 d . . . C18B C 0.98093(14) 0.8448(8) 0.16402(11) 0.0468(11) Uani 1 1 d . . . H18B H 0.9942 0.9480 0.1529 0.056 Uiso 1 1 calc R . . C19B C 0.96955(13) 0.8746(7) 0.19534(10) 0.0378(9) Uani 1 1 d . . . H19B H 0.9749 0.9984 0.2056 0.045 Uiso 1 1 calc R . . C20B C 0.98799(17) 0.6265(10) 0.11590(12) 0.0618(15) Uani 1 1 d . . . O4S O 0.0000 0.2718(6) 0.2500 0.0442(11) Uani 1 2 d S . . O1S O 0.8696(4) 1.1071(17) 0.1296(2) 0.077(2) Uani 0.656(6) 1 d PD A 1 O2S O 0.9082(4) 1.1122(15) 0.0772(3) 0.155(5) Uani 0.656(6) 1 d PD A 1 H2S H 0.9313 1.0473 0.0777 0.232 Uiso 0.656(6) 1 calc PR A 1 O3S O 0.8456(4) 0.7433(16) 0.1238(6) 0.097(4) Uani 0.656(6) 1 d PD A 1 H3S H 0.8599 0.7539 0.1419 0.146 Uiso 0.656(6) 1 calc PR A 1 C1S C 0.8799(2) 1.0358(12) 0.10422(18) 0.0548(19) Uani 0.656(6) 1 d PD A 1 C2S C 0.86760(19) 0.8462(9) 0.09943(15) 0.0272(13) Uani 0.656(6) 1 d PD A 1 H2S1 H 0.8939 0.7697 0.0957 0.033 Uiso 0.656(6) 1 calc PR A 1 H2S2 H 0.8486 0.8413 0.0790 0.033 Uiso 0.656(6) 1 calc PR A 1 O1D O 0.8946(4) 0.888(2) 0.0939(3) 0.077(2) Uani 0.344(6) 1 d PD A 2 O2D O 0.8703(11) 1.106(4) 0.1270(9) 0.155(5) Uani 0.344(6) 1 d PD A 2 H2D H 0.8596 1.1063 0.1451 0.232 Uiso 0.344(6) 1 calc PR A 2 O3D O 0.8439(2) 0.5394(10) 0.11867(18) 0.030(2) Uani 0.344(6) 1 d PD A 2 H3D H 0.8269 0.4798 0.1302 0.044 Uiso 0.344(6) 1 calc PR A 2 C1D C 0.8705(5) 0.902(3) 0.1139(4) 0.0548(19) Uani 0.344(6) 1 d PD A 2 C2D C 0.8357(14) 0.751(3) 0.120(2) 0.097(4) Uani 0.344(6) 1 d PD A 2 H2D1 H 0.8262 0.7791 0.1420 0.117 Uiso 0.344(6) 1 calc PR A 2 H2D2 H 0.8107 0.7790 0.1043 0.117 Uiso 0.344(6) 1 calc PR A 2 H4S H 0.0184(16) 0.360(8) 0.2428(13) 0.056(15) 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 S1A 0.0331(5) 0.0259(5) 0.0280(5) -0.0029(3) 0.0099(4) 0.0001(4) F1A 0.0327(14) 0.089(2) 0.0600(18) -0.0088(15) 0.0011(12) 0.0034(13) F2A 0.0537(18) 0.094(2) 0.076(2) -0.0391(18) 0.0285(15) 0.0001(16) F3A 0.0489(17) 0.105(3) 0.077(2) 0.0338(19) 0.0320(15) 0.0096(16) O1A 0.0420(17) 0.063(2) 0.0297(15) -0.0011(13) 0.0082(13) 0.0012(14) O2A 0.0370(15) 0.0420(17) 0.0303(14) 0.0032(11) 0.0123(11) 0.0052(12) N1A 0.0295(17) 0.041(2) 0.0330(17) -0.0041(14) 0.0077(13) -0.0030(14) N2A 0.0306(17) 0.0330(19) 0.0306(17) -0.0023(13) 0.0095(13) -0.0012(13) N3A 0.0357(18) 0.043(2) 0.0308(17) -0.0037(14) 0.0104(14) -0.0053(15) N4A 0.0397(19) 0.044(2) 0.0356(18) -0.0016(15) 0.0124(15) -0.0011(15) C1A 0.033(2) 0.023(2) 0.032(2) -0.0024(15) 0.0076(15) -0.0019(15) C2A 0.034(2) 0.0193(19) 0.0279(18) -0.0003(14) 0.0086(15) 0.0024(14) C3A 0.032(2) 0.024(2) 0.0330(19) 0.0011(15) 0.0087(15) -0.0002(15) C4A 0.036(2) 0.030(2) 0.0290(19) -0.0025(15) 0.0125(16) -0.0001(16) C5A 0.037(2) 0.035(2) 0.033(2) 0.0019(16) 0.0044(16) -0.0007(17) C6A 0.030(2) 0.032(2) 0.043(2) -0.0013(17) 0.0048(16) 0.0009(16) C7A 0.033(2) 0.023(2) 0.038(2) -0.0028(15) 0.0126(16) 0.0011(15) C8A 0.040(2) 0.033(2) 0.035(2) -0.0027(16) 0.0023(17) 0.0018(17) C9A 0.041(2) 0.060(3) 0.042(2) -0.005(2) -0.0003(19) 0.003(2) C10A 0.046(2) 0.039(3) 0.041(2) -0.0025(18) 0.0139(19) -0.0048(19) C11A 0.031(2) 0.045(3) 0.0200(17) -0.0040(16) 0.0036(14) -0.0001(17) C12A 0.034(2) 0.045(3) 0.0278(19) 0.0036(17) 0.0077(16) -0.0009(17) C13A 0.032(2) 0.052(3) 0.0236(18) 0.0004(17) 0.0049(15) -0.0001(17) C14A 0.031(2) 0.050(3) 0.0250(18) -0.0013(17) 0.0067(15) 0.0024(17) C15A 0.042(2) 0.048(3) 0.035(2) 0.0060(18) 0.0109(18) 0.0069(19) C16A 0.043(2) 0.056(3) 0.038(2) 0.002(2) 0.0078(18) 0.014(2) C17A 0.033(2) 0.048(3) 0.030(2) -0.0063(17) 0.0062(16) 0.0023(17) C18A 0.040(2) 0.056(3) 0.030(2) 0.0065(19) 0.0123(17) 0.0022(19) C19A 0.035(2) 0.056(3) 0.033(2) 0.0092(19) 0.0083(17) 0.0097(19) C20A 0.038(2) 0.065(3) 0.042(2) -0.005(2) 0.0105(19) 0.004(2) S1B 0.0353(5) 0.0281(5) 0.0289(5) -0.0001(4) 0.0131(4) 0.0032(4) F1B 0.076(2) 0.185(4) 0.0416(17) -0.040(2) 0.0125(16) -0.026(3) F2B 0.173(5) 0.139(4) 0.067(2) -0.025(2) 0.073(3) -0.058(3) F3B 0.137(4) 0.214(6) 0.069(3) -0.001(3) 0.044(3) 0.105(4) O1B 0.0390(17) 0.070(2) 0.0397(17) 0.0025(15) 0.0143(13) 0.0056(15) O2B 0.0357(14) 0.0270(15) 0.0359(14) -0.0014(11) 0.0142(11) -0.0010(11) N1B 0.0348(18) 0.038(2) 0.0275(16) 0.0021(13) 0.0077(13) 0.0022(14) N2B 0.0354(17) 0.0242(17) 0.0273(16) 0.0013(12) 0.0093(13) 0.0006(12) N3B 0.0336(17) 0.0268(18) 0.0304(16) 0.0023(13) 0.0061(13) 0.0016(13) N4B 0.0337(17) 0.0286(19) 0.0371(18) -0.0019(14) 0.0064(14) 0.0001(13) C1B 0.037(2) 0.024(2) 0.0274(18) 0.0009(14) 0.0120(15) 0.0016(15) C2B 0.038(2) 0.018(2) 0.033(2) 0.0000(14) 0.0120(16) 0.0006(15) C3B 0.037(2) 0.019(2) 0.0279(18) -0.0003(14) 0.0091(15) -0.0016(14) C4B 0.038(2) 0.022(2) 0.0307(19) -0.0015(15) 0.0105(16) -0.0017(15) C5B 0.037(2) 0.025(2) 0.040(2) -0.0029(16) 0.0034(17) 0.0008(16) C6B 0.049(2) 0.029(2) 0.029(2) -0.0037(16) 0.0010(17) 0.0018(17) C7B 0.050(2) 0.023(2) 0.0277(19) -0.0040(15) 0.0109(17) 0.0018(16) C8B 0.036(2) 0.042(3) 0.038(2) 0.0038(18) 0.0088(17) 0.0064(18) C9B 0.034(2) 0.068(3) 0.042(2) 0.002(2) 0.0051(18) 0.005(2) C10B 0.039(2) 0.027(2) 0.034(2) 0.0042(16) 0.0088(16) 0.0015(16) C11B 0.0212(17) 0.026(2) 0.0304(18) -0.0023(15) 0.0038(14) -0.0011(14) C12B 0.0233(18) 0.029(2) 0.034(2) 0.0047(15) 0.0042(14) -0.0011(14) C13B 0.0215(17) 0.031(2) 0.0327(19) -0.0006(16) 0.0022(14) -0.0020(14) C14B 0.0223(18) 0.043(2) 0.032(2) -0.0016(17) 0.0034(15) 0.0012(15) C15B 0.042(2) 0.043(3) 0.041(2) -0.0041(19) 0.0082(18) -0.0038(19) C16B 0.050(3) 0.054(3) 0.039(2) -0.016(2) 0.004(2) 0.002(2) C17B 0.032(2) 0.069(3) 0.032(2) -0.007(2) 0.0049(17) 0.002(2) C18B 0.034(2) 0.070(3) 0.037(2) 0.004(2) 0.0088(18) -0.008(2) C19B 0.032(2) 0.046(3) 0.036(2) -0.0038(18) 0.0063(16) -0.0047(17) C20B 0.045(3) 0.105(5) 0.036(3) -0.009(3) 0.012(2) 0.001(3) O4S 0.042(2) 0.027(2) 0.066(3) 0.000 0.020(2) 0.000 O1S 0.062(4) 0.119(5) 0.053(3) -0.035(3) 0.011(3) 0.016(3) O2S 0.165(9) 0.140(8) 0.177(9) -0.089(7) 0.122(8) -0.100(7) O3S 0.091(8) 0.135(6) 0.069(7) 0.020(4) 0.026(8) -0.019(4) C1S 0.045(4) 0.073(6) 0.048(4) -0.006(4) 0.018(3) -0.015(4) C2S 0.028(3) 0.031(3) 0.026(3) -0.008(2) 0.017(2) -0.006(2) O1D 0.062(4) 0.119(5) 0.053(3) -0.035(3) 0.011(3) 0.016(3) O2D 0.165(9) 0.140(8) 0.177(9) -0.089(7) 0.122(8) -0.100(7) O3D 0.041(4) 0.012(4) 0.039(4) 0.004(3) 0.019(3) 0.000(3) C1D 0.045(4) 0.073(6) 0.048(4) -0.006(4) 0.018(3) -0.015(4) C2D 0.091(8) 0.135(6) 0.069(7) 0.020(4) 0.026(8) -0.019(4) _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 S1A C2A 1.741(4) . ? S1A C1A 1.754(4) . ? F1A C20A 1.331(5) . ? F2A C20A 1.351(6) . ? F3A C20A 1.325(6) . ? O1A C8A 1.216(5) . ? O2A C11A 1.365(5) . ? O2A C4A 1.410(4) . ? N1A C8A 1.358(5) . ? N1A C1A 1.383(5) . ? N1A H1A 0.8800 . ? N2A C1A 1.292(5) . ? N2A C3A 1.388(5) . ? N3A C11A 1.321(5) . ? N3A C10A 1.332(6) . ? N4A C10A 1.329(5) . ? N4A C13A 1.349(5) . ? C2A C7A 1.395(5) . ? C2A C3A 1.399(5) . ? C3A C4A 1.394(5) . ? C4A C5A 1.371(6) . ? C5A C6A 1.403(6) . ? C5A H5A 0.9500 . ? C6A C7A 1.383(6) . ? C6A H6A 0.9500 . ? C7A H7A 0.9500 . ? C8A C9A 1.501(6) . ? C9A H9A1 0.9800 . ? C9A H9A2 0.9800 . ? C9A H9A3 0.9800 . ? C10A H10A 0.9500 . ? C11A C12A 1.391(5) . ? C12A C13A 1.375(6) . ? C12A H12A 0.9500 . ? C13A C14A 1.495(5) . ? C14A C19A 1.385(6) . ? C14A C15A 1.397(6) . ? C15A C16A 1.378(6) . ? C15A H15A 0.9500 . ? C16A C17A 1.393(6) . ? C16A H16A 0.9500 . ? C17A C18A 1.372(6) . ? C17A C20A 1.498(6) . ? C18A C19A 1.386(6) . ? C18A H18A 0.9500 . ? C19A H19A 0.9500 . ? S1B C2B 1.745(4) . ? S1B C1B 1.754(4) . ? F1B C20B 1.310(6) . ? F2B C20B 1.304(7) . ? F3B C20B 1.301(7) . ? O1B C8B 1.221(5) . ? O2B C11B 1.363(4) . ? O2B C4B 1.407(4) . ? N1B C8B 1.365(5) . ? N1B C1B 1.375(5) . ? N1B H1B 0.8800 . ? N2B C1B 1.300(5) . ? N2B C3B 1.383(5) . ? N3B C11B 1.321(5) . ? N3B C10B 1.326(5) . ? N4B C10B 1.329(5) . ? N4B C13B 1.359(5) . ? C2B C7B 1.382(6) . ? C2B C3B 1.406(5) . ? C3B C4B 1.391(5) . ? C4B C5B 1.369(6) . ? C5B C6B 1.405(6) . ? C5B H5B 0.9500 . ? C6B C7B 1.376(6) . ? C6B H6B 0.9500 . ? C7B H7B 0.9500 . ? C8B C9B 1.494(6) . ? C9B H9B1 0.9800 . ? C9B H9B2 0.9800 . ? C9B H9B3 0.9800 . ? C10B H10B 0.9500 . ? C11B C12B 1.386(5) . ? C12B C13B 1.379(6) . ? C12B H12B 0.9500 . ? C13B C14B 1.475(5) . ? C14B C15B 1.396(6) . ? C14B C19B 1.398(6) . ? C15B C16B 1.383(6) . ? C15B H15B 0.9500 . ? C16B C17B 1.395(7) . ? C16B H16B 0.9500 . ? C17B C18B 1.372(7) . ? C17B C20B 1.496(6) . ? C18B C19B 1.381(6) . ? C18B H18B 0.9500 . ? C19B H19B 0.9500 . ? O4S H4S 0.89(5) . ? O1S C1S 1.219(11) . ? O2S C1S 1.562(9) . ? O2S H2S 0.8400 . ? O3S C2S 1.442(15) . ? O3S H3S 0.8400 . ? C1S C2S 1.353(10) . ? C2S H2S1 0.9900 . ? C2S H2S2 0.9900 . ? O1D C1D 1.164(15) . ? O2D C1D 1.488(18) . ? O2D H2D 0.8400 . ? O3D C2D 1.46(2) . ? O3D H3D 0.8400 . ? C1D C2D 1.52(2) . ? C2D H2D1 0.9900 . ? C2D H2D2 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2A S1A C1A 88.13(17) . . ? C11A O2A C4A 117.1(3) . . ? C8A N1A C1A 125.7(3) . . ? C8A N1A H1A 117.2 . . ? C1A N1A H1A 117.2 . . ? C1A N2A C3A 109.1(3) . . ? C11A N3A C10A 114.7(3) . . ? C10A N4A C13A 115.3(4) . . ? N2A C1A N1A 120.3(3) . . ? N2A C1A S1A 117.4(3) . . ? N1A C1A S1A 122.3(3) . . ? C7A C2A C3A 122.3(3) . . ? C7A C2A S1A 128.6(3) . . ? C3A C2A S1A 109.0(3) . . ? N2A C3A C4A 125.6(3) . . ? N2A C3A C2A 116.3(3) . . ? C4A C3A C2A 118.1(3) . . ? C5A C4A C3A 120.7(3) . . ? C5A C4A O2A 119.9(3) . . ? C3A C4A O2A 119.2(3) . . ? C4A C5A C6A 120.1(4) . . ? C4A C5A H5A 120.0 . . ? C6A C5A H5A 120.0 . . ? C7A C6A C5A 121.0(4) . . ? C7A C6A H6A 119.5 . . ? C5A C6A H6A 119.5 . . ? C6A C7A C2A 117.7(3) . . ? C6A C7A H7A 121.1 . . ? C2A C7A H7A 121.1 . . ? O1A C8A N1A 121.1(4) . . ? O1A C8A C9A 123.8(4) . . ? N1A C8A C9A 115.1(4) . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? N4A C10A N3A 128.1(4) . . ? N4A C10A H10A 116.0 . . ? N3A C10A H10A 116.0 . . ? N3A C11A O2A 119.4(3) . . ? N3A C11A C12A 123.6(4) . . ? O2A C11A C12A 117.0(4) . . ? C13A C12A C11A 116.3(4) . . ? C13A C12A H12A 121.9 . . ? C11A C12A H12A 121.9 . . ? N4A C13A C12A 122.0(4) . . ? N4A C13A C14A 115.9(4) . . ? C12A C13A C14A 122.0(4) . . ? C19A C14A C15A 119.0(4) . . ? C19A C14A C13A 121.7(4) . . ? C15A C14A C13A 119.2(4) . . ? C16A C15A C14A 120.2(4) . . ? C16A C15A H15A 119.9 . . ? C14A C15A H15A 119.9 . . ? C15A C16A C17A 120.2(4) . . ? C15A C16A H16A 119.9 . . ? C17A C16A H16A 119.9 . . ? C18A C17A C16A 119.8(4) . . ? C18A C17A C20A 121.3(4) . . ? C16A C17A C20A 118.9(4) . . ? C17A C18A C19A 120.3(4) . . ? C17A C18A H18A 119.9 . . ? C19A C18A H18A 119.9 . . ? C14A C19A C18A 120.5(4) . . ? C14A C19A H19A 119.7 . . ? C18A C19A H19A 119.7 . . ? F3A C20A F1A 106.9(4) . . ? F3A C20A F2A 107.4(4) . . ? F1A C20A F2A 104.5(4) . . ? F3A C20A C17A 112.9(4) . . ? F1A C20A C17A 113.1(4) . . ? F2A C20A C17A 111.5(4) . . ? C2B S1B C1B 88.16(18) . . ? C11B O2B C4B 117.4(3) . . ? C8B N1B C1B 125.1(3) . . ? C8B N1B H1B 117.5 . . ? C1B N1B H1B 117.5 . . ? C1B N2B C3B 109.2(3) . . ? C11B N3B C10B 114.8(3) . . ? C10B N4B C13B 116.0(3) . . ? N2B C1B N1B 120.3(3) . . ? N2B C1B S1B 117.3(3) . . ? N1B C1B S1B 122.4(3) . . ? C7B C2B C3B 122.0(4) . . ? C7B C2B S1B 129.0(3) . . ? C3B C2B S1B 109.0(3) . . ? N2B C3B C4B 125.5(3) . . ? N2B C3B C2B 116.3(3) . . ? C4B C3B C2B 118.2(3) . . ? C5B C4B C3B 120.9(3) . . ? C5B C4B O2B 120.6(3) . . ? C3B C4B O2B 118.3(3) . . ? C4B C5B C6B 119.3(4) . . ? C4B C5B H5B 120.4 . . ? C6B C5B H5B 120.4 . . ? C7B C6B C5B 121.7(4) . . ? C7B C6B H6B 119.2 . . ? C5B C6B H6B 119.2 . . ? C6B C7B C2B 117.9(4) . . ? C6B C7B H7B 121.1 . . ? C2B C7B H7B 121.1 . . ? O1B C8B N1B 121.8(4) . . ? O1B C8B C9B 123.6(4) . . ? N1B C8B C9B 114.6(4) . . ? C8B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C8B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? N3B C10B N4B 127.9(4) . . ? N3B C10B H10B 116.1 . . ? N4B C10B H10B 116.1 . . ? N3B C11B O2B 119.8(3) . . ? N3B C11B C12B 123.7(3) . . ? O2B C11B C12B 116.5(3) . . ? C13B C12B C11B 116.8(3) . . ? C13B C12B H12B 121.6 . . ? C11B C12B H12B 121.6 . . ? N4B C13B C12B 120.7(3) . . ? N4B C13B C14B 116.8(3) . . ? C12B C13B C14B 122.5(3) . . ? C15B C14B C19B 118.7(4) . . ? C15B C14B C13B 120.1(4) . . ? C19B C14B C13B 121.2(4) . . ? C16B C15B C14B 120.8(4) . . ? C16B C15B H15B 119.6 . . ? C14B C15B H15B 119.6 . . ? C15B C16B C17B 119.4(4) . . ? C15B C16B H16B 120.3 . . ? C17B C16B H16B 120.3 . . ? C18B C17B C16B 120.4(4) . . ? C18B C17B C20B 121.3(5) . . ? C16B C17B C20B 118.3(5) . . ? C17B C18B C19B 120.4(4) . . ? C17B C18B H18B 119.8 . . ? C19B C18B H18B 119.8 . . ? C18B C19B C14B 120.3(4) . . ? C18B C19B H19B 119.8 . . ? C14B C19B H19B 119.8 . . ? F3B C20B F2B 102.0(5) . . ? F3B C20B F1B 107.2(6) . . ? F2B C20B F1B 106.4(5) . . ? F3B C20B C17B 112.8(5) . . ? F2B C20B C17B 113.7(5) . . ? F1B C20B C17B 113.7(4) . . ? O1S C1S C2S 114.4(9) . . ? O1S C1S O2S 133.0(9) . . ? C2S C1S O2S 112.3(6) . . ? C1S C2S O3S 120.2(9) . . ? C1S C2S H2S1 107.3 . . ? O3S C2S H2S1 107.3 . . ? C1S C2S H2S2 107.3 . . ? O3S C2S H2S2 107.3 . . ? H2S1 C2S H2S2 106.9 . . ? C1D O2D H2D 109.5 . . ? C2D O3D H3D 109.5 . . ? O1D C1D O2D 110.7(18) . . ? O1D C1D C2D 125(3) . . ? O2D C1D C2D 123(2) . . ? O3D C2D C1D 122(2) . . ? O3D C2D H2D1 106.8 . . ? C1D C2D H2D1 106.8 . . ? O3D C2D H2D2 106.8 . . ? C1D C2D H2D2 106.8 . . ? H2D1 C2D H2D2 106.7 . . ? 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 C3A N2A C1A N1A 179.7(3) . . . . ? C3A N2A C1A S1A 0.0(4) . . . . ? C8A N1A C1A N2A -174.9(4) . . . . ? C8A N1A C1A S1A 4.8(5) . . . . ? C2A S1A C1A N2A -1.0(3) . . . . ? C2A S1A C1A N1A 179.3(3) . . . . ? C1A S1A C2A C7A -179.8(4) . . . . ? C1A S1A C2A C3A 1.5(3) . . . . ? C1A N2A C3A C4A -177.5(4) . . . . ? C1A N2A C3A C2A 1.3(5) . . . . ? C7A C2A C3A N2A 179.3(3) . . . . ? S1A C2A C3A N2A -2.0(4) . . . . ? C7A C2A C3A C4A -1.8(5) . . . . ? S1A C2A C3A C4A 176.9(3) . . . . ? N2A C3A C4A C5A -180.0(4) . . . . ? C2A C3A C4A C5A 1.2(6) . . . . ? N2A C3A C4A O2A -5.0(6) . . . . ? C2A C3A C4A O2A 176.2(3) . . . . ? C11A O2A C4A C5A -116.4(4) . . . . ? C11A O2A C4A C3A 68.6(5) . . . . ? C3A C4A C5A C6A 0.2(6) . . . . ? O2A C4A C5A C6A -174.7(4) . . . . ? C4A C5A C6A C7A -1.1(6) . . . . ? C5A C6A C7A C2A 0.5(6) . . . . ? C3A C2A C7A C6A 1.0(5) . . . . ? S1A C2A C7A C6A -177.5(3) . . . . ? C1A N1A C8A O1A -1.7(6) . . . . ? C1A N1A C8A C9A 178.8(4) . . . . ? C13A N4A C10A N3A 0.0(7) . . . . ? C11A N3A C10A N4A 0.8(7) . . . . ? C10A N3A C11A O2A 178.6(3) . . . . ? C10A N3A C11A C12A -0.5(6) . . . . ? C4A O2A C11A N3A 20.1(5) . . . . ? C4A O2A C11A C12A -160.7(3) . . . . ? N3A C11A C12A C13A -0.4(6) . . . . ? O2A C11A C12A C13A -179.6(3) . . . . ? C10A N4A C13A C12A -1.1(6) . . . . ? C10A N4A C13A C14A 177.2(4) . . . . ? C11A C12A C13A N4A 1.3(6) . . . . ? C11A C12A C13A C14A -176.9(4) . . . . ? N4A C13A C14A C19A 157.3(4) . . . . ? C12A C13A C14A C19A -24.4(6) . . . . ? N4A C13A C14A C15A -25.2(6) . . . . ? C12A C13A C14A C15A 153.0(4) . . . . ? C19A C14A C15A C16A -0.7(7) . . . . ? C13A C14A C15A C16A -178.2(4) . . . . ? C14A C15A C16A C17A 0.1(7) . . . . ? C15A C16A C17A C18A 0.7(7) . . . . ? C15A C16A C17A C20A -177.1(4) . . . . ? C16A C17A C18A C19A -0.9(7) . . . . ? C20A C17A C18A C19A 176.8(4) . . . . ? C15A C14A C19A C18A 0.5(7) . . . . ? C13A C14A C19A C18A 177.9(4) . . . . ? C17A C18A C19A C14A 0.3(7) . . . . ? C18A C17A C20A F3A 7.4(6) . . . . ? C16A C17A C20A F3A -174.9(4) . . . . ? C18A C17A C20A F1A 129.0(5) . . . . ? C16A C17A C20A F1A -53.3(6) . . . . ? C18A C17A C20A F2A -113.7(5) . . . . ? C16A C17A C20A F2A 64.1(5) . . . . ? C3B N2B C1B N1B 178.8(3) . . . . ? C3B N2B C1B S1B -0.7(4) . . . . ? C8B N1B C1B N2B 177.7(4) . . . . ? C8B N1B C1B S1B -2.8(5) . . . . ? C2B S1B C1B N2B 1.0(3) . . . . ? C2B S1B C1B N1B -178.6(3) . . . . ? C1B S1B C2B C7B 178.2(4) . . . . ? C1B S1B C2B C3B -0.9(3) . . . . ? C1B N2B C3B C4B -179.3(4) . . . . ? C1B N2B C3B C2B 0.0(4) . . . . ? C7B C2B C3B N2B -178.4(3) . . . . ? S1B C2B C3B N2B 0.7(4) . . . . ? C7B C2B C3B C4B 0.9(5) . . . . ? S1B C2B C3B C4B -180.0(3) . . . . ? N2B C3B C4B C5B 177.5(4) . . . . ? C2B C3B C4B C5B -1.7(5) . . . . ? N2B C3B C4B O2B 2.4(5) . . . . ? C2B C3B C4B O2B -176.8(3) . . . . ? C11B O2B C4B C5B 100.2(4) . . . . ? C11B O2B C4B C3B -84.7(4) . . . . ? C3B C4B C5B C6B 1.5(6) . . . . ? O2B C4B C5B C6B 176.4(3) . . . . ? C4B C5B C6B C7B -0.3(6) . . . . ? C5B C6B C7B C2B -0.6(6) . . . . ? C3B C2B C7B C6B 0.3(6) . . . . ? S1B C2B C7B C6B -178.7(3) . . . . ? C1B N1B C8B O1B -0.3(7) . . . . ? C1B N1B C8B C9B 179.9(4) . . . . ? C11B N3B C10B N4B -1.7(6) . . . . ? C13B N4B C10B N3B -1.1(6) . . . . ? C10B N3B C11B O2B -175.1(3) . . . . ? C10B N3B C11B C12B 2.8(5) . . . . ? C4B O2B C11B N3B -19.0(5) . . . . ? C4B O2B C11B C12B 162.9(3) . . . . ? N3B C11B C12B C13B -1.2(5) . . . . ? O2B C11B C12B C13B 176.8(3) . . . . ? C10B N4B C13B C12B 2.7(5) . . . . ? C10B N4B C13B C14B -176.5(3) . . . . ? C11B C12B C13B N4B -1.7(5) . . . . ? C11B C12B C13B C14B 177.5(3) . . . . ? N4B C13B C14B C15B 25.4(5) . . . . ? C12B C13B C14B C15B -153.8(4) . . . . ? N4B C13B C14B C19B -154.3(4) . . . . ? C12B C13B C14B C19B 26.4(6) . . . . ? C19B C14B C15B C16B 1.3(6) . . . . ? C13B C14B C15B C16B -178.4(4) . . . . ? C14B C15B C16B C17B 0.5(7) . . . . ? C15B C16B C17B C18B -2.0(7) . . . . ? C15B C16B C17B C20B 175.5(4) . . . . ? C16B C17B C18B C19B 1.7(7) . . . . ? C20B C17B C18B C19B -175.7(4) . . . . ? C17B C18B C19B C14B 0.2(7) . . . . ? C15B C14B C19B C18B -1.7(6) . . . . ? C13B C14B C19B C18B 178.1(4) . . . . ? C18B C17B C20B F3B 112.2(6) . . . . ? C16B C17B C20B F3B -65.2(7) . . . . ? C18B C17B C20B F2B -3.4(7) . . . . ? C16B C17B C20B F2B 179.2(5) . . . . ? C18B C17B C20B F1B -125.4(6) . . . . ? C16B C17B C20B F1B 57.1(7) . . . . ? O1S C1S C2S O3S -2.0(14) . . . . ? O2S C1S C2S O3S 172.8(10) . . . . ? O1D C1D C2D O3D 40(8) . . . . ? O2D C1D C2D O3D -156(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 N1A H1A O1S 0.88 2.03 2.902(11) 171.2 . N1A H1A O2D 0.88 2.11 2.98(3) 172.6 . N1B H1B O1A 0.88 1.96 2.827(4) 168.2 . O2D H2D N1A 0.84 2.33 2.98(3) 134.3 . O4S H4S N4B 0.89(5) 2.10(5) 2.979(4) 168(5) 2_655 _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 68.00 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 1.156 _refine_diff_density_min -0.635 _refine_diff_density_rms 0.078 # Attachment 'HCA_1.cif' data_HCA_1 _database_code_depnum_ccdc_archive 'CCDC 791328' #TrackingRef 'HCA_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C20 H13 F3 N4 O2 S, C6 H11 O3' _chemical_formula_sum 'C26 H24 F3 N4 O5 S' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colourless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 561.55 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.7288(11) _cell_length_b 9.1387(19) _cell_length_c 30.731(6) _cell_angle_alpha 93.847(14) _cell_angle_beta 94.068(15) _cell_angle_gamma 98.881(14) _cell_volume 1304.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 402 _cell_measurement_theta_min 4.34 _cell_measurement_theta_max 30.74 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 582 _exptl_absorpt_coefficient_mu 1.691 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5213 _exptl_absorpt_correction_T_max 0.9172 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83 to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Scaling and absorption corrections were performed by the SADABS program. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V6.1. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_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 836.6 _diffrn_reflns_number 15978 _diffrn_reflns_av_R_equivalents 0.1657 _diffrn_reflns_av_sigmaI/netI 0.1646 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 67.99 _reflns_number_total 4520 _reflns_number_gt 2051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.58, 2007)' _computing_cell_refinement 'APEX2 (BRUKER, V5-0, 2008)' _computing_data_reduction 'SAINT (BRUKER, V7.56A, 2008)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.1593P)^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 4520 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1900 _refine_ls_R_factor_gt 0.1015 _refine_ls_wR_factor_ref 0.3340 _refine_ls_wR_factor_gt 0.2674 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.7154(4) 0.51915(19) 0.45543(6) 0.0630(6) Uani 1 1 d . . . F1 F 1.312(3) 0.8521(19) 0.0322(3) 0.260(7) Uani 1 1 d . . . F2 F 0.906(3) 0.793(4) 0.0207(4) 0.44(2) Uani 1 1 d . . . F3 F 1.145(7) 0.6553(14) 0.0267(4) 0.367(15) Uani 1 1 d . . . O1 O 1.2631(10) 0.6688(5) 0.32896(16) 0.0685(13) Uani 1 1 d . . . O2 O 0.2633(10) 0.2953(6) 0.45450(17) 0.0740(14) Uani 1 1 d . . . N1 N 0.8180(12) 0.4989(6) 0.37330(18) 0.0599(14) Uani 1 1 d . . . N2 N 0.4350(11) 0.3272(6) 0.38881(19) 0.0633(15) Uani 1 1 d . . . H2 H 0.4168 0.2939 0.3611 0.076 Uiso 1 1 calc R . . N3 N 0.9469(14) 0.8338(7) 0.3172(2) 0.0733(17) Uani 1 1 d . . . N4 N 0.8201(14) 0.8893(8) 0.2446(2) 0.0800(18) Uani 1 1 d . . . C1 C 0.6480(14) 0.4450(7) 0.4019(2) 0.0624(17) Uani 1 1 d . . . C2 C 0.9973(14) 0.6437(7) 0.4387(2) 0.0582(16) Uani 1 1 d . . . C3 C 1.0223(14) 0.6137(7) 0.3944(2) 0.0600(17) Uani 1 1 d . . . C4 C 1.2391(14) 0.7006(7) 0.3742(2) 0.0597(17) Uani 1 1 d . . . C5 C 1.4242(15) 0.8076(7) 0.3983(2) 0.0644(18) Uani 1 1 d . . . H5A H 1.5739 0.8642 0.3847 0.077 Uiso 1 1 calc R . . C6 C 1.4004(15) 0.8363(8) 0.4421(2) 0.0656(18) Uani 1 1 d . . . H6 H 1.5342 0.9126 0.4582 0.079 Uiso 1 1 calc R . . C7 C 1.1838(15) 0.7561(7) 0.4639(2) 0.0632(17) Uani 1 1 d . . . H7 H 1.1649 0.7772 0.4941 0.076 Uiso 1 1 calc R . . C8 C 0.2476(15) 0.2575(8) 0.4162(3) 0.0649(18) Uani 1 1 d . . . C9 C 0.0298(16) 0.1348(8) 0.3941(3) 0.0725(19) Uani 1 1 d . . . H9A H 0.1270 0.0565 0.3817 0.109 Uiso 1 1 calc R . . H9B H -0.0821 0.1733 0.3707 0.109 Uiso 1 1 calc R . . H9C H -0.0989 0.0940 0.4155 0.109 Uiso 1 1 calc R . . C10 C 1.1120(16) 0.7414(8) 0.3011(2) 0.0657(18) Uani 1 1 d . . . C11 C 1.1424(17) 0.7170(9) 0.2569(3) 0.076(2) Uani 1 1 d . . . H11 H 1.2586 0.6484 0.2464 0.092 Uiso 1 1 calc R . . C12 C 0.9968(18) 0.7964(9) 0.2286(3) 0.080(2) Uani 1 1 d . . . C13 C 0.8070(18) 0.9017(9) 0.2870(3) 0.076(2) Uani 1 1 d . . . H13 H 0.6840 0.9663 0.2976 0.091 Uiso 1 1 calc R . . C14 C 1.016(2) 0.7860(11) 0.1812(3) 0.093(3) Uani 1 1 d . . . C15 C 1.166(3) 0.6888(18) 0.1599(4) 0.158(6) Uani 1 1 d . . . H15 H 1.2558 0.6215 0.1763 0.189 Uiso 1 1 calc R . . C16 C 1.188(4) 0.688(2) 0.1144(4) 0.182(7) Uani 1 1 d . . . H16 H 1.2927 0.6191 0.1007 0.218 Uiso 1 1 calc R . . C17 C 1.067(3) 0.7795(15) 0.0903(3) 0.120(4) Uani 1 1 d . . . C18 C 0.923(4) 0.8755(17) 0.1109(4) 0.155(5) Uani 1 1 d . . . H18 H 0.8338 0.9425 0.0943 0.186 Uiso 1 1 calc R . . C19 C 0.901(3) 0.8794(15) 0.1552(3) 0.133(4) Uani 1 1 d . . . H19 H 0.8002 0.9508 0.1683 0.159 Uiso 1 1 calc R . . C20 C 1.083(5) 0.794(3) 0.0417(6) 0.211(11) Uani 1 1 d . . . O3 O 0.7934(16) 0.4095(7) 0.2872(2) 0.110(2) Uani 1 1 d . . . H3 H 0.7482 0.4491 0.3106 0.165 Uiso 1 1 calc R . . O4 O 0.4752(13) 0.2163(6) 0.30221(18) 0.0916(17) Uani 1 1 d . . . O5 O 0.4409(15) 0.0908(7) 0.2193(2) 0.106(2) Uani 1 1 d . . . H5 H 0.5193 0.0170 0.2249 0.159 Uiso 1 1 calc R . . C21 C 0.620(2) 0.2832(9) 0.2766(3) 0.081(2) Uani 1 1 d . . . C22 C 0.645(2) 0.2252(9) 0.2301(3) 0.093(3) Uani 1 1 d . . . H22 H 0.8446 0.2074 0.2259 0.112 Uiso 1 1 calc R . . C23 C 0.553(3) 0.3294(13) 0.1986(3) 0.135(4) Uani 1 1 d . . . H23A H 0.6644 0.4301 0.2060 0.162 Uiso 1 1 calc R . . H23B H 0.3470 0.3351 0.2003 0.162 Uiso 1 1 calc R . . C24 C 0.607(5) 0.2715(17) 0.1513(4) 0.203(9) Uani 1 1 d . . . H24 H 0.6724 0.1793 0.1459 0.244 Uiso 1 1 calc R . . C25 C 0.561(6) 0.351(3) 0.1213(5) 0.279(14) Uani 1 1 d . . . H25A H 0.6882 0.4476 0.1284 0.335 Uiso 1 1 calc R . . H25B H 0.3616 0.3700 0.1224 0.335 Uiso 1 1 calc R . . C26 C 0.599(4) 0.300(2) 0.0730(4) 0.218(9) Uani 1 1 d . . . H26A H 0.7251 0.2250 0.0724 0.326 Uiso 1 1 calc R . . H26B H 0.6834 0.3861 0.0581 0.326 Uiso 1 1 calc R . . H26C H 0.4107 0.2584 0.0581 0.326 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0604(10) 0.0652(10) 0.0661(11) 0.0084(8) 0.0201(8) 0.0100(8) F1 0.248(13) 0.42(2) 0.092(6) 0.032(9) 0.060(7) -0.022(13) F2 0.167(10) 1.10(6) 0.066(6) 0.016(15) 0.011(6) 0.13(2) F3 0.81(5) 0.180(9) 0.100(7) -0.002(7) 0.136(16) 0.022(17) O1 0.067(3) 0.075(3) 0.068(3) 0.008(2) 0.026(2) 0.014(2) O2 0.074(3) 0.077(3) 0.071(3) 0.005(3) 0.022(3) 0.003(3) N1 0.063(3) 0.061(3) 0.061(3) 0.009(3) 0.020(3) 0.016(3) N2 0.054(3) 0.070(3) 0.067(4) -0.003(3) 0.014(3) 0.013(3) N3 0.077(4) 0.071(4) 0.073(4) 0.009(3) 0.026(3) 0.004(3) N4 0.087(4) 0.086(4) 0.069(4) 0.008(3) 0.017(3) 0.013(4) C1 0.054(4) 0.058(4) 0.080(5) 0.011(3) 0.013(3) 0.018(3) C2 0.058(4) 0.059(4) 0.062(4) 0.010(3) 0.014(3) 0.019(3) C3 0.053(4) 0.064(4) 0.068(4) 0.008(3) 0.015(3) 0.019(3) C4 0.058(4) 0.062(4) 0.066(4) 0.014(3) 0.020(3) 0.020(3) C5 0.065(4) 0.059(4) 0.074(5) 0.012(3) 0.025(4) 0.011(3) C6 0.063(4) 0.064(4) 0.070(5) 0.011(3) 0.009(3) 0.004(3) C7 0.071(4) 0.062(4) 0.063(4) 0.010(3) 0.016(3) 0.021(4) C8 0.062(4) 0.062(4) 0.077(5) 0.008(4) 0.028(4) 0.016(3) C9 0.070(4) 0.068(4) 0.078(5) 0.009(4) 0.015(4) 0.003(4) C10 0.066(4) 0.060(4) 0.072(5) 0.013(3) 0.018(4) 0.004(4) C11 0.074(5) 0.082(5) 0.077(5) 0.007(4) 0.026(4) 0.013(4) C12 0.087(5) 0.082(5) 0.068(5) -0.002(4) 0.020(4) -0.001(4) C13 0.084(5) 0.070(4) 0.076(5) 0.011(4) 0.018(4) 0.010(4) C14 0.108(7) 0.095(6) 0.071(5) 0.005(5) 0.021(5) -0.002(5) C15 0.221(15) 0.203(14) 0.079(7) 0.015(8) 0.038(8) 0.117(13) C16 0.27(2) 0.223(16) 0.089(9) 0.015(10) 0.060(10) 0.143(17) C17 0.156(10) 0.137(9) 0.068(6) 0.021(6) 0.028(6) 0.013(8) C18 0.228(16) 0.166(13) 0.086(8) 0.014(8) 0.024(9) 0.071(12) C19 0.192(12) 0.145(10) 0.078(7) 0.010(6) 0.031(7) 0.069(10) C20 0.176(17) 0.32(3) 0.095(12) -0.095(15) 0.055(12) -0.049(17) O3 0.150(6) 0.092(4) 0.076(4) -0.010(3) 0.041(4) -0.026(4) O4 0.109(4) 0.083(3) 0.079(4) 0.006(3) 0.029(3) -0.004(3) O5 0.122(5) 0.104(4) 0.089(4) -0.005(4) 0.021(4) 0.010(4) C21 0.100(6) 0.073(5) 0.069(5) 0.008(4) 0.014(4) 0.008(5) C22 0.124(7) 0.082(5) 0.071(5) 0.005(4) 0.022(5) 0.002(5) C23 0.197(13) 0.118(8) 0.081(7) 0.007(6) 0.000(7) 0.000(9) C24 0.39(3) 0.142(11) 0.056(6) 0.017(7) -0.006(11) -0.007(14) C25 0.32(3) 0.39(4) 0.106(13) -0.044(18) 0.057(16) -0.02(3) C26 0.25(2) 0.31(3) 0.094(10) 0.001(12) 0.020(11) 0.067(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.725(7) . ? S1 C2 1.744(7) . ? F1 C20 1.194(19) . ? F2 C20 1.02(2) . ? F3 C20 1.40(3) . ? O1 C10 1.350(9) . ? O1 C4 1.417(8) . ? O2 C8 1.199(8) . ? N1 C1 1.303(9) . ? N1 C3 1.400(9) . ? N2 C1 1.373(9) . ? N2 C8 1.379(9) . ? N2 H2 0.8800 . ? N3 C10 1.331(9) . ? N3 C13 1.343(10) . ? N4 C13 1.307(10) . ? N4 C12 1.371(10) . ? C2 C3 1.390(9) . ? C2 C7 1.395(10) . ? C3 C4 1.404(9) . ? C4 C5 1.348(10) . ? C5 C6 1.370(10) . ? C5 H5A 0.9500 . ? C6 C7 1.402(9) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.490(10) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.381(10) . ? C11 C12 1.383(12) . ? C11 H11 0.9500 . ? C12 C14 1.465(11) . ? C13 H13 0.9500 . ? C14 C19 1.354(14) . ? C14 C15 1.378(14) . ? C15 C16 1.409(16) . ? C15 H15 0.9500 . ? C16 C17 1.326(17) . ? C16 H16 0.9500 . ? C17 C18 1.343(17) . ? C17 C20 1.51(2) . ? C18 C19 1.373(15) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? O3 C21 1.316(10) . ? O3 H3 0.8400 . ? O4 C21 1.213(9) . ? O5 C22 1.442(10) . ? O5 H5 0.8400 . ? C21 C22 1.510(11) . ? C22 C23 1.489(14) . ? C22 H22 1.0000 . ? C23 C24 1.564(18) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.24(3) . ? C24 H24 0.9500 . ? C25 C26 1.555(19) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C2 88.3(3) . . ? C10 O1 C4 116.6(5) . . ? C1 N1 C3 108.7(6) . . ? C1 N2 C8 124.5(6) . . ? C1 N2 H2 117.8 . . ? C8 N2 H2 117.8 . . ? C10 N3 C13 114.6(7) . . ? C13 N4 C12 116.9(7) . . ? N1 C1 N2 118.9(7) . . ? N1 C1 S1 118.0(5) . . ? N2 C1 S1 123.0(5) . . ? C3 C2 C7 121.9(6) . . ? C3 C2 S1 109.5(5) . . ? C7 C2 S1 128.6(5) . . ? C2 C3 N1 115.5(6) . . ? C2 C3 C4 118.9(6) . . ? N1 C3 C4 125.5(6) . . ? C5 C4 C3 119.7(6) . . ? C5 C4 O1 121.8(6) . . ? C3 C4 O1 118.4(6) . . ? C4 C5 C6 121.3(6) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C5 C6 C7 121.7(6) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C2 C7 C6 116.4(6) . . ? C2 C7 H7 121.8 . . ? C6 C7 H7 121.8 . . ? O2 C8 N2 121.3(6) . . ? O2 C8 C9 124.0(7) . . ? N2 C8 C9 114.6(7) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 O1 119.0(7) . . ? N3 C10 C11 123.5(7) . . ? O1 C10 C11 117.5(7) . . ? C10 C11 C12 117.3(7) . . ? C10 C11 H11 121.4 . . ? C12 C11 H11 121.4 . . ? N4 C12 C11 120.0(7) . . ? N4 C12 C14 116.6(8) . . ? C11 C12 C14 123.4(8) . . ? N4 C13 N3 127.7(8) . . ? N4 C13 H13 116.2 . . ? N3 C13 H13 116.2 . . ? C19 C14 C15 115.0(10) . . ? C19 C14 C12 121.6(9) . . ? C15 C14 C12 123.3(10) . . ? C14 C15 C16 121.1(12) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C17 C16 C15 121.7(12) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C16 C17 C18 117.5(11) . . ? C16 C17 C20 127.1(17) . . ? C18 C17 C20 115.4(16) . . ? C17 C18 C19 121.8(13) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? C14 C19 C18 123.0(12) . . ? C14 C19 H19 118.5 . . ? C18 C19 H19 118.5 . . ? F2 C20 F1 119(3) . . ? F2 C20 F3 97(2) . . ? F1 C20 F3 90(2) . . ? F2 C20 C17 123(2) . . ? F1 C20 C17 113.9(16) . . ? F3 C20 C17 103(2) . . ? C21 O3 H3 109.5 . . ? C22 O5 H5 109.5 . . ? O4 C21 O3 123.9(7) . . ? O4 C21 C22 124.3(7) . . ? O3 C21 C22 111.6(7) . . ? O5 C22 C23 103.7(8) . . ? O5 C22 C21 109.6(7) . . ? C23 C22 C21 110.7(8) . . ? O5 C22 H22 110.9 . . ? C23 C22 H22 110.9 . . ? C21 C22 H22 110.9 . . ? C22 C23 C24 108.8(11) . . ? C22 C23 H23A 109.9 . . ? C24 C23 H23A 109.9 . . ? C22 C23 H23B 109.9 . . ? C24 C23 H23B 109.9 . . ? H23A C23 H23B 108.3 . . ? C25 C24 C23 117.3(19) . . ? C25 C24 H24 121.3 . . ? C23 C24 H24 121.3 . . ? C24 C25 C26 121(2) . . ? C24 C25 H25A 107.0 . . ? C26 C25 H25A 107.0 . . ? C24 C25 H25B 107.0 . . ? C26 C25 H25B 107.0 . . ? H25A C25 H25B 106.8 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 C3 N1 C1 N2 -177.9(6) . . . . ? C3 N1 C1 S1 -1.5(7) . . . . ? C8 N2 C1 N1 177.9(6) . . . . ? C8 N2 C1 S1 1.7(9) . . . . ? C2 S1 C1 N1 2.4(6) . . . . ? C2 S1 C1 N2 178.6(6) . . . . ? C1 S1 C2 C3 -2.4(5) . . . . ? C1 S1 C2 C7 179.2(7) . . . . ? C7 C2 C3 N1 -179.3(6) . . . . ? S1 C2 C3 N1 2.2(7) . . . . ? C7 C2 C3 C4 -0.9(10) . . . . ? S1 C2 C3 C4 -179.4(5) . . . . ? C1 N1 C3 C2 -0.5(8) . . . . ? C1 N1 C3 C4 -178.8(7) . . . . ? C2 C3 C4 C5 2.2(10) . . . . ? N1 C3 C4 C5 -179.6(6) . . . . ? C2 C3 C4 O1 179.8(6) . . . . ? N1 C3 C4 O1 -2.0(10) . . . . ? C10 O1 C4 C5 -92.1(8) . . . . ? C10 O1 C4 C3 90.3(7) . . . . ? C3 C4 C5 C6 -1.8(10) . . . . ? O1 C4 C5 C6 -179.4(6) . . . . ? C4 C5 C6 C7 0.1(11) . . . . ? C3 C2 C7 C6 -0.8(10) . . . . ? S1 C2 C7 C6 177.4(5) . . . . ? C5 C6 C7 C2 1.2(10) . . . . ? C1 N2 C8 O2 -1.4(11) . . . . ? C1 N2 C8 C9 178.4(6) . . . . ? C13 N3 C10 O1 179.5(6) . . . . ? C13 N3 C10 C11 0.7(10) . . . . ? C4 O1 C10 N3 -1.7(8) . . . . ? C4 O1 C10 C11 177.2(6) . . . . ? N3 C10 C11 C12 1.5(11) . . . . ? O1 C10 C11 C12 -177.3(6) . . . . ? C13 N4 C12 C11 2.4(11) . . . . ? C13 N4 C12 C14 -178.5(7) . . . . ? C10 C11 C12 N4 -3.1(11) . . . . ? C10 C11 C12 C14 177.8(7) . . . . ? C12 N4 C13 N3 0.0(11) . . . . ? C10 N3 C13 N4 -1.5(11) . . . . ? N4 C12 C14 C19 9.6(13) . . . . ? C11 C12 C14 C19 -171.2(10) . . . . ? N4 C12 C14 C15 -174.6(11) . . . . ? C11 C12 C14 C15 4.5(15) . . . . ? C19 C14 C15 C16 -1(2) . . . . ? C12 C14 C15 C16 -177.3(13) . . . . ? C14 C15 C16 C17 0(3) . . . . ? C15 C16 C17 C18 1(3) . . . . ? C15 C16 C17 C20 177.5(16) . . . . ? C16 C17 C18 C19 0(2) . . . . ? C20 C17 C18 C19 -177.2(15) . . . . ? C15 C14 C19 C18 2(2) . . . . ? C12 C14 C19 C18 178.0(12) . . . . ? C17 C18 C19 C14 -1(2) . . . . ? C16 C17 C20 F2 130(4) . . . . ? C18 C17 C20 F2 -53(4) . . . . ? C16 C17 C20 F1 -72(3) . . . . ? C18 C17 C20 F1 105(3) . . . . ? C16 C17 C20 F3 23(3) . . . . ? C18 C17 C20 F3 -160(2) . . . . ? O4 C21 C22 O5 8.3(14) . . . . ? O3 C21 C22 O5 -177.3(8) . . . . ? O4 C21 C22 C23 122.1(11) . . . . ? O3 C21 C22 C23 -63.5(12) . . . . ? O5 C22 C23 C24 -67.2(13) . . . . ? C21 C22 C23 C24 175.3(11) . . . . ? C22 C23 C24 C25 -175(2) . . . . ? C23 C24 C25 C26 -177.9(16) . . . . ? 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 N2 H2 O4 0.88 1.95 2.813(8) 166.0 . O3 H3 N1 0.84 1.94 2.705(8) 150.6 . O5 H5 N4 0.84 2.06 2.867(10) 161.7 1_545 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.446 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.075 # Attachment 'HCA_2.cif' data_HCA_2 _database_code_depnum_ccdc_archive 'CCDC 791329' #TrackingRef 'HCA_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety '(C20 H13 F3 N4 O2 S), (C6 H12 O6)' _chemical_formula_sum 'C26 H25 F3 N4 O5 S' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour colourless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 562.56 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.83410(10) _cell_length_b 20.1082(5) _cell_length_c 27.8986(9) _cell_angle_alpha 76.1140(10) _cell_angle_beta 88.138(2) _cell_angle_gamma 88.3180(10) _cell_volume 2630.59(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4209 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 1.677 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4883 _exptl_absorpt_correction_T_max 0.9003 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83 to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Scaling and absorption corrections were performed by the SADABS program. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V6.1. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_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 836.6 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32594 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 68.17 _reflns_number_total 9097 _reflns_number_gt 7355 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V5.007, 2006)' _computing_cell_refinement 'APEX2 (BRUKER, V2.1-0, 2006)' _computing_data_reduction 'SAINT (BRUKER, V7.34A, 2006)' _computing_structure_solution 'BRUKER, SHELXS-90, V6.14)' _computing_structure_refinement 'BRUKER, SHELXL-01, V6.14)' _computing_molecular_graphics 'SHELXTL (BRUKER, 2000, V6.14)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, v6.12, 2001,)' _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^)+(0.0708P)^2^+0.6569P] 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 9097 _refine_ls_number_parameters 721 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1323 _refine_ls_wR_factor_gt 0.1243 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.059 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1A S 0.34709(11) 0.39005(3) 0.424092(19) 0.02626(14) Uani 1 1 d . . . F1A F -0.5717(9) -0.1570(2) 0.77060(15) 0.1049(14) Uani 0.706(4) 1 d PD A 1 F2A F -0.1678(11) -0.1806(3) 0.78105(15) 0.1162(16) Uani 0.706(4) 1 d PD A 1 F3A F -0.372(2) -0.2357(2) 0.7379(2) 0.189(5) Uani 0.706(4) 1 d PD A 1 F1AA F -0.589(2) -0.2048(6) 0.7351(4) 0.1049(14) Uani 0.294(4) 1 d PD A 2 F2AA F -0.350(3) -0.1638(7) 0.7832(4) 0.1162(16) Uani 0.294(4) 1 d PD A 2 F3AA F -0.181(4) -0.2292(6) 0.7489(6) 0.189(5) Uani 0.294(4) 1 d PD A 2 O1A O -0.2643(3) 0.19578(7) 0.49788(6) 0.0279(3) Uani 1 1 d . . . O2A O 0.7073(4) 0.44993(8) 0.47103(6) 0.0362(4) Uani 1 1 d . . . N1A N 0.1512(4) 0.29589(9) 0.49750(7) 0.0246(4) Uani 1 1 d . . . N2A N 0.4820(4) 0.36229(9) 0.52143(7) 0.0269(4) Uani 1 1 d . . . H2A H 0.4613 0.3377 0.5519 0.032 Uiso 1 1 calc R . . N3A N 0.1073(4) 0.12570(9) 0.48621(7) 0.0277(4) Uani 1 1 d . . . N4A N 0.1823(4) 0.01912(10) 0.54529(7) 0.0321(4) Uani 1 1 d . . . C1A C 0.3255(4) 0.34620(10) 0.48575(8) 0.0242(4) Uani 1 1 d . . . C2A C 0.0185(4) 0.28933(10) 0.45549(8) 0.0242(4) Uani 1 1 d . . . C3A C 0.0966(5) 0.33607(11) 0.41173(8) 0.0260(5) Uani 1 1 d . . . C4A C -0.0191(5) 0.33521(11) 0.36682(8) 0.0301(5) Uani 1 1 d . . . H4A1 H 0.0379 0.3665 0.3371 0.036 Uiso 1 1 calc R . . C5A C -0.2183(5) 0.28778(12) 0.36672(9) 0.0328(5) Uani 1 1 d . . . H5A1 H -0.3028 0.2871 0.3366 0.039 Uiso 1 1 calc R . . C6A C -0.2994(5) 0.24030(11) 0.41019(9) 0.0305(5) Uani 1 1 d . . . H6A H -0.4369 0.2078 0.4094 0.037 Uiso 1 1 calc R . . C7A C -0.1788(5) 0.24111(10) 0.45376(8) 0.0256(4) Uani 1 1 d . . . C8A C 0.6693(5) 0.41454(11) 0.51255(9) 0.0287(5) Uani 1 1 d . . . C9A C 0.8137(5) 0.42378(12) 0.55679(9) 0.0333(5) Uani 1 1 d . . . H9A1 H 1.0143 0.4231 0.5505 0.050 Uiso 1 1 calc R . . H9A2 H 0.7657 0.3865 0.5853 0.050 Uiso 1 1 calc R . . H9A3 H 0.7562 0.4678 0.5636 0.050 Uiso 1 1 calc R . . C10A C -0.1085(5) 0.13788(10) 0.51317(8) 0.0254(4) Uani 1 1 d . . . C11A C 0.2404(5) 0.06585(11) 0.50431(9) 0.0299(5) Uani 1 1 d . . . H11A H 0.3958 0.0558 0.4853 0.036 Uiso 1 1 calc R . . C12A C -0.1926(5) 0.09356(11) 0.55744(8) 0.0288(5) Uani 1 1 d . . . H12A H -0.3469 0.1043 0.5764 0.035 Uiso 1 1 calc R . . C13A C -0.0406(5) 0.03334(11) 0.57230(8) 0.0289(5) Uani 1 1 d . . . C14A C -0.1172(5) -0.01990(12) 0.61755(9) 0.0330(5) Uani 1 1 d . . . C15A C -0.3076(8) -0.00655(17) 0.65210(14) 0.0732(12) Uani 1 1 d . . . H15A H -0.3892 0.0380 0.6475 0.088 Uiso 1 1 calc R . . C16A C -0.3820(9) -0.0568(2) 0.69327(15) 0.0844(14) Uani 1 1 d . . . H16A H -0.5119 -0.0465 0.7169 0.101 Uiso 1 1 calc R . . C17A C -0.2690(7) -0.12127(15) 0.70005(11) 0.0520(7) Uani 1 1 d . A . C18A C -0.0854(10) -0.13522(15) 0.66662(12) 0.0714(11) Uani 1 1 d . . . H18A H -0.0072 -0.1801 0.6712 0.086 Uiso 1 1 calc R . . C19A C -0.0080(9) -0.08471(15) 0.62538(11) 0.0648(10) Uani 1 1 d . . . H19A H 0.1234 -0.0956 0.6022 0.078 Uiso 1 1 calc R . . C20A C -0.3483(9) -0.17599(19) 0.74423(14) 0.0738(11) Uani 1 1 d D . . S1B S 1.34356(12) 0.60372(3) 0.76079(2) 0.03081(15) Uani 1 1 d . . . F1B F 0.1180(5) 0.04998(10) 1.03581(12) 0.0954(8) Uani 1 1 d . . . F2B F -0.2553(5) 0.09138(10) 1.00063(8) 0.0739(6) Uani 1 1 d . . . F3B F -0.1964(5) 0.09239(11) 1.07534(8) 0.0779(6) Uani 1 1 d . . . O1B O 0.5875(3) 0.51321(8) 0.87938(6) 0.0311(4) Uani 1 1 d . . . O2B O 1.5521(4) 0.54628(9) 0.68752(6) 0.0408(4) Uani 1 1 d . . . N1B N 0.9681(4) 0.51477(9) 0.79963(7) 0.0269(4) Uani 1 1 d . . . N2B N 1.1854(4) 0.49194(10) 0.72972(7) 0.0305(4) Uani 1 1 d . . . H2B H 1.0754 0.4570 0.7326 0.037 Uiso 1 1 calc R . . N3B N 0.7809(4) 0.47792(10) 0.95628(7) 0.0332(4) Uani 1 1 d . . . N4B N 0.6456(5) 0.37213(11) 1.00999(7) 0.0368(5) Uani 1 1 d . . . C1B C 1.1523(5) 0.53045(11) 0.76387(8) 0.0270(5) Uani 1 1 d . . . C2B C 0.9596(5) 0.56413(11) 0.82709(8) 0.0265(5) Uani 1 1 d . . . C3B C 1.1476(5) 0.61711(11) 0.81154(8) 0.0290(5) Uani 1 1 d . . . C4B C 1.1616(5) 0.67044(12) 0.83498(9) 0.0346(5) Uani 1 1 d . . . H4B H 1.2931 0.7055 0.8246 0.042 Uiso 1 1 calc R . . C5B C 0.9788(6) 0.67084(12) 0.87374(9) 0.0379(6) Uani 1 1 d . . . H5B H 0.9839 0.7071 0.8901 0.045 Uiso 1 1 calc R . . C6B C 0.7857(5) 0.61917(12) 0.88961(9) 0.0336(5) Uani 1 1 d . . . H6B H 0.6587 0.6210 0.9160 0.040 Uiso 1 1 calc R . . C7B C 0.7806(5) 0.56564(11) 0.86672(8) 0.0284(5) Uani 1 1 d . . . C8B C 1.3757(5) 0.50323(12) 0.69133(9) 0.0335(5) Uani 1 1 d . . . C9B C 1.3456(7) 0.45892(15) 0.65587(10) 0.0473(7) Uani 1 1 d . . . H9B1 H 1.2785 0.4869 0.6245 0.071 Uiso 1 1 calc R . . H9B2 H 1.2129 0.4229 0.6696 0.071 Uiso 1 1 calc R . . H9B3 H 1.5256 0.4379 0.6503 0.071 Uiso 1 1 calc R . . C10B C 0.6096(5) 0.46692(11) 0.92335(8) 0.0272(5) Uani 1 1 d . . . C11B C 0.7856(6) 0.42959(13) 0.99862(9) 0.0386(6) Uani 1 1 d . . . H11B H 0.9026 0.4374 1.0233 0.046 Uiso 1 1 calc R . . C12B C 0.4481(5) 0.40919(12) 0.93100(8) 0.0303(5) Uani 1 1 d . . . H12B H 0.3247 0.4029 0.9067 0.036 Uiso 1 1 calc R . . C13B C 0.4742(5) 0.36161(12) 0.97516(8) 0.0302(5) Uani 1 1 d . . . C14B C 0.3267(5) 0.29549(12) 0.98871(9) 0.0323(5) Uani 1 1 d . . . C15B C 0.3764(6) 0.25031(14) 1.03375(10) 0.0441(6) Uani 1 1 d . . . H15B H 0.5023 0.2623 1.0556 0.053 Uiso 1 1 calc R . . C16B C 0.2456(7) 0.18799(14) 1.04740(11) 0.0475(7) Uani 1 1 d . . . H16B H 0.2800 0.1578 1.0785 0.057 Uiso 1 1 calc R . . C17B C 0.0648(6) 0.16992(13) 1.01560(10) 0.0422(6) Uani 1 1 d . . . C18B C 0.0124(7) 0.21411(15) 0.97098(11) 0.0510(7) Uani 1 1 d . . . H18B H -0.1133 0.2018 0.9493 0.061 Uiso 1 1 calc R . . C19B C 0.1426(6) 0.27703(14) 0.95726(10) 0.0439(6) Uani 1 1 d . . . H19B H 0.1053 0.3074 0.9263 0.053 Uiso 1 1 calc R . . C20B C -0.0656(7) 0.10108(15) 1.03101(13) 0.0543(8) Uani 1 1 d . . . O3A O 0.2782(4) 0.29067(10) 0.62002(6) 0.0406(4) Uani 1 1 d . . . O4A O -0.0159(5) 0.23097(10) 0.58774(6) 0.0502(5) Uani 1 1 d . . . H4A H 0.0623 0.2509 0.5611 0.075 Uiso 1 1 calc R . . O5A O -0.0658(4) 0.26371(10) 0.70493(7) 0.0416(4) Uani 1 1 d . . . H5A H 0.0961 0.2732 0.7106 0.062 Uiso 1 1 calc R . . C21A C 0.0889(5) 0.25135(12) 0.62419(9) 0.0316(5) Uani 1 1 d . . . C22A C -0.0561(5) 0.21885(13) 0.67320(9) 0.0342(5) Uani 1 1 d . . . H22A H -0.2512 0.2101 0.6660 0.041 Uiso 1 1 calc R . . C23A C 0.0805(6) 0.15020(14) 0.69605(10) 0.0429(6) Uani 1 1 d . . . H23A H 0.2696 0.1580 0.7058 0.051 Uiso 1 1 calc R . . H23B H 0.0981 0.1230 0.6708 0.051 Uiso 1 1 calc R . . C24A C -0.0773(6) 0.10877(16) 0.74111(11) 0.0484(7) Uani 1 1 d . . . H24C H -0.0960 0.1359 0.7664 0.058 Uiso 1 1 calc R . . H24D H -0.2658 0.1004 0.7314 0.058 Uiso 1 1 calc R . . C25A C 0.0632(7) 0.04109(19) 0.76343(14) 0.0688(10) Uani 1 1 d . . . H25A H 0.2498 0.0497 0.7740 0.083 Uiso 1 1 calc R . . H25B H 0.0872 0.0147 0.7378 0.083 Uiso 1 1 calc R . . C26A C -0.0953(9) -0.0020(2) 0.80762(16) 0.0846(13) Uani 1 1 d . . . H26D H -0.1222 0.0239 0.8331 0.127 Uiso 1 1 calc R . . H26E H 0.0103 -0.0443 0.8211 0.127 Uiso 1 1 calc R . . H26F H -0.2759 -0.0133 0.7971 0.127 Uiso 1 1 calc R . . O3B O 0.7936(4) 0.39023(9) 0.74453(6) 0.0381(4) Uani 1 1 d . . . O4B O 0.6174(4) 0.40895(9) 0.81526(6) 0.0389(4) Uani 1 1 d . . . H4B H 0.7296 0.4412 0.8093 0.058 Uiso 1 1 calc R . . O5B O 0.4253(4) 0.29339(10) 0.74397(6) 0.0383(4) Uani 1 1 d . . . H5B H 0.5837 0.2884 0.7319 0.057 Uiso 1 1 calc R . . C21B C 0.6374(5) 0.37597(12) 0.78009(8) 0.0294(5) Uani 1 1 d . . . C22B C 0.4499(5) 0.31487(12) 0.78836(9) 0.0317(5) Uani 1 1 d . . . H22B H 0.2620 0.3290 0.7989 0.038 Uiso 1 1 calc R . . C23B C 0.5639(5) 0.25802(13) 0.82983(10) 0.0380(6) Uani 1 1 d . . . H23C H 0.7527 0.2451 0.8200 0.046 Uiso 1 1 calc R . . H23D H 0.5795 0.2761 0.8596 0.046 Uiso 1 1 calc R . . C24B C 0.3903(6) 0.19409(14) 0.84310(11) 0.0426(6) Uani 1 1 d . . . H24A H 0.2008 0.2066 0.8528 0.051 Uiso 1 1 calc R . . H24B H 0.3770 0.1751 0.8137 0.051 Uiso 1 1 calc R . . C25B C 0.5117(7) 0.13983(15) 0.88488(14) 0.0569(8) Uani 1 1 d . . . H25C H 0.5195 0.1589 0.9144 0.068 Uiso 1 1 calc R . . H25D H 0.7040 0.1291 0.8754 0.068 Uiso 1 1 calc R . . C26B C 0.3525(8) 0.07361(16) 0.89868(16) 0.0677(10) Uani 1 1 d . . . H26A H 0.1632 0.0832 0.9092 0.102 Uiso 1 1 calc R . . H26B H 0.4445 0.0413 0.9258 0.102 Uiso 1 1 calc R . . H26C H 0.3471 0.0536 0.8700 0.102 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 S1A 0.0284(3) 0.0213(2) 0.0264(3) -0.0009(2) 0.0041(2) -0.0016(2) F1A 0.097(3) 0.095(3) 0.086(2) 0.0436(18) 0.041(2) 0.007(2) F2A 0.104(3) 0.134(3) 0.0697(19) 0.059(2) -0.011(3) -0.011(3) F3A 0.419(14) 0.053(2) 0.091(3) -0.0046(19) 0.071(6) -0.125(4) F1AA 0.097(3) 0.095(3) 0.086(2) 0.0436(18) 0.041(2) 0.007(2) F2AA 0.104(3) 0.134(3) 0.0697(19) 0.059(2) -0.011(3) -0.011(3) F3AA 0.419(14) 0.053(2) 0.091(3) -0.0046(19) 0.071(6) -0.125(4) O1A 0.0280(8) 0.0205(7) 0.0321(8) -0.0002(6) 0.0004(6) -0.0009(6) O2A 0.0362(9) 0.0326(9) 0.0379(9) -0.0040(7) 0.0061(7) -0.0099(7) N1A 0.0247(9) 0.0209(8) 0.0265(9) -0.0026(7) 0.0009(7) -0.0005(7) N2A 0.0267(9) 0.0247(9) 0.0274(9) -0.0023(7) 0.0012(8) -0.0040(7) N3A 0.0271(10) 0.0225(9) 0.0323(10) -0.0036(8) -0.0040(8) -0.0031(7) N4A 0.0337(11) 0.0254(9) 0.0350(11) -0.0028(8) -0.0047(9) 0.0013(8) C1A 0.0228(10) 0.0199(10) 0.0280(11) -0.0027(8) 0.0019(9) 0.0024(8) C2A 0.0250(11) 0.0195(10) 0.0264(11) -0.0032(8) -0.0002(9) 0.0047(8) C3A 0.0261(11) 0.0206(10) 0.0296(11) -0.0035(8) 0.0018(9) 0.0030(8) C4A 0.0355(12) 0.0254(11) 0.0263(11) -0.0013(9) -0.0001(9) 0.0065(9) C5A 0.0410(13) 0.0289(11) 0.0285(12) -0.0073(9) -0.0067(10) 0.0062(10) C6A 0.0326(12) 0.0217(10) 0.0377(13) -0.0081(9) -0.0059(10) 0.0029(9) C7A 0.0265(11) 0.0192(10) 0.0283(11) -0.0008(8) 0.0000(9) 0.0034(8) C8A 0.0244(11) 0.0240(10) 0.0381(13) -0.0093(10) 0.0044(9) 0.0002(9) C9A 0.0302(12) 0.0316(12) 0.0401(13) -0.0124(10) 0.0009(10) -0.0029(10) C10A 0.0268(11) 0.0174(10) 0.0317(11) -0.0043(8) -0.0072(9) -0.0040(8) C11A 0.0273(11) 0.0263(11) 0.0344(12) -0.0039(9) -0.0023(9) 0.0011(9) C12A 0.0327(12) 0.0236(11) 0.0297(11) -0.0051(9) -0.0009(9) -0.0051(9) C13A 0.0351(12) 0.0221(10) 0.0298(11) -0.0055(9) -0.0061(10) -0.0052(9) C14A 0.0400(13) 0.0255(11) 0.0317(12) -0.0028(9) -0.0038(10) -0.0053(10) C15A 0.087(3) 0.0463(17) 0.065(2) 0.0204(15) 0.031(2) 0.0256(17) C16A 0.090(3) 0.067(2) 0.070(2) 0.0254(19) 0.041(2) 0.024(2) C17A 0.0639(19) 0.0413(15) 0.0420(16) 0.0087(12) -0.0036(14) -0.0100(14) C18A 0.128(3) 0.0282(14) 0.0476(18) 0.0080(12) 0.015(2) 0.0150(17) C19A 0.110(3) 0.0354(15) 0.0391(16) 0.0046(12) 0.0210(18) 0.0225(17) C20A 0.084(3) 0.058(2) 0.057(2) 0.0294(18) 0.000(2) -0.0053(19) S1B 0.0312(3) 0.0294(3) 0.0281(3) 0.0011(2) 0.0003(2) -0.0080(2) F1B 0.0724(14) 0.0304(9) 0.177(3) -0.0123(12) -0.0058(16) -0.0081(9) F2B 0.0857(14) 0.0527(11) 0.0798(13) -0.0027(10) -0.0148(11) -0.0390(10) F3B 0.0967(16) 0.0600(12) 0.0674(12) 0.0060(10) 0.0090(12) -0.0370(11) O1B 0.0325(8) 0.0333(8) 0.0259(8) -0.0032(7) -0.0002(7) -0.0091(7) O2B 0.0395(10) 0.0421(10) 0.0356(9) 0.0000(8) 0.0094(8) -0.0075(8) N1B 0.0266(9) 0.0266(9) 0.0257(9) -0.0025(7) -0.0016(8) -0.0028(7) N2B 0.0318(10) 0.0298(10) 0.0280(10) -0.0032(8) 0.0025(8) -0.0049(8) N3B 0.0383(11) 0.0303(10) 0.0303(10) -0.0048(8) -0.0038(8) -0.0068(9) N4B 0.0458(12) 0.0317(10) 0.0321(11) -0.0045(8) -0.0041(9) -0.0082(9) C1B 0.0276(11) 0.0255(10) 0.0246(11) 0.0011(8) -0.0041(9) -0.0009(9) C2B 0.0296(11) 0.0232(10) 0.0241(11) 0.0000(8) -0.0060(9) -0.0017(9) C3B 0.0297(12) 0.0279(11) 0.0257(11) 0.0018(9) -0.0043(9) -0.0030(9) C4B 0.0422(14) 0.0260(11) 0.0328(12) 0.0000(9) -0.0065(10) -0.0087(10) C5B 0.0523(16) 0.0271(12) 0.0341(13) -0.0056(10) -0.0057(11) -0.0063(11) C6B 0.0426(14) 0.0311(12) 0.0262(11) -0.0053(9) -0.0011(10) -0.0016(10) C7B 0.0290(11) 0.0270(11) 0.0268(11) -0.0006(9) -0.0038(9) -0.0050(9) C8B 0.0363(13) 0.0317(12) 0.0272(12) 0.0030(9) 0.0039(10) 0.0002(10) C9B 0.0606(18) 0.0469(15) 0.0332(13) -0.0080(11) 0.0135(13) -0.0085(13) C10B 0.0285(11) 0.0286(11) 0.0246(11) -0.0070(9) 0.0040(9) -0.0011(9) C11B 0.0486(15) 0.0356(13) 0.0310(13) -0.0044(10) -0.0089(11) -0.0112(11) C12B 0.0310(12) 0.0327(12) 0.0281(11) -0.0087(10) 0.0000(9) -0.0060(10) C13B 0.0323(12) 0.0292(11) 0.0304(12) -0.0101(9) 0.0046(10) -0.0049(9) C14B 0.0355(13) 0.0286(11) 0.0336(12) -0.0095(10) 0.0049(10) -0.0037(10) C15B 0.0556(17) 0.0345(13) 0.0414(15) -0.0054(11) -0.0068(13) -0.0116(12) C16B 0.0615(18) 0.0321(13) 0.0450(15) -0.0001(11) -0.0031(13) -0.0091(13) C17B 0.0454(15) 0.0318(13) 0.0485(15) -0.0079(11) 0.0037(12) -0.0079(11) C18B 0.0582(18) 0.0429(15) 0.0513(17) -0.0069(13) -0.0086(14) -0.0225(14) C19B 0.0493(16) 0.0382(14) 0.0421(14) -0.0032(11) -0.0034(12) -0.0159(12) C20B 0.0557(18) 0.0365(15) 0.067(2) -0.0035(14) -0.0030(16) -0.0112(14) O3A 0.0402(10) 0.0461(10) 0.0345(9) -0.0061(8) -0.0024(8) -0.0129(8) O4A 0.0749(14) 0.0497(11) 0.0268(9) -0.0080(8) 0.0052(9) -0.0332(10) O5A 0.0353(9) 0.0549(11) 0.0415(10) -0.0248(9) 0.0027(8) -0.0060(8) C21A 0.0367(13) 0.0258(11) 0.0328(12) -0.0075(9) -0.0027(10) -0.0014(10) C22A 0.0352(13) 0.0373(13) 0.0308(12) -0.0095(10) -0.0005(10) -0.0028(10) C23A 0.0383(14) 0.0453(15) 0.0390(14) 0.0005(11) 0.0044(11) 0.0030(12) C24A 0.0438(15) 0.0526(17) 0.0411(15) 0.0033(12) 0.0056(12) -0.0013(13) C25A 0.0521(19) 0.067(2) 0.069(2) 0.0189(17) 0.0028(17) 0.0063(16) C26A 0.081(3) 0.075(3) 0.073(3) 0.031(2) -0.006(2) -0.004(2) O3B 0.0425(10) 0.0340(9) 0.0392(9) -0.0122(7) 0.0101(8) -0.0091(7) O4B 0.0480(11) 0.0364(9) 0.0350(9) -0.0129(7) 0.0071(8) -0.0157(8) O5B 0.0329(9) 0.0464(10) 0.0404(9) -0.0191(8) 0.0000(7) -0.0088(8) C21B 0.0307(12) 0.0278(11) 0.0287(12) -0.0046(9) -0.0049(10) 0.0015(9) C22B 0.0291(12) 0.0329(12) 0.0338(12) -0.0093(10) -0.0011(10) -0.0033(10) C23B 0.0349(13) 0.0306(12) 0.0469(15) -0.0048(11) -0.0075(11) -0.0050(10) C24B 0.0363(14) 0.0350(13) 0.0531(16) -0.0018(12) -0.0094(12) -0.0087(11) C25B 0.0472(17) 0.0355(15) 0.079(2) 0.0064(14) -0.0186(16) -0.0091(13) C26B 0.060(2) 0.0380(16) 0.093(3) 0.0109(16) -0.0177(19) -0.0116(15) _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 S1A C1A 1.736(2) . ? S1A C3A 1.746(2) . ? F1A C20A 1.383(5) . ? F2A C20A 1.354(6) . ? F3A C20A 1.263(6) . ? F1AA C20A 1.371(12) . ? F2AA C20A 1.170(12) . ? F3AA C20A 1.304(17) . ? O1A C10A 1.355(3) . ? O1A C7A 1.403(3) . ? O2A C8A 1.216(3) . ? N1A C1A 1.309(3) . ? N1A C2A 1.389(3) . ? N2A C1A 1.373(3) . ? N2A C8A 1.379(3) . ? N2A H2A 0.8800 . ? N3A C10A 1.317(3) . ? N3A C11A 1.342(3) . ? N4A C11A 1.322(3) . ? N4A C13A 1.357(3) . ? C2A C7A 1.390(3) . ? C2A C3A 1.399(3) . ? C3A C4A 1.393(3) . ? C4A C5A 1.376(4) . ? C4A H4A1 0.9500 . ? C5A C6A 1.404(3) . ? C5A H5A1 0.9500 . ? C6A C7A 1.368(3) . ? C6A H6A 0.9500 . ? C8A C9A 1.490(3) . ? C9A H9A1 0.9800 . ? C9A H9A2 0.9800 . ? C9A H9A3 0.9800 . ? C10A C12A 1.395(3) . ? C11A H11A 0.9500 . ? C12A C13A 1.380(3) . ? C12A H12A 0.9500 . ? C13A C14A 1.490(3) . ? C14A C19A 1.362(4) . ? C14A C15A 1.379(4) . ? C15A C16A 1.381(4) . ? C15A H15A 0.9500 . ? C16A C17A 1.365(5) . ? C16A H16A 0.9500 . ? C17A C18A 1.339(5) . ? C17A C20A 1.490(4) . ? C18A C19A 1.389(4) . ? C18A H18A 0.9500 . ? C19A H19A 0.9500 . ? S1B C1B 1.745(2) . ? S1B C3B 1.748(2) . ? F1B C20B 1.323(4) . ? F2B C20B 1.318(4) . ? F3B C20B 1.346(4) . ? O1B C10B 1.356(3) . ? O1B C7B 1.402(3) . ? O2B C8B 1.217(3) . ? N1B C1B 1.302(3) . ? N1B C2B 1.391(3) . ? N2B C1B 1.368(3) . ? N2B C8B 1.370(3) . ? N2B H2B 0.8800 . ? N3B C10B 1.318(3) . ? N3B C11B 1.338(3) . ? N4B C11B 1.323(3) . ? N4B C13B 1.355(3) . ? C2B C7B 1.387(3) . ? C2B C3B 1.399(3) . ? C3B C4B 1.388(3) . ? C4B C5B 1.375(4) . ? C4B H4B 0.9500 . ? C5B C6B 1.399(4) . ? C5B H5B 0.9500 . ? C6B C7B 1.378(3) . ? C6B H6B 0.9500 . ? C8B C9B 1.495(4) . ? C9B H9B1 0.9800 . ? C9B H9B2 0.9800 . ? C9B H9B3 0.9800 . ? C10B C12B 1.388(3) . ? C11B H11B 0.9500 . ? C12B C13B 1.373(3) . ? C12B H12B 0.9500 . ? C13B C14B 1.489(3) . ? C14B C15B 1.386(4) . ? C14B C19B 1.388(4) . ? C15B C16B 1.385(4) . ? C15B H15B 0.9500 . ? C16B C17B 1.380(4) . ? C16B H16B 0.9500 . ? C17B C18B 1.371(4) . ? C17B C20B 1.499(4) . ? C18B C19B 1.394(4) . ? C18B H18B 0.9500 . ? C19B H19B 0.9500 . ? O3A C21A 1.212(3) . ? O4A C21A 1.305(3) . ? O4A H4A 0.8400 . ? O5A C22A 1.406(3) . ? O5A H5A 0.8400 . ? C21A C22A 1.524(3) . ? C22A C23A 1.516(4) . ? C22A H22A 1.0000 . ? C23A C24A 1.526(4) . ? C23A H23A 0.9900 . ? C23A H23B 0.9900 . ? C24A C25A 1.506(5) . ? C24A H24C 0.9900 . ? C24A H24D 0.9900 . ? C25A C26A 1.524(5) . ? C25A H25A 0.9900 . ? C25A H25B 0.9900 . ? C26A H26D 0.9800 . ? C26A H26E 0.9800 . ? C26A H26F 0.9800 . ? O3B C21B 1.210(3) . ? O4B C21B 1.309(3) . ? O4B H4B 0.8400 . ? O5B C22B 1.415(3) . ? O5B H5B 0.8400 . ? C21B C22B 1.517(3) . ? C22B C23B 1.523(4) . ? C22B H22B 1.0000 . ? C23B C24B 1.519(3) . ? C23B H23C 0.9900 . ? C23B H23D 0.9900 . ? C24B C25B 1.513(4) . ? C24B H24A 0.9900 . ? C24B H24B 0.9900 . ? C25B C26B 1.519(4) . ? C25B H25C 0.9900 . ? C25B H25D 0.9900 . ? C26B H26A 0.9800 . ? C26B H26B 0.9800 . ? C26B H26C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1A S1A C3A 88.43(10) . . ? C10A O1A C7A 116.78(17) . . ? C1A N1A C2A 109.64(17) . . ? C1A N2A C8A 124.23(19) . . ? C1A N2A H2A 117.9 . . ? C8A N2A H2A 117.9 . . ? C10A N3A C11A 114.53(19) . . ? C11A N4A C13A 115.9(2) . . ? N1A C1A N2A 120.20(19) . . ? N1A C1A S1A 117.05(16) . . ? N2A C1A S1A 122.75(15) . . ? N1A C2A C7A 125.80(19) . . ? N1A C2A C3A 115.32(19) . . ? C7A C2A C3A 118.9(2) . . ? C4A C3A C2A 121.4(2) . . ? C4A C3A S1A 129.00(17) . . ? C2A C3A S1A 109.57(17) . . ? C5A C4A C3A 118.0(2) . . ? C5A C4A H4A1 121.0 . . ? C3A C4A H4A1 121.0 . . ? C4A C5A C6A 121.5(2) . . ? C4A C5A H5A1 119.3 . . ? C6A C5A H5A1 119.3 . . ? C7A C6A C5A 119.5(2) . . ? C7A C6A H6A 120.2 . . ? C5A C6A H6A 120.2 . . ? C6A C7A C2A 120.6(2) . . ? C6A C7A O1A 120.4(2) . . ? C2A C7A O1A 118.90(19) . . ? O2A C8A N2A 120.7(2) . . ? O2A C8A C9A 124.0(2) . . ? N2A C8A C9A 115.3(2) . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? N3A C10A O1A 119.91(19) . . ? N3A C10A C12A 123.7(2) . . ? O1A C10A C12A 116.4(2) . . ? N4A C11A N3A 128.1(2) . . ? N4A C11A H11A 116.0 . . ? N3A C11A H11A 116.0 . . ? C13A C12A C10A 116.7(2) . . ? C13A C12A H12A 121.7 . . ? C10A C12A H12A 121.7 . . ? N4A C13A C12A 121.1(2) . . ? N4A C13A C14A 116.9(2) . . ? C12A C13A C14A 122.0(2) . . ? C19A C14A C15A 117.4(2) . . ? C19A C14A C13A 120.8(2) . . ? C15A C14A C13A 121.7(2) . . ? C14A C15A C16A 121.2(3) . . ? C14A C15A H15A 119.4 . . ? C16A C15A H15A 119.4 . . ? C17A C16A C15A 120.0(3) . . ? C17A C16A H16A 120.0 . . ? C15A C16A H16A 120.0 . . ? C18A C17A C16A 119.5(3) . . ? C18A C17A C20A 120.0(3) . . ? C16A C17A C20A 120.5(3) . . ? C17A C18A C19A 120.7(3) . . ? C17A C18A H18A 119.7 . . ? C19A C18A H18A 119.7 . . ? C14A C19A C18A 121.2(3) . . ? C14A C19A H19A 119.4 . . ? C18A C19A H19A 119.4 . . ? F2AA C20A F3A 123.4(7) . . ? F2AA C20A F3AA 103.8(10) . . ? F3A C20A F3AA 45.9(8) . . ? F2AA C20A F2A 42.9(7) . . ? F3A C20A F2A 107.1(6) . . ? F3AA C20A F2A 67.7(8) . . ? F2AA C20A F1AA 112.9(9) . . ? F3A C20A F1AA 53.9(6) . . ? F3AA C20A F1AA 99.4(8) . . ? F2A C20A F1AA 139.7(5) . . ? F2AA C20A F1A 51.9(7) . . ? F3A C20A F1A 111.9(5) . . ? F3AA C20A F1A 136.3(7) . . ? F2A C20A F1A 94.5(4) . . ? F1AA C20A F1A 68.1(6) . . ? F2AA C20A C17A 118.9(7) . . ? F3A C20A C17A 116.9(4) . . ? F3AA C20A C17A 110.9(7) . . ? F2A C20A C17A 111.2(3) . . ? F1AA C20A C17A 109.1(5) . . ? F1A C20A C17A 112.8(3) . . ? C1B S1B C3B 88.23(11) . . ? C10B O1B C7B 118.69(17) . . ? C1B N1B C2B 109.96(19) . . ? C1B N2B C8B 125.4(2) . . ? C1B N2B H2B 117.3 . . ? C8B N2B H2B 117.3 . . ? C10B N3B C11B 115.1(2) . . ? C11B N4B C13B 116.3(2) . . ? N1B C1B N2B 120.8(2) . . ? N1B C1B S1B 116.93(17) . . ? N2B C1B S1B 122.28(16) . . ? C7B C2B N1B 126.0(2) . . ? C7B C2B C3B 118.8(2) . . ? N1B C2B C3B 115.2(2) . . ? C4B C3B C2B 121.8(2) . . ? C4B C3B S1B 128.53(18) . . ? C2B C3B S1B 109.62(17) . . ? C5B C4B C3B 117.8(2) . . ? C5B C4B H4B 121.1 . . ? C3B C4B H4B 121.1 . . ? C4B C5B C6B 121.6(2) . . ? C4B C5B H5B 119.2 . . ? C6B C5B H5B 119.2 . . ? C7B C6B C5B 119.6(2) . . ? C7B C6B H6B 120.2 . . ? C5B C6B H6B 120.2 . . ? C6B C7B C2B 120.3(2) . . ? C6B C7B O1B 123.0(2) . . ? C2B C7B O1B 116.63(19) . . ? O2B C8B N2B 121.2(2) . . ? O2B C8B C9B 124.3(2) . . ? N2B C8B C9B 114.5(2) . . ? C8B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C8B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? N3B C10B O1B 119.64(19) . . ? N3B C10B C12B 123.2(2) . . ? O1B C10B C12B 117.1(2) . . ? N4B C11B N3B 127.3(2) . . ? N4B C11B H11B 116.3 . . ? N3B C11B H11B 116.3 . . ? C13B C12B C10B 117.2(2) . . ? C13B C12B H12B 121.4 . . ? C10B C12B H12B 121.4 . . ? N4B C13B C12B 120.8(2) . . ? N4B C13B C14B 114.8(2) . . ? C12B C13B C14B 124.4(2) . . ? C15B C14B C19B 118.6(2) . . ? C15B C14B C13B 119.4(2) . . ? C19B C14B C13B 122.0(2) . . ? C16B C15B C14B 121.0(3) . . ? C16B C15B H15B 119.5 . . ? C14B C15B H15B 119.5 . . ? C17B C16B C15B 119.8(3) . . ? C17B C16B H16B 120.1 . . ? C15B C16B H16B 120.1 . . ? C18B C17B C16B 119.9(2) . . ? C18B C17B C20B 121.8(3) . . ? C16B C17B C20B 118.2(3) . . ? C17B C18B C19B 120.4(3) . . ? C17B C18B H18B 119.8 . . ? C19B C18B H18B 119.8 . . ? C14B C19B C18B 120.2(3) . . ? C14B C19B H19B 119.9 . . ? C18B C19B H19B 119.9 . . ? F2B C20B F1B 107.7(3) . . ? F2B C20B F3B 105.3(3) . . ? F1B C20B F3B 105.6(3) . . ? F2B C20B C17B 113.6(3) . . ? F1B C20B C17B 112.6(3) . . ? F3B C20B C17B 111.5(3) . . ? C21A O4A H4A 109.5 . . ? C22A O5A H5A 109.5 . . ? O3A C21A O4A 124.8(2) . . ? O3A C21A C22A 123.9(2) . . ? O4A C21A C22A 111.3(2) . . ? O5A C22A C23A 112.9(2) . . ? O5A C22A C21A 111.1(2) . . ? C23A C22A C21A 109.9(2) . . ? O5A C22A H22A 107.6 . . ? C23A C22A H22A 107.6 . . ? C21A C22A H22A 107.6 . . ? C22A C23A C24A 113.7(2) . . ? C22A C23A H23A 108.8 . . ? C24A C23A H23A 108.8 . . ? C22A C23A H23B 108.8 . . ? C24A C23A H23B 108.8 . . ? H23A C23A H23B 107.7 . . ? C25A C24A C23A 112.8(2) . . ? C25A C24A H24C 109.0 . . ? C23A C24A H24C 109.0 . . ? C25A C24A H24D 109.0 . . ? C23A C24A H24D 109.0 . . ? H24C C24A H24D 107.8 . . ? C24A C25A C26A 113.6(3) . . ? C24A C25A H25A 108.8 . . ? C26A C25A H25A 108.8 . . ? C24A C25A H25B 108.8 . . ? C26A C25A H25B 108.8 . . ? H25A C25A H25B 107.7 . . ? C25A C26A H26D 109.5 . . ? C25A C26A H26E 109.5 . . ? H26D C26A H26E 109.5 . . ? C25A C26A H26F 109.5 . . ? H26D C26A H26F 109.5 . . ? H26E C26A H26F 109.5 . . ? C21B O4B H4B 109.5 . . ? C22B O5B H5B 109.5 . . ? O3B C21B O4B 124.9(2) . . ? O3B C21B C22B 121.4(2) . . ? O4B C21B C22B 113.66(19) . . ? O5B C22B C21B 110.30(18) . . ? O5B C22B C23B 112.2(2) . . ? C21B C22B C23B 108.90(19) . . ? O5B C22B H22B 108.4 . . ? C21B C22B H22B 108.4 . . ? C23B C22B H22B 108.4 . . ? C24B C23B C22B 114.5(2) . . ? C24B C23B H23C 108.6 . . ? C22B C23B H23C 108.6 . . ? C24B C23B H23D 108.6 . . ? C22B C23B H23D 108.6 . . ? H23C C23B H23D 107.6 . . ? C25B C24B C23B 112.1(2) . . ? C25B C24B H24A 109.2 . . ? C23B C24B H24A 109.2 . . ? C25B C24B H24B 109.2 . . ? C23B C24B H24B 109.2 . . ? H24A C24B H24B 107.9 . . ? C24B C25B C26B 114.6(3) . . ? C24B C25B H25C 108.6 . . ? C26B C25B H25C 108.6 . . ? C24B C25B H25D 108.6 . . ? C26B C25B H25D 108.6 . . ? H25C C25B H25D 107.6 . . ? C25B C26B H26A 109.5 . . ? C25B C26B H26B 109.5 . . ? H26A C26B H26B 109.5 . . ? C25B C26B H26C 109.5 . . ? H26A C26B H26C 109.5 . . ? H26B C26B H26C 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 C2A N1A C1A N2A -179.82(18) . . . . ? C2A N1A C1A S1A 0.1(2) . . . . ? C8A N2A C1A N1A -179.63(19) . . . . ? C8A N2A C1A S1A 0.5(3) . . . . ? C3A S1A C1A N1A 0.00(17) . . . . ? C3A S1A C1A N2A 179.90(18) . . . . ? C1A N1A C2A C7A 179.6(2) . . . . ? C1A N1A C2A C3A -0.2(3) . . . . ? N1A C2A C3A C4A 179.79(19) . . . . ? C7A C2A C3A C4A 0.1(3) . . . . ? N1A C2A C3A S1A 0.2(2) . . . . ? C7A C2A C3A S1A -179.58(15) . . . . ? C1A S1A C3A C4A -179.7(2) . . . . ? C1A S1A C3A C2A -0.09(16) . . . . ? C2A C3A C4A C5A 1.4(3) . . . . ? S1A C3A C4A C5A -179.05(17) . . . . ? C3A C4A C5A C6A -1.5(3) . . . . ? C4A C5A C6A C7A 0.2(3) . . . . ? C5A C6A C7A C2A 1.3(3) . . . . ? C5A C6A C7A O1A 177.64(19) . . . . ? N1A C2A C7A C6A 178.8(2) . . . . ? C3A C2A C7A C6A -1.4(3) . . . . ? N1A C2A C7A O1A 2.5(3) . . . . ? C3A C2A C7A O1A -177.80(18) . . . . ? C10A O1A C7A C6A 97.9(2) . . . . ? C10A O1A C7A C2A -85.7(2) . . . . ? C1A N2A C8A O2A -0.4(3) . . . . ? C1A N2A C8A C9A 179.1(2) . . . . ? C11A N3A C10A O1A -178.05(19) . . . . ? C11A N3A C10A C12A 1.1(3) . . . . ? C7A O1A C10A N3A -1.7(3) . . . . ? C7A O1A C10A C12A 179.12(19) . . . . ? C13A N4A C11A N3A 0.3(4) . . . . ? C10A N3A C11A N4A -0.5(3) . . . . ? N3A C10A C12A C13A -1.4(3) . . . . ? O1A C10A C12A C13A 177.74(19) . . . . ? C11A N4A C13A C12A -0.6(3) . . . . ? C11A N4A C13A C14A 177.5(2) . . . . ? C10A C12A C13A N4A 1.1(3) . . . . ? C10A C12A C13A C14A -176.9(2) . . . . ? N4A C13A C14A C19A -13.8(4) . . . . ? C12A C13A C14A C19A 164.4(3) . . . . ? N4A C13A C14A C15A 168.7(3) . . . . ? C12A C13A C14A C15A -13.2(4) . . . . ? C19A C14A C15A C16A 0.7(6) . . . . ? C13A C14A C15A C16A 178.4(4) . . . . ? C14A C15A C16A C17A -0.8(8) . . . . ? C15A C16A C17A C18A 0.2(7) . . . . ? C15A C16A C17A C20A -179.8(4) . . . . ? C16A C17A C18A C19A 0.3(7) . . . . ? C20A C17A C18A C19A -179.6(4) . . . . ? C15A C14A C19A C18A -0.2(6) . . . . ? C13A C14A C19A C18A -177.8(3) . . . . ? C17A C18A C19A C14A -0.4(7) . . . . ? C18A C17A C20A F2AA 132.3(10) . . . . ? C16A C17A C20A F2AA -47.6(11) . . . . ? C18A C17A C20A F3A -37.9(8) . . . . ? C16A C17A C20A F3A 142.2(7) . . . . ? C18A C17A C20A F3AA 12.3(10) . . . . ? C16A C17A C20A F3AA -167.7(9) . . . . ? C18A C17A C20A F2A 85.5(5) . . . . ? C16A C17A C20A F2A -94.5(5) . . . . ? C18A C17A C20A F1AA -96.3(7) . . . . ? C16A C17A C20A F1AA 83.8(7) . . . . ? C18A C17A C20A F1A -169.8(4) . . . . ? C16A C17A C20A F1A 10.2(6) . . . . ? C2B N1B C1B N2B -175.5(2) . . . . ? C2B N1B C1B S1B 2.4(2) . . . . ? C8B N2B C1B N1B -178.8(2) . . . . ? C8B N2B C1B S1B 3.4(3) . . . . ? C3B S1B C1B N1B -2.33(19) . . . . ? C3B S1B C1B N2B 175.6(2) . . . . ? C1B N1B C2B C7B 177.3(2) . . . . ? C1B N1B C2B C3B -1.2(3) . . . . ? C7B C2B C3B C4B 0.7(3) . . . . ? N1B C2B C3B C4B 179.3(2) . . . . ? C7B C2B C3B S1B -179.06(18) . . . . ? N1B C2B C3B S1B -0.5(2) . . . . ? C1B S1B C3B C4B -178.3(2) . . . . ? C1B S1B C3B C2B 1.44(17) . . . . ? C2B C3B C4B C5B -1.5(4) . . . . ? S1B C3B C4B C5B 178.2(2) . . . . ? C3B C4B C5B C6B 0.5(4) . . . . ? C4B C5B C6B C7B 1.3(4) . . . . ? C5B C6B C7B C2B -2.2(4) . . . . ? C5B C6B C7B O1B -177.8(2) . . . . ? N1B C2B C7B C6B -177.3(2) . . . . ? C3B C2B C7B C6B 1.1(3) . . . . ? N1B C2B C7B O1B -1.4(3) . . . . ? C3B C2B C7B O1B 177.05(19) . . . . ? C10B O1B C7B C6B -70.8(3) . . . . ? C10B O1B C7B C2B 113.4(2) . . . . ? C1B N2B C8B O2B 7.1(4) . . . . ? C1B N2B C8B C9B -172.9(2) . . . . ? C11B N3B C10B O1B 179.4(2) . . . . ? C11B N3B C10B C12B -1.1(3) . . . . ? C7B O1B C10B N3B 10.7(3) . . . . ? C7B O1B C10B C12B -168.85(19) . . . . ? C13B N4B C11B N3B -1.3(4) . . . . ? C10B N3B C11B N4B 2.3(4) . . . . ? N3B C10B C12B C13B -0.7(3) . . . . ? O1B C10B C12B C13B 178.8(2) . . . . ? C11B N4B C13B C12B -0.8(3) . . . . ? C11B N4B C13B C14B 178.3(2) . . . . ? C10B C12B C13B N4B 1.8(3) . . . . ? C10B C12B C13B C14B -177.3(2) . . . . ? N4B C13B C14B C15B -1.3(3) . . . . ? C12B C13B C14B C15B 177.8(2) . . . . ? N4B C13B C14B C19B 179.7(2) . . . . ? C12B C13B C14B C19B -1.3(4) . . . . ? C19B C14B C15B C16B -0.1(4) . . . . ? C13B C14B C15B C16B -179.2(3) . . . . ? C14B C15B C16B C17B 0.7(5) . . . . ? C15B C16B C17B C18B -0.9(5) . . . . ? C15B C16B C17B C20B 178.0(3) . . . . ? C16B C17B C18B C19B 0.6(5) . . . . ? C20B C17B C18B C19B -178.4(3) . . . . ? C15B C14B C19B C18B -0.2(4) . . . . ? C13B C14B C19B C18B 178.8(3) . . . . ? C17B C18B C19B C14B 0.0(5) . . . . ? C18B C17B C20B F2B -7.5(4) . . . . ? C16B C17B C20B F2B 173.5(3) . . . . ? C18B C17B C20B F1B 115.3(4) . . . . ? C16B C17B C20B F1B -63.7(4) . . . . ? C18B C17B C20B F3B -126.3(3) . . . . ? C16B C17B C20B F3B 54.8(4) . . . . ? O3A C21A C22A O5A 33.4(3) . . . . ? O4A C21A C22A O5A -147.1(2) . . . . ? O3A C21A C22A C23A -92.3(3) . . . . ? O4A C21A C22A C23A 87.2(3) . . . . ? O5A C22A C23A C24A 64.3(3) . . . . ? C21A C22A C23A C24A -171.0(2) . . . . ? C22A C23A C24A C25A -179.5(3) . . . . ? C23A C24A C25A C26A -178.3(3) . . . . ? O3B C21B C22B O5B -17.7(3) . . . . ? O4B C21B C22B O5B 164.2(2) . . . . ? O3B C21B C22B C23B 105.9(3) . . . . ? O4B C21B C22B C23B -72.3(3) . . . . ? O5B C22B C23B C24B -59.3(3) . . . . ? C21B C22B C23B C24B 178.3(2) . . . . ? C22B C23B C24B C25B -179.3(3) . . . . ? C23B C24B C25B C26B -178.0(3) . . . . ? 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 N2A H2A O3A 0.88 2.09 2.935(2) 161.1 . N2B H2B O3B 0.88 1.91 2.777(3) 170.1 . O4A H4A N1A 0.84 1.83 2.654(2) 166.7 . O5A H5A O5B 0.84 1.97 2.782(2) 162.6 . O4B H4B N1B 0.84 1.86 2.704(2) 176.1 . O5B H5B O5A 0.84 1.93 2.765(3) 171.9 1_655 _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.651 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.055 # Attachment 'LCA_1.cif' data_LCA_1 _database_code_depnum_ccdc_archive 'CCDC 791330' #TrackingRef 'LCA_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C20 H13 F3 N4 O2 S, C3 H6 O3 ' _chemical_formula_sum 'C23 H19 F3 N4 O5 S' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour colourless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 520.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_int_tables_number 1 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 4.26530(10) _cell_length_b 10.5529(4) _cell_length_c 26.0208(7) _cell_angle_alpha 79.685(3) _cell_angle_beta 86.626(3) _cell_angle_gamma 85.887(3) _cell_volume 1148.07(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6020 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 1.874 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5617 _exptl_absorpt_correction_T_max 0.8319 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83 to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Scaling and absorption corrections were performed by the SADABS program. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V6.1. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 14586 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0510 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 67.25 _reflns_number_total 5667 _reflns_number_gt 4974 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.58, 2007)' _computing_cell_refinement 'APEX2 (BRUKER, V5-0, 2008)' _computing_data_reduction 'SAINT (BRUKER, V7.56A, 2008)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.0685P)^2^+1.6016P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(3) _refine_ls_number_reflns 5667 _refine_ls_number_parameters 657 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1544 _refine_ls_wR_factor_gt 0.1481 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 S1A S -0.3332(3) 0.61174(13) -0.00764(6) 0.0322(4) Uani 1 1 d . . . F1A F 0.9210(14) 0.9520(6) 0.4476(2) 0.0848(18) Uani 1 1 d . . . F2A F 0.5405(13) 0.8489(10) 0.4800(2) 0.130(3) Uani 1 1 d . . . F3A F 0.9531(13) 0.7527(5) 0.4506(2) 0.0762(15) Uani 1 1 d . . . O1A O 0.2184(11) 0.7722(4) 0.12724(17) 0.0355(11) Uani 1 1 d . . . O2A O -0.6490(13) 0.3900(5) 0.0064(2) 0.0490(14) Uani 1 1 d . . . N1A N -0.1663(13) 0.6048(5) 0.0879(2) 0.0298(12) Uani 1 1 d . . . N2A N -0.4525(13) 0.4312(5) 0.0799(2) 0.0334(13) Uani 1 1 d . . . H2A1 H -0.4373 0.4036 0.1137 0.040 Uiso 1 1 calc R . . N3A N -0.0694(12) 0.9548(5) 0.1457(2) 0.0319(12) Uani 1 1 d . . . N4A N 0.0125(12) 1.0257(5) 0.2256(2) 0.0280(11) Uani 1 1 d . . . C1A C 0.1263(15) 0.8032(6) 0.0748(2) 0.0282(14) Uani 1 1 d . . . C2A C 0.2382(16) 0.9075(7) 0.0409(3) 0.0344(15) Uani 1 1 d . . . H2A H 0.3669 0.9650 0.0529 0.041 Uiso 1 1 calc R . . C3A C 0.1592(17) 0.9272(7) -0.0113(3) 0.0377(16) Uani 1 1 d . . . H3A H 0.2264 1.0016 -0.0344 0.045 Uiso 1 1 calc R . . C4A C -0.0149(16) 0.8412(7) -0.0306(3) 0.0346(15) Uani 1 1 d . . . H4A H -0.0607 0.8532 -0.0665 0.041 Uiso 1 1 calc R . . C5A C -0.1181(15) 0.7376(6) 0.0048(3) 0.0322(15) Uani 1 1 d . . . C6A C -0.0546(15) 0.7150(6) 0.0578(2) 0.0262(13) Uani 1 1 d . . . C7A C -0.3136(16) 0.5458(6) 0.0587(2) 0.0302(14) Uani 1 1 d . . . C8A C -0.6079(15) 0.3587(7) 0.0534(3) 0.0356(16) Uani 1 1 d . . . C9A C -0.717(2) 0.2354(7) 0.0853(3) 0.0480(19) Uani 1 1 d . . . H9A1 H -0.8905 0.2061 0.0682 0.072 Uiso 1 1 calc R . . H9A2 H -0.7898 0.2503 0.1203 0.072 Uiso 1 1 calc R . . H9A3 H -0.5425 0.1693 0.0882 0.072 Uiso 1 1 calc R . . C10A C 0.1351(14) 0.8547(5) 0.1596(2) 0.0236(12) Uani 1 1 d . . . C11A C 0.2733(15) 0.8306(6) 0.2085(3) 0.0296(14) Uani 1 1 d . . . H11A H 0.4070 0.7554 0.2187 0.036 Uiso 1 1 calc R . . C12A C 0.2091(14) 0.9186(6) 0.2408(2) 0.0266(13) Uani 1 1 d . . . C13A C -0.1159(15) 1.0345(6) 0.1796(2) 0.0316(14) Uani 1 1 d . . . H13A H -0.2586 1.1071 0.1699 0.038 Uiso 1 1 calc R . . C14A C 0.3479(14) 0.9045(6) 0.2923(2) 0.0285(13) Uani 1 1 d . . . C15A C 0.4207(17) 0.7823(7) 0.3206(3) 0.0403(16) Uani 1 1 d . . . H15A H 0.3744 0.7083 0.3070 0.048 Uiso 1 1 calc R . . C16A C 0.5596(18) 0.7672(8) 0.3681(3) 0.0476(18) Uani 1 1 d . . . H16A H 0.6136 0.6830 0.3864 0.057 Uiso 1 1 calc R . . C17A C 0.6207(16) 0.8736(8) 0.3893(3) 0.0402(16) Uani 1 1 d . . . C18A C 0.5415(17) 0.9949(7) 0.3626(3) 0.0413(16) Uani 1 1 d . . . H18A H 0.5796 1.0686 0.3770 0.050 Uiso 1 1 calc R . . C19A C 0.4065(17) 1.0097(7) 0.3148(2) 0.0366(15) Uani 1 1 d . . . H19A H 0.3522 1.0942 0.2967 0.044 Uiso 1 1 calc R . . C20A C 0.7548(18) 0.8558(10) 0.4419(3) 0.056(2) Uani 1 1 d . . . S1B S 1.2447(3) 0.54509(14) 0.88955(6) 0.0346(4) Uani 1 1 d . . . F1B F 0.0317(19) 0.2661(7) 0.4208(2) 0.109(2) Uani 1 1 d . . . F2B F 0.4131(15) 0.3766(14) 0.3945(2) 0.230(8) Uani 1 1 d . . . F3B F 0.0085(19) 0.4608(6) 0.4207(2) 0.105(2) Uani 1 1 d . . . O1B O 0.6817(13) 0.3939(5) 0.75356(17) 0.0416(12) Uani 1 1 d . . . O2B O 1.5673(12) 0.7662(5) 0.87704(19) 0.0466(13) Uani 1 1 d . . . N1B N 1.0596(13) 0.5615(5) 0.7949(2) 0.0308(12) Uani 1 1 d . . . N2B N 1.3321(14) 0.7367(5) 0.8054(2) 0.0354(13) Uani 1 1 d . . . H2B H 1.2930 0.7705 0.7728 0.042 Uiso 1 1 calc R . . N3B N 0.9499(14) 0.2097(5) 0.7327(2) 0.0354(13) Uani 1 1 d . . . N4B N 0.8835(14) 0.1548(5) 0.6490(2) 0.0375(13) Uani 1 1 d . . . C1B C 0.7744(17) 0.3614(7) 0.8050(3) 0.0355(16) Uani 1 1 d . . . C2B C 0.6739(19) 0.2535(7) 0.8385(3) 0.0427(18) Uani 1 1 d . . . H2B1 H 0.5459 0.1961 0.8263 0.051 Uiso 1 1 calc R . . C3B C 0.7624(18) 0.2291(7) 0.8910(3) 0.0424(18) Uani 1 1 d . . . H3B H 0.6977 0.1534 0.9135 0.051 Uiso 1 1 calc R . . C4B C 0.9367(17) 0.3107(7) 0.9101(3) 0.0389(17) Uani 1 1 d . . . H4B H 0.9929 0.2929 0.9456 0.047 Uiso 1 1 calc R . . C5B C 1.0333(16) 0.4222(6) 0.8765(3) 0.0319(15) Uani 1 1 d . . . C6B C 0.9485(15) 0.4476(6) 0.8241(3) 0.0308(14) Uani 1 1 d . . . C7B C 1.2140(15) 0.6203(7) 0.8255(3) 0.0340(15) Uani 1 1 d . . . C8G C 1.5073(18) 0.8052(7) 0.8322(3) 0.0383(17) Uani 1 1 d . . . C9E C 1.602(2) 0.9311(8) 0.8013(3) 0.051(2) Uani 1 1 d . . . H9E1 H 1.4374 0.9987 0.8054 0.076 Uiso 1 1 calc R . . H9E2 H 1.6318 0.9239 0.7642 0.076 Uiso 1 1 calc R . . H9E3 H 1.7997 0.9534 0.8139 0.076 Uiso 1 1 calc R . . C10B C 0.7651(17) 0.3138(6) 0.7190(3) 0.0379(17) Uani 1 1 d . . . C11B C 0.6346(16) 0.3480(7) 0.6703(2) 0.0348(15) Uani 1 1 d . . . H11B H 0.5051 0.4250 0.6615 0.042 Uiso 1 1 calc R . . C12B C 0.7032(16) 0.2644(6) 0.6356(3) 0.0333(15) Uani 1 1 d . . . C13B C 1.0037(18) 0.1359(7) 0.6958(3) 0.0381(16) Uani 1 1 d . . . H13B H 1.1434 0.0617 0.7041 0.046 Uiso 1 1 calc R . . C14B C 0.5689(17) 0.2906(7) 0.5819(3) 0.0383(16) Uani 1 1 d . . . C15B C 0.5124(19) 0.1880(7) 0.5579(3) 0.0471(19) Uani 1 1 d . . . H15B H 0.5589 0.1020 0.5751 0.057 Uiso 1 1 calc R . . C16B C 0.3886(19) 0.2102(8) 0.5089(3) 0.0475(18) Uani 1 1 d . . . H16B H 0.3487 0.1398 0.4925 0.057 Uiso 1 1 calc R . . C17B C 0.3239(17) 0.3344(7) 0.4842(3) 0.0432(17) Uani 1 1 d . . . C18B C 0.3763(18) 0.4374(7) 0.5078(3) 0.0455(18) Uani 1 1 d . . . H18B H 0.3280 0.5233 0.4907 0.055 Uiso 1 1 calc R . . C19B C 0.4993(19) 0.4145(7) 0.5566(3) 0.0459(19) Uani 1 1 d . . . H19B H 0.5366 0.4852 0.5730 0.055 Uiso 1 1 calc R . . C20B C 0.1980(19) 0.3589(10) 0.4299(3) 0.058(2) Uani 1 1 d . . . O1C O 0.1163(11) 0.9333(4) 0.60053(17) 0.0406(10) Uani 1 1 d . . . H1C H 0.3102 0.9206 0.6050 0.061 Uiso 1 1 calc R . . O2C O 0.1820(15) 0.8272(5) 0.7025(2) 0.0534(15) Uani 1 1 d . . . O3C O -0.0698(13) 0.6536(5) 0.69429(17) 0.0529(14) Uani 1 1 d . . . H3C H -0.0386 0.6319 0.7263 0.079 Uiso 1 1 calc R . . C1C C 0.0682(19) 0.7208(7) 0.5856(3) 0.0455(17) Uani 1 1 d . . . H1C1 H 0.0133 0.7552 0.5495 0.068 Uiso 1 1 calc R . . H1C2 H -0.0377 0.6409 0.5981 0.068 Uiso 1 1 calc R . . H1C3 H 0.2965 0.7028 0.5869 0.068 Uiso 1 1 calc R . . C2C C -0.0348(15) 0.8179(6) 0.6196(2) 0.0361(14) Uani 1 1 d . . . H2C H -0.2675 0.8364 0.6176 0.043 Uiso 1 1 calc R . . C3C C 0.0420(16) 0.7667(6) 0.6769(2) 0.0368(15) Uani 1 1 d . . . O1D O 0.7081(10) 0.5779(4) 0.19838(15) 0.0357(9) Uani 1 1 d . . . H1D H 0.7393 0.5781 0.1662 0.054 Uiso 1 1 calc R . . O2D O 0.6923(13) 0.3254(4) 0.18543(18) 0.0429(12) Uani 1 1 d . . . O3D O 0.9724(11) 0.2576(4) 0.25489(17) 0.0437(11) Uani 1 1 d . . . H3D H 1.1609 0.2417 0.2456 0.066 Uiso 1 1 calc R . . C1D C 0.8907(18) 0.5001(6) 0.2835(3) 0.0448(16) Uani 1 1 d . . . H1D1 H 0.9391 0.5879 0.2863 0.067 Uiso 1 1 calc R . . H1D2 H 1.0404 0.4379 0.3033 0.067 Uiso 1 1 calc R . . H1D3 H 0.6764 0.4842 0.2977 0.067 Uiso 1 1 calc R . . C2D C 0.9161(14) 0.4848(6) 0.2264(2) 0.0317(13) Uani 1 1 d . . . H2D H 1.1357 0.5012 0.2124 0.038 Uiso 1 1 calc R . . C3D C 0.8444(13) 0.3485(6) 0.2200(2) 0.0281(12) 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 S1A 0.0363(9) 0.0365(9) 0.0250(8) -0.0069(6) -0.0068(6) -0.0014(6) F1A 0.084(4) 0.104(5) 0.076(3) -0.030(3) -0.043(3) -0.005(3) F2A 0.044(3) 0.313(11) 0.034(3) -0.038(4) -0.001(2) 0.003(4) F3A 0.082(4) 0.085(4) 0.062(3) -0.009(3) -0.041(3) 0.010(3) O1A 0.046(3) 0.028(2) 0.034(3) -0.0118(19) -0.006(2) 0.007(2) O2A 0.060(4) 0.052(3) 0.039(3) -0.009(2) -0.013(3) -0.017(3) N1A 0.037(3) 0.029(3) 0.024(3) -0.008(2) -0.007(2) 0.002(2) N2A 0.039(3) 0.035(3) 0.026(3) -0.005(2) -0.005(2) 0.002(2) N3A 0.033(3) 0.031(3) 0.031(3) -0.004(2) -0.003(2) 0.000(2) N4A 0.030(3) 0.023(3) 0.030(3) -0.003(2) 0.001(2) 0.000(2) C1A 0.030(3) 0.032(3) 0.024(3) -0.011(2) -0.005(3) 0.006(3) C2A 0.031(3) 0.032(4) 0.042(4) -0.011(3) -0.004(3) -0.003(3) C3A 0.045(4) 0.029(4) 0.036(4) -0.002(3) 0.004(3) 0.002(3) C4A 0.032(4) 0.041(4) 0.031(3) -0.009(3) 0.001(3) 0.003(3) C5A 0.033(4) 0.033(4) 0.030(4) -0.005(3) -0.002(3) 0.003(3) C6A 0.028(3) 0.027(3) 0.024(3) -0.009(2) -0.001(2) 0.006(2) C7A 0.038(4) 0.028(3) 0.021(3) -0.002(2) 0.002(3) 0.011(3) C8A 0.028(4) 0.042(4) 0.038(4) -0.009(3) -0.004(3) 0.000(3) C9A 0.060(5) 0.040(4) 0.044(4) -0.004(3) -0.011(4) -0.005(4) C10A 0.028(3) 0.018(3) 0.024(3) 0.000(2) 0.004(2) -0.008(2) C11A 0.029(3) 0.024(3) 0.034(3) -0.001(2) -0.001(3) 0.003(2) C12A 0.029(3) 0.025(3) 0.027(3) -0.006(2) 0.004(2) -0.009(2) C13A 0.036(4) 0.023(3) 0.032(3) 0.002(2) -0.001(3) 0.006(2) C14A 0.026(3) 0.031(3) 0.028(3) -0.007(2) 0.005(2) -0.003(2) C15A 0.052(4) 0.032(4) 0.035(4) -0.006(3) -0.007(3) 0.005(3) C16A 0.049(4) 0.048(4) 0.043(4) -0.001(3) -0.010(3) 0.007(3) C17A 0.030(3) 0.059(5) 0.035(4) -0.016(3) -0.004(3) 0.000(3) C18A 0.041(4) 0.045(4) 0.041(4) -0.016(3) -0.005(3) -0.003(3) C19A 0.050(4) 0.034(4) 0.028(3) -0.012(3) -0.005(3) 0.001(3) C20A 0.027(4) 0.098(7) 0.045(4) -0.012(4) -0.013(3) -0.001(4) S1B 0.0369(9) 0.0399(9) 0.0270(8) -0.0043(6) -0.0052(7) -0.0026(7) F1B 0.159(7) 0.095(5) 0.084(4) -0.030(3) -0.070(4) 0.005(4) F2B 0.049(4) 0.59(2) 0.033(3) 0.018(6) -0.009(3) -0.046(7) F3B 0.164(7) 0.066(4) 0.088(4) -0.010(3) -0.070(4) 0.012(4) O1B 0.067(4) 0.032(3) 0.027(2) -0.0057(19) -0.009(2) -0.003(2) O2B 0.051(3) 0.055(3) 0.035(3) -0.007(2) -0.013(2) -0.010(3) N1B 0.034(3) 0.029(3) 0.029(3) -0.006(2) -0.003(2) 0.002(2) N2B 0.049(3) 0.028(3) 0.028(3) -0.001(2) -0.003(2) -0.005(2) N3B 0.048(3) 0.028(3) 0.030(3) -0.003(2) 0.001(2) -0.006(2) N4B 0.053(4) 0.033(3) 0.027(3) -0.005(2) 0.002(3) -0.008(3) C1B 0.041(4) 0.038(4) 0.027(3) -0.004(3) -0.001(3) -0.003(3) C2B 0.060(5) 0.031(4) 0.037(4) -0.006(3) 0.002(3) -0.007(3) C3B 0.049(4) 0.036(4) 0.041(4) 0.000(3) 0.001(3) -0.011(3) C4B 0.043(4) 0.039(4) 0.030(4) 0.008(3) 0.002(3) -0.005(3) C5B 0.039(4) 0.026(3) 0.031(3) -0.009(3) -0.003(3) 0.006(3) C6B 0.032(3) 0.030(4) 0.028(3) -0.001(3) 0.000(3) 0.002(3) C7B 0.029(3) 0.039(4) 0.038(4) -0.015(3) -0.005(3) -0.008(3) C8G 0.050(4) 0.037(4) 0.031(4) -0.011(3) -0.004(3) -0.006(3) C9E 0.066(5) 0.041(4) 0.050(5) -0.011(3) -0.005(4) -0.024(4) C10B 0.047(4) 0.029(4) 0.039(4) -0.007(3) 0.000(3) -0.013(3) C11B 0.044(4) 0.033(4) 0.030(3) -0.010(3) -0.003(3) -0.009(3) C12B 0.033(4) 0.033(3) 0.034(3) -0.005(3) 0.007(3) -0.006(3) C13B 0.051(4) 0.030(4) 0.032(4) -0.003(3) 0.002(3) -0.005(3) C14B 0.046(4) 0.042(4) 0.028(3) -0.006(3) -0.003(3) -0.007(3) C15B 0.059(5) 0.037(4) 0.045(4) -0.007(3) 0.004(4) -0.006(3) C16B 0.060(5) 0.049(5) 0.038(4) -0.020(3) -0.001(3) -0.008(4) C17B 0.039(4) 0.055(5) 0.037(4) -0.011(3) 0.000(3) -0.007(3) C18B 0.055(4) 0.040(4) 0.039(4) -0.002(3) -0.007(3) 0.008(3) C19B 0.066(5) 0.035(4) 0.041(4) -0.013(3) -0.012(4) -0.002(3) C20B 0.037(4) 0.098(7) 0.039(4) -0.011(4) 0.000(3) -0.012(4) O1C 0.044(3) 0.041(3) 0.035(2) 0.0012(18) -0.003(2) -0.008(2) O2C 0.092(4) 0.033(3) 0.039(3) -0.002(2) -0.026(3) -0.015(3) O3C 0.087(4) 0.042(3) 0.030(2) 0.005(2) -0.017(2) -0.027(3) C1C 0.071(5) 0.033(4) 0.034(3) -0.010(3) -0.001(3) -0.009(3) C2C 0.038(3) 0.031(3) 0.039(3) -0.004(3) -0.010(3) -0.001(3) C3C 0.044(4) 0.034(4) 0.031(3) -0.002(3) -0.005(3) -0.002(3) O1D 0.046(2) 0.033(2) 0.026(2) -0.0033(17) -0.0015(18) 0.0046(18) O2D 0.062(3) 0.031(3) 0.037(3) -0.008(2) -0.014(2) 0.004(2) O3D 0.055(3) 0.034(3) 0.039(2) -0.0041(19) -0.015(2) 0.016(2) C1D 0.068(5) 0.029(4) 0.038(4) -0.009(3) -0.011(3) 0.002(3) C2D 0.033(3) 0.027(3) 0.034(3) -0.005(2) -0.003(2) 0.001(2) C3D 0.028(3) 0.029(3) 0.027(3) -0.009(2) 0.002(2) 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 S1A C7A 1.747(6) . ? S1A C5A 1.753(7) . ? F1A C20A 1.313(10) . ? F2A C20A 1.303(10) . ? F3A C20A 1.324(10) . ? O1A C10A 1.333(7) . ? O1A C1A 1.417(7) . ? O2A C8A 1.227(8) . ? N1A C7A 1.281(8) . ? N1A C6A 1.379(8) . ? N2A C8A 1.348(9) . ? N2A C7A 1.394(8) . ? N2A H2A1 0.8800 . ? N3A C13A 1.321(9) . ? N3A C10A 1.333(8) . ? N4A C13A 1.332(8) . ? N4A C12A 1.371(8) . ? C1A C2A 1.376(9) . ? C1A C6A 1.396(9) . ? C2A C3A 1.396(10) . ? C2A H2A 0.9500 . ? C3A C4A 1.389(10) . ? C3A H3A 0.9500 . ? C4A C5A 1.378(9) . ? C4A H4A 0.9500 . ? C5A C6A 1.396(9) . ? C8A C9A 1.501(10) . ? C9A H9A1 0.9800 . ? C9A H9A2 0.9800 . ? C9A H9A3 0.9800 . ? C10A C11A 1.408(9) . ? C11A C12A 1.364(9) . ? C11A H11A 0.9500 . ? C12A C14A 1.476(9) . ? C13A H13A 0.9500 . ? C14A C19A 1.387(9) . ? C14A C15A 1.388(9) . ? C15A C16A 1.381(10) . ? C15A H15A 0.9500 . ? C16A C17A 1.383(11) . ? C16A H16A 0.9500 . ? C17A C18A 1.371(10) . ? C17A C20A 1.491(10) . ? C18A C19A 1.381(10) . ? C18A H18A 0.9500 . ? C19A H19A 0.9500 . ? S1B C7B 1.722(7) . ? S1B C5B 1.724(7) . ? F1B C20B 1.312(11) . ? F2B C20B 1.260(10) . ? F3B C20B 1.293(11) . ? O1B C10B 1.357(9) . ? O1B C1B 1.394(8) . ? O2B C8G 1.202(8) . ? N1B C7B 1.322(8) . ? N1B C6B 1.398(8) . ? N2B C7B 1.365(8) . ? N2B C8G 1.373(9) . ? N2B H2B 0.8800 . ? N3B C10B 1.313(9) . ? N3B C13B 1.341(9) . ? N4B C13B 1.326(9) . ? N4B C12B 1.345(9) . ? C1B C2B 1.383(9) . ? C1B C6B 1.389(10) . ? C2B C3B 1.412(10) . ? C2B H2B1 0.9500 . ? C3B C4B 1.353(10) . ? C3B H3B 0.9500 . ? C4B C5B 1.407(9) . ? C4B H4B 0.9500 . ? C5B C6B 1.406(9) . ? C8G C9E 1.495(10) . ? C9E H9E1 0.9800 . ? C9E H9E2 0.9800 . ? C9E H9E3 0.9800 . ? C10B C11B 1.391(10) . ? C11B C12B 1.377(9) . ? C11B H11B 0.9500 . ? C12B C14B 1.514(9) . ? C13B H13B 0.9500 . ? C14B C19B 1.374(10) . ? C14B C15B 1.386(10) . ? C15B C16B 1.384(11) . ? C15B H15B 0.9500 . ? C16B C17B 1.369(11) . ? C16B H16B 0.9500 . ? C17B C18B 1.379(11) . ? C17B C20B 1.513(10) . ? C18B C19B 1.377(10) . ? C18B H18B 0.9500 . ? C19B H19B 0.9500 . ? O1C C2C 1.415(7) . ? O1C H1C 0.8400 . ? O2C C3C 1.209(8) . ? O3C C3C 1.311(8) . ? O3C H3C 0.8400 . ? C1C C2C 1.497(9) . ? C1C H1C1 0.9800 . ? C1C H1C2 0.9800 . ? C1C H1C3 0.9800 . ? C2C C3C 1.538(8) . ? C2C H2C 1.0000 . ? O1D C2D 1.407(7) . ? O1D H1D 0.8400 . ? O2D C3D 1.207(7) . ? O3D C3D 1.310(7) . ? O3D H3D 0.8400 . ? C1D C2D 1.519(9) . ? C1D H1D1 0.9800 . ? C1D H1D2 0.9800 . ? C1D H1D3 0.9800 . ? C2D C3D 1.532(8) . ? C2D H2D 1.0000 . ? 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 C7A S1A C5A 87.4(3) . . ? C10A O1A C1A 118.9(5) . . ? C7A N1A C6A 108.7(5) . . ? C8A N2A C7A 126.0(6) . . ? C8A N2A H2A1 117.0 . . ? C7A N2A H2A1 117.0 . . ? C13A N3A C10A 115.0(5) . . ? C13A N4A C12A 116.4(5) . . ? C2A C1A C6A 121.6(6) . . ? C2A C1A O1A 121.5(6) . . ? C6A C1A O1A 116.5(5) . . ? C1A C2A C3A 118.8(6) . . ? C1A C2A H2A 120.6 . . ? C3A C2A H2A 120.6 . . ? C4A C3A C2A 121.9(6) . . ? C4A C3A H3A 119.0 . . ? C2A C3A H3A 119.0 . . ? C5A C4A C3A 116.9(6) . . ? C5A C4A H4A 121.6 . . ? C3A C4A H4A 121.6 . . ? C4A C5A C6A 123.7(6) . . ? C4A C5A S1A 127.6(5) . . ? C6A C5A S1A 108.7(5) . . ? N1A C6A C1A 126.3(6) . . ? N1A C6A C5A 116.7(6) . . ? C1A C6A C5A 116.9(6) . . ? N1A C7A N2A 120.2(5) . . ? N1A C7A S1A 118.5(5) . . ? N2A C7A S1A 121.3(5) . . ? O2A C8A N2A 122.2(6) . . ? O2A C8A C9A 122.9(6) . . ? N2A C8A C9A 114.9(6) . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? O1A C10A N3A 120.8(5) . . ? O1A C10A C11A 116.8(5) . . ? N3A C10A C11A 122.4(6) . . ? C12A C11A C10A 117.9(6) . . ? C12A C11A H11A 121.1 . . ? C10A C11A H11A 121.1 . . ? C11A C12A N4A 120.1(6) . . ? C11A C12A C14A 122.3(6) . . ? N4A C12A C14A 117.6(5) . . ? N3A C13A N4A 128.0(6) . . ? N3A C13A H13A 116.0 . . ? N4A C13A H13A 116.0 . . ? C19A C14A C15A 117.6(6) . . ? C19A C14A C12A 122.5(6) . . ? C15A C14A C12A 120.0(6) . . ? C16A C15A C14A 120.8(7) . . ? C16A C15A H15A 119.6 . . ? C14A C15A H15A 119.6 . . ? C15A C16A C17A 120.6(7) . . ? C15A C16A H16A 119.7 . . ? C17A C16A H16A 119.7 . . ? C18A C17A C16A 119.3(6) . . ? C18A C17A C20A 120.6(7) . . ? C16A C17A C20A 120.0(7) . . ? C17A C18A C19A 120.0(7) . . ? C17A C18A H18A 120.0 . . ? C19A C18A H18A 120.0 . . ? C18A C19A C14A 121.8(6) . . ? C18A C19A H19A 119.1 . . ? C14A C19A H19A 119.1 . . ? F2A C20A F1A 104.7(8) . . ? F2A C20A F3A 109.0(8) . . ? F1A C20A F3A 104.5(6) . . ? F2A C20A C17A 113.2(6) . . ? F1A C20A C17A 112.7(7) . . ? F3A C20A C17A 112.1(7) . . ? C7B S1B C5B 89.1(3) . . ? C10B O1B C1B 120.0(6) . . ? C7B N1B C6B 109.4(6) . . ? C7B N2B C8G 125.1(6) . . ? C7B N2B H2B 117.5 . . ? C8G N2B H2B 117.5 . . ? C10B N3B C13B 114.6(6) . . ? C13B N4B C12B 116.5(6) . . ? C2B C1B C6B 119.4(6) . . ? C2B C1B O1B 122.2(6) . . ? C6B C1B O1B 118.1(5) . . ? C1B C2B C3B 119.7(7) . . ? C1B C2B H2B1 120.2 . . ? C3B C2B H2B1 120.2 . . ? C4B C3B C2B 121.8(6) . . ? C4B C3B H3B 119.1 . . ? C2B C3B H3B 119.1 . . ? C3B C4B C5B 118.8(6) . . ? C3B C4B H4B 120.6 . . ? C5B C4B H4B 120.6 . . ? C6B C5B C4B 120.2(6) . . ? C6B C5B S1B 110.2(5) . . ? C4B C5B S1B 129.5(5) . . ? C1B C6B N1B 125.5(6) . . ? C1B C6B C5B 120.1(6) . . ? N1B C6B C5B 114.4(6) . . ? N1B C7B N2B 119.2(6) . . ? N1B C7B S1B 116.9(5) . . ? N2B C7B S1B 123.8(5) . . ? O2B C8G N2B 121.4(6) . . ? O2B C8G C9E 124.5(6) . . ? N2B C8G C9E 114.1(6) . . ? C8G C9E H9E1 109.5 . . ? C8G C9E H9E2 109.5 . . ? H9E1 C9E H9E2 109.5 . . ? C8G C9E H9E3 109.5 . . ? H9E1 C9E H9E3 109.5 . . ? H9E2 C9E H9E3 109.5 . . ? N3B C10B O1B 120.4(6) . . ? N3B C10B C11B 124.0(7) . . ? O1B C10B C11B 115.6(6) . . ? C12B C11B C10B 116.5(7) . . ? C12B C11B H11B 121.8 . . ? C10B C11B H11B 121.8 . . ? N4B C12B C11B 121.1(6) . . ? N4B C12B C14B 117.8(6) . . ? C11B C12B C14B 121.0(6) . . ? N4B C13B N3B 127.2(7) . . ? N4B C13B H13B 116.4 . . ? N3B C13B H13B 116.4 . . ? C19B C14B C15B 119.3(7) . . ? C19B C14B C12B 121.2(6) . . ? C15B C14B C12B 119.5(6) . . ? C16B C15B C14B 120.2(7) . . ? C16B C15B H15B 119.9 . . ? C14B C15B H15B 119.9 . . ? C17B C16B C15B 119.5(7) . . ? C17B C16B H16B 120.2 . . ? C15B C16B H16B 120.2 . . ? C16B C17B C18B 120.8(7) . . ? C16B C17B C20B 119.6(7) . . ? C18B C17B C20B 119.6(7) . . ? C19B C18B C17B 119.4(7) . . ? C19B C18B H18B 120.3 . . ? C17B C18B H18B 120.3 . . ? C14B C19B C18B 120.8(7) . . ? C14B C19B H19B 119.6 . . ? C18B C19B H19B 119.6 . . ? F2B C20B F3B 104.8(10) . . ? F2B C20B F1B 108.0(10) . . ? F3B C20B F1B 103.8(7) . . ? F2B C20B C17B 112.4(7) . . ? F3B C20B C17B 113.7(8) . . ? F1B C20B C17B 113.4(7) . . ? C2C O1C H1C 109.5 . . ? C3C O3C H3C 109.5 . . ? C2C C1C H1C1 109.5 . . ? C2C C1C H1C2 109.5 . . ? H1C1 C1C H1C2 109.5 . . ? C2C C1C H1C3 109.5 . . ? H1C1 C1C H1C3 109.5 . . ? H1C2 C1C H1C3 109.5 . . ? O1C C2C C1C 108.8(5) . . ? O1C C2C C3C 110.5(5) . . ? C1C C2C C3C 111.1(5) . . ? O1C C2C H2C 108.8 . . ? C1C C2C H2C 108.8 . . ? C3C C2C H2C 108.8 . . ? O2C C3C O3C 125.1(6) . . ? O2C C3C C2C 122.8(6) . . ? O3C C3C C2C 112.1(5) . . ? C2D O1D H1D 109.5 . . ? C3D O3D H3D 109.5 . . ? C2D C1D H1D1 109.5 . . ? C2D C1D H1D2 109.5 . . ? H1D1 C1D H1D2 109.5 . . ? C2D C1D H1D3 109.5 . . ? H1D1 C1D H1D3 109.5 . . ? H1D2 C1D H1D3 109.5 . . ? O1D C2D C1D 108.5(5) . . ? O1D C2D C3D 111.0(5) . . ? C1D C2D C3D 111.5(5) . . ? O1D C2D H2D 108.6 . . ? C1D C2D H2D 108.6 . . ? C3D C2D H2D 108.6 . . ? O2D C3D O3D 122.6(6) . . ? O2D C3D C2D 123.9(5) . . ? O3D C3D C2D 113.4(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 C10A O1A C1A C2A 65.0(8) . . . . ? C10A O1A C1A C6A -121.9(6) . . . . ? C6A C1A C2A C3A 2.1(11) . . . . ? O1A C1A C2A C3A 174.9(6) . . . . ? C1A C2A C3A C4A -3.4(11) . . . . ? C2A C3A C4A C5A 2.6(11) . . . . ? C3A C4A C5A C6A -0.6(11) . . . . ? C3A C4A C5A S1A -178.5(5) . . . . ? C7A S1A C5A C4A 178.4(7) . . . . ? C7A S1A C5A C6A 0.2(5) . . . . ? C7A N1A C6A C1A -177.9(6) . . . . ? C7A N1A C6A C5A -0.7(8) . . . . ? C2A C1A C6A N1A 177.0(6) . . . . ? O1A C1A C6A N1A 3.9(10) . . . . ? C2A C1A C6A C5A -0.2(10) . . . . ? O1A C1A C6A C5A -173.3(5) . . . . ? C4A C5A C6A N1A -178.0(7) . . . . ? S1A C5A C6A N1A 0.2(7) . . . . ? C4A C5A C6A C1A -0.6(10) . . . . ? S1A C5A C6A C1A 177.6(5) . . . . ? C6A N1A C7A N2A -179.5(6) . . . . ? C6A N1A C7A S1A 0.9(8) . . . . ? C8A N2A C7A N1A -178.6(6) . . . . ? C8A N2A C7A S1A 1.1(10) . . . . ? C5A S1A C7A N1A -0.7(6) . . . . ? C5A S1A C7A N2A 179.7(6) . . . . ? C7A N2A C8A O2A -1.8(11) . . . . ? C7A N2A C8A C9A 176.4(7) . . . . ? C1A O1A C10A N3A 9.9(8) . . . . ? C1A O1A C10A C11A -170.0(5) . . . . ? C13A N3A C10A O1A -175.4(5) . . . . ? C13A N3A C10A C11A 4.5(8) . . . . ? O1A C10A C11A C12A 175.4(5) . . . . ? N3A C10A C11A C12A -4.5(8) . . . . ? C10A C11A C12A N4A 0.8(8) . . . . ? C10A C11A C12A C14A -178.4(5) . . . . ? C13A N4A C12A C11A 2.4(8) . . . . ? C13A N4A C12A C14A -178.3(5) . . . . ? C10A N3A C13A N4A -1.0(9) . . . . ? C12A N4A C13A N3A -2.5(9) . . . . ? C11A C12A C14A C19A 150.3(7) . . . . ? N4A C12A C14A C19A -28.9(9) . . . . ? C11A C12A C14A C15A -30.6(9) . . . . ? N4A C12A C14A C15A 150.2(6) . . . . ? C19A C14A C15A C16A -2.9(10) . . . . ? C12A C14A C15A C16A 178.0(6) . . . . ? C14A C15A C16A C17A 1.9(11) . . . . ? C15A C16A C17A C18A 0.1(11) . . . . ? C15A C16A C17A C20A 176.7(7) . . . . ? C16A C17A C18A C19A -1.0(11) . . . . ? C20A C17A C18A C19A -177.5(7) . . . . ? C17A C18A C19A C14A -0.2(11) . . . . ? C15A C14A C19A C18A 2.0(10) . . . . ? C12A C14A C19A C18A -178.8(6) . . . . ? C18A C17A C20A F2A 87.7(10) . . . . ? C16A C17A C20A F2A -88.9(11) . . . . ? C18A C17A C20A F1A -31.0(10) . . . . ? C16A C17A C20A F1A 152.5(8) . . . . ? C18A C17A C20A F3A -148.5(7) . . . . ? C16A C17A C20A F3A 34.9(10) . . . . ? C10B O1B C1B C2B -63.5(10) . . . . ? C10B O1B C1B C6B 122.8(7) . . . . ? C6B C1B C2B C3B -3.1(12) . . . . ? O1B C1B C2B C3B -176.7(7) . . . . ? C1B C2B C3B C4B 1.9(12) . . . . ? C2B C3B C4B C5B -0.4(12) . . . . ? C3B C4B C5B C6B 0.1(11) . . . . ? C3B C4B C5B S1B 178.0(6) . . . . ? C7B S1B C5B C6B -0.9(5) . . . . ? C7B S1B C5B C4B -179.0(7) . . . . ? C2B C1B C6B N1B -178.7(7) . . . . ? O1B C1B C6B N1B -4.8(11) . . . . ? C2B C1B C6B C5B 2.8(11) . . . . ? O1B C1B C6B C5B 176.7(6) . . . . ? C7B N1B C6B C1B 179.6(7) . . . . ? C7B N1B C6B C5B -1.8(8) . . . . ? C4B C5B C6B C1B -1.3(10) . . . . ? S1B C5B C6B C1B -179.5(6) . . . . ? C4B C5B C6B N1B -180.0(7) . . . . ? S1B C5B C6B N1B 1.8(7) . . . . ? C6B N1B C7B N2B -177.3(6) . . . . ? C6B N1B C7B S1B 1.1(8) . . . . ? C8G N2B C7B N1B -177.2(7) . . . . ? C8G N2B C7B S1B 4.5(11) . . . . ? C5B S1B C7B N1B -0.1(6) . . . . ? C5B S1B C7B N2B 178.2(6) . . . . ? C7B N2B C8G O2B -0.9(12) . . . . ? C7B N2B C8G C9E -178.9(7) . . . . ? C13B N3B C10B O1B 177.3(6) . . . . ? C13B N3B C10B C11B -0.6(9) . . . . ? C1B O1B C10B N3B -4.4(9) . . . . ? C1B O1B C10B C11B 173.6(6) . . . . ? N3B C10B C11B C12B 1.3(10) . . . . ? O1B C10B C11B C12B -176.7(6) . . . . ? C13B N4B C12B C11B -3.5(9) . . . . ? C13B N4B C12B C14B 178.5(6) . . . . ? C10B C11B C12B N4B 0.9(9) . . . . ? C10B C11B C12B C14B 178.8(6) . . . . ? C12B N4B C13B N3B 4.5(10) . . . . ? C10B N3B C13B N4B -2.4(10) . . . . ? N4B C12B C14B C19B -152.7(7) . . . . ? C11B C12B C14B C19B 29.3(10) . . . . ? N4B C12B C14B C15B 27.9(10) . . . . ? C11B C12B C14B C15B -150.1(7) . . . . ? C19B C14B C15B C16B 0.3(12) . . . . ? C12B C14B C15B C16B 179.7(7) . . . . ? C14B C15B C16B C17B 0.4(12) . . . . ? C15B C16B C17B C18B -1.0(12) . . . . ? C15B C16B C17B C20B 178.1(7) . . . . ? C16B C17B C18B C19B 0.9(12) . . . . ? C20B C17B C18B C19B -178.2(7) . . . . ? C15B C14B C19B C18B -0.3(12) . . . . ? C12B C14B C19B C18B -179.8(7) . . . . ? C17B C18B C19B C14B -0.2(12) . . . . ? C16B C17B C20B F2B -93.4(12) . . . . ? C18B C17B C20B F2B 85.7(13) . . . . ? C16B C17B C20B F3B 147.7(8) . . . . ? C18B C17B C20B F3B -33.2(10) . . . . ? C16B C17B C20B F1B 29.5(11) . . . . ? C18B C17B C20B F1B -151.4(8) . . . . ? O1C C2C C3C O2C 7.9(10) . . . . ? C1C C2C C3C O2C 128.8(8) . . . . ? O1C C2C C3C O3C -174.0(6) . . . . ? C1C C2C C3C O3C -53.1(8) . . . . ? O1D C2D C3D O2D 18.4(8) . . . . ? C1D C2D C3D O2D 139.5(6) . . . . ? O1D C2D C3D O3D -163.5(5) . . . . ? C1D C2D C3D O3D -42.4(7) . . . . ? 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 N2A H2A1 O2D 0.88 1.99 2.858(7) 167.1 1_455 N2B H2B O2C 0.88 1.90 2.774(7) 173.6 1_655 O3C H3C N1B 0.84 1.87 2.700(7) 171.6 1_455 O1D H1D N1A 0.84 2.03 2.860(6) 171.7 1_655 _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 67.25 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.697 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.068 # Attachment 'LCA_2.cif' data_LCA_2 _database_code_depnum_ccdc_archive 'CCDC 791331' #TrackingRef 'LCA_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H19 F3 N4 O5 S' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour colourless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 520.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_int_tables_number 4 _chemical_absolute_configuration ad _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 19.0132(4) _cell_length_b 4.51900(10) _cell_length_c 26.8556(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.8140(10) _cell_angle_gamma 90.00 _cell_volume 2280.20(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2747 _cell_measurement_theta_min 5.00 _cell_measurement_theta_max 65.20 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 1.887 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4873 _exptl_absorpt_correction_T_max 0.9050 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83 to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Scaling and absorption corrections were performed by the SADABS program. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V6.1. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_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 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14895 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0708 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 68.08 _reflns_number_total 7014 _reflns_number_gt 5201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V5.007, 2006)' _computing_cell_refinement 'APEX2 (BRUKER, V2.1-0, 2006)' _computing_data_reduction 'SAINT (BRUKER, V7.34A, 2006)' _computing_structure_solution 'BRUKER, SHELXS-90, V6.14)' _computing_structure_refinement 'BRUKER, SHELXL-01, V6.14)' _computing_molecular_graphics 'SHELXTL (BRUKER, 2000, V6.14)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, v6.12, 2001,)' _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^)+(0.0807P)^2^+1.3625P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(3) _refine_ls_number_reflns 7014 _refine_ls_number_parameters 653 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1712 _refine_ls_wR_factor_gt 0.1546 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1A S 0.76996(7) 0.0485(3) 0.69363(4) 0.0385(3) Uani 1 1 d . . . F1A F 0.6877(2) 1.3623(12) 0.22740(14) 0.0748(14) Uani 1 1 d . . . F2A F 0.6440(2) 0.9671(10) 0.19172(13) 0.0611(11) Uani 1 1 d . . . F3A F 0.5749(2) 1.3137(11) 0.20707(14) 0.0648(11) Uani 1 1 d . . . O1A O 0.8854(2) -0.3241(11) 0.69991(14) 0.0495(11) Uani 1 1 d . . . O2A O 0.6810(2) 0.7115(10) 0.55131(13) 0.0399(10) Uani 1 1 d . . . N1A N 0.8598(2) -0.0842(12) 0.62611(15) 0.0367(11) Uani 1 1 d . . . H1A H 0.8718 -0.0631 0.5959 0.044 Uiso 1 1 calc R . . N2A N 0.7692(2) 0.2624(11) 0.60345(15) 0.0329(11) Uani 1 1 d . . . N3A N 0.5928(2) 0.4069(12) 0.51035(16) 0.0382(12) Uani 1 1 d . . . N4A N 0.5630(2) 0.4428(12) 0.42044(16) 0.0371(12) Uani 1 1 d . . . C1A C 0.8028(3) 0.0800(14) 0.63672(18) 0.0337(12) Uani 1 1 d . . . C2A C 0.7040(3) 0.3057(14) 0.67116(18) 0.0364(13) Uani 1 1 d . . . C3A C 0.7133(3) 0.3916(15) 0.62254(19) 0.0387(14) Uani 1 1 d . . . C4A C 0.6662(3) 0.6029(15) 0.59781(18) 0.0372(13) Uani 1 1 d . . . C5A C 0.6129(3) 0.7196(16) 0.6203(2) 0.0461(16) Uani 1 1 d . . . H5A H 0.5817 0.8642 0.6033 0.055 Uiso 1 1 calc R . . C6A C 0.6044(3) 0.6238(16) 0.6688(2) 0.0459(16) Uani 1 1 d . . . H6A H 0.5665 0.7021 0.6841 0.055 Uiso 1 1 calc R . . C7A C 0.6503(3) 0.4163(14) 0.6953(2) 0.0410(14) Uani 1 1 d . . . H7A H 0.6449 0.3541 0.7283 0.049 Uiso 1 1 calc R . . C8A C 0.8989(3) -0.2750(14) 0.6579(2) 0.0382(13) Uani 1 1 d . . . C9A C 0.9594(3) -0.4170(16) 0.63675(19) 0.0427(14) Uani 1 1 d . . . H9A H 1.0046 -0.3317 0.6529 0.064 Uiso 1 1 calc R . . H9B H 0.9537 -0.3813 0.6004 0.064 Uiso 1 1 calc R . . H9C H 0.9594 -0.6305 0.6431 0.064 Uiso 1 1 calc R . . C10A C 0.6422(3) 0.6128(13) 0.50825(18) 0.0328(13) Uani 1 1 d . . . C11A C 0.5560(3) 0.3360(15) 0.46418(19) 0.0393(14) Uani 1 1 d . . . H11A H 0.5204 0.1884 0.4641 0.047 Uiso 1 1 calc R . . C12A C 0.6561(3) 0.7416(13) 0.46389(18) 0.0320(12) Uani 1 1 d . . . H12A H 0.6925 0.8855 0.4638 0.038 Uiso 1 1 calc R . . C13A C 0.6143(3) 0.6500(15) 0.41987(19) 0.0368(14) Uani 1 1 d . . . C14A C 0.6217(3) 0.7794(14) 0.36972(19) 0.0350(13) Uani 1 1 d . . . C15A C 0.5644(3) 0.7598(15) 0.33011(19) 0.0389(14) Uani 1 1 d . . . H15A H 0.5226 0.6551 0.3349 0.047 Uiso 1 1 calc R . . C16A C 0.5684(3) 0.8918(16) 0.2842(2) 0.0456(16) Uani 1 1 d . . . H16A H 0.5289 0.8824 0.2579 0.055 Uiso 1 1 calc R . . C17A C 0.6309(3) 1.0403(15) 0.27644(19) 0.0398(13) Uani 1 1 d . . . C18A C 0.6873(3) 1.0541(17) 0.3151(2) 0.0456(15) Uani 1 1 d . . . H18A H 0.7299 1.1527 0.3102 0.055 Uiso 1 1 calc R . . C19A C 0.6823(3) 0.9244(16) 0.3612(2) 0.0454(16) Uani 1 1 d . . . H19A H 0.7216 0.9361 0.3876 0.054 Uiso 1 1 calc R . . C20A C 0.6337(3) 1.1697(16) 0.2265(2) 0.0439(15) Uani 1 1 d . . . S1B S 0.71170(9) 0.8446(4) -0.18773(5) 0.0514(4) Uani 1 1 d . . . F1B F 0.9400(2) -0.4445(10) 0.29495(12) 0.0600(10) Uani 1 1 d . . . F2B F 0.8710(2) -0.1014(9) 0.31196(12) 0.0589(11) Uani 1 1 d . . . F3B F 0.8277(2) -0.4924(11) 0.27565(13) 0.0706(13) Uani 1 1 d . . . O1B O 0.5954(3) 1.2028(15) -0.1917(2) 0.0863(19) Uani 1 1 d . . . O2B O 0.8122(2) 0.2020(10) -0.04576(13) 0.0421(10) Uani 1 1 d . . . N1B N 0.6247(3) 0.9577(13) -0.1181(2) 0.0514(14) Uani 1 1 d . . . H1B H 0.6132 0.9255 -0.0881 0.062 Uiso 1 1 calc R . . N2B N 0.7190(3) 0.6367(12) -0.09661(17) 0.0427(12) Uani 1 1 d . . . N3B N 0.9059(2) 0.4901(12) -0.00741(15) 0.0374(12) Uani 1 1 d . . . N4B N 0.9438(2) 0.4405(12) 0.08169(16) 0.0411(12) Uani 1 1 d . . . C1B C 0.6817(3) 0.8172(17) -0.1300(2) 0.0464(15) Uani 1 1 d . . . C2B C 0.7794(3) 0.5970(16) -0.1664(2) 0.0463(16) Uani 1 1 d . . . C3B C 0.7752(3) 0.5089(14) -0.11717(19) 0.0365(13) Uani 1 1 d . . . C4B C 0.8229(3) 0.3079(16) -0.09330(19) 0.0427(15) Uani 1 1 d . . . C5B C 0.8752(3) 0.1903(17) -0.1176(2) 0.0473(16) Uani 1 1 d . . . H5B H 0.9074 0.0472 -0.1013 0.057 Uiso 1 1 calc R . . C6B C 0.8803(4) 0.2829(18) -0.1662(2) 0.0554(19) Uani 1 1 d . . . H6B H 0.9173 0.2057 -0.1826 0.067 Uiso 1 1 calc R . . C7B C 0.8330(4) 0.4850(18) -0.1915(2) 0.0556(19) Uani 1 1 d . . . H7B H 0.8367 0.5457 -0.2248 0.067 Uiso 1 1 calc R . . C8B C 0.5820(4) 1.1524(17) -0.1501(3) 0.063(2) Uani 1 1 d . . . C9B C 0.5216(4) 1.279(2) -0.1289(3) 0.080(3) Uani 1 1 d . . . H9B1 H 0.4841 1.1294 -0.1295 0.119 Uiso 1 1 calc R . . H9B2 H 0.5028 1.4503 -0.1490 0.119 Uiso 1 1 calc R . . H9B3 H 0.5376 1.3415 -0.0941 0.119 Uiso 1 1 calc R . . C10B C 0.8567(3) 0.2903(16) -0.00374(19) 0.0391(14) Uani 1 1 d . . . C11B C 0.9462(3) 0.5543(16) 0.03649(19) 0.0434(15) Uani 1 1 d . . . H11B H 0.9814 0.7019 0.0351 0.052 Uiso 1 1 calc R . . C12B C 0.8468(3) 0.1564(14) 0.04096(19) 0.0372(14) Uani 1 1 d . . . H12B H 0.8104 0.0138 0.0421 0.045 Uiso 1 1 calc R . . C13B C 0.8922(3) 0.2391(14) 0.08378(19) 0.0349(13) Uani 1 1 d . . . C14B C 0.8882(3) 0.1033(15) 0.13426(18) 0.0363(13) Uani 1 1 d . . . C15B C 0.8280(3) -0.0418(17) 0.1432(2) 0.0501(18) Uani 1 1 d . . . H15B H 0.7882 -0.0536 0.1171 0.060 Uiso 1 1 calc R . . C16B C 0.8240(3) -0.1709(18) 0.1893(2) 0.0488(16) Uani 1 1 d . . . H16B H 0.7814 -0.2641 0.1957 0.059 Uiso 1 1 calc R . . C17B C 0.8837(3) -0.1609(15) 0.22609(19) 0.0387(13) Uani 1 1 d . . . C18B C 0.9447(3) -0.0188(16) 0.2177(2) 0.0464(16) Uani 1 1 d . . . H18B H 0.9851 -0.0124 0.2433 0.056 Uiso 1 1 calc R . . C19B C 0.9468(3) 0.1144(16) 0.17175(19) 0.0436(16) Uani 1 1 d . . . H19B H 0.9887 0.2142 0.1658 0.052 Uiso 1 1 calc R . . C20B C 0.8803(3) -0.2998(17) 0.2763(2) 0.0481(16) Uani 1 1 d . . . O1S O 0.8980(2) 0.1035(10) 0.53394(13) 0.0454(10) Uani 1 1 d . . . O2S O 0.8116(2) 0.4371(11) 0.51781(14) 0.0510(12) Uani 1 1 d . . . H2S1 H 0.7987 0.3585 0.5433 0.076 Uiso 1 1 calc R . . O3S O 0.9688(2) 0.3283(11) 0.46451(16) 0.0517(11) Uani 1 1 d . . . H3S H 0.9981 0.4680 0.4657 0.078 Uiso 1 1 calc R . . C1S C 0.8519(3) 0.3605(19) 0.41620(19) 0.0520(17) Uani 1 1 d . . . H1S1 H 0.8682 0.4609 0.3877 0.078 Uiso 1 1 calc R . . H1S2 H 0.8030 0.4216 0.4184 0.078 Uiso 1 1 calc R . . H1S3 H 0.8533 0.1459 0.4112 0.078 Uiso 1 1 calc R . . C2S C 0.9003(3) 0.4431(12) 0.46484(17) 0.0325(11) Uani 1 1 d . . . H2S H 0.9029 0.6633 0.4683 0.039 Uiso 1 1 calc R . . C4S C 0.8700(3) 0.3119(13) 0.50870(18) 0.0338(12) Uani 1 1 d . . . O1E O 0.5844(4) 0.830(2) -0.0293(3) 0.0422(18) Uiso 0.50 1 d PD A 1 O2E O 0.6932(8) 0.552(5) -0.0079(6) 0.135(6) Uiso 0.50 1 d PD A 1 H2E H 0.6900 0.4068 -0.0278 0.202 Uiso 0.50 1 calc PR A 1 O3E O 0.6592(12) 0.525(7) 0.0895(6) 0.165(10) Uiso 0.50 1 d PD A 1 H3E H 0.6426 0.6513 0.1074 0.248 Uiso 0.50 1 calc PR A 1 C1E C 0.6265(7) 0.661(4) -0.0056(6) 0.089(5) Uiso 0.50 1 d PD A 1 C2E C 0.6146(11) 0.503(8) 0.0426(6) 0.197(15) Uiso 0.50 1 d PD A 1 H2E1 H 0.6393 0.3204 0.0334 0.236 Uiso 0.50 1 calc PR A 1 C3E C 0.5423(7) 0.351(3) 0.0341(5) 0.059(3) Uiso 0.50 1 d PD A 1 H3E1 H 0.5488 0.1386 0.0292 0.088 Uiso 0.50 1 calc PR A 1 H3E2 H 0.5133 0.4347 0.0041 0.088 Uiso 0.50 1 calc PR A 1 H3E3 H 0.5184 0.3825 0.0635 0.088 Uiso 0.50 1 calc PR A 1 O1F O 0.5704(6) 0.613(3) -0.0276(4) 0.078(3) Uiso 0.50 1 d PD B 2 O3F O 0.7097(3) 0.7266(16) 0.0094(3) 0.0295(15) Uiso 0.50 1 d PD B 2 H3F H 0.6916 0.8934 0.0130 0.044 Uiso 0.50 1 calc PR B 2 O2F O 0.5909(9) 0.164(4) 0.0306(6) 0.133(6) Uiso 0.50 1 d PD B 2 H2F H 0.6052 0.0468 0.0101 0.200 Uiso 0.50 1 d PR B 2 C2F C 0.6652(5) 0.503(2) 0.0247(3) 0.034(2) Uiso 0.50 1 d PD B 2 H2F1 H 0.6847 0.3141 0.0131 0.041 Uiso 0.50 1 calc PR B 2 C1F C 0.5844(5) 0.475(4) 0.0096(6) 0.087(5) Uiso 0.50 1 d PD B 2 C3F C 0.6781(9) 0.482(4) 0.0822(3) 0.054(4) Uiso 0.50 1 d PD B 2 H3F1 H 0.7283 0.4355 0.0938 0.081 Uiso 0.50 1 calc PR B 2 H3F2 H 0.6481 0.3264 0.0931 0.081 Uiso 0.50 1 calc PR B 2 H3F3 H 0.6664 0.6721 0.0966 0.081 Uiso 0.50 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1A 0.0434(7) 0.0447(9) 0.0299(6) 0.0013(6) 0.0134(5) -0.0040(7) F1A 0.079(3) 0.081(4) 0.061(2) 0.027(2) -0.0027(19) -0.036(3) F2A 0.085(3) 0.057(3) 0.0451(19) 0.0034(19) 0.0241(18) 0.005(2) F3A 0.065(2) 0.067(3) 0.059(2) 0.015(2) 0.0015(18) 0.013(2) O1A 0.054(3) 0.058(3) 0.038(2) 0.012(2) 0.0140(18) 0.003(2) O2A 0.039(2) 0.044(3) 0.036(2) -0.0004(19) 0.0053(16) -0.0078(18) N1A 0.037(3) 0.047(3) 0.028(2) 0.005(2) 0.0096(18) -0.002(2) N2A 0.034(2) 0.036(3) 0.029(2) 0.000(2) 0.0062(18) -0.005(2) N3A 0.028(2) 0.048(4) 0.040(2) -0.002(2) 0.0099(18) 0.001(2) N4A 0.030(2) 0.044(3) 0.038(2) -0.006(2) 0.0093(18) -0.004(2) C1A 0.038(3) 0.032(3) 0.032(2) -0.002(2) 0.007(2) -0.008(3) C2A 0.039(3) 0.036(4) 0.035(3) 0.001(3) 0.010(2) -0.007(3) C3A 0.033(3) 0.051(4) 0.033(3) -0.011(3) 0.010(2) -0.011(3) C4A 0.037(3) 0.041(4) 0.034(3) -0.001(3) 0.005(2) -0.008(3) C5A 0.038(3) 0.050(4) 0.050(4) -0.008(3) 0.005(3) -0.007(3) C6A 0.041(3) 0.055(5) 0.046(3) -0.017(3) 0.020(3) -0.008(3) C7A 0.047(3) 0.036(4) 0.042(3) -0.008(3) 0.016(2) -0.009(3) C8A 0.037(3) 0.043(4) 0.035(3) 0.002(3) 0.005(2) -0.007(3) C9A 0.032(3) 0.050(4) 0.046(3) 0.012(3) 0.005(2) 0.001(3) C10A 0.026(3) 0.036(4) 0.037(3) 0.000(3) 0.007(2) 0.005(2) C11A 0.033(3) 0.042(4) 0.045(3) -0.001(3) 0.013(2) -0.007(3) C12A 0.022(3) 0.034(3) 0.040(3) -0.001(2) 0.003(2) -0.003(2) C13A 0.028(3) 0.050(4) 0.034(3) -0.002(3) 0.009(2) 0.002(2) C14A 0.032(3) 0.037(4) 0.036(3) -0.005(2) 0.005(2) 0.000(2) C15A 0.031(3) 0.050(4) 0.037(3) -0.001(3) 0.010(2) -0.006(3) C16A 0.038(3) 0.059(5) 0.038(3) -0.008(3) 0.003(2) -0.003(3) C17A 0.039(3) 0.040(4) 0.041(3) 0.002(3) 0.010(2) 0.001(3) C18A 0.032(3) 0.054(4) 0.051(3) 0.010(3) 0.009(2) -0.012(3) C19A 0.035(3) 0.053(4) 0.045(3) 0.006(3) -0.002(2) -0.007(3) C20A 0.045(4) 0.043(4) 0.044(3) 0.007(3) 0.008(3) -0.004(3) S1B 0.0643(10) 0.0485(10) 0.0388(7) 0.0102(7) -0.0006(7) -0.0105(8) F1B 0.067(2) 0.060(3) 0.0502(19) 0.012(2) 0.0016(17) 0.008(2) F2B 0.083(3) 0.057(3) 0.0400(17) 0.0025(18) 0.0197(17) 0.002(2) F3B 0.077(3) 0.075(3) 0.055(2) 0.021(2) -0.0030(18) -0.031(2) O1B 0.067(4) 0.081(5) 0.104(4) 0.044(4) -0.008(3) -0.002(3) O2B 0.037(2) 0.056(3) 0.0327(19) 0.0039(19) 0.0022(15) -0.0076(19) N1B 0.047(3) 0.044(3) 0.060(3) 0.001(3) 0.000(2) -0.001(2) N2B 0.043(3) 0.039(3) 0.046(3) 0.004(2) 0.006(2) -0.006(2) N3B 0.034(2) 0.045(3) 0.035(2) 0.002(2) 0.0095(18) -0.001(2) N4B 0.041(3) 0.045(3) 0.040(2) -0.001(2) 0.011(2) -0.004(2) C1B 0.045(3) 0.047(4) 0.044(3) 0.004(3) -0.002(3) -0.008(3) C2B 0.059(4) 0.043(4) 0.037(3) -0.004(3) 0.006(3) -0.018(3) C3B 0.039(3) 0.037(4) 0.034(3) 0.005(3) 0.010(2) -0.009(3) C4B 0.041(3) 0.056(4) 0.029(3) 0.002(3) 0.002(2) -0.014(3) C5B 0.038(3) 0.058(5) 0.045(3) -0.003(3) 0.007(3) -0.002(3) C6B 0.053(4) 0.067(5) 0.050(4) -0.010(4) 0.021(3) -0.012(4) C7B 0.066(4) 0.068(5) 0.036(3) -0.002(3) 0.020(3) -0.021(4) C8B 0.048(4) 0.040(4) 0.091(5) 0.008(4) -0.017(4) -0.011(3) C9B 0.058(5) 0.058(6) 0.114(6) -0.012(5) -0.018(4) 0.014(4) C10B 0.032(3) 0.051(4) 0.033(3) -0.002(3) 0.005(2) 0.008(3) C11B 0.042(3) 0.047(4) 0.043(3) -0.006(3) 0.012(2) -0.009(3) C12B 0.029(3) 0.043(4) 0.041(3) 0.005(3) 0.008(2) 0.000(2) C13B 0.034(3) 0.037(4) 0.034(3) 0.002(2) 0.008(2) 0.005(2) C14B 0.035(3) 0.042(4) 0.033(3) 0.003(3) 0.010(2) 0.004(3) C15B 0.045(3) 0.068(5) 0.037(3) 0.006(3) 0.004(2) -0.006(3) C16B 0.040(3) 0.059(5) 0.048(3) 0.010(3) 0.007(2) -0.011(3) C17B 0.040(3) 0.040(4) 0.035(3) -0.004(3) 0.003(2) 0.000(3) C18B 0.047(3) 0.055(5) 0.036(3) 0.002(3) 0.005(2) -0.005(3) C19B 0.035(3) 0.059(5) 0.038(3) -0.003(3) 0.008(2) -0.004(3) C20B 0.050(4) 0.046(4) 0.047(3) 0.005(3) 0.004(3) -0.003(3) O1S 0.051(2) 0.049(3) 0.041(2) 0.011(2) 0.0234(17) 0.014(2) O2S 0.043(2) 0.070(3) 0.044(2) 0.020(2) 0.0207(17) 0.018(2) O3S 0.034(2) 0.063(3) 0.062(3) 0.004(2) 0.0209(18) -0.003(2) C1S 0.048(3) 0.074(5) 0.035(3) 0.009(3) 0.008(2) 0.001(3) C2S 0.037(3) 0.030(3) 0.033(3) 0.000(2) 0.010(2) -0.001(2) C4S 0.036(3) 0.031(3) 0.034(3) -0.005(2) 0.005(2) -0.005(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 S1A C1A 1.743(5) . ? S1A C2A 1.749(6) . ? F1A C20A 1.343(7) . ? F2A C20A 1.344(7) . ? F3A C20A 1.330(7) . ? O1A C8A 1.214(6) . ? O2A C10A 1.349(6) . ? O2A C4A 1.409(6) . ? N1A C8A 1.354(7) . ? N1A C1A 1.378(7) . ? N1A H1A 0.8800 . ? N2A C1A 1.308(7) . ? N2A C3A 1.377(7) . ? N3A C10A 1.329(8) . ? N3A C11A 1.366(7) . ? N4A C11A 1.296(7) . ? N4A C13A 1.355(7) . ? C2A C7A 1.383(8) . ? C2A C3A 1.399(7) . ? C3A C4A 1.405(9) . ? C4A C5A 1.363(8) . ? C5A C6A 1.407(8) . ? C5A H5A 0.9500 . ? C6A C7A 1.398(9) . ? C6A H6A 0.9500 . ? C7A H7A 0.9500 . ? C8A C9A 1.504(8) . ? C9A H9A 0.9800 . ? C9A H9B 0.9800 . ? C9A H9C 0.9800 . ? C10A C12A 1.387(7) . ? C11A H11A 0.9500 . ? C12A C13A 1.383(7) . ? C12A H12A 0.9500 . ? C13A C14A 1.494(7) . ? C14A C19A 1.374(8) . ? C14A C15A 1.404(7) . ? C15A C16A 1.381(8) . ? C15A H15A 0.9500 . ? C16A C17A 1.410(8) . ? C16A H16A 0.9500 . ? C17A C18A 1.374(8) . ? C17A C20A 1.472(7) . ? C18A C19A 1.388(8) . ? C18A H18A 0.9500 . ? C19A H19A 0.9500 . ? S1B C2B 1.735(7) . ? S1B C1B 1.736(6) . ? F1B C20B 1.341(8) . ? F2B C20B 1.344(8) . ? F3B C20B 1.324(8) . ? O1B C8B 1.205(9) . ? O2B C10B 1.363(6) . ? O2B C4B 1.407(6) . ? N1B C1B 1.336(8) . ? N1B C8B 1.399(9) . ? N1B H1B 0.8800 . ? N2B C1B 1.334(8) . ? N2B C3B 1.401(7) . ? N3B C10B 1.315(8) . ? N3B C11B 1.335(7) . ? N4B C11B 1.326(7) . ? N4B C13B 1.345(8) . ? C2B C3B 1.395(7) . ? C2B C7B 1.399(9) . ? C3B C4B 1.371(9) . ? C4B C5B 1.378(8) . ? C5B C6B 1.388(8) . ? C5B H5B 0.9500 . ? C6B C7B 1.385(10) . ? C6B H6B 0.9500 . ? C7B H7B 0.9500 . ? C8B C9B 1.475(11) . ? C9B H9B1 0.9800 . ? C9B H9B2 0.9800 . ? C9B H9B3 0.9800 . ? C10B C12B 1.383(7) . ? C11B H11B 0.9500 . ? C12B C13B 1.380(8) . ? C12B H12B 0.9500 . ? C13B C14B 1.501(7) . ? C14B C15B 1.372(8) . ? C14B C19B 1.383(8) . ? C15B C16B 1.383(8) . ? C15B H15B 0.9500 . ? C16B C17B 1.387(8) . ? C16B H16B 0.9500 . ? C17B C18B 1.374(8) . ? C17B C20B 1.497(8) . ? C18B C19B 1.378(8) . ? C18B H18B 0.9500 . ? C19B H19B 0.9500 . ? O1S C4S 1.232(7) . ? O2S C4S 1.303(6) . ? O2S H2S1 0.8400 . ? O3S C2S 1.403(6) . ? O3S H3S 0.8400 . ? C1S C2S 1.525(7) . ? C1S H1S1 0.9800 . ? C1S H1S2 0.9800 . ? C1S H1S3 0.9800 . ? C2S C4S 1.509(7) . ? C2S H2S 1.0000 . ? O1E C1E 1.214(14) . ? O2E C1E 1.370(15) . ? O2E H2E 0.8400 . ? O3E C2E 1.408(15) . ? O3E H3E 0.8400 . ? C1E C2E 1.525(5) . ? C2E C3E 1.522(5) . ? C2E H2E1 1.0000 . ? C3E H3E1 0.9800 . ? C3E H3E2 0.9800 . ? C3E H3E3 0.9800 . ? O1F C1F 1.172(14) . ? O3F C2F 1.418(11) . ? O3F H3F 0.8400 . ? O2F C1F 1.510(16) . ? O2F H2F 0.8400 . ? C2F C3F 1.530(5) . ? C2F C1F 1.532(5) . ? C2F H2F1 1.0000 . ? C3F H3F1 0.9800 . ? C3F H3F2 0.9800 . ? C3F H3F3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1A S1A C2A 88.7(3) . . ? C10A O2A C4A 119.2(4) . . ? C8A N1A C1A 125.8(4) . . ? C8A N1A H1A 117.1 . . ? C1A N1A H1A 117.1 . . ? C1A N2A C3A 109.7(4) . . ? C10A N3A C11A 113.2(5) . . ? C11A N4A C13A 116.2(5) . . ? N2A C1A N1A 121.0(4) . . ? N2A C1A S1A 116.6(4) . . ? N1A C1A S1A 122.4(4) . . ? C7A C2A C3A 123.1(6) . . ? C7A C2A S1A 128.3(4) . . ? C3A C2A S1A 108.6(4) . . ? N2A C3A C2A 116.5(6) . . ? N2A C3A C4A 125.7(5) . . ? C2A C3A C4A 117.8(5) . . ? C5A C4A C3A 121.2(5) . . ? C5A C4A O2A 121.4(6) . . ? C3A C4A O2A 117.2(5) . . ? C4A C5A C6A 119.3(6) . . ? C4A C5A H5A 120.3 . . ? C6A C5A H5A 120.3 . . ? C7A C6A C5A 121.8(6) . . ? C7A C6A H6A 119.1 . . ? C5A C6A H6A 119.1 . . ? C2A C7A C6A 116.9(5) . . ? C2A C7A H7A 121.6 . . ? C6A C7A H7A 121.6 . . ? O1A C8A N1A 122.0(6) . . ? O1A C8A C9A 123.8(6) . . ? N1A C8A C9A 114.3(5) . . ? C8A C9A H9A 109.5 . . ? C8A C9A H9B 109.5 . . ? H9A C9A H9B 109.5 . . ? C8A C9A H9C 109.5 . . ? H9A C9A H9C 109.5 . . ? H9B C9A H9C 109.5 . . ? N3A C10A O2A 119.5(5) . . ? N3A C10A C12A 124.0(5) . . ? O2A C10A C12A 116.5(5) . . ? N4A C11A N3A 128.8(6) . . ? N4A C11A H11A 115.6 . . ? N3A C11A H11A 115.6 . . ? C13A C12A C10A 116.6(5) . . ? C13A C12A H12A 121.7 . . ? C10A C12A H12A 121.7 . . ? N4A C13A C12A 121.2(5) . . ? N4A C13A C14A 116.6(5) . . ? C12A C13A C14A 122.2(5) . . ? C19A C14A C15A 118.5(5) . . ? C19A C14A C13A 122.2(5) . . ? C15A C14A C13A 119.3(5) . . ? C16A C15A C14A 120.5(5) . . ? C16A C15A H15A 119.8 . . ? C14A C15A H15A 119.8 . . ? C15A C16A C17A 120.0(5) . . ? C15A C16A H16A 120.0 . . ? C17A C16A H16A 120.0 . . ? C18A C17A C16A 119.2(5) . . ? C18A C17A C20A 122.5(5) . . ? C16A C17A C20A 118.3(5) . . ? C17A C18A C19A 120.1(5) . . ? C17A C18A H18A 119.9 . . ? C19A C18A H18A 119.9 . . ? C14A C19A C18A 121.6(5) . . ? C14A C19A H19A 119.2 . . ? C18A C19A H19A 119.2 . . ? F3A C20A F1A 106.6(6) . . ? F3A C20A F2A 105.3(5) . . ? F1A C20A F2A 105.2(5) . . ? F3A C20A C17A 114.0(5) . . ? F1A C20A C17A 112.0(5) . . ? F2A C20A C17A 113.1(6) . . ? C2B S1B C1B 89.3(3) . . ? C10B O2B C4B 119.6(5) . . ? C1B N1B C8B 124.5(6) . . ? C1B N1B H1B 117.7 . . ? C8B N1B H1B 117.7 . . ? C1B N2B C3B 110.2(5) . . ? C10B N3B C11B 113.7(5) . . ? C11B N4B C13B 115.4(5) . . ? N2B C1B N1B 119.7(6) . . ? N2B C1B S1B 115.5(5) . . ? N1B C1B S1B 124.7(5) . . ? C3B C2B C7B 120.3(6) . . ? C3B C2B S1B 110.5(4) . . ? C7B C2B S1B 129.2(5) . . ? C4B C3B C2B 120.2(5) . . ? C4B C3B N2B 125.4(5) . . ? C2B C3B N2B 114.5(5) . . ? C3B C4B C5B 120.5(5) . . ? C3B C4B O2B 118.2(5) . . ? C5B C4B O2B 121.0(6) . . ? C4B C5B C6B 119.3(6) . . ? C4B C5B H5B 120.3 . . ? C6B C5B H5B 120.3 . . ? C7B C6B C5B 121.7(6) . . ? C7B C6B H6B 119.2 . . ? C5B C6B H6B 119.2 . . ? C6B C7B C2B 118.0(6) . . ? C6B C7B H7B 121.0 . . ? C2B C7B H7B 121.0 . . ? O1B C8B N1B 120.3(8) . . ? O1B C8B C9B 124.9(8) . . ? N1B C8B C9B 114.8(7) . . ? C8B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C8B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? N3B C10B O2B 119.9(5) . . ? N3B C10B C12B 124.0(5) . . ? O2B C10B C12B 116.1(6) . . ? N4B C11B N3B 128.9(6) . . ? N4B C11B H11B 115.5 . . ? N3B C11B H11B 115.5 . . ? C13B C12B C10B 117.0(6) . . ? C13B C12B H12B 121.5 . . ? C10B C12B H12B 121.5 . . ? N4B C13B C12B 121.0(5) . . ? N4B C13B C14B 116.9(5) . . ? C12B C13B C14B 122.0(5) . . ? C15B C14B C19B 119.4(5) . . ? C15B C14B C13B 120.8(5) . . ? C19B C14B C13B 119.7(5) . . ? C14B C15B C16B 121.4(5) . . ? C14B C15B H15B 119.3 . . ? C16B C15B H15B 119.3 . . ? C15B C16B C17B 118.2(6) . . ? C15B C16B H16B 120.9 . . ? C17B C16B H16B 120.9 . . ? C18B C17B C16B 121.2(5) . . ? C18B C17B C20B 119.9(5) . . ? C16B C17B C20B 118.8(5) . . ? C17B C18B C19B 119.5(5) . . ? C17B C18B H18B 120.3 . . ? C19B C18B H18B 120.3 . . ? C18B C19B C14B 120.3(5) . . ? C18B C19B H19B 119.8 . . ? C14B C19B H19B 119.8 . . ? F3B C20B F1B 106.3(6) . . ? F3B C20B F2B 105.5(5) . . ? F1B C20B F2B 104.7(5) . . ? F3B C20B C17B 113.7(5) . . ? F1B C20B C17B 112.9(5) . . ? F2B C20B C17B 113.0(6) . . ? C4S O2S H2S1 109.5 . . ? C2S O3S H3S 109.5 . . ? C2S C1S H1S1 109.5 . . ? C2S C1S H1S2 109.5 . . ? H1S1 C1S H1S2 109.5 . . ? C2S C1S H1S3 109.5 . . ? H1S1 C1S H1S3 109.5 . . ? H1S2 C1S H1S3 109.5 . . ? O3S C2S C4S 109.0(4) . . ? O3S C2S C1S 110.1(4) . . ? C4S C2S C1S 108.7(5) . . ? O3S C2S H2S 109.7 . . ? C4S C2S H2S 109.7 . . ? C1S C2S H2S 109.7 . . ? O1S C4S O2S 122.4(5) . . ? O1S C4S C2S 123.1(5) . . ? O2S C4S C2S 114.5(5) . . ? O1E C1E O2E 138.0(15) . . ? O1E C1E C2E 124.6(16) . . ? O2E C1E C2E 97.4(17) . . ? O3E C2E C3E 124.9(16) . . ? O3E C2E C1E 125.3(16) . . ? C3E C2E C1E 109.3(5) . . ? O3E C2E H2E1 92.2 . . ? C3E C2E H2E1 92.2 . . ? C1E C2E H2E1 92.2 . . ? C2F O3F H3F 109.5 . . ? C1F O2F H2F 111.0 . . ? O3F C2F C3F 109.0(9) . . ? O3F C2F C1F 127.0(10) . . ? C3F C2F C1F 105.2(10) . . ? O3F C2F H2F1 104.6 . . ? C3F C2F H2F1 104.6 . . ? C1F C2F H2F1 104.6 . . ? O1F C1F O2F 143.8(18) . . ? O1F C1F C2F 105.5(11) . . ? O2F C1F C2F 87.6(10) . . ? C2F C3F H3F1 109.5 . . ? C2F C3F H3F2 109.5 . . ? H3F1 C3F H3F2 109.5 . . ? C2F C3F H3F3 109.5 . . ? H3F1 C3F H3F3 109.5 . . ? H3F2 C3F H3F3 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 C3A N2A C1A N1A 178.1(5) . . . . ? C3A N2A C1A S1A 0.1(6) . . . . ? C8A N1A C1A N2A 178.9(5) . . . . ? C8A N1A C1A S1A -3.2(8) . . . . ? C2A S1A C1A N2A 0.0(5) . . . . ? C2A S1A C1A N1A -178.0(5) . . . . ? C1A S1A C2A C7A -179.9(6) . . . . ? C1A S1A C2A C3A -0.1(4) . . . . ? C1A N2A C3A C2A -0.2(7) . . . . ? C1A N2A C3A C4A 178.8(6) . . . . ? C7A C2A C3A N2A 180.0(5) . . . . ? S1A C2A C3A N2A 0.2(6) . . . . ? C7A C2A C3A C4A 0.9(9) . . . . ? S1A C2A C3A C4A -178.9(5) . . . . ? N2A C3A C4A C5A -179.4(6) . . . . ? C2A C3A C4A C5A -0.3(9) . . . . ? N2A C3A C4A O2A -5.9(9) . . . . ? C2A C3A C4A O2A 173.1(5) . . . . ? C10A O2A C4A C5A -82.8(7) . . . . ? C10A O2A C4A C3A 103.7(6) . . . . ? C3A C4A C5A C6A -0.8(9) . . . . ? O2A C4A C5A C6A -174.0(5) . . . . ? C4A C5A C6A C7A 1.4(10) . . . . ? C3A C2A C7A C6A -0.2(9) . . . . ? S1A C2A C7A C6A 179.5(5) . . . . ? C5A C6A C7A C2A -0.9(9) . . . . ? C1A N1A C8A O1A 1.7(10) . . . . ? C1A N1A C8A C9A -178.2(5) . . . . ? C11A N3A C10A O2A 177.8(5) . . . . ? C11A N3A C10A C12A -0.8(8) . . . . ? C4A O2A C10A N3A -2.7(8) . . . . ? C4A O2A C10A C12A 176.0(5) . . . . ? C13A N4A C11A N3A 1.0(10) . . . . ? C10A N3A C11A N4A -0.4(9) . . . . ? N3A C10A C12A C13A 1.3(9) . . . . ? O2A C10A C12A C13A -177.4(5) . . . . ? C11A N4A C13A C12A -0.5(8) . . . . ? C11A N4A C13A C14A -178.6(5) . . . . ? C10A C12A C13A N4A -0.6(8) . . . . ? C10A C12A C13A C14A 177.5(5) . . . . ? N4A C13A C14A C19A -161.3(6) . . . . ? C12A C13A C14A C19A 20.6(9) . . . . ? N4A C13A C14A C15A 20.3(8) . . . . ? C12A C13A C14A C15A -157.8(6) . . . . ? C19A C14A C15A C16A -2.0(10) . . . . ? C13A C14A C15A C16A 176.4(6) . . . . ? C14A C15A C16A C17A 1.8(10) . . . . ? C15A C16A C17A C18A -0.6(10) . . . . ? C15A C16A C17A C20A 178.1(6) . . . . ? C16A C17A C18A C19A -0.3(11) . . . . ? C20A C17A C18A C19A -179.0(6) . . . . ? C15A C14A C19A C18A 1.0(10) . . . . ? C13A C14A C19A C18A -177.3(6) . . . . ? C17A C18A C19A C14A 0.1(11) . . . . ? C18A C17A C20A F3A -137.5(7) . . . . ? C16A C17A C20A F3A 43.9(9) . . . . ? C18A C17A C20A F1A -16.3(10) . . . . ? C16A C17A C20A F1A 165.0(6) . . . . ? C18A C17A C20A F2A 102.3(8) . . . . ? C16A C17A C20A F2A -76.4(7) . . . . ? C3B N2B C1B N1B 178.8(6) . . . . ? C3B N2B C1B S1B -0.1(7) . . . . ? C8B N1B C1B N2B 179.7(6) . . . . ? C8B N1B C1B S1B -1.5(10) . . . . ? C2B S1B C1B N2B 0.0(5) . . . . ? C2B S1B C1B N1B -178.7(6) . . . . ? C1B S1B C2B C3B 0.0(5) . . . . ? C1B S1B C2B C7B 179.7(7) . . . . ? C7B C2B C3B C4B -1.1(9) . . . . ? S1B C2B C3B C4B 178.6(5) . . . . ? C7B C2B C3B N2B -179.8(6) . . . . ? S1B C2B C3B N2B -0.1(7) . . . . ? C1B N2B C3B C4B -178.5(6) . . . . ? C1B N2B C3B C2B 0.1(7) . . . . ? C2B C3B C4B C5B -0.2(10) . . . . ? N2B C3B C4B C5B 178.3(6) . . . . ? C2B C3B C4B O2B -173.4(5) . . . . ? N2B C3B C4B O2B 5.1(9) . . . . ? C10B O2B C4B C3B -108.4(6) . . . . ? C10B O2B C4B C5B 78.4(8) . . . . ? C3B C4B C5B C6B 1.6(10) . . . . ? O2B C4B C5B C6B 174.7(6) . . . . ? C4B C5B C6B C7B -1.8(10) . . . . ? C5B C6B C7B C2B 0.5(11) . . . . ? C3B C2B C7B C6B 0.9(10) . . . . ? S1B C2B C7B C6B -178.7(5) . . . . ? C1B N1B C8B O1B 0.3(11) . . . . ? C1B N1B C8B C9B 179.5(6) . . . . ? C11B N3B C10B O2B -179.5(6) . . . . ? C11B N3B C10B C12B -0.1(9) . . . . ? C4B O2B C10B N3B 5.1(9) . . . . ? C4B O2B C10B C12B -174.3(5) . . . . ? C13B N4B C11B N3B -2.2(10) . . . . ? C10B N3B C11B N4B 1.6(10) . . . . ? N3B C10B C12B C13B -0.5(9) . . . . ? O2B C10B C12B C13B 178.9(5) . . . . ? C11B N4B C13B C12B 1.4(8) . . . . ? C11B N4B C13B C14B 179.5(5) . . . . ? C10B C12B C13B N4B -0.2(9) . . . . ? C10B C12B C13B C14B -178.2(5) . . . . ? N4B C13B C14B C15B 162.8(6) . . . . ? C12B C13B C14B C15B -19.1(9) . . . . ? N4B C13B C14B C19B -19.6(9) . . . . ? C12B C13B C14B C19B 158.5(6) . . . . ? C19B C14B C15B C16B 1.6(11) . . . . ? C13B C14B C15B C16B 179.2(6) . . . . ? C14B C15B C16B C17B -2.6(11) . . . . ? C15B C16B C17B C18B 2.0(11) . . . . ? C15B C16B C17B C20B -180.0(7) . . . . ? C16B C17B C18B C19B -0.5(10) . . . . ? C20B C17B C18B C19B -178.5(6) . . . . ? C17B C18B C19B C14B -0.5(10) . . . . ? C15B C14B C19B C18B -0.1(10) . . . . ? C13B C14B C19B C18B -177.7(6) . . . . ? C18B C17B C20B F3B -163.1(6) . . . . ? C16B C17B C20B F3B 18.8(9) . . . . ? C18B C17B C20B F1B -42.0(9) . . . . ? C16B C17B C20B F1B 140.0(7) . . . . ? C18B C17B C20B F2B 76.7(8) . . . . ? C16B C17B C20B F2B -101.4(7) . . . . ? O3S C2S C4S O1S -10.7(7) . . . . ? C1S C2S C4S O1S 109.3(6) . . . . ? O3S C2S C4S O2S 169.4(5) . . . . ? C1S C2S C4S O2S -70.6(6) . . . . ? O1E C1E C2E O3E -122(3) . . . . ? O2E C1E C2E O3E 57(4) . . . . ? O1E C1E C2E C3E 51(3) . . . . ? O2E C1E C2E C3E -130(2) . . . . ? O3F C2F C1F O1F 21(2) . . . . ? C3F C2F C1F O1F 149.7(15) . . . . ? O3F C2F C1F O2F 166.7(11) . . . . ? C3F C2F C1F O2F -64.5(13) . . . . ? 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 N1A H1A O1S 0.88 1.96 2.815(5) 163.6 . N1B H1B O1E 0.88 1.80 2.678(9) 174.4 . O2S H2S1 N2A 0.84 1.84 2.671(5) 168.6 . O3S H3S O1S 0.84 2.07 2.817(5) 148.4 2_756 O2E H2E O2B 0.84 2.61 3.058(16) 114.4 . _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 68.08 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 1.085 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.062 # Attachment 'MEA.cif' data_MEA _database_code_depnum_ccdc_archive 'CCDC 791332' #TrackingRef 'MEA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C20 H13 F3 N4 O2 S), C4 H3 O4 ' _chemical_formula_sum 'C44 H29 F6 N8 O8 S2' _chemical_formula_weight 975.87 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.396(6) _cell_length_b 13.535(8) _cell_length_c 17.036(10) _cell_angle_alpha 104.757(8) _cell_angle_beta 91.076(7) _cell_angle_gamma 90.354(8) _cell_volume 2094(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 877 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 26.19 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 998 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9613 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83 to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Scaling and absorption corrections were performed by the SADABS program. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V6.1. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 10600 _diffrn_reflns_av_R_equivalents 0.0834 _diffrn_reflns_av_sigmaI/netI 0.1906 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7236 _reflns_number_gt 3036 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.58, 2007)' _computing_cell_refinement 'APEX2 (BRUKER, V5-0, 2008)' _computing_data_reduction 'SAINT (BRUKER, V7.56A, 2008)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.1300P)^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 7236 _refine_ls_number_parameters 616 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2087 _refine_ls_R_factor_gt 0.1016 _refine_ls_wR_factor_ref 0.2929 _refine_ls_wR_factor_gt 0.2283 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _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 S1A S 0.3523(2) 0.95825(16) 0.42905(11) 0.0335(5) Uani 1 1 d . . . F1A F 0.8174(7) 0.5316(9) -0.3755(3) 0.167(5) Uani 1 1 d . . . F2A F 0.6413(10) 0.4438(6) -0.4073(4) 0.148(4) Uani 1 1 d . . . F3A F 0.6367(9) 0.5889(6) -0.4115(3) 0.129(3) Uani 1 1 d . . . O1A O 0.5749(5) 0.8195(4) 0.1612(3) 0.0393(14) Uani 1 1 d . . . O2A O 0.1617(5) 1.1100(4) 0.4694(3) 0.0447(15) Uani 1 1 d . . . N1A N 0.3801(6) 0.9459(5) 0.2737(3) 0.0302(15) Uani 1 1 d . . . N2A N 0.2131(6) 1.0661(5) 0.3361(3) 0.0334(16) Uani 1 1 d . . . H2A H 0.1945 1.0779 0.2885 0.040 Uiso 1 1 calc R . . N3A N 0.4182(6) 0.6825(5) 0.1225(4) 0.0367(17) Uani 1 1 d . . . N4A N 0.3966(6) 0.5914(5) -0.0173(3) 0.0313(15) Uani 1 1 d . . . C1A C 0.3121(8) 0.9908(6) 0.3395(4) 0.035(2) Uani 1 1 d . . . C2A C 0.4716(8) 0.8748(6) 0.2946(5) 0.036(2) Uani 1 1 d . . . C3A C 0.4698(7) 0.8700(6) 0.3752(4) 0.0313(19) Uani 1 1 d . . . C4A C 0.5544(8) 0.8011(6) 0.4042(5) 0.037(2) Uani 1 1 d . . . H4A H 0.5502 0.7963 0.4588 0.045 Uiso 1 1 calc R . . C5A C 0.6442(8) 0.7406(6) 0.3490(5) 0.037(2) Uani 1 1 d . . . H5A H 0.7043 0.6941 0.3668 0.045 Uiso 1 1 calc R . . C6A C 0.6501(8) 0.7451(6) 0.2689(4) 0.036(2) Uani 1 1 d . . . H6A H 0.7130 0.7023 0.2327 0.044 Uiso 1 1 calc R . . C7A C 0.5633(8) 0.8126(6) 0.2422(4) 0.0321(19) Uani 1 1 d . . . C8A C 0.1437(7) 1.1224(6) 0.4013(4) 0.0310(19) Uani 1 1 d . . . C9A C 0.0477(9) 1.2039(7) 0.3848(5) 0.052(2) Uani 1 1 d . . . H9A1 H -0.0452 1.1992 0.4089 0.078 Uiso 1 1 calc R . . H9A2 H 0.0355 1.1941 0.3261 0.078 Uiso 1 1 calc R . . H9A3 H 0.0905 1.2713 0.4088 0.078 Uiso 1 1 calc R . . C10A C 0.5163(8) 0.7427(6) 0.1008(5) 0.0331(19) Uani 1 1 d . . . C11A C 0.3647(8) 0.6109(6) 0.0596(4) 0.035(2) Uani 1 1 d . . . H11A H 0.2932 0.5680 0.0724 0.042 Uiso 1 1 calc R . . C12A C 0.5587(8) 0.7320(6) 0.0226(4) 0.0315(19) Uani 1 1 d . . . H12A H 0.6271 0.7772 0.0099 0.038 Uiso 1 1 calc R . . C13A C 0.4990(7) 0.6538(6) -0.0366(4) 0.0317(19) Uani 1 1 d . . . C14A C 0.5450(7) 0.6263(6) -0.1215(4) 0.0293(18) Uani 1 1 d . . . C15A C 0.6582(8) 0.6748(6) -0.1484(5) 0.040(2) Uani 1 1 d . . . H15A H 0.7057 0.7301 -0.1114 0.048 Uiso 1 1 calc R . . C16A C 0.7037(8) 0.6444(7) -0.2277(5) 0.041(2) Uani 1 1 d . . . H16A H 0.7815 0.6789 -0.2442 0.049 Uiso 1 1 calc R . . C17A C 0.6373(8) 0.5651(6) -0.2823(4) 0.0331(19) Uani 1 1 d . . . C18A C 0.5252(9) 0.5155(7) -0.2575(5) 0.045(2) Uani 1 1 d . . . H18A H 0.4790 0.4598 -0.2949 0.054 Uiso 1 1 calc R . . C19A C 0.4798(9) 0.5459(7) -0.1790(5) 0.044(2) Uani 1 1 d . . . H19A H 0.4015 0.5110 -0.1633 0.053 Uiso 1 1 calc R . . C20A C 0.6847(9) 0.5343(7) -0.3656(5) 0.046(2) Uani 1 1 d . . . S1B S 0.1742(2) 0.02397(16) 0.61871(11) 0.0343(5) Uani 1 1 d . . . F1B F -0.1504(10) 0.5627(6) 1.4369(4) 0.136(3) Uani 1 1 d . . . F2B F -0.3134(7) 0.4604(10) 1.4053(3) 0.198(6) Uani 1 1 d . . . F3B F -0.1202(8) 0.4155(6) 1.4395(3) 0.113(3) Uani 1 1 d . . . O1B O -0.0779(5) 0.1901(4) 0.8699(3) 0.0386(14) Uani 1 1 d . . . O2B O 0.3695(6) -0.1233(5) 0.5981(3) 0.0504(16) Uani 1 1 d . . . N1B N 0.1267(6) 0.0583(5) 0.7729(3) 0.0307(15) Uani 1 1 d . . . N2B N 0.2964(6) -0.0683(5) 0.7278(4) 0.0359(16) Uani 1 1 d . . . H2B H 0.3050 -0.0751 0.7777 0.043 Uiso 1 1 calc R . . N3B N 0.0859(6) 0.3235(5) 0.9062(4) 0.0353(16) Uani 1 1 d . . . N4B N 0.0979(6) 0.4262(5) 1.0443(4) 0.0322(15) Uani 1 1 d . . . C1B C 0.2014(8) 0.0003(6) 0.7121(5) 0.037(2) Uani 1 1 d . . . C2B C 0.0367(8) 0.1229(6) 0.7445(4) 0.0304(18) Uani 1 1 d . . . C3B C 0.0494(8) 0.1168(6) 0.6621(5) 0.0332(19) Uani 1 1 d . . . C4B C -0.0307(8) 0.1773(6) 0.6238(4) 0.035(2) Uani 1 1 d . . . H4B H -0.0209 0.1730 0.5676 0.042 Uiso 1 1 calc R . . C5B C -0.1252(8) 0.2441(6) 0.6704(5) 0.038(2) Uani 1 1 d . . . H5B H -0.1814 0.2865 0.6458 0.046 Uiso 1 1 calc R . . C6B C -0.1401(8) 0.2506(6) 0.7524(4) 0.036(2) Uani 1 1 d . . . H6B H -0.2062 0.2969 0.7831 0.044 Uiso 1 1 calc R . . C7B C -0.0586(8) 0.1896(6) 0.7895(4) 0.0332(19) Uani 1 1 d . . . C8B C 0.3804(8) -0.1281(6) 0.6677(5) 0.042(2) Uani 1 1 d . . . C9B C 0.4823(9) -0.1953(7) 0.6994(5) 0.056(3) Uani 1 1 d . . . H9B1 H 0.4295 -0.2359 0.7295 0.084 Uiso 1 1 calc R . . H9B2 H 0.5535 -0.1526 0.7355 0.084 Uiso 1 1 calc R . . H9B3 H 0.5299 -0.2411 0.6537 0.084 Uiso 1 1 calc R . . C10B C -0.0185(8) 0.2699(6) 0.9285(4) 0.0303(18) Uani 1 1 d . . . C11B C 0.1374(8) 0.4001(6) 0.9680(4) 0.036(2) Uani 1 1 d . . . H11B H 0.2118 0.4403 0.9546 0.043 Uiso 1 1 calc R . . C12B C -0.0695(8) 0.2874(6) 1.0064(4) 0.0334(19) Uani 1 1 d . . . H12B H -0.1437 0.2466 1.0195 0.040 Uiso 1 1 calc R . . C13B C -0.0075(7) 0.3670(6) 1.0642(4) 0.0292(18) Uani 1 1 d . . . C14B C -0.0517(8) 0.3940(6) 1.1499(4) 0.0302(18) Uani 1 1 d . . . C15B C -0.0379(8) 0.4918(6) 1.1983(4) 0.036(2) Uani 1 1 d . . . H15B H 0.0027 0.5432 1.1763 0.043 Uiso 1 1 calc R . . C16B C -0.0809(9) 0.5176(7) 1.2774(5) 0.042(2) Uani 1 1 d . . . H16B H -0.0724 0.5862 1.3091 0.051 Uiso 1 1 calc R . . C17B C -0.1370(8) 0.4427(7) 1.3107(4) 0.036(2) Uani 1 1 d . . . C18B C -0.1523(8) 0.3440(7) 1.2630(5) 0.041(2) Uani 1 1 d . . . H18B H -0.1925 0.2931 1.2856 0.049 Uiso 1 1 calc R . . C19B C -0.1105(8) 0.3177(6) 1.1833(5) 0.039(2) Uani 1 1 d . . . H19B H -0.1210 0.2494 1.1512 0.047 Uiso 1 1 calc R . . C20B C -0.1822(9) 0.4652(8) 1.3949(5) 0.050(3) Uani 1 1 d . . . O1 O 0.8150(6) 0.9572(5) 1.0711(3) 0.0439(15) Uani 1 1 d . . . O2 O 0.6742(7) 1.0888(5) 1.1219(3) 0.0587(18) Uani 1 1 d . . . O3 O 0.9188(6) 0.8842(5) 0.9366(3) 0.0504(16) Uani 1 1 d . . . H3 H 0.8879 0.9107 0.9832 0.076 Uiso 1 1 calc R . . O4 O 0.8870(6) 0.8977(5) 0.8120(3) 0.0539(17) Uani 1 1 d . . . C1 C 0.7307(9) 1.0286(8) 1.0636(5) 0.048(2) Uani 1 1 d . . . C2 C 0.6876(9) 1.0374(7) 0.9812(5) 0.044(2) Uani 1 1 d . . . H2 H 0.6075 1.0797 0.9809 0.053 Uiso 1 1 calc R . . C3 C 0.7382(9) 0.9984(7) 0.9091(5) 0.045(2) Uani 1 1 d . . . H3A H 0.6942 1.0217 0.8666 0.054 Uiso 1 1 calc R . . C4 C 0.8528(9) 0.9239(7) 0.8832(5) 0.041(2) 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 S1A 0.0332(11) 0.0357(13) 0.0322(11) 0.0102(9) -0.0005(9) -0.0038(10) F1A 0.050(4) 0.372(15) 0.050(4) -0.004(6) 0.016(3) 0.026(6) F2A 0.254(10) 0.094(6) 0.071(5) -0.030(4) 0.092(5) -0.064(6) F3A 0.204(8) 0.149(8) 0.047(4) 0.042(4) 0.045(4) 0.104(7) O1A 0.047(3) 0.025(3) 0.043(3) 0.003(3) 0.007(3) -0.015(3) O2A 0.048(4) 0.051(4) 0.035(3) 0.010(3) 0.003(3) 0.003(3) N1A 0.033(4) 0.027(4) 0.030(4) 0.005(3) -0.001(3) -0.009(3) N2A 0.035(4) 0.037(4) 0.031(4) 0.012(3) 0.004(3) 0.000(3) N3A 0.029(4) 0.039(5) 0.039(4) 0.003(3) 0.004(3) -0.009(3) N4A 0.026(3) 0.033(4) 0.034(4) 0.006(3) 0.002(3) -0.009(3) C1A 0.033(5) 0.039(5) 0.031(4) 0.009(4) -0.009(4) -0.007(4) C2A 0.038(5) 0.029(5) 0.040(5) 0.008(4) 0.001(4) -0.010(4) C3A 0.027(4) 0.038(5) 0.027(4) 0.003(4) 0.003(3) -0.008(4) C4A 0.033(5) 0.034(5) 0.046(5) 0.016(4) -0.011(4) -0.018(4) C5A 0.033(5) 0.023(5) 0.055(5) 0.007(4) -0.003(4) -0.007(4) C6A 0.036(5) 0.034(5) 0.035(5) -0.001(4) 0.005(4) -0.005(4) C7A 0.033(4) 0.035(5) 0.024(4) 0.002(4) -0.001(3) -0.008(4) C8A 0.021(4) 0.038(5) 0.032(5) 0.007(4) -0.005(3) -0.010(4) C9A 0.058(6) 0.043(6) 0.056(6) 0.016(5) 0.003(5) 0.012(5) C10A 0.033(5) 0.017(4) 0.046(5) 0.002(4) -0.008(4) -0.008(4) C11A 0.030(4) 0.039(5) 0.035(5) 0.008(4) 0.004(4) -0.009(4) C12A 0.040(5) 0.028(5) 0.027(4) 0.006(3) 0.008(4) -0.004(4) C13A 0.027(4) 0.037(5) 0.032(4) 0.010(4) 0.003(3) -0.002(4) C14A 0.021(4) 0.035(5) 0.033(4) 0.011(4) -0.002(3) -0.005(4) C15A 0.040(5) 0.039(6) 0.040(5) 0.007(4) -0.001(4) -0.011(4) C16A 0.036(5) 0.048(6) 0.039(5) 0.014(4) 0.004(4) -0.010(4) C17A 0.030(4) 0.043(5) 0.027(4) 0.009(4) 0.002(3) -0.001(4) C18A 0.055(6) 0.044(6) 0.034(5) 0.004(4) 0.001(4) -0.013(5) C19A 0.047(5) 0.045(6) 0.040(5) 0.012(4) 0.005(4) -0.022(5) C20A 0.042(6) 0.042(6) 0.052(6) 0.011(5) -0.001(5) 0.009(5) S1B 0.0364(12) 0.0315(13) 0.0351(11) 0.0083(9) 0.0057(9) -0.0033(10) F1B 0.275(11) 0.073(5) 0.058(4) 0.007(4) 0.068(5) 0.013(6) F2B 0.051(4) 0.474(18) 0.041(4) 0.016(6) 0.016(3) -0.032(7) F3B 0.181(7) 0.127(7) 0.045(4) 0.041(4) 0.035(4) 0.084(6) O1B 0.047(3) 0.029(3) 0.037(3) 0.004(2) 0.011(3) -0.012(3) O2B 0.058(4) 0.052(4) 0.042(4) 0.011(3) 0.010(3) 0.005(3) N1B 0.029(4) 0.030(4) 0.033(4) 0.008(3) 0.000(3) -0.004(3) N2B 0.035(4) 0.036(4) 0.042(4) 0.021(3) 0.003(3) -0.005(3) N3B 0.031(4) 0.036(4) 0.040(4) 0.012(3) 0.001(3) -0.006(3) N4B 0.038(4) 0.023(4) 0.037(4) 0.010(3) 0.004(3) -0.005(3) C1B 0.033(5) 0.037(5) 0.041(5) 0.013(4) -0.006(4) -0.013(4) C2B 0.029(4) 0.031(5) 0.029(4) 0.003(3) -0.001(3) -0.006(4) C3B 0.026(4) 0.027(5) 0.047(5) 0.010(4) 0.003(4) -0.009(4) C4B 0.031(4) 0.036(5) 0.036(5) 0.008(4) 0.003(4) -0.007(4) C5B 0.034(5) 0.036(5) 0.042(5) 0.004(4) 0.002(4) -0.004(4) C6B 0.023(4) 0.041(6) 0.037(5) -0.004(4) 0.006(4) -0.006(4) C7B 0.034(5) 0.035(5) 0.028(4) 0.003(4) 0.004(4) -0.008(4) C8B 0.040(5) 0.030(5) 0.052(6) 0.005(4) 0.010(4) -0.013(4) C9B 0.046(6) 0.042(6) 0.087(7) 0.030(5) 0.013(5) 0.002(5) C10B 0.029(4) 0.026(5) 0.034(4) 0.004(4) 0.001(3) -0.002(4) C11B 0.032(5) 0.033(5) 0.041(5) 0.010(4) 0.000(4) -0.012(4) C12B 0.035(5) 0.030(5) 0.035(5) 0.009(4) 0.007(4) -0.009(4) C13B 0.022(4) 0.032(5) 0.036(4) 0.012(4) 0.001(3) -0.004(4) C14B 0.034(4) 0.027(5) 0.030(4) 0.009(3) -0.005(3) -0.009(4) C15B 0.042(5) 0.035(5) 0.031(4) 0.009(4) 0.000(4) 0.001(4) C16B 0.059(6) 0.031(5) 0.037(5) 0.007(4) 0.000(4) 0.001(4) C17B 0.038(5) 0.048(6) 0.023(4) 0.009(4) 0.004(4) 0.011(4) C18B 0.047(5) 0.044(6) 0.035(5) 0.014(4) 0.011(4) -0.004(4) C19B 0.044(5) 0.027(5) 0.046(5) 0.009(4) 0.001(4) -0.007(4) C20B 0.038(5) 0.067(8) 0.043(6) 0.012(5) 0.003(4) 0.009(5) O1 0.049(4) 0.044(4) 0.045(3) 0.022(3) 0.000(3) -0.003(3) O2 0.085(5) 0.053(4) 0.042(4) 0.018(3) 0.011(3) 0.021(4) O3 0.061(4) 0.052(4) 0.042(3) 0.018(3) -0.006(3) 0.001(3) O4 0.076(4) 0.053(4) 0.037(4) 0.018(3) 0.004(3) 0.011(3) C1 0.048(6) 0.048(7) 0.048(6) 0.016(5) 0.005(5) -0.017(5) C2 0.042(5) 0.058(7) 0.038(5) 0.024(4) -0.002(4) 0.000(5) C3 0.048(5) 0.045(6) 0.048(6) 0.022(4) -0.002(4) -0.002(5) C4 0.053(6) 0.032(5) 0.039(5) 0.014(4) -0.001(4) -0.004(4) _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 S1A C3A 1.727(8) . ? S1A C1A 1.729(8) . ? F1A C20A 1.260(9) . ? F2A C20A 1.308(10) . ? F3A C20A 1.282(10) . ? O1A C10A 1.368(8) . ? O1A C7A 1.413(8) . ? O2A C8A 1.224(8) . ? N1A C1A 1.310(9) . ? N1A C2A 1.402(10) . ? N2A C8A 1.357(9) . ? N2A C1A 1.395(10) . ? N2A H2A 0.8800 . ? N3A C11A 1.336(9) . ? N3A C10A 1.345(9) . ? N4A C11A 1.308(9) . ? N4A C13A 1.374(9) . ? C2A C7A 1.380(10) . ? C2A C3A 1.391(10) . ? C3A C4A 1.406(10) . ? C4A C5A 1.383(10) . ? C4A H4A 0.9500 . ? C5A C6A 1.383(10) . ? C5A H5A 0.9500 . ? C6A C7A 1.384(10) . ? C6A H6A 0.9500 . ? C8A C9A 1.506(11) . ? C9A H9A1 0.9800 . ? C9A H9A2 0.9800 . ? C9A H9A3 0.9800 . ? C10A C12A 1.369(10) . ? C11A H11A 0.9500 . ? C12A C13A 1.372(9) . ? C12A H12A 0.9500 . ? C13A C14A 1.473(9) . ? C14A C15A 1.390(10) . ? C14A C19A 1.395(10) . ? C15A C16A 1.384(10) . ? C15A H15A 0.9500 . ? C16A C17A 1.367(10) . ? C16A H16A 0.9500 . ? C17A C18A 1.375(11) . ? C17A C20A 1.454(11) . ? C18A C19A 1.373(10) . ? C18A H18A 0.9500 . ? C19A H19A 0.9500 . ? S1B C1B 1.716(8) . ? S1B C3B 1.754(8) . ? F1B C20B 1.360(11) . ? F2B C20B 1.253(9) . ? F3B C20B 1.271(10) . ? O1B C10B 1.377(8) . ? O1B C7B 1.383(8) . ? O2B C8B 1.207(9) . ? N1B C1B 1.342(9) . ? N1B C2B 1.386(9) . ? N2B C1B 1.363(10) . ? N2B C8B 1.394(10) . ? N2B H2B 0.8800 . ? N3B C10B 1.333(9) . ? N3B C11B 1.354(9) . ? N4B C11B 1.319(9) . ? N4B C13B 1.370(9) . ? C2B C7B 1.374(10) . ? C2B C3B 1.392(10) . ? C3B C4B 1.388(11) . ? C4B C5B 1.381(10) . ? C4B H4B 0.9500 . ? C5B C6B 1.386(10) . ? C5B H5B 0.9500 . ? C6B C7B 1.388(11) . ? C6B H6B 0.9500 . ? C8B C9B 1.509(11) . ? C9B H9B1 0.9800 . ? C9B H9B2 0.9800 . ? C9B H9B3 0.9800 . ? C10B C12B 1.384(10) . ? C11B H11B 0.9500 . ? C12B C13B 1.378(10) . ? C12B H12B 0.9500 . ? C13B C14B 1.480(10) . ? C14B C15B 1.374(10) . ? C14B C19B 1.413(10) . ? C15B C16B 1.372(10) . ? C15B H15B 0.9500 . ? C16B C17B 1.387(11) . ? C16B H16B 0.9500 . ? C17B C18B 1.381(11) . ? C17B C20B 1.460(11) . ? C18B C19B 1.380(10) . ? C18B H18B 0.9500 . ? C19B H19B 0.9500 . ? O1 C1 1.284(10) . ? O2 C1 1.242(10) . ? O3 C4 1.317(9) . ? O3 H3 0.8400 . ? O4 C4 1.223(9) . ? C1 C2 1.487(11) . ? C2 C3 1.307(11) . ? C2 H2 0.9500 . ? C3 C4 1.475(12) . ? C3 H3A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3A S1A C1A 87.8(4) . . ? C10A O1A C7A 118.2(6) . . ? C1A N1A C2A 107.0(6) . . ? C8A N2A C1A 124.4(6) . . ? C8A N2A H2A 117.8 . . ? C1A N2A H2A 117.8 . . ? C11A N3A C10A 112.9(6) . . ? C11A N4A C13A 115.7(6) . . ? N1A C1A N2A 119.2(7) . . ? N1A C1A S1A 119.0(6) . . ? N2A C1A S1A 121.8(6) . . ? C7A C2A C3A 118.9(8) . . ? C7A C2A N1A 125.0(7) . . ? C3A C2A N1A 116.1(7) . . ? C2A C3A C4A 122.1(7) . . ? C2A C3A S1A 110.1(6) . . ? C4A C3A S1A 127.7(6) . . ? C5A C4A C3A 116.4(7) . . ? C5A C4A H4A 121.8 . . ? C3A C4A H4A 121.8 . . ? C4A C5A C6A 122.7(8) . . ? C4A C5A H5A 118.7 . . ? C6A C5A H5A 118.7 . . ? C5A C6A C7A 119.3(7) . . ? C5A C6A H6A 120.4 . . ? C7A C6A H6A 120.4 . . ? C2A C7A C6A 120.5(7) . . ? C2A C7A O1A 120.8(7) . . ? C6A C7A O1A 118.6(7) . . ? O2A C8A N2A 122.1(7) . . ? O2A C8A C9A 122.2(7) . . ? N2A C8A C9A 115.6(7) . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? N3A C10A O1A 117.0(7) . . ? N3A C10A C12A 124.0(7) . . ? O1A C10A C12A 118.9(7) . . ? N4A C11A N3A 129.4(7) . . ? N4A C11A H11A 115.3 . . ? N3A C11A H11A 115.3 . . ? C10A C12A C13A 117.7(7) . . ? C10A C12A H12A 121.2 . . ? C13A C12A H12A 121.2 . . ? C12A C13A N4A 120.2(7) . . ? C12A C13A C14A 123.6(7) . . ? N4A C13A C14A 116.0(6) . . ? C15A C14A C19A 116.2(7) . . ? C15A C14A C13A 122.8(7) . . ? C19A C14A C13A 120.9(7) . . ? C16A C15A C14A 121.7(7) . . ? C16A C15A H15A 119.1 . . ? C14A C15A H15A 119.1 . . ? C17A C16A C15A 120.4(8) . . ? C17A C16A H16A 119.8 . . ? C15A C16A H16A 119.8 . . ? C16A C17A C18A 119.2(7) . . ? C16A C17A C20A 120.1(8) . . ? C18A C17A C20A 120.6(7) . . ? C19A C18A C17A 120.3(8) . . ? C19A C18A H18A 119.8 . . ? C17A C18A H18A 119.8 . . ? C18A C19A C14A 122.1(8) . . ? C18A C19A H19A 119.0 . . ? C14A C19A H19A 119.0 . . ? F1A C20A F3A 105.1(9) . . ? F1A C20A F2A 103.3(9) . . ? F3A C20A F2A 100.0(8) . . ? F1A C20A C17A 116.5(7) . . ? F3A C20A C17A 114.6(8) . . ? F2A C20A C17A 115.4(8) . . ? C1B S1B C3B 89.0(4) . . ? C10B O1B C7B 117.6(6) . . ? C1B N1B C2B 110.8(6) . . ? C1B N2B C8B 122.3(7) . . ? C1B N2B H2B 118.8 . . ? C8B N2B H2B 118.8 . . ? C10B N3B C11B 113.1(6) . . ? C11B N4B C13B 115.8(6) . . ? N1B C1B N2B 119.8(7) . . ? N1B C1B S1B 115.7(6) . . ? N2B C1B S1B 124.5(6) . . ? C7B C2B N1B 126.3(7) . . ? C7B C2B C3B 119.6(7) . . ? N1B C2B C3B 114.1(7) . . ? C4B C3B C2B 121.8(7) . . ? C4B C3B S1B 127.8(6) . . ? C2B C3B S1B 110.4(6) . . ? C5B C4B C3B 117.5(7) . . ? C5B C4B H4B 121.3 . . ? C3B C4B H4B 121.3 . . ? C4B C5B C6B 121.5(8) . . ? C4B C5B H5B 119.2 . . ? C6B C5B H5B 119.2 . . ? C5B C6B C7B 120.1(7) . . ? C5B C6B H6B 120.0 . . ? C7B C6B H6B 120.0 . . ? C2B C7B O1B 119.3(7) . . ? C2B C7B C6B 119.5(7) . . ? O1B C7B C6B 121.0(7) . . ? O2B C8B N2B 121.1(8) . . ? O2B C8B C9B 125.6(8) . . ? N2B C8B C9B 113.3(7) . . ? C8B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C8B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? N3B C10B O1B 117.6(6) . . ? N3B C10B C12B 124.8(7) . . ? O1B C10B C12B 117.7(7) . . ? N4B C11B N3B 128.6(7) . . ? N4B C11B H11B 115.7 . . ? N3B C11B H11B 115.7 . . ? C13B C12B C10B 116.7(7) . . ? C13B C12B H12B 121.7 . . ? C10B C12B H12B 121.7 . . ? N4B C13B C12B 121.1(7) . . ? N4B C13B C14B 116.7(6) . . ? C12B C13B C14B 122.3(7) . . ? C15B C14B C19B 118.7(7) . . ? C15B C14B C13B 121.7(7) . . ? C19B C14B C13B 119.6(7) . . ? C16B C15B C14B 121.9(8) . . ? C16B C15B H15B 119.0 . . ? C14B C15B H15B 119.0 . . ? C15B C16B C17B 119.5(8) . . ? C15B C16B H16B 120.2 . . ? C17B C16B H16B 120.2 . . ? C18B C17B C16B 119.4(7) . . ? C18B C17B C20B 118.6(8) . . ? C16B C17B C20B 122.0(8) . . ? C19B C18B C17B 121.4(8) . . ? C19B C18B H18B 119.3 . . ? C17B C18B H18B 119.3 . . ? C18B C19B C14B 119.0(8) . . ? C18B C19B H19B 120.5 . . ? C14B C19B H19B 120.5 . . ? F2B C20B F3B 107.7(10) . . ? F2B C20B F1B 101.8(9) . . ? F3B C20B F1B 100.6(8) . . ? F2B C20B C17B 116.1(8) . . ? F3B C20B C17B 116.0(8) . . ? F1B C20B C17B 112.6(9) . . ? C4 O3 H3 109.5 . . ? O2 C1 O1 123.6(8) . . ? O2 C1 C2 116.6(9) . . ? O1 C1 C2 119.7(8) . . ? C3 C2 C1 132.7(9) . . ? C3 C2 H2 113.6 . . ? C1 C2 H2 113.6 . . ? C2 C3 C4 130.3(8) . . ? C2 C3 H3A 114.8 . . ? C4 C3 H3A 114.8 . . ? O4 C4 O3 119.3(8) . . ? O4 C4 C3 120.7(7) . . ? O3 C4 C3 120.1(7) . . ? 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 C2A N1A C1A N2A 179.9(7) . . . . ? C2A N1A C1A S1A 2.2(8) . . . . ? C8A N2A C1A N1A -175.4(7) . . . . ? C8A N2A C1A S1A 2.2(10) . . . . ? C3A S1A C1A N1A -2.5(6) . . . . ? C3A S1A C1A N2A 180.0(7) . . . . ? C1A N1A C2A C7A -179.1(7) . . . . ? C1A N1A C2A C3A -0.7(9) . . . . ? C7A C2A C3A C4A -2.5(11) . . . . ? N1A C2A C3A C4A 179.0(7) . . . . ? C7A C2A C3A S1A 177.5(6) . . . . ? N1A C2A C3A S1A -1.0(9) . . . . ? C1A S1A C3A C2A 1.8(6) . . . . ? C1A S1A C3A C4A -178.3(7) . . . . ? C2A C3A C4A C5A 2.4(11) . . . . ? S1A C3A C4A C5A -177.6(6) . . . . ? C3A C4A C5A C6A -1.2(11) . . . . ? C4A C5A C6A C7A 0.1(12) . . . . ? C3A C2A C7A C6A 1.3(11) . . . . ? N1A C2A C7A C6A 179.7(7) . . . . ? C3A C2A C7A O1A -176.1(7) . . . . ? N1A C2A C7A O1A 2.2(11) . . . . ? C5A C6A C7A C2A -0.1(11) . . . . ? C5A C6A C7A O1A 177.3(6) . . . . ? C10A O1A C7A C2A -106.9(8) . . . . ? C10A O1A C7A C6A 75.6(9) . . . . ? C1A N2A C8A O2A -1.1(11) . . . . ? C1A N2A C8A C9A 176.6(7) . . . . ? C11A N3A C10A O1A 178.8(6) . . . . ? C11A N3A C10A C12A -0.5(11) . . . . ? C7A O1A C10A N3A 18.7(10) . . . . ? C7A O1A C10A C12A -162.0(7) . . . . ? C13A N4A C11A N3A -0.6(12) . . . . ? C10A N3A C11A N4A 1.6(12) . . . . ? N3A C10A C12A C13A -1.3(11) . . . . ? O1A C10A C12A C13A 179.4(7) . . . . ? C10A C12A C13A N4A 2.3(11) . . . . ? C10A C12A C13A C14A -173.3(7) . . . . ? C11A N4A C13A C12A -1.4(10) . . . . ? C11A N4A C13A C14A 174.5(6) . . . . ? C12A C13A C14A C15A 3.1(12) . . . . ? N4A C13A C14A C15A -172.7(7) . . . . ? C12A C13A C14A C19A -179.9(7) . . . . ? N4A C13A C14A C19A 4.3(10) . . . . ? C19A C14A C15A C16A -0.2(12) . . . . ? C13A C14A C15A C16A 176.9(7) . . . . ? C14A C15A C16A C17A 0.1(12) . . . . ? C15A C16A C17A C18A -0.3(12) . . . . ? C15A C16A C17A C20A 179.4(8) . . . . ? C16A C17A C18A C19A 0.6(13) . . . . ? C20A C17A C18A C19A -179.2(8) . . . . ? C17A C18A C19A C14A -0.7(13) . . . . ? C15A C14A C19A C18A 0.5(12) . . . . ? C13A C14A C19A C18A -176.7(8) . . . . ? C16A C17A C20A F1A 41.8(13) . . . . ? C18A C17A C20A F1A -138.4(10) . . . . ? C16A C17A C20A F3A -81.4(11) . . . . ? C18A C17A C20A F3A 98.3(11) . . . . ? C16A C17A C20A F2A 163.2(9) . . . . ? C18A C17A C20A F2A -17.0(13) . . . . ? C2B N1B C1B N2B 179.9(7) . . . . ? C2B N1B C1B S1B 2.9(8) . . . . ? C8B N2B C1B N1B -177.7(7) . . . . ? C8B N2B C1B S1B -1.1(11) . . . . ? C3B S1B C1B N1B -1.6(6) . . . . ? C3B S1B C1B N2B -178.3(7) . . . . ? C1B N1B C2B C7B 177.3(7) . . . . ? C1B N1B C2B C3B -3.1(9) . . . . ? C7B C2B C3B C4B 0.8(12) . . . . ? N1B C2B C3B C4B -178.8(7) . . . . ? C7B C2B C3B S1B -178.4(6) . . . . ? N1B C2B C3B S1B 2.0(8) . . . . ? C1B S1B C3B C4B -179.4(8) . . . . ? C1B S1B C3B C2B -0.3(6) . . . . ? C2B C3B C4B C5B -0.5(11) . . . . ? S1B C3B C4B C5B 178.6(6) . . . . ? C3B C4B C5B C6B -0.1(11) . . . . ? C4B C5B C6B C7B 0.3(12) . . . . ? N1B C2B C7B O1B -5.0(12) . . . . ? C3B C2B C7B O1B 175.4(7) . . . . ? N1B C2B C7B C6B 179.0(7) . . . . ? C3B C2B C7B C6B -0.5(11) . . . . ? C10B O1B C7B C2B 105.1(8) . . . . ? C10B O1B C7B C6B -79.0(9) . . . . ? C5B C6B C7B C2B 0.0(12) . . . . ? C5B C6B C7B O1B -175.9(7) . . . . ? C1B N2B C8B O2B -2.0(12) . . . . ? C1B N2B C8B C9B 177.5(7) . . . . ? C11B N3B C10B O1B -179.9(6) . . . . ? C11B N3B C10B C12B -1.2(11) . . . . ? C7B O1B C10B N3B -19.3(9) . . . . ? C7B O1B C10B C12B 161.9(7) . . . . ? C13B N4B C11B N3B 1.2(11) . . . . ? C10B N3B C11B N4B 0.2(11) . . . . ? N3B C10B C12B C13B 0.6(11) . . . . ? O1B C10B C12B C13B 179.4(6) . . . . ? C11B N4B C13B C12B -1.8(10) . . . . ? C11B N4B C13B C14B 179.0(6) . . . . ? C10B C12B C13B N4B 1.0(11) . . . . ? C10B C12B C13B C14B -179.9(7) . . . . ? N4B C13B C14B C15B 26.8(10) . . . . ? C12B C13B C14B C15B -152.4(8) . . . . ? N4B C13B C14B C19B -153.5(7) . . . . ? C12B C13B C14B C19B 27.3(11) . . . . ? C19B C14B C15B C16B -0.8(12) . . . . ? C13B C14B C15B C16B 178.9(7) . . . . ? C14B C15B C16B C17B 1.6(12) . . . . ? C15B C16B C17B C18B -1.8(12) . . . . ? C15B C16B C17B C20B 178.9(7) . . . . ? C16B C17B C18B C19B 1.3(12) . . . . ? C20B C17B C18B C19B -179.4(7) . . . . ? C17B C18B C19B C14B -0.4(12) . . . . ? C15B C14B C19B C18B 0.2(11) . . . . ? C13B C14B C19B C18B -179.5(7) . . . . ? C18B C17B C20B F2B -68.4(13) . . . . ? C16B C17B C20B F2B 110.9(12) . . . . ? C18B C17B C20B F3B 59.7(12) . . . . ? C16B C17B C20B F3B -121.0(10) . . . . ? C18B C17B C20B F1B 174.8(8) . . . . ? C16B C17B C20B F1B -5.9(12) . . . . ? O2 C1 C2 C3 168.7(9) . . . . ? O1 C1 C2 C3 -15.6(15) . . . . ? C1 C2 C3 C4 5.2(17) . . . . ? C2 C3 C4 O4 -178.7(9) . . . . ? C2 C3 C4 O3 1.9(15) . . . . ? 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 N2A H2A O4 0.88 1.97 2.835(8) 168.6 2_676 N2B H2B O2 0.88 1.77 2.654(8) 178.9 2_667 O3 H3 O1 0.84 1.64 2.474(8) 175.1 . _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.790 _refine_diff_density_min -0.640 _refine_diff_density_rms 0.117 # Attachment 'SCA_2.cif' data_SCA_2 _database_code_depnum_ccdc_archive 'CCDC 791333' #TrackingRef 'SCA_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety '2(C20 H13 F3 N4 O2 S), C4 H6 O4' _chemical_formula_sum 'C22 H16 F3 N4 O4 S' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour colorless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 489.45 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3294(2) _cell_length_b 13.7454(3) _cell_length_c 15.9536(4) _cell_angle_alpha 112.0290(10) _cell_angle_beta 90.006(2) _cell_angle_gamma 112.2800(10) _cell_volume 2101.56(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 389 _cell_measurement_theta_min 4.76 _cell_measurement_theta_max 22.34 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1004 _exptl_absorpt_coefficient_mu 1.972 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6801 _exptl_absorpt_correction_T_max 0.7530 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83 to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Scaling and absorption corrections were performed by the SADABS program. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V6.1. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 24552 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 67.87 _reflns_number_total 7316 _reflns_number_gt 5729 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.58, 2007)' _computing_cell_refinement 'APEX2 (BRUKER, V5-0, 2008)' _computing_data_reduction 'SAINT (BRUKER, V7.56A, 2008)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.0754P)^2^+0.5352P] 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 7316 _refine_ls_number_parameters 617 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1204 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 S1A S 0.32926(6) 1.11701(5) 0.64883(4) 0.02899(16) Uani 1 1 d . . . O1A O 0.18193(16) 0.89097(14) 0.31244(12) 0.0310(4) Uani 1 1 d . . . O2A O 0.17445(18) 1.12521(16) 0.78030(13) 0.0408(5) Uani 1 1 d . . . F1A F -0.52291(17) 0.3095(2) -0.11640(14) 0.0829(8) Uani 1 1 d . . . F2A F -0.37138(18) 0.33101(18) -0.19401(12) 0.0601(5) Uani 1 1 d . . . F3A F -0.4368(3) 0.18897(17) -0.15687(16) 0.0877(8) Uani 1 1 d . . . N1A N 0.15471(19) 0.96327(16) 0.50495(14) 0.0270(5) Uani 1 1 d . . . N2A N 0.07166(19) 0.98774(17) 0.64080(14) 0.0302(5) Uani 1 1 d . . . H2A H -0.0025 0.9315 0.6089 0.036 Uiso 1 1 calc R . . N3A N 0.19017(19) 0.73530(17) 0.33275(14) 0.0300(5) Uani 1 1 d . . . N4A N 0.0431(2) 0.54440(18) 0.23157(15) 0.0339(5) Uani 1 1 d . . . C1A C 0.2887(2) 0.96669(19) 0.38290(17) 0.0274(5) Uani 1 1 d . . . C2A C 0.4085(2) 1.0133(2) 0.36028(19) 0.0320(6) Uani 1 1 d . . . H2A1 H 0.4199 0.9887 0.2979 0.038 Uiso 1 1 calc R . . C3A C 0.5133(2) 1.0970(2) 0.4292(2) 0.0341(6) Uani 1 1 d . . . H3A H 0.5956 1.1285 0.4130 0.041 Uiso 1 1 calc R . . C4A C 0.4996(2) 1.1344(2) 0.51985(19) 0.0307(6) Uani 1 1 d . . . H4A H 0.5710 1.1913 0.5665 0.037 Uiso 1 1 calc R . . C5A C 0.3777(2) 1.08647(19) 0.54123(17) 0.0270(5) Uani 1 1 d . . . C6A C 0.2707(2) 1.00251(19) 0.47410(17) 0.0253(5) Uani 1 1 d . . . C7A C 0.1726(2) 1.01484(19) 0.59315(17) 0.0275(5) Uani 1 1 d . . . C8A C 0.0774(2) 1.0407(2) 0.73275(18) 0.0318(6) Uani 1 1 d . . . C9A C -0.0394(3) 0.9886(2) 0.7709(2) 0.0392(6) Uani 1 1 d . . . H9A1 H -0.0257 0.9374 0.7952 0.059 Uiso 1 1 calc R . . H9A2 H -0.1152 0.9446 0.7222 0.059 Uiso 1 1 calc R . . H9A3 H -0.0538 1.0498 0.8202 0.059 Uiso 1 1 calc R . . C10A C 0.1365(2) 0.7764(2) 0.28907(17) 0.0271(5) Uani 1 1 d . . . C11A C 0.0329(2) 0.7079(2) 0.21676(17) 0.0299(5) Uani 1 1 d . . . H11A H -0.0048 0.7404 0.1874 0.036 Uiso 1 1 calc R . . C12A C -0.0120(2) 0.5906(2) 0.18999(17) 0.0291(5) Uani 1 1 d . . . C13A C 0.1391(2) 0.6195(2) 0.30048(19) 0.0336(6) Uani 1 1 d . . . H13A H 0.1767 0.5880 0.3309 0.040 Uiso 1 1 calc R . . C14A C -0.1200(2) 0.5109(2) 0.11253(18) 0.0308(6) Uani 1 1 d . . . C15A C -0.2266(3) 0.5355(2) 0.10318(19) 0.0359(6) Uani 1 1 d . . . H15A H -0.2328 0.6010 0.1489 0.043 Uiso 1 1 calc R . . C16A C -0.3231(3) 0.4652(2) 0.02778(19) 0.0382(6) Uani 1 1 d . . . H16A H -0.3962 0.4816 0.0220 0.046 Uiso 1 1 calc R . . C17A C -0.3132(3) 0.3704(2) -0.03964(18) 0.0364(6) Uani 1 1 d . . . C18A C -0.2095(3) 0.3442(2) -0.02992(19) 0.0392(7) Uani 1 1 d . . . H18A H -0.2042 0.2781 -0.0755 0.047 Uiso 1 1 calc R . . C19A C -0.1130(3) 0.4138(2) 0.04602(19) 0.0364(6) Uani 1 1 d . . . H19A H -0.0419 0.3952 0.0527 0.044 Uiso 1 1 calc R . . C20A C -0.4115(3) 0.2996(3) -0.1261(2) 0.0457(7) Uani 1 1 d . . . S1B S 0.37695(6) 0.27686(5) 0.38190(4) 0.03020(16) Uani 1 1 d . . . O1B O 0.81847(15) 0.52839(14) 0.54605(12) 0.0309(4) Uani 1 1 d . . . O2B O 0.16621(16) 0.20608(15) 0.45507(13) 0.0352(4) Uani 1 1 d . . . F1B F 1.2778(2) 1.11045(19) 1.11436(14) 0.0770(7) Uani 1 1 d . . . F2B F 1.3367(3) 0.9856(2) 1.12035(16) 0.1058(10) Uani 1 1 d . . . F3B F 1.4605(2) 1.1166(2) 1.08112(16) 0.1029(10) Uani 1 1 d . . . N1B N 0.55223(18) 0.41012(16) 0.52860(14) 0.0252(4) Uani 1 1 d . . . N2B N 0.34454(19) 0.33283(16) 0.56046(14) 0.0274(4) Uani 1 1 d . . . H2B H 0.3760 0.3726 0.6193 0.033 Uiso 1 1 calc R . . N3B N 1.0077(2) 0.63962(18) 0.50928(15) 0.0318(5) Uani 1 1 d . . . N4B N 1.1766(2) 0.79107(18) 0.63081(15) 0.0327(5) Uani 1 1 d . . . C1B C 0.7495(2) 0.46585(19) 0.45692(17) 0.0264(5) Uani 1 1 d . . . C2B C 0.7981(2) 0.4535(2) 0.37636(18) 0.0304(6) Uani 1 1 d . . . H2B1 H 0.8884 0.4912 0.3781 0.036 Uiso 1 1 calc R . . C3B C 0.7158(3) 0.3858(2) 0.29201(18) 0.0341(6) Uani 1 1 d . . . H3B H 0.7511 0.3790 0.2371 0.041 Uiso 1 1 calc R . . C4B C 0.5846(3) 0.3285(2) 0.28644(18) 0.0344(6) Uani 1 1 d . . . H4B H 0.5289 0.2827 0.2289 0.041 Uiso 1 1 calc R . . C5B C 0.5371(2) 0.3403(2) 0.36776(18) 0.0298(5) Uani 1 1 d . . . C6B C 0.6165(2) 0.40774(19) 0.45386(17) 0.0258(5) Uani 1 1 d . . . C7B C 0.4287(2) 0.34499(19) 0.49949(17) 0.0257(5) Uani 1 1 d . . . C8B C 0.2152(2) 0.2632(2) 0.53621(18) 0.0290(5) Uani 1 1 d . . . C9B C 0.1410(2) 0.2652(2) 0.61336(19) 0.0331(6) Uani 1 1 d . . . H9B1 H 0.1074 0.3245 0.6265 0.050 Uiso 1 1 calc R . . H9B2 H 0.1980 0.2824 0.6679 0.050 Uiso 1 1 calc R . . H9B3 H 0.0688 0.1900 0.5964 0.050 Uiso 1 1 calc R . . C10B C 0.9394(2) 0.6152(2) 0.57113(17) 0.0264(5) Uani 1 1 d . . . C11B C 0.9827(2) 0.6742(2) 0.66477(18) 0.0291(5) Uani 1 1 d . . . H11B H 0.9309 0.6548 0.7077 0.035 Uiso 1 1 calc R . . C12B C 1.1051(2) 0.7629(2) 0.69280(18) 0.0280(5) Uani 1 1 d . . . C13B C 1.1235(2) 0.7278(2) 0.54377(19) 0.0333(6) Uani 1 1 d . . . H13B H 1.1738 0.7473 0.5003 0.040 Uiso 1 1 calc R . . C14B C 1.1653(2) 0.8335(2) 0.79052(18) 0.0299(5) Uani 1 1 d . . . C15B C 1.1201(3) 0.7972(2) 0.85900(19) 0.0381(6) Uani 1 1 d . . . H15B H 1.0500 0.7245 0.8433 0.046 Uiso 1 1 calc R . . C16B C 1.1756(3) 0.8651(3) 0.9497(2) 0.0435(7) Uani 1 1 d . . . H16B H 1.1429 0.8395 0.9960 0.052 Uiso 1 1 calc R . . C17B C 1.2788(3) 0.9706(2) 0.9734(2) 0.0411(7) Uani 1 1 d . . . C18B C 1.3251(3) 1.0072(2) 0.9056(2) 0.0458(7) Uani 1 1 d . . . H18B H 1.3956 1.0797 0.9216 0.055 Uiso 1 1 calc R . . C19B C 1.2698(3) 0.9390(2) 0.8149(2) 0.0414(7) Uani 1 1 d . . . H19B H 1.3034 0.9645 0.7687 0.050 Uiso 1 1 calc R . . C20B C 1.3384(3) 1.0442(3) 1.0711(2) 0.0556(9) Uani 1 1 d . . . O3 O 0.46814(18) 0.45547(17) 0.74136(13) 0.0434(5) Uani 1 1 d . . . O4 O 0.66421(17) 0.53860(16) 0.70982(13) 0.0378(4) Uani 1 1 d . . . H4 H 0.6259 0.4993 0.6553 0.057 Uiso 1 1 calc R . . O5 O 0.7517(2) 0.7644(2) 1.03770(14) 0.0523(6) Uani 1 1 d . . . H5 H 0.7846 0.8023 1.0934 0.078 Uiso 1 1 calc R . . O6 O 0.93370(18) 0.73741(17) 1.02837(13) 0.0417(5) Uani 1 1 d . . . C21 C 0.5804(2) 0.5234(2) 0.76595(18) 0.0322(6) Uani 1 1 d . . . C22 C 0.6349(3) 0.5994(2) 0.86568(18) 0.0380(6) Uani 1 1 d . . . H22A H 0.5994 0.5531 0.9018 0.046 Uiso 1 1 calc R . . H22B H 0.6034 0.6613 0.8846 0.046 Uiso 1 1 calc R . . C23 C 0.7804(3) 0.6546(3) 0.89115(19) 0.0398(7) Uani 1 1 d . . . H23A H 0.8131 0.5936 0.8681 0.048 Uiso 1 1 calc R . . H23B H 0.8161 0.7066 0.8595 0.048 Uiso 1 1 calc R . . C24 C 0.8308(3) 0.7223(2) 0.99243(19) 0.0346(6) 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 S1A 0.0245(3) 0.0271(3) 0.0246(4) 0.0041(2) -0.0026(2) 0.0060(2) O1A 0.0323(9) 0.0282(9) 0.0260(10) 0.0079(7) -0.0021(7) 0.0087(7) O2A 0.0358(10) 0.0442(11) 0.0260(11) 0.0038(8) 0.0028(8) 0.0101(9) F1A 0.0307(10) 0.1232(19) 0.0429(13) 0.0001(11) -0.0036(8) 0.0118(11) F2A 0.0528(11) 0.0785(13) 0.0318(11) 0.0206(9) 0.0014(8) 0.0112(10) F3A 0.1058(19) 0.0415(11) 0.0652(16) 0.0041(10) -0.0394(13) -0.0040(11) N1A 0.0252(10) 0.0256(10) 0.0231(12) 0.0056(9) -0.0005(8) 0.0073(8) N2A 0.0248(10) 0.0306(10) 0.0259(13) 0.0063(9) 0.0015(8) 0.0069(9) N3A 0.0283(11) 0.0318(11) 0.0270(12) 0.0106(9) 0.0029(8) 0.0105(9) N4A 0.0346(12) 0.0310(11) 0.0305(13) 0.0099(9) 0.0013(9) 0.0102(9) C1A 0.0298(13) 0.0224(11) 0.0251(14) 0.0058(10) -0.0013(10) 0.0097(10) C2A 0.0346(14) 0.0341(13) 0.0301(15) 0.0144(11) 0.0082(10) 0.0155(11) C3A 0.0270(13) 0.0328(13) 0.0445(18) 0.0183(12) 0.0088(11) 0.0117(11) C4A 0.0244(12) 0.0247(12) 0.0379(16) 0.0101(11) -0.0011(10) 0.0073(10) C5A 0.0280(12) 0.0234(11) 0.0276(14) 0.0088(10) -0.0002(10) 0.0099(10) C6A 0.0226(11) 0.0237(11) 0.0277(14) 0.0096(10) 0.0008(9) 0.0082(9) C7A 0.0242(12) 0.0218(11) 0.0300(16) 0.0070(10) -0.0012(10) 0.0062(9) C8A 0.0319(13) 0.0346(13) 0.0274(16) 0.0092(11) 0.0036(10) 0.0152(11) C9A 0.0388(15) 0.0435(15) 0.0331(17) 0.0130(12) 0.0100(11) 0.0171(13) C10A 0.0262(12) 0.0301(12) 0.0215(14) 0.0080(10) 0.0061(9) 0.0105(10) C11A 0.0291(13) 0.0340(13) 0.0253(15) 0.0110(10) 0.0028(10) 0.0126(10) C12A 0.0273(12) 0.0327(12) 0.0250(15) 0.0107(10) 0.0077(10) 0.0111(10) C13A 0.0324(13) 0.0333(13) 0.0355(16) 0.0146(11) 0.0024(11) 0.0131(11) C14A 0.0296(13) 0.0301(12) 0.0276(15) 0.0119(11) 0.0068(10) 0.0066(10) C15A 0.0334(14) 0.0375(14) 0.0271(16) 0.0052(11) 0.0028(10) 0.0124(11) C16A 0.0271(13) 0.0474(16) 0.0335(17) 0.0125(12) 0.0038(11) 0.0123(12) C17A 0.0329(14) 0.0366(14) 0.0249(15) 0.0108(11) 0.0045(10) 0.0008(11) C18A 0.0427(16) 0.0311(13) 0.0302(16) 0.0047(11) 0.0073(11) 0.0087(12) C19A 0.0343(14) 0.0339(13) 0.0348(17) 0.0106(11) 0.0062(11) 0.0111(11) C20A 0.0404(16) 0.0454(16) 0.0294(18) 0.0088(13) 0.0009(12) 0.0014(13) S1B 0.0245(3) 0.0300(3) 0.0260(4) 0.0065(2) -0.0019(2) 0.0057(2) O1B 0.0220(8) 0.0346(9) 0.0265(10) 0.0097(7) 0.0015(7) 0.0044(7) O2B 0.0251(9) 0.0376(10) 0.0309(11) 0.0084(8) 0.0005(7) 0.0062(8) F1B 0.0941(17) 0.0740(14) 0.0423(13) -0.0006(10) 0.0139(11) 0.0374(13) F2B 0.165(3) 0.0735(15) 0.0437(15) 0.0090(11) -0.0426(15) 0.0279(16) F3B 0.0560(13) 0.115(2) 0.0463(15) -0.0167(12) -0.0067(10) -0.0096(13) N1B 0.0224(10) 0.0241(9) 0.0243(12) 0.0069(8) -0.0002(8) 0.0075(8) N2B 0.0250(10) 0.0268(10) 0.0234(12) 0.0062(8) -0.0008(8) 0.0076(8) N3B 0.0280(11) 0.0342(11) 0.0294(13) 0.0127(9) 0.0031(9) 0.0092(9) N4B 0.0287(11) 0.0336(11) 0.0310(13) 0.0136(10) 0.0036(9) 0.0076(9) C1B 0.0258(12) 0.0248(11) 0.0239(14) 0.0057(10) -0.0008(9) 0.0097(10) C2B 0.0269(12) 0.0299(12) 0.0318(15) 0.0103(10) 0.0046(10) 0.0113(10) C3B 0.0394(15) 0.0335(13) 0.0257(15) 0.0076(11) 0.0067(11) 0.0154(12) C4B 0.0359(14) 0.0337(13) 0.0241(15) 0.0061(11) 0.0011(10) 0.0101(11) C5B 0.0275(12) 0.0260(12) 0.0296(15) 0.0074(10) -0.0010(10) 0.0085(10) C6B 0.0279(12) 0.0219(11) 0.0268(14) 0.0080(10) 0.0037(10) 0.0113(10) C7B 0.0270(12) 0.0211(11) 0.0282(15) 0.0091(10) 0.0027(9) 0.0098(9) C8B 0.0242(12) 0.0258(11) 0.0348(16) 0.0111(11) 0.0017(10) 0.0093(10) C9B 0.0256(12) 0.0355(13) 0.0366(16) 0.0159(11) 0.0047(10) 0.0096(11) C10B 0.0212(11) 0.0270(12) 0.0281(15) 0.0084(10) 0.0012(9) 0.0095(9) C11B 0.0254(12) 0.0317(12) 0.0283(15) 0.0123(11) 0.0051(10) 0.0096(10) C12B 0.0250(12) 0.0281(12) 0.0296(15) 0.0115(10) 0.0031(10) 0.0094(10) C13B 0.0307(13) 0.0329(13) 0.0297(16) 0.0136(11) 0.0051(10) 0.0054(11) C14B 0.0243(12) 0.0293(12) 0.0316(15) 0.0092(11) 0.0022(10) 0.0095(10) C15B 0.0309(14) 0.0366(14) 0.0318(17) 0.0098(12) 0.0007(11) 0.0025(11) C16B 0.0387(15) 0.0488(17) 0.0313(17) 0.0145(13) 0.0044(12) 0.0077(13) C17B 0.0390(15) 0.0390(15) 0.0338(17) 0.0056(12) -0.0003(12) 0.0133(12) C18B 0.0425(16) 0.0315(14) 0.0415(19) 0.0069(12) -0.0024(13) 0.0006(12) C19B 0.0384(15) 0.0359(14) 0.0375(18) 0.0133(12) 0.0026(12) 0.0043(12) C20B 0.0526(19) 0.0509(18) 0.037(2) 0.0022(15) -0.0022(14) 0.0099(16) O3 0.0316(10) 0.0531(12) 0.0298(12) 0.0119(9) -0.0002(8) 0.0062(9) O4 0.0320(10) 0.0469(11) 0.0228(11) 0.0091(8) 0.0014(7) 0.0092(8) O5 0.0425(12) 0.0728(15) 0.0263(12) -0.0020(10) -0.0010(8) 0.0299(11) O6 0.0335(10) 0.0514(11) 0.0310(12) 0.0102(9) 0.0011(8) 0.0145(9) C21 0.0324(14) 0.0361(13) 0.0284(15) 0.0122(11) 0.0035(10) 0.0150(11) C22 0.0343(14) 0.0484(16) 0.0272(16) 0.0116(12) 0.0050(11) 0.0163(12) C23 0.0335(14) 0.0497(16) 0.0278(16) 0.0084(12) 0.0055(11) 0.0158(12) C24 0.0316(14) 0.0382(14) 0.0265(15) 0.0094(11) 0.0051(11) 0.0103(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1A C5A 1.749(3) . ? S1A C7A 1.757(2) . ? O1A C10A 1.353(3) . ? O1A C1A 1.406(3) . ? O2A C8A 1.227(3) . ? F1A C20A 1.323(4) . ? F2A C20A 1.331(4) . ? F3A C20A 1.321(4) . ? N1A C7A 1.291(3) . ? N1A C6A 1.386(3) . ? N2A C8A 1.360(3) . ? N2A C7A 1.383(3) . ? N2A H2A 0.8800 . ? N3A C10A 1.315(3) . ? N3A C13A 1.349(3) . ? N4A C13A 1.325(3) . ? N4A C12A 1.359(3) . ? C1A C2A 1.378(4) . ? C1A C6A 1.393(4) . ? C2A C3A 1.399(4) . ? C2A H2A1 0.9500 . ? C3A C4A 1.372(4) . ? C3A H3A 0.9500 . ? C4A C5A 1.391(4) . ? C4A H4A 0.9500 . ? C5A C6A 1.401(3) . ? C8A C9A 1.497(4) . ? C9A H9A1 0.9800 . ? C9A H9A2 0.9800 . ? C9A H9A3 0.9800 . ? C10A C11A 1.393(3) . ? C11A C12A 1.380(4) . ? C11A H11A 0.9500 . ? C12A C14A 1.481(3) . ? C13A H13A 0.9500 . ? C14A C19A 1.390(4) . ? C14A C15A 1.393(4) . ? C15A C16A 1.380(4) . ? C15A H15A 0.9500 . ? C16A C17A 1.387(4) . ? C16A H16A 0.9500 . ? C17A C18A 1.379(4) . ? C17A C20A 1.503(4) . ? C18A C19A 1.384(4) . ? C18A H18A 0.9500 . ? C19A H19A 0.9500 . ? S1B C7B 1.734(3) . ? S1B C5B 1.747(3) . ? O1B C10B 1.365(3) . ? O1B C1B 1.395(3) . ? O2B C8B 1.228(3) . ? F1B C20B 1.334(4) . ? F2B C20B 1.314(4) . ? F3B C20B 1.329(4) . ? N1B C7B 1.309(3) . ? N1B C6B 1.394(3) . ? N2B C8B 1.368(3) . ? N2B C7B 1.373(3) . ? N2B H2B 0.8800 . ? N3B C10B 1.318(3) . ? N3B C13B 1.337(3) . ? N4B C13B 1.320(3) . ? N4B C12B 1.355(3) . ? C1B C2B 1.375(4) . ? C1B C6B 1.403(3) . ? C2B C3B 1.396(4) . ? C2B H2B1 0.9500 . ? C3B C4B 1.378(4) . ? C3B H3B 0.9500 . ? C4B C5B 1.381(4) . ? C4B H4B 0.9500 . ? C5B C6B 1.403(3) . ? C8B C9B 1.488(4) . ? C9B H9B1 0.9800 . ? C9B H9B2 0.9800 . ? C9B H9B3 0.9800 . ? C10B C11B 1.385(4) . ? C11B C12B 1.385(3) . ? C11B H11B 0.9500 . ? C12B C14B 1.483(4) . ? C13B H13B 0.9500 . ? C14B C15B 1.385(4) . ? C14B C19B 1.390(4) . ? C15B C16B 1.379(4) . ? C15B H15B 0.9500 . ? C16B C17B 1.384(4) . ? C16B H16B 0.9500 . ? C17B C18B 1.380(4) . ? C17B C20B 1.486(4) . ? C18B C19B 1.380(4) . ? C18B H18B 0.9500 . ? C19B H19B 0.9500 . ? O3 C21 1.211(3) . ? O4 C21 1.318(3) . ? O4 H4 0.8400 . ? O5 C24 1.319(3) . ? O5 H5 0.8400 . ? O6 C24 1.207(3) . ? C21 C22 1.506(4) . ? C22 C23 1.509(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.507(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5A S1A C7A 88.05(12) . . ? C10A O1A C1A 119.82(19) . . ? C7A N1A C6A 109.3(2) . . ? C8A N2A C7A 125.5(2) . . ? C8A N2A H2A 117.3 . . ? C7A N2A H2A 117.3 . . ? C10A N3A C13A 114.6(2) . . ? C13A N4A C12A 115.5(2) . . ? C2A C1A C6A 120.5(2) . . ? C2A C1A O1A 119.2(2) . . ? C6A C1A O1A 120.0(2) . . ? C1A C2A C3A 120.0(2) . . ? C1A C2A H2A1 120.0 . . ? C3A C2A H2A1 120.0 . . ? C4A C3A C2A 121.3(2) . . ? C4A C3A H3A 119.3 . . ? C2A C3A H3A 119.3 . . ? C3A C4A C5A 117.8(2) . . ? C3A C4A H4A 121.1 . . ? C5A C4A H4A 121.1 . . ? C4A C5A C6A 122.5(2) . . ? C4A C5A S1A 128.68(19) . . ? C6A C5A S1A 108.86(18) . . ? N1A C6A C1A 125.7(2) . . ? N1A C6A C5A 116.4(2) . . ? C1A C6A C5A 117.9(2) . . ? N1A C7A N2A 120.4(2) . . ? N1A C7A S1A 117.36(19) . . ? N2A C7A S1A 122.18(19) . . ? O2A C8A N2A 120.7(2) . . ? O2A C8A C9A 123.2(2) . . ? N2A C8A C9A 116.1(2) . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? N3A C10A O1A 120.5(2) . . ? N3A C10A C11A 123.8(2) . . ? O1A C10A C11A 115.7(2) . . ? C12A C11A C10A 116.6(2) . . ? C12A C11A H11A 121.7 . . ? C10A C11A H11A 121.7 . . ? N4A C12A C11A 121.6(2) . . ? N4A C12A C14A 118.0(2) . . ? C11A C12A C14A 120.4(2) . . ? N4A C13A N3A 128.0(2) . . ? N4A C13A H13A 116.0 . . ? N3A C13A H13A 116.0 . . ? C19A C14A C15A 119.4(2) . . ? C19A C14A C12A 120.1(2) . . ? C15A C14A C12A 120.4(2) . . ? C16A C15A C14A 120.3(2) . . ? C16A C15A H15A 119.9 . . ? C14A C15A H15A 119.9 . . ? C15A C16A C17A 119.9(3) . . ? C15A C16A H16A 120.1 . . ? C17A C16A H16A 120.1 . . ? C18A C17A C16A 120.2(2) . . ? C18A C17A C20A 119.5(3) . . ? C16A C17A C20A 120.3(3) . . ? C17A C18A C19A 120.2(2) . . ? C17A C18A H18A 119.9 . . ? C19A C18A H18A 119.9 . . ? C18A C19A C14A 120.1(3) . . ? C18A C19A H19A 120.0 . . ? C14A C19A H19A 120.0 . . ? F3A C20A F1A 107.3(3) . . ? F3A C20A F2A 106.0(3) . . ? F1A C20A F2A 105.5(3) . . ? F3A C20A C17A 112.6(3) . . ? F1A C20A C17A 113.1(3) . . ? F2A C20A C17A 111.9(2) . . ? C7B S1B C5B 88.40(12) . . ? C10B O1B C1B 125.3(2) . . ? C7B N1B C6B 109.6(2) . . ? C8B N2B C7B 124.6(2) . . ? C8B N2B H2B 117.7 . . ? C7B N2B H2B 117.7 . . ? C10B N3B C13B 114.7(2) . . ? C13B N4B C12B 116.0(2) . . ? C2B C1B O1B 127.5(2) . . ? C2B C1B C6B 119.5(2) . . ? O1B C1B C6B 113.0(2) . . ? C1B C2B C3B 120.5(2) . . ? C1B C2B H2B1 119.8 . . ? C3B C2B H2B1 119.8 . . ? C4B C3B C2B 121.6(3) . . ? C4B C3B H3B 119.2 . . ? C2B C3B H3B 119.2 . . ? C3B C4B C5B 117.4(2) . . ? C3B C4B H4B 121.3 . . ? C5B C4B H4B 121.3 . . ? C4B C5B C6B 122.7(2) . . ? C4B C5B S1B 127.60(19) . . ? C6B C5B S1B 109.67(19) . . ? N1B C6B C5B 115.0(2) . . ? N1B C6B C1B 126.7(2) . . ? C5B C6B C1B 118.3(2) . . ? N1B C7B N2B 120.7(2) . . ? N1B C7B S1B 117.30(19) . . ? N2B C7B S1B 121.99(17) . . ? O2B C8B N2B 120.4(2) . . ? O2B C8B C9B 123.8(2) . . ? N2B C8B C9B 115.8(2) . . ? C8B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C8B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? N3B C10B O1B 121.2(2) . . ? N3B C10B C11B 123.6(2) . . ? O1B C10B C11B 115.1(2) . . ? C12B C11B C10B 116.8(2) . . ? C12B C11B H11B 121.6 . . ? C10B C11B H11B 121.6 . . ? N4B C12B C11B 120.9(2) . . ? N4B C12B C14B 115.9(2) . . ? C11B C12B C14B 123.2(2) . . ? N4B C13B N3B 128.0(2) . . ? N4B C13B H13B 116.0 . . ? N3B C13B H13B 116.0 . . ? C15B C14B C19B 118.6(3) . . ? C15B C14B C12B 121.8(2) . . ? C19B C14B C12B 119.7(2) . . ? C16B C15B C14B 120.9(3) . . ? C16B C15B H15B 119.5 . . ? C14B C15B H15B 119.5 . . ? C15B C16B C17B 120.1(3) . . ? C15B C16B H16B 120.0 . . ? C17B C16B H16B 120.0 . . ? C18B C17B C16B 119.5(3) . . ? C18B C17B C20B 120.3(3) . . ? C16B C17B C20B 120.2(3) . . ? C17B C18B C19B 120.4(3) . . ? C17B C18B H18B 119.8 . . ? C19B C18B H18B 119.8 . . ? C18B C19B C14B 120.5(3) . . ? C18B C19B H19B 119.7 . . ? C14B C19B H19B 119.7 . . ? F2B C20B F3B 107.2(3) . . ? F2B C20B F1B 104.6(3) . . ? F3B C20B F1B 105.1(3) . . ? F2B C20B C17B 113.7(3) . . ? F3B C20B C17B 112.7(3) . . ? F1B C20B C17B 112.8(3) . . ? C21 O4 H4 109.5 . . ? C24 O5 H5 109.5 . . ? O3 C21 O4 124.2(2) . . ? O3 C21 C22 121.5(2) . . ? O4 C21 C22 114.3(2) . . ? C21 C22 C23 116.5(2) . . ? C21 C22 H22A 108.2 . . ? C23 C22 H22A 108.2 . . ? C21 C22 H22B 108.2 . . ? C23 C22 H22B 108.2 . . ? H22A C22 H22B 107.3 . . ? C24 C23 C22 114.8(2) . . ? C24 C23 H23A 108.6 . . ? C22 C23 H23A 108.6 . . ? C24 C23 H23B 108.6 . . ? C22 C23 H23B 108.6 . . ? H23A C23 H23B 107.5 . . ? O6 C24 O5 123.4(3) . . ? O6 C24 C23 123.5(2) . . ? O5 C24 C23 113.1(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 C10A O1A C1A C2A 102.7(3) . . . . ? C10A O1A C1A C6A -83.6(3) . . . . ? C6A C1A C2A C3A 0.3(4) . . . . ? O1A C1A C2A C3A 174.0(2) . . . . ? C1A C2A C3A C4A -0.2(4) . . . . ? C2A C3A C4A C5A 0.0(4) . . . . ? C3A C4A C5A C6A 0.0(4) . . . . ? C3A C4A C5A S1A -179.16(19) . . . . ? C7A S1A C5A C4A 179.5(2) . . . . ? C7A S1A C5A C6A 0.20(18) . . . . ? C7A N1A C6A C1A -179.7(2) . . . . ? C7A N1A C6A C5A -0.5(3) . . . . ? C2A C1A C6A N1A 179.0(2) . . . . ? O1A C1A C6A N1A 5.3(4) . . . . ? C2A C1A C6A C5A -0.2(3) . . . . ? O1A C1A C6A C5A -173.9(2) . . . . ? C4A C5A C6A N1A -179.2(2) . . . . ? S1A C5A C6A N1A 0.1(3) . . . . ? C4A C5A C6A C1A 0.1(3) . . . . ? S1A C5A C6A C1A 179.40(18) . . . . ? C6A N1A C7A N2A -178.0(2) . . . . ? C6A N1A C7A S1A 0.7(3) . . . . ? C8A N2A C7A N1A -176.1(2) . . . . ? C8A N2A C7A S1A 5.2(3) . . . . ? C5A S1A C7A N1A -0.6(2) . . . . ? C5A S1A C7A N2A 178.1(2) . . . . ? C7A N2A C8A O2A 5.5(4) . . . . ? C7A N2A C8A C9A -173.6(2) . . . . ? C13A N3A C10A O1A -177.5(2) . . . . ? C13A N3A C10A C11A 1.7(4) . . . . ? C1A O1A C10A N3A 1.0(3) . . . . ? C1A O1A C10A C11A -178.2(2) . . . . ? N3A C10A C11A C12A -1.3(4) . . . . ? O1A C10A C11A C12A 177.9(2) . . . . ? C13A N4A C12A C11A 1.9(4) . . . . ? C13A N4A C12A C14A -179.9(2) . . . . ? C10A C11A C12A N4A -0.6(4) . . . . ? C10A C11A C12A C14A -178.8(2) . . . . ? C12A N4A C13A N3A -1.5(4) . . . . ? C10A N3A C13A N4A -0.2(4) . . . . ? N4A C12A C14A C19A -43.1(4) . . . . ? C11A C12A C14A C19A 135.1(3) . . . . ? N4A C12A C14A C15A 140.1(3) . . . . ? C11A C12A C14A C15A -41.7(4) . . . . ? C19A C14A C15A C16A -1.1(4) . . . . ? C12A C14A C15A C16A 175.7(3) . . . . ? C14A C15A C16A C17A -0.8(4) . . . . ? C15A C16A C17A C18A 2.2(4) . . . . ? C15A C16A C17A C20A -174.4(3) . . . . ? C16A C17A C18A C19A -1.6(4) . . . . ? C20A C17A C18A C19A 175.0(3) . . . . ? C17A C18A C19A C14A -0.4(4) . . . . ? C15A C14A C19A C18A 1.8(4) . . . . ? C12A C14A C19A C18A -175.1(3) . . . . ? C18A C17A C20A F3A 38.8(4) . . . . ? C16A C17A C20A F3A -144.6(3) . . . . ? C18A C17A C20A F1A 160.6(3) . . . . ? C16A C17A C20A F1A -22.7(4) . . . . ? C18A C17A C20A F2A -80.5(4) . . . . ? C16A C17A C20A F2A 96.2(3) . . . . ? C10B O1B C1B C2B 20.7(4) . . . . ? C10B O1B C1B C6B -161.7(2) . . . . ? O1B C1B C2B C3B 178.9(2) . . . . ? C6B C1B C2B C3B 1.4(4) . . . . ? C1B C2B C3B C4B -0.7(4) . . . . ? C2B C3B C4B C5B -0.2(4) . . . . ? C3B C4B C5B C6B 0.3(4) . . . . ? C3B C4B C5B S1B -179.0(2) . . . . ? C7B S1B C5B C4B 179.6(2) . . . . ? C7B S1B C5B C6B 0.22(18) . . . . ? C7B N1B C6B C5B 1.0(3) . . . . ? C7B N1B C6B C1B -179.6(2) . . . . ? C4B C5B C6B N1B 179.8(2) . . . . ? S1B C5B C6B N1B -0.7(3) . . . . ? C4B C5B C6B C1B 0.4(4) . . . . ? S1B C5B C6B C1B 179.80(17) . . . . ? C2B C1B C6B N1B 179.3(2) . . . . ? O1B C1B C6B N1B 1.6(3) . . . . ? C2B C1B C6B C5B -1.3(3) . . . . ? O1B C1B C6B C5B -179.0(2) . . . . ? C6B N1B C7B N2B 179.8(2) . . . . ? C6B N1B C7B S1B -0.8(3) . . . . ? C8B N2B C7B N1B -177.3(2) . . . . ? C8B N2B C7B S1B 3.3(3) . . . . ? C5B S1B C7B N1B 0.38(19) . . . . ? C5B S1B C7B N2B 179.8(2) . . . . ? C7B N2B C8B O2B -0.2(4) . . . . ? C7B N2B C8B C9B -178.5(2) . . . . ? C13B N3B C10B O1B 179.1(2) . . . . ? C13B N3B C10B C11B -0.7(4) . . . . ? C1B O1B C10B N3B -7.2(3) . . . . ? C1B O1B C10B C11B 172.6(2) . . . . ? N3B C10B C11B C12B -0.3(4) . . . . ? O1B C10B C11B C12B 179.9(2) . . . . ? C13B N4B C12B C11B -1.4(4) . . . . ? C13B N4B C12B C14B 179.6(2) . . . . ? C10B C11B C12B N4B 1.4(4) . . . . ? C10B C11B C12B C14B -179.6(2) . . . . ? C12B N4B C13B N3B 0.3(4) . . . . ? C10B N3B C13B N4B 0.7(4) . . . . ? N4B C12B C14B C15B -163.0(2) . . . . ? C11B C12B C14B C15B 18.0(4) . . . . ? N4B C12B C14B C19B 17.0(3) . . . . ? C11B C12B C14B C19B -162.0(3) . . . . ? C19B C14B C15B C16B 1.4(4) . . . . ? C12B C14B C15B C16B -178.6(3) . . . . ? C14B C15B C16B C17B -0.7(5) . . . . ? C15B C16B C17B C18B 0.2(5) . . . . ? C15B C16B C17B C20B 179.7(3) . . . . ? C16B C17B C18B C19B -0.4(5) . . . . ? C20B C17B C18B C19B -179.9(3) . . . . ? C17B C18B C19B C14B 1.0(5) . . . . ? C15B C14B C19B C18B -1.5(4) . . . . ? C12B C14B C19B C18B 178.5(3) . . . . ? C18B C17B C20B F2B -147.3(3) . . . . ? C16B C17B C20B F2B 33.2(5) . . . . ? C18B C17B C20B F3B -25.0(5) . . . . ? C16B C17B C20B F3B 155.5(3) . . . . ? C18B C17B C20B F1B 93.9(4) . . . . ? C16B C17B C20B F1B -85.6(4) . . . . ? O3 C21 C22 C23 163.0(3) . . . . ? O4 C21 C22 C23 -17.7(4) . . . . ? C21 C22 C23 C24 -175.3(2) . . . . ? C22 C23 C24 O6 153.0(3) . . . . ? C22 C23 C24 O5 -27.6(4) . . . . ? 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 O4 H4 N1B 0.84 1.91 2.749(3) 175.3 . O5 H5 O2A 0.84 1.85 2.677(3) 169.2 2_677 N2B H2B O3 0.88 1.90 2.773(3) 171.0 . N2A H2A O2B 0.88 1.99 2.863(3) 173.1 2_566 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 67.87 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.323 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.060