data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Paul Blakemore' _publ_contact_author_email PAUL.BLAKEMORE@SCIENCE.OREGONSTATE.EDU _publ_section_title ; Spontaneous symmetry breaking during interrupted crystallization of an axially chiral amino acid derivative ; loop_ _publ_author_name 'Paul Blakemore' 'Christopher R. Emerson' 'M Sephton' 'Lev N. Zakharov' # Attachment 'Blakemore_CC_XRD_1.cif' data_pb13(bisamide1) _database_code_depnum_ccdc_archive 'CCDC 748439' #TrackingRef 'Blakemore_CC_XRD_1.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H36 N2 O4' _chemical_formula_weight 440.57 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.5558(7) _cell_length_b 10.4979(7) _cell_length_c 11.4257(8) _cell_angle_alpha 90.00 _cell_angle_beta 103.6910(10) _cell_angle_gamma 90.00 _cell_volume 1230.15(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3998 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 28.11 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9726 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'Bruker Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8028 _diffrn_reflns_av_R_equivalents 0.0121 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5304 _reflns_number_gt 5024 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.1137P] 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 refall _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 0.2(7) _refine_ls_number_reflns 5304 _refine_ls_number_parameters 433 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 O1 O 0.58879(10) 0.83546(9) 0.37419(9) 0.0319(2) Uani 1 1 d . . . O2 O 0.80542(11) 0.95055(11) 0.01241(11) 0.0393(3) Uani 1 1 d . . . O3 O 0.44236(10) 0.86390(9) 0.08074(10) 0.0306(2) Uani 1 1 d . . . O4 O 0.89044(11) 1.19086(13) 0.16768(12) 0.0487(3) Uani 1 1 d . . . N1 N 0.51351(11) 0.64515(11) 0.28689(10) 0.0257(2) Uani 1 1 d . . . N2 N 0.91148(11) 1.05158(11) 0.32376(11) 0.0266(2) Uani 1 1 d . . . C1 C 0.59038(14) 0.75121(12) 0.30066(12) 0.0246(3) Uani 1 1 d . . . C2 C 0.69111(13) 0.75348(13) 0.22553(12) 0.0248(3) Uani 1 1 d . . . C3 C 0.77220(15) 0.64692(14) 0.23301(14) 0.0319(3) Uani 1 1 d . . . C4 C 0.86903(16) 0.64379(15) 0.17034(15) 0.0366(3) Uani 1 1 d . . . C5 C 0.88302(15) 0.74414(16) 0.09532(14) 0.0348(3) Uani 1 1 d . . . C6 C 0.80306(14) 0.84986(14) 0.08731(13) 0.0290(3) Uani 1 1 d . . . C7 C 0.70886(13) 0.85949(13) 0.15723(12) 0.0248(3) Uani 1 1 d . . . C8 C 0.63351(13) 0.98087(13) 0.15594(12) 0.0241(3) Uani 1 1 d . . . C9 C 0.49627(13) 0.97947(13) 0.11826(12) 0.0251(3) Uani 1 1 d . . . C10 C 0.42365(13) 1.08945(14) 0.11979(13) 0.0287(3) Uani 1 1 d . . . C11 C 0.48672(15) 1.20322(14) 0.15779(14) 0.0328(3) Uani 1 1 d . . . C12 C 0.62096(15) 1.20754(15) 0.19319(15) 0.0331(3) Uani 1 1 d . . . C13 C 0.69478(13) 1.09769(14) 0.19253(13) 0.0278(3) Uani 1 1 d . . . C14 C 0.84193(14) 1.11616(14) 0.22732(14) 0.0310(3) Uani 1 1 d . . . C15 C 0.48141(17) 0.57983(15) 0.16987(14) 0.0335(3) Uani 1 1 d . . . C16 C 0.42991(14) 0.61781(13) 0.37357(13) 0.0273(3) Uani 1 1 d . . . C17 C 0.51115(19) 0.62628(18) 0.50330(15) 0.0394(4) Uani 1 1 d . . . C18 C 0.38017(18) 0.48029(16) 0.35493(16) 0.0381(4) Uani 1 1 d . . . C19 C 0.31562(19) 0.71047(19) 0.3518(2) 0.0466(4) Uani 1 1 d . . . C20 C 0.90280(17) 0.9511(2) -0.05512(17) 0.0435(4) Uani 1 1 d . . . C21 C 0.30352(15) 0.85777(17) 0.04190(16) 0.0359(3) Uani 1 1 d . . . C22 C 0.84630(15) 1.00166(16) 0.41399(14) 0.0336(3) Uani 1 1 d . . . C23 C 1.05708(13) 1.06453(14) 0.36114(13) 0.0298(3) Uani 1 1 d . . . C24 C 1.11779(17) 1.0399(2) 0.25464(17) 0.0429(4) Uani 1 1 d . . . C25 C 1.09220(18) 1.19606(18) 0.4159(2) 0.0459(4) Uani 1 1 d . . . C26 C 1.11175(16) 0.96218(19) 0.45533(18) 0.0433(4) Uani 1 1 d . . . H3 H 0.7587(15) 0.5771(17) 0.2803(15) 0.027(4) Uiso 1 1 d . . . H4 H 0.9246(19) 0.568(2) 0.1724(17) 0.041(5) Uiso 1 1 d . . . H5 H 0.9474(19) 0.7393(18) 0.0493(18) 0.041(5) Uiso 1 1 d . . . H10 H 0.3293(17) 1.0897(17) 0.0924(15) 0.031(4) Uiso 1 1 d . . . H11 H 0.4363(16) 1.2792(16) 0.1540(15) 0.026(4) Uiso 1 1 d . . . H12 H 0.6642(17) 1.2886(18) 0.2142(16) 0.031(4) Uiso 1 1 d . . . H15A H 0.3851(19) 0.5743(18) 0.1378(17) 0.036(4) Uiso 1 1 d . . . H15B H 0.5157(18) 0.495(2) 0.1783(17) 0.039(5) Uiso 1 1 d . . . H15C H 0.5203(18) 0.6254(18) 0.1162(17) 0.034(4) Uiso 1 1 d . . . H17A H 0.4541(19) 0.5976(19) 0.5530(18) 0.044(5) Uiso 1 1 d . . . H17B H 0.594(3) 0.566(3) 0.516(2) 0.073(7) Uiso 1 1 d . . . H17C H 0.545(2) 0.708(3) 0.527(2) 0.061(6) Uiso 1 1 d . . . H18A H 0.320(2) 0.470(2) 0.277(2) 0.050(5) Uiso 1 1 d . . . H18B H 0.455(2) 0.421(2) 0.3641(18) 0.048(5) Uiso 1 1 d . . . H18C H 0.3377(19) 0.457(2) 0.4220(18) 0.043(5) Uiso 1 1 d . . . H19A H 0.345(2) 0.797(2) 0.3640(19) 0.048(5) Uiso 1 1 d . . . H19B H 0.258(2) 0.693(2) 0.408(2) 0.058(6) Uiso 1 1 d . . . H19C H 0.259(2) 0.702(2) 0.271(2) 0.066(7) Uiso 1 1 d . . . H20A H 0.888(2) 0.875(2) -0.108(2) 0.047(5) Uiso 1 1 d . . . H20B H 0.890(2) 1.034(2) -0.103(2) 0.063(7) Uiso 1 1 d . . . H20C H 0.988(2) 0.950(2) -0.004(2) 0.045(5) Uiso 1 1 d . . . H21A H 0.277(2) 0.916(2) -0.0263(19) 0.046(5) Uiso 1 1 d . . . H21B H 0.2611(17) 0.8873(17) 0.1060(16) 0.033(4) Uiso 1 1 d . . . H21C H 0.2818(16) 0.7722(17) 0.0173(16) 0.028(4) Uiso 1 1 d . . . H22A H 0.869(2) 0.910(2) 0.4312(19) 0.049(5) Uiso 1 1 d . . . H22B H 0.8743(17) 1.0527(18) 0.4875(17) 0.035(4) Uiso 1 1 d . . . H22C H 0.7547(18) 1.0129(16) 0.3877(15) 0.028(4) Uiso 1 1 d . . . H24A H 1.092(2) 1.104(2) 0.192(2) 0.050(6) Uiso 1 1 d . . . H24B H 1.089(2) 0.957(2) 0.218(2) 0.051(6) Uiso 1 1 d . . . H24C H 1.211(2) 1.041(2) 0.2844(19) 0.052(6) Uiso 1 1 d . . . H25A H 1.050(2) 1.212(2) 0.487(2) 0.056(6) Uiso 1 1 d . . . H25B H 1.0639(19) 1.2590(19) 0.3545(18) 0.037(5) Uiso 1 1 d . . . H25C H 1.188(2) 1.205(2) 0.4434(18) 0.043(5) Uiso 1 1 d . . . H26A H 1.207(2) 0.971(2) 0.4787(18) 0.044(5) Uiso 1 1 d . . . H26B H 1.083(2) 0.982(2) 0.529(2) 0.051(6) Uiso 1 1 d . . . H26C H 1.084(2) 0.877(2) 0.421(2) 0.048(5) 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 O1 0.0399(6) 0.0272(5) 0.0335(5) -0.0072(4) 0.0183(4) -0.0063(4) O2 0.0355(6) 0.0466(6) 0.0429(6) 0.0142(5) 0.0236(5) 0.0044(5) O3 0.0236(5) 0.0307(5) 0.0372(5) -0.0053(4) 0.0064(4) -0.0007(4) O4 0.0301(5) 0.0524(7) 0.0611(8) 0.0277(6) 0.0057(5) -0.0090(5) N1 0.0307(6) 0.0238(5) 0.0252(5) -0.0027(4) 0.0121(5) -0.0025(5) N2 0.0229(5) 0.0265(5) 0.0311(6) -0.0005(5) 0.0076(4) -0.0013(5) C1 0.0291(7) 0.0224(6) 0.0243(6) 0.0018(5) 0.0107(5) 0.0019(5) C2 0.0258(7) 0.0249(6) 0.0247(6) -0.0031(5) 0.0082(5) -0.0011(5) C3 0.0364(8) 0.0273(7) 0.0345(8) 0.0022(6) 0.0135(6) 0.0038(6) C4 0.0355(8) 0.0321(7) 0.0448(9) -0.0017(7) 0.0149(7) 0.0094(7) C5 0.0290(7) 0.0418(8) 0.0383(8) -0.0035(7) 0.0171(6) 0.0029(6) C6 0.0252(6) 0.0343(7) 0.0289(7) 0.0011(6) 0.0092(5) -0.0022(6) C7 0.0231(6) 0.0272(6) 0.0245(6) -0.0009(5) 0.0065(5) 0.0003(5) C8 0.0237(6) 0.0263(6) 0.0242(6) 0.0038(5) 0.0093(5) 0.0020(5) C9 0.0249(6) 0.0286(6) 0.0231(6) 0.0021(5) 0.0082(5) -0.0014(5) C10 0.0225(7) 0.0339(7) 0.0305(7) 0.0039(6) 0.0077(5) 0.0031(6) C11 0.0337(7) 0.0257(7) 0.0405(8) 0.0052(6) 0.0120(6) 0.0079(6) C12 0.0328(7) 0.0258(7) 0.0411(8) 0.0037(6) 0.0096(6) -0.0016(6) C13 0.0244(6) 0.0286(7) 0.0312(7) 0.0074(6) 0.0082(5) -0.0006(5) C14 0.0252(7) 0.0285(7) 0.0399(8) 0.0037(6) 0.0091(6) -0.0016(6) C15 0.0436(9) 0.0288(7) 0.0308(8) -0.0069(6) 0.0140(7) -0.0078(7) C16 0.0293(7) 0.0255(6) 0.0308(7) 0.0023(5) 0.0146(6) -0.0015(5) C17 0.0465(9) 0.0454(9) 0.0305(7) -0.0023(7) 0.0173(7) -0.0129(8) C18 0.0475(9) 0.0329(8) 0.0364(8) 0.0030(7) 0.0148(7) -0.0108(8) C19 0.0403(9) 0.0413(9) 0.0660(13) 0.0158(9) 0.0280(9) 0.0091(8) C20 0.0347(9) 0.0633(12) 0.0377(9) 0.0099(9) 0.0189(7) -0.0031(8) C21 0.0251(7) 0.0411(9) 0.0399(8) -0.0055(7) 0.0044(6) -0.0028(7) C22 0.0271(7) 0.0432(9) 0.0315(8) 0.0022(7) 0.0091(6) -0.0031(7) C23 0.0218(6) 0.0318(7) 0.0352(7) -0.0041(6) 0.0057(5) -0.0017(6) C24 0.0274(8) 0.0598(11) 0.0431(9) -0.0052(9) 0.0115(7) -0.0022(8) C25 0.0348(9) 0.0367(8) 0.0632(12) -0.0122(9) 0.0056(8) -0.0081(7) C26 0.0292(8) 0.0479(10) 0.0500(10) 0.0056(8) 0.0040(7) 0.0045(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 O1 C1 1.2227(17) . ? O2 C6 1.3640(18) . ? O2 C20 1.4239(18) . ? O3 C9 1.3653(17) . ? O3 C21 1.4286(18) . ? O4 C14 1.2275(18) . ? N1 C1 1.3647(17) . ? N1 C15 1.4691(19) . ? N1 C16 1.5019(17) . ? N2 C14 1.3527(19) . ? N2 C22 1.4652(19) . ? N2 C23 1.5008(17) . ? C1 C2 1.5167(18) . ? C2 C7 1.3971(19) . ? C2 C3 1.3988(19) . ? C3 C4 1.380(2) . ? C3 H3 0.941(18) . ? C4 C5 1.388(2) . ? C4 H4 0.99(2) . ? C5 C6 1.384(2) . ? C5 H5 0.95(2) . ? C6 C7 1.4188(18) . ? C7 C8 1.5004(18) . ? C8 C13 1.403(2) . ? C8 C9 1.4103(18) . ? C9 C10 1.388(2) . ? C10 C11 1.386(2) . ? C10 H10 0.971(18) . ? C11 C12 1.379(2) . ? C11 H11 0.954(17) . ? C12 C13 1.393(2) . ? C12 H12 0.969(18) . ? C13 C14 1.5219(19) . ? C15 H15A 0.997(19) . ? C15 H15B 0.96(2) . ? C15 H15C 0.944(19) . ? C16 C19 1.524(2) . ? C16 C17 1.529(2) . ? C16 C18 1.534(2) . ? C17 H17A 0.97(2) . ? C17 H17B 1.06(3) . ? C17 H17C 0.95(3) . ? C18 H18A 0.97(2) . ? C18 H18B 0.99(2) . ? C18 H18C 1.01(2) . ? C19 H19A 0.96(2) . ? C19 H19B 1.00(2) . ? C19 H19C 0.98(3) . ? C20 H20A 0.99(2) . ? C20 H20B 1.02(3) . ? C20 H20C 0.95(2) . ? C21 H21A 0.98(2) . ? C21 H21B 0.994(18) . ? C21 H21C 0.953(18) . ? C22 H22A 1.00(2) . ? C22 H22B 0.981(19) . ? C22 H22C 0.950(18) . ? C23 C25 1.525(2) . ? C23 C24 1.526(2) . ? C23 C26 1.533(2) . ? C24 H24A 0.97(2) . ? C24 H24B 0.98(2) . ? C24 H24C 0.96(2) . ? C25 H25A 1.02(2) . ? C25 H25B 0.96(2) . ? C25 H25C 0.99(2) . ? C26 H26A 0.99(2) . ? C26 H26B 0.98(2) . ? C26 H26C 0.99(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O2 C20 117.75(13) . . ? C9 O3 C21 117.28(11) . . ? C1 N1 C15 119.24(11) . . ? C1 N1 C16 120.40(11) . . ? C15 N1 C16 117.77(11) . . ? C14 N2 C22 119.85(12) . . ? C14 N2 C23 120.55(11) . . ? C22 N2 C23 116.87(12) . . ? O1 C1 N1 124.40(12) . . ? O1 C1 C2 120.20(12) . . ? N1 C1 C2 115.14(11) . . ? C7 C2 C3 120.67(13) . . ? C7 C2 C1 122.23(12) . . ? C3 C2 C1 116.98(12) . . ? C4 C3 C2 120.32(14) . . ? C4 C3 H3 120.7(10) . . ? C2 C3 H3 119.0(10) . . ? C3 C4 C5 120.17(14) . . ? C3 C4 H4 121.0(11) . . ? C5 C4 H4 118.7(11) . . ? C6 C5 C4 119.80(13) . . ? C6 C5 H5 120.6(12) . . ? C4 C5 H5 119.6(12) . . ? O2 C6 C5 124.16(13) . . ? O2 C6 C7 114.67(12) . . ? C5 C6 C7 121.17(13) . . ? C2 C7 C6 117.53(12) . . ? C2 C7 C8 122.76(11) . . ? C6 C7 C8 119.70(12) . . ? C13 C8 C9 117.89(12) . . ? C13 C8 C7 122.24(11) . . ? C9 C8 C7 119.87(12) . . ? O3 C9 C10 123.54(12) . . ? O3 C9 C8 115.27(11) . . ? C10 C9 C8 121.19(12) . . ? C11 C10 C9 119.66(13) . . ? C11 C10 H10 118.6(11) . . ? C9 C10 H10 121.7(11) . . ? C12 C11 C10 120.27(14) . . ? C12 C11 H11 120.6(10) . . ? C10 C11 H11 119.0(10) . . ? C11 C12 C13 120.56(14) . . ? C11 C12 H12 119.5(10) . . ? C13 C12 H12 119.8(10) . . ? C12 C13 C8 120.42(12) . . ? C12 C13 C14 115.52(13) . . ? C8 C13 C14 123.99(12) . . ? O4 C14 N2 123.72(13) . . ? O4 C14 C13 118.06(13) . . ? N2 C14 C13 118.20(12) . . ? N1 C15 H15A 110.9(11) . . ? N1 C15 H15B 110.0(12) . . ? H15A C15 H15B 108.2(16) . . ? N1 C15 H15C 108.2(11) . . ? H15A C15 H15C 110.7(15) . . ? H15B C15 H15C 108.9(16) . . ? N1 C16 C19 109.65(12) . . ? N1 C16 C17 110.23(12) . . ? C19 C16 C17 111.22(14) . . ? N1 C16 C18 108.88(11) . . ? C19 C16 C18 110.27(14) . . ? C17 C16 C18 106.52(13) . . ? C16 C17 H17A 105.4(12) . . ? C16 C17 H17B 110.7(14) . . ? H17A C17 H17B 109.9(18) . . ? C16 C17 H17C 114.8(14) . . ? H17A C17 H17C 111.2(18) . . ? H17B C17 H17C 104.8(19) . . ? C16 C18 H18A 110.8(14) . . ? C16 C18 H18B 109.7(12) . . ? H18A C18 H18B 111.1(18) . . ? C16 C18 H18C 109.0(12) . . ? H18A C18 H18C 111.4(17) . . ? H18B C18 H18C 104.6(17) . . ? C16 C19 H19A 111.3(12) . . ? C16 C19 H19B 110.9(13) . . ? H19A C19 H19B 108.1(18) . . ? C16 C19 H19C 112.7(15) . . ? H19A C19 H19C 109(2) . . ? H19B C19 H19C 105(2) . . ? O2 C20 H20A 107.5(12) . . ? O2 C20 H20B 105.6(14) . . ? H20A C20 H20B 112.3(18) . . ? O2 C20 H20C 111.3(13) . . ? H20A C20 H20C 110.6(18) . . ? H20B C20 H20C 109.3(19) . . ? O3 C21 H21A 107.5(12) . . ? O3 C21 H21B 111.4(10) . . ? H21A C21 H21B 107.2(16) . . ? O3 C21 H21C 106.9(10) . . ? H21A C21 H21C 110.6(16) . . ? H21B C21 H21C 113.1(15) . . ? N2 C22 H22A 110.6(12) . . ? N2 C22 H22B 108.1(11) . . ? H22A C22 H22B 110.3(16) . . ? N2 C22 H22C 110.2(10) . . ? H22A C22 H22C 111.1(16) . . ? H22B C22 H22C 106.3(14) . . ? N2 C23 C25 109.38(12) . . ? N2 C23 C24 110.66(12) . . ? C25 C23 C24 111.93(14) . . ? N2 C23 C26 109.04(12) . . ? C25 C23 C26 109.39(14) . . ? C24 C23 C26 106.36(14) . . ? C23 C24 H24A 111.9(13) . . ? C23 C24 H24B 110.3(13) . . ? H24A C24 H24B 107.0(19) . . ? C23 C24 H24C 107.8(13) . . ? H24A C24 H24C 109.9(18) . . ? H24B C24 H24C 110.1(18) . . ? C23 C25 H25A 111.0(13) . . ? C23 C25 H25B 108.7(12) . . ? H25A C25 H25B 110.5(17) . . ? C23 C25 H25C 110.1(12) . . ? H25A C25 H25C 109.7(17) . . ? H25B C25 H25C 106.7(16) . . ? C23 C26 H26A 108.5(12) . . ? C23 C26 H26B 107.9(13) . . ? H26A C26 H26B 104.9(17) . . ? C23 C26 H26C 109.1(13) . . ? H26A C26 H26C 112.5(17) . . ? H26B C26 H26C 113.7(18) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.217 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.029 # Attachment 'Blakemore_CC_XRD_3TFA.cif' data_pbr12(amideamine3TFAsalt) _database_code_depnum_ccdc_archive 'CCDC 748440' #TrackingRef 'Blakemore_CC_XRD_3TFA.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H23 F3 N2 O5' _chemical_formula_weight 428.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.5061(6) _cell_length_b 12.7978(9) _cell_length_c 19.4743(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2120.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6826 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 23.85 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9614 _exptl_absorpt_correction_T_max 0.9888 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'Bruker Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20323 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3731 _reflns_number_gt 3521 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+1.0609P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(13) _refine_ls_number_reflns 3731 _refine_ls_number_parameters 349 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1304 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.201 _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 O1 O -0.1671(2) 0.54549(18) 0.13549(11) 0.0382(5) Uani 1 1 d . . . O2 O -0.7241(2) 0.37363(16) 0.16864(11) 0.0348(5) Uani 1 1 d . . . O3 O -0.4139(3) 0.3303(2) 0.02787(11) 0.0446(6) Uani 1 1 d . . . N1 N -0.2196(3) 0.5776(2) 0.02450(14) 0.0346(6) Uani 1 1 d . . . N2 N -0.2930(3) 0.5192(2) 0.26581(14) 0.0319(6) Uani 1 1 d . . . C1 C -0.0555(4) 0.5864(3) 0.0044(2) 0.0448(8) Uani 1 1 d . . . C2 C -0.2633(3) 0.5592(2) 0.08810(15) 0.0301(6) Uani 1 1 d . . . C3 C -0.4368(3) 0.5555(2) 0.10142(14) 0.0269(6) Uani 1 1 d . . . C4 C -0.5279(4) 0.6426(2) 0.08764(16) 0.0337(7) Uani 1 1 d . . . C5 C -0.6863(4) 0.6419(2) 0.10303(16) 0.0349(7) Uani 1 1 d . . . C6 C -0.7559(3) 0.5536(2) 0.13060(14) 0.0302(6) Uani 1 1 d . . . C7 C -0.6655(3) 0.4651(2) 0.14301(13) 0.0263(6) Uani 1 1 d . . . C8 C -0.5036(3) 0.4649(2) 0.12944(13) 0.0252(6) Uani 1 1 d . . . C9 C -0.4063(3) 0.3704(2) 0.14465(15) 0.0273(6) Uani 1 1 d . . . C10 C -0.3609(3) 0.3028(2) 0.09155(16) 0.0336(7) Uani 1 1 d . . . C11 C -0.2681(4) 0.2169(3) 0.1051(2) 0.0437(8) Uani 1 1 d . . . C12 C -0.2206(4) 0.1967(3) 0.1718(2) 0.0452(8) Uani 1 1 d . . . C13 C -0.2616(4) 0.2621(2) 0.2246(2) 0.0391(8) Uani 1 1 d . . . C14 C -0.3545(3) 0.3498(2) 0.21181(15) 0.0288(6) Uani 1 1 d . . . C15 C -0.3953(4) 0.4238(3) 0.26851(16) 0.0337(7) Uani 1 1 d . . . C16 C -0.3694(5) 0.6134(3) 0.2933(3) 0.0658(11) Uani 1 1 d . . . H16A H -0.2970 0.6727 0.2900 0.099 Uiso 1 1 calc R . . H16B H -0.3974 0.6019 0.3416 0.099 Uiso 1 1 calc R . . H16C H -0.4647 0.6284 0.2668 0.099 Uiso 1 1 calc R . . C17 C -0.8880(4) 0.3716(3) 0.1858(2) 0.0417(8) Uani 1 1 d . . . C18 C -0.3528(6) 0.2751(4) -0.0294(2) 0.0742(14) Uani 1 1 d . . . H18A H -0.4000 0.3023 -0.0717 0.111 Uiso 1 1 calc R . . H18B H -0.3778 0.2006 -0.0248 0.111 Uiso 1 1 calc R . . H18C H -0.2385 0.2841 -0.0313 0.111 Uiso 1 1 calc R . . C1S C -0.0069(3) 0.4199(2) 0.37529(15) 0.0336(7) Uani 1 1 d . A . C2S C 0.1628(5) 0.3904(4) 0.3929(2) 0.0699(14) Uani 1 1 d D . . O1S O -0.1090(3) 0.3685(2) 0.40422(12) 0.0482(6) Uani 1 1 d . . . O2S O -0.0192(3) 0.49162(19) 0.33344(13) 0.0452(6) Uani 1 1 d . . . F1 F 0.1805(4) 0.3089(3) 0.43090(18) 0.0598(8) Uani 0.743(4) 1 d PD A 1 F2 F 0.2081(6) 0.4686(3) 0.4450(3) 0.1084(18) Uani 0.743(4) 1 d PD A 1 F3 F 0.2656(4) 0.4147(5) 0.3486(2) 0.111(2) Uani 0.743(4) 1 d PD A 1 F1A F 0.2093(19) 0.3486(11) 0.4492(7) 0.1084(18) Uani 0.257(4) 1 d PD A 2 F2A F 0.2705(14) 0.4545(11) 0.3867(6) 0.111(2) Uani 0.257(4) 1 d PD A 2 F3A F 0.2136(11) 0.3132(6) 0.3370(4) 0.0598(8) Uani 0.257(4) 1 d PD A 2 H1N H -0.281(5) 0.585(3) -0.0060(19) 0.041(10) Uiso 1 1 d . . . H2NA H -0.266(4) 0.529(2) 0.2219(17) 0.025(8) Uiso 1 1 d . . . H2NB H -0.200(5) 0.509(3) 0.290(2) 0.049(10) Uiso 1 1 d . . . H1A H -0.012(5) 0.642(4) 0.033(2) 0.060(12) Uiso 1 1 d . . . H1B H -0.001(4) 0.522(3) 0.0193(18) 0.039(9) Uiso 1 1 d . . . H1C H -0.045(4) 0.596(3) -0.0452(18) 0.031(8) Uiso 1 1 d . . . H4 H -0.476(4) 0.704(3) 0.0670(18) 0.043(9) Uiso 1 1 d . . . H5 H -0.752(5) 0.705(3) 0.0983(18) 0.047(10) Uiso 1 1 d . . . H6 H -0.873(4) 0.551(3) 0.1432(17) 0.036(8) Uiso 1 1 d . . . H11 H -0.238(6) 0.171(3) 0.067(2) 0.066(13) Uiso 1 1 d . . . H12 H -0.162(5) 0.133(3) 0.179(2) 0.066(12) Uiso 1 1 d . . . H13 H -0.228(5) 0.254(3) 0.269(2) 0.061(12) Uiso 1 1 d . . . H15A H -0.371(4) 0.388(3) 0.3106(17) 0.033(8) Uiso 1 1 d . . . H15B H -0.507(4) 0.445(2) 0.2643(15) 0.031(8) Uiso 1 1 d . . . H17A H -0.908(4) 0.418(3) 0.222(2) 0.045(10) Uiso 1 1 d . . . H17B H -0.904(4) 0.301(3) 0.2046(16) 0.027(8) Uiso 1 1 d . . . H17C H -0.953(5) 0.391(3) 0.145(2) 0.057(11) 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 O1 0.0224(10) 0.0508(13) 0.0413(12) 0.0181(10) -0.0053(9) -0.0018(9) O2 0.0211(10) 0.0353(11) 0.0482(12) 0.0034(9) 0.0048(9) -0.0023(9) O3 0.0426(13) 0.0548(14) 0.0363(11) -0.0152(11) -0.0021(10) 0.0084(11) N1 0.0235(12) 0.0439(15) 0.0364(14) 0.0088(12) -0.0040(11) -0.0032(11) N2 0.0254(13) 0.0363(13) 0.0338(14) 0.0000(11) -0.0012(11) 0.0029(11) C1 0.0296(17) 0.062(2) 0.042(2) 0.0171(18) 0.0022(14) -0.0036(16) C2 0.0259(14) 0.0267(14) 0.0377(15) 0.0083(12) -0.0035(13) 0.0009(11) C3 0.0234(13) 0.0308(14) 0.0266(13) 0.0026(11) -0.0030(11) -0.0012(11) C4 0.0311(16) 0.0293(15) 0.0406(16) 0.0065(13) -0.0056(13) 0.0001(12) C5 0.0294(16) 0.0371(16) 0.0382(15) 0.0000(13) -0.0059(13) 0.0105(13) C6 0.0207(14) 0.0369(15) 0.0331(14) -0.0043(12) -0.0027(12) 0.0066(12) C7 0.0229(13) 0.0323(14) 0.0238(12) -0.0025(11) -0.0007(11) 0.0005(11) C8 0.0207(13) 0.0279(14) 0.0268(13) -0.0021(11) -0.0041(11) 0.0022(10) C9 0.0171(12) 0.0275(14) 0.0372(15) 0.0024(12) 0.0023(11) -0.0030(11) C10 0.0233(14) 0.0329(15) 0.0444(17) -0.0087(13) 0.0011(13) -0.0009(12) C11 0.0315(17) 0.0329(16) 0.067(2) -0.0105(16) 0.0031(16) 0.0003(14) C12 0.0306(16) 0.0275(15) 0.078(2) 0.0064(16) -0.0007(17) 0.0049(13) C13 0.0252(15) 0.0353(16) 0.057(2) 0.0185(15) -0.0036(15) -0.0020(13) C14 0.0192(13) 0.0293(14) 0.0379(15) 0.0069(12) 0.0018(12) -0.0032(11) C15 0.0224(15) 0.0458(18) 0.0330(15) 0.0094(14) -0.0001(12) -0.0007(13) C16 0.058(2) 0.050(2) 0.090(3) -0.019(2) 0.007(2) 0.0107(19) C17 0.0218(15) 0.0438(19) 0.059(2) 0.0054(18) 0.0081(14) -0.0017(14) C18 0.066(3) 0.103(4) 0.053(2) -0.031(3) 0.002(2) 0.021(3) C1S 0.0295(16) 0.0381(16) 0.0333(14) -0.0031(13) 0.0017(12) -0.0095(13) C2S 0.040(2) 0.095(3) 0.075(3) 0.050(3) -0.009(2) -0.011(2) O1S 0.0438(13) 0.0578(14) 0.0431(12) -0.0070(11) 0.0127(10) -0.0207(12) O2S 0.0308(12) 0.0491(14) 0.0558(14) 0.0155(11) -0.0115(11) -0.0092(10) F1 0.062(2) 0.0549(17) 0.0621(18) 0.0147(14) -0.0062(15) 0.0182(15) F2 0.092(3) 0.096(3) 0.137(4) 0.039(3) -0.075(3) -0.036(2) F3 0.0351(15) 0.214(6) 0.085(3) 0.084(4) 0.030(2) 0.034(3) F1A 0.092(3) 0.096(3) 0.137(4) 0.039(3) -0.075(3) -0.036(2) F2A 0.0351(15) 0.214(6) 0.085(3) 0.084(4) 0.030(2) 0.034(3) F3A 0.062(2) 0.0549(17) 0.0621(18) 0.0147(14) -0.0062(15) 0.0182(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 O1 C2 1.246(3) . ? O2 C7 1.367(3) . ? O2 C17 1.434(4) . ? O3 C10 1.366(4) . ? O3 C18 1.419(4) . ? N1 C2 1.314(4) . ? N1 C1 1.454(4) . ? N1 H1N 0.80(4) . ? N2 C16 1.471(4) . ? N2 C15 1.500(4) . ? N2 H2NA 0.89(3) . ? N2 H2NB 0.93(4) . ? C1 H1A 0.97(5) . ? C1 H1B 0.98(4) . ? C1 H1C 0.98(3) . ? C2 C3 1.499(4) . ? C3 C4 1.385(4) . ? C3 C8 1.401(4) . ? C4 C5 1.380(4) . ? C4 H4 0.98(4) . ? C5 C6 1.384(4) . ? C5 H5 0.99(4) . ? C6 C7 1.389(4) . ? C6 H6 1.03(4) . ? C7 C8 1.402(4) . ? C8 C9 1.494(4) . ? C9 C10 1.403(4) . ? C9 C14 1.405(4) . ? C10 C11 1.379(5) . ? C11 C12 1.384(5) . ? C11 H11 0.98(4) . ? C12 C13 1.371(5) . ? C12 H12 0.97(5) . ? C13 C14 1.395(4) . ? C13 H13 0.91(4) . ? C14 C15 1.496(4) . ? C15 H15A 0.96(3) . ? C15 H15B 0.99(4) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.94(4) . ? C17 H17B 0.99(3) . ? C17 H17C 1.00(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C1S O1S 1.227(4) . ? C1S O2S 1.232(4) . ? C1S C2S 1.531(5) . ? C2S F3 1.267(5) . ? C2S F2A 1.236(13) . ? C2S F1A 1.281(11) . ? C2S F1 1.287(5) . ? C2S F3A 1.532(9) . ? C2S F2 1.476(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O2 C17 117.1(2) . . ? C10 O3 C18 117.7(3) . . ? C2 N1 C1 122.6(3) . . ? C2 N1 H1N 122(3) . . ? C1 N1 H1N 115(3) . . ? C16 N2 C15 113.5(3) . . ? C16 N2 H2NA 110.6(19) . . ? C15 N2 H2NA 107(2) . . ? C16 N2 H2NB 108(2) . . ? C15 N2 H2NB 111(2) . . ? H2NA N2 H2NB 107(3) . . ? N1 C1 H1A 106(3) . . ? N1 C1 H1B 108(2) . . ? H1A C1 H1B 105(3) . . ? N1 C1 H1C 111(2) . . ? H1A C1 H1C 116(3) . . ? H1B C1 H1C 111(3) . . ? O1 C2 N1 122.5(3) . . ? O1 C2 C3 120.9(3) . . ? N1 C2 C3 116.6(2) . . ? C4 C3 C8 121.0(3) . . ? C4 C3 C2 119.5(3) . . ? C8 C3 C2 119.5(2) . . ? C5 C4 C3 119.9(3) . . ? C5 C4 H4 122(2) . . ? C3 C4 H4 118(2) . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 122(2) . . ? C6 C5 H5 117(2) . . ? C7 C6 C5 119.7(3) . . ? C7 C6 H6 117.7(19) . . ? C5 C6 H6 122.6(19) . . ? O2 C7 C6 124.0(2) . . ? O2 C7 C8 115.2(2) . . ? C6 C7 C8 120.8(3) . . ? C3 C8 C7 118.0(2) . . ? C3 C8 C9 121.5(2) . . ? C7 C8 C9 120.5(2) . . ? C10 C9 C14 118.9(3) . . ? C10 C9 C8 120.4(3) . . ? C14 C9 C8 120.7(2) . . ? O3 C10 C11 124.6(3) . . ? O3 C10 C9 114.8(3) . . ? C11 C10 C9 120.6(3) . . ? C12 C11 C10 119.6(3) . . ? C12 C11 H11 121(3) . . ? C10 C11 H11 119(3) . . ? C13 C12 C11 121.1(3) . . ? C13 C12 H12 122(2) . . ? C11 C12 H12 117(2) . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13 124(3) . . ? C14 C13 H13 116(3) . . ? C9 C14 C13 119.7(3) . . ? C9 C14 C15 119.7(3) . . ? C13 C14 C15 120.6(3) . . ? C14 C15 N2 110.8(2) . . ? C14 C15 H15A 105.8(19) . . ? N2 C15 H15A 107(2) . . ? C14 C15 H15B 109.8(18) . . ? N2 C15 H15B 108.9(19) . . ? H15A C15 H15B 114(3) . . ? N2 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 H17A 110(2) . . ? O2 C17 H17B 103.7(19) . . ? H17A C17 H17B 106(3) . . ? O2 C17 H17C 110(2) . . ? H17A C17 H17C 110(3) . . ? H17B C17 H17C 116(3) . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1S C1S O2S 130.0(3) . . ? O1S C1S C2S 115.6(3) . . ? O2S C1S C2S 114.4(3) . . ? F3 C2S F2A 42.1(6) . . ? F3 C2S F1A 118.1(8) . . ? F2A C2S F1A 97.6(8) . . ? F3 C2S F1 120.6(5) . . ? F2A C2S F1 120.5(7) . . ? F1A C2S F1 30.1(5) . . ? F3 C2S F3A 58.6(5) . . ? F2A C2S F3A 98.5(7) . . ? F1A C2S F3A 104.6(9) . . ? F1 C2S F3A 81.6(4) . . ? F3 C2S F2 97.0(4) . . ? F2A C2S F2 54.8(6) . . ? F1A C2S F2 67.4(7) . . ? F1 C2S F2 97.1(3) . . ? F3A C2S F2 148.4(5) . . ? F3 C2S C1S 115.9(3) . . ? F2A C2S C1S 120.8(7) . . ? F1A C2S C1S 125.9(8) . . ? F1 C2S C1S 116.1(3) . . ? F3A C2S C1S 105.4(5) . . ? F2 C2S C1S 103.5(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C2 O1 -1.7(5) . . . . ? C1 N1 C2 C3 178.2(3) . . . . ? O1 C2 C3 C4 119.8(3) . . . . ? N1 C2 C3 C4 -60.1(4) . . . . ? O1 C2 C3 C8 -58.3(4) . . . . ? N1 C2 C3 C8 121.7(3) . . . . ? C8 C3 C4 C5 1.5(4) . . . . ? C2 C3 C4 C5 -176.7(3) . . . . ? C3 C4 C5 C6 -1.6(5) . . . . ? C4 C5 C6 C7 0.2(4) . . . . ? C17 O2 C7 C6 -2.4(4) . . . . ? C17 O2 C7 C8 177.7(3) . . . . ? C5 C6 C7 O2 -178.5(3) . . . . ? C5 C6 C7 C8 1.5(4) . . . . ? C4 C3 C8 C7 0.1(4) . . . . ? C2 C3 C8 C7 178.3(3) . . . . ? C4 C3 C8 C9 -179.9(3) . . . . ? C2 C3 C8 C9 -1.7(4) . . . . ? O2 C7 C8 C3 178.4(2) . . . . ? C6 C7 C8 C3 -1.6(4) . . . . ? O2 C7 C8 C9 -1.6(4) . . . . ? C6 C7 C8 C9 178.4(2) . . . . ? C3 C8 C9 C10 -78.1(3) . . . . ? C7 C8 C9 C10 102.0(3) . . . . ? C3 C8 C9 C14 99.8(3) . . . . ? C7 C8 C9 C14 -80.2(3) . . . . ? C18 O3 C10 C11 -8.7(5) . . . . ? C18 O3 C10 C9 170.4(3) . . . . ? C14 C9 C10 O3 -178.6(3) . . . . ? C8 C9 C10 O3 -0.7(4) . . . . ? C14 C9 C10 C11 0.6(4) . . . . ? C8 C9 C10 C11 178.5(3) . . . . ? O3 C10 C11 C12 179.7(3) . . . . ? C9 C10 C11 C12 0.6(5) . . . . ? C10 C11 C12 C13 -1.4(5) . . . . ? C11 C12 C13 C14 0.9(5) . . . . ? C10 C9 C14 C13 -1.0(4) . . . . ? C8 C9 C14 C13 -178.9(3) . . . . ? C10 C9 C14 C15 177.1(2) . . . . ? C8 C9 C14 C15 -0.8(4) . . . . ? C12 C13 C14 C9 0.3(4) . . . . ? C12 C13 C14 C15 -177.8(3) . . . . ? C9 C14 C15 N2 -77.2(3) . . . . ? C13 C14 C15 N2 100.8(3) . . . . ? C16 N2 C15 C14 150.9(3) . . . . ? O1S C1S C2S F3 156.5(5) . . . . ? O2S C1S C2S F3 -22.9(6) . . . . ? O1S C1S C2S F2A -155.5(8) . . . . ? O2S C1S C2S F2A 25.1(9) . . . . ? O1S C1S C2S F1A -27.1(10) . . . . ? O2S C1S C2S F1A 153.5(9) . . . . ? O1S C1S C2S F1 6.3(6) . . . . ? O2S C1S C2S F1 -173.1(4) . . . . ? O1S C1S C2S F3A 94.4(5) . . . . ? O2S C1S C2S F3A -85.0(5) . . . . ? O1S C1S C2S F2 -98.7(4) . . . . ? O2S C1S C2S F2 81.9(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 N1 H1N O1S 0.80(4) 2.07(4) 2.844(4) 164(4) 2_464 N2 H2NA O1 0.89(3) 1.89(3) 2.775(3) 168(3) . N2 H2NB O2S 0.93(4) 1.77(5) 2.699(3) 178(4) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.684 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.047