# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 915729' #TrackingRef 'web_deposit_cif_file_0_TanyaleRoex_1358257029.submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,3-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 13.7904(6) _cell_length_b 13.0290(5) _cell_length_c 16.7784(7) _cell_angle_alpha 90.00 _cell_angle_beta 110.7860(10) _cell_angle_gamma 90.00 _cell_volume 2818.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4498 _cell_measurement_theta_min 2.223 _cell_measurement_theta_max 27.598 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _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 0.9770 _exptl_absorpt_correction_T_max 0.9834 _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 16583 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.92 _reflns_number_total 6133 _reflns_number_gt 4631 _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)' _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. The THF molecule is disordered and was modelled over two positions with site occupancies which refined to 0.59 and 0.41. SIMU and DELU restraints were used to restrain the anisotropic displacement parameters of the disordered THF molecule as best possible. An anti-bumping restraint was also used. The long N-H bond has been restrained, but is still longer than expected, presumably as a result of strong hydrogen bonding between the cation and anion. Restraining the bond further resulted in a less satisfactory geometry in other parts of the structure. There is a large residual electron density peak which is likely to be as a result of disordered lutidine. However, this disorder could not be modelled. ; _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^)+(0.0933P)^2^+2.2464P] 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 6133 _refine_ls_number_parameters 435 _refine_ls_number_restraints 22 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1909 _refine_ls_wR_factor_gt 0.1745 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O224 O 1.25126(11) 0.67920(11) 0.26874(9) 0.0235(3) Uani 1 1 d . . . O211 O 0.92734(11) 0.68438(11) 0.39738(9) 0.0230(3) Uani 1 1 d . . . O233 O 1.42542(11) 0.74221(12) 0.26373(10) 0.0276(4) Uani 1 1 d . . . O234 O 1.52000(11) 0.85285(12) 0.36266(10) 0.0275(4) Uani 1 1 d . . . O221 O 0.65486(11) 0.84957(12) 0.29816(10) 0.0269(4) Uani 1 1 d . . . C212 C 0.82032(15) 0.80707(15) 0.29667(13) 0.0194(4) Uani 1 1 d . . . C225 C 1.35814(14) 0.80380(15) 0.36782(13) 0.0191(4) Uani 1 1 d . . . O222 O 0.75403(13) 0.74634(13) 0.40127(11) 0.0345(4) Uani 1 1 d . . . C222 C 1.08880(14) 0.68981(15) 0.33269(13) 0.0188(4) Uani 1 1 d . . . H22A H 1.0810 0.6453 0.3779 0.023 Uiso 1 1 calc R . . H22B H 1.0959 0.6444 0.2877 0.023 Uiso 1 1 calc R . . C232 C 1.20739(14) 0.81361(15) 0.44492(12) 0.0172(4) Uani 1 1 d . . . C226 C 1.37347(14) 0.86702(15) 0.43641(13) 0.0190(4) Uani 1 1 d . . . H226 H 1.4342 0.9082 0.4563 0.023 Uiso 1 1 calc R . . C213 C 0.80536(15) 0.86886(15) 0.22697(13) 0.0201(4) Uani 1 1 d . . . H213 H 0.7447 0.9100 0.2062 0.024 Uiso 1 1 calc R . . C217 C 1.01812(16) 0.86945(16) 0.09949(13) 0.0229(4) Uani 1 1 d . . . H217 H 1.0652 0.8682 0.0697 0.027 Uiso 1 1 calc R . . C214 C 0.87838(15) 0.87245(15) 0.18564(13) 0.0188(4) Uani 1 1 d . . . C224 C 1.26545(15) 0.74417(15) 0.33543(12) 0.0183(4) Uani 1 1 d . . . C219 C 0.97116(14) 0.81310(14) 0.21924(12) 0.0173(4) Uani 1 1 d . . . C227 C 1.30080(15) 0.87226(15) 0.47826(12) 0.0188(4) Uani 1 1 d . . . C211 C 0.91351(15) 0.74778(15) 0.33000(12) 0.0177(4) Uani 1 1 d . . . C218 C 1.04019(15) 0.81392(15) 0.17303(13) 0.0202(4) Uani 1 1 d . . . H218 H 1.1026 0.7753 0.1936 0.024 Uiso 1 1 calc R . . C231 C 1.13725(16) 0.81782(15) 0.49031(13) 0.0205(4) Uani 1 1 d . . . H231 H 1.0740 0.7805 0.4697 0.025 Uiso 1 1 calc R . . C230 C 1.16029(16) 0.87514(16) 0.56328(13) 0.0226(4) Uani 1 1 d . . . H230 H 1.1129 0.8760 0.5928 0.027 Uiso 1 1 calc R . . C215 C 0.85872(16) 0.93001(16) 0.10972(13) 0.0222(4) Uani 1 1 d . . . H215 H 0.7974 0.9702 0.0883 0.027 Uiso 1 1 calc R . . C220 C 0.99006(15) 0.75302(14) 0.29435(12) 0.0175(4) Uani 1 1 d . . . C233 C 1.43797(15) 0.79722(16) 0.32668(13) 0.0209(4) Uani 1 1 d . . . C228 C 1.32099(16) 0.93178(15) 0.55327(13) 0.0216(4) Uani 1 1 d . . . H228 H 1.3827 0.9714 0.5743 0.026 Uiso 1 1 calc R . . C223 C 1.18855(15) 0.75156(14) 0.37071(12) 0.0176(4) Uani 1 1 d . . . C221 C 0.73752(15) 0.80037(16) 0.33513(14) 0.0221(4) Uani 1 1 d . . . C229 C 1.25261(16) 0.93280(16) 0.59559(13) 0.0233(4) Uani 1 1 d . . . H229 H 1.2671 0.9720 0.6463 0.028 Uiso 1 1 calc R . . C216 C 0.92664(17) 0.92852(16) 0.06703(13) 0.0239(4) Uani 1 1 d . . . H216 H 0.9124 0.9669 0.0160 0.029 Uiso 1 1 calc R . . N11 N 0.70605(18) 0.80404(17) 0.54599(15) 0.0438(6) Uani 1 1 d D . . C14 C 0.6667(2) 0.8809(2) 0.68242(17) 0.0395(6) Uani 1 1 d . . . H14 H 0.6515 0.9087 0.7290 0.047 Uiso 1 1 calc R . . C12 C 0.77338(19) 0.86872(18) 0.59846(16) 0.0342(6) Uani 1 1 d . . . C13 C 0.75591(18) 0.90997(17) 0.66861(14) 0.0286(5) Uani 1 1 d . . . C17 C 0.86960(19) 0.89592(19) 0.57818(17) 0.0354(6) Uani 1 1 d . . . H17A H 0.8670 0.9686 0.5625 0.053 Uiso 1 1 calc R . . H17B H 0.8719 0.8536 0.5306 0.053 Uiso 1 1 calc R . . H17C H 0.9318 0.8831 0.6284 0.053 Uiso 1 1 calc R . . C16 C 0.6211(2) 0.7733(2) 0.55961(19) 0.0456(7) Uani 1 1 d . . . H16 H 0.5759 0.7252 0.5218 0.055 Uiso 1 1 calc R . . C18 C 0.8290(2) 0.9843(2) 0.72684(18) 0.0419(6) Uani 1 1 d . . . H18A H 0.8053 1.0011 0.7739 0.063 Uiso 1 1 calc R . . H18B H 0.8314 1.0469 0.6953 0.063 Uiso 1 1 calc R . . H18C H 0.8983 0.9537 0.7497 0.063 Uiso 1 1 calc R . . C15 C 0.5984(2) 0.8097(3) 0.6268(2) 0.0569(9) Uani 1 1 d . . . H15 H 0.5377 0.7876 0.6363 0.068 Uiso 1 1 calc R . . C7 C 0.6227(10) 1.1201(8) 0.9258(7) 0.059(3) Uani 0.417(7) 1 d PU A 1 H7A H 0.6050 1.1929 0.9106 0.071 Uiso 0.417(7) 1 calc PR A 1 H7B H 0.6483 1.1135 0.9887 0.071 Uiso 0.417(7) 1 calc PR A 1 C3 C 0.6675(7) 1.0249(8) 0.8848(5) 0.080(2) Uani 0.583(7) 1 d PU A 2 H3A H 0.6554 1.0515 0.8268 0.096 Uiso 0.583(7) 1 calc PR A 2 H3B H 0.7399 1.0011 0.9124 0.096 Uiso 0.583(7) 1 calc PR A 2 C5 C 0.4901(6) 0.9994(7) 0.8902(4) 0.0603(17) Uani 0.583(7) 1 d PU A 2 H5A H 0.4441 1.0212 0.8327 0.072 Uiso 0.583(7) 1 calc PR A 2 H5B H 0.4519 0.9525 0.9150 0.072 Uiso 0.583(7) 1 calc PR A 2 O2 O 0.5482(5) 0.9812(5) 0.8323(4) 0.0603(19) Uani 0.417(7) 1 d P A 1 O1 O 0.5324(6) 1.0864(5) 0.9452(4) 0.106(2) Uani 0.583(7) 1 d PU A 2 H211 H 0.871(3) 0.694(2) 0.409(2) 0.053(9) Uiso 1 1 d . . . C4 C 0.5902(6) 0.9510(6) 0.8887(6) 0.0700(19) Uani 0.583(7) 1 d PU A 2 H4A H 0.6206 0.9085 0.9405 0.084 Uiso 0.583(7) 1 calc PR A 2 H4B H 0.5731 0.9049 0.8387 0.084 Uiso 0.583(7) 1 calc PR A 2 C9 C 0.6395(6) 1.0187(7) 0.8342(8) 0.107(6) Uani 0.417(7) 1 d P A 1 H9A H 0.6261 1.0514 0.7781 0.128 Uiso 0.417(7) 1 calc PR A 1 H9B H 0.6842 0.9585 0.8366 0.128 Uiso 0.417(7) 1 calc PR A 1 C6 C 0.5233(9) 1.0482(9) 0.8831(7) 0.067(3) Uani 0.417(7) 1 d P A 1 H6A H 0.5057 1.0111 0.9276 0.080 Uiso 0.417(7) 1 calc PR A 1 H6B H 0.4628 1.0901 0.8493 0.080 Uiso 0.417(7) 1 calc PR A 1 C8 C 0.6986(7) 1.0861(9) 0.8934(6) 0.072(3) Uani 0.417(7) 1 d P A 1 H8A H 0.7249 1.1426 0.8672 0.087 Uiso 0.417(7) 1 calc PR A 1 H8B H 0.7574 1.0518 0.9376 0.087 Uiso 0.417(7) 1 calc PR A 1 C2 C 0.6285(8) 1.1007(9) 0.9432(6) 0.115(5) Uani 0.583(7) 1 d PU A 2 H2A H 0.6785 1.0956 1.0024 0.138 Uiso 0.583(7) 1 calc PR A 2 H2B H 0.6323 1.1718 0.9237 0.138 Uiso 0.583(7) 1 calc PR A 2 H224 H 1.3056 0.6881 0.2594 0.055(9) Uiso 1 1 d R . . H234 H 1.5677 0.8452 0.3354 0.079(12) Uiso 1 1 d R . . H11 H 0.7170 0.7754 0.4855 0.102(14) Uiso 1 1 d RD . . 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 O224 0.0196(7) 0.0283(8) 0.0247(8) -0.0075(6) 0.0107(6) -0.0014(6) O211 0.0213(7) 0.0274(8) 0.0240(8) 0.0053(6) 0.0125(6) -0.0007(6) O233 0.0215(7) 0.0349(9) 0.0296(8) -0.0068(7) 0.0131(6) -0.0007(6) O234 0.0168(7) 0.0388(9) 0.0295(8) -0.0060(7) 0.0113(6) -0.0042(6) O221 0.0179(7) 0.0346(8) 0.0306(8) -0.0029(7) 0.0118(6) 0.0002(6) C212 0.0172(9) 0.0214(10) 0.0216(10) -0.0049(8) 0.0094(8) -0.0032(7) C225 0.0146(9) 0.0219(10) 0.0208(10) 0.0029(8) 0.0065(8) 0.0044(7) O222 0.0297(9) 0.0414(10) 0.0416(10) 0.0125(8) 0.0240(8) 0.0058(7) C222 0.0176(9) 0.0186(9) 0.0210(10) 0.0002(8) 0.0077(8) -0.0008(7) C232 0.0168(9) 0.0176(9) 0.0175(9) 0.0039(7) 0.0065(7) 0.0022(7) C226 0.0135(9) 0.0207(10) 0.0217(10) 0.0036(8) 0.0048(8) 0.0012(7) C213 0.0163(9) 0.0205(10) 0.0228(10) -0.0032(8) 0.0062(8) -0.0003(7) C217 0.0260(10) 0.0244(10) 0.0225(10) -0.0032(8) 0.0137(9) -0.0029(8) C214 0.0186(9) 0.0173(9) 0.0204(10) -0.0034(8) 0.0069(8) -0.0014(7) C224 0.0170(9) 0.0201(9) 0.0172(9) -0.0008(7) 0.0052(8) 0.0015(7) C219 0.0165(9) 0.0173(9) 0.0183(9) -0.0040(7) 0.0065(7) -0.0043(7) C227 0.0183(9) 0.0187(9) 0.0179(9) 0.0034(8) 0.0048(8) 0.0030(7) C211 0.0183(9) 0.0183(9) 0.0176(9) -0.0025(7) 0.0078(8) -0.0035(7) C218 0.0200(9) 0.0206(10) 0.0217(10) -0.0028(8) 0.0093(8) -0.0007(7) C231 0.0211(10) 0.0219(10) 0.0194(10) 0.0037(8) 0.0084(8) 0.0004(8) C230 0.0253(10) 0.0252(10) 0.0214(10) 0.0024(8) 0.0133(8) -0.0002(8) C215 0.0234(10) 0.0209(10) 0.0207(10) -0.0005(8) 0.0059(8) 0.0011(8) C220 0.0167(9) 0.0171(9) 0.0183(9) -0.0025(7) 0.0057(8) -0.0024(7) C233 0.0151(9) 0.0244(10) 0.0235(10) 0.0027(8) 0.0071(8) 0.0040(8) C228 0.0210(10) 0.0205(10) 0.0217(10) 0.0000(8) 0.0054(8) -0.0008(8) C223 0.0161(9) 0.0174(9) 0.0185(9) 0.0031(7) 0.0051(8) 0.0008(7) C221 0.0181(9) 0.0241(10) 0.0271(11) -0.0050(9) 0.0116(8) -0.0031(8) C229 0.0294(11) 0.0236(10) 0.0165(10) -0.0003(8) 0.0077(8) 0.0011(8) C216 0.0313(11) 0.0230(10) 0.0184(10) 0.0022(8) 0.0101(9) -0.0001(8) N11 0.0448(13) 0.0371(12) 0.0420(13) 0.0035(10) 0.0060(10) 0.0055(10) C14 0.0362(13) 0.0436(14) 0.0415(14) 0.0193(12) 0.0172(11) 0.0141(11) C12 0.0375(13) 0.0260(11) 0.0308(12) 0.0082(10) 0.0019(10) 0.0107(10) C13 0.0347(12) 0.0225(11) 0.0257(11) 0.0086(9) 0.0073(9) 0.0075(9) C17 0.0332(13) 0.0324(12) 0.0379(14) 0.0101(11) 0.0092(11) 0.0072(10) C16 0.0390(15) 0.0413(15) 0.0431(16) 0.0095(12) -0.0019(12) -0.0027(12) C18 0.0487(15) 0.0315(13) 0.0399(15) 0.0038(11) 0.0087(12) 0.0004(11) C15 0.0269(13) 0.0608(19) 0.075(2) 0.0335(18) 0.0087(14) 0.0010(13) C7 0.114(9) 0.033(4) 0.057(6) -0.017(4) 0.063(7) -0.023(5) C3 0.070(5) 0.091(6) 0.045(4) 0.006(4) -0.023(3) -0.045(4) C5 0.053(4) 0.080(5) 0.043(3) -0.002(3) 0.011(3) 0.010(3) O2 0.067(4) 0.058(4) 0.060(4) -0.008(3) 0.027(3) -0.012(3) O1 0.153(5) 0.093(4) 0.081(4) -0.036(3) 0.053(4) 0.023(4) C4 0.084(5) 0.062(4) 0.069(5) 0.003(3) 0.034(4) 0.003(3) C9 0.029(5) 0.044(6) 0.245(18) 0.060(9) 0.047(8) 0.011(4) C6 0.061(6) 0.077(7) 0.050(5) 0.002(5) 0.005(5) -0.005(5) C8 0.047(5) 0.085(7) 0.073(6) 0.028(6) 0.006(5) 0.006(5) C2 0.071(5) 0.098(7) 0.104(8) -0.032(6) -0.060(5) 0.021(5) _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 O224 C224 1.361(2) . ? O224 H224 0.8270 . ? O211 C211 1.358(2) . ? O211 H211 0.88(3) . ? O233 C233 1.237(3) . ? O234 C233 1.298(2) . ? O234 H234 0.9310 . ? O221 C221 1.262(3) . ? C212 C213 1.374(3) . ? C212 C211 1.432(3) . ? C212 C221 1.500(3) . ? C225 C226 1.369(3) . ? C225 C224 1.428(3) . ? C225 C233 1.495(3) . ? O222 C221 1.265(3) . ? C222 C223 1.524(3) . ? C222 C220 1.525(3) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C232 C231 1.429(3) . ? C232 C223 1.429(3) . ? C232 C227 1.430(3) . ? C226 C227 1.415(3) . ? C226 H226 0.9500 . ? C213 C214 1.412(3) . ? C213 H213 0.9500 . ? C217 C218 1.368(3) . ? C217 C216 1.412(3) . ? C217 H217 0.9500 . ? C214 C215 1.419(3) . ? C214 C219 1.429(3) . ? C224 C223 1.389(3) . ? C219 C218 1.425(3) . ? C219 C220 1.427(3) . ? C227 C228 1.419(3) . ? C211 C220 1.387(3) . ? C218 H218 0.9500 . ? C231 C230 1.372(3) . ? C231 H231 0.9500 . ? C230 C229 1.410(3) . ? C230 H230 0.9500 . ? C215 C216 1.366(3) . ? C215 H215 0.9500 . ? C228 C229 1.367(3) . ? C228 H228 0.9500 . ? C229 H229 0.9500 . ? C216 H216 0.9500 . ? N11 C12 1.329(3) . ? N11 C16 1.332(4) . ? N11 H11 1.1405 . ? C14 C13 1.382(3) . ? C14 C15 1.412(4) . ? C14 H14 0.9500 . ? C12 C13 1.391(3) . ? C12 C17 1.524(4) . ? C13 C18 1.486(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C16 C15 1.359(5) . ? C16 H16 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C15 H15 0.9500 . ? C7 C8 1.412(15) . ? C7 C6 1.604(16) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C3 C4 1.455(11) . ? C3 C2 1.613(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 O1 1.447(10) . ? C5 C4 1.526(10) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? O2 C9 1.340(10) . ? O2 C6 1.347(13) . ? O1 C2 1.350(13) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C9 C8 1.359(11) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C224 O224 H224 101.2 . . ? C211 O211 H211 104(2) . . ? C233 O234 H234 111.3 . . ? C213 C212 C211 119.42(18) . . ? C213 C212 C221 119.54(18) . . ? C211 C212 C221 121.01(18) . . ? C226 C225 C224 119.83(18) . . ? C226 C225 C233 120.22(18) . . ? C224 C225 C233 119.96(18) . . ? C223 C222 C220 115.45(16) . . ? C223 C222 H22A 108.4 . . ? C220 C222 H22A 108.4 . . ? C223 C222 H22B 108.4 . . ? C220 C222 H22B 108.4 . . ? H22A C222 H22B 107.5 . . ? C231 C232 C223 122.55(18) . . ? C231 C232 C227 117.21(18) . . ? C223 C232 C227 120.22(17) . . ? C225 C226 C227 121.40(18) . . ? C225 C226 H226 119.3 . . ? C227 C226 H226 119.3 . . ? C212 C213 C214 121.33(18) . . ? C212 C213 H213 119.3 . . ? C214 C213 H213 119.3 . . ? C218 C217 C216 121.23(19) . . ? C218 C217 H217 119.4 . . ? C216 C217 H217 119.4 . . ? C213 C214 C215 121.07(18) . . ? C213 C214 C219 118.89(18) . . ? C215 C214 C219 119.97(18) . . ? O224 C224 C223 119.00(17) . . ? O224 C224 C225 119.96(17) . . ? C223 C224 C225 121.04(18) . . ? C218 C219 C220 122.46(18) . . ? C218 C219 C214 117.31(18) . . ? C220 C219 C214 120.19(18) . . ? C226 C227 C228 121.06(18) . . ? C226 C227 C232 118.58(18) . . ? C228 C227 C232 120.33(18) . . ? O211 C211 C220 119.04(17) . . ? O211 C211 C212 119.64(17) . . ? C220 C211 C212 121.32(18) . . ? C217 C218 C219 121.12(19) . . ? C217 C218 H218 119.4 . . ? C219 C218 H218 119.4 . . ? C230 C231 C232 120.69(19) . . ? C230 C231 H231 119.7 . . ? C232 C231 H231 119.7 . . ? C231 C230 C229 121.65(19) . . ? C231 C230 H230 119.2 . . ? C229 C230 H230 119.2 . . ? C216 C215 C214 120.99(19) . . ? C216 C215 H215 119.5 . . ? C214 C215 H215 119.5 . . ? C211 C220 C219 118.65(18) . . ? C211 C220 C222 119.59(17) . . ? C219 C220 C222 121.66(17) . . ? O233 C233 O234 123.74(18) . . ? O233 C233 C225 121.66(18) . . ? O234 C233 C225 114.60(18) . . ? C229 C228 C227 120.76(19) . . ? C229 C228 H228 119.6 . . ? C227 C228 H228 119.6 . . ? C224 C223 C232 118.70(17) . . ? C224 C223 C222 119.80(17) . . ? C232 C223 C222 121.42(17) . . ? O221 C221 O222 124.32(18) . . ? O221 C221 C212 116.85(19) . . ? O222 C221 C212 118.83(18) . . ? C228 C229 C230 119.34(19) . . ? C228 C229 H229 120.3 . . ? C230 C229 H229 120.3 . . ? C215 C216 C217 119.37(19) . . ? C215 C216 H216 120.3 . . ? C217 C216 H216 120.3 . . ? C12 N11 C16 121.8(3) . . ? C12 N11 H11 121.0 . . ? C16 N11 H11 117.2 . . ? C13 C14 C15 119.6(3) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? N11 C12 C13 121.0(2) . . ? N11 C12 C17 117.3(2) . . ? C13 C12 C17 121.7(2) . . ? C14 C13 C12 117.9(2) . . ? C14 C13 C18 120.3(2) . . ? C12 C13 C18 121.8(2) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N11 C16 C15 120.9(3) . . ? N11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C15 C14 118.8(3) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C8 C7 C6 106.1(9) . . ? C8 C7 H7A 110.5 . . ? C6 C7 H7A 110.5 . . ? C8 C7 H7B 110.5 . . ? C6 C7 H7B 110.5 . . ? H7A C7 H7B 108.7 . . ? C4 C3 C2 88.3(8) . . ? C4 C3 H3A 113.9 . . ? C2 C3 H3A 113.9 . . ? C4 C3 H3B 113.9 . . ? C2 C3 H3B 113.9 . . ? H3A C3 H3B 111.1 . . ? O1 C5 C4 99.9(6) . . ? O1 C5 H5A 111.8 . . ? C4 C5 H5A 111.8 . . ? O1 C5 H5B 111.8 . . ? C4 C5 H5B 111.8 . . ? H5A C5 H5B 109.5 . . ? C9 O2 C6 101.3(8) . . ? C2 O1 C5 105.6(6) . . ? C3 C4 C5 114.2(7) . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? O2 C9 C8 124.7(10) . . ? O2 C9 H9A 106.2 . . ? C8 C9 H9A 106.2 . . ? O2 C9 H9B 106.2 . . ? C8 C9 H9B 106.2 . . ? H9A C9 H9B 106.3 . . ? O2 C6 C7 107.0(9) . . ? O2 C6 H6A 110.3 . . ? C7 C6 H6A 110.3 . . ? O2 C6 H6B 110.3 . . ? C7 C6 H6B 110.3 . . ? H6A C6 H6B 108.6 . . ? C9 C8 C7 98.6(9) . . ? C9 C8 H8A 112.1 . . ? C7 C8 H8A 112.1 . . ? C9 C8 H8B 112.1 . . ? C7 C8 H8B 112.1 . . ? H8A C8 H8B 109.7 . . ? O1 C2 C3 118.2(8) . . ? O1 C2 H2A 107.8 . . ? C3 C2 H2A 107.8 . . ? O1 C2 H2B 107.8 . . ? C3 C2 H2B 107.8 . . ? H2A C2 H2B 107.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C224 C225 C226 C227 2.2(3) . . . . ? C233 C225 C226 C227 -177.94(17) . . . . ? C211 C212 C213 C214 2.2(3) . . . . ? C221 C212 C213 C214 -176.01(18) . . . . ? C212 C213 C214 C215 174.91(18) . . . . ? C212 C213 C214 C219 -2.2(3) . . . . ? C226 C225 C224 O224 -178.22(17) . . . . ? C233 C225 C224 O224 1.9(3) . . . . ? C226 C225 C224 C223 2.1(3) . . . . ? C233 C225 C224 C223 -177.79(17) . . . . ? C213 C214 C219 C218 176.42(17) . . . . ? C215 C214 C219 C218 -0.7(3) . . . . ? C213 C214 C219 C220 -1.3(3) . . . . ? C215 C214 C219 C220 -178.40(17) . . . . ? C225 C226 C227 C228 175.02(18) . . . . ? C225 C226 C227 C232 -3.1(3) . . . . ? C231 C232 C227 C226 177.92(17) . . . . ? C223 C232 C227 C226 -0.2(3) . . . . ? C231 C232 C227 C228 -0.2(3) . . . . ? C223 C232 C227 C228 -178.29(17) . . . . ? C213 C212 C211 O211 -178.13(17) . . . . ? C221 C212 C211 O211 0.1(3) . . . . ? C213 C212 C211 C220 1.3(3) . . . . ? C221 C212 C211 C220 179.52(17) . . . . ? C216 C217 C218 C219 0.5(3) . . . . ? C220 C219 C218 C217 177.62(18) . . . . ? C214 C219 C218 C217 0.0(3) . . . . ? C223 C232 C231 C230 177.31(18) . . . . ? C227 C232 C231 C230 -0.8(3) . . . . ? C232 C231 C230 C229 0.8(3) . . . . ? C213 C214 C215 C216 -176.07(19) . . . . ? C219 C214 C215 C216 1.0(3) . . . . ? O211 C211 C220 C219 174.78(16) . . . . ? C212 C211 C220 C219 -4.7(3) . . . . ? O211 C211 C220 C222 -1.5(3) . . . . ? C212 C211 C220 C222 179.07(17) . . . . ? C218 C219 C220 C211 -172.93(17) . . . . ? C214 C219 C220 C211 4.6(3) . . . . ? C218 C219 C220 C222 3.2(3) . . . . ? C214 C219 C220 C222 -179.21(17) . . . . ? C223 C222 C220 C211 -116.1(2) . . . . ? C223 C222 C220 C219 67.8(2) . . . . ? C226 C225 C233 O233 -178.69(19) . . . . ? C224 C225 C233 O233 1.2(3) . . . . ? C226 C225 C233 O234 1.7(3) . . . . ? C224 C225 C233 O234 -178.44(18) . . . . ? C226 C227 C228 C229 -176.99(18) . . . . ? C232 C227 C228 C229 1.1(3) . . . . ? O224 C224 C223 C232 175.07(17) . . . . ? C225 C224 C223 C232 -5.2(3) . . . . ? O224 C224 C223 C222 -1.9(3) . . . . ? C225 C224 C223 C222 177.80(17) . . . . ? C231 C232 C223 C224 -173.75(18) . . . . ? C227 C232 C223 C224 4.3(3) . . . . ? C231 C232 C223 C222 3.2(3) . . . . ? C227 C232 C223 C222 -178.81(17) . . . . ? C220 C222 C223 C224 -116.3(2) . . . . ? C220 C222 C223 C232 66.8(2) . . . . ? C213 C212 C221 O221 3.1(3) . . . . ? C211 C212 C221 O221 -175.12(18) . . . . ? C213 C212 C221 O222 -177.27(19) . . . . ? C211 C212 C221 O222 4.5(3) . . . . ? C227 C228 C229 C230 -1.0(3) . . . . ? C231 C230 C229 C228 0.0(3) . . . . ? C214 C215 C216 C217 -0.5(3) . . . . ? C218 C217 C216 C215 -0.2(3) . . . . ? C16 N11 C12 C13 -2.3(4) . . . . ? C16 N11 C12 C17 178.0(2) . . . . ? C15 C14 C13 C12 1.4(3) . . . . ? C15 C14 C13 C18 -179.6(2) . . . . ? N11 C12 C13 C14 0.5(3) . . . . ? C17 C12 C13 C14 -179.8(2) . . . . ? N11 C12 C13 C18 -178.5(2) . . . . ? C17 C12 C13 C18 1.1(3) . . . . ? C12 N11 C16 C15 2.1(4) . . . . ? N11 C16 C15 C14 -0.1(4) . . . . ? C13 C14 C15 C16 -1.6(4) . . . . ? C4 C5 O1 C2 20.0(8) . . . . ? C2 C3 C4 C5 34.7(8) . . . . ? O1 C5 C4 C3 -39.3(8) . . . . ? C6 O2 C9 C8 17.2(12) . . . . ? C9 O2 C6 C7 -8.4(11) . . . . ? C8 C7 C6 O2 0.4(12) . . . . ? O2 C9 C8 C7 -16.6(13) . . . . ? C6 C7 C8 C9 7.7(11) . . . . ? C5 O1 C2 C3 0.5(11) . . . . ? C4 C3 C2 O1 -21.5(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 O222 1.14 1.71 2.835(3) 169.2 . O211 H211 O222 0.88(3) 1.72(3) 2.545(2) 157(3) . O224 H224 O233 0.83 1.77 2.568(2) 160.4 . O234 H234 O221 0.93 1.54 2.462(2) 170.3 1_655 _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.042 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.062 data_2 _database_code_depnum_ccdc_archive 'CCDC 915730' #TrackingRef 'web_deposit_cif_file_0_TanyaleRoex_1358257029.submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,4-lutidinium pamoate dihydrate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H14 O6 2- , 2(C7 H10 N 1+) , 2(H2 O)' _chemical_formula_sum 'C37 H37.36 N2 O7.68' _chemical_formula_weight 632.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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)/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 10.8660(12) _cell_length_b 24.737(3) _cell_length_c 11.8896(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.5840(10) _cell_angle_gamma 90.00 _cell_volume 3174.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7401 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.66 _exptl_crystal_description shard _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1339 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9620 _exptl_absorpt_correction_T_max 0.9837 _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 18850 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.85 _reflns_number_total 6903 _reflns_number_gt 5712 _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)' _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. The occupancy of the water molecule containing atom O2 refined to an occupancy of 0.68 and the geometry of this water molecule was restrained using DFIX and DANG restraints. ; _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^)+(0.0484P)^2^+1.2098P] 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 6903 _refine_ls_number_parameters 461 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.59394(13) 0.04756(5) 0.37262(11) 0.0406(3) Uani 1 1 d . . . H11 H 0.0553(17) 0.5308(8) 0.6265(15) 0.040(5) Uiso 1 1 d . . . H211 H 0.333(2) 0.4444(9) 0.4653(18) 0.055(6) Uiso 1 1 d . . . H224 H 0.6054(19) 0.1668(9) 0.4558(17) 0.052(6) Uiso 1 1 d . . . H19 H 0.9008(19) 0.0813(9) 0.6474(17) 0.055(6) Uiso 1 1 d . . . H1A H 0.601(2) 0.0478(9) 0.298(2) 0.058(6) Uiso 1 1 d . . . H1B H 0.643(2) 0.0743(10) 0.4018(19) 0.062(7) Uiso 1 1 d . . . N11 N 0.03946(10) 0.56885(5) 0.62476(9) 0.0195(2) Uani 1 1 d . . . C12 C -0.04701(12) 0.58862(5) 0.68613(11) 0.0207(3) Uani 1 1 d . . . C13 C -0.06462(13) 0.64404(5) 0.68831(12) 0.0226(3) Uani 1 1 d . . . H13 H -0.1260 0.6586 0.7305 0.027 Uiso 1 1 calc R . . C14 C 0.00587(13) 0.67862(5) 0.62997(11) 0.0219(3) Uani 1 1 d . . . C15 C 0.09340(13) 0.65591(6) 0.56676(12) 0.0231(3) Uani 1 1 d . . . H15 H 0.1427 0.6785 0.5254 0.028 Uiso 1 1 calc R . . C221 C 0.18078(12) 0.45073(5) 0.57777(11) 0.0205(3) Uani 1 1 d . . . C16 C 0.10794(12) 0.60089(6) 0.56463(11) 0.0224(3) Uani 1 1 d . . . H16 H 0.1665 0.5853 0.5206 0.027 Uiso 1 1 calc R . . C17 C -0.11938(15) 0.54946(6) 0.74837(13) 0.0303(3) Uani 1 1 d . . . H17A H -0.1140 0.5133 0.7154 0.045 Uiso 1 1 calc R . . H17B H -0.2063 0.5608 0.7422 0.045 Uiso 1 1 calc R . . H17C H -0.0853 0.5485 0.8283 0.045 Uiso 1 1 calc R . . C18 C -0.01036(16) 0.73879(6) 0.63436(14) 0.0308(3) Uani 1 1 d . . . H18A H -0.0755 0.7475 0.6820 0.046 Uiso 1 1 calc R . . H18B H -0.0338 0.7526 0.5577 0.046 Uiso 1 1 calc R . . H18C H 0.0676 0.7556 0.6662 0.046 Uiso 1 1 calc R . . N19 N 0.92689(11) 0.04063(5) 0.64342(10) 0.0208(2) Uani 1 1 d . . . C20 C 1.02896(13) 0.02192(5) 0.70636(11) 0.0216(3) Uani 1 1 d . . . C21 C 1.05835(13) -0.03248(5) 0.70010(12) 0.0233(3) Uani 1 1 d . . . H21 H 1.1305 -0.0460 0.7437 0.028 Uiso 1 1 calc R . . C22 C 0.98394(13) -0.06754(5) 0.63108(12) 0.0236(3) Uani 1 1 d . . . C23 C 0.87982(13) -0.04620(6) 0.56696(12) 0.0247(3) Uani 1 1 d . . . H23 H 0.8273 -0.0689 0.5182 0.030 Uiso 1 1 calc R . . C24 C 0.85350(13) 0.00793(6) 0.57469(12) 0.0237(3) Uani 1 1 d . . . H24 H 0.7825 0.0224 0.5309 0.028 Uiso 1 1 calc R . . C25 C 1.10589(14) 0.06149(6) 0.77869(13) 0.0287(3) Uani 1 1 d . . . H25A H 1.1641 0.0793 0.7336 0.043 Uiso 1 1 calc R . . H25B H 1.1521 0.0425 0.8424 0.043 Uiso 1 1 calc R . . H25C H 1.0519 0.0887 0.8076 0.043 Uiso 1 1 calc R . . C26 C 1.01225(15) -0.12692(6) 0.62779(14) 0.0317(3) Uani 1 1 d . . . H26A H 1.0967 -0.1334 0.6638 0.048 Uiso 1 1 calc R . . H26B H 1.0053 -0.1392 0.5489 0.048 Uiso 1 1 calc R . . H26C H 0.9533 -0.1469 0.6685 0.048 Uiso 1 1 calc R . . C32 C 0.77386(12) 0.15692(5) 0.58488(11) 0.0180(3) Uani 1 1 d . . . O211 O 0.37266(9) 0.41258(4) 0.45073(8) 0.0236(2) Uani 1 1 d . . . C211 C 0.31943(11) 0.37546(5) 0.51476(11) 0.0181(3) Uani 1 1 d . . . C212 C 0.22225(12) 0.39256(5) 0.57902(11) 0.0185(3) Uani 1 1 d . . . C213 C 0.16618(12) 0.35512(5) 0.64125(11) 0.0201(3) Uani 1 1 d . . . H213 H 0.1031 0.3665 0.6851 0.024 Uiso 1 1 calc R . . C214 C 0.20011(12) 0.30006(5) 0.64154(11) 0.0198(3) Uani 1 1 d . . . C215 C 0.13798(13) 0.26118(6) 0.70183(13) 0.0265(3) Uani 1 1 d . . . H215 H 0.0751 0.2726 0.7459 0.032 Uiso 1 1 calc R . . C216 C 0.16672(15) 0.20756(6) 0.69780(14) 0.0316(3) Uani 1 1 d . . . H216 H 0.1238 0.1819 0.7383 0.038 Uiso 1 1 calc R . . C217 C 0.26054(13) 0.19051(6) 0.63311(13) 0.0267(3) Uani 1 1 d . . . H217 H 0.2799 0.1531 0.6296 0.032 Uiso 1 1 calc R . . C218 C 0.32419(12) 0.22695(5) 0.57529(11) 0.0209(3) Uani 1 1 d . . . H218 H 0.3874 0.2145 0.5328 0.025 Uiso 1 1 calc R . . C219 C 0.29712(11) 0.28340(5) 0.57783(11) 0.0179(3) Uani 1 1 d . . . C220 C 0.36006(11) 0.32237(5) 0.51689(11) 0.0173(3) Uani 1 1 d . . . O221 O 0.22961(9) 0.48365(4) 0.51497(8) 0.0257(2) Uani 1 1 d . . . O222 O 0.09894(9) 0.46400(4) 0.64038(8) 0.0254(2) Uani 1 1 d . . . C222 C 0.46698(12) 0.30543(5) 0.45224(11) 0.0181(3) Uani 1 1 d . . . H22A H 0.4892 0.3363 0.4057 0.022 Uiso 1 1 calc R . . H22B H 0.4383 0.2757 0.3999 0.022 Uiso 1 1 calc R . . C223 C 0.58313(11) 0.28679(5) 0.52636(10) 0.0164(3) Uani 1 1 d . . . O224 O 0.56113(9) 0.19897(4) 0.44631(8) 0.0214(2) Uani 1 1 d . . . C224 C 0.62409(11) 0.23381(5) 0.52037(10) 0.0167(3) Uani 1 1 d . . . C225 C 0.73025(11) 0.21462(5) 0.59183(10) 0.0170(3) Uani 1 1 d . . . C226 C 0.79222(11) 0.24925(5) 0.66816(11) 0.0175(3) Uani 1 1 d . . . H226 H 0.8603 0.2361 0.7179 0.021 Uiso 1 1 calc R . . C227 C 0.75731(11) 0.30408(5) 0.67478(11) 0.0173(3) Uani 1 1 d . . . C228 C 0.82675(12) 0.34068(5) 0.74954(11) 0.0208(3) Uani 1 1 d . . . H228 H 0.8929 0.3274 0.8014 0.025 Uiso 1 1 calc R . . C229 C 0.79956(12) 0.39466(6) 0.74780(12) 0.0224(3) Uani 1 1 d . . . H229 H 0.8470 0.4188 0.7975 0.027 Uiso 1 1 calc R . . C230 C 0.70038(12) 0.41419(5) 0.67160(11) 0.0212(3) Uani 1 1 d . . . H230 H 0.6834 0.4519 0.6687 0.025 Uiso 1 1 calc R . . C231 C 0.62820(12) 0.37991(5) 0.60176(11) 0.0185(3) Uani 1 1 d . . . H231 H 0.5602 0.3940 0.5532 0.022 Uiso 1 1 calc R . . C232 C 0.65368(11) 0.32335(5) 0.60083(10) 0.0162(3) Uani 1 1 d . . . O233 O 0.71635(9) 0.12622(4) 0.51149(8) 0.0255(2) Uani 1 1 d . . . O234 O 0.86444(9) 0.14205(4) 0.65319(8) 0.0240(2) Uani 1 1 d . . . O2 O 0.10121(19) 0.55769(8) 0.96318(19) 0.0538(9) Uani 0.677(5) 1 d PD A 1 H2A H 0.048(3) 0.5531(14) 1.021(3) 0.088(14) Uiso 0.677(5) 1 d PD . . H2B H 0.099(3) 0.5220(9) 0.931(3) 0.085(13) Uiso 0.677(5) 1 d PD . . 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 0.0560(8) 0.0340(7) 0.0300(6) 0.0001(5) -0.0030(6) -0.0180(6) N11 0.0219(6) 0.0151(5) 0.0214(6) -0.0014(4) 0.0018(4) 0.0034(4) C12 0.0216(6) 0.0194(7) 0.0211(6) -0.0007(5) 0.0029(5) 0.0012(5) C13 0.0259(7) 0.0184(7) 0.0245(7) -0.0022(5) 0.0076(5) 0.0034(5) C14 0.0259(7) 0.0175(7) 0.0219(7) -0.0001(5) 0.0001(5) 0.0011(5) C15 0.0241(7) 0.0210(7) 0.0249(7) 0.0032(5) 0.0052(5) -0.0013(5) C221 0.0199(6) 0.0167(6) 0.0236(7) -0.0027(5) -0.0030(5) 0.0030(5) C16 0.0202(6) 0.0243(7) 0.0231(7) -0.0010(5) 0.0045(5) 0.0036(5) C17 0.0362(8) 0.0220(7) 0.0349(8) 0.0023(6) 0.0133(7) -0.0017(6) C18 0.0421(9) 0.0154(7) 0.0358(8) 0.0000(6) 0.0080(7) 0.0019(6) N19 0.0237(6) 0.0158(6) 0.0239(6) 0.0011(4) 0.0064(5) 0.0018(4) C20 0.0237(7) 0.0186(7) 0.0233(7) 0.0030(5) 0.0064(5) 0.0006(5) C21 0.0250(7) 0.0186(7) 0.0267(7) 0.0030(5) 0.0053(6) 0.0029(5) C22 0.0294(7) 0.0168(7) 0.0272(7) 0.0010(5) 0.0136(6) 0.0004(5) C23 0.0281(7) 0.0217(7) 0.0255(7) -0.0034(6) 0.0080(6) -0.0040(6) C24 0.0228(7) 0.0246(7) 0.0245(7) 0.0009(6) 0.0054(5) 0.0004(5) C25 0.0321(8) 0.0193(7) 0.0336(8) -0.0012(6) -0.0010(6) 0.0006(6) C26 0.0394(9) 0.0159(7) 0.0418(9) -0.0021(6) 0.0132(7) 0.0023(6) C32 0.0176(6) 0.0162(6) 0.0211(6) 0.0013(5) 0.0054(5) 0.0008(5) O211 0.0238(5) 0.0176(5) 0.0301(5) 0.0062(4) 0.0066(4) 0.0048(4) C211 0.0160(6) 0.0175(6) 0.0199(6) 0.0006(5) -0.0011(5) 0.0006(5) C212 0.0174(6) 0.0159(6) 0.0213(6) -0.0023(5) -0.0021(5) 0.0026(5) C213 0.0177(6) 0.0194(7) 0.0232(7) -0.0040(5) 0.0031(5) 0.0019(5) C214 0.0184(6) 0.0182(6) 0.0227(6) -0.0023(5) 0.0014(5) -0.0005(5) C215 0.0247(7) 0.0225(7) 0.0343(8) -0.0026(6) 0.0119(6) -0.0001(6) C216 0.0327(8) 0.0193(7) 0.0455(9) 0.0039(6) 0.0164(7) -0.0029(6) C217 0.0270(7) 0.0156(6) 0.0383(8) -0.0007(6) 0.0068(6) 0.0009(5) C218 0.0190(6) 0.0175(6) 0.0261(7) -0.0022(5) 0.0026(5) 0.0017(5) C219 0.0161(6) 0.0171(6) 0.0199(6) -0.0022(5) -0.0010(5) 0.0007(5) C220 0.0154(6) 0.0181(6) 0.0178(6) -0.0011(5) -0.0014(5) 0.0019(5) O221 0.0284(5) 0.0164(5) 0.0327(5) 0.0025(4) 0.0050(4) 0.0039(4) O222 0.0279(5) 0.0176(5) 0.0316(5) -0.0013(4) 0.0064(4) 0.0076(4) C222 0.0185(6) 0.0171(6) 0.0184(6) 0.0007(5) 0.0013(5) 0.0033(5) C223 0.0153(6) 0.0183(6) 0.0163(6) 0.0021(5) 0.0043(5) 0.0015(5) O224 0.0207(5) 0.0183(5) 0.0240(5) -0.0050(4) -0.0027(4) 0.0032(4) C224 0.0163(6) 0.0178(6) 0.0166(6) -0.0010(5) 0.0040(5) -0.0003(5) C225 0.0171(6) 0.0161(6) 0.0183(6) 0.0017(5) 0.0050(5) 0.0018(5) C226 0.0159(6) 0.0189(6) 0.0178(6) 0.0029(5) 0.0022(5) 0.0015(5) C227 0.0162(6) 0.0180(6) 0.0182(6) 0.0008(5) 0.0042(5) 0.0000(5) C228 0.0188(6) 0.0219(7) 0.0214(6) -0.0011(5) 0.0014(5) 0.0008(5) C229 0.0222(7) 0.0201(7) 0.0252(7) -0.0051(5) 0.0036(5) -0.0034(5) C230 0.0231(7) 0.0144(6) 0.0272(7) -0.0003(5) 0.0081(5) 0.0005(5) C231 0.0172(6) 0.0177(6) 0.0212(6) 0.0027(5) 0.0052(5) 0.0013(5) C232 0.0153(6) 0.0164(6) 0.0178(6) 0.0017(5) 0.0062(5) 0.0003(5) O233 0.0261(5) 0.0188(5) 0.0303(5) -0.0055(4) -0.0025(4) 0.0035(4) O234 0.0238(5) 0.0166(5) 0.0300(5) 0.0007(4) -0.0031(4) 0.0050(4) O2 0.0409(12) 0.0488(14) 0.0664(16) -0.0225(11) -0.0166(10) 0.0086(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 H1A 0.90(2) . ? O1 H1B 0.89(2) . ? N11 C12 1.3458(17) . ? N11 C16 1.3473(18) . ? N11 H11 0.957(19) . ? C12 C13 1.3851(19) . ? C12 C17 1.4959(19) . ? C13 C14 1.3861(19) . ? C13 H13 0.9500 . ? C14 C15 1.3960(19) . ? C14 C18 1.5005(19) . ? C15 C16 1.3707(19) . ? C15 H15 0.9500 . ? C221 O221 1.2622(17) . ? C221 O222 1.2667(16) . ? C221 C212 1.5075(18) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? N19 C24 1.3448(18) . ? N19 C20 1.3468(17) . ? N19 H19 1.05(2) . ? C20 C21 1.3869(19) . ? C20 C25 1.494(2) . ? C21 C22 1.388(2) . ? C21 H21 0.9500 . ? C22 C23 1.394(2) . ? C22 C26 1.5021(19) . ? C23 C24 1.375(2) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C32 O234 1.2572(16) . ? C32 O233 1.2662(16) . ? C32 C225 1.5092(18) . ? O211 C211 1.3631(16) . ? O211 H211 0.92(2) . ? C211 C220 1.3850(18) . ? C211 C212 1.4362(18) . ? C212 C213 1.3710(19) . ? C213 C214 1.4109(18) . ? C213 H213 0.9500 . ? C214 C215 1.4163(19) . ? C214 C219 1.4275(18) . ? C215 C216 1.365(2) . ? C215 H215 0.9500 . ? C216 C217 1.410(2) . ? C216 H216 0.9500 . ? C217 C218 1.368(2) . ? C217 H217 0.9500 . ? C218 C219 1.4280(18) . ? C218 H218 0.9500 . ? C219 C220 1.4267(18) . ? C220 C222 1.5235(18) . ? C222 C223 1.5255(17) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C223 C224 1.3886(18) . ? C223 C232 1.4260(18) . ? O224 C224 1.3594(15) . ? O224 H224 0.93(2) . ? C224 C225 1.4328(17) . ? C225 C226 1.3677(18) . ? C226 C227 1.4131(18) . ? C226 H226 0.9500 . ? C227 C228 1.4231(18) . ? C227 C232 1.4288(17) . ? C228 C229 1.3671(19) . ? C228 H228 0.9500 . ? C229 C230 1.4113(19) . ? C229 H229 0.9500 . ? C230 C231 1.3692(18) . ? C230 H230 0.9500 . ? C231 C232 1.4266(18) . ? C231 H231 0.9500 . ? O2 H2A 0.959(18) . ? O2 H2B 0.963(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 H1A O1 H1B 105(2) . . ? C12 N11 C16 122.44(12) . . ? C12 N11 H11 118.7(11) . . ? C16 N11 H11 118.8(11) . . ? N11 C12 C13 118.45(12) . . ? N11 C12 C17 118.18(12) . . ? C13 C12 C17 123.37(13) . . ? C12 C13 C14 121.07(13) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 C15 118.08(12) . . ? C13 C14 C18 121.39(13) . . ? C15 C14 C18 120.53(13) . . ? C16 C15 C14 119.78(13) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? O221 C221 O222 123.47(12) . . ? O221 C221 C212 118.44(12) . . ? O222 C221 C212 118.08(12) . . ? N11 C16 C15 120.16(13) . . ? N11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 N19 C20 121.61(12) . . ? C24 N19 H19 117.4(11) . . ? C20 N19 H19 120.9(11) . . ? N19 C20 C21 118.92(13) . . ? N19 C20 C25 117.74(12) . . ? C21 C20 C25 123.34(13) . . ? C20 C21 C22 121.05(13) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C21 C22 C23 117.90(13) . . ? C21 C22 C26 121.28(13) . . ? C23 C22 C26 120.80(13) . . ? C24 C23 C22 119.65(13) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? N19 C24 C23 120.87(13) . . ? N19 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O234 C32 O233 123.89(12) . . ? O234 C32 C225 117.96(11) . . ? O233 C32 C225 118.14(11) . . ? C211 O211 H211 103.5(13) . . ? O211 C211 C220 119.62(12) . . ? O211 C211 C212 118.93(11) . . ? C220 C211 C212 121.45(12) . . ? C213 C212 C211 119.18(12) . . ? C213 C212 C221 119.95(12) . . ? C211 C212 C221 120.87(12) . . ? C212 C213 C214 121.41(12) . . ? C212 C213 H213 119.3 . . ? C214 C213 H213 119.3 . . ? C213 C214 C215 121.15(12) . . ? C213 C214 C219 119.09(12) . . ? C215 C214 C219 119.75(12) . . ? C216 C215 C214 121.20(13) . . ? C216 C215 H215 119.4 . . ? C214 C215 H215 119.4 . . ? C215 C216 C217 119.50(14) . . ? C215 C216 H216 120.2 . . ? C217 C216 H216 120.2 . . ? C218 C217 C216 121.04(13) . . ? C218 C217 H217 119.5 . . ? C216 C217 H217 119.5 . . ? C217 C218 C219 121.08(13) . . ? C217 C218 H218 119.5 . . ? C219 C218 H218 119.5 . . ? C220 C219 C214 120.03(12) . . ? C220 C219 C218 122.55(12) . . ? C214 C219 C218 117.39(12) . . ? C211 C220 C219 118.66(12) . . ? C211 C220 C222 120.76(12) . . ? C219 C220 C222 120.54(11) . . ? C220 C222 C223 114.83(10) . . ? C220 C222 H22A 108.6 . . ? C223 C222 H22A 108.6 . . ? C220 C222 H22B 108.6 . . ? C223 C222 H22B 108.6 . . ? H22A C222 H22B 107.5 . . ? C224 C223 C232 118.54(11) . . ? C224 C223 C222 120.29(11) . . ? C232 C223 C222 121.15(11) . . ? C224 O224 H224 104.4(12) . . ? O224 C224 C223 119.42(11) . . ? O224 C224 C225 119.03(11) . . ? C223 C224 C225 121.55(11) . . ? C226 C225 C224 119.18(11) . . ? C226 C225 C32 119.66(11) . . ? C224 C225 C32 121.15(11) . . ? C225 C226 C227 121.56(12) . . ? C225 C226 H226 119.2 . . ? C227 C226 H226 119.2 . . ? C226 C227 C228 121.27(12) . . ? C226 C227 C232 118.91(11) . . ? C228 C227 C232 119.75(12) . . ? C229 C228 C227 120.91(12) . . ? C229 C228 H228 119.5 . . ? C227 C228 H228 119.5 . . ? C228 C229 C230 119.47(12) . . ? C228 C229 H229 120.3 . . ? C230 C229 H229 120.3 . . ? C231 C230 C229 121.29(12) . . ? C231 C230 H230 119.4 . . ? C229 C230 H230 119.4 . . ? C230 C231 C232 120.94(12) . . ? C230 C231 H231 119.5 . . ? C232 C231 H231 119.5 . . ? C223 C232 C231 122.40(11) . . ? C223 C232 C227 120.02(11) . . ? C231 C232 C227 117.53(11) . . ? H2A O2 H2B 101(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 -0.84(19) . . . . ? C16 N11 C12 C17 179.04(13) . . . . ? N11 C12 C13 C14 -0.8(2) . . . . ? C17 C12 C13 C14 179.34(13) . . . . ? C12 C13 C14 C15 1.4(2) . . . . ? C12 C13 C14 C18 -178.38(13) . . . . ? C13 C14 C15 C16 -0.5(2) . . . . ? C18 C14 C15 C16 179.31(13) . . . . ? C12 N11 C16 C15 1.8(2) . . . . ? C14 C15 C16 N11 -1.1(2) . . . . ? C24 N19 C20 C21 -0.25(19) . . . . ? C24 N19 C20 C25 178.99(13) . . . . ? N19 C20 C21 C22 -0.5(2) . . . . ? C25 C20 C21 C22 -179.70(13) . . . . ? C20 C21 C22 C23 1.0(2) . . . . ? C20 C21 C22 C26 -177.31(13) . . . . ? C21 C22 C23 C24 -0.7(2) . . . . ? C26 C22 C23 C24 177.60(13) . . . . ? C20 N19 C24 C23 0.5(2) . . . . ? C22 C23 C24 N19 0.0(2) . . . . ? O211 C211 C212 C213 178.32(11) . . . . ? C220 C211 C212 C213 -1.88(19) . . . . ? O211 C211 C212 C221 -1.07(18) . . . . ? C220 C211 C212 C221 178.73(11) . . . . ? O221 C221 C212 C213 -176.28(12) . . . . ? O222 C221 C212 C213 4.03(18) . . . . ? O221 C221 C212 C211 3.10(18) . . . . ? O222 C221 C212 C211 -176.59(12) . . . . ? C211 C212 C213 C214 -1.36(19) . . . . ? C221 C212 C213 C214 178.03(12) . . . . ? C212 C213 C214 C215 -177.07(13) . . . . ? C212 C213 C214 C219 1.61(19) . . . . ? C213 C214 C215 C216 176.84(14) . . . . ? C219 C214 C215 C216 -1.8(2) . . . . ? C214 C215 C216 C217 0.4(2) . . . . ? C215 C216 C217 C218 0.7(2) . . . . ? C216 C217 C218 C219 -0.5(2) . . . . ? C213 C214 C219 C220 1.28(18) . . . . ? C215 C214 C219 C220 179.99(12) . . . . ? C213 C214 C219 C218 -176.69(12) . . . . ? C215 C214 C219 C218 2.02(19) . . . . ? C217 C218 C219 C220 -178.81(13) . . . . ? C217 C218 C219 C214 -0.90(19) . . . . ? O211 C211 C220 C219 -175.51(11) . . . . ? C212 C211 C220 C219 4.69(18) . . . . ? O211 C211 C220 C222 2.44(18) . . . . ? C212 C211 C220 C222 -177.36(11) . . . . ? C214 C219 C220 C211 -4.37(18) . . . . ? C218 C219 C220 C211 173.49(12) . . . . ? C214 C219 C220 C222 177.68(11) . . . . ? C218 C219 C220 C222 -4.46(18) . . . . ? C211 C220 C222 C223 114.49(13) . . . . ? C219 C220 C222 C223 -67.60(15) . . . . ? C220 C222 C223 C224 115.80(13) . . . . ? C220 C222 C223 C232 -65.82(15) . . . . ? C232 C223 C224 O224 -177.16(11) . . . . ? C222 C223 C224 O224 1.26(18) . . . . ? C232 C223 C224 C225 3.86(18) . . . . ? C222 C223 C224 C225 -177.72(11) . . . . ? O224 C224 C225 C226 -178.60(11) . . . . ? C223 C224 C225 C226 0.39(19) . . . . ? O224 C224 C225 C32 0.86(18) . . . . ? C223 C224 C225 C32 179.85(11) . . . . ? O234 C32 C225 C226 2.39(18) . . . . ? O233 C32 C225 C226 -178.33(12) . . . . ? O234 C32 C225 C224 -177.07(11) . . . . ? O233 C32 C225 C224 2.21(18) . . . . ? C224 C225 C226 C227 -2.81(18) . . . . ? C32 C225 C226 C227 177.72(11) . . . . ? C225 C226 C227 C228 -176.10(12) . . . . ? C225 C226 C227 C232 0.89(18) . . . . ? C226 C227 C228 C229 173.71(12) . . . . ? C232 C227 C228 C229 -3.26(19) . . . . ? C227 C228 C229 C230 0.7(2) . . . . ? C228 C229 C230 C231 2.1(2) . . . . ? C229 C230 C231 C232 -2.27(19) . . . . ? C224 C223 C232 C231 171.59(11) . . . . ? C222 C223 C232 C231 -6.81(18) . . . . ? C224 C223 C232 C227 -5.74(18) . . . . ? C222 C223 C232 C227 175.85(11) . . . . ? C230 C231 C232 C223 -177.73(12) . . . . ? C230 C231 C232 C227 -0.33(18) . . . . ? C226 C227 C232 C223 3.46(18) . . . . ? C228 C227 C232 C223 -179.50(11) . . . . ? C226 C227 C232 C231 -174.00(11) . . . . ? C228 C227 C232 C231 3.04(18) . . . . ? 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 0.957(19) 1.72(2) 2.6743(15) 173.4(17) . O211 H211 O221 0.92(2) 1.65(2) 2.5224(14) 157(2) . O224 H224 O233 0.93(2) 1.65(2) 2.5267(13) 156.1(19) . N19 H19 O234 1.05(2) 1.56(2) 2.6050(15) 179.0(19) . O1 H1A O222 0.90(2) 1.89(2) 2.7826(17) 169(2) 4_665 O1 H1B O233 0.89(2) 1.94(2) 2.7890(16) 159(2) . _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.303 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.044 data_3 _database_code_depnum_ccdc_archive 'CCDC 915731' #TrackingRef 'web_deposit_cif_file_0_TanyaleRoex_1358257029.submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3-picolinium pamoate hydrate THF solvate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N 1+ , C23 H15 O6 1- , 1/2(H2 O), C4 H8 O' _chemical_formula_sum 'C33 H32 N O7.50' _chemical_formula_weight 562.60 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 22.064(3) _cell_length_b 19.904(2) _cell_length_c 14.5130(17) _cell_angle_alpha 90.00 _cell_angle_beta 115.221(2) _cell_angle_gamma 90.00 _cell_volume 5765.9(12) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3061 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 27.41 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2376 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9808 _exptl_absorpt_correction_T_max 0.9871 _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 17239 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.06 _reflns_number_total 6302 _reflns_number_gt 4292 _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)' _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. The asymmetric unit contains two half THF molecules, both located on a special position. One of these half THF molecules is disordered over two positions, which were each modelled with a site occupancy of 0.25, with the two partial molecules sharing two common carbon sites. On allowing the site occupancies to refine these were found to be the best values for the model. Appropriate ADP restraints (SIMU and DELU) were used during the refinement for the disordered THF moieties. The water molecule was refined using DFIX and DANG restraints and bond lengths C3-C4 and O1-C4, in one of the partial THF molecules, were also refined using DFIX restraints. ; _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^)+(0.0627P)^2^+4.8782P] 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 6302 _refine_ls_number_parameters 456 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.0862 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1295 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.055 _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 O4 O 0.0000 0.15902(10) 0.2500 0.0244(4) Uani 1 2 d SD . . H11 H 0.5772(13) 0.4897(12) 0.1256(19) 0.040(7) Uiso 1 1 d . . . H224 H 0.1220(14) 0.2699(14) 0.062(2) 0.050(8) Uiso 1 1 d . . . H234 H 0.0698(16) 0.2008(15) 0.268(2) 0.065(9) Uiso 1 1 d . . . H211 H 0.4563(16) 0.3923(15) 0.125(2) 0.060(9) Uiso 1 1 d . . . N11 N 0.61751(9) 0.50683(9) 0.12900(13) 0.0255(4) Uani 1 1 d . . . C12 C 0.66858(11) 0.46543(11) 0.14425(16) 0.0299(5) Uani 1 1 d . . . H12 H 0.6632 0.4185 0.1505 0.036 Uiso 1 1 calc R . . C13 C 0.72975(11) 0.48991(11) 0.15122(16) 0.0297(5) Uani 1 1 d . . . C14 C 0.73396(11) 0.55909(12) 0.14148(16) 0.0314(5) Uani 1 1 d . . . H14 H 0.7748 0.5783 0.1471 0.038 Uiso 1 1 calc R . . C15 C 0.67992(11) 0.60025(11) 0.12384(16) 0.0317(5) Uani 1 1 d . . . H15 H 0.6833 0.6473 0.1158 0.038 Uiso 1 1 calc R . . C16 C 0.62130(11) 0.57312(11) 0.11798(16) 0.0294(5) Uani 1 1 d . . . H16 H 0.5838 0.6011 0.1062 0.035 Uiso 1 1 calc R . . C17 C 0.78693(12) 0.44381(13) 0.1674(2) 0.0411(6) Uani 1 1 d . . . H17A H 0.7897 0.4366 0.1025 0.062 Uiso 1 1 calc R . . H17B H 0.7798 0.4007 0.1938 0.062 Uiso 1 1 calc R . . H17C H 0.8288 0.4640 0.2165 0.062 Uiso 1 1 calc R . . C20 C 0.12295(10) 0.23772(10) 0.21175(15) 0.0244(4) Uani 1 1 d . . . C28 C 0.46503(10) 0.50527(11) 0.12099(15) 0.0255(4) Uani 1 1 d . . . O211 O 0.41961(8) 0.36930(7) 0.11993(11) 0.0273(3) Uani 1 1 d . . . C211 C 0.37706(10) 0.41968(10) 0.11629(14) 0.0225(4) Uani 1 1 d . . . C212 C 0.39800(10) 0.48795(10) 0.11886(15) 0.0233(4) Uani 1 1 d . . . C213 C 0.35505(11) 0.53866(11) 0.11542(15) 0.0260(4) Uani 1 1 d . . . H213 H 0.3695 0.5840 0.1197 0.031 Uiso 1 1 calc R . . C214 C 0.28996(10) 0.52508(10) 0.10571(15) 0.0257(4) Uani 1 1 d . . . C215 C 0.24532(11) 0.57813(11) 0.09989(16) 0.0305(5) Uani 1 1 d . . . H215 H 0.2607 0.6233 0.1077 0.037 Uiso 1 1 calc R . . C216 C 0.18074(12) 0.56541(12) 0.08333(18) 0.0351(5) Uani 1 1 d . . . H216 H 0.1516 0.6013 0.0803 0.042 Uiso 1 1 calc R . . C217 C 0.15764(11) 0.49870(12) 0.07073(17) 0.0329(5) Uani 1 1 d . . . H217 H 0.1123 0.4899 0.0570 0.040 Uiso 1 1 calc R . . C218 C 0.19963(10) 0.44599(11) 0.07799(16) 0.0273(5) Uani 1 1 d . . . H218 H 0.1828 0.4014 0.0697 0.033 Uiso 1 1 calc R . . C219 C 0.26792(10) 0.45682(10) 0.09776(14) 0.0229(4) Uani 1 1 d . . . C220 C 0.31316(10) 0.40343(10) 0.10570(14) 0.0224(4) Uani 1 1 d . . . O221 O 0.50392(7) 0.45645(7) 0.12586(11) 0.0294(3) Uani 1 1 d . . . O222 O 0.47978(8) 0.56549(7) 0.11559(12) 0.0317(4) Uani 1 1 d . . . C222 C 0.29128(10) 0.33022(10) 0.09482(15) 0.0238(4) Uani 1 1 d . . . H22A H 0.3274 0.3024 0.0914 0.029 Uiso 1 1 calc R . . H22B H 0.2513 0.3250 0.0292 0.029 Uiso 1 1 calc R . . C223 C 0.27466(10) 0.30263(10) 0.17958(15) 0.0227(4) Uani 1 1 d . . . O224 O 0.16249(7) 0.28485(7) 0.05966(10) 0.0272(3) Uani 1 1 d . . . C224 C 0.20990(10) 0.28289(10) 0.15817(15) 0.0223(4) Uani 1 1 d . . . C225 C 0.19216(9) 0.26066(10) 0.23713(15) 0.0222(4) Uani 1 1 d . . . C226 C 0.24022(10) 0.25749(10) 0.33541(15) 0.0229(4) Uani 1 1 d . . . H226 H 0.2278 0.2444 0.3880 0.027 Uiso 1 1 calc R . . C227 C 0.30748(10) 0.27325(10) 0.36024(15) 0.0228(4) Uani 1 1 d . . . C228 C 0.35733(10) 0.26706(11) 0.46203(16) 0.0289(5) Uani 1 1 d . . . H228 H 0.3449 0.2533 0.5143 0.035 Uiso 1 1 calc R . . C229 C 0.42276(10) 0.28068(11) 0.48524(17) 0.0314(5) Uani 1 1 d . . . H229 H 0.4558 0.2767 0.5534 0.038 Uiso 1 1 calc R . . C230 C 0.44099(10) 0.30068(11) 0.40766(17) 0.0310(5) Uani 1 1 d . . . H230 H 0.4868 0.3095 0.4241 0.037 Uiso 1 1 calc R . . C231 C 0.39439(10) 0.30773(10) 0.30883(16) 0.0262(5) Uani 1 1 d . . . H231 H 0.4083 0.3211 0.2580 0.031 Uiso 1 1 calc R . . C232 C 0.32525(10) 0.29518(10) 0.28143(15) 0.0220(4) Uani 1 1 d . . . O233 O 0.07920(7) 0.23464(8) 0.12398(11) 0.0304(4) Uani 1 1 d . . . O234 O 0.11287(7) 0.21879(8) 0.29138(11) 0.0300(4) Uani 1 1 d . . . O1 O 0.9191(3) 0.5944(3) 0.2578(6) 0.116(2) Uani 0.50 1 d PDU . . C2 C 0.9104(5) 0.6430(5) 0.1873(7) 0.105(3) Uani 0.50 1 d PU . . H2A H 0.8874 0.6821 0.2002 0.126 Uiso 0.50 1 calc PR . . H2B H 0.8818 0.6255 0.1184 0.126 Uiso 0.50 1 calc PR . . C4 C 0.9752(5) 0.6232(6) 0.3385(7) 0.167(5) Uani 0.50 1 d PDU . . H4A H 1.0018 0.5866 0.3838 0.200 Uiso 0.50 1 calc PR . . H4B H 0.9589 0.6521 0.3787 0.200 Uiso 0.50 1 calc PR . . C3 C 1.0219(3) 0.6651(4) 0.3079(5) 0.172(3) Uani 1 1 d DU . . C8 C 1.0131(5) 0.6134(5) 0.6271(10) 0.116(3) Uani 0.50 1 d PU . . O2 O 1.0084(5) 0.5488(5) 0.5951(10) 0.094(4) Uani 0.25 1 d P A 1 C6 C 1.0000 0.5579(10) 0.7500 0.153(9) Uani 0.50 2 d SP . 1 C9 C 0.9559(17) 0.6217(15) 0.681(2) 0.100(8) Uani 0.25 1 d PU . 2 C5 C 1.0025(10) 0.5147(11) 0.6747(17) 0.116(7) Uani 0.25 1 d P A 1 O3 O 1.0670(7) 0.6174(8) 0.7182(12) 0.133(5) Uani 0.25 1 d PU . 2 C7 C 1.0043(10) 0.6279(11) 0.7127(13) 0.179(7) Uani 0.50 1 d P . . C10 C 1.059(2) 0.602(3) 0.823(4) 0.146(13) Uani 0.25 1 d PU . 2 H4 H 0.0113(14) 0.1281(11) 0.3059(8) 0.065(9) Uiso 1 1 d 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 O4 0.0191(10) 0.0264(11) 0.0276(11) 0.000 0.0098(9) 0.000 N11 0.0239(9) 0.0326(10) 0.0208(9) -0.0006(7) 0.0102(7) -0.0043(8) C12 0.0355(12) 0.0311(11) 0.0249(11) 0.0022(9) 0.0145(10) -0.0003(9) C13 0.0313(12) 0.0380(12) 0.0211(11) 0.0003(9) 0.0123(9) -0.0009(10) C14 0.0291(12) 0.0412(13) 0.0258(11) -0.0047(10) 0.0135(9) -0.0106(10) C15 0.0369(13) 0.0303(11) 0.0300(12) -0.0038(9) 0.0162(10) -0.0060(10) C16 0.0351(12) 0.0310(12) 0.0248(11) -0.0014(9) 0.0152(9) -0.0025(9) C17 0.0336(13) 0.0501(15) 0.0412(14) 0.0034(12) 0.0175(11) 0.0064(11) C20 0.0216(10) 0.0266(11) 0.0244(11) -0.0001(8) 0.0093(9) -0.0017(8) C28 0.0258(11) 0.0314(11) 0.0194(10) -0.0017(9) 0.0095(8) -0.0030(9) O211 0.0238(8) 0.0267(8) 0.0353(9) 0.0006(6) 0.0162(7) 0.0007(6) C211 0.0240(10) 0.0275(10) 0.0178(10) 0.0017(8) 0.0106(8) 0.0015(8) C212 0.0241(10) 0.0276(11) 0.0180(10) -0.0005(8) 0.0089(8) -0.0018(8) C213 0.0309(11) 0.0263(10) 0.0204(10) -0.0009(8) 0.0107(9) -0.0019(9) C214 0.0283(11) 0.0299(11) 0.0181(10) 0.0017(8) 0.0092(8) 0.0022(9) C215 0.0350(12) 0.0294(11) 0.0282(11) 0.0016(9) 0.0146(10) 0.0054(9) C216 0.0354(13) 0.0373(13) 0.0345(13) 0.0044(10) 0.0166(10) 0.0114(10) C217 0.0240(11) 0.0436(13) 0.0316(12) 0.0067(10) 0.0122(9) 0.0056(10) C218 0.0245(11) 0.0333(11) 0.0244(11) 0.0035(9) 0.0106(9) 0.0026(9) C219 0.0235(10) 0.0296(11) 0.0160(10) 0.0019(8) 0.0087(8) 0.0012(8) C220 0.0225(10) 0.0274(10) 0.0177(10) 0.0002(8) 0.0088(8) -0.0007(8) O221 0.0241(8) 0.0313(8) 0.0342(9) -0.0009(7) 0.0138(7) -0.0016(6) O222 0.0368(9) 0.0280(8) 0.0359(9) -0.0030(7) 0.0206(7) -0.0082(7) C222 0.0208(10) 0.0275(11) 0.0230(10) -0.0011(8) 0.0093(8) -0.0015(8) C223 0.0214(10) 0.0230(10) 0.0243(11) -0.0018(8) 0.0103(8) -0.0005(8) O224 0.0187(7) 0.0373(9) 0.0212(7) 0.0010(6) 0.0044(6) -0.0044(6) C224 0.0196(10) 0.0241(10) 0.0210(10) -0.0016(8) 0.0066(8) -0.0002(8) C225 0.0181(10) 0.0235(10) 0.0231(10) -0.0015(8) 0.0069(8) -0.0015(8) C226 0.0201(10) 0.0260(10) 0.0233(10) 0.0001(8) 0.0102(8) -0.0023(8) C227 0.0192(10) 0.0233(10) 0.0245(10) -0.0009(8) 0.0080(8) -0.0016(8) C228 0.0245(11) 0.0361(12) 0.0252(11) 0.0014(9) 0.0098(9) -0.0026(9) C229 0.0197(10) 0.0423(13) 0.0251(11) 0.0026(10) 0.0026(9) -0.0023(9) C230 0.0171(10) 0.0369(12) 0.0359(13) 0.0054(10) 0.0082(9) -0.0022(9) C231 0.0206(10) 0.0290(11) 0.0297(11) 0.0047(9) 0.0114(9) -0.0005(8) C232 0.0185(10) 0.0217(10) 0.0235(10) 0.0010(8) 0.0067(8) 0.0010(8) O233 0.0181(7) 0.0434(9) 0.0243(8) 0.0007(7) 0.0039(6) -0.0046(6) O234 0.0183(7) 0.0446(9) 0.0261(8) -0.0005(7) 0.0087(6) -0.0086(7) O1 0.121(5) 0.102(4) 0.145(6) 0.020(4) 0.077(4) -0.006(4) C2 0.120(7) 0.097(6) 0.077(5) -0.005(4) 0.021(5) -0.035(6) C4 0.230(13) 0.114(9) 0.098(7) -0.003(6) 0.014(7) 0.015(8) C3 0.097(5) 0.203(7) 0.192(7) -0.077(5) 0.039(4) 0.013(4) C8 0.097(7) 0.077(6) 0.134(8) -0.017(6) 0.009(6) -0.011(5) O2 0.062(6) 0.050(5) 0.183(12) 0.020(7) 0.065(7) -0.005(5) C6 0.16(2) 0.079(11) 0.28(3) 0.000 0.15(2) 0.000 C9 0.072(10) 0.093(18) 0.071(11) -0.020(12) -0.032(8) 0.011(15) C5 0.114(15) 0.093(14) 0.109(16) 0.061(12) 0.016(12) -0.008(12) O3 0.091(8) 0.153(12) 0.134(10) 0.048(10) 0.027(7) 0.008(9) C7 0.142(13) 0.28(2) 0.133(15) 0.019(14) 0.078(12) -0.049(16) C10 0.12(2) 0.17(3) 0.139(13) 0.05(2) 0.043(16) 0.057(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O4 H4 0.963(15) . ? N11 C12 1.336(3) . ? N11 C16 1.336(3) . ? N11 H11 0.93(3) . ? C12 C13 1.398(3) . ? C12 H12 0.9500 . ? C13 C14 1.391(3) . ? C13 C17 1.495(3) . ? C14 C15 1.378(3) . ? C14 H14 0.9500 . ? C15 C16 1.370(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C20 O233 1.229(2) . ? C20 O234 1.321(2) . ? C20 C225 1.482(3) . ? C28 O222 1.253(2) . ? C28 O221 1.278(3) . ? C28 C212 1.506(3) . ? O211 C211 1.359(2) . ? O211 H211 0.91(3) . ? C211 C220 1.390(3) . ? C211 C212 1.431(3) . ? C212 C213 1.371(3) . ? C213 C214 1.408(3) . ? C213 H213 0.9500 . ? C214 C215 1.422(3) . ? C214 C219 1.431(3) . ? C215 C216 1.364(3) . ? C215 H215 0.9500 . ? C216 C217 1.406(3) . ? C216 H216 0.9500 . ? C217 C218 1.374(3) . ? C217 H217 0.9500 . ? C218 C219 1.425(3) . ? C218 H218 0.9500 . ? C219 C220 1.429(3) . ? C220 C222 1.522(3) . ? C222 C223 1.527(3) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C223 C224 1.384(3) . ? C223 C232 1.431(3) . ? O224 C224 1.366(2) . ? O224 H224 0.95(3) . ? C224 C225 1.430(3) . ? C225 C226 1.369(3) . ? C226 C227 1.405(3) . ? C226 H226 0.9500 . ? C227 C228 1.422(3) . ? C227 C232 1.426(3) . ? C228 C229 1.362(3) . ? C228 H228 0.9500 . ? C229 C230 1.405(3) . ? C229 H229 0.9500 . ? C230 C231 1.370(3) . ? C230 H230 0.9500 . ? C231 C232 1.425(3) . ? C231 H231 0.9500 . ? O234 H234 0.93(3) . ? O1 C2 1.361(10) . ? O1 C4 1.414(5) . ? C2 C3 1.532(11) 2_755 ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C4 C3 1.529(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C3 C2 1.532(11) 2_755 ? C3 C3 1.542(13) 2_755 ? C8 O3 1.351(17) . ? C8 O2 1.357(13) . ? C8 C7 1.368(16) . ? C8 C9 1.76(5) . ? C8 C10 2.02(5) 2_756 ? O2 C5 1.39(2) . ? C6 C5 1.41(3) . ? C6 C5 1.41(3) 2_756 ? C6 C7 1.51(2) 2_756 ? C6 C7 1.51(2) . ? C9 C10 0.50(6) 2_756 ? C9 C7 0.97(3) . ? C9 C7 1.41(3) 2_756 ? C9 O3 1.74(5) 2_756 ? O3 C7 1.37(2) . ? O3 C10 1.64(5) . ? O3 C9 1.74(5) 2_756 ? C7 C7 1.18(3) 2_756 ? C7 C10 1.37(4) 2_756 ? C7 C9 1.41(3) 2_756 ? C7 C10 1.63(5) . ? C10 C9 0.50(6) 2_756 ? C10 C7 1.37(4) 2_756 ? C10 C8 2.02(5) 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 122.52(19) . . ? C12 N11 H11 120.0(15) . . ? C16 N11 H11 117.5(15) . . ? N11 C12 C13 121.2(2) . . ? N11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 116.2(2) . . ? C14 C13 C17 122.3(2) . . ? C12 C13 C17 121.4(2) . . ? C15 C14 C13 121.2(2) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C16 C15 C14 119.8(2) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? N11 C16 C15 119.2(2) . . ? N11 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O233 C20 O234 122.80(18) . . ? O233 C20 C225 122.96(18) . . ? O234 C20 C225 114.21(17) . . ? O222 C28 O221 122.99(19) . . ? O222 C28 C212 119.78(18) . . ? O221 C28 C212 117.21(18) . . ? C211 O211 H211 102.1(19) . . ? O211 C211 C220 118.94(18) . . ? O211 C211 C212 119.32(17) . . ? C220 C211 C212 121.68(18) . . ? C213 C212 C211 119.20(18) . . ? C213 C212 C28 119.33(18) . . ? C211 C212 C28 121.43(18) . . ? C212 C213 C214 121.47(19) . . ? C212 C213 H213 119.3 . . ? C214 C213 H213 119.3 . . ? C213 C214 C215 120.97(19) . . ? C213 C214 C219 119.17(18) . . ? C215 C214 C219 119.82(19) . . ? C216 C215 C214 121.2(2) . . ? C216 C215 H215 119.4 . . ? C214 C215 H215 119.4 . . ? C215 C216 C217 119.5(2) . . ? C215 C216 H216 120.3 . . ? C217 C216 H216 120.3 . . ? C218 C217 C216 121.1(2) . . ? C218 C217 H217 119.5 . . ? C216 C217 H217 119.5 . . ? C217 C218 C219 121.4(2) . . ? C217 C218 H218 119.3 . . ? C219 C218 H218 119.3 . . ? C218 C219 C220 123.11(18) . . ? C218 C219 C214 116.98(18) . . ? C220 C219 C214 119.86(18) . . ? C211 C220 C219 118.48(18) . . ? C211 C220 C222 119.76(17) . . ? C219 C220 C222 121.59(17) . . ? C220 C222 C223 115.79(16) . . ? C220 C222 H22A 108.3 . . ? C223 C222 H22A 108.3 . . ? C220 C222 H22B 108.3 . . ? C223 C222 H22B 108.3 . . ? H22A C222 H22B 107.4 . . ? C224 C223 C232 118.62(18) . . ? C224 C223 C222 120.04(18) . . ? C232 C223 C222 121.33(17) . . ? C224 O224 H224 105.6(16) . . ? O224 C224 C223 118.94(18) . . ? O224 C224 C225 119.92(17) . . ? C223 C224 C225 121.14(18) . . ? C226 C225 C224 119.62(18) . . ? C226 C225 C20 120.22(18) . . ? C224 C225 C20 120.07(17) . . ? C225 C226 C227 121.43(18) . . ? C225 C226 H226 119.3 . . ? C227 C226 H226 119.3 . . ? C226 C227 C228 120.79(18) . . ? C226 C227 C232 118.93(18) . . ? C228 C227 C232 120.28(18) . . ? C229 C228 C227 120.6(2) . . ? C229 C228 H228 119.7 . . ? C227 C228 H228 119.7 . . ? C228 C229 C230 119.5(2) . . ? C228 C229 H229 120.2 . . ? C230 C229 H229 120.2 . . ? C231 C230 C229 121.64(19) . . ? C231 C230 H230 119.2 . . ? C229 C230 H230 119.2 . . ? C230 C231 C232 120.72(19) . . ? C230 C231 H231 119.6 . . ? C232 C231 H231 119.6 . . ? C231 C232 C227 117.21(18) . . ? C231 C232 C223 122.78(18) . . ? C227 C232 C223 120.01(17) . . ? C20 O234 H234 108.5(18) . . ? C2 O1 C4 97.3(7) . . ? O1 C2 C3 110.4(8) . 2_755 ? O1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 2_755 . ? O1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 2_755 . ? H2A C2 H2B 108.1 . . ? O1 C4 C3 116.2(7) . . ? O1 C4 H4A 108.2 . . ? C3 C4 H4A 108.2 . . ? O1 C4 H4B 108.2 . . ? C3 C4 H4B 108.2 . . ? H4A C4 H4B 107.4 . . ? C4 C3 C2 126.5(9) . 2_755 ? C4 C3 C3 97.5(6) . 2_755 ? C2 C3 C3 101.2(8) 2_755 2_755 ? O3 C8 O2 107.3(12) . . ? O3 C8 C7 60.4(12) . . ? O2 C8 C7 119.4(14) . . ? O3 C8 C9 93.2(14) . . ? O2 C8 C9 106.1(13) . . ? C7 C8 C9 33.4(10) . . ? O3 C8 C10 99.0(17) . 2_756 ? O2 C8 C10 93.3(17) . 2_756 ? C7 C8 C10 42.4(15) . 2_756 ? C9 C8 C10 13(2) . 2_756 ? C8 O2 C5 101.4(15) . . ? C5 C6 C5 104.8(19) . 2_756 ? C5 C6 C7 150.3(13) . 2_756 ? C5 C6 C7 104.8(10) 2_756 2_756 ? C5 C6 C7 104.8(10) . . ? C5 C6 C7 150.3(13) 2_756 . ? C7 C6 C7 45.8(14) 2_756 . ? C10 C9 C7 134(10) 2_756 . ? C10 C9 C7 107(10) 2_756 2_756 ? C7 C9 C7 55.4(19) . 2_756 ? C10 C9 O3 71(10) 2_756 2_756 ? C7 C9 O3 106(3) . 2_756 ? C7 C9 O3 50.2(16) 2_756 2_756 ? C10 C9 C8 115(10) 2_756 . ? C7 C9 C8 51(3) . . ? C7 C9 C8 105(2) 2_756 . ? O3 C9 C8 153.3(16) 2_756 . ? O2 C5 C6 113.2(14) . . ? C8 O3 C7 60.4(10) . . ? C8 O3 C10 120(2) . . ? C7 O3 C10 64.8(15) . . ? C8 O3 C9 112.0(15) . 2_756 ? C7 O3 C9 52.6(14) . 2_756 ? C10 O3 C9 17(2) . 2_756 ? C9 C7 C7 82(3) . 2_756 ? C9 C7 C10 15(4) . 2_756 ? C7 C7 C10 79(3) 2_756 2_756 ? C9 C7 O3 153(3) . . ? C7 C7 O3 120(3) 2_756 . ? C10 C7 O3 144(3) 2_756 . ? C9 C7 C8 96(3) . . ? C7 C7 C8 167.8(10) 2_756 . ? C10 C7 C8 95(3) 2_756 . ? O3 C7 C8 59.2(11) . . ? C9 C7 C9 123.1(19) . 2_756 ? C7 C7 C9 43(2) 2_756 2_756 ? C10 C7 C9 116(3) 2_756 2_756 ? O3 C7 C9 77(3) . 2_756 ? C8 C7 C9 135(3) . 2_756 ? C9 C7 C6 80(2) . . ? C7 C7 C6 67.1(7) 2_756 . ? C10 C7 C6 65(3) 2_756 . ? O3 C7 C6 93.1(15) . . ? C8 C7 C6 100.7(15) . . ? C9 C7 C6 68.6(15) 2_756 . ? C9 C7 C10 129(4) . . ? C7 C7 C10 56(2) 2_756 . ? C10 C7 C10 118(4) 2_756 . ? O3 C7 C10 66(2) . . ? C8 C7 C10 120(2) . . ? C9 C7 C10 17(3) 2_756 . ? C6 C7 C10 59(2) . . ? C9 C10 C7 31(7) 2_756 2_756 ? C9 C10 C7 56(8) 2_756 . ? C7 C10 C7 45.1(17) 2_756 . ? C9 C10 O3 92(10) 2_756 . ? C7 C10 O3 94(3) 2_756 . ? C7 C10 O3 49.4(16) . . ? C9 C10 C8 52(10) 2_756 2_756 ? C7 C10 C8 42.5(15) 2_756 2_756 ? C7 C10 C8 87.1(18) . 2_756 ? O3 C10 C8 136(2) . 2_756 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 1.1(3) . . . . ? N11 C12 C13 C14 0.1(3) . . . . ? N11 C12 C13 C17 -179.5(2) . . . . ? C12 C13 C14 C15 -1.3(3) . . . . ? C17 C13 C14 C15 178.2(2) . . . . ? C13 C14 C15 C16 1.5(3) . . . . ? C12 N11 C16 C15 -0.9(3) . . . . ? C14 C15 C16 N11 -0.4(3) . . . . ? O211 C211 C212 C213 -179.84(18) . . . . ? C220 C211 C212 C213 3.0(3) . . . . ? O211 C211 C212 C28 2.7(3) . . . . ? C220 C211 C212 C28 -174.51(18) . . . . ? O222 C28 C212 C213 -2.8(3) . . . . ? O221 C28 C212 C213 178.89(18) . . . . ? O222 C28 C212 C211 174.71(19) . . . . ? O221 C28 C212 C211 -3.6(3) . . . . ? C211 C212 C213 C214 -2.3(3) . . . . ? C28 C212 C213 C214 175.23(18) . . . . ? C212 C213 C214 C215 -178.56(19) . . . . ? C212 C213 C214 C219 -0.9(3) . . . . ? C213 C214 C215 C216 175.3(2) . . . . ? C219 C214 C215 C216 -2.3(3) . . . . ? C214 C215 C216 C217 -0.7(3) . . . . ? C215 C216 C217 C218 2.1(3) . . . . ? C216 C217 C218 C219 -0.5(3) . . . . ? C217 C218 C219 C220 -179.89(19) . . . . ? C217 C218 C219 C214 -2.4(3) . . . . ? C213 C214 C219 C218 -173.97(18) . . . . ? C215 C214 C219 C218 3.7(3) . . . . ? C213 C214 C219 C220 3.6(3) . . . . ? C215 C214 C219 C220 -178.71(18) . . . . ? O211 C211 C220 C219 -177.48(17) . . . . ? C212 C211 C220 C219 -0.3(3) . . . . ? O211 C211 C220 C222 -2.1(3) . . . . ? C212 C211 C220 C222 175.11(18) . . . . ? C218 C219 C220 C211 174.46(18) . . . . ? C214 C219 C220 C211 -3.0(3) . . . . ? C218 C219 C220 C222 -0.9(3) . . . . ? C214 C219 C220 C222 -178.32(17) . . . . ? C211 C220 C222 C223 117.3(2) . . . . ? C219 C220 C222 C223 -67.4(2) . . . . ? C220 C222 C223 C224 115.0(2) . . . . ? C220 C222 C223 C232 -66.4(2) . . . . ? C232 C223 C224 O224 -174.87(17) . . . . ? C222 C223 C224 O224 3.8(3) . . . . ? C232 C223 C224 C225 5.1(3) . . . . ? C222 C223 C224 C225 -176.25(18) . . . . ? O224 C224 C225 C226 178.65(18) . . . . ? C223 C224 C225 C226 -1.3(3) . . . . ? O224 C224 C225 C20 1.9(3) . . . . ? C223 C224 C225 C20 -178.05(18) . . . . ? O233 C20 C225 C226 -174.3(2) . . . . ? O234 C20 C225 C226 3.6(3) . . . . ? O233 C20 C225 C224 2.4(3) . . . . ? O234 C20 C225 C224 -179.69(18) . . . . ? C224 C225 C226 C227 -2.4(3) . . . . ? C20 C225 C226 C227 174.31(18) . . . . ? C225 C226 C227 C228 -177.38(19) . . . . ? C225 C226 C227 C232 2.2(3) . . . . ? C226 C227 C228 C229 178.2(2) . . . . ? C232 C227 C228 C229 -1.3(3) . . . . ? C227 C228 C229 C230 -0.3(3) . . . . ? C228 C229 C230 C231 0.8(3) . . . . ? C229 C230 C231 C232 0.3(3) . . . . ? C230 C231 C232 C227 -1.8(3) . . . . ? C230 C231 C232 C223 179.2(2) . . . . ? C226 C227 C232 C231 -177.22(18) . . . . ? C228 C227 C232 C231 2.3(3) . . . . ? C226 C227 C232 C223 1.7(3) . . . . ? C228 C227 C232 C223 -178.72(19) . . . . ? C224 C223 C232 C231 173.60(19) . . . . ? C222 C223 C232 C231 -5.0(3) . . . . ? C224 C223 C232 C227 -5.3(3) . . . . ? C222 C223 C232 C227 176.08(18) . . . . ? C4 O1 C2 C3 41.8(11) . . . 2_755 ? C2 O1 C4 C3 -30.7(12) . . . . ? O1 C4 C3 C2 -102.2(11) . . . 2_755 ? O1 C4 C3 C3 7.8(11) . . . 2_755 ? O3 C8 O2 C5 58.6(16) . . . . ? C7 C8 O2 C5 -6.6(18) . . . . ? C9 C8 O2 C5 -40.1(15) . . . . ? C10 C8 O2 C5 -41.9(17) 2_756 . . . ? O3 C8 C9 C10 -117(9) . . . 2_756 ? O2 C8 C9 C10 -8(10) . . . 2_756 ? C7 C8 C9 C10 -127(10) . . . 2_756 ? O3 C8 C9 C7 10(3) . . . . ? O2 C8 C9 C7 119(3) . . . . ? C10 C8 C9 C7 127(10) 2_756 . . . ? O3 C8 C9 C7 0(2) . . . 2_756 ? O2 C8 C9 C7 109(2) . . . 2_756 ? C7 C8 C9 C7 -10.2(9) . . . 2_756 ? C10 C8 C9 C7 117(10) 2_756 . . 2_756 ? O3 C8 C9 O3 -21(5) . . . 2_756 ? O2 C8 C9 O3 88(5) . . . 2_756 ? C7 C8 C9 O3 -31(3) . . . 2_756 ? C10 C8 C9 O3 96(11) 2_756 . . 2_756 ? C8 O2 C5 C6 3.2(17) . . . . ? C5 C6 C5 O2 -177(2) 2_756 . . . ? C7 C6 C5 O2 7(3) 2_756 . . . ? C7 C6 C5 O2 0.5(17) . . . . ? O2 C8 O3 C7 -114.5(16) . . . . ? C9 C8 O3 C7 -6.5(16) . . . . ? C10 C8 O3 C7 -18(2) 2_756 . . . ? O2 C8 O3 C10 -88(3) . . . . ? C7 C8 O3 C10 27(3) . . . . ? C9 C8 O3 C10 20(3) . . . . ? C10 C8 O3 C10 8.5(15) 2_756 . . . ? O2 C8 O3 C9 -104.1(16) . . . 2_756 ? C7 C8 O3 C9 10.4(17) . . . 2_756 ? C9 C8 O3 C9 3.9(11) . . . 2_756 ? C10 C8 O3 C9 -8(3) 2_756 . . 2_756 ? C10 C9 C7 C7 -80(17) 2_756 . . 2_756 ? O3 C9 C7 C7 -2.0(15) 2_756 . . 2_756 ? C8 C9 C7 C7 -168.0(11) . . . 2_756 ? C7 C9 C7 C10 80(17) 2_756 . . 2_756 ? O3 C9 C7 C10 78(17) 2_756 . . 2_756 ? C8 C9 C7 C10 -88(17) . . . 2_756 ? C10 C9 C7 O3 65(21) 2_756 . . . ? C7 C9 C7 O3 145(6) 2_756 . . . ? O3 C9 C7 O3 143(6) 2_756 . . . ? C8 C9 C7 O3 -23(6) . . . . ? C10 C9 C7 C8 88(17) 2_756 . . . ? C7 C9 C7 C8 168.0(11) 2_756 . . . ? O3 C9 C7 C8 166.0(16) 2_756 . . . ? C10 C9 C7 C9 -68(17) 2_756 . . 2_756 ? C7 C9 C7 C9 12(4) 2_756 . . 2_756 ? O3 C9 C7 C9 10(5) 2_756 . . 2_756 ? C8 C9 C7 C9 -156(4) . . . 2_756 ? C10 C9 C7 C6 -12(16) 2_756 . . . ? C7 C9 C7 C6 68.1(8) 2_756 . . . ? O3 C9 C7 C6 66.1(18) 2_756 . . . ? C8 C9 C7 C6 -99.9(16) . . . . ? C10 C9 C7 C10 -48(19) 2_756 . . . ? C7 C9 C7 C10 32(4) 2_756 . . . ? O3 C9 C7 C10 30(4) 2_756 . . . ? C8 C9 C7 C10 -136(4) . . . . ? C8 O3 C7 C9 27(7) . . . . ? C10 O3 C7 C9 -128(7) . . . . ? C9 O3 C7 C9 -141(8) 2_756 . . . ? C8 O3 C7 C7 165.9(12) . . . 2_756 ? C10 O3 C7 C7 11(2) . . . 2_756 ? C9 O3 C7 C7 -2.0(15) 2_756 . . 2_756 ? C8 O3 C7 C10 50(5) . . . 2_756 ? C10 O3 C7 C10 -104(7) . . . 2_756 ? C9 O3 C7 C10 -117(5) 2_756 . . 2_756 ? C10 O3 C7 C8 -155(3) . . . . ? C9 O3 C7 C8 -167.8(19) 2_756 . . . ? C8 O3 C7 C9 167.8(19) . . . 2_756 ? C10 O3 C7 C9 13(3) . . . 2_756 ? C8 O3 C7 C6 100.6(12) . . . . ? C10 O3 C7 C6 -54(2) . . . . ? C9 O3 C7 C6 -67.2(16) 2_756 . . . ? C8 O3 C7 C10 155(3) . . . . ? C9 O3 C7 C10 -13(3) 2_756 . . . ? O3 C8 C7 C9 -168(3) . . . . ? O2 C8 C7 C9 -74(3) . . . . ? C10 C8 C7 C9 -15(4) 2_756 . . . ? O3 C8 C7 C7 -91(14) . . . 2_756 ? O2 C8 C7 C7 3(14) . . . 2_756 ? C9 C8 C7 C7 77(13) . . . 2_756 ? C10 C8 C7 C7 62(13) 2_756 . . 2_756 ? O3 C8 C7 C10 -153(3) . . . 2_756 ? O2 C8 C7 C10 -59(3) . . . 2_756 ? C9 C8 C7 C10 15(4) . . . 2_756 ? O2 C8 C7 O3 94.1(14) . . . . ? C9 C8 C7 O3 168(3) . . . . ? C10 C8 C7 O3 153(3) 2_756 . . . ? O3 C8 C7 C9 -17(3) . . . 2_756 ? O2 C8 C7 C9 77(3) . . . 2_756 ? C9 C8 C7 C9 151(5) . . . 2_756 ? C10 C8 C7 C9 136(4) 2_756 . . 2_756 ? O3 C8 C7 C6 -87.2(14) . . . . ? O2 C8 C7 C6 6.9(18) . . . . ? C9 C8 C7 C6 81(2) . . . . ? C10 C8 C7 C6 66(3) 2_756 . . . ? O3 C8 C7 C10 -27(3) . . . . ? O2 C8 C7 C10 67(3) . . . . ? C9 C8 C7 C10 141(4) . . . . ? C10 C8 C7 C10 126(6) 2_756 . . . ? C5 C6 C7 C9 90(3) . . . . ? C5 C6 C7 C9 -94(4) 2_756 . . . ? C7 C6 C7 C9 -85(3) 2_756 . . . ? C5 C6 C7 C7 175.3(18) . . . 2_756 ? C5 C6 C7 C7 -9(4) 2_756 . . 2_756 ? C5 C6 C7 C10 87(3) . . . 2_756 ? C5 C6 C7 C10 -98(3) 2_756 . . 2_756 ? C7 C6 C7 C10 -89(3) 2_756 . . 2_756 ? C5 C6 C7 O3 -63.2(14) . . . . ? C5 C6 C7 O3 112(2) 2_756 . . . ? C7 C6 C7 O3 122(2) 2_756 . . . ? C5 C6 C7 C8 -4.0(15) . . . . ? C5 C6 C7 C8 171.5(18) 2_756 . . . ? C7 C6 C7 C8 -179(3) 2_756 . . . ? C5 C6 C7 C9 -138(2) . . . 2_756 ? C5 C6 C7 C9 37(4) 2_756 . . 2_756 ? C7 C6 C7 C9 47(2) 2_756 . . 2_756 ? C5 C6 C7 C10 -122(2) . . . . ? C5 C6 C7 C10 53(3) 2_756 . . . ? C7 C6 C7 C10 62(2) 2_756 . . . ? C9 C7 C10 C9 -77(10) . . . 2_756 ? C7 C7 C10 C9 -38(10) 2_756 . . 2_756 ? C10 C7 C10 C9 -90(14) 2_756 . . 2_756 ? O3 C7 C10 C9 130(12) . . . 2_756 ? C8 C7 C10 C9 155(10) . . . 2_756 ? C6 C7 C10 C9 -120(12) . . . 2_756 ? C9 C7 C10 C7 -39(5) . . . 2_756 ? C10 C7 C10 C7 -52(5) 2_756 . . 2_756 ? O3 C7 C10 C7 168(3) . . . 2_756 ? C8 C7 C10 C7 -166.7(16) . . . 2_756 ? C9 C7 C10 C7 38(10) 2_756 . . 2_756 ? C6 C7 C10 C7 -82(2) . . . 2_756 ? C9 C7 C10 O3 152(4) . . . . ? C7 C7 C10 O3 -168(3) 2_756 . . . ? C10 C7 C10 O3 140(3) 2_756 . . . ? C8 C7 C10 O3 25(2) . . . . ? C9 C7 C10 O3 -130(12) 2_756 . . . ? C6 C7 C10 O3 109.8(19) . . . . ? C9 C7 C10 C8 -32(4) . . . 2_756 ? C7 C7 C10 C8 7.4(10) 2_756 . . 2_756 ? C10 C7 C10 C8 -45(5) 2_756 . . 2_756 ? O3 C7 C10 C8 176(3) . . . 2_756 ? C8 C7 C10 C8 -159.3(16) . . . 2_756 ? C9 C7 C10 C8 45(10) 2_756 . . 2_756 ? C6 C7 C10 C8 -74.7(19) . . . 2_756 ? C8 O3 C10 C9 -65(10) . . . 2_756 ? C7 O3 C10 C9 -39(8) . . . 2_756 ? C8 O3 C10 C7 -34(4) . . . 2_756 ? C7 O3 C10 C7 -8(2) . . . 2_756 ? C9 O3 C10 C7 31(6) 2_756 . . 2_756 ? C8 O3 C10 C7 -26(3) . . . . ? C9 O3 C10 C7 39(8) 2_756 . . . ? C8 O3 C10 C8 -32(6) . . . 2_756 ? C7 O3 C10 C8 -7(4) . . . 2_756 ? C9 O3 C10 C8 33(5) 2_756 . . 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 0.93(3) 1.75(3) 2.682(2) 177(2) . O224 H224 O233 0.95(3) 1.71(3) 2.590(2) 152(2) . O234 H234 O4 0.93(3) 1.67(3) 2.5890(17) 167(3) . O211 H211 O221 0.91(3) 1.65(3) 2.518(2) 159(3) . O4 H4 O222 0.963(15) 1.643(17) 2.594(2) 169(2) 4_545 _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.571 _refine_diff_density_min -0.506 _refine_diff_density_rms 0.052 data_4 _database_code_depnum_ccdc_archive 'CCDC 915732' #TrackingRef 'web_deposit_cif_file_0_TanyaleRoex_1358257029.submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-picolinium pamoate hydrate THF solvate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N 1+ , C23 H15 O6 1- , 1/2(H2 O), C4 H8 O' _chemical_formula_sum 'C33 H32 N O7.50' _chemical_formula_weight 562.60 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 22.221(3) _cell_length_b 19.525(3) _cell_length_c 14.438(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.645(2) _cell_angle_gamma 90.00 _cell_volume 5646.8(14) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2899 _cell_measurement_theta_min 2.439 _cell_measurement_theta_max 27.467 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2376 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9842 _exptl_absorpt_correction_T_max 0.9914 _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 SMART 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 16936 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.05 _reflns_number_total 6200 _reflns_number_gt 4107 _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)' _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. Anti-bumping restraints were applied and the water molecule was refined using DFIX and DANG restraints. The N11-H11 bond length was restrained using DFIX. ; _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^)+(0.0573P)^2^+2.6344P] 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 6200 _refine_ls_number_parameters 418 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.047 _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 O221 O 1.00105(6) 0.04248(7) 0.61991(11) 0.0282(3) Uani 1 1 d . . . O224 O 0.65914(6) 0.21116(7) 0.55292(10) 0.0281(3) Uani 1 1 d . . . O222 O 0.98001(7) -0.06895(7) 0.61486(11) 0.0306(3) Uani 1 1 d . . . O211 O 0.91562(6) 0.12997(7) 0.61128(11) 0.0279(3) Uani 1 1 d . . . O233 O 0.57677(6) 0.25978(7) 0.62006(10) 0.0324(3) Uani 1 1 d . . . O234 O 0.61094(6) 0.27182(7) 0.78928(10) 0.0296(3) Uani 1 1 d . . . C212 C 0.89593(9) 0.00871(10) 0.61180(14) 0.0216(4) Uani 1 1 d . . . C232 C 0.82257(9) 0.20313(9) 0.77474(14) 0.0219(4) Uani 1 1 d . . . C219 C 0.76608(9) 0.03835(9) 0.58880(14) 0.0223(4) Uani 1 1 d . . . C213 C 0.85344(9) -0.04345(10) 0.60579(14) 0.0231(4) Uani 1 1 d . . . H213 H 0.8684 -0.0894 0.6096 0.028 Uiso 1 1 calc R . . C225 C 0.68947(9) 0.23238(9) 0.73252(14) 0.0226(4) Uani 1 1 d . . . C228 C 0.85528(9) 0.22821(10) 0.95773(15) 0.0275(4) Uani 1 1 d . . . H228 H 0.8431 0.2399 1.0112 0.033 Uiso 1 1 calc R . . C226 C 0.73792(9) 0.23451(9) 0.83207(14) 0.0231(4) Uani 1 1 d . . . H226 H 0.7257 0.2450 0.8859 0.028 Uiso 1 1 calc R . . C231 C 0.89173(9) 0.19356(9) 0.80110(15) 0.0258(4) Uani 1 1 d . . . H231 H 0.9053 0.1819 0.7491 0.031 Uiso 1 1 calc R . . C223 C 0.77188(9) 0.19494(9) 0.67253(14) 0.0227(4) Uani 1 1 d . . . C214 C 0.78786(9) -0.03088(10) 0.59397(14) 0.0237(4) Uani 1 1 d . . . C224 C 0.70692(9) 0.21273(9) 0.65220(14) 0.0228(4) Uani 1 1 d . . . C222 C 0.78780(9) 0.16817(9) 0.58678(15) 0.0247(4) Uani 1 1 d . . . H22A H 0.8234 0.1971 0.5834 0.030 Uiso 1 1 calc R . . H22B H 0.7476 0.1735 0.5208 0.030 Uiso 1 1 calc R . . C211 C 0.87405(9) 0.07790(10) 0.60800(14) 0.0231(4) Uani 1 1 d . . . C227 C 0.80533(9) 0.22141(9) 0.85591(14) 0.0231(4) Uani 1 1 d . . . C220 C 0.81025(9) 0.09354(9) 0.59717(14) 0.0223(4) Uani 1 1 d . . . C230 C 0.93871(9) 0.20101(10) 0.90032(16) 0.0288(5) Uani 1 1 d . . . H230 H 0.9845 0.1945 0.9158 0.035 Uiso 1 1 calc R . . C233 C 0.62057(9) 0.25470(10) 0.70844(15) 0.0249(4) Uani 1 1 d . . . C221 C 0.96355(9) -0.00801(10) 0.61677(14) 0.0245(4) Uani 1 1 d . . . C217 C 0.65684(10) -0.00581(11) 0.56133(15) 0.0304(5) Uani 1 1 d . . . H217 H 0.6120 0.0026 0.5497 0.036 Uiso 1 1 calc R . . C229 C 0.92115(9) 0.21807(10) 0.97993(16) 0.0299(5) Uani 1 1 d . . . H229 H 0.9546 0.2225 1.0485 0.036 Uiso 1 1 calc R . . C215 C 0.74338(10) -0.08553(10) 0.58308(15) 0.0296(5) Uani 1 1 d . . . H215 H 0.7585 -0.1314 0.5869 0.035 Uiso 1 1 calc R . . C216 C 0.67912(10) -0.07346(11) 0.56713(16) 0.0320(5) Uani 1 1 d . . . H216 H 0.6498 -0.1106 0.5600 0.038 Uiso 1 1 calc R . . C218 C 0.69839(9) 0.04871(10) 0.57203(15) 0.0266(4) Uani 1 1 d . . . H218 H 0.6819 0.0940 0.5682 0.032 Uiso 1 1 calc R . . O1 O 0.5000 0.33526(9) 0.7500 0.0240(4) Uani 1 2 d SD . . N11 N 1.11577(8) -0.00717(8) 0.63082(12) 0.0252(4) Uani 1 1 d D . . C12 C 1.16463(10) 0.03727(11) 0.64573(16) 0.0316(5) Uani 1 1 d . . . H12 H 1.1560 0.0850 0.6448 0.038 Uiso 1 1 calc R . . C13 C 1.22726(10) 0.01525(12) 0.66248(16) 0.0342(5) Uani 1 1 d . . . H13 H 1.2618 0.0475 0.6739 0.041 Uiso 1 1 calc R . . C14 C 1.23976(10) -0.05443(12) 0.66259(15) 0.0327(5) Uani 1 1 d . . . C15 C 1.18714(11) -0.09884(11) 0.64337(17) 0.0351(5) Uani 1 1 d . . . H15 H 1.1936 -0.1467 0.6404 0.042 Uiso 1 1 calc R . . C16 C 1.12567(10) -0.07448(10) 0.62858(16) 0.0305(5) Uani 1 1 d . . . H16 H 1.0902 -0.1055 0.6167 0.037 Uiso 1 1 calc R . . C17 C 1.30775(11) -0.08118(14) 0.68207(19) 0.0478(6) Uani 1 1 d . . . H17A H 1.3421 -0.0544 0.7370 0.072 Uiso 1 1 calc R . . H17B H 1.3141 -0.0771 0.6192 0.072 Uiso 1 1 calc R . . H17C H 1.3114 -0.1294 0.7027 0.072 Uiso 1 1 calc R . . O2 O 0.58711(19) 0.1089(2) 0.6996(3) 0.0649(10) Uani 0.50 1 d P . . C1 C 0.5921(3) 0.0958(3) 0.8004(4) 0.0626(16) Uani 0.50 1 d P . . H1A H 0.6294 0.1228 0.8515 0.075 Uiso 0.50 1 calc PR . . H1B H 0.6019 0.0466 0.8172 0.075 Uiso 0.50 1 calc PR . . C2 C 0.5195(3) 0.1001(3) 0.6298(4) 0.0716(18) Uani 0.50 1 d P . . H2A H 0.5117 0.0529 0.6023 0.086 Uiso 0.50 1 calc PR . . H2B H 0.5072 0.1325 0.5716 0.086 Uiso 0.50 1 calc PR . . H211 H 0.9532 0.1019 0.6114 0.070(8) Uiso 1 1 d R . . H234 H 0.5676 0.2919 0.7701 0.068(8) Uiso 1 1 d RD . . H224 H 0.6216 0.2324 0.5513 0.071(9) Uiso 1 1 d R . . H11 H 1.0722 0.0086 0.6239 0.052(7) Uiso 1 1 d RD . . C6 C 0.9721(7) 0.3198(7) 0.7037(13) 0.060(3) Uani 0.50 1 d P A -1 H6A H 0.9244 0.3235 0.6889 0.072 Uiso 0.50 1 calc PR A -1 H6B H 0.9817 0.2727 0.6885 0.072 Uiso 0.50 1 calc PR A -1 O3 O 1.0161(4) 0.4298(3) 0.7116(10) 0.110(3) Uani 0.50 1 d P A -1 C5 C 0.9918(4) 0.3731(4) 0.6450(6) 0.089(3) Uani 0.50 1 d P A -1 H5A H 1.0268 0.3548 0.6267 0.107 Uiso 0.50 1 calc PR A -1 H5B H 0.9527 0.3864 0.5811 0.107 Uiso 0.50 1 calc PR A -1 H1 H 0.4908 0.3646 0.6992 0.070(9) Uiso 1 1 d RD . . C8 C 1.0204(5) 0.4164(6) 0.8080(9) 0.079(3) Uani 0.50 1 d P A -1 H8A H 0.9827 0.4378 0.8167 0.095 Uiso 0.50 1 calc PR A -1 H8B H 1.0628 0.4339 0.8621 0.095 Uiso 0.50 1 calc PR A -1 C7 C 1.0172(9) 0.3404(7) 0.8133(14) 0.086(5) Uani 0.50 1 d P A -1 H7A H 0.9981 0.3262 0.8607 0.103 Uiso 0.50 1 calc PR A -1 H7B H 1.0621 0.3199 0.8363 0.103 Uiso 0.50 1 calc PR A -1 C3 C 0.52511(16) 0.11534(19) 0.8062(3) 0.0817(10) 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 O221 0.0231(7) 0.0273(8) 0.0370(8) 0.0005(6) 0.0156(6) 0.0014(6) O224 0.0210(7) 0.0359(8) 0.0222(7) 0.0006(6) 0.0046(6) 0.0060(6) O222 0.0326(8) 0.0287(8) 0.0367(8) 0.0020(6) 0.0207(7) 0.0065(6) O211 0.0244(7) 0.0242(7) 0.0392(8) 0.0001(6) 0.0177(6) -0.0008(6) O233 0.0184(7) 0.0460(9) 0.0265(8) -0.0024(6) 0.0039(6) 0.0065(6) O234 0.0185(7) 0.0413(8) 0.0273(8) -0.0013(6) 0.0082(6) 0.0072(6) C212 0.0228(9) 0.0259(10) 0.0174(9) 0.0014(7) 0.0098(8) 0.0017(8) C232 0.0188(9) 0.0176(9) 0.0274(10) 0.0010(7) 0.0083(8) 0.0008(7) C219 0.0221(9) 0.0278(10) 0.0172(9) -0.0015(7) 0.0088(8) -0.0016(8) C213 0.0275(10) 0.0233(10) 0.0194(10) -0.0002(7) 0.0109(8) 0.0018(8) C225 0.0187(9) 0.0212(10) 0.0262(10) -0.0001(8) 0.0082(8) 0.0010(7) C228 0.0221(10) 0.0305(11) 0.0267(10) -0.0012(8) 0.0076(9) 0.0007(8) C226 0.0195(9) 0.0241(10) 0.0252(10) 0.0007(8) 0.0090(8) 0.0017(7) C231 0.0200(9) 0.0228(10) 0.0348(11) -0.0021(8) 0.0120(9) -0.0009(8) C223 0.0208(9) 0.0209(10) 0.0266(10) 0.0020(8) 0.0103(8) 0.0015(7) C214 0.0244(10) 0.0281(11) 0.0179(9) 0.0003(8) 0.0086(8) -0.0008(8) C224 0.0198(9) 0.0211(10) 0.0229(10) 0.0006(7) 0.0049(8) 0.0011(7) C222 0.0228(9) 0.0253(10) 0.0257(10) 0.0011(8) 0.0103(8) 0.0021(8) C211 0.0230(9) 0.0262(10) 0.0207(10) 0.0005(8) 0.0099(8) -0.0017(8) C227 0.0183(9) 0.0217(10) 0.0264(10) 0.0006(7) 0.0070(8) 0.0009(7) C220 0.0243(9) 0.0245(10) 0.0192(9) 0.0003(7) 0.0106(8) 0.0003(8) C230 0.0153(9) 0.0283(11) 0.0385(12) -0.0036(9) 0.0076(9) 0.0005(8) C233 0.0182(9) 0.0259(10) 0.0272(11) -0.0012(8) 0.0066(9) 0.0005(8) C221 0.0253(10) 0.0297(11) 0.0194(10) 0.0022(8) 0.0105(8) 0.0029(8) C217 0.0219(10) 0.0366(12) 0.0321(11) -0.0034(9) 0.0112(9) -0.0034(8) C229 0.0197(9) 0.0320(11) 0.0298(11) -0.0008(9) 0.0030(9) 0.0004(8) C215 0.0326(11) 0.0264(11) 0.0306(11) -0.0001(8) 0.0144(10) -0.0023(8) C216 0.0296(11) 0.0331(12) 0.0330(12) -0.0025(9) 0.0134(10) -0.0092(9) C218 0.0238(10) 0.0300(11) 0.0255(11) -0.0023(8) 0.0102(9) 0.0002(8) O1 0.0173(9) 0.0266(10) 0.0274(10) 0.000 0.0091(8) 0.000 N11 0.0234(8) 0.0308(9) 0.0218(8) -0.0005(7) 0.0100(7) 0.0032(7) C12 0.0318(11) 0.0287(11) 0.0337(12) -0.0064(9) 0.0135(10) -0.0019(9) C13 0.0280(11) 0.0464(14) 0.0277(11) -0.0058(9) 0.0117(9) -0.0062(9) C14 0.0277(11) 0.0518(14) 0.0209(11) 0.0037(9) 0.0125(9) 0.0100(10) C15 0.0422(13) 0.0322(12) 0.0398(13) 0.0074(9) 0.0261(11) 0.0110(10) C16 0.0352(11) 0.0291(11) 0.0338(12) 0.0019(9) 0.0211(10) -0.0001(9) C17 0.0330(12) 0.0761(19) 0.0378(14) 0.0046(12) 0.0187(11) 0.0155(12) O2 0.061(2) 0.073(3) 0.057(3) -0.007(2) 0.023(2) 0.002(2) C1 0.070(4) 0.050(3) 0.051(3) 0.016(3) 0.010(3) -0.001(3) C2 0.090(5) 0.059(4) 0.051(4) -0.007(3) 0.017(4) -0.028(3) C6 0.052(4) 0.034(5) 0.085(8) -0.012(5) 0.021(4) 0.000(4) O3 0.078(5) 0.057(3) 0.162(10) 0.011(4) 0.020(5) -0.016(3) C5 0.092(6) 0.060(6) 0.081(6) 0.013(4) 0.006(5) -0.022(5) C8 0.059(5) 0.079(7) 0.091(8) -0.030(6) 0.024(6) -0.025(5) C7 0.098(11) 0.066(11) 0.095(8) -0.003(8) 0.043(7) -0.024(8) C3 0.067(2) 0.093(3) 0.073(2) -0.0049(18) 0.0192(18) -0.0168(18) _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 O221 C221 1.279(2) . ? O224 C224 1.366(2) . ? O224 H224 0.9230 . ? O222 C221 1.249(2) . ? O211 C211 1.361(2) . ? O211 H211 0.9993 . ? O233 C233 1.229(2) . ? O234 C233 1.318(2) . ? O234 H234 0.9635 . ? C212 C213 1.366(3) . ? C212 C211 1.429(3) . ? C212 C221 1.509(3) . ? C232 C223 1.426(3) . ? C232 C231 1.427(2) . ? C232 C227 1.427(3) . ? C219 C214 1.427(3) . ? C219 C220 1.427(2) . ? C219 C218 1.431(3) . ? C213 C214 1.413(3) . ? C213 H213 0.9500 . ? C225 C226 1.374(3) . ? C225 C224 1.425(3) . ? C225 C233 1.481(2) . ? C228 C229 1.371(3) . ? C228 C227 1.414(3) . ? C228 H228 0.9500 . ? C226 C227 1.408(2) . ? C226 H226 0.9500 . ? C231 C230 1.367(3) . ? C231 H231 0.9500 . ? C223 C224 1.387(2) . ? C223 C222 1.520(3) . ? C214 C215 1.416(3) . ? C222 C220 1.526(3) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C211 C220 1.391(2) . ? C230 C229 1.404(3) . ? C230 H230 0.9500 . ? C217 C218 1.373(3) . ? C217 C216 1.400(3) . ? C217 H217 0.9500 . ? C229 H229 0.9500 . ? C215 C216 1.365(3) . ? C215 H215 0.9500 . ? C216 H216 0.9500 . ? C218 H218 0.9500 . ? O1 H1 0.8814 . ? N11 C12 1.333(2) . ? N11 C16 1.335(2) . ? N11 H11 0.9798 . ? C12 C13 1.374(3) . ? C12 H12 0.9500 . ? C13 C14 1.388(3) . ? C13 H13 0.9500 . ? C14 C15 1.384(3) . ? C14 C17 1.506(3) . ? C15 C16 1.373(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? O2 C2 1.410(6) . ? O2 C1 1.433(6) . ? C1 C3 1.575(7) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.649(6) 2_656 ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C6 C7 1.515(11) . ? C6 C5 1.520(13) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? O3 C8 1.380(9) . ? O3 C5 1.411(12) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C8 C7 1.487(17) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C3 C3 1.521(6) 2_656 ? C3 C2 1.649(6) 2_656 ? 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 C224 O224 H224 107.5 . . ? C211 O211 H211 98.3 . . ? C233 O234 H234 112.0 . . ? C213 C212 C211 119.22(17) . . ? C213 C212 C221 119.25(17) . . ? C211 C212 C221 121.45(16) . . ? C223 C232 C231 122.59(17) . . ? C223 C232 C227 120.35(16) . . ? C231 C232 C227 117.06(17) . . ? C214 C219 C220 120.37(16) . . ? C214 C219 C218 116.79(17) . . ? C220 C219 C218 122.81(17) . . ? C212 C213 C214 121.77(17) . . ? C212 C213 H213 119.1 . . ? C214 C213 H213 119.1 . . ? C226 C225 C224 119.56(16) . . ? C226 C225 C233 119.94(17) . . ? C224 C225 C233 120.38(16) . . ? C229 C228 C227 120.53(19) . . ? C229 C228 H228 119.7 . . ? C227 C228 H228 119.7 . . ? C225 C226 C227 121.30(18) . . ? C225 C226 H226 119.4 . . ? C227 C226 H226 119.4 . . ? C230 C231 C232 120.76(18) . . ? C230 C231 H231 119.6 . . ? C232 C231 H231 119.6 . . ? C224 C223 C232 118.34(17) . . ? C224 C223 C222 120.10(17) . . ? C232 C223 C222 121.56(16) . . ? C213 C214 C215 121.07(18) . . ? C213 C214 C219 118.65(17) . . ? C215 C214 C219 120.23(17) . . ? O224 C224 C223 118.80(17) . . ? O224 C224 C225 119.88(15) . . ? C223 C224 C225 121.33(17) . . ? C223 C222 C220 115.44(15) . . ? C223 C222 H22A 108.4 . . ? C220 C222 H22A 108.4 . . ? C223 C222 H22B 108.4 . . ? C220 C222 H22B 108.4 . . ? H22A C222 H22B 107.5 . . ? O211 C211 C220 118.90(16) . . ? O211 C211 C212 119.37(16) . . ? C220 C211 C212 121.68(17) . . ? C226 C227 C228 120.71(17) . . ? C226 C227 C232 118.71(17) . . ? C228 C227 C232 120.56(16) . . ? C211 C220 C219 118.29(17) . . ? C211 C220 C222 119.63(16) . . ? C219 C220 C222 121.93(16) . . ? C231 C230 C229 121.75(17) . . ? C231 C230 H230 119.1 . . ? C229 C230 H230 119.1 . . ? O233 C233 O234 122.68(16) . . ? O233 C233 C225 122.77(17) . . ? O234 C233 C225 114.48(16) . . ? O222 C221 O221 122.88(17) . . ? O222 C221 C212 120.01(17) . . ? O221 C221 C212 117.08(16) . . ? C218 C217 C216 121.42(18) . . ? C218 C217 H217 119.3 . . ? C216 C217 H217 119.3 . . ? C228 C229 C230 119.32(19) . . ? C228 C229 H229 120.3 . . ? C230 C229 H229 120.3 . . ? C216 C215 C214 121.16(19) . . ? C216 C215 H215 119.4 . . ? C214 C215 H215 119.4 . . ? C215 C216 C217 119.34(19) . . ? C215 C216 H216 120.3 . . ? C217 C216 H216 120.3 . . ? C217 C218 C219 121.05(18) . . ? C217 C218 H218 119.5 . . ? C219 C218 H218 119.5 . . ? C12 N11 C16 120.90(17) . . ? C12 N11 H11 120.8 . . ? C16 N11 H11 118.2 . . ? N11 C12 C13 121.1(2) . . ? N11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C14 119.6(2) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 117.54(18) . . ? C15 C14 C17 120.8(2) . . ? C13 C14 C17 121.6(2) . . ? C16 C15 C14 120.8(2) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? N11 C16 C15 120.02(19) . . ? N11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C2 O2 C1 107.2(4) . . ? O2 C1 C3 110.6(4) . . ? O2 C1 H1A 109.5 . . ? C3 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? O2 C2 C3 106.9(4) . 2_656 ? O2 C2 H2A 110.3 . . ? C3 C2 H2A 110.3 2_656 . ? O2 C2 H2B 110.3 . . ? C3 C2 H2B 110.3 2_656 . ? H2A C2 H2B 108.6 . . ? C7 C6 C5 100.4(12) . . ? C7 C6 H6A 111.7 . . ? C5 C6 H6A 111.7 . . ? C7 C6 H6B 111.7 . . ? C5 C6 H6B 111.7 . . ? H6A C6 H6B 109.5 . . ? C8 O3 C5 112.1(8) . . ? O3 C5 C6 106.0(10) . . ? O3 C5 H5A 110.5 . . ? C6 C5 H5A 110.5 . . ? O3 C5 H5B 110.5 . . ? C6 C5 H5B 110.5 . . ? H5A C5 H5B 108.7 . . ? O3 C8 C7 104.9(10) . . ? O3 C8 H8A 110.8 . . ? C7 C8 H8A 110.8 . . ? O3 C8 H8B 110.8 . . ? C7 C8 H8B 110.8 . . ? H8A C8 H8B 108.9 . . ? C8 C7 C6 103.6(13) . . ? C8 C7 H7A 111.0 . . ? C6 C7 H7A 111.0 . . ? C8 C7 H7B 111.0 . . ? C6 C7 H7B 111.0 . . ? H7A C7 H7B 109.0 . . ? C3 C3 C1 102.5(4) 2_656 . ? C3 C3 C2 104.9(4) 2_656 2_656 ? C1 C3 C2 143.0(4) . 2_656 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C211 C212 C213 C214 1.2(3) . . . . ? C221 C212 C213 C214 -175.66(17) . . . . ? C224 C225 C226 C227 3.6(3) . . . . ? C233 C225 C226 C227 -172.45(17) . . . . ? C223 C232 C231 C230 -179.11(17) . . . . ? C227 C232 C231 C230 0.7(3) . . . . ? C231 C232 C223 C224 -172.89(17) . . . . ? C227 C232 C223 C224 7.3(3) . . . . ? C231 C232 C223 C222 6.5(3) . . . . ? C227 C232 C223 C222 -173.36(16) . . . . ? C212 C213 C214 C215 177.04(18) . . . . ? C212 C213 C214 C219 -0.3(3) . . . . ? C220 C219 C214 C213 -1.0(3) . . . . ? C218 C219 C214 C213 177.17(17) . . . . ? C220 C219 C214 C215 -178.42(17) . . . . ? C218 C219 C214 C215 -0.2(3) . . . . ? C232 C223 C224 O224 173.98(16) . . . . ? C222 C223 C224 O224 -5.4(3) . . . . ? C232 C223 C224 C225 -6.1(3) . . . . ? C222 C223 C224 C225 174.57(17) . . . . ? C226 C225 C224 O224 -179.34(16) . . . . ? C233 C225 C224 O224 -3.3(3) . . . . ? C226 C225 C224 C223 0.7(3) . . . . ? C233 C225 C224 C223 176.75(17) . . . . ? C224 C223 C222 C220 -113.41(19) . . . . ? C232 C223 C222 C220 67.2(2) . . . . ? C213 C212 C211 O211 -178.30(16) . . . . ? C221 C212 C211 O211 -1.5(3) . . . . ? C213 C212 C211 C220 -0.7(3) . . . . ? C221 C212 C211 C220 176.06(17) . . . . ? C225 C226 C227 C228 175.77(18) . . . . ? C225 C226 C227 C232 -2.4(3) . . . . ? C229 C228 C227 C226 -177.39(19) . . . . ? C229 C228 C227 C232 0.7(3) . . . . ? C223 C232 C227 C226 -3.2(3) . . . . ? C231 C232 C227 C226 176.98(17) . . . . ? C223 C232 C227 C228 178.69(17) . . . . ? C231 C232 C227 C228 -1.2(3) . . . . ? O211 C211 C220 C219 176.99(16) . . . . ? C212 C211 C220 C219 -0.6(3) . . . . ? O211 C211 C220 C222 1.4(3) . . . . ? C212 C211 C220 C222 -176.19(16) . . . . ? C214 C219 C220 C211 1.5(3) . . . . ? C218 C219 C220 C211 -176.62(18) . . . . ? C214 C219 C220 C222 176.95(16) . . . . ? C218 C219 C220 C222 -1.1(3) . . . . ? C223 C222 C220 C211 -117.02(19) . . . . ? C223 C222 C220 C219 67.6(2) . . . . ? C232 C231 C230 C229 0.2(3) . . . . ? C226 C225 C233 O233 173.25(18) . . . . ? C224 C225 C233 O233 -2.8(3) . . . . ? C226 C225 C233 O234 -3.6(3) . . . . ? C224 C225 C233 O234 -179.68(16) . . . . ? C213 C212 C221 O222 0.3(3) . . . . ? C211 C212 C221 O222 -176.44(17) . . . . ? C213 C212 C221 O221 178.41(16) . . . . ? C211 C212 C221 O221 1.6(3) . . . . ? C227 C228 C229 C230 0.2(3) . . . . ? C231 C230 C229 C228 -0.6(3) . . . . ? C213 C214 C215 C216 -177.08(19) . . . . ? C219 C214 C215 C216 0.3(3) . . . . ? C214 C215 C216 C217 0.1(3) . . . . ? C218 C217 C216 C215 -0.4(3) . . . . ? C216 C217 C218 C219 0.5(3) . . . . ? C214 C219 C218 C217 -0.1(3) . . . . ? C220 C219 C218 C217 178.02(18) . . . . ? C16 N11 C12 C13 -2.1(3) . . . . ? N11 C12 C13 C14 0.9(3) . . . . ? C12 C13 C14 C15 1.3(3) . . . . ? C12 C13 C14 C17 -179.1(2) . . . . ? C13 C14 C15 C16 -2.3(3) . . . . ? C17 C14 C15 C16 178.1(2) . . . . ? C12 N11 C16 C15 1.0(3) . . . . ? C14 C15 C16 N11 1.2(3) . . . . ? C2 O2 C1 C3 -30.0(5) . . . . ? C1 O2 C2 C3 26.2(5) . . . 2_656 ? C8 O3 C5 C6 6.0(15) . . . . ? C7 C6 C5 O3 -25.5(12) . . . . ? C5 O3 C8 C7 17.0(15) . . . . ? O3 C8 C7 C6 -32.9(12) . . . . ? C5 C6 C7 C8 35.0(10) . . . . ? O2 C1 C3 C3 20.1(4) . . . 2_656 ? O2 C1 C3 C2 157.1(5) . . . 2_656 ? 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 1.00 1.54 2.5165(18) 163.9 . O234 H234 O1 0.96 1.64 2.5929(15) 171.2 . O224 H224 O233 0.92 1.77 2.5935(18) 147.7 . N11 H11 O221 0.98 1.69 2.667(2) 174.2 . O1 H1 O222 0.88 1.72 2.5983(19) 170.9 3_455 _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.259 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.049 data_5 _database_code_depnum_ccdc_archive 'CCDC 915733' #TrackingRef 'web_deposit_cif_file_0_TanyaleRoex_1358257029.submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,3-lutidinium pamoate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 O6 1- , C7 H10 N 1+' _chemical_formula_sum 'C30 H25 N O6' _chemical_formula_weight 495.51 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 13.4450(13) _cell_length_b 14.0000(13) _cell_length_c 13.8229(13) _cell_angle_alpha 90.00 _cell_angle_beta 114.6120(10) _cell_angle_gamma 90.00 _cell_volume 2365.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4732 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 27.63 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9733 _exptl_absorpt_correction_T_max 0.9742 _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 13800 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.79 _reflns_number_total 5143 _reflns_number_gt 4157 _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)' _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. Anti-bumping restraints were applied in an effort to remove short intermolecular contacts, but this was not effective. ; _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^)+(0.0460P)^2^+0.7815P] 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 5143 _refine_ls_number_parameters 343 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.060 _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 0.61200(10) 0.69735(8) 0.64076(9) 0.0197(2) Uani 1 1 d . . . H11 H 0.5540(16) 0.6487(14) 0.6305(15) 0.045(5) Uiso 1 1 d . . . C12 C 0.58211(11) 0.79018(10) 0.62980(11) 0.0196(3) Uani 1 1 d . . . C13 C 0.66190(12) 0.86006(10) 0.64842(11) 0.0204(3) Uani 1 1 d . . . C14 C 0.76911(12) 0.83021(10) 0.67510(11) 0.0222(3) Uani 1 1 d . . . H14 H 0.8247 0.8766 0.6879 0.027 Uiso 1 1 calc R . . C15 C 0.79602(12) 0.73424(11) 0.68328(11) 0.0241(3) Uani 1 1 d . . . H15 H 0.8691 0.7146 0.7004 0.029 Uiso 1 1 calc R . . C16 C 0.71504(12) 0.66765(10) 0.66616(11) 0.0220(3) Uani 1 1 d . . . H16 H 0.7318 0.6014 0.6722 0.026 Uiso 1 1 calc R . . C17 C 0.46362(12) 0.81093(11) 0.59624(13) 0.0275(3) Uani 1 1 d . . . H17A H 0.4238 0.7509 0.5894 0.041 Uiso 1 1 calc R . . H17B H 0.4348 0.8441 0.5276 0.041 Uiso 1 1 calc R . . H17C H 0.4543 0.8515 0.6497 0.041 Uiso 1 1 calc R . . H211 H 0.3234 0.5582 0.6032 0.056(6) Uiso 1 1 d R . . H224 H -0.1335 0.2091 0.4792 0.058(6) Uiso 1 1 d R . . H234 H -0.3477 0.1266 0.1926 0.079(8) Uiso 1 1 d RD . . C18 C 0.63277(13) 0.96418(10) 0.63926(12) 0.0270(3) Uani 1 1 d . . . H18A H 0.5867 0.9770 0.6772 0.041 Uiso 1 1 calc R . . H18B H 0.5928 0.9811 0.5641 0.041 Uiso 1 1 calc R . . H18C H 0.6998 1.0024 0.6705 0.041 Uiso 1 1 calc R . . C233 C -0.23442(11) 0.19884(10) 0.30079(12) 0.0223(3) Uani 1 1 d . . . O211 O 0.25986(8) 0.52391(6) 0.59263(8) 0.0222(2) Uani 1 1 d . . . C211 C 0.28980(11) 0.43112(9) 0.59097(10) 0.0178(3) Uani 1 1 d . . . C212 C 0.40103(11) 0.40908(9) 0.61201(10) 0.0176(3) Uani 1 1 d . . . C213 C 0.43128(11) 0.31502(9) 0.61582(10) 0.0188(3) Uani 1 1 d . . . H213 H 0.5046 0.3001 0.6285 0.023 Uiso 1 1 calc R . . C214 C 0.35658(11) 0.24011(9) 0.60151(10) 0.0178(3) Uani 1 1 d . . . C215 C 0.39170(12) 0.14341(9) 0.61351(11) 0.0204(3) Uani 1 1 d . . . H215 H 0.4658 0.1292 0.6286 0.024 Uiso 1 1 calc R . . C216 C 0.32046(12) 0.07068(10) 0.60366(11) 0.0209(3) Uani 1 1 d . . . H216 H 0.3448 0.0063 0.6124 0.025 Uiso 1 1 calc R . . C217 C 0.21045(12) 0.09216(10) 0.58034(11) 0.0208(3) Uani 1 1 d . . . H217 H 0.1609 0.0415 0.5736 0.025 Uiso 1 1 calc R . . C218 C 0.17322(11) 0.18459(10) 0.56716(10) 0.0193(3) Uani 1 1 d . . . H218 H 0.0984 0.1968 0.5506 0.023 Uiso 1 1 calc R . . C219 C 0.24521(11) 0.26266(9) 0.57799(10) 0.0170(3) Uani 1 1 d . . . C220 C 0.21159(11) 0.35998(9) 0.57055(10) 0.0175(3) Uani 1 1 d . . . O221 O 0.45114(8) 0.57263(7) 0.61925(8) 0.0239(2) Uani 1 1 d . . . C221 C 0.48470(11) 0.48654(10) 0.62956(11) 0.0197(3) Uani 1 1 d . . . O222 O 0.58300(8) 0.46602(7) 0.65377(8) 0.0245(2) Uani 1 1 d . . . C222 C 0.09382(11) 0.38664(10) 0.54855(11) 0.0186(3) Uani 1 1 d . . . H22A H 0.0733 0.3521 0.6000 0.022 Uiso 1 1 calc R . . H22B H 0.0915 0.4558 0.5624 0.022 Uiso 1 1 calc R . . C223 C 0.00781(11) 0.36564(9) 0.43680(11) 0.0177(3) Uani 1 1 d . . . O224 O -0.07789(8) 0.25528(7) 0.50701(8) 0.0249(2) Uani 1 1 d . . . C224 C -0.07397(11) 0.29925(9) 0.42062(11) 0.0193(3) Uani 1 1 d . . . C225 C -0.15264(11) 0.27577(9) 0.31610(11) 0.0197(3) Uani 1 1 d . . . C226 C -0.15026(11) 0.32225(9) 0.22963(11) 0.0203(3) Uani 1 1 d . . . H226 H -0.2015 0.3052 0.1602 0.024 Uiso 1 1 calc R . . C227 C -0.07319(11) 0.39476(9) 0.24199(11) 0.0191(3) Uani 1 1 d . . . C228 C -0.07393(12) 0.44637(10) 0.15333(11) 0.0219(3) Uani 1 1 d . . . H228 H -0.1257 0.4304 0.0837 0.026 Uiso 1 1 calc R . . C229 C -0.00111(12) 0.51879(10) 0.16680(12) 0.0240(3) Uani 1 1 d . . . H229 H -0.0018 0.5526 0.1070 0.029 Uiso 1 1 calc R . . C230 C 0.07501(12) 0.54280(10) 0.27029(12) 0.0242(3) Uani 1 1 d . . . H230 H 0.1244 0.5942 0.2797 0.029 Uiso 1 1 calc R . . C231 C 0.07920(11) 0.49362(10) 0.35736(11) 0.0202(3) Uani 1 1 d . . . H231 H 0.1320 0.5109 0.4261 0.024 Uiso 1 1 calc R . . C232 C 0.00585(11) 0.41705(9) 0.34674(11) 0.0176(3) Uani 1 1 d . . . O233 O -0.23890(9) 0.15446(7) 0.37583(9) 0.0285(2) Uani 1 1 d . . . O234 O -0.29919(8) 0.18164(7) 0.20091(9) 0.0264(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 0.0206(6) 0.0165(6) 0.0207(6) 0.0002(4) 0.0073(5) 0.0005(5) C12 0.0208(7) 0.0190(7) 0.0186(7) 0.0008(5) 0.0077(6) 0.0013(5) C13 0.0241(7) 0.0195(7) 0.0176(7) 0.0010(5) 0.0087(6) 0.0005(6) C14 0.0213(7) 0.0246(7) 0.0204(7) 0.0003(6) 0.0085(6) -0.0036(6) C15 0.0203(7) 0.0292(8) 0.0226(7) 0.0009(6) 0.0089(6) 0.0035(6) C16 0.0242(7) 0.0203(7) 0.0206(7) 0.0008(5) 0.0084(6) 0.0045(6) C17 0.0213(7) 0.0226(7) 0.0375(9) 0.0023(6) 0.0110(7) 0.0026(6) C18 0.0325(8) 0.0190(7) 0.0295(8) 0.0012(6) 0.0128(7) -0.0007(6) C233 0.0145(6) 0.0165(7) 0.0357(8) -0.0008(6) 0.0102(6) 0.0030(5) O211 0.0186(5) 0.0137(5) 0.0309(6) -0.0022(4) 0.0069(4) 0.0018(4) C211 0.0190(7) 0.0147(6) 0.0176(7) -0.0007(5) 0.0054(5) 0.0021(5) C212 0.0172(7) 0.0173(6) 0.0157(6) -0.0004(5) 0.0043(5) -0.0002(5) C213 0.0162(6) 0.0191(7) 0.0183(7) -0.0007(5) 0.0046(5) 0.0015(5) C214 0.0180(7) 0.0173(6) 0.0158(6) -0.0009(5) 0.0048(5) 0.0009(5) C215 0.0198(7) 0.0172(7) 0.0221(7) -0.0002(5) 0.0067(6) 0.0035(5) C216 0.0257(7) 0.0146(6) 0.0202(7) -0.0006(5) 0.0074(6) 0.0018(5) C217 0.0240(7) 0.0179(7) 0.0193(7) -0.0014(5) 0.0076(6) -0.0034(6) C218 0.0188(7) 0.0200(7) 0.0174(7) -0.0009(5) 0.0059(5) -0.0007(5) C219 0.0183(7) 0.0177(6) 0.0139(6) -0.0006(5) 0.0057(5) 0.0000(5) C220 0.0176(7) 0.0174(6) 0.0156(6) 0.0001(5) 0.0051(5) 0.0020(5) O221 0.0181(5) 0.0143(5) 0.0341(6) 0.0004(4) 0.0057(4) 0.0001(4) C221 0.0186(7) 0.0184(7) 0.0181(7) -0.0003(5) 0.0037(5) 0.0009(5) O222 0.0166(5) 0.0182(5) 0.0345(6) 0.0010(4) 0.0065(4) 0.0012(4) C222 0.0168(7) 0.0165(6) 0.0223(7) 0.0000(5) 0.0079(6) 0.0012(5) C223 0.0146(6) 0.0153(6) 0.0236(7) 0.0003(5) 0.0081(5) 0.0032(5) O224 0.0227(5) 0.0243(5) 0.0285(6) 0.0050(4) 0.0113(4) -0.0027(4) C224 0.0164(6) 0.0164(6) 0.0264(7) 0.0035(5) 0.0102(6) 0.0040(5) C225 0.0142(6) 0.0140(6) 0.0312(8) 0.0000(5) 0.0099(6) 0.0020(5) C226 0.0153(6) 0.0171(6) 0.0254(7) -0.0018(5) 0.0053(6) 0.0026(5) C227 0.0162(6) 0.0158(6) 0.0258(7) -0.0003(5) 0.0092(6) 0.0031(5) C228 0.0200(7) 0.0216(7) 0.0224(7) 0.0002(5) 0.0070(6) 0.0039(6) C229 0.0228(7) 0.0242(7) 0.0267(8) 0.0061(6) 0.0121(6) 0.0021(6) C230 0.0177(7) 0.0207(7) 0.0341(8) 0.0032(6) 0.0106(6) -0.0014(6) C231 0.0149(6) 0.0181(7) 0.0264(7) 0.0011(5) 0.0075(6) 0.0019(5) C232 0.0133(6) 0.0144(6) 0.0255(7) 0.0004(5) 0.0085(5) 0.0037(5) O233 0.0248(6) 0.0234(5) 0.0396(6) 0.0011(5) 0.0157(5) -0.0049(4) O234 0.0163(5) 0.0207(5) 0.0368(6) -0.0007(4) 0.0058(4) -0.0030(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 1.3456(18) . ? N11 C12 1.3500(18) . ? N11 H11 1.00(2) . ? C12 C13 1.394(2) . ? C12 C17 1.491(2) . ? C13 C14 1.395(2) . ? C13 C18 1.5010(19) . ? C14 C15 1.384(2) . ? C14 H14 0.9500 . ? C15 C16 1.377(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C233 O233 1.2320(18) . ? C233 O234 1.3118(18) . ? C233 C225 1.4900(19) . ? O211 C211 1.3629(16) . ? O211 H211 0.9370 . ? C211 C220 1.3893(19) . ? C211 C212 1.4332(19) . ? C212 C213 1.3727(19) . ? C212 C221 1.5077(19) . ? C213 C214 1.4079(19) . ? C213 H213 0.9500 . ? C214 C215 1.4206(18) . ? C214 C219 1.4290(19) . ? C215 C216 1.3654(19) . ? C215 H215 0.9500 . ? C216 C217 1.409(2) . ? C216 H216 0.9500 . ? C217 C218 1.3719(19) . ? C217 H217 0.9500 . ? C218 C219 1.4258(19) . ? C218 H218 0.9500 . ? C219 C220 1.4257(18) . ? C220 C222 1.5291(18) . ? O221 C221 1.2739(17) . ? C221 O222 1.2541(17) . ? C222 C223 1.5238(19) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C223 C224 1.3849(19) . ? C223 C232 1.4286(19) . ? O224 C224 1.3639(16) . ? O224 H224 0.9411 . ? C224 C225 1.429(2) . ? C225 C226 1.373(2) . ? C226 C227 1.4091(19) . ? C226 H226 0.9500 . ? C227 C228 1.4192(19) . ? C227 C232 1.4288(19) . ? C228 C229 1.367(2) . ? C228 H228 0.9500 . ? C229 C230 1.410(2) . ? C229 H229 0.9500 . ? C230 C231 1.367(2) . ? C230 H230 0.9500 . ? C231 C232 1.4223(19) . ? C231 H231 0.9500 . ? O234 H234 0.9848 . ? 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 123.56(13) . . ? C16 N11 H11 119.0(11) . . ? C12 N11 H11 117.5(11) . . ? N11 C12 C13 118.99(13) . . ? N11 C12 C17 116.88(12) . . ? C13 C12 C17 124.13(13) . . ? C12 C13 C14 118.00(13) . . ? C12 C13 C18 120.80(13) . . ? C14 C13 C18 121.20(13) . . ? C15 C14 C13 121.25(13) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C16 C15 C14 118.83(13) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? N11 C16 C15 119.35(13) . . ? N11 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O233 C233 O234 123.36(13) . . ? O233 C233 C225 122.47(13) . . ? O234 C233 C225 114.16(12) . . ? C211 O211 H211 103.5 . . ? O211 C211 C220 118.87(12) . . ? O211 C211 C212 119.50(12) . . ? C220 C211 C212 121.62(12) . . ? C213 C212 C211 118.81(12) . . ? C213 C212 C221 119.64(12) . . ? C211 C212 C221 121.55(12) . . ? C212 C213 C214 121.77(13) . . ? C212 C213 H213 119.1 . . ? C214 C213 H213 119.1 . . ? C213 C214 C215 120.70(12) . . ? C213 C214 C219 119.08(12) . . ? C215 C214 C219 120.19(12) . . ? C216 C215 C214 120.92(13) . . ? C216 C215 H215 119.5 . . ? C214 C215 H215 119.5 . . ? C215 C216 C217 119.32(12) . . ? C215 C216 H216 120.3 . . ? C217 C216 H216 120.3 . . ? C218 C217 C216 121.46(13) . . ? C218 C217 H217 119.3 . . ? C216 C217 H217 119.3 . . ? C217 C218 C219 120.99(13) . . ? C217 C218 H218 119.5 . . ? C219 C218 H218 119.5 . . ? C220 C219 C218 122.96(12) . . ? C220 C219 C214 119.88(12) . . ? C218 C219 C214 117.11(12) . . ? C211 C220 C219 118.70(12) . . ? C211 C220 C222 119.93(12) . . ? C219 C220 C222 121.23(12) . . ? O222 C221 O221 122.09(13) . . ? O222 C221 C212 120.72(12) . . ? O221 C221 C212 117.18(12) . . ? C223 C222 C220 116.12(11) . . ? C223 C222 H22A 108.3 . . ? C220 C222 H22A 108.3 . . ? C223 C222 H22B 108.3 . . ? C220 C222 H22B 108.3 . . ? H22A C222 H22B 107.4 . . ? C224 C223 C232 118.17(12) . . ? C224 C223 C222 120.63(12) . . ? C232 C223 C222 121.13(12) . . ? C224 O224 H224 105.4 . . ? O224 C224 C223 118.63(12) . . ? O224 C224 C225 119.95(12) . . ? C223 C224 C225 121.42(12) . . ? C226 C225 C224 119.70(12) . . ? C226 C225 C233 120.15(13) . . ? C224 C225 C233 120.11(12) . . ? C225 C226 C227 121.22(13) . . ? C225 C226 H226 119.4 . . ? C227 C226 H226 119.4 . . ? C226 C227 C228 121.45(13) . . ? C226 C227 C232 118.64(12) . . ? C228 C227 C232 119.91(12) . . ? C229 C228 C227 120.86(13) . . ? C229 C228 H228 119.6 . . ? C227 C228 H228 119.6 . . ? C228 C229 C230 119.41(13) . . ? C228 C229 H229 120.3 . . ? C230 C229 H229 120.3 . . ? C231 C230 C229 121.31(13) . . ? C231 C230 H230 119.3 . . ? C229 C230 H230 119.3 . . ? C230 C231 C232 121.07(13) . . ? C230 C231 H231 119.5 . . ? C232 C231 H231 119.5 . . ? C231 C232 C223 121.97(12) . . ? C231 C232 C227 117.41(12) . . ? C223 C232 C227 120.60(12) . . ? C233 O234 H234 112.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 -1.9(2) . . . . ? C16 N11 C12 C17 177.12(13) . . . . ? N11 C12 C13 C14 1.57(19) . . . . ? C17 C12 C13 C14 -177.33(13) . . . . ? N11 C12 C13 C18 -178.80(12) . . . . ? C17 C12 C13 C18 2.3(2) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? C18 C13 C14 C15 -179.82(13) . . . . ? C13 C14 C15 C16 -1.0(2) . . . . ? C12 N11 C16 C15 0.6(2) . . . . ? C14 C15 C16 N11 0.8(2) . . . . ? O211 C211 C212 C213 176.47(12) . . . . ? C220 C211 C212 C213 -2.4(2) . . . . ? O211 C211 C212 C221 -3.72(19) . . . . ? C220 C211 C212 C221 177.37(12) . . . . ? C211 C212 C213 C214 -1.1(2) . . . . ? C221 C212 C213 C214 179.05(12) . . . . ? C212 C213 C214 C215 -175.37(13) . . . . ? C212 C213 C214 C219 2.65(19) . . . . ? C213 C214 C215 C216 177.51(13) . . . . ? C219 C214 C215 C216 -0.5(2) . . . . ? C214 C215 C216 C217 0.6(2) . . . . ? C215 C216 C217 C218 0.1(2) . . . . ? C216 C217 C218 C219 -0.8(2) . . . . ? C217 C218 C219 C220 -176.60(13) . . . . ? C217 C218 C219 C214 0.85(19) . . . . ? C213 C214 C219 C220 -0.71(19) . . . . ? C215 C214 C219 C220 177.32(12) . . . . ? C213 C214 C219 C218 -178.25(12) . . . . ? C215 C214 C219 C218 -0.22(18) . . . . ? O211 C211 C220 C219 -174.62(11) . . . . ? C212 C211 C220 C219 4.30(19) . . . . ? O211 C211 C220 C222 1.05(19) . . . . ? C212 C211 C220 C222 179.96(12) . . . . ? C218 C219 C220 C211 174.71(12) . . . . ? C214 C219 C220 C211 -2.69(19) . . . . ? C218 C219 C220 C222 -0.90(19) . . . . ? C214 C219 C220 C222 -178.29(12) . . . . ? C213 C212 C221 O222 -4.2(2) . . . . ? C211 C212 C221 O222 175.97(12) . . . . ? C213 C212 C221 O221 176.12(12) . . . . ? C211 C212 C221 O221 -3.69(19) . . . . ? C211 C220 C222 C223 113.90(14) . . . . ? C219 C220 C222 C223 -70.55(16) . . . . ? C220 C222 C223 C224 115.35(14) . . . . ? C220 C222 C223 C232 -67.86(16) . . . . ? C232 C223 C224 O224 -174.88(11) . . . . ? C222 C223 C224 O224 2.00(19) . . . . ? C232 C223 C224 C225 5.71(19) . . . . ? C222 C223 C224 C225 -177.41(12) . . . . ? O224 C224 C225 C226 178.11(12) . . . . ? C223 C224 C225 C226 -2.5(2) . . . . ? O224 C224 C225 C233 -4.01(19) . . . . ? C223 C224 C225 C233 175.39(12) . . . . ? O233 C233 C225 C226 179.19(13) . . . . ? O234 C233 C225 C226 0.42(18) . . . . ? O233 C233 C225 C224 1.3(2) . . . . ? O234 C233 C225 C224 -177.45(12) . . . . ? C224 C225 C226 C227 -1.6(2) . . . . ? C233 C225 C226 C227 -179.53(12) . . . . ? C225 C226 C227 C228 -176.74(13) . . . . ? C225 C226 C227 C232 2.26(19) . . . . ? C226 C227 C228 C229 177.71(13) . . . . ? C232 C227 C228 C229 -1.3(2) . . . . ? C227 C228 C229 C230 -0.5(2) . . . . ? C228 C229 C230 C231 1.6(2) . . . . ? C229 C230 C231 C232 -0.8(2) . . . . ? C230 C231 C232 C223 -179.09(13) . . . . ? C230 C231 C232 C227 -1.00(19) . . . . ? C224 C223 C232 C231 173.02(12) . . . . ? C222 C223 C232 C231 -3.84(19) . . . . ? C224 C223 C232 C227 -5.01(19) . . . . ? C222 C223 C232 C227 178.13(12) . . . . ? C226 C227 C232 C231 -177.01(12) . . . . ? C228 C227 C232 C231 2.00(18) . . . . ? C226 C227 C232 C223 1.11(19) . . . . ? C228 C227 C232 C223 -179.88(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 O221 1.00(2) 1.70(2) 2.6980(15) 174.9(17) . O211 H211 O221 0.94 1.65 2.5351(14) 156.1 . O224 H224 O233 0.94 1.72 2.5879(15) 152.4 . O234 H234 O222 0.98 1.56 2.5195(14) 164.7 4_465 _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.267 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.045 data_6 _database_code_depnum_ccdc_archive 'CCDC 915734' #TrackingRef 'web_deposit_cif_file_0_TanyaleRoex_1358257029.submission.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2-picolinium pamoate NMP solvate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 O6 1- , C6 H8 N 1+ , C5 H9 N O' _chemical_formula_sum 'C34 H32 N2 O7' _chemical_formula_weight 580.62 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' 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 13.7002(10) _cell_length_b 13.2762(10) _cell_length_c 16.7596(12) _cell_angle_alpha 90.00 _cell_angle_beta 112.4180(10) _cell_angle_gamma 90.00 _cell_volume 2818.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2482 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 26.94 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9748 _exptl_absorpt_correction_T_max 0.9895 _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 16492 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.10 _reflns_number_total 6003 _reflns_number_gt 3888 _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)' _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. The N11-H11 bond length was restrained, but despite this is still longer than expected. This appears to be because of strong hydrogen bonding between the cation and the solvent. ; _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^)+(0.0590P)^2^+1.2872P] 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 6003 _refine_ls_number_parameters 394 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0892 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1440 _refine_ls_wR_factor_gt 0.1222 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.068 _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 O224 O 0.26520(11) 0.79684(12) 0.24390(9) 0.0220(4) Uani 1 1 d . . . O211 O 0.59301(12) 0.80330(12) 0.12098(9) 0.0230(4) Uani 1 1 d . . . O233 O 0.08938(11) 0.73441(12) 0.24381(9) 0.0218(4) Uani 1 1 d . . . O221 O 0.76925(12) 0.74693(12) 0.12001(10) 0.0262(4) Uani 1 1 d . . . O222 O 0.86465(12) 0.63034(12) 0.21351(10) 0.0247(4) Uani 1 1 d . . . O234 O -0.00840(12) 0.62696(12) 0.14203(10) 0.0261(4) Uani 1 1 d . . . C225 C 0.15533(16) 0.67726(16) 0.13919(13) 0.0166(4) Uani 1 1 d . . . C211 C 0.60718(16) 0.73791(16) 0.18681(13) 0.0175(5) Uani 1 1 d . . . C224 C 0.25085(16) 0.73534(16) 0.17510(13) 0.0174(5) Uani 1 1 d . . . C212 C 0.70134(16) 0.67860(17) 0.21980(13) 0.0185(5) Uani 1 1 d . . . C226 C 0.13977(16) 0.61903(16) 0.06758(13) 0.0168(4) Uani 1 1 d . . . H226 H 0.0775 0.5795 0.0443 0.020 Uiso 1 1 calc R . . C214 C 0.64606(16) 0.61411(17) 0.33141(13) 0.0186(5) Uani 1 1 d . . . C220 C 0.53031(16) 0.73163(16) 0.22165(13) 0.0172(5) Uani 1 1 d . . . C228 C 0.19209(17) 0.56218(17) -0.05046(13) 0.0197(5) Uani 1 1 d . . . H228 H 0.1292 0.5236 -0.0744 0.024 Uiso 1 1 calc R . . C222 C 0.42884(16) 0.79279(16) 0.18229(13) 0.0178(4) Uani 1 1 d . . . H22A H 0.4214 0.8356 0.2280 0.021 Uiso 1 1 calc R . . H22B H 0.4356 0.8381 0.1378 0.021 Uiso 1 1 calc R . . C232 C 0.30897(16) 0.67246(16) 0.06514(13) 0.0168(4) Uani 1 1 d . . . C213 C 0.71774(16) 0.61662(17) 0.28922(13) 0.0197(5) Uani 1 1 d . . . H213 H 0.7784 0.5746 0.3093 0.024 Uiso 1 1 calc R . . C227 C 0.21320(16) 0.61626(16) 0.02782(13) 0.0171(4) Uani 1 1 d . . . C217 C 0.51092(18) 0.62024(18) 0.42038(14) 0.0234(5) Uani 1 1 d . . . H217 H 0.4655 0.6226 0.4513 0.028 Uiso 1 1 calc R . . C223 C 0.32848(16) 0.73072(16) 0.14135(13) 0.0167(5) Uani 1 1 d . . . C218 C 0.48394(16) 0.67217(17) 0.34467(13) 0.0195(5) Uani 1 1 d . . . H218 H 0.4195 0.7088 0.3231 0.023 Uiso 1 1 calc R . . C219 C 0.55160(16) 0.67201(17) 0.29738(13) 0.0175(5) Uani 1 1 d . . . C215 C 0.66994(18) 0.55932(18) 0.40961(14) 0.0241(5) Uani 1 1 d . . . H215 H 0.7322 0.5196 0.4313 0.029 Uiso 1 1 calc R . . C231 C 0.37989(17) 0.67202(17) 0.02099(13) 0.0190(5) Uani 1 1 d . . . H231 H 0.4448 0.7077 0.0447 0.023 Uiso 1 1 calc R . . C230 C 0.35546(17) 0.62079(17) -0.05517(13) 0.0216(5) Uani 1 1 d . . . H230 H 0.4031 0.6229 -0.0841 0.026 Uiso 1 1 calc R . . C233 C 0.07507(16) 0.68153(17) 0.17907(14) 0.0194(5) Uani 1 1 d . . . O1 O 0.78520(13) 0.49400(13) 0.69360(10) 0.0305(4) Uani 1 1 d . . . C221 C 0.78306(17) 0.68669(18) 0.18077(13) 0.0208(5) Uani 1 1 d . . . N2 N 0.86613(15) 0.43967(15) 0.60617(12) 0.0265(5) Uani 1 1 d . . . C229 C 0.26110(17) 0.56505(17) -0.09150(14) 0.0214(5) Uani 1 1 d . . . H229 H 0.2456 0.5297 -0.1442 0.026 Uiso 1 1 calc R . . C216 C 0.60470(18) 0.56314(18) 0.45371(14) 0.0256(5) Uani 1 1 d . . . H216 H 0.6222 0.5276 0.5066 0.031 Uiso 1 1 calc R . . C4 C 0.95191(18) 0.56974(18) 0.69770(15) 0.0275(5) Uani 1 1 d . . . H4A H 1.0032 0.5495 0.7553 0.033 Uiso 1 1 calc R . . H4B H 0.9292 0.6399 0.7008 0.033 Uiso 1 1 calc R . . C3 C 0.85842(19) 0.49923(18) 0.66704(14) 0.0254(5) Uani 1 1 d . . . C7 C 0.7972(2) 0.35440(18) 0.56997(15) 0.0301(6) Uani 1 1 d . . . H7A H 0.7395 0.3546 0.5909 0.045 Uiso 1 1 calc R . . H7B H 0.8376 0.2918 0.5877 0.045 Uiso 1 1 calc R . . H7C H 0.7680 0.3592 0.5068 0.045 Uiso 1 1 calc R . . C6 C 0.9626(2) 0.4537(2) 0.59075(16) 0.0318(6) Uani 1 1 d . . . H6A H 0.9486 0.4521 0.5283 0.038 Uiso 1 1 calc R . . H6B H 1.0156 0.4015 0.6206 0.038 Uiso 1 1 calc R . . C5 C 0.9996(2) 0.5592(2) 0.62937(17) 0.0360(6) Uani 1 1 d . . . H5A H 1.0776 0.5631 0.6557 0.043 Uiso 1 1 calc R . . H5B H 0.9727 0.6122 0.5847 0.043 Uiso 1 1 calc R . . N11 N 0.72612(16) 0.57217(15) 0.81223(12) 0.0295(5) Uani 1 1 d D . . C12 C 0.7800(2) 0.63072(19) 0.87949(15) 0.0311(6) Uani 1 1 d . . . C14 C 0.6376(2) 0.6161(2) 0.92769(16) 0.0361(6) Uani 1 1 d . . . H14 H 0.6077 0.6318 0.9689 0.043 Uiso 1 1 calc R . . C16 C 0.63050(18) 0.53407(18) 0.79905(15) 0.0258(5) Uani 1 1 d . . . H16 H 0.5950 0.4933 0.7499 0.031 Uiso 1 1 calc R . . C17 C 0.88811(19) 0.6654(2) 0.88587(17) 0.0379(7) Uani 1 1 d . . . H17A H 0.8805 0.7095 0.8369 0.057 Uiso 1 1 calc R . . H17B H 0.9310 0.6067 0.8849 0.057 Uiso 1 1 calc R . . H17C H 0.9227 0.7025 0.9399 0.057 Uiso 1 1 calc R . . C13 C 0.7355(2) 0.65453(19) 0.93705(16) 0.0307(6) Uani 1 1 d . . . H13 H 0.7718 0.6979 0.9841 0.037 Uiso 1 1 calc R . . C15 C 0.5834(2) 0.55453(19) 0.85780(16) 0.0338(6) Uani 1 1 d . . . H15 H 0.5164 0.5272 0.8503 0.041 Uiso 1 1 calc R . . H211 H 0.6551 0.8010 0.1068 0.050(9) Uiso 1 1 d R . . H224 H 0.2044 0.7870 0.2620 0.059(9) Uiso 1 1 d R . . H11 H 0.7611 0.5496 0.7675 0.093(12) Uiso 1 1 d RD . . H234 H -0.0609 0.6321 0.1711 0.092(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 O224 0.0178(8) 0.0291(9) 0.0209(8) -0.0079(7) 0.0092(6) -0.0016(7) O211 0.0186(8) 0.0307(9) 0.0215(8) 0.0052(7) 0.0097(6) -0.0019(7) O233 0.0186(8) 0.0279(9) 0.0207(8) -0.0021(7) 0.0095(6) 0.0016(7) O221 0.0247(9) 0.0329(10) 0.0263(9) 0.0005(8) 0.0159(7) -0.0022(7) O222 0.0170(8) 0.0329(10) 0.0278(8) -0.0026(7) 0.0126(7) 0.0003(7) O234 0.0177(8) 0.0350(10) 0.0294(9) -0.0076(8) 0.0134(7) -0.0057(7) C225 0.0139(10) 0.0186(11) 0.0170(10) 0.0032(9) 0.0055(8) 0.0032(9) C211 0.0171(10) 0.0198(12) 0.0152(10) -0.0042(9) 0.0055(8) -0.0062(9) C224 0.0159(10) 0.0187(11) 0.0162(10) -0.0005(9) 0.0046(8) 0.0008(9) C212 0.0149(10) 0.0217(12) 0.0199(11) -0.0064(9) 0.0076(9) -0.0044(9) C226 0.0131(10) 0.0171(11) 0.0169(10) 0.0025(9) 0.0021(8) 0.0010(9) C214 0.0167(10) 0.0199(11) 0.0192(11) -0.0025(9) 0.0068(9) -0.0021(9) C220 0.0148(10) 0.0202(11) 0.0154(10) -0.0042(9) 0.0045(8) -0.0036(9) C228 0.0186(11) 0.0197(12) 0.0181(11) 0.0001(9) 0.0038(9) -0.0008(9) C222 0.0169(10) 0.0186(11) 0.0181(10) -0.0012(9) 0.0070(8) -0.0004(9) C232 0.0156(10) 0.0173(11) 0.0166(10) 0.0040(9) 0.0052(8) 0.0022(9) C213 0.0153(10) 0.0211(12) 0.0216(11) -0.0028(9) 0.0059(9) 0.0016(9) C227 0.0174(11) 0.0162(11) 0.0169(10) 0.0027(9) 0.0057(8) 0.0022(9) C217 0.0232(12) 0.0284(13) 0.0233(11) -0.0031(10) 0.0139(10) -0.0040(10) C223 0.0133(10) 0.0191(11) 0.0167(10) 0.0030(9) 0.0044(8) 0.0015(9) C218 0.0159(10) 0.0230(12) 0.0204(11) -0.0038(9) 0.0079(9) -0.0023(9) C219 0.0152(10) 0.0208(11) 0.0168(10) -0.0054(9) 0.0065(8) -0.0049(9) C215 0.0195(11) 0.0266(13) 0.0260(12) 0.0027(10) 0.0087(9) 0.0035(10) C231 0.0164(10) 0.0231(12) 0.0173(11) 0.0031(9) 0.0061(8) 0.0011(9) C230 0.0212(11) 0.0274(13) 0.0203(11) 0.0021(10) 0.0126(9) 0.0030(10) C233 0.0165(11) 0.0214(12) 0.0204(11) 0.0041(9) 0.0073(9) 0.0041(9) O1 0.0296(9) 0.0316(10) 0.0348(9) -0.0052(8) 0.0175(8) -0.0046(8) C221 0.0175(11) 0.0267(13) 0.0188(11) -0.0082(10) 0.0074(9) -0.0047(9) N2 0.0272(11) 0.0269(11) 0.0230(10) -0.0010(9) 0.0069(8) -0.0020(9) C229 0.0256(12) 0.0216(12) 0.0171(10) -0.0025(9) 0.0081(9) -0.0001(10) C216 0.0293(13) 0.0274(13) 0.0218(11) 0.0040(10) 0.0116(10) -0.0004(10) C4 0.0248(12) 0.0265(13) 0.0312(13) -0.0035(11) 0.0105(10) -0.0025(10) C3 0.0280(13) 0.0228(13) 0.0217(12) 0.0024(10) 0.0054(10) 0.0035(10) C7 0.0356(14) 0.0252(13) 0.0235(12) -0.0025(10) 0.0044(10) -0.0049(11) C6 0.0298(13) 0.0370(15) 0.0324(13) -0.0037(12) 0.0160(11) -0.0020(12) C5 0.0306(14) 0.0372(16) 0.0439(15) -0.0066(13) 0.0183(12) -0.0066(12) N11 0.0295(11) 0.0283(12) 0.0278(11) 0.0075(9) 0.0077(9) 0.0076(9) C12 0.0356(14) 0.0259(14) 0.0271(13) 0.0068(11) 0.0068(11) 0.0074(11) C14 0.0414(16) 0.0373(16) 0.0325(14) 0.0063(12) 0.0172(12) 0.0124(13) C16 0.0258(12) 0.0215(12) 0.0284(12) 0.0026(10) 0.0084(10) 0.0024(10) C17 0.0270(13) 0.0353(15) 0.0429(16) 0.0077(13) 0.0037(12) 0.0024(12) C13 0.0364(14) 0.0242(13) 0.0274(13) 0.0023(11) 0.0076(11) 0.0077(11) C15 0.0322(14) 0.0310(15) 0.0388(14) 0.0085(12) 0.0141(12) 0.0057(12) _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 O224 C224 1.364(2) . ? O224 H224 0.9980 . ? O211 C211 1.358(2) . ? O211 H211 0.9669 . ? O233 C233 1.244(2) . ? O221 C221 1.251(3) . ? O222 C221 1.282(3) . ? O234 C233 1.295(3) . ? O234 H234 1.0133 . ? C225 C226 1.374(3) . ? C225 C224 1.438(3) . ? C225 C233 1.490(3) . ? C211 C220 1.388(3) . ? C211 C212 1.430(3) . ? C224 C223 1.383(3) . ? C212 C213 1.372(3) . ? C212 C221 1.501(3) . ? C226 C227 1.403(3) . ? C226 H226 0.9500 . ? C214 C213 1.412(3) . ? C214 C215 1.424(3) . ? C214 C219 1.424(3) . ? C220 C219 1.428(3) . ? C220 C222 1.526(3) . ? C228 C229 1.365(3) . ? C228 C227 1.425(3) . ? C228 H228 0.9500 . ? C222 C223 1.523(3) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C232 C231 1.428(3) . ? C232 C223 1.428(3) . ? C232 C227 1.429(3) . ? C213 H213 0.9500 . ? C217 C218 1.365(3) . ? C217 C216 1.411(3) . ? C217 H217 0.9500 . ? C218 C219 1.431(3) . ? C218 H218 0.9500 . ? C215 C216 1.361(3) . ? C215 H215 0.9500 . ? C231 C230 1.370(3) . ? C231 H231 0.9500 . ? C230 C229 1.410(3) . ? C230 H230 0.9500 . ? O1 C3 1.245(3) . ? N2 C3 1.326(3) . ? N2 C7 1.451(3) . ? N2 C6 1.452(3) . ? C229 H229 0.9500 . ? C216 H216 0.9500 . ? C4 C3 1.510(3) . ? C4 C5 1.526(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C6 C5 1.545(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? N11 C12 1.336(3) . ? N11 C16 1.342(3) . ? N11 H11 1.0755 . ? C12 C13 1.361(3) . ? C12 C17 1.515(4) . ? C14 C13 1.387(4) . ? C14 C15 1.388(4) . ? C14 H14 0.9500 . ? C16 C15 1.394(3) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C13 H13 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C224 O224 H224 108.1 . . ? C211 O211 H211 108.2 . . ? C233 O234 H234 113.0 . . ? C226 C225 C224 118.72(19) . . ? C226 C225 C233 121.19(19) . . ? C224 C225 C233 120.09(18) . . ? O211 C211 C220 118.94(19) . . ? O211 C211 C212 119.62(18) . . ? C220 C211 C212 121.43(19) . . ? O224 C224 C223 119.12(18) . . ? O224 C224 C225 119.29(18) . . ? C223 C224 C225 121.59(19) . . ? C213 C212 C211 119.33(19) . . ? C213 C212 C221 120.31(19) . . ? C211 C212 C221 120.33(19) . . ? C225 C226 C227 121.93(19) . . ? C225 C226 H226 119.0 . . ? C227 C226 H226 119.0 . . ? C213 C214 C215 120.9(2) . . ? C213 C214 C219 119.07(19) . . ? C215 C214 C219 119.94(19) . . ? C211 C220 C219 118.47(19) . . ? C211 C220 C222 119.91(18) . . ? C219 C220 C222 121.51(18) . . ? C229 C228 C227 120.9(2) . . ? C229 C228 H228 119.6 . . ? C227 C228 H228 119.6 . . ? C223 C222 C220 115.08(17) . . ? C223 C222 H22A 108.5 . . ? C220 C222 H22A 108.5 . . ? C223 C222 H22B 108.5 . . ? C220 C222 H22B 108.5 . . ? H22A C222 H22B 107.5 . . ? C231 C232 C223 122.21(19) . . ? C231 C232 C227 117.60(19) . . ? C223 C232 C227 120.10(18) . . ? C212 C213 C214 121.2(2) . . ? C212 C213 H213 119.4 . . ? C214 C213 H213 119.4 . . ? C226 C227 C228 121.32(19) . . ? C226 C227 C232 118.89(19) . . ? C228 C227 C232 119.74(19) . . ? C218 C217 C216 121.5(2) . . ? C218 C217 H217 119.3 . . ? C216 C217 H217 119.3 . . ? C224 C223 C232 118.60(19) . . ? C224 C223 C222 119.63(18) . . ? C232 C223 C222 121.64(18) . . ? C217 C218 C219 120.7(2) . . ? C217 C218 H218 119.6 . . ? C219 C218 H218 119.6 . . ? C214 C219 C220 120.09(18) . . ? C214 C219 C218 117.43(19) . . ? C220 C219 C218 122.38(19) . . ? C216 C215 C214 120.9(2) . . ? C216 C215 H215 119.6 . . ? C214 C215 H215 119.6 . . ? C230 C231 C232 120.8(2) . . ? C230 C231 H231 119.6 . . ? C232 C231 H231 119.6 . . ? C231 C230 C229 121.4(2) . . ? C231 C230 H230 119.3 . . ? C229 C230 H230 119.3 . . ? O233 C233 O234 123.42(19) . . ? O233 C233 C225 121.01(19) . . ? O234 C233 C225 115.58(18) . . ? O221 C221 O222 123.93(19) . . ? O221 C221 C212 119.6(2) . . ? O222 C221 C212 116.45(19) . . ? C3 N2 C7 123.8(2) . . ? C3 N2 C6 113.9(2) . . ? C7 N2 C6 121.1(2) . . ? C228 C229 C230 119.6(2) . . ? C228 C229 H229 120.2 . . ? C230 C229 H229 120.2 . . ? C215 C216 C217 119.5(2) . . ? C215 C216 H216 120.2 . . ? C217 C216 H216 120.2 . . ? C3 C4 C5 103.76(19) . . ? C3 C4 H4A 111.0 . . ? C5 C4 H4A 111.0 . . ? C3 C4 H4B 111.0 . . ? C5 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? O1 C3 N2 123.6(2) . . ? O1 C3 C4 127.4(2) . . ? N2 C3 C4 109.0(2) . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C6 C5 102.53(19) . . ? N2 C6 H6A 111.3 . . ? C5 C6 H6A 111.3 . . ? N2 C6 H6B 111.3 . . ? C5 C6 H6B 111.3 . . ? H6A C6 H6B 109.2 . . ? C4 C5 C6 103.4(2) . . ? C4 C5 H5A 111.1 . . ? C6 C5 H5A 111.1 . . ? C4 C5 H5B 111.1 . . ? C6 C5 H5B 111.1 . . ? H5A C5 H5B 109.0 . . ? C12 N11 C16 123.3(2) . . ? C12 N11 H11 120.1 . . ? C16 N11 H11 116.5 . . ? N11 C12 C13 118.7(2) . . ? N11 C12 C17 116.6(2) . . ? C13 C12 C17 124.7(2) . . ? C13 C14 C15 119.7(2) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? N11 C16 C15 119.7(2) . . ? N11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C12 C13 C14 120.7(2) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C14 C15 C16 117.9(2) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C226 C225 C224 O224 177.17(18) . . . . ? C233 C225 C224 O224 -2.3(3) . . . . ? C226 C225 C224 C223 -2.6(3) . . . . ? C233 C225 C224 C223 177.95(19) . . . . ? O211 C211 C212 C213 176.60(18) . . . . ? C220 C211 C212 C213 -2.2(3) . . . . ? O211 C211 C212 C221 -1.4(3) . . . . ? C220 C211 C212 C221 179.85(19) . . . . ? C224 C225 C226 C227 -1.2(3) . . . . ? C233 C225 C226 C227 178.24(19) . . . . ? O211 C211 C220 C219 -172.50(18) . . . . ? C212 C211 C220 C219 6.3(3) . . . . ? O211 C211 C220 C222 3.8(3) . . . . ? C212 C211 C220 C222 -177.43(19) . . . . ? C211 C220 C222 C223 114.9(2) . . . . ? C219 C220 C222 C223 -68.9(2) . . . . ? C211 C212 C213 C214 -3.2(3) . . . . ? C221 C212 C213 C214 174.71(19) . . . . ? C215 C214 C213 C212 -172.1(2) . . . . ? C219 C214 C213 C212 4.3(3) . . . . ? C225 C226 C227 C228 -174.7(2) . . . . ? C225 C226 C227 C232 2.7(3) . . . . ? C229 C228 C227 C226 175.9(2) . . . . ? C229 C228 C227 C232 -1.5(3) . . . . ? C231 C232 C227 C226 -177.10(19) . . . . ? C223 C232 C227 C226 -0.4(3) . . . . ? C231 C232 C227 C228 0.3(3) . . . . ? C223 C232 C227 C228 177.04(19) . . . . ? O224 C224 C223 C232 -175.01(18) . . . . ? C225 C224 C223 C232 4.7(3) . . . . ? O224 C224 C223 C222 1.0(3) . . . . ? C225 C224 C223 C222 -179.32(18) . . . . ? C231 C232 C223 C224 173.3(2) . . . . ? C227 C232 C223 C224 -3.2(3) . . . . ? C231 C232 C223 C222 -2.5(3) . . . . ? C227 C232 C223 C222 -179.10(19) . . . . ? C220 C222 C223 C224 116.7(2) . . . . ? C220 C222 C223 C232 -67.5(2) . . . . ? C216 C217 C218 C219 -1.3(3) . . . . ? C213 C214 C219 C220 0.0(3) . . . . ? C215 C214 C219 C220 176.43(19) . . . . ? C213 C214 C219 C218 -176.45(19) . . . . ? C215 C214 C219 C218 0.0(3) . . . . ? C211 C220 C219 C214 -5.1(3) . . . . ? C222 C220 C219 C214 178.66(19) . . . . ? C211 C220 C219 C218 171.1(2) . . . . ? C222 C220 C219 C218 -5.1(3) . . . . ? C217 C218 C219 C214 1.4(3) . . . . ? C217 C218 C219 C220 -175.0(2) . . . . ? C213 C214 C215 C216 174.9(2) . . . . ? C219 C214 C215 C216 -1.5(3) . . . . ? C223 C232 C231 C230 -175.5(2) . . . . ? C227 C232 C231 C230 1.1(3) . . . . ? C232 C231 C230 C229 -1.5(3) . . . . ? C226 C225 C233 O233 -179.9(2) . . . . ? C224 C225 C233 O233 -0.4(3) . . . . ? C226 C225 C233 O234 0.3(3) . . . . ? C224 C225 C233 O234 179.77(19) . . . . ? C213 C212 C221 O221 -176.75(19) . . . . ? C211 C212 C221 O221 1.2(3) . . . . ? C213 C212 C221 O222 2.7(3) . . . . ? C211 C212 C221 O222 -179.37(19) . . . . ? C227 C228 C229 C230 1.1(3) . . . . ? C231 C230 C229 C228 0.3(3) . . . . ? C214 C215 C216 C217 1.5(3) . . . . ? C218 C217 C216 C215 -0.1(3) . . . . ? C7 N2 C3 O1 -7.1(4) . . . . ? C6 N2 C3 O1 -175.1(2) . . . . ? C7 N2 C3 C4 171.9(2) . . . . ? C6 N2 C3 C4 3.9(3) . . . . ? C5 C4 C3 O1 -167.3(2) . . . . ? C5 C4 C3 N2 13.8(3) . . . . ? C3 N2 C6 C5 -19.5(3) . . . . ? C7 N2 C6 C5 172.1(2) . . . . ? C3 C4 C5 C6 -24.5(2) . . . . ? N2 C6 C5 C4 26.3(2) . . . . ? C16 N11 C12 C13 -1.1(3) . . . . ? C16 N11 C12 C17 178.6(2) . . . . ? C12 N11 C16 C15 -0.6(3) . . . . ? N11 C12 C13 C14 2.1(4) . . . . ? C17 C12 C13 C14 -177.5(2) . . . . ? C15 C14 C13 C12 -1.5(4) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? N11 C16 C15 C14 1.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O1 1.08 1.58 2.629(3) 163.4 . O211 H211 O221 0.97 1.66 2.534(2) 148.7 . O224 H224 O233 1.00 1.64 2.547(2) 148.4 . O234 H234 O222 1.01 1.45 2.460(2) 175.2 1_455 _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.794 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.055 #=== END