Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm loop_ _publ_author_name 'Delia Haynes' 'William Jones' W.Motherwell _publ_contact_author_name 'Delia Haynes' _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EP UNITED KINGDOM ; _publ_contact_author_email DELIAHAYNES@CANTAB.NET _publ_section_title ; Cocrystallisation of succinic and fumaric acids with lutidines: a systematic study ; # Attachment '2,3 lutidine fumarate.CIF' data_wj0418 _database_code_depnum_ccdc_archive 'CCDC 615309' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,3 lutidine fumarate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N, C4 H3 O4, C4 H4 O4' _chemical_formula_sum 'C15 H17 N O8' _chemical_formula_weight 339.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0541(18) _cell_length_b 18.159(4) _cell_length_c 9.7343(19) _cell_angle_alpha 90.00 _cell_angle_beta 91.20(3) _cell_angle_gamma 90.00 _cell_volume 1600.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 8808 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.883 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The NH+ hydrogen in the major component of the disordered lutidine and the COOH hydrogen atoms were located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 13037 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3655 _reflns_number_gt 2724 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0308P)^2^+0.8229P] 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 3655 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1188 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 N11 N 0.2270(3) 0.01478(12) -0.2650(2) 0.0303(5) Uani 0.797(4) 1 d P A 1 H11 H 0.242(3) 0.0497(14) -0.198(3) 0.033(7) Uiso 0.797(4) 1 d P A 1 C12 C 0.0943(3) -0.01742(16) -0.2872(3) 0.0301(7) Uani 0.797(4) 1 d P A 1 C13 C 0.0814(5) -0.07103(14) -0.3885(3) 0.0321(6) Uani 0.797(4) 1 d P A 1 C14 C 0.2047(4) -0.08928(16) -0.4615(3) 0.0359(7) Uani 0.797(4) 1 d P A 1 H14 H 0.1969 -0.1253 -0.5321 0.043 Uiso 0.797(4) 1 calc PR A 1 C15 C 0.3405(3) -0.05599(13) -0.4339(2) 0.0374(6) Uani 0.797(4) 1 d P A 1 H15 H 0.4256 -0.0698 -0.4831 0.045 Uiso 0.797(4) 1 calc PR A 1 C16 C 0.3486(8) -0.0024(4) -0.3336(7) 0.0388(11) Uani 0.797(4) 1 d P A 1 H16 H 0.4394 0.0220 -0.3136 0.047 Uiso 0.797(4) 1 calc PR A 1 C17 C -0.0275(4) 0.00652(18) -0.1978(3) 0.0377(8) Uani 0.797(4) 1 d P A 1 H17A H 0.0070 0.0468 -0.1383 0.057 Uiso 0.797(4) 1 calc PR A 1 H17B H -0.0589 -0.0350 -0.1410 0.057 Uiso 0.797(4) 1 calc PR A 1 H17C H -0.1111 0.0235 -0.2550 0.057 Uiso 0.797(4) 1 calc PR A 1 C18 C -0.0657(4) -0.10817(15) -0.4134(3) 0.0427(7) Uani 0.797(4) 1 d P A 1 H18A H -0.0599 -0.1403 -0.4940 0.064 Uiso 0.797(4) 1 calc PR A 1 H18B H -0.1421 -0.0707 -0.4297 0.064 Uiso 0.797(4) 1 calc PR A 1 H18C H -0.0907 -0.1376 -0.3328 0.064 Uiso 0.797(4) 1 calc PR A 1 C1 C -0.0823(10) -0.0627(5) -0.3226(9) 0.0325(15) Uani 0.203(4) 1 d P A 2 H1 H -0.1819 -0.0791 -0.3233 0.039 Uiso 0.203(4) 1 calc PR A 2 N2 N 0.1100(12) 0.0072(6) -0.2328(11) 0.037(2) Uani 0.203(4) 1 d P A 2 H2 H 0.1396 0.0393 -0.1703 0.044 Uiso 0.203(4) 1 calc PR A 2 C3 C 0.2098(12) -0.0161(6) -0.3162(11) 0.0325(15) Uani 0.203(4) 1 d P A 2 C4 C 0.366(3) 0.0062(18) -0.310(3) 0.044(3) Uani 0.203(4) 1 d P A 2 H4A H 0.3910 0.0237 -0.2172 0.066 Uiso 0.203(4) 1 calc PR A 2 H4B H 0.3819 0.0459 -0.3763 0.066 Uiso 0.203(4) 1 calc PR A 2 H4C H 0.4281 -0.0360 -0.3323 0.066 Uiso 0.203(4) 1 calc PR A 2 C5 C 0.2714(13) -0.0966(7) -0.5228(13) 0.044(3) Uani 0.203(4) 1 d P A 2 H5A H 0.2184 -0.1238 -0.5954 0.066 Uiso 0.203(4) 1 calc PR A 2 H5B H 0.3443 -0.1289 -0.4780 0.066 Uiso 0.203(4) 1 calc PR A 2 H5C H 0.3217 -0.0542 -0.5629 0.066 Uiso 0.203(4) 1 calc PR A 2 C6 C 0.1617(19) -0.0697(7) -0.4169(14) 0.0325(15) Uani 0.203(4) 1 d P A 2 C7 C 0.0212(17) -0.0887(7) -0.4146(11) 0.0325(15) Uani 0.203(4) 1 d P A 2 H7 H -0.0125 -0.1231 -0.4817 0.039 Uiso 0.203(4) 1 calc PR A 2 C8 C -0.0288(19) -0.0115(8) -0.2308(15) 0.0325(15) Uani 0.203(4) 1 d P A 2 H8 H -0.0927 0.0102 -0.1660 0.039 Uiso 0.203(4) 1 calc PR A 2 C21 C 0.3244(2) 0.11543(9) 0.04310(17) 0.0287(4) Uani 1 1 d . . . O21 O 0.23583(16) 0.11824(7) -0.05842(14) 0.0425(4) Uani 1 1 d . . . O22 O 0.37275(15) 0.05725(7) 0.09626(13) 0.0372(3) Uani 1 1 d . . . C22 C 0.3750(2) 0.18686(9) 0.10334(18) 0.0313(4) Uani 1 1 d . . . H22 H 0.3323 0.2311 0.0687 0.038 Uiso 1 1 calc R . . C23 C 0.4758(2) 0.19159(9) 0.20196(18) 0.0313(4) Uani 1 1 d . . . H23 H 0.5153 0.1475 0.2404 0.038 Uiso 1 1 calc R . . C24 C 0.5302(2) 0.26324(10) 0.25529(17) 0.0304(4) Uani 1 1 d . . . O23 O 0.48157(17) 0.32213(7) 0.21946(14) 0.0435(4) Uani 1 1 d . . . O24 O 0.63874(16) 0.25544(7) 0.34782(14) 0.0426(4) Uani 1 1 d . . . H24 H 0.674(3) 0.3034(15) 0.382(3) 0.073(8) Uiso 1 1 d . . . C31 C 0.9090(2) 0.26964(10) 0.10879(19) 0.0341(4) Uani 1 1 d . . . O31 O 0.87284(17) 0.32740(7) 0.05821(15) 0.0473(4) Uani 1 1 d . . . O32 O 1.00937(19) 0.26291(8) 0.20905(16) 0.0528(4) Uani 1 1 d . . . H3B H 1.041(3) 0.3082(16) 0.240(3) 0.078(9) Uiso 1 1 d . . . C32 C 0.8476(2) 0.19677(10) 0.06721(18) 0.0327(4) Uani 1 1 d . . . H32 H 0.8797 0.1540 0.1153 0.039 Uiso 1 1 calc R . . C33 C 0.7505(2) 0.18986(9) -0.03382(18) 0.0302(4) Uani 1 1 d . . . H33 H 0.7186 0.2332 -0.0804 0.036 Uiso 1 1 calc R . . C34 C 0.68750(19) 0.11824(9) -0.07974(17) 0.0279(4) Uani 1 1 d . . . O33 O 0.72569(15) 0.06204(7) -0.00538(13) 0.0331(3) Uani 1 1 d . . . H3A H 0.693(3) 0.0176(17) -0.039(3) 0.088(10) Uiso 1 1 d . . . O34 O 0.60612(16) 0.11399(7) -0.18187(14) 0.0424(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0400(15) 0.0240(11) 0.0266(10) -0.0023(8) -0.0077(9) -0.0035(9) C12 0.0379(18) 0.0244(14) 0.0275(14) 0.0045(10) -0.0079(12) -0.0029(11) C13 0.0394(19) 0.0272(13) 0.0293(12) 0.0031(9) -0.0112(12) -0.0042(12) C14 0.051(2) 0.0279(14) 0.0290(15) 0.0003(11) -0.0023(13) -0.0020(12) C15 0.0402(14) 0.0357(13) 0.0365(13) -0.0008(10) 0.0025(10) 0.0033(11) C16 0.035(2) 0.039(2) 0.042(3) 0.0075(17) -0.0051(16) -0.0033(15) C17 0.0416(17) 0.0361(18) 0.0355(17) -0.0024(11) -0.0015(14) -0.0011(14) C18 0.0507(19) 0.0374(14) 0.0395(14) 0.0003(11) -0.0109(12) -0.0124(13) C1 0.032(3) 0.033(3) 0.032(3) -0.001(2) -0.006(2) 0.002(2) N2 0.040(7) 0.029(5) 0.041(6) 0.002(4) -0.011(5) 0.001(4) C3 0.032(3) 0.033(3) 0.032(3) -0.001(2) -0.006(2) 0.002(2) C4 0.041(6) 0.050(6) 0.041(6) 0.014(5) -0.003(4) 0.003(5) C5 0.041(6) 0.050(6) 0.041(6) 0.014(5) -0.003(4) 0.003(5) C6 0.032(3) 0.033(3) 0.032(3) -0.001(2) -0.006(2) 0.002(2) C7 0.032(3) 0.033(3) 0.032(3) -0.001(2) -0.006(2) 0.002(2) C8 0.032(3) 0.033(3) 0.032(3) -0.001(2) -0.006(2) 0.002(2) C21 0.0316(9) 0.0232(8) 0.0310(9) -0.0013(7) -0.0074(7) -0.0003(7) O21 0.0570(9) 0.0261(7) 0.0431(7) -0.0065(5) -0.0284(7) 0.0062(6) O22 0.0433(8) 0.0223(6) 0.0453(7) 0.0020(5) -0.0177(6) -0.0012(6) C22 0.0391(10) 0.0205(8) 0.0338(9) -0.0004(7) -0.0099(8) 0.0018(7) C23 0.0378(10) 0.0230(8) 0.0328(9) 0.0015(7) -0.0082(8) -0.0021(7) C24 0.0373(10) 0.0281(9) 0.0256(8) 0.0007(7) -0.0069(7) -0.0037(8) O23 0.0625(10) 0.0258(7) 0.0413(8) 0.0007(6) -0.0212(7) -0.0017(6) O24 0.0512(9) 0.0269(7) 0.0486(8) -0.0003(6) -0.0264(7) -0.0046(6) C31 0.0372(11) 0.0279(9) 0.0365(9) -0.0020(7) -0.0105(8) -0.0001(8) O31 0.0558(9) 0.0283(7) 0.0568(9) 0.0016(6) -0.0233(7) -0.0018(6) O32 0.0673(11) 0.0308(8) 0.0587(9) -0.0028(7) -0.0380(8) -0.0035(7) C32 0.0397(11) 0.0244(9) 0.0335(9) -0.0008(7) -0.0091(8) 0.0010(8) C33 0.0330(10) 0.0230(8) 0.0342(9) 0.0011(7) -0.0056(7) 0.0015(7) C34 0.0272(9) 0.0253(8) 0.0309(9) 0.0001(7) -0.0042(7) 0.0011(7) O33 0.0407(8) 0.0234(6) 0.0346(7) 0.0023(5) -0.0119(5) -0.0003(6) O34 0.0515(9) 0.0276(7) 0.0469(8) 0.0028(6) -0.0274(7) -0.0016(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.336(8) . ? N11 C12 1.350(4) . ? N11 H11 0.92(3) . ? C12 C13 1.389(4) . ? C12 C17 1.484(5) . ? C13 C14 1.377(4) . ? C13 C18 1.508(4) . ? C14 C15 1.391(4) . ? C14 H14 0.9500 . ? C15 C16 1.380(6) . ? 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 . ? C1 C8 1.371(16) . ? C1 C7 1.392(15) . ? C1 H1 0.9500 . ? N2 C8 1.30(2) . ? N2 C3 1.298(17) . ? N2 H11 1.46(3) . ? N2 H2 0.8800 . ? C3 C6 1.443(18) . ? C3 C4 1.47(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.526(19) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.319(18) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C21 O22 1.252(2) . ? C21 O21 1.260(2) . ? C21 C22 1.492(2) . ? C22 C23 1.313(2) . ? C22 H22 0.9500 . ? C23 C24 1.481(2) . ? C23 H23 0.9500 . ? C24 O23 1.205(2) . ? C24 O24 1.327(2) . ? O24 H24 0.98(3) . ? C31 O31 1.201(2) . ? C31 O32 1.325(2) . ? C31 C32 1.488(2) . ? O32 H3B 0.92(3) . ? C32 C33 1.311(2) . ? C32 H32 0.9500 . ? C33 C34 1.485(2) . ? C33 H33 0.9500 . ? C34 O34 1.227(2) . ? C34 O33 1.294(2) . ? O33 H3A 0.92(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 124.0(3) . . ? C16 N11 H11 113.9(16) . . ? C12 N11 H11 122.1(16) . . ? N11 C12 C13 118.6(3) . . ? N11 C12 C17 116.7(3) . . ? C13 C12 C17 124.7(3) . . ? C14 C13 C12 118.6(4) . . ? C14 C13 C18 122.2(3) . . ? C12 C13 C18 119.2(3) . . ? C13 C14 C15 121.2(3) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 118.5(4) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? N11 C16 C15 119.1(4) . . ? N11 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? C8 C1 C7 114.6(12) . . ? C8 C1 H1 122.7 . . ? C7 C1 H1 122.7 . . ? C8 N2 C3 127.5(15) . . ? C8 N2 H11 157.2(16) . . ? C3 N2 H11 74.9(13) . . ? C8 N2 H2 116.2 . . ? C3 N2 H2 116.2 . . ? H11 N2 H2 41.5 . . ? N2 C3 C6 116.1(13) . . ? N2 C3 C4 124.4(18) . . ? C6 C3 C4 119.4(16) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C6 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C3 116.2(15) . . ? C7 C6 C5 124.7(12) . . ? C3 C6 C5 118.9(13) . . ? C6 C7 C1 125.8(15) . . ? C6 C7 H7 117.1 . . ? C1 C7 H7 117.1 . . ? N2 C8 C1 119.7(14) . . ? N2 C8 H8 120.2 . . ? C1 C8 H8 120.2 . . ? O22 C21 O21 124.73(15) . . ? O22 C21 C22 118.00(14) . . ? O21 C21 C22 117.27(15) . . ? C23 C22 C21 123.18(16) . . ? C23 C22 H22 118.4 . . ? C21 C22 H22 118.4 . . ? C22 C23 C24 122.29(16) . . ? C22 C23 H23 118.9 . . ? C24 C23 H23 118.9 . . ? O23 C24 O24 123.49(16) . . ? O23 C24 C23 124.16(16) . . ? O24 C24 C23 112.34(15) . . ? C24 O24 H24 111.3(15) . . ? O31 C31 O32 124.01(17) . . ? O31 C31 C32 124.58(16) . . ? O32 C31 C32 111.40(15) . . ? C31 O32 H3B 111.2(17) . . ? C33 C32 C31 122.01(16) . . ? C33 C32 H32 119.0 . . ? C31 C32 H32 119.0 . . ? C32 C33 C34 123.83(16) . . ? C32 C33 H33 118.1 . . ? C34 C33 H33 118.1 . . ? O34 C34 O33 123.53(15) . . ? O34 C34 C33 121.27(15) . . ? O33 C34 C33 115.20(14) . . ? C34 O33 H3A 114.2(18) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.189 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.057 # Attachment '2,3 lutidine fumaric acid co-crystal.cif' data_wj0422 _database_code_depnum_ccdc_archive 'CCDC 615310' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,3 lutidine fumaric acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N2,C4 H4 O4' _chemical_formula_sum 'C18 H22 N2 O4' _chemical_formula_weight 330.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.8746(4) _cell_length_b 7.1925(4) _cell_length_c 12.2559(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.810(3) _cell_angle_gamma 90.00 _cell_volume 864.31(7) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4919 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.870 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atom was located and its position was refined without any restraints. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5654 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 27.43 _reflns_number_total 1973 _reflns_number_gt 1502 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+0.3671P] 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 1973 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0723 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1310 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.50270(13) 0.25807(19) 0.01528(10) 0.0312(3) Uani 1 1 d . . . C11 C 0.58967(15) 0.2126(2) -0.05676(12) 0.0289(4) Uani 1 1 d . . . C12 C 0.71870(16) 0.1382(2) -0.02071(13) 0.0314(4) Uani 1 1 d . . . C13 C 0.75374(17) 0.1171(3) 0.09094(14) 0.0379(4) Uani 1 1 d . . . H13 H 0.8405 0.0674 0.1176 0.045 Uiso 1 1 calc R . . C14 C 0.66411(18) 0.1675(3) 0.16490(13) 0.0409(4) Uani 1 1 d . . . H14 H 0.6889 0.1547 0.2418 0.049 Uiso 1 1 calc R . . C15 C 0.53911(17) 0.2360(3) 0.12391(13) 0.0366(4) Uani 1 1 d . . . H15 H 0.4762 0.2691 0.1735 0.044 Uiso 1 1 calc R . . C16 C 0.54269(17) 0.2489(3) -0.17545(12) 0.0382(4) Uani 1 1 d . . . H16A H 0.4430 0.2589 -0.1861 0.057 Uiso 1 1 calc R . . H16B H 0.5714 0.1463 -0.2200 0.057 Uiso 1 1 calc R . . H16C H 0.5829 0.3653 -0.1979 0.057 Uiso 1 1 calc R . . C17 C 0.81374(18) 0.0843(3) -0.10256(15) 0.0444(5) Uani 1 1 d . . . H17A H 0.9003 0.0408 -0.0635 0.067 Uiso 1 1 calc R . . H17B H 0.8305 0.1923 -0.1478 0.067 Uiso 1 1 calc R . . H17C H 0.7724 -0.0155 -0.1498 0.067 Uiso 1 1 calc R . . O21 O 0.26277(11) 0.36537(18) -0.05863(9) 0.0383(3) Uani 1 1 d . . . H21 H 0.369(2) 0.322(3) -0.0221(16) 0.057 Uiso 1 1 d . . . C21 C 0.18662(16) 0.4151(2) 0.01622(12) 0.0309(4) Uani 1 1 d . . . O22 O 0.22254(11) 0.41188(19) 0.11504(9) 0.0403(3) Uani 1 1 d . . . C22 C 0.04792(15) 0.4770(2) -0.03052(12) 0.0316(4) Uani 1 1 d . . . H22 H 0.0276 0.4837 -0.1081 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0278(6) 0.0383(8) 0.0280(7) 0.0007(6) 0.0050(5) 0.0004(6) C11 0.0277(8) 0.0311(8) 0.0282(8) -0.0017(6) 0.0045(6) -0.0027(6) C12 0.0278(8) 0.0337(9) 0.0326(8) -0.0017(6) 0.0028(6) -0.0004(6) C13 0.0302(8) 0.0440(10) 0.0380(9) 0.0030(7) -0.0018(7) 0.0022(7) C14 0.0411(9) 0.0541(11) 0.0270(8) 0.0036(8) 0.0013(7) -0.0040(8) C15 0.0354(9) 0.0474(10) 0.0281(8) 0.0006(7) 0.0085(6) -0.0028(8) C16 0.0354(9) 0.0516(11) 0.0275(8) 0.0006(7) 0.0032(6) 0.0026(8) C17 0.0347(9) 0.0561(12) 0.0428(10) -0.0084(9) 0.0059(7) 0.0082(8) O21 0.0290(6) 0.0584(8) 0.0278(6) -0.0023(5) 0.0044(4) 0.0103(6) C21 0.0271(8) 0.0359(9) 0.0298(8) 0.0025(7) 0.0045(6) -0.0009(7) O22 0.0328(6) 0.0620(9) 0.0260(6) 0.0028(5) 0.0030(5) 0.0045(6) C22 0.0290(8) 0.0400(9) 0.0257(7) 0.0017(6) 0.0026(6) 0.0001(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C11 1.3430(19) . ? N11 C15 1.3467(19) . ? N11 H21 1.42(2) . ? C11 C12 1.404(2) . ? C11 C16 1.496(2) . ? C12 C13 1.379(2) . ? C12 C17 1.504(2) . ? C13 C14 1.388(2) . ? C13 H13 0.9500 . ? C14 C15 1.368(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? O21 C21 1.3032(18) . ? O21 H21 1.13(2) . ? C21 O22 1.2212(18) . ? C21 C22 1.489(2) . ? C22 C22 1.316(3) 3_565 ? C22 H22 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N11 C15 120.31(13) . . ? C11 N11 H21 120.6(8) . . ? C15 N11 H21 119.0(8) . . ? N11 C11 C12 120.87(14) . . ? N11 C11 C16 116.61(14) . . ? C12 C11 C16 122.52(14) . . ? C13 C12 C11 117.75(15) . . ? C13 C12 C17 122.03(15) . . ? C11 C12 C17 120.22(14) . . ? C12 C13 C14 120.98(16) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 118.14(15) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? N11 C15 C14 121.93(15) . . ? N11 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C21 O21 H21 112.4(10) . . ? O22 C21 O21 124.68(14) . . ? O22 C21 C22 122.21(14) . . ? O21 C21 C22 113.11(13) . . ? C22 C22 C21 123.17(18) 3_565 . ? C22 C22 H22 118.4 3_565 . ? C21 C22 H22 118.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N11 C11 C12 1.2(2) . . . . ? C15 N11 C11 C16 -177.61(15) . . . . ? N11 C11 C12 C13 -1.2(2) . . . . ? C16 C11 C12 C13 177.50(16) . . . . ? N11 C11 C12 C17 178.70(16) . . . . ? C16 C11 C12 C17 -2.6(2) . . . . ? C11 C12 C13 C14 0.1(3) . . . . ? C17 C12 C13 C14 -179.81(17) . . . . ? C12 C13 C14 C15 1.0(3) . . . . ? C11 N11 C15 C14 0.0(3) . . . . ? C13 C14 C15 N11 -1.1(3) . . . . ? O22 C21 C22 C22 -3.8(3) . . . 3_565 ? O21 C21 C22 C22 176.0(2) . . . 3_565 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.161 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.046 # Attachment '2,3 lutidine succinic acid co-crystal.cif' data_wj0510 _database_code_depnum_ccdc_archive 'CCDC 615311' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,3 lutidine succinic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety '2(C7 H9 N), C4 H6 O4' _chemical_formula_sum 'C18 H24 N2 O4' _chemical_formula_weight 332.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.0598(3) _cell_length_b 7.3023(3) _cell_length_c 12.2512(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.470(2) _cell_angle_gamma 90.00 _cell_volume 892.33(5) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3801 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.901 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atom was located and its position was refined without any restraints. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 6035 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2018 _reflns_number_gt 1622 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0511P)^2^+0.1958P] 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 2018 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.1073 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 O11 O 0.76474(9) 0.62194(15) 0.43963(7) 0.0454(3) Uani 1 1 d . . . H11 H 0.8542(19) 0.661(2) 0.4750(14) 0.068 Uiso 1 1 d . . . O12 O 0.71891(9) 0.58204(15) 0.61128(7) 0.0463(3) Uani 1 1 d . . . C11 C 0.68562(12) 0.57722(18) 0.51266(9) 0.0346(3) Uani 1 1 d . . . C12 C 0.54890(11) 0.5177(2) 0.45949(9) 0.0391(3) Uani 1 1 d . . . H12A H 0.5585 0.4045 0.4167 0.047 Uiso 1 1 calc R . . H12B H 0.5116 0.6138 0.4072 0.047 Uiso 1 1 calc R . . N21 N 0.99734(10) 0.26123(15) 0.48421(8) 0.0361(3) Uani 1 1 d . . . C21 C 0.91392(12) 0.21153(17) 0.55586(9) 0.0333(3) Uani 1 1 d . . . C22 C 0.79014(12) 0.12803(18) 0.52054(10) 0.0369(3) Uani 1 1 d . . . C23 C 0.75602(13) 0.1011(2) 0.40879(11) 0.0431(3) Uani 1 1 d . . . H23A H 0.6731 0.0444 0.3824 0.052 Uiso 1 1 calc R . . C24 C 0.84123(14) 0.1557(2) 0.33491(11) 0.0469(4) Uani 1 1 d . . . H24A H 0.8171 0.1396 0.2579 0.056 Uiso 1 1 calc R . . C25 C 0.96171(13) 0.2340(2) 0.37600(10) 0.0431(3) Uani 1 1 d . . . H25A H 1.0217 0.2699 0.3262 0.052 Uiso 1 1 calc R . . C26 C 0.95869(13) 0.2525(2) 0.67473(10) 0.0429(3) Uani 1 1 d . . . H26A H 1.0553 0.2770 0.6854 0.064 Uiso 1 1 calc R . . H26B H 0.9395 0.1472 0.7197 0.064 Uiso 1 1 calc R . . H26C H 0.9106 0.3602 0.6969 0.064 Uiso 1 1 calc R . . C27 C 0.69936(14) 0.0691(2) 0.60240(12) 0.0516(4) Uani 1 1 d . . . H27A H 0.6147 0.0236 0.5631 0.077 Uiso 1 1 calc R . . H27B H 0.6814 0.1738 0.6483 0.077 Uiso 1 1 calc R . . H27C H 0.7428 -0.0284 0.6491 0.077 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O11 0.0327(5) 0.0712(7) 0.0322(5) 0.0039(4) 0.0039(4) -0.0102(4) O12 0.0362(5) 0.0721(7) 0.0302(5) -0.0025(4) 0.0031(4) -0.0040(4) C11 0.0303(6) 0.0419(7) 0.0316(6) -0.0004(5) 0.0046(4) 0.0029(5) C12 0.0294(6) 0.0560(8) 0.0316(6) -0.0009(5) 0.0034(5) -0.0001(5) N21 0.0317(5) 0.0452(6) 0.0316(5) 0.0008(4) 0.0047(4) 0.0019(4) C21 0.0311(6) 0.0372(7) 0.0315(6) 0.0019(5) 0.0037(4) 0.0042(5) C22 0.0310(6) 0.0393(7) 0.0398(7) 0.0022(5) 0.0027(5) 0.0028(5) C23 0.0342(7) 0.0488(8) 0.0442(7) -0.0046(6) -0.0032(5) 0.0008(6) C24 0.0473(7) 0.0606(9) 0.0307(6) -0.0048(6) -0.0031(5) 0.0084(7) C25 0.0419(7) 0.0563(9) 0.0320(6) 0.0018(5) 0.0082(5) 0.0056(6) C26 0.0391(7) 0.0582(9) 0.0309(6) -0.0005(6) 0.0033(5) -0.0001(6) C27 0.0397(7) 0.0617(10) 0.0543(9) 0.0064(7) 0.0098(6) -0.0083(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 O11 C11 1.3137(14) . ? O11 H11 0.989(19) . ? O12 C11 1.2116(14) . ? C11 C12 1.5073(16) . ? C12 C12 1.508(2) 3_666 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? N21 C21 1.3409(15) . ? N21 C25 1.3424(16) . ? C21 C22 1.4034(17) . ? C21 C26 1.4976(17) . ? C22 C23 1.3816(18) . ? C22 C27 1.5042(18) . ? C23 C24 1.384(2) . ? C23 H23A 0.9500 . ? C24 C25 1.375(2) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 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 C11 O11 H11 111.8(10) . . ? O12 C11 O11 123.95(11) . . ? O12 C11 C12 123.90(11) . . ? O11 C11 C12 112.15(10) . . ? C11 C12 C12 113.69(12) . 3_666 ? C11 C12 H12A 108.8 . . ? C12 C12 H12A 108.8 3_666 . ? C11 C12 H12B 108.8 . . ? C12 C12 H12B 108.8 3_666 . ? H12A C12 H12B 107.7 . . ? C21 N21 C25 119.80(11) . . ? N21 C21 C22 121.44(11) . . ? N21 C21 C26 116.61(11) . . ? C22 C21 C26 121.95(11) . . ? C23 C22 C21 117.61(12) . . ? C23 C22 C27 121.72(12) . . ? C21 C22 C27 120.66(11) . . ? C22 C23 C24 120.79(12) . . ? C22 C23 H23A 119.6 . . ? C24 C23 H23A 119.6 . . ? C25 C24 C23 118.15(12) . . ? C25 C24 H24A 120.9 . . ? C23 C24 H24A 120.9 . . ? N21 C25 C24 122.19(12) . . ? N21 C25 H25A 118.9 . . ? C24 C25 H25A 118.9 . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 C11 C12 C12 5.9(2) . . . 3_666 ? O11 C11 C12 C12 -174.56(14) . . . 3_666 ? C25 N21 C21 C22 1.14(19) . . . . ? C25 N21 C21 C26 -177.88(12) . . . . ? N21 C21 C22 C23 -0.95(19) . . . . ? C26 C21 C22 C23 178.02(12) . . . . ? N21 C21 C22 C27 178.53(12) . . . . ? C26 C21 C22 C27 -2.5(2) . . . . ? C21 C22 C23 C24 -0.3(2) . . . . ? C27 C22 C23 C24 -179.77(13) . . . . ? C22 C23 C24 C25 1.3(2) . . . . ? C21 N21 C25 C24 -0.1(2) . . . . ? C23 C24 C25 N21 -1.2(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 O11 H11 N21 0.989(19) 1.615(19) 2.5974(14) 171.7(16) 3_766 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.201 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.036 # Attachment '2,4 lutidine fumarate.CIF' data_wj0401 _database_code_depnum_ccdc_archive 'CCDC 615312' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,4 lutidine fumarate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N 1+,0.5(C4 H2 O4 1-),0.5(C4 H4 O4)' _chemical_formula_sum 'C11 H13 N O4' _chemical_formula_weight 223.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 3.96530(10) _cell_length_b 13.7652(4) _cell_length_c 20.0488(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.6030(10) _cell_angle_gamma 90.00 _cell_volume 1093.90(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5393 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.887 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH and -NH(+) hydrogen atoms were located unambiguously. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 8728 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2485 _reflns_number_gt 1899 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+0.4130P] 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 2485 _refine_ls_number_parameters 150 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1327 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N -0.4347(3) 0.13857(10) -0.21698(6) 0.0258(3) Uani 1 1 d . . . H11 H -0.3613 0.1013 -0.1840 0.031 Uiso 1 1 calc R . . C11 C -0.4082(4) 0.10690(12) -0.27992(8) 0.0231(4) Uani 1 1 d . . . C12 C -0.5272(4) 0.16545(13) -0.33164(8) 0.0270(4) Uani 1 1 d . . . H12 H -0.5090 0.1438 -0.3764 0.032 Uiso 1 1 calc R . . C13 C -0.6724(4) 0.25512(13) -0.31925(9) 0.0276(4) Uani 1 1 d . . . C14 C -0.6906(4) 0.28426(13) -0.25276(9) 0.0310(4) Uani 1 1 d . . . H14 H -0.7874 0.3453 -0.2422 0.037 Uiso 1 1 calc R . . C15 C -0.5694(4) 0.22510(13) -0.20283(9) 0.0319(4) Uani 1 1 d . . . H15 H -0.5809 0.2456 -0.1577 0.038 Uiso 1 1 calc R . . C16 C -0.2517(5) 0.00954(13) -0.29016(9) 0.0308(4) Uani 1 1 d . . . H16A H -0.2169 -0.0227 -0.2469 0.046 Uiso 1 1 calc R . . H16B H -0.0341 0.0175 -0.3115 0.046 Uiso 1 1 calc R . . H16C H -0.4014 -0.0301 -0.3188 0.046 Uiso 1 1 calc R . . C17 C -0.8001(5) 0.31932(15) -0.37486(10) 0.0401(5) Uani 1 1 d . . . H17A H -0.8222 0.2814 -0.4161 0.060 Uiso 1 1 calc R . . H17B H -0.6409 0.3728 -0.3812 0.060 Uiso 1 1 calc R . . H17C H -1.0208 0.3458 -0.3636 0.060 Uiso 1 1 calc R . . O21B O -0.7615(3) -0.10420(9) -0.40507(6) 0.0380(3) Uani 1 1 d . . . O21A O -0.6898(4) -0.19338(9) -0.49699(6) 0.0395(4) Uani 1 1 d D . . H21A H -0.596(5) -0.2426(14) -0.4655(9) 0.047 Uiso 1 1 d D . . C21 C -0.7900(4) -0.11573(12) -0.46469(8) 0.0271(4) Uani 1 1 d . . . C22 C -0.9432(4) -0.04161(12) -0.51048(8) 0.0291(4) Uani 1 1 d . . . H22 H -0.9587 -0.0556 -0.5569 0.035 Uiso 1 1 calc R . . O31A O -0.2241(3) 0.03376(9) -0.11719(6) 0.0343(3) Uani 1 1 d . . . O31B O -0.0679(4) 0.17877(9) -0.08014(6) 0.0384(4) Uani 1 1 d . . . C31 C -0.0891(4) 0.08845(12) -0.07338(8) 0.0261(4) Uani 1 1 d . . . C32 C 0.0466(4) 0.04327(12) -0.01058(8) 0.0249(4) Uani 1 1 d . . . H32 H 0.2083 0.0785 0.0155 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0314(8) 0.0252(8) 0.0205(7) 0.0021(5) -0.0029(5) -0.0022(6) C11 0.0221(8) 0.0248(9) 0.0223(8) -0.0001(6) -0.0006(6) -0.0036(6) C12 0.0288(9) 0.0308(9) 0.0214(8) 0.0009(7) 0.0007(6) -0.0019(7) C13 0.0229(8) 0.0274(9) 0.0326(9) 0.0066(7) 0.0003(6) -0.0038(7) C14 0.0327(9) 0.0216(9) 0.0388(10) -0.0018(7) 0.0040(7) 0.0022(7) C15 0.0389(10) 0.0302(10) 0.0269(9) -0.0055(7) 0.0032(7) -0.0015(8) C16 0.0349(10) 0.0254(9) 0.0321(9) -0.0007(7) 0.0005(7) 0.0023(7) C17 0.0369(10) 0.0403(12) 0.0429(11) 0.0164(8) -0.0037(8) 0.0032(8) O21B 0.0567(9) 0.0343(8) 0.0227(7) 0.0000(5) -0.0033(5) 0.0093(6) O21A 0.0637(9) 0.0279(7) 0.0263(7) -0.0017(5) -0.0054(6) 0.0154(6) C21 0.0317(9) 0.0247(9) 0.0249(9) 0.0018(7) 0.0013(6) 0.0020(7) C22 0.0376(10) 0.0290(9) 0.0206(8) 0.0013(7) -0.0009(7) 0.0033(7) O31A 0.0544(8) 0.0246(7) 0.0232(6) 0.0000(5) -0.0127(5) -0.0072(6) O31B 0.0614(9) 0.0231(7) 0.0299(7) 0.0015(5) -0.0131(6) -0.0092(6) C31 0.0341(9) 0.0233(9) 0.0208(8) 0.0000(6) -0.0014(6) -0.0044(7) C32 0.0300(9) 0.0260(9) 0.0186(8) -0.0033(6) -0.0036(6) -0.0037(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C15 1.339(2) . ? N11 C11 1.342(2) . ? N11 H11 0.8800 . ? C11 C12 1.386(2) . ? C11 C16 1.493(2) . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 C14 1.396(3) . ? C13 C17 1.500(2) . ? C14 C15 1.367(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? O21B C21 1.208(2) . ? O21A C21 1.317(2) . ? O21A H21A 0.991(15) . ? C21 C22 1.490(2) . ? C22 C22 1.305(3) 3_354 ? C22 H22 0.9500 . ? O31A C31 1.264(2) . ? O31B C31 1.254(2) . ? C31 C32 1.491(2) . ? C32 C32 1.321(3) 3 ? C32 H32 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 N11 C11 122.02(14) . . ? C15 N11 H11 119.0 . . ? C11 N11 H11 119.0 . . ? N11 C11 C12 118.74(15) . . ? N11 C11 C16 117.67(14) . . ? C12 C11 C16 123.59(15) . . ? C11 C12 C13 121.18(15) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C14 117.36(15) . . ? C12 C13 C17 121.63(16) . . ? C14 C13 C17 121.01(17) . . ? C15 C14 C13 120.10(16) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? N11 C15 C14 120.60(16) . . ? N11 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 . . ? C21 O21A H21A 110.8(12) . . ? O21B C21 O21A 124.90(16) . . ? O21B C21 C22 123.00(16) . . ? O21A C21 C22 112.09(14) . . ? C22 C22 C21 122.8(2) 3_354 . ? C22 C22 H22 118.6 3_354 . ? C21 C22 H22 118.6 . . ? O31B C31 O31A 122.93(15) . . ? O31B C31 C32 118.76(14) . . ? O31A C31 C32 118.30(15) . . ? C32 C32 C31 123.35(19) 3 . ? C32 C32 H32 118.3 3 . ? C31 C32 H32 118.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N11 C11 C12 -0.6(2) . . . . ? C15 N11 C11 C16 179.59(15) . . . . ? N11 C11 C12 C13 -0.2(2) . . . . ? C16 C11 C12 C13 179.59(15) . . . . ? C11 C12 C13 C14 0.6(2) . . . . ? C11 C12 C13 C17 179.63(15) . . . . ? C12 C13 C14 C15 -0.3(2) . . . . ? C17 C13 C14 C15 -179.29(16) . . . . ? C11 N11 C15 C14 1.0(3) . . . . ? C13 C14 C15 N11 -0.5(3) . . . . ? O21B C21 C22 C22 0.3(3) . . . 3_354 ? O21A C21 C22 C22 -179.3(2) . . . 3_354 ? O31B C31 C32 C32 159.3(2) . . . 3 ? O31A C31 C32 C32 -19.9(3) . . . 3 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O31A 0.88 1.71 2.5861(18) 177.0 . O21A H21A O31B 0.991(15) 1.550(16) 2.5386(17) 176(2) 2_444 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.202 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.058 # Attachment '2,4 lutidine succinic acid co-crystal.cif' data_wj0431 _database_code_depnum_ccdc_archive 'CCDC 615313' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,4 lutidine succinic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety '2(C7 H9 N), C4 H6 O4' _chemical_formula_sum 'C18 H24 N2 O4' _chemical_formula_weight 332.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.8672(10) _cell_length_b 12.763(3) _cell_length_c 14.374(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.20(3) _cell_angle_gamma 90.00 _cell_volume 887.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4728 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.786 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atom was located and its position was refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5023 _diffrn_reflns_av_R_equivalents 0.0631 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.28 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2011 _reflns_number_gt 1406 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0685P)^2^+0.2305P] 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 2011 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1423 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 C11 C 0.1215(3) 1.08935(12) 1.35623(12) 0.0314(4) Uani 1 1 d . . . C12 C 0.0463(4) 1.12758(13) 1.44050(12) 0.0338(4) Uani 1 1 d . . . H12 H 0.1312 1.1007 1.4982 0.041 Uiso 1 1 calc R . . C13 C -0.1520(3) 1.20456(13) 1.43983(11) 0.0332(4) Uani 1 1 d . . . H13 H -0.2033 1.2288 1.4980 0.040 Uiso 1 1 calc R . . N14 N -0.2759(3) 1.24681(11) 1.36093(9) 0.0305(3) Uani 1 1 d . . . C15 C -0.2023(3) 1.21237(13) 1.27868(11) 0.0307(4) Uani 1 1 d . . . C16 C -0.0085(3) 1.13345(13) 1.27456(11) 0.0319(4) Uani 1 1 d . . . H16 H 0.0359 1.1093 1.2155 0.038 Uiso 1 1 calc R . . C17 C 0.3353(4) 1.00472(14) 1.35347(13) 0.0388(4) Uani 1 1 d . . . H17A H 0.3176 0.9546 1.4041 0.058 Uiso 1 1 calc R . . H17B H 0.5202 1.0360 1.3614 0.058 Uiso 1 1 calc R . . H17C H 0.3074 0.9684 1.2931 0.058 Uiso 1 1 calc R . . C18 C -0.3405(4) 1.26489(15) 1.19303(12) 0.0428(5) Uani 1 1 d . . . H18A H -0.2999 1.3401 1.1959 0.064 Uiso 1 1 calc R . . H18B H -0.5407 1.2542 1.1898 0.064 Uiso 1 1 calc R . . H18C H -0.2716 1.2348 1.1373 0.064 Uiso 1 1 calc R . . C21 C 0.2297(3) 0.91134(12) 1.05006(11) 0.0282(4) Uani 1 1 d . . . C22 C 0.4622(3) 0.98855(13) 1.04882(11) 0.0310(4) Uani 1 1 d . . . H22A H 0.6270 0.9608 1.0874 0.037 Uiso 1 1 calc R . . H22B H 0.4089 1.0549 1.0777 0.037 Uiso 1 1 calc R . . O21 O 0.1761(3) 0.88745(10) 1.13584(8) 0.0367(3) Uani 1 1 d . . . H21 H 0.022(5) 0.8349(17) 1.1326(15) 0.055 Uiso 1 1 d . . . O22 O 0.1023(2) 0.87429(9) 0.98025(8) 0.0349(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.0252(8) 0.0299(8) 0.0386(9) -0.0026(7) 0.0015(7) -0.0038(6) C12 0.0353(9) 0.0362(9) 0.0289(8) -0.0012(7) -0.0011(7) -0.0020(7) C13 0.0360(10) 0.0369(9) 0.0268(8) -0.0047(7) 0.0039(7) -0.0011(7) N14 0.0312(7) 0.0316(7) 0.0295(7) -0.0038(6) 0.0059(5) 0.0003(6) C15 0.0305(9) 0.0342(9) 0.0277(8) -0.0026(7) 0.0049(6) -0.0024(7) C16 0.0311(9) 0.0354(9) 0.0300(8) -0.0061(7) 0.0074(7) -0.0007(7) C17 0.0319(9) 0.0362(9) 0.0476(11) -0.0048(8) 0.0009(7) 0.0019(7) C18 0.0484(11) 0.0469(11) 0.0332(10) 0.0016(8) 0.0057(8) 0.0118(9) C21 0.0268(8) 0.0294(8) 0.0291(8) 0.0025(7) 0.0065(6) 0.0037(6) C22 0.0272(8) 0.0348(9) 0.0314(9) 0.0016(7) 0.0048(7) -0.0019(7) O21 0.0368(7) 0.0445(7) 0.0295(6) 0.0024(5) 0.0069(5) -0.0108(6) O22 0.0355(7) 0.0373(7) 0.0324(6) -0.0014(5) 0.0061(5) -0.0042(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 C11 C16 1.391(2) . ? C11 C12 1.391(2) . ? C11 C17 1.503(2) . ? C12 C13 1.376(2) . ? C12 H12 0.9500 . ? C13 N14 1.339(2) . ? C13 H13 0.9500 . ? N14 C15 1.346(2) . ? C15 C16 1.386(2) . ? C15 C18 1.496(2) . ? 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 . ? C21 O22 1.2169(19) . ? C21 O21 1.3231(19) . ? C21 C22 1.502(2) . ? C22 C22 1.517(3) 3_677 ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? O21 H21 1.00(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C11 C12 117.02(15) . . ? C16 C11 C17 121.44(16) . . ? C12 C11 C17 121.54(15) . . ? C13 C12 C11 119.64(15) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? N14 C13 C12 123.00(15) . . ? N14 C13 H13 118.5 . . ? C12 C13 H13 118.5 . . ? C13 N14 C15 118.31(14) . . ? N14 C15 C16 121.47(15) . . ? N14 C15 C18 115.95(15) . . ? C16 C15 C18 122.57(15) . . ? C15 C16 C11 120.52(15) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C11 C17 H17A 109.5 . . ? C11 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C11 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O22 C21 O21 123.00(15) . . ? O22 C21 C22 124.24(14) . . ? O21 C21 C22 112.75(14) . . ? C21 C22 C22 113.30(17) . 3_677 ? C21 C22 H22A 108.9 . . ? C22 C22 H22A 108.9 3_677 . ? C21 C22 H22B 108.9 . . ? C22 C22 H22B 108.9 3_677 . ? H22A C22 H22B 107.7 . . ? C21 O21 H21 109.4(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C12 C13 0.9(2) . . . . ? C17 C11 C12 C13 -179.49(15) . . . . ? C11 C12 C13 N14 -1.1(3) . . . . ? C12 C13 N14 C15 -0.1(2) . . . . ? C13 N14 C15 C16 1.6(2) . . . . ? C13 N14 C15 C18 -178.02(15) . . . . ? N14 C15 C16 C11 -1.8(3) . . . . ? C18 C15 C16 C11 177.81(16) . . . . ? C12 C11 C16 C15 0.4(2) . . . . ? C17 C11 C16 C15 -179.13(15) . . . . ? O22 C21 C22 C22 -3.7(3) . . . 3_677 ? O21 C21 C22 C22 176.38(17) . . . 3_677 ? 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 O21 H21 N14 1.00(2) 1.65(2) 2.6528(19) 174.0(19) 2_447 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.286 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.109 # Attachment '2,5 lutidine fumarate.CIF' data_wj0329 _database_code_depnum_ccdc_archive 'CCDC 615314' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,5 lutidine fumarate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N 1+,C4 H4 O4,0.5(C4 H2 O4 2-)' _chemical_formula_sum 'C13 H15 N O6' _chemical_formula_weight 281.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2696(2) _cell_length_b 9.1353(3) _cell_length_c 11.6311(3) _cell_angle_alpha 84.115(2) _cell_angle_beta 72.513(2) _cell_angle_gamma 88.763(2) _cell_volume 732.81(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5351 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.926 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atoms were located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7801 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3333 _reflns_number_gt 2879 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0682P)^2^+0.1496P] 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 3333 _refine_ls_number_parameters 189 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.062 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.23324(16) 0.46707(12) 0.01520(11) 0.0346(3) Uani 1 1 d . . . H11 H 0.2654 0.5436 0.0423 0.042 Uiso 1 1 calc R . . C12 C 0.1393(2) 0.35702(15) 0.09588(15) 0.0401(3) Uani 1 1 d . . . C13 C 0.0825(2) 0.23655(16) 0.04993(18) 0.0494(4) Uani 1 1 d . . . H13 H 0.0131 0.1597 0.1028 0.059 Uiso 1 1 calc R . . C14 C 0.1283(2) 0.23059(16) -0.07278(17) 0.0488(4) Uani 1 1 d . . . H14 H 0.0898 0.1493 -0.1022 0.059 Uiso 1 1 calc R . . C15 C 0.2315(2) 0.34413(16) -0.15410(16) 0.0434(4) Uani 1 1 d . . . C16 C 0.2796(2) 0.46406(15) -0.10516(13) 0.0376(3) Uani 1 1 d . . . H16 H 0.3449 0.5437 -0.1564 0.045 Uiso 1 1 calc R . . C17 C 0.1069(3) 0.3706(2) 0.22629(16) 0.0534(4) Uani 1 1 d . . . H17A H 0.1304 0.4705 0.2372 0.080 Uiso 1 1 calc R . . H17B H 0.1933 0.3067 0.2554 0.080 Uiso 1 1 calc R . . H17C H -0.0239 0.3435 0.2707 0.080 Uiso 1 1 calc R . . C18 C 0.2923(3) 0.3384(2) -0.28885(19) 0.0659(5) Uani 1 1 d . . . H18A H 0.3469 0.4317 -0.3286 0.099 Uiso 1 1 calc R . . H18B H 0.1821 0.3169 -0.3137 0.099 Uiso 1 1 calc R . . H18C H 0.3867 0.2628 -0.3104 0.099 Uiso 1 1 calc R . . O21 O 0.6212(2) 0.27440(14) 0.34108(11) 0.0625(4) Uani 1 1 d . . . C21 C 0.52934(19) 0.06933(16) 0.48610(11) 0.0347(3) Uani 1 1 d . . . H21 H 0.5557 0.1183 0.5457 0.042 Uiso 1 1 calc R . . C22 C 0.5554(2) 0.15112(16) 0.36562(12) 0.0369(3) Uani 1 1 d . . . O22 O 0.50276(18) 0.07742(13) 0.28897(9) 0.0494(3) Uani 1 1 d D . . H22 H 0.522(3) 0.141(2) 0.2140(15) 0.059 Uiso 1 1 d D . . O31 O 0.55446(15) 0.23639(10) 0.08458(8) 0.0378(2) Uani 1 1 d . . . C31 C 0.60715(17) 0.19655(13) -0.01985(10) 0.0264(3) Uani 1 1 d . . . O32 O 0.69539(14) 0.28229(10) -0.11184(8) 0.0336(2) Uani 1 1 d . . . C32 C 0.56341(18) 0.04391(13) -0.04050(11) 0.0284(3) Uani 1 1 d . . . H32 H 0.6290 0.0093 -0.1141 0.034 Uiso 1 1 calc R . . O41 O 0.81194(15) 0.21625(11) -0.33431(8) 0.0402(3) Uani 1 1 d D . . H41 H 0.778(2) 0.229(2) -0.2481(13) 0.048 Uiso 1 1 d D . . C41 C 0.91716(19) 0.09677(15) -0.35453(11) 0.0323(3) Uani 1 1 d . . . O42 O 0.97031(16) 0.02247(12) -0.27860(9) 0.0426(3) Uani 1 1 d . . . C42 C 0.96267(18) 0.06362(16) -0.48273(11) 0.0338(3) Uani 1 1 d . . . H42 H 0.9380 0.1341 -0.5397 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0360(6) 0.0227(5) 0.0468(7) -0.0035(5) -0.0149(5) -0.0003(4) C12 0.0371(7) 0.0283(7) 0.0549(9) 0.0031(6) -0.0161(6) 0.0003(5) C13 0.0485(8) 0.0258(7) 0.0772(12) 0.0049(7) -0.0266(8) -0.0056(6) C14 0.0501(9) 0.0259(7) 0.0799(12) -0.0117(7) -0.0318(8) 0.0025(6) C15 0.0411(7) 0.0334(7) 0.0618(9) -0.0168(6) -0.0210(7) 0.0068(6) C16 0.0380(7) 0.0295(7) 0.0462(8) -0.0080(6) -0.0127(6) 0.0004(5) C17 0.0597(10) 0.0433(9) 0.0533(10) 0.0086(7) -0.0150(8) -0.0061(7) C18 0.0721(12) 0.0650(12) 0.0674(12) -0.0362(10) -0.0215(10) 0.0047(10) O21 0.1027(10) 0.0468(7) 0.0424(6) 0.0039(5) -0.0290(6) -0.0283(7) C21 0.0375(7) 0.0423(7) 0.0255(6) -0.0062(5) -0.0100(5) -0.0039(5) C22 0.0435(7) 0.0382(7) 0.0293(6) -0.0035(5) -0.0108(5) -0.0072(6) O22 0.0780(8) 0.0453(6) 0.0290(5) 0.0038(4) -0.0229(5) -0.0229(5) O31 0.0568(6) 0.0313(5) 0.0238(4) -0.0051(3) -0.0082(4) -0.0095(4) C31 0.0293(6) 0.0256(6) 0.0250(5) -0.0024(4) -0.0090(4) -0.0015(4) O32 0.0455(5) 0.0274(5) 0.0249(4) -0.0018(3) -0.0056(4) -0.0075(4) C32 0.0340(6) 0.0262(6) 0.0244(5) -0.0046(4) -0.0071(4) -0.0016(5) O41 0.0543(6) 0.0380(5) 0.0254(5) -0.0052(4) -0.0072(4) 0.0022(4) C41 0.0351(6) 0.0350(7) 0.0246(6) -0.0031(5) -0.0051(5) -0.0070(5) O42 0.0540(6) 0.0461(6) 0.0284(5) -0.0051(4) -0.0133(4) 0.0039(5) C42 0.0348(6) 0.0413(7) 0.0236(6) -0.0023(5) -0.0060(5) -0.0052(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 N11 C16 1.3409(18) . ? N11 C12 1.3449(18) . ? N11 H11 0.8600 . ? C12 C13 1.393(2) . ? C12 C17 1.481(2) . ? C13 C14 1.371(3) . ? C13 H13 0.9300 . ? C14 C15 1.392(2) . ? C14 H14 0.9300 . ? C15 C16 1.382(2) . ? C15 C18 1.501(3) . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O21 C22 1.2056(18) . ? C21 C21 1.322(3) 2_656 ? C21 C22 1.4797(18) . ? C21 H21 0.9300 . ? C22 O22 1.3169(17) . ? O22 H22 0.970(15) . ? O31 C31 1.2488(14) . ? C31 O32 1.2677(15) . ? C31 C32 1.4957(17) . ? C32 C32 1.318(2) 2_655 ? C32 H32 0.9300 . ? O41 C41 1.3192(17) . ? O41 H41 0.977(14) . ? C41 O42 1.2086(17) . ? C41 C42 1.4887(17) . ? C42 C42 1.321(3) 2_754 ? C42 H42 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 123.64(12) . . ? C16 N11 H11 118.2 . . ? C12 N11 H11 118.2 . . ? N11 C12 C13 117.14(15) . . ? N11 C12 C17 118.16(13) . . ? C13 C12 C17 124.69(14) . . ? C14 C13 C12 120.36(14) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 121.13(14) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 116.84(15) . . ? C16 C15 C18 120.50(16) . . ? C14 C15 C18 122.66(15) . . ? N11 C16 C15 120.82(14) . . ? N11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C21 C21 C22 123.79(15) 2_656 . ? C21 C21 H21 118.1 2_656 . ? C22 C21 H21 118.1 . . ? O21 C22 O22 123.73(13) . . ? O21 C22 C21 121.92(12) . . ? O22 C22 C21 114.35(12) . . ? C22 O22 H22 108.0(12) . . ? O31 C31 O32 122.34(11) . . ? O31 C31 C32 120.19(11) . . ? O32 C31 C32 117.46(10) . . ? C32 C32 C31 123.25(14) 2_655 . ? C32 C32 H32 118.4 2_655 . ? C31 C32 H32 118.4 . . ? C41 O41 H41 108.7(11) . . ? O42 C41 O41 124.44(12) . . ? O42 C41 C42 123.75(12) . . ? O41 C41 C42 111.81(11) . . ? C42 C42 C41 121.45(16) 2_754 . ? C42 C42 H42 119.3 2_754 . ? C41 C42 H42 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 -2.3(2) . . . . ? C16 N11 C12 C17 176.53(13) . . . . ? N11 C12 C13 C14 2.3(2) . . . . ? C17 C12 C13 C14 -176.43(15) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? C13 C14 C15 C16 -1.9(2) . . . . ? C13 C14 C15 C18 177.07(16) . . . . ? C12 N11 C16 C15 0.1(2) . . . . ? C14 C15 C16 N11 2.0(2) . . . . ? C18 C15 C16 N11 -177.00(14) . . . . ? C21 C21 C22 O21 -175.05(19) 2_656 . . . ? C21 C21 C22 O22 4.4(3) 2_656 . . . ? O31 C31 C32 C32 15.0(2) . . . 2_655 ? O32 C31 C32 C32 -163.83(15) . . . 2_655 ? O42 C41 C42 C42 11.6(2) . . . 2_754 ? O41 C41 C42 C42 -168.20(16) . . . 2_754 ? 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 O32 0.86 1.92 2.7758(15) 173.1 2_665 O41 H41 O32 0.977(14) 1.637(14) 2.5995(13) 167.4(17) . O22 H22 O31 0.970(15) 1.616(15) 2.5847(14) 176.1(19) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.262 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.059 # Attachment '2,5 lutidine succinic acid co-crystal.cif' data_wj0526 _database_code_depnum_ccdc_archive 'CCDC 615315' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,5 lutidine succinic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety '2(C7 H9 N), C4 H6 O4' _chemical_formula_sum 'C18 H24 N2 O4' _chemical_formula_weight 332.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.7197(9) _cell_length_b 15.272(3) _cell_length_c 12.819(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.38(3) _cell_angle_gamma 90.00 _cell_volume 916.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 26835 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description rods _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.713 _exptl_absorpt_correction_T_max 1.007 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atom was located and its position was refined without any restraints. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5082 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.31 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2060 _reflns_number_gt 1598 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0695P)^2^+0.1909P] 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 2060 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1507 _refine_ls_wR_factor_gt 0.1402 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.046 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N -0.2712(3) 0.69908(9) 0.27881(11) 0.0474(4) Uani 1 1 d . . . C12 C -0.3315(3) 0.78267(11) 0.25184(13) 0.0478(4) Uani 1 1 d . . . C13 C -0.5469(4) 0.80213(12) 0.17119(14) 0.0544(4) Uani 1 1 d . . . H13 H -0.5853 0.8613 0.1513 0.065 Uiso 1 1 calc R . . C14 C -0.7049(4) 0.73566(13) 0.12005(14) 0.0564(4) Uani 1 1 d . . . H14 H -0.8544 0.7490 0.0654 0.068 Uiso 1 1 calc R . . C15 C -0.6465(4) 0.64913(12) 0.14799(13) 0.0501(4) Uani 1 1 d . . . C16 C -0.4247(4) 0.63542(11) 0.22771(14) 0.0497(4) Uani 1 1 d . . . H16 H -0.3784 0.5767 0.2474 0.060 Uiso 1 1 calc R . . C17 C -0.1580(4) 0.85266(12) 0.31208(16) 0.0605(5) Uani 1 1 d . . . H17A H -0.1440 0.8402 0.3876 0.091 Uiso 1 1 calc R . . H17B H -0.2505 0.9096 0.2974 0.091 Uiso 1 1 calc R . . H17C H 0.0339 0.8540 0.2906 0.091 Uiso 1 1 calc R . . C18 C -0.8126(5) 0.57306(14) 0.09673(17) 0.0644(5) Uani 1 1 d . . . H18A H -0.6901 0.5391 0.0556 0.097 Uiso 1 1 calc R . . H18B H -0.9785 0.5949 0.0502 0.097 Uiso 1 1 calc R . . H18C H -0.8776 0.5356 0.1510 0.097 Uiso 1 1 calc R . . O21 O 0.1536(3) 0.65718(7) 0.42356(10) 0.0515(3) Uani 1 1 d . . . H21 H -0.018(6) 0.6722(16) 0.365(2) 0.093(8) Uiso 1 1 d . . . O22 O 0.0787(3) 0.52100(8) 0.36304(10) 0.0542(4) Uani 1 1 d . . . C21 C 0.2124(3) 0.57282(10) 0.42209(12) 0.0425(4) Uani 1 1 d . . . C22 C 0.4640(3) 0.54838(10) 0.50046(13) 0.0435(4) Uani 1 1 d . . . H22A H 0.4232 0.5648 0.5718 0.052 Uiso 1 1 calc R . . H22B H 0.6325 0.5824 0.4853 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0466(7) 0.0444(8) 0.0510(8) 0.0060(6) 0.0054(6) 0.0058(6) C12 0.0499(9) 0.0441(9) 0.0503(9) 0.0037(7) 0.0107(7) 0.0063(7) C13 0.0602(10) 0.0455(9) 0.0569(10) 0.0080(7) 0.0047(8) 0.0113(8) C14 0.0551(9) 0.0601(10) 0.0524(9) 0.0075(8) 0.0005(8) 0.0097(8) C15 0.0488(9) 0.0537(9) 0.0486(9) 0.0017(7) 0.0093(7) 0.0017(7) C16 0.0517(9) 0.0423(8) 0.0553(10) 0.0052(7) 0.0079(7) 0.0035(7) C17 0.0684(12) 0.0472(10) 0.0650(11) -0.0007(8) 0.0048(9) 0.0033(8) C18 0.0661(11) 0.0635(11) 0.0620(11) -0.0031(9) 0.0018(9) -0.0069(10) O21 0.0534(7) 0.0404(6) 0.0574(7) -0.0012(5) -0.0050(5) 0.0055(5) O22 0.0527(7) 0.0427(6) 0.0616(7) 0.0002(5) -0.0138(6) -0.0020(5) C21 0.0412(8) 0.0392(8) 0.0465(8) 0.0018(6) 0.0040(6) -0.0019(6) C22 0.0403(8) 0.0409(8) 0.0475(8) -0.0013(6) -0.0009(6) -0.0015(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.333(2) . ? N11 C12 1.344(2) . ? C12 C13 1.386(2) . ? C12 C17 1.499(3) . ? C13 C14 1.375(3) . ? C13 H13 0.9500 . ? C14 C15 1.388(3) . ? C14 H14 0.9500 . ? C15 C16 1.382(3) . ? C15 C18 1.505(3) . ? 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 . ? O21 C21 1.3186(19) . ? O21 H21 1.06(3) . ? O22 C21 1.2144(19) . ? C21 C22 1.501(2) . ? C22 C22 1.517(3) 3_666 ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 118.87(15) . . ? N11 C12 C13 120.43(16) . . ? N11 C12 C17 117.48(15) . . ? C13 C12 C17 122.09(16) . . ? C14 C13 C12 119.89(16) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.17(16) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 116.21(16) . . ? C16 C15 C18 120.58(16) . . ? C14 C15 C18 123.20(17) . . ? N11 C16 C15 124.41(16) . . ? N11 C16 H16 117.8 . . ? C15 C16 H16 117.8 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C21 O21 H21 110.2(14) . . ? O22 C21 O21 123.52(14) . . ? O22 C21 C22 123.93(14) . . ? O21 C21 C22 112.55(13) . . ? C21 C22 C22 113.32(16) . 3_666 ? C21 C22 H22A 108.9 . . ? C22 C22 H22A 108.9 3_666 . ? C21 C22 H22B 108.9 . . ? C22 C22 H22B 108.9 3_666 . ? H22A C22 H22B 107.7 . . ? 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 O21 H21 N11 1.06(3) 1.57(3) 2.6300(19) 177(2) . _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.221 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.041 # Attachment '2,6 lutidine succinic acid co-crystal.cif' data_wj0511 _database_code_depnum_ccdc_archive 'CCDC 615316' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,6 lutidine succinic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety '2(C7 H9 N), C4 H6 O4' _chemical_formula_sum 'C18 H24 N2 O4' _chemical_formula_weight 332.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.733(3) _cell_length_b 15.106(3) _cell_length_c 7.6047(15) _cell_angle_alpha 90.00 _cell_angle_beta 98.56(3) _cell_angle_gamma 90.00 _cell_volume 1787.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6344 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.929 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atom was located and its position was refined without any restraints. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 9805 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.25 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4014 _reflns_number_gt 3379 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.5256P] 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 4014 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1138 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.08290(7) -0.18362(7) -0.20629(14) 0.0331(2) Uani 1 1 d . . . C12 C 0.00214(8) -0.18978(9) -0.16878(17) 0.0355(3) Uani 1 1 d . . . C13 C -0.03372(9) -0.27106(10) -0.13802(19) 0.0414(3) Uani 1 1 d . . . H13 H -0.0899 -0.2744 -0.1069 0.050 Uiso 1 1 calc R . . C14 C 0.01294(10) -0.34680(10) -0.1530(2) 0.0460(4) Uani 1 1 d . . . H14 H -0.0108 -0.4031 -0.1328 0.055 Uiso 1 1 calc R . . C15 C 0.09475(9) -0.34050(9) -0.19765(19) 0.0428(3) Uani 1 1 d . . . H15 H 0.1271 -0.3924 -0.2122 0.051 Uiso 1 1 calc R . . C16 C 0.12893(8) -0.25746(9) -0.22090(17) 0.0344(3) Uani 1 1 d . . . C17 C -0.04777(10) -0.10557(10) -0.1648(2) 0.0508(4) Uani 1 1 d . . . H17A H -0.0314 -0.0762 -0.0499 0.076 Uiso 1 1 calc R . . H17B H -0.1094 -0.1190 -0.1815 0.076 Uiso 1 1 calc R . . H17C H -0.0352 -0.0664 -0.2605 0.076 Uiso 1 1 calc R . . C18 C 0.21844(9) -0.24524(11) -0.2629(2) 0.0450(3) Uani 1 1 d . . . H18A H 0.2177 -0.2019 -0.3591 0.068 Uiso 1 1 calc R . . H18B H 0.2402 -0.3019 -0.3002 0.068 Uiso 1 1 calc R . . H18C H 0.2559 -0.2238 -0.1568 0.068 Uiso 1 1 calc R . . N21 N 0.41827(6) 0.43604(7) 0.13707(14) 0.0304(2) Uani 1 1 d . . . C22 C 0.38069(8) 0.51444(8) 0.09178(17) 0.0319(3) Uani 1 1 d . . . C23 C 0.41926(9) 0.59358(9) 0.15454(18) 0.0377(3) Uani 1 1 d . . . H23 H 0.3913 0.6484 0.1241 0.045 Uiso 1 1 calc R . . C24 C 0.49818(10) 0.59194(9) 0.26112(19) 0.0403(3) Uani 1 1 d . . . H24 H 0.5257 0.6455 0.3030 0.048 Uiso 1 1 calc R . . C25 C 0.53673(9) 0.51109(9) 0.30620(17) 0.0361(3) Uani 1 1 d . . . H25 H 0.5911 0.5084 0.3795 0.043 Uiso 1 1 calc R . . C26 C 0.49511(8) 0.43438(8) 0.24332(16) 0.0306(3) Uani 1 1 d . . . C27 C 0.29714(9) 0.51333(9) -0.03167(19) 0.0400(3) Uani 1 1 d . . . H27A H 0.2773 0.4521 -0.0505 0.060 Uiso 1 1 calc R . . H27B H 0.3052 0.5396 -0.1458 0.060 Uiso 1 1 calc R . . H27C H 0.2542 0.5476 0.0206 0.060 Uiso 1 1 calc R . . C28 C 0.53445(9) 0.34519(9) 0.2906(2) 0.0398(3) Uani 1 1 d . . . H28A H 0.4958 0.3104 0.3533 0.060 Uiso 1 1 calc R . . H28B H 0.5897 0.3529 0.3676 0.060 Uiso 1 1 calc R . . H28C H 0.5435 0.3142 0.1818 0.060 Uiso 1 1 calc R . . O31 O 0.37269(6) 0.27007(6) 0.05370(15) 0.0464(3) Uani 1 1 d . . . H31 H 0.3774(14) 0.3348(16) 0.073(3) 0.088(7) Uiso 1 1 d . . . O32 O 0.24074(7) 0.29216(6) -0.09173(16) 0.0512(3) Uani 1 1 d . . . O33 O 0.24351(7) -0.03590(7) -0.01950(15) 0.0540(3) Uani 1 1 d . . . O34 O 0.13607(6) -0.02014(6) -0.24439(14) 0.0420(2) Uani 1 1 d . . . H34 H 0.1241(14) -0.0825(16) -0.223(3) 0.088(7) Uiso 1 1 d . . . C31 C 0.29740(8) 0.24300(8) -0.02884(17) 0.0317(3) Uani 1 1 d . . . C32 C 0.29165(8) 0.14366(8) -0.03002(17) 0.0326(3) Uani 1 1 d . . . H32A H 0.2892 0.1228 0.0926 0.039 Uiso 1 1 calc R . . H32B H 0.3445 0.1192 -0.0673 0.039 Uiso 1 1 calc R . . C33 C 0.21459(8) 0.10771(8) -0.15166(17) 0.0315(3) Uani 1 1 d . . . H33A H 0.1626 0.1398 -0.1282 0.038 Uiso 1 1 calc R . . H33B H 0.2221 0.1195 -0.2765 0.038 Uiso 1 1 calc R . . C34 C 0.20086(8) 0.00990(8) -0.12949(17) 0.0323(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0328(5) 0.0318(5) 0.0337(5) -0.0029(4) 0.0014(4) -0.0059(4) C12 0.0332(6) 0.0381(7) 0.0341(6) -0.0065(5) 0.0016(5) -0.0074(5) C13 0.0362(7) 0.0455(8) 0.0416(7) -0.0040(6) 0.0022(6) -0.0144(6) C14 0.0474(8) 0.0371(7) 0.0498(8) 0.0039(6) -0.0053(6) -0.0164(6) C15 0.0434(8) 0.0328(7) 0.0477(8) 0.0008(6) -0.0081(6) -0.0014(6) C16 0.0337(6) 0.0365(7) 0.0306(6) -0.0001(5) -0.0035(5) -0.0016(5) C17 0.0409(8) 0.0444(8) 0.0689(11) -0.0101(7) 0.0139(7) -0.0022(6) C18 0.0360(7) 0.0522(8) 0.0463(8) 0.0027(6) 0.0041(6) 0.0020(6) N21 0.0310(5) 0.0260(5) 0.0344(5) -0.0007(4) 0.0053(4) -0.0013(4) C22 0.0344(6) 0.0287(6) 0.0343(6) 0.0017(5) 0.0104(5) 0.0013(5) C23 0.0463(8) 0.0268(6) 0.0414(7) 0.0006(5) 0.0113(6) 0.0025(5) C24 0.0491(8) 0.0285(6) 0.0439(7) -0.0063(5) 0.0092(6) -0.0081(6) C25 0.0359(7) 0.0342(7) 0.0377(7) -0.0035(5) 0.0039(5) -0.0070(5) C26 0.0312(6) 0.0286(6) 0.0326(6) -0.0009(5) 0.0065(5) -0.0024(5) C27 0.0372(7) 0.0356(7) 0.0464(8) 0.0041(6) 0.0036(6) 0.0043(6) C28 0.0349(7) 0.0324(7) 0.0494(8) 0.0007(6) -0.0023(6) 0.0012(5) O31 0.0359(5) 0.0267(5) 0.0704(7) -0.0037(4) -0.0128(5) -0.0017(4) O32 0.0405(5) 0.0290(5) 0.0772(8) -0.0010(5) -0.0143(5) 0.0042(4) O33 0.0608(7) 0.0309(5) 0.0612(7) 0.0083(5) -0.0205(5) -0.0060(5) O34 0.0374(5) 0.0320(5) 0.0524(6) 0.0032(4) -0.0067(4) -0.0088(4) C31 0.0300(6) 0.0276(6) 0.0364(6) -0.0021(5) 0.0019(5) 0.0001(5) C32 0.0307(6) 0.0257(6) 0.0395(7) 0.0000(5) -0.0015(5) 0.0005(5) C33 0.0297(6) 0.0273(6) 0.0362(6) 0.0000(5) 0.0006(5) -0.0006(5) C34 0.0304(6) 0.0293(6) 0.0365(6) -0.0010(5) 0.0027(5) -0.0025(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 N11 C16 1.3435(17) . ? N11 C12 1.3463(17) . ? C12 C13 1.3856(19) . ? C12 C17 1.498(2) . ? C13 C14 1.373(2) . ? C13 H13 0.9500 . ? C14 C15 1.383(2) . ? C14 H14 0.9500 . ? C15 C16 1.3864(19) . ? C15 H15 0.9500 . ? C16 C18 1.5012(19) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? N21 C22 1.3455(16) . ? N21 C26 1.3506(17) . ? C22 C23 1.3924(18) . ? C22 C27 1.4974(19) . ? C23 C24 1.378(2) . ? C23 H23 0.9500 . ? C24 C25 1.3839(19) . ? C24 H24 0.9500 . ? C25 C26 1.3810(17) . ? C25 H25 0.9500 . ? C26 C28 1.5037(18) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? O31 C31 1.3203(15) . ? O31 H31 0.99(2) . ? O32 C31 1.2033(16) . ? O33 C34 1.2089(16) . ? O34 C34 1.3204(15) . ? O34 H34 0.98(2) . ? C31 C32 1.5034(17) . ? C32 C33 1.5121(17) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.5063(17) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 119.83(11) . . ? N11 C12 C13 121.19(13) . . ? N11 C12 C17 117.37(12) . . ? C13 C12 C17 121.43(13) . . ? C14 C13 C12 119.22(13) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 119.45(13) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C16 119.12(14) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? N11 C16 C15 121.10(13) . . ? N11 C16 C18 116.73(12) . . ? C15 C16 C18 122.17(13) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C22 N21 C26 119.31(11) . . ? N21 C22 C23 121.03(12) . . ? N21 C22 C27 117.51(11) . . ? C23 C22 C27 121.44(12) . . ? C24 C23 C22 119.64(12) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C23 C24 C25 119.00(12) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? C26 C25 C24 119.14(13) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? N21 C26 C25 121.85(12) . . ? N21 C26 C28 117.36(11) . . ? C25 C26 C28 120.79(12) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C31 O31 H31 114.8(13) . . ? C34 O34 H34 111.7(13) . . ? O32 C31 O31 123.85(12) . . ? O32 C31 C32 124.98(12) . . ? O31 C31 C32 111.16(10) . . ? C31 C32 C33 113.84(10) . . ? C31 C32 H32A 108.8 . . ? C33 C32 H32A 108.8 . . ? C31 C32 H32B 108.8 . . ? C33 C32 H32B 108.8 . . ? H32A C32 H32B 107.7 . . ? C34 C33 C32 113.52(10) . . ? C34 C33 H33A 108.9 . . ? C32 C33 H33A 108.9 . . ? C34 C33 H33B 108.9 . . ? C32 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? O33 C34 O34 123.75(12) . . ? O33 C34 C33 124.38(11) . . ? O34 C34 C33 111.87(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 2.49(19) . . . . ? C16 N11 C12 C17 -176.46(12) . . . . ? N11 C12 C13 C14 -2.6(2) . . . . ? C17 C12 C13 C14 176.35(14) . . . . ? C12 C13 C14 C15 0.3(2) . . . . ? C13 C14 C15 C16 2.0(2) . . . . ? C12 N11 C16 C15 -0.12(19) . . . . ? C12 N11 C16 C18 -179.98(11) . . . . ? C14 C15 C16 N11 -2.1(2) . . . . ? C14 C15 C16 C18 177.72(13) . . . . ? C26 N21 C22 C23 -0.82(18) . . . . ? C26 N21 C22 C27 177.78(11) . . . . ? N21 C22 C23 C24 1.65(19) . . . . ? C27 C22 C23 C24 -176.90(12) . . . . ? C22 C23 C24 C25 -1.2(2) . . . . ? C23 C24 C25 C26 0.0(2) . . . . ? C22 N21 C26 C25 -0.45(18) . . . . ? C22 N21 C26 C28 179.86(11) . . . . ? C24 C25 C26 N21 0.9(2) . . . . ? C24 C25 C26 C28 -179.45(13) . . . . ? O32 C31 C32 C33 12.3(2) . . . . ? O31 C31 C32 C33 -168.91(11) . . . . ? C31 C32 C33 C34 -170.29(11) . . . . ? C32 C33 C34 O33 3.85(19) . . . . ? C32 C33 C34 O34 -176.46(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O34 H34 N11 0.98(2) 1.67(2) 2.6371(15) 168(2) . O31 H31 N21 0.99(2) 1.70(2) 2.6582(14) 161(2) . _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.188 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.033 # Attachment '3,4 lutidine fumarate.CIF' data_wj0324 _database_code_depnum_ccdc_archive 'CCDC 615317' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,4 lutidine fumarate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N 1+,0.5(C4 H2 O4 2-),C4 H4 O4' _chemical_formula_sum 'C13 H15 N O6' _chemical_formula_weight 281.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0478(2) _cell_length_b 10.0870(3) _cell_length_c 10.8570(3) _cell_angle_alpha 102.305(2) _cell_angle_beta 104.584(2) _cell_angle_gamma 107.975(2) _cell_volume 674.12(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3656 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.907 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -NH(+) and -COOH hydrogen atoms were located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 6479 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.45 _reflns_number_total 3049 _reflns_number_gt 2565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0302P)^2^+0.3119P] 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 3049 _refine_ls_number_parameters 189 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.20706(19) 0.20194(13) 0.40151(12) 0.0271(3) Uani 1 1 d . . . H11N H 0.1133 0.2009 0.4421 0.032 Uiso 1 1 calc R . . C11 C 0.1509(2) 0.09657(16) 0.28507(15) 0.0270(3) Uani 1 1 d . . . H11 H 0.0123 0.0220 0.2488 0.032 Uiso 1 1 calc R . . C12 C 0.2925(2) 0.09517(16) 0.21714(14) 0.0255(3) Uani 1 1 d . . . C13 C 0.4950(2) 0.20926(16) 0.27226(15) 0.0260(3) Uani 1 1 d . . . C14 C 0.5458(2) 0.31398(16) 0.39362(15) 0.0292(3) Uani 1 1 d . . . H14 H 0.6827 0.3906 0.4329 0.035 Uiso 1 1 calc R . . C15 C 0.4002(2) 0.30810(16) 0.45772(15) 0.0294(3) Uani 1 1 d . . . H15 H 0.4369 0.3793 0.5417 0.035 Uiso 1 1 calc R . . C16 C 0.2314(3) -0.02772(19) 0.09203(16) 0.0399(4) Uani 1 1 d . . . H16A H 0.0849 -0.0953 0.0702 0.060 Uiso 1 1 calc R . . H16B H 0.3265 -0.0806 0.1056 0.060 Uiso 1 1 calc R . . H16C H 0.2427 0.0120 0.0181 0.060 Uiso 1 1 calc R . . C17 C 0.6558(3) 0.2140(2) 0.20310(18) 0.0398(4) Uani 1 1 d . . . H17A H 0.7908 0.2951 0.2592 0.060 Uiso 1 1 calc R . . H17B H 0.6047 0.2291 0.1165 0.060 Uiso 1 1 calc R . . H17C H 0.6768 0.1211 0.1886 0.060 Uiso 1 1 calc R . . C21 C 0.7711(2) 0.08890(14) 0.47855(13) 0.0197(3) Uani 1 1 d . . . C22 C 0.5920(2) 0.05604(14) 0.53269(13) 0.0204(3) Uani 1 1 d . . . H22 H 0.6114 0.1184 0.6177 0.025 Uiso 1 1 calc R . . O21 O 0.92674(15) 0.21056(10) 0.53914(10) 0.0253(2) Uani 1 1 d . . . O22 O 0.76103(16) -0.00068(11) 0.37568(10) 0.0295(2) Uani 1 1 d . . . C31 C 0.0748(2) 0.53480(16) 0.19180(15) 0.0270(3) Uani 1 1 d . . . C32 C 0.0337(2) 0.47078(16) 0.04635(14) 0.0275(3) Uani 1 1 d . . . H32 H 0.0570 0.3831 0.0180 0.033 Uiso 1 1 calc R . . O31 O 0.01917(17) 0.64843(12) 0.21885(11) 0.0347(3) Uani 1 1 d D . . H31 H 0.049(3) 0.693(2) 0.3172(15) 0.042 Uiso 1 1 d D . . O32 O 0.15194(19) 0.48558(13) 0.27476(11) 0.0383(3) Uani 1 1 d . . . C41 C -0.3961(2) 0.68900(15) 0.13213(13) 0.0237(3) Uani 1 1 d . . . C42 C -0.4862(2) 0.52797(15) 0.06400(14) 0.0237(3) Uani 1 1 d . . . H42 H -0.5251 0.4634 0.1136 0.028 Uiso 1 1 calc R . . O41 O -0.41013(17) 0.72113(11) 0.25343(10) 0.0316(3) Uani 1 1 d D . . H41 H -0.348(3) 0.8259(16) 0.2969(17) 0.038 Uiso 1 1 d D . . O42 O -0.32139(18) 0.77960(11) 0.08213(11) 0.0345(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0292(6) 0.0320(7) 0.0308(7) 0.0137(5) 0.0181(5) 0.0168(5) C11 0.0235(7) 0.0294(7) 0.0302(8) 0.0121(6) 0.0102(6) 0.0103(6) C12 0.0290(7) 0.0286(7) 0.0238(7) 0.0117(6) 0.0115(6) 0.0132(6) C13 0.0264(7) 0.0332(8) 0.0300(7) 0.0187(6) 0.0151(6) 0.0164(6) C14 0.0270(7) 0.0270(7) 0.0341(8) 0.0133(6) 0.0103(6) 0.0087(6) C15 0.0362(8) 0.0255(7) 0.0293(8) 0.0093(6) 0.0124(6) 0.0140(6) C16 0.0490(10) 0.0409(9) 0.0291(8) 0.0069(7) 0.0152(7) 0.0177(8) C17 0.0340(8) 0.0592(11) 0.0430(10) 0.0276(8) 0.0250(7) 0.0228(8) C21 0.0207(6) 0.0196(6) 0.0192(6) 0.0052(5) 0.0073(5) 0.0085(5) C22 0.0234(6) 0.0206(6) 0.0189(6) 0.0046(5) 0.0097(5) 0.0096(5) O21 0.0213(5) 0.0237(5) 0.0240(5) -0.0009(4) 0.0101(4) 0.0035(4) O22 0.0318(5) 0.0238(5) 0.0275(5) -0.0020(4) 0.0172(4) 0.0048(4) C31 0.0186(6) 0.0274(7) 0.0257(7) -0.0004(6) 0.0072(5) 0.0027(5) C32 0.0203(7) 0.0264(7) 0.0272(7) -0.0032(6) 0.0086(5) 0.0051(5) O31 0.0365(6) 0.0396(6) 0.0221(5) -0.0033(5) 0.0070(4) 0.0180(5) O32 0.0429(7) 0.0384(6) 0.0299(6) 0.0085(5) 0.0101(5) 0.0141(5) C41 0.0210(6) 0.0244(7) 0.0213(7) 0.0024(5) 0.0050(5) 0.0081(5) C42 0.0210(6) 0.0227(7) 0.0247(7) 0.0039(5) 0.0072(5) 0.0078(5) O41 0.0403(6) 0.0216(5) 0.0258(5) -0.0013(4) 0.0165(5) 0.0043(4) O42 0.0469(7) 0.0256(5) 0.0265(6) 0.0073(4) 0.0128(5) 0.0086(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 N11 C15 1.3325(19) . ? N11 C11 1.3418(19) . ? N11 H11N 0.8800 . ? C11 C12 1.3837(19) . ? C11 H11 0.9500 . ? C12 C13 1.408(2) . ? C12 C16 1.492(2) . ? C13 C14 1.384(2) . ? C13 C17 1.5036(19) . ? C14 C15 1.371(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C21 O22 1.2488(16) . ? C21 O21 1.2665(16) . ? C21 C22 1.4990(17) . ? C22 C22 1.324(3) 2_656 ? C22 H22 0.9500 . ? C31 O32 1.2099(19) . ? C31 O31 1.3213(19) . ? C31 C32 1.4880(19) . ? C32 C32 1.331(3) 2_565 ? C32 H32 0.9500 . ? O31 H31 1.005(14) . ? C41 O42 1.2105(17) . ? C41 O41 1.3240(16) . ? C41 C42 1.4844(19) . ? C42 C42 1.323(3) 2_465 ? C42 H42 0.9500 . ? O41 H41 0.964(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 N11 C11 122.09(12) . . ? C15 N11 H11N 119.0 . . ? C11 N11 H11N 119.0 . . ? N11 C11 C12 120.84(13) . . ? N11 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C13 118.03(13) . . ? C11 C12 C16 119.99(13) . . ? C13 C12 C16 121.94(13) . . ? C14 C13 C12 118.75(12) . . ? C14 C13 C17 120.63(14) . . ? C12 C13 C17 120.58(14) . . ? C15 C14 C13 120.59(13) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? N11 C15 C14 119.64(14) . . ? N11 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 . . ? O22 C21 O21 122.49(12) . . ? O22 C21 C22 120.04(11) . . ? O21 C21 C22 117.45(11) . . ? C22 C22 C21 122.92(15) 2_656 . ? C22 C22 H22 118.5 2_656 . ? C21 C22 H22 118.5 . . ? O32 C31 O31 124.71(13) . . ? O32 C31 C32 122.09(14) . . ? O31 C31 C32 113.20(13) . . ? C32 C32 C31 123.80(17) 2_565 . ? C32 C32 H32 118.1 2_565 . ? C31 C32 H32 118.1 . . ? C31 O31 H31 113.1(11) . . ? O42 C41 O41 124.28(13) . . ? O42 C41 C42 124.08(13) . . ? O41 C41 C42 111.63(12) . . ? C42 C42 C41 121.69(17) 2_465 . ? C42 C42 H42 119.2 2_465 . ? C41 C42 H42 119.2 . . ? C41 O41 H41 110.5(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N11 C11 C12 -0.8(2) . . . . ? N11 C11 C12 C13 -1.4(2) . . . . ? N11 C11 C12 C16 176.43(14) . . . . ? C11 C12 C13 C14 2.4(2) . . . . ? C16 C12 C13 C14 -175.45(14) . . . . ? C11 C12 C13 C17 -179.90(14) . . . . ? C16 C12 C13 C17 2.3(2) . . . . ? C12 C13 C14 C15 -1.1(2) . . . . ? C17 C13 C14 C15 -178.90(14) . . . . ? C11 N11 C15 C14 2.1(2) . . . . ? C13 C14 C15 N11 -1.1(2) . . . . ? O22 C21 C22 C22 -9.0(3) . . . 2_656 ? O21 C21 C22 C22 169.48(17) . . . 2_656 ? O32 C31 C32 C32 -174.04(17) . . . 2_565 ? O31 C31 C32 C32 5.9(2) . . . 2_565 ? O42 C41 C42 C42 -8.1(3) . . . 2_465 ? O41 C41 C42 C42 171.07(16) . . . 2_465 ? 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 H11N O21 0.88 1.89 2.7715(14) 175.9 1_455 O31 H31 O21 1.005(14) 1.591(15) 2.5769(14) 166.0(18) 2_666 O41 H41 O22 0.964(14) 1.607(14) 2.5706(14) 177.3(18) 1_465 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.278 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.045 # Attachment '3,4 lutidine succinic acid co-crystal.cif' data_wj0432 _database_code_depnum_ccdc_archive 'CCDC 615318' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,4 lutidine succinic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety '2(C7 H9 N), C4 H6 O4' _chemical_formula_sum 'C18 H24 N2 O4' _chemical_formula_weight 332.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.802(2) _cell_length_b 6.0385(12) _cell_length_c 15.626(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.49(3) _cell_angle_gamma 90.00 _cell_volume 903.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4680 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.10 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.922 _exptl_absorpt_correction_T_max 1.015 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atom was located and its position was refined without any restraints. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 4607 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0645 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 27.10 _reflns_number_total 1970 _reflns_number_gt 1217 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.1953P] 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 0.072(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1970 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1148 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.1578 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.72411(18) -0.1889(3) 0.86919(12) 0.0425(5) Uani 1 1 d . . . C12 C 0.6980(2) -0.3518(4) 0.80960(14) 0.0407(6) Uani 1 1 d . . . H12 H 0.602(2) -0.352(4) 0.7709(15) 0.050(6) Uiso 1 1 d . . . C13 C 0.7942(2) -0.5096(4) 0.79790(13) 0.0367(5) Uani 1 1 d . . . C14 C 0.9283(2) -0.4968(4) 0.85134(13) 0.0365(5) Uani 1 1 d . . . C15 C 0.9566(2) -0.3269(4) 0.91258(14) 0.0401(6) Uani 1 1 d . . . H15 H 1.049(2) -0.314(4) 0.9497(15) 0.049(6) Uiso 1 1 d . . . C16 C 0.8530(2) -0.1794(4) 0.91967(14) 0.0421(6) Uani 1 1 d . . . H16 H 0.869(2) -0.064(4) 0.9618(14) 0.041(6) Uiso 1 1 d . . . C17 C 1.0406(2) -0.6603(4) 0.84289(16) 0.0497(6) Uani 1 1 d . . . H17A H 1.0098 -0.8103 0.8535 0.075 Uiso 1 1 calc R . . H17B H 1.1264 -0.6253 0.8860 0.075 Uiso 1 1 calc R . . H17C H 1.0587 -0.6518 0.7837 0.075 Uiso 1 1 calc R . . C18 C 0.7540(3) -0.6855(4) 0.72880(16) 0.0514(7) Uani 1 1 d . . . H18A H 0.6575 -0.6615 0.6970 0.077 Uiso 1 1 calc R . . H18B H 0.7619 -0.8317 0.7567 0.077 Uiso 1 1 calc R . . H18C H 0.8166 -0.6780 0.6877 0.077 Uiso 1 1 calc R . . C21 C 0.5846(2) 0.2531(4) 0.95282(13) 0.0397(6) Uani 1 1 d . . . C22 C 0.4744(2) 0.4142(4) 0.96528(14) 0.0440(6) Uani 1 1 d . . . H22A H 0.3964 0.3313 0.9812 0.053 Uiso 1 1 calc R . . H22B H 0.4374 0.4903 0.9089 0.053 Uiso 1 1 calc R . . O21 O 0.53826(17) 0.1096(3) 0.88980(11) 0.0562(5) Uani 1 1 d . . . H21 H 0.614(3) 0.001(5) 0.8831(17) 0.073(8) Uiso 1 1 d . . . O22 O 0.70322(15) 0.2533(3) 0.99568(10) 0.0538(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0402(10) 0.0455(12) 0.0399(10) -0.0024(9) 0.0046(8) 0.0020(9) C12 0.0366(12) 0.0442(13) 0.0392(12) -0.0018(11) 0.0032(10) 0.0013(10) C13 0.0373(11) 0.0383(12) 0.0337(11) 0.0017(9) 0.0054(9) -0.0024(10) C14 0.0353(11) 0.0384(12) 0.0358(11) 0.0069(9) 0.0079(9) -0.0001(10) C15 0.0358(12) 0.0440(13) 0.0382(12) 0.0029(11) 0.0027(10) -0.0031(10) C16 0.0429(13) 0.0438(14) 0.0376(12) -0.0064(11) 0.0042(10) -0.0019(11) C17 0.0445(13) 0.0505(15) 0.0532(15) 0.0008(12) 0.0086(11) 0.0059(11) C18 0.0512(14) 0.0508(15) 0.0481(14) -0.0107(12) 0.0018(11) 0.0033(12) C21 0.0347(11) 0.0460(14) 0.0365(12) 0.0001(11) 0.0033(9) 0.0016(10) C22 0.0338(11) 0.0521(15) 0.0433(12) -0.0030(11) 0.0021(9) 0.0067(10) O21 0.0399(9) 0.0626(11) 0.0582(11) -0.0219(9) -0.0068(8) 0.0114(8) O22 0.0359(9) 0.0658(12) 0.0537(10) -0.0134(9) -0.0034(7) 0.0093(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.338(3) . ? N11 C12 1.341(3) . ? C12 C13 1.380(3) . ? C12 H12 1.00(2) . ? C13 C14 1.399(3) . ? C13 C18 1.505(3) . ? C14 C15 1.390(3) . ? C14 C17 1.506(3) . ? C15 C16 1.373(3) . ? C15 H15 0.97(2) . ? C16 H16 0.95(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C21 O22 1.210(2) . ? C21 O21 1.317(3) . ? C21 C22 1.497(3) . ? C22 C22 1.506(4) 3_667 ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? O21 H21 1.01(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 117.07(19) . . ? N11 C12 C13 124.4(2) . . ? N11 C12 H12 115.8(13) . . ? C13 C12 H12 119.7(13) . . ? C12 C13 C14 117.6(2) . . ? C12 C13 C18 120.16(19) . . ? C14 C13 C18 122.2(2) . . ? C15 C14 C13 118.3(2) . . ? C15 C14 C17 120.24(19) . . ? C13 C14 C17 121.5(2) . . ? C16 C15 C14 119.6(2) . . ? C16 C15 H15 120.8(14) . . ? C14 C15 H15 119.6(13) . . ? N11 C16 C15 123.0(2) . . ? N11 C16 H16 115.6(13) . . ? C15 C16 H16 121.4(13) . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O22 C21 O21 123.3(2) . . ? O22 C21 C22 124.1(2) . . ? O21 C21 C22 112.53(18) . . ? C21 C22 C22 113.8(2) . 3_667 ? C21 C22 H22A 108.8 . . ? C22 C22 H22A 108.8 3_667 . ? C21 C22 H22B 108.8 . . ? C22 C22 H22B 108.8 3_667 . ? H22A C22 H22B 107.7 . . ? C21 O21 H21 111.2(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 O21 H21 N11 1.01(3) 1.62(3) 2.631(2) 175(2) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.275 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.112 # Attachment '3,5 lutidine fumaraic acid co-crystal.cif' data_wj0527b _database_code_depnum_ccdc_archive 'CCDC 615319' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,5 lutidine fumaric acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety '2(C7 H9 N), C4 H4 O4' _chemical_formula_sum 'C18 H22 N2 O4' _chemical_formula_weight 330.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2345(16) _cell_length_b 16.299(3) _cell_length_c 6.9681(14) _cell_angle_alpha 90.00 _cell_angle_beta 108.17(3) _cell_angle_gamma 90.00 _cell_volume 888.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5030 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.907 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; COOH proton was located and refined without any restraints. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7827 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2009 _reflns_number_gt 1853 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0576P)^2^+0.1740P] 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 2009 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1069 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.98176(11) 0.16476(5) 0.56672(12) 0.0290(2) Uani 1 1 d . . . C12 C 0.81897(13) 0.14246(6) 0.53362(14) 0.0281(2) Uani 1 1 d . . . H12 H 0.7916 0.0857 0.5265 0.034 Uiso 1 1 calc R . . C13 C 0.68867(13) 0.19931(6) 0.50936(15) 0.0279(2) Uani 1 1 d . . . C14 C 0.73373(13) 0.28194(6) 0.51998(15) 0.0282(2) Uani 1 1 d . . . H14 H 0.6478 0.3225 0.5042 0.034 Uiso 1 1 calc R . . C15 C 0.90219(13) 0.30606(6) 0.55325(15) 0.0276(2) Uani 1 1 d . . . C16 C 1.02302(13) 0.24432(6) 0.57623(15) 0.0298(2) Uani 1 1 d . . . H16 H 1.1392 0.2592 0.5995 0.036 Uiso 1 1 calc R . . C17 C 0.50702(15) 0.17226(8) 0.4740(2) 0.0424(3) Uani 1 1 d . . . H17A H 0.4291 0.2166 0.4082 0.064 Uiso 0.227(18) 1 calc PR . . H17B H 0.4901 0.1590 0.6036 0.064 Uiso 0.227(18) 1 calc PR . . H17C H 0.4835 0.1236 0.3871 0.064 Uiso 0.227(18) 1 calc PR . . H17D H 0.5061 0.1162 0.5244 0.064 Uiso 0.773(18) 1 calc PR . . H17E H 0.4450 0.1738 0.3290 0.064 Uiso 0.773(18) 1 calc PR . . H17F H 0.4516 0.2092 0.5455 0.064 Uiso 0.773(18) 1 calc PR . . C18 C 0.95502(17) 0.39478(7) 0.56710(19) 0.0382(3) Uani 1 1 d . . . H18A H 1.0680 0.3994 0.5489 0.057 Uiso 0.699(17) 1 calc PR . . H18B H 0.9599 0.4165 0.6999 0.057 Uiso 0.699(17) 1 calc PR . . H18C H 0.8716 0.4262 0.4615 0.057 Uiso 0.699(17) 1 calc PR . . H18D H 0.8650 0.4286 0.5913 0.057 Uiso 0.301(17) 1 calc PR . . H18E H 0.9731 0.4116 0.4403 0.057 Uiso 0.301(17) 1 calc PR . . H18F H 1.0614 0.4019 0.6787 0.057 Uiso 0.301(17) 1 calc PR . . C21 C 1.32232(12) 0.06932(6) 0.83058(15) 0.0261(2) Uani 1 1 d . . . C22 C 1.44500(12) 0.00033(6) 0.90820(16) 0.0281(2) Uani 1 1 d . . . H22 H 1.4435 -0.0449 0.8215 0.034 Uiso 1 1 calc R . . O21 O 1.33018(10) 0.13275(5) 0.92618(13) 0.0385(2) Uani 1 1 d . . . O22 O 1.21059(10) 0.05404(5) 0.65598(12) 0.0343(2) Uani 1 1 d . . . H2A H 1.111(3) 0.1034(13) 0.613(3) 0.086(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 N11 0.0295(4) 0.0281(4) 0.0254(4) -0.0008(3) 0.0026(3) 0.0068(3) C12 0.0332(5) 0.0258(5) 0.0225(5) 0.0001(4) 0.0049(4) 0.0027(4) C13 0.0293(5) 0.0320(5) 0.0220(4) -0.0001(4) 0.0075(4) 0.0024(4) C14 0.0311(5) 0.0290(5) 0.0248(5) 0.0019(4) 0.0093(4) 0.0081(4) C15 0.0341(5) 0.0259(5) 0.0237(5) 0.0002(3) 0.0103(4) 0.0033(4) C16 0.0274(5) 0.0306(5) 0.0294(5) -0.0030(4) 0.0060(4) 0.0024(4) C17 0.0327(6) 0.0453(7) 0.0509(7) -0.0053(5) 0.0157(5) -0.0029(5) C18 0.0473(7) 0.0276(5) 0.0440(6) -0.0016(4) 0.0203(5) -0.0009(4) C21 0.0204(4) 0.0230(5) 0.0340(5) 0.0022(4) 0.0071(4) 0.0001(3) C22 0.0235(5) 0.0226(5) 0.0364(5) 0.0000(4) 0.0068(4) 0.0027(3) O21 0.0332(4) 0.0271(4) 0.0460(5) -0.0063(3) -0.0006(3) 0.0067(3) O22 0.0306(4) 0.0280(4) 0.0363(4) -0.0020(3) -0.0011(3) 0.0083(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.3369(14) . ? N11 C12 1.3377(14) . ? N11 H2A 1.42(2) . ? C12 C13 1.3875(14) . ? C12 H12 0.9500 . ? C13 C14 1.3927(15) . ? C13 C17 1.5042(15) . ? C14 C15 1.3900(15) . ? C14 H14 0.9500 . ? C15 C16 1.3889(14) . ? C15 C18 1.5044(15) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C17 H17D 0.9800 . ? C17 H17E 0.9800 . ? C17 H17F 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C18 H18D 0.9800 . ? C18 H18E 0.9800 . ? C18 H18F 0.9800 . ? C21 O21 1.2205(13) . ? C21 O22 1.3002(13) . ? C21 C22 1.4956(13) . ? C22 C22 1.317(2) 3_857 ? C22 H22 0.9500 . ? O22 H2A 1.12(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 119.84(9) . . ? C16 N11 H2A 120.8(9) . . ? C12 N11 H2A 119.0(9) . . ? N11 C12 C13 122.33(10) . . ? N11 C12 H12 118.8 . . ? C13 C12 H12 118.8 . . ? C12 C13 C14 117.14(10) . . ? C12 C13 C17 121.06(10) . . ? C14 C13 C17 121.80(10) . . ? C15 C14 C13 121.19(9) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C16 C15 C14 117.13(9) . . ? C16 C15 C18 120.44(10) . . ? C14 C15 C18 122.43(10) . . ? N11 C16 C15 122.36(10) . . ? N11 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? 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 . . ? C13 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? C13 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? C13 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 C18 H18D 109.5 . . ? H18A C18 H18D 141.1 . . ? H18B C18 H18D 56.3 . . ? H18C C18 H18D 56.3 . . ? C15 C18 H18E 109.5 . . ? H18A C18 H18E 56.3 . . ? H18B C18 H18E 141.1 . . ? H18C C18 H18E 56.3 . . ? H18D C18 H18E 109.5 . . ? C15 C18 H18F 109.5 . . ? H18A C18 H18F 56.3 . . ? H18B C18 H18F 56.3 . . ? H18C C18 H18F 141.1 . . ? H18D C18 H18F 109.5 . . ? H18E C18 H18F 109.5 . . ? O21 C21 O22 125.07(9) . . ? O21 C21 C22 121.64(9) . . ? O22 C21 C22 113.28(9) . . ? C22 C22 C21 122.66(12) 3_857 . ? C22 C22 H22 118.7 3_857 . ? C21 C22 H22 118.7 . . ? C21 O22 H2A 111.0(11) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O22 H2A N11 1.12(2) 1.42(2) 2.5423(11) 177.4(19) . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.222 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.047 # Attachment '3,5 lutidine succinic acid co-crystal.cif' data_wj0433 _database_code_depnum_ccdc_archive 'CCDC 615320' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,5 lutidine succinic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety '2(C7 H9 N), C4 H6 O4' _chemical_formula_sum 'C18 H24 N2 O4' _chemical_formula_weight 332.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.464(2) _cell_length_b 4.9696(10) _cell_length_c 17.113(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.67(3) _cell_angle_gamma 90.00 _cell_volume 885.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9867 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_T_max 1.004 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atom was located and its position was refined without any restraints. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5880 _diffrn_reflns_av_R_equivalents 0.0570 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 27.55 _reflns_number_total 2025 _reflns_number_gt 1336 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.2795P] 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 2025 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1453 _refine_ls_wR_factor_gt 0.1263 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.81915(16) -0.2285(3) 0.89971(10) 0.0347(4) Uani 1 1 d . . . C12 C 0.7347(2) -0.3291(4) 0.84321(12) 0.0344(5) Uani 1 1 d . . . H12 H 0.650(2) -0.242(4) 0.8401(12) 0.033(5) Uiso 1 1 d . . . C13 C 0.76253(19) -0.5379(4) 0.79426(12) 0.0350(5) Uani 1 1 d . . . C14 C 0.8852(2) -0.6450(4) 0.80545(12) 0.0337(5) Uani 1 1 d . . . H14 H 0.907(2) -0.794(5) 0.7736(13) 0.046(6) Uiso 1 1 d . . . C15 C 0.97546(18) -0.5455(4) 0.86302(11) 0.0306(5) Uani 1 1 d . . . C16 C 0.9371(2) -0.3367(4) 0.90862(12) 0.0330(5) Uani 1 1 d . . . H16 H 0.996(2) -0.262(4) 0.9507(13) 0.038(6) Uiso 1 1 d . . . C17 C 0.6622(2) -0.6430(5) 0.73233(15) 0.0517(6) Uani 1 1 d . . . H17A H 0.6826 -0.8292 0.7194 0.078 Uiso 0.50 1 calc PR . . H17B H 0.6612 -0.5313 0.6851 0.078 Uiso 0.50 1 calc PR . . H17C H 0.5776 -0.6367 0.7523 0.078 Uiso 0.50 1 calc PR . . H17D H 0.5983 -0.5022 0.7185 0.078 Uiso 0.50 1 calc PR . . H17E H 0.6197 -0.8001 0.7528 0.078 Uiso 0.50 1 calc PR . . H17F H 0.7033 -0.6948 0.6855 0.078 Uiso 0.50 1 calc PR . . C18 C 1.1087(2) -0.6604(5) 0.87691(13) 0.0413(5) Uani 1 1 d . . . H18A H 1.1047 -0.8393 0.9006 0.062 Uiso 1 1 calc R . . H18B H 1.1622 -0.5420 0.9124 0.062 Uiso 1 1 calc R . . H18C H 1.1461 -0.6749 0.8268 0.062 Uiso 1 1 calc R . . C21 C 0.61601(18) 0.2336(4) 0.96575(11) 0.0303(5) Uani 1 1 d . . . C22 C 0.56752(18) 0.4557(4) 1.01413(12) 0.0315(5) Uani 1 1 d . . . H22A H 0.6259 0.6121 1.0130 0.038 Uiso 1 1 calc R . . H22B H 0.5694 0.3945 1.0693 0.038 Uiso 1 1 calc R . . O21 O 0.55295(14) 0.1270(3) 0.91129(9) 0.0417(4) Uani 1 1 d . . . O22 O 0.73648(13) 0.1645(3) 0.98904(9) 0.0383(4) Uani 1 1 d . . . H22 H 0.771(3) 0.012(7) 0.954(2) 0.100(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0343(10) 0.0321(9) 0.0376(10) -0.0003(7) 0.0027(8) 0.0026(7) C12 0.0293(11) 0.0365(11) 0.0373(11) 0.0036(9) 0.0022(9) 0.0039(9) C13 0.0333(11) 0.0383(11) 0.0326(11) 0.0001(9) -0.0010(9) 0.0007(9) C14 0.0340(11) 0.0368(11) 0.0308(11) -0.0035(9) 0.0055(9) 0.0016(9) C15 0.0297(10) 0.0340(10) 0.0286(10) 0.0040(8) 0.0049(8) 0.0004(8) C16 0.0320(11) 0.0331(10) 0.0334(11) -0.0007(8) 0.0010(9) -0.0026(9) C17 0.0422(14) 0.0607(15) 0.0490(14) -0.0112(12) -0.0113(11) 0.0039(11) C18 0.0321(11) 0.0503(13) 0.0413(12) -0.0015(10) 0.0026(9) 0.0052(10) C21 0.0274(10) 0.0290(10) 0.0340(11) -0.0001(8) 0.0002(8) -0.0010(8) C22 0.0296(11) 0.0303(10) 0.0336(10) -0.0030(8) -0.0016(8) 0.0019(8) O21 0.0332(8) 0.0456(9) 0.0443(9) -0.0139(7) -0.0059(7) 0.0052(7) O22 0.0300(8) 0.0379(8) 0.0449(9) -0.0081(7) -0.0066(7) 0.0078(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.340(3) . ? N11 C16 1.341(3) . ? C12 C13 1.383(3) . ? C12 H12 0.99(2) . ? C13 C14 1.386(3) . ? C13 C17 1.510(3) . ? C14 C15 1.387(3) . ? C14 H14 0.96(2) . ? C15 C16 1.381(3) . ? C15 C18 1.504(3) . ? C16 H16 0.97(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C17 H17D 0.9800 . ? C17 H17E 0.9800 . ? C17 H17F 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C21 O21 1.210(2) . ? C21 O22 1.329(2) . ? C21 C22 1.498(3) . ? C22 C22 1.513(4) 3_667 ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? O22 H22 1.05(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C16 117.78(18) . . ? N11 C12 C13 123.64(19) . . ? N11 C12 H12 113.8(12) . . ? C13 C12 H12 122.6(12) . . ? C12 C13 C14 116.89(18) . . ? C12 C13 C17 120.77(19) . . ? C14 C13 C17 122.3(2) . . ? C13 C14 C15 121.17(19) . . ? C13 C14 H14 119.3(13) . . ? C15 C14 H14 119.5(13) . . ? C16 C15 C14 117.01(18) . . ? C16 C15 C18 120.83(18) . . ? C14 C15 C18 122.16(19) . . ? N11 C16 C15 123.51(19) . . ? N11 C16 H16 116.1(13) . . ? C15 C16 H16 120.3(13) . . ? 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 . . ? C13 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? C13 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? C13 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O21 C21 O22 123.14(18) . . ? O21 C21 C22 124.05(18) . . ? O22 C21 C22 112.82(16) . . ? C21 C22 C22 113.2(2) . 3_667 ? C21 C22 H22A 108.9 . . ? C22 C22 H22A 108.9 3_667 . ? C21 C22 H22B 108.9 . . ? C22 C22 H22B 108.9 3_667 . ? H22A C22 H22B 107.7 . . ? C21 O22 H22 112.5(17) . . ? 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 O22 H22 N11 1.05(4) 1.62(4) 2.676(2) 178(3) . _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.194 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.060