# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'le Roex, Tanya' 'Haynes, Delia' _publ_contact_author_name 'Dr le Roex, Tanya' _publ_contact_author_email tlr@sun.ac.za _publ_section_title ; Solvate formation in lutidinium pamoate salts: a systematic study ; # Attachment '- submission.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 788706' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,5 lutidinium pamoate THF solvate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N 1+ , C23 H15 O6 1- , C4 H8 O' _chemical_formula_sum 'C34 H33 N O7' _chemical_formula_weight 567.61 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.820(8) _cell_length_b 12.922(8) _cell_length_c 17.143(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.830(8) _cell_angle_gamma 90.00 _cell_volume 2822(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2536 _cell_measurement_theta_min 2.451 _cell_measurement_theta_max 26.104 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9854 _exptl_absorpt_correction_T_max 0.9899 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 15747 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 26.24 _reflns_number_total 5679 _reflns_number_gt 3154 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5679 _refine_ls_number_parameters 378 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1676 _refine_ls_R_factor_gt 0.1191 _refine_ls_wR_factor_ref 0.4166 _refine_ls_wR_factor_gt 0.3655 _refine_ls_goodness_of_fit_ref 1.426 _refine_ls_restrained_S_all 1.426 _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 N11 N 0.7271(5) 0.6409(4) -0.0672(4) 0.0965(19) Uani 1 1 d . . . H11 H 0.7257 0.6693 -0.0210 0.116 Uiso 1 1 calc R . . C12 C 0.6407(6) 0.5779(5) -0.1188(5) 0.096(2) Uani 1 1 d . . . C13 C 0.6530(5) 0.5388(4) -0.1885(4) 0.0730(15) Uani 1 1 d . . . H13 H 0.5999 0.4953 -0.2261 0.088 Uiso 1 1 calc R . . C14 C 0.7355(6) 0.5595(6) -0.2045(6) 0.113(3) Uani 1 1 d . . . H14 H 0.7376 0.5302 -0.2547 0.135 Uiso 1 1 calc R . . C15 C 0.8176(5) 0.6177(6) -0.1582(4) 0.0900(19) Uani 1 1 d . . . C16 C 0.8076(5) 0.6571(5) -0.0870(4) 0.0850(18) Uani 1 1 d . . . H16 H 0.8631 0.6988 -0.0501 0.102 Uiso 1 1 calc R . . C17 C 0.5568(7) 0.5614(7) -0.0911(6) 0.136(3) Uani 1 1 d . . . H17A H 0.5854 0.5374 -0.0323 0.205 Uiso 1 1 calc R . . H17B H 0.5088 0.5091 -0.1271 0.205 Uiso 1 1 calc R . . H17C H 0.5187 0.6264 -0.0950 0.205 Uiso 1 1 calc R . . C18 C 0.9133(8) 0.6336(11) -0.1749(8) 0.208(7) Uani 1 1 d . . . H18A H 0.9654 0.5809 -0.1449 0.311 Uiso 1 1 calc R . . H18B H 0.9421 0.7025 -0.1551 0.311 Uiso 1 1 calc R . . H18C H 0.8961 0.6281 -0.2358 0.311 Uiso 1 1 calc R . . O31 O 0.8044(7) 0.5035(8) -0.3757(6) 0.145(3) Uiso 0.68 1 d P A 1 C31 C 0.8112(9) 0.4111(10) -0.4057(7) 0.110(3) Uiso 0.68 1 d P A 1 C32 C 0.9026(10) 0.3857(11) -0.4105(8) 0.177(4) Uiso 1 1 d . . . C33 C 0.8890(9) 0.5597(9) -0.3886(8) 0.109(3) Uiso 0.68 1 d P A 1 C34 C 0.9765(12) 0.4903(12) -0.3607(10) 0.144(5) Uiso 0.68 1 d P A 1 C35 C 1.031(2) 0.508(2) -0.402(2) 0.133(9) Uiso 0.33 1 d P A -1 C36 C 0.867(2) 0.472(2) -0.4764(19) 0.133(9) Uiso 0.33 1 d P A -1 C37 C 1.007(3) 0.411(3) -0.421(2) 0.149(10) Uiso 0.33 1 d P A -1 O41 O 0.924(3) 0.560(3) -0.440(2) 0.236(13) Uiso 0.33 1 d P A -1 O211 O 0.5608(2) 0.8177(2) 0.0972(2) 0.0622(10) Uani 1 1 d . . . H211 H 0.6111 0.8127 0.0815 0.075 Uiso 1 1 calc R . . C211 C 0.5775(3) 0.7537(3) 0.1641(3) 0.0475(11) Uani 1 1 d . . . C212 C 0.6729(3) 0.6931(3) 0.1972(3) 0.0493(11) Uani 1 1 d . . . C213 C 0.6918(3) 0.6339(3) 0.2665(3) 0.0476(11) Uani 1 1 d . . . H213 H 0.7540 0.5933 0.2876 0.057 Uiso 1 1 calc R . . C214 C 0.6216(3) 0.6306(3) 0.3086(3) 0.0427(10) Uani 1 1 d . . . C215 C 0.6445(4) 0.5737(3) 0.3839(3) 0.0515(11) Uani 1 1 d . . . H215 H 0.7078 0.5349 0.4062 0.062 Uiso 1 1 calc R . . C216 C 0.5789(4) 0.5730(3) 0.4249(3) 0.0556(12) Uani 1 1 d . . . H216 H 0.5958 0.5341 0.4755 0.067 Uiso 1 1 calc R . . C217 C 0.4848(4) 0.6304(3) 0.3923(3) 0.0506(11) Uani 1 1 d . . . H217 H 0.4388 0.6303 0.4215 0.061 Uiso 1 1 calc R . . C218 C 0.4590(3) 0.6858(3) 0.3197(3) 0.0444(10) Uani 1 1 d . . . H218 H 0.3948 0.7232 0.2987 0.053 Uiso 1 1 calc R . . C219 C 0.5265(3) 0.6892(3) 0.2741(2) 0.0396(9) Uani 1 1 d . . . C220 C 0.5043(3) 0.7490(3) 0.2009(3) 0.0402(9) Uani 1 1 d . . . C221 C 0.7494(4) 0.6961(4) 0.1540(4) 0.0676(15) Uani 1 1 d . . . O221 O 0.7230(3) 0.7380(4) 0.0834(3) 0.1083(18) Uani 1 1 d . . . O222 O 0.8381(2) 0.6538(3) 0.1944(2) 0.0664(10) Uani 1 1 d . . . C222 C 0.4034(3) 0.8136(3) 0.1629(3) 0.0419(10) Uani 1 1 d . . . H22A H 0.3989 0.8592 0.2078 0.050 Uiso 1 1 calc R . . H22B H 0.4092 0.8586 0.1182 0.050 Uiso 1 1 calc R . . C223 C 0.3022(3) 0.7527(3) 0.1253(2) 0.0372(9) Uani 1 1 d . . . C224 C 0.2275(3) 0.7580(3) 0.1604(3) 0.0384(9) Uani 1 1 d . . . O224 O 0.2447(2) 0.8226(2) 0.22701(18) 0.0459(8) Uani 1 1 d . . . H224 H 0.190(3) 0.811(3) 0.238(3) 0.051(13) Uiso 1 1 d . . . C225 C 0.1333(3) 0.6983(3) 0.1268(3) 0.0431(10) Uani 1 1 d . . . C226 C 0.1165(3) 0.6340(3) 0.0595(3) 0.0416(10) Uani 1 1 d . . . H226 H 0.0557 0.5915 0.0398 0.050 Uiso 1 1 calc R . . C227 C 0.1869(3) 0.6296(3) 0.0191(3) 0.0436(10) Uani 1 1 d . . . C228 C 0.1661(4) 0.5679(3) -0.0540(3) 0.0562(12) Uani 1 1 d . . . H228 H 0.1067 0.5234 -0.0728 0.067 Uiso 1 1 calc R . . C229 C 0.2291(5) 0.5713(4) -0.0974(3) 0.0669(14) Uani 1 1 d . . . H229 H 0.2132 0.5305 -0.1469 0.080 Uiso 1 1 calc R . . C230 C 0.3177(4) 0.6348(4) -0.0695(3) 0.0608(13) Uani 1 1 d . . . H230 H 0.3597 0.6391 -0.1020 0.073 Uiso 1 1 calc R . . C231 C 0.3453(3) 0.6912(3) 0.0040(3) 0.0500(11) Uani 1 1 d . . . H231 H 0.4083 0.7306 0.0235 0.060 Uiso 1 1 calc R . . C232 C 0.2800(3) 0.6911(3) 0.0512(3) 0.0408(9) Uani 1 1 d . . . C233 C 0.0546(3) 0.7056(3) 0.1664(3) 0.0490(11) Uani 1 1 d . . . O233 O 0.0692(2) 0.7606(2) 0.2284(2) 0.0577(9) Uani 1 1 d . . . O234 O -0.0300(2) 0.6522(3) 0.1280(3) 0.0688(11) Uani 1 1 d . . . H234 H -0.0707 0.6591 0.1536 0.083 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.107(4) 0.095(4) 0.104(4) 0.051(3) 0.059(4) 0.047(3) C12 0.084(4) 0.069(4) 0.116(6) 0.029(4) 0.016(4) 0.018(3) C13 0.079(4) 0.064(3) 0.072(4) 0.001(3) 0.026(3) 0.003(3) C14 0.080(5) 0.121(6) 0.123(6) 0.052(5) 0.024(5) 0.024(4) C15 0.082(4) 0.105(5) 0.080(4) 0.031(4) 0.028(4) 0.017(4) C16 0.097(5) 0.078(4) 0.081(4) 0.015(3) 0.036(4) -0.016(3) C17 0.131(7) 0.128(7) 0.177(9) 0.073(6) 0.089(7) 0.054(5) C18 0.121(7) 0.302(16) 0.184(11) 0.143(11) 0.042(7) -0.031(8) O211 0.0503(18) 0.067(2) 0.086(3) 0.0295(18) 0.0443(18) 0.0067(15) C211 0.036(2) 0.049(2) 0.061(3) 0.012(2) 0.023(2) -0.0021(17) C212 0.034(2) 0.047(2) 0.073(3) 0.003(2) 0.027(2) -0.0054(18) C213 0.033(2) 0.044(2) 0.061(3) -0.002(2) 0.0131(19) -0.0036(17) C214 0.042(2) 0.034(2) 0.046(2) -0.0051(17) 0.0112(18) -0.0041(16) C215 0.058(3) 0.045(2) 0.047(3) -0.003(2) 0.016(2) 0.008(2) C216 0.080(3) 0.047(2) 0.038(2) 0.0030(19) 0.020(2) 0.014(2) C217 0.067(3) 0.046(2) 0.043(2) -0.0027(19) 0.027(2) 0.006(2) C218 0.051(2) 0.043(2) 0.042(2) -0.0066(18) 0.0213(19) -0.0015(18) C219 0.037(2) 0.038(2) 0.042(2) -0.0085(17) 0.0138(17) -0.0083(16) C220 0.0327(19) 0.042(2) 0.048(2) -0.0018(17) 0.0170(18) -0.0057(16) C221 0.048(3) 0.056(3) 0.115(5) 0.019(3) 0.049(3) 0.002(2) O221 0.078(3) 0.133(4) 0.152(4) 0.083(3) 0.087(3) 0.042(2) O222 0.0357(17) 0.069(2) 0.101(3) -0.0010(18) 0.0333(18) -0.0019(14) C222 0.040(2) 0.044(2) 0.048(2) 0.0048(18) 0.0237(18) -0.0022(16) C223 0.0361(19) 0.040(2) 0.037(2) 0.0068(16) 0.0155(17) 0.0043(15) C224 0.036(2) 0.039(2) 0.043(2) 0.0019(17) 0.0177(17) 0.0016(16) O224 0.0405(16) 0.0567(18) 0.0486(18) -0.0073(14) 0.0261(14) -0.0042(13) C225 0.035(2) 0.042(2) 0.055(3) 0.0051(19) 0.0204(18) 0.0035(17) C226 0.036(2) 0.042(2) 0.041(2) 0.0029(18) 0.0082(17) -0.0030(16) C227 0.046(2) 0.043(2) 0.039(2) 0.0033(18) 0.0121(18) -0.0001(17) C228 0.078(3) 0.052(3) 0.039(2) 0.0009(19) 0.022(2) -0.005(2) C229 0.107(4) 0.058(3) 0.042(3) -0.003(2) 0.036(3) -0.002(3) C230 0.077(3) 0.070(3) 0.049(3) 0.004(2) 0.039(3) 0.009(3) C231 0.056(3) 0.057(3) 0.045(2) 0.013(2) 0.029(2) 0.004(2) C232 0.040(2) 0.044(2) 0.041(2) 0.0114(18) 0.0178(17) 0.0057(17) C233 0.033(2) 0.047(2) 0.070(3) 0.003(2) 0.023(2) 0.0022(18) O233 0.0435(17) 0.071(2) 0.069(2) -0.0038(17) 0.0333(16) -0.0029(14) O234 0.0396(17) 0.069(2) 0.109(3) -0.0171(19) 0.0416(18) -0.0094(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 N11 C16 1.301(8) . ? N11 C12 1.432(9) . ? C12 C13 1.367(10) . ? C12 C17 1.428(9) . ? C13 C14 1.301(9) . ? C14 C15 1.336(10) . ? C15 C16 1.377(9) . ? C15 C18 1.473(11) . ? O31 C31 1.317(14) . ? O31 C33 1.464(14) . ? C31 C32 1.338(15) . ? C31 C36 1.84(3) . ? C32 C36 1.53(3) . ? C32 C37 1.56(3) . ? C32 C34 1.709(19) . ? C33 O41 1.17(3) . ? C33 C34 1.430(17) . ? C33 C36 1.81(3) . ? C34 C35 1.24(3) . ? C34 O41 1.56(4) . ? C34 C37 1.63(4) . ? C34 C36 1.99(3) . ? C35 C37 1.31(4) . ? C35 O41 1.53(4) . ? C36 O41 1.39(4) . ? C36 C37 1.97(4) . ? O211 C211 1.358(5) . ? C211 C220 1.386(5) . ? C211 C212 1.446(6) . ? C212 C213 1.351(6) . ? C212 C221 1.509(6) . ? C213 C214 1.416(6) . ? C214 C215 1.411(6) . ? C214 C219 1.432(6) . ? C215 C216 1.347(6) . ? C216 C217 1.410(6) . ? C217 C218 1.359(6) . ? C218 C219 1.431(6) . ? C219 C220 1.402(6) . ? C220 C222 1.537(5) . ? C221 O221 1.245(7) . ? C221 O222 1.274(6) . ? C222 C223 1.513(5) . ? C223 C224 1.383(5) . ? C223 C232 1.429(6) . ? C224 O224 1.359(5) . ? C224 C225 1.429(5) . ? C225 C226 1.367(6) . ? C225 C233 1.491(6) . ? C226 C227 1.397(6) . ? C227 C228 1.418(6) . ? C227 C232 1.429(6) . ? C228 C229 1.347(6) . ? C229 C230 1.395(7) . ? C230 C231 1.377(6) . ? C231 C232 1.426(6) . ? C233 O233 1.229(5) . ? C233 O234 1.296(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 121.5(7) . . ? C13 C12 C17 128.8(8) . . ? C13 C12 N11 113.2(7) . . ? C17 C12 N11 118.0(8) . . ? C14 C13 C12 121.7(7) . . ? C13 C14 C15 127.0(9) . . ? C14 C15 C16 112.4(7) . . ? C14 C15 C18 125.6(9) . . ? C16 C15 C18 121.8(9) . . ? N11 C16 C15 124.2(7) . . ? C31 O31 C33 102.0(10) . . ? O31 C31 C32 117.3(12) . . ? O31 C31 C36 88.7(12) . . ? C32 C31 C36 54.8(10) . . ? C31 C32 C36 79.7(14) . . ? C31 C32 C37 153.6(18) . . ? C36 C32 C37 79.2(18) . . ? C31 C32 C34 99.8(11) . . ? C36 C32 C34 75.5(14) . . ? C37 C32 C34 59.6(14) . . ? O41 C33 C34 73.3(19) . . ? O41 C33 O31 135(2) . . ? C34 C33 O31 105.1(11) . . ? O41 C33 C36 50.0(19) . . ? C34 C33 C36 74.8(12) . . ? O31 C33 C36 85.8(12) . . ? C35 C34 C33 109(2) . . ? C35 C34 O41 64.9(19) . . ? C33 C34 O41 45.5(13) . . ? C35 C34 C37 52.0(18) . . ? C33 C34 C37 125.3(16) . . ? O41 C34 C37 87(2) . . ? C35 C34 C32 103.9(19) . . ? C33 C34 C32 93.7(10) . . ? O41 C34 C32 92.1(16) . . ? C37 C34 C32 55.7(13) . . ? C35 C34 C36 81.6(19) . . ? C33 C34 C36 61.3(11) . . ? O41 C34 C36 43.9(15) . . ? C37 C34 C36 65.1(15) . . ? C32 C34 C36 48.2(10) . . ? C34 C35 C37 80(2) . . ? C34 C35 O41 68(2) . . ? C37 C35 O41 102(3) . . ? O41 C36 C32 108(3) . . ? O41 C36 C33 40.1(17) . . ? C32 C36 C33 86.6(16) . . ? O41 C36 C31 112(2) . . ? C32 C36 C31 45.6(10) . . ? C33 C36 C31 72.7(13) . . ? O41 C36 C37 80(2) . . ? C32 C36 C37 51.2(13) . . ? C33 C36 C37 92.0(17) . . ? C31 C36 C37 95.5(17) . . ? O41 C36 C34 51.5(18) . . ? C32 C36 C34 56.3(11) . . ? C33 C36 C34 43.9(9) . . ? C31 C36 C34 75.3(13) . . ? C37 C36 C34 48.6(12) . . ? C35 C37 C32 109(3) . . ? C35 C37 C34 48.3(18) . . ? C32 C37 C34 64.7(14) . . ? C35 C37 C36 81(2) . . ? C32 C37 C36 49.7(13) . . ? C34 C37 C36 66.2(16) . . ? C33 O41 C36 90(3) . . ? C33 O41 C35 106(3) . . ? C36 O41 C35 97(3) . . ? C33 O41 C34 61.1(19) . . ? C36 O41 C34 85(2) . . ? C35 O41 C34 47.1(16) . . ? O211 C211 C220 119.8(4) . . ? O211 C211 C212 119.4(4) . . ? C220 C211 C212 120.8(4) . . ? C213 C212 C211 119.2(4) . . ? C213 C212 C221 120.8(4) . . ? C211 C212 C221 119.9(4) . . ? C212 C213 C214 121.8(4) . . ? C215 C214 C213 121.8(4) . . ? C215 C214 C219 119.8(4) . . ? C213 C214 C219 118.4(4) . . ? C216 C215 C214 121.6(4) . . ? C215 C216 C217 119.5(4) . . ? C218 C217 C216 121.0(4) . . ? C217 C218 C219 121.4(4) . . ? C220 C219 C218 122.9(4) . . ? C220 C219 C214 120.5(4) . . ? C218 C219 C214 116.6(4) . . ? C211 C220 C219 119.2(4) . . ? C211 C220 C222 119.0(4) . . ? C219 C220 C222 121.7(3) . . ? O221 C221 O222 124.9(5) . . ? O221 C221 C212 119.4(4) . . ? O222 C221 C212 115.6(5) . . ? C223 C222 C220 115.8(3) . . ? C224 C223 C232 118.4(3) . . ? C224 C223 C222 120.7(3) . . ? C232 C223 C222 120.8(3) . . ? O224 C224 C223 118.7(3) . . ? O224 C224 C225 120.2(3) . . ? C223 C224 C225 121.1(4) . . ? C226 C225 C224 119.8(4) . . ? C226 C225 C233 120.5(4) . . ? C224 C225 C233 119.7(4) . . ? C225 C226 C227 121.4(4) . . ? C226 C227 C228 121.3(4) . . ? C226 C227 C232 118.8(4) . . ? C228 C227 C232 119.8(4) . . ? C229 C228 C227 121.1(4) . . ? C228 C229 C230 120.0(4) . . ? C231 C230 C229 121.3(4) . . ? C230 C231 C232 120.4(4) . . ? C231 C232 C223 122.6(4) . . ? C231 C232 C227 117.1(4) . . ? C223 C232 C227 120.2(4) . . ? O233 C233 O234 124.0(4) . . ? O233 C233 C225 121.8(4) . . ? O234 C233 C225 114.2(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.24 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.003 _refine_diff_density_min -0.537 _refine_diff_density_rms 0.096 #=== END data_2 _database_code_depnum_ccdc_archive 'CCDC 788707' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,3 lutidine pamoate DMF solvate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H14 O6 2- , 2(C7 H10 N 1+) , C3 H7 N O' _chemical_formula_sum 'C40 H41 N3 O7' _chemical_formula_weight 675.76 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.8950(7) _cell_length_b 11.6523(6) _cell_length_c 21.2968(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.1310(10) _cell_angle_gamma 90.00 _cell_volume 3371.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2836 _cell_measurement_theta_min 2.303 _cell_measurement_theta_max 26.112 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9816 _exptl_absorpt_correction_T_max 0.9880 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 9520 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.15 _reflns_number_total 3378 _reflns_number_gt 2666 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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. All protons involved in proton transfer reactions were located in the difference map. ; _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^)+(0.0528P)^2^+1.7295P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3378 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1118 _refine_ls_wR_factor_gt 0.1024 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 -0.08562(16) 1.2233(2) 0.13221(11) 0.0401(6) Uani 0.50 1 d P A -1 N1 N -0.0022(3) 1.1850(2) 0.23398(11) 0.0314(7) Uani 0.50 1 d P A -1 C1 C -0.0098(2) 1.2012(3) 0.17100(15) 0.0313(7) Uani 0.50 1 d P A -1 H1 H 0.0488 1.1950 0.1550 0.038 Uiso 0.50 1 calc PR A -1 C2 C 0.0898(3) 1.1489(4) 0.2750(2) 0.0498(10) Uani 0.50 1 d P A -1 H2A H 0.1416 1.1475 0.2501 0.075 Uiso 0.50 1 calc PR A -1 H2B H 0.0819 1.0720 0.2918 0.075 Uiso 0.50 1 calc PR A -1 H2C H 0.1080 1.2029 0.3108 0.075 Uiso 0.50 1 calc PR A -1 C3 C -0.0890(3) 1.1875(4) 0.26200(19) 0.0442(9) Uani 0.50 1 d P A -1 H3A H -0.1441 1.2216 0.2313 0.066 Uiso 0.50 1 calc PR A -1 H3B H -0.0753 1.2336 0.3014 0.066 Uiso 0.50 1 calc PR A -1 H3C H -0.1061 1.1091 0.2722 0.066 Uiso 0.50 1 calc PR A -1 N11 N 0.48092(9) 0.86945(11) 0.53942(5) 0.0260(3) Uani 1 1 d . . . H11 H 0.4020(16) 0.8771(17) 0.5196(10) 0.065(6) Uiso 1 1 d . . . C12 C 0.52248(11) 0.92832(13) 0.59240(7) 0.0292(3) Uani 1 1 d . . . C13 C 0.62355(11) 0.91892(15) 0.61706(7) 0.0337(4) Uani 1 1 d . . . C14 C 0.67680(11) 0.84669(18) 0.58537(8) 0.0441(5) Uani 1 1 d . . . H14 H 0.7457 0.8388 0.6011 0.053 Uiso 1 1 calc R . . C15 C 0.63182(12) 0.78596(17) 0.53140(8) 0.0427(4) Uani 1 1 d . . . H15 H 0.6689 0.7362 0.5103 0.051 Uiso 1 1 calc R . . C16 C 0.53225(11) 0.79915(14) 0.50897(7) 0.0316(4) Uani 1 1 d . . . H16 H 0.4998 0.7584 0.4719 0.038 Uiso 1 1 calc R . . C17 C 0.45551(14) 1.00237(15) 0.62142(8) 0.0424(4) Uani 1 1 d . . . H17A H 0.3887 0.9985 0.5950 0.064 Uiso 1 1 calc R . . H17B H 0.4789 1.0819 0.6234 0.064 Uiso 1 1 calc R . . H17C H 0.4550 0.9752 0.6649 0.064 Uiso 1 1 calc R . . C18 C 0.67269(13) 0.98278(18) 0.67658(8) 0.0487(5) Uani 1 1 d . . . H18A H 0.6643 0.9399 0.7147 0.073 Uiso 1 1 calc R . . H18B H 0.6427 1.0589 0.6768 0.073 Uiso 1 1 calc R . . H18C H 0.7430 0.9912 0.6771 0.073 Uiso 1 1 calc R . . O211 O 0.19418(7) 0.71150(9) 0.32257(5) 0.0250(2) Uani 1 1 d . . . C211 C 0.13103(10) 0.78350(11) 0.34440(6) 0.0187(3) Uani 1 1 d . . . H211 H 0.2541(15) 0.7251(17) 0.3509(9) 0.051(6) Uiso 1 1 d . . . C212 C 0.16637(9) 0.84920(12) 0.40148(6) 0.0197(3) Uani 1 1 d . . . C213 C 0.10337(10) 0.92257(12) 0.42284(6) 0.0206(3) Uani 1 1 d . . . H213 H 0.1276 0.9695 0.4592 0.025 Uiso 1 1 calc R . . C214 C 0.00309(10) 0.93006(12) 0.39208(6) 0.0202(3) Uani 1 1 d . . . C215 C -0.06367(10) 1.00024(12) 0.41694(6) 0.0246(3) Uani 1 1 d . . . H215 H -0.0393 1.0491 0.4524 0.029 Uiso 1 1 calc R . . C216 C -0.16219(10) 0.99885(13) 0.39089(7) 0.0273(3) Uani 1 1 d . . . H216 H -0.2062 1.0443 0.4090 0.033 Uiso 1 1 calc R . . C217 C -0.19804(10) 0.92922(13) 0.33688(6) 0.0266(3) Uani 1 1 d . . . H217 H -0.2667 0.9274 0.3191 0.032 Uiso 1 1 calc R . . C218 C -0.13548(10) 0.86411(12) 0.30967(6) 0.0225(3) Uani 1 1 d . . . H218 H -0.1612 0.8201 0.2724 0.027 Uiso 1 1 calc R . . C219 C -0.03255(9) 0.86140(11) 0.33646(6) 0.0190(3) Uani 1 1 d . . . C220 C 0.03450(9) 0.79095(11) 0.31121(6) 0.0179(3) Uani 1 1 d . . . O221 O 0.29608(7) 0.89188(9) 0.49024(4) 0.0285(3) Uani 1 1 d . . . C221 C 0.27163(10) 0.83885(12) 0.43718(6) 0.0231(3) Uani 1 1 d . . . O222 O 0.33022(7) 0.77953(9) 0.41270(5) 0.0294(3) Uani 1 1 d . . . C222 C 0.0000 0.72139(16) 0.2500 0.0195(4) Uani 1 2 d S . . H22A H -0.0547 0.6711 0.2561 0.023 Uiso 0.50 1 calc PR . . H22B H 0.0547 0.6711 0.2439 0.023 Uiso 0.50 1 calc PR . . 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 0.0352(13) 0.0468(14) 0.0371(12) 0.0053(11) 0.0051(10) -0.0050(11) N1 0.0254(12) 0.0390(13) 0.032(2) 0.0022(10) 0.010(2) -0.0003(14) C1 0.0263(16) 0.0359(18) 0.0332(17) -0.0025(13) 0.0096(13) -0.0044(13) C2 0.038(2) 0.066(3) 0.043(2) 0.012(2) 0.0034(18) 0.0036(19) C3 0.036(2) 0.063(3) 0.037(2) 0.0035(19) 0.0145(17) -0.0023(18) N11 0.0222(6) 0.0318(7) 0.0225(6) 0.0055(5) 0.0010(5) -0.0024(5) C12 0.0321(8) 0.0298(8) 0.0242(7) 0.0088(6) 0.0023(6) -0.0059(7) C13 0.0297(8) 0.0440(10) 0.0257(7) 0.0117(7) 0.0016(6) -0.0152(7) C14 0.0196(8) 0.0745(13) 0.0363(9) 0.0104(9) 0.0018(7) -0.0098(8) C15 0.0250(8) 0.0641(12) 0.0398(9) 0.0044(9) 0.0090(7) 0.0026(8) C16 0.0268(8) 0.0388(9) 0.0290(8) 0.0033(7) 0.0055(6) -0.0020(7) C17 0.0529(11) 0.0403(10) 0.0303(8) 0.0003(7) 0.0006(8) 0.0059(8) C18 0.0452(10) 0.0633(13) 0.0329(9) 0.0081(8) -0.0027(8) -0.0287(9) O211 0.0220(5) 0.0312(6) 0.0208(5) -0.0031(4) 0.0023(4) 0.0098(4) C211 0.0217(7) 0.0192(7) 0.0161(6) 0.0029(5) 0.0059(5) 0.0039(5) C212 0.0195(7) 0.0224(7) 0.0172(6) 0.0029(5) 0.0037(5) 0.0012(5) C213 0.0238(7) 0.0217(7) 0.0158(6) 0.0007(5) 0.0033(5) 0.0006(6) C214 0.0230(7) 0.0213(7) 0.0167(6) 0.0036(5) 0.0047(5) 0.0034(6) C215 0.0298(7) 0.0255(8) 0.0181(6) 0.0003(6) 0.0047(6) 0.0078(6) C216 0.0273(7) 0.0337(8) 0.0220(7) 0.0045(6) 0.0078(6) 0.0134(6) C217 0.0192(7) 0.0389(9) 0.0212(7) 0.0061(6) 0.0036(5) 0.0071(6) C218 0.0219(7) 0.0285(8) 0.0167(6) 0.0031(5) 0.0032(5) 0.0024(6) C219 0.0211(7) 0.0210(7) 0.0155(6) 0.0041(5) 0.0047(5) 0.0021(5) C220 0.0212(7) 0.0173(7) 0.0156(6) 0.0030(5) 0.0048(5) 0.0004(5) O221 0.0234(5) 0.0385(6) 0.0211(5) -0.0048(4) -0.0008(4) 0.0028(4) C221 0.0220(7) 0.0272(7) 0.0198(7) 0.0035(6) 0.0036(5) 0.0018(6) O222 0.0207(5) 0.0415(6) 0.0246(5) -0.0031(4) 0.0018(4) 0.0089(4) C222 0.0195(9) 0.0202(10) 0.0192(9) 0.000 0.0048(7) 0.000 _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 1.221(4) . ? N1 C1 1.336(4) . ? N1 C2 1.451(5) . ? N1 C3 1.454(5) . ? N11 C16 1.3396(19) . ? N11 C12 1.3429(19) . ? C12 C13 1.396(2) . ? C12 C17 1.495(2) . ? C13 C14 1.386(3) . ? C13 C18 1.504(2) . ? C14 C15 1.382(2) . ? C15 C16 1.374(2) . ? O211 C211 1.3643(15) . ? C211 C220 1.3811(18) . ? C211 C212 1.4333(18) . ? C212 C213 1.3681(18) . ? C212 C221 1.5049(18) . ? C213 C214 1.4123(18) . ? C214 C215 1.4197(18) . ? C214 C219 1.4289(18) . ? C215 C216 1.365(2) . ? C216 C217 1.410(2) . ? C217 C218 1.3708(19) . ? C218 C219 1.4244(18) . ? C219 C220 1.4290(18) . ? C220 C222 1.5242(16) . ? O221 C221 1.2699(17) . ? C221 O222 1.2613(16) . ? C222 C220 1.5242(16) 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 C1 N1 C2 121.3(4) . . ? C1 N1 C3 120.8(4) . . ? C2 N1 C3 117.4(3) . . ? O1 C1 N1 125.7(3) . . ? C16 N11 C12 122.71(13) . . ? N11 C12 C13 119.79(15) . . ? N11 C12 C17 116.56(13) . . ? C13 C12 C17 123.64(14) . . ? C14 C13 C12 117.52(14) . . ? C14 C13 C18 121.10(15) . . ? C12 C13 C18 121.38(16) . . ? C15 C14 C13 121.43(15) . . ? C16 C15 C14 118.56(16) . . ? N11 C16 C15 119.98(15) . . ? O211 C211 C220 119.29(12) . . ? O211 C211 C212 119.15(11) . . ? C220 C211 C212 121.55(12) . . ? C213 C212 C211 119.13(12) . . ? C213 C212 C221 120.26(12) . . ? C211 C212 C221 120.61(12) . . ? C212 C213 C214 121.48(12) . . ? C213 C214 C215 121.39(12) . . ? C213 C214 C219 119.09(12) . . ? C215 C214 C219 119.45(12) . . ? C216 C215 C214 121.32(13) . . ? C215 C216 C217 119.37(13) . . ? C218 C217 C216 121.10(13) . . ? C217 C218 C219 121.03(13) . . ? C218 C219 C214 117.62(12) . . ? C218 C219 C220 122.76(12) . . ? C214 C219 C220 119.59(12) . . ? C211 C220 C219 118.90(12) . . ? C211 C220 C222 120.09(10) . . ? C219 C220 C222 120.97(10) . . ? O222 C221 O221 124.01(12) . . ? O222 C221 C212 118.57(12) . . ? O221 C221 C212 117.42(12) . . ? C220 C222 C220 115.75(15) . 2 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O221 1.09(2) 1.48(2) 2.5750(15) 177.0(19) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.15 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.261 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.040 #=== END data_3 _database_code_depnum_ccdc_archive 'CCDC 788708' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,4 lutidinium pamoate DMF solvate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 O6 1- , C7 H10 N 1+ , C3 H7 N O' _chemical_formula_sum 'C33 H32 N2 O7' _chemical_formula_weight 568.61 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.9767(12) _cell_length_b 12.6966(11) _cell_length_c 16.7676(15) _cell_angle_alpha 90.00 _cell_angle_beta 108.7730(10) _cell_angle_gamma 90.00 _cell_volume 2817.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3918 _cell_measurement_theta_min 2.223 _cell_measurement_theta_max 27.524 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9731 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 16490 _diffrn_reflns_av_R_equivalents 0.0663 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.88 _reflns_number_total 6121 _reflns_number_gt 4032 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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. All protons involved in proton transfer reactions were located in the difference map. ; _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^)+(0.0622P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6121 _refine_ls_number_parameters 413 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 N11 N 0.24529(11) 0.66792(11) 0.56393(9) 0.0252(3) Uani 1 1 d . . . H11 H 0.2543(15) 0.6978(16) 0.5133(13) 0.055(6) Uiso 1 1 d . . . C12 C 0.31804(13) 0.60577(13) 0.61466(10) 0.0258(4) Uani 1 1 d . . . C13 C 0.30187(13) 0.56226(14) 0.68444(10) 0.0285(4) Uani 1 1 d . . . H13 H 0.3522 0.5182 0.7207 0.034 Uiso 1 1 calc R . . C14 C 0.21375(14) 0.58135(14) 0.70277(10) 0.0294(4) Uani 1 1 d . . . C15 C 0.14086(13) 0.64621(14) 0.64831(10) 0.0280(4) Uani 1 1 d . . . H15 H 0.0794 0.6607 0.6590 0.034 Uiso 1 1 calc R . . C16 C 0.15884(13) 0.68864(14) 0.57948(10) 0.0272(4) Uani 1 1 d . . . H16 H 0.1097 0.7331 0.5424 0.033 Uiso 1 1 calc R . . C17 C 0.41140(13) 0.58901(15) 0.59137(12) 0.0365(5) Uani 1 1 d . . . H17A H 0.3942 0.5508 0.5378 0.055 Uiso 1 1 calc R . . H17B H 0.4602 0.5478 0.6355 0.055 Uiso 1 1 calc R . . H17C H 0.4411 0.6574 0.5856 0.055 Uiso 1 1 calc R . . C18 C 0.19683(17) 0.53427(17) 0.77929(11) 0.0447(5) Uani 1 1 d . . . H18A H 0.1412 0.5711 0.7909 0.067 Uiso 1 1 calc R . . H18B H 0.2585 0.5414 0.8277 0.067 Uiso 1 1 calc R . . H18C H 0.1798 0.4595 0.7691 0.067 Uiso 1 1 calc R . . O211 O 0.45914(9) 0.81555(9) 0.41665(7) 0.0226(3) Uani 1 1 d . . . H211 H 0.4091(18) 0.8049(18) 0.4359(14) 0.068(8) Uiso 1 1 d . . . O221 O 0.29111(8) 0.74587(9) 0.42731(7) 0.0252(3) Uani 1 1 d . . . O222 O 0.18038(8) 0.67857(9) 0.31074(7) 0.0238(3) Uani 1 1 d . . . O224 O 0.77325(9) 0.81871(9) 0.27604(7) 0.0230(3) Uani 1 1 d . . . H224 H 0.8272(17) 0.8103(17) 0.2592(13) 0.059(7) Uiso 1 1 d . . . O233 O 0.94698(8) 0.76213(9) 0.27050(7) 0.0269(3) Uani 1 1 d . . . O234 O 1.04659(8) 0.66409(9) 0.37538(7) 0.0253(3) Uani 1 1 d . . . H234 H 1.1086(17) 0.6770(19) 0.3460(13) 0.081(8) Uiso 1 1 d . . . C211 C 0.44257(11) 0.75513(12) 0.34636(9) 0.0173(3) Uani 1 1 d . . . C212 C 0.34764(11) 0.70264(12) 0.31170(9) 0.0180(3) Uani 1 1 d . . . C213 C 0.32979(12) 0.64557(12) 0.23921(9) 0.0191(3) Uani 1 1 d . . . H213 H 0.2666 0.6109 0.2162 0.023 Uiso 1 1 calc R . . C214 C 0.40257(11) 0.63680(12) 0.19780(9) 0.0181(3) Uani 1 1 d . . . C215 C 0.38167(12) 0.58083(13) 0.12140(10) 0.0216(4) Uani 1 1 d . . . H215 H 0.3179 0.5474 0.0981 0.026 Uiso 1 1 calc R . . C216 C 0.45147(12) 0.57382(13) 0.08041(10) 0.0222(4) Uani 1 1 d . . . H216 H 0.4367 0.5353 0.0293 0.027 Uiso 1 1 calc R . . C217 C 0.54589(12) 0.62435(12) 0.11479(9) 0.0206(4) Uani 1 1 d . . . H217 H 0.5946 0.6195 0.0864 0.025 Uiso 1 1 calc R . . C218 C 0.56839(12) 0.68016(12) 0.18829(9) 0.0185(3) Uani 1 1 d . . . H218 H 0.6322 0.7139 0.2098 0.022 Uiso 1 1 calc R . . C219 C 0.49790(11) 0.68857(12) 0.23325(9) 0.0166(3) Uani 1 1 d . . . C220 C 0.51747(11) 0.74790(12) 0.30898(9) 0.0170(3) Uani 1 1 d . . . C221 C 0.26804(12) 0.71010(12) 0.35352(10) 0.0192(3) Uani 1 1 d . . . C222 C 0.61583(11) 0.80917(12) 0.34592(9) 0.0185(3) Uani 1 1 d . . . H22A H 0.6239 0.8566 0.3016 0.022 Uiso 1 1 calc R . . H22B H 0.6090 0.8542 0.3920 0.022 Uiso 1 1 calc R . . C223 C 0.71233(11) 0.74479(12) 0.38032(9) 0.0174(3) Uani 1 1 d . . . C224 C 0.78774(12) 0.75349(12) 0.34334(9) 0.0181(3) Uani 1 1 d . . . C225 C 0.88078(11) 0.69677(12) 0.37568(9) 0.0183(3) Uani 1 1 d . . . C226 C 0.89557(11) 0.63236(12) 0.44409(9) 0.0191(3) Uani 1 1 d . . . H226 H 0.9563 0.5928 0.4641 0.023 Uiso 1 1 calc R . . C227 C 0.82276(11) 0.62340(12) 0.48559(9) 0.0179(3) Uani 1 1 d . . . C228 C 0.84171(12) 0.56261(13) 0.55996(10) 0.0214(4) Uani 1 1 d . . . H228 H 0.9021 0.5224 0.5797 0.026 Uiso 1 1 calc R . . C229 C 0.77430(12) 0.56086(13) 0.60386(10) 0.0232(4) Uani 1 1 d . . . H229 H 0.7880 0.5203 0.6539 0.028 Uiso 1 1 calc R . . C230 C 0.68431(12) 0.61999(13) 0.57389(9) 0.0220(4) Uani 1 1 d . . . H230 H 0.6381 0.6200 0.6048 0.026 Uiso 1 1 calc R . . C231 C 0.66231(12) 0.67735(12) 0.50112(9) 0.0199(4) Uani 1 1 d . . . H231 H 0.6004 0.7150 0.4818 0.024 Uiso 1 1 calc R . . C232 C 0.73064(11) 0.68172(12) 0.45383(9) 0.0174(3) Uani 1 1 d . . . C233 C 0.96152(12) 0.71010(13) 0.33582(10) 0.0201(4) Uani 1 1 d . . . C1 C 1.03479(15) 0.55096(18) 0.16239(12) 0.0463(5) Uani 1 1 d . A . H1A H 1.0777 0.4881 0.1728 0.069 Uiso 1 1 calc R . . H1B H 1.0162 0.5669 0.2127 0.069 Uiso 1 1 calc R . . H1C H 1.0717 0.6107 0.1495 0.069 Uiso 1 1 calc R . . N2 N 0.94439(11) 0.53195(11) 0.09192(8) 0.0259(3) Uani 1 1 d . . . C3 C 0.87270(17) 0.61664(17) 0.06387(14) 0.0500(6) Uani 1 1 d . A . H3A H 0.8982 0.6675 0.0316 0.075 Uiso 1 1 calc R . . H3B H 0.8632 0.6518 0.1128 0.075 Uiso 1 1 calc R . . H3C H 0.8079 0.5882 0.0281 0.075 Uiso 1 1 calc R . . C4A C 0.9360(4) 0.4405(4) 0.0503(3) 0.0275(10) Uani 0.777(6) 1 d P A 1 H4A H 0.9885 0.3905 0.0718 0.033 Uiso 0.777(6) 1 calc PR A 1 O5A O 0.86704(14) 0.41560(15) -0.01259(12) 0.0432(8) Uani 0.777(6) 1 d P A 1 C4B C 0.9089(18) 0.453(2) 0.0396(18) 0.070(10) Uiso 0.223(6) 1 d P A 2 H4B H 0.8452 0.4597 -0.0031 0.084 Uiso 0.223(6) 1 calc PR A 2 O5B O 0.9577(5) 0.3718(6) 0.0456(4) 0.048(3) Uani 0.223(6) 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0281(8) 0.0257(8) 0.0230(7) -0.0024(6) 0.0100(6) -0.0062(6) C12 0.0266(9) 0.0216(9) 0.0270(9) -0.0082(7) 0.0059(8) -0.0052(7) C13 0.0329(10) 0.0219(9) 0.0264(9) -0.0020(8) 0.0033(8) -0.0034(8) C14 0.0409(11) 0.0233(10) 0.0234(9) -0.0049(8) 0.0096(8) -0.0112(8) C15 0.0280(10) 0.0272(10) 0.0315(9) -0.0062(8) 0.0132(8) -0.0079(8) C16 0.0267(10) 0.0260(10) 0.0266(9) -0.0030(8) 0.0055(8) -0.0024(8) C17 0.0297(10) 0.0384(11) 0.0420(11) -0.0126(9) 0.0122(9) -0.0050(9) C18 0.0635(15) 0.0420(13) 0.0326(10) 0.0025(10) 0.0209(10) -0.0119(11) O211 0.0196(6) 0.0292(7) 0.0212(6) -0.0061(5) 0.0096(5) -0.0016(5) O221 0.0222(6) 0.0346(7) 0.0222(6) -0.0039(5) 0.0118(5) -0.0035(5) O222 0.0169(6) 0.0324(7) 0.0243(6) -0.0008(5) 0.0098(5) -0.0011(5) O224 0.0182(6) 0.0294(7) 0.0236(6) 0.0057(5) 0.0097(5) 0.0012(5) O233 0.0222(6) 0.0368(7) 0.0247(6) 0.0066(6) 0.0116(5) 0.0038(5) O234 0.0174(6) 0.0350(7) 0.0264(6) 0.0048(5) 0.0112(5) 0.0052(5) C211 0.0173(8) 0.0180(8) 0.0159(8) 0.0020(6) 0.0047(6) 0.0033(6) C212 0.0178(8) 0.0186(8) 0.0188(8) 0.0037(7) 0.0077(6) 0.0036(6) C213 0.0153(8) 0.0202(9) 0.0217(8) 0.0029(7) 0.0056(6) -0.0006(6) C214 0.0187(8) 0.0172(8) 0.0189(8) 0.0030(7) 0.0067(6) 0.0020(6) C215 0.0218(9) 0.0199(9) 0.0227(8) 0.0002(7) 0.0068(7) -0.0019(7) C216 0.0276(9) 0.0210(9) 0.0194(8) -0.0017(7) 0.0094(7) 0.0019(7) C217 0.0225(9) 0.0219(9) 0.0215(8) 0.0033(7) 0.0126(7) 0.0048(7) C218 0.0173(8) 0.0193(9) 0.0196(8) 0.0026(7) 0.0067(7) 0.0009(6) C219 0.0168(8) 0.0150(8) 0.0186(8) 0.0041(6) 0.0064(6) 0.0033(6) C220 0.0148(8) 0.0176(8) 0.0182(8) 0.0030(7) 0.0046(6) 0.0015(6) C221 0.0174(8) 0.0193(9) 0.0218(8) 0.0023(7) 0.0077(7) 0.0008(7) C222 0.0181(8) 0.0187(8) 0.0197(8) 0.0001(7) 0.0076(7) 0.0006(6) C223 0.0153(8) 0.0174(8) 0.0194(8) -0.0029(7) 0.0054(6) -0.0018(6) C224 0.0180(8) 0.0183(9) 0.0173(8) -0.0020(6) 0.0047(6) -0.0019(6) C225 0.0161(8) 0.0202(9) 0.0195(8) -0.0039(7) 0.0069(6) -0.0020(6) C226 0.0154(8) 0.0194(9) 0.0216(8) -0.0019(7) 0.0048(6) 0.0007(6) C227 0.0178(8) 0.0161(8) 0.0201(8) -0.0025(7) 0.0065(7) -0.0018(6) C228 0.0217(9) 0.0195(9) 0.0225(8) -0.0003(7) 0.0063(7) 0.0021(7) C229 0.0274(9) 0.0216(9) 0.0208(8) 0.0007(7) 0.0078(7) -0.0019(7) C230 0.0220(9) 0.0249(9) 0.0214(8) -0.0030(7) 0.0103(7) -0.0037(7) C231 0.0174(8) 0.0218(9) 0.0207(8) -0.0032(7) 0.0065(7) 0.0000(7) C232 0.0159(8) 0.0171(8) 0.0187(8) -0.0056(7) 0.0049(6) -0.0030(6) C233 0.0168(8) 0.0223(9) 0.0216(8) -0.0031(7) 0.0066(7) -0.0005(7) C1 0.0363(12) 0.0587(15) 0.0377(11) -0.0034(11) 0.0032(9) -0.0054(10) N2 0.0271(8) 0.0244(8) 0.0239(7) -0.0008(6) 0.0053(6) -0.0011(6) C3 0.0544(14) 0.0477(14) 0.0496(13) 0.0132(11) 0.0191(11) 0.0209(11) C4A 0.035(2) 0.025(2) 0.0280(17) 0.0031(13) 0.0167(17) -0.0009(16) O5A 0.0426(13) 0.0464(13) 0.0378(12) -0.0156(9) 0.0090(10) -0.0123(9) O5B 0.070(6) 0.025(5) 0.052(4) 0.001(3) 0.026(4) 0.010(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.342(2) . ? N11 C12 1.350(2) . ? C12 C13 1.377(2) . ? C12 C17 1.493(2) . ? C13 C14 1.383(2) . ? C14 C15 1.397(2) . ? C14 C18 1.502(2) . ? C15 C16 1.368(2) . ? O211 C211 1.3623(18) . ? O221 C221 1.2587(18) . ? O222 C221 1.2689(18) . ? O224 C224 1.3612(18) . ? O233 C233 1.2387(18) . ? O234 C233 1.2991(18) . ? C211 C220 1.385(2) . ? C211 C212 1.430(2) . ? C212 C213 1.367(2) . ? C212 C221 1.497(2) . ? C213 C214 1.408(2) . ? C214 C215 1.411(2) . ? C214 C219 1.432(2) . ? C215 C216 1.365(2) . ? C216 C217 1.413(2) . ? C217 C218 1.368(2) . ? C218 C219 1.424(2) . ? C219 C220 1.425(2) . ? C220 C222 1.527(2) . ? C222 C223 1.523(2) . ? C223 C224 1.389(2) . ? C223 C232 1.422(2) . ? C224 C225 1.432(2) . ? C225 C226 1.369(2) . ? C225 C233 1.495(2) . ? C226 C227 1.410(2) . ? C227 C228 1.417(2) . ? C227 C232 1.431(2) . ? C228 C229 1.370(2) . ? C229 C230 1.411(2) . ? C230 C231 1.368(2) . ? C231 C232 1.425(2) . ? C1 N2 1.446(2) . ? N2 C4B 1.32(3) . ? N2 C4A 1.340(5) . ? N2 C3 1.442(2) . ? C4A O5A 1.219(5) . ? C4B O5B 1.22(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 C16 N11 C12 122.33(15) . . ? N11 C12 C13 118.27(16) . . ? N11 C12 C17 117.57(15) . . ? C13 C12 C17 124.16(17) . . ? C12 C13 C14 121.32(17) . . ? C13 C14 C15 118.18(16) . . ? C13 C14 C18 121.09(17) . . ? C15 C14 C18 120.73(17) . . ? C16 C15 C14 119.36(17) . . ? N11 C16 C15 120.54(17) . . ? O211 C211 C220 119.08(14) . . ? O211 C211 C212 119.41(13) . . ? C220 C211 C212 121.50(14) . . ? C213 C212 C211 119.21(14) . . ? C213 C212 C221 119.97(14) . . ? C211 C212 C221 120.82(14) . . ? C212 C213 C214 121.74(15) . . ? C213 C214 C215 121.07(14) . . ? C213 C214 C219 118.82(14) . . ? C215 C214 C219 120.08(14) . . ? C216 C215 C214 121.15(15) . . ? C215 C216 C217 119.34(15) . . ? C218 C217 C216 121.10(14) . . ? C217 C218 C219 121.22(14) . . ? C218 C219 C220 122.97(14) . . ? C218 C219 C214 117.10(14) . . ? C220 C219 C214 119.91(13) . . ? C211 C220 C219 118.81(14) . . ? C211 C220 C222 119.71(13) . . ? C219 C220 C222 121.36(13) . . ? O221 C221 O222 124.38(14) . . ? O221 C221 C212 119.31(14) . . ? O222 C221 C212 116.31(13) . . ? C223 C222 C220 116.89(13) . . ? C224 C223 C232 118.76(14) . . ? C224 C223 C222 119.67(14) . . ? C232 C223 C222 121.39(13) . . ? O224 C224 C223 119.13(14) . . ? O224 C224 C225 119.64(13) . . ? C223 C224 C225 121.21(14) . . ? C226 C225 C224 119.44(14) . . ? C226 C225 C233 120.67(14) . . ? C224 C225 C233 119.88(14) . . ? C225 C226 C227 121.55(14) . . ? C226 C227 C228 121.20(14) . . ? C226 C227 C232 118.71(14) . . ? C228 C227 C232 120.01(14) . . ? C229 C228 C227 121.04(15) . . ? C228 C229 C230 119.23(15) . . ? C231 C230 C229 121.30(14) . . ? C230 C231 C232 121.22(15) . . ? C223 C232 C231 122.56(14) . . ? C223 C232 C227 120.20(13) . . ? C231 C232 C227 117.17(14) . . ? O233 C233 O234 123.65(14) . . ? O233 C233 C225 121.55(14) . . ? O234 C233 C225 114.80(14) . . ? C4B N2 C3 106.0(10) . . ? C4A N2 C3 122.7(3) . . ? C4B N2 C1 135.6(10) . . ? C4A N2 C1 118.5(3) . . ? C3 N2 C1 118.36(16) . . ? O5A C4A N2 126.0(5) . . ? O5B C4B N2 120(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O221 0.97(2) 1.79(2) 2.7534(17) 171.0(18) . O234 H234 O222 1.14(2) 1.32(2) 2.4514(15) 173(2) 1_655 _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.294 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.048 #=== END data_4 _database_code_depnum_ccdc_archive 'CCDC 788709' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,4 lutidinium pamoate DMF solvate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 O6 1- , C7 H10 N 1+ , C3 H7 N O' _chemical_formula_sum 'C33 H32 N2 O7' _chemical_formula_weight 568.61 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.794(3) _cell_length_b 13.334(3) _cell_length_c 16.615(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.507(3) _cell_angle_gamma 90.00 _cell_volume 2862.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3156 _cell_measurement_theta_min 2.195 _cell_measurement_theta_max 27.433 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 17002 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.04 _reflns_number_total 6269 _reflns_number_gt 4043 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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. All protons involved in proton transfer reactions were located in the difference map. ; _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^)+(0.0753P)^2^+0.6499P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6269 _refine_ls_number_parameters 491 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1589 _refine_ls_wR_factor_gt 0.1350 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.07715(15) 0.48009(15) 0.40627(13) 0.0509(5) Uani 1 1 d . . . C5 C 0.1443(3) 0.3948(3) 0.4170(3) 0.0983(12) Uani 1 1 d . A . H5A H 0.1356 0.3660 0.3606 0.147 Uiso 1 1 calc R . . H5B H 0.1268 0.3443 0.4525 0.147 Uiso 1 1 calc R . . H5C H 0.2164 0.4160 0.4451 0.147 Uiso 1 1 calc R . . C2 C 0.0922(5) 0.5635(4) 0.4681(5) 0.0590(16) Uani 0.547(8) 1 d P A 1 H2 H 0.1578 0.5677 0.5128 0.071 Uiso 0.547(8) 1 calc PR A 1 O3 O 0.0296(3) 0.6263(2) 0.4674(2) 0.0540(14) Uani 0.547(8) 1 d P A 1 C4 C -0.0179(7) 0.4758(7) 0.3383(5) 0.063(2) Uani 0.547(8) 1 d P A 1 H4A H -0.0573 0.4177 0.3459 0.095 Uiso 0.547(8) 1 calc PR A 1 H4B H -0.0057 0.4694 0.2839 0.095 Uiso 0.547(8) 1 calc PR A 1 H4C H -0.0571 0.5372 0.3375 0.095 Uiso 0.547(8) 1 calc PR A 1 C2A C 0.1250(6) 0.5600(4) 0.4335(5) 0.0472(17) Uani 0.453(8) 1 d P A 2 H2A H 0.1980 0.5603 0.4481 0.057 Uiso 0.453(8) 1 calc PR A 2 O3A O 0.0836(4) 0.6366(3) 0.4422(3) 0.0584(16) Uani 0.453(8) 1 d P A 2 C4A C -0.0354(8) 0.4687(8) 0.3729(7) 0.063(3) Uani 0.453(8) 1 d P A 2 H4A1 H -0.0680 0.5351 0.3621 0.095 Uiso 0.453(8) 1 calc PR A 2 H4A2 H -0.0575 0.4329 0.4150 0.095 Uiso 0.453(8) 1 calc PR A 2 H4A3 H -0.0563 0.4305 0.3191 0.095 Uiso 0.453(8) 1 calc PR A 2 O211 O 0.44059(10) 0.67474(9) 0.40290(8) 0.0302(3) Uani 1 1 d . . . H211 H 0.379(2) 0.6880(18) 0.4155(15) 0.056(7) Uiso 1 1 d . . . C211 C 0.42690(13) 0.73712(13) 0.33524(11) 0.0237(4) Uani 1 1 d . . . C212 C 0.33470(13) 0.79556(13) 0.30276(12) 0.0249(4) Uani 1 1 d . . . C213 C 0.32127(14) 0.85869(13) 0.23477(12) 0.0260(4) Uani 1 1 d . . . H213 H 0.2614 0.8999 0.2150 0.031 Uiso 1 1 calc R . . C214 C 0.39477(13) 0.86373(13) 0.19344(12) 0.0243(4) Uani 1 1 d . . . C215 C 0.37801(15) 0.92519(14) 0.12034(12) 0.0301(4) Uani 1 1 d . . . H215 H 0.3185 0.9670 0.1011 0.036 Uiso 1 1 calc R . . C216 C 0.44559(16) 0.92557(14) 0.07695(13) 0.0338(5) Uani 1 1 d . . . H216 H 0.4334 0.9671 0.0279 0.041 Uiso 1 1 calc R . . C217 C 0.53409(15) 0.86332(14) 0.10585(12) 0.0315(4) Uani 1 1 d . . . H217 H 0.5803 0.8621 0.0748 0.038 Uiso 1 1 calc R . . C218 C 0.55461(14) 0.80491(13) 0.17748(12) 0.0262(4) Uani 1 1 d . . . H218 H 0.6154 0.7649 0.1960 0.031 Uiso 1 1 calc R . . C219 C 0.48585(13) 0.80319(12) 0.22494(11) 0.0220(4) Uani 1 1 d . . . C220 C 0.50388(13) 0.74285(12) 0.29932(11) 0.0219(4) Uani 1 1 d . . . O221 O 0.26681(11) 0.73289(11) 0.40652(9) 0.0415(4) Uani 1 1 d . . . C221 C 0.25184(14) 0.78751(14) 0.34211(13) 0.0299(4) Uani 1 1 d . . . O222 O 0.17003(10) 0.83767(10) 0.30522(9) 0.0344(3) Uani 1 1 d . . . C222 C 0.60353(12) 0.68330(13) 0.33880(11) 0.0235(4) Uani 1 1 d . . . H22A H 0.6115 0.6380 0.2943 0.028 Uiso 1 1 calc R . . H22B H 0.5967 0.6408 0.3854 0.028 Uiso 1 1 calc R . . C223 C 0.70167(13) 0.74599(12) 0.37532(11) 0.0223(4) Uani 1 1 d . . . O224 O 0.76712(10) 0.67199(9) 0.27489(8) 0.0289(3) Uani 1 1 d . . . H224 H 0.831(2) 0.681(2) 0.2612(17) 0.073(8) Uiso 1 1 d . . . C224 C 0.77921(13) 0.73804(12) 0.34051(11) 0.0229(4) Uani 1 1 d . . . C225 C 0.87084(13) 0.79783(13) 0.37152(11) 0.0244(4) Uani 1 1 d . . . C226 C 0.88286(13) 0.86345(13) 0.43784(12) 0.0248(4) Uani 1 1 d . . . H226 H 0.9428 0.9046 0.4572 0.030 Uiso 1 1 calc R . . C227 C 0.80863(13) 0.87152(12) 0.47823(11) 0.0230(4) Uani 1 1 d . . . C228 C 0.82393(14) 0.93634(13) 0.54929(12) 0.0276(4) Uani 1 1 d . . . H228 H 0.8844 0.9768 0.5692 0.033 Uiso 1 1 calc R . . C229 C 0.75310(15) 0.94149(14) 0.58962(12) 0.0297(4) Uani 1 1 d . . . H229 H 0.7642 0.9850 0.6373 0.036 Uiso 1 1 calc R . . C230 C 0.66321(15) 0.88145(14) 0.55978(12) 0.0295(4) Uani 1 1 d . . . H230 H 0.6142 0.8847 0.5881 0.035 Uiso 1 1 calc R . . C231 C 0.64520(14) 0.81863(13) 0.49080(11) 0.0261(4) Uani 1 1 d . . . H231 H 0.5838 0.7794 0.4719 0.031 Uiso 1 1 calc R . . C232 C 0.71730(13) 0.81122(12) 0.44677(11) 0.0218(4) Uani 1 1 d . . . O233 O 0.93908(10) 0.73594(11) 0.26751(9) 0.0402(4) Uani 1 1 d . . . C233 C 0.95179(14) 0.78994(14) 0.33108(13) 0.0307(4) Uani 1 1 d . . . O234 O 1.03361(10) 0.84423(10) 0.36743(9) 0.0365(4) Uani 1 1 d . . . H234 H 1.096(3) 0.833(3) 0.338(2) 0.107(11) Uiso 1 1 d . . . N11 N 0.12009(17) 0.78287(16) 0.57718(13) 0.0548(5) Uani 1 1 d . . . C16 C 0.0890(5) 0.8131(4) 0.6388(3) 0.0372(12) Uani 0.518(4) 1 d P B 3 H16 H 0.0289 0.7854 0.6457 0.045 Uiso 0.518(4) 1 calc PR B 3 C15 C 0.1456(5) 0.8862(4) 0.6936(3) 0.0436(16) Uani 0.518(4) 1 d P B 3 H15 H 0.1240 0.9138 0.7373 0.052 Uiso 0.518(4) 1 calc PR B 3 C14 C 0.2392(12) 0.9191(10) 0.6818(8) 0.055(5) Uani 0.518(4) 1 d P B 3 C13 C 0.2679(7) 0.8782(7) 0.6172(6) 0.048(3) Uani 0.518(4) 1 d P B 3 C12 C 0.2016(7) 0.8063(7) 0.5659(5) 0.0238(14) Uani 0.518(4) 1 d P B 3 H12 H 0.2190 0.7745 0.5216 0.029 Uiso 0.518(4) 1 calc PR B 3 C17 C 0.3640(3) 0.9112(3) 0.6077(3) 0.0490(14) Uani 0.518(4) 1 d P B 3 H17A H 0.4225 0.8937 0.6595 0.074 Uiso 0.518(4) 1 calc PR B 3 H17B H 0.3620 0.9840 0.5993 0.074 Uiso 0.518(4) 1 calc PR B 3 H17C H 0.3721 0.8780 0.5578 0.074 Uiso 0.518(4) 1 calc PR B 3 C18 C 0.3038(5) 0.9978(3) 0.7432(3) 0.0553(16) Uani 0.518(4) 1 d P B 3 H18A H 0.3134 1.0557 0.7105 0.083 Uiso 0.518(4) 1 calc PR B 3 H18B H 0.3715 0.9694 0.7767 0.083 Uiso 0.518(4) 1 calc PR B 3 H18C H 0.2684 1.0191 0.7822 0.083 Uiso 0.518(4) 1 calc PR B 3 C18A C 0.3897(4) 0.9707(4) 0.6808(3) 0.0519(15) Uani 0.482(4) 1 d P B 4 H18D H 0.3703 1.0417 0.6739 0.078 Uiso 0.482(4) 1 calc PR B 4 H18E H 0.4364 0.9560 0.6494 0.078 Uiso 0.482(4) 1 calc PR B 4 H18F H 0.4247 0.9558 0.7419 0.078 Uiso 0.482(4) 1 calc PR B 4 C15A C 0.2771(6) 0.8465(5) 0.5736(4) 0.054(2) Uani 0.482(4) 1 d P B 4 H15A H 0.3292 0.8456 0.5484 0.064 Uiso 0.482(4) 1 calc PR B 4 C14A C 0.2935(7) 0.9067(7) 0.6456(7) 0.0366(18) Uani 0.482(4) 1 d P B 4 C17A C 0.2315(5) 0.9736(4) 0.7625(3) 0.0601(17) Uani 0.482(4) 1 d P B 4 H17D H 0.1723 0.9621 0.7810 0.090 Uiso 0.482(4) 1 calc PR B 4 H17E H 0.2339 1.0445 0.7479 0.090 Uiso 0.482(4) 1 calc PR B 4 H17F H 0.2955 0.9555 0.8091 0.090 Uiso 0.482(4) 1 calc PR B 4 C12A C 0.1323(6) 0.8529(6) 0.6511(5) 0.0528(18) Uani 0.482(4) 1 d P B 4 H12A H 0.0787 0.8575 0.6746 0.063 Uiso 0.482(4) 1 calc PR B 4 C13A C 0.2202(10) 0.9104(11) 0.6853(9) 0.040(4) Uani 0.482(4) 1 d P B 4 C16A C 0.1977(10) 0.7928(8) 0.5395(5) 0.034(2) Uani 0.482(4) 1 d P B 4 H16A H 0.1896 0.7583 0.4875 0.041 Uiso 0.482(4) 1 calc PR B 4 H11 H 0.0728 0.7271 0.5384 0.124(13) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0408(11) 0.0470(11) 0.0547(12) -0.0017(10) 0.0040(9) 0.0005(10) C5 0.079(2) 0.095(2) 0.112(3) 0.011(2) 0.021(2) 0.042(2) C2 0.046(3) 0.049(3) 0.078(4) 0.000(3) 0.018(3) 0.012(3) O3 0.044(2) 0.0455(19) 0.065(2) -0.0088(16) 0.0097(18) -0.0016(16) C4 0.051(5) 0.060(4) 0.064(5) 0.002(4) 0.002(3) 0.001(3) C2A 0.040(3) 0.043(3) 0.056(4) -0.002(3) 0.013(3) 0.000(3) O3A 0.050(3) 0.043(2) 0.087(3) -0.013(2) 0.030(3) -0.012(2) C4A 0.042(4) 0.051(4) 0.085(8) -0.009(5) 0.007(5) -0.019(3) O211 0.0255(7) 0.0351(7) 0.0341(8) 0.0043(6) 0.0156(6) -0.0019(6) C211 0.0198(9) 0.0252(9) 0.0256(9) -0.0036(7) 0.0075(7) -0.0058(7) C212 0.0179(9) 0.0277(9) 0.0297(10) -0.0077(8) 0.0091(7) -0.0062(7) C213 0.0186(9) 0.0268(9) 0.0311(10) -0.0079(8) 0.0069(7) -0.0008(7) C214 0.0197(9) 0.0251(9) 0.0272(9) -0.0055(8) 0.0072(7) -0.0014(7) C215 0.0287(10) 0.0302(10) 0.0316(11) -0.0005(8) 0.0106(8) 0.0067(8) C216 0.0407(12) 0.0343(11) 0.0290(10) 0.0040(8) 0.0152(9) 0.0069(9) C217 0.0339(11) 0.0364(10) 0.0307(11) -0.0019(9) 0.0195(9) 0.0018(9) C218 0.0220(9) 0.0296(9) 0.0275(10) -0.0036(8) 0.0094(7) -0.0001(8) C219 0.0180(8) 0.0226(8) 0.0255(9) -0.0065(7) 0.0079(7) -0.0044(7) C220 0.0178(8) 0.0222(8) 0.0252(9) -0.0053(7) 0.0068(7) -0.0049(7) O221 0.0284(8) 0.0589(9) 0.0442(9) 0.0067(8) 0.0216(7) -0.0004(7) C221 0.0204(9) 0.0350(10) 0.0369(11) -0.0093(9) 0.0131(8) -0.0068(8) O222 0.0211(7) 0.0419(8) 0.0441(9) -0.0062(6) 0.0163(6) -0.0013(6) C222 0.0183(8) 0.0258(9) 0.0271(10) -0.0006(7) 0.0090(7) -0.0018(7) C223 0.0176(8) 0.0233(8) 0.0246(9) 0.0018(7) 0.0059(7) -0.0004(7) O224 0.0218(7) 0.0344(7) 0.0322(7) -0.0100(6) 0.0114(6) -0.0020(6) C224 0.0180(8) 0.0246(9) 0.0252(9) -0.0015(7) 0.0063(7) 0.0008(7) C225 0.0172(8) 0.0276(9) 0.0283(10) 0.0014(8) 0.0077(7) 0.0027(7) C226 0.0172(8) 0.0245(9) 0.0301(10) 0.0004(8) 0.0049(7) -0.0010(7) C227 0.0191(9) 0.0236(8) 0.0242(9) 0.0019(7) 0.0049(7) 0.0018(7) C228 0.0256(10) 0.0258(9) 0.0293(10) 0.0002(8) 0.0068(8) -0.0026(8) C229 0.0351(11) 0.0290(9) 0.0251(10) -0.0032(8) 0.0107(8) -0.0014(8) C230 0.0302(10) 0.0342(10) 0.0282(10) 0.0016(8) 0.0154(8) 0.0000(8) C231 0.0225(9) 0.0297(9) 0.0261(10) 0.0010(8) 0.0085(7) -0.0027(7) C232 0.0196(8) 0.0225(8) 0.0225(9) 0.0050(7) 0.0063(7) 0.0026(7) O233 0.0249(7) 0.0551(9) 0.0456(9) -0.0190(7) 0.0185(6) -0.0061(7) C233 0.0188(9) 0.0359(10) 0.0378(11) -0.0043(9) 0.0105(8) 0.0005(8) O234 0.0202(7) 0.0450(8) 0.0484(9) -0.0132(7) 0.0170(6) -0.0076(6) N11 0.0508(13) 0.0524(12) 0.0492(13) 0.0005(10) 0.0026(10) 0.0060(10) C16 0.039(3) 0.034(3) 0.035(3) 0.002(2) 0.009(2) 0.010(2) C15 0.073(4) 0.025(3) 0.026(3) -0.004(2) 0.009(3) 0.006(3) C14 0.079(9) 0.021(3) 0.029(6) -0.002(4) -0.027(5) -0.006(5) C13 0.035(4) 0.042(6) 0.051(7) 0.019(4) -0.008(4) -0.005(3) C12 0.031(3) 0.026(3) 0.017(4) 0.002(3) 0.012(3) -0.001(2) C17 0.035(2) 0.042(2) 0.057(3) 0.016(2) 0.000(2) 0.001(2) C18 0.068(4) 0.032(2) 0.044(3) -0.002(2) -0.008(3) -0.006(2) C18A 0.056(3) 0.041(3) 0.049(3) 0.005(2) 0.006(2) -0.008(2) C15A 0.085(6) 0.031(3) 0.034(4) 0.004(3) 0.007(3) 0.009(3) C14A 0.044(5) 0.029(4) 0.033(5) 0.014(3) 0.010(4) 0.010(3) C17A 0.081(5) 0.050(3) 0.045(3) 0.002(3) 0.016(3) 0.022(3) C12A 0.040(4) 0.050(5) 0.057(5) 0.007(4) 0.003(4) 0.014(3) C13A 0.041(5) 0.038(6) 0.049(6) 0.022(4) 0.028(4) 0.028(4) C16A 0.051(4) 0.030(3) 0.017(4) -0.008(3) 0.006(4) 0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2A 1.252(6) . ? N1 C4 1.400(9) . ? N1 C5 1.438(3) . ? N1 C4A 1.462(10) . ? N1 C2 1.478(7) . ? C2 O3 1.199(6) . ? C2A O3A 1.203(8) . ? O211 C211 1.357(2) . ? C211 C220 1.391(2) . ? C211 C212 1.427(2) . ? C212 C213 1.368(3) . ? C212 C221 1.506(2) . ? C213 C214 1.411(2) . ? C214 C215 1.415(3) . ? C214 C219 1.429(2) . ? C215 C216 1.364(3) . ? C216 C217 1.414(3) . ? C217 C218 1.366(3) . ? C218 C219 1.430(2) . ? C219 C220 1.422(2) . ? C220 C222 1.523(2) . ? O221 C221 1.250(2) . ? C221 O222 1.270(2) . ? C222 C223 1.525(2) . ? C223 C224 1.387(2) . ? C223 C232 1.426(2) . ? O224 C224 1.366(2) . ? C224 C225 1.429(2) . ? C225 C226 1.371(2) . ? C225 C233 1.495(2) . ? C226 C227 1.411(2) . ? C227 C228 1.418(2) . ? C227 C232 1.430(2) . ? C228 C229 1.366(2) . ? C229 C230 1.412(3) . ? C230 C231 1.370(2) . ? C231 C232 1.430(2) . ? O233 C233 1.239(2) . ? C233 O234 1.298(2) . ? N11 C12 1.242(9) . ? N11 C16 1.305(6) . ? N11 C16A 1.423(12) . ? N11 C12A 1.505(9) . ? C16 C15 1.375(7) . ? C15 C14 1.440(18) . ? C14 C13 1.379(16) . ? C14 C18 1.517(12) . ? C13 C12 1.392(12) . ? C13 C17 1.457(11) . ? C18A C14A 1.512(9) . ? C15A C16A 1.265(14) . ? C15A C14A 1.393(11) . ? C14A C13A 1.387(16) . ? C17A C13A 1.497(13) . ? C12A C13A 1.377(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2A N1 C5 113.2(4) . . ? C4 N1 C5 116.6(5) . . ? C2A N1 C4A 125.5(6) . . ? C5 N1 C4A 121.2(5) . . ? C4 N1 C2 117.1(5) . . ? C5 N1 C2 125.5(3) . . ? O3 C2 N1 126.4(5) . . ? O3A C2A N1 123.6(6) . . ? O211 C211 C220 118.92(16) . . ? O211 C211 C212 119.67(15) . . ? C220 C211 C212 121.41(16) . . ? C213 C212 C211 119.56(16) . . ? C213 C212 C221 119.89(17) . . ? C211 C212 C221 120.54(16) . . ? C212 C213 C214 121.23(17) . . ? C213 C214 C215 121.06(16) . . ? C213 C214 C219 118.94(16) . . ? C215 C214 C219 119.97(16) . . ? C216 C215 C214 121.29(17) . . ? C215 C216 C217 119.15(18) . . ? C218 C217 C216 121.41(17) . . ? C217 C218 C219 120.95(17) . . ? C220 C219 C214 120.11(15) . . ? C220 C219 C218 122.71(16) . . ? C214 C219 C218 117.16(16) . . ? C211 C220 C219 118.48(16) . . ? C211 C220 C222 119.75(15) . . ? C219 C220 C222 121.75(14) . . ? O221 C221 O222 124.92(17) . . ? O221 C221 C212 119.35(17) . . ? O222 C221 C212 115.73(17) . . ? C220 C222 C223 115.29(14) . . ? C224 C223 C232 118.70(15) . . ? C224 C223 C222 119.95(15) . . ? C232 C223 C222 121.33(15) . . ? O224 C224 C223 119.07(15) . . ? O224 C224 C225 119.53(15) . . ? C223 C224 C225 121.39(16) . . ? C226 C225 C224 119.24(16) . . ? C226 C225 C233 120.47(16) . . ? C224 C225 C233 120.28(16) . . ? C225 C226 C227 121.82(16) . . ? C226 C227 C228 121.41(16) . . ? C226 C227 C232 118.44(16) . . ? C228 C227 C232 120.14(16) . . ? C229 C228 C227 121.03(17) . . ? C228 C229 C230 119.35(17) . . ? C231 C230 C229 121.33(17) . . ? C230 C231 C232 121.03(17) . . ? C223 C232 C231 122.61(16) . . ? C223 C232 C227 120.27(15) . . ? C231 C232 C227 117.11(16) . . ? O233 C233 O234 124.13(17) . . ? O233 C233 C225 121.27(16) . . ? O234 C233 C225 114.59(16) . . ? C12 N11 C16 127.1(4) . . ? C12 N11 C16A 18.3(5) . . ? C16 N11 C16A 145.2(5) . . ? C12 N11 C12A 96.8(5) . . ? C16 N11 C12A 30.8(3) . . ? C16A N11 C12A 114.6(5) . . ? N11 C16 C15 118.2(5) . . ? C16 C15 C14 117.0(6) . . ? C13 C14 C15 120.1(9) . . ? C13 C14 C18 122.4(14) . . ? C15 C14 C18 117.5(11) . . ? C14 C13 C12 116.3(10) . . ? C14 C13 C17 119.0(11) . . ? C12 C13 C17 124.7(9) . . ? N11 C12 C13 121.1(7) . . ? C16A C15A C14A 124.5(8) . . ? C13A C14A C15A 120.2(10) . . ? C13A C14A C18A 118.9(10) . . ? C15A C14A C18A 120.9(8) . . ? C13A C12A N11 120.8(8) . . ? C12A C13A C14A 117.9(11) . . ? C12A C13A C17A 118.6(10) . . ? C14A C13A C17A 123.5(12) . . ? C15A C16A N11 121.5(6) . . ? 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 N11 H11 O3 1.05 1.75 2.766(4) 162.0 . N11 H11 O3A 1.05 2.05 2.880(5) 134.2 . _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.278 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.047 #=== END data_5 _database_code_depnum_ccdc_archive 'CCDC 788710' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,5 lutidinium pamoate DMF solvate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 O6 1- , C7 H10 N 1+ , C3 H7 N O' _chemical_formula_sum 'C33 H32 N2 O7' _chemical_formula_weight 568.61 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.8721(11) _cell_length_b 12.9708(10) _cell_length_c 16.9195(14) _cell_angle_alpha 90.00 _cell_angle_beta 111.3370(10) _cell_angle_gamma 90.00 _cell_volume 2835.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5306 _cell_measurement_theta_min 2.267 _cell_measurement_theta_max 27.783 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9732 _exptl_absorpt_correction_T_max 0.9857 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 16925 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.04 _reflns_number_total 6243 _reflns_number_gt 4881 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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. All protons involved in proton transfer reactions were located in the difference map. ; _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^)+(0.0609P)^2^+1.0367P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6243 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.44876(10) 0.51577(10) 0.41083(8) 0.0253(3) Uani 1 1 d . . . O2 O -0.37638(9) 0.39183(9) 0.51014(7) 0.0344(3) Uani 1 1 d . . . C3 C -0.44648(12) 0.42430(12) 0.44594(10) 0.0261(3) Uani 1 1 d . . . H3 H -0.5035 0.3797 0.4197 0.031 Uiso 1 1 calc R . . C4 C -0.53771(13) 0.54801(14) 0.33774(10) 0.0317(4) Uani 1 1 d . . . H4A H -0.5859 0.4901 0.3179 0.048 Uiso 1 1 calc R . . H4C H -0.5145 0.5702 0.2922 0.048 Uiso 1 1 calc R . . H4B H -0.5726 0.6054 0.3539 0.048 Uiso 1 1 calc R . . C5 C -0.36685(15) 0.59029(15) 0.44693(13) 0.0475(5) Uani 1 1 d . . . H5C H -0.3915 0.6457 0.4741 0.071 Uiso 1 1 calc R . . H5B H -0.3464 0.6193 0.4019 0.071 Uiso 1 1 calc R . . H5A H -0.3072 0.5564 0.4892 0.071 Uiso 1 1 calc R . . N11 N -0.31690(12) 0.20452(11) 0.58220(9) 0.0339(3) Uani 1 1 d . . . H11 H -0.3509(17) 0.2618(18) 0.5510(14) 0.053(6) Uiso 1 1 d . . . C12 C -0.23017(15) 0.17011(13) 0.57435(10) 0.0339(4) Uani 1 1 d . . . H12 H -0.2071 0.1992 0.5328 0.041 Uiso 1 1 calc R . . C13 C -0.17339(13) 0.09139(12) 0.62706(10) 0.0291(4) Uani 1 1 d . . . C14 C -0.21263(13) 0.05209(12) 0.68544(10) 0.0283(4) Uani 1 1 d . . . H14 H -0.1762 -0.0020 0.7220 0.034 Uiso 1 1 calc R . . C15 C -0.30366(13) 0.08912(12) 0.69239(10) 0.0310(4) Uani 1 1 d . . . C16 C -0.35438(14) 0.16740(13) 0.63881(11) 0.0341(4) Uani 1 1 d . . . H16 H -0.4162 0.1952 0.6420 0.041 Uiso 1 1 calc R . . C17 C -0.07445(15) 0.05293(15) 0.62147(13) 0.0445(5) Uani 1 1 d . . . H17B H -0.0164 0.0724 0.6730 0.067 Uiso 1 1 calc R . . H17A H -0.0648 0.0835 0.5719 0.067 Uiso 1 1 calc R . . H17C H -0.0772 -0.0223 0.6159 0.067 Uiso 1 1 calc R . . C18 C -0.34542(17) 0.04786(16) 0.75688(13) 0.0471(5) Uani 1 1 d . . . H18A H -0.4098 0.0838 0.7510 0.071 Uiso 1 1 calc R . . H18B H -0.2945 0.0591 0.8141 0.071 Uiso 1 1 calc R . . H18C H -0.3591 -0.0261 0.7475 0.071 Uiso 1 1 calc R . . O211 O -0.02880(8) 0.32604(8) 0.40264(6) 0.0212(2) Uani 1 1 d . . . H211 H -0.0891(18) 0.3169(17) 0.4160(13) 0.054(6) Uiso 1 1 d . . . C211 C -0.04610(10) 0.26258(10) 0.33496(8) 0.0167(3) Uani 1 1 d . . . C212 C -0.14107(10) 0.20583(11) 0.30240(8) 0.0166(3) Uani 1 1 d . . . C213 C -0.16013(10) 0.14443(11) 0.23254(9) 0.0171(3) Uani 1 1 d . . . H213 H -0.2227 0.1060 0.2116 0.021 Uiso 1 1 calc R . . C214 C -0.08876(10) 0.13707(10) 0.19096(8) 0.0165(3) Uani 1 1 d . . . C215 C -0.11284(11) 0.07972(11) 0.11502(9) 0.0191(3) Uani 1 1 d . . . H215 H -0.1768 0.0439 0.0929 0.023 Uiso 1 1 calc R . . C216 C -0.04527(11) 0.07525(11) 0.07314(9) 0.0203(3) Uani 1 1 d . . . H216 H -0.0621 0.0364 0.0223 0.024 Uiso 1 1 calc R . . C217 C 0.04962(11) 0.12865(11) 0.10587(9) 0.0199(3) Uani 1 1 d . . . H217 H 0.0965 0.1252 0.0767 0.024 Uiso 1 1 calc R . . C218 C 0.07545(10) 0.18533(11) 0.17894(9) 0.0175(3) Uani 1 1 d . . . H218 H 0.1399 0.2205 0.1996 0.021 Uiso 1 1 calc R . . C219 C 0.00688(10) 0.19233(10) 0.22449(8) 0.0155(3) Uani 1 1 d . . . C220 C 0.02875(10) 0.25401(10) 0.29872(8) 0.0158(3) Uani 1 1 d . . . C221 C -0.21980(10) 0.21543(11) 0.34335(9) 0.0181(3) Uani 1 1 d . . . O221 O -0.20176(8) 0.26812(9) 0.40860(6) 0.0253(2) Uani 1 1 d . . . O222 O -0.30530(7) 0.16708(8) 0.30579(6) 0.0221(2) Uani 1 1 d . . . H222 H -0.3687(19) 0.175(2) 0.3384(14) 0.074(8) Uiso 1 1 d . . . C222 C 0.12909(10) 0.31497(11) 0.33566(8) 0.0171(3) Uani 1 1 d . . . H22A H 0.1237 0.3609 0.3806 0.021 Uiso 1 1 calc R . . H22B H 0.1358 0.3595 0.2904 0.021 Uiso 1 1 calc R . . C223 C 0.22776(10) 0.25149(10) 0.37307(9) 0.0166(3) Uani 1 1 d . . . O224 O 0.28774(8) 0.31874(8) 0.26863(6) 0.0210(2) Uani 1 1 d . . . H224 H 0.3460(18) 0.3078(17) 0.2535(14) 0.053(6) Uiso 1 1 d . . . C224 C 0.30324(10) 0.25685(10) 0.33741(8) 0.0164(3) Uani 1 1 d . . . C225 C 0.39791(10) 0.19967(10) 0.37192(9) 0.0168(3) Uani 1 1 d . . . C226 C 0.41417(10) 0.13868(11) 0.44201(9) 0.0175(3) Uani 1 1 d . . . H226 H 0.4765 0.1001 0.4644 0.021 Uiso 1 1 calc R . . C227 C 0.34061(10) 0.13194(10) 0.48156(8) 0.0169(3) Uani 1 1 d . . . C228 C 0.35903(11) 0.07009(11) 0.55508(9) 0.0207(3) Uani 1 1 d . . . H228 H 0.4205 0.0301 0.5767 0.025 Uiso 1 1 calc R . . C229 C 0.28915(12) 0.06764(12) 0.59505(9) 0.0229(3) Uani 1 1 d . . . H229 H 0.3015 0.0253 0.6435 0.027 Uiso 1 1 calc R . . C230 C 0.19854(11) 0.12854(11) 0.56372(9) 0.0216(3) Uani 1 1 d . . . H230 H 0.1514 0.1286 0.5927 0.026 Uiso 1 1 calc R . . C231 C 0.17767(11) 0.18733(11) 0.49238(9) 0.0189(3) Uani 1 1 d . . . H231 H 0.1158 0.2268 0.4722 0.023 Uiso 1 1 calc R . . C232 C 0.24717(10) 0.19044(10) 0.44772(8) 0.0165(3) Uani 1 1 d . . . C233 C 0.47880(11) 0.20784(11) 0.33243(9) 0.0183(3) Uani 1 1 d . . . O233 O 0.45956(8) 0.25597(9) 0.26458(7) 0.0254(2) Uani 1 1 d . . . O234 O 0.56527(8) 0.16374(8) 0.37296(6) 0.0234(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0246(7) 0.0246(7) 0.0232(6) 0.0004(5) 0.0044(5) -0.0002(5) O2 0.0373(7) 0.0300(6) 0.0319(6) 0.0061(5) 0.0078(5) 0.0075(5) C3 0.0277(8) 0.0235(8) 0.0265(8) -0.0033(6) 0.0090(6) -0.0005(6) C4 0.0292(9) 0.0378(9) 0.0238(8) 0.0033(7) 0.0046(7) 0.0035(7) C5 0.0403(11) 0.0373(10) 0.0507(12) 0.0059(9) -0.0004(9) -0.0152(8) N11 0.0352(8) 0.0251(7) 0.0283(7) 0.0030(6) -0.0041(6) -0.0010(6) C12 0.0472(11) 0.0285(9) 0.0235(8) -0.0044(7) 0.0099(7) -0.0151(8) C13 0.0349(9) 0.0218(8) 0.0257(8) -0.0072(6) 0.0052(7) -0.0079(7) C14 0.0347(9) 0.0181(7) 0.0246(8) -0.0019(6) 0.0021(7) -0.0021(6) C15 0.0363(9) 0.0232(8) 0.0297(8) -0.0061(7) 0.0075(7) -0.0083(7) C16 0.0286(9) 0.0285(9) 0.0382(9) -0.0052(7) 0.0038(7) -0.0041(7) C17 0.0464(11) 0.0371(10) 0.0548(12) -0.0183(9) 0.0241(10) -0.0117(9) C18 0.0628(13) 0.0390(11) 0.0476(12) -0.0075(9) 0.0296(10) -0.0155(9) O211 0.0181(5) 0.0266(6) 0.0210(5) -0.0074(4) 0.0098(4) -0.0026(4) C211 0.0159(6) 0.0180(7) 0.0159(6) 0.0008(5) 0.0056(5) 0.0023(5) C212 0.0140(6) 0.0191(7) 0.0172(6) 0.0038(5) 0.0062(5) 0.0030(5) C213 0.0133(6) 0.0183(7) 0.0188(7) 0.0024(5) 0.0049(5) -0.0007(5) C214 0.0154(6) 0.0169(7) 0.0172(7) 0.0028(5) 0.0059(5) 0.0016(5) C215 0.0180(7) 0.0179(7) 0.0209(7) 0.0001(5) 0.0063(6) -0.0006(5) C216 0.0236(7) 0.0199(7) 0.0181(7) -0.0016(5) 0.0085(6) 0.0014(6) C217 0.0206(7) 0.0228(7) 0.0195(7) 0.0025(6) 0.0111(6) 0.0027(6) C218 0.0146(6) 0.0194(7) 0.0194(7) 0.0031(5) 0.0072(5) 0.0008(5) C219 0.0143(6) 0.0161(6) 0.0165(6) 0.0038(5) 0.0060(5) 0.0034(5) C220 0.0135(6) 0.0165(6) 0.0170(7) 0.0023(5) 0.0050(5) 0.0013(5) C221 0.0155(6) 0.0215(7) 0.0181(7) 0.0030(5) 0.0071(5) 0.0014(5) O221 0.0213(5) 0.0350(6) 0.0235(5) -0.0071(5) 0.0129(4) -0.0043(4) O222 0.0153(5) 0.0302(6) 0.0236(5) -0.0027(4) 0.0102(4) -0.0028(4) C222 0.0146(6) 0.0184(7) 0.0196(7) -0.0010(5) 0.0076(5) -0.0009(5) C223 0.0129(6) 0.0172(7) 0.0190(7) -0.0033(5) 0.0050(5) -0.0022(5) O224 0.0169(5) 0.0261(6) 0.0221(5) 0.0055(4) 0.0096(4) 0.0009(4) C224 0.0161(7) 0.0166(7) 0.0164(6) -0.0015(5) 0.0059(5) -0.0028(5) C225 0.0145(6) 0.0185(7) 0.0184(7) -0.0043(5) 0.0072(5) -0.0029(5) C226 0.0155(6) 0.0183(7) 0.0199(7) -0.0027(5) 0.0076(5) 0.0004(5) C227 0.0169(7) 0.0166(7) 0.0176(7) -0.0035(5) 0.0069(5) -0.0024(5) C228 0.0213(7) 0.0208(7) 0.0208(7) 0.0005(6) 0.0085(6) 0.0033(6) C229 0.0280(8) 0.0235(7) 0.0189(7) 0.0017(6) 0.0107(6) -0.0003(6) C230 0.0216(7) 0.0266(8) 0.0200(7) -0.0034(6) 0.0118(6) -0.0033(6) C231 0.0155(7) 0.0228(7) 0.0189(7) -0.0039(5) 0.0068(5) -0.0007(5) C232 0.0146(6) 0.0176(7) 0.0174(7) -0.0050(5) 0.0061(5) -0.0032(5) C233 0.0163(7) 0.0187(7) 0.0214(7) -0.0028(6) 0.0088(6) -0.0018(5) O233 0.0205(5) 0.0341(6) 0.0254(6) 0.0062(5) 0.0128(4) 0.0030(4) O234 0.0164(5) 0.0307(6) 0.0265(5) 0.0033(4) 0.0119(4) 0.0031(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.322(2) . ? N1 C5 1.447(2) . ? N1 C4 1.4547(19) . ? O2 C3 1.2387(19) . ? N11 C12 1.335(2) . ? N11 C16 1.335(2) . ? C12 C13 1.395(2) . ? C13 C14 1.387(2) . ? C13 C17 1.495(3) . ? C14 C15 1.395(2) . ? C15 C16 1.372(2) . ? C15 C18 1.507(3) . ? O211 C211 1.3589(17) . ? C211 C220 1.3890(18) . ? C211 C212 1.4329(19) . ? C212 C213 1.3689(19) . ? C212 C221 1.4962(18) . ? C213 C214 1.4112(18) . ? C214 C215 1.4153(19) . ? C214 C219 1.4312(19) . ? C215 C216 1.367(2) . ? C216 C217 1.410(2) . ? C217 C218 1.369(2) . ? C218 C219 1.4285(18) . ? C219 C220 1.4255(19) . ? C220 C222 1.5233(18) . ? C221 O221 1.2440(17) . ? C221 O222 1.2866(17) . ? C222 C223 1.5236(18) . ? C223 C224 1.3874(18) . ? C223 C232 1.4309(19) . ? O224 C224 1.3647(17) . ? C224 C225 1.4344(19) . ? C225 C226 1.374(2) . ? C225 C233 1.5040(18) . ? C226 C227 1.4119(18) . ? C227 C228 1.423(2) . ? C227 C232 1.4295(19) . ? C228 C229 1.369(2) . ? C229 C230 1.414(2) . ? C230 C231 1.367(2) . ? C231 C232 1.4256(19) . ? C233 O233 1.2474(17) . ? C233 O234 1.2798(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C5 121.54(14) . . ? C3 N1 C4 120.94(13) . . ? C5 N1 C4 117.37(14) . . ? O2 C3 N1 125.60(15) . . ? C12 N11 C16 123.47(15) . . ? N11 C12 C13 120.05(16) . . ? C14 C13 C12 116.59(16) . . ? C14 C13 C17 121.98(16) . . ? C12 C13 C17 121.42(17) . . ? C13 C14 C15 122.36(15) . . ? C16 C15 C14 117.46(16) . . ? C16 C15 C18 120.07(17) . . ? C14 C15 C18 122.46(17) . . ? N11 C16 C15 120.05(17) . . ? O211 C211 C220 119.29(12) . . ? O211 C211 C212 119.40(12) . . ? C220 C211 C212 121.31(12) . . ? C213 C212 C211 119.51(12) . . ? C213 C212 C221 120.27(12) . . ? C211 C212 C221 120.21(12) . . ? C212 C213 C214 121.32(12) . . ? C213 C214 C215 120.77(12) . . ? C213 C214 C219 119.06(12) . . ? C215 C214 C219 120.11(12) . . ? C216 C215 C214 120.88(13) . . ? C215 C216 C217 119.59(13) . . ? C218 C217 C216 121.24(13) . . ? C217 C218 C219 120.95(13) . . ? C220 C219 C218 122.75(12) . . ? C220 C219 C214 119.99(12) . . ? C218 C219 C214 117.22(12) . . ? C211 C220 C219 118.70(12) . . ? C211 C220 C222 119.71(12) . . ? C219 C220 C222 121.50(12) . . ? O221 C221 O222 123.90(12) . . ? O221 C221 C212 120.77(12) . . ? O222 C221 C212 115.32(12) . . ? C220 C222 C223 116.01(11) . . ? C224 C223 C232 118.82(12) . . ? C224 C223 C222 119.89(12) . . ? C232 C223 C222 121.19(12) . . ? O224 C224 C223 119.37(12) . . ? O224 C224 C225 119.22(12) . . ? C223 C224 C225 121.41(12) . . ? C226 C225 C224 119.17(12) . . ? C226 C225 C233 120.61(12) . . ? C224 C225 C233 120.22(12) . . ? C225 C226 C227 121.65(13) . . ? C226 C227 C228 121.22(13) . . ? C226 C227 C232 118.92(12) . . ? C228 C227 C232 119.84(12) . . ? C229 C228 C227 120.70(13) . . ? C228 C229 C230 119.63(13) . . ? C231 C230 C229 121.08(13) . . ? C230 C231 C232 121.14(13) . . ? C231 C232 C227 117.53(12) . . ? C231 C232 C223 122.49(12) . . ? C227 C232 C223 119.96(12) . . ? O233 C233 O234 124.17(13) . . ? O233 C233 C225 119.98(12) . . ? O234 C233 C225 115.85(12) . . ? 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 N11 H11 O2 0.93(2) 1.81(2) 2.7088(19) 161(2) . O222 H222 O234 1.20(2) 1.26(2) 2.4499(14) 169(2) 1_455 _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.328 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.047 #=== END data_6 _database_code_depnum_ccdc_archive 'CCDC 788711' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,3 lutidinium pamoate NMP solvate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 O6 1- , C7 H10 N 1+ , C5 H9 N O' _chemical_formula_sum 'C35 H34 N2 O7' _chemical_formula_weight 594.64 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.6610(19) _cell_length_b 13.7621(19) _cell_length_c 16.906(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.929(2) _cell_angle_gamma 90.00 _cell_volume 2927.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3868 _cell_measurement_theta_min 2.207 _cell_measurement_theta_max 27.452 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9759 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 17075 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 26.64 _reflns_number_total 6102 _reflns_number_gt 4329 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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^)+(0.0843P)^2^+1.6923P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6102 _refine_ls_number_parameters 477 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1812 _refine_ls_wR_factor_gt 0.1615 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.1971(2) 1.10792(19) 0.18377(19) 0.0648(8) Uani 1 1 d . . . H11 H 0.1961 1.0812 0.2307 0.078 Uiso 1 1 calc R . . C12 C 0.2798(2) 1.08875(18) 0.16649(18) 0.0443(6) Uani 1 1 d . . . C13 C 0.2870(2) 1.13074(18) 0.09205(16) 0.0434(6) Uani 1 1 d . . . C14 C 0.2073(2) 1.18770(19) 0.0425(2) 0.0521(7) Uani 1 1 d . . . H14 H 0.2102 1.2159 -0.0078 0.063 Uiso 1 1 calc R . . C15 C 0.1198(3) 1.2065(2) 0.0638(3) 0.1003(18) Uani 1 1 d . . . H15 H 0.0641 1.2479 0.0287 0.120 Uiso 1 1 calc R . . C16 C 0.1151(3) 1.1620(3) 0.1400(3) 0.0706(10) Uani 1 1 d . . . H16 H 0.0570 1.1714 0.1568 0.085 Uiso 1 1 calc R . . C17 C 0.3637(2) 1.02461(18) 0.22247(19) 0.0512(7) Uani 1 1 d . . . H17A H 0.3445 1.0009 0.2692 0.077 Uiso 1 1 calc R . . H17B H 0.4308 1.0607 0.2466 0.077 Uiso 1 1 calc R . . H17C H 0.3721 0.9693 0.1891 0.077 Uiso 1 1 calc R . . C18 C 0.3792(2) 1.1102(2) 0.0705(2) 0.0594(8) Uani 1 1 d . . . H18A H 0.3740 1.1484 0.0201 0.089 Uiso 1 1 calc R . . H18B H 0.3807 1.0409 0.0578 0.089 Uiso 1 1 calc R . . H18C H 0.4446 1.1277 0.1192 0.089 Uiso 1 1 calc R . . O211 O 0.25327(12) 0.70344(11) 0.24613(9) 0.0279(3) Uani 1 1 d . . . C211 C 0.23864(15) 0.76398(14) 0.17882(12) 0.0220(4) Uani 1 1 d . . . H211 H 0.193(3) 0.718(2) 0.262(2) 0.069(10) Uiso 1 1 d . . . C212 C 0.14505(15) 0.82298(14) 0.14539(13) 0.0225(4) Uani 1 1 d . . . C213 C 0.12855(15) 0.88074(14) 0.07508(13) 0.0225(4) Uani 1 1 d . . . H213 H 0.0672 0.9210 0.0538 0.027 Uiso 1 1 calc R . . C214 C 0.20064(15) 0.88172(14) 0.03373(12) 0.0219(4) Uani 1 1 d . . . C215 C 0.17844(16) 0.93533(15) -0.04298(13) 0.0250(4) Uani 1 1 d . . . H215 H 0.1163 0.9744 -0.0650 0.030 Uiso 1 1 calc R . . C216 C 0.24544(17) 0.93149(15) -0.08582(13) 0.0283(5) Uani 1 1 d . . . H216 H 0.2292 0.9665 -0.1378 0.034 Uiso 1 1 calc R . . C217 C 0.33880(17) 0.87490(16) -0.05176(13) 0.0281(5) Uani 1 1 d . . . H217 H 0.3850 0.8719 -0.0816 0.034 Uiso 1 1 calc R . . C218 C 0.36413(16) 0.82421(15) 0.02330(13) 0.0248(4) Uani 1 1 d . . . H218 H 0.4286 0.7883 0.0455 0.030 Uiso 1 1 calc R . . C219 C 0.29532(15) 0.82443(14) 0.06884(12) 0.0221(4) Uani 1 1 d . . . C220 C 0.31541(15) 0.76724(14) 0.14391(13) 0.0221(4) Uani 1 1 d . . . C221 C 0.06581(15) 0.82071(15) 0.18658(13) 0.0243(4) Uani 1 1 d . . . O221 O 0.07990(11) 0.76751(11) 0.24946(9) 0.0291(3) Uani 1 1 d . . . O222 O -0.01619(12) 0.87584(12) 0.15169(10) 0.0331(4) Uani 1 1 d . . . H222 H -0.079(3) 0.872(3) 0.183(2) 0.097(13) Uiso 1 1 d . . . C222 C 0.41632(15) 0.70665(15) 0.18371(13) 0.0241(4) Uani 1 1 d . . . H22A H 0.4227 0.6641 0.1387 0.029 Uiso 1 1 calc R . . H22B H 0.4093 0.6642 0.2285 0.029 Uiso 1 1 calc R . . C223 C 0.51826(15) 0.76596(14) 0.22387(13) 0.0227(4) Uani 1 1 d . . . C224 C 0.59516(15) 0.76120(14) 0.18956(13) 0.0237(4) Uani 1 1 d . . . O224 O 0.58071(12) 0.69939(11) 0.12313(10) 0.0299(4) Uani 1 1 d . . . H224 H 0.638(2) 0.707(2) 0.1097(19) 0.059(9) Uiso 1 1 d . . . C225 C 0.68942(15) 0.81934(14) 0.22295(13) 0.0244(4) Uani 1 1 d . . . C226 C 0.70594(16) 0.87835(15) 0.29218(14) 0.0274(5) Uani 1 1 d . . . H226 H 0.7671 0.9188 0.3128 0.033 Uiso 1 1 calc R . . C227 C 0.63399(16) 0.88043(15) 0.33361(13) 0.0264(5) Uani 1 1 d . . . C228 C 0.65724(18) 0.93356(17) 0.41062(15) 0.0336(5) Uani 1 1 d . . . H228 H 0.7198 0.9721 0.4325 0.040 Uiso 1 1 calc R . . C229 C 0.59134(19) 0.93033(17) 0.45397(15) 0.0354(5) Uani 1 1 d . . . H229 H 0.6084 0.9656 0.5060 0.043 Uiso 1 1 calc R . . C230 C 0.49770(17) 0.87420(16) 0.42085(14) 0.0306(5) Uani 1 1 d . . . H230 H 0.4518 0.8718 0.4510 0.037 Uiso 1 1 calc R . . C231 C 0.47171(16) 0.82298(15) 0.34577(13) 0.0264(5) Uani 1 1 d . . . H231 H 0.4075 0.7867 0.3243 0.032 Uiso 1 1 calc R . . C232 C 0.53946(15) 0.82322(14) 0.29930(13) 0.0231(4) Uani 1 1 d . . . C233 C 0.77132(17) 0.81370(16) 0.18434(15) 0.0295(5) Uani 1 1 d . . . O233 O 0.76003(13) 0.75445(13) 0.12586(12) 0.0442(5) Uani 1 1 d . . . O234 O 0.85090(12) 0.87114(11) 0.21625(10) 0.0336(4) Uani 1 1 d . . . O1 O 0.2121(2) 0.9978(2) 0.3248(2) 0.0557(10) Uani 0.699(5) 1 d P A 1 C1 C 0.1336(4) 0.9990(3) 0.3438(3) 0.0366(11) Uani 0.699(5) 1 d P A 1 N2 N 0.1156(3) 0.9385(2) 0.4006(2) 0.0443(10) Uani 0.699(5) 1 d P A 1 C3 C 0.0148(6) 0.9519(5) 0.4072(5) 0.0468(16) Uani 0.699(5) 1 d P A 1 H3A H 0.0226 0.9515 0.4680 0.056 Uiso 0.699(5) 1 calc PR A 1 H3B H -0.0363 0.9006 0.3755 0.056 Uiso 0.699(5) 1 calc PR A 1 C4 C -0.0215(5) 1.0529(3) 0.3658(4) 0.0574(13) Uani 0.699(5) 1 d P A 1 H4A H -0.0993 1.0543 0.3323 0.069 Uiso 0.699(5) 1 calc PR A 1 H4B H -0.0025 1.1046 0.4100 0.069 Uiso 0.699(5) 1 calc PR A 1 C5 C 0.0390(4) 1.0655(4) 0.3073(4) 0.0374(11) Uani 0.699(5) 1 d P A 1 H5A H -0.0060 1.0469 0.2476 0.045 Uiso 0.699(5) 1 calc PR A 1 H5B H 0.0621 1.1337 0.3078 0.045 Uiso 0.699(5) 1 calc PR A 1 C6 C 0.1831(9) 0.8587(8) 0.4420(7) 0.086(5) Uani 0.699(5) 1 d P A 1 H6A H 0.1447 0.7975 0.4217 0.129 Uiso 0.699(5) 1 calc PR A 1 H6B H 0.2043 0.8639 0.5043 0.129 Uiso 0.699(5) 1 calc PR A 1 H6C H 0.2466 0.8599 0.4284 0.129 Uiso 0.699(5) 1 calc PR A 1 O1A O -0.0437(5) 0.9232(5) 0.4381(4) 0.052(2) Uani 0.301(5) 1 d P A 2 C1A C 0.0360(15) 0.9192(13) 0.4140(13) 0.056(5) Uani 0.301(5) 1 d P A 2 N2A N 0.0717(6) 0.9883(6) 0.3741(4) 0.0345(18) Uani 0.301(5) 1 d P A 2 C3A C 0.1672(9) 0.9675(8) 0.3724(8) 0.038(3) Uani 0.301(5) 1 d P A 2 H3C H 0.2186 1.0207 0.3984 0.046 Uiso 0.301(5) 1 calc PR A 2 H3D H 0.1614 0.9565 0.3129 0.046 Uiso 0.301(5) 1 calc PR A 2 C4A C 0.2026(13) 0.8692(19) 0.4289(11) 0.039(4) Uani 0.301(5) 1 d P A 2 H4D H 0.2147 0.8160 0.3944 0.046 Uiso 0.301(5) 1 calc PR A 2 H4C H 0.2689 0.8801 0.4801 0.046 Uiso 0.301(5) 1 calc PR A 2 C5A C 0.1165(9) 0.8454(10) 0.4542(11) 0.083(6) Uani 0.301(5) 1 d P A 2 H5C H 0.1402 0.8474 0.5175 0.100 Uiso 0.301(5) 1 calc PR A 2 H5D H 0.0885 0.7797 0.4337 0.100 Uiso 0.301(5) 1 calc PR A 2 C6A C 0.0097(12) 1.0718(10) 0.3306(9) 0.055(4) Uani 0.301(5) 1 d P A 2 H6E H 0.0575 1.1257 0.3324 0.082 Uiso 0.301(5) 1 calc PR A 2 H6D H -0.0373 1.0914 0.3591 0.082 Uiso 0.301(5) 1 calc PR A 2 H6F H -0.0331 1.0550 0.2706 0.082 Uiso 0.301(5) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0555(16) 0.0599(16) 0.0764(19) -0.0270(14) 0.0229(14) -0.0251(13) C12 0.0384(14) 0.0319(13) 0.0550(16) -0.0171(12) 0.0100(12) -0.0098(11) C13 0.0549(16) 0.0299(12) 0.0334(13) -0.0090(10) 0.0041(12) -0.0137(11) C14 0.0541(18) 0.0328(13) 0.0548(17) -0.0084(12) 0.0052(14) -0.0118(13) C15 0.058(2) 0.0414(18) 0.125(4) -0.037(2) -0.048(2) 0.0197(16) C16 0.0427(17) 0.064(2) 0.087(3) -0.029(2) 0.0058(17) -0.0021(16) C17 0.0544(16) 0.0316(13) 0.0536(17) -0.0084(12) 0.0058(13) -0.0074(12) C18 0.0567(18) 0.0592(18) 0.0572(18) -0.0202(15) 0.0166(15) -0.0171(15) O211 0.0243(8) 0.0321(8) 0.0297(8) 0.0077(6) 0.0132(6) 0.0020(6) C211 0.0208(10) 0.0215(10) 0.0231(10) -0.0007(8) 0.0079(8) -0.0029(8) C212 0.0188(9) 0.0235(10) 0.0246(10) -0.0032(8) 0.0077(8) -0.0042(8) C213 0.0181(9) 0.0231(10) 0.0242(10) -0.0023(8) 0.0059(8) -0.0009(8) C214 0.0207(10) 0.0212(9) 0.0225(10) -0.0040(8) 0.0071(8) -0.0044(8) C215 0.0222(10) 0.0250(10) 0.0245(10) 0.0000(8) 0.0057(8) 0.0003(8) C216 0.0317(11) 0.0293(11) 0.0229(10) 0.0022(9) 0.0097(9) -0.0028(9) C217 0.0270(11) 0.0341(11) 0.0263(11) -0.0008(9) 0.0139(9) -0.0018(9) C218 0.0207(10) 0.0271(10) 0.0271(11) -0.0032(8) 0.0096(8) -0.0015(8) C219 0.0208(10) 0.0227(10) 0.0223(10) -0.0034(8) 0.0077(8) -0.0040(8) C220 0.0197(9) 0.0213(9) 0.0246(10) -0.0006(8) 0.0079(8) -0.0012(8) C221 0.0195(10) 0.0262(10) 0.0272(11) -0.0044(9) 0.0091(8) -0.0046(8) O221 0.0263(8) 0.0348(8) 0.0301(8) 0.0032(7) 0.0154(6) -0.0005(6) O222 0.0220(8) 0.0406(9) 0.0404(9) 0.0086(7) 0.0162(7) 0.0047(6) C222 0.0225(10) 0.0249(10) 0.0271(11) 0.0022(8) 0.0120(8) 0.0019(8) C223 0.0191(9) 0.0233(10) 0.0255(10) 0.0062(8) 0.0085(8) 0.0056(8) C224 0.0226(10) 0.0230(10) 0.0267(11) 0.0050(8) 0.0109(8) 0.0066(8) O224 0.0284(8) 0.0321(8) 0.0346(9) -0.0027(7) 0.0181(7) 0.0017(6) C225 0.0207(10) 0.0255(10) 0.0297(11) 0.0080(8) 0.0127(8) 0.0066(8) C226 0.0214(10) 0.0285(11) 0.0322(12) 0.0033(9) 0.0102(9) 0.0008(8) C227 0.0220(10) 0.0286(11) 0.0286(11) 0.0036(9) 0.0099(9) 0.0029(8) C228 0.0291(12) 0.0364(12) 0.0347(12) -0.0035(10) 0.0118(10) -0.0036(9) C229 0.0382(13) 0.0375(12) 0.0324(12) -0.0057(10) 0.0156(10) 0.0000(10) C230 0.0288(11) 0.0380(12) 0.0298(11) 0.0055(9) 0.0165(9) 0.0048(9) C231 0.0232(10) 0.0293(11) 0.0281(11) 0.0048(9) 0.0116(8) 0.0030(8) C232 0.0193(9) 0.0250(10) 0.0258(10) 0.0069(8) 0.0097(8) 0.0051(8) C233 0.0246(11) 0.0309(11) 0.0367(12) 0.0066(10) 0.0158(9) 0.0058(9) O233 0.0392(10) 0.0475(10) 0.0604(12) -0.0154(9) 0.0351(9) -0.0061(8) O234 0.0245(8) 0.0386(9) 0.0433(9) 0.0025(7) 0.0193(7) -0.0003(7) O1 0.0372(15) 0.0501(17) 0.083(2) 0.0342(15) 0.0265(14) 0.0093(12) C1 0.039(3) 0.027(2) 0.036(3) 0.0048(17) 0.007(2) -0.0013(18) N2 0.063(3) 0.0243(17) 0.0311(17) 0.0032(14) 0.0023(18) -0.0018(19) C3 0.054(5) 0.053(4) 0.036(3) 0.000(3) 0.020(3) -0.003(3) C4 0.083(3) 0.040(2) 0.070(3) 0.006(2) 0.054(3) 0.009(2) C5 0.041(3) 0.031(2) 0.040(3) 0.0032(19) 0.0154(18) 0.0011(19) C6 0.121(10) 0.033(3) 0.056(5) 0.006(3) -0.017(5) 0.021(6) O1A 0.045(4) 0.042(4) 0.062(4) -0.003(3) 0.015(3) -0.005(3) C1A 0.043(7) 0.085(13) 0.049(7) 0.041(8) 0.027(5) 0.045(8) N2A 0.038(4) 0.034(4) 0.029(4) 0.011(3) 0.010(3) 0.004(3) C3A 0.043(7) 0.024(5) 0.037(6) 0.006(4) 0.003(5) -0.009(5) C4A 0.024(5) 0.067(12) 0.013(5) -0.012(6) -0.007(4) 0.011(5) C5A 0.030(6) 0.066(8) 0.155(14) 0.055(8) 0.036(7) 0.007(5) C6A 0.070(11) 0.038(6) 0.052(9) 0.021(6) 0.020(6) 0.032(7) _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 N11 C12 1.300(4) . ? N11 C16 1.308(4) . ? C12 C13 1.423(4) . ? C12 C17 1.464(4) . ? C13 C14 1.338(4) . ? C13 C18 1.468(4) . ? C14 C15 1.401(6) . ? C15 C16 1.450(6) . ? O211 C211 1.361(2) . ? C211 C220 1.390(3) . ? C211 C212 1.432(3) . ? C212 C213 1.374(3) . ? C212 C221 1.498(3) . ? C213 C214 1.413(3) . ? C214 C215 1.418(3) . ? C214 C219 1.431(3) . ? C215 C216 1.372(3) . ? C216 C217 1.411(3) . ? C217 C218 1.369(3) . ? C218 C219 1.428(3) . ? C219 C220 1.426(3) . ? C220 C222 1.525(3) . ? C221 O221 1.243(2) . ? C221 O222 1.290(2) . ? C222 C223 1.526(3) . ? C223 C224 1.385(3) . ? C223 C232 1.429(3) . ? C224 O224 1.361(2) . ? C224 C225 1.432(3) . ? C225 C226 1.369(3) . ? C225 C233 1.501(3) . ? C226 C227 1.412(3) . ? C227 C228 1.417(3) . ? C227 C232 1.428(3) . ? C228 C229 1.365(3) . ? C229 C230 1.410(3) . ? C230 C231 1.372(3) . ? C231 C232 1.428(3) . ? C233 O233 1.244(3) . ? C233 O234 1.281(3) . ? O1 C1 1.235(5) . ? C1 N2 1.363(6) . ? C1 C5 1.506(7) . ? N2 C6 1.430(11) . ? N2 C3 1.436(9) . ? C3 C4 1.549(8) . ? C4 C5 1.525(6) . ? O1A C1A 1.30(2) . ? C1A N2A 1.36(2) . ? C1A C5A 1.457(16) . ? N2A C3A 1.346(15) . ? N2A C6A 1.448(14) . ? C3A C4A 1.62(3) . ? C4A C5A 1.44(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 C12 N11 C16 128.0(3) . . ? N11 C12 C13 118.8(3) . . ? N11 C12 C17 120.5(3) . . ? C13 C12 C17 120.6(3) . . ? C14 C13 C12 118.1(3) . . ? C14 C13 C18 121.7(3) . . ? C12 C13 C18 120.2(3) . . ? C13 C14 C15 121.0(3) . . ? C14 C15 C16 119.2(3) . . ? N11 C16 C15 114.7(3) . . ? O211 C211 C220 119.05(17) . . ? O211 C211 C212 119.67(17) . . ? C220 C211 C212 121.28(18) . . ? C213 C212 C211 119.35(18) . . ? C213 C212 C221 120.63(18) . . ? C211 C212 C221 120.02(18) . . ? C212 C213 C214 121.52(18) . . ? C213 C214 C215 121.04(18) . . ? C213 C214 C219 118.75(18) . . ? C215 C214 C219 120.16(18) . . ? C216 C215 C214 120.91(19) . . ? C215 C216 C217 119.25(19) . . ? C218 C217 C216 121.41(19) . . ? C217 C218 C219 121.11(19) . . ? C220 C219 C218 122.65(18) . . ? C220 C219 C214 120.17(17) . . ? C218 C219 C214 117.12(18) . . ? C211 C220 C219 118.70(17) . . ? C211 C220 C222 119.79(17) . . ? C219 C220 C222 121.45(17) . . ? O221 C221 O222 123.73(18) . . ? O221 C221 C212 120.71(18) . . ? O222 C221 C212 115.55(18) . . ? C220 C222 C223 114.53(16) . . ? C224 C223 C232 118.46(18) . . ? C224 C223 C222 119.85(18) . . ? C232 C223 C222 121.62(17) . . ? O224 C224 C223 119.04(18) . . ? O224 C224 C225 119.59(17) . . ? C223 C224 C225 121.37(19) . . ? C226 C225 C224 119.47(18) . . ? C226 C225 C233 119.99(19) . . ? C224 C225 C233 120.52(19) . . ? C225 C226 C227 121.41(19) . . ? C226 C227 C228 121.06(19) . . ? C226 C227 C232 118.77(19) . . ? C228 C227 C232 120.07(19) . . ? C229 C228 C227 121.2(2) . . ? C228 C229 C230 119.4(2) . . ? C231 C230 C229 121.1(2) . . ? C230 C231 C232 121.2(2) . . ? C227 C232 C231 117.05(19) . . ? C227 C232 C223 120.20(18) . . ? C231 C232 C223 122.68(18) . . ? O233 C233 O234 124.15(19) . . ? O233 C233 C225 119.79(19) . . ? O234 C233 C225 116.04(19) . . ? O1 C1 N2 126.1(5) . . ? O1 C1 C5 126.5(4) . . ? N2 C1 C5 107.4(4) . . ? C1 N2 C6 123.7(7) . . ? C1 N2 C3 114.7(5) . . ? C6 N2 C3 121.1(6) . . ? N2 C3 C4 103.1(6) . . ? C5 C4 C3 103.7(5) . . ? C1 C5 C4 105.1(5) . . ? O1A C1A N2A 128.9(11) . . ? O1A C1A C5A 117.1(15) . . ? N2A C1A C5A 111.5(14) . . ? C3A N2A C1A 113.5(11) . . ? C3A N2A C6A 122.5(11) . . ? C1A N2A C6A 123.7(10) . . ? N2A C3A C4A 103.5(11) . . ? C5A C4A C3A 106.0(14) . . ? C4A C5A C1A 105.0(15) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O211 H211 O221 0.98(3) 1.63(3) 2.548(2) 155(3) . N11 H11 O1 0.88 1.90 2.764(4) 165.6 . O224 H224 O233 0.90(3) 1.71(3) 2.547(2) 153(3) . O222 H222 O234 1.18(4) 1.28(4) 2.457(2) 177(4) 1_455 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.64 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.840 _refine_diff_density_min -0.485 _refine_diff_density_rms 0.053 #=== END data_7 _database_code_depnum_ccdc_archive 'CCDC 788712' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,4 lutidinium pamoate NMP solvate' _chemical_melting_point ? _chemical_formula_moiety ' C23 H15 O6 1- , C7 H10 N 1+ , C5 H9 N O' _chemical_formula_sum 'C35 H34 N2 O7' _chemical_formula_weight 594.64 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6968(8) _cell_length_b 9.0998(9) _cell_length_c 21.112(2) _cell_angle_alpha 82.0410(10) _cell_angle_beta 86.5460(10) _cell_angle_gamma 79.8830(10) _cell_volume 1440.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7785 _cell_measurement_theta_min 2.372 _cell_measurement_theta_max 27.743 _exptl_crystal_description shard _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9746 _exptl_absorpt_correction_T_max 0.9848 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 16345 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 0.97 _diffrn_reflns_theta_max 27.95 _reflns_number_total 6274 _reflns_number_gt 5491 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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. All protons involved in proton transfer reactions were located in the difference map. ; _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^)+(0.0583P)^2^+1.0138P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6274 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 N1 N 0.83452(17) 1.14659(14) -0.13140(6) 0.0206(3) Uani 1 1 d . . . O2 O 1.00573(14) 0.94381(12) -0.07751(5) 0.0231(2) Uani 1 1 d . . . C2 C 0.8621(2) 1.03009(17) -0.08489(7) 0.0194(3) Uani 1 1 d . . . C3 C 0.6947(2) 1.02176(17) -0.04489(7) 0.0214(3) Uani 1 1 d . . . H3A H 0.7159 1.0209 0.0010 0.026 Uiso 1 1 calc R . . H3B H 0.6471 0.9300 -0.0501 0.026 Uiso 1 1 calc R . . C4 C 0.5670(2) 1.16406(19) -0.07034(8) 0.0268(3) Uani 1 1 d . . . H4A H 0.5539 1.2400 -0.0403 0.032 Uiso 1 1 calc R . . H4B H 0.4492 1.1398 -0.0765 0.032 Uiso 1 1 calc R . . C5 C 0.6515(2) 1.22253(17) -0.13458(8) 0.0233(3) Uani 1 1 d . . . H5B H 0.5933 1.1959 -0.1709 0.028 Uiso 1 1 calc R . . H5A H 0.6441 1.3332 -0.1392 0.028 Uiso 1 1 calc R . . C6 C 0.9642(2) 1.18046(18) -0.18144(7) 0.0251(3) Uani 1 1 d . . . H6A H 1.0825 1.1336 -0.1674 0.038 Uiso 1 1 calc R . . H6C H 0.9583 1.2898 -0.1906 0.038 Uiso 1 1 calc R . . H6B H 0.9397 1.1410 -0.2203 0.038 Uiso 1 1 calc R . . N11 N 1.36918(19) -0.22435(16) 0.57077(7) 0.0277(3) Uani 1 1 d . . . H11 H 1.295(4) -0.113(4) 0.5341(16) 0.096(11) Uiso 1 1 d . . . C12 C 1.4337(2) -0.2029(2) 0.62653(8) 0.0277(4) Uani 1 1 d . . . C13 C 1.5135(2) -0.3246(2) 0.66627(9) 0.0302(4) Uani 1 1 d . . . H13 H 1.5581 -0.3094 0.7054 0.036 Uiso 1 1 calc R . . C14 C 1.5305(2) -0.4703(2) 0.65058(9) 0.0311(4) Uani 1 1 d . . . C15 C 1.4635(3) -0.4880(2) 0.59341(9) 0.0338(4) Uani 1 1 d . . . H15 H 1.4728 -0.5854 0.5808 0.041 Uiso 1 1 calc R . . C16 C 1.3817(2) -0.3608(2) 0.55428(8) 0.0326(4) Uani 1 1 d . . . H16 H 1.3343 -0.3728 0.5152 0.039 Uiso 1 1 calc R . . C17 C 1.4099(3) -0.0450(2) 0.64074(9) 0.0340(4) Uani 1 1 d . . . H17B H 1.2977 -0.0212 0.6647 0.051 Uiso 1 1 calc R . . H17A H 1.4089 0.0234 0.6005 0.051 Uiso 1 1 calc R . . H17C H 1.5073 -0.0331 0.6664 0.051 Uiso 1 1 calc R . . C18 C 1.6161(3) -0.6022(2) 0.69467(10) 0.0400(5) Uani 1 1 d . . . H18A H 1.6298 -0.6932 0.6736 0.060 Uiso 1 1 calc R . . H18C H 1.5422 -0.6147 0.7339 0.060 Uiso 1 1 calc R . . H18B H 1.7324 -0.5853 0.7055 0.060 Uiso 1 1 calc R . . O211 O 1.07436(15) -0.00648(12) 0.31877(5) 0.0235(2) Uani 1 1 d . . . H211 H 1.119(3) -0.072(3) 0.3545(12) 0.054(7) Uiso 1 1 d . . . C211 C 1.06000(19) 0.13025(17) 0.33992(7) 0.0186(3) Uani 1 1 d . . . C212 C 1.1145(2) 0.13647(17) 0.40303(7) 0.0207(3) Uani 1 1 d . . . C213 C 1.1010(2) 0.27293(18) 0.42493(7) 0.0216(3) Uani 1 1 d . . . H213 H 1.1424 0.2771 0.4660 0.026 Uiso 1 1 calc R . . C214 C 1.0265(2) 0.40785(17) 0.38745(7) 0.0205(3) Uani 1 1 d . . . C215 C 1.0042(2) 0.54853(18) 0.41138(8) 0.0249(3) Uani 1 1 d . . . H215 H 1.0501 0.5536 0.4516 0.030 Uiso 1 1 calc R . . C216 C 0.9176(2) 0.67693(18) 0.37750(8) 0.0263(3) Uani 1 1 d . . . H216 H 0.9008 0.7699 0.3945 0.032 Uiso 1 1 calc R . . C217 C 0.8538(2) 0.66955(18) 0.31711(8) 0.0245(3) Uani 1 1 d . . . H217 H 0.7912 0.7580 0.2940 0.029 Uiso 1 1 calc R . . C218 C 0.8803(2) 0.53673(17) 0.29097(7) 0.0209(3) Uani 1 1 d . . . H218 H 0.8393 0.5358 0.2495 0.025 Uiso 1 1 calc R . . C219 C 0.96845(19) 0.40047(17) 0.32512(7) 0.0182(3) Uani 1 1 d . . . C220 C 0.99395(19) 0.25968(17) 0.29997(7) 0.0179(3) Uani 1 1 d . . . C221 C 1.1899(2) -0.00515(18) 0.44485(8) 0.0243(3) Uani 1 1 d . . . O222 O 1.21051(16) -0.12887(13) 0.42319(6) 0.0285(3) Uani 1 1 d . . . O221 O 1.23024(17) 0.01078(14) 0.50093(6) 0.0317(3) Uani 1 1 d . . . C222 C 0.94247(19) 0.25089(16) 0.23190(7) 0.0180(3) Uani 1 1 d . . . H22A H 0.9501 0.1435 0.2266 0.022 Uiso 1 1 calc R . . H22B H 0.8176 0.2994 0.2270 0.022 Uiso 1 1 calc R . . C223 C 1.05382(19) 0.32383(16) 0.17810(7) 0.0175(3) Uani 1 1 d . . . O224 O 0.80248(14) 0.50251(13) 0.14419(5) 0.0221(2) Uani 1 1 d . . . H224 H 0.781(3) 0.581(3) 0.1104(12) 0.051(7) Uiso 1 1 d . . . C224 C 0.97736(19) 0.44677(17) 0.13648(7) 0.0182(3) Uani 1 1 d . . . C225 C 1.07952(19) 0.51660(16) 0.08544(7) 0.0182(3) Uani 1 1 d . . . C226 C 1.2548(2) 0.46009(17) 0.07677(7) 0.0194(3) Uani 1 1 d . . . H226 H 1.3217 0.5072 0.0431 0.023 Uiso 1 1 calc R . . C227 C 1.33804(19) 0.33393(17) 0.11656(7) 0.0186(3) Uani 1 1 d . . . C228 C 1.5200(2) 0.27485(18) 0.10665(7) 0.0216(3) Uani 1 1 d . . . H228 H 1.5875 0.3243 0.0739 0.026 Uiso 1 1 calc R . . C229 C 1.5990(2) 0.14838(18) 0.14343(8) 0.0230(3) Uani 1 1 d . . . H229 H 1.7206 0.1101 0.1365 0.028 Uiso 1 1 calc R . . C230 C 1.4979(2) 0.07509(18) 0.19184(7) 0.0225(3) Uani 1 1 d . . . H230 H 1.5523 -0.0142 0.2168 0.027 Uiso 1 1 calc R . . C231 C 1.3224(2) 0.12984(17) 0.20374(7) 0.0209(3) Uani 1 1 d . . . H231 H 1.2582 0.0782 0.2368 0.025 Uiso 1 1 calc R . . C232 C 1.23584(19) 0.26311(16) 0.16707(7) 0.0178(3) Uani 1 1 d . . . C233 C 0.9949(2) 0.65118(17) 0.04269(7) 0.0194(3) Uani 1 1 d . . . O233 O 0.83902(15) 0.70670(13) 0.04912(5) 0.0263(3) Uani 1 1 d . . . O234 O 1.10259(14) 0.70545(13) -0.00181(5) 0.0232(2) Uani 1 1 d . . . H234 H 1.037(4) 0.798(4) -0.0303(16) 0.098(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 N1 0.0234(7) 0.0195(6) 0.0178(6) -0.0007(5) 0.0007(5) -0.0024(5) O2 0.0204(5) 0.0235(6) 0.0223(5) 0.0025(4) 0.0028(4) -0.0003(4) C2 0.0220(7) 0.0203(7) 0.0162(7) -0.0021(5) -0.0002(5) -0.0051(6) C3 0.0191(7) 0.0230(7) 0.0213(7) -0.0008(6) 0.0014(6) -0.0037(6) C4 0.0219(8) 0.0260(8) 0.0302(9) -0.0015(7) 0.0025(6) -0.0004(6) C5 0.0253(8) 0.0192(7) 0.0244(8) -0.0009(6) -0.0042(6) -0.0017(6) C6 0.0324(9) 0.0229(8) 0.0191(7) -0.0007(6) 0.0055(6) -0.0061(6) N11 0.0289(7) 0.0289(7) 0.0236(7) 0.0011(6) -0.0006(6) -0.0041(6) C12 0.0225(8) 0.0357(9) 0.0257(8) -0.0066(7) 0.0022(6) -0.0067(7) C13 0.0271(9) 0.0345(9) 0.0302(9) -0.0063(7) 0.0037(7) -0.0085(7) C14 0.0235(8) 0.0322(9) 0.0339(9) 0.0030(7) 0.0068(7) -0.0025(7) C15 0.0426(10) 0.0246(8) 0.0327(9) -0.0049(7) 0.0110(8) -0.0054(7) C16 0.0346(9) 0.0411(10) 0.0226(8) -0.0087(7) -0.0002(7) -0.0043(8) C17 0.0355(10) 0.0373(10) 0.0291(9) -0.0056(7) -0.0065(7) -0.0033(8) C18 0.0359(10) 0.0410(11) 0.0379(10) 0.0065(8) 0.0010(8) -0.0023(8) O211 0.0317(6) 0.0170(5) 0.0213(6) -0.0011(4) -0.0014(5) -0.0040(4) C211 0.0183(7) 0.0190(7) 0.0185(7) -0.0022(5) 0.0035(5) -0.0051(5) C212 0.0196(7) 0.0236(8) 0.0179(7) 0.0011(6) 0.0013(6) -0.0047(6) C213 0.0231(7) 0.0272(8) 0.0153(7) -0.0021(6) 0.0007(6) -0.0072(6) C214 0.0221(7) 0.0227(7) 0.0172(7) -0.0030(6) 0.0050(6) -0.0070(6) C215 0.0304(8) 0.0278(8) 0.0186(7) -0.0059(6) 0.0051(6) -0.0107(7) C216 0.0342(9) 0.0200(7) 0.0258(8) -0.0064(6) 0.0096(7) -0.0084(6) C217 0.0282(8) 0.0198(7) 0.0232(8) 0.0010(6) 0.0078(6) -0.0038(6) C218 0.0233(7) 0.0214(7) 0.0168(7) -0.0002(6) 0.0048(6) -0.0040(6) C219 0.0180(7) 0.0204(7) 0.0161(7) -0.0015(5) 0.0048(5) -0.0054(5) C220 0.0164(7) 0.0205(7) 0.0168(7) -0.0017(5) 0.0022(5) -0.0044(5) C221 0.0235(8) 0.0262(8) 0.0221(8) 0.0035(6) -0.0011(6) -0.0059(6) O222 0.0339(6) 0.0228(6) 0.0266(6) 0.0031(5) -0.0050(5) -0.0029(5) O221 0.0411(7) 0.0299(6) 0.0230(6) 0.0034(5) -0.0108(5) -0.0052(5) C222 0.0183(7) 0.0183(7) 0.0171(7) -0.0018(5) 0.0007(5) -0.0035(5) C223 0.0196(7) 0.0193(7) 0.0147(7) -0.0045(5) 0.0001(5) -0.0050(5) O224 0.0176(5) 0.0254(6) 0.0206(5) 0.0018(4) -0.0002(4) -0.0008(4) C224 0.0187(7) 0.0206(7) 0.0163(7) -0.0049(5) -0.0005(5) -0.0044(6) C225 0.0207(7) 0.0187(7) 0.0155(7) -0.0027(5) -0.0012(5) -0.0032(6) C226 0.0219(7) 0.0200(7) 0.0171(7) -0.0035(5) 0.0006(5) -0.0049(6) C227 0.0181(7) 0.0207(7) 0.0179(7) -0.0056(6) -0.0012(5) -0.0034(6) C228 0.0197(7) 0.0249(8) 0.0206(7) -0.0049(6) 0.0010(6) -0.0041(6) C229 0.0175(7) 0.0275(8) 0.0239(8) -0.0085(6) -0.0019(6) 0.0008(6) C230 0.0251(8) 0.0212(7) 0.0202(7) -0.0040(6) -0.0059(6) 0.0015(6) C231 0.0235(8) 0.0219(7) 0.0179(7) -0.0047(6) -0.0009(6) -0.0034(6) C232 0.0195(7) 0.0194(7) 0.0156(7) -0.0056(5) -0.0018(5) -0.0034(5) C233 0.0224(7) 0.0202(7) 0.0154(7) -0.0030(5) -0.0012(5) -0.0028(6) O233 0.0214(6) 0.0275(6) 0.0255(6) 0.0045(5) 0.0004(4) 0.0018(4) O234 0.0231(6) 0.0247(6) 0.0192(5) 0.0036(4) 0.0004(4) -0.0019(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.3383(19) . ? N1 C6 1.4488(19) . ? N1 C5 1.457(2) . ? O2 C2 1.2427(19) . ? C2 C3 1.505(2) . ? C3 C4 1.535(2) . ? C4 C5 1.537(2) . ? N11 C16 1.322(2) . ? N11 C12 1.356(2) . ? C12 C13 1.369(3) . ? C12 C17 1.486(3) . ? C13 C14 1.393(3) . ? C14 C15 1.381(3) . ? C14 C18 1.492(3) . ? C15 C16 1.400(3) . ? O211 C211 1.3636(18) . ? C211 C220 1.387(2) . ? C211 C212 1.432(2) . ? C212 C213 1.369(2) . ? C212 C221 1.504(2) . ? C213 C214 1.414(2) . ? C214 C215 1.419(2) . ? C214 C219 1.429(2) . ? C215 C216 1.369(2) . ? C216 C217 1.408(2) . ? C217 C218 1.375(2) . ? C218 C219 1.426(2) . ? C219 C220 1.432(2) . ? C220 C222 1.530(2) . ? C221 O222 1.254(2) . ? C221 O221 1.276(2) . ? C222 C223 1.5294(19) . ? C223 C224 1.389(2) . ? C223 C232 1.431(2) . ? O224 C224 1.3610(18) . ? C224 C225 1.438(2) . ? C225 C226 1.368(2) . ? C225 C233 1.491(2) . ? C226 C227 1.405(2) . ? C227 C228 1.423(2) . ? C227 C232 1.435(2) . ? C228 C229 1.364(2) . ? C229 C230 1.412(2) . ? C230 C231 1.376(2) . ? C231 C232 1.426(2) . ? C233 O233 1.2246(19) . ? C233 O234 1.3172(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 123.99(13) . . ? C2 N1 C5 113.91(13) . . ? C6 N1 C5 121.28(13) . . ? O2 C2 N1 123.70(14) . . ? O2 C2 C3 126.77(14) . . ? N1 C2 C3 109.53(13) . . ? C2 C3 C4 104.64(12) . . ? C3 C4 C5 105.00(12) . . ? N1 C5 C4 103.77(12) . . ? C16 N11 C12 121.07(15) . . ? N11 C12 C13 119.42(16) . . ? N11 C12 C17 116.52(16) . . ? C13 C12 C17 124.06(16) . . ? C12 C13 C14 121.42(17) . . ? C15 C14 C13 117.62(16) . . ? C15 C14 C18 121.50(17) . . ? C13 C14 C18 120.87(18) . . ? C14 C15 C16 119.25(17) . . ? N11 C16 C15 121.21(16) . . ? O211 C211 C220 119.48(13) . . ? O211 C211 C212 118.94(13) . . ? C220 C211 C212 121.58(14) . . ? C213 C212 C211 119.62(14) . . ? C213 C212 C221 119.78(14) . . ? C211 C212 C221 120.58(14) . . ? C212 C213 C214 121.17(14) . . ? C213 C214 C215 121.23(14) . . ? C213 C214 C219 118.87(14) . . ? C215 C214 C219 119.87(14) . . ? C216 C215 C214 121.19(15) . . ? C215 C216 C217 119.21(15) . . ? C218 C217 C216 121.29(15) . . ? C217 C218 C219 121.03(14) . . ? C218 C219 C214 117.26(13) . . ? C218 C219 C220 122.39(14) . . ? C214 C219 C220 120.31(13) . . ? C211 C220 C219 118.15(13) . . ? C211 C220 C222 120.71(13) . . ? C219 C220 C222 121.08(13) . . ? O222 C221 O221 124.39(15) . . ? O222 C221 C212 119.38(14) . . ? O221 C221 C212 116.22(14) . . ? C223 C222 C220 115.70(12) . . ? C224 C223 C232 118.25(13) . . ? C224 C223 C222 120.38(13) . . ? C232 C223 C222 121.29(13) . . ? O224 C224 C223 119.42(13) . . ? O224 C224 C225 119.31(13) . . ? C223 C224 C225 121.26(13) . . ? C226 C225 C224 119.73(13) . . ? C226 C225 C233 120.25(13) . . ? C224 C225 C233 120.02(13) . . ? C225 C226 C227 121.41(14) . . ? C226 C227 C228 120.98(14) . . ? C226 C227 C232 118.92(13) . . ? C228 C227 C232 120.09(14) . . ? C229 C228 C227 121.03(14) . . ? C228 C229 C230 119.24(14) . . ? C231 C230 C229 121.61(14) . . ? C230 C231 C232 120.84(14) . . ? C231 C232 C223 122.51(13) . . ? C231 C232 C227 117.14(13) . . ? C223 C232 C227 120.33(13) . . ? O233 C233 O234 123.26(14) . . ? O233 C233 C225 122.52(13) . . ? O234 C233 C225 114.21(13) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O221 1.26(3) 1.28(3) 2.5315(18) 173(3) . O234 H234 O2 1.04(3) 1.54(3) 2.5358(15) 160(3) . _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.626 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.050 #=== END data_8 _database_code_depnum_ccdc_archive 'CCDC 788713' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,5 lutidinium pamoate NMP solvate' _chemical_melting_point ? _chemical_formula_moiety '0.5(C46H30O12H -1), 0.5(C7H10N +1) , C5H9N' _chemical_formula_sum 'C28 H24.50 N O7' _chemical_formula_weight 486.99 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6370(6) _cell_length_b 10.4230(8) _cell_length_c 20.0330(16) _cell_angle_alpha 89.2920(10) _cell_angle_beta 85.4450(10) _cell_angle_gamma 74.6440(10) _cell_volume 1532.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6547 _cell_measurement_theta_min 2.261 _cell_measurement_theta_max 27.489 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.055 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 511 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9764 _exptl_absorpt_correction_T_max 0.9797 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 17437 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.02 _diffrn_reflns_theta_max 27.90 _reflns_number_total 6680 _reflns_number_gt 5357 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement ; SHELXL (Sheldrick, 2008), Platon/SQUEEZE (Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.) ; _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. H234 was located in the difference map. H221 was located in the difference map after application of the program SQUEEZE. ; _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^)+(0.0619P)^2^+0.1589P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6680 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1175 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.04281(11) 0.92143(8) -0.08028(4) 0.0295(2) Uani 1 1 d . . . C1 C 0.89341(16) 1.00408(12) -0.08564(6) 0.0278(3) Uani 1 1 d . . . N2 N 0.86791(14) 1.10256(10) -0.12982(5) 0.0307(2) Uani 1 1 d . . . C3 C 0.68170(17) 1.18459(12) -0.13042(7) 0.0313(3) Uani 1 1 d . . . H3A H 0.6295 1.1727 -0.1729 0.038 Uiso 1 1 calc R . . H3B H 0.6758 1.2799 -0.1246 0.038 Uiso 1 1 calc R . . C4 C 0.58007(17) 1.13374(13) -0.07038(7) 0.0335(3) Uani 1 1 d . . . H4B H 0.5394 1.2032 -0.0351 0.040 Uiso 1 1 calc R . . H4A H 0.4721 1.1092 -0.0847 0.040 Uiso 1 1 calc R . . C5 C 0.71588(16) 1.01215(12) -0.04434(6) 0.0295(3) Uani 1 1 d . . . H5B H 0.7298 1.0231 0.0038 0.035 Uiso 1 1 calc R . . H5A H 0.6752 0.9307 -0.0504 0.035 Uiso 1 1 calc R . . C6 C 1.00921(18) 1.12281(13) -0.17813(7) 0.0354(3) Uani 1 1 d . . . H6A H 0.9799 1.1055 -0.2233 0.053 Uiso 1 1 calc R . . H6B H 1.1262 1.0618 -0.1688 0.053 Uiso 1 1 calc R . . H6C H 1.0171 1.2148 -0.1749 0.053 Uiso 1 1 calc R . . O211 O 0.85356(13) 0.14303(8) 0.27648(5) 0.0327(2) Uani 1 1 d . . . H211 H 0.869(3) 0.079(2) 0.3075(11) 0.077(6) Uiso 1 1 d . . . C211 C 0.86178(16) 0.25366(11) 0.31007(6) 0.0248(2) Uani 1 1 d . . . C212 C 0.89325(17) 0.24475(11) 0.37946(6) 0.0280(3) Uani 1 1 d . . . C213 C 0.89783(17) 0.35662(11) 0.41394(6) 0.0292(3) Uani 1 1 d . . . H213 H 0.9194 0.3504 0.4601 0.035 Uiso 1 1 calc R . . C214 C 0.87101(16) 0.48069(11) 0.38185(6) 0.0264(3) Uani 1 1 d . . . C215 C 0.87201(18) 0.59652(12) 0.41809(7) 0.0328(3) Uani 1 1 d . . . H215 H 0.8915 0.5899 0.4644 0.039 Uiso 1 1 calc R . . C216 C 0.84550(19) 0.71725(12) 0.38768(7) 0.0353(3) Uani 1 1 d . . . H216 H 0.8495 0.7938 0.4122 0.042 Uiso 1 1 calc R . . C217 C 0.81211(18) 0.72671(12) 0.31944(7) 0.0336(3) Uani 1 1 d . . . H217 H 0.7902 0.8111 0.2985 0.040 Uiso 1 1 calc R . . C218 C 0.81036(16) 0.61738(11) 0.28247(6) 0.0278(3) Uani 1 1 d . . . H218 H 0.7873 0.6273 0.2365 0.033 Uiso 1 1 calc R . . C219 C 0.84270(15) 0.48874(11) 0.31210(6) 0.0232(2) Uani 1 1 d . . . C220 C 0.84351(15) 0.37239(11) 0.27549(6) 0.0229(2) Uani 1 1 d . . . C221 C 0.9243(2) 0.11305(12) 0.41409(7) 0.0378(3) Uani 1 1 d . . . O221 O 0.90628(17) 0.01451(9) 0.38376(5) 0.0495(3) Uani 1 1 d . . . O222 O 0.96964(18) 0.11094(9) 0.47437(5) 0.0548(3) Uani 1 1 d . . . H222 H 1.0000 0.0000 0.5000 0.110(11) Uiso 1 2 d S . . C222 C 0.81989(15) 0.37473(11) 0.20093(6) 0.0248(2) Uani 1 1 d . . . H22A H 0.7016 0.4381 0.1932 0.030 Uiso 1 1 calc R . . H22B H 0.8135 0.2853 0.1871 0.030 Uiso 1 1 calc R . . C223 C 0.96796(15) 0.41299(11) 0.15587(6) 0.0233(2) Uani 1 1 d . . . O224 O 0.74533(11) 0.59618(9) 0.11707(5) 0.0313(2) Uani 1 1 d . . . H224 H 0.743(2) 0.6636(18) 0.0867(9) 0.063(5) Uiso 1 1 d . . . C224 C 0.92247(15) 0.52362(11) 0.11536(6) 0.0241(2) Uani 1 1 d . . . C225 C 1.05842(15) 0.56255(11) 0.07221(6) 0.0237(2) Uani 1 1 d . . . C226 C 1.23667(16) 0.48887(11) 0.07110(6) 0.0245(2) Uani 1 1 d . . . H226 H 1.3268 0.5162 0.0434 0.029 Uiso 1 1 calc R . . C227 C 1.28899(15) 0.37368(11) 0.11007(6) 0.0238(2) Uani 1 1 d . . . C228 C 1.47200(16) 0.29618(12) 0.10748(6) 0.0272(3) Uani 1 1 d . . . H228 H 1.5624 0.3239 0.0801 0.033 Uiso 1 1 calc R . . C229 C 1.52099(16) 0.18210(12) 0.14378(6) 0.0303(3) Uani 1 1 d . . . H229 H 1.6447 0.1316 0.1421 0.036 Uiso 1 1 calc R . . C230 C 1.38640(17) 0.14019(12) 0.18363(7) 0.0315(3) Uani 1 1 d . . . H230 H 1.4201 0.0602 0.2083 0.038 Uiso 1 1 calc R . . C231 C 1.20752(16) 0.21273(11) 0.18744(6) 0.0271(3) Uani 1 1 d . . . H231 H 1.1193 0.1816 0.2143 0.032 Uiso 1 1 calc R . . C232 C 1.15202(15) 0.33378(11) 0.15189(6) 0.0231(2) Uani 1 1 d . . . C233 C 1.00392(16) 0.68294(11) 0.03034(6) 0.0252(2) Uani 1 1 d . . . O233 O 0.84471(12) 0.75005(9) 0.03105(5) 0.0351(2) Uani 1 1 d . . . O234 O 1.13574(11) 0.71378(8) -0.00702(4) 0.0292(2) Uani 1 1 d . . . H234 H 1.079(3) 0.796(2) -0.0337(12) 0.104(8) 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 0.0243(4) 0.0295(4) 0.0321(5) 0.0057(4) 0.0009(3) -0.0037(3) C1 0.0280(6) 0.0274(6) 0.0281(6) -0.0001(5) -0.0016(5) -0.0080(5) N2 0.0314(6) 0.0269(5) 0.0320(6) 0.0023(4) 0.0026(4) -0.0063(4) C3 0.0288(6) 0.0263(6) 0.0369(7) 0.0042(5) -0.0025(5) -0.0039(5) C4 0.0287(6) 0.0339(7) 0.0355(7) 0.0032(5) 0.0002(5) -0.0048(5) C5 0.0266(6) 0.0335(6) 0.0280(6) 0.0042(5) -0.0002(5) -0.0079(5) C6 0.0370(7) 0.0292(6) 0.0380(7) 0.0016(5) 0.0108(6) -0.0094(5) O211 0.0482(6) 0.0223(4) 0.0319(5) 0.0006(4) -0.0028(4) -0.0168(4) C211 0.0268(6) 0.0206(5) 0.0286(6) 0.0001(4) -0.0009(5) -0.0094(4) C212 0.0355(6) 0.0201(6) 0.0299(6) 0.0053(5) -0.0021(5) -0.0102(5) C213 0.0388(7) 0.0234(6) 0.0260(6) 0.0033(5) -0.0029(5) -0.0096(5) C214 0.0288(6) 0.0211(5) 0.0302(6) 0.0022(5) -0.0001(5) -0.0087(5) C215 0.0430(7) 0.0248(6) 0.0319(7) -0.0001(5) -0.0011(5) -0.0116(5) C216 0.0445(8) 0.0211(6) 0.0407(7) -0.0032(5) 0.0053(6) -0.0121(5) C217 0.0388(7) 0.0189(6) 0.0398(7) 0.0040(5) 0.0109(6) -0.0060(5) C218 0.0282(6) 0.0230(6) 0.0295(6) 0.0058(5) 0.0057(5) -0.0046(5) C219 0.0201(5) 0.0208(5) 0.0285(6) 0.0046(4) 0.0019(4) -0.0061(4) C220 0.0188(5) 0.0237(5) 0.0265(6) 0.0042(4) -0.0002(4) -0.0068(4) C221 0.0585(9) 0.0230(6) 0.0333(7) 0.0073(5) -0.0037(6) -0.0135(6) O221 0.0896(8) 0.0234(5) 0.0410(6) 0.0068(4) -0.0084(5) -0.0242(5) O222 0.1077(10) 0.0253(5) 0.0335(5) 0.0112(4) -0.0173(6) -0.0185(6) C222 0.0208(5) 0.0269(6) 0.0277(6) 0.0030(5) -0.0022(4) -0.0080(4) C223 0.0221(6) 0.0257(6) 0.0224(5) 0.0002(4) -0.0028(4) -0.0069(4) O224 0.0200(4) 0.0347(5) 0.0357(5) 0.0128(4) -0.0011(3) -0.0019(3) C224 0.0198(5) 0.0283(6) 0.0234(6) 0.0005(5) -0.0027(4) -0.0051(4) C225 0.0246(6) 0.0255(6) 0.0206(5) 0.0012(4) -0.0020(4) -0.0061(4) C226 0.0240(6) 0.0281(6) 0.0223(5) 0.0007(4) -0.0010(4) -0.0087(5) C227 0.0226(6) 0.0258(6) 0.0231(6) -0.0013(4) -0.0030(4) -0.0063(4) C228 0.0225(6) 0.0304(6) 0.0286(6) -0.0013(5) -0.0008(5) -0.0071(5) C229 0.0228(6) 0.0290(6) 0.0367(7) -0.0020(5) -0.0048(5) -0.0017(5) C230 0.0321(7) 0.0248(6) 0.0363(7) 0.0055(5) -0.0063(5) -0.0046(5) C231 0.0251(6) 0.0261(6) 0.0298(6) 0.0014(5) -0.0017(5) -0.0066(5) C232 0.0227(6) 0.0250(6) 0.0221(5) -0.0003(4) -0.0037(4) -0.0066(4) C233 0.0249(6) 0.0277(6) 0.0224(6) 0.0018(4) -0.0010(4) -0.0063(5) O233 0.0261(5) 0.0352(5) 0.0395(5) 0.0137(4) 0.0001(4) -0.0013(4) O234 0.0276(4) 0.0304(4) 0.0283(4) 0.0067(4) 0.0010(3) -0.0065(3) _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 1.2458(14) . ? C1 N2 1.3318(16) . ? C1 C5 1.5143(17) . ? N2 C6 1.4475(16) . ? N2 C3 1.4533(15) . ? C3 C4 1.5440(18) . ? C4 C5 1.5256(17) . ? O211 C211 1.3604(14) . ? C211 C220 1.3906(15) . ? C211 C212 1.4271(17) . ? C212 C213 1.3724(17) . ? C212 C221 1.5007(16) . ? C213 C214 1.4098(16) . ? C214 C215 1.4185(17) . ? C214 C219 1.4288(17) . ? C215 C216 1.3643(17) . ? C216 C217 1.4079(19) . ? C217 C218 1.3704(17) . ? C218 C219 1.4280(15) . ? C219 C220 1.4233(16) . ? C220 C222 1.5180(16) . ? C221 O221 1.2437(16) . ? C221 O222 1.2807(17) . ? C222 C223 1.5232(15) . ? C223 C224 1.3852(16) . ? C223 C232 1.4258(15) . ? O224 C224 1.3618(13) . ? C224 C225 1.4359(16) . ? C225 C226 1.3731(16) . ? C225 C233 1.4846(15) . ? C226 C227 1.4083(16) . ? C227 C228 1.4143(16) . ? C227 C232 1.4324(16) . ? C228 C229 1.3671(17) . ? C229 C230 1.4083(18) . ? C230 C231 1.3717(16) . ? C231 C232 1.4217(16) . ? C233 O233 1.2308(14) . ? C233 O234 1.3125(14) . ? 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 O1 C1 N2 123.59(11) . . ? O1 C1 C5 127.22(11) . . ? N2 C1 C5 109.18(10) . . ? C1 N2 C6 123.71(11) . . ? C1 N2 C3 115.24(10) . . ? C6 N2 C3 120.88(10) . . ? N2 C3 C4 103.86(10) . . ? C5 C4 C3 106.11(10) . . ? C1 C5 C4 105.14(10) . . ? O211 C211 C220 119.08(10) . . ? O211 C211 C212 119.44(10) . . ? C220 C211 C212 121.46(10) . . ? C213 C212 C211 119.69(10) . . ? C213 C212 C221 120.31(11) . . ? C211 C212 C221 120.00(11) . . ? C212 C213 C214 120.91(11) . . ? C213 C214 C215 120.66(11) . . ? C213 C214 C219 119.22(11) . . ? C215 C214 C219 120.12(10) . . ? C216 C215 C214 121.22(12) . . ? C215 C216 C217 118.98(12) . . ? C218 C217 C216 121.73(11) . . ? C217 C218 C219 120.87(11) . . ? C220 C219 C218 122.76(11) . . ? C220 C219 C214 120.21(10) . . ? C218 C219 C214 117.02(10) . . ? C211 C220 C219 118.35(10) . . ? C211 C220 C222 119.32(10) . . ? C219 C220 C222 122.31(10) . . ? O221 C221 O222 124.29(11) . . ? O221 C221 C212 119.66(12) . . ? O222 C221 C212 116.05(11) . . ? C220 C222 C223 115.99(9) . . ? C224 C223 C232 118.81(10) . . ? C224 C223 C222 119.63(10) . . ? C232 C223 C222 121.49(10) . . ? O224 C224 C223 118.87(10) . . ? O224 C224 C225 119.98(10) . . ? C223 C224 C225 121.16(10) . . ? C226 C225 C224 119.44(10) . . ? C226 C225 C233 121.23(10) . . ? C224 C225 C233 119.33(10) . . ? C225 C226 C227 121.53(11) . . ? C226 C227 C228 121.34(11) . . ? C226 C227 C232 118.72(10) . . ? C228 C227 C232 119.92(10) . . ? C229 C228 C227 121.08(11) . . ? C228 C229 C230 119.37(11) . . ? C231 C230 C229 121.23(11) . . ? C230 C231 C232 121.07(11) . . ? C231 C232 C223 122.50(10) . . ? C231 C232 C227 117.27(10) . . ? C223 C232 C227 120.22(10) . . ? O233 C233 O234 122.15(10) . . ? O233 C233 C225 121.85(10) . . ? O234 C233 C225 115.99(10) . . ? 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 O234 H234 O1 1.02(2) 1.57(2) 2.5721(11) 166(2) . _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.303 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.039 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.684 1.000 458 152 ' ' _platon_squeeze_details ; ; #=== END data_9 _database_code_depnum_ccdc_archive 'CCDC 788714' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'pamoic acid NMP solvate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H16 O6, 2(C5 H9 N O)' _chemical_formula_sum 'C33 H34 N2 O8' _chemical_formula_weight 586.62 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.4128(7) _cell_length_b 24.7372(11) _cell_length_c 16.1320(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.6300(10) _cell_angle_gamma 90.00 _cell_volume 5749.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6217 _cell_measurement_theta_min 2.170 _cell_measurement_theta_max 23.232 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2480 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9814 _exptl_absorpt_correction_T_max 0.9878 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 32695 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 26.00 _reflns_number_total 11246 _reflns_number_gt 7149 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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. All hydroxy protons were located in the difference map. ; _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^)+(0.0351P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11246 _refine_ls_number_parameters 876 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_restrained_S_all 0.905 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O11 O 0.04944(8) -0.11061(5) 1.15560(7) 0.0341(3) Uani 1 1 d . . . C12 C -0.01816(12) -0.08014(7) 1.16586(10) 0.0267(4) Uani 1 1 d . . . N13 N -0.10458(9) -0.09716(6) 1.17647(8) 0.0275(3) Uani 1 1 d . . . C14 C -0.17037(11) -0.05407(7) 1.19327(10) 0.0290(4) Uani 1 1 d . . . H14A H -0.1882 -0.0545 1.2521 0.035 Uiso 1 1 calc R . . H14B H -0.2270 -0.0576 1.1575 0.035 Uiso 1 1 calc R . . C15 C -0.11710(11) -0.00206(7) 1.17301(10) 0.0300(4) Uani 1 1 d . . . H15A H -0.1393 0.0133 1.1193 0.036 Uiso 1 1 calc R . . H15B H -0.1248 0.0254 1.2169 0.036 Uiso 1 1 calc R . . C16 C -0.01528(11) -0.01975(7) 1.16864(10) 0.0285(4) Uani 1 1 d . . . H16A H 0.0133 -0.0051 1.1183 0.034 Uiso 1 1 calc R . . H16B H 0.0208 -0.0071 1.2180 0.034 Uiso 1 1 calc R . . C17 C -0.13082(13) -0.15370(7) 1.18253(11) 0.0389(5) Uani 1 1 d . . . H17A H -0.0790 -0.1765 1.1659 0.058 Uiso 1 1 calc R . . H17B H -0.1849 -0.1607 1.1459 0.058 Uiso 1 1 calc R . . H17C H -0.1463 -0.1621 1.2399 0.058 Uiso 1 1 calc R . . O21A O 0.8508(8) 0.3465(5) 1.0196(6) 0.056(2) Uani 0.498(5) 1 d P A 1 C22A C 0.9263(4) 0.3662(3) 0.9970(3) 0.0416(13) Uani 0.498(5) 1 d P A 1 N23A N 0.9986(4) 0.3394(2) 0.9695(3) 0.0397(14) Uani 0.498(5) 1 d P A 1 C24A C 1.0803(4) 0.3722(3) 0.9584(4) 0.0482(15) Uani 0.498(5) 1 d P A 1 H24A H 1.1095 0.3639 0.9051 0.058 Uiso 0.498(5) 1 calc PR A 1 H24B H 1.1264 0.3665 1.0042 0.058 Uiso 0.498(5) 1 calc PR A 1 C25A C 1.0427(4) 0.4299(2) 0.9591(3) 0.0565(16) Uani 0.498(5) 1 d P A 1 H25A H 1.0858 0.4543 0.9901 0.068 Uiso 0.498(5) 1 calc PR A 1 H25B H 1.0336 0.4438 0.9019 0.068 Uiso 0.498(5) 1 calc PR A 1 C26A C 0.9510(5) 0.4258(3) 1.0019(4) 0.0480(19) Uani 0.498(5) 1 d P A 1 H26A H 0.9030 0.4481 0.9730 0.058 Uiso 0.498(5) 1 calc PR A 1 H26B H 0.9573 0.4379 1.0603 0.058 Uiso 0.498(5) 1 calc PR A 1 C27A C 1.0012(4) 0.2803(3) 0.9675(5) 0.056(3) Uani 0.498(5) 1 d P A 1 H27A H 1.0359 0.2669 1.0164 0.085 Uiso 0.498(5) 1 calc PR A 1 H27B H 1.0316 0.2682 0.9172 0.085 Uiso 0.498(5) 1 calc PR A 1 H27C H 0.9377 0.2661 0.9676 0.085 Uiso 0.498(5) 1 calc PR A 1 O21B O 0.8383(8) 0.3494(4) 0.9885(6) 0.048(2) Uani 0.502(5) 1 d P A 2 C22B C 0.9189(3) 0.3340(2) 0.9816(3) 0.0353(13) Uani 0.502(5) 1 d P A 2 N23B N 0.9878(4) 0.3678(2) 0.9671(3) 0.0344(13) Uani 0.502(5) 1 d P A 2 C24B C 1.0774(4) 0.3409(2) 0.9588(3) 0.0373(13) Uani 0.502(5) 1 d P A 2 H24C H 1.1188 0.3481 1.0076 0.045 Uiso 0.502(5) 1 calc PR A 2 H24D H 1.1084 0.3530 0.9081 0.045 Uiso 0.502(5) 1 calc PR A 2 C25B C 1.0525(3) 0.2819(3) 0.9534(6) 0.063(2) Uani 0.502(5) 1 d P A 2 H25C H 1.0953 0.2602 0.9891 0.076 Uiso 0.502(5) 1 calc PR A 2 H25D H 1.0565 0.2689 0.8956 0.076 Uiso 0.502(5) 1 calc PR A 2 C26B C 0.9543(4) 0.2770(3) 0.9827(5) 0.0445(16) Uani 0.502(5) 1 d P A 2 H26C H 0.9165 0.2538 0.9449 0.053 Uiso 0.502(5) 1 calc PR A 2 H26D H 0.9533 0.2617 1.0394 0.053 Uiso 0.502(5) 1 calc PR A 2 C27B C 0.9803(5) 0.4258(3) 0.9679(4) 0.0410(16) Uani 0.502(5) 1 d P A 2 H27D H 0.9157 0.4361 0.9772 0.062 Uiso 0.502(5) 1 calc PR A 2 H27E H 0.9996 0.4403 0.9145 0.062 Uiso 0.502(5) 1 calc PR A 2 H27F H 1.0204 0.4405 1.0125 0.062 Uiso 0.502(5) 1 calc PR A 2 O31 O 0.94081(9) 0.61908(5) 0.83853(8) 0.0420(3) Uani 1 1 d . . . C32 C 0.96324(13) 0.65676(8) 0.79246(11) 0.0353(5) Uani 1 1 d . . . N33 N 1.04842(12) 0.66799(7) 0.77143(10) 0.0485(5) Uani 1 1 d . . . C34 C 1.0541(2) 0.71395(10) 0.71449(13) 0.0740(8) Uani 1 1 d . . . H34A H 1.0619 0.7017 0.6567 0.089 Uiso 1 1 calc R . . H34B H 1.1060 0.7383 0.7306 0.089 Uiso 1 1 calc R . . C35 C 0.9611(2) 0.74130(10) 0.72480(16) 0.0863(9) Uani 1 1 d . . . H35A H 0.9385 0.7575 0.6718 0.104 Uiso 1 1 calc R . . H35B H 0.9655 0.7700 0.7675 0.104 Uiso 1 1 calc R . . C36 C 0.89706(15) 0.69631(8) 0.75164(12) 0.0543(6) Uani 1 1 d . . . H36A H 0.8511 0.7097 0.7912 0.065 Uiso 1 1 calc R . . H36B H 0.8639 0.6798 0.7034 0.065 Uiso 1 1 calc R . . C37 C 1.12827(16) 0.63567(10) 0.79127(18) 0.0854(9) Uani 1 1 d . . . H37A H 1.1121 0.6081 0.8321 0.128 Uiso 1 1 calc R . . H37B H 1.1779 0.6587 0.8144 0.128 Uiso 1 1 calc R . . H37C H 1.1496 0.6180 0.7409 0.128 Uiso 1 1 calc R . . O41 O 0.02653(9) 0.25767(5) 0.72235(8) 0.0407(3) Uani 1 1 d . . . C42 C -0.03974(13) 0.28816(8) 0.73699(11) 0.0341(4) Uani 1 1 d . . . N43 N -0.12207(10) 0.27123(6) 0.76140(9) 0.0387(4) Uani 1 1 d . . . C44 C -0.19043(13) 0.31417(8) 0.76946(13) 0.0468(5) Uani 1 1 d . . . H44A H -0.2184 0.3132 0.8248 0.056 Uiso 1 1 calc R . . H44B H -0.2404 0.3108 0.7263 0.056 Uiso 1 1 calc R . . C45 C -0.13526(13) 0.36625(8) 0.75804(13) 0.0499(6) Uani 1 1 d . . . H45A H -0.1662 0.3898 0.7160 0.060 Uiso 1 1 calc R . . H45B H -0.1294 0.3864 0.8110 0.060 Uiso 1 1 calc R . . C46 C -0.04063(13) 0.34854(7) 0.72944(11) 0.0385(5) Uani 1 1 d . . . H46A H -0.0316 0.3596 0.6713 0.046 Uiso 1 1 calc R . . H46B H 0.0092 0.3647 0.7648 0.046 Uiso 1 1 calc R . . C47 C -0.14519(13) 0.21471(8) 0.77280(13) 0.0496(6) Uani 1 1 d . . . H47A H -0.1857 0.2026 0.7266 0.074 Uiso 1 1 calc R . . H47B H -0.1773 0.2103 0.8251 0.074 Uiso 1 1 calc R . . H47C H -0.0882 0.1931 0.7744 0.074 Uiso 1 1 calc R . . O211 O 0.29030(8) 0.03637(5) 0.97771(6) 0.0279(3) Uani 1 1 d . . . C211 C 0.34998(11) 0.02701(6) 1.04347(9) 0.0229(4) Uani 1 1 d . . . C212 C 0.32172(11) -0.00813(6) 1.10834(9) 0.0229(4) Uani 1 1 d . . . C213 C 0.38042(11) -0.01598(6) 1.17591(10) 0.0252(4) Uani 1 1 d . . . H213 H 0.3611 -0.0383 1.2201 0.030 Uiso 1 1 calc R . . C214 C 0.46858(11) 0.00846(6) 1.18073(10) 0.0246(4) Uani 1 1 d . . . C215 C 0.52904(12) -0.00033(7) 1.25032(10) 0.0309(4) Uani 1 1 d . . . H215 H 0.5084 -0.0212 1.2957 0.037 Uiso 1 1 calc R . . C216 C 0.61648(12) 0.02075(7) 1.25294(11) 0.0354(5) Uani 1 1 d . . . H216 H 0.6563 0.0148 1.3000 0.042 Uiso 1 1 calc R . . C217 C 0.64731(12) 0.05136(7) 1.18561(11) 0.0326(4) Uani 1 1 d . . . H217 H 0.7086 0.0655 1.1871 0.039 Uiso 1 1 calc R . . C218 C 0.59060(11) 0.06110(6) 1.11818(10) 0.0273(4) Uani 1 1 d . . . H218 H 0.6133 0.0817 1.0734 0.033 Uiso 1 1 calc R . . C219 C 0.49829(11) 0.04111(6) 1.11362(9) 0.0230(4) Uani 1 1 d . . . C220 C 0.43583(11) 0.05173(6) 1.04498(9) 0.0228(4) Uani 1 1 d . . . O221 O 0.17859(8) -0.03142(5) 1.04011(7) 0.0335(3) Uani 1 1 d . . . C221 C 0.23111(11) -0.03636(7) 1.10120(10) 0.0265(4) Uani 1 1 d . . . O222 O 0.21058(8) -0.06713(5) 1.16476(7) 0.0325(3) Uani 1 1 d . . . C222 C 0.46478(12) 0.08681(6) 0.97241(10) 0.0265(4) Uani 1 1 d . . . H22A H 0.5219 0.0711 0.9497 0.032 Uiso 1 1 calc R . . H22B H 0.4156 0.0844 0.9284 0.032 Uiso 1 1 calc R . . C223 C 0.48277(12) 0.14623(7) 0.99028(10) 0.0274(4) Uani 1 1 d . . . O224 O 0.64041(9) 0.13437(5) 0.95652(7) 0.0361(3) Uani 1 1 d . . . C224 C 0.57071(12) 0.16760(7) 0.98175(10) 0.0304(4) Uani 1 1 d . . . C225 C 0.59046(13) 0.22321(7) 0.99795(11) 0.0340(4) Uani 1 1 d . . . C226 C 0.51970(13) 0.25669(7) 1.01969(10) 0.0361(5) Uani 1 1 d . . . H226 H 0.5328 0.2937 1.0305 0.043 Uiso 1 1 calc R . . C227 C 0.42856(12) 0.23809(7) 1.02653(10) 0.0309(4) Uani 1 1 d . . . C228 C 0.35596(13) 0.27379(7) 1.04705(10) 0.0361(5) Uani 1 1 d . . . H228 H 0.3695 0.3108 1.0574 0.043 Uiso 1 1 calc R . . C229 C 0.26756(14) 0.25593(7) 1.05213(11) 0.0407(5) Uani 1 1 d . . . H229 H 0.2195 0.2802 1.0665 0.049 Uiso 1 1 calc R . . C230 C 0.24706(13) 0.20113(7) 1.03604(11) 0.0394(5) Uani 1 1 d . . . H230 H 0.1847 0.1889 1.0386 0.047 Uiso 1 1 calc R . . C231 C 0.31580(12) 0.16525(7) 1.01675(10) 0.0326(4) Uani 1 1 d . . . H231 H 0.3004 0.1284 1.0068 0.039 Uiso 1 1 calc R . . C232 C 0.40926(12) 0.18222(7) 1.01141(10) 0.0285(4) Uani 1 1 d . . . O233 O 0.75208(9) 0.21623(5) 0.97003(8) 0.0461(4) Uani 1 1 d . . . C233 C 0.68595(14) 0.24416(8) 0.99143(12) 0.0413(5) Uani 1 1 d . . . O234 O 0.69403(11) 0.29596(5) 1.00974(10) 0.0583(4) Uani 1 1 d . . . O311 O 0.70363(8) 0.43444(5) 0.87002(7) 0.0308(3) Uani 1 1 d . . . C311 C 0.63401(11) 0.47175(7) 0.87429(9) 0.0258(4) Uani 1 1 d . . . C312 C 0.65574(11) 0.52815(7) 0.87255(9) 0.0258(4) Uani 1 1 d . . . C313 C 0.58500(12) 0.56500(7) 0.87764(9) 0.0271(4) Uani 1 1 d . . . H313 H 0.5986 0.6025 0.8734 0.033 Uiso 1 1 calc R . . C314 C 0.49269(12) 0.54865(7) 0.88904(9) 0.0264(4) Uani 1 1 d . . . C315 C 0.42106(12) 0.58692(7) 0.90220(10) 0.0312(4) Uani 1 1 d . . . H315 H 0.4346 0.6244 0.8985 0.037 Uiso 1 1 calc R . . C316 C 0.33351(12) 0.57097(8) 0.91993(10) 0.0343(5) Uani 1 1 d . . . H316 H 0.2868 0.5970 0.9302 0.041 Uiso 1 1 calc R . . C317 C 0.31307(12) 0.51529(8) 0.92286(10) 0.0327(4) Uani 1 1 d . . . H317 H 0.2522 0.5040 0.9358 0.039 Uiso 1 1 calc R . . C318 C 0.37937(12) 0.47715(7) 0.90744(9) 0.0289(4) Uani 1 1 d . . . H318 H 0.3630 0.4400 0.9080 0.035 Uiso 1 1 calc R . . C319 C 0.47181(11) 0.49218(7) 0.89065(9) 0.0248(4) Uani 1 1 d . . . C320 C 0.54384(11) 0.45349(7) 0.87883(9) 0.0243(4) Uani 1 1 d . . . O321 O 0.81896(8) 0.51370(5) 0.87169(7) 0.0343(3) Uani 1 1 d . . . C321 C 0.75318(12) 0.54569(7) 0.86840(9) 0.0288(4) Uani 1 1 d . . . O322 O 0.76661(9) 0.59851(5) 0.86165(7) 0.0349(3) Uani 1 1 d . . . C322 C 0.52340(12) 0.39323(6) 0.87460(10) 0.0271(4) Uani 1 1 d . . . H32A H 0.4903 0.3827 0.9251 0.033 Uiso 1 1 calc R . . H32B H 0.5831 0.3734 0.8751 0.033 Uiso 1 1 calc R . . C323 C 0.46538(11) 0.37549(6) 0.79858(10) 0.0247(4) Uani 1 1 d . . . O324 O 0.34925(9) 0.34455(5) 0.88671(7) 0.0372(3) Uani 1 1 d . . . C324 C 0.37955(12) 0.35251(7) 0.80823(10) 0.0272(4) Uani 1 1 d . . . C325 C 0.32188(12) 0.33668(7) 0.73844(10) 0.0280(4) Uani 1 1 d . . . C326 C 0.35345(11) 0.34515(7) 0.65970(10) 0.0284(4) Uani 1 1 d . . . H326 H 0.3146 0.3361 0.6132 0.034 Uiso 1 1 calc R . . C327 C 0.44193(11) 0.36692(6) 0.64671(10) 0.0254(4) Uani 1 1 d . . . C328 C 0.47451(12) 0.37522(7) 0.56533(10) 0.0291(4) Uani 1 1 d . . . H328 H 0.4348 0.3675 0.5188 0.035 Uiso 1 1 calc R . . C329 C 0.56172(12) 0.39401(7) 0.55319(10) 0.0307(4) Uani 1 1 d . . . H329 H 0.5824 0.4000 0.4986 0.037 Uiso 1 1 calc R . . C330 C 0.62152(12) 0.40456(7) 0.62245(10) 0.0293(4) Uani 1 1 d . . . H330 H 0.6833 0.4163 0.6138 0.035 Uiso 1 1 calc R . . C331 C 0.59176(11) 0.39813(6) 0.70140(10) 0.0257(4) Uani 1 1 d . . . H331 H 0.6332 0.4055 0.7469 0.031 Uiso 1 1 calc R . . C332 C 0.50018(11) 0.38068(6) 0.71672(10) 0.0240(4) Uani 1 1 d . . . O333 O 0.20447(9) 0.29985(5) 0.82209(8) 0.0479(4) Uani 1 1 d . . . C333 C 0.23116(12) 0.31038(7) 0.75201(12) 0.0330(4) Uani 1 1 d . . . O334 O 0.18198(9) 0.29867(5) 0.68491(7) 0.0377(3) Uani 1 1 d . . . H334 H 0.1175(16) 0.2824(9) 0.7023(13) 0.084(7) Uiso 1 1 d . . . H222 H 0.1431(16) -0.0832(9) 1.1580(12) 0.083(7) Uiso 1 1 d . . . H224 H 0.6974(15) 0.1550(9) 0.9553(12) 0.074(7) Uiso 1 1 d . . . H311 H 0.7582(14) 0.4544(8) 0.8689(12) 0.067(7) Uiso 1 1 d . . . H324 H 0.2909(16) 0.3260(9) 0.8802(13) 0.086(8) Uiso 1 1 d . . . H211 H 0.2372(14) 0.0132(8) 0.9883(12) 0.064(7) Uiso 1 1 d . . . H322 H 0.8375(18) 0.6053(10) 0.8511(14) 0.100(9) Uiso 1 1 d . . . H234 H 0.7620(19) 0.3089(10) 1.0022(15) 0.108(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O11 0.0261(7) 0.0314(7) 0.0452(8) -0.0002(6) 0.0079(6) -0.0004(6) C12 0.0268(10) 0.0313(10) 0.0220(10) 0.0009(7) 0.0022(7) -0.0018(8) N13 0.0260(8) 0.0281(8) 0.0284(8) -0.0002(6) 0.0021(6) -0.0035(7) C14 0.0270(10) 0.0347(11) 0.0252(10) 0.0033(8) 0.0005(7) 0.0018(8) C15 0.0299(10) 0.0314(11) 0.0284(10) 0.0006(8) -0.0038(8) -0.0012(8) C16 0.0302(10) 0.0299(10) 0.0253(10) 0.0016(7) 0.0010(7) -0.0032(8) C17 0.0351(11) 0.0301(11) 0.0517(13) -0.0003(9) 0.0053(9) -0.0064(9) O21A 0.030(4) 0.056(4) 0.084(6) -0.018(4) 0.013(4) -0.008(3) C22A 0.031(3) 0.040(4) 0.053(3) -0.003(3) -0.005(3) -0.001(3) N23A 0.030(4) 0.046(4) 0.043(2) -0.004(3) -0.0042(18) 0.003(3) C24A 0.034(3) 0.069(4) 0.042(3) -0.008(3) 0.006(2) -0.009(4) C25A 0.066(4) 0.052(3) 0.051(3) 0.010(2) -0.004(3) -0.017(3) C26A 0.057(5) 0.034(3) 0.052(5) 0.002(3) -0.021(3) 0.004(3) C27A 0.046(6) 0.035(4) 0.087(7) -0.021(4) -0.028(6) 0.011(6) O21B 0.031(3) 0.027(2) 0.085(6) 0.000(4) 0.007(4) -0.0006(19) C22B 0.036(4) 0.024(3) 0.045(3) -0.002(2) 0.000(2) 0.002(2) N23B 0.029(3) 0.031(3) 0.044(2) 0.004(2) -0.0006(19) 0.002(2) C24B 0.028(3) 0.040(3) 0.043(3) -0.007(3) -0.0028(19) 0.004(3) C25B 0.028(3) 0.042(3) 0.120(5) -0.011(3) -0.012(4) 0.006(4) C26B 0.038(4) 0.033(3) 0.062(4) 0.002(2) -0.003(3) 0.005(4) C27B 0.044(4) 0.030(3) 0.049(5) 0.005(3) 0.000(3) -0.001(3) O31 0.0331(8) 0.0407(8) 0.0524(9) 0.0101(7) 0.0068(6) -0.0055(6) C32 0.0408(12) 0.0351(11) 0.0303(11) -0.0093(9) 0.0076(9) -0.0084(9) N33 0.0475(11) 0.0468(11) 0.0520(11) -0.0128(9) 0.0164(9) -0.0168(9) C34 0.103(2) 0.0789(19) 0.0403(14) 0.0003(12) 0.0119(14) -0.0599(17) C35 0.131(3) 0.0597(18) 0.0664(18) 0.0240(13) -0.0281(17) -0.0310(18) C36 0.0685(16) 0.0498(14) 0.0438(13) 0.0067(10) -0.0118(11) -0.0020(12) C37 0.0398(15) 0.0689(19) 0.149(3) -0.0255(17) 0.0254(15) -0.0038(14) O41 0.0273(7) 0.0398(8) 0.0553(9) 0.0118(6) 0.0021(6) -0.0036(6) C42 0.0294(11) 0.0383(12) 0.0342(11) 0.0113(8) -0.0050(8) -0.0075(9) N43 0.0258(9) 0.0387(10) 0.0515(11) 0.0179(8) 0.0011(7) -0.0040(8) C44 0.0341(12) 0.0521(14) 0.0544(14) 0.0178(10) 0.0067(10) 0.0024(10) C45 0.0403(13) 0.0462(14) 0.0628(15) 0.0114(10) -0.0045(10) 0.0017(10) C46 0.0420(12) 0.0366(12) 0.0369(12) 0.0072(9) 0.0018(9) -0.0085(9) C47 0.0367(12) 0.0418(13) 0.0702(15) 0.0236(11) 0.0007(10) -0.0100(10) O211 0.0293(7) 0.0303(7) 0.0241(7) 0.0008(5) -0.0022(5) -0.0008(6) C211 0.0273(10) 0.0219(9) 0.0195(9) -0.0043(7) 0.0005(7) 0.0041(7) C212 0.0225(9) 0.0224(9) 0.0242(9) -0.0043(7) 0.0049(7) 0.0027(7) C213 0.0291(10) 0.0251(9) 0.0217(9) -0.0011(7) 0.0057(7) 0.0021(8) C214 0.0244(9) 0.0244(9) 0.0253(10) -0.0034(7) 0.0039(7) 0.0023(8) C215 0.0312(10) 0.0334(11) 0.0280(10) 0.0010(8) -0.0009(8) 0.0015(8) C216 0.0304(11) 0.0395(12) 0.0357(11) -0.0012(9) -0.0081(8) 0.0037(9) C217 0.0220(10) 0.0295(10) 0.0463(12) -0.0070(9) -0.0003(8) 0.0000(8) C218 0.0258(10) 0.0229(10) 0.0336(10) -0.0043(7) 0.0059(8) 0.0007(8) C219 0.0248(9) 0.0182(9) 0.0261(10) -0.0052(7) 0.0050(7) 0.0029(7) C220 0.0279(10) 0.0181(9) 0.0225(9) -0.0037(7) 0.0048(7) 0.0018(7) O221 0.0285(7) 0.0431(8) 0.0287(7) 0.0008(6) -0.0022(5) -0.0051(6) C221 0.0245(10) 0.0279(10) 0.0273(10) -0.0031(8) 0.0059(8) 0.0022(8) O222 0.0264(7) 0.0371(8) 0.0341(7) 0.0081(6) 0.0042(5) -0.0038(6) C222 0.0284(10) 0.0245(10) 0.0268(10) -0.0015(7) 0.0062(7) 0.0004(8) C223 0.0337(11) 0.0240(10) 0.0246(10) 0.0022(7) 0.0053(8) 0.0005(8) O224 0.0323(8) 0.0297(7) 0.0472(8) -0.0015(6) 0.0158(6) -0.0017(6) C224 0.0346(11) 0.0253(10) 0.0315(11) 0.0017(8) 0.0076(8) 0.0010(8) C225 0.0377(11) 0.0261(10) 0.0385(11) 0.0006(8) 0.0079(9) -0.0033(9) C226 0.0468(12) 0.0224(10) 0.0394(12) -0.0009(8) 0.0069(9) -0.0041(9) C227 0.0387(11) 0.0254(10) 0.0289(10) 0.0033(8) 0.0058(8) 0.0020(9) C228 0.0463(13) 0.0234(10) 0.0388(12) 0.0001(8) 0.0065(9) 0.0022(9) C229 0.0454(13) 0.0304(11) 0.0470(13) 0.0002(9) 0.0119(9) 0.0101(10) C230 0.0372(12) 0.0303(11) 0.0511(13) 0.0047(9) 0.0081(9) 0.0032(9) C231 0.0375(11) 0.0244(10) 0.0363(11) 0.0021(8) 0.0046(8) 0.0020(9) C232 0.0361(11) 0.0254(10) 0.0241(10) 0.0024(7) 0.0052(8) -0.0002(8) O233 0.0419(9) 0.0339(8) 0.0632(10) -0.0035(7) 0.0173(7) -0.0057(7) C233 0.0463(13) 0.0273(11) 0.0507(13) 0.0009(9) 0.0111(10) -0.0056(10) O234 0.0462(10) 0.0285(8) 0.1012(13) -0.0095(7) 0.0187(8) -0.0099(7) O311 0.0260(7) 0.0321(7) 0.0342(7) -0.0014(5) 0.0007(5) 0.0046(6) C311 0.0284(10) 0.0311(10) 0.0178(9) -0.0019(7) 0.0005(7) 0.0059(8) C312 0.0296(10) 0.0313(10) 0.0165(9) -0.0019(7) 0.0005(7) -0.0009(8) C313 0.0341(10) 0.0266(10) 0.0206(9) -0.0022(7) -0.0016(7) 0.0002(8) C314 0.0307(10) 0.0318(10) 0.0165(9) -0.0034(7) -0.0010(7) 0.0026(8) C315 0.0364(11) 0.0319(11) 0.0251(10) -0.0057(8) -0.0036(8) 0.0063(9) C316 0.0338(11) 0.0416(12) 0.0271(10) -0.0075(8) -0.0032(8) 0.0128(9) C317 0.0285(10) 0.0479(12) 0.0219(10) -0.0030(8) 0.0025(7) 0.0026(9) C318 0.0306(10) 0.0366(11) 0.0197(9) -0.0003(7) 0.0019(7) 0.0000(8) C319 0.0279(10) 0.0326(10) 0.0138(9) -0.0002(7) 0.0001(7) 0.0022(8) C320 0.0291(10) 0.0285(10) 0.0152(9) -0.0005(7) 0.0005(7) 0.0019(8) O321 0.0277(7) 0.0396(8) 0.0358(8) 0.0006(6) 0.0011(5) 0.0006(6) C321 0.0342(11) 0.0342(11) 0.0181(9) -0.0026(8) 0.0007(7) -0.0013(9) O322 0.0360(8) 0.0323(8) 0.0366(8) -0.0016(6) 0.0027(6) -0.0050(6) C322 0.0289(10) 0.0287(10) 0.0239(10) 0.0023(7) 0.0022(7) 0.0022(8) C323 0.0289(10) 0.0224(9) 0.0228(9) 0.0027(7) 0.0015(7) 0.0041(8) O324 0.0401(8) 0.0446(8) 0.0271(7) 0.0058(6) 0.0073(6) -0.0101(7) C324 0.0314(10) 0.0262(10) 0.0242(10) 0.0043(7) 0.0061(8) 0.0021(8) C325 0.0274(10) 0.0254(10) 0.0314(11) 0.0029(8) 0.0037(8) 0.0015(8) C326 0.0273(10) 0.0277(10) 0.0299(10) -0.0002(8) -0.0026(8) 0.0023(8) C327 0.0263(10) 0.0241(9) 0.0259(10) 0.0016(7) 0.0034(7) 0.0044(8) C328 0.0303(10) 0.0324(10) 0.0246(10) 0.0000(8) 0.0006(8) 0.0048(8) C329 0.0335(11) 0.0370(11) 0.0219(10) -0.0008(8) 0.0063(8) 0.0015(9) C330 0.0272(10) 0.0291(10) 0.0318(11) -0.0012(8) 0.0064(8) 0.0023(8) C331 0.0266(10) 0.0251(10) 0.0255(10) -0.0026(7) -0.0002(7) 0.0019(8) C332 0.0268(10) 0.0210(9) 0.0245(10) 0.0012(7) 0.0030(7) 0.0037(7) O333 0.0423(9) 0.0633(10) 0.0386(9) 0.0048(7) 0.0084(7) -0.0172(7) C333 0.0303(11) 0.0307(11) 0.0382(12) 0.0009(9) 0.0027(9) 0.0011(8) O334 0.0275(7) 0.0448(8) 0.0407(8) 0.0008(6) 0.0004(6) -0.0056(6) _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 O11 C12 1.2466(19) . ? C12 N13 1.330(2) . ? C12 C16 1.495(2) . ? N13 C17 1.453(2) . ? N13 C14 1.457(2) . ? C14 C15 1.538(2) . ? C15 C16 1.535(2) . ? O21A C22A 1.257(15) . ? C22A N23A 1.322(8) . ? C22A C26A 1.519(11) . ? N23A C24A 1.444(9) . ? N23A C27A 1.464(9) . ? C24A C25A 1.528(8) . ? C25A C26A 1.512(8) . ? O21B C22B 1.231(13) . ? C22B N23B 1.324(8) . ? C22B C26B 1.500(10) . ? N23B C27B 1.439(9) . ? N23B C24B 1.463(8) . ? C24B C25B 1.504(9) . ? C25B C26B 1.510(8) . ? O31 C32 1.241(2) . ? C32 N33 1.313(2) . ? C32 C36 1.505(3) . ? N33 C37 1.430(3) . ? N33 C34 1.465(3) . ? C34 C35 1.516(3) . ? C35 C36 1.516(3) . ? O41 C42 1.245(2) . ? C42 N43 1.329(2) . ? C42 C46 1.498(2) . ? N43 C47 1.450(2) . ? N43 C44 1.457(2) . ? C44 C45 1.528(3) . ? C45 C46 1.517(2) . ? O211 C211 1.3663(17) . ? C211 C220 1.380(2) . ? C211 C212 1.429(2) . ? C212 C213 1.374(2) . ? C212 C221 1.482(2) . ? C213 C214 1.407(2) . ? C214 C215 1.418(2) . ? C214 C219 1.426(2) . ? C215 C216 1.363(2) . ? C216 C217 1.407(2) . ? C217 C218 1.363(2) . ? C218 C219 1.419(2) . ? C219 C220 1.431(2) . ? C220 C222 1.525(2) . ? O221 C221 1.2316(18) . ? C221 O222 1.3174(19) . ? C222 C223 1.519(2) . ? C223 C224 1.384(2) . ? C223 C232 1.432(2) . ? O224 C224 1.3687(19) . ? C224 C225 1.427(2) . ? C225 C226 1.367(2) . ? C225 C233 1.477(3) . ? C226 C227 1.399(2) . ? C227 C228 1.416(2) . ? C227 C232 1.429(2) . ? C228 C229 1.353(2) . ? C229 C230 1.410(2) . ? C230 C231 1.373(2) . ? C231 C232 1.416(2) . ? O233 C233 1.234(2) . ? C233 O234 1.319(2) . ? O311 C311 1.3666(18) . ? C311 C320 1.380(2) . ? C311 C312 1.430(2) . ? C312 C313 1.372(2) . ? C312 C321 1.473(2) . ? C313 C314 1.408(2) . ? C314 C315 1.421(2) . ? C314 C319 1.429(2) . ? C315 C316 1.360(2) . ? C316 C317 1.410(2) . ? C317 C318 1.371(2) . ? C318 C319 1.417(2) . ? C319 C320 1.429(2) . ? C320 C322 1.521(2) . ? O321 C321 1.2349(19) . ? C321 O322 1.326(2) . ? C322 C323 1.529(2) . ? C323 C324 1.374(2) . ? C323 C332 1.432(2) . ? O324 C324 1.3654(18) . ? C324 C325 1.435(2) . ? C325 C326 1.377(2) . ? C325 C333 1.482(2) . ? C326 C327 1.405(2) . ? C327 C328 1.422(2) . ? C327 C332 1.429(2) . ? C328 C329 1.360(2) . ? C329 C330 1.416(2) . ? C330 C331 1.365(2) . ? C331 C332 1.417(2) . ? O333 C333 1.2324(19) . ? C333 O334 1.309(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 O11 C12 N13 124.31(16) . . ? O11 C12 C16 125.95(15) . . ? N13 C12 C16 109.73(15) . . ? C12 N13 C17 124.05(15) . . ? C12 N13 C14 114.14(14) . . ? C17 N13 C14 121.30(14) . . ? N13 C14 C15 103.94(13) . . ? C16 C15 C14 104.77(13) . . ? C12 C16 C15 105.10(13) . . ? O21A C22A N23A 127.0(10) . . ? O21A C22A C26A 124.4(8) . . ? N23A C22A C26A 108.6(7) . . ? C22A N23A C24A 114.4(8) . . ? C22A N23A C27A 121.9(7) . . ? C24A N23A C27A 122.5(6) . . ? N23A C24A C25A 103.5(6) . . ? C26A C25A C24A 104.8(5) . . ? C25A C26A C22A 104.3(6) . . ? O21B C22B N23B 122.3(8) . . ? O21B C22B C26B 127.7(7) . . ? N23B C22B C26B 109.8(6) . . ? C22B N23B C27B 124.8(7) . . ? C22B N23B C24B 113.4(7) . . ? C27B N23B C24B 121.5(5) . . ? N23B C24B C25B 103.8(5) . . ? C24B C25B C26B 106.4(7) . . ? C22B C26B C25B 104.1(7) . . ? O31 C32 N33 125.13(19) . . ? O31 C32 C36 125.30(18) . . ? N33 C32 C36 109.57(18) . . ? C32 N33 C37 125.19(19) . . ? C32 N33 C34 113.32(19) . . ? C37 N33 C34 121.0(2) . . ? N33 C34 C35 102.23(18) . . ? C34 C35 C36 104.6(2) . . ? C32 C36 C35 102.65(19) . . ? O41 C42 N43 124.17(17) . . ? O41 C42 C46 126.40(16) . . ? N43 C42 C46 109.43(17) . . ? C42 N43 C47 123.49(17) . . ? C42 N43 C44 114.11(15) . . ? C47 N43 C44 122.22(15) . . ? N43 C44 C45 104.38(15) . . ? C46 C45 C44 105.58(16) . . ? C42 C46 C45 105.60(15) . . ? O211 C211 C220 118.88(14) . . ? O211 C211 C212 119.05(14) . . ? C220 C211 C212 122.07(14) . . ? C213 C212 C211 119.01(15) . . ? C213 C212 C221 121.07(15) . . ? C211 C212 C221 119.90(14) . . ? C212 C213 C214 121.18(15) . . ? C213 C214 C215 120.76(15) . . ? C213 C214 C219 119.43(14) . . ? C215 C214 C219 119.78(15) . . ? C216 C215 C214 120.84(16) . . ? C215 C216 C217 119.60(16) . . ? C218 C217 C216 121.06(17) . . ? C217 C218 C219 121.31(16) . . ? C218 C219 C214 117.33(15) . . ? C218 C219 C220 122.97(15) . . ? C214 C219 C220 119.70(15) . . ? C211 C220 C219 118.44(14) . . ? C211 C220 C222 120.23(14) . . ? C219 C220 C222 121.24(15) . . ? O221 C221 O222 122.25(16) . . ? O221 C221 C212 122.38(15) . . ? O222 C221 C212 115.37(15) . . ? C223 C222 C220 116.99(13) . . ? C224 C223 C232 118.17(15) . . ? C224 C223 C222 120.18(15) . . ? C232 C223 C222 121.55(15) . . ? O224 C224 C223 118.83(15) . . ? O224 C224 C225 119.28(16) . . ? C223 C224 C225 121.89(16) . . ? C226 C225 C224 118.98(17) . . ? C226 C225 C233 120.59(17) . . ? C224 C225 C233 120.43(17) . . ? C225 C226 C227 121.98(17) . . ? C226 C227 C228 121.00(17) . . ? C226 C227 C232 118.90(16) . . ? C228 C227 C232 120.10(17) . . ? C229 C228 C227 120.93(17) . . ? C228 C229 C230 119.71(18) . . ? C231 C230 C229 120.97(18) . . ? C230 C231 C232 121.08(17) . . ? C231 C232 C227 117.20(16) . . ? C231 C232 C223 122.79(16) . . ? C227 C232 C223 119.99(16) . . ? O233 C233 O234 122.85(18) . . ? O233 C233 C225 123.49(17) . . ? O234 C233 C225 113.66(17) . . ? O311 C311 C320 118.39(15) . . ? O311 C311 C312 119.76(15) . . ? C320 C311 C312 121.84(15) . . ? C313 C312 C311 118.91(15) . . ? C313 C312 C321 121.20(16) . . ? C311 C312 C321 119.85(15) . . ? C312 C313 C314 121.57(16) . . ? C313 C314 C315 121.43(16) . . ? C313 C314 C319 118.92(15) . . ? C315 C314 C319 119.61(16) . . ? C316 C315 C314 121.35(17) . . ? C315 C316 C317 119.12(17) . . ? C318 C317 C316 121.26(17) . . ? C317 C318 C319 121.23(17) . . ? C318 C319 C320 122.73(16) . . ? C318 C319 C314 117.36(15) . . ? C320 C319 C314 119.87(15) . . ? C311 C320 C319 118.48(15) . . ? C311 C320 C322 120.01(15) . . ? C319 C320 C322 121.47(15) . . ? O321 C321 O322 121.41(16) . . ? O321 C321 C312 122.76(16) . . ? O322 C321 C312 115.83(16) . . ? C320 C322 C323 114.72(13) . . ? C324 C323 C332 118.79(15) . . ? C324 C323 C322 120.10(15) . . ? C332 C323 C322 121.07(15) . . ? O324 C324 C323 118.52(15) . . ? O324 C324 C325 119.66(15) . . ? C323 C324 C325 121.82(15) . . ? C326 C325 C324 118.88(16) . . ? C326 C325 C333 121.26(15) . . ? C324 C325 C333 119.84(15) . . ? C325 C326 C327 121.37(15) . . ? C326 C327 C328 121.19(15) . . ? C326 C327 C332 119.26(15) . . ? C328 C327 C332 119.55(15) . . ? C329 C328 C327 120.88(16) . . ? C328 C329 C330 119.60(16) . . ? C331 C330 C329 120.97(16) . . ? C330 C331 C332 121.15(15) . . ? C331 C332 C327 117.64(15) . . ? C331 C332 C323 122.73(14) . . ? C327 C332 C323 119.61(15) . . ? O333 C333 O334 122.41(17) . . ? O333 C333 C325 121.87(16) . . ? O334 C333 C325 115.72(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 O222 H222 O11 1.05(2) 1.51(2) 2.5600(16) 174(2) . O234 H234 O21A 1.04(3) 1.60(3) 2.582(12) 155(2) . O234 H234 O21B 1.04(3) 1.51(3) 2.496(12) 156(2) . O322 H322 O31 1.05(3) 1.55(3) 2.5990(17) 176(2) . O334 H334 O41 1.06(2) 1.49(2) 2.5477(17) 177(2) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.217 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.040 #=== END data_1a _database_code_depnum_ccdc_archive 'CCDC 788715' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,4 lutidinium pamoate NMP solvate' _chemical_melting_point ? _chemical_formula_moiety '0.5(C46H30O12H -1), 0.5(C7H10N +1) , C5H9N' _chemical_formula_sum 'C28 H24.50 N O7' _chemical_formula_weight 486.99 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6795(14) _cell_length_b 10.384(2) _cell_length_c 20.335(4) _cell_angle_alpha 88.829(2) _cell_angle_beta 83.310(2) _cell_angle_gamma 74.932(2) _cell_volume 1555.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5323 _cell_measurement_theta_min 2.259 _cell_measurement_theta_max 27.753 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.040 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 511 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9879 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 12984 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.01 _diffrn_reflns_theta_max 27.95 _reflns_number_total 6623 _reflns_number_gt 5246 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement ; SHELXL (Sheldrick, 2008), Platon/SQUEEZE (Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.) ; _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. H221 and H234 were located in the difference map after application of the program SQUEEZE. ; _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^)+(0.0769P)^2^+0.1129P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6623 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1384 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.04689(12) 0.91800(9) -0.07861(5) 0.0336(2) Uani 1 1 d . . . C1 C 0.89998(18) 1.00168(12) -0.08354(7) 0.0314(3) Uani 1 1 d . . . N2 N 0.88047(15) 1.10013(11) -0.12730(6) 0.0339(3) Uani 1 1 d . . . C3 C 0.69575(18) 1.18234(13) -0.12773(7) 0.0351(3) Uani 1 1 d . . . H3A H 0.6479 1.1704 -0.1697 0.042 Uiso 1 1 calc R . . H3B H 0.6902 1.2778 -0.1220 0.042 Uiso 1 1 calc R . . C4 C 0.58802(19) 1.13220(14) -0.06861(7) 0.0376(3) Uani 1 1 d . . . H4A H 0.5446 1.2021 -0.0338 0.045 Uiso 1 1 calc R . . H4B H 0.4819 1.1076 -0.0829 0.045 Uiso 1 1 calc R . . C5 C 0.71987(18) 1.00999(13) -0.04273(7) 0.0332(3) Uani 1 1 d . . . H5A H 0.7291 1.0211 0.0049 0.040 Uiso 1 1 calc R . . H5B H 0.6793 0.9284 -0.0487 0.040 Uiso 1 1 calc R . . C6 C 1.0257(2) 1.11900(14) -0.17543(7) 0.0404(3) Uani 1 1 d . . . H6A H 1.0012 1.0997 -0.2199 0.061 Uiso 1 1 calc R . . H6B H 1.1408 1.0586 -0.1658 0.061 Uiso 1 1 calc R . . H6C H 1.0336 1.2115 -0.1732 0.061 Uiso 1 1 calc R . . O211 O 0.85130(15) 0.13813(9) 0.28092(5) 0.0392(2) Uani 1 1 d . . . H211 H 0.873(3) 0.070(3) 0.3147(14) 0.108(8) Uiso 1 1 d . . . C211 C 0.86104(17) 0.25000(12) 0.31246(6) 0.0287(3) Uani 1 1 d . . . C212 C 0.89643(19) 0.24226(12) 0.37988(7) 0.0324(3) Uani 1 1 d . . . C213 C 0.90251(19) 0.35506(12) 0.41245(7) 0.0319(3) Uani 1 1 d . . . H213 H 0.9275 0.3495 0.4572 0.038 Uiso 1 1 calc R . . C214 C 0.87212(17) 0.47944(12) 0.38027(6) 0.0283(3) Uani 1 1 d . . . C215 C 0.87297(19) 0.59691(13) 0.41471(7) 0.0353(3) Uani 1 1 d . . . H215 H 0.8969 0.5911 0.4596 0.042 Uiso 1 1 calc R . . C216 C 0.8401(2) 0.71766(13) 0.38454(8) 0.0400(3) Uani 1 1 d . . . H216 H 0.8434 0.7952 0.4078 0.048 Uiso 1 1 calc R . . C217 C 0.8012(2) 0.72601(12) 0.31861(7) 0.0389(3) Uani 1 1 d . . . H217 H 0.7747 0.8107 0.2980 0.047 Uiso 1 1 calc R . . C218 C 0.80028(17) 0.61504(12) 0.28307(7) 0.0308(3) Uani 1 1 d . . . H218 H 0.7738 0.6241 0.2385 0.037 Uiso 1 1 calc R . . C219 C 0.83877(16) 0.48622(11) 0.31267(6) 0.0254(3) Uani 1 1 d . . . C220 C 0.83970(16) 0.36856(12) 0.27759(6) 0.0251(3) Uani 1 1 d . . . C221 C 0.9279(2) 0.11147(13) 0.41504(8) 0.0460(4) Uani 1 1 d . . . O221 O 0.9133(2) 0.01084(10) 0.38618(6) 0.0653(4) Uani 1 1 d . . . O222 O 0.9702(2) 0.11095(10) 0.47401(6) 0.0653(4) Uani 1 1 d . . . H222 H 1.0000 0.0000 0.5000 0.148(16) Uiso 1 2 d S . . C222 C 0.81429(17) 0.36953(13) 0.20443(6) 0.0283(3) Uani 1 1 d . . . H22A H 0.6961 0.4323 0.1982 0.034 Uiso 1 1 calc R . . H22B H 0.8082 0.2795 0.1916 0.034 Uiso 1 1 calc R . . C223 C 0.96181(16) 0.40852(12) 0.15756(6) 0.0263(3) Uani 1 1 d . . . O224 O 0.73936(12) 0.59093(10) 0.12140(5) 0.0352(2) Uani 1 1 d . . . H224 H 0.732(3) 0.660(2) 0.0907(11) 0.077(6) Uiso 1 1 d . . . C224 C 0.91605(16) 0.51946(12) 0.11781(6) 0.0273(3) Uani 1 1 d . . . C225 C 1.05191(17) 0.55968(12) 0.07355(6) 0.0269(3) Uani 1 1 d . . . C226 C 1.22978(17) 0.48726(12) 0.07060(6) 0.0274(3) Uani 1 1 d . . . H226 H 1.3195 0.5155 0.0420 0.033 Uiso 1 1 calc R . . C227 C 1.28247(16) 0.37225(12) 0.10885(6) 0.0265(3) Uani 1 1 d . . . C228 C 1.46610(17) 0.29704(13) 0.10516(6) 0.0306(3) Uani 1 1 d . . . H228 H 1.5564 0.3267 0.0776 0.037 Uiso 1 1 calc R . . C229 C 1.51538(18) 0.18260(13) 0.14055(7) 0.0343(3) Uani 1 1 d . . . H229 H 1.6389 0.1332 0.1379 0.041 Uiso 1 1 calc R . . C230 C 1.37995(19) 0.13865(13) 0.18114(7) 0.0364(3) Uani 1 1 d . . . H230 H 1.4138 0.0583 0.2052 0.044 Uiso 1 1 calc R . . C231 C 1.20165(17) 0.20895(12) 0.18658(7) 0.0306(3) Uani 1 1 d . . . H231 H 1.1139 0.1765 0.2140 0.037 Uiso 1 1 calc R . . C232 C 1.14569(16) 0.33030(12) 0.15165(6) 0.0262(3) Uani 1 1 d . . . C233 C 0.99749(17) 0.68026(12) 0.03238(6) 0.0289(3) Uani 1 1 d . . . O233 O 0.83911(13) 0.74698(10) 0.03487(5) 0.0382(2) Uani 1 1 d . . . O234 O 1.13039(12) 0.71092(9) -0.00617(5) 0.0327(2) Uani 1 1 d . . . H234 H 1.087(3) 0.794(2) -0.0296(12) 0.094(7) 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 0.0272(5) 0.0350(5) 0.0352(5) 0.0053(4) 0.0029(4) -0.0050(4) C1 0.0319(7) 0.0311(6) 0.0317(7) 0.0003(5) -0.0014(5) -0.0098(5) N2 0.0344(6) 0.0301(5) 0.0343(6) 0.0026(4) 0.0040(5) -0.0072(5) C3 0.0320(7) 0.0329(7) 0.0396(8) 0.0042(6) -0.0030(6) -0.0074(6) C4 0.0327(7) 0.0372(7) 0.0394(8) 0.0020(6) 0.0015(6) -0.0058(6) C5 0.0307(7) 0.0384(7) 0.0309(7) 0.0044(5) 0.0006(5) -0.0115(5) C6 0.0443(8) 0.0337(7) 0.0408(8) 0.0021(6) 0.0105(6) -0.0128(6) O211 0.0572(7) 0.0291(5) 0.0371(5) -0.0004(4) -0.0048(5) -0.0222(4) C211 0.0337(7) 0.0254(6) 0.0299(6) 0.0003(5) -0.0011(5) -0.0137(5) C212 0.0427(8) 0.0239(6) 0.0318(7) 0.0074(5) -0.0039(6) -0.0116(5) C213 0.0416(8) 0.0280(6) 0.0272(6) 0.0035(5) -0.0055(5) -0.0105(5) C214 0.0287(6) 0.0254(6) 0.0317(7) 0.0019(5) -0.0008(5) -0.0098(5) C215 0.0400(8) 0.0318(6) 0.0354(7) -0.0027(5) -0.0004(6) -0.0132(6) C216 0.0474(8) 0.0259(6) 0.0463(8) -0.0056(6) 0.0085(7) -0.0147(6) C217 0.0435(8) 0.0220(6) 0.0457(8) 0.0058(5) 0.0140(6) -0.0074(5) C218 0.0303(7) 0.0270(6) 0.0310(7) 0.0065(5) 0.0068(5) -0.0052(5) C219 0.0211(6) 0.0243(6) 0.0301(6) 0.0035(5) 0.0024(5) -0.0074(4) C220 0.0221(6) 0.0277(6) 0.0268(6) 0.0040(5) 0.0000(5) -0.0099(5) C221 0.0748(11) 0.0265(7) 0.0379(8) 0.0074(6) -0.0070(7) -0.0157(7) O221 0.1264(12) 0.0283(5) 0.0493(7) 0.0102(5) -0.0180(7) -0.0320(6) O222 0.1266(12) 0.0309(5) 0.0399(7) 0.0139(5) -0.0243(7) -0.0176(6) C222 0.0243(6) 0.0345(6) 0.0275(6) 0.0039(5) -0.0034(5) -0.0104(5) C223 0.0253(6) 0.0331(6) 0.0218(6) 0.0008(5) -0.0032(5) -0.0097(5) O224 0.0224(5) 0.0452(5) 0.0342(5) 0.0127(4) -0.0016(4) -0.0036(4) C224 0.0225(6) 0.0339(6) 0.0245(6) 0.0005(5) -0.0024(5) -0.0058(5) C225 0.0260(6) 0.0320(6) 0.0219(6) 0.0009(5) -0.0018(5) -0.0066(5) C226 0.0265(6) 0.0326(6) 0.0226(6) -0.0012(5) 0.0010(5) -0.0087(5) C227 0.0240(6) 0.0318(6) 0.0234(6) -0.0037(5) -0.0023(5) -0.0067(5) C228 0.0253(6) 0.0357(6) 0.0308(7) -0.0023(5) -0.0026(5) -0.0079(5) C229 0.0243(6) 0.0351(7) 0.0413(8) -0.0026(6) -0.0060(6) -0.0026(5) C230 0.0347(7) 0.0309(6) 0.0430(8) 0.0048(6) -0.0076(6) -0.0063(6) C231 0.0290(7) 0.0319(6) 0.0311(7) 0.0021(5) -0.0028(5) -0.0084(5) C232 0.0256(6) 0.0312(6) 0.0227(6) -0.0014(5) -0.0047(5) -0.0082(5) C233 0.0285(6) 0.0325(6) 0.0244(6) 0.0007(5) -0.0016(5) -0.0063(5) O233 0.0297(5) 0.0412(5) 0.0385(5) 0.0124(4) -0.0007(4) -0.0022(4) O234 0.0294(5) 0.0360(5) 0.0299(5) 0.0062(4) 0.0024(4) -0.0065(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2454(15) . ? C1 N2 1.3318(17) . ? C1 C5 1.5108(19) . ? N2 C6 1.4466(17) . ? N2 C3 1.4540(17) . ? C3 C4 1.5386(19) . ? C4 C5 1.5302(19) . ? O211 C211 1.3613(15) . ? C211 C220 1.3898(16) . ? C211 C212 1.4251(19) . ? C212 C213 1.3711(18) . ? C212 C221 1.4980(17) . ? C213 C214 1.4125(17) . ? C214 C215 1.4207(18) . ? C214 C219 1.4244(18) . ? C215 C216 1.3609(19) . ? C216 C217 1.403(2) . ? C217 C218 1.3746(19) . ? C218 C219 1.4289(16) . ? C219 C220 1.4253(17) . ? C220 C222 1.5223(17) . ? C221 O221 1.2450(18) . ? C221 O222 1.2779(19) . ? C222 C223 1.5253(17) . ? C223 C224 1.3863(17) . ? C223 C232 1.4270(17) . ? O224 C224 1.3612(15) . ? C224 C225 1.4371(17) . ? C225 C226 1.3725(17) . ? C225 C233 1.4866(17) . ? C226 C227 1.4067(17) . ? C227 C228 1.4175(17) . ? C227 C232 1.4352(17) . ? C228 C229 1.3668(19) . ? C229 C230 1.415(2) . ? C230 C231 1.3668(18) . ? C231 C232 1.4248(17) . ? C233 O233 1.2292(15) . ? C233 O234 1.3153(15) . ? 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 O1 C1 N2 123.43(12) . . ? O1 C1 C5 127.15(11) . . ? N2 C1 C5 109.42(11) . . ? C1 N2 C6 123.75(12) . . ? C1 N2 C3 114.87(11) . . ? C6 N2 C3 121.15(11) . . ? N2 C3 C4 104.24(10) . . ? C5 C4 C3 105.92(11) . . ? C1 C5 C4 105.09(11) . . ? O211 C211 C220 119.04(11) . . ? O211 C211 C212 119.34(11) . . ? C220 C211 C212 121.61(11) . . ? C213 C212 C211 119.71(11) . . ? C213 C212 C221 120.03(12) . . ? C211 C212 C221 120.26(12) . . ? C212 C213 C214 120.86(12) . . ? C213 C214 C215 120.77(12) . . ? C213 C214 C219 119.14(11) . . ? C215 C214 C219 120.09(11) . . ? C216 C215 C214 121.21(13) . . ? C215 C216 C217 119.10(12) . . ? C218 C217 C216 121.81(12) . . ? C217 C218 C219 120.56(12) . . ? C214 C219 C220 120.41(10) . . ? C214 C219 C218 117.17(11) . . ? C220 C219 C218 122.40(11) . . ? C211 C220 C219 118.08(11) . . ? C211 C220 C222 119.54(11) . . ? C219 C220 C222 122.36(10) . . ? O221 C221 O222 123.84(13) . . ? O221 C221 C212 119.62(13) . . ? O222 C221 C212 116.55(12) . . ? C220 C222 C223 115.40(10) . . ? C224 C223 C232 118.87(11) . . ? C224 C223 C222 119.59(11) . . ? C232 C223 C222 121.50(11) . . ? O224 C224 C223 118.93(11) . . ? O224 C224 C225 120.04(11) . . ? C223 C224 C225 121.03(11) . . ? C226 C225 C224 119.53(11) . . ? C226 C225 C233 121.13(11) . . ? C224 C225 C233 119.33(11) . . ? C225 C226 C227 121.59(11) . . ? C226 C227 C228 121.39(11) . . ? C226 C227 C232 118.72(11) . . ? C228 C227 C232 119.89(11) . . ? C229 C228 C227 121.09(12) . . ? C228 C229 C230 119.13(12) . . ? C231 C230 C229 121.60(12) . . ? C230 C231 C232 120.89(12) . . ? C231 C232 C223 122.54(11) . . ? C231 C232 C227 117.34(11) . . ? C223 C232 C227 120.12(11) . . ? O233 C233 O234 122.60(11) . . ? O233 C233 C225 121.98(11) . . ? O234 C233 C225 115.41(11) . . ? 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 O234 H234 O1 0.98(2) 1.60(2) 2.5648(13) 169(2) . _diffrn_measured_fraction_theta_max 0.885 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.290 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.041 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.489 0.500 484 156 ' ' _platon_squeeze_details ; ; #=== END data_1b _database_code_depnum_ccdc_archive 'CCDC 788716' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'bis(2-picoline) pamoaic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C23 H16 O6, 2(C6 H7 N)' _chemical_formula_sum 'C35 H30 N2 O6' _chemical_formula_weight 574.61 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.404(2) _cell_length_b 4.7782(4) _cell_length_c 24.059(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.175(2) _cell_angle_gamma 90.00 _cell_volume 2747.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4010 _cell_measurement_theta_min 3.020 _cell_measurement_theta_max 27.368 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9771 _exptl_absorpt_correction_T_max 0.9929 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 14659 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28.02 _reflns_number_total 3113 _reflns_number_gt 2450 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXS-97 (Sheldrick, 1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997' _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^)+(0.0462P)^2^+2.6911P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3113 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 N11 N 0.12373(5) 1.2424(2) 0.51523(5) 0.0218(3) Uani 1 1 d . . . C12 C 0.16350(6) 1.4185(3) 0.55244(6) 0.0227(3) Uani 1 1 d . . . C13 C 0.15442(6) 1.5796(3) 0.59543(7) 0.0277(3) Uani 1 1 d . . . H13 H 0.1828 1.7027 0.6216 0.033 Uiso 1 1 calc R . . C14 C 0.10398(6) 1.5605(3) 0.60005(7) 0.0281(3) Uani 1 1 d . . . H14 H 0.0974 1.6696 0.6294 0.034 Uiso 1 1 calc R . . C15 C 0.06339(6) 1.3802(3) 0.56135(7) 0.0292(3) Uani 1 1 d . . . H15 H 0.0284 1.3631 0.5634 0.035 Uiso 1 1 calc R . . C16 C 0.07498(6) 1.2253(3) 0.51965(7) 0.0271(3) Uani 1 1 d . . . H16 H 0.0471 1.1012 0.4930 0.033 Uiso 1 1 calc R . . C17 C 0.21653(6) 1.4317(4) 0.54410(7) 0.0321(4) Uani 1 1 d . . . H17A H 0.2102 1.5407 0.5072 0.048 Uiso 1 1 calc R . . H17B H 0.2283 1.2417 0.5396 0.048 Uiso 1 1 calc R . . H17C H 0.2459 1.5213 0.5800 0.048 Uiso 1 1 calc R . . O211 O 0.00378(4) 0.3861(2) 0.33940(4) 0.0213(2) Uani 1 1 d . . . H211 H 0.0123(8) 0.528(5) 0.3695(10) 0.058(6) Uiso 1 1 d . . . C211 C 0.05104(5) 0.3740(3) 0.33008(6) 0.0172(3) Uani 1 1 d . . . C212 C 0.09794(5) 0.5482(3) 0.36494(6) 0.0177(3) Uani 1 1 d . . . C213 C 0.14582(5) 0.5260(3) 0.35617(6) 0.0184(3) Uani 1 1 d . . . H213 H 0.1769 0.6423 0.3791 0.022 Uiso 1 1 calc R . . C214 C 0.14975(5) 0.3337(3) 0.31370(6) 0.0176(3) Uani 1 1 d . . . C215 C 0.19976(5) 0.3092(3) 0.30561(6) 0.0207(3) Uani 1 1 d . . . H215 H 0.2309 0.4240 0.3292 0.025 Uiso 1 1 calc R . . C216 C 0.20402(6) 0.1238(3) 0.26456(6) 0.0221(3) Uani 1 1 d . . . H216 H 0.2379 0.1083 0.2599 0.027 Uiso 1 1 calc R . . C217 C 0.15739(6) -0.0445(3) 0.22909(6) 0.0216(3) Uani 1 1 d . . . H217 H 0.1602 -0.1741 0.2006 0.026 Uiso 1 1 calc R . . C218 C 0.10824(6) -0.0244(3) 0.23500(6) 0.0202(3) Uani 1 1 d . . . H218 H 0.0775 -0.1390 0.2102 0.024 Uiso 1 1 calc R . . C219 C 0.10212(5) 0.1654(3) 0.27773(6) 0.0168(3) Uani 1 1 d . . . C220 C 0.05220(5) 0.1902(3) 0.28619(6) 0.0172(3) Uani 1 1 d . . . O221 O 0.05138(4) 0.7717(2) 0.41842(4) 0.0241(2) Uani 1 1 d . . . C221 C 0.09420(5) 0.7524(3) 0.40969(6) 0.0190(3) Uani 1 1 d . . . O222 O 0.13862(4) 0.9057(2) 0.43906(4) 0.0220(2) Uani 1 1 d . . . H222 H 0.1322(9) 1.050(5) 0.4717(11) 0.074(7) Uiso 1 1 d . . . C222 C 0.0000 0.0173(4) 0.2500 0.0201(4) Uani 1 2 d S . . H22A H 0.0070(6) -0.109(3) 0.2213(7) 0.023(4) 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 N11 0.0220(6) 0.0228(6) 0.0217(6) -0.0004(5) 0.0103(5) 0.0008(5) C12 0.0208(7) 0.0253(7) 0.0209(7) 0.0030(6) 0.0080(5) 0.0021(6) C13 0.0278(8) 0.0295(8) 0.0241(7) -0.0052(6) 0.0094(6) -0.0042(6) C14 0.0327(8) 0.0302(8) 0.0251(7) -0.0050(6) 0.0157(6) 0.0012(6) C15 0.0261(7) 0.0353(8) 0.0328(8) -0.0033(7) 0.0189(7) -0.0015(6) C16 0.0246(7) 0.0302(8) 0.0299(8) -0.0065(6) 0.0149(6) -0.0053(6) C17 0.0222(7) 0.0441(10) 0.0305(8) -0.0010(7) 0.0115(6) -0.0022(7) O211 0.0168(5) 0.0254(5) 0.0240(5) -0.0027(4) 0.0110(4) -0.0015(4) C211 0.0148(6) 0.0182(6) 0.0188(6) 0.0044(5) 0.0074(5) 0.0024(5) C212 0.0183(6) 0.0174(6) 0.0168(6) 0.0029(5) 0.0069(5) 0.0015(5) C213 0.0167(6) 0.0176(6) 0.0197(6) 0.0018(5) 0.0067(5) -0.0009(5) C214 0.0180(6) 0.0163(6) 0.0191(6) 0.0036(5) 0.0084(5) 0.0015(5) C215 0.0172(6) 0.0206(7) 0.0247(7) 0.0015(5) 0.0094(6) -0.0013(5) C216 0.0200(6) 0.0231(7) 0.0277(7) 0.0030(6) 0.0142(6) 0.0026(5) C217 0.0241(7) 0.0207(7) 0.0221(7) 0.0002(5) 0.0118(6) 0.0029(5) C218 0.0190(7) 0.0196(7) 0.0205(7) 0.0002(5) 0.0069(5) 0.0003(5) C219 0.0163(6) 0.0155(6) 0.0178(6) 0.0049(5) 0.0065(5) 0.0026(5) C220 0.0162(6) 0.0158(6) 0.0184(6) 0.0039(5) 0.0061(5) 0.0011(5) O221 0.0213(5) 0.0276(5) 0.0270(5) -0.0053(4) 0.0138(4) -0.0016(4) C221 0.0188(6) 0.0197(7) 0.0185(6) 0.0026(5) 0.0078(5) 0.0015(5) O222 0.0195(5) 0.0232(5) 0.0237(5) -0.0048(4) 0.0096(4) -0.0017(4) C222 0.0176(9) 0.0174(9) 0.0249(10) 0.000 0.0087(8) 0.000 _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 N11 C16 1.3384(18) . ? N11 C12 1.3463(18) . ? C12 C13 1.389(2) . ? C12 C17 1.4981(19) . ? C13 C14 1.386(2) . ? C14 C15 1.382(2) . ? C15 C16 1.382(2) . ? O211 C211 1.3596(15) . ? C211 C220 1.3839(18) . ? C211 C212 1.4302(18) . ? C212 C213 1.3714(18) . ? C212 C221 1.4873(18) . ? C213 C214 1.4105(18) . ? C214 C215 1.4191(18) . ? C214 C219 1.4322(18) . ? C215 C216 1.3663(19) . ? C216 C217 1.413(2) . ? C217 C218 1.3677(19) . ? C218 C219 1.4306(19) . ? C219 C220 1.4216(17) . ? C220 C222 1.5229(16) . ? O221 C221 1.2381(16) . ? C221 O222 1.3060(16) . ? C222 C220 1.5229(16) 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 C16 N11 C12 119.32(12) . . ? N11 C12 C13 120.57(13) . . ? N11 C12 C17 116.50(13) . . ? C13 C12 C17 122.93(13) . . ? C14 C13 C12 119.96(14) . . ? C15 C14 C13 118.90(14) . . ? C14 C15 C16 118.40(14) . . ? N11 C16 C15 122.86(14) . . ? O211 C211 C220 118.19(11) . . ? O211 C211 C212 120.34(12) . . ? C220 C211 C212 121.47(12) . . ? C213 C212 C211 119.32(12) . . ? C213 C212 C221 120.75(12) . . ? C211 C212 C221 119.92(12) . . ? C212 C213 C214 121.23(12) . . ? C213 C214 C215 120.84(12) . . ? C213 C214 C219 119.16(12) . . ? C215 C214 C219 119.99(12) . . ? C216 C215 C214 121.35(12) . . ? C215 C216 C217 119.14(12) . . ? C218 C217 C216 121.24(13) . . ? C217 C218 C219 121.43(12) . . ? C220 C219 C218 123.42(12) . . ? C220 C219 C214 119.74(12) . . ? C218 C219 C214 116.84(12) . . ? C211 C220 C219 119.01(12) . . ? C211 C220 C222 118.17(11) . . ? C219 C220 C222 122.80(11) . . ? O221 C221 O222 122.78(12) . . ? O221 C221 C212 121.20(12) . . ? O222 C221 C212 116.02(11) . . ? C220 C222 C220 114.29(16) . 2 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O211 H211 O221 0.95(2) 1.67(2) 2.5605(14) 156.2(19) . O222 H222 N11 1.11(2) 1.48(2) 2.5912(15) 180(2) . _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.276 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.046 #=== END data_1c _database_code_depnum_ccdc_archive 'CCDC 788717' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'bis(3-picolinium) pamoate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H14 O6 1- , 2(C6 H8 N 1+)' _chemical_formula_sum 'C35 H30 N2 O6' _chemical_formula_weight 574.61 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5321(9) _cell_length_b 10.0301(10) _cell_length_c 14.9869(15) _cell_angle_alpha 81.5400(10) _cell_angle_beta 87.4450(10) _cell_angle_gamma 87.2800(10) _cell_volume 1414.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6824 _cell_measurement_theta_min 2.500 _cell_measurement_theta_max 27.596 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9773 _exptl_absorpt_correction_T_max 0.9794 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 16129 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.93 _reflns_number_total 6176 _reflns_number_gt 5183 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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. All protons involved in proton transfer reactions were located in the difference map. ; _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^)+(0.0498P)^2^+0.3754P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6176 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1025 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.41463(10) 0.10236(10) 0.28531(7) 0.0221(2) Uani 1 1 d . . . H11 H 0.401(2) 0.086(2) 0.3683(14) 0.075(6) Uiso 1 1 d . . . C12 C 0.38699(12) 0.00229(12) 0.23960(8) 0.0222(2) Uani 1 1 d . . . H12 H 0.3671 -0.0836 0.2724 0.027 Uiso 1 1 calc R . . C13 C 0.38619(13) 0.01915(13) 0.14594(8) 0.0254(3) Uani 1 1 d . . . C14 C 0.41559(14) 0.14695(13) 0.10069(8) 0.0269(3) Uani 1 1 d . . . H14 H 0.4129 0.1641 0.0367 0.032 Uiso 1 1 calc R . . C15 C 0.44863(13) 0.24922(13) 0.14788(9) 0.0261(3) Uani 1 1 d . . . H15 H 0.4718 0.3354 0.1169 0.031 Uiso 1 1 calc R . . C16 C 0.44717(13) 0.22343(13) 0.24120(9) 0.0244(3) Uani 1 1 d . . . H16 H 0.4696 0.2927 0.2744 0.029 Uiso 1 1 calc R . . C17 C 0.35358(17) -0.09680(14) 0.09818(9) 0.0353(3) Uani 1 1 d . . . H17A H 0.2531 -0.1138 0.1062 0.053 Uiso 1 1 calc R . . H17B H 0.4083 -0.1777 0.1235 0.053 Uiso 1 1 calc R . . H17C H 0.3782 -0.0745 0.0337 0.053 Uiso 1 1 calc R . . N21 N 0.12552(10) 0.68431(10) 1.23063(7) 0.0220(2) Uani 1 1 d . . . H21 H 0.096(2) 0.681(2) 1.1506(15) 0.077(7) Uiso 1 1 d . . . C22 C 0.07457(13) 0.78371(12) 1.27557(8) 0.0226(3) Uani 1 1 d . . . H22 H 0.0066 0.8470 1.2479 0.027 Uiso 1 1 calc R . . C23 C 0.11757(13) 0.79734(13) 1.36096(8) 0.0238(3) Uani 1 1 d . . . C24 C 0.21689(13) 0.70174(14) 1.39967(8) 0.0270(3) Uani 1 1 d . . . H24 H 0.2501 0.7080 1.4577 0.032 Uiso 1 1 calc R . . C25 C 0.26720(14) 0.59797(14) 1.35399(9) 0.0282(3) Uani 1 1 d . . . H25 H 0.3331 0.5316 1.3807 0.034 Uiso 1 1 calc R . . C26 C 0.21980(13) 0.59264(13) 1.26865(8) 0.0250(3) Uani 1 1 d . . . H26 H 0.2549 0.5225 1.2364 0.030 Uiso 1 1 calc R . . C27 C 0.06035(15) 0.91118(14) 1.40877(9) 0.0315(3) Uani 1 1 d . . . H27A H 0.0245 0.9852 1.3644 0.047 Uiso 1 1 calc R . . H27B H 0.1354 0.9434 1.4418 0.047 Uiso 1 1 calc R . . H27C H -0.0161 0.8792 1.4513 0.047 Uiso 1 1 calc R . . O211 O 0.42905(9) 0.41232(9) 0.56884(6) 0.02326(19) Uani 1 1 d . . . H211 H 0.451(2) 0.3816(19) 0.5110(13) 0.062(6) Uiso 1 1 d . . . C211 C 0.37995(12) 0.30188(12) 0.62254(8) 0.0190(2) Uani 1 1 d . . . C212 C 0.36232(12) 0.18069(12) 0.58467(8) 0.0199(2) Uani 1 1 d . . . C213 C 0.30920(12) 0.07021(12) 0.63833(8) 0.0206(2) Uani 1 1 d . . . H213 H 0.2981 -0.0101 0.6133 0.025 Uiso 1 1 calc R . . C214 C 0.27085(12) 0.07373(12) 0.72988(8) 0.0200(2) Uani 1 1 d . . . C215 C 0.21287(13) -0.03967(12) 0.78493(8) 0.0234(3) Uani 1 1 d . . . H215 H 0.2032 -0.1207 0.7603 0.028 Uiso 1 1 calc R . . C216 C 0.17083(14) -0.03387(12) 0.87272(9) 0.0258(3) Uani 1 1 d . . . H216 H 0.1306 -0.1097 0.9085 0.031 Uiso 1 1 calc R . . C217 C 0.18759(13) 0.08555(12) 0.90990(8) 0.0247(3) Uani 1 1 d . . . H217 H 0.1571 0.0899 0.9707 0.030 Uiso 1 1 calc R . . C218 C 0.24706(13) 0.19524(12) 0.85976(8) 0.0223(3) Uani 1 1 d . . . H218 H 0.2604 0.2732 0.8870 0.027 Uiso 1 1 calc R . . C219 C 0.28921(12) 0.19458(11) 0.76763(8) 0.0187(2) Uani 1 1 d . . . C220 C 0.34580(12) 0.30986(12) 0.71258(8) 0.0186(2) Uani 1 1 d . . . O221 O 0.36825(9) 0.07057(9) 0.45470(6) 0.02378(19) Uani 1 1 d . . . C221 C 0.40109(12) 0.17615(12) 0.48738(8) 0.0211(2) Uani 1 1 d . . . O222 O 0.45947(10) 0.27341(9) 0.44111(6) 0.0288(2) Uani 1 1 d . . . C222 C 0.37678(12) 0.43772(11) 0.75079(8) 0.0191(2) Uani 1 1 d . . . H22A H 0.4513 0.4143 0.7951 0.023 Uiso 1 1 calc R . . H22B H 0.4162 0.5025 0.7008 0.023 Uiso 1 1 calc R . . C223 C 0.25627(12) 0.51028(11) 0.79654(8) 0.0180(2) Uani 1 1 d . . . O224 O 0.37476(9) 0.46480(8) 0.93396(6) 0.02187(19) Uani 1 1 d . . . H224 H 0.356(2) 0.4845(19) 0.9913(14) 0.059(6) Uiso 1 1 d . . . C224 C 0.26279(12) 0.52274(11) 0.88725(8) 0.0179(2) Uani 1 1 d . . . C225 C 0.15396(12) 0.59306(11) 0.93280(8) 0.0184(2) Uani 1 1 d . . . C226 C 0.04119(12) 0.65062(11) 0.88547(8) 0.0193(2) Uani 1 1 d . . . H226 H -0.0322 0.6954 0.9160 0.023 Uiso 1 1 calc R . . C227 C 0.03190(12) 0.64470(11) 0.79257(8) 0.0200(2) Uani 1 1 d . . . C228 C -0.08045(13) 0.71189(13) 0.74268(9) 0.0245(3) Uani 1 1 d . . . H228 H -0.1512 0.7608 0.7726 0.029 Uiso 1 1 calc R . . C229 C -0.08858(14) 0.70742(13) 0.65241(9) 0.0280(3) Uani 1 1 d . . . H229 H -0.1641 0.7532 0.6197 0.034 Uiso 1 1 calc R . . C230 C 0.01622(14) 0.63411(13) 0.60800(8) 0.0268(3) Uani 1 1 d . . . H230 H 0.0092 0.6293 0.5455 0.032 Uiso 1 1 calc R . . C231 C 0.12766(13) 0.56987(12) 0.65330(8) 0.0226(3) Uani 1 1 d . . . H231 H 0.1975 0.5226 0.6216 0.027 Uiso 1 1 calc R . . C232 C 0.14019(12) 0.57304(11) 0.74744(8) 0.0186(2) Uani 1 1 d . . . O233 O 0.07003(9) 0.67700(9) 1.06626(6) 0.02340(19) Uani 1 1 d . . . C233 C 0.16505(12) 0.60442(11) 1.03074(8) 0.0199(2) Uani 1 1 d . . . O234 O 0.26545(9) 0.54485(9) 1.07326(6) 0.0271(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0205(5) 0.0262(5) 0.0200(5) -0.0053(4) -0.0024(4) 0.0035(4) C12 0.0216(6) 0.0245(6) 0.0202(6) -0.0034(5) -0.0008(5) 0.0009(5) C13 0.0253(6) 0.0306(7) 0.0209(6) -0.0060(5) -0.0008(5) -0.0008(5) C14 0.0283(7) 0.0343(7) 0.0177(6) -0.0020(5) 0.0004(5) -0.0029(5) C15 0.0239(6) 0.0277(6) 0.0256(6) 0.0003(5) -0.0014(5) -0.0015(5) C16 0.0223(6) 0.0252(6) 0.0266(6) -0.0064(5) -0.0039(5) 0.0008(5) C17 0.0515(9) 0.0343(8) 0.0221(7) -0.0083(6) -0.0012(6) -0.0076(7) N21 0.0210(5) 0.0256(5) 0.0197(5) -0.0050(4) 0.0000(4) -0.0010(4) C22 0.0206(6) 0.0248(6) 0.0228(6) -0.0051(5) -0.0005(5) -0.0002(5) C23 0.0222(6) 0.0277(6) 0.0225(6) -0.0068(5) 0.0022(5) -0.0060(5) C24 0.0240(6) 0.0380(7) 0.0192(6) -0.0043(5) -0.0009(5) -0.0048(5) C25 0.0242(6) 0.0349(7) 0.0239(6) -0.0008(5) -0.0017(5) 0.0038(5) C26 0.0250(6) 0.0263(6) 0.0236(6) -0.0044(5) 0.0015(5) 0.0016(5) C27 0.0350(7) 0.0337(7) 0.0283(7) -0.0122(6) -0.0028(6) -0.0010(6) O211 0.0285(5) 0.0233(4) 0.0179(4) -0.0027(3) 0.0020(3) -0.0037(3) C211 0.0171(5) 0.0203(6) 0.0193(6) -0.0021(4) -0.0008(4) 0.0006(4) C212 0.0175(5) 0.0235(6) 0.0191(6) -0.0052(5) -0.0032(4) 0.0030(4) C213 0.0201(6) 0.0201(6) 0.0227(6) -0.0072(5) -0.0040(5) 0.0030(4) C214 0.0185(6) 0.0195(6) 0.0221(6) -0.0039(4) -0.0022(4) 0.0024(4) C215 0.0253(6) 0.0183(6) 0.0271(6) -0.0048(5) -0.0022(5) 0.0005(5) C216 0.0309(7) 0.0190(6) 0.0263(6) 0.0001(5) 0.0012(5) -0.0017(5) C217 0.0301(7) 0.0235(6) 0.0199(6) -0.0026(5) 0.0025(5) 0.0012(5) C218 0.0267(6) 0.0190(6) 0.0215(6) -0.0047(5) 0.0000(5) 0.0012(5) C219 0.0176(5) 0.0187(5) 0.0196(6) -0.0031(4) -0.0012(4) 0.0026(4) C220 0.0173(5) 0.0198(6) 0.0188(6) -0.0038(4) -0.0010(4) 0.0020(4) O221 0.0284(5) 0.0256(4) 0.0184(4) -0.0067(3) -0.0043(3) 0.0022(4) C221 0.0197(6) 0.0251(6) 0.0189(6) -0.0056(5) -0.0039(4) 0.0044(5) O222 0.0367(5) 0.0304(5) 0.0201(4) -0.0061(4) 0.0023(4) -0.0065(4) C222 0.0193(5) 0.0186(5) 0.0196(6) -0.0038(4) 0.0003(4) -0.0001(4) C223 0.0186(5) 0.0148(5) 0.0208(6) -0.0031(4) 0.0016(4) -0.0019(4) O224 0.0218(4) 0.0250(4) 0.0189(4) -0.0047(3) -0.0021(3) 0.0041(3) C224 0.0176(5) 0.0156(5) 0.0205(6) -0.0025(4) -0.0009(4) -0.0014(4) C225 0.0204(6) 0.0158(5) 0.0192(6) -0.0031(4) 0.0010(4) -0.0035(4) C226 0.0186(5) 0.0164(5) 0.0235(6) -0.0053(4) 0.0012(4) -0.0009(4) C227 0.0205(6) 0.0169(5) 0.0227(6) -0.0027(4) -0.0013(5) -0.0021(4) C228 0.0213(6) 0.0250(6) 0.0275(6) -0.0053(5) -0.0011(5) 0.0023(5) C229 0.0245(6) 0.0305(7) 0.0280(7) -0.0009(5) -0.0070(5) 0.0047(5) C230 0.0295(7) 0.0310(7) 0.0191(6) -0.0012(5) -0.0025(5) -0.0002(5) C231 0.0242(6) 0.0227(6) 0.0205(6) -0.0027(5) 0.0010(5) 0.0004(5) C232 0.0205(6) 0.0152(5) 0.0199(6) -0.0017(4) 0.0004(4) -0.0030(4) O233 0.0243(4) 0.0261(4) 0.0210(4) -0.0089(3) -0.0009(3) 0.0037(3) C233 0.0205(6) 0.0186(5) 0.0210(6) -0.0042(4) 0.0003(4) -0.0023(4) O234 0.0264(5) 0.0349(5) 0.0201(4) -0.0070(4) -0.0025(4) 0.0073(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.3376(16) . ? N11 C12 1.3377(16) . ? C12 C13 1.3892(17) . ? C13 C14 1.3940(18) . ? C13 C17 1.5035(18) . ? C14 C15 1.3841(18) . ? C15 C16 1.3839(18) . ? N21 C26 1.3382(16) . ? N21 C22 1.3439(16) . ? C22 C23 1.3885(17) . ? C23 C24 1.3970(18) . ? C23 C27 1.5038(18) . ? C24 C25 1.3838(19) . ? C25 C26 1.3844(18) . ? O211 C211 1.3591(14) . ? C211 C220 1.3869(16) . ? C211 C212 1.4349(16) . ? C212 C213 1.3733(17) . ? C212 C221 1.4947(16) . ? C213 C214 1.4090(17) . ? C214 C215 1.4223(17) . ? C214 C219 1.4321(16) . ? C215 C216 1.3669(18) . ? C216 C217 1.4118(17) . ? C217 C218 1.3691(17) . ? C218 C219 1.4216(16) . ? C219 C220 1.4308(16) . ? C220 C222 1.5255(15) . ? O221 C221 1.2873(14) . ? C221 O222 1.2491(15) . ? C222 C223 1.5220(15) . ? C223 C224 1.3878(16) . ? C223 C232 1.4256(16) . ? O224 C224 1.3620(14) . ? C224 C225 1.4312(16) . ? C225 C226 1.3714(16) . ? C225 C233 1.4977(16) . ? C226 C227 1.4092(16) . ? C227 C228 1.4194(16) . ? C227 C232 1.4318(16) . ? C228 C229 1.3660(18) . ? C229 C230 1.4130(18) . ? C230 C231 1.3693(17) . ? C231 C232 1.4263(16) . ? O233 C233 1.2815(14) . ? C233 O234 1.2518(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 120.35(11) . . ? N11 C12 C13 122.52(12) . . ? C12 C13 C14 116.68(11) . . ? C12 C13 C17 120.19(12) . . ? C14 C13 C17 123.12(11) . . ? C15 C14 C13 120.75(12) . . ? C16 C15 C14 118.65(12) . . ? N11 C16 C15 120.98(11) . . ? C26 N21 C22 119.98(11) . . ? N21 C22 C23 122.45(12) . . ? C22 C23 C24 117.06(11) . . ? C22 C23 C27 121.13(12) . . ? C24 C23 C27 121.80(11) . . ? C25 C24 C23 120.38(12) . . ? C24 C25 C26 118.81(12) . . ? N21 C26 C25 121.30(12) . . ? O211 C211 C220 119.04(10) . . ? O211 C211 C212 119.44(10) . . ? C220 C211 C212 121.52(11) . . ? C213 C212 C211 119.45(11) . . ? C213 C212 C221 120.74(11) . . ? C211 C212 C221 119.80(11) . . ? C212 C213 C214 121.27(11) . . ? C213 C214 C215 121.27(11) . . ? C213 C214 C219 119.16(11) . . ? C215 C214 C219 119.56(11) . . ? C216 C215 C214 120.98(11) . . ? C215 C216 C217 119.58(11) . . ? C218 C217 C216 121.04(11) . . ? C217 C218 C219 121.19(11) . . ? C218 C219 C220 122.34(10) . . ? C218 C219 C214 117.60(11) . . ? C220 C219 C214 120.05(10) . . ? C211 C220 C219 118.53(10) . . ? C211 C220 C222 119.17(10) . . ? C219 C220 C222 122.21(10) . . ? O222 C221 O221 122.96(11) . . ? O222 C221 C212 120.09(11) . . ? O221 C221 C212 116.93(11) . . ? C223 C222 C220 118.20(10) . . ? C224 C223 C232 118.76(10) . . ? C224 C223 C222 119.42(10) . . ? C232 C223 C222 121.71(10) . . ? O224 C224 C223 118.89(10) . . ? O224 C224 C225 119.52(10) . . ? C223 C224 C225 121.58(10) . . ? C226 C225 C224 119.22(10) . . ? C226 C225 C233 120.84(10) . . ? C224 C225 C233 119.94(10) . . ? C225 C226 C227 121.39(11) . . ? C226 C227 C228 121.12(11) . . ? C226 C227 C232 119.22(11) . . ? C228 C227 C232 119.63(11) . . ? C229 C228 C227 121.11(11) . . ? C228 C229 C230 119.47(12) . . ? C231 C230 C229 121.26(12) . . ? C230 C231 C232 120.87(11) . . ? C223 C232 C231 122.58(10) . . ? C223 C232 C227 119.78(10) . . ? C231 C232 C227 117.64(11) . . ? O234 C233 O233 123.50(11) . . ? O234 C233 C225 119.32(10) . . ? O233 C233 C225 117.18(10) . . ? 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 N11 H11 O221 1.23(2) 1.31(2) 2.5331(13) 172.3(19) . N21 H21 O233 1.25(2) 1.31(2) 2.5546(13) 178(2) . _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.311 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.040 #=== END data_1d _database_code_depnum_ccdc_archive 'CCDC 788718' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2-picolinium pamoate THF solvate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 O6 1- , C6 H8 N 1+ , C4 H8 O' _chemical_formula_sum 'C33 H31 N O7' _chemical_formula_weight 553.59 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.8694(11) _cell_length_b 12.7194(10) _cell_length_c 16.5587(13) _cell_angle_alpha 90.00 _cell_angle_beta 111.1600(10) _cell_angle_gamma 90.00 _cell_volume 2724.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4640 _cell_measurement_theta_min 2.246 _cell_measurement_theta_max 26.488 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9565 _exptl_absorpt_correction_T_max 0.9835 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 15695 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 26.51 _reflns_number_total 5611 _reflns_number_gt 4327 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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. All protons involved in proton transfer reactions were located in the difference map for the major compnent of the disorder. ; _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^)+(0.0546P)^2^+0.8290P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5611 _refine_ls_number_parameters 495 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1188 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 N11 N 0.76941(17) 0.34327(16) -0.06405(16) 0.0320(5) Uani 0.852(4) 1 d PD A 1 C12 C 0.69000(16) 0.40025(14) -0.11777(13) 0.0347(5) Uani 0.852(4) 1 d PD A 1 C13 C 0.7000(3) 0.4414(3) -0.1918(2) 0.0390(9) Uani 0.852(4) 1 d PD A 1 H13 H 0.6455 0.4820 -0.2308 0.047 Uiso 0.852(4) 1 calc PR A 1 C14 C 0.78895(19) 0.42369(16) -0.20895(14) 0.0441(6) Uani 0.852(4) 1 d PD A 1 H14 H 0.7958 0.4525 -0.2595 0.053 Uiso 0.852(4) 1 calc PR A 1 C15 C 0.86844(17) 0.36379(16) -0.15242(14) 0.0383(5) Uani 0.852(4) 1 d PD A 1 H15 H 0.9298 0.3508 -0.1637 0.046 Uiso 0.852(4) 1 calc PR A 1 C16 C 0.8559(3) 0.3235(2) -0.0791(2) 0.0332(7) Uani 0.852(4) 1 d PD A 1 H16 H 0.9088 0.2818 -0.0395 0.040 Uiso 0.852(4) 1 calc PR A 1 C17 C 0.5972(3) 0.4145(4) -0.0930(3) 0.0421(9) Uani 0.852(4) 1 d P A 1 H17A H 0.5680 0.3456 -0.0884 0.063 Uiso 0.852(4) 1 calc PR A 1 H17B H 0.5453 0.4565 -0.1373 0.063 Uiso 0.852(4) 1 calc PR A 1 H17C H 0.6175 0.4508 -0.0371 0.063 Uiso 0.852(4) 1 calc PR A 1 N21 N 0.7169(11) 0.3458(8) -0.0563(7) 0.040(3) Uani 0.148(4) 1 d PD A 2 H21 H 0.7419 0.3102 -0.0076 0.048 Uiso 0.148(4) 1 calc PR A 2 C22 C 0.7741(16) 0.3466(13) -0.1081(10) 0.061(7) Uani 0.148(4) 1 d PD A 2 C23 C 0.7343(16) 0.4097(15) -0.1817(12) 0.040(5) Uani 0.148(4) 1 d PD A 2 H23 H 0.7717 0.4177 -0.2194 0.048 Uiso 0.148(4) 1 calc PR A 2 C24 C 0.6406(14) 0.4606(11) -0.2000(10) 0.044(4) Uani 0.148(4) 1 d PD A 2 H24 H 0.6136 0.5006 -0.2518 0.053 Uiso 0.148(4) 1 calc PR A 2 C25 C 0.5848(11) 0.4554(11) -0.1457(10) 0.050(4) Uani 0.148(4) 1 d PD A 2 H25 H 0.5214 0.4921 -0.1579 0.060 Uiso 0.148(4) 1 calc PR A 2 C26 C 0.6265(15) 0.3941(18) -0.0730(16) 0.052(8) Uani 0.148(4) 1 d PD A 2 H26 H 0.5905 0.3860 -0.0342 0.063 Uiso 0.148(4) 1 calc PR A 2 O211 O 0.57139(8) 0.18984(8) 0.09087(7) 0.0293(2) Uani 1 1 d . . . H211 H 0.6290(17) 0.2026(17) 0.0757(14) 0.066(6) Uiso 1 1 d . . . C211 C 0.58777(10) 0.25289(10) 0.16097(9) 0.0232(3) Uani 1 1 d . . . C212 C 0.68307(11) 0.30837(11) 0.19740(9) 0.0244(3) Uani 1 1 d . . . C213 C 0.70106(11) 0.36744(11) 0.27067(9) 0.0253(3) Uani 1 1 d . . . H213 H 0.7644 0.4047 0.2946 0.030 Uiso 1 1 calc R . . C214 C 0.62755(11) 0.37418(11) 0.31136(9) 0.0240(3) Uani 1 1 d . . . C215 C 0.64900(12) 0.43024(11) 0.38979(9) 0.0286(3) Uani 1 1 d . . . H215 H 0.7129 0.4663 0.4144 0.034 Uiso 1 1 calc R . . C216 C 0.57931(13) 0.43329(11) 0.43062(10) 0.0315(3) Uani 1 1 d . . . H216 H 0.5950 0.4705 0.4836 0.038 Uiso 1 1 calc R . . C217 C 0.48403(12) 0.38089(12) 0.39354(10) 0.0304(3) Uani 1 1 d . . . H217 H 0.4352 0.3837 0.4216 0.037 Uiso 1 1 calc R . . C218 C 0.46042(11) 0.32592(11) 0.31778(9) 0.0256(3) Uani 1 1 d . . . H218 H 0.3956 0.2913 0.2942 0.031 Uiso 1 1 calc R . . C219 C 0.53164(10) 0.31985(10) 0.27368(9) 0.0217(3) Uani 1 1 d . . . C220 C 0.51143(10) 0.25913(10) 0.19674(9) 0.0219(3) Uani 1 1 d . . . O221 O 0.73919(8) 0.26441(9) 0.08142(8) 0.0382(3) Uani 1 1 d . . . C221 C 0.76404(11) 0.30238(11) 0.15701(10) 0.0285(3) Uani 1 1 d . . . O222 O 0.85284(8) 0.33689(8) 0.20142(7) 0.0324(3) Uani 1 1 d . . . C222 C 0.41319(10) 0.19434(11) 0.15800(9) 0.0226(3) Uani 1 1 d . . . H22A H 0.4074 0.1473 0.2037 0.027 Uiso 1 1 calc R . . H22B H 0.4206 0.1492 0.1119 0.027 Uiso 1 1 calc R . . C223 C 0.31260(10) 0.25570(10) 0.11990(9) 0.0216(3) Uani 1 1 d . . . O224 O 0.25349(8) 0.17853(8) 0.22353(6) 0.0275(2) Uani 1 1 d . . . H224 H 0.1960(17) 0.1854(17) 0.2369(14) 0.064(6) Uiso 1 1 d . . . C224 C 0.23659(10) 0.24523(11) 0.15563(9) 0.0226(3) Uani 1 1 d . . . C225 C 0.14236(10) 0.30318(11) 0.12290(9) 0.0225(3) Uani 1 1 d . . . C226 C 0.12445(11) 0.36786(11) 0.05251(9) 0.0235(3) Uani 1 1 d . . . H226 H 0.0627 0.4082 0.0320 0.028 Uiso 1 1 calc R . . C227 C 0.19588(10) 0.37555(10) 0.01003(9) 0.0228(3) Uani 1 1 d . . . C228 C 0.17312(11) 0.43521(11) -0.06714(9) 0.0261(3) Uani 1 1 d . . . H228 H 0.1106 0.4742 -0.0887 0.031 Uiso 1 1 calc R . . C229 C 0.24002(12) 0.43722(11) -0.11063(9) 0.0285(3) Uani 1 1 d . . . H229 H 0.2237 0.4765 -0.1627 0.034 Uiso 1 1 calc R . . C230 C 0.33347(11) 0.38067(11) -0.07787(9) 0.0279(3) Uani 1 1 d . . . H230 H 0.3796 0.3819 -0.1086 0.033 Uiso 1 1 calc R . . C231 C 0.35929(11) 0.32398(11) -0.00273(9) 0.0247(3) Uani 1 1 d . . . H231 H 0.4235 0.2877 0.0185 0.030 Uiso 1 1 calc R . . C232 C 0.29083(10) 0.31870(10) 0.04417(9) 0.0217(3) Uani 1 1 d . . . O233 O 0.07899(7) 0.23545(8) 0.22851(7) 0.0301(2) Uani 1 1 d . . . C233 C 0.06404(11) 0.29277(11) 0.16482(9) 0.0249(3) Uani 1 1 d . . . O234 O -0.02059(8) 0.34661(9) 0.12837(7) 0.0334(3) Uani 1 1 d . . . H234 H -0.0764(19) 0.334(2) 0.1633(16) 0.093(9) Uiso 1 1 d . . . O1 O 0.1852(2) 0.5024(3) 0.3916(2) 0.0500(9) Uani 0.595(7) 1 d P B 3 C2 C 0.1001(3) 0.5595(3) 0.3980(3) 0.0480(12) Uani 0.595(7) 1 d P B 3 H2A H 0.1208 0.5935 0.4556 0.058 Uiso 0.595(7) 1 calc PR B 3 H2B H 0.0792 0.6152 0.3533 0.058 Uiso 0.595(7) 1 calc PR B 3 C3 C 0.1760(8) 0.3951(8) 0.4059(6) 0.095(4) Uani 0.595(7) 1 d P B 3 H3A H 0.2288 0.3724 0.4615 0.114 Uiso 0.595(7) 1 calc PR B 3 H3B H 0.1832 0.3524 0.3584 0.114 Uiso 0.595(7) 1 calc PR B 3 C4 C 0.0592(10) 0.3849(5) 0.4083(6) 0.071(3) Uani 0.595(7) 1 d P B 3 H4B H 0.0146 0.3371 0.3629 0.086 Uiso 0.595(7) 1 calc PR B 3 H4A H 0.0597 0.3630 0.4658 0.086 Uiso 0.595(7) 1 calc PR B 3 C5 C 0.0290(6) 0.5017(5) 0.3884(8) 0.116(4) Uani 0.595(7) 1 d P B 3 H5A H -0.0197 0.5074 0.3278 0.139 Uiso 0.595(7) 1 calc PR B 3 H5B H -0.0078 0.5254 0.4264 0.139 Uiso 0.595(7) 1 calc PR B 3 O6 O 0.1592(5) 0.4678(5) 0.3414(8) 0.120(3) Uani 0.405(7) 1 d P B 4 C7 C 0.0701(4) 0.5327(4) 0.3301(6) 0.070(2) Uani 0.405(7) 1 d P B 4 H7A H 0.0284 0.5393 0.2676 0.084 Uiso 0.405(7) 1 calc PR B 4 H7B H 0.0929 0.6039 0.3532 0.084 Uiso 0.405(7) 1 calc PR B 4 C8 C 0.1578(14) 0.3925(10) 0.4125(6) 0.073(5) Uani 0.405(7) 1 d P B 4 H8A H 0.1760 0.3210 0.3992 0.088 Uiso 0.405(7) 1 calc PR B 4 H8B H 0.2105 0.4147 0.4683 0.088 Uiso 0.405(7) 1 calc PR B 4 C9 C 0.070(2) 0.3901(18) 0.4198(16) 0.167(11) Uani 0.405(7) 1 d P B 4 H9A H 0.0795 0.3886 0.4819 0.201 Uiso 0.405(7) 1 calc PR B 4 H9B H 0.0336 0.3250 0.3927 0.201 Uiso 0.405(7) 1 calc PR B 4 C10 C 0.0041(9) 0.4853(10) 0.3768(7) 0.099(5) Uani 0.405(7) 1 d P B 4 H10A H -0.0649 0.4640 0.3359 0.118 Uiso 0.405(7) 1 calc PR B 4 H10B H -0.0043 0.5344 0.4202 0.118 Uiso 0.405(7) 1 calc PR B 4 H1 H 0.7600 0.3131 -0.0115 0.067(8) Uiso 0.852(4) 1 d PR A 1 C27 C 0.871(2) 0.293(3) -0.083(3) 0.142(19) Uani 0.148(4) 1 d P A 2 H27A H 0.9075 0.3008 -0.0201 0.213 Uiso 0.148(4) 1 calc PR A 2 H27B H 0.9135 0.3244 -0.1131 0.213 Uiso 0.148(4) 1 calc PR A 2 H27C H 0.8599 0.2188 -0.0977 0.213 Uiso 0.148(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0299(12) 0.0314(9) 0.0329(13) -0.0064(9) 0.0092(11) -0.0065(9) C12 0.0334(11) 0.0257(9) 0.0372(12) -0.0095(9) 0.0035(9) -0.0053(8) C13 0.039(2) 0.030(2) 0.0385(14) -0.0033(13) 0.0023(18) -0.0054(16) C14 0.0551(14) 0.0409(12) 0.0336(11) -0.0039(9) 0.0129(11) -0.0167(10) C15 0.0412(12) 0.0427(11) 0.0319(11) -0.0091(9) 0.0142(9) -0.0160(9) C16 0.0303(18) 0.0395(12) 0.0284(12) -0.0073(10) 0.0090(12) -0.0075(11) C17 0.034(2) 0.038(2) 0.051(2) -0.0115(16) 0.0110(19) -0.0010(15) N21 0.055(9) 0.025(5) 0.028(6) -0.004(4) 0.000(6) -0.015(7) C22 0.102(19) 0.057(10) 0.029(9) -0.017(8) 0.030(11) -0.040(11) C23 0.041(12) 0.046(13) 0.032(10) -0.016(8) 0.013(9) -0.004(8) C24 0.083(12) 0.022(6) 0.031(7) 0.002(5) 0.025(9) -0.016(8) C25 0.059(9) 0.034(7) 0.049(9) -0.013(6) 0.010(7) -0.002(6) C26 0.046(15) 0.022(9) 0.059(12) -0.022(8) -0.017(9) -0.005(9) O211 0.0263(5) 0.0336(6) 0.0319(6) -0.0095(5) 0.0152(5) -0.0019(5) C211 0.0221(7) 0.0232(7) 0.0239(7) 0.0009(6) 0.0081(6) 0.0035(6) C212 0.0210(7) 0.0243(7) 0.0286(8) 0.0037(6) 0.0099(6) 0.0041(6) C213 0.0202(7) 0.0252(7) 0.0277(7) 0.0033(6) 0.0055(6) -0.0006(6) C214 0.0252(7) 0.0230(7) 0.0227(7) 0.0049(6) 0.0074(6) 0.0024(6) C215 0.0324(8) 0.0253(7) 0.0256(8) -0.0002(6) 0.0072(6) -0.0044(6) C216 0.0461(9) 0.0262(7) 0.0231(7) -0.0017(6) 0.0138(7) -0.0037(7) C217 0.0386(9) 0.0306(8) 0.0269(8) 0.0022(6) 0.0178(7) -0.0007(7) C218 0.0264(7) 0.0272(7) 0.0244(7) 0.0025(6) 0.0108(6) 0.0001(6) C219 0.0230(7) 0.0216(6) 0.0201(7) 0.0050(5) 0.0074(5) 0.0035(5) C220 0.0196(7) 0.0226(6) 0.0232(7) 0.0033(5) 0.0071(5) 0.0041(5) O221 0.0323(6) 0.0459(7) 0.0445(7) -0.0128(6) 0.0237(5) -0.0059(5) C221 0.0234(7) 0.0269(7) 0.0382(9) 0.0018(6) 0.0146(7) 0.0025(6) O222 0.0207(5) 0.0394(6) 0.0382(6) 0.0043(5) 0.0121(5) 0.0015(4) C222 0.0219(7) 0.0241(7) 0.0229(7) -0.0007(6) 0.0092(6) 0.0016(5) C223 0.0191(7) 0.0231(7) 0.0217(7) -0.0044(5) 0.0063(5) -0.0021(5) O224 0.0232(5) 0.0341(6) 0.0277(6) 0.0081(4) 0.0121(4) 0.0038(4) C224 0.0217(7) 0.0236(7) 0.0211(7) -0.0018(5) 0.0062(5) -0.0020(5) C225 0.0196(7) 0.0236(7) 0.0241(7) -0.0039(6) 0.0075(5) -0.0028(5) C226 0.0200(7) 0.0227(7) 0.0254(7) -0.0025(6) 0.0054(6) 0.0007(5) C227 0.0235(7) 0.0213(6) 0.0225(7) -0.0043(5) 0.0071(6) -0.0028(6) C228 0.0273(7) 0.0238(7) 0.0243(7) -0.0009(6) 0.0060(6) 0.0009(6) C229 0.0363(8) 0.0274(7) 0.0215(7) 0.0001(6) 0.0102(6) -0.0010(6) C230 0.0325(8) 0.0312(7) 0.0234(7) -0.0049(6) 0.0144(6) -0.0039(6) C231 0.0243(7) 0.0267(7) 0.0237(7) -0.0045(6) 0.0093(6) -0.0010(6) C232 0.0225(7) 0.0214(6) 0.0208(7) -0.0061(5) 0.0074(5) -0.0041(5) O233 0.0241(5) 0.0376(6) 0.0310(6) 0.0050(5) 0.0129(4) 0.0014(4) C233 0.0208(7) 0.0266(7) 0.0268(7) -0.0017(6) 0.0081(6) -0.0019(6) O234 0.0221(5) 0.0404(6) 0.0406(6) 0.0102(5) 0.0147(5) 0.0061(5) O1 0.0530(17) 0.0407(17) 0.0593(18) 0.0171(12) 0.0239(14) 0.0165(13) C2 0.0352(18) 0.0332(17) 0.069(3) 0.0061(16) 0.0105(18) 0.0071(14) C3 0.089(5) 0.042(5) 0.095(7) -0.010(4) -0.037(5) 0.033(4) C4 0.112(7) 0.029(3) 0.057(3) 0.008(2) 0.012(4) -0.020(3) C5 0.078(5) 0.057(4) 0.236(11) 0.065(5) 0.086(6) 0.022(4) O6 0.078(4) 0.055(3) 0.203(9) -0.014(4) 0.022(5) 0.016(3) C7 0.047(3) 0.036(3) 0.106(6) 0.007(3) 0.002(3) 0.016(2) C8 0.167(15) 0.024(5) 0.021(4) 0.003(3) 0.024(7) -0.006(6) C9 0.20(3) 0.142(16) 0.164(19) 0.069(13) 0.068(18) -0.001(15) C10 0.100(7) 0.093(7) 0.075(5) 0.004(5) -0.001(5) -0.079(6) C27 0.016(9) 0.25(4) 0.17(3) -0.13(3) 0.037(12) -0.009(17) _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 N11 C16 1.334(4) . ? N11 C12 1.350(3) . ? C12 C13 1.385(4) . ? C12 C17 1.497(4) . ? C13 C14 1.381(4) . ? C14 C15 1.388(3) . ? C15 C16 1.386(4) . ? N21 C26 1.333(17) . ? N21 C22 1.362(15) . ? C22 C23 1.396(17) . ? C22 C27 1.43(3) . ? C23 C24 1.384(16) . ? C24 C25 1.384(15) . ? C25 C26 1.375(17) . ? O211 C211 1.3608(16) . ? C211 C220 1.3896(19) . ? C211 C212 1.4259(19) . ? C212 C213 1.371(2) . ? C212 C221 1.5021(19) . ? C213 C214 1.4130(19) . ? C214 C215 1.416(2) . ? C214 C219 1.4274(19) . ? C215 C216 1.366(2) . ? C216 C217 1.408(2) . ? C217 C218 1.369(2) . ? C218 C219 1.4266(19) . ? C219 C220 1.4284(19) . ? C220 C222 1.5218(19) . ? O221 C221 1.2678(18) . ? C221 O222 1.2635(18) . ? C222 C223 1.5225(18) . ? C223 C224 1.3890(19) . ? C223 C232 1.4257(19) . ? O224 C224 1.3596(16) . ? C224 C225 1.4261(19) . ? C225 C226 1.374(2) . ? C225 C233 1.4913(19) . ? C226 C227 1.4104(19) . ? C227 C228 1.4202(19) . ? C227 C232 1.4279(19) . ? C228 C229 1.365(2) . ? C229 C230 1.409(2) . ? C230 C231 1.369(2) . ? C231 C232 1.4289(19) . ? O233 C233 1.2365(17) . ? C233 O234 1.3037(17) . ? O1 C3 1.399(11) . ? O1 C2 1.422(4) . ? C2 C5 1.193(9) . ? C3 C4 1.640(19) . ? C4 C5 1.547(10) . ? O6 C7 1.441(8) . ? O6 C8 1.524(15) . ? C7 C10 1.520(14) . ? C8 C9 1.26(4) . ? C9 C10 1.53(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 123.6(3) . . ? N11 C12 C13 117.9(3) . . ? N11 C12 C17 117.5(2) . . ? C13 C12 C17 124.6(3) . . ? C14 C13 C12 120.2(3) . . ? C13 C14 C15 120.1(2) . . ? C16 C15 C14 118.3(2) . . ? N11 C16 C15 120.0(3) . . ? C26 N21 C22 125.8(17) . . ? N21 C22 C23 114.7(19) . . ? N21 C22 C27 121(2) . . ? C23 C22 C27 124(2) . . ? C24 C23 C22 120(2) . . ? C25 C24 C23 122.4(18) . . ? C26 C25 C24 116.1(18) . . ? N21 C26 C25 121(2) . . ? O211 C211 C220 118.62(12) . . ? O211 C211 C212 119.76(12) . . ? C220 C211 C212 121.60(13) . . ? C213 C212 C211 119.36(12) . . ? C213 C212 C221 119.68(13) . . ? C211 C212 C221 120.95(13) . . ? C212 C213 C214 121.53(13) . . ? C213 C214 C215 121.27(13) . . ? C213 C214 C219 118.77(13) . . ? C215 C214 C219 119.92(13) . . ? C216 C215 C214 121.10(14) . . ? C215 C216 C217 119.44(14) . . ? C218 C217 C216 121.19(14) . . ? C217 C218 C219 121.07(13) . . ? C218 C219 C214 117.28(12) . . ? C218 C219 C220 122.45(12) . . ? C214 C219 C220 120.23(12) . . ? C211 C220 C219 118.47(12) . . ? C211 C220 C222 119.57(12) . . ? C219 C220 C222 121.75(12) . . ? O222 C221 O221 124.57(13) . . ? O222 C221 C212 116.85(13) . . ? O221 C221 C212 118.58(13) . . ? C220 C222 C223 116.37(11) . . ? C224 C223 C232 118.44(12) . . ? C224 C223 C222 119.81(12) . . ? C232 C223 C222 121.61(12) . . ? O224 C224 C223 118.77(12) . . ? O224 C224 C225 119.84(12) . . ? C223 C224 C225 121.39(12) . . ? C226 C225 C224 119.49(12) . . ? C226 C225 C233 120.60(12) . . ? C224 C225 C233 119.91(12) . . ? C225 C226 C227 121.34(12) . . ? C226 C227 C228 121.18(12) . . ? C226 C227 C232 118.74(12) . . ? C228 C227 C232 120.04(12) . . ? C229 C228 C227 120.80(13) . . ? C228 C229 C230 119.58(13) . . ? C231 C230 C229 121.42(13) . . ? C230 C231 C232 120.77(13) . . ? C223 C232 C227 120.34(12) . . ? C223 C232 C231 122.22(12) . . ? C227 C232 C231 117.37(12) . . ? O233 C233 O234 123.39(12) . . ? O233 C233 C225 121.56(12) . . ? O234 C233 C225 115.04(12) . . ? C3 O1 C2 110.9(6) . . ? C5 C2 O1 110.1(4) . . ? O1 C3 C4 103.4(6) . . ? C5 C4 C3 96.5(7) . . ? C2 C5 C4 114.6(7) . . ? C7 O6 C8 102.1(9) . . ? O6 C7 C10 110.7(7) . . ? C9 C8 O6 111.7(15) . . ? C8 C9 C10 111.8(18) . . ? C7 C10 C9 100.4(14) . . ? 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 N11 H1 O221 1.00 1.78 2.777(3) 177.3 . O234 H234 O222 1.13(2) 1.35(3) 2.4684(14) 170(2) 1_455 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.51 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.291 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.041 #=== END data_1e _database_code_depnum_ccdc_archive 'CCDC 788719' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'bis(4-picolinium) pamoate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H14 O6 2- , 2(C6 H8 N 1+)' _chemical_formula_sum 'C35 H30 N2 O6' _chemical_formula_weight 574.61 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.3324(14) _cell_length_b 12.9301(15) _cell_length_c 18.078(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.542(2) _cell_angle_gamma 90.00 _cell_volume 2842.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2935 _cell_measurement_theta_min 2.299 _cell_measurement_theta_max 27.512 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9804 _exptl_absorpt_correction_T_max 0.9872 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 8320 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.86 _reflns_number_total 3110 _reflns_number_gt 2513 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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. All protons involved in proton transfer reactions were located in the difference map. ; _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^)+(0.0476P)^2^+1.3205P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3110 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 N11 N 0.38752(9) 0.13314(8) 0.48780(6) 0.0246(3) Uani 1 1 d . . . H11 H 0.4539(18) 0.1032(17) 0.5361(12) 0.083(7) Uiso 1 1 d . . . H17C H 0.055(3) 0.250(3) 0.341(2) 0.025(12) Uiso 0.36(3) 1 d P A -1 H17B H 0.148(4) 0.295(4) 0.288(2) 0.033(13) Uiso 0.36(3) 1 d P A -1 H17A H 0.109(4) 0.175(4) 0.276(3) 0.041(15) Uiso 0.36(3) 1 d P A -1 C12 C 0.40966(11) 0.19045(10) 0.43053(8) 0.0272(3) Uani 1 1 d . . . H12 H 0.4837 0.2083 0.4281 0.033 Uiso 1 1 calc R . . C13 C 0.32679(11) 0.22397(10) 0.37499(8) 0.0275(3) Uani 1 1 d . . . H13 H 0.3441 0.2648 0.3348 0.033 Uiso 1 1 calc R . . C14 C 0.21774(11) 0.19821(10) 0.37748(7) 0.0248(3) Uani 1 1 d . . . C15 C 0.19753(11) 0.13867(10) 0.43770(7) 0.0253(3) Uani 1 1 d . . . H15 H 0.1243 0.1194 0.4416 0.030 Uiso 1 1 calc R . . C16 C 0.28332(10) 0.10755(10) 0.49165(7) 0.0249(3) Uani 1 1 d . . . H16 H 0.2684 0.0670 0.5326 0.030 Uiso 1 1 calc R . . C17 C 0.12618(13) 0.23287(13) 0.31731(9) 0.0354(3) Uani 1 1 d . . . H17E H 0.0638 0.1854 0.3152 0.053 Uiso 0.64(3) 1 calc PR A 1 H17D H 0.1518 0.2330 0.2688 0.053 Uiso 0.64(3) 1 calc PR A 1 H17F H 0.1031 0.3028 0.3287 0.053 Uiso 0.64(3) 1 calc PR A 1 H22 H 1.0004 0.1926 0.7074 0.024(3) Uiso 1 1 d R . . H211 H 0.7878 0.1722 0.5840 0.063(6) Uiso 1 1 d R . . O211 O 0.84785(7) 0.16650(7) 0.61791(5) 0.0260(2) Uani 1 1 d . . . C211 C 0.81623(10) 0.10847(9) 0.67342(7) 0.0211(3) Uani 1 1 d . . . C212 C 0.70622(10) 0.06974(10) 0.66432(7) 0.0216(3) Uani 1 1 d . . . C213 C 0.67592(10) 0.00731(10) 0.71870(7) 0.0228(3) Uani 1 1 d . . . H213 H 0.6031 -0.0191 0.7123 0.027 Uiso 1 1 calc R . . C214 C 0.75066(10) -0.01857(9) 0.78402(7) 0.0216(3) Uani 1 1 d . . . C215 C 0.71950(11) -0.08482(10) 0.83927(7) 0.0254(3) Uani 1 1 d . . . H215 H 0.6481 -0.1147 0.8313 0.031 Uiso 1 1 calc R . . C216 C 0.79053(11) -0.10645(10) 0.90382(7) 0.0258(3) Uani 1 1 d . . . H216 H 0.7691 -0.1518 0.9402 0.031 Uiso 1 1 calc R . . C217 C 0.89586(10) -0.06080(10) 0.91599(7) 0.0240(3) Uani 1 1 d . . . H217 H 0.9446 -0.0747 0.9614 0.029 Uiso 1 1 calc R . . C218 C 0.92942(10) 0.00320(10) 0.86365(7) 0.0226(3) Uani 1 1 d . . . H218 H 1.0006 0.0334 0.8735 0.027 Uiso 1 1 calc R . . C219 C 0.85886(10) 0.02493(9) 0.79472(7) 0.0201(3) Uani 1 1 d . . . C220 C 0.89116(10) 0.08941(9) 0.73822(7) 0.0204(3) Uani 1 1 d . . . O221 O 0.52535(7) 0.06719(8) 0.59613(5) 0.0305(2) Uani 1 1 d . . . C221 C 0.62369(10) 0.09865(10) 0.59693(7) 0.0235(3) Uani 1 1 d . . . O222 O 0.65320(8) 0.15140(7) 0.54563(5) 0.0285(2) Uani 1 1 d . . . C222 C 1.0000 0.14735(14) 0.7500 0.0223(4) Uani 1 2 d S . . 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 N11 0.0210(6) 0.0257(6) 0.0260(6) -0.0014(4) 0.0008(4) 0.0003(4) C12 0.0190(6) 0.0302(7) 0.0336(7) -0.0017(6) 0.0076(6) -0.0026(5) C13 0.0278(7) 0.0278(7) 0.0281(7) 0.0039(5) 0.0080(6) -0.0014(6) C14 0.0234(6) 0.0238(6) 0.0261(7) -0.0020(5) 0.0012(5) 0.0017(5) C15 0.0181(6) 0.0273(7) 0.0303(7) -0.0024(5) 0.0034(5) -0.0043(5) C16 0.0235(7) 0.0250(6) 0.0263(7) 0.0012(5) 0.0048(5) -0.0044(5) C17 0.0308(8) 0.0402(9) 0.0327(8) 0.0035(7) -0.0022(6) 0.0054(7) O211 0.0203(5) 0.0319(5) 0.0258(5) 0.0064(4) 0.0040(4) 0.0017(4) C211 0.0195(6) 0.0213(6) 0.0233(6) -0.0008(5) 0.0059(5) 0.0020(5) C212 0.0180(6) 0.0231(6) 0.0235(6) -0.0042(5) 0.0030(5) 0.0024(5) C213 0.0165(6) 0.0253(6) 0.0265(7) -0.0049(5) 0.0032(5) -0.0011(5) C214 0.0195(6) 0.0220(6) 0.0236(6) -0.0037(5) 0.0046(5) 0.0001(5) C215 0.0217(6) 0.0271(7) 0.0282(7) -0.0040(5) 0.0065(5) -0.0047(5) C216 0.0283(7) 0.0253(7) 0.0255(7) 0.0009(5) 0.0093(5) -0.0010(5) C217 0.0221(6) 0.0271(6) 0.0230(6) 0.0004(5) 0.0040(5) 0.0041(5) C218 0.0174(6) 0.0247(6) 0.0258(7) -0.0017(5) 0.0040(5) 0.0008(5) C219 0.0170(6) 0.0202(6) 0.0234(6) -0.0032(5) 0.0045(5) 0.0017(5) C220 0.0158(6) 0.0210(6) 0.0252(6) -0.0026(5) 0.0051(5) 0.0014(5) O221 0.0190(5) 0.0401(6) 0.0307(5) 0.0017(4) -0.0007(4) -0.0003(4) C221 0.0204(6) 0.0253(6) 0.0239(7) -0.0051(5) 0.0016(5) 0.0034(5) O222 0.0248(5) 0.0349(5) 0.0247(5) 0.0019(4) 0.0013(4) 0.0016(4) C222 0.0182(9) 0.0232(9) 0.0258(9) 0.000 0.0050(7) 0.000 _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 N11 C12 1.3376(17) . ? N11 C16 1.3399(17) . ? C12 C13 1.3786(19) . ? C13 C14 1.3935(19) . ? C14 C15 1.3892(19) . ? C14 C17 1.5006(19) . ? C15 C16 1.3749(18) . ? O211 C211 1.3609(15) . ? C211 C220 1.3885(17) . ? C211 C212 1.4299(17) . ? C212 C213 1.3709(18) . ? C212 C221 1.4995(17) . ? C213 C214 1.4125(17) . ? C214 C215 1.4164(18) . ? C214 C219 1.4314(17) . ? C215 C216 1.3668(18) . ? C216 C217 1.4106(18) . ? C217 C218 1.3715(18) . ? C218 C219 1.4246(17) . ? C219 C220 1.4255(17) . ? C220 C222 1.5210(15) . ? O221 C221 1.2769(16) . ? C221 O222 1.2529(16) . ? C222 C220 1.5210(15) 2_756 ? 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 C12 N11 C16 119.84(11) . . ? N11 C12 C13 121.07(12) . . ? C12 C13 C14 120.28(12) . . ? C15 C14 C13 117.21(12) . . ? C15 C14 C17 121.49(13) . . ? C13 C14 C17 121.30(13) . . ? C16 C15 C14 120.07(12) . . ? N11 C16 C15 121.52(12) . . ? O211 C211 C220 119.21(11) . . ? O211 C211 C212 119.38(11) . . ? C220 C211 C212 121.40(11) . . ? C213 C212 C211 119.33(11) . . ? C213 C212 C221 120.02(11) . . ? C211 C212 C221 120.63(11) . . ? C212 C213 C214 121.42(12) . . ? C213 C214 C215 121.14(11) . . ? C213 C214 C219 118.97(11) . . ? C215 C214 C219 119.88(11) . . ? C216 C215 C214 121.02(12) . . ? C215 C216 C217 119.39(12) . . ? C218 C217 C216 121.35(12) . . ? C217 C218 C219 120.80(12) . . ? C218 C219 C220 122.64(11) . . ? C218 C219 C214 117.47(11) . . ? C220 C219 C214 119.87(11) . . ? C211 C220 C219 118.84(11) . . ? C211 C220 C222 118.63(10) . . ? C219 C220 C222 122.19(10) . . ? O222 C221 O221 123.84(11) . . ? O222 C221 C212 119.72(11) . . ? O221 C221 C212 116.44(11) . . ? C220 C222 C220 120.98(15) . 2_756 ? 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 N11 H11 O221 1.16(2) 1.36(2) 2.5195(14) 175(2) . _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.284 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.040 #=== END data_1f _database_code_depnum_ccdc_archive 'CCDC 788720' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'bis(3-picolinium) pamoate 3-picoline co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C23 H14 O6 2-, 2(C6 H8 N 1+), C6 H7 N' _chemical_formula_sum 'C41 H37 N3 O6' _chemical_formula_weight 667.74 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.108(2) _cell_length_b 11.5703(18) _cell_length_c 21.107(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.733(2) _cell_angle_gamma 90.00 _cell_volume 3373.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5562 _cell_measurement_theta_min 2.296 _cell_measurement_theta_max 27.612 _exptl_crystal_description shard _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9782 _exptl_absorpt_correction_T_max 0.9906 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 19883 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 28.04 _reflns_number_total 7380 _reflns_number_gt 5571 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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. All protons involved in proton transfer reactions were located in the difference map (in the major component of the disorder). ; _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^)+(0.0456P)^2^+0.8028P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7380 _refine_ls_number_parameters 524 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.004 _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 N11 N 0.24714(8) 0.42431(10) 0.53237(6) 0.0265(3) Uani 1 1 d . . . H11 H 0.1619(16) 0.4004(19) 0.5097(10) 0.082(7) Uiso 1 1 d . . . C12 C 0.29618(10) 0.37021(12) 0.58515(7) 0.0276(3) Uani 1 1 d . . . H12 H 0.2636 0.3137 0.6055 0.033 Uiso 1 1 calc R . . C13 C 0.39266(10) 0.39368(12) 0.61117(7) 0.0269(3) Uani 1 1 d . . . C14 C 0.43716(10) 0.47823(13) 0.58046(7) 0.0301(3) Uani 1 1 d . . . H14 H 0.5030 0.4975 0.5970 0.036 Uiso 1 1 calc R . . C15 C 0.38666(10) 0.53446(13) 0.52622(7) 0.0313(3) Uani 1 1 d . . . H15 H 0.4170 0.5923 0.5053 0.038 Uiso 1 1 calc R . . C16 C 0.29077(10) 0.50469(13) 0.50299(7) 0.0291(3) Uani 1 1 d . . . H16 H 0.2554 0.5421 0.4655 0.035 Uiso 1 1 calc R . . C17 C 0.44566(11) 0.33292(14) 0.67090(7) 0.0347(4) Uani 1 1 d . . . H17C H 0.5061 0.3003 0.6626 0.052 Uiso 1 1 calc R . . H17A H 0.4051 0.2707 0.6823 0.052 Uiso 1 1 calc R . . H17B H 0.4604 0.3882 0.7067 0.052 Uiso 1 1 calc R . . N21 N -0.66731(13) 0.30433(17) -0.05329(8) 0.0290(4) Uani 0.875(3) 1 d P A 1 H21 H -0.5837(18) 0.312(2) -0.0188(12) 0.073(7) Uiso 0.875(3) 1 d P A 1 C22 C -0.73691(16) 0.3621(2) -0.03189(11) 0.0303(4) Uani 0.875(3) 1 d P A 1 H22 H -0.7196 0.4088 0.0057 0.036 Uiso 0.875(3) 1 calc PR A 1 C23 C -0.83340(14) 0.35620(17) -0.06280(11) 0.0336(5) Uani 0.875(3) 1 d P A 1 C24 C -0.85532(19) 0.2890(2) -0.11808(12) 0.0373(7) Uani 0.875(3) 1 d P A 1 H24 H -0.9205 0.2836 -0.1410 0.045 Uiso 0.875(3) 1 calc PR A 1 C25 C -0.78346(15) 0.22966(18) -0.14048(9) 0.0376(5) Uani 0.875(3) 1 d P A 1 H25 H -0.7988 0.1836 -0.1784 0.045 Uiso 0.875(3) 1 calc PR A 1 C26 C -0.68898(14) 0.23875(17) -0.10657(9) 0.0324(4) Uani 0.875(3) 1 d P A 1 H26 H -0.6390 0.1981 -0.1212 0.039 Uiso 0.875(3) 1 calc PR A 1 C27 C -0.90994(15) 0.41807(18) -0.03571(11) 0.0460(6) Uani 0.875(3) 1 d P A 1 H27A H -0.9592 0.4487 -0.0713 0.069 Uiso 0.875(3) 1 calc PR A 1 H27C H -0.8803 0.4819 -0.0081 0.069 Uiso 0.875(3) 1 calc PR A 1 H27B H -0.9402 0.3640 -0.0101 0.069 Uiso 0.875(3) 1 calc PR A 1 N31 N -0.6935(13) 0.3313(14) -0.0424(7) 0.026(4) Uiso 0.125(3) 1 d P A 2 H31 H -0.6312 0.3261 -0.0258 0.032 Uiso 0.125(3) 1 calc PR A 2 C32 C -0.7260(11) 0.2763(12) -0.0949(6) 0.030(3) Uiso 0.125(3) 1 d P A 2 H32 H -0.6823 0.2312 -0.1134 0.035 Uiso 0.125(3) 1 calc PR A 2 C33 C -0.8237(12) 0.2799(17) -0.1263(8) 0.021(4) Uiso 0.125(3) 1 d P A 2 C34 C -0.8819(13) 0.3458(13) -0.0920(8) 0.035(3) Uiso 0.125(3) 1 d P A 2 H34 H -0.9494 0.3499 -0.1096 0.042 Uiso 0.125(3) 1 calc PR A 2 C35 C -0.8484(11) 0.4021(13) -0.0372(7) 0.030(3) Uiso 0.125(3) 1 d P A 2 H35 H -0.8906 0.4452 -0.0164 0.036 Uiso 0.125(3) 1 calc PR A 2 C36 C -0.7475(12) 0.3961(14) -0.0105(8) 0.034(4) Uiso 0.125(3) 1 d P A 2 H36 H -0.7195 0.4362 0.0280 0.041 Uiso 0.125(3) 1 calc PR A 2 C37 C -0.8659(10) 0.2199(12) -0.1848(6) 0.041(4) Uiso 0.125(3) 1 d P A 2 H37A H -0.9096 0.1596 -0.1751 0.061 Uiso 0.125(3) 1 calc PR A 2 H37B H -0.8144 0.1845 -0.2032 0.061 Uiso 0.125(3) 1 calc PR A 2 H37C H -0.9023 0.2747 -0.2160 0.061 Uiso 0.125(3) 1 calc PR A 2 N41 N -0.3437(7) -0.0033(9) 0.1872(4) 0.052(2) Uani 0.820(3) 1 d P B 3 C42 C -0.26233(18) 0.0601(2) 0.19741(13) 0.0374(6) Uani 0.820(3) 1 d P B 3 H42 H -0.2463 0.0986 0.1612 0.045 Uiso 0.820(3) 1 calc PR B 3 C43 C -0.19983(17) 0.07355(18) 0.25678(14) 0.0248(5) Uani 0.820(3) 1 d P B 3 C44 C -0.22526(16) 0.0164(2) 0.30868(11) 0.0281(5) Uani 0.820(3) 1 d P B 3 H44 H -0.1842 0.0210 0.3503 0.034 Uiso 0.820(3) 1 calc PR B 3 C45 C -0.30977(16) -0.04710(17) 0.30029(11) 0.0378(5) Uani 0.820(3) 1 d P B 3 H45 H -0.3283 -0.0854 0.3357 0.045 Uiso 0.820(3) 1 calc PR B 3 C46 C -0.3662(2) -0.0533(2) 0.23923(15) 0.0448(7) Uani 0.820(3) 1 d P B 3 H46 H -0.4249 -0.0958 0.2336 0.054 Uiso 0.820(3) 1 calc PR B 3 H224 H -0.4895 0.4873 0.1435 0.058(6) Uiso 1 1 d R . . H211 H -0.0021 0.5649 0.3558 0.057(6) Uiso 1 1 d R . . C47 C -0.11157(13) 0.14749(15) 0.26420(9) 0.0310(5) Uani 0.820(3) 1 d P B 3 H47A H -0.1238 0.2219 0.2833 0.047 Uiso 0.820(3) 1 calc PR B 3 H47B H -0.0957 0.1605 0.2217 0.047 Uiso 0.820(3) 1 calc PR B 3 H47C H -0.0573 0.1086 0.2925 0.047 Uiso 0.820(3) 1 calc PR B 3 N51 N -0.348(3) 0.005(3) 0.1903(16) 0.026(5) Uiso 0.180(3) 1 d P B 4 C52 C -0.3277(10) -0.0469(12) 0.2529(7) 0.043(4) Uiso 0.180(3) 1 d P B 4 H52 H -0.3723 -0.1009 0.2640 0.052 Uiso 0.180(3) 1 calc PR B 4 C53 C -0.2468(10) -0.0216(11) 0.2969(6) 0.032(3) Uiso 0.180(3) 1 d P B 4 C54 C -0.1889(10) 0.0613(12) 0.2794(6) 0.028(3) Uiso 0.180(3) 1 d P B 4 H54 H -0.1341 0.0848 0.3107 0.034 Uiso 0.180(3) 1 calc PR B 4 C55 C -0.2030(8) 0.1121(10) 0.2218(6) 0.043(3) Uiso 0.180(3) 1 d P B 4 H55 H -0.1592 0.1680 0.2116 0.052 Uiso 0.180(3) 1 calc PR B 4 C56 C -0.2849(11) 0.0793(14) 0.1776(7) 0.049(4) Uiso 0.180(3) 1 d P B 4 H56 H -0.2957 0.1128 0.1357 0.059 Uiso 0.180(3) 1 calc PR B 4 C57 C -0.2248(7) -0.0801(9) 0.3608(5) 0.048(3) Uiso 0.180(3) 1 d P B 4 H57A H -0.2849 -0.0909 0.3767 0.071 Uiso 0.180(3) 1 calc PR B 4 H57B H -0.1799 -0.0324 0.3916 0.071 Uiso 0.180(3) 1 calc PR B 4 H57C H -0.1952 -0.1555 0.3564 0.071 Uiso 0.180(3) 1 calc PR B 4 O211 O -0.06146(7) 0.56823(8) 0.32887(5) 0.0280(2) Uani 1 1 d . . . C211 C -0.11069(10) 0.47830(11) 0.34834(6) 0.0220(3) Uani 1 1 d . . . C212 C -0.06578(9) 0.41097(11) 0.40297(6) 0.0217(3) Uani 1 1 d . . . C213 C -0.11648(10) 0.32219(12) 0.42329(6) 0.0227(3) Uani 1 1 d . . . H213 H -0.0861 0.2760 0.4589 0.027 Uiso 1 1 calc R . . C214 C -0.21302(10) 0.29779(12) 0.39242(6) 0.0224(3) Uani 1 1 d . . . C215 C -0.26693(10) 0.21049(12) 0.41616(7) 0.0265(3) Uani 1 1 d . . . H215 H -0.2368 0.1655 0.4523 0.032 Uiso 1 1 calc R . . C216 C -0.36163(11) 0.18972(13) 0.38796(7) 0.0295(3) Uani 1 1 d . . . H216 H -0.3976 0.1324 0.4051 0.035 Uiso 1 1 calc R . . C217 C -0.40499(10) 0.25423(13) 0.33332(7) 0.0285(3) Uani 1 1 d . . . H217 H -0.4704 0.2392 0.3133 0.034 Uiso 1 1 calc R . . C218 C -0.35497(10) 0.33839(12) 0.30826(6) 0.0250(3) Uani 1 1 d . . . H218 H -0.3860 0.3800 0.2710 0.030 Uiso 1 1 calc R . . C219 C -0.25680(9) 0.36452(11) 0.33734(6) 0.0220(3) Uani 1 1 d . . . C220 C -0.20327(9) 0.45438(11) 0.31421(6) 0.0216(3) Uani 1 1 d . . . O221 O 0.08420(7) 0.51064(9) 0.41474(5) 0.0289(2) Uani 1 1 d . . . C221 C 0.03595(10) 0.43606(12) 0.43708(6) 0.0225(3) Uani 1 1 d . . . O222 O 0.06955(7) 0.37677(8) 0.48820(4) 0.0263(2) Uani 1 1 d . . . C222 C -0.24630(10) 0.52666(12) 0.25504(6) 0.0236(3) Uani 1 1 d . . . H22A H -0.2012 0.5907 0.2514 0.028 Uiso 1 1 calc R . . H22B H -0.3076 0.5614 0.2618 0.028 Uiso 1 1 calc R . . C223 C -0.26665(10) 0.46018(11) 0.19138(6) 0.0217(3) Uani 1 1 d . . . O224 O -0.43339(7) 0.50565(9) 0.17778(5) 0.0285(2) Uani 1 1 d . . . C224 C -0.36054(10) 0.45051(12) 0.15624(6) 0.0227(3) Uani 1 1 d . . . C225 C -0.38259(10) 0.38230(12) 0.09860(6) 0.0225(3) Uani 1 1 d . . . C226 C -0.30948(10) 0.32576(12) 0.07758(6) 0.0240(3) Uani 1 1 d . . . H226 H -0.3246 0.2777 0.0404 0.029 Uiso 1 1 calc R . . C227 C -0.21222(10) 0.33741(11) 0.10997(6) 0.0222(3) Uani 1 1 d . . . C228 C -0.13632(10) 0.28158(12) 0.08695(7) 0.0253(3) Uani 1 1 d . . . H228 H -0.1517 0.2319 0.0505 0.030 Uiso 1 1 calc R . . C229 C -0.04175(10) 0.29778(12) 0.11615(7) 0.0268(3) Uani 1 1 d . . . H229 H 0.0084 0.2604 0.1000 0.032 Uiso 1 1 calc R . . C230 C -0.01953(10) 0.37074(12) 0.17057(7) 0.0275(3) Uani 1 1 d . . . H230 H 0.0463 0.3837 0.1904 0.033 Uiso 1 1 calc R . . C231 C -0.09087(10) 0.42330(12) 0.19541(6) 0.0244(3) Uani 1 1 d . . . H231 H -0.0737 0.4709 0.2326 0.029 Uiso 1 1 calc R . . C232 C -0.19025(9) 0.40791(11) 0.16650(6) 0.0211(3) Uani 1 1 d . . . O233 O -0.49734(7) 0.30768(10) 0.01078(5) 0.0351(3) Uani 1 1 d . . . C233 C -0.48470(10) 0.37133(12) 0.06168(7) 0.0262(3) Uani 1 1 d . . . O234 O -0.55179(7) 0.42168(9) 0.08106(5) 0.0316(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0225(6) 0.0291(6) 0.0262(6) -0.0060(5) 0.0009(5) 0.0026(5) C12 0.0280(7) 0.0258(7) 0.0281(7) -0.0052(6) 0.0034(6) 0.0010(6) C13 0.0254(7) 0.0269(7) 0.0267(7) -0.0079(6) 0.0015(6) 0.0053(6) C14 0.0216(7) 0.0349(8) 0.0328(8) -0.0069(6) 0.0030(6) 0.0014(6) C15 0.0247(7) 0.0353(8) 0.0336(8) -0.0010(6) 0.0053(6) -0.0005(6) C16 0.0254(7) 0.0325(8) 0.0285(7) -0.0012(6) 0.0038(6) 0.0039(6) C17 0.0332(8) 0.0339(8) 0.0341(8) -0.0010(7) -0.0003(7) 0.0041(7) N21 0.0210(9) 0.0336(10) 0.0305(9) 0.0034(7) 0.0009(7) -0.0019(7) C22 0.0308(11) 0.0276(11) 0.0323(11) 0.0057(9) 0.0060(9) -0.0008(9) C23 0.0265(10) 0.0301(10) 0.0428(12) 0.0161(9) 0.0043(10) -0.0001(8) C24 0.0230(12) 0.0387(14) 0.0454(14) 0.0152(11) -0.0039(11) -0.0040(11) C25 0.0353(11) 0.0369(11) 0.0343(10) 0.0043(8) -0.0076(8) -0.0060(9) C26 0.0305(10) 0.0341(10) 0.0298(9) 0.0009(8) -0.0001(8) -0.0021(8) C27 0.0302(11) 0.0410(12) 0.0674(14) 0.0162(10) 0.0110(10) 0.0051(9) N41 0.037(2) 0.052(3) 0.058(3) -0.0008(16) -0.0157(14) -0.0017(16) C42 0.0364(13) 0.0363(13) 0.0361(14) 0.0036(11) -0.0003(11) -0.0004(10) C43 0.0252(11) 0.0211(11) 0.0295(14) 0.0021(10) 0.0085(11) 0.0032(8) C44 0.0269(11) 0.0288(12) 0.0299(11) -0.0033(10) 0.0089(9) -0.0013(9) C45 0.0344(12) 0.0346(11) 0.0496(14) -0.0033(9) 0.0206(10) -0.0067(9) C46 0.0263(13) 0.0399(14) 0.0663(19) -0.0070(12) 0.0049(13) -0.0046(11) C47 0.0257(9) 0.0270(10) 0.0419(11) -0.0002(8) 0.0103(8) -0.0010(7) O211 0.0265(5) 0.0281(5) 0.0272(5) 0.0017(4) 0.0000(4) -0.0093(4) C211 0.0243(7) 0.0216(7) 0.0208(6) -0.0034(5) 0.0062(5) -0.0033(5) C212 0.0207(6) 0.0245(7) 0.0198(6) -0.0057(5) 0.0039(5) -0.0011(5) C213 0.0232(7) 0.0257(7) 0.0193(6) -0.0019(5) 0.0047(5) 0.0006(6) C214 0.0235(7) 0.0238(7) 0.0200(6) -0.0047(5) 0.0049(5) -0.0016(6) C215 0.0286(7) 0.0275(7) 0.0230(7) -0.0018(6) 0.0042(6) -0.0035(6) C216 0.0314(8) 0.0311(8) 0.0265(7) -0.0035(6) 0.0070(6) -0.0104(6) C217 0.0224(7) 0.0351(8) 0.0274(7) -0.0073(6) 0.0037(6) -0.0072(6) C218 0.0240(7) 0.0302(8) 0.0202(6) -0.0042(6) 0.0028(5) -0.0008(6) C219 0.0214(7) 0.0241(7) 0.0207(6) -0.0068(5) 0.0052(5) -0.0017(5) C220 0.0229(7) 0.0229(7) 0.0189(6) -0.0042(5) 0.0042(5) -0.0003(5) O221 0.0232(5) 0.0312(6) 0.0311(5) 0.0008(4) 0.0024(4) -0.0053(4) C221 0.0214(7) 0.0243(7) 0.0220(7) -0.0051(5) 0.0048(5) -0.0003(6) O222 0.0226(5) 0.0293(5) 0.0251(5) -0.0010(4) 0.0007(4) -0.0013(4) C222 0.0238(7) 0.0228(7) 0.0236(7) -0.0016(5) 0.0034(6) 0.0002(6) C223 0.0238(7) 0.0196(6) 0.0209(6) 0.0017(5) 0.0025(5) -0.0002(5) O224 0.0227(5) 0.0346(6) 0.0266(5) -0.0060(4) 0.0016(4) 0.0079(4) C224 0.0235(7) 0.0228(7) 0.0223(7) 0.0013(5) 0.0055(6) 0.0038(5) C225 0.0221(7) 0.0237(7) 0.0208(6) 0.0018(5) 0.0022(5) 0.0000(5) C226 0.0265(7) 0.0240(7) 0.0212(7) -0.0019(5) 0.0039(6) -0.0015(6) C227 0.0240(7) 0.0208(7) 0.0222(6) 0.0031(5) 0.0056(5) 0.0005(5) C228 0.0294(7) 0.0235(7) 0.0237(7) 0.0002(6) 0.0070(6) 0.0018(6) C229 0.0247(7) 0.0279(8) 0.0294(7) 0.0051(6) 0.0093(6) 0.0045(6) C230 0.0210(7) 0.0317(8) 0.0290(7) 0.0061(6) 0.0036(6) -0.0007(6) C231 0.0239(7) 0.0253(7) 0.0228(7) 0.0025(5) 0.0025(6) -0.0018(6) C232 0.0223(7) 0.0192(6) 0.0218(6) 0.0044(5) 0.0044(5) -0.0002(5) O233 0.0267(5) 0.0480(7) 0.0286(5) -0.0104(5) 0.0006(4) -0.0024(5) C233 0.0247(7) 0.0300(8) 0.0224(7) 0.0014(6) 0.0015(6) -0.0006(6) O234 0.0226(5) 0.0379(6) 0.0322(5) -0.0038(5) 0.0004(4) 0.0056(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.3355(19) . ? N11 C12 1.3409(18) . ? C12 C13 1.387(2) . ? C13 C14 1.392(2) . ? C13 C17 1.503(2) . ? C14 C15 1.382(2) . ? C15 C16 1.385(2) . ? N21 C26 1.339(3) . ? N21 C22 1.340(3) . ? C22 C23 1.386(3) . ? C23 C24 1.383(3) . ? C23 C27 1.502(3) . ? C24 C25 1.385(3) . ? C25 C26 1.383(3) . ? N31 C32 1.28(2) . ? N31 C36 1.342(19) . ? C32 C33 1.40(2) . ? C33 C34 1.42(2) . ? C33 C37 1.44(2) . ? C34 C35 1.33(2) . ? C35 C36 1.42(2) . ? N41 C46 1.335(9) . ? N41 C42 1.342(11) . ? C42 C43 1.387(4) . ? C43 C44 1.388(3) . ? C43 C47 1.493(3) . ? C44 C45 1.381(3) . ? C45 C46 1.372(4) . ? N51 C56 1.31(4) . ? N51 C52 1.43(4) . ? C52 C53 1.349(18) . ? C53 C54 1.359(18) . ? C53 C57 1.484(15) . ? C54 C55 1.327(14) . ? C55 C56 1.382(17) . ? O211 C211 1.3602(16) . ? C211 C220 1.3852(19) . ? C211 C212 1.4285(19) . ? C212 C213 1.3695(19) . ? C212 C221 1.4974(18) . ? C213 C214 1.4137(19) . ? C214 C215 1.4158(19) . ? C214 C219 1.4273(19) . ? C215 C216 1.369(2) . ? C216 C217 1.405(2) . ? C217 C218 1.3704(19) . ? C218 C219 1.4284(18) . ? C219 C220 1.4281(18) . ? C220 C222 1.5230(18) . ? O221 C221 1.2493(16) . ? C221 O222 1.2852(16) . ? C222 C223 1.5241(18) . ? C223 C224 1.3848(19) . ? C223 C232 1.4259(18) . ? O224 C224 1.3639(16) . ? C224 C225 1.4303(18) . ? C225 C226 1.3692(19) . ? C225 C233 1.4974(19) . ? C226 C227 1.4095(19) . ? C227 C228 1.4182(18) . ? C227 C232 1.4265(18) . ? C228 C229 1.364(2) . ? C229 C230 1.408(2) . ? C230 C231 1.3683(19) . ? C231 C232 1.4219(18) . ? O233 C233 1.2846(17) . ? C233 O234 1.2490(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 120.14(13) . . ? N11 C12 C13 122.45(14) . . ? C12 C13 C14 116.90(13) . . ? C12 C13 C17 121.42(14) . . ? C14 C13 C17 121.66(13) . . ? C15 C14 C13 120.76(14) . . ? C14 C15 C16 118.55(14) . . ? N11 C16 C15 121.19(14) . . ? C26 N21 C22 120.52(17) . . ? N21 C22 C23 122.2(2) . . ? C24 C23 C22 117.0(2) . . ? C24 C23 C27 122.3(2) . . ? C22 C23 C27 120.7(2) . . ? C23 C24 C25 120.9(2) . . ? C26 C25 C24 118.8(2) . . ? N21 C26 C25 120.6(2) . . ? C32 N31 C36 124.9(17) . . ? N31 C32 C33 122.5(16) . . ? C32 C33 C34 113.0(15) . . ? C32 C33 C37 125.9(17) . . ? C34 C33 C37 121.1(16) . . ? C35 C34 C33 124.5(18) . . ? C34 C35 C36 118.1(18) . . ? N31 C36 C35 117.0(15) . . ? C46 N41 C42 116.3(7) . . ? N41 C42 C43 124.9(5) . . ? C42 C43 C44 116.2(2) . . ? C42 C43 C47 121.5(2) . . ? C44 C43 C47 122.3(3) . . ? C45 C44 C43 120.5(2) . . ? C46 C45 C44 118.0(2) . . ? N41 C46 C45 124.1(5) . . ? C56 N51 C52 116(3) . . ? C53 C52 N51 122(2) . . ? C52 C53 C54 115.9(12) . . ? C52 C53 C57 121.2(13) . . ? C54 C53 C57 122.9(12) . . ? C55 C54 C53 125.1(13) . . ? C54 C55 C56 116.5(12) . . ? N51 C56 C55 124(2) . . ? O211 C211 C220 118.76(12) . . ? O211 C211 C212 119.41(12) . . ? C220 C211 C212 121.83(12) . . ? C213 C212 C211 119.19(12) . . ? C213 C212 C221 120.36(12) . . ? C211 C212 C221 120.45(12) . . ? C212 C213 C214 121.40(13) . . ? C213 C214 C215 121.06(12) . . ? C213 C214 C219 118.96(12) . . ? C215 C214 C219 119.97(12) . . ? C216 C215 C214 121.23(13) . . ? C215 C216 C217 119.15(13) . . ? C218 C217 C216 121.45(13) . . ? C217 C218 C219 121.00(13) . . ? C214 C219 C220 120.06(12) . . ? C214 C219 C218 117.17(12) . . ? C220 C219 C218 122.77(12) . . ? C211 C220 C219 118.43(12) . . ? C211 C220 C222 119.55(12) . . ? C219 C220 C222 121.99(12) . . ? O221 C221 O222 123.32(12) . . ? O221 C221 C212 119.67(12) . . ? O222 C221 C212 117.00(12) . . ? C220 C222 C223 114.71(11) . . ? C224 C223 C232 118.74(12) . . ? C224 C223 C222 120.08(12) . . ? C232 C223 C222 121.18(12) . . ? O224 C224 C223 119.16(12) . . ? O224 C224 C225 119.56(12) . . ? C223 C224 C225 121.27(12) . . ? C226 C225 C224 119.43(12) . . ? C226 C225 C233 119.95(12) . . ? C224 C225 C233 120.62(12) . . ? C225 C226 C227 121.36(12) . . ? C226 C227 C228 121.24(12) . . ? C226 C227 C232 119.00(12) . . ? C228 C227 C232 119.75(12) . . ? C229 C228 C227 121.33(13) . . ? C228 C229 C230 119.06(13) . . ? C231 C230 C229 121.31(13) . . ? C230 C231 C232 121.20(13) . . ? C231 C232 C223 122.83(12) . . ? C231 C232 C227 117.26(12) . . ? C223 C232 C227 119.91(12) . . ? O234 C233 O233 123.76(13) . . ? O234 C233 C225 120.19(12) . . ? O233 C233 C225 116.05(12) . . ? 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 N11 H11 O222 1.23(2) 1.32(2) 2.5494(15) 177.0(19) . N31 H31 O233 0.88 1.90 2.781(17) 177.3 . _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.246 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.040 #=== END data_1g _database_code_depnum_ccdc_archive 'CCDC 788721' #TrackingRef '- submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'dimethylammonium pamoate DMF solvate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 O6 1-, C3 H7 N O , C2 H8 N 1+' _chemical_formula_sum 'C28 H30 N2 O7' _chemical_formula_weight 506.54 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8970(9) _cell_length_b 13.7462(13) _cell_length_c 21.261(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.5190(10) _cell_angle_gamma 90.00 _cell_volume 2588.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2834 _cell_measurement_theta_min 2.429 _cell_measurement_theta_max 27.309 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9849 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 15381 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.78 _reflns_number_total 5687 _reflns_number_gt 3885 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _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. All protons involved in proton transfer reactions were located in the difference map. ; _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^)+(0.0495P)^2^+0.7284P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5687 _refine_ls_number_parameters 358 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3750(3) 0.35281(16) 0.16751(8) 0.0747(6) Uani 1 1 d . . . C2 C 0.3531(3) 0.2639(2) 0.17595(12) 0.0558(7) Uani 1 1 d . . . H2 H 0.2804 0.2315 0.1477 0.067 Uiso 1 1 calc R . . N3 N 0.4256(2) 0.21297(14) 0.22192(8) 0.0392(5) Uani 1 1 d . . . C4 C 0.3938(3) 0.11064(17) 0.23096(11) 0.0441(6) Uani 1 1 d . . . H4A H 0.3173 0.0887 0.1977 0.066 Uiso 1 1 calc R . . H4B H 0.3561 0.1013 0.2724 0.066 Uiso 1 1 calc R . . H4C H 0.4865 0.0728 0.2289 0.066 Uiso 1 1 calc R . . C5 C 0.5429(3) 0.25714(17) 0.26516(10) 0.0440(6) Uani 1 1 d . . . H5A H 0.6410 0.2289 0.2581 0.066 Uiso 1 1 calc R . . H5B H 0.5214 0.2449 0.3088 0.066 Uiso 1 1 calc R . . H5C H 0.5452 0.3274 0.2576 0.066 Uiso 1 1 calc R . . N11 N 0.31426(18) 0.49015(13) 0.07950(8) 0.0266(4) Uani 1 1 d . . . H1N H 0.354(2) 0.4882(14) 0.0398(10) 0.030(5) Uiso 1 1 d . . . H2N H 0.344(2) 0.4324(17) 0.1025(10) 0.042(6) Uiso 1 1 d . . . C12 C 0.1478(2) 0.49080(17) 0.07045(9) 0.0355(5) Uani 1 1 d . . . H12A H 0.1075 0.4953 0.1116 0.053 Uiso 1 1 calc R . . H12B H 0.1119 0.4307 0.0492 0.053 Uiso 1 1 calc R . . H12C H 0.1134 0.5469 0.0444 0.053 Uiso 1 1 calc R . . C13 C 0.3755(3) 0.57798(17) 0.11254(10) 0.0432(6) Uani 1 1 d . . . H13A H 0.3430 0.6358 0.0879 0.065 Uiso 1 1 calc R . . H13B H 0.4861 0.5748 0.1173 0.065 Uiso 1 1 calc R . . H13C H 0.3382 0.5817 0.1544 0.065 Uiso 1 1 calc R . . O211 O 0.44782(13) 0.78196(9) 0.46295(6) 0.0219(3) Uani 1 1 d . . . H211 H 0.442(2) 0.8493(18) 0.4698(10) 0.046(7) Uiso 1 1 d . . . C211 C 0.33811(19) 0.76581(12) 0.41449(8) 0.0176(4) Uani 1 1 d . . . C212 C 0.24669(18) 0.84517(12) 0.38979(8) 0.0179(4) Uani 1 1 d . . . C213 C 0.13854(19) 0.82861(13) 0.34060(8) 0.0205(4) Uani 1 1 d . . . H213 H 0.0751 0.8807 0.3252 0.025 Uiso 1 1 calc R . . C214 C 0.11895(19) 0.73607(13) 0.31214(8) 0.0200(4) Uani 1 1 d . . . C215 C 0.0139(2) 0.72105(14) 0.25836(8) 0.0242(4) Uani 1 1 d . . . H215 H -0.0488 0.7733 0.2426 0.029 Uiso 1 1 calc R . . C216 C 0.0017(2) 0.63281(14) 0.22902(9) 0.0270(4) Uani 1 1 d . . . H216 H -0.0686 0.6235 0.1930 0.032 Uiso 1 1 calc R . . C217 C 0.0949(2) 0.55541(13) 0.25291(8) 0.0255(4) Uani 1 1 d . . . H217 H 0.0877 0.4942 0.2321 0.031 Uiso 1 1 calc R . . C218 C 0.1953(2) 0.56674(13) 0.30522(8) 0.0213(4) Uani 1 1 d . . . H218 H 0.2558 0.5131 0.3203 0.026 Uiso 1 1 calc R . . C219 C 0.21085(19) 0.65738(12) 0.33742(8) 0.0177(4) Uani 1 1 d . . . C220 C 0.31784(19) 0.67234(12) 0.39107(8) 0.0177(4) Uani 1 1 d . . . O221 O 0.17279(14) 1.01009(9) 0.39756(6) 0.0238(3) Uani 1 1 d . . . C221 C 0.2655(2) 0.94518(13) 0.41725(8) 0.0196(4) Uani 1 1 d . . . O222 O 0.37456(13) 0.95990(9) 0.45955(6) 0.0228(3) Uani 1 1 d . . . C222 C 0.4140(2) 0.58970(12) 0.42093(8) 0.0187(4) Uani 1 1 d . . . H22A H 0.4708 0.5602 0.3879 0.022 Uiso 1 1 calc R . . H22B H 0.4888 0.6176 0.4535 0.022 Uiso 1 1 calc R . . C223 C 0.32797(19) 0.50937(12) 0.45138(8) 0.0178(4) Uani 1 1 d . . . O224 O 0.40150(14) 0.39916(9) 0.37492(6) 0.0240(3) Uani 1 1 d . . . H224 H 0.391(3) 0.3340(19) 0.3656(12) 0.061(8) Uiso 1 1 d . . . C224 C 0.32678(19) 0.41619(13) 0.42690(8) 0.0195(4) Uani 1 1 d . . . C225 C 0.24892(19) 0.33816(12) 0.45427(8) 0.0191(4) Uani 1 1 d . . . C226 C 0.17261(19) 0.35620(13) 0.50633(8) 0.0199(4) Uani 1 1 d . . . H226 H 0.1190 0.3048 0.5240 0.024 Uiso 1 1 calc R . . C227 C 0.17250(19) 0.44941(13) 0.53388(8) 0.0192(4) Uani 1 1 d . . . C228 C 0.0958(2) 0.46797(13) 0.58828(8) 0.0230(4) Uani 1 1 d . . . H228 H 0.0410 0.4170 0.6058 0.028 Uiso 1 1 calc R . . C229 C 0.0995(2) 0.55746(14) 0.61574(9) 0.0258(4) Uani 1 1 d . . . H229 H 0.0475 0.5688 0.6520 0.031 Uiso 1 1 calc R . . C230 C 0.1808(2) 0.63312(14) 0.59002(8) 0.0248(4) Uani 1 1 d . . . H230 H 0.1842 0.6953 0.6096 0.030 Uiso 1 1 calc R . . C231 C 0.2552(2) 0.61877(13) 0.53738(8) 0.0221(4) Uani 1 1 d . . . H231 H 0.3094 0.6711 0.5210 0.026 Uiso 1 1 calc R . . C232 C 0.25248(19) 0.52663(12) 0.50669(8) 0.0176(4) Uani 1 1 d . . . O233 O 0.31277(15) 0.22258(9) 0.37790(6) 0.0295(3) Uani 1 1 d . . . C233 C 0.2504(2) 0.23981(13) 0.42594(8) 0.0217(4) Uani 1 1 d . . . O234 O 0.17992(15) 0.17138(9) 0.45482(6) 0.0256(3) Uani 1 1 d . . . H234 H 0.184(3) 0.1055(19) 0.4305(12) 0.064(8) 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 0.1087(17) 0.0722(15) 0.0459(11) 0.0242(10) 0.0218(11) 0.0359(13) C2 0.0678(18) 0.0633(19) 0.0383(14) 0.0131(13) 0.0156(12) 0.0227(15) N3 0.0389(11) 0.0509(12) 0.0288(9) 0.0032(8) 0.0085(8) 0.0046(9) C4 0.0414(13) 0.0529(15) 0.0385(13) 0.0007(11) 0.0059(10) 0.0031(11) C5 0.0500(14) 0.0460(14) 0.0380(13) -0.0027(11) 0.0141(11) 0.0031(11) N11 0.0263(9) 0.0319(10) 0.0217(8) 0.0001(7) 0.0032(7) 0.0013(7) C12 0.0245(11) 0.0514(14) 0.0306(11) -0.0077(10) 0.0020(8) 0.0016(10) C13 0.0390(13) 0.0533(15) 0.0379(12) -0.0172(11) 0.0068(10) -0.0088(11) O211 0.0232(7) 0.0172(7) 0.0236(7) -0.0011(5) -0.0054(5) -0.0005(5) C211 0.0170(9) 0.0189(9) 0.0170(8) 0.0015(7) 0.0015(7) -0.0008(7) C212 0.0182(9) 0.0172(9) 0.0182(9) 0.0001(7) 0.0018(7) -0.0014(7) C213 0.0210(9) 0.0193(9) 0.0209(9) 0.0009(7) 0.0009(7) 0.0011(7) C214 0.0207(9) 0.0201(9) 0.0189(9) 0.0004(7) 0.0013(7) -0.0007(7) C215 0.0254(10) 0.0242(10) 0.0224(9) 0.0000(8) -0.0017(7) 0.0001(8) C216 0.0292(10) 0.0307(11) 0.0201(9) -0.0021(8) -0.0022(8) -0.0076(8) C217 0.0343(11) 0.0201(10) 0.0223(10) -0.0061(8) 0.0045(8) -0.0080(8) C218 0.0250(10) 0.0184(9) 0.0208(9) 0.0002(7) 0.0042(7) -0.0010(7) C219 0.0195(9) 0.0170(9) 0.0173(9) 0.0000(7) 0.0051(7) -0.0047(7) C220 0.0186(9) 0.0164(9) 0.0183(9) 0.0007(7) 0.0032(7) -0.0003(7) O221 0.0268(7) 0.0155(7) 0.0282(7) -0.0007(5) -0.0025(5) 0.0025(5) C221 0.0217(9) 0.0177(9) 0.0196(9) 0.0014(7) 0.0032(7) -0.0022(7) O222 0.0227(7) 0.0193(7) 0.0254(7) -0.0038(5) -0.0034(5) -0.0005(5) C222 0.0220(9) 0.0144(9) 0.0201(9) -0.0005(7) 0.0040(7) -0.0005(7) C223 0.0175(9) 0.0149(9) 0.0207(9) 0.0010(7) 0.0006(7) 0.0001(7) O224 0.0309(7) 0.0163(7) 0.0264(7) -0.0024(5) 0.0110(6) 0.0015(6) C224 0.0213(9) 0.0179(9) 0.0194(9) 0.0019(7) 0.0030(7) 0.0027(7) C225 0.0203(9) 0.0143(9) 0.0225(9) 0.0015(7) 0.0007(7) 0.0017(7) C226 0.0197(9) 0.0173(9) 0.0224(9) 0.0045(7) 0.0003(7) 0.0002(7) C227 0.0173(9) 0.0187(9) 0.0214(9) 0.0020(7) 0.0006(7) 0.0024(7) C228 0.0233(10) 0.0213(10) 0.0250(10) 0.0019(8) 0.0058(7) -0.0002(8) C229 0.0285(11) 0.0269(11) 0.0228(9) -0.0011(8) 0.0063(8) 0.0030(8) C230 0.0314(11) 0.0184(10) 0.0244(10) -0.0033(8) 0.0018(8) 0.0000(8) C231 0.0235(10) 0.0192(9) 0.0233(9) 0.0006(7) 0.0010(7) 0.0007(7) C232 0.0179(9) 0.0161(9) 0.0182(8) 0.0007(7) -0.0008(7) 0.0014(7) O233 0.0403(8) 0.0183(7) 0.0317(7) -0.0034(6) 0.0137(6) -0.0020(6) C233 0.0223(10) 0.0183(9) 0.0241(9) 0.0018(7) 0.0000(8) 0.0004(7) O234 0.0339(8) 0.0153(7) 0.0283(7) -0.0008(5) 0.0073(6) -0.0028(6) _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 1.253(3) . ? C2 N3 1.319(3) . ? N3 C4 1.451(3) . ? N3 C5 1.455(3) . ? N11 C13 1.475(3) . ? N11 C12 1.475(2) . ? O211 C211 1.368(2) . ? C211 C220 1.383(2) . ? C211 C212 1.430(2) . ? C212 C213 1.370(2) . ? C212 C221 1.497(2) . ? C213 C214 1.412(2) . ? C214 C215 1.421(2) . ? C214 C219 1.429(2) . ? C215 C216 1.363(3) . ? C216 C217 1.413(3) . ? C217 C218 1.367(2) . ? C218 C219 1.422(2) . ? C219 C220 1.429(2) . ? C220 C222 1.524(2) . ? O221 C221 1.259(2) . ? C221 O222 1.274(2) . ? C222 C223 1.523(2) . ? C223 C224 1.382(2) . ? C223 C232 1.429(2) . ? O224 C224 1.364(2) . ? C224 C225 1.431(2) . ? C225 C226 1.376(2) . ? C225 C233 1.481(2) . ? C226 C227 1.409(2) . ? C227 C228 1.422(2) . ? C227 C232 1.431(2) . ? C228 C229 1.361(3) . ? C229 C230 1.407(3) . ? C230 C231 1.368(3) . ? C231 C232 1.424(2) . ? O233 C233 1.232(2) . ? C233 O234 1.315(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 O1 C2 N3 123.5(3) . . ? C2 N3 C4 121.7(2) . . ? C2 N3 C5 121.1(2) . . ? C4 N3 C5 117.25(18) . . ? C13 N11 C12 112.18(17) . . ? O211 C211 C220 118.74(15) . . ? O211 C211 C212 119.49(15) . . ? C220 C211 C212 121.76(15) . . ? C213 C212 C211 119.10(16) . . ? C213 C212 C221 119.62(15) . . ? C211 C212 C221 121.28(15) . . ? C212 C213 C214 121.69(16) . . ? C213 C214 C215 121.35(16) . . ? C213 C214 C219 118.56(15) . . ? C215 C214 C219 120.06(16) . . ? C216 C215 C214 120.98(17) . . ? C215 C216 C217 119.16(17) . . ? C218 C217 C216 121.45(17) . . ? C217 C218 C219 121.15(17) . . ? C218 C219 C220 122.49(16) . . ? C218 C219 C214 117.16(15) . . ? C220 C219 C214 120.29(15) . . ? C211 C220 C219 118.36(15) . . ? C211 C220 C222 119.59(15) . . ? C219 C220 C222 121.99(15) . . ? O221 C221 O222 123.52(16) . . ? O221 C221 C212 118.44(15) . . ? O222 C221 C212 118.04(15) . . ? C223 C222 C220 115.63(14) . . ? C224 C223 C232 118.46(15) . . ? C224 C223 C222 119.85(15) . . ? C232 C223 C222 121.64(15) . . ? O224 C224 C223 118.52(15) . . ? O224 C224 C225 119.59(15) . . ? C223 C224 C225 121.89(15) . . ? C226 C225 C224 119.20(16) . . ? C226 C225 C233 121.07(16) . . ? C224 C225 C233 119.72(15) . . ? C225 C226 C227 121.25(16) . . ? C226 C227 C228 121.41(16) . . ? C226 C227 C232 119.11(15) . . ? C228 C227 C232 119.48(16) . . ? C229 C228 C227 121.17(17) . . ? C228 C229 C230 119.57(17) . . ? C231 C230 C229 121.23(17) . . ? C230 C231 C232 121.00(17) . . ? C231 C232 C223 122.43(16) . . ? C231 C232 C227 117.51(15) . . ? C223 C232 C227 120.05(15) . . ? O233 C233 O234 121.53(16) . . ? O233 C233 C225 122.35(16) . . ? O234 C233 C225 116.12(15) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H2N O1 0.96(2) 1.76(2) 2.676(3) 158.4(19) . O234 H234 O221 1.05(3) 1.49(3) 2.5272(17) 174(2) 1_545 N11 H1N O222 0.95(2) 1.87(2) 2.743(2) 151.6(18) 4_575 N11 H1N O222 0.95(2) 2.45(2) 2.995(2) 116.8(15) 2_645 _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.309 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.051 #=== END