# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Lemmerer, Andreas' 'Caira, M.' 'Bourne, Susan' 'Cotton, Jonathan' 'Hendricks, Umraan' 'Peinke, Laura' 'Trollope, Lee' _publ_contact_author_name 'Lemmerer, Andreas' _publ_contact_author_email andreas.lemmerer@gmail.com _publ_section_title ; Incorporating active pharmaceutical ingredients into a molecular salt using a chiral counterion. ; _publ_requested_category FO # Attachment '- API 1-4.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-09-20 at 17:42:52 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : 8alt2_p nonius data_1 _database_code_depnum_ccdc_archive 'CCDC 771710' #TrackingRef '- API 1-4.cif' _audit_creation_date 2008-09-20T17:42:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ((R)-1-phenylethylammonium).((2S)-[2-(4-isobutylphenyl)propanoate]) ; _chemical_formula_moiety 'C13 H17 O2, C8 H12 N' _chemical_formula_sum 'C21 H29 N O2' _chemical_formula_weight 327.45 _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 6.8664(5) _cell_length_b 12.4548(12) _cell_length_c 23.4659(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2006.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 24213 _cell_measurement_theta_min 0.4 _cell_measurement_theta_max 28.28 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.084 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.23 -1 0 0 0.26 0 0 1 0.05 0 0 -1 0.1 0 2 1 0.07 0 -2 3 0.03 0 -3 -4 0.09 0 1 -2 0.1 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.9406 _exptl_absorpt_correction_T_max 0.9932 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '1.3\% \p and \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_unetI/netI 0.0281 _diffrn_reflns_number 19997 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 2163 _reflns_number_gt 1747 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0848P)^2^+0.3384P] 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_number_reflns 2163 _refine_ls_number_parameters 230 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1461 _refine_ls_wR_factor_gt 0.1332 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881; 1568 friedel pairs measured' _refine_ls_abs_structure_Flack 10(10) _refine_diff_density_max 0.303 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0618(5) 0.0229(3) 0.08743(12) 0.0546(8) Uani 1 1 d . . . C2 C 0.9330(6) 0.0246(3) 0.13271(13) 0.0649(10) Uani 1 1 d . . . H2 H 0.8074 0.0553 0.128 0.078 Uiso 1 1 calc R . . C3 C 0.9867(7) -0.0186(3) 0.18524(15) 0.0796(12) Uani 1 1 d . . . H3 H 0.8972 -0.0179 0.2161 0.095 Uiso 1 1 calc R . . C4 C 1.1660(8) -0.0614(4) 0.19227(18) 0.0920(15) Uani 1 1 d . . . H4 H 1.2018 -0.0908 0.2281 0.11 Uiso 1 1 calc R . . C5 C 1.2943(8) -0.0628(4) 0.14895(19) 0.0956(15) Uani 1 1 d . . . H5 H 1.4202 -0.0926 0.1545 0.115 Uiso 1 1 calc R . . C6 C 1.2435(7) -0.0203(3) 0.09553(17) 0.0745(11) Uani 1 1 d . . . H6 H 1.3347 -0.0215 0.0651 0.089 Uiso 1 1 calc R . . C7 C 1.0075(5) 0.0723(3) 0.03037(11) 0.0519(8) Uani 1 1 d . . . H7 H 1.1171 0.0594 0.0031 0.062 Uiso 1 1 calc R . . C8 C 0.8221(7) 0.0261(3) 0.00451(16) 0.0813(13) Uani 1 1 d . . . H8A H 0.7121 0.0398 0.0301 0.122 Uiso 1 1 calc R . . H8B H 0.8375 -0.0515 -0.0008 0.122 Uiso 1 1 calc R . . H8C H 0.7973 0.0601 -0.0324 0.122 Uiso 1 1 calc R . . N1 N 0.9842(4) 0.1913(2) 0.03768(9) 0.0425(6) Uani 1 1 d . . . H1A H 0.869(6) 0.214(3) 0.0605(15) 0.064 Uiso 1 1 d . . . H1B H 1.111(6) 0.218(3) 0.0555(15) 0.064 Uiso 1 1 d . . . H1C H 0.959(5) 0.216(3) 0.0048(16) 0.064 Uiso 1 1 d . . . C11 C 0.2575(4) 0.3463(2) 0.16623(11) 0.0418(7) Uani 1 1 d . . . C12 C 0.3439(5) 0.4476(3) 0.17112(12) 0.0535(8) Uani 1 1 d . . . H12 H 0.4808 0.4531 0.1761 0.064 Uiso 1 1 calc R . . C13 C 0.2327(5) 0.5390(3) 0.16881(14) 0.0590(9) Uani 1 1 d . . . H13 H 0.2948 0.6068 0.1726 0.071 Uiso 1 1 calc R . . C14 C 0.0331(5) 0.5356(3) 0.16112(13) 0.0550(8) Uani 1 1 d . . . C15 C -0.0517(5) 0.4354(3) 0.15625(13) 0.0540(8) Uani 1 1 d . . . H15 H -0.1884 0.4303 0.1505 0.065 Uiso 1 1 calc R . . C16 C 0.0570(4) 0.3429(3) 0.15952(12) 0.0476(7) Uani 1 1 d . . . H16 H -0.0065 0.2753 0.1571 0.057 Uiso 1 1 calc R . . C17 C 0.3762(4) 0.2444(2) 0.16499(10) 0.0429(7) Uani 1 1 d . . . H17 H 0.2829 0.1828 0.1668 0.052 Uiso 1 1 calc R . . C18 C 0.5174(5) 0.2323(3) 0.21497(11) 0.0604(9) Uani 1 1 d . . . H18A H 0.619 0.2873 0.2123 0.091 Uiso 1 1 calc R . . H18B H 0.5774 0.1609 0.2138 0.091 Uiso 1 1 calc R . . H18C H 0.4464 0.2409 0.2509 0.091 Uiso 1 1 calc R . . C19 C 0.4799(4) 0.2383(2) 0.10717(10) 0.0372(6) Uani 1 1 d . . . C20 C -0.0914(6) 0.6349(3) 0.15820(16) 0.0714(10) Uani 1 1 d . . . H20A H -0.0108 0.6975 0.1692 0.086 Uiso 1 1 calc R . . H20B H -0.1973 0.6282 0.1866 0.086 Uiso 1 1 calc R . . C21 C -0.1827(9) 0.6574(4) 0.0998(2) 0.0989(17) Uani 1 1 d . . . H21 H -0.2533 0.5905 0.0884 0.119 Uiso 1 1 calc R . . C22 C -0.3332(10) 0.7451(4) 0.1027(2) 0.120(2) Uani 1 1 d U . . H22A H -0.2709 0.8124 0.1145 0.18 Uiso 1 1 calc R . . H22B H -0.4337 0.7255 0.1305 0.18 Uiso 1 1 calc R . . H22C H -0.3931 0.7546 0.0652 0.18 Uiso 1 1 calc R . . C23 C -0.0382(14) 0.6780(7) 0.0551(3) 0.192(4) Uani 1 1 d U . . H23A H -0.1051 0.6947 0.0193 0.288 Uiso 1 1 calc R . . H23B H 0.0434 0.6142 0.0499 0.288 Uiso 1 1 calc R . . H23C H 0.0436 0.739 0.0662 0.288 Uiso 1 1 calc R . . O1 O 0.6579(3) 0.2419(2) 0.10491(8) 0.0576(6) Uani 1 1 d . . . O2 O 0.3699(3) 0.23067(19) 0.06406(7) 0.0498(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 C1 0.066(2) 0.0548(18) 0.0430(15) -0.0002(12) -0.0030(14) 0.0025(17) C2 0.078(3) 0.070(2) 0.0460(17) 0.0085(15) 0.0008(17) 0.000(2) C3 0.103(3) 0.083(3) 0.053(2) 0.0132(18) 0.004(2) 0.007(3) C4 0.126(4) 0.085(3) 0.065(2) 0.017(2) -0.012(3) 0.030(3) C5 0.110(4) 0.092(3) 0.085(3) 0.010(2) -0.015(3) 0.045(3) C6 0.080(3) 0.077(3) 0.066(2) 0.0019(18) 0.000(2) 0.024(2) C7 0.0581(19) 0.0613(19) 0.0362(13) -0.0041(12) -0.0013(13) 0.0000(16) C8 0.105(3) 0.083(3) 0.056(2) 0.0015(17) -0.027(2) -0.030(3) N1 0.0350(13) 0.0641(15) 0.0283(11) 0.0056(10) -0.0027(10) -0.0012(12) C11 0.0392(16) 0.0565(17) 0.0297(13) -0.0053(12) 0.0053(11) -0.0074(13) C12 0.0413(16) 0.066(2) 0.0532(17) -0.0094(14) 0.0032(14) -0.0138(16) C13 0.061(2) 0.055(2) 0.0606(19) -0.0140(15) 0.0079(17) -0.0129(17) C14 0.055(2) 0.058(2) 0.0514(16) -0.0101(14) 0.0103(15) -0.0001(16) C15 0.0370(16) 0.065(2) 0.0598(18) -0.0083(15) 0.0057(14) -0.0001(16) C16 0.0403(16) 0.0589(19) 0.0437(15) -0.0054(13) 0.0054(13) -0.0089(14) C17 0.0378(14) 0.0593(18) 0.0317(12) 0.0026(11) 0.0005(11) -0.0067(13) C18 0.0580(19) 0.089(2) 0.0340(14) 0.0050(14) -0.0065(14) -0.0032(19) C19 0.0308(14) 0.0476(15) 0.0332(12) 0.0009(11) 0.0008(11) -0.0017(12) C20 0.076(3) 0.064(2) 0.075(2) -0.0061(17) 0.015(2) 0.010(2) C21 0.124(4) 0.078(3) 0.095(3) 0.012(2) 0.029(3) 0.041(3) C22 0.136(5) 0.099(4) 0.124(4) 0.021(3) 0.021(4) 0.038(4) C23 0.253(10) 0.211(7) 0.113(4) 0.043(5) 0.085(6) 0.149(8) O1 0.0289(11) 0.0982(18) 0.0457(11) -0.0076(11) -0.0002(8) -0.0027(12) O2 0.0339(10) 0.0846(15) 0.0308(9) 0.0054(9) -0.0013(8) -0.0053(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C6 1.372(6) . ? C1 C2 1.382(5) . ? C1 C7 1.520(4) . ? C2 C3 1.394(5) . ? C2 H2 0.95 . ? C3 C4 1.352(7) . ? C3 H3 0.95 . ? C4 C5 1.345(7) . ? C4 H4 0.95 . ? C5 C6 1.405(6) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 N1 1.500(4) . ? C7 C8 1.524(5) . ? C7 H7 1 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? N1 H1A 1.00(4) . ? N1 H1B 1.02(4) . ? N1 H1C 0.85(4) . ? C11 C16 1.386(4) . ? C11 C12 1.399(4) . ? C11 C17 1.509(4) . ? C12 C13 1.372(5) . ? C12 H12 0.95 . ? C13 C14 1.383(5) . ? C13 H13 0.95 . ? C14 C15 1.382(5) . ? C14 C20 1.505(5) . ? C15 C16 1.375(5) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 C18 1.529(4) . ? C17 C19 1.534(3) . ? C17 H17 1 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 O1 1.224(3) . ? C19 O2 1.266(3) . ? C20 C21 1.534(6) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 C23 1.466(9) . ? C21 C22 1.506(7) . ? C21 H21 1 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? 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 C1 C2 118.7(3) . . ? C6 C1 C7 120.2(3) . . ? C2 C1 C7 121.0(3) . . ? C1 C2 C3 120.3(4) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 120.0(4) . . ? C4 C3 H3 120 . . ? C2 C3 H3 120 . . ? C5 C4 C3 120.6(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.5(4) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 119.8(4) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? N1 C7 C1 109.0(2) . . ? N1 C7 C8 109.3(3) . . ? C1 C7 C8 113.7(3) . . ? N1 C7 H7 108.2 . . ? C1 C7 H7 108.2 . . ? C8 C7 H7 108.2 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 N1 H1A 115(2) . . ? C7 N1 H1B 106(2) . . ? H1A N1 H1B 111(3) . . ? C7 N1 H1C 106(2) . . ? H1A N1 H1C 103(3) . . ? H1B N1 H1C 116(3) . . ? C16 C11 C12 117.2(3) . . ? C16 C11 C17 120.6(3) . . ? C12 C11 C17 122.1(3) . . ? C13 C12 C11 120.7(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 122.0(3) . . ? C12 C13 H13 119 . . ? C14 C13 H13 119 . . ? C15 C14 C13 117.2(3) . . ? C15 C14 C20 119.9(3) . . ? C13 C14 C20 122.9(3) . . ? C16 C15 C14 121.5(3) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C15 C16 C11 121.4(3) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? C11 C17 C18 114.2(2) . . ? C11 C17 C19 108.0(2) . . ? C18 C17 C19 112.3(2) . . ? C11 C17 H17 107.3 . . ? C18 C17 H17 107.3 . . ? C19 C17 H17 107.3 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1 C19 O2 124.3(2) . . ? O1 C19 C17 120.0(2) . . ? O2 C19 C17 115.7(2) . . ? C14 C20 C21 115.0(3) . . ? C14 C20 H20A 108.5 . . ? C21 C20 H20A 108.5 . . ? C14 C20 H20B 108.5 . . ? C21 C20 H20B 108.5 . . ? H20A C20 H20B 107.5 . . ? C23 C21 C22 111.8(4) . . ? C23 C21 C20 113.3(6) . . ? C22 C21 C20 111.8(4) . . ? C23 C21 H21 106.5 . . ? C22 C21 H21 106.5 . . ? C20 C21 H21 106.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C6 C1 C2 C3 -1.0(6) . . . . ? C7 C1 C2 C3 -178.3(3) . . . . ? C1 C2 C3 C4 0.6(6) . . . . ? C2 C3 C4 C5 0.1(8) . . . . ? C3 C4 C5 C6 -0.4(8) . . . . ? C2 C1 C6 C5 0.7(6) . . . . ? C7 C1 C6 C5 178.0(4) . . . . ? C4 C5 C6 C1 0.0(7) . . . . ? C6 C1 C7 N1 -111.9(4) . . . . ? C2 C1 C7 N1 65.4(4) . . . . ? C6 C1 C7 C8 125.9(4) . . . . ? C2 C1 C7 C8 -56.8(4) . . . . ? C16 C11 C12 C13 -0.5(4) . . . . ? C17 C11 C12 C13 176.2(3) . . . . ? C11 C12 C13 C14 -0.6(5) . . . . ? C12 C13 C14 C15 0.5(5) . . . . ? C12 C13 C14 C20 -179.7(3) . . . . ? C13 C14 C15 C16 0.7(5) . . . . ? C20 C14 C15 C16 -179.1(3) . . . . ? C14 C15 C16 C11 -1.9(4) . . . . ? C12 C11 C16 C15 1.7(4) . . . . ? C17 C11 C16 C15 -175.1(2) . . . . ? C16 C11 C17 C18 -130.0(3) . . . . ? C12 C11 C17 C18 53.3(3) . . . . ? C16 C11 C17 C19 104.3(3) . . . . ? C12 C11 C17 C19 -72.4(3) . . . . ? C11 C17 C19 O1 115.5(3) . . . . ? C18 C17 C19 O1 -11.3(4) . . . . ? C11 C17 C19 O2 -63.9(3) . . . . ? C18 C17 C19 O2 169.3(3) . . . . ? C15 C14 C20 C21 -68.2(5) . . . . ? C13 C14 C20 C21 112.1(5) . . . . ? C14 C20 C21 C23 -63.2(6) . . . . ? C14 C20 C21 C22 169.4(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 H1A O1 1.00(4) 1.82(4) 2.812(3) 174(3) . N1 H1B O2 1.02(4) 1.80(4) 2.764(3) 157(3) 1_655 N1 H1C O2 0.85(4) 1.85(4) 2.695(3) 173(4) 4 ###END data_2 _database_code_depnum_ccdc_archive 'CCDC 771711' #TrackingRef '- API 1-4.cif' _audit_creation_date 2008-09-20T17:44:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ((S)-1-phenylethylammonium).((2S)-[2-(4-isobutylphenyl)propanoate]) ; _chemical_formula_moiety 'C13 H17 O2, C8 H12 N' _chemical_formula_sum 'C21 H29 N O2' _chemical_formula_weight 327.45 _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 5.8810(5) _cell_length_b 15.2590(6) _cell_length_c 22.318(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2002.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16551 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 25.68 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.086 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.277 1 0 0 0.236 0 1 0 0.073 0 -1 0 0.029 0 0 1 0.082 0 0 -1 0.017 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.9505 _exptl_absorpt_correction_T_max 0.9934 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '1.0\% \p and \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.1252 _diffrn_reflns_av_unetI/netI 0.0564 _diffrn_reflns_number 16454 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 2139 _reflns_number_gt 1693 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.1160P)^2^] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.049(9) _refine_ls_number_reflns 2139 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0864 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.1703 _refine_ls_wR_factor_gt 0.157 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881; 1548 friedel pairs measured' _refine_ls_abs_structure_Flack -10(10) _refine_diff_density_max 0.278 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.071 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5251(6) 0.9259(2) 0.11068(13) 0.0354(8) Uani 1 1 d . . . C2 C 0.3510(7) 0.9122(2) 0.15102(15) 0.0425(9) Uani 1 1 d . . . H2 H 0.2146 0.8845 0.1383 0.051 Uiso 1 1 calc R . . C3 C 0.3751(9) 0.9391(3) 0.21062(17) 0.0578(12) Uani 1 1 d . . . H3 H 0.2564 0.9288 0.2386 0.069 Uiso 1 1 calc R . . C4 C 0.5698(9) 0.9801(3) 0.22822(19) 0.0706(14) Uani 1 1 d . . . H4 H 0.5844 0.9994 0.2685 0.085 Uiso 1 1 calc R . . C5 C 0.7427(9) 0.9938(4) 0.1893(2) 0.0757(16) Uani 1 1 d . . . H5 H 0.8788 1.0214 0.2024 0.091 Uiso 1 1 calc R . . C6 C 0.7189(8) 0.9668(3) 0.12931(18) 0.0562(11) Uani 1 1 d . . . H6 H 0.8385 0.9771 0.1016 0.067 Uiso 1 1 calc R . . C7 C 0.5052(7) 0.8949(2) 0.04618(13) 0.0348(8) Uani 1 1 d . . . H7 H 0.6545 0.9046 0.0258 0.042 Uiso 1 1 calc R . . C8 C 0.3207(8) 0.9429(2) 0.01102(14) 0.0487(10) Uani 1 1 d . . . H8A H 0.3153 0.9202 -0.03 0.073 Uiso 1 1 calc R . . H8B H 0.3553 1.0057 0.0101 0.073 Uiso 1 1 calc R . . H8C H 0.1732 0.9337 0.0304 0.073 Uiso 1 1 calc R . . N1 N 0.4549(6) 0.79902(17) 0.04582(12) 0.0326(7) Uani 1 1 d . . . H1B H 0.568(7) 0.771(3) 0.0701(19) 0.049 Uiso 1 1 d . . . H1C H 0.477(7) 0.779(2) 0.007(2) 0.049 Uiso 1 1 d . . . H1A H 0.286(7) 0.787(2) 0.0583(18) 0.049 Uiso 1 1 d . . . C11 C 0.1223(6) 0.5840(2) 0.14067(13) 0.0340(8) Uani 1 1 d . . . C12 C -0.0488(7) 0.5226(2) 0.15181(15) 0.0388(8) Uani 1 1 d . . . H12 H -0.1798 0.5394 0.1739 0.047 Uiso 1 1 calc R . . C13 C -0.0296(7) 0.4378(2) 0.13110(15) 0.0450(9) Uani 1 1 d . . . H13 H -0.1473 0.3971 0.1397 0.054 Uiso 1 1 calc R . . C14 C 0.1583(7) 0.4103(2) 0.09783(15) 0.0429(9) Uani 1 1 d . . . C15 C 0.3274(8) 0.4711(2) 0.08709(16) 0.0437(9) Uani 1 1 d . . . H15 H 0.4572 0.4542 0.0645 0.052 Uiso 1 1 calc R . . C16 C 0.3122(7) 0.5564(2) 0.10852(15) 0.0394(8) Uani 1 1 d . . . H16 H 0.4328 0.5964 0.1012 0.047 Uiso 1 1 calc R . . C17 C 0.0977(6) 0.6797(2) 0.15907(13) 0.0349(8) Uani 1 1 d . . . H17 H 0.248 0.7092 0.1536 0.042 Uiso 1 1 calc R . . C18 C 0.0216(9) 0.6927(3) 0.22412(14) 0.0535(11) Uani 1 1 d . . . H18A H -0.1246 0.6633 0.2304 0.08 Uiso 1 1 calc R . . H18B H 0.005 0.7555 0.2323 0.08 Uiso 1 1 calc R . . H18C H 0.1356 0.6677 0.2512 0.08 Uiso 1 1 calc R . . C19 C -0.0723(6) 0.72115(19) 0.11570(13) 0.0307(7) Uani 1 1 d . . . C20 C 0.1713(9) 0.3177(2) 0.07450(18) 0.0555(11) Uani 1 1 d . . . H20A H 0.2934 0.3148 0.044 0.067 Uiso 1 1 calc R . . H20B H 0.0262 0.3037 0.0541 0.067 Uiso 1 1 calc R . . C21 C 0.2167(9) 0.2474(2) 0.12187(18) 0.0555(11) Uani 1 1 d . . . H21 H 0.0942 0.2517 0.1528 0.067 Uiso 1 1 calc R . . C22 C 0.2010(13) 0.1568(3) 0.0931(3) 0.0909(19) Uani 1 1 d . . . H22A H 0.3267 0.1491 0.0648 0.136 Uiso 1 1 calc R . . H22B H 0.056 0.1513 0.0718 0.136 Uiso 1 1 calc R . . H22C H 0.2102 0.1117 0.1243 0.136 Uiso 1 1 calc R . . C23 C 0.4408(11) 0.2595(4) 0.1529(3) 0.0897(18) Uani 1 1 d . . . H23A H 0.5642 0.2553 0.1236 0.135 Uiso 1 1 calc R . . H23B H 0.4597 0.2139 0.1834 0.135 Uiso 1 1 calc R . . H23C H 0.4447 0.3173 0.1721 0.135 Uiso 1 1 calc R . . O1 O -0.2777(4) 0.71017(15) 0.12443(10) 0.0415(7) Uani 1 1 d . . . O2 O 0.0083(4) 0.76336(13) 0.07101(9) 0.0340(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 C1 0.046(2) 0.0306(16) 0.0297(16) -0.0066(12) -0.0003(16) 0.0028(15) C2 0.059(2) 0.0397(19) 0.0292(17) -0.0077(14) 0.0002(17) -0.0071(17) C3 0.087(3) 0.058(2) 0.0291(18) -0.0127(16) 0.005(2) -0.004(2) C4 0.086(4) 0.085(3) 0.041(2) -0.033(2) -0.013(3) 0.006(3) C5 0.060(3) 0.094(4) 0.074(3) -0.052(3) -0.012(3) -0.006(2) C6 0.055(3) 0.063(3) 0.050(2) -0.0261(18) 0.003(2) -0.006(2) C7 0.048(2) 0.0327(18) 0.0238(15) -0.0008(11) 0.0002(15) -0.0013(15) C8 0.082(3) 0.0380(18) 0.0262(17) 0.0020(13) -0.0003(18) 0.0134(19) N1 0.0472(19) 0.0306(15) 0.0201(13) -0.0032(10) -0.0024(13) 0.0036(13) C11 0.043(2) 0.0371(18) 0.0221(15) 0.0070(12) -0.0052(14) 0.0017(14) C12 0.048(2) 0.0377(19) 0.0301(17) 0.0083(13) 0.0010(16) 0.0014(16) C13 0.061(2) 0.0359(19) 0.0377(18) 0.0085(14) -0.0033(19) -0.0067(17) C14 0.065(3) 0.0353(19) 0.0283(17) 0.0038(13) 0.0008(17) 0.0009(18) C15 0.058(2) 0.0393(19) 0.0344(18) 0.0053(13) 0.0078(18) 0.0041(17) C16 0.047(2) 0.0339(18) 0.0368(18) 0.0101(14) 0.0011(17) -0.0023(16) C17 0.049(2) 0.0336(18) 0.0222(15) 0.0033(12) -0.0038(14) 0.0005(14) C18 0.092(3) 0.049(2) 0.0204(16) -0.0018(13) -0.0066(19) 0.005(2) C19 0.042(2) 0.0292(16) 0.0212(14) -0.0035(11) -0.0014(14) -0.0003(13) C20 0.088(3) 0.037(2) 0.042(2) -0.0036(15) 0.008(2) -0.001(2) C21 0.081(3) 0.0284(19) 0.057(2) 0.0055(15) 0.007(2) 0.0018(17) C22 0.137(5) 0.034(2) 0.102(4) 0.000(2) 0.010(4) -0.001(3) C23 0.096(4) 0.058(3) 0.115(4) 0.017(3) -0.017(4) 0.008(3) O1 0.0467(17) 0.0400(14) 0.0378(13) 0.0097(9) -0.0004(12) -0.0011(11) O2 0.0491(14) 0.0339(11) 0.0190(10) 0.0018(8) 0.0005(10) -0.0013(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C6 1.364(5) . ? C1 C2 1.379(5) . ? C1 C7 1.520(4) . ? C2 C3 1.399(5) . ? C2 H2 0.95 . ? C3 C4 1.363(7) . ? C3 H3 0.95 . ? C4 C5 1.353(7) . ? C4 H4 0.95 . ? C5 C6 1.409(6) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 N1 1.492(4) . ? C7 C8 1.527(5) . ? C7 H7 1 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? N1 H1B 0.96(4) . ? N1 H1C 0.93(4) . ? N1 H1A 1.05(4) . ? C11 C16 1.392(5) . ? C11 C12 1.398(5) . ? C11 C17 1.523(5) . ? C12 C13 1.378(5) . ? C12 H12 0.95 . ? C13 C14 1.396(6) . ? C13 H13 0.95 . ? C14 C15 1.381(6) . ? C14 C20 1.507(5) . ? C15 C16 1.390(5) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 C19 1.529(5) . ? C17 C18 1.532(5) . ? C17 H17 1 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 O1 1.235(4) . ? C19 O2 1.279(4) . ? C20 C21 1.530(5) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 C23 1.500(7) . ? C21 C22 1.527(6) . ? C21 H21 1 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? 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 C1 C2 119.4(3) . . ? C6 C1 C7 119.7(3) . . ? C2 C1 C7 120.9(3) . . ? C1 C2 C3 120.1(4) . . ? C1 C2 H2 120 . . ? C3 C2 H2 120 . . ? C4 C3 C2 119.6(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 121.2(3) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 119.3(4) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 120.5(4) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? N1 C7 C1 109.0(2) . . ? N1 C7 C8 109.1(3) . . ? C1 C7 C8 113.1(3) . . ? N1 C7 H7 108.5 . . ? C1 C7 H7 108.5 . . ? C8 C7 H7 108.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 N1 H1B 107(2) . . ? C7 N1 H1C 108(2) . . ? H1B N1 H1C 106(3) . . ? C7 N1 H1A 111(2) . . ? H1B N1 H1A 116(3) . . ? H1C N1 H1A 109(3) . . ? C16 C11 C12 117.8(3) . . ? C16 C11 C17 120.3(3) . . ? C12 C11 C17 121.7(3) . . ? C13 C12 C11 120.7(4) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 121.7(3) . . ? C12 C13 H13 119.1 . . ? C14 C13 H13 119.1 . . ? C15 C14 C13 117.4(3) . . ? C15 C14 C20 122.2(4) . . ? C13 C14 C20 120.4(4) . . ? C14 C15 C16 121.5(4) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C15 C16 C11 120.8(3) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? C11 C17 C19 106.8(2) . . ? C11 C17 C18 114.1(3) . . ? C19 C17 C18 110.8(3) . . ? C11 C17 H17 108.4 . . ? C19 C17 H17 108.4 . . ? C18 C17 H17 108.4 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1 C19 O2 123.7(3) . . ? O1 C19 C17 118.9(3) . . ? O2 C19 C17 117.4(3) . . ? C14 C20 C21 115.3(3) . . ? C14 C20 H20A 108.4 . . ? C21 C20 H20A 108.4 . . ? C14 C20 H20B 108.4 . . ? C21 C20 H20B 108.4 . . ? H20A C20 H20B 107.5 . . ? C23 C21 C22 111.0(4) . . ? C23 C21 C20 112.7(4) . . ? C22 C21 C20 109.5(4) . . ? C23 C21 H21 107.8 . . ? C22 C21 H21 107.8 . . ? C20 C21 H21 107.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C6 C1 C2 C3 -0.9(6) . . . . ? C7 C1 C2 C3 178.2(4) . . . . ? C1 C2 C3 C4 1.1(6) . . . . ? C2 C3 C4 C5 -1.4(8) . . . . ? C3 C4 C5 C6 1.3(9) . . . . ? C2 C1 C6 C5 0.9(6) . . . . ? C7 C1 C6 C5 -178.2(4) . . . . ? C4 C5 C6 C1 -1.1(8) . . . . ? C6 C1 C7 N1 123.6(4) . . . . ? C2 C1 C7 N1 -55.5(4) . . . . ? C6 C1 C7 C8 -114.9(4) . . . . ? C2 C1 C7 C8 66.0(4) . . . . ? C16 C11 C12 C13 -0.5(5) . . . . ? C17 C11 C12 C13 175.5(3) . . . . ? C11 C12 C13 C14 -0.8(5) . . . . ? C12 C13 C14 C15 1.0(5) . . . . ? C12 C13 C14 C20 -178.4(4) . . . . ? C13 C14 C15 C16 0.1(5) . . . . ? C20 C14 C15 C16 179.5(4) . . . . ? C14 C15 C16 C11 -1.4(6) . . . . ? C12 C11 C16 C15 1.5(5) . . . . ? C17 C11 C16 C15 -174.5(3) . . . . ? C16 C11 C17 C19 102.4(3) . . . . ? C12 C11 C17 C19 -73.4(4) . . . . ? C16 C11 C17 C18 -134.9(4) . . . . ? C12 C11 C17 C18 49.3(5) . . . . ? C11 C17 C19 O1 80.8(4) . . . . ? C18 C17 C19 O1 -43.9(4) . . . . ? C11 C17 C19 O2 -97.1(3) . . . . ? C18 C17 C19 O2 138.2(3) . . . . ? C15 C14 C20 C21 108.1(4) . . . . ? C13 C14 C20 C21 -72.5(5) . . . . ? C14 C20 C21 C23 -61.7(6) . . . . ? C14 C20 C21 C22 174.2(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 N1 H1A O2 1.05(4) 1.69(4) 2.740(4) 174(4) . N1 H1B O1 0.96(4) 1.78(4) 2.719(4) 167(4) 1_655 N1 H1C O2 0.93(4) 1.86(4) 2.794(3) 178(4) 4_565 ###END data_3 _database_code_depnum_ccdc_archive 'CCDC 771712' #TrackingRef '- API 1-4.cif' _audit_creation_date 2008-09-24T14:49:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ((R)-1-phenylethylammonium).(2-(2-(2,6-dichlorophenylamino)phenyl)acetate) ; _chemical_formula_moiety 'C14 H10 Cl2 N O2, C8 H12 N' _chemical_formula_sum 'C22 H22 Cl2 N2 O2' _chemical_formula_weight 417.32 _chemical_absolute_configuration rmad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.499(5) _cell_length_b 6.8934(15) _cell_length_c 13.411(6) _cell_angle_alpha 90 _cell_angle_beta 113.73(3) _cell_angle_gamma 90 _cell_volume 1057.8(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 19639 _cell_measurement_theta_min 1 _cell_measurement_theta_max 28.28 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.31 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.15 0 0 -1 0.15 -5 0 -1 0.025 4 0 1 0.025 0 1 0 0.19 0 -1 0 0.15 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.327 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.8958 _exptl_absorpt_correction_T_max 0.9842 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '2.0\% \p and \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_unetI/netI 0.0317 _diffrn_reflns_number 16888 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3939 _reflns_number_gt 3579 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0377P)^2^+0.0964P] 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_number_reflns 3939 _refine_ls_number_parameters 266 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.029 _refine_ls_wR_factor_ref 0.0691 _refine_ls_wR_factor_gt 0.0662 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881; 1791 friedel pairs measured' _refine_ls_abs_structure_Flack -0.02(4) _refine_diff_density_max 0.145 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.033 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.21368(15) 0.4970(3) -0.05282(14) 0.0293(4) Uani 1 1 d . . . C2 C 0.27056(17) 0.4159(3) 0.05028(15) 0.0366(4) Uani 1 1 d . . . H2A H 0.3478 0.4558 0.0953 0.044 Uiso 1 1 calc R . . C3 C 0.2151(2) 0.2775(3) 0.08745(18) 0.0436(5) Uani 1 1 d . . . H3 H 0.2544 0.2221 0.1577 0.052 Uiso 1 1 calc R . . C4 C 0.10220(19) 0.2200(3) 0.02220(19) 0.0445(5) Uani 1 1 d . . . H4 H 0.0633 0.1279 0.0486 0.053 Uiso 1 1 calc R . . C5 C 0.04625(19) 0.2960(3) -0.08089(19) 0.0448(5) Uani 1 1 d . . . H5 H -0.0303 0.2536 -0.1263 0.054 Uiso 1 1 calc R . . C6 C 0.10160(16) 0.4344(3) -0.11829(16) 0.0367(4) Uani 1 1 d . . . H6 H 0.0626 0.4869 -0.1893 0.044 Uiso 1 1 calc R . . C7 C 0.26557(16) 0.6632(3) -0.09171(15) 0.0300(4) Uani 1 1 d . . . H7 H 0.217 0.6832 -0.1711 0.036 Uiso 1 1 calc R . . C8 C 0.2634(2) 0.8501(3) -0.03193(18) 0.0436(5) Uani 1 1 d . . . H8A H 0.3091 0.8326 0.0464 0.065 Uiso 1 1 calc R . . H8B H 0.1825 0.8824 -0.0449 0.065 Uiso 1 1 calc R . . H8C H 0.2973 0.9557 -0.0588 0.065 Uiso 1 1 calc R . . N1 N 0.38872(14) 0.6232(2) -0.07774(13) 0.0266(3) Uani 1 1 d . . . H1A H 0.4425(18) 0.645(3) -0.014(2) 0.04 Uiso 1 1 d . . . H1B H 0.3979(17) 0.500(4) -0.1050(17) 0.04 Uiso 1 1 d . . . H1C H 0.4102(19) 0.711(3) -0.1157(18) 0.04 Uiso 1 1 d . . . C11 C 0.80575(14) 0.5008(3) 0.32898(13) 0.0259(4) Uani 1 1 d . . . C12 C 0.78709(14) 0.3435(2) 0.38676(13) 0.0260(4) Uani 1 1 d . . . C13 C 0.87151(16) 0.1995(3) 0.42753(15) 0.0328(4) Uani 1 1 d . . . H13 H 0.8589 0.094 0.4671 0.039 Uiso 1 1 calc R . . C14 C 0.97379(17) 0.2084(3) 0.41093(15) 0.0382(5) Uani 1 1 d . . . H14 H 1.0313 0.11 0.4397 0.046 Uiso 1 1 calc R . . C15 C 0.99225(16) 0.3599(3) 0.35273(15) 0.0384(5) Uani 1 1 d . . . H15 H 1.0618 0.3652 0.3402 0.046 Uiso 1 1 calc R . . C16 C 0.90873(16) 0.5045(3) 0.31259(14) 0.0338(4) Uani 1 1 d . . . H16 H 0.9222 0.6088 0.2728 0.041 Uiso 1 1 calc R . . C17 C 0.71838(16) 0.6636(3) 0.28836(15) 0.0306(4) Uani 1 1 d . . . H17A H 0.7568 0.7762 0.2707 0.037 Uiso 1 1 calc R . . H17B H 0.6953 0.7034 0.3478 0.037 Uiso 1 1 calc R . . C18 C 0.60798(15) 0.6134(2) 0.18794(14) 0.0247(4) Uani 1 1 d . . . C19 C 0.66485(15) 0.1973(3) 0.46993(15) 0.0299(4) Uani 1 1 d . . . C20 C 0.72173(16) 0.2133(3) 0.58348(16) 0.0383(5) Uani 1 1 d . . . C21 C 0.70607(19) 0.0780(3) 0.65288(18) 0.0504(6) Uani 1 1 d . . . H21 H 0.7464 0.0914 0.7295 0.06 Uiso 1 1 calc R . . C22 C 0.63142(19) -0.0764(4) 0.60965(18) 0.0545(6) Uani 1 1 d . . . H22 H 0.6204 -0.1694 0.6569 0.065 Uiso 1 1 calc R . . C23 C 0.57278(18) -0.0968(3) 0.49873(17) 0.0441(5) Uani 1 1 d . . . H23 H 0.5219 -0.2039 0.4693 0.053 Uiso 1 1 calc R . . C24 C 0.58865(16) 0.0402(3) 0.43063(15) 0.0321(4) Uani 1 1 d . . . N2 N 0.68115(13) 0.3367(2) 0.40139(13) 0.0302(3) Uani 1 1 d . . . H2 H 0.6227(18) 0.353(3) 0.3427(17) 0.036 Uiso 1 1 d . . . O1 O 0.56595(11) 0.74124(16) 0.11547(10) 0.0317(3) Uani 1 1 d . . . O2 O 0.56355(10) 0.44802(16) 0.18263(9) 0.0298(3) Uani 1 1 d . . . Cl1 Cl 0.51032(4) 0.01577(7) 0.29098(4) 0.03949(13) Uani 1 1 d . . . Cl2 Cl 0.81040(5) 0.41212(9) 0.63906(4) 0.05740(17) 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 C1 0.0313(9) 0.0271(9) 0.0306(9) -0.0046(8) 0.0135(8) 0.0039(8) C2 0.0393(11) 0.0343(10) 0.0320(10) -0.0027(9) 0.0101(8) -0.0033(9) C3 0.0577(14) 0.0356(11) 0.0395(11) 0.0022(9) 0.0216(10) -0.0017(10) C4 0.0510(13) 0.0320(11) 0.0654(15) -0.0067(10) 0.0390(12) -0.0050(10) C5 0.0323(11) 0.0430(12) 0.0589(15) -0.0125(11) 0.0181(10) -0.0036(9) C6 0.0308(10) 0.0366(10) 0.0386(10) -0.0035(9) 0.0099(8) 0.0045(9) C7 0.0312(10) 0.0283(9) 0.0284(9) 0.0005(8) 0.0100(8) 0.0065(8) C8 0.0581(13) 0.0256(10) 0.0569(13) 0.0008(9) 0.0335(11) 0.0094(9) N1 0.0321(9) 0.0205(8) 0.0250(8) -0.0010(7) 0.0091(7) 0.0005(7) C11 0.0259(9) 0.0258(9) 0.0210(8) 0.0020(7) 0.0045(7) -0.0030(8) C12 0.0223(9) 0.0293(9) 0.0238(9) 0.0032(7) 0.0066(7) -0.0003(7) C13 0.0311(10) 0.0336(10) 0.0320(10) 0.0093(8) 0.0109(8) 0.0071(8) C14 0.0303(10) 0.0482(12) 0.0327(10) 0.0021(9) 0.0089(8) 0.0110(9) C15 0.0237(9) 0.0582(13) 0.0330(10) -0.0052(9) 0.0111(8) -0.0067(9) C16 0.0333(10) 0.0386(10) 0.0275(9) -0.0008(9) 0.0101(8) -0.0128(9) C17 0.0356(10) 0.0198(8) 0.0296(9) 0.0016(7) 0.0059(8) -0.0038(8) C18 0.0305(9) 0.0193(9) 0.0238(9) 0.0003(7) 0.0103(7) 0.0030(7) C19 0.0243(9) 0.0339(10) 0.0330(10) 0.0108(8) 0.0130(7) 0.0043(7) C20 0.0262(9) 0.0502(12) 0.0349(11) 0.0091(9) 0.0085(8) -0.0046(9) C21 0.0372(12) 0.0757(17) 0.0341(11) 0.0203(10) 0.0100(9) -0.0087(11) C22 0.0477(13) 0.0656(15) 0.0504(13) 0.0280(13) 0.0200(10) -0.0081(12) C23 0.0409(11) 0.0402(11) 0.0545(13) 0.0100(10) 0.0226(10) -0.0055(10) C24 0.0292(9) 0.0345(10) 0.0361(10) 0.0075(9) 0.0167(8) 0.0060(8) N2 0.0235(8) 0.0367(9) 0.0291(8) 0.0129(7) 0.0091(6) 0.0045(7) O1 0.0409(7) 0.0220(6) 0.0242(7) 0.0028(5) 0.0046(6) -0.0006(5) O2 0.0313(7) 0.0205(6) 0.0304(6) 0.0014(5) 0.0049(5) -0.0036(5) Cl1 0.0470(3) 0.0358(2) 0.0380(3) -0.0046(2) 0.0194(2) -0.0014(2) Cl2 0.0495(3) 0.0766(4) 0.0359(3) 0.0041(3) 0.0065(2) -0.0270(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C6 1.389(3) . ? C1 C2 1.392(3) . ? C1 C7 1.509(3) . ? C2 C3 1.385(3) . ? C2 H2A 0.95 . ? C3 C4 1.386(3) . ? C3 H3 0.95 . ? C4 C5 1.377(3) . ? C4 H4 0.95 . ? C5 C6 1.385(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 N1 1.500(2) . ? C7 C8 1.524(3) . ? C7 H7 1 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? N1 H1A 0.86(2) . ? N1 H1B 0.95(2) . ? N1 H1C 0.90(2) . ? C11 C16 1.391(3) . ? C11 C12 1.406(2) . ? C11 C17 1.507(3) . ? C12 C13 1.391(2) . ? C12 N2 1.415(2) . ? C13 C14 1.384(3) . ? C13 H13 0.95 . ? C14 C15 1.378(3) . ? C14 H14 0.95 . ? C15 C16 1.386(3) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 C18 1.530(3) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 O2 1.257(2) . ? C18 O1 1.260(2) . ? C19 C24 1.398(3) . ? C19 N2 1.401(2) . ? C19 C20 1.402(3) . ? C20 C21 1.386(3) . ? C20 Cl2 1.731(2) . ? C21 C22 1.380(3) . ? C21 H21 0.95 . ? C22 C23 1.376(3) . ? C22 H22 0.95 . ? C23 C24 1.382(3) . ? C23 H23 0.95 . ? C24 Cl1 1.737(2) . ? N2 H2 0.84(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 C1 C2 119.02(18) . . ? C6 C1 C7 118.80(17) . . ? C2 C1 C7 121.95(17) . . ? C3 C2 C1 120.30(19) . . ? C3 C2 H2A 119.9 . . ? C1 C2 H2A 119.9 . . ? C2 C3 C4 120.0(2) . . ? C2 C3 H3 120 . . ? C4 C3 H3 120 . . ? C5 C4 C3 120.10(19) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120 . . ? C6 C5 H5 120 . . ? C5 C6 C1 120.57(19) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? N1 C7 C1 112.31(15) . . ? N1 C7 C8 108.92(16) . . ? C1 C7 C8 111.07(15) . . ? N1 C7 H7 108.1 . . ? C1 C7 H7 108.1 . . ? C8 C7 H7 108.1 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 N1 H1A 116.2(13) . . ? C7 N1 H1B 113.2(12) . . ? H1A N1 H1B 112.0(19) . . ? C7 N1 H1C 109.3(14) . . ? H1A N1 H1C 98.7(19) . . ? H1B N1 H1C 106.0(19) . . ? C16 C11 C12 118.08(17) . . ? C16 C11 C17 120.77(17) . . ? C12 C11 C17 121.13(15) . . ? C13 C12 C11 119.97(16) . . ? C13 C12 N2 121.74(15) . . ? C11 C12 N2 118.29(15) . . ? C14 C13 C12 120.57(18) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 120.06(18) . . ? C15 C14 H14 120 . . ? C13 C14 H14 120 . . ? C14 C15 C16 119.56(17) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C11 121.74(18) . . ? C15 C16 H16 119.1 . . ? C11 C16 H16 119.1 . . ? C11 C17 C18 114.53(15) . . ? C11 C17 H17A 108.6 . . ? C18 C17 H17A 108.6 . . ? C11 C17 H17B 108.6 . . ? C18 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? O2 C18 O1 123.58(16) . . ? O2 C18 C17 118.44(15) . . ? O1 C18 C17 117.98(15) . . ? C24 C19 N2 122.78(17) . . ? C24 C19 C20 116.19(16) . . ? N2 C19 C20 120.98(17) . . ? C21 C20 C19 121.97(19) . . ? C21 C20 Cl2 118.86(16) . . ? C19 C20 Cl2 119.14(14) . . ? C22 C21 C20 119.4(2) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C23 C22 C21 120.6(2) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 119.3(2) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? C23 C24 C19 122.49(18) . . ? C23 C24 Cl1 118.54(16) . . ? C19 C24 Cl1 118.97(14) . . ? C19 N2 C12 120.33(14) . . ? C19 N2 H2 113.9(14) . . ? C12 N2 H2 112.1(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.1(3) . . . . ? C7 C1 C2 C3 173.25(17) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 1.9(3) . . . . ? C3 C4 C5 C6 -1.8(3) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C2 C1 C6 C5 1.2(3) . . . . ? C7 C1 C6 C5 -173.37(16) . . . . ? C6 C1 C7 N1 -133.93(17) . . . . ? C2 C1 C7 N1 51.7(2) . . . . ? C6 C1 C7 C8 103.8(2) . . . . ? C2 C1 C7 C8 -70.6(2) . . . . ? C16 C11 C12 C13 1.3(2) . . . . ? C17 C11 C12 C13 -177.14(17) . . . . ? C16 C11 C12 N2 -178.51(15) . . . . ? C17 C11 C12 N2 3.1(2) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? N2 C12 C13 C14 179.21(17) . . . . ? C12 C13 C14 C15 -0.6(3) . . . . ? C13 C14 C15 C16 1.1(3) . . . . ? C14 C15 C16 C11 -0.3(3) . . . . ? C12 C11 C16 C15 -0.9(3) . . . . ? C17 C11 C16 C15 177.57(17) . . . . ? C16 C11 C17 C18 106.10(19) . . . . ? C12 C11 C17 C18 -75.5(2) . . . . ? C11 C17 C18 O2 39.9(2) . . . . ? C11 C17 C18 O1 -140.73(16) . . . . ? C24 C19 C20 C21 1.9(3) . . . . ? N2 C19 C20 C21 179.40(19) . . . . ? C24 C19 C20 Cl2 -175.92(14) . . . . ? N2 C19 C20 Cl2 1.6(3) . . . . ? C19 C20 C21 C22 -0.7(3) . . . . ? Cl2 C20 C21 C22 177.04(19) . . . . ? C20 C21 C22 C23 0.0(4) . . . . ? C21 C22 C23 C24 -0.5(4) . . . . ? C22 C23 C24 C19 1.8(3) . . . . ? C22 C23 C24 Cl1 -178.03(18) . . . . ? N2 C19 C24 C23 -179.87(18) . . . . ? C20 C19 C24 C23 -2.4(3) . . . . ? N2 C19 C24 Cl1 -0.1(2) . . . . ? C20 C19 C24 Cl1 177.41(14) . . . . ? C24 C19 N2 C12 -108.8(2) . . . . ? C20 C19 N2 C12 73.9(2) . . . . ? C13 C12 N2 C19 8.4(3) . . . . ? C11 C12 N2 C19 -171.78(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 N1 H1A O1 0.86(2) 1.92(2) 2.768(2) 169(2) . N1 H1B O1 0.95(2) 1.86(2) 2.782(2) 163(2) 2_645 N1 H1C O2 0.90(2) 1.95(2) 2.833(2) 165(2) 2_655 N2 H2 O2 0.84(2) 2.08(2) 2.808(2) 146(2) . ###END data_4 _database_code_depnum_ccdc_archive 'CCDC 771713' #TrackingRef '- API 1-4.cif' _audit_creation_date 2010-03-19T08:30:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ((R)-1-phenylethylammonium)). (2-[[3-(trifluoromethyl)phenyl]amino]pyridine-3-carboxylate) ; _chemical_formula_moiety 'C13 H8 F3 N2 O2, C8 H12 N' _chemical_formula_sum 'C21 H20 F3 N3 O2' _chemical_formula_weight 403.4 _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.4158(6) _cell_length_b 5.5535(2) _cell_length_c 28.1619(14) _cell_angle_alpha 90 _cell_angle_beta 94.203(2) _cell_angle_gamma 90 _cell_volume 1936.57(15) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 17475 _cell_measurement_theta_min 1 _cell_measurement_theta_max 28.28 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.376 0 -1 0 0.218 18 -1 2 0.05 -17 1 -2 0.05 0 0 -1 0.05 0 0 1 0.05 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.11 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.9586 _exptl_absorpt_correction_T_max 0.9904 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 143(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '1.1\% \p and \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_unetI/netI 0.0476 _diffrn_reflns_number 14273 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 3971 _reflns_number_gt 3369 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0574P)^2^+0.4227P] 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_number_reflns 3971 _refine_ls_number_parameters 549 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881; 2551 friedel pairs measured' _refine_ls_abs_structure_Flack 10(10) _refine_diff_density_max 0.355 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1A C 0.3082(2) 0.4747(6) 0.47955(11) 0.0290(7) Uani 1 1 d . . . C2A C 0.3150(3) 0.6614(6) 0.44716(11) 0.0325(7) Uani 1 1 d . . . H2D H 0.2656 0.792 0.4472 0.039 Uiso 1 1 calc R . . C3A C 0.3944(3) 0.6574(7) 0.41454(12) 0.0384(8) Uani 1 1 d . . . H3A H 0.3986 0.785 0.3923 0.046 Uiso 1 1 calc R . . C4A C 0.4670(3) 0.4684(7) 0.41450(13) 0.0422(9) Uani 1 1 d . . . H4A H 0.5207 0.465 0.3921 0.051 Uiso 1 1 calc R . . C5A C 0.4608(3) 0.2852(7) 0.44714(14) 0.0437(9) Uani 1 1 d . . . H5A H 0.5111 0.1561 0.4475 0.052 Uiso 1 1 calc R . . C6A C 0.3818(3) 0.2874(6) 0.47948(13) 0.0369(8) Uani 1 1 d . . . H6A H 0.3782 0.1596 0.5017 0.044 Uiso 1 1 calc R . . C7A C 0.2215(3) 0.4703(6) 0.51471(11) 0.0302(7) Uani 1 1 d . . . H7A H 0.2415 0.3448 0.5392 0.036 Uiso 1 1 calc R . . C8A C 0.2048(3) 0.7072(7) 0.54041(12) 0.0372(8) Uani 1 1 d . . . H8A1 H 0.1472 0.688 0.5621 0.056 Uiso 1 1 calc R . . H8A2 H 0.1845 0.833 0.517 0.056 Uiso 1 1 calc R . . H8A3 H 0.2719 0.7531 0.5586 0.056 Uiso 1 1 calc R . . N1 N 0.1163(2) 0.3972(5) 0.48879(10) 0.0269(6) Uani 1 1 d . . . H1A H 0.080(3) 0.526(7) 0.4681(13) 0.04 Uiso 1 1 d . . . H1B H 0.127(3) 0.259(7) 0.4664(12) 0.04 Uiso 1 1 d . . . H1C H 0.075(3) 0.352(7) 0.5083(14) 0.04 Uiso 1 1 d . . . C1B C 0.7955(2) -0.2900(6) 0.00971(11) 0.0286(7) Uani 1 1 d . . . C2B C 0.8216(2) -0.4624(6) 0.04486(11) 0.0294(7) Uani 1 1 d . . . H2E H 0.7781 -0.6024 0.0467 0.035 Uiso 1 1 calc R . . C3B C 0.9107(2) -0.4305(7) 0.07702(12) 0.0350(8) Uani 1 1 d . . . H3B H 0.9272 -0.5466 0.1012 0.042 Uiso 1 1 calc R . . C4B C 0.9748(3) -0.2300(7) 0.07371(13) 0.0393(9) Uani 1 1 d . . . H4B H 1.0356 -0.208 0.0958 0.047 Uiso 1 1 calc R . . C5B C 0.9513(3) -0.0602(6) 0.03846(14) 0.0386(8) Uani 1 1 d . . . H5B H 0.9965 0.0765 0.0361 0.046 Uiso 1 1 calc R . . C6B C 0.8616(3) -0.0899(6) 0.00667(12) 0.0350(8) Uani 1 1 d . . . H6B H 0.8453 0.0275 -0.0173 0.042 Uiso 1 1 calc R . . C7B C 0.6947(3) -0.3155(6) -0.02349(11) 0.0317(7) Uani 1 1 d . . . H7B H 0.6964 -0.1885 -0.0486 0.038 Uiso 1 1 calc R . . C8B C 0.6821(3) -0.5585(7) -0.04810(13) 0.0439(9) Uani 1 1 d . . . H8B1 H 0.6161 -0.5587 -0.0694 0.066 Uiso 1 1 calc R . . H8B2 H 0.6776 -0.6854 -0.0241 0.066 Uiso 1 1 calc R . . H8B3 H 0.7446 -0.5883 -0.0666 0.066 Uiso 1 1 calc R . . N2 N 0.5971(2) -0.2716(6) 0.00423(10) 0.0331(6) Uani 1 1 d . . . H2A H 0.593(3) -0.392(8) 0.0253(15) 0.05 Uiso 1 1 d . . . H2B H 0.602(3) -0.123(8) 0.0181(15) 0.05 Uiso 1 1 d . . . H2C H 0.524(3) -0.263(7) -0.0189(12) 0.05 Uiso 1 1 d . . . C11A C 0.0276(2) 0.7994(6) 0.35829(10) 0.0233(6) Uani 1 1 d . . . C12A C 0.0640(2) 0.9103(6) 0.31673(10) 0.0249(7) Uani 1 1 d . . . C13A C -0.0344(3) 0.6446(6) 0.26870(11) 0.0318(7) Uani 1 1 d . . . H13A H -0.0576 0.5924 0.2375 0.038 Uiso 1 1 calc R . . C14A C -0.0715(3) 0.5198(6) 0.30642(11) 0.0327(7) Uani 1 1 d . . . H14A H -0.1168 0.3828 0.3016 0.039 Uiso 1 1 calc R . . C15A C -0.0400(2) 0.6024(6) 0.35161(11) 0.0305(7) Uani 1 1 d . . . H15A H -0.0651 0.5226 0.3785 0.037 Uiso 1 1 calc R . . C16A C 0.0537(2) 0.8908(6) 0.40795(10) 0.0263(7) Uani 1 1 d . . . C17A C 0.1806(2) 1.2472(6) 0.28851(10) 0.0268(7) Uani 1 1 d . . . C18A C 0.1658(2) 1.2178(6) 0.23923(11) 0.0300(7) Uani 1 1 d . . . H18A H 0.1238 1.0881 0.2259 0.036 Uiso 1 1 calc R . . C19A C 0.2139(2) 1.3826(6) 0.20981(11) 0.0321(7) Uani 1 1 d . . . C20A C 0.2751(3) 1.5732(7) 0.22805(13) 0.0373(8) Uani 1 1 d . . . H20A H 0.3058 1.6856 0.2075 0.045 Uiso 1 1 calc R . . C21A C 0.2907(3) 1.5968(6) 0.27722(13) 0.0387(8) Uani 1 1 d . . . H21A H 0.334 1.7247 0.2904 0.046 Uiso 1 1 calc R . . C22A C 0.2443(3) 1.4377(6) 0.30690(12) 0.0335(8) Uani 1 1 d . . . H22A H 0.2557 1.4572 0.3404 0.04 Uiso 1 1 calc R . . C23A C 0.2033(3) 1.3403(8) 0.15781(13) 0.0486(10) Uani 1 1 d . . . N3 N 0.0319(2) 0.8341(5) 0.27285(8) 0.0292(6) Uani 1 1 d . . . N4 N 0.1355(2) 1.0977(5) 0.32181(9) 0.0290(6) Uani 1 1 d . . . H4 H 0.144(3) 1.139(7) 0.3463(12) 0.035 Uiso 1 1 d . . . O1A O 0.11246(19) 1.0737(4) 0.41467(7) 0.0355(5) Uani 1 1 d . . . O2A O 0.01502(17) 0.7731(4) 0.44147(7) 0.0350(5) Uani 1 1 d . . . F1A F 0.2789(3) 1.1890(8) 0.14388(9) 0.1214(16) Uani 1 1 d . . . F2A F 0.1121(2) 1.2424(8) 0.14158(9) 0.1026(13) Uani 1 1 d . . . F3A F 0.2153(3) 1.5326(6) 0.13170(9) 0.0966(11) Uani 1 1 d . . . C11B C 0.6660(2) -0.7589(6) 0.13130(10) 0.0259(7) Uani 1 1 d . . . C12B C 0.6707(2) -0.6205(6) 0.17379(11) 0.0258(7) Uani 1 1 d . . . C13B C 0.8082(3) -0.8538(6) 0.20664(11) 0.0342(8) Uani 1 1 d . . . H13B H 0.8577 -0.8886 0.2331 0.041 Uiso 1 1 calc R . . C14B C 0.8114(3) -0.9984(7) 0.16736(12) 0.0357(8) Uani 1 1 d . . . H14B H 0.8616 -1.1269 0.1662 0.043 Uiso 1 1 calc R . . C15B C 0.7374(2) -0.9477(6) 0.12921(11) 0.0306(7) Uani 1 1 d . . . H15B H 0.7361 -1.0445 0.1014 0.037 Uiso 1 1 calc R . . C16B C 0.5907(2) -0.7034(6) 0.08856(11) 0.0297(7) Uani 1 1 d . . . C17B C 0.5834(2) -0.2728(6) 0.21449(11) 0.0268(7) Uani 1 1 d . . . C18B C 0.6358(2) -0.2827(6) 0.26040(11) 0.0298(7) Uani 1 1 d . . . H18B H 0.6874 -0.405 0.2685 0.036 Uiso 1 1 calc R . . C19B C 0.6110(2) -0.1116(6) 0.29374(11) 0.0314(7) Uani 1 1 d . . . C20B C 0.5365(3) 0.0703(7) 0.28357(13) 0.0374(8) Uani 1 1 d . . . H20B H 0.5207 0.1849 0.3071 0.045 Uiso 1 1 calc R . . C21B C 0.4855(3) 0.0810(7) 0.23810(13) 0.0367(8) Uani 1 1 d . . . H21B H 0.4343 0.2043 0.2302 0.044 Uiso 1 1 calc R . . C22B C 0.5092(2) -0.0881(6) 0.20421(11) 0.0306(7) Uani 1 1 d . . . H22B H 0.4741 -0.0779 0.1732 0.037 Uiso 1 1 calc R . . C23B C 0.6716(3) -0.1181(7) 0.34152(12) 0.0393(9) Uani 1 1 d . . . N5 N 0.7416(2) -0.6688(5) 0.21086(9) 0.0309(6) Uani 1 1 d . . . N6 N 0.5998(2) -0.4332(5) 0.17764(10) 0.0313(6) Uani 1 1 d . . . H6 H 0.562(3) -0.403(7) 0.1509(13) 0.038 Uiso 1 1 d . . . O1B O 0.5325(2) -0.5199(5) 0.08747(8) 0.0449(6) Uani 1 1 d . . . O2B O 0.59243(18) -0.8398(5) 0.05267(8) 0.0407(6) Uani 1 1 d . . . F1B F 0.76412(16) 0.0076(5) 0.34274(8) 0.0543(6) Uani 1 1 d . . . F2B F 0.61418(17) -0.0219(5) 0.37596(7) 0.0600(7) Uani 1 1 d . . . F3B F 0.69844(17) -0.3388(4) 0.35652(7) 0.0475(5) 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 C1A 0.0281(17) 0.0287(17) 0.0298(16) -0.0068(14) -0.0014(13) 0.0007(14) C2A 0.0300(17) 0.0328(19) 0.0343(17) -0.0027(15) 0.0004(13) 0.0018(15) C3A 0.0348(19) 0.043(2) 0.0384(18) 0.0000(16) 0.0066(14) -0.0061(17) C4A 0.0304(18) 0.050(2) 0.048(2) -0.0137(18) 0.0121(15) -0.0089(17) C5A 0.0283(18) 0.042(2) 0.061(2) -0.0141(19) 0.0024(16) 0.0058(17) C6A 0.0318(18) 0.0306(19) 0.047(2) -0.0013(16) -0.0017(15) 0.0030(16) C7A 0.0317(17) 0.0314(17) 0.0272(16) -0.0001(14) 0.0013(13) 0.0019(15) C8A 0.0400(19) 0.0400(19) 0.0317(17) -0.0088(15) 0.0038(14) 0.0000(17) N1 0.0303(15) 0.0284(15) 0.0229(14) -0.0005(12) 0.0081(11) -0.0038(13) C1B 0.0251(16) 0.0292(17) 0.0325(17) -0.0006(14) 0.0099(13) 0.0045(14) C2B 0.0247(16) 0.0286(18) 0.0355(17) -0.0011(14) 0.0058(13) -0.0009(14) C3B 0.0292(18) 0.0362(19) 0.0395(19) 0.0011(15) 0.0014(14) 0.0053(16) C4B 0.0240(17) 0.045(2) 0.048(2) -0.0121(18) 0.0026(14) 0.0000(17) C5B 0.0285(18) 0.0292(19) 0.060(2) -0.0061(16) 0.0135(16) -0.0027(15) C6B 0.0328(18) 0.0300(18) 0.043(2) 0.0024(15) 0.0116(15) 0.0040(16) C7B 0.0339(18) 0.0363(19) 0.0254(16) 0.0015(14) 0.0063(13) 0.0039(16) C8B 0.051(2) 0.041(2) 0.039(2) -0.0074(16) -0.0010(16) 0.0047(19) N2 0.0270(14) 0.0419(18) 0.0296(15) 0.0026(13) -0.0018(12) 0.0018(14) C11A 0.0212(15) 0.0262(16) 0.0228(14) 0.0011(12) 0.0043(11) 0.0042(13) C12A 0.0234(15) 0.0281(17) 0.0230(15) -0.0011(12) 0.0004(11) 0.0050(14) C13A 0.0341(18) 0.0341(19) 0.0260(16) -0.0015(14) -0.0048(13) -0.0032(16) C14A 0.0312(17) 0.0304(19) 0.0364(18) -0.0009(14) 0.0023(14) -0.0068(15) C15A 0.0303(17) 0.0355(19) 0.0265(16) 0.0027(14) 0.0071(13) 0.0018(15) C16A 0.0276(16) 0.0311(17) 0.0210(15) 0.0007(13) 0.0065(12) 0.0107(15) C17A 0.0263(16) 0.0267(17) 0.0274(16) 0.0039(13) 0.0023(12) 0.0032(14) C18A 0.0289(16) 0.0322(17) 0.0289(16) 0.0005(14) 0.0023(13) -0.0004(15) C19A 0.0256(16) 0.0388(19) 0.0323(17) 0.0100(15) 0.0043(13) 0.0055(15) C20A 0.0300(18) 0.0347(19) 0.048(2) 0.0086(16) 0.0083(15) 0.0012(16) C21A 0.0341(19) 0.0308(19) 0.052(2) -0.0028(16) 0.0054(15) -0.0041(16) C22A 0.0332(18) 0.0357(19) 0.0318(17) -0.0018(14) 0.0035(13) -0.0019(16) C23A 0.045(2) 0.065(3) 0.036(2) 0.014(2) 0.0065(16) -0.006(2) N3 0.0296(14) 0.0345(16) 0.0229(13) 0.0004(11) -0.0017(10) -0.0012(13) N4 0.0367(15) 0.0295(15) 0.0209(13) -0.0013(12) 0.0014(11) -0.0043(13) O1A 0.0473(14) 0.0354(13) 0.0241(11) -0.0051(10) 0.0043(10) -0.0016(12) O2A 0.0389(13) 0.0427(14) 0.0245(12) 0.0039(10) 0.0103(9) 0.0086(11) F1A 0.148(3) 0.179(4) 0.0370(15) -0.0158(19) 0.0068(17) 0.087(3) F2A 0.099(2) 0.172(4) 0.0350(13) 0.0125(18) -0.0063(13) -0.065(2) F3A 0.157(3) 0.086(2) 0.0460(15) 0.0304(15) 0.0015(17) -0.028(2) C11B 0.0219(15) 0.0338(18) 0.0224(15) 0.0034(13) 0.0038(11) -0.0016(14) C12B 0.0225(15) 0.0261(17) 0.0287(16) 0.0014(13) -0.0002(12) -0.0008(13) C13B 0.0337(18) 0.039(2) 0.0285(17) -0.0030(15) -0.0060(13) 0.0071(16) C14B 0.0340(18) 0.038(2) 0.0350(18) -0.0019(15) 0.0002(14) 0.0089(16) C15B 0.0310(17) 0.0373(19) 0.0241(15) -0.0045(14) 0.0062(13) -0.0021(16) C16B 0.0272(17) 0.0379(19) 0.0241(16) -0.0006(14) 0.0028(12) -0.0070(16) C17B 0.0254(16) 0.0251(16) 0.0301(16) -0.0021(13) 0.0027(12) -0.0042(14) C18B 0.0240(16) 0.0310(17) 0.0345(17) -0.0013(14) 0.0039(13) 0.0004(14) C19B 0.0240(16) 0.0376(19) 0.0333(17) -0.0072(15) 0.0062(13) -0.0048(16) C20B 0.0308(18) 0.0371(19) 0.046(2) -0.0096(16) 0.0117(15) -0.0028(17) C21B 0.0291(18) 0.0311(18) 0.050(2) -0.0005(16) 0.0036(15) 0.0044(16) C22B 0.0232(16) 0.0314(18) 0.0368(18) 0.0050(14) -0.0009(13) -0.0027(15) C23B 0.0325(19) 0.051(2) 0.0355(19) -0.0134(17) 0.0079(14) -0.0006(18) N5 0.0295(15) 0.0359(16) 0.0268(14) -0.0040(12) -0.0030(11) 0.0039(13) N6 0.0311(15) 0.0323(15) 0.0293(14) -0.0007(12) -0.0049(11) 0.0044(13) O1B 0.0521(15) 0.0476(15) 0.0329(13) -0.0013(11) -0.0119(11) 0.0134(13) O2B 0.0339(13) 0.0613(16) 0.0262(12) -0.0109(12) -0.0017(9) 0.0016(12) F1B 0.0398(12) 0.0696(16) 0.0528(13) -0.0130(12) -0.0022(10) -0.0138(12) F2B 0.0508(13) 0.0901(18) 0.0403(12) -0.0275(12) 0.0114(10) 0.0125(13) F3B 0.0514(13) 0.0591(15) 0.0318(10) -0.0009(10) 0.0024(9) 0.0026(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1A C6A 1.385(5) . ? C1A C2A 1.388(5) . ? C1A C7A 1.516(4) . ? C2A C3A 1.396(5) . ? C2A H2D 0.95 . ? C3A C4A 1.384(5) . ? C3A H3A 0.95 . ? C4A C5A 1.377(5) . ? C4A H4A 0.95 . ? C5A C6A 1.386(5) . ? C5A H5A 0.95 . ? C6A H6A 0.95 . ? C7A N1 1.504(4) . ? C7A C8A 1.523(5) . ? C7A H7A 1 . ? C8A H8A1 0.98 . ? C8A H8A2 0.98 . ? C8A H8A3 0.98 . ? N1 H1A 1.01(4) . ? N1 H1B 1.01(4) . ? N1 H1C 0.82(4) . ? C1B C6B 1.388(5) . ? C1B C2B 1.398(4) . ? C1B C7B 1.513(4) . ? C2B C3B 1.388(4) . ? C2B H2E 0.95 . ? C3B C4B 1.376(5) . ? C3B H3B 0.95 . ? C4B C5B 1.385(5) . ? C4B H4B 0.95 . ? C5B C6B 1.386(5) . ? C5B H5B 0.95 . ? C6B H6B 0.95 . ? C7B N2 1.509(4) . ? C7B C8B 1.520(5) . ? C7B H7B 1 . ? C8B H8B1 0.98 . ? C8B H8B2 0.98 . ? C8B H8B3 0.98 . ? N2 H2A 0.90(5) . ? N2 H2B 0.92(5) . ? N2 H2C 1.08(4) . ? C11A C15A 1.383(5) . ? C11A C12A 1.425(4) . ? C11A C16A 1.500(4) . ? C12A N3 1.339(4) . ? C12A N4 1.369(4) . ? C13A N3 1.336(4) . ? C13A C14A 1.376(4) . ? C13A H13A 0.95 . ? C14A C15A 1.382(4) . ? C14A H14A 0.95 . ? C15A H15A 0.95 . ? C16A O1A 1.257(4) . ? C16A O2A 1.271(4) . ? C17A C18A 1.396(4) . ? C17A C22A 1.398(5) . ? C17A N4 1.400(4) . ? C18A C19A 1.397(5) . ? C18A H18A 0.95 . ? C19A C20A 1.380(5) . ? C19A C23A 1.479(5) . ? C20A C21A 1.390(5) . ? C20A H20A 0.95 . ? C21A C22A 1.372(5) . ? C21A H21A 0.95 . ? C22A H22A 0.95 . ? C23A F2A 1.308(5) . ? C23A F3A 1.312(5) . ? C23A F1A 1.340(5) . ? N4 H4 0.73(3) . ? C11B C15B 1.378(5) . ? C11B C12B 1.420(4) . ? C11B C16B 1.501(4) . ? C12B N5 1.342(4) . ? C12B N6 1.373(4) . ? C13B N5 1.330(4) . ? C13B C14B 1.370(5) . ? C13B H13B 0.95 . ? C14B C15B 1.390(5) . ? C14B H14B 0.95 . ? C15B H15B 0.95 . ? C16B O1B 1.248(4) . ? C16B O2B 1.264(4) . ? C17B N6 1.394(4) . ? C17B C22B 1.394(4) . ? C17B C18B 1.405(4) . ? C18B C19B 1.386(4) . ? C18B H18B 0.95 . ? C19B C20B 1.386(5) . ? C19B C23B 1.493(5) . ? C20B C21B 1.387(5) . ? C20B H20B 0.95 . ? C21B C22B 1.386(5) . ? C21B H21B 0.95 . ? C22B H22B 0.95 . ? C23B F3B 1.331(5) . ? C23B F1B 1.342(4) . ? C23B F2B 1.355(4) . ? N6 H6 0.87(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 C6A C1A C2A 119.2(3) . . ? C6A C1A C7A 119.3(3) . . ? C2A C1A C7A 121.4(3) . . ? C1A C2A C3A 120.0(3) . . ? C1A C2A H2D 120 . . ? C3A C2A H2D 120 . . ? C4A C3A C2A 120.3(3) . . ? C4A C3A H3A 119.9 . . ? C2A C3A H3A 119.9 . . ? C5A C4A C3A 119.4(3) . . ? C5A C4A H4A 120.3 . . ? C3A C4A H4A 120.3 . . ? C4A C5A C6A 120.6(3) . . ? C4A C5A H5A 119.7 . . ? C6A C5A H5A 119.7 . . ? C1A C6A C5A 120.4(3) . . ? C1A C6A H6A 119.8 . . ? C5A C6A H6A 119.8 . . ? N1 C7A C1A 108.7(2) . . ? N1 C7A C8A 108.7(3) . . ? C1A C7A C8A 115.1(3) . . ? N1 C7A H7A 108 . . ? C1A C7A H7A 108 . . ? C8A C7A H7A 108 . . ? C7A C8A H8A1 109.5 . . ? C7A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C7A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C7A N1 H1A 115(2) . . ? C7A N1 H1B 111.3(19) . . ? H1A N1 H1B 105(3) . . ? C7A N1 H1C 109(3) . . ? H1A N1 H1C 110(3) . . ? H1B N1 H1C 107(3) . . ? C6B C1B C2B 119.0(3) . . ? C6B C1B C7B 120.2(3) . . ? C2B C1B C7B 120.8(3) . . ? C3B C2B C1B 120.4(3) . . ? C3B C2B H2E 119.8 . . ? C1B C2B H2E 119.8 . . ? C4B C3B C2B 119.7(3) . . ? C4B C3B H3B 120.1 . . ? C2B C3B H3B 120.1 . . ? C3B C4B C5B 120.5(3) . . ? C3B C4B H4B 119.8 . . ? C5B C4B H4B 119.8 . . ? C4B C5B C6B 119.9(3) . . ? C4B C5B H5B 120 . . ? C6B C5B H5B 120 . . ? C5B C6B C1B 120.4(3) . . ? C5B C6B H6B 119.8 . . ? C1B C6B H6B 119.8 . . ? N2 C7B C1B 108.9(2) . . ? N2 C7B C8B 108.6(3) . . ? C1B C7B C8B 114.7(3) . . ? N2 C7B H7B 108.1 . . ? C1B C7B H7B 108.1 . . ? C8B C7B H7B 108.1 . . ? C7B C8B H8B1 109.5 . . ? C7B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? C7B C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 109.5 . . ? C7B N2 H2A 108(3) . . ? C7B N2 H2B 110(3) . . ? H2A N2 H2B 113(3) . . ? C7B N2 H2C 111.7(18) . . ? H2A N2 H2C 110(3) . . ? H2B N2 H2C 104(3) . . ? C15A C11A C12A 117.1(3) . . ? C15A C11A C16A 118.8(3) . . ? C12A C11A C16A 124.0(3) . . ? N3 C12A N4 118.9(3) . . ? N3 C12A C11A 122.1(3) . . ? N4 C12A C11A 119.0(3) . . ? N3 C13A C14A 124.6(3) . . ? N3 C13A H13A 117.7 . . ? C14A C13A H13A 117.7 . . ? C13A C14A C15A 117.1(3) . . ? C13A C14A H14A 121.5 . . ? C15A C14A H14A 121.5 . . ? C14A C15A C11A 121.1(3) . . ? C14A C15A H15A 119.5 . . ? C11A C15A H15A 119.5 . . ? O1A C16A O2A 123.4(3) . . ? O1A C16A C11A 119.8(3) . . ? O2A C16A C11A 116.8(3) . . ? C18A C17A C22A 119.1(3) . . ? C18A C17A N4 124.5(3) . . ? C22A C17A N4 116.4(3) . . ? C17A C18A C19A 118.8(3) . . ? C17A C18A H18A 120.6 . . ? C19A C18A H18A 120.6 . . ? C20A C19A C18A 121.9(3) . . ? C20A C19A C23A 119.8(3) . . ? C18A C19A C23A 118.2(3) . . ? C19A C20A C21A 118.4(3) . . ? C19A C20A H20A 120.8 . . ? C21A C20A H20A 120.8 . . ? C22A C21A C20A 120.8(3) . . ? C22A C21A H21A 119.6 . . ? C20A C21A H21A 119.6 . . ? C21A C22A C17A 120.9(3) . . ? C21A C22A H22A 119.6 . . ? C17A C22A H22A 119.6 . . ? F2A C23A F3A 105.9(3) . . ? F2A C23A F1A 104.2(4) . . ? F3A C23A F1A 103.6(3) . . ? F2A C23A C19A 115.1(3) . . ? F3A C23A C19A 114.8(4) . . ? F1A C23A C19A 112.1(3) . . ? C13A N3 C12A 118.0(3) . . ? C12A N4 C17A 132.0(3) . . ? C12A N4 H4 112(3) . . ? C17A N4 H4 115(3) . . ? C15B C11B C12B 117.4(3) . . ? C15B C11B C16B 119.2(3) . . ? C12B C11B C16B 123.4(3) . . ? N5 C12B N6 118.6(3) . . ? N5 C12B C11B 122.1(3) . . ? N6 C12B C11B 119.3(3) . . ? N5 C13B C14B 125.4(3) . . ? N5 C13B H13B 117.3 . . ? C14B C13B H13B 117.3 . . ? C13B C14B C15B 116.7(3) . . ? C13B C14B H14B 121.6 . . ? C15B C14B H14B 121.6 . . ? C11B C15B C14B 120.8(3) . . ? C11B C15B H15B 119.6 . . ? C14B C15B H15B 119.6 . . ? O1B C16B O2B 120.9(3) . . ? O1B C16B C11B 120.8(3) . . ? O2B C16B C11B 118.1(3) . . ? N6 C17B C22B 116.5(3) . . ? N6 C17B C18B 125.2(3) . . ? C22B C17B C18B 118.3(3) . . ? C19B C18B C17B 119.0(3) . . ? C19B C18B H18B 120.5 . . ? C17B C18B H18B 120.5 . . ? C20B C19B C18B 122.5(3) . . ? C20B C19B C23B 119.2(3) . . ? C18B C19B C23B 118.1(3) . . ? C19B C20B C21B 118.3(3) . . ? C19B C20B H20B 120.8 . . ? C21B C20B H20B 120.8 . . ? C22B C21B C20B 120.1(3) . . ? C22B C21B H21B 120 . . ? C20B C21B H21B 120 . . ? C21B C22B C17B 121.7(3) . . ? C21B C22B H22B 119.1 . . ? C17B C22B H22B 119.1 . . ? F3B C23B F1B 106.1(3) . . ? F3B C23B F2B 105.6(3) . . ? F1B C23B F2B 105.7(3) . . ? F3B C23B C19B 114.0(3) . . ? F1B C23B C19B 112.6(3) . . ? F2B C23B C19B 112.3(3) . . ? C13B N5 C12B 117.5(3) . . ? C12B N6 C17B 132.3(3) . . ? C12B N6 H6 113(2) . . ? C17B N6 H6 115(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 C6A C1A C2A C3A 0.9(5) . . . . ? C7A C1A C2A C3A -178.6(3) . . . . ? C1A C2A C3A C4A -0.4(5) . . . . ? C2A C3A C4A C5A -0.5(5) . . . . ? C3A C4A C5A C6A 0.8(5) . . . . ? C2A C1A C6A C5A -0.6(5) . . . . ? C7A C1A C6A C5A 178.9(3) . . . . ? C4A C5A C6A C1A -0.3(5) . . . . ? C6A C1A C7A N1 -103.2(3) . . . . ? C2A C1A C7A N1 76.2(4) . . . . ? C6A C1A C7A C8A 134.6(3) . . . . ? C2A C1A C7A C8A -45.9(4) . . . . ? C6B C1B C2B C3B 1.7(4) . . . . ? C7B C1B C2B C3B -176.1(3) . . . . ? C1B C2B C3B C4B -1.2(5) . . . . ? C2B C3B C4B C5B -0.1(5) . . . . ? C3B C4B C5B C6B 1.0(5) . . . . ? C4B C5B C6B C1B -0.5(5) . . . . ? C2B C1B C6B C5B -0.9(4) . . . . ? C7B C1B C6B C5B 177.0(3) . . . . ? C6B C1B C7B N2 -107.1(3) . . . . ? C2B C1B C7B N2 70.7(4) . . . . ? C6B C1B C7B C8B 130.9(3) . . . . ? C2B C1B C7B C8B -51.3(4) . . . . ? C15A C11A C12A N3 2.2(4) . . . . ? C16A C11A C12A N3 -174.6(3) . . . . ? C15A C11A C12A N4 -176.5(3) . . . . ? C16A C11A C12A N4 6.7(4) . . . . ? N3 C13A C14A C15A 2.0(5) . . . . ? C13A C14A C15A C11A -1.2(5) . . . . ? C12A C11A C15A C14A -0.8(4) . . . . ? C16A C11A C15A C14A 176.2(3) . . . . ? C15A C11A C16A O1A -178.0(3) . . . . ? C12A C11A C16A O1A -1.3(4) . . . . ? C15A C11A C16A O2A 3.0(4) . . . . ? C12A C11A C16A O2A 179.7(3) . . . . ? C22A C17A C18A C19A -1.0(5) . . . . ? N4 C17A C18A C19A 178.9(3) . . . . ? C17A C18A C19A C20A -0.2(5) . . . . ? C17A C18A C19A C23A 176.2(3) . . . . ? C18A C19A C20A C21A 1.4(5) . . . . ? C23A C19A C20A C21A -174.9(3) . . . . ? C19A C20A C21A C22A -1.5(5) . . . . ? C20A C21A C22A C17A 0.3(5) . . . . ? C18A C17A C22A C21A 1.0(5) . . . . ? N4 C17A C22A C21A -178.9(3) . . . . ? C20A C19A C23A F2A -149.5(4) . . . . ? C18A C19A C23A F2A 34.0(5) . . . . ? C20A C19A C23A F3A -26.1(5) . . . . ? C18A C19A C23A F3A 157.4(4) . . . . ? C20A C19A C23A F1A 91.7(5) . . . . ? C18A C19A C23A F1A -84.7(4) . . . . ? C14A C13A N3 C12A -0.7(5) . . . . ? N4 C12A N3 C13A 177.3(3) . . . . ? C11A C12A N3 C13A -1.4(4) . . . . ? N3 C12A N4 C17A 4.9(5) . . . . ? C11A C12A N4 C17A -176.4(3) . . . . ? C18A C17A N4 C12A -5.7(5) . . . . ? C22A C17A N4 C12A 174.2(3) . . . . ? C15B C11B C12B N5 0.0(4) . . . . ? C16B C11B C12B N5 -177.5(3) . . . . ? C15B C11B C12B N6 -178.9(3) . . . . ? C16B C11B C12B N6 3.5(4) . . . . ? N5 C13B C14B C15B -0.9(5) . . . . ? C12B C11B C15B C14B -0.3(4) . . . . ? C16B C11B C15B C14B 177.3(3) . . . . ? C13B C14B C15B C11B 0.7(5) . . . . ? C15B C11B C16B O1B -172.9(3) . . . . ? C12B C11B C16B O1B 4.6(5) . . . . ? C15B C11B C16B O2B 3.1(4) . . . . ? C12B C11B C16B O2B -179.4(3) . . . . ? N6 C17B C18B C19B -179.6(3) . . . . ? C22B C17B C18B C19B 0.8(4) . . . . ? C17B C18B C19B C20B -0.1(5) . . . . ? C17B C18B C19B C23B -177.0(3) . . . . ? C18B C19B C20B C21B -0.4(5) . . . . ? C23B C19B C20B C21B 176.4(3) . . . . ? C19B C20B C21B C22B 0.2(5) . . . . ? C20B C21B C22B C17B 0.4(5) . . . . ? N6 C17B C22B C21B 179.4(3) . . . . ? C18B C17B C22B C21B -0.9(5) . . . . ? C20B C19B C23B F3B 149.4(3) . . . . ? C18B C19B C23B F3B -33.6(4) . . . . ? C20B C19B C23B F1B -89.7(4) . . . . ? C18B C19B C23B F1B 87.2(4) . . . . ? C20B C19B C23B F2B 29.5(5) . . . . ? C18B C19B C23B F2B -153.6(3) . . . . ? C14B C13B N5 C12B 0.6(5) . . . . ? N6 C12B N5 C13B 178.8(3) . . . . ? C11B C12B N5 C13B -0.2(4) . . . . ? N5 C12B N6 C17B -0.9(5) . . . . ? C11B C12B N6 C17B 178.1(3) . . . . ? C22B C17B N6 C12B 174.3(3) . . . . ? C18B C17B N6 C12B -5.3(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4 O1A 0.73(3) 2.02(4) 2.655(3) 145(4) . N1 H1A O2A 1.01(4) 1.74(4) 2.733(4) 170(3) . N1 H1B O1A 1.01(4) 1.78(4) 2.752(3) 160(3) 1_545 N1 H1C O2A 0.82(4) 1.92(4) 2.731(3) 174(4) 2_546 N6 H6 O1B 0.87(3) 1.91(4) 2.658(3) 143(3) . N2 H2A O1B 0.90(5) 2.08(4) 2.884(4) 148(4) . N2 H2B O2B 0.92(5) 1.86(5) 2.762(4) 170(4) 1_565 N2 H2C O2B 1.08(4) 1.72(4) 2.774(4) 163(3) 2_655 ###END