# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'Dr Delia Haynes, Dr Tanya le Roex' _publ_contact_author_address ; Department of Chemistry and Polymer Science Stellenbosch University P. Bag X1 Matieland 7602 Republic of South Africa ; _publ_contact_author_email 'dhaynes@sun.ac.za, tlr@sun.ac.za' loop_ _publ_author_name _publ_author_address H.Wahl ; Department of Chemistry and Polymer Science Stellenbosch University P. Bag X1 Matieland 7602 Republic of South Africa ; D.Haynes ; Department of Chemistry and Polymer Science Stellenbosch University P. Bag X1 Matieland 7602 Republic of South Africa ; 'T.le Roex' ; Department of Chemistry and Polymer Science Stellenbosch University P. Bag X1 Matieland 7602 Republic of South Africa ; _publ_section_title ; Porous salts based on the pamoate ion ; data_1.THF _database_code_depnum_ccdc_archive 'CCDC 837700' #TrackingRef '- revision_2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,4 lutidinium pamoate hydrate THF solvate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N 1+ , C23 H15 O6 1- , 1/2(H2 O), C4 H8 O' _chemical_formula_sum 'C34 H34 N O7.50' _chemical_formula_weight 576.62 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 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 22.1174(13) _cell_length_b 19.8568(12) _cell_length_c 14.6154(8) _cell_angle_alpha 90.00 _cell_angle_beta 115.2400(10) _cell_angle_gamma 90.00 _cell_volume 5806.0(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6065 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.16 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2440 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6900 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _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 '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 17384 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.18 _reflns_number_total 6253 _reflns_number_gt 5081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0721P)^2^+3.6256P] 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 6253 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1185 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.007 _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 0.5000 0.34065(7) 0.2500 0.0226(3) Uani 1 2 d S . . H1 H 0.5093(10) 0.3710(10) 0.3021(15) 0.049(6) Uiso 1 1 d . . . O2 O 0.56201(18) -0.1047(3) 0.7094(3) 0.1022(15) Uani 0.50 1 d P A -1 C2 C 0.4992(2) -0.1111(3) 0.6308(4) 0.0669(13) Uani 0.50 1 d P A -1 H2A H 0.4981 -0.1492 0.5865 0.080 Uiso 0.50 1 calc PR A -1 H2B H 0.4867 -0.0694 0.5897 0.080 Uiso 0.50 1 calc PR A -1 O3 O -0.0215(3) 0.4246(3) 0.2964(6) 0.120(2) Uani 0.50 1 d P B -1 C3 C 0.4535(5) -0.1231(6) 0.6761(8) 0.099(3) Uani 0.50 1 d P A -1 H3A H 0.4183 -0.0880 0.6540 0.119 Uiso 0.50 1 calc PR A -1 H3B H 0.4317 -0.1675 0.6544 0.119 Uiso 0.50 1 calc PR A -1 C4 C 0.4902(3) -0.1216(5) 0.7849(5) 0.114(3) Uani 0.50 1 d P A -1 H4A H 0.4895 -0.1663 0.8144 0.137 Uiso 0.50 1 calc PR A -1 H4B H 0.4709 -0.0879 0.8149 0.137 Uiso 0.50 1 calc PR A -1 C5 C 0.5584(4) -0.1029(4) 0.8032(6) 0.0586(17) Uani 0.50 1 d P A -1 H5A H 0.5690 -0.0572 0.8327 0.070 Uiso 0.50 1 calc PR A -1 H5B H 0.5908 -0.1350 0.8509 0.070 Uiso 0.50 1 calc PR A -1 C6 C -0.0225(5) 0.4129(4) 0.2012(7) 0.100(2) Uani 0.50 1 d P B -1 H6A H 0.0135 0.4384 0.1936 0.120 Uiso 0.50 1 calc PR B -1 H6B H -0.0660 0.4265 0.1466 0.120 Uiso 0.50 1 calc PR B -1 C7 C -0.0123(9) 0.3413(7) 0.1978(16) 0.155(8) Uani 0.50 1 d P B -1 H7A H 0.0130 0.3317 0.1573 0.186 Uiso 0.50 1 calc PR B -1 H7B H -0.0558 0.3177 0.1664 0.186 Uiso 0.50 1 calc PR B -1 C8 C 0.0261(4) 0.3181(5) 0.3040(13) 0.082(3) Uani 0.50 1 d P B -1 H8A H 0.0151 0.2709 0.3127 0.099 Uiso 0.50 1 calc PR B -1 H8B H 0.0749 0.3219 0.3251 0.099 Uiso 0.50 1 calc PR B -1 C9 C 0.0036(5) 0.3649(5) 0.3612(7) 0.109(3) Uani 0.50 1 d P B -1 H9A H -0.0324 0.3443 0.3752 0.131 Uiso 0.50 1 calc PR B -1 H9B H 0.0411 0.3772 0.4263 0.131 Uiso 0.50 1 calc PR B -1 N11 N -0.11658(6) -0.00801(6) 0.37402(9) 0.0236(3) Uani 1 1 d . . . H11 H -0.0766(11) 0.0127(10) 0.3751(15) 0.047(6) Uiso 1 1 d . . . C12 C -0.16857(7) 0.03214(8) 0.35938(11) 0.0262(3) Uani 1 1 d . . . H12 H -0.1636 0.0795 0.3564 0.031 Uiso 1 1 calc R . . C13 C -0.22961(7) 0.00623(8) 0.34850(11) 0.0256(3) Uani 1 1 d . . . C14 C -0.23531(7) -0.06384(8) 0.35284(10) 0.0248(3) Uani 1 1 d . . . C15 C -0.17924(8) -0.10338(8) 0.37227(11) 0.0274(3) Uani 1 1 d . . . H15 H -0.1818 -0.1508 0.3788 0.033 Uiso 1 1 calc R . . C16 C -0.12026(7) -0.07462(8) 0.38213(11) 0.0259(3) Uani 1 1 d . . . H16 H -0.0823 -0.1020 0.3947 0.031 Uiso 1 1 calc R . . C17 C -0.28641(8) 0.05272(9) 0.33384(13) 0.0343(4) Uani 1 1 d . . . H17A H -0.2978 0.0486 0.3915 0.051 Uiso 1 1 calc R . . H17B H -0.3254 0.0407 0.2714 0.051 Uiso 1 1 calc R . . H17C H -0.2732 0.0992 0.3290 0.051 Uiso 1 1 calc R . . C18 C -0.30064(8) -0.09605(9) 0.33708(12) 0.0327(4) Uani 1 1 d . . . H18A H -0.3357 -0.0816 0.2719 0.049 Uiso 1 1 calc R . . H18B H -0.3126 -0.0824 0.3916 0.049 Uiso 1 1 calc R . . H18C H -0.2961 -0.1452 0.3374 0.049 Uiso 1 1 calc R . . O211 O 0.08038(5) 0.13038(5) 0.37853(8) 0.0250(2) Uani 1 1 d . . . C211 C 0.12270(7) 0.07969(7) 0.38274(10) 0.0212(3) Uani 1 1 d . . . H211 H 0.0429(13) 0.1068(12) 0.3716(18) 0.066(7) Uiso 1 1 d . . . C212 C 0.10152(7) 0.01140(7) 0.38077(10) 0.0207(3) Uani 1 1 d . . . C213 C 0.14427(7) -0.03976(7) 0.38508(10) 0.0228(3) Uani 1 1 d . . . H213 H 0.1298 -0.0851 0.3820 0.027 Uiso 1 1 calc R . . C214 C 0.20924(7) -0.02650(7) 0.39401(10) 0.0222(3) Uani 1 1 d . . . C215 C 0.25365(8) -0.08008(8) 0.40139(11) 0.0269(3) Uani 1 1 d . . . H215 H 0.2382 -0.1252 0.3952 0.032 Uiso 1 1 calc R . . C216 C 0.31836(8) -0.06788(8) 0.41727(12) 0.0295(3) Uani 1 1 d . . . H216 H 0.3476 -0.1041 0.4222 0.035 Uiso 1 1 calc R . . C217 C 0.34079(7) -0.00082(8) 0.42625(11) 0.0282(3) Uani 1 1 d . . . H217 H 0.3859 0.0079 0.4386 0.034 Uiso 1 1 calc R . . C218 C 0.29894(7) 0.05230(8) 0.41751(11) 0.0247(3) Uani 1 1 d . . . H218 H 0.3155 0.0970 0.4233 0.030 Uiso 1 1 calc R . . C219 C 0.23106(7) 0.04168(7) 0.39990(10) 0.0213(3) Uani 1 1 d . . . C220 C 0.18632(7) 0.09556(7) 0.39186(10) 0.0213(3) Uani 1 1 d . . . O221 O -0.00314(5) 0.04361(5) 0.37648(8) 0.0265(2) Uani 1 1 d . . . C221 C 0.03469(7) -0.00568(7) 0.37942(10) 0.0220(3) Uani 1 1 d . . . O222 O 0.01982(5) -0.06576(5) 0.38421(8) 0.0282(2) Uani 1 1 d . . . C222 C 0.20796(7) 0.16903(7) 0.40111(10) 0.0223(3) Uani 1 1 d . . . H22A H 0.1717 0.1971 0.4034 0.027 Uiso 1 1 calc R . . H22B H 0.2476 0.1749 0.4664 0.027 Uiso 1 1 calc R . . C223 C 0.22492(7) 0.19563(7) 0.31719(10) 0.0210(3) Uani 1 1 d . . . O224 O 0.33665(5) 0.21315(6) 0.43689(7) 0.0267(2) Uani 1 1 d . . . C224 C 0.28975(7) 0.21533(7) 0.33889(10) 0.0214(3) Uani 1 1 d . . . H224 H 0.3738(11) 0.2277(11) 0.4342(16) 0.053(6) Uiso 1 1 d . . . C225 C 0.30776(7) 0.23774(7) 0.26127(10) 0.0209(3) Uani 1 1 d . . . C226 C 0.25991(7) 0.24102(7) 0.16295(11) 0.0220(3) Uani 1 1 d . . . H226 H 0.2725 0.2542 0.1110 0.026 Uiso 1 1 calc R . . C227 C 0.19274(7) 0.22521(7) 0.13777(11) 0.0215(3) Uani 1 1 d . . . C228 C 0.14323(7) 0.23153(8) 0.03676(11) 0.0263(3) Uani 1 1 d . . . H228 H 0.1558 0.2454 -0.0149 0.032 Uiso 1 1 calc R . . C229 C 0.07787(7) 0.21784(8) 0.01324(12) 0.0290(3) Uani 1 1 d . . . H229 H 0.0450 0.2221 -0.0545 0.035 Uiso 1 1 calc R . . C230 C 0.05934(7) 0.19737(8) 0.09001(12) 0.0276(3) Uani 1 1 d . . . H230 H 0.0136 0.1885 0.0734 0.033 Uiso 1 1 calc R . . C231 C 0.10572(7) 0.18997(7) 0.18813(11) 0.0243(3) Uani 1 1 d . . . H231 H 0.0918 0.1759 0.2382 0.029 Uiso 1 1 calc R . . C232 C 0.17463(7) 0.20318(7) 0.21592(10) 0.0207(3) Uani 1 1 d . . . O233 O 0.42048(5) 0.26283(5) 0.37396(8) 0.0272(2) Uani 1 1 d . . . C233 C 0.37697(7) 0.26062(7) 0.28684(11) 0.0218(3) Uani 1 1 d . . . O234 O 0.38701(5) 0.28078(6) 0.20864(8) 0.0296(3) Uani 1 1 d . . . H234 H 0.4307(11) 0.3011(11) 0.2325(16) 0.059(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0167(7) 0.0247(8) 0.0272(8) 0.000 0.0101(6) 0.000 O2 0.049(2) 0.181(5) 0.070(3) -0.031(3) 0.0186(18) -0.037(3) C2 0.056(3) 0.058(3) 0.072(3) -0.007(2) 0.013(2) 0.002(2) O3 0.105(5) 0.072(3) 0.159(7) -0.003(3) 0.034(4) 0.000(3) C3 0.047(5) 0.162(11) 0.079(5) -0.023(6) 0.019(4) -0.019(5) C4 0.063(4) 0.200(9) 0.070(4) 0.013(4) 0.018(3) -0.063(5) C5 0.044(3) 0.066(3) 0.058(4) -0.005(3) 0.014(3) -0.018(2) C6 0.082(5) 0.096(6) 0.119(7) 0.024(5) 0.040(5) 0.032(4) C7 0.214(17) 0.086(11) 0.135(11) -0.009(9) 0.047(15) 0.060(10) C8 0.053(3) 0.065(6) 0.136(7) 0.034(5) 0.047(4) -0.003(3) C9 0.119(6) 0.084(6) 0.098(6) 0.002(5) 0.021(5) -0.008(5) N11 0.0225(6) 0.0288(7) 0.0221(6) -0.0010(5) 0.0119(5) -0.0032(5) C12 0.0293(8) 0.0254(8) 0.0254(7) 0.0013(6) 0.0129(6) -0.0012(6) C13 0.0260(7) 0.0326(8) 0.0191(7) 0.0011(6) 0.0105(6) 0.0001(6) C14 0.0239(7) 0.0340(8) 0.0179(7) -0.0026(6) 0.0103(6) -0.0055(6) C15 0.0315(8) 0.0274(8) 0.0277(7) -0.0026(6) 0.0166(6) -0.0041(6) C16 0.0277(7) 0.0280(8) 0.0251(7) -0.0015(6) 0.0141(6) -0.0003(6) C17 0.0292(8) 0.0398(9) 0.0359(9) 0.0030(7) 0.0158(7) 0.0052(7) C18 0.0270(8) 0.0427(10) 0.0309(8) -0.0030(7) 0.0147(6) -0.0097(7) O211 0.0211(5) 0.0236(5) 0.0345(6) 0.0000(4) 0.0159(4) 0.0002(4) C211 0.0217(7) 0.0238(7) 0.0197(7) 0.0007(5) 0.0104(5) 0.0015(5) C212 0.0208(7) 0.0252(7) 0.0169(6) -0.0005(5) 0.0088(5) -0.0022(5) C213 0.0254(7) 0.0233(7) 0.0205(7) -0.0006(5) 0.0107(6) -0.0031(6) C214 0.0232(7) 0.0262(7) 0.0174(7) 0.0002(5) 0.0089(5) 0.0009(6) C215 0.0299(8) 0.0265(8) 0.0255(7) -0.0005(6) 0.0131(6) 0.0027(6) C216 0.0284(8) 0.0347(9) 0.0279(8) 0.0026(6) 0.0144(6) 0.0091(6) C217 0.0220(7) 0.0368(9) 0.0271(8) 0.0036(6) 0.0118(6) 0.0039(6) C218 0.0228(7) 0.0293(8) 0.0232(7) 0.0036(6) 0.0109(6) 0.0000(6) C219 0.0219(7) 0.0275(7) 0.0155(6) 0.0018(5) 0.0091(5) 0.0003(5) C220 0.0223(7) 0.0249(7) 0.0183(6) 0.0009(5) 0.0101(5) -0.0005(5) O221 0.0216(5) 0.0269(6) 0.0345(6) -0.0013(4) 0.0153(4) -0.0016(4) C221 0.0222(7) 0.0271(7) 0.0189(6) -0.0025(5) 0.0110(5) -0.0032(6) O222 0.0312(6) 0.0255(6) 0.0351(6) -0.0030(4) 0.0209(5) -0.0053(4) C222 0.0203(7) 0.0253(7) 0.0224(7) -0.0002(5) 0.0102(5) -0.0010(5) C223 0.0206(7) 0.0195(7) 0.0244(7) 0.0000(5) 0.0109(6) -0.0013(5) O224 0.0191(5) 0.0356(6) 0.0214(5) 0.0012(4) 0.0049(4) -0.0064(4) C224 0.0191(6) 0.0212(7) 0.0212(7) 0.0002(5) 0.0061(5) -0.0009(5) C225 0.0179(6) 0.0199(7) 0.0245(7) -0.0021(5) 0.0087(5) -0.0029(5) C226 0.0204(7) 0.0218(7) 0.0244(7) 0.0004(5) 0.0102(6) -0.0032(5) C227 0.0178(6) 0.0212(7) 0.0246(7) -0.0007(5) 0.0082(6) -0.0017(5) C228 0.0219(7) 0.0316(8) 0.0244(7) 0.0022(6) 0.0091(6) -0.0029(6) C229 0.0184(7) 0.0366(9) 0.0261(8) 0.0019(6) 0.0039(6) -0.0023(6) C230 0.0165(6) 0.0291(8) 0.0346(8) 0.0034(6) 0.0083(6) -0.0022(6) C231 0.0197(7) 0.0235(7) 0.0311(8) 0.0030(6) 0.0121(6) -0.0012(5) C232 0.0186(6) 0.0181(7) 0.0246(7) -0.0004(5) 0.0084(5) -0.0010(5) O233 0.0177(5) 0.0349(6) 0.0260(5) 0.0007(4) 0.0064(4) -0.0035(4) C233 0.0181(7) 0.0220(7) 0.0246(7) -0.0014(5) 0.0084(6) -0.0023(5) O234 0.0193(5) 0.0420(7) 0.0270(6) 0.0006(5) 0.0094(4) -0.0096(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 O1 H1 0.92(2) . ? O2 C2 1.381(6) . ? O2 C5 1.407(8) . ? C2 C3 1.445(11) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? O3 C6 1.401(9) . ? O3 C9 1.471(11) . ? C3 C4 1.444(11) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.463(8) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.444(15) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.490(13) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.473(18) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N11 C16 1.334(2) . ? N11 C12 1.3393(19) . ? N11 H11 0.97(2) . ? C12 C13 1.389(2) . ? C12 H12 0.9500 . ? C13 C14 1.401(2) . ? C13 C17 1.499(2) . ? C14 C15 1.391(2) . ? C14 C18 1.505(2) . ? C15 C16 1.374(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 . ? O211 C211 1.3577(17) . ? O211 H211 0.92(3) . ? C211 C220 1.3918(19) . ? C211 C212 1.431(2) . ? C212 C213 1.371(2) . ? C212 C221 1.5084(19) . ? C213 C214 1.411(2) . ? C213 H213 0.9500 . ? C214 C215 1.421(2) . ? C214 C219 1.428(2) . ? C215 C216 1.370(2) . ? C215 H215 0.9500 . ? C216 C217 1.407(2) . ? C216 H216 0.9500 . ? C217 C218 1.373(2) . ? C217 H217 0.9500 . ? C218 C219 1.427(2) . ? C218 H218 0.9500 . ? C219 C220 1.428(2) . ? C220 C222 1.523(2) . ? O221 C221 1.2764(17) . ? C221 O222 1.2473(18) . ? C222 C223 1.5220(19) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C223 C224 1.3864(19) . ? C223 C232 1.4305(19) . ? O224 C224 1.3646(16) . ? O224 H224 0.89(2) . ? C224 C225 1.424(2) . ? C225 C226 1.3756(19) . ? C225 C233 1.4837(18) . ? C226 C227 1.4053(19) . ? C226 H226 0.9500 . ? C227 C228 1.4197(19) . ? C227 C232 1.431(2) . ? C228 C229 1.363(2) . ? C228 H228 0.9500 . ? C229 C230 1.409(2) . ? C229 H229 0.9500 . ? C230 C231 1.370(2) . ? C230 H230 0.9500 . ? C231 C232 1.4242(19) . ? C231 H231 0.9500 . ? O233 C233 1.2265(17) . ? C233 O234 1.3162(17) . ? O234 H234 0.96(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 C5 110.9(5) . . ? O2 C2 C3 106.6(6) . . ? O2 C2 H2A 110.4 . . ? C3 C2 H2A 110.4 . . ? O2 C2 H2B 110.4 . . ? C3 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? C6 O3 C9 110.4(7) . . ? C4 C3 C2 109.1(7) . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? C4 C3 H3B 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C3 C4 C5 104.9(6) . . ? C3 C4 H4A 110.8 . . ? C5 C4 H4A 110.8 . . ? C3 C4 H4B 110.8 . . ? C5 C4 H4B 110.8 . . ? H4A C4 H4B 108.8 . . ? O2 C5 C4 107.4(6) . . ? O2 C5 H5A 110.2 . . ? C4 C5 H5A 110.2 . . ? O2 C5 H5B 110.2 . . ? C4 C5 H5B 110.2 . . ? H5A C5 H5B 108.5 . . ? O3 C6 C7 105.2(11) . . ? O3 C6 H6A 110.7 . . ? C7 C6 H6A 110.7 . . ? O3 C6 H6B 110.7 . . ? C7 C6 H6B 110.7 . . ? H6A C6 H6B 108.8 . . ? C6 C7 C8 107.2(11) . . ? C6 C7 H7A 110.3 . . ? C8 C7 H7A 110.3 . . ? C6 C7 H7B 110.3 . . ? C8 C7 H7B 110.3 . . ? H7A C7 H7B 108.5 . . ? C9 C8 C7 102.4(9) . . ? C9 C8 H8A 111.3 . . ? C7 C8 H8A 111.3 . . ? C9 C8 H8B 111.3 . . ? C7 C8 H8B 111.3 . . ? H8A C8 H8B 109.2 . . ? O3 C9 C8 105.6(7) . . ? O3 C9 H9A 110.6 . . ? C8 C9 H9A 110.6 . . ? O3 C9 H9B 110.6 . . ? C8 C9 H9B 110.6 . . ? H9A C9 H9B 108.8 . . ? C16 N11 C12 121.59(13) . . ? C16 N11 H11 120.6(12) . . ? C12 N11 H11 117.7(12) . . ? N11 C12 C13 121.60(14) . . ? N11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C12 C13 C14 117.68(14) . . ? C12 C13 C17 120.17(14) . . ? C14 C13 C17 122.15(14) . . ? C15 C14 C13 118.71(13) . . ? C15 C14 C18 120.35(14) . . ? C13 C14 C18 120.94(14) . . ? C16 C15 C14 120.71(14) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? N11 C16 C15 119.60(14) . . ? N11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? 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 . . ? 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 . . ? C211 O211 H211 101.5(15) . . ? O211 C211 C220 119.07(13) . . ? O211 C211 C212 119.21(12) . . ? C220 C211 C212 121.69(13) . . ? C213 C212 C211 119.19(13) . . ? C213 C212 C221 119.14(13) . . ? C211 C212 C221 121.59(13) . . ? C212 C213 C214 121.42(13) . . ? C212 C213 H213 119.3 . . ? C214 C213 H213 119.3 . . ? C213 C214 C215 120.74(13) . . ? C213 C214 C219 119.16(13) . . ? C215 C214 C219 120.04(13) . . ? C216 C215 C214 121.26(14) . . ? C216 C215 H215 119.4 . . ? C214 C215 H215 119.4 . . ? C215 C216 C217 118.96(14) . . ? C215 C216 H216 120.5 . . ? C217 C216 H216 120.5 . . ? C218 C217 C216 121.43(14) . . ? C218 C217 H217 119.3 . . ? C216 C217 H217 119.3 . . ? C217 C218 C219 121.26(14) . . ? C217 C218 H218 119.4 . . ? C219 C218 H218 119.4 . . ? C218 C219 C214 116.99(13) . . ? C218 C219 C220 122.90(13) . . ? C214 C219 C220 120.07(13) . . ? C211 C220 C219 118.38(13) . . ? C211 C220 C222 119.46(12) . . ? C219 C220 C222 121.99(12) . . ? O222 C221 O221 123.41(13) . . ? O222 C221 C212 119.64(13) . . ? O221 C221 C212 116.92(12) . . ? C223 C222 C220 115.90(12) . . ? 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 118.63(12) . . ? C224 C223 C222 119.99(12) . . ? C232 C223 C222 121.34(12) . . ? C224 O224 H224 104.3(14) . . ? O224 C224 C223 118.70(12) . . ? O224 C224 C225 120.02(12) . . ? C223 C224 C225 121.28(12) . . ? C226 C225 C224 119.66(12) . . ? C226 C225 C233 120.02(12) . . ? C224 C225 C233 120.25(12) . . ? C225 C226 C227 121.30(13) . . ? C225 C226 H226 119.4 . . ? C227 C226 H226 119.4 . . ? C226 C227 C228 120.86(13) . . ? C226 C227 C232 118.94(13) . . ? C228 C227 C232 120.20(12) . . ? C229 C228 C227 120.62(14) . . ? C229 C228 H228 119.7 . . ? C227 C228 H228 119.7 . . ? C228 C229 C230 119.61(14) . . ? C228 C229 H229 120.2 . . ? C230 C229 H229 120.2 . . ? C231 C230 C229 121.49(13) . . ? C231 C230 H230 119.3 . . ? C229 C230 H230 119.3 . . ? C230 C231 C232 120.77(13) . . ? C230 C231 H231 119.6 . . ? C232 C231 H231 119.6 . . ? C231 C232 C223 122.76(13) . . ? C231 C232 C227 117.28(12) . . ? C223 C232 C227 119.95(12) . . ? O233 C233 O234 122.85(12) . . ? O233 C233 C225 122.75(13) . . ? O234 C233 C225 114.35(12) . . ? C233 O234 H234 109.1(13) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O222 0.92(2) 1.68(2) 2.6000(15) 172(2) 3 N11 H11 O221 0.97(2) 1.73(2) 2.6963(16) 175.7(19) . O211 H211 O221 0.92(3) 1.64(3) 2.5169(14) 159(2) . O224 H224 O233 0.89(2) 1.76(2) 2.5905(15) 154(2) . O234 H234 O1 0.96(2) 1.64(2) 2.5954(12) 169(2) . _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 27.18 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.463 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.046 #=== END data_1.Ether _database_code_depnum_ccdc_archive 'CCDC 837701' #TrackingRef '- revision_2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,4 lutidinium pamoate hydrate diethyl ether solvate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N 1+ , C23 H15 O6 1- , 1/2(H2 O), C4 H10 O' _chemical_formula_sum 'C34 H36 N O7.50' _chemical_formula_weight 578.64 # formula weight is given including disordered channel contents 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 21.9738(14) _cell_length_b 19.9094(13) _cell_length_c 14.7487(10) _cell_angle_alpha 90.00 _cell_angle_beta 114.2870(10) _cell_angle_gamma 90.00 _cell_volume 5881.3(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3149 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 24.60 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2456 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6647 _exptl_absorpt_correction_T_max 0.7451 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _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 '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 15168 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 24.90 _reflns_number_total 5118 _reflns_number_gt 3641 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement ; SHELXL (Sheldrick, 2008), Platon/SQUEEZE (Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The O1-H1 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^)+(0.0833P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5118 _refine_ls_number_parameters 361 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1409 _refine_ls_wR_factor_gt 0.1303 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.0000 0.33701(11) 0.2500 0.0306(5) Uani 1 2 d SD . . N11 N 0.38026(9) -0.01164(9) 0.37717(12) 0.0346(4) Uani 1 1 d . . . H11 H 0.4233(11) 0.0080(10) 0.3821(14) 0.037(6) Uiso 1 1 d . . . C12 C 0.32811(10) 0.02863(11) 0.36385(15) 0.0372(5) Uani 1 1 d . . . H12 H 0.3332 0.0758 0.3605 0.045 Uiso 1 1 calc R . . C13 C 0.26731(10) 0.00323(12) 0.35493(14) 0.0363(5) Uani 1 1 d . . . C14 C 0.26135(10) -0.06695(12) 0.35930(14) 0.0364(5) Uani 1 1 d . . . C15 C 0.31672(11) -0.10626(12) 0.37599(15) 0.0395(5) Uani 1 1 d . . . H15 H 0.3139 -0.1536 0.3816 0.047 Uiso 1 1 calc R . . C16 C 0.37588(11) -0.07798(11) 0.38465(14) 0.0370(5) Uani 1 1 d . . . H16 H 0.4135 -0.1056 0.3959 0.044 Uiso 1 1 calc R . . C17 C 0.21062(11) 0.04985(13) 0.34128(17) 0.0454(6) Uani 1 1 d . . . H17A H 0.2245 0.0963 0.3384 0.068 Uiso 1 1 calc R . . H17B H 0.1979 0.0449 0.3973 0.068 Uiso 1 1 calc R . . H17C H 0.1723 0.0388 0.2792 0.068 Uiso 1 1 calc R . . C18 C 0.19588(11) -0.09841(13) 0.34555(16) 0.0472(6) Uani 1 1 d . . . H18A H 0.1833 -0.0833 0.3987 0.071 Uiso 1 1 calc R . . H18B H 0.2004 -0.1474 0.3480 0.071 Uiso 1 1 calc R . . H18C H 0.1613 -0.0850 0.2809 0.071 Uiso 1 1 calc R . . O211 O 0.57603(6) 0.12584(7) 0.37436(10) 0.0332(4) Uani 1 1 d . . . C211 C 0.61864(9) 0.07520(11) 0.37840(13) 0.0298(5) Uani 1 1 d . . . H211 H 0.5377(14) 0.1006(14) 0.3746(19) 0.071(8) Uiso 1 1 d . . . C212 C 0.59779(10) 0.00697(11) 0.37736(13) 0.0298(5) Uani 1 1 d . . . C213 C 0.64080(10) -0.04377(11) 0.38108(14) 0.0332(5) Uani 1 1 d . . . H213 H 0.6267 -0.0891 0.3792 0.040 Uiso 1 1 calc R . . C214 C 0.70560(10) -0.03035(11) 0.38761(14) 0.0323(5) Uani 1 1 d . . . C215 C 0.74961(10) -0.08350(12) 0.39367(15) 0.0387(5) Uani 1 1 d . . . H215 H 0.7342 -0.1285 0.3884 0.046 Uiso 1 1 calc R . . C216 C 0.81418(11) -0.07152(12) 0.40696(15) 0.0415(6) Uani 1 1 d . . . H216 H 0.8434 -0.1077 0.4107 0.050 Uiso 1 1 calc R . . C217 C 0.83632(11) -0.00471(13) 0.41488(15) 0.0425(6) Uani 1 1 d . . . H217 H 0.8813 0.0038 0.4257 0.051 Uiso 1 1 calc R . . C218 C 0.79489(10) 0.04863(12) 0.40745(14) 0.0359(5) Uani 1 1 d . . . H218 H 0.8115 0.0932 0.4125 0.043 Uiso 1 1 calc R . . C219 C 0.72679(9) 0.03764(11) 0.39208(13) 0.0311(5) Uani 1 1 d . . . C220 C 0.68201(9) 0.09138(10) 0.38534(13) 0.0291(5) Uani 1 1 d . . . O221 O 0.49330(7) 0.03910(7) 0.37677(10) 0.0356(4) Uani 1 1 d . . . C221 C 0.53127(10) -0.01003(11) 0.37796(14) 0.0323(5) Uani 1 1 d . . . O222 O 0.51585(7) -0.07007(8) 0.38160(10) 0.0397(4) Uani 1 1 d . . . C222 C 0.70286(9) 0.16469(11) 0.39339(14) 0.0322(5) Uani 1 1 d . . . H22A H 0.7418 0.1711 0.4577 0.039 Uiso 1 1 calc R . . H22B H 0.6659 0.1923 0.3952 0.039 Uiso 1 1 calc R . . C223 C 0.72103(9) 0.19171(10) 0.31119(14) 0.0284(5) Uani 1 1 d . . . O224 O 0.83141(7) 0.21070(8) 0.42945(10) 0.0380(4) Uani 1 1 d . . . C224 C 0.78560(9) 0.21225(10) 0.33270(14) 0.0296(5) Uani 1 1 d . . . H224 H 0.8739(13) 0.2281(13) 0.4334(18) 0.068(8) Uiso 1 1 d . . . C225 C 0.80525(9) 0.23501(10) 0.25665(14) 0.0290(5) Uani 1 1 d . . . C226 C 0.75852(9) 0.23812(10) 0.16036(14) 0.0297(5) Uani 1 1 d . . . H226 H 0.7718 0.2516 0.1095 0.036 Uiso 1 1 calc R . . C227 C 0.69112(9) 0.22169(10) 0.13510(14) 0.0282(5) Uani 1 1 d . . . C228 C 0.64244(9) 0.22829(11) 0.03565(14) 0.0351(5) Uani 1 1 d . . . H228 H 0.6556 0.2430 -0.0149 0.042 Uiso 1 1 calc R . . C229 C 0.57750(9) 0.21388(11) 0.01219(15) 0.0369(5) Uani 1 1 d . . . H229 H 0.5452 0.2184 -0.0544 0.044 Uiso 1 1 calc R . . C230 C 0.55816(9) 0.19205(10) 0.08737(15) 0.0331(5) Uani 1 1 d . . . H230 H 0.5124 0.1825 0.0706 0.040 Uiso 1 1 calc R . . C231 C 0.60302(9) 0.18428(10) 0.18313(14) 0.0292(5) Uani 1 1 d . . . H231 H 0.5883 0.1690 0.2318 0.035 Uiso 1 1 calc R . . C232 C 0.67177(9) 0.19877(10) 0.21112(14) 0.0271(4) Uani 1 1 d . . . O233 O 0.91689(6) 0.26077(8) 0.36853(10) 0.0411(4) Uani 1 1 d . . . C233 C 0.87444(9) 0.25792(11) 0.28270(14) 0.0307(5) Uani 1 1 d . . . O234 O 0.88661(7) 0.27676(8) 0.20618(10) 0.0368(4) Uani 1 1 d . . . H234 H 0.9332(13) 0.3020(13) 0.2302(18) 0.069(8) Uiso 1 1 d . . . H1 H 1.0053(18) 0.3691(13) 0.3003(18) 0.130(14) 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 O1 0.0164(9) 0.0454(13) 0.0287(11) 0.000 0.0080(9) 0.000 N11 0.0297(10) 0.0502(12) 0.0261(9) -0.0044(8) 0.0135(8) -0.0124(9) C12 0.0352(12) 0.0475(14) 0.0266(11) 0.0009(9) 0.0102(10) -0.0103(10) C13 0.0319(12) 0.0538(15) 0.0216(10) 0.0018(10) 0.0093(9) -0.0097(10) C14 0.0354(12) 0.0563(15) 0.0181(10) -0.0024(10) 0.0117(9) -0.0165(11) C15 0.0449(13) 0.0483(14) 0.0267(12) -0.0055(10) 0.0161(10) -0.0154(11) C16 0.0410(12) 0.0467(14) 0.0278(11) -0.0034(10) 0.0187(10) -0.0095(11) C17 0.0341(12) 0.0609(16) 0.0395(13) 0.0074(11) 0.0133(11) -0.0071(11) C18 0.0411(13) 0.0639(17) 0.0353(13) -0.0002(11) 0.0144(11) -0.0224(12) O211 0.0250(7) 0.0433(9) 0.0343(8) -0.0021(6) 0.0154(6) -0.0028(7) C211 0.0270(10) 0.0441(13) 0.0189(10) -0.0017(9) 0.0102(8) 0.0004(9) C212 0.0272(10) 0.0433(13) 0.0179(10) 0.0011(9) 0.0083(8) -0.0034(9) C213 0.0353(12) 0.0440(13) 0.0209(10) 0.0008(9) 0.0122(9) -0.0014(10) C214 0.0299(11) 0.0473(14) 0.0179(10) 0.0026(9) 0.0079(9) 0.0032(9) C215 0.0357(12) 0.0477(14) 0.0282(12) 0.0033(10) 0.0087(10) 0.0056(10) C216 0.0326(12) 0.0558(16) 0.0326(12) 0.0041(10) 0.0101(10) 0.0109(11) C217 0.0264(11) 0.0691(17) 0.0299(12) 0.0041(11) 0.0095(9) 0.0056(11) C218 0.0263(11) 0.0518(14) 0.0264(11) 0.0059(10) 0.0076(9) 0.0010(10) C219 0.0235(10) 0.0499(13) 0.0166(10) 0.0035(9) 0.0050(8) 0.0006(9) C220 0.0252(10) 0.0439(12) 0.0177(10) 0.0008(9) 0.0083(8) -0.0018(9) O221 0.0282(7) 0.0450(9) 0.0362(8) -0.0031(7) 0.0159(7) -0.0058(7) C221 0.0330(11) 0.0458(14) 0.0200(10) -0.0023(9) 0.0127(9) -0.0047(10) O222 0.0446(9) 0.0438(10) 0.0406(9) -0.0033(7) 0.0276(7) -0.0084(7) C222 0.0239(10) 0.0489(13) 0.0228(11) -0.0007(9) 0.0085(9) -0.0042(9) C223 0.0222(10) 0.0376(12) 0.0264(11) 0.0007(9) 0.0109(9) 0.0009(8) O224 0.0228(7) 0.0647(11) 0.0221(8) 0.0029(7) 0.0046(6) -0.0082(7) C224 0.0209(10) 0.0425(12) 0.0225(11) 0.0015(9) 0.0060(8) 0.0001(9) C225 0.0190(10) 0.0403(12) 0.0269(11) 0.0010(9) 0.0085(9) 0.0017(8) C226 0.0197(10) 0.0432(12) 0.0277(11) 0.0023(9) 0.0112(9) -0.0015(9) C227 0.0190(9) 0.0395(12) 0.0247(11) -0.0010(9) 0.0077(8) -0.0008(8) C228 0.0217(10) 0.0565(14) 0.0237(11) 0.0027(10) 0.0061(9) -0.0012(10) C229 0.0195(10) 0.0574(14) 0.0286(12) 0.0047(10) 0.0048(9) -0.0020(10) C230 0.0170(10) 0.0444(13) 0.0352(12) 0.0027(10) 0.0080(9) -0.0023(9) C231 0.0200(10) 0.0365(12) 0.0326(11) 0.0009(9) 0.0123(9) -0.0004(8) C232 0.0219(10) 0.0339(12) 0.0257(11) -0.0015(8) 0.0099(8) 0.0029(8) O233 0.0198(7) 0.0722(11) 0.0263(8) 0.0042(7) 0.0043(7) -0.0056(7) C233 0.0206(10) 0.0441(13) 0.0252(11) 0.0020(9) 0.0071(9) 0.0018(9) O234 0.0198(7) 0.0628(10) 0.0278(8) 0.0017(7) 0.0097(6) -0.0060(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 H1 0.949(10) . ? N11 C16 1.332(3) . ? N11 C12 1.345(3) . ? N11 H11 1.00(2) . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 C14 1.407(3) . ? C13 C17 1.499(3) . ? C14 C15 1.381(3) . ? C14 C18 1.504(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 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O211 C211 1.360(2) . ? O211 H211 0.98(3) . ? C211 C220 1.391(3) . ? C211 C212 1.432(3) . ? C212 C213 1.369(3) . ? C212 C221 1.504(3) . ? C213 C214 1.413(3) . ? C213 H213 0.9500 . ? C214 C215 1.411(3) . ? C214 C219 1.424(3) . ? C215 C216 1.371(3) . ? C215 H215 0.9500 . ? C216 C217 1.405(3) . ? C216 H216 0.9500 . ? C217 C218 1.373(3) . ? C217 H217 0.9500 . ? C218 C219 1.435(3) . ? C218 H218 0.9500 . ? C219 C220 1.429(3) . ? C220 C222 1.520(3) . ? O221 C221 1.281(2) . ? C221 O222 1.250(2) . ? C222 C223 1.522(3) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C223 C224 1.382(3) . ? C223 C232 1.434(3) . ? O224 C224 1.367(2) . ? O224 H224 0.97(3) . ? C224 C225 1.431(3) . ? C225 C226 1.370(3) . ? C225 C233 1.479(3) . ? C226 C227 1.409(3) . ? C226 H226 0.9500 . ? C227 C228 1.422(3) . ? C227 C232 1.428(3) . ? C228 C229 1.353(3) . ? C228 H228 0.9500 . ? C229 C230 1.410(3) . ? C229 H229 0.9500 . ? C230 C231 1.358(3) . ? C230 H230 0.9500 . ? C231 C232 1.422(3) . ? C231 H231 0.9500 . ? O233 C233 1.227(2) . ? C233 O234 1.317(2) . ? O234 H234 1.06(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 121.12(18) . . ? C16 N11 H11 118.8(12) . . ? C12 N11 H11 120.1(12) . . ? N11 C12 C13 121.8(2) . . ? N11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C12 C13 C14 117.6(2) . . ? C12 C13 C17 120.2(2) . . ? C14 C13 C17 122.21(19) . . ? C15 C14 C13 118.63(19) . . ? C15 C14 C18 120.8(2) . . ? C13 C14 C18 120.6(2) . . ? C16 C15 C14 121.0(2) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? N11 C16 C15 119.8(2) . . ? N11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? 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 . . ? 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 . . ? C211 O211 H211 101.3(15) . . ? O211 C211 C220 118.79(19) . . ? O211 C211 C212 119.43(17) . . ? C220 C211 C212 121.77(19) . . ? C213 C212 C211 119.16(18) . . ? C213 C212 C221 119.36(19) . . ? C211 C212 C221 121.40(18) . . ? C212 C213 C214 121.5(2) . . ? C212 C213 H213 119.2 . . ? C214 C213 H213 119.2 . . ? C215 C214 C213 120.5(2) . . ? C215 C214 C219 120.47(18) . . ? C213 C214 C219 118.96(19) . . ? C216 C215 C214 121.4(2) . . ? C216 C215 H215 119.3 . . ? C214 C215 H215 119.3 . . ? C215 C216 C217 118.6(2) . . ? C215 C216 H216 120.7 . . ? C217 C216 H216 120.7 . . ? C218 C217 C216 122.0(2) . . ? C218 C217 H217 119.0 . . ? C216 C217 H217 119.0 . . ? C217 C218 C219 120.6(2) . . ? C217 C218 H218 119.7 . . ? C219 C218 H218 119.7 . . ? C214 C219 C220 120.38(17) . . ? C214 C219 C218 116.88(19) . . ? C220 C219 C218 122.70(19) . . ? C211 C220 C219 118.13(19) . . ? C211 C220 C222 119.24(18) . . ? C219 C220 C222 122.46(17) . . ? O222 C221 O221 122.99(18) . . ? O222 C221 C212 119.79(19) . . ? O221 C221 C212 117.21(18) . . ? C220 C222 C223 116.53(16) . . ? C220 C222 H22A 108.2 . . ? C223 C222 H22A 108.2 . . ? C220 C222 H22B 108.2 . . ? C223 C222 H22B 108.2 . . ? H22A C222 H22B 107.3 . . ? C224 C223 C232 118.45(17) . . ? C224 C223 C222 120.16(17) . . ? C232 C223 C222 121.35(16) . . ? C224 O224 H224 109.3(15) . . ? O224 C224 C223 118.60(17) . . ? O224 C224 C225 119.67(16) . . ? C223 C224 C225 121.73(17) . . ? C226 C225 C224 119.19(17) . . ? C226 C225 C233 120.52(17) . . ? C224 C225 C233 120.23(17) . . ? C225 C226 C227 121.47(18) . . ? C225 C226 H226 119.3 . . ? C227 C226 H226 119.3 . . ? C226 C227 C228 120.95(17) . . ? C226 C227 C232 119.12(17) . . ? C228 C227 C232 119.92(17) . . ? C229 C228 C227 120.72(19) . . ? C229 C228 H228 119.6 . . ? C227 C228 H228 119.6 . . ? C228 C229 C230 119.44(18) . . ? C228 C229 H229 120.3 . . ? C230 C229 H229 120.3 . . ? C231 C230 C229 121.90(17) . . ? C231 C230 H230 119.1 . . ? C229 C230 H230 119.1 . . ? C230 C231 C232 120.58(18) . . ? C230 C231 H231 119.7 . . ? C232 C231 H231 119.7 . . ? C231 C232 C227 117.44(17) . . ? C231 C232 C223 122.75(17) . . ? C227 C232 C223 119.81(16) . . ? O233 C233 O234 122.33(17) . . ? O233 C233 C225 123.15(18) . . ? O234 C233 C225 114.50(17) . . ? C233 O234 H234 110.9(13) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O221 1.00(2) 1.69(2) 2.684(2) 173.6(18) . O211 H211 O221 0.98(3) 1.57(3) 2.5184(19) 160(2) . O224 H224 O233 0.97(3) 1.72(3) 2.5919(19) 146(2) . O234 H234 O1 1.06(3) 1.54(3) 2.5962(16) 172(2) . O1 H1 O222 0.949(10) 1.652(11) 2.599(2) 175(3) 3 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.90 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.273 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.065 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.011 690 255 ' ' 2 0.500 0.500 -0.003 690 255 ' ' _platon_squeeze_details ; ; #=== END data_1.Acetone _database_code_depnum_ccdc_archive 'CCDC 837702' #TrackingRef '- revision_2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,4 lutidinium pamoate hydrate acetone solvate' _chemical_melting_point ? _chemical_formula_moiety ; C7 H10 N 1+ , C23 H15 O6 1- , 1/2(H2 O), C3 H6 O ' ; _chemical_formula_sum 'C33 H32 N O7.50' _chemical_formula_weight 562.60 # formula weight is given including disordered channel contents 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 22.120(15) _cell_length_b 19.805(14) _cell_length_c 14.745(10) _cell_angle_alpha 90.00 _cell_angle_beta 114.847(9) _cell_angle_gamma 90.00 _cell_volume 5862(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2353 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 24.29 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2376 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6240 _exptl_absorpt_correction_T_max 0.7451 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _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 '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 14703 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0570 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 24.78 _reflns_number_total 4996 _reflns_number_gt 3355 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement ; SHELXL (Sheldrick, 2008) Platon/SQUEEZE (Spek, A. L. (2003).J. Appl. Cryst. 36, 7-13.) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The channel in this structure contains two half molecules of acetone, as confirmed by NMR. One molecule was highly disordered, so SQUEEZE was applied. The second acetone molecule has been restrained using SIMU, DELU, SADI and FLAT. ; _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^)+(0.0854P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00064(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4996 _refine_ls_number_parameters 400 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.0848 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1591 _refine_ls_wR_factor_gt 0.1410 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.0000 0.65986(13) 0.7500 0.0281(6) Uani 1 2 d S . . H1 H -0.0104(16) 0.6296(17) 0.698(2) 0.072(11) Uiso 1 1 d . . . N11 N 0.61659(11) 1.00666(10) 0.62357(15) 0.0274(5) Uani 1 1 d . . . C12 C 0.66820(14) 0.96621(13) 0.63688(18) 0.0308(6) Uani 1 1 d . . . H12 H 0.6630 0.9187 0.6395 0.037 Uiso 1 1 calc R . . C13 C 0.72957(13) 0.99221(13) 0.64695(17) 0.0286(6) Uani 1 1 d . . . C14 C 0.73512(13) 1.06264(13) 0.64274(17) 0.0275(6) Uani 1 1 d . . . C15 C 0.67903(13) 1.10220(13) 0.62450(18) 0.0296(6) Uani 1 1 d . . . H15 H 0.6814 1.1497 0.6179 0.036 Uiso 1 1 calc R . . C16 C 0.62081(14) 1.07353(12) 0.61599(18) 0.0307(6) Uani 1 1 d . . . H16 H 0.5832 1.1012 0.6047 0.037 Uiso 1 1 calc R . . C17 C 0.78577(14) 0.94568(14) 0.6603(2) 0.0381(7) Uani 1 1 d . . . H17A H 0.8242 0.9566 0.7227 0.057 Uiso 1 1 calc R . . H17B H 0.7980 0.9509 0.6040 0.057 Uiso 1 1 calc R . . H17C H 0.7720 0.8989 0.6628 0.057 Uiso 1 1 calc R . . C18 C 0.80012(14) 1.09495(14) 0.6571(2) 0.0385(7) Uani 1 1 d . . . H18A H 0.8121 1.0809 0.6031 0.058 Uiso 1 1 calc R . . H18B H 0.8351 1.0808 0.7215 0.058 Uiso 1 1 calc R . . H18C H 0.7955 1.1442 0.6561 0.058 Uiso 1 1 calc R . . C31 C 0.46635(13) 1.00460(13) 0.62139(18) 0.0268(6) Uani 1 1 d . . . O211 O 0.42046(9) 0.86803(8) 0.62181(13) 0.0287(4) Uani 1 1 d . . . H211 H 0.4621(18) 0.8949(18) 0.625(2) 0.073(10) Uiso 1 1 d . . . C211 C 0.37889(12) 0.91908(12) 0.61913(17) 0.0236(6) Uani 1 1 d . . . C212 C 0.39976(12) 0.98769(12) 0.62101(17) 0.0238(6) Uani 1 1 d . . . C213 C 0.35760(13) 1.03896(12) 0.61834(17) 0.0261(6) Uani 1 1 d . . . H213 H 0.3722 1.0844 0.6217 0.031 Uiso 1 1 calc R . . C214 C 0.29318(13) 1.02606(12) 0.61072(17) 0.0241(6) Uani 1 1 d . . . C215 C 0.24903(13) 1.07957(13) 0.60485(18) 0.0306(6) Uani 1 1 d . . . H215 H 0.2645 1.1248 0.6110 0.037 Uiso 1 1 calc R . . C216 C 0.18489(14) 1.06765(13) 0.59064(19) 0.0316(6) Uani 1 1 d . . . H216 H 0.1561 1.1041 0.5873 0.038 Uiso 1 1 calc R . . C217 C 0.16204(14) 1.00044(13) 0.58106(19) 0.0321(6) Uani 1 1 d . . . H217 H 0.1171 0.9918 0.5694 0.039 Uiso 1 1 calc R . . C218 C 0.20344(13) 0.94734(13) 0.58821(18) 0.0281(6) Uani 1 1 d . . . H218 H 0.1867 0.9026 0.5822 0.034 Uiso 1 1 calc R . . C219 C 0.27106(13) 0.95749(12) 0.60453(17) 0.0246(6) Uani 1 1 d . . . C220 C 0.31534(12) 0.90347(12) 0.61095(17) 0.0237(6) Uani 1 1 d . . . O221 O 0.50400(9) 0.95523(8) 0.62299(13) 0.0303(4) Uani 1 1 d . . . O222 O 0.48203(9) 1.06515(8) 0.61760(13) 0.0321(5) Uani 1 1 d . . . C222 C 0.29304(12) 0.82940(11) 0.60134(18) 0.0256(6) Uani 1 1 d . . . H22A H 0.2532 0.8240 0.5373 0.031 Uiso 1 1 calc R . . H22B H 0.3289 0.8010 0.5979 0.031 Uiso 1 1 calc R . . C223 C 0.27640(12) 0.80264(11) 0.68498(18) 0.0249(6) Uani 1 1 d . . . O224 O 0.16457(9) 0.78559(9) 0.56635(12) 0.0303(4) Uani 1 1 d . . . H224 H 0.1237(18) 0.7701(17) 0.568(3) 0.074(11) Uiso 1 1 d . . . C224 C 0.21144(13) 0.78312(11) 0.66347(18) 0.0254(6) Uani 1 1 d . . . C225 C 0.19324(12) 0.76144(11) 0.74125(18) 0.0236(6) Uani 1 1 d . . . C226 C 0.24065(12) 0.75773(11) 0.83787(18) 0.0248(6) Uani 1 1 d . . . H226 H 0.2278 0.7446 0.8892 0.030 Uiso 1 1 calc R . . C227 C 0.30797(12) 0.77287(11) 0.86277(18) 0.0248(6) Uani 1 1 d . . . C228 C 0.35722(13) 0.76610(13) 0.96226(19) 0.0306(6) Uani 1 1 d . . . H228 H 0.3444 0.7524 1.0134 0.037 Uiso 1 1 calc R . . C229 C 0.42271(13) 0.77892(13) 0.9857(2) 0.0329(6) Uani 1 1 d . . . H229 H 0.4554 0.7743 1.0525 0.039 Uiso 1 1 calc R . . C230 C 0.44097(14) 0.79914(12) 0.9087(2) 0.0319(6) Uani 1 1 d . . . H230 H 0.4866 0.8073 0.9244 0.038 Uiso 1 1 calc R . . C231 C 0.39506(12) 0.80723(12) 0.81243(19) 0.0280(6) Uani 1 1 d . . . H231 H 0.4094 0.8214 0.7631 0.034 Uiso 1 1 calc R . . C232 C 0.32618(12) 0.79483(11) 0.78455(18) 0.0243(6) Uani 1 1 d . . . O233 O 0.08043(9) 0.73752(9) 0.62971(13) 0.0350(5) Uani 1 1 d . . . C233 C 0.12358(12) 0.73945(12) 0.71582(19) 0.0249(6) Uani 1 1 d . . . O234 O 0.11278(9) 0.72068(9) 0.79367(13) 0.0327(5) Uani 1 1 d . . . H234 H 0.0672(17) 0.6974(16) 0.774(2) 0.071(11) Uiso 1 1 d . . . H11 H 0.5754(18) 0.9821(17) 0.624(2) 0.073(11) Uiso 1 1 d . . . C2 C 0.0217(6) 0.8908(6) 0.7149(9) 0.125(4) Uani 0.50 1 d PDU A -1 C3 C -0.0463(10) 0.8874(12) 0.6423(16) 0.205(10) Uani 0.50 1 d PDU A -1 H3A H -0.0689 0.9298 0.6427 0.307 Uiso 0.50 1 calc PR A -1 H3B H -0.0688 0.8499 0.6589 0.307 Uiso 0.50 1 calc PR A -1 H3C H -0.0475 0.8801 0.5758 0.307 Uiso 0.50 1 calc PR A -1 C4 C 0.0423(7) 0.8915(13) 0.8222(11) 0.127(6) Uani 0.50 1 d PDU A -1 H4A H 0.0266 0.8502 0.8423 0.190 Uiso 0.50 1 calc PR A -1 H4B H 0.0231 0.9310 0.8404 0.190 Uiso 0.50 1 calc PR A -1 H4C H 0.0910 0.8937 0.8563 0.190 Uiso 0.50 1 calc PR A -1 O2 O 0.0641(6) 0.8879(6) 0.6750(8) 0.186(4) Uani 0.50 1 d PDU A -1 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 0.0225(15) 0.0284(14) 0.0340(15) 0.000 0.0123(12) 0.000 N11 0.0277(14) 0.0285(12) 0.0286(12) -0.0008(9) 0.0143(10) -0.0015(10) C12 0.0377(18) 0.0275(14) 0.0279(15) 0.0014(11) 0.0144(13) -0.0026(13) C13 0.0333(17) 0.0294(14) 0.0228(13) 0.0017(10) 0.0117(12) 0.0023(12) C14 0.0305(16) 0.0320(14) 0.0209(13) -0.0016(10) 0.0116(12) -0.0026(12) C15 0.0361(17) 0.0255(13) 0.0306(15) -0.0020(11) 0.0174(13) -0.0066(12) C16 0.0360(17) 0.0288(14) 0.0296(14) -0.0012(11) 0.0161(13) 0.0005(12) C17 0.0294(17) 0.0452(17) 0.0394(17) 0.0027(13) 0.0141(13) 0.0046(13) C18 0.0380(18) 0.0440(17) 0.0371(16) -0.0024(13) 0.0195(14) -0.0132(14) C31 0.0288(16) 0.0298(14) 0.0233(13) -0.0033(11) 0.0125(11) -0.0035(12) O211 0.0256(11) 0.0245(9) 0.0398(11) 0.0004(7) 0.0175(9) 0.0029(8) C211 0.0261(15) 0.0233(13) 0.0217(13) 0.0007(10) 0.0103(11) 0.0012(11) C212 0.0237(15) 0.0286(13) 0.0196(13) -0.0005(10) 0.0096(11) -0.0021(11) C213 0.0306(16) 0.0253(13) 0.0223(13) -0.0019(10) 0.0111(12) -0.0049(11) C214 0.0248(15) 0.0266(13) 0.0210(13) 0.0005(10) 0.0097(11) 0.0003(11) C215 0.0347(17) 0.0287(14) 0.0284(14) -0.0014(11) 0.0134(12) 0.0013(12) C216 0.0301(17) 0.0327(15) 0.0350(15) 0.0026(11) 0.0167(13) 0.0073(12) C217 0.0288(16) 0.0385(15) 0.0320(15) 0.0016(12) 0.0157(12) 0.0025(13) C218 0.0293(16) 0.0273(13) 0.0299(14) 0.0015(11) 0.0146(12) 0.0006(12) C219 0.0248(15) 0.0298(13) 0.0194(13) 0.0026(10) 0.0096(11) 0.0006(11) C220 0.0232(15) 0.0256(13) 0.0233(13) -0.0004(10) 0.0105(11) -0.0008(11) O221 0.0253(11) 0.0285(10) 0.0392(11) -0.0006(8) 0.0155(9) 0.0007(8) O222 0.0351(12) 0.0283(10) 0.0375(11) -0.0021(8) 0.0197(9) -0.0062(8) C222 0.0235(15) 0.0261(13) 0.0270(14) -0.0007(10) 0.0104(11) -0.0001(11) C223 0.0235(15) 0.0199(12) 0.0314(14) 0.0000(10) 0.0116(12) -0.0007(11) O224 0.0232(11) 0.0342(10) 0.0291(10) 0.0018(8) 0.0067(8) -0.0047(8) C224 0.0252(15) 0.0187(12) 0.0285(14) -0.0009(10) 0.0078(12) 0.0008(10) C225 0.0200(14) 0.0205(12) 0.0296(14) -0.0025(10) 0.0096(11) -0.0015(10) C226 0.0227(15) 0.0235(13) 0.0307(14) -0.0004(10) 0.0135(12) -0.0028(11) C227 0.0201(14) 0.0211(12) 0.0322(14) -0.0001(10) 0.0100(11) -0.0020(10) C228 0.0266(16) 0.0344(14) 0.0314(15) 0.0014(11) 0.0128(12) -0.0031(12) C229 0.0210(15) 0.0369(15) 0.0336(15) 0.0031(12) 0.0045(12) -0.0021(12) C230 0.0227(15) 0.0305(14) 0.0385(16) 0.0034(12) 0.0090(13) -0.0020(11) C231 0.0233(15) 0.0241(13) 0.0396(16) 0.0018(11) 0.0161(13) -0.0036(11) C232 0.0232(15) 0.0181(12) 0.0319(14) -0.0006(10) 0.0117(12) 0.0002(10) O233 0.0219(11) 0.0447(11) 0.0327(11) 0.0034(8) 0.0059(9) -0.0054(8) C233 0.0197(14) 0.0220(13) 0.0318(15) -0.0005(10) 0.0098(12) -0.0002(10) O234 0.0232(11) 0.0422(11) 0.0344(11) 0.0012(8) 0.0138(9) -0.0082(9) C2 0.080(7) 0.165(10) 0.105(7) -0.020(8) 0.015(5) -0.029(8) C3 0.135(8) 0.147(14) 0.186(17) -0.086(13) -0.076(10) 0.079(10) C4 0.059(8) 0.206(18) 0.099(7) 0.050(10) 0.016(7) 0.018(9) O2 0.204(9) 0.220(10) 0.159(8) -0.024(7) 0.100(7) -0.059(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 H1 0.93(3) . ? N11 C16 1.336(3) . ? N11 C12 1.340(3) . ? N11 H11 1.04(4) . ? C12 C13 1.400(4) . ? C12 H12 0.9500 . ? C13 C14 1.404(4) . ? C13 C17 1.493(4) . ? C14 C15 1.395(4) . ? C14 C18 1.505(4) . ? C15 C16 1.364(4) . ? 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 . ? C31 O222 1.256(3) . ? C31 O221 1.278(3) . ? C31 C212 1.508(4) . ? O211 C211 1.356(3) . ? O211 H211 1.05(4) . ? C211 C220 1.394(3) . ? C211 C212 1.432(3) . ? C212 C213 1.368(3) . ? C213 C214 1.405(4) . ? C213 H213 0.9500 . ? C214 C215 1.419(3) . ? C214 C219 1.433(3) . ? C215 C216 1.365(4) . ? C215 H215 0.9500 . ? C216 C217 1.410(4) . ? C216 H216 0.9500 . ? C217 C218 1.369(4) . ? C217 H217 0.9500 . ? C218 C219 1.426(4) . ? C218 H218 0.9500 . ? C219 C220 1.427(3) . ? C220 C222 1.535(3) . ? C222 C223 1.523(3) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C223 C224 1.390(3) . ? C223 C232 1.426(3) . ? O224 C224 1.371(3) . ? O224 H224 0.96(4) . ? C224 C225 1.432(3) . ? C225 C226 1.371(3) . ? C225 C233 1.490(4) . ? C226 C227 1.408(3) . ? C226 H226 0.9500 . ? C227 C228 1.419(4) . ? C227 C232 1.439(3) . ? C228 C229 1.364(4) . ? C228 H228 0.9500 . ? C229 C230 1.414(4) . ? C229 H229 0.9500 . ? C230 C231 1.364(4) . ? C230 H230 0.9500 . ? C231 C232 1.423(3) . ? C231 H231 0.9500 . ? O233 C233 1.227(3) . ? C233 O234 1.320(3) . ? O234 H234 1.03(4) . ? C2 O2 1.300(13) . ? C2 C3 1.435(15) . ? C2 C4 1.451(14) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 121.3(2) . . ? C16 N11 H11 123.9(18) . . ? C12 N11 H11 114.6(18) . . ? N11 C12 C13 121.6(2) . . ? N11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C12 C13 C14 117.4(2) . . ? C12 C13 C17 120.2(2) . . ? C14 C13 C17 122.4(2) . . ? C15 C14 C13 118.6(2) . . ? C15 C14 C18 120.5(2) . . ? C13 C14 C18 120.8(2) . . ? C16 C15 C14 120.9(2) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? N11 C16 C15 120.1(2) . . ? N11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? 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 . . ? 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 . . ? O222 C31 O221 122.8(2) . . ? O222 C31 C212 120.0(2) . . ? O221 C31 C212 117.3(2) . . ? C211 O211 H211 101.4(18) . . ? O211 C211 C220 118.9(2) . . ? O211 C211 C212 119.9(2) . . ? C220 C211 C212 121.1(2) . . ? C213 C212 C211 119.6(2) . . ? C213 C212 C31 119.2(2) . . ? C211 C212 C31 121.1(2) . . ? C212 C213 C214 121.6(2) . . ? C212 C213 H213 119.2 . . ? C214 C213 H213 119.2 . . ? C213 C214 C215 121.2(2) . . ? C213 C214 C219 119.0(2) . . ? C215 C214 C219 119.7(2) . . ? C216 C215 C214 121.6(2) . . ? C216 C215 H215 119.2 . . ? C214 C215 H215 119.2 . . ? C215 C216 C217 119.0(2) . . ? C215 C216 H216 120.5 . . ? C217 C216 H216 120.5 . . ? C218 C217 C216 121.2(3) . . ? C218 C217 H217 119.4 . . ? C216 C217 H217 119.4 . . ? C217 C218 C219 121.7(2) . . ? C217 C218 H218 119.2 . . ? C219 C218 H218 119.2 . . ? C218 C219 C220 123.2(2) . . ? C218 C219 C214 116.8(2) . . ? C220 C219 C214 120.0(2) . . ? C211 C220 C219 118.6(2) . . ? C211 C220 C222 119.5(2) . . ? C219 C220 C222 121.7(2) . . ? C223 C222 C220 115.82(19) . . ? 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 118.8(2) . . ? C224 C223 C222 119.4(2) . . ? C232 C223 C222 121.8(2) . . ? C224 O224 H224 106(2) . . ? O224 C224 C223 118.9(2) . . ? O224 C224 C225 120.2(2) . . ? C223 C224 C225 120.8(2) . . ? C226 C225 C224 119.9(2) . . ? C226 C225 C233 120.3(2) . . ? C224 C225 C233 119.7(2) . . ? C225 C226 C227 121.5(2) . . ? C225 C226 H226 119.2 . . ? C227 C226 H226 119.2 . . ? C226 C227 C228 121.2(2) . . ? C226 C227 C232 118.5(2) . . ? C228 C227 C232 120.3(2) . . ? C229 C228 C227 121.1(2) . . ? C229 C228 H228 119.5 . . ? C227 C228 H228 119.5 . . ? C228 C229 C230 118.7(2) . . ? C228 C229 H229 120.6 . . ? C230 C229 H229 120.6 . . ? C231 C230 C229 122.0(3) . . ? C231 C230 H230 119.0 . . ? C229 C230 H230 119.0 . . ? C230 C231 C232 121.3(2) . . ? C230 C231 H231 119.4 . . ? C232 C231 H231 119.4 . . ? C231 C232 C223 123.3(2) . . ? C231 C232 C227 116.5(2) . . ? C223 C232 C227 120.2(2) . . ? O233 C233 O234 123.0(2) . . ? O233 C233 C225 122.8(2) . . ? O234 C233 C225 114.2(2) . . ? C233 O234 H234 112.9(18) . . ? O2 C2 C3 112.9(15) . . ? O2 C2 C4 122.6(12) . . ? C3 C2 C4 124(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O222 0.93(3) 1.70(3) 2.615(3) 169(3) 3_445 O234 H234 O1 1.03(4) 1.56(4) 2.596(3) 176(3) . O211 H211 O221 1.05(4) 1.52(4) 2.524(3) 158(3) . N11 H11 O221 1.04(4) 1.66(4) 2.687(3) 171(3) . O224 H224 O233 0.96(4) 1.70(4) 2.589(3) 151(3) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 24.78 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.420 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.057 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.500 0.059 393 64 ' ' 2 1.000 1.000 0.059 393 64 ' ' _platon_squeeze_details ; ; #=== END data_1.DCM _database_code_depnum_ccdc_archive 'CCDC 837703' #TrackingRef '- revision_2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,4 lutidinium pamoate hydrate dichloromethane solvate' _chemical_melting_point ? _chemical_formula_moiety ; C7 H10 N 1+ , C23 H15 O6 1- , 0.764(H2 O), 0.868(C H2 Cl2) ; _chemical_formula_sum 'C30.87 H28.26 Cl1.74 N O6.76' _chemical_formula_weight 582.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 21.952(7) _cell_length_b 19.780(7) _cell_length_c 14.411(5) _cell_angle_alpha 90.00 _cell_angle_beta 114.883(4) _cell_angle_gamma 90.00 _cell_volume 5676(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1660 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 21.23 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2433 _exptl_absorpt_coefficient_mu 0.252 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5784 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _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 '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 14538 _diffrn_reflns_av_R_equivalents 0.0827 _diffrn_reflns_av_sigmaI/netI 0.1051 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4988 _reflns_number_gt 2811 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The model contains one dichloromethane molecule on a special position. The second dichloromethane molecule, also on a special position, has been modelled with partial occupancy. A water with partial occupancy has been modelled on the same site. An ISOR restarint was used on the carbon of the partially occupied DCM. O-H distances in the hydrogen bonded water molecule have been restrained using DFIX. This structure has been included despite the high R(obs) for the purposes of comparison. The crystals were not excellent quality, but it is clear that they do contain dichloromethane. This has also been confirmed by NMR. ; _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^)+(0.1205P)^2^+39.4902P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0037(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4988 _refine_ls_number_parameters 400 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1664 _refine_ls_R_factor_gt 0.1050 _refine_ls_wR_factor_ref 0.3092 _refine_ls_wR_factor_gt 0.2758 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.074 _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 O1 O 0.0000 0.6697(3) 0.7500 0.0313(14) Uani 1 2 d SD . . H1 H -0.007(3) 0.644(3) 0.691(3) 0.032(17) Uiso 1 1 d D . . Cl2 Cl 0.9872(3) 0.8989(3) 0.8462(6) 0.240(3) Uani 1 1 d . . . C2 C 1.0000 0.9577(18) 0.7500 0.29(2) Uani 1 2 d S . . H2A H 1.0398 0.9868 0.7849 0.350 Uiso 0.50 1 calc PR . . H2B H 0.9602 0.9868 0.7151 0.350 Uiso 0.50 1 calc PR . . Cl1 Cl 1.0100(2) 1.1266(3) 0.8604(5) 0.141(3) Uani 0.736(12) 1 d P A 1 C1 C 1.0000 1.1775(14) 0.7500 0.141(12) Uani 0.736(12) 2 d SPU . 1 H1A H 0.9602 1.2070 0.7318 0.169 Uiso 0.368(6) 1 calc PR A 1 H1B H 1.0398 1.2070 0.7682 0.169 Uiso 0.368(6) 1 calc PR A 1 N11 N 0.6215(3) 1.0164(3) 0.6331(4) 0.0336(13) Uani 1 1 d . . . H11 H 0.591(4) 0.992(4) 0.635(6) 0.07(3) Uiso 1 1 d . . . C12 C 0.6740(3) 0.9755(3) 0.6500(5) 0.0383(16) Uani 1 1 d . . . H12 H 0.6687 0.9280 0.6532 0.046 Uiso 1 1 calc R . . C13 C 0.7357(3) 1.0010(3) 0.6627(5) 0.0352(15) Uani 1 1 d . . . C14 C 0.7415(3) 1.0715(3) 0.6591(5) 0.0369(16) Uani 1 1 d . . . C15 C 0.6855(3) 1.1118(3) 0.6382(5) 0.0400(17) Uani 1 1 d . . . H15 H 0.6884 1.1594 0.6324 0.048 Uiso 1 1 calc R . . C16 C 0.6257(3) 1.0826(3) 0.6258(5) 0.0386(16) Uani 1 1 d . . . H16 H 0.5874 1.1100 0.6119 0.046 Uiso 1 1 calc R . . C17 C 0.7931(3) 0.9548(4) 0.6800(6) 0.0451(18) Uani 1 1 d . . . H17A H 0.8301 0.9650 0.7462 0.068 Uiso 1 1 calc R . . H17B H 0.8080 0.9610 0.6254 0.068 Uiso 1 1 calc R . . H17C H 0.7787 0.9078 0.6798 0.068 Uiso 1 1 calc R . . C18 C 0.8076(3) 1.1038(4) 0.6778(6) 0.0449(18) Uani 1 1 d . . . H18A H 0.8227 1.0877 0.6266 0.067 Uiso 1 1 calc R . . H18B H 0.8410 1.0918 0.7463 0.067 Uiso 1 1 calc R . . H18C H 0.8023 1.1531 0.6726 0.067 Uiso 1 1 calc R . . O211 O 0.4211(2) 0.8776(2) 0.6174(4) 0.0369(12) Uani 1 1 d . . . C211 C 0.3777(3) 0.9291(3) 0.6108(5) 0.0315(14) Uani 1 1 d . . . H211 H 0.448(4) 0.896(4) 0.607(5) 0.04(2) Uiso 1 1 d . . . C212 C 0.3991(3) 0.9977(3) 0.6140(5) 0.0317(14) Uani 1 1 d . . . C213 C 0.3554(3) 1.0485(3) 0.6065(5) 0.0321(14) Uani 1 1 d . . . H213 H 0.3698 1.0941 0.6091 0.039 Uiso 1 1 calc R . . C214 C 0.2901(3) 1.0356(3) 0.5951(5) 0.0337(15) Uani 1 1 d . . . C215 C 0.2454(3) 1.0888(3) 0.5846(5) 0.0390(16) Uani 1 1 d . . . H215 H 0.2610 1.1341 0.5910 0.047 Uiso 1 1 calc R . . C216 C 0.1797(3) 1.0765(4) 0.5652(5) 0.0409(17) Uani 1 1 d . . . H216 H 0.1498 1.1130 0.5576 0.049 Uiso 1 1 calc R . . C217 C 0.1572(3) 1.0101(3) 0.5569(5) 0.0404(17) Uani 1 1 d . . . H217 H 0.1116 1.0017 0.5431 0.049 Uiso 1 1 calc R . . C218 C 0.1993(3) 0.9563(4) 0.5680(5) 0.0387(16) Uani 1 1 d . . . H218 H 0.1823 0.9115 0.5615 0.046 Uiso 1 1 calc R . . C219 C 0.2688(3) 0.9671(3) 0.5895(5) 0.0323(15) Uani 1 1 d . . . C220 C 0.3137(3) 0.9124(3) 0.6008(5) 0.0321(14) Uani 1 1 d . . . O221 O 0.5059(2) 0.9645(2) 0.6233(3) 0.0364(11) Uani 1 1 d . . . C221 C 0.4678(3) 1.0148(3) 0.6198(5) 0.0339(15) Uani 1 1 d . . . O222 O 0.4832(2) 1.0747(2) 0.6163(4) 0.0395(11) Uani 1 1 d . . . C222 C 0.2922(3) 0.8393(3) 0.5924(5) 0.0345(15) Uani 1 1 d . . . H22A H 0.2526 0.8333 0.5263 0.041 Uiso 1 1 calc R . . H22B H 0.3289 0.8111 0.5901 0.041 Uiso 1 1 calc R . . C223 C 0.2749(3) 0.8124(3) 0.6760(5) 0.0303(14) Uani 1 1 d . . . O224 O 0.1628(2) 0.7962(2) 0.5579(3) 0.0344(11) Uani 1 1 d . . . C224 C 0.2100(3) 0.7937(3) 0.6574(5) 0.0294(14) Uani 1 1 d . . . H224 H 0.121(4) 0.774(3) 0.558(5) 0.045(19) Uiso 1 1 d . . . C225 C 0.1926(3) 0.7724(3) 0.7364(5) 0.0285(14) Uani 1 1 d . . . C226 C 0.2401(3) 0.7674(3) 0.8338(5) 0.0304(14) Uani 1 1 d . . . H226 H 0.2275 0.7548 0.8869 0.036 Uiso 1 1 calc R . . C227 C 0.3081(3) 0.7808(3) 0.8572(5) 0.0304(14) Uani 1 1 d . . . C228 C 0.3581(3) 0.7712(3) 0.9595(5) 0.0321(14) Uani 1 1 d . . . H228 H 0.3456 0.7580 1.0125 0.039 Uiso 1 1 calc R . . C229 C 0.4239(3) 0.7813(3) 0.9796(5) 0.0380(16) Uani 1 1 d . . . H229 H 0.4574 0.7739 1.0469 0.046 Uiso 1 1 calc R . . C230 C 0.4425(3) 0.8019(3) 0.9042(5) 0.0394(17) Uani 1 1 d . . . H230 H 0.4888 0.8080 0.9206 0.047 Uiso 1 1 calc R . . C231 C 0.3958(3) 0.8140(3) 0.8050(5) 0.0337(15) Uani 1 1 d . . . H231 H 0.4098 0.8291 0.7545 0.040 Uiso 1 1 calc R . . C232 C 0.3261(3) 0.8033(3) 0.7798(5) 0.0305(14) Uani 1 1 d . . . O233 O 0.07937(19) 0.7469(2) 0.6236(3) 0.0375(11) Uani 1 1 d . . . C233 C 0.1225(3) 0.7499(3) 0.7118(5) 0.0309(14) Uani 1 1 d . . . O234 O 0.11226(19) 0.7315(2) 0.7910(3) 0.0388(12) Uani 1 1 d D . . H234 H 0.076(3) 0.704(5) 0.786(8) 0.12(4) Uiso 1 1 d D . . O2 O 1.0542(15) 1.1849(14) 0.832(3) 0.113(13) Uani 0.264(12) 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.014(3) 0.040(4) 0.040(4) 0.000 0.012(3) 0.000 Cl2 0.135(4) 0.184(5) 0.328(8) 0.083(5) 0.026(5) -0.044(4) C2 0.36(5) 0.21(3) 0.49(7) 0.000 0.36(6) 0.000 Cl1 0.097(4) 0.114(4) 0.177(6) -0.005(4) 0.022(3) 0.004(3) C1 0.067(18) 0.11(2) 0.22(4) 0.000 0.04(2) 0.000 N11 0.026(3) 0.037(3) 0.042(3) 0.000(2) 0.020(3) -0.002(2) C12 0.046(4) 0.035(4) 0.040(4) 0.003(3) 0.024(3) -0.001(3) C13 0.031(3) 0.039(4) 0.038(4) 0.002(3) 0.017(3) 0.000(3) C14 0.034(4) 0.045(4) 0.042(4) -0.003(3) 0.026(3) -0.005(3) C15 0.039(4) 0.037(4) 0.057(5) -0.001(3) 0.032(3) -0.003(3) C16 0.038(4) 0.040(4) 0.046(4) 0.008(3) 0.026(3) 0.006(3) C17 0.036(4) 0.044(4) 0.056(5) 0.009(3) 0.020(3) 0.004(3) C18 0.040(4) 0.045(4) 0.058(5) -0.001(3) 0.030(4) -0.007(3) O211 0.023(2) 0.035(3) 0.057(3) -0.005(2) 0.021(2) -0.003(2) C211 0.026(3) 0.032(3) 0.039(4) 0.001(3) 0.016(3) 0.006(3) C212 0.028(3) 0.038(4) 0.032(4) -0.002(3) 0.016(3) -0.004(3) C213 0.029(3) 0.032(3) 0.036(4) -0.001(3) 0.015(3) 0.001(3) C214 0.028(3) 0.042(4) 0.035(4) -0.003(3) 0.017(3) -0.002(3) C215 0.042(4) 0.036(4) 0.045(4) -0.004(3) 0.024(3) 0.005(3) C216 0.028(3) 0.044(4) 0.055(5) 0.001(3) 0.021(3) 0.007(3) C217 0.029(3) 0.046(4) 0.050(4) 0.006(3) 0.021(3) 0.008(3) C218 0.029(3) 0.046(4) 0.046(4) 0.000(3) 0.020(3) 0.000(3) C219 0.025(3) 0.038(4) 0.036(4) -0.004(3) 0.015(3) -0.001(3) C220 0.023(3) 0.039(4) 0.033(4) -0.003(3) 0.011(3) 0.001(3) O221 0.028(2) 0.033(2) 0.049(3) -0.002(2) 0.017(2) -0.0013(19) C221 0.026(3) 0.042(4) 0.033(4) 0.000(3) 0.012(3) 0.003(3) O222 0.036(2) 0.034(3) 0.057(3) 0.001(2) 0.029(2) -0.002(2) C222 0.022(3) 0.036(4) 0.047(4) -0.004(3) 0.016(3) 0.001(3) C223 0.027(3) 0.024(3) 0.039(4) -0.004(3) 0.013(3) 0.002(2) O224 0.019(2) 0.041(3) 0.039(3) 0.001(2) 0.0079(19) -0.0041(19) C224 0.014(3) 0.030(3) 0.038(4) -0.004(3) 0.005(3) 0.001(2) C225 0.017(3) 0.029(3) 0.035(4) -0.002(3) 0.006(3) -0.004(2) C226 0.020(3) 0.034(3) 0.036(4) -0.001(3) 0.011(3) -0.002(3) C227 0.021(3) 0.030(3) 0.039(4) 0.003(3) 0.011(3) 0.000(3) C228 0.018(3) 0.037(4) 0.037(4) 0.000(3) 0.007(3) 0.000(3) C229 0.018(3) 0.038(4) 0.050(4) 0.006(3) 0.006(3) 0.002(3) C230 0.021(3) 0.040(4) 0.052(4) 0.004(3) 0.010(3) -0.005(3) C231 0.018(3) 0.032(3) 0.052(4) 0.002(3) 0.016(3) 0.000(3) C232 0.018(3) 0.029(3) 0.042(4) -0.001(3) 0.010(3) 0.004(2) O233 0.018(2) 0.048(3) 0.041(3) -0.003(2) 0.007(2) -0.0057(19) C233 0.016(3) 0.035(4) 0.038(4) 0.002(3) 0.009(3) 0.001(2) O234 0.016(2) 0.057(3) 0.040(3) 0.001(2) 0.0082(19) -0.010(2) O2 0.063(19) 0.07(2) 0.15(3) 0.003(18) 0.000(19) 0.017(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 H1 0.949(10) . ? Cl2 C2 1.92(2) . ? C2 Cl2 1.92(2) 2_756 ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? Cl1 C1 1.816(16) . ? C1 Cl1 1.816(16) 2_756 ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? N11 C16 1.320(8) . ? N11 C12 1.343(8) . ? N11 H11 0.85(9) . ? C12 C13 1.382(9) . ? C12 H12 0.9500 . ? C13 C14 1.404(9) . ? C13 C17 1.491(9) . ? C14 C15 1.387(9) . ? C14 C18 1.503(9) . ? C15 C16 1.375(9) . ? 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 . ? O211 C211 1.371(7) . ? O211 H211 0.75(7) . ? C211 C220 1.389(8) . ? C211 C212 1.430(9) . ? C212 C213 1.363(9) . ? C212 C221 1.513(9) . ? C213 C214 1.397(8) . ? C213 H213 0.9500 . ? C214 C215 1.403(9) . ? C214 C219 1.424(9) . ? C215 C216 1.371(9) . ? C215 H215 0.9500 . ? C216 C217 1.390(9) . ? C216 H216 0.9500 . ? C217 C218 1.374(9) . ? C217 H217 0.9500 . ? C218 C219 1.440(9) . ? C218 H218 0.9500 . ? C219 C220 1.426(8) . ? C220 C222 1.511(9) . ? O221 C221 1.286(7) . ? C221 O222 1.238(8) . ? C222 C223 1.505(9) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C223 C224 1.383(8) . ? C223 C232 1.456(9) . ? O224 C224 1.371(7) . ? O224 H224 1.02(7) . ? C224 C225 1.410(9) . ? C225 C226 1.355(8) . ? C225 C233 1.493(8) . ? C226 C227 1.411(8) . ? C226 H226 0.9500 . ? C227 C232 1.403(9) . ? C227 C228 1.433(9) . ? C228 C229 1.363(8) . ? C228 H228 0.9500 . ? C229 C230 1.374(9) . ? C229 H229 0.9500 . ? C230 C231 1.385(9) . ? C230 H230 0.9500 . ? C231 C232 1.432(8) . ? C231 H231 0.9500 . ? O233 C233 1.227(7) . ? C233 O234 1.304(8) . ? O234 H234 0.951(10) . ? 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 Cl2 C2 Cl2 105.5(18) . 2_756 ? Cl2 C2 H2A 110.6 . . ? Cl2 C2 H2A 110.6 2_756 . ? Cl2 C2 H2B 110.6 . . ? Cl2 C2 H2B 110.6 2_756 . ? H2A C2 H2B 108.8 . . ? Cl1 C1 Cl1 112.7(16) 2_756 . ? Cl1 C1 H1A 109.1 2_756 . ? Cl1 C1 H1A 109.1 . . ? Cl1 C1 H1B 109.1 2_756 . ? Cl1 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? C16 N11 C12 121.9(6) . . ? C16 N11 H11 131(6) . . ? C12 N11 H11 107(6) . . ? N11 C12 C13 121.5(6) . . ? N11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C12 C13 C14 117.2(6) . . ? C12 C13 C17 120.6(6) . . ? C14 C13 C17 122.2(6) . . ? C15 C14 C13 119.5(6) . . ? C15 C14 C18 119.7(6) . . ? C13 C14 C18 120.8(6) . . ? C16 C15 C14 119.8(6) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? N11 C16 C15 120.1(6) . . ? N11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? 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 . . ? 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 . . ? C211 O211 H211 102(5) . . ? O211 C211 C220 118.3(6) . . ? O211 C211 C212 119.5(5) . . ? C220 C211 C212 122.3(5) . . ? C213 C212 C211 119.1(5) . . ? C213 C212 C221 119.4(6) . . ? C211 C212 C221 121.4(5) . . ? C212 C213 C214 121.8(6) . . ? C212 C213 H213 119.1 . . ? C214 C213 H213 119.1 . . ? C213 C214 C215 120.8(6) . . ? C213 C214 C219 118.6(6) . . ? C215 C214 C219 120.6(6) . . ? C216 C215 C214 121.1(6) . . ? C216 C215 H215 119.4 . . ? C214 C215 H215 119.4 . . ? C215 C216 C217 119.3(6) . . ? C215 C216 H216 120.3 . . ? C217 C216 H216 120.3 . . ? C218 C217 C216 121.7(6) . . ? C218 C217 H217 119.1 . . ? C216 C217 H217 119.1 . . ? C217 C218 C219 120.6(6) . . ? C217 C218 H218 119.7 . . ? C219 C218 H218 119.7 . . ? C214 C219 C220 121.3(5) . . ? C214 C219 C218 116.6(6) . . ? C220 C219 C218 122.1(6) . . ? C211 C220 C219 116.9(6) . . ? C211 C220 C222 120.3(5) . . ? C219 C220 C222 122.6(5) . . ? O222 C221 O221 123.9(6) . . ? O222 C221 C212 119.6(6) . . ? O221 C221 C212 116.5(6) . . ? C223 C222 C220 116.7(5) . . ? C223 C222 H22A 108.1 . . ? C220 C222 H22A 108.1 . . ? C223 C222 H22B 108.1 . . ? C220 C222 H22B 108.1 . . ? H22A C222 H22B 107.3 . . ? C224 C223 C232 117.0(6) . . ? C224 C223 C222 121.7(6) . . ? C232 C223 C222 121.3(5) . . ? C224 O224 H224 105(4) . . ? O224 C224 C223 117.2(6) . . ? O224 C224 C225 120.8(5) . . ? C223 C224 C225 122.0(5) . . ? C226 C225 C224 120.4(5) . . ? C226 C225 C233 119.4(6) . . ? C224 C225 C233 120.1(5) . . ? C225 C226 C227 120.6(6) . . ? C225 C226 H226 119.7 . . ? C227 C226 H226 119.7 . . ? C232 C227 C226 119.6(6) . . ? C232 C227 C228 120.7(5) . . ? C226 C227 C228 119.7(6) . . ? C229 C228 C227 118.9(6) . . ? C229 C228 H228 120.6 . . ? C227 C228 H228 120.6 . . ? C228 C229 C230 121.1(6) . . ? C228 C229 H229 119.5 . . ? C230 C229 H229 119.5 . . ? C229 C230 C231 122.1(6) . . ? C229 C230 H230 119.0 . . ? C231 C230 H230 119.0 . . ? C230 C231 C232 118.9(6) . . ? C230 C231 H231 120.5 . . ? C232 C231 H231 120.5 . . ? C227 C232 C231 118.3(6) . . ? C227 C232 C223 120.1(5) . . ? C231 C232 C223 121.6(6) . . ? O233 C233 O234 123.5(5) . . ? O233 C233 C225 121.9(6) . . ? O234 C233 C225 114.6(5) . . ? C233 O234 H234 123(7) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O222 0.949(10) 1.70(3) 2.605(6) 158(6) 3_445 N11 H11 O221 0.85(9) 1.87(9) 2.684(7) 161(8) . O211 H211 O221 0.75(7) 1.81(7) 2.510(6) 153(7) . O224 H224 O233 1.02(7) 1.65(7) 2.581(6) 149(6) . O234 H234 O1 0.951(10) 1.66(3) 2.586(5) 164(10) . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.413 _refine_diff_density_min -0.768 _refine_diff_density_rms 0.122 #=== END data_1.THF_b _database_code_depnum_ccdc_archive 'CCDC 837704' #TrackingRef '- revision_2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;3,4 lutidinium pamoate hydrate THF solvate after immersion in supercritical CO2 ; _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N 1+ , C23 H15 O6 1- , 1/2(H2 O) , 1/2(C4 H8 O) ' _chemical_formula_sum 'C32 H30 N O7' _chemical_formula_weight 540.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 22.110(6) _cell_length_b 19.808(5) _cell_length_c 14.613(4) _cell_angle_alpha 90.00 _cell_angle_beta 114.992(4) _cell_angle_gamma 90.00 _cell_volume 5801(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1929 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 24.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2280 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6655 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _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 '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 15212 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5120 _reflns_number_gt 3386 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The C3-C4 bond length was restrained using DFIX. SIMU and DELU restraints were applied to both THF molecules. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.4622P] 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 5120 _refine_ls_number_parameters 451 _refine_ls_number_restraints 81 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.0000 0.33839(11) 0.7500 0.0232(5) Uani 1 2 d S . . H1 H 1.0108(13) 0.3699(13) 0.8073(19) 0.056(9) Uiso 1 1 d . . . H11 H 0.4279(14) 0.0126(13) 0.880(2) 0.064(9) Uiso 1 1 d . . . O2 O -0.0570(7) 0.1022(9) 0.6962(12) 0.106(5) Uani 0.25 1 d PU A -1 C2 C -0.0612(6) 0.1059(6) 0.7922(9) 0.050(3) Uani 0.25 1 d PU A -1 H2A H -0.0872 0.1465 0.7928 0.060 Uiso 0.25 1 calc PR A -1 H2B H -0.0855 0.0658 0.7997 0.060 Uiso 0.25 1 calc PR A -1 O3 O 0.5210(7) 0.4264(6) 0.7039(13) 0.108(4) Uani 0.25 1 d PU B -1 C3 C -0.0009(6) 0.1088(7) 0.8714(11) 0.063(3) Uani 0.25 1 d PDU A -1 H3A H 0.0113 0.0648 0.9065 0.076 Uiso 0.25 1 calc PR A -1 H3B H 0.0002 0.1440 0.9202 0.076 Uiso 0.25 1 calc PR A -1 C4 C 0.0408(12) 0.1249(15) 0.8271(17) 0.110(7) Uani 0.25 1 d PDU A -1 H4A H 0.0807 0.0956 0.8565 0.132 Uiso 0.25 1 calc PR A -1 H4B H 0.0559 0.1721 0.8451 0.132 Uiso 0.25 1 calc PR A -1 C5 C 0.0115(9) 0.1182(11) 0.7139(12) 0.108(6) Uani 0.25 1 d PU A -1 H5A H 0.0144 0.1609 0.6807 0.130 Uiso 0.25 1 calc PR A -1 H5B H 0.0326 0.0812 0.6921 0.130 Uiso 0.25 1 calc PR A -1 C6 C 0.4980(10) 0.3669(8) 0.6413(17) 0.096(5) Uani 0.25 1 d PU B -1 H6A H 0.5350 0.3453 0.6310 0.115 Uiso 0.25 1 calc PR B -1 H6B H 0.4620 0.3786 0.5746 0.115 Uiso 0.25 1 calc PR B -1 C7 C 0.4725(15) 0.3214(14) 0.698(3) 0.082(6) Uani 0.25 1 d PU B -1 H7A H 0.4795 0.2735 0.6857 0.099 Uiso 0.25 1 calc PR B -1 H7B H 0.4244 0.3291 0.6782 0.099 Uiso 0.25 1 calc PR B -1 C8 C 0.5137(18) 0.3403(16) 0.808(3) 0.106(10) Uani 0.25 1 d PU B -1 H8A H 0.4897 0.3300 0.8508 0.127 Uiso 0.25 1 calc PR B -1 H8B H 0.5577 0.3177 0.8369 0.127 Uiso 0.25 1 calc PR B -1 C9 C 0.5196(9) 0.4136(10) 0.7964(18) 0.098(5) Uani 0.25 1 d PU B -1 H9A H 0.4812 0.4373 0.8001 0.117 Uiso 0.25 1 calc PR B -1 H9B H 0.5610 0.4307 0.8517 0.117 Uiso 0.25 1 calc PR B -1 N11 N 0.38313(10) -0.00922(9) 0.87380(14) 0.0240(4) Uani 1 1 d . . . C12 C 0.33106(11) 0.03100(11) 0.85887(17) 0.0263(6) Uani 1 1 d . . . H12 H 0.3361 0.0785 0.8557 0.032 Uiso 1 1 calc R . . C13 C 0.26991(11) 0.00514(12) 0.84794(16) 0.0251(5) Uani 1 1 d . . . C14 C 0.26437(11) -0.06533(12) 0.85246(16) 0.0242(5) Uani 1 1 d . . . C15 C 0.32032(11) -0.10458(12) 0.87180(17) 0.0277(6) Uani 1 1 d . . . H15 H 0.3178 -0.1521 0.8782 0.033 Uiso 1 1 calc R . . C16 C 0.37929(12) -0.07588(12) 0.88190(17) 0.0277(6) Uani 1 1 d . . . H16 H 0.4172 -0.1034 0.8946 0.033 Uiso 1 1 calc R . . C17 C 0.21311(12) 0.05149(13) 0.83330(19) 0.0347(6) Uani 1 1 d . . . H17A H 0.1744 0.0394 0.7710 0.052 Uiso 1 1 calc R . . H17B H 0.2262 0.0982 0.8286 0.052 Uiso 1 1 calc R . . H17C H 0.2015 0.0473 0.8908 0.052 Uiso 1 1 calc R . . C18 C 0.19928(11) -0.09768(12) 0.83657(18) 0.0327(6) Uani 1 1 d . . . H18A H 0.2041 -0.1469 0.8382 0.049 Uiso 1 1 calc R . . H18B H 0.1647 -0.0839 0.7709 0.049 Uiso 1 1 calc R . . H18C H 0.1866 -0.0834 0.8902 0.049 Uiso 1 1 calc R . . O211 O 0.58004(8) 0.12914(7) 0.87927(12) 0.0260(4) Uani 1 1 d . . . C211 C 0.62252(10) 0.07825(11) 0.88334(16) 0.0216(5) Uani 1 1 d . . . H211 H 0.5407(16) 0.1037(15) 0.876(2) 0.080(10) Uiso 1 1 d . . . C212 C 0.60088(10) 0.00984(11) 0.88110(16) 0.0211(5) Uani 1 1 d . . . C213 C 0.64362(11) -0.04120(11) 0.88549(16) 0.0231(5) Uani 1 1 d . . . H213 H 0.6291 -0.0866 0.8823 0.028 Uiso 1 1 calc R . . C214 C 0.70873(11) -0.02821(11) 0.89467(16) 0.0217(5) Uani 1 1 d . . . C215 C 0.75308(11) -0.08183(11) 0.90216(17) 0.0267(6) Uani 1 1 d . . . H215 H 0.7376 -0.1271 0.8956 0.032 Uiso 1 1 calc R . . C216 C 0.81750(11) -0.06966(12) 0.91862(18) 0.0296(6) Uani 1 1 d . . . H216 H 0.8467 -0.1061 0.9239 0.036 Uiso 1 1 calc R . . C217 C 0.84036(11) -0.00265(12) 0.92773(17) 0.0284(6) Uani 1 1 d . . . H217 H 0.8854 0.0059 0.9402 0.034 Uiso 1 1 calc R . . C218 C 0.79838(11) 0.05051(11) 0.91889(17) 0.0238(5) Uani 1 1 d . . . H218 H 0.8150 0.0953 0.9253 0.029 Uiso 1 1 calc R . . C219 C 0.73062(10) 0.04015(11) 0.90047(16) 0.0208(5) Uani 1 1 d . . . C220 C 0.68582(10) 0.09405(11) 0.89217(16) 0.0212(5) Uani 1 1 d . . . O221 O 0.49620(7) 0.04225(8) 0.87661(12) 0.0277(4) Uani 1 1 d . . . C221 C 0.53432(11) -0.00715(12) 0.87935(16) 0.0225(5) Uani 1 1 d . . . O222 O 0.51890(8) -0.06759(8) 0.88348(12) 0.0291(4) Uani 1 1 d . . . C222 C 0.70769(11) 0.16800(10) 0.90152(17) 0.0234(5) Uani 1 1 d . . . H22A H 0.6715 0.1963 0.9040 0.028 Uiso 1 1 calc R . . H22B H 0.7473 0.1738 0.9666 0.028 Uiso 1 1 calc R . . C223 C 0.72469(10) 0.19425(10) 0.81789(17) 0.0207(5) Uani 1 1 d . . . O224 O 0.83609(8) 0.21147(8) 0.93645(11) 0.0270(4) Uani 1 1 d . . . C224 C 0.78938(10) 0.21368(10) 0.83871(16) 0.0203(5) Uani 1 1 d . . . H224 H 0.8767(14) 0.2274(14) 0.935(2) 0.062(9) Uiso 1 1 d . . . C225 C 0.80737(10) 0.23585(10) 0.76070(16) 0.0199(5) Uani 1 1 d . . . C226 C 0.75966(10) 0.23934(10) 0.66343(16) 0.0211(5) Uani 1 1 d . . . H226 H 0.7723 0.2524 0.6114 0.025 Uiso 1 1 calc R . . C227 C 0.69249(10) 0.22416(10) 0.63840(16) 0.0202(5) Uani 1 1 d . . . C228 C 0.64289(11) 0.23095(11) 0.53815(18) 0.0274(6) Uani 1 1 d . . . H228 H 0.6554 0.2443 0.4862 0.033 Uiso 1 1 calc R . . C229 C 0.57761(11) 0.21859(11) 0.51536(18) 0.0295(6) Uani 1 1 d . . . H229 H 0.5447 0.2234 0.4480 0.035 Uiso 1 1 calc R . . C230 C 0.55939(11) 0.19857(11) 0.59262(19) 0.0288(6) Uani 1 1 d . . . H230 H 0.5136 0.1907 0.5767 0.035 Uiso 1 1 calc R . . C231 C 0.60551(10) 0.19017(10) 0.68965(18) 0.0248(5) Uani 1 1 d . . . H231 H 0.5915 0.1761 0.7397 0.030 Uiso 1 1 calc R . . C232 C 0.67456(10) 0.20225(10) 0.71700(17) 0.0208(5) Uani 1 1 d . . . O233 O 0.92022(7) 0.26029(8) 0.87316(12) 0.0285(4) Uani 1 1 d . . . C233 C 0.87659(11) 0.25810(11) 0.78633(18) 0.0231(5) Uani 1 1 d . . . O234 O 0.88699(8) 0.27800(8) 0.70810(12) 0.0286(4) Uani 1 1 d . . . H234 H 0.9304(13) 0.2993(12) 0.7287(19) 0.052(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0171(12) 0.0242(13) 0.0294(14) 0.000 0.0110(10) 0.000 O2 0.073(7) 0.166(12) 0.075(7) -0.016(9) 0.027(6) -0.042(8) C2 0.029(5) 0.071(8) 0.044(7) -0.010(6) 0.010(5) -0.016(6) O3 0.092(9) 0.061(6) 0.151(11) -0.004(7) 0.032(10) -0.009(7) C3 0.053(7) 0.066(8) 0.064(7) -0.011(7) 0.017(5) 0.000(6) C4 0.065(9) 0.18(2) 0.087(10) -0.045(13) 0.036(7) -0.031(13) C5 0.057(9) 0.191(16) 0.058(9) 0.020(10) 0.006(7) -0.058(11) C6 0.092(12) 0.058(10) 0.129(12) -0.010(9) 0.038(11) 0.007(9) C7 0.048(10) 0.060(11) 0.146(13) -0.031(10) 0.049(8) -0.002(8) C8 0.08(2) 0.101(16) 0.134(10) 0.000(14) 0.045(15) -0.016(16) C9 0.052(10) 0.090(12) 0.149(12) -0.044(10) 0.042(11) -0.018(9) N11 0.0262(11) 0.0259(12) 0.0222(11) -0.0004(8) 0.0124(9) -0.0024(9) C12 0.0307(14) 0.0255(13) 0.0243(14) 0.0008(10) 0.0131(11) -0.0018(11) C13 0.0274(13) 0.0293(14) 0.0187(13) 0.0017(10) 0.0098(10) 0.0006(10) C14 0.0254(13) 0.0317(14) 0.0170(12) -0.0019(10) 0.0105(10) -0.0038(10) C15 0.0319(14) 0.0247(13) 0.0321(15) -0.0032(10) 0.0192(11) -0.0049(11) C16 0.0315(14) 0.0288(14) 0.0253(14) -0.0014(10) 0.0145(11) 0.0005(11) C17 0.0302(14) 0.0383(16) 0.0378(16) 0.0045(12) 0.0165(12) 0.0057(11) C18 0.0287(14) 0.0398(15) 0.0322(15) -0.0019(12) 0.0153(12) -0.0093(11) O211 0.0214(9) 0.0234(9) 0.0377(10) 0.0005(7) 0.0170(8) 0.0011(7) C211 0.0237(12) 0.0260(13) 0.0167(12) 0.0014(9) 0.0101(10) 0.0049(10) C212 0.0215(12) 0.0244(13) 0.0174(12) -0.0011(9) 0.0082(10) -0.0024(10) C213 0.0263(13) 0.0235(13) 0.0198(13) -0.0011(9) 0.0101(10) -0.0016(10) C214 0.0233(12) 0.0257(13) 0.0165(12) -0.0006(9) 0.0088(10) 0.0008(10) C215 0.0307(14) 0.0256(13) 0.0258(14) -0.0019(10) 0.0141(11) 0.0013(10) C216 0.0277(13) 0.0323(15) 0.0298(14) 0.0015(11) 0.0131(11) 0.0079(11) C217 0.0221(12) 0.0371(15) 0.0285(14) 0.0041(11) 0.0129(11) 0.0042(11) C218 0.0236(12) 0.0260(13) 0.0222(13) 0.0029(10) 0.0102(10) 0.0008(10) C219 0.0198(12) 0.0271(13) 0.0169(12) 0.0019(9) 0.0092(10) 0.0001(10) C220 0.0215(12) 0.0263(13) 0.0174(12) 0.0016(9) 0.0099(10) -0.0007(10) O221 0.0229(9) 0.0270(9) 0.0376(10) -0.0024(7) 0.0170(8) -0.0015(7) C221 0.0216(12) 0.0294(14) 0.0176(12) -0.0044(10) 0.0093(10) -0.0019(11) O222 0.0323(9) 0.0255(10) 0.0372(10) -0.0035(7) 0.0220(8) -0.0065(7) C222 0.0224(12) 0.0235(13) 0.0255(13) 0.0004(10) 0.0114(10) -0.0004(10) C223 0.0207(12) 0.0188(12) 0.0243(13) -0.0007(9) 0.0112(10) -0.0005(9) O224 0.0209(9) 0.0357(10) 0.0215(9) 0.0015(7) 0.0060(7) -0.0052(7) C224 0.0194(12) 0.0178(12) 0.0219(13) 0.0004(9) 0.0069(10) 0.0012(9) C225 0.0178(12) 0.0183(12) 0.0241(13) -0.0002(9) 0.0092(10) -0.0006(9) C226 0.0186(12) 0.0216(12) 0.0237(13) -0.0001(9) 0.0096(10) -0.0028(9) C227 0.0190(12) 0.0188(12) 0.0229(13) 0.0006(9) 0.0089(10) 0.0004(9) C228 0.0215(13) 0.0315(14) 0.0284(14) 0.0012(11) 0.0099(11) -0.0023(10) C229 0.0189(12) 0.0341(14) 0.0289(14) 0.0038(11) 0.0037(11) -0.0014(10) C230 0.0172(12) 0.0294(14) 0.0383(16) 0.0058(11) 0.0101(11) 0.0002(10) C231 0.0199(12) 0.0231(13) 0.0341(15) 0.0044(10) 0.0140(11) -0.0002(9) C232 0.0202(12) 0.0163(12) 0.0254(13) -0.0017(9) 0.0092(10) -0.0004(9) O233 0.0177(8) 0.0367(10) 0.0276(10) 0.0018(7) 0.0061(8) -0.0036(7) C233 0.0200(12) 0.0217(13) 0.0281(14) 0.0011(10) 0.0106(11) 0.0012(9) O234 0.0188(9) 0.0412(10) 0.0272(10) 0.0017(8) 0.0109(7) -0.0080(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 H1 0.99(3) . ? O2 C2 1.446(18) . ? O2 C5 1.46(2) . ? C2 C3 1.348(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? O3 C9 1.39(2) . ? O3 C6 1.45(2) . ? C3 C4 1.37(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.51(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.49(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.53(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.48(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N11 C16 1.332(3) . ? N11 C12 1.340(3) . ? N11 H11 1.05(3) . ? C12 C13 1.390(3) . ? C12 H12 0.9500 . ? C13 C14 1.405(3) . ? C13 C17 1.496(3) . ? C14 C15 1.385(3) . ? C14 C18 1.501(3) . ? C15 C16 1.372(3) . ? 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 . ? O211 C211 1.362(3) . ? O211 H211 0.99(3) . ? C211 C220 1.386(3) . ? C211 C212 1.433(3) . ? C212 C213 1.367(3) . ? C212 C221 1.499(3) . ? C213 C214 1.412(3) . ? C213 H213 0.9500 . ? C214 C215 1.418(3) . ? C214 C219 1.428(3) . ? C215 C216 1.362(3) . ? C215 H215 0.9500 . ? C216 C217 1.406(3) . ? C216 H216 0.9500 . ? C217 C218 1.373(3) . ? C217 H217 0.9500 . ? C218 C219 1.421(3) . ? C218 H218 0.9500 . ? C219 C220 1.426(3) . ? C220 C222 1.530(3) . ? O221 C221 1.281(3) . ? C221 O222 1.253(3) . ? C222 C223 1.514(3) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C223 C224 1.385(3) . ? C223 C232 1.431(3) . ? O224 C224 1.365(3) . ? O224 H224 0.96(3) . ? C224 C225 1.426(3) . ? C225 C226 1.368(3) . ? C225 C233 1.481(3) . ? C226 C227 1.404(3) . ? C226 H226 0.9500 . ? C227 C228 1.418(3) . ? C227 C232 1.432(3) . ? C228 C229 1.359(3) . ? C228 H228 0.9500 . ? C229 C230 1.407(3) . ? C229 H229 0.9500 . ? C230 C231 1.362(3) . ? C230 H230 0.9500 . ? C231 C232 1.425(3) . ? C231 H231 0.9500 . ? O233 C233 1.228(3) . ? C233 O234 1.318(3) . ? O234 H234 0.97(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 C5 107.7(13) . . ? C3 C2 O2 112.9(12) . . ? C3 C2 H2A 109.0 . . ? O2 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? O2 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C9 O3 C6 108.8(15) . . ? C2 C3 C4 102.9(16) . . ? C2 C3 H3A 111.2 . . ? C4 C3 H3A 111.2 . . ? C2 C3 H3B 111.2 . . ? C4 C3 H3B 111.2 . . ? H3A C3 H3B 109.1 . . ? C3 C4 C5 116(2) . . ? C3 C4 H4A 108.3 . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4B 108.3 . . ? C5 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? O2 C5 C4 98.3(14) . . ? O2 C5 H5A 112.1 . . ? C4 C5 H5A 112.1 . . ? O2 C5 H5B 112.1 . . ? C4 C5 H5B 112.1 . . ? H5A C5 H5B 109.7 . . ? O3 C6 C7 105(2) . . ? O3 C6 H6A 110.8 . . ? C7 C6 H6A 110.8 . . ? O3 C6 H6B 110.8 . . ? C7 C6 H6B 110.8 . . ? H6A C6 H6B 108.9 . . ? C6 C7 C8 104(2) . . ? C6 C7 H7A 110.9 . . ? C8 C7 H7A 110.9 . . ? C6 C7 H7B 110.9 . . ? C8 C7 H7B 110.9 . . ? H7A C7 H7B 108.9 . . ? C9 C8 C7 99(3) . . ? C9 C8 H8A 111.9 . . ? C7 C8 H8A 111.9 . . ? C9 C8 H8B 111.9 . . ? C7 C8 H8B 111.9 . . ? H8A C8 H8B 109.6 . . ? O3 C9 C8 110(2) . . ? O3 C9 H9A 109.8 . . ? C8 C9 H9A 109.8 . . ? O3 C9 H9B 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? C16 N11 C12 121.4(2) . . ? C16 N11 H11 119.7(15) . . ? C12 N11 H11 118.9(15) . . ? N11 C12 C13 121.8(2) . . ? N11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C12 C13 C14 117.4(2) . . ? C12 C13 C17 120.5(2) . . ? C14 C13 C17 122.1(2) . . ? C15 C14 C13 118.6(2) . . ? C15 C14 C18 120.5(2) . . ? C13 C14 C18 120.9(2) . . ? C16 C15 C14 121.0(2) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? N11 C16 C15 119.6(2) . . ? N11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? 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 . . ? 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 . . ? C211 O211 H211 101.7(18) . . ? O211 C211 C220 119.2(2) . . ? O211 C211 C212 118.79(19) . . ? C220 C211 C212 122.01(19) . . ? C213 C212 C211 118.7(2) . . ? C213 C212 C221 119.3(2) . . ? C211 C212 C221 121.90(19) . . ? C212 C213 C214 121.8(2) . . ? C212 C213 H213 119.1 . . ? C214 C213 H213 119.1 . . ? C213 C214 C215 121.0(2) . . ? C213 C214 C219 118.98(19) . . ? C215 C214 C219 120.0(2) . . ? C216 C215 C214 121.2(2) . . ? C216 C215 H215 119.4 . . ? C214 C215 H215 119.4 . . ? C215 C216 C217 119.4(2) . . ? C215 C216 H216 120.3 . . ? C217 C216 H216 120.3 . . ? C218 C217 C216 120.9(2) . . ? C218 C217 H217 119.6 . . ? C216 C217 H217 119.6 . . ? C217 C218 C219 121.6(2) . . ? C217 C218 H218 119.2 . . ? C219 C218 H218 119.2 . . ? C218 C219 C220 123.2(2) . . ? C218 C219 C214 116.86(19) . . ? C220 C219 C214 119.93(19) . . ? C211 C220 C219 118.46(19) . . ? C211 C220 C222 119.54(19) . . ? C219 C220 C222 121.80(19) . . ? O222 C221 O221 122.9(2) . . ? O222 C221 C212 119.9(2) . . ? O221 C221 C212 117.2(2) . . ? C223 C222 C220 115.68(18) . . ? C223 C222 H22A 108.4 . . ? C220 C222 H22A 108.4 . . ? C223 C222 H22B 108.4 . . ? C220 C222 H22B 108.4 . . ? H22A C222 H22B 107.4 . . ? C224 C223 C232 118.3(2) . . ? C224 C223 C222 120.23(19) . . ? C232 C223 C222 121.42(19) . . ? C224 O224 H224 105.6(17) . . ? O224 C224 C223 118.4(2) . . ? O224 C224 C225 120.21(19) . . ? C223 C224 C225 121.39(19) . . ? C226 C225 C224 119.53(19) . . ? C226 C225 C233 120.6(2) . . ? C224 C225 C233 119.81(19) . . ? C225 C226 C227 121.8(2) . . ? C225 C226 H226 119.1 . . ? C227 C226 H226 119.1 . . ? C226 C227 C228 121.4(2) . . ? C226 C227 C232 118.49(19) . . ? C228 C227 C232 120.1(2) . . ? C229 C228 C227 120.9(2) . . ? C229 C228 H228 119.5 . . ? C227 C228 H228 119.5 . . ? C228 C229 C230 119.3(2) . . ? C228 C229 H229 120.4 . . ? C230 C229 H229 120.4 . . ? C231 C230 C229 121.8(2) . . ? C231 C230 H230 119.1 . . ? C229 C230 H230 119.1 . . ? C230 C231 C232 120.9(2) . . ? C230 C231 H231 119.6 . . ? C232 C231 H231 119.6 . . ? C231 C232 C223 122.8(2) . . ? C231 C232 C227 116.9(2) . . ? C223 C232 C227 120.25(19) . . ? O233 C233 O234 122.5(2) . . ? O233 C233 C225 123.3(2) . . ? O234 C233 C225 114.21(19) . . ? C233 O234 H234 111.9(15) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O222 0.99(3) 1.62(3) 2.600(2) 168(2) 3 N11 H11 O221 1.05(3) 1.64(3) 2.684(2) 173(3) . O211 H211 O221 0.99(3) 1.57(3) 2.518(2) 159(3) . O224 H224 O233 0.96(3) 1.70(3) 2.589(2) 152(3) . O234 H234 O1 0.97(3) 1.63(3) 2.5992(19) 173(2) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.232 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.048 #=== END data_2b _database_code_depnum_ccdc_archive 'CCDC 837705' #TrackingRef '- revision_2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;2,5 lutidinium pamoate NMP solvate after immersion in supercritical CO2 ; _chemical_melting_point ? _chemical_formula_moiety '0.5(C46H31O12 -1), 0.5(C7H10N +1) , 1.75(C5H9NO)' _chemical_formula_sum 'C36.25 H36.25 N2.25 O7.75' _chemical_formula_weight 627.43 # formula weight is given including disordered channel contents # number of NMP molecules in the channel is an approximation based in part on NMR data loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6349(5) _cell_length_b 10.4211(7) _cell_length_c 19.9971(13) _cell_angle_alpha 89.2820(10) _cell_angle_beta 85.5280(10) _cell_angle_gamma 74.5590(10) _cell_volume 1528.90(17) _cell_formula_units_Z 2 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 4346 _cell_measurement_theta_min 2.263 _cell_measurement_theta_max 20.077 _exptl_crystal_description shard _exptl_crystal_colour yellow _exptl_crystal_size_max 0.610 _exptl_crystal_size_mid 0.547 _exptl_crystal_size_min 0.545 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 663 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9525 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_special_details ; Crystals were immmersed in supercritical CO2 for 10 minutes before collecting this data. ; _diffrn_ambient_temperature 105(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 9811 _diffrn_reflns_av_R_equivalents 0.0128 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.30 _reflns_number_total 6900 _reflns_number_gt 5488 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008), Platon/SQUEEZE (Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H211, 222, 224 and 234 were found in the difference map before application of SQUEEZE. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0871P)^2^+0.1291P] 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 6900 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1455 _refine_ls_wR_factor_gt 0.1372 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.04223(12) 0.92160(9) -0.08046(5) 0.0274(2) Uani 1 1 d . . . C1 C 0.89285(17) 1.00429(13) -0.08547(6) 0.0253(3) Uani 1 1 d . . . N2 N 0.86704(15) 1.10295(11) -0.13006(6) 0.0277(2) Uani 1 1 d . . . C3 C 0.68045(18) 1.18479(13) -0.13054(7) 0.0286(3) Uani 1 1 d . . . H3A H 0.6281 1.1729 -0.1731 0.034 Uiso 1 1 calc R . . H3B H 0.6743 1.2801 -0.1247 0.034 Uiso 1 1 calc R . . C4 C 0.57883(18) 1.13408(14) -0.07059(7) 0.0303(3) Uani 1 1 d . . . H4A H 0.5377 1.2036 -0.0353 0.036 Uiso 1 1 calc R . . H4B H 0.4711 1.1091 -0.0851 0.036 Uiso 1 1 calc R . . C5 C 0.71582(17) 1.01257(13) -0.04446(6) 0.0268(3) Uani 1 1 d . . . H5A H 0.7297 1.0237 0.0038 0.032 Uiso 1 1 calc R . . H5B H 0.6756 0.9310 -0.0505 0.032 Uiso 1 1 calc R . . C6 C 1.0083(2) 1.12351(14) -0.17861(7) 0.0332(3) Uani 1 1 d . . . H6A H 0.9790 1.1061 -0.2239 0.050 Uiso 1 1 calc R . . H6B H 1.1257 1.0627 -0.1692 0.050 Uiso 1 1 calc R . . H6C H 1.0157 1.2157 -0.1755 0.050 Uiso 1 1 calc R . . O211 O 0.85331(14) 0.14329(9) 0.27636(5) 0.0311(2) Uani 1 1 d . . . H211 H 0.863(3) 0.082(2) 0.3086(13) 0.081(7) Uiso 1 1 d . . . C211 C 0.86169(17) 0.25414(12) 0.30994(6) 0.0234(3) Uani 1 1 d . . . C212 C 0.89345(18) 0.24486(12) 0.37943(6) 0.0266(3) Uani 1 1 d . . . C213 C 0.89743(19) 0.35647(13) 0.41374(7) 0.0273(3) Uani 1 1 d . . . H213 H 0.9184 0.3501 0.4600 0.033 Uiso 1 1 calc R . . C214 C 0.87111(17) 0.48106(12) 0.38190(6) 0.0252(3) Uani 1 1 d . . . C215 C 0.8717(2) 0.59676(13) 0.41837(7) 0.0314(3) Uani 1 1 d . . . H215 H 0.8909 0.5901 0.4648 0.038 Uiso 1 1 calc R . . C216 C 0.8450(2) 0.71756(13) 0.38780(7) 0.0341(3) Uani 1 1 d . . . H216 H 0.8488 0.7941 0.4124 0.041 Uiso 1 1 calc R . . C217 C 0.8119(2) 0.72727(13) 0.31946(7) 0.0323(3) Uani 1 1 d . . . H217 H 0.7903 0.8117 0.2985 0.039 Uiso 1 1 calc R . . C218 C 0.81001(17) 0.61742(12) 0.28225(7) 0.0262(3) Uani 1 1 d . . . H218 H 0.7866 0.6273 0.2362 0.031 Uiso 1 1 calc R . . C219 C 0.84282(16) 0.48894(12) 0.31205(6) 0.0218(3) Uani 1 1 d . . . C220 C 0.84353(15) 0.37281(12) 0.27533(6) 0.0213(2) Uani 1 1 d . . . O221 O 0.90515(19) 0.01492(10) 0.38372(6) 0.0480(3) Uani 1 1 d . . . C221 C 0.9237(2) 0.11366(14) 0.41418(7) 0.0372(3) Uani 1 1 d . . . O222 O 0.9696(2) 0.11092(10) 0.47431(5) 0.0556(4) Uani 1 1 d . . . H222 H 1.0000 0.0000 0.5000 0.098(12) Uiso 1 2 d S . . C222 C 0.82022(16) 0.37502(12) 0.20052(6) 0.0229(3) Uani 1 1 d . . . H22A H 0.8141 0.2856 0.1867 0.027 Uiso 1 1 calc R . . H22B H 0.7018 0.4384 0.1926 0.027 Uiso 1 1 calc R . . C223 C 0.96786(16) 0.41306(12) 0.15577(6) 0.0213(2) Uani 1 1 d . . . O224 O 0.74582(12) 0.59649(10) 0.11674(5) 0.0292(2) Uani 1 1 d . . . C224 C 0.92308(16) 0.52376(12) 0.11512(6) 0.0225(3) Uani 1 1 d . . . H224 H 0.742(3) 0.663(2) 0.0849(10) 0.059(6) Uiso 1 1 d . . . C225 C 1.05892(16) 0.56271(12) 0.07209(6) 0.0214(2) Uani 1 1 d . . . C226 C 1.23740(17) 0.48893(12) 0.07091(6) 0.0225(3) Uani 1 1 d . . . H226 H 1.3275 0.5161 0.0431 0.027 Uiso 1 1 calc R . . C227 C 1.28951(16) 0.37365(12) 0.11013(6) 0.0215(2) Uani 1 1 d . . . C228 C 1.47276(16) 0.29612(13) 0.10761(6) 0.0246(3) Uani 1 1 d . . . H228 H 1.5632 0.3239 0.0803 0.030 Uiso 1 1 calc R . . C229 C 1.52174(17) 0.18177(13) 0.14386(7) 0.0283(3) Uani 1 1 d . . . H229 H 1.6455 0.1312 0.1423 0.034 Uiso 1 1 calc R . . C230 C 1.38684(18) 0.13966(13) 0.18356(7) 0.0289(3) Uani 1 1 d . . . H230 H 1.4206 0.0592 0.2080 0.035 Uiso 1 1 calc R . . C231 C 1.20809(17) 0.21236(12) 0.18767(6) 0.0254(3) Uani 1 1 d . . . H231 H 1.1201 0.1815 0.2148 0.030 Uiso 1 1 calc R . . C232 C 1.15214(16) 0.33385(12) 0.15183(6) 0.0215(2) Uani 1 1 d . . . O233 O 0.84530(13) 0.75025(10) 0.03080(5) 0.0333(2) Uani 1 1 d . . . C233 C 1.00398(17) 0.68325(12) 0.03024(6) 0.0235(3) Uani 1 1 d . . . O234 O 1.13620(12) 0.71406(9) -0.00713(4) 0.0266(2) Uani 1 1 d . . . H234 H 1.083(3) 0.793(2) -0.0313(12) 0.076(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0227(4) 0.0279(5) 0.0291(5) 0.0058(4) 0.0008(3) -0.0036(4) C1 0.0263(6) 0.0245(6) 0.0253(6) 0.0005(5) -0.0012(5) -0.0073(5) N2 0.0286(6) 0.0237(6) 0.0285(6) 0.0039(4) 0.0042(4) -0.0051(5) C3 0.0265(6) 0.0242(6) 0.0330(7) 0.0040(5) -0.0017(5) -0.0036(5) C4 0.0257(6) 0.0296(7) 0.0327(7) 0.0042(5) 0.0011(5) -0.0036(5) C5 0.0240(6) 0.0303(7) 0.0262(6) 0.0044(5) 0.0003(5) -0.0082(5) C6 0.0352(7) 0.0271(7) 0.0356(7) 0.0034(5) 0.0103(6) -0.0089(6) O211 0.0473(6) 0.0216(5) 0.0289(5) 0.0000(4) -0.0029(4) -0.0169(4) C211 0.0263(6) 0.0198(6) 0.0261(6) 0.0003(5) -0.0009(5) -0.0099(5) C212 0.0348(7) 0.0192(6) 0.0268(6) 0.0054(5) -0.0019(5) -0.0094(5) C213 0.0376(7) 0.0222(6) 0.0239(6) 0.0035(5) -0.0041(5) -0.0105(5) C214 0.0286(6) 0.0197(6) 0.0282(6) 0.0019(5) 0.0000(5) -0.0088(5) C215 0.0430(8) 0.0232(7) 0.0297(7) 0.0002(5) -0.0022(6) -0.0122(6) C216 0.0443(8) 0.0192(6) 0.0393(8) -0.0028(5) 0.0060(6) -0.0119(6) C217 0.0378(7) 0.0163(6) 0.0393(8) 0.0048(5) 0.0109(6) -0.0055(5) C218 0.0269(6) 0.0216(6) 0.0279(6) 0.0054(5) 0.0051(5) -0.0048(5) C219 0.0189(5) 0.0196(6) 0.0271(6) 0.0045(5) 0.0018(4) -0.0064(5) C220 0.0185(5) 0.0221(6) 0.0241(6) 0.0040(5) -0.0004(4) -0.0074(5) O221 0.0901(9) 0.0217(5) 0.0376(6) 0.0069(4) -0.0090(6) -0.0237(6) C221 0.0607(10) 0.0214(7) 0.0315(7) 0.0074(5) -0.0049(7) -0.0142(7) O222 0.1132(11) 0.0244(5) 0.0322(6) 0.0124(4) -0.0197(6) -0.0203(6) C222 0.0189(5) 0.0255(6) 0.0250(6) 0.0032(5) -0.0017(4) -0.0074(5) C223 0.0194(6) 0.0247(6) 0.0204(6) 0.0011(4) -0.0021(4) -0.0068(5) O224 0.0179(4) 0.0339(5) 0.0325(5) 0.0124(4) -0.0006(4) -0.0018(4) C224 0.0186(6) 0.0271(6) 0.0210(6) 0.0013(5) -0.0023(4) -0.0044(5) C225 0.0227(6) 0.0229(6) 0.0185(6) 0.0023(4) -0.0020(4) -0.0056(5) C226 0.0226(6) 0.0254(6) 0.0201(6) -0.0001(4) -0.0002(4) -0.0079(5) C227 0.0213(6) 0.0237(6) 0.0199(6) -0.0012(4) -0.0030(4) -0.0061(5) C228 0.0196(6) 0.0280(6) 0.0263(6) -0.0011(5) -0.0018(5) -0.0064(5) C229 0.0207(6) 0.0279(7) 0.0339(7) -0.0011(5) -0.0037(5) -0.0018(5) C230 0.0282(7) 0.0241(6) 0.0326(7) 0.0045(5) -0.0048(5) -0.0037(5) C231 0.0256(6) 0.0239(6) 0.0263(6) 0.0029(5) -0.0021(5) -0.0061(5) C232 0.0219(6) 0.0227(6) 0.0200(6) 0.0001(4) -0.0035(4) -0.0056(5) O233 0.0243(5) 0.0334(5) 0.0375(5) 0.0146(4) 0.0006(4) -0.0011(4) C233 0.0241(6) 0.0251(6) 0.0206(6) 0.0019(5) -0.0013(4) -0.0056(5) O234 0.0254(4) 0.0273(5) 0.0261(5) 0.0074(4) 0.0007(3) -0.0064(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2432(15) . ? C1 N2 1.3370(16) . ? C1 C5 1.5079(17) . ? N2 C6 1.4514(16) . ? N2 C3 1.4533(16) . ? C3 C4 1.5414(18) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5277(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? O211 C211 1.3620(15) . ? O211 H211 0.90(2) . ? C211 C220 1.3892(16) . ? C211 C212 1.4267(18) . ? C212 C213 1.3663(18) . ? C212 C221 1.4963(17) . ? C213 C214 1.4113(17) . ? C213 H213 0.9500 . ? C214 C215 1.4182(18) . ? C214 C219 1.4280(18) . ? C215 C216 1.3652(18) . ? C215 H215 0.9500 . ? C216 C217 1.406(2) . ? C216 H216 0.9500 . ? C217 C218 1.3770(19) . ? C217 H217 0.9500 . ? C218 C219 1.4266(16) . ? C218 H218 0.9500 . ? C219 C220 1.4220(17) . ? C220 C222 1.5195(17) . ? O221 C221 1.2478(18) . ? C221 O222 1.2763(18) . ? O222 H222 1.2307(10) . ? C222 C223 1.5167(16) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C223 C224 1.3851(17) . ? C223 C232 1.4258(16) . ? O224 C224 1.3619(14) . ? O224 H224 0.93(2) . ? C224 C225 1.4341(16) . ? C225 C226 1.3734(17) . ? C225 C233 1.4840(16) . ? C226 C227 1.4096(17) . ? C226 H226 0.9500 . ? C227 C228 1.4146(17) . ? C227 C232 1.4331(17) . ? C228 C229 1.3670(18) . ? C228 H228 0.9500 . ? C229 C230 1.4101(19) . ? C229 H229 0.9500 . ? C230 C231 1.3699(18) . ? C230 H230 0.9500 . ? C231 C232 1.4269(17) . ? C231 H231 0.9500 . ? O233 C233 1.2260(15) . ? C233 O234 1.3151(15) . ? O234 H234 0.96(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N2 123.30(11) . . ? O1 C1 C5 127.59(11) . . ? N2 C1 C5 109.10(11) . . ? C1 N2 C6 123.90(11) . . ? C1 N2 C3 114.99(10) . . ? C6 N2 C3 120.94(11) . . ? N2 C3 C4 104.15(10) . . ? N2 C3 H3A 110.9 . . ? C4 C3 H3A 110.9 . . ? N2 C3 H3B 110.9 . . ? C4 C3 H3B 110.9 . . ? H3A C3 H3B 108.9 . . ? C5 C4 C3 105.83(10) . . ? C5 C4 H4A 110.6 . . ? C3 C4 H4A 110.6 . . ? C5 C4 H4B 110.6 . . ? C3 C4 H4B 110.6 . . ? H4A C4 H4B 108.7 . . ? C1 C5 C4 105.49(10) . . ? C1 C5 H5A 110.6 . . ? C4 C5 H5A 110.6 . . ? C1 C5 H5B 110.6 . . ? C4 C5 H5B 110.6 . . ? H5A C5 H5B 108.8 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C211 O211 H211 103.4(16) . . ? O211 C211 C220 119.20(11) . . ? O211 C211 C212 119.23(11) . . ? C220 C211 C212 121.56(11) . . ? C213 C212 C211 119.45(11) . . ? C213 C212 C221 120.36(12) . . ? C211 C212 C221 120.18(12) . . ? C212 C213 C214 121.41(12) . . ? C212 C213 H213 119.3 . . ? C214 C213 H213 119.3 . . ? C213 C214 C215 120.89(12) . . ? C213 C214 C219 118.76(11) . . ? C215 C214 C219 120.34(11) . . ? C216 C215 C214 121.02(13) . . ? C216 C215 H215 119.5 . . ? C214 C215 H215 119.5 . . ? C215 C216 C217 119.15(13) . . ? C215 C216 H216 120.4 . . ? C217 C216 H216 120.4 . . ? C218 C217 C216 121.65(12) . . ? C218 C217 H217 119.2 . . ? C216 C217 H217 119.2 . . ? C217 C218 C219 120.71(12) . . ? C217 C218 H218 119.6 . . ? C219 C218 H218 119.6 . . ? C220 C219 C218 122.53(11) . . ? C220 C219 C214 120.38(10) . . ? C218 C219 C214 117.07(11) . . ? C211 C220 C219 118.28(11) . . ? C211 C220 C222 119.26(11) . . ? C219 C220 C222 122.44(10) . . ? O221 C221 O222 124.11(12) . . ? O221 C221 C212 119.59(13) . . ? O222 C221 C212 116.30(12) . . ? C221 O222 H222 114.06(10) . . ? C223 C222 C220 115.95(10) . . ? 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 118.48(10) . . ? C224 C223 C222 119.83(10) . . ? C232 C223 C222 121.63(10) . . ? C224 O224 H224 106.1(12) . . ? O224 C224 C223 118.63(10) . . ? O224 C224 C225 119.96(10) . . ? C223 C224 C225 121.41(11) . . ? C226 C225 C224 119.54(11) . . ? C226 C225 C233 121.22(11) . . ? C224 C225 C233 119.23(11) . . ? C225 C226 C227 121.29(11) . . ? C225 C226 H226 119.4 . . ? C227 C226 H226 119.4 . . ? C226 C227 C228 121.15(11) . . ? C226 C227 C232 118.75(11) . . ? C228 C227 C232 120.09(11) . . ? C229 C228 C227 121.01(11) . . ? C229 C228 H228 119.5 . . ? C227 C228 H228 119.5 . . ? C228 C229 C230 119.38(12) . . ? C228 C229 H229 120.3 . . ? C230 C229 H229 120.3 . . ? C231 C230 C229 121.38(12) . . ? C231 C230 H230 119.3 . . ? C229 C230 H230 119.3 . . ? C230 C231 C232 120.95(11) . . ? C230 C231 H231 119.5 . . ? C232 C231 H231 119.5 . . ? C223 C232 C231 122.43(11) . . ? C223 C232 C227 120.41(11) . . ? C231 C232 C227 117.15(11) . . ? O233 C233 O234 122.16(11) . . ? O233 C233 C225 122.00(11) . . ? O234 C233 C225 115.84(11) . . ? C233 O234 H234 107.5(14) . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.306 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.064 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.686 0.500 457 96 ' ' _platon_squeeze_details ; ; #=== END data_3b _database_code_depnum_ccdc_archive 'CCDC 837706' #TrackingRef '- revision_2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;3,4 lutidinium pamoate NMP solvate after immersion in supercritical CO2 ; _chemical_melting_point ? _chemical_formula_moiety '0.5(C46H31O12 -1), 0.5(C7H10N +1) , 1.75(C5H9NO)' _chemical_formula_sum 'C36.25 H36.25 N2.25 O7.75' _chemical_formula_weight 627.43 # formula weight is given including disordered channel contents # number of NMP molecules in the channel is an approximation based in part on NMR data loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6792(6) _cell_length_b 10.3679(8) _cell_length_c 20.3093(17) _cell_angle_alpha 88.8600(10) _cell_angle_beta 83.3130(10) _cell_angle_gamma 74.8060(10) _cell_volume 1549.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4337 _cell_measurement_theta_min 2.263 _cell_measurement_theta_max 27.996 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 663 _exptl_absorpt_correction_type numerical _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_min 0.9398 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_special_details ; Crystals were immmersed in supercritical CO2 for 10 minutes before collecting this data. ; _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 9930 _diffrn_reflns_av_R_equivalents 0.0121 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 28.22 _reflns_number_total 7013 _reflns_number_gt 5549 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008), Platon/SQUEEZE (Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H211, 224 and 234 were found in the difference map before application of SQUEEZE. H222 was found in the difference map after SQUEEZE. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0881P)^2^+0.2300P] 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 7013 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1563 _refine_ls_wR_factor_gt 0.1490 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.04682(13) 0.91798(10) -0.07874(5) 0.0316(2) Uani 1 1 d . . . C1 C 0.89960(19) 1.00186(14) -0.08351(7) 0.0289(3) Uani 1 1 d . . . N2 N 0.88004(16) 1.10034(12) -0.12759(6) 0.0313(3) Uani 1 1 d . . . C3 C 0.6951(2) 1.18291(15) -0.12786(8) 0.0326(3) Uani 1 1 d . . . H3A H 0.6469 1.1711 -0.1698 0.039 Uiso 1 1 calc R . . H3B H 0.6894 1.2786 -0.1221 0.039 Uiso 1 1 calc R . . C4 C 0.5878(2) 1.13240(16) -0.06855(8) 0.0350(3) Uani 1 1 d . . . H4A H 0.5443 1.2024 -0.0336 0.042 Uiso 1 1 calc R . . H4B H 0.4815 1.1079 -0.0828 0.042 Uiso 1 1 calc R . . C5 C 0.71952(18) 1.01016(15) -0.04280(7) 0.0305(3) Uani 1 1 d . . . H5A H 0.7286 1.0212 0.0049 0.037 Uiso 1 1 calc R . . H5B H 0.6792 0.9284 -0.0489 0.037 Uiso 1 1 calc R . . C6 C 1.0250(2) 1.11969(16) -0.17575(8) 0.0380(4) Uani 1 1 d . . . H6A H 1.0040 1.0957 -0.2200 0.057 Uiso 1 1 calc R . . H6B H 1.1413 1.0628 -0.1648 0.057 Uiso 1 1 calc R . . H6C H 1.0279 1.2136 -0.1751 0.057 Uiso 1 1 calc R . . O211 O 0.85147(16) 0.13806(11) 0.28090(5) 0.0366(3) Uani 1 1 d . . . H211 H 0.876(4) 0.068(3) 0.3173(17) 0.124(11) Uiso 1 1 d . . . C211 C 0.86128(19) 0.25009(14) 0.31223(7) 0.0264(3) Uani 1 1 d . . . C212 C 0.8962(2) 0.24226(14) 0.37999(7) 0.0301(3) Uani 1 1 d . . . C213 C 0.9022(2) 0.35550(14) 0.41238(7) 0.0292(3) Uani 1 1 d . . . H213 H 0.9273 0.3500 0.4572 0.035 Uiso 1 1 calc R . . C214 C 0.87179(18) 0.47985(13) 0.38033(7) 0.0261(3) Uani 1 1 d . . . C215 C 0.8724(2) 0.59720(15) 0.41502(8) 0.0334(3) Uani 1 1 d . . . H215 H 0.8959 0.5912 0.4600 0.040 Uiso 1 1 calc R . . C216 C 0.8396(2) 0.71850(15) 0.38470(8) 0.0376(4) Uani 1 1 d . . . H216 H 0.8430 0.7962 0.4080 0.045 Uiso 1 1 calc R . . C217 C 0.8007(2) 0.72696(15) 0.31859(8) 0.0376(4) Uani 1 1 d . . . H217 H 0.7742 0.8118 0.2979 0.045 Uiso 1 1 calc R . . C218 C 0.79997(19) 0.61582(14) 0.28312(7) 0.0291(3) Uani 1 1 d . . . H218 H 0.7737 0.6249 0.2384 0.035 Uiso 1 1 calc R . . C219 C 0.83818(17) 0.48686(13) 0.31262(6) 0.0234(3) Uani 1 1 d . . . C220 C 0.83972(17) 0.36909(13) 0.27747(6) 0.0234(3) Uani 1 1 d . . . O221 O 0.9135(2) 0.01102(12) 0.38620(7) 0.0630(4) Uani 1 1 d . . . C221 C 0.9283(3) 0.11161(16) 0.41490(8) 0.0435(4) Uani 1 1 d . . . O222 O 0.9704(2) 0.11114(12) 0.47397(6) 0.0625(4) Uani 1 1 d . . . H222 H 1.0000 0.0000 0.5000 0.16(2) Uiso 1 2 d S . . C222 C 0.81473(17) 0.36965(14) 0.20435(6) 0.0260(3) Uani 1 1 d . . . H22A H 0.6964 0.4324 0.1980 0.031 Uiso 1 1 calc R . . H22B H 0.8091 0.2793 0.1916 0.031 Uiso 1 1 calc R . . C223 C 0.96206(17) 0.40854(14) 0.15758(6) 0.0238(3) Uani 1 1 d . . . O224 O 0.73969(13) 0.59149(11) 0.12120(5) 0.0331(2) Uani 1 1 d . . . H224 H 0.736(3) 0.659(2) 0.0899(12) 0.066(7) Uiso 1 1 d . . . C224 C 0.91685(17) 0.51922(14) 0.11769(6) 0.0251(3) Uani 1 1 d . . . C225 C 1.05196(18) 0.55988(14) 0.07357(6) 0.0248(3) Uani 1 1 d . . . C226 C 1.23046(18) 0.48728(14) 0.07056(6) 0.0251(3) Uani 1 1 d . . . H226 H 1.3203 0.5155 0.0420 0.030 Uiso 1 1 calc R . . C227 C 1.28259(17) 0.37216(14) 0.10887(6) 0.0245(3) Uani 1 1 d . . . C228 C 1.46636(18) 0.29675(14) 0.10523(7) 0.0283(3) Uani 1 1 d . . . H228 H 1.5567 0.3261 0.0776 0.034 Uiso 1 1 calc R . . C229 C 1.51548(19) 0.18246(15) 0.14083(8) 0.0326(3) Uani 1 1 d . . . H229 H 1.6393 0.1332 0.1384 0.039 Uiso 1 1 calc R . . C230 C 1.3805(2) 0.13822(15) 0.18125(8) 0.0344(3) Uani 1 1 d . . . H230 H 1.4146 0.0577 0.2053 0.041 Uiso 1 1 calc R . . C231 C 1.20161(19) 0.20872(14) 0.18654(7) 0.0282(3) Uani 1 1 d . . . H231 H 1.1137 0.1761 0.2138 0.034 Uiso 1 1 calc R . . C232 C 1.14591(17) 0.33018(14) 0.15174(6) 0.0238(3) Uani 1 1 d . . . O233 O 0.83988(13) 0.74707(11) 0.03463(5) 0.0360(3) Uani 1 1 d . . . C233 C 0.99824(18) 0.68030(14) 0.03233(6) 0.0266(3) Uani 1 1 d . . . O234 O 1.13067(13) 0.71110(11) -0.00624(5) 0.0306(2) Uani 1 1 d . . . H234 H 1.086(3) 0.785(2) -0.0304(13) 0.075(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0248(5) 0.0332(6) 0.0333(5) 0.0070(4) 0.0022(4) -0.0041(4) C1 0.0284(7) 0.0292(7) 0.0293(7) 0.0018(5) -0.0003(5) -0.0089(6) N2 0.0308(6) 0.0283(6) 0.0321(6) 0.0044(5) 0.0045(5) -0.0065(5) C3 0.0303(7) 0.0285(7) 0.0373(8) 0.0060(6) -0.0024(6) -0.0060(6) C4 0.0294(7) 0.0340(8) 0.0384(8) 0.0049(6) -0.0001(6) -0.0049(6) C5 0.0265(7) 0.0347(8) 0.0293(7) 0.0059(6) 0.0003(5) -0.0079(6) C6 0.0394(8) 0.0324(8) 0.0391(8) 0.0029(6) 0.0121(7) -0.0116(7) O211 0.0545(7) 0.0253(5) 0.0352(6) -0.0005(4) -0.0040(5) -0.0202(5) C211 0.0308(7) 0.0225(7) 0.0278(6) 0.0011(5) -0.0009(5) -0.0113(5) C212 0.0401(8) 0.0208(7) 0.0297(7) 0.0070(5) -0.0023(6) -0.0095(6) C213 0.0383(8) 0.0240(7) 0.0257(6) 0.0039(5) -0.0046(6) -0.0089(6) C214 0.0270(6) 0.0222(7) 0.0296(7) 0.0026(5) -0.0009(5) -0.0084(5) C215 0.0389(8) 0.0276(7) 0.0346(7) -0.0019(6) 0.0009(6) -0.0126(6) C216 0.0452(9) 0.0238(7) 0.0432(8) -0.0040(6) 0.0087(7) -0.0136(7) C217 0.0425(8) 0.0196(7) 0.0442(8) 0.0057(6) 0.0153(7) -0.0059(6) C218 0.0289(7) 0.0250(7) 0.0292(7) 0.0069(5) 0.0071(5) -0.0044(5) C219 0.0206(6) 0.0219(6) 0.0268(6) 0.0035(5) 0.0033(5) -0.0066(5) C220 0.0207(6) 0.0241(7) 0.0263(6) 0.0043(5) -0.0003(5) -0.0086(5) O221 0.1259(13) 0.0256(6) 0.0457(7) 0.0114(5) -0.0176(8) -0.0318(7) C221 0.0730(12) 0.0235(8) 0.0355(8) 0.0099(6) -0.0088(8) -0.0148(8) O222 0.1215(13) 0.0268(6) 0.0392(7) 0.0136(5) -0.0240(7) -0.0141(7) C222 0.0210(6) 0.0312(7) 0.0270(6) 0.0040(5) -0.0023(5) -0.0094(5) C223 0.0216(6) 0.0297(7) 0.0207(6) 0.0019(5) -0.0027(5) -0.0074(5) O224 0.0198(5) 0.0419(6) 0.0331(5) 0.0146(5) -0.0007(4) -0.0020(4) C224 0.0185(6) 0.0320(7) 0.0232(6) 0.0019(5) -0.0016(5) -0.0042(5) C225 0.0230(6) 0.0289(7) 0.0209(6) 0.0017(5) -0.0011(5) -0.0046(5) C226 0.0234(6) 0.0295(7) 0.0217(6) -0.0005(5) 0.0004(5) -0.0070(5) C227 0.0219(6) 0.0281(7) 0.0223(6) -0.0011(5) -0.0024(5) -0.0047(5) C228 0.0223(6) 0.0321(7) 0.0291(7) 0.0001(6) -0.0011(5) -0.0051(6) C229 0.0219(6) 0.0329(8) 0.0403(8) 0.0006(6) -0.0048(6) -0.0019(6) C230 0.0314(7) 0.0279(7) 0.0425(8) 0.0070(6) -0.0060(6) -0.0047(6) C231 0.0268(7) 0.0270(7) 0.0303(7) 0.0034(5) -0.0029(5) -0.0068(6) C232 0.0228(6) 0.0281(7) 0.0211(6) 0.0006(5) -0.0036(5) -0.0072(5) O233 0.0269(5) 0.0374(6) 0.0382(6) 0.0137(5) -0.0001(4) -0.0012(4) C233 0.0260(7) 0.0303(7) 0.0222(6) 0.0021(5) 0.0001(5) -0.0065(5) O234 0.0277(5) 0.0324(6) 0.0286(5) 0.0073(4) 0.0020(4) -0.0053(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2453(17) . ? C1 N2 1.3345(19) . ? C1 C5 1.5091(19) . ? N2 C6 1.4463(18) . ? N2 C3 1.4542(19) . ? C3 C4 1.541(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.526(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? O211 C211 1.3587(16) . ? O211 H211 1.02(3) . ? C211 C220 1.3905(18) . ? C211 C212 1.429(2) . ? C212 C213 1.371(2) . ? C212 C221 1.492(2) . ? C213 C214 1.4087(19) . ? C213 H213 0.9500 . ? C214 C215 1.4194(19) . ? C214 C219 1.4254(19) . ? C215 C216 1.365(2) . ? C215 H215 0.9500 . ? C216 C217 1.405(2) . ? C216 H216 0.9500 . ? C217 C218 1.373(2) . ? C217 H217 0.9500 . ? C218 C219 1.4269(18) . ? C218 H218 0.9500 . ? C219 C220 1.4233(18) . ? C220 C222 1.5191(18) . ? O221 C221 1.242(2) . ? C221 O222 1.278(2) . ? O222 H222 1.2350(11) . ? C222 C223 1.5227(17) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C223 C224 1.3831(19) . ? C223 C232 1.4251(18) . ? O224 C224 1.3648(16) . ? O224 H224 0.93(2) . ? C224 C225 1.4335(18) . ? C225 C226 1.3750(18) . ? C225 C233 1.4831(19) . ? C226 C227 1.4055(19) . ? C226 H226 0.9500 . ? C227 C228 1.4170(18) . ? C227 C232 1.4355(18) . ? C228 C229 1.365(2) . ? C228 H228 0.9500 . ? C229 C230 1.412(2) . ? C229 H229 0.9500 . ? C230 C231 1.370(2) . ? C230 H230 0.9500 . ? C231 C232 1.4216(19) . ? C231 H231 0.9500 . ? O233 C233 1.2276(17) . ? C233 O234 1.3131(16) . ? O234 H234 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N2 123.20(13) . . ? O1 C1 C5 127.28(13) . . ? N2 C1 C5 109.52(12) . . ? C1 N2 C6 124.05(13) . . ? C1 N2 C3 114.72(11) . . ? C6 N2 C3 121.04(12) . . ? N2 C3 C4 104.14(11) . . ? N2 C3 H3A 110.9 . . ? C4 C3 H3A 110.9 . . ? N2 C3 H3B 110.9 . . ? C4 C3 H3B 110.9 . . ? H3A C3 H3B 108.9 . . ? C5 C4 C3 106.07(11) . . ? C5 C4 H4A 110.5 . . ? C3 C4 H4A 110.5 . . ? C5 C4 H4B 110.5 . . ? C3 C4 H4B 110.5 . . ? H4A C4 H4B 108.7 . . ? C1 C5 C4 105.11(11) . . ? C1 C5 H5A 110.7 . . ? C4 C5 H5A 110.7 . . ? C1 C5 H5B 110.7 . . ? C4 C5 H5B 110.7 . . ? H5A C5 H5B 108.8 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C211 O211 H211 101.9(18) . . ? O211 C211 C220 119.35(12) . . ? O211 C211 C212 119.10(12) . . ? C220 C211 C212 121.54(12) . . ? C213 C212 C211 119.43(12) . . ? C213 C212 C221 120.30(13) . . ? C211 C212 C221 120.27(13) . . ? C212 C213 C214 121.14(13) . . ? C212 C213 H213 119.4 . . ? C214 C213 H213 119.4 . . ? C213 C214 C215 120.63(13) . . ? C213 C214 C219 119.16(12) . . ? C215 C214 C219 120.21(12) . . ? C216 C215 C214 121.01(14) . . ? C216 C215 H215 119.5 . . ? C214 C215 H215 119.5 . . ? C215 C216 C217 119.15(14) . . ? C215 C216 H216 120.4 . . ? C217 C216 H216 120.4 . . ? C218 C217 C216 121.69(13) . . ? C218 C217 H217 119.2 . . ? C216 C217 H217 119.2 . . ? C217 C218 C219 120.74(13) . . ? C217 C218 H218 119.6 . . ? C219 C218 H218 119.6 . . ? C220 C219 C214 120.33(12) . . ? C220 C219 C218 122.50(12) . . ? C214 C219 C218 117.16(12) . . ? C211 C220 C219 118.20(12) . . ? C211 C220 C222 119.28(12) . . ? C219 C220 C222 122.51(11) . . ? O221 C221 O222 123.75(14) . . ? O221 C221 C212 119.75(14) . . ? O222 C221 C212 116.50(14) . . ? C221 O222 H222 113.91(12) . . ? C220 C222 C223 115.36(10) . . ? C220 C222 H22A 108.4 . . ? C223 C222 H22A 108.4 . . ? C220 C222 H22B 108.4 . . ? C223 C222 H22B 108.4 . . ? H22A C222 H22B 107.5 . . ? C224 C223 C232 118.67(11) . . ? C224 C223 C222 119.79(11) . . ? C232 C223 C222 121.48(12) . . ? C224 O224 H224 106.0(14) . . ? O224 C224 C223 118.90(11) . . ? O224 C224 C225 119.66(12) . . ? C223 C224 C225 121.44(12) . . ? C226 C225 C224 119.44(12) . . ? C226 C225 C233 120.79(12) . . ? C224 C225 C233 119.76(12) . . ? C225 C226 C227 121.26(12) . . ? C225 C226 H226 119.4 . . ? C227 C226 H226 119.4 . . ? C226 C227 C228 121.18(12) . . ? C226 C227 C232 118.98(12) . . ? C228 C227 C232 119.84(12) . . ? C229 C228 C227 120.97(13) . . ? C229 C228 H228 119.5 . . ? C227 C228 H228 119.5 . . ? C228 C229 C230 119.36(13) . . ? C228 C229 H229 120.3 . . ? C230 C229 H229 120.3 . . ? C231 C230 C229 121.48(14) . . ? C231 C230 H230 119.3 . . ? C229 C230 H230 119.3 . . ? C230 C231 C232 120.80(13) . . ? C230 C231 H231 119.6 . . ? C232 C231 H231 119.6 . . ? C231 C232 C223 122.48(12) . . ? C231 C232 C227 117.46(12) . . ? C223 C232 C227 120.05(12) . . ? O233 C233 O234 122.39(13) . . ? O233 C233 C225 121.82(12) . . ? O234 C233 C225 115.78(12) . . ? C233 O234 H234 110.3(15) . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.283 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.067 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.479 0.500 478 99 ' ' _platon_squeeze_details ; ; #=== END data_4 _database_code_depnum_ccdc_archive 'CCDC 837707' #TrackingRef '- revision_2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3-picolinium pamoate NMP solvate' _chemical_melting_point ? _chemical_formula_moiety '0.5(C46H31O12 -1), 0.5(C6H8N +1) , 2(C5H9NO)' _chemical_formula_sum 'C36 H37.50 N2.50 O8' _chemical_formula_weight 633.18 # formula weight is given including disordered channel contents loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6538(7) _cell_length_b 10.3862(10) _cell_length_c 20.0151(19) _cell_angle_alpha 89.1230(10) _cell_angle_beta 85.4010(10) _cell_angle_gamma 74.2900(10) _cell_volume 1526.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5976 _cell_measurement_theta_min 2.273 _cell_measurement_theta_max 27.567 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 670 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6705 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _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 17282 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.02 _diffrn_reflns_theta_max 27.91 _reflns_number_total 6659 _reflns_number_gt 5287 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement ; SHELXL (Sheldrick, 2008), Platon/SQUEEZE (Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0634P)^2^+0.1836P] 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 6659 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1246 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.04248(11) 0.92378(8) -0.08094(4) 0.0282(2) Uani 1 1 d . . . C1 C 0.89245(17) 1.00666(12) -0.08622(6) 0.0272(3) Uani 1 1 d . . . N2 N 0.86612(15) 1.10558(10) -0.13089(5) 0.0300(2) Uani 1 1 d . . . C3 C 0.67924(17) 1.18742(13) -0.13161(7) 0.0300(3) Uani 1 1 d . . . H3A H 0.6273 1.1748 -0.1740 0.036 Uiso 1 1 calc R . . H3B H 0.6720 1.2834 -0.1262 0.036 Uiso 1 1 calc R . . C4 C 0.57856(18) 1.13652(13) -0.07123(7) 0.0324(3) Uani 1 1 d . . . H4A H 0.5378 1.2064 -0.0360 0.039 Uiso 1 1 calc R . . H4B H 0.4708 1.1119 -0.0854 0.039 Uiso 1 1 calc R . . C5 C 0.71533(17) 1.01418(13) -0.04515(6) 0.0285(3) Uani 1 1 d . . . H5A H 0.7287 1.0248 0.0031 0.034 Uiso 1 1 calc R . . H5B H 0.6758 0.9322 -0.0514 0.034 Uiso 1 1 calc R . . C6 C 1.00676(19) 1.12644(13) -0.17906(7) 0.0355(3) Uani 1 1 d . . . H6A H 0.9772 1.1103 -0.2244 0.053 Uiso 1 1 calc R . . H6B H 1.1239 1.0644 -0.1700 0.053 Uiso 1 1 calc R . . H6C H 1.0146 1.2187 -0.1754 0.053 Uiso 1 1 calc R . . O211 O 0.85295(14) 0.14258(9) 0.27640(5) 0.0334(2) Uani 1 1 d . . . H211 H 0.864(3) 0.078(2) 0.3094(11) 0.079(7) Uiso 1 1 d . . . C211 C 0.86136(17) 0.25385(12) 0.30954(6) 0.0253(3) Uani 1 1 d . . . C212 C 0.89382(18) 0.24546(12) 0.37889(6) 0.0300(3) Uani 1 1 d . . . C213 C 0.89801(19) 0.35786(13) 0.41283(6) 0.0315(3) Uani 1 1 d . . . H213 H 0.9211 0.3515 0.4589 0.038 Uiso 1 1 calc R . . C214 C 0.86870(17) 0.48280(12) 0.38075(6) 0.0288(3) Uani 1 1 d . . . C215 C 0.8677(2) 0.59956(14) 0.41670(7) 0.0368(3) Uani 1 1 d . . . H215 H 0.8888 0.5930 0.4629 0.044 Uiso 1 1 calc R . . C216 C 0.8369(2) 0.72122(14) 0.38616(8) 0.0401(3) Uani 1 1 d . . . H216 H 0.8393 0.7985 0.4105 0.048 Uiso 1 1 calc R . . C217 C 0.8017(2) 0.73029(13) 0.31795(7) 0.0366(3) Uani 1 1 d . . . H217 H 0.7766 0.8152 0.2969 0.044 Uiso 1 1 calc R . . C218 C 0.80273(17) 0.61983(12) 0.28126(7) 0.0291(3) Uani 1 1 d . . . H218 H 0.7791 0.6294 0.2353 0.035 Uiso 1 1 calc R . . C219 C 0.83883(15) 0.49046(12) 0.31103(6) 0.0235(3) Uani 1 1 d . . . C220 C 0.84170(15) 0.37301(12) 0.27473(6) 0.0232(3) Uani 1 1 d . . . O221 O 0.9127(2) 0.01354(10) 0.38374(6) 0.0588(3) Uani 1 1 d . . . C221 C 0.9264(2) 0.11361(14) 0.41398(7) 0.0429(4) Uani 1 1 d . . . O222 O 0.9688(2) 0.11220(11) 0.47441(6) 0.0643(4) Uani 1 1 d . . . H222 H 1.0000 0.0000 0.5000 0.158(17) Uiso 1 2 d S . . C222 C 0.81899(16) 0.37468(12) 0.19977(6) 0.0244(3) Uani 1 1 d . . . H22A H 0.8134 0.2848 0.1861 0.029 Uiso 1 1 calc R . . H22B H 0.7008 0.4384 0.1916 0.029 Uiso 1 1 calc R . . C223 C 0.96764(16) 0.41257(12) 0.15522(6) 0.0225(2) Uani 1 1 d . . . O224 O 0.74585(11) 0.59685(9) 0.11558(5) 0.0305(2) Uani 1 1 d . . . H224 H 0.740(3) 0.6654(19) 0.0859(10) 0.062(5) Uiso 1 1 d . . . C224 C 0.92312(16) 0.52386(12) 0.11440(6) 0.0236(3) Uani 1 1 d . . . C225 C 1.05940(16) 0.56272(12) 0.07161(6) 0.0229(2) Uani 1 1 d . . . C226 C 1.23810(16) 0.48799(12) 0.07091(6) 0.0234(2) Uani 1 1 d . . . H226 H 1.3287 0.5150 0.0434 0.028 Uiso 1 1 calc R . . C227 C 1.28903(16) 0.37229(12) 0.11021(6) 0.0224(2) Uani 1 1 d . . . C228 C 1.47299(16) 0.29368(12) 0.10829(6) 0.0259(3) Uani 1 1 d . . . H228 H 1.5638 0.3212 0.0811 0.031 Uiso 1 1 calc R . . C229 C 1.52124(17) 0.17923(12) 0.14483(7) 0.0289(3) Uani 1 1 d . . . H229 H 1.6448 0.1280 0.1436 0.035 Uiso 1 1 calc R . . C230 C 1.38575(17) 0.13776(12) 0.18451(7) 0.0296(3) Uani 1 1 d . . . H230 H 1.4193 0.0575 0.2095 0.036 Uiso 1 1 calc R . . C231 C 1.20704(17) 0.21067(12) 0.18783(6) 0.0258(3) Uani 1 1 d . . . H231 H 1.1186 0.1796 0.2145 0.031 Uiso 1 1 calc R . . C232 C 1.15168(15) 0.33261(12) 0.15176(6) 0.0223(2) Uani 1 1 d . . . O233 O 0.84627(12) 0.75131(9) 0.02985(5) 0.0340(2) Uani 1 1 d . . . C233 C 1.00539(16) 0.68375(12) 0.02964(6) 0.0243(3) Uani 1 1 d . . . O234 O 1.13745(12) 0.71493(9) -0.00732(4) 0.0277(2) Uani 1 1 d . . . H234 H 1.086(3) 0.793(2) -0.0331(11) 0.075(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0233(4) 0.0282(5) 0.0306(5) 0.0071(4) 0.0017(3) -0.0037(4) C1 0.0273(6) 0.0260(6) 0.0279(6) 0.0002(5) -0.0019(5) -0.0064(5) N2 0.0301(6) 0.0261(5) 0.0316(6) 0.0040(4) 0.0030(4) -0.0054(4) C3 0.0273(6) 0.0257(6) 0.0341(7) 0.0050(5) -0.0019(5) -0.0029(5) C4 0.0272(7) 0.0319(7) 0.0354(7) 0.0033(5) 0.0002(5) -0.0042(5) C5 0.0271(6) 0.0317(7) 0.0271(6) 0.0036(5) -0.0001(5) -0.0094(5) C6 0.0370(7) 0.0289(7) 0.0379(7) 0.0039(6) 0.0110(6) -0.0084(6) O211 0.0487(6) 0.0239(5) 0.0319(5) 0.0043(4) -0.0053(4) -0.0170(4) C211 0.0273(6) 0.0221(6) 0.0277(6) 0.0041(5) -0.0017(5) -0.0090(5) C212 0.0383(7) 0.0239(6) 0.0289(7) 0.0090(5) -0.0037(5) -0.0101(5) C213 0.0410(7) 0.0294(7) 0.0246(6) 0.0064(5) -0.0054(5) -0.0098(6) C214 0.0322(7) 0.0245(6) 0.0305(7) 0.0031(5) 0.0001(5) -0.0099(5) C215 0.0480(8) 0.0306(7) 0.0331(7) -0.0007(6) -0.0013(6) -0.0133(6) C216 0.0517(9) 0.0261(7) 0.0436(8) -0.0048(6) 0.0093(7) -0.0157(6) C217 0.0426(8) 0.0208(6) 0.0425(8) 0.0061(6) 0.0140(6) -0.0072(6) C218 0.0299(6) 0.0240(6) 0.0302(7) 0.0070(5) 0.0080(5) -0.0051(5) C219 0.0201(6) 0.0226(6) 0.0268(6) 0.0064(5) 0.0022(4) -0.0058(5) C220 0.0190(5) 0.0247(6) 0.0261(6) 0.0064(5) -0.0013(4) -0.0067(5) O221 0.1124(11) 0.0270(5) 0.0440(6) 0.0147(5) -0.0172(6) -0.0286(6) C221 0.0695(11) 0.0266(7) 0.0332(7) 0.0122(6) -0.0078(7) -0.0135(7) O222 0.1249(12) 0.0335(6) 0.0348(6) 0.0167(5) -0.0227(6) -0.0183(7) C222 0.0205(6) 0.0269(6) 0.0265(6) 0.0056(5) -0.0028(5) -0.0075(5) C223 0.0217(6) 0.0256(6) 0.0206(5) 0.0026(4) -0.0028(4) -0.0067(5) O224 0.0190(4) 0.0353(5) 0.0331(5) 0.0153(4) -0.0010(3) -0.0017(4) C224 0.0200(6) 0.0274(6) 0.0226(6) 0.0031(5) -0.0022(4) -0.0050(5) C225 0.0246(6) 0.0251(6) 0.0190(5) 0.0024(4) -0.0021(4) -0.0067(5) C226 0.0228(6) 0.0268(6) 0.0209(6) 0.0013(5) -0.0001(4) -0.0078(5) C227 0.0218(6) 0.0242(6) 0.0218(6) -0.0003(4) -0.0029(4) -0.0067(5) C228 0.0213(6) 0.0285(6) 0.0280(6) -0.0012(5) -0.0013(5) -0.0069(5) C229 0.0207(6) 0.0268(6) 0.0367(7) -0.0006(5) -0.0046(5) -0.0015(5) C230 0.0298(7) 0.0231(6) 0.0350(7) 0.0049(5) -0.0060(5) -0.0047(5) C231 0.0256(6) 0.0248(6) 0.0274(6) 0.0032(5) -0.0034(5) -0.0074(5) C232 0.0222(6) 0.0242(6) 0.0209(6) 0.0010(4) -0.0041(4) -0.0067(5) O233 0.0246(5) 0.0353(5) 0.0380(5) 0.0168(4) 0.0006(4) -0.0030(4) C233 0.0245(6) 0.0266(6) 0.0207(6) 0.0031(5) -0.0008(4) -0.0054(5) O234 0.0255(4) 0.0289(5) 0.0271(4) 0.0077(4) 0.0018(3) -0.0059(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2459(15) . ? C1 N2 1.3357(16) . ? C1 C5 1.5118(17) . ? N2 C6 1.4452(16) . ? N2 C3 1.4537(16) . ? C3 C4 1.5445(18) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5264(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? O211 C211 1.3603(15) . ? O211 H211 0.92(2) . ? C211 C220 1.3890(16) . ? C211 C212 1.4268(18) . ? C212 C213 1.3688(18) . ? C212 C221 1.4982(17) . ? C213 C214 1.4094(17) . ? C213 H213 0.9500 . ? C214 C215 1.4174(18) . ? C214 C219 1.4296(18) . ? C215 C216 1.3654(19) . ? C215 H215 0.9500 . ? C216 C217 1.409(2) . ? C216 H216 0.9500 . ? C217 C218 1.3696(19) . ? C217 H217 0.9500 . ? C218 C219 1.4275(16) . ? C218 H218 0.9500 . ? C219 C220 1.4235(17) . ? C220 C222 1.5235(16) . ? O221 C221 1.2436(18) . ? C221 O222 1.2761(18) . ? O222 H222 1.2361(10) . ? C222 C223 1.5209(16) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C223 C224 1.3865(16) . ? C223 C232 1.4252(16) . ? O224 C224 1.3618(14) . ? O224 H224 0.914(19) . ? C224 C225 1.4348(16) . ? C225 C226 1.3768(16) . ? C225 C233 1.4827(16) . ? C226 C227 1.4076(16) . ? C226 H226 0.9500 . ? C227 C228 1.4213(16) . ? C227 C232 1.4320(16) . ? C228 C229 1.3650(17) . ? C228 H228 0.9500 . ? C229 C230 1.4110(18) . ? C229 H229 0.9500 . ? C230 C231 1.3692(17) . ? C230 H230 0.9500 . ? C231 C232 1.4265(16) . ? C231 H231 0.9500 . ? O233 C233 1.2297(14) . ? C233 O234 1.3129(14) . ? O234 H234 0.96(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N2 123.34(11) . . ? O1 C1 C5 127.37(11) . . ? N2 C1 C5 109.29(11) . . ? C1 N2 C6 123.86(11) . . ? C1 N2 C3 115.01(10) . . ? C6 N2 C3 120.97(10) . . ? N2 C3 C4 103.94(10) . . ? N2 C3 H3A 111.0 . . ? C4 C3 H3A 111.0 . . ? N2 C3 H3B 111.0 . . ? C4 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? C5 C4 C3 106.07(10) . . ? C5 C4 H4A 110.5 . . ? C3 C4 H4A 110.5 . . ? C5 C4 H4B 110.5 . . ? C3 C4 H4B 110.5 . . ? H4A C4 H4B 108.7 . . ? C1 C5 C4 105.17(10) . . ? C1 C5 H5A 110.7 . . ? C4 C5 H5A 110.7 . . ? C1 C5 H5B 110.7 . . ? C4 C5 H5B 110.7 . . ? H5A C5 H5B 108.8 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C211 O211 H211 103.8(13) . . ? O211 C211 C220 119.20(11) . . ? O211 C211 C212 119.51(10) . . ? C220 C211 C212 121.28(11) . . ? C213 C212 C211 119.71(11) . . ? C213 C212 C221 120.24(12) . . ? C211 C212 C221 120.04(12) . . ? C212 C213 C214 121.22(12) . . ? C212 C213 H213 119.4 . . ? C214 C213 H213 119.4 . . ? C213 C214 C215 120.93(12) . . ? C213 C214 C219 118.90(11) . . ? C215 C214 C219 120.18(11) . . ? C216 C215 C214 121.24(13) . . ? C216 C215 H215 119.4 . . ? C214 C215 H215 119.4 . . ? C215 C216 C217 118.92(13) . . ? C215 C216 H216 120.5 . . ? C217 C216 H216 120.5 . . ? C218 C217 C216 121.70(12) . . ? C218 C217 H217 119.2 . . ? C216 C217 H217 119.2 . . ? C217 C218 C219 120.97(12) . . ? C217 C218 H218 119.5 . . ? C219 C218 H218 119.5 . . ? C220 C219 C218 122.83(11) . . ? C220 C219 C214 120.21(10) . . ? C218 C219 C214 116.95(11) . . ? C211 C220 C219 118.48(11) . . ? C211 C220 C222 119.22(11) . . ? C219 C220 C222 122.27(10) . . ? O221 C221 O222 123.99(12) . . ? O221 C221 C212 119.73(13) . . ? O222 C221 C212 116.28(13) . . ? C221 O222 H222 113.35(11) . . ? C223 C222 C220 115.56(10) . . ? 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 . . ? C224 C223 C232 118.64(10) . . ? C224 C223 C222 119.70(10) . . ? C232 C223 C222 121.60(10) . . ? C224 O224 H224 107.7(12) . . ? O224 C224 C223 118.60(10) . . ? O224 C224 C225 120.05(10) . . ? C223 C224 C225 121.35(10) . . ? C226 C225 C224 119.43(10) . . ? C226 C225 C233 121.24(10) . . ? C224 C225 C233 119.32(10) . . ? C225 C226 C227 121.22(11) . . ? C225 C226 H226 119.4 . . ? C227 C226 H226 119.4 . . ? C226 C227 C228 121.12(11) . . ? C226 C227 C232 119.02(10) . . ? C228 C227 C232 119.86(11) . . ? C229 C228 C227 121.05(11) . . ? C229 C228 H228 119.5 . . ? C227 C228 H228 119.5 . . ? C228 C229 C230 119.35(11) . . ? C228 C229 H229 120.3 . . ? C230 C229 H229 120.3 . . ? C231 C230 C229 121.45(11) . . ? C231 C230 H230 119.3 . . ? C229 C230 H230 119.3 . . ? C230 C231 C232 120.95(11) . . ? C230 C231 H231 119.5 . . ? C232 C231 H231 119.5 . . ? C223 C232 C231 122.48(10) . . ? C223 C232 C227 120.22(10) . . ? C231 C232 C227 117.30(10) . . ? O233 C233 O234 122.06(11) . . ? O233 C233 C225 121.84(10) . . ? O234 C233 C225 116.10(10) . . ? C233 O234 H234 108.6(12) . . ? _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.338 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.041 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.677 1.000 456 145 ' ' _platon_squeeze_details ; ; #=== END data_4b _database_code_depnum_ccdc_archive 'CCDC 837708' #TrackingRef '- revision_2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;3-picolinium pamoate NMP solvate after immersion in supercritical CO2 ; _chemical_melting_point ? _chemical_formula_moiety '0.5(C46H31O12 -1), 0.5(C6H8N +1) ,1.75(C5H9NO)' _chemical_formula_sum 'C34.75 H35.25 N2.25 O7.75' _chemical_formula_weight 608.40 # formula weight is given including disordered channel contents # number of NMP molecules in the channel is an approximation # based in part on NMR data loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6539(11) _cell_length_b 10.4086(15) _cell_length_c 19.985(3) _cell_angle_alpha 89.076(2) _cell_angle_beta 85.488(2) _cell_angle_gamma 74.237(2) _cell_volume 1527.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4063 _cell_measurement_theta_min 2.271 _cell_measurement_theta_max 28.542 _exptl_crystal_description shard _exptl_crystal_colour yellow _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 643 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7024 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_special_details ; Crystals were immmersed in supercritical CO2 for 10 minutes before collecting this data. Some of the NMP in the channels has been removed. ; _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 9938 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.77 _reflns_number_total 6960 _reflns_number_gt 5570 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement ; SHELXL (Sheldrick, 2008), Platon/SQUEEZE (Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H224 was found in the difference map before application of SQUEEZE. H234,211 and 222 were identified in the difference map after application of SQUEEZE. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0919P)^2^+0.2449P] 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 6960 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1581 _refine_ls_wR_factor_gt 0.1498 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.04237(13) 0.92292(10) -0.08076(5) 0.0269(2) Uani 1 1 d . . . C1 C 0.89204(19) 1.00603(14) -0.08576(7) 0.0260(3) Uani 1 1 d . . . N2 N 0.86569(16) 1.10503(12) -0.13047(6) 0.0279(3) Uani 1 1 d . . . C3 C 0.6785(2) 1.18719(14) -0.13103(8) 0.0286(3) Uani 1 1 d . . . H3A H 0.6263 1.1752 -0.1735 0.034 Uiso 1 1 calc R . . H3B H 0.6714 1.2828 -0.1254 0.034 Uiso 1 1 calc R . . C4 C 0.5783(2) 1.13600(15) -0.07089(8) 0.0297(3) Uani 1 1 d . . . H4A H 0.5373 1.2056 -0.0355 0.036 Uiso 1 1 calc R . . H4B H 0.4706 1.1114 -0.0852 0.036 Uiso 1 1 calc R . . C5 C 0.71556(19) 1.01365(14) -0.04477(7) 0.0267(3) Uani 1 1 d . . . H5A H 0.7292 1.0242 0.0035 0.032 Uiso 1 1 calc R . . H5B H 0.6760 0.9319 -0.0510 0.032 Uiso 1 1 calc R . . C6 C 1.0060(2) 1.12590(15) -0.17883(8) 0.0338(3) Uani 1 1 d . . . H6A H 0.9761 1.1100 -0.2242 0.051 Uiso 1 1 calc R . . H6B H 1.1232 1.0639 -0.1699 0.051 Uiso 1 1 calc R . . H6C H 1.0139 1.2179 -0.1752 0.051 Uiso 1 1 calc R . . O211 O 0.85301(16) 0.14303(10) 0.27617(5) 0.0311(3) Uani 1 1 d . . . H211 H 0.863(4) 0.079(3) 0.3092(14) 0.080(8) Uiso 1 1 d . . . C211 C 0.86199(19) 0.25381(13) 0.30926(7) 0.0231(3) Uani 1 1 d . . . C212 C 0.8945(2) 0.24503(13) 0.37883(7) 0.0278(3) Uani 1 1 d . . . C213 C 0.8997(2) 0.35688(14) 0.41287(7) 0.0287(3) Uani 1 1 d . . . H213 H 0.9226 0.3505 0.4590 0.034 Uiso 1 1 calc R . . C214 C 0.87157(19) 0.48140(13) 0.38051(7) 0.0253(3) Uani 1 1 d . . . C215 C 0.8713(2) 0.59746(15) 0.41666(8) 0.0337(3) Uani 1 1 d . . . H215 H 0.8922 0.5908 0.4630 0.040 Uiso 1 1 calc R . . C216 C 0.8413(2) 0.71898(15) 0.38590(8) 0.0360(4) Uani 1 1 d . . . H216 H 0.8439 0.7960 0.4102 0.043 Uiso 1 1 calc R . . C217 C 0.8064(2) 0.72829(14) 0.31754(8) 0.0336(4) Uani 1 1 d . . . H217 H 0.7823 0.8131 0.2964 0.040 Uiso 1 1 calc R . . C218 C 0.80623(19) 0.61854(13) 0.28077(7) 0.0264(3) Uani 1 1 d . . . H218 H 0.7824 0.6283 0.2348 0.032 Uiso 1 1 calc R . . C219 C 0.84149(17) 0.48937(13) 0.31083(7) 0.0212(3) Uani 1 1 d . . . C220 C 0.84345(17) 0.37242(13) 0.27427(7) 0.0210(3) Uani 1 1 d . . . O221 O 0.9094(2) 0.01425(11) 0.38362(6) 0.0554(4) Uani 1 1 d . . . C221 C 0.9263(3) 0.11320(16) 0.41401(8) 0.0409(4) Uani 1 1 d . . . O222 O 0.9696(2) 0.11141(12) 0.47430(6) 0.0600(4) Uani 1 1 d . . . H222 H 1.0000 0.0000 0.5000 0.131(17) Uiso 1 2 d S . . C222 C 0.82016(18) 0.37473(13) 0.19947(7) 0.0226(3) Uani 1 1 d . . . H22A H 0.8141 0.2852 0.1857 0.027 Uiso 1 1 calc R . . H22B H 0.7020 0.4387 0.1913 0.027 Uiso 1 1 calc R . . C223 C 0.96821(17) 0.41226(13) 0.15510(6) 0.0207(3) Uani 1 1 d . . . O224 O 0.74658(13) 0.59656(10) 0.11540(5) 0.0284(2) Uani 1 1 d . . . H224 H 0.742(3) 0.667(2) 0.0842(12) 0.061(6) Uiso 1 1 d . . . C224 C 0.92410(17) 0.52332(13) 0.11414(6) 0.0217(3) Uani 1 1 d . . . C225 C 1.05979(18) 0.56206(13) 0.07156(6) 0.0210(3) Uani 1 1 d . . . C226 C 1.23832(18) 0.48759(13) 0.07076(6) 0.0221(3) Uani 1 1 d . . . H226 H 1.3288 0.5147 0.0432 0.026 Uiso 1 1 calc R . . C227 C 1.28944(18) 0.37177(13) 0.11006(6) 0.0211(3) Uani 1 1 d . . . C228 C 1.47303(18) 0.29339(14) 0.10807(7) 0.0246(3) Uani 1 1 d . . . H228 H 1.5636 0.3209 0.0808 0.030 Uiso 1 1 calc R . . C229 C 1.52187(19) 0.17898(14) 0.14464(8) 0.0281(3) Uani 1 1 d . . . H229 H 1.6455 0.1279 0.1434 0.034 Uiso 1 1 calc R . . C230 C 1.3867(2) 0.13743(14) 0.18433(8) 0.0288(3) Uani 1 1 d . . . H230 H 1.4203 0.0573 0.2093 0.035 Uiso 1 1 calc R . . C231 C 1.20786(19) 0.21036(13) 0.18754(7) 0.0242(3) Uani 1 1 d . . . H231 H 1.1194 0.1794 0.2142 0.029 Uiso 1 1 calc R . . C232 C 1.15258(17) 0.33217(13) 0.15140(6) 0.0207(3) Uani 1 1 d . . . C233 C 1.00570(18) 0.68327(13) 0.02966(6) 0.0229(3) Uani 1 1 d . . . O233 O 0.84628(14) 0.75104(11) 0.02997(5) 0.0325(3) Uani 1 1 d . . . O234 O 1.13750(13) 0.71418(10) -0.00721(5) 0.0264(2) Uani 1 1 d . . . H234 H 1.088(3) 0.792(3) -0.0333(13) 0.074(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0207(5) 0.0268(5) 0.0301(5) 0.0068(4) 0.0022(4) -0.0028(4) C1 0.0250(7) 0.0245(7) 0.0279(7) 0.0004(5) -0.0006(5) -0.0060(5) N2 0.0271(6) 0.0233(6) 0.0308(6) 0.0035(5) 0.0048(5) -0.0047(5) C3 0.0261(7) 0.0237(7) 0.0328(8) 0.0042(5) -0.0005(6) -0.0017(6) C4 0.0239(7) 0.0301(7) 0.0320(8) 0.0041(6) 0.0010(6) -0.0030(6) C5 0.0242(7) 0.0293(7) 0.0259(7) 0.0037(5) 0.0006(5) -0.0071(6) C6 0.0347(8) 0.0260(7) 0.0378(8) 0.0036(6) 0.0115(6) -0.0075(6) O211 0.0474(7) 0.0213(5) 0.0287(5) 0.0024(4) -0.0042(5) -0.0161(5) C211 0.0261(7) 0.0193(6) 0.0258(7) 0.0017(5) -0.0023(5) -0.0093(5) C212 0.0373(8) 0.0194(6) 0.0277(7) 0.0074(5) -0.0043(6) -0.0095(6) C213 0.0399(8) 0.0248(7) 0.0227(7) 0.0050(5) -0.0060(6) -0.0100(6) C214 0.0289(7) 0.0204(6) 0.0275(7) 0.0024(5) -0.0015(5) -0.0087(5) C215 0.0451(9) 0.0270(7) 0.0309(8) -0.0006(6) -0.0023(7) -0.0133(7) C216 0.0477(9) 0.0208(7) 0.0400(9) -0.0041(6) 0.0071(7) -0.0130(6) C217 0.0388(8) 0.0181(6) 0.0404(8) 0.0053(6) 0.0132(7) -0.0066(6) C218 0.0272(7) 0.0219(6) 0.0273(7) 0.0073(5) 0.0066(5) -0.0045(5) C219 0.0185(6) 0.0199(6) 0.0251(6) 0.0050(5) 0.0017(5) -0.0061(5) C220 0.0179(6) 0.0218(6) 0.0235(6) 0.0039(5) -0.0016(5) -0.0059(5) O221 0.1105(12) 0.0230(6) 0.0396(7) 0.0110(5) -0.0170(7) -0.0271(7) C221 0.0672(12) 0.0249(8) 0.0328(8) 0.0120(6) -0.0118(8) -0.0148(8) O222 0.1200(14) 0.0281(6) 0.0346(7) 0.0156(5) -0.0269(7) -0.0195(7) C222 0.0187(6) 0.0258(7) 0.0239(6) 0.0045(5) -0.0021(5) -0.0073(5) C223 0.0192(6) 0.0235(6) 0.0194(6) 0.0015(5) -0.0027(5) -0.0056(5) O224 0.0163(5) 0.0325(5) 0.0323(5) 0.0140(4) -0.0001(4) -0.0009(4) C224 0.0179(6) 0.0249(6) 0.0211(6) 0.0022(5) -0.0017(5) -0.0038(5) C225 0.0208(6) 0.0231(6) 0.0190(6) 0.0025(5) -0.0013(5) -0.0059(5) C226 0.0212(6) 0.0250(6) 0.0201(6) 0.0012(5) 0.0000(5) -0.0070(5) C227 0.0198(6) 0.0232(6) 0.0199(6) -0.0011(5) -0.0019(5) -0.0050(5) C228 0.0199(6) 0.0266(7) 0.0266(7) -0.0009(5) -0.0012(5) -0.0051(5) C229 0.0202(6) 0.0249(7) 0.0371(8) -0.0012(6) -0.0043(6) -0.0016(5) C230 0.0257(7) 0.0233(7) 0.0356(8) 0.0057(6) -0.0046(6) -0.0035(5) C231 0.0239(7) 0.0218(6) 0.0266(7) 0.0028(5) -0.0030(5) -0.0058(5) C232 0.0202(6) 0.0220(6) 0.0200(6) -0.0003(5) -0.0028(5) -0.0056(5) C233 0.0231(6) 0.0257(6) 0.0191(6) 0.0020(5) -0.0007(5) -0.0059(5) O233 0.0234(5) 0.0331(6) 0.0367(6) 0.0165(4) 0.0003(4) -0.0020(4) O234 0.0243(5) 0.0274(5) 0.0259(5) 0.0073(4) 0.0020(4) -0.0059(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2477(17) . ? C1 N2 1.3366(18) . ? C1 C5 1.5073(19) . ? N2 C6 1.4463(18) . ? N2 C3 1.4564(18) . ? C3 C4 1.541(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.528(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? O211 C211 1.3588(16) . ? O211 H211 0.92(3) . ? C211 C220 1.3878(17) . ? C211 C212 1.429(2) . ? C212 C213 1.369(2) . ? C212 C221 1.5003(18) . ? C213 C214 1.4099(18) . ? C213 H213 0.9500 . ? C214 C215 1.417(2) . ? C214 C219 1.4267(19) . ? C215 C216 1.367(2) . ? C215 H215 0.9500 . ? C216 C217 1.409(2) . ? C216 H216 0.9500 . ? C217 C218 1.369(2) . ? C217 H217 0.9500 . ? C218 C219 1.4296(17) . ? C218 H218 0.9500 . ? C219 C220 1.4259(19) . ? C220 C222 1.5183(18) . ? O221 C221 1.245(2) . ? C221 O222 1.273(2) . ? O222 H222 1.2311(11) . ? C222 C223 1.5146(17) . ? C222 H22A 0.9900 . ? C222 H22B 0.9900 . ? C223 C224 1.3861(18) . ? C223 C232 1.4276(18) . ? O224 C224 1.3640(15) . ? O224 H224 0.95(2) . ? C224 C225 1.4293(18) . ? C225 C226 1.3747(18) . ? C225 C233 1.4836(18) . ? C226 C227 1.4088(18) . ? C226 H226 0.9500 . ? C227 C228 1.4182(18) . ? C227 C232 1.4273(18) . ? C228 C229 1.366(2) . ? C228 H228 0.9500 . ? C229 C230 1.411(2) . ? C229 H229 0.9500 . ? C230 C231 1.3699(19) . ? C230 H230 0.9500 . ? C231 C232 1.4265(18) . ? C231 H231 0.9500 . ? C233 O233 1.2320(17) . ? C233 O234 1.3098(16) . ? O234 H234 0.96(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N2 123.14(13) . . ? O1 C1 C5 127.56(12) . . ? N2 C1 C5 109.30(12) . . ? C1 N2 C6 123.97(13) . . ? C1 N2 C3 114.94(12) . . ? C6 N2 C3 120.93(12) . . ? N2 C3 C4 103.95(11) . . ? N2 C3 H3A 111.0 . . ? C4 C3 H3A 111.0 . . ? N2 C3 H3B 111.0 . . ? C4 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? C5 C4 C3 106.07(11) . . ? C5 C4 H4A 110.5 . . ? C3 C4 H4A 110.5 . . ? C5 C4 H4B 110.5 . . ? C3 C4 H4B 110.5 . . ? H4A C4 H4B 108.7 . . ? C1 C5 C4 105.27(11) . . ? C1 C5 H5A 110.7 . . ? C4 C5 H5A 110.7 . . ? C1 C5 H5B 110.7 . . ? C4 C5 H5B 110.7 . . ? H5A C5 H5B 108.8 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C211 O211 H211 104.1(17) . . ? O211 C211 C220 119.17(12) . . ? O211 C211 C212 119.39(11) . . ? C220 C211 C212 121.43(12) . . ? C213 C212 C211 119.72(12) . . ? C213 C212 C221 120.22(13) . . ? C211 C212 C221 120.05(13) . . ? C212 C213 C214 121.02(13) . . ? C212 C213 H213 119.5 . . ? C214 C213 H213 119.5 . . ? C213 C214 C215 120.64(13) . . ? C213 C214 C219 119.06(12) . . ? C215 C214 C219 120.30(12) . . ? C216 C215 C214 121.01(14) . . ? C216 C215 H215 119.5 . . ? C214 C215 H215 119.5 . . ? C215 C216 C217 119.02(14) . . ? C215 C216 H216 120.5 . . ? C217 C216 H216 120.5 . . ? C218 C217 C216 121.78(13) . . ? C218 C217 H217 119.1 . . ? C216 C217 H217 119.1 . . ? C217 C218 C219 120.74(13) . . ? C217 C218 H218 119.6 . . ? C219 C218 H218 119.6 . . ? C220 C219 C214 120.34(11) . . ? C220 C219 C218 122.53(12) . . ? C214 C219 C218 117.12(12) . . ? C211 C220 C219 118.21(12) . . ? C211 C220 C222 119.45(12) . . ? C219 C220 C222 122.31(11) . . ? O221 C221 O222 124.38(13) . . ? O221 C221 C212 119.42(14) . . ? O222 C221 C212 116.20(14) . . ? C221 O222 H222 113.50(12) . . ? C223 C222 C220 115.52(11) . . ? 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 . . ? C224 C223 C232 118.33(11) . . ? C224 C223 C222 119.81(11) . . ? C232 C223 C222 121.77(11) . . ? C224 O224 H224 106.6(14) . . ? O224 C224 C223 118.43(11) . . ? O224 C224 C225 120.04(11) . . ? C223 C224 C225 121.53(12) . . ? C226 C225 C224 119.54(12) . . ? C226 C225 C233 121.12(11) . . ? C224 C225 C233 119.33(11) . . ? C225 C226 C227 121.13(12) . . ? C225 C226 H226 119.4 . . ? C227 C226 H226 119.4 . . ? C226 C227 C228 121.07(12) . . ? C226 C227 C232 118.99(12) . . ? C228 C227 C232 119.92(12) . . ? C229 C228 C227 121.12(13) . . ? C229 C228 H228 119.4 . . ? C227 C228 H228 119.4 . . ? C228 C229 C230 119.28(13) . . ? C228 C229 H229 120.4 . . ? C230 C229 H229 120.4 . . ? C231 C230 C229 121.33(12) . . ? C231 C230 H230 119.3 . . ? C229 C230 H230 119.3 . . ? C230 C231 C232 120.94(12) . . ? C230 C231 H231 119.5 . . ? C232 C231 H231 119.5 . . ? C231 C232 C227 117.36(12) . . ? C231 C232 C223 122.30(12) . . ? C227 C232 C223 120.34(11) . . ? O233 C233 O234 122.16(12) . . ? O233 C233 C225 121.80(12) . . ? O234 C233 C225 116.04(12) . . ? C233 O234 H234 109.4(15) . . ? _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 23.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.304 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.069 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.176 1.000 457 90 ' ' _platon_squeeze_details ; ; #=== END