Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'C. Aakeroy' _publ_contact_author_address ; Department of Chemistry Kansas State University Manhattan Kansas 66506-3701 UNITED STATES OF AMERICA ; _publ_contact_author_email AAKEROY@KSU.EDU _publ_section_title ; Exploring the hydrogen-bond preference of N-H moieties in co-crystals assembled via O-H(acid)***N(py) intermolecular interactions ; loop_ _publ_author_name 'C. Aakeroy' 'John Desper' 'Safiyyah Forbes' 'Izhar Hussain' # Attachment 'all17.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 624060' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis[N-(3-pyridyl)acetamide] fumaric acid ; _chemical_name_common 'bis(N-(3-pyridyl)acetamide) fumaric acid' _chemical_melting_point ? _chemical_formula_moiety ; (C7 H8 N2 O)2 (C4 H4 O4) ; _chemical_formula_sum 'C18 H20 N4 O6' _chemical_formula_weight 388.38 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 Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 17.930(4) _cell_length_b 3.9380(10) _cell_length_c 25.723(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1816.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2163 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 26.25 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.01 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11419 _diffrn_reflns_av_R_equivalents 0.0776 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.22 _reflns_number_total 2172 _reflns_number_gt 1612 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1350P)^2^+1.2000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2172 _refine_ls_number_parameters 255 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1140 _refine_ls_R_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.2264 _refine_ls_wR_factor_gt 0.2101 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 0.4163(3) 0.0730(14) 0.7999(2) 0.0185(12) Uani 1 1 d . . . C12 C 0.4311(3) -0.0278(17) 0.8488(3) 0.0215(16) Uani 1 1 d . . . H12 H 0.4777 0.0285 0.8641 0.026 Uiso 1 1 calc R . . C13 C 0.3789(3) -0.2143(15) 0.8774(3) 0.0173(12) Uani 1 1 d . . . N13 N 0.4021(3) -0.3194(13) 0.9271(2) 0.0220(12) Uani 1 1 d . . . H13 H 0.4488 -0.2776 0.9354 0.026 Uiso 1 1 calc R . . C14 C 0.3108(3) -0.2932(16) 0.8543(3) 0.0209(13) Uani 1 1 d . . . H14 H 0.2744 -0.4213 0.8726 0.025 Uiso 1 1 calc R . . C15 C 0.2972(3) -0.1825(15) 0.8045(3) 0.0212(14) Uani 1 1 d . . . H15 H 0.2511 -0.2345 0.7881 0.025 Uiso 1 1 calc R . . C16 C 0.3501(4) 0.0033(16) 0.7784(3) 0.0202(16) Uani 1 1 d . . . H16 H 0.3395 0.0840 0.7444 0.024 Uiso 1 1 calc R . . C17 C 0.3590(4) -0.4822(18) 0.9644(3) 0.0224(14) Uani 1 1 d . . . O17 O 0.2950(3) -0.5495(14) 0.9575(2) 0.0311(13) Uani 1 1 d . . . C18 C 0.3998(4) -0.5594(17) 1.0147(3) 0.0226(15) Uani 1 1 d . . . H18A H 0.3976 -0.3607 1.0376 0.034 Uiso 1 1 calc R . . H18B H 0.4520 -0.6139 1.0071 0.034 Uiso 1 1 calc R . . H18C H 0.3761 -0.7534 1.0320 0.034 Uiso 1 1 calc R . . N21 N 0.8258(3) 1.4124(13) 0.6278(2) 0.0188(12) Uani 1 1 d . . . C22 C 0.8138(3) 1.5037(14) 0.5797(3) 0.0144(14) Uani 1 1 d . . . H22 H 0.7678 1.4403 0.5642 0.017 Uiso 1 1 calc R . . C23 C 0.8646(3) 1.6891(17) 0.5497(3) 0.0208(14) Uani 1 1 d . . . N23 N 0.8441(3) 1.7732(14) 0.4986(2) 0.0207(12) Uani 1 1 d . . . H23 H 0.7965 1.7533 0.4908 0.025 Uiso 1 1 calc R . . C24 C 0.9323(3) 1.7817(16) 0.5724(3) 0.0191(13) Uani 1 1 d . . . H24 H 0.9683 1.9093 0.5536 0.023 Uiso 1 1 calc R . . C25 C 0.9450(3) 1.6808(16) 0.6232(3) 0.0217(14) Uani 1 1 d . . . H25 H 0.9903 1.7405 0.6400 0.026 Uiso 1 1 calc R . . C26 C 0.8919(4) 1.4936(15) 0.6494(3) 0.0157(14) Uani 1 1 d . . . H26 H 0.9023 1.4197 0.6838 0.019 Uiso 1 1 calc R . . C27 C 0.8902(3) 1.8832(17) 0.4592(3) 0.0258(15) Uani 1 1 d . . . O27 O 0.9582(2) 1.9309(13) 0.4661(2) 0.0282(12) Uani 1 1 d . . . C28 C 0.8533(4) 1.9366(19) 0.4098(3) 0.0290(18) Uani 1 1 d . . . H28A H 0.8668 2.1606 0.3961 0.044 Uiso 1 1 calc R . . H28B H 0.7991 1.9248 0.4146 0.044 Uiso 1 1 calc R . . H28C H 0.8690 1.7606 0.3852 0.044 Uiso 1 1 calc R . . C31 C 0.6713(4) 0.9944(14) 0.6581(3) 0.0180(15) Uani 1 1 d . . . O31 O 0.7328(2) 1.0531(12) 0.6823(2) 0.0233(12) Uani 1 1 d . . . H31 H 0.7618 1.1616 0.6627 0.035 Uiso 1 1 calc R . . O32 O 0.6556(3) 1.0876(13) 0.6140(2) 0.0280(12) Uani 1 1 d . . . C32 C 0.6140(3) 0.7972(16) 0.6888(3) 0.0196(13) Uani 1 1 d . . . H32 H 0.5676 0.7441 0.6729 0.024 Uiso 1 1 calc R . . C33 C 0.6259(3) 0.6953(15) 0.7373(3) 0.0192(13) Uani 1 1 d . . . H33 H 0.6720 0.7556 0.7530 0.023 Uiso 1 1 calc R . . C34 C 0.5734(4) 0.4977(17) 0.7683(3) 0.0184(15) Uani 1 1 d . . . O33 O 0.5857(3) 0.4073(14) 0.8122(2) 0.0289(12) Uani 1 1 d . . . O34 O 0.5091(3) 0.4368(12) 0.7440(2) 0.0214(11) Uani 1 1 d . . . H34 H 0.4812 0.3222 0.7635 0.032 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 0.014(2) 0.019(3) 0.022(3) 0.000(2) 0.001(2) -0.005(2) C12 0.011(3) 0.031(4) 0.022(5) -0.002(3) 0.001(3) -0.002(2) C13 0.013(3) 0.017(3) 0.022(3) -0.004(2) -0.001(2) 0.000(2) N13 0.015(2) 0.028(3) 0.022(3) 0.007(2) -0.003(2) -0.012(2) C14 0.017(3) 0.021(3) 0.025(4) 0.000(3) -0.001(3) 0.000(2) C15 0.019(3) 0.016(3) 0.029(4) -0.006(3) -0.002(3) -0.003(2) C16 0.021(3) 0.017(3) 0.023(5) -0.003(2) -0.009(3) 0.005(2) C17 0.021(3) 0.034(4) 0.012(3) -0.003(3) 0.002(3) -0.004(2) O17 0.025(3) 0.053(3) 0.016(3) -0.001(3) 0.004(2) -0.016(2) C18 0.024(3) 0.022(3) 0.022(4) 0.007(3) -0.006(3) -0.009(3) N21 0.019(3) 0.016(2) 0.021(3) -0.006(2) 0.001(2) 0.0001(19) C22 0.017(3) 0.009(3) 0.018(4) -0.002(2) 0.000(3) -0.004(2) C23 0.013(3) 0.020(3) 0.029(4) -0.004(3) 0.005(3) 0.007(2) N23 0.009(2) 0.028(3) 0.025(3) 0.004(2) -0.004(2) -0.002(2) C24 0.014(3) 0.018(3) 0.026(4) -0.002(3) 0.001(2) -0.003(2) C25 0.017(3) 0.018(3) 0.030(4) -0.002(3) -0.006(3) 0.000(2) C26 0.025(3) 0.013(3) 0.010(4) -0.002(2) 0.004(3) -0.001(2) C27 0.013(3) 0.027(3) 0.038(4) 0.003(3) 0.003(3) -0.005(2) O27 0.010(2) 0.044(3) 0.030(3) 0.005(3) 0.004(2) -0.0050(18) C28 0.026(3) 0.027(4) 0.034(5) 0.007(3) 0.005(3) -0.013(3) C31 0.022(3) 0.008(3) 0.024(5) -0.003(2) -0.010(3) 0.003(2) O31 0.022(2) 0.027(2) 0.020(3) 0.005(2) -0.001(2) -0.0090(19) O32 0.028(2) 0.029(3) 0.027(3) 0.006(2) -0.006(2) -0.0107(19) C32 0.017(3) 0.020(3) 0.022(4) -0.002(3) 0.001(2) -0.001(2) C33 0.012(2) 0.017(3) 0.028(4) 0.002(3) -0.003(2) 0.000(2) C34 0.022(3) 0.025(3) 0.009(4) -0.003(2) 0.006(3) 0.004(2) O33 0.029(2) 0.040(3) 0.018(3) 0.002(2) -0.004(2) -0.005(2) O34 0.0136(19) 0.033(3) 0.017(3) 0.003(2) 0.0008(18) 0.0003(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.336(9) . ? N11 C12 1.346(10) . ? C12 C13 1.399(9) . ? C12 H12 0.9500 . ? C13 C14 1.393(8) . ? C13 N13 1.407(8) . ? N13 C17 1.389(9) . ? N13 H13 0.8800 . ? C14 C15 1.375(10) . ? C14 H14 0.9500 . ? C15 C16 1.374(10) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.192(8) . ? C17 C18 1.517(10) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? N21 C22 1.305(10) . ? N21 C26 1.349(9) . ? C22 C23 1.398(9) . ? C22 H22 0.9500 . ? C23 C24 1.395(9) . ? C23 N23 1.407(9) . ? N23 C27 1.376(9) . ? N23 H23 0.8800 . ? C24 C25 1.386(10) . ? C24 H24 0.9500 . ? C25 C26 1.380(9) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O27 1.247(7) . ? C27 C28 1.449(11) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C31 O32 1.224(10) . ? C31 O31 1.287(8) . ? C31 C32 1.511(10) . ? O31 H31 0.8400 . ? C32 C33 1.327(8) . ? C32 H32 0.9500 . ? C33 C34 1.457(9) . ? C33 H33 0.9500 . ? C34 O33 1.205(10) . ? C34 O34 1.334(9) . ? O34 H34 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 120.0(6) . . ? N11 C12 C13 121.0(6) . . ? N11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 118.6(6) . . ? C14 C13 N13 125.6(6) . . ? C12 C13 N13 115.7(5) . . ? C17 N13 C13 126.8(5) . . ? C17 N13 H13 116.6 . . ? C13 N13 H13 116.6 . . ? C15 C14 C13 118.9(6) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C16 C15 C14 120.1(6) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? N11 C16 C15 121.4(7) . . ? N11 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? O17 C17 N13 122.4(7) . . ? O17 C17 C18 123.1(7) . . ? N13 C17 C18 114.5(6) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C22 N21 C26 118.1(6) . . ? N21 C22 C23 124.0(6) . . ? N21 C22 H22 118.0 . . ? C23 C22 H22 118.0 . . ? C24 C23 C22 118.2(6) . . ? C24 C23 N23 123.8(6) . . ? C22 C23 N23 118.0(6) . . ? C27 N23 C23 127.3(5) . . ? C27 N23 H23 116.4 . . ? C23 N23 H23 116.4 . . ? C25 C24 C23 117.5(6) . . ? C25 C24 H24 121.2 . . ? C23 C24 H24 121.2 . . ? C26 C25 C24 120.1(6) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? N21 C26 C25 122.1(7) . . ? N21 C26 H26 119.0 . . ? C25 C26 H26 119.0 . . ? O27 C27 N23 122.1(7) . . ? O27 C27 C28 123.3(7) . . ? N23 C27 C28 114.6(6) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O32 C31 O31 126.2(7) . . ? O32 C31 C32 118.9(6) . . ? O31 C31 C32 115.0(7) . . ? C31 O31 H31 109.5 . . ? C33 C32 C31 122.5(5) . . ? C33 C32 H32 118.7 . . ? C31 C32 H32 118.7 . . ? C32 C33 C34 124.9(5) . . ? C32 C33 H33 117.6 . . ? C34 C33 H33 117.6 . . ? O33 C34 O34 122.9(7) . . ? O33 C34 C33 123.6(7) . . ? O34 C34 C33 113.5(7) . . ? C34 O34 H34 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 C16 N11 C12 C13 1.8(10) . . . . ? N11 C12 C13 C14 -0.2(9) . . . . ? N11 C12 C13 N13 177.0(6) . . . . ? C14 C13 N13 C17 -8.6(10) . . . . ? C12 C13 N13 C17 174.4(7) . . . . ? C12 C13 C14 C15 -0.6(9) . . . . ? N13 C13 C14 C15 -177.5(6) . . . . ? C13 C14 C15 C16 -0.2(9) . . . . ? C12 N11 C16 C15 -2.7(10) . . . . ? C14 C15 C16 N11 1.8(10) . . . . ? C13 N13 C17 O17 -0.5(11) . . . . ? C13 N13 C17 C18 -179.2(6) . . . . ? C26 N21 C22 C23 -1.9(9) . . . . ? N21 C22 C23 C24 0.2(9) . . . . ? N21 C22 C23 N23 -179.4(5) . . . . ? C24 C23 N23 C27 16.2(10) . . . . ? C22 C23 N23 C27 -164.2(6) . . . . ? C22 C23 C24 C25 0.5(9) . . . . ? N23 C23 C24 C25 -179.9(6) . . . . ? C23 C24 C25 C26 0.5(9) . . . . ? C22 N21 C26 C25 2.9(9) . . . . ? C24 C25 C26 N21 -2.2(9) . . . . ? C23 N23 C27 O27 -2.2(11) . . . . ? C23 N23 C27 C28 177.5(6) . . . . ? O32 C31 C32 C33 -178.1(6) . . . . ? O31 C31 C32 C33 0.7(9) . . . . ? C31 C32 C33 C34 -178.4(6) . . . . ? C32 C33 C34 O33 179.8(6) . . . . ? C32 C33 C34 O34 -2.7(9) . . . . ? 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 O31 H31 N21 0.84 1.76 2.597(7) 173.8 . O34 H34 N11 0.84 1.79 2.623(7) 174.7 . N13 H13 O27 0.88 2.02 2.872(7) 163.2 4_635 N23 H23 O17 0.88 2.02 2.847(7) 157.0 2_664 _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 28.22 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.922 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.143 #END data_2 _database_code_depnum_ccdc_archive 'CCDC 624061' _audit_creation_method SHELXL-97 _chemical_name_systematic ; {N-[(4-pyridyl)methyl]acetamide}2, fumaric acid ; _chemical_name_common '(N-((4-pyridyl)methyl)acetamide)2, fumaric acid' _chemical_melting_point ? _chemical_formula_moiety ; (C8 H10 N2 O)2 (C4 H4 O4) ; _chemical_formula_sum 'C20 H24 N4 O6' _chemical_formula_weight 416.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9718(10) _cell_length_b 7.0047(11) _cell_length_c 15.101(2) _cell_angle_alpha 77.032(10) _cell_angle_beta 89.414(12) _cell_angle_gamma 82.324(12) _cell_volume 507.80(15) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 737 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 23.25 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3376 _diffrn_reflns_av_R_equivalents 0.1207 _diffrn_reflns_av_sigmaI/netI 0.1470 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 28.23 _reflns_number_total 2078 _reflns_number_gt 1054 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2078 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1513 _refine_ls_R_factor_gt 0.0883 _refine_ls_wR_factor_ref 0.2920 _refine_ls_wR_factor_gt 0.2423 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _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 0.2387(7) 0.3449(5) 0.1645(3) 0.0372(10) Uani 1 1 d . . . C12 C 0.4103(9) 0.2674(6) 0.2333(3) 0.0361(11) Uani 1 1 d . . . H12 H 0.5381 0.3462 0.2474 0.043 Uiso 1 1 calc R . . C13 C 0.4146(9) 0.0787(7) 0.2859(3) 0.0404(12) Uani 1 1 d . . . H13 H 0.5406 0.0302 0.3353 0.048 Uiso 1 1 calc R . . C14 C 0.2321(8) -0.0387(6) 0.2656(3) 0.0304(10) Uani 1 1 d . . . C15 C 0.0512(9) 0.0427(7) 0.1951(3) 0.0376(11) Uani 1 1 d . . . H15 H -0.0804 -0.0324 0.1803 0.045 Uiso 1 1 calc R . . C16 C 0.0590(9) 0.2316(6) 0.1459(3) 0.0385(11) Uani 1 1 d . . . H16 H -0.0672 0.2843 0.0969 0.046 Uiso 1 1 calc R . . C17 C 0.2363(10) -0.2482(7) 0.3187(3) 0.0400(12) Uani 1 1 d . . . H17A H 0.0611 -0.2933 0.3084 0.048 Uiso 1 1 calc R . . H17B H 0.3814 -0.3335 0.2950 0.048 Uiso 1 1 calc R . . N17 N 0.2803(6) -0.2737(5) 0.4145(2) 0.0303(9) Uani 1 1 d . . . H17 H 0.4483 -0.2953 0.4359 0.036 Uiso 1 1 calc R . . C21 C 0.0761(8) -0.2659(6) 0.4729(3) 0.0279(9) Uani 1 1 d . . . O21 O -0.1616(6) -0.2436(5) 0.4480(2) 0.0408(9) Uani 1 1 d . . . C22 C 0.1566(10) -0.2844(7) 0.5695(3) 0.0416(12) Uani 1 1 d . . . H22A H 0.3525 -0.2814 0.5738 0.062 Uiso 1 1 calc R . . H22B H 0.1114 -0.4096 0.6063 0.062 Uiso 1 1 calc R . . H22C H 0.0589 -0.1742 0.5919 0.062 Uiso 1 1 calc R . . C31 C 0.5224(9) 0.7487(7) 0.0867(3) 0.0343(10) Uani 1 1 d . . . O31 O 0.2988(6) 0.6918(5) 0.0637(2) 0.0436(9) Uani 1 1 d . . . H31 H 0.2856 0.5779 0.0947 0.052 Uiso 1 1 calc R . . O32 O 0.6658(6) 0.6638(5) 0.1516(2) 0.0428(9) Uani 1 1 d . . . C32 C 0.5868(9) 0.9351(6) 0.0282(3) 0.0358(11) Uani 1 1 d . . . H32 H 0.7671 0.9643 0.0312 0.043 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 0.040(2) 0.032(2) 0.038(2) -0.0006(16) -0.0023(16) -0.0111(17) C12 0.038(2) 0.030(2) 0.040(3) -0.005(2) -0.0018(19) -0.011(2) C13 0.045(3) 0.035(3) 0.039(3) 0.002(2) -0.008(2) -0.014(2) C14 0.037(2) 0.028(2) 0.028(2) -0.0054(18) 0.0053(17) -0.0092(19) C15 0.040(2) 0.037(3) 0.035(2) -0.001(2) 0.0001(19) -0.014(2) C16 0.041(3) 0.030(2) 0.040(3) 0.003(2) -0.006(2) -0.008(2) C17 0.052(3) 0.032(3) 0.035(3) -0.002(2) 0.007(2) -0.013(2) N17 0.0239(18) 0.0263(19) 0.038(2) -0.0003(15) 0.0005(14) -0.0034(15) C21 0.023(2) 0.021(2) 0.038(2) -0.0015(17) 0.0008(17) -0.0043(16) O21 0.0247(16) 0.0393(19) 0.055(2) -0.0020(16) -0.0034(14) -0.0050(14) C22 0.049(3) 0.035(3) 0.040(3) -0.003(2) 0.000(2) -0.009(2) C31 0.035(2) 0.033(2) 0.033(2) -0.0020(19) 0.0045(18) -0.0077(19) O31 0.049(2) 0.0342(18) 0.0417(19) 0.0111(14) -0.0097(15) -0.0188(15) O32 0.0453(19) 0.0360(18) 0.0413(19) 0.0077(15) -0.0075(15) -0.0122(15) C32 0.042(3) 0.031(2) 0.034(2) -0.0012(19) 0.0004(17) -0.014(2) _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 1.321(6) . ? N11 C16 1.342(5) . ? C12 C13 1.378(6) . ? C12 H12 0.9500 . ? C13 C14 1.383(5) . ? C13 H13 0.9500 . ? C14 C15 1.369(6) . ? C14 C17 1.504(6) . ? C15 C16 1.370(6) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N17 1.434(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? N17 C21 1.342(5) . ? N17 H17 0.8800 . ? C21 O21 1.223(4) . ? C21 C22 1.489(6) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C31 O32 1.209(5) . ? C31 O31 1.305(5) . ? C31 C32 1.475(6) . ? O31 H31 0.8400 . ? C32 C32 1.324(9) 2_675 ? 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 C12 N11 C16 117.3(4) . . ? N11 C12 C13 123.8(4) . . ? N11 C12 H12 118.1 . . ? C13 C12 H12 118.1 . . ? C12 C13 C14 118.8(4) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 117.5(4) . . ? C15 C14 C17 121.8(4) . . ? C13 C14 C17 120.7(4) . . ? C14 C15 C16 120.4(4) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? N11 C16 C15 122.3(4) . . ? N11 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? N17 C17 C14 114.0(4) . . ? N17 C17 H17A 108.8 . . ? C14 C17 H17A 108.8 . . ? N17 C17 H17B 108.8 . . ? C14 C17 H17B 108.8 . . ? H17A C17 H17B 107.6 . . ? C21 N17 C17 122.7(3) . . ? C21 N17 H17 118.6 . . ? C17 N17 H17 118.6 . . ? O21 C21 N17 121.8(4) . . ? O21 C21 C22 122.2(4) . . ? N17 C21 C22 115.9(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O32 C31 O31 124.8(4) . . ? O32 C31 C32 120.8(4) . . ? O31 C31 C32 114.4(4) . . ? C31 O31 H31 109.5 . . ? C32 C32 C31 125.2(5) 2_675 . ? C32 C32 H32 117.4 2_675 . ? C31 C32 H32 117.4 . . ? 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 C16 N11 C12 C13 0.3(7) . . . . ? N11 C12 C13 C14 0.8(8) . . . . ? C12 C13 C14 C15 -1.8(7) . . . . ? C12 C13 C14 C17 177.6(4) . . . . ? C13 C14 C15 C16 1.8(7) . . . . ? C17 C14 C15 C16 -177.6(4) . . . . ? C12 N11 C16 C15 -0.3(7) . . . . ? C14 C15 C16 N11 -0.7(8) . . . . ? C15 C14 C17 N17 -140.0(4) . . . . ? C13 C14 C17 N17 40.7(6) . . . . ? C14 C17 N17 C21 92.7(5) . . . . ? C17 N17 C21 O21 2.7(6) . . . . ? C17 N17 C21 C22 -176.8(4) . . . . ? O32 C31 C32 C32 -161.1(6) . . . 2_675 ? O31 C31 C32 C32 16.6(9) . . . 2_675 ? 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 O31 H31 N11 0.84 1.78 2.614(5) 176.0 . N17 H17 O21 0.88 2.04 2.869(4) 157.2 1_655 _diffrn_measured_fraction_theta_max 0.827 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.913 _refine_diff_density_max 0.378 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.113 #END data_3 _database_code_depnum_ccdc_archive 'CCDC 624062' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(4-pyridyl)acetamide, sebacic acid ; _chemical_name_common 'N-(4-pyridyl)acetamide, sebacic acid' _chemical_melting_point ? _chemical_formula_moiety ; (C7 H8 N2 O)2 (C10 H18 O4) ; _chemical_formula_sum 'C24 H34 N4 O6' _chemical_formula_weight 474.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.532(3) _cell_length_b 8.2965(8) _cell_length_c 10.6120(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.987(2) _cell_angle_gamma 90.00 _cell_volume 2457.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1717 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 26.65 _exptl_crystal_description Irregular _exptl_crystal_colour Colorless _exptl_crystal_size_min 0.22 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14481 _diffrn_reflns_av_R_equivalents 0.0727 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 30.53 _reflns_number_total 3740 _reflns_number_gt 3007 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0900P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3740 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1600 _refine_ls_wR_factor_gt 0.1544 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.27526(4) 0.44681(14) 0.50826(11) 0.0187(2) Uani 1 1 d . . . C12 C 0.26614(4) 0.39198(16) 0.38623(12) 0.0183(3) Uani 1 1 d . . . H12 H 0.2364 0.4185 0.3314 0.022 Uiso 1 1 calc R . . C13 C 0.29829(4) 0.29880(16) 0.33766(12) 0.0177(3) Uani 1 1 d . . . H13 H 0.2905 0.2616 0.2511 0.021 Uiso 1 1 calc R . . C14 C 0.34252(4) 0.25933(15) 0.41701(12) 0.0161(2) Uani 1 1 d . . . C15 C 0.35179(5) 0.31372(17) 0.54485(13) 0.0198(3) Uani 1 1 d . . . H15 H 0.3810 0.2878 0.6025 0.024 Uiso 1 1 calc R . . C16 C 0.31716(5) 0.40630(17) 0.58448(13) 0.0205(3) Uani 1 1 d . . . H16 H 0.3235 0.4434 0.6711 0.025 Uiso 1 1 calc R . . C17 C 0.42033(4) 0.12258(15) 0.42039(13) 0.0180(3) Uani 1 1 d . . . N17 N 0.37454(4) 0.17047(14) 0.36232(11) 0.0175(2) Uani 1 1 d . . . H17 H 0.3656(6) 0.151(2) 0.2828(18) 0.021 Uiso 1 1 d . . . O17 O 0.43793(4) 0.14497(13) 0.53349(9) 0.0239(2) Uani 1 1 d . . . C18 C 0.44709(5) 0.04294(18) 0.32863(13) 0.0224(3) Uani 1 1 d . . . H18A H 0.4724 -0.0260 0.3772 0.034 Uiso 1 1 calc R . . H18B H 0.4614 0.1258 0.2826 0.034 Uiso 1 1 calc R . . H18C H 0.4248 -0.0228 0.2666 0.034 Uiso 1 1 calc R . . C21 C 0.17508(4) 0.65193(16) 0.51364(12) 0.0169(2) Uani 1 1 d . . . O21 O 0.21454(3) 0.61651(13) 0.59567(9) 0.0227(2) Uani 1 1 d . . . H21 H 0.2396(7) 0.540(2) 0.5498(17) 0.027 Uiso 1 1 d . . . O22 O 0.16650(4) 0.60678(12) 0.40136(9) 0.0223(2) Uani 1 1 d . . . C22 C 0.14173(5) 0.75547(16) 0.57235(13) 0.0201(3) Uani 1 1 d . . . H22A H 0.1584 0.8578 0.6013 0.024 Uiso 1 1 calc R . . H22B H 0.1356 0.6998 0.6498 0.024 Uiso 1 1 calc R . . C23 C 0.09401(5) 0.79547(18) 0.48578(15) 0.0247(3) Uani 1 1 d . . . H23A H 0.0768 0.6941 0.4568 0.030 Uiso 1 1 calc R . . H23B H 0.0996 0.8530 0.4085 0.030 Uiso 1 1 calc R . . C24 C 0.06286(5) 0.89970(18) 0.55361(16) 0.0274(3) Uani 1 1 d . . . H24A H 0.0550 0.8382 0.6265 0.033 Uiso 1 1 calc R . . H24B H 0.0813 0.9962 0.5895 0.033 Uiso 1 1 calc R . . C25 C 0.01647(5) 0.95348(19) 0.46502(17) 0.0300(3) Uani 1 1 d . . . H25A H -0.0007 0.8573 0.4237 0.045 Uiso 1 1 calc R . . H25B H 0.0243 1.0224 0.3960 0.045 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 0.0177(5) 0.0207(5) 0.0182(5) 0.0016(4) 0.0049(4) 0.0037(4) C12 0.0154(5) 0.0204(6) 0.0191(6) 0.0017(5) 0.0034(4) 0.0015(4) C13 0.0155(5) 0.0198(6) 0.0172(6) -0.0001(4) 0.0022(4) 0.0005(4) C14 0.0151(5) 0.0154(6) 0.0181(6) 0.0014(4) 0.0045(4) 0.0010(4) C15 0.0177(6) 0.0234(6) 0.0178(6) 0.0002(5) 0.0026(4) 0.0057(5) C16 0.0213(6) 0.0246(6) 0.0158(6) 0.0001(5) 0.0043(5) 0.0051(5) C17 0.0155(5) 0.0179(6) 0.0209(6) 0.0009(4) 0.0045(4) 0.0019(4) N17 0.0159(5) 0.0212(5) 0.0154(5) -0.0024(4) 0.0032(4) 0.0034(4) O17 0.0202(5) 0.0312(5) 0.0194(5) -0.0008(4) 0.0020(4) 0.0063(4) C18 0.0192(6) 0.0264(7) 0.0226(6) -0.0018(5) 0.0067(5) 0.0051(5) C21 0.0152(5) 0.0179(6) 0.0177(6) 0.0021(4) 0.0039(4) 0.0010(4) O21 0.0173(5) 0.0315(5) 0.0182(5) -0.0029(4) 0.0012(3) 0.0083(4) O22 0.0200(5) 0.0288(5) 0.0171(5) 0.0005(4) 0.0018(3) 0.0044(4) C22 0.0170(6) 0.0205(6) 0.0237(6) 0.0000(5) 0.0060(5) 0.0033(4) C23 0.0182(6) 0.0225(7) 0.0331(8) -0.0023(5) 0.0045(5) 0.0027(5) C24 0.0186(6) 0.0235(7) 0.0401(8) -0.0047(6) 0.0061(6) 0.0029(5) C25 0.0176(6) 0.0258(7) 0.0460(9) -0.0054(6) 0.0051(6) 0.0031(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 1.3398(17) . ? N11 C12 1.3460(17) . ? N11 H21 1.421(19) . ? C12 C13 1.3788(17) . ? C12 H12 0.9500 . ? C13 C14 1.4027(17) . ? C13 H13 0.9500 . ? C14 N17 1.3911(16) . ? C14 C15 1.4018(17) . ? C15 C16 1.3841(18) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.2152(16) . ? C17 N17 1.3821(16) . ? C17 C18 1.5089(18) . ? N17 H17 0.845(19) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C21 O22 1.2243(16) . ? C21 O21 1.3056(15) . ? C21 C22 1.5092(17) . ? O21 H21 1.136(19) . ? C22 C23 1.5129(18) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.524(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.523(2) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C25 1.523(3) 5_576 ? C25 H25A 0.9900 . ? C25 H25B 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 117.78(11) . . ? C16 N11 H21 123.8(8) . . ? C12 N11 H21 118.4(8) . . ? N11 C12 C13 122.59(12) . . ? N11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C12 C13 C14 119.46(12) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? N17 C14 C15 124.47(11) . . ? N17 C14 C13 117.40(11) . . ? C15 C14 C13 118.12(11) . . ? C16 C15 C14 118.01(12) . . ? C16 C15 H15 121.0 . . ? C14 C15 H15 121.0 . . ? N11 C16 C15 124.03(12) . . ? N11 C16 H16 118.0 . . ? C15 C16 H16 118.0 . . ? O17 C17 N17 123.70(12) . . ? O17 C17 C18 122.93(12) . . ? N17 C17 C18 113.35(11) . . ? C17 N17 C14 127.46(11) . . ? C17 N17 H17 116.9(12) . . ? C14 N17 H17 115.4(12) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O22 C21 O21 123.39(12) . . ? O22 C21 C22 124.07(11) . . ? O21 C21 C22 112.53(11) . . ? C21 O21 H21 111.8(9) . . ? C21 C22 C23 116.06(11) . . ? C21 C22 H22A 108.3 . . ? C23 C22 H22A 108.3 . . ? C21 C22 H22B 108.3 . . ? C23 C22 H22B 108.3 . . ? H22A C22 H22B 107.4 . . ? C22 C23 C24 112.16(12) . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23A 109.2 . . ? C22 C23 H23B 109.2 . . ? C24 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C25 C24 C23 113.09(13) . . ? C25 C24 H24A 109.0 . . ? C23 C24 H24A 109.0 . . ? C25 C24 H24B 109.0 . . ? C23 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? C24 C25 C25 113.13(17) . 5_576 ? C24 C25 H25A 109.0 . . ? C25 C25 H25A 109.0 5_576 . ? C24 C25 H25B 109.0 . . ? C25 C25 H25B 109.0 5_576 . ? H25A C25 H25B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 -0.84(19) . . . . ? N11 C12 C13 C14 -0.4(2) . . . . ? C12 C13 C14 N17 -177.52(12) . . . . ? C12 C13 C14 C15 1.53(19) . . . . ? N17 C14 C15 C16 177.57(12) . . . . ? C13 C14 C15 C16 -1.41(19) . . . . ? C12 N11 C16 C15 1.0(2) . . . . ? C14 C15 C16 N11 0.2(2) . . . . ? O17 C17 N17 C14 4.8(2) . . . . ? C18 C17 N17 C14 -173.77(12) . . . . ? C15 C14 N17 C17 -1.2(2) . . . . ? C13 C14 N17 C17 177.83(12) . . . . ? O22 C21 C22 C23 3.47(19) . . . . ? O21 C21 C22 C23 -177.09(12) . . . . ? C21 C22 C23 C24 179.81(12) . . . . ? C22 C23 C24 C25 175.05(13) . . . . ? C23 C24 C25 C25 175.47(16) . . . 5_576 ? 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 1.136(19) 1.421(19) 2.5516(15) 172.5(17) . N17 H17 O22 0.845(19) 2.012(19) 2.8494(15) 170.8(17) 4_545 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.510 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.080 #END data_4 _database_code_depnum_ccdc_archive 'CCDC 624063' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(acetamidomethyl)pyridine, adipic acid ; _chemical_name_common '4-(acetamidomethyl)pyridine, adipic acid' _chemical_melting_point ? _chemical_formula_moiety '(C8 H10 N2 O)2 (C6 H10 O4)' _chemical_formula_sum 'C22 H30 N4 O6' _chemical_formula_weight 446.50 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 4.7523(7) _cell_length_b 24.295(3) _cell_length_c 10.0355(12) _cell_angle_alpha 90.00 _cell_angle_beta 97.944(10) _cell_angle_gamma 90.00 _cell_volume 1147.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1056 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 26.00 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8215 _diffrn_reflns_av_R_equivalents 0.1423 _diffrn_reflns_av_sigmaI/netI 0.1049 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 28.24 _reflns_number_total 2669 _reflns_number_gt 1557 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.055(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2669 _refine_ls_number_parameters 195 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0990 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1486 _refine_ls_wR_factor_gt 0.1318 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.963 _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 N11A N 0.0313(19) 0.1824(5) 0.3396(12) 0.0325(13) Uani 0.477(10) 1 d PD A 1 C12A C -0.1898(15) 0.2065(2) 0.2743(7) 0.0438(15) Uani 0.477(10) 1 d PD A 1 H12A H -0.3149 0.1849 0.2133 0.053 Uiso 0.477(10) 1 calc PR A 1 C13A C -0.2550(14) 0.2611(2) 0.2874(6) 0.0378(13) Uani 0.477(10) 1 d PD A 1 H13A H -0.4385 0.2749 0.2543 0.045 Uiso 0.477(10) 1 calc PR A 1 C14A C -0.039(3) 0.2964(5) 0.3520(13) 0.0224(17) Uani 0.477(10) 1 d PD A 1 C15A C 0.1899(13) 0.2720(2) 0.4219(8) 0.0401(15) Uani 0.477(10) 1 d PD A 1 H15A H 0.3178 0.2929 0.4833 0.048 Uiso 0.477(10) 1 calc PR A 1 C16A C 0.2387(14) 0.2164(3) 0.4039(9) 0.0457(17) Uani 0.477(10) 1 d PD A 1 H16A H 0.4197 0.2014 0.4368 0.055 Uiso 0.477(10) 1 calc PR A 1 N11B N 0.0990(18) 0.1821(4) 0.3328(10) 0.0325(13) Uani 0.523(10) 1 d PD A 2 C12B C -0.0721(16) 0.2082(2) 0.2442(6) 0.0458(15) Uani 0.523(10) 1 d PD A 2 H12B H -0.1600 0.1881 0.1685 0.055 Uiso 0.523(10) 1 calc PR A 2 C13B C -0.1373(15) 0.26361(19) 0.2516(6) 0.0439(14) Uani 0.523(10) 1 d PD A 2 H13B H -0.2307 0.2827 0.1754 0.053 Uiso 0.523(10) 1 calc PR A 2 C14B C -0.061(3) 0.2911(4) 0.3760(11) 0.0224(17) Uani 0.523(10) 1 d PD A 2 C15B C 0.1167(13) 0.2638(2) 0.4700(6) 0.0374(13) Uani 0.523(10) 1 d PD A 2 H15B H 0.2050 0.2826 0.5477 0.045 Uiso 0.523(10) 1 calc PR A 2 C16B C 0.1699(14) 0.2085(2) 0.4535(6) 0.0423(14) Uani 0.523(10) 1 d PD A 2 H16B H 0.2589 0.1881 0.5284 0.051 Uiso 0.523(10) 1 calc PR A 2 C21 C -0.1122(4) 0.35396(8) 0.3826(2) 0.0382(5) Uani 1 1 d . . . H21A H -0.2518 0.3542 0.4473 0.046 Uiso 1 1 calc R A 1 H21B H 0.0603 0.3737 0.4240 0.046 Uiso 1 1 calc R A 1 N21 N -0.2307(3) 0.38120(6) 0.26010(16) 0.0332(4) Uani 1 1 d . A . H21 H -0.419(5) 0.3875(8) 0.240(2) 0.040 Uiso 1 1 d . . . C22 C -0.0681(4) 0.39899(8) 0.1712(2) 0.0357(5) Uani 1 1 d . . . O22 O 0.1899(3) 0.39193(7) 0.18909(18) 0.0585(5) Uani 1 1 d . A . C23 C -0.2133(4) 0.42796(9) 0.0507(2) 0.0473(6) Uani 1 1 d . A . H23A H -0.4194 0.4257 0.0497 0.071 Uiso 1 1 calc R . . H23B H -0.1615 0.4106 -0.0307 0.071 Uiso 1 1 calc R . . H23C H -0.1547 0.4667 0.0536 0.071 Uiso 1 1 calc R . . C31 C 0.3856(4) 0.07477(7) 0.19413(17) 0.0297(4) Uani 1 1 d . . . O31 O 0.2253(3) 0.07960(5) 0.29041(14) 0.0432(4) Uani 1 1 d . . . H31 H 0.170(5) 0.1168(9) 0.302(2) 0.052 Uiso 1 1 d . . . O32 O 0.4304(3) 0.11224(5) 0.12188(14) 0.0405(4) Uani 1 1 d . . . C32 C 0.5093(4) 0.01823(8) 0.18831(19) 0.0402(5) Uani 1 1 d . . . H32A H 0.3624 -0.0091 0.2036 0.048 Uiso 1 1 calc R . . H32B H 0.6682 0.0144 0.2627 0.048 Uiso 1 1 calc R . . C33 C 0.6174(4) 0.00456(8) 0.05747(18) 0.0344(5) Uani 1 1 d . . . H33A H 0.7399 0.0350 0.0339 0.041 Uiso 1 1 calc R . . H33B H 0.7358 -0.0291 0.0702 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 N11A 0.025(4) 0.0321(10) 0.0463(14) -0.0038(9) 0.026(2) 0.003(2) C12A 0.045(3) 0.041(3) 0.048(3) -0.011(2) 0.013(3) -0.010(3) C13A 0.033(3) 0.035(3) 0.047(3) -0.005(2) 0.010(2) 0.001(2) C14A 0.0293(16) 0.0243(19) 0.017(3) 0.005(2) 0.015(2) -0.0036(14) C15A 0.038(3) 0.032(3) 0.049(4) -0.007(3) 0.003(2) 0.003(2) C16A 0.043(3) 0.034(3) 0.059(5) -0.002(3) 0.004(3) 0.014(2) N11B 0.025(4) 0.0321(10) 0.0463(14) -0.0038(9) 0.026(2) 0.003(2) C12B 0.059(4) 0.033(3) 0.042(3) -0.016(2) -0.002(3) 0.000(3) C13B 0.050(3) 0.038(3) 0.040(3) -0.004(2) -0.007(2) 0.006(2) C14B 0.0293(16) 0.0243(19) 0.017(3) 0.005(2) 0.015(2) -0.0036(14) C15B 0.043(3) 0.033(3) 0.035(3) -0.010(2) 0.005(2) 0.001(2) C16B 0.051(3) 0.041(3) 0.035(3) 0.000(2) 0.006(2) 0.004(2) C21 0.0417(10) 0.0331(11) 0.0396(11) -0.0067(9) 0.0048(9) 0.0015(8) N21 0.0257(8) 0.0321(9) 0.0420(10) 0.0014(7) 0.0057(7) 0.0053(6) C22 0.0253(9) 0.0384(11) 0.0442(12) -0.0087(9) 0.0077(8) -0.0019(7) O22 0.0234(7) 0.0893(13) 0.0636(11) -0.0007(9) 0.0087(7) 0.0020(7) C23 0.0460(12) 0.0565(14) 0.0406(12) 0.0028(10) 0.0103(10) 0.0015(10) C31 0.0368(9) 0.0281(10) 0.0239(9) -0.0018(8) 0.0028(7) 0.0008(7) O31 0.0606(9) 0.0291(8) 0.0450(9) -0.0023(6) 0.0251(7) 0.0034(6) O32 0.0553(9) 0.0304(7) 0.0379(8) 0.0044(6) 0.0138(7) 0.0051(6) C32 0.0603(13) 0.0307(11) 0.0299(11) 0.0012(8) 0.0071(9) 0.0132(9) C33 0.0371(10) 0.0300(10) 0.0365(11) -0.0017(8) 0.0060(8) 0.0072(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 N11A C12A 1.299(10) . ? N11A C16A 1.376(10) . ? C12A C13A 1.373(7) . ? C12A H12A 0.9500 . ? C13A C14A 1.423(11) . ? C13A H13A 0.9500 . ? C14A C15A 1.348(10) . ? C14A C21 1.482(12) . ? C15A C16A 1.387(7) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? N11B C12B 1.287(9) . ? N11B C16B 1.371(10) . ? C12B C13B 1.385(7) . ? C12B H12B 0.9500 . ? C13B C14B 1.419(10) . ? C13B H13B 0.9500 . ? C14B C15B 1.349(9) . ? C14B C21 1.550(11) . ? C15B C16B 1.380(7) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C21 N21 1.440(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? N21 C22 1.331(2) . ? N21 H21 0.90(2) . ? C22 O22 1.227(2) . ? C22 C23 1.484(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C31 O32 1.201(2) . ? C31 O31 1.316(2) . ? C31 C32 1.498(3) . ? O31 H31 0.95(2) . ? C32 C33 1.512(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C33 1.506(4) 3_655 ? 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 C12A N11A C16A 116.3(9) . . ? N11A C12A C13A 124.4(7) . . ? N11A C12A H12A 117.8 . . ? C13A C12A H12A 117.8 . . ? C12A C13A C14A 117.9(6) . . ? C12A C13A H13A 121.0 . . ? C14A C13A H13A 121.0 . . ? C15A C14A C13A 116.8(9) . . ? C15A C14A C21 120.2(8) . . ? C13A C14A C21 119.2(9) . . ? C14A C15A C16A 119.9(7) . . ? C14A C15A H15A 120.0 . . ? C16A C15A H15A 120.0 . . ? N11A C16A C15A 121.6(6) . . ? N11A C16A H16A 119.2 . . ? C15A C16A H16A 119.2 . . ? C12B N11B C16B 115.7(7) . . ? N11B C12B C13B 124.6(6) . . ? N11B C12B H12B 117.7 . . ? C13B C12B H12B 117.7 . . ? C12B C13B C14B 118.2(6) . . ? C12B C13B H13B 120.9 . . ? C14B C13B H13B 120.9 . . ? C15B C14B C13B 116.3(8) . . ? C15B C14B C21 122.8(7) . . ? C13B C14B C21 118.6(7) . . ? C14B C15B C16B 120.1(6) . . ? C14B C15B H15B 119.9 . . ? C16B C15B H15B 119.9 . . ? N11B C16B C15B 122.3(6) . . ? N11B C16B H16B 118.8 . . ? C15B C16B H16B 118.8 . . ? N21 C21 C14A 109.4(5) . . ? N21 C21 C14B 117.5(4) . . ? N21 C21 H21A 109.8 . . ? C14A C21 H21A 109.8 . . ? C14B C21 H21A 99.1 . . ? N21 C21 H21B 109.8 . . ? C14A C21 H21B 109.8 . . ? C14B C21 H21B 111.6 . . ? H21A C21 H21B 108.2 . . ? C22 N21 C21 121.79(16) . . ? C22 N21 H21 116.2(13) . . ? C21 N21 H21 122.0(13) . . ? O22 C22 N21 121.2(2) . . ? O22 C22 C23 121.89(18) . . ? N21 C22 C23 116.92(16) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O32 C31 O31 123.01(16) . . ? O32 C31 C32 124.61(16) . . ? O31 C31 C32 112.37(15) . . ? C31 O31 H31 112.0(13) . . ? C31 C32 C33 114.68(16) . . ? C31 C32 H32A 108.6 . . ? C33 C32 H32A 108.6 . . ? C31 C32 H32B 108.6 . . ? C33 C32 H32B 108.6 . . ? H32A C32 H32B 107.6 . . ? C33 C33 C32 113.12(17) 3_655 . ? C33 C33 H33A 109.0 3_655 . ? C32 C33 H33A 109.0 . . ? C33 C33 H33B 109.0 3_655 . ? C32 C33 H33B 109.0 . . ? H33A C33 H33B 107.8 . . ? 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 C16A N11A C12A C13A -13.7(13) . . . . ? N11A C12A C13A C14A 14.8(12) . . . . ? C12A C13A C14A C15A -14.5(15) . . . . ? C12A C13A C14A C21 -172.6(7) . . . . ? C13A C14A C15A C16A 14.6(15) . . . . ? C21 C14A C15A C16A 172.5(8) . . . . ? C12A N11A C16A C15A 13.0(13) . . . . ? C14A C15A C16A N11A -14.3(13) . . . . ? C16B N11B C12B C13B 14.3(12) . . . . ? N11B C12B C13B C14B -13.9(12) . . . . ? C12B C13B C14B C15B 12.1(14) . . . . ? C12B C13B C14B C21 175.5(7) . . . . ? C13B C14B C15B C16B -12.6(14) . . . . ? C21 C14B C15B C16B -175.2(7) . . . . ? C12B N11B C16B C15B -14.2(12) . . . . ? C14B C15B C16B N11B 14.1(11) . . . . ? C15A C14A C21 N21 145.4(10) . . . . ? C13A C14A C21 N21 -57.2(12) . . . . ? C15A C14A C21 C14B -76(4) . . . . ? C13A C14A C21 C14B 81(4) . . . . ? C15B C14B C21 N21 161.0(8) . . . . ? C13B C14B C21 N21 -1.2(13) . . . . ? C15B C14B C21 C14A 116(5) . . . . ? C13B C14B C21 C14A -46(3) . . . . ? C14A C21 N21 C22 -76.9(6) . . . . ? C14B C21 N21 C22 -85.3(6) . . . . ? C21 N21 C22 O22 1.3(3) . . . . ? C21 N21 C22 C23 -178.17(17) . . . . ? O32 C31 C32 C33 -19.5(3) . . . . ? O31 C31 C32 C33 162.06(16) . . . . ? C31 C32 C33 C33 -72.4(3) . . . 3_655 ? 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 N21 H21 O22 0.90(2) 1.86(2) 2.759(2) 173.1(19) 1_455 O31 H31 N11A 0.95(2) 1.78(2) 2.731(11) 172(2) . O31 H31 N11B 0.95(2) 1.66(2) 2.610(9) 175(2) . _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.297 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.078 #END data_5 _database_code_depnum_ccdc_archive 'CCDC 624064' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [4-(aminomethyl)pyridine acetate]2, isophthalic acid ; _chemical_name_common '(4-(aminomethyl)pyridine acetate)2, isophthalic acid' _chemical_melting_point ? _chemical_formula_moiety ; (C8 H6 O4) (C8 H10 N2 O)2 ; _chemical_formula_sum 'C24 H26 N4 O6' _chemical_formula_weight 466.49 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 Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 34.784(6) _cell_length_b 57.476(12) _cell_length_c 4.7674(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9531(3) _cell_formula_units_Z 16 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1847 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 20.35 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3936 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16779 _diffrn_reflns_av_R_equivalents 0.2638 _diffrn_reflns_av_sigmaI/netI 0.1727 _diffrn_reflns_limit_h_min -45 _diffrn_reflns_limit_h_max 43 _diffrn_reflns_limit_k_min -72 _diffrn_reflns_limit_k_max 74 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 28.43 _reflns_number_total 3203 _reflns_number_gt 1325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0036(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3203 _refine_ls_number_parameters 311 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1642 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.1904 _refine_ls_wR_factor_gt 0.1559 _refine_ls_goodness_of_fit_ref 0.824 _refine_ls_restrained_S_all 0.823 _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 0.09069(12) 0.37347(8) 0.1194(12) 0.0620(14) Uani 1 1 d . . . C12 C 0.1208(2) 0.37063(11) -0.030(2) 0.117(4) Uani 1 1 d . . . H12 H 0.1345 0.3841 -0.0894 0.140 Uiso 1 1 calc R . . C13 C 0.1348(2) 0.34884(11) -0.111(2) 0.121(4) Uani 1 1 d . . . H13 H 0.1568 0.3479 -0.2292 0.145 Uiso 1 1 calc R . . C14 C 0.11797(14) 0.32976(9) -0.0271(12) 0.0494(13) Uani 1 1 d . . . C15 C 0.0859(2) 0.33235(11) 0.1301(17) 0.086(2) Uani 1 1 d . . . H15 H 0.0723 0.3191 0.1953 0.103 Uiso 1 1 calc R . . C16 C 0.0734(2) 0.35416(11) 0.1940(19) 0.092(3) Uani 1 1 d . . . H16 H 0.0504 0.3555 0.3003 0.111 Uiso 1 1 calc R . . C17 C 0.13109(16) 0.30526(9) -0.1048(14) 0.0653(16) Uani 1 1 d . . . H17A H 0.1269 0.2949 0.0588 0.078 Uiso 1 1 calc R . . H17B H 0.1147 0.2995 -0.2594 0.078 Uiso 1 1 calc R . . N17 N 0.17044(11) 0.30341(8) -0.1893(9) 0.0535(12) Uani 1 1 d . A . H17 H 0.1760 0.3041 -0.3692 0.064 Uiso 1 1 calc R . . C18 C 0.19859(17) 0.30073(11) -0.0067(13) 0.0625(16) Uani 1 1 d D . . O18 O 0.19212(14) 0.30192(10) 0.2536(9) 0.0928(16) Uani 1 1 d . A . C19A C 0.2361(4) 0.2927(6) -0.121(4) 0.055(2) Uiso 0.52(7) 1 d PD A 1 H19A H 0.2432 0.2779 -0.0344 0.083 Uiso 0.52(7) 1 calc PR A 1 H19B H 0.2560 0.3044 -0.0796 0.083 Uiso 0.52(7) 1 calc PR A 1 H19C H 0.2340 0.2907 -0.3246 0.083 Uiso 0.52(7) 1 calc PR A 1 C19B C 0.2394(4) 0.3000(7) -0.101(4) 0.055(2) Uiso 0.48(7) 1 d PD A 2 H19D H 0.2528 0.3139 -0.0349 0.083 Uiso 0.48(7) 1 calc PR A 2 H19E H 0.2402 0.2994 -0.3066 0.083 Uiso 0.48(7) 1 calc PR A 2 H19F H 0.2518 0.2861 -0.0246 0.083 Uiso 0.48(7) 1 calc PR A 2 N21 N 0.23772(14) 0.53130(9) 0.1902(14) 0.0687(15) Uani 1 1 d . . . C22 C 0.2287(2) 0.54633(12) -0.004(3) 0.104(3) Uani 1 1 d . . . H22 H 0.2066 0.5434 -0.1162 0.125 Uiso 1 1 calc R . . C23 C 0.25000(18) 0.56639(13) -0.056(2) 0.111(4) Uani 1 1 d . . . H23 H 0.2420 0.5771 -0.1956 0.133 Uiso 1 1 calc R . . C24 C 0.28261(14) 0.57045(9) 0.0986(14) 0.0542(14) Uani 1 1 d . . . C25 C 0.29279(19) 0.55406(12) 0.2782(19) 0.088(2) Uani 1 1 d . . . H25 H 0.3162 0.5556 0.3795 0.106 Uiso 1 1 calc R . . C26 C 0.2699(2) 0.53481(14) 0.320(2) 0.110(3) Uani 1 1 d . . . H26 H 0.2782 0.5235 0.4522 0.132 Uiso 1 1 calc R . . C27 C 0.30680(15) 0.59183(10) 0.0466(15) 0.0627(16) Uani 1 1 d . . . H27A H 0.3304 0.5909 0.1623 0.075 Uiso 1 1 calc R . . H27B H 0.3147 0.5921 -0.1529 0.075 Uiso 1 1 calc R . . N27 N 0.28657(11) 0.61316(7) 0.1121(10) 0.0467(11) Uani 1 1 d . . . H27 H 0.2849 0.6174 0.2891 0.056 Uiso 1 1 calc R . . C28 C 0.27057(17) 0.62650(11) -0.0782(11) 0.0551(14) Uani 1 1 d . . . O28 O 0.27120(15) 0.62116(9) -0.3325(9) 0.0943(16) Uani 1 1 d . . . C29 C 0.25157(18) 0.64779(10) 0.0177(15) 0.0719(17) Uani 1 1 d . . . H29A H 0.2260 0.6489 -0.0674 0.108 Uiso 1 1 calc R . . H29B H 0.2669 0.6613 -0.0378 0.108 Uiso 1 1 calc R . . H29C H 0.2491 0.6474 0.2224 0.108 Uiso 1 1 calc R . . C31 C 0.10156(13) 0.45156(9) 0.4213(12) 0.0486(14) Uani 1 1 d . . . C37 C 0.10274(14) 0.42948(9) 0.2609(13) 0.0474(13) Uani 1 1 d . . . O31 O 0.07453(9) 0.41500(6) 0.3201(10) 0.0656(12) Uani 1 1 d . . . H31 H 0.0793 0.4019 0.2503 0.079 Uiso 1 1 calc R . . O32 O 0.12819(10) 0.42468(6) 0.0975(10) 0.0603(10) Uani 1 1 d . . . C32 C 0.13043(14) 0.46742(9) 0.3750(13) 0.0542(14) Uani 1 1 d . . . H32 H 0.1499 0.4641 0.2413 0.065 Uiso 1 1 calc R . . C33 C 0.13129(15) 0.48839(8) 0.5233(12) 0.0510(14) Uani 1 1 d . . . C38 C 0.16283(15) 0.50586(10) 0.4830(14) 0.0569(16) Uani 1 1 d . . . O33 O 0.18831(11) 0.49903(7) 0.3000(13) 0.0860(16) Uani 1 1 d . . . H33 H 0.2062 0.5088 0.2918 0.103 Uiso 1 1 calc R . . O34 O 0.16420(11) 0.52377(7) 0.6064(10) 0.0687(12) Uani 1 1 d . . . C34 C 0.10241(16) 0.49342(10) 0.7080(13) 0.0610(16) Uani 1 1 d . . . H34 H 0.1022 0.5079 0.8042 0.073 Uiso 1 1 calc R . . C35 C 0.0732(2) 0.47717(11) 0.7550(16) 0.0763(19) Uani 1 1 d . . . H35 H 0.0535 0.4805 0.8871 0.092 Uiso 1 1 calc R . . C36 C 0.07280(16) 0.45660(10) 0.6120(14) 0.0592(15) Uani 1 1 d . . . H36 H 0.0527 0.4457 0.6436 0.071 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 0.047(2) 0.064(3) 0.075(3) -0.002(3) 0.017(3) -0.007(2) C12 0.116(6) 0.064(4) 0.170(9) -0.022(5) 0.096(7) -0.030(4) C13 0.126(6) 0.068(4) 0.170(9) -0.035(5) 0.117(7) -0.026(4) C14 0.046(3) 0.058(3) 0.044(3) -0.011(3) 0.009(3) -0.007(3) C15 0.107(5) 0.060(4) 0.092(5) 0.005(4) 0.070(5) 0.005(4) C16 0.100(5) 0.052(4) 0.124(7) -0.002(4) 0.077(5) 0.004(3) C17 0.064(3) 0.072(4) 0.059(4) -0.023(3) 0.011(3) -0.003(3) N17 0.053(3) 0.078(3) 0.029(2) -0.008(2) 0.009(2) 0.009(2) C18 0.070(4) 0.088(4) 0.030(3) 0.003(3) 0.009(3) -0.010(3) O18 0.110(4) 0.142(4) 0.026(2) 0.000(2) 0.009(2) -0.028(3) N21 0.058(3) 0.055(3) 0.093(4) -0.021(3) 0.007(3) -0.009(3) C22 0.067(4) 0.083(5) 0.161(9) 0.004(6) -0.040(6) -0.024(4) C23 0.069(4) 0.095(5) 0.169(11) 0.032(6) -0.048(6) -0.036(4) C24 0.044(3) 0.057(3) 0.062(4) -0.021(3) 0.006(3) -0.013(3) C25 0.085(4) 0.092(5) 0.087(5) 0.021(5) -0.030(5) -0.044(4) C26 0.109(6) 0.110(6) 0.110(7) 0.039(6) -0.046(6) -0.058(5) C27 0.054(3) 0.072(4) 0.062(4) -0.012(3) 0.007(3) -0.013(3) N27 0.057(2) 0.048(2) 0.035(2) -0.008(2) 0.003(2) -0.008(2) C28 0.067(3) 0.070(4) 0.029(3) -0.003(3) 0.001(3) -0.013(3) O28 0.120(4) 0.135(4) 0.028(2) -0.012(3) 0.000(3) -0.013(3) C29 0.084(4) 0.083(4) 0.048(3) 0.014(4) -0.003(4) 0.001(4) C31 0.036(3) 0.057(3) 0.053(3) 0.009(3) -0.009(3) -0.003(2) C37 0.036(3) 0.048(3) 0.059(3) 0.003(3) -0.003(3) -0.002(2) O31 0.050(2) 0.055(2) 0.092(3) -0.011(2) 0.013(2) -0.0134(17) O32 0.0459(19) 0.054(2) 0.081(3) -0.009(2) 0.015(2) -0.0079(17) C32 0.045(3) 0.059(3) 0.059(4) 0.006(3) -0.007(3) -0.003(3) C33 0.050(3) 0.048(3) 0.055(3) 0.006(3) -0.017(3) -0.002(3) C38 0.045(3) 0.056(4) 0.070(4) 0.009(3) -0.017(3) 0.002(3) O33 0.065(2) 0.069(3) 0.125(5) -0.025(3) 0.020(3) -0.027(2) O34 0.078(3) 0.052(2) 0.077(3) -0.006(2) -0.014(3) -0.014(2) C34 0.072(4) 0.055(3) 0.055(4) -0.001(3) 0.001(3) -0.008(3) C35 0.092(5) 0.063(4) 0.074(4) -0.011(4) 0.024(4) -0.016(3) C36 0.058(3) 0.066(4) 0.053(3) 0.003(3) 0.005(3) -0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.278(8) . ? N11 C16 1.312(8) . ? C12 C13 1.398(9) . ? C12 H12 0.9500 . ? C13 C14 1.306(8) . ? C13 H13 0.9500 . ? C14 C15 1.351(7) . ? C14 C17 1.526(7) . ? C15 C16 1.362(8) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N17 1.431(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? N17 C18 1.320(7) . ? N17 H17 0.8800 . ? C18 O18 1.263(8) . ? C18 C19A 1.488(12) . ? C18 C19B 1.488(13) . ? C19A H19A 0.9800 . ? C19A H19B 0.9800 . ? C19A H19C 0.9800 . ? C19B H19D 0.9800 . ? C19B H19E 0.9800 . ? C19B H19F 0.9800 . ? N21 C26 1.296(9) . ? N21 C22 1.306(11) . ? C22 C23 1.391(9) . ? C22 H22 0.9500 . ? C23 C24 1.372(9) . ? C23 H23 0.9500 . ? C24 C25 1.321(9) . ? C24 C27 1.510(7) . ? C25 C26 1.378(9) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 N27 1.448(7) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? N27 C28 1.312(7) . ? N27 H27 0.8800 . ? C28 O28 1.251(7) . ? C28 C29 1.463(8) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C31 C32 1.374(7) . ? C31 C36 1.382(8) . ? C31 C37 1.482(7) . ? C37 O32 1.211(6) . ? C37 O31 1.317(6) . ? O31 H31 0.8400 . ? C32 C33 1.397(7) . ? C32 H32 0.9500 . ? C33 C34 1.367(8) . ? C33 C38 1.500(8) . ? C38 O34 1.187(7) . ? C38 O33 1.304(7) . ? O33 H33 0.8400 . ? C34 C35 1.399(8) . ? C34 H34 0.9500 . ? C35 C36 1.365(8) . ? C35 H35 0.9500 . ? C36 H36 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 C12 N11 C16 114.8(6) . . ? N11 C12 C13 123.7(6) . . ? N11 C12 H12 118.2 . . ? C13 C12 H12 118.2 . . ? C14 C13 C12 120.7(6) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 116.6(6) . . ? C13 C14 C17 124.5(5) . . ? C15 C14 C17 118.9(5) . . ? C14 C15 C16 119.4(6) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? N11 C16 C15 124.7(6) . . ? N11 C16 H16 117.6 . . ? C15 C16 H16 117.6 . . ? N17 C17 C14 115.0(4) . . ? N17 C17 H17A 108.5 . . ? C14 C17 H17A 108.5 . . ? N17 C17 H17B 108.5 . . ? C14 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C18 N17 C17 122.2(5) . . ? C18 N17 H17 118.9 . . ? C17 N17 H17 118.9 . . ? O18 C18 N17 120.6(6) . . ? O18 C18 C19A 122.2(9) . . ? N17 C18 C19A 116.5(9) . . ? O18 C18 C19B 118.0(10) . . ? N17 C18 C19B 120.7(9) . . ? C18 C19A H19A 109.5 . . ? C18 C19A H19B 109.5 . . ? C18 C19A H19C 109.5 . . ? C18 C19B H19D 109.5 . . ? C18 C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C18 C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? C26 N21 C22 116.4(6) . . ? N21 C22 C23 123.1(7) . . ? N21 C22 H22 118.5 . . ? C23 C22 H22 118.5 . . ? C24 C23 C22 119.1(8) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C25 C24 C23 116.6(6) . . ? C25 C24 C27 122.5(5) . . ? C23 C24 C27 120.7(6) . . ? C24 C25 C26 120.8(7) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? N21 C26 C25 123.6(8) . . ? N21 C26 H26 118.2 . . ? C25 C26 H26 118.2 . . ? N27 C27 C24 112.5(4) . . ? N27 C27 H27A 109.1 . . ? C24 C27 H27A 109.1 . . ? N27 C27 H27B 109.1 . . ? C24 C27 H27B 109.1 . . ? H27A C27 H27B 107.8 . . ? C28 N27 C27 123.5(5) . . ? C28 N27 H27 118.2 . . ? C27 N27 H27 118.2 . . ? O28 C28 N27 121.3(6) . . ? O28 C28 C29 121.0(6) . . ? N27 C28 C29 117.7(5) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C32 C31 C36 119.7(5) . . ? C32 C31 C37 117.7(5) . . ? C36 C31 C37 122.6(5) . . ? O32 C37 O31 122.6(5) . . ? O32 C37 C31 123.2(4) . . ? O31 C37 C31 114.2(5) . . ? C37 O31 H31 109.5 . . ? C31 C32 C33 120.4(6) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C34 C33 C32 119.5(5) . . ? C34 C33 C38 118.6(5) . . ? C32 C33 C38 121.9(6) . . ? O34 C38 O33 124.4(5) . . ? O34 C38 C33 123.1(6) . . ? O33 C38 C33 112.4(6) . . ? C38 O33 H33 109.5 . . ? C33 C34 C35 119.8(6) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C36 C35 C34 120.3(6) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C35 C36 C31 120.2(5) . . ? C35 C36 H36 119.9 . . ? C31 C36 H36 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 0.1(14) . . . . ? N11 C12 C13 C14 -2.6(17) . . . . ? C12 C13 C14 C15 2.7(14) . . . . ? C12 C13 C14 C17 180.0(8) . . . . ? C13 C14 C15 C16 -0.8(12) . . . . ? C17 C14 C15 C16 -178.2(7) . . . . ? C12 N11 C16 C15 2.0(13) . . . . ? C14 C15 C16 N11 -1.7(14) . . . . ? C13 C14 C17 N17 22.1(10) . . . . ? C15 C14 C17 N17 -160.8(6) . . . . ? C14 C17 N17 C18 85.8(7) . . . . ? C17 N17 C18 O18 -6.8(10) . . . . ? C17 N17 C18 C19A 164.1(15) . . . . ? C17 N17 C18 C19B -177.2(18) . . . . ? C26 N21 C22 C23 -6.1(14) . . . . ? N21 C22 C23 C24 1.9(15) . . . . ? C22 C23 C24 C25 3.5(12) . . . . ? C22 C23 C24 C27 179.1(8) . . . . ? C23 C24 C25 C26 -4.6(12) . . . . ? C27 C24 C25 C26 179.9(8) . . . . ? C22 N21 C26 C25 5.0(14) . . . . ? C24 C25 C26 N21 0.4(15) . . . . ? C25 C24 C27 N27 -119.9(7) . . . . ? C23 C24 C27 N27 64.8(8) . . . . ? C24 C27 N27 C28 -100.6(7) . . . . ? C27 N27 C28 O28 1.6(9) . . . . ? C27 N27 C28 C29 -179.0(5) . . . . ? C32 C31 C37 O32 1.7(8) . . . . ? C36 C31 C37 O32 -178.5(5) . . . . ? C32 C31 C37 O31 178.9(5) . . . . ? C36 C31 C37 O31 -1.3(7) . . . . ? C36 C31 C32 C33 1.2(8) . . . . ? C37 C31 C32 C33 -178.9(5) . . . . ? C31 C32 C33 C34 -2.3(8) . . . . ? C31 C32 C33 C38 178.6(5) . . . . ? C34 C33 C38 O34 0.9(8) . . . . ? C32 C33 C38 O34 -180.0(5) . . . . ? C34 C33 C38 O33 -179.5(5) . . . . ? C32 C33 C38 O33 -0.4(7) . . . . ? C32 C33 C34 C35 2.5(8) . . . . ? C38 C33 C34 C35 -178.4(6) . . . . ? C33 C34 C35 C36 -1.7(10) . . . . ? C34 C35 C36 C31 0.6(10) . . . . ? C32 C31 C36 C35 -0.4(9) . . . . ? C37 C31 C36 C35 179.8(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O31 H31 N11 0.84 1.79 2.632(6) 176.9 . O33 H33 N21 0.84 1.76 2.582(6) 164.7 . N17 H17 O18 0.88 1.89 2.762(6) 172.3 1_554 N27 H27 O28 0.88 1.88 2.740(6) 165.7 1_556 _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.280 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.076 #END data_6 _database_code_depnum_ccdc_archive 'CCDC 624065' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(4-pyridylmethyl)acetamide, 5-nitroisophthalic acid hydrate ; _chemical_name_common 'N-(4-pyridylmethyl)acetamide, 5-nitroisophthalic acid hydrate' _chemical_melting_point ? _chemical_formula_moiety ; (C8 H10 N2 O) (C8 H5 N O6) (H2 O) ; _chemical_formula_sum 'C16 H17 N3 O8' _chemical_formula_weight 379.33 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 18.5868(12) _cell_length_b 6.8213(5) _cell_length_c 14.0335(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.406(4) _cell_angle_gamma 90.00 _cell_volume 1730.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4290 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.65 _exptl_crystal_description prism _exptl_crystal_colour amber _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21273 _diffrn_reflns_av_R_equivalents 0.1247 _diffrn_reflns_av_sigmaI/netI 0.0828 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4088 _reflns_number_gt 2360 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.025(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4088 _refine_ls_number_parameters 267 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1282 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.2112 _refine_ls_wR_factor_gt 0.1736 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 O1A O 0.42073(14) -0.0022(4) 0.4079(2) 0.0658(8) Uani 0.50 1 d PD A 1 H1A H 0.475(3) 0.025(13) 0.458(6) 0.079 Uiso 0.50 1 d PD B 1 H1B H 0.429(4) -0.134(8) 0.364(5) 0.079 Uiso 0.50 1 d PD C 1 O1B O 0.42073(14) -0.0022(4) 0.4079(2) 0.0658(8) Uani 0.50 1 d PD D 2 H1C H 0.406(4) 0.036(12) 0.330(3) 0.079 Uiso 0.50 1 d PD E 2 H1D H 0.480(2) -0.006(15) 0.438(5) 0.079 Uiso 0.50 1 d PD F 2 N11 N 0.24952(13) 0.0096(4) 0.56018(16) 0.0342(6) Uani 1 1 d . . . H11 H 0.2167(16) 0.016(4) 0.485(2) 0.041 Uiso 1 1 d . . . C12 C 0.31882(17) 0.0730(4) 0.5803(2) 0.0378(7) Uani 1 1 d . . . H12 H 0.3403 0.1146 0.5285 0.045 Uiso 1 1 calc R . . C13 C 0.36005(15) 0.0790(4) 0.67583(19) 0.0330(6) Uani 1 1 d . . . H13 H 0.4095 0.1257 0.6902 0.040 Uiso 1 1 calc R . . C14 C 0.32808(14) 0.0159(4) 0.75024(18) 0.0269(6) Uani 1 1 d . . . C15 C 0.25602(14) -0.0516(4) 0.7263(2) 0.0306(6) Uani 1 1 d . . . H15 H 0.2335 -0.0981 0.7762 0.037 Uiso 1 1 calc R . . C16 C 0.21710(15) -0.0515(4) 0.6305(2) 0.0337(7) Uani 1 1 d . . . H16 H 0.1672 -0.0947 0.6141 0.040 Uiso 1 1 calc R . . C17 C 0.36851(14) 0.0217(4) 0.85650(19) 0.0323(6) Uani 1 1 d . . . H17A H 0.3395 0.1021 0.8928 0.039 Uiso 1 1 calc R . . H17B H 0.3708 -0.1132 0.8832 0.039 Uiso 1 1 calc R . . N17 N 0.44251(13) 0.0992(4) 0.87467(16) 0.0341(6) Uani 1 1 d . . . H17 H 0.4498(16) 0.225(5) 0.887(2) 0.041 Uiso 1 1 d . . . C18 C 0.50041(15) -0.0088(4) 0.8665(2) 0.0339(7) Uani 1 1 d . . . O18 O 0.49421(11) -0.1835(3) 0.84541(16) 0.0444(6) Uani 1 1 d . . . C19 C 0.57259(16) 0.0948(5) 0.8818(2) 0.0458(8) Uani 1 1 d . . . H19A H 0.5679 0.2262 0.9079 0.069 Uiso 1 1 calc R . . H19B H 0.5871 0.1057 0.8192 0.069 Uiso 1 1 calc R . . H19C H 0.6103 0.0208 0.9283 0.069 Uiso 1 1 calc R . . C21 C 0.16033(14) 0.1038(4) 0.21147(18) 0.0255(6) Uani 1 1 d . . . C27 C 0.20538(14) 0.0652(4) 0.31339(19) 0.0287(6) Uani 1 1 d . . . O21 O 0.27270(11) 0.0482(3) 0.32727(15) 0.0464(6) Uani 1 1 d . . . O22 O 0.16942(10) 0.0540(3) 0.38026(13) 0.0354(5) Uani 1 1 d . . . C22 C 0.09227(13) 0.1949(4) 0.19435(17) 0.0270(6) Uani 1 1 d . . . H22 H 0.0732 0.2361 0.2483 0.032 Uiso 1 1 calc R . . C23 C 0.05109(13) 0.2276(4) 0.09981(17) 0.0256(6) Uani 1 1 d . . . C28 C -0.02113(14) 0.3279(4) 0.07984(18) 0.0286(6) Uani 1 1 d . . . O23 O -0.03611(11) 0.4104(3) 0.15759(14) 0.0394(5) Uani 1 1 d . . . H23 H -0.0791(19) 0.468(5) 0.150(3) 0.047 Uiso 1 1 d . . . O24 O -0.06280(10) 0.3319(3) -0.00060(13) 0.0346(5) Uani 1 1 d . . . C24 C 0.07765(13) 0.1617(4) 0.02047(17) 0.0275(6) Uani 1 1 d . . . H24 H 0.0495 0.1787 -0.0447 0.033 Uiso 1 1 calc R . . C25 C 0.14529(14) 0.0718(4) 0.03870(18) 0.0276(6) Uani 1 1 d . . . N25 N 0.17360(13) -0.0013(4) -0.04348(16) 0.0353(6) Uani 1 1 d . . . O25 O 0.13033(12) -0.0099(3) -0.12399(14) 0.0439(6) Uani 1 1 d . . . O26 O 0.23785(12) -0.0526(4) -0.02829(16) 0.0558(7) Uani 1 1 d . . . C26 C 0.18852(14) 0.0456(4) 0.13253(19) 0.0271(6) Uani 1 1 d . . . H26 H 0.2364 -0.0110 0.1426 0.032 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 O1A 0.0580(16) 0.0528(16) 0.086(2) 0.0028(14) 0.0147(15) 0.0030(12) O1B 0.0580(16) 0.0528(16) 0.086(2) 0.0028(14) 0.0147(15) 0.0030(12) N11 0.0425(14) 0.0360(13) 0.0194(11) 0.0001(10) -0.0029(10) 0.0067(10) C12 0.0435(17) 0.0467(18) 0.0232(14) 0.0058(12) 0.0077(12) 0.0023(13) C13 0.0284(14) 0.0456(17) 0.0235(13) 0.0037(12) 0.0029(11) -0.0014(12) C14 0.0278(13) 0.0299(14) 0.0218(13) 0.0003(11) 0.0031(10) 0.0054(10) C15 0.0295(14) 0.0371(16) 0.0241(13) -0.0015(11) 0.0041(11) 0.0025(11) C16 0.0299(14) 0.0380(16) 0.0288(14) -0.0041(12) -0.0019(11) 0.0009(11) C17 0.0273(13) 0.0452(17) 0.0212(13) -0.0011(12) -0.0011(11) 0.0042(12) N17 0.0329(13) 0.0368(13) 0.0276(12) -0.0021(11) -0.0032(9) -0.0001(10) C18 0.0322(14) 0.0445(18) 0.0221(13) 0.0062(12) 0.0001(11) -0.0003(12) O18 0.0380(11) 0.0403(13) 0.0569(14) -0.0026(10) 0.0150(10) -0.0011(9) C19 0.0327(16) 0.060(2) 0.0393(17) 0.0084(15) -0.0029(13) -0.0068(14) C21 0.0252(12) 0.0299(14) 0.0195(12) 0.0015(11) 0.0016(10) -0.0039(10) C27 0.0282(14) 0.0344(15) 0.0223(13) 0.0024(11) 0.0038(11) -0.0015(11) O21 0.0276(11) 0.0776(17) 0.0306(11) 0.0082(10) -0.0003(8) 0.0006(10) O22 0.0302(10) 0.0553(14) 0.0181(9) 0.0051(8) 0.0003(8) -0.0023(8) C22 0.0276(13) 0.0341(14) 0.0192(12) -0.0008(11) 0.0050(10) -0.0030(11) C23 0.0266(12) 0.0291(14) 0.0192(12) -0.0001(10) 0.0017(10) -0.0015(10) C28 0.0307(13) 0.0338(15) 0.0204(12) 0.0011(11) 0.0041(10) -0.0032(11) O23 0.0309(11) 0.0581(14) 0.0264(10) -0.0060(9) 0.0010(8) 0.0127(9) O24 0.0315(10) 0.0456(12) 0.0220(9) 0.0009(8) -0.0035(8) 0.0044(8) C24 0.0322(14) 0.0321(14) 0.0164(11) 0.0015(10) 0.0023(10) -0.0028(11) C25 0.0330(14) 0.0329(15) 0.0182(12) -0.0012(10) 0.0089(10) -0.0028(11) N25 0.0407(14) 0.0424(14) 0.0253(12) 0.0026(10) 0.0127(11) 0.0018(11) O25 0.0540(13) 0.0591(14) 0.0178(10) -0.0017(9) 0.0068(9) 0.0023(10) O26 0.0409(13) 0.0903(19) 0.0391(13) -0.0036(12) 0.0154(10) 0.0179(12) C26 0.0257(13) 0.0317(14) 0.0234(13) 0.0016(11) 0.0049(10) -0.0007(10) _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 O1A H1A 1.11(3) . ? O1A H1B 1.12(4) . ? O1A H1C 1.09(4) . ? O1A H1D 1.08(4) . ? N11 C12 1.326(4) . ? N11 C16 1.336(4) . ? N11 H11 1.09(3) . ? C12 C13 1.382(4) . ? C12 H12 0.9500 . ? C13 C14 1.384(4) . ? C13 H13 0.9500 . ? C14 C15 1.382(4) . ? C14 C17 1.507(3) . ? C15 C16 1.371(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N17 1.440(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? N17 C18 1.331(4) . ? N17 H17 0.88(3) . ? C18 O18 1.227(3) . ? C18 C19 1.487(4) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C21 C22 1.380(4) . ? C21 C26 1.389(4) . ? C21 C27 1.504(3) . ? C27 O21 1.226(3) . ? C27 O22 1.274(3) . ? C22 C23 1.387(3) . ? C22 H22 0.9500 . ? C23 C24 1.393(3) . ? C23 C28 1.474(4) . ? C28 O24 1.212(3) . ? C28 O23 1.314(3) . ? O23 H23 0.87(3) . ? C24 C25 1.368(4) . ? C24 H24 0.9500 . ? C25 C26 1.386(4) . ? C25 N25 1.462(3) . ? N25 O26 1.215(3) . ? N25 O25 1.227(3) . ? C26 H26 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 H1A O1A H1B 106(2) . . ? H1A O1A H1C 125(8) . . ? H1B O1A H1C 71(5) . . ? H1A O1A H1D 20(6) . . ? H1B O1A H1D 87(6) . . ? H1C O1A H1D 113(3) . . ? C12 N11 C16 121.8(2) . . ? C12 N11 H11 119.4(16) . . ? C16 N11 H11 118.7(16) . . ? N11 C12 C13 120.6(3) . . ? N11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C14 119.0(3) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C15 C14 C13 118.8(2) . . ? C15 C14 C17 118.8(2) . . ? C13 C14 C17 122.4(2) . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? N11 C16 C15 119.9(3) . . ? N11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? N17 C17 C14 114.9(2) . . ? N17 C17 H17A 108.5 . . ? C14 C17 H17A 108.5 . . ? N17 C17 H17B 108.5 . . ? C14 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C18 N17 C17 122.7(3) . . ? C18 N17 H17 118(2) . . ? C17 N17 H17 119.4(19) . . ? O18 C18 N17 121.7(3) . . ? O18 C18 C19 121.8(3) . . ? N17 C18 C19 116.4(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C21 C26 119.4(2) . . ? C22 C21 C27 122.0(2) . . ? C26 C21 C27 118.6(2) . . ? O21 C27 O22 124.6(2) . . ? O21 C27 C21 119.4(2) . . ? O22 C27 C21 116.1(2) . . ? C21 C22 C23 121.3(2) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C22 C23 C24 119.6(2) . . ? C22 C23 C28 122.2(2) . . ? C24 C23 C28 118.3(2) . . ? O24 C28 O23 123.4(2) . . ? O24 C28 C23 123.0(2) . . ? O23 C28 C23 113.6(2) . . ? C28 O23 H23 117(2) . . ? C25 C24 C23 118.4(2) . . ? C25 C24 H24 120.8 . . ? C23 C24 H24 120.8 . . ? C24 C25 C26 122.7(2) . . ? C24 C25 N25 119.2(2) . . ? C26 C25 N25 118.0(2) . . ? O26 N25 O25 123.7(2) . . ? O26 N25 C25 118.6(2) . . ? O25 N25 C25 117.6(2) . . ? C25 C26 C21 118.6(2) . . ? C25 C26 H26 120.7 . . ? C21 C26 H26 120.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 -0.4(4) . . . . ? N11 C12 C13 C14 0.7(4) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? C12 C13 C14 C17 -178.6(3) . . . . ? C13 C14 C15 C16 -1.3(4) . . . . ? C17 C14 C15 C16 177.6(2) . . . . ? C12 N11 C16 C15 -0.8(4) . . . . ? C14 C15 C16 N11 1.6(4) . . . . ? C15 C14 C17 N17 -178.3(2) . . . . ? C13 C14 C17 N17 0.5(4) . . . . ? C14 C17 N17 C18 -82.5(3) . . . . ? C17 N17 C18 O18 -2.1(4) . . . . ? C17 N17 C18 C19 176.5(2) . . . . ? C22 C21 C27 O21 -155.2(3) . . . . ? C26 C21 C27 O21 24.8(4) . . . . ? C22 C21 C27 O22 24.2(4) . . . . ? C26 C21 C27 O22 -155.8(2) . . . . ? C26 C21 C22 C23 0.7(4) . . . . ? C27 C21 C22 C23 -179.3(2) . . . . ? C21 C22 C23 C24 2.1(4) . . . . ? C21 C22 C23 C28 -178.9(2) . . . . ? C22 C23 C28 O24 -168.6(2) . . . . ? C24 C23 C28 O24 10.5(4) . . . . ? C22 C23 C28 O23 10.8(4) . . . . ? C24 C23 C28 O23 -170.2(2) . . . . ? C22 C23 C24 C25 -2.1(4) . . . . ? C28 C23 C24 C25 178.8(2) . . . . ? C23 C24 C25 C26 -0.6(4) . . . . ? C23 C24 C25 N25 179.0(2) . . . . ? C24 C25 N25 O26 168.6(3) . . . . ? C26 C25 N25 O26 -11.8(4) . . . . ? C24 C25 N25 O25 -12.4(4) . . . . ? C26 C25 N25 O25 167.2(2) . . . . ? C24 C25 C26 C21 3.4(4) . . . . ? N25 C25 C26 C21 -176.2(2) . . . . ? C22 C21 C26 C25 -3.4(4) . . . . ? C27 C21 C26 C25 176.6(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 O1A H1A O1A 1.11(3) 2.37(4) 3.440(6) 162(8) 3_656 O1A H1B O18 1.12(4) 1.80(5) 2.790(3) 145(5) 4 O1B H1C O21 1.09(4) 2.48(7) 2.743(3) 92(4) . O1B H1D O18 1.08(4) 2.53(9) 2.790(3) 92(5) 4 N11 H11 O22 1.09(3) 1.55(3) 2.635(3) 173(3) . N17 H17 O1A 0.88(3) 2.01(3) 2.833(4) 156(3) 4_566 O23 H23 O22 0.87(3) 1.74(3) 2.602(3) 171(3) 2 _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.637 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.087 #END data_7 _database_code_depnum_ccdc_archive 'CCDC 624066' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(4-pyridyl)acetamide, glutaric acid ; _chemical_name_common 'N-(4-pyridyl)acetamide, glutaric acid' _chemical_melting_point ? _chemical_formula_moiety ; (C7 H8 N2 O) (C5 H8 O4) ; _chemical_formula_sum 'C12 H16 N2 O5' _chemical_formula_weight 268.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1730(8) _cell_length_b 7.6117(8) _cell_length_c 11.9194(13) _cell_angle_alpha 80.462(7) _cell_angle_beta 75.807(7) _cell_angle_gamma 87.896(7) _cell_volume 622.19(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1663 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.10 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3381 _diffrn_reflns_av_R_equivalents 0.0867 _diffrn_reflns_av_sigmaI/netI 0.0695 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2213 _reflns_number_gt 1710 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2213 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1483 _refine_ls_wR_factor_gt 0.1396 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.4933(2) 0.5584(2) 0.64876(15) 0.0246(4) Uani 1 1 d . . . H11 H 0.419(4) 0.482(3) 0.704(2) 0.030 Uiso 1 1 d . . . C12 C 0.6838(3) 0.5540(3) 0.63750(19) 0.0275(5) Uani 1 1 d . . . H12 H 0.7359 0.4726 0.6912 0.033 Uiso 1 1 calc R . . C13 C 0.8041(3) 0.6646(3) 0.55018(19) 0.0268(5) Uani 1 1 d . . . H13 H 0.9389 0.6613 0.5435 0.032 Uiso 1 1 calc R . . C14 C 0.7277(3) 0.7820(2) 0.47129(17) 0.0223(4) Uani 1 1 d . . . N14 N 0.8340(2) 0.8987(2) 0.37911(16) 0.0241(4) Uani 1 1 d . . . H14 H 0.772(3) 0.955(3) 0.332(2) 0.029 Uiso 1 1 d . . . C15 C 0.5277(3) 0.7822(2) 0.48436(18) 0.0236(5) Uani 1 1 d . . . H15 H 0.4715 0.8599 0.4309 0.028 Uiso 1 1 calc R . . C16 C 0.4151(3) 0.6702(2) 0.57414(18) 0.0247(5) Uani 1 1 d . . . H16 H 0.2796 0.6715 0.5840 0.030 Uiso 1 1 calc R . . C17 C 1.0280(3) 0.9336(3) 0.35399(19) 0.0263(5) Uani 1 1 d . . . O17 O 1.1326(2) 0.8598(2) 0.41218(15) 0.0402(4) Uani 1 1 d . . . C18 C 1.0970(3) 1.0728(3) 0.2482(2) 0.0327(5) Uani 1 1 d . . . H18A H 1.2313 1.1028 0.2417 0.049 Uiso 1 1 calc R . . H18B H 1.0175 1.1797 0.2560 0.049 Uiso 1 1 calc R . . H18C H 1.0872 1.0268 0.1778 0.049 Uiso 1 1 calc R . . C21 C 0.0945(3) 0.3779(3) 0.82751(19) 0.0255(5) Uani 1 1 d . . . O21 O 0.27151(18) 0.33236(18) 0.82203(13) 0.0294(4) Uani 1 1 d . . . O22 O 0.0436(2) 0.4848(2) 0.75337(14) 0.0376(4) Uani 1 1 d . . . C22 C -0.0505(3) 0.2927(3) 0.93779(19) 0.0266(5) Uani 1 1 d . . . H22A H -0.0226 0.1638 0.9527 0.032 Uiso 1 1 calc R . . H22B H -0.0321 0.3448 1.0051 0.032 Uiso 1 1 calc R . . C23 C -0.2587(3) 0.3153(3) 0.93248(18) 0.0249(5) Uani 1 1 d . . . H23A H -0.2872 0.2356 0.8810 0.030 Uiso 1 1 calc R . . H23B H -0.2790 0.4395 0.8971 0.030 Uiso 1 1 calc R . . C24 C -0.3987(3) 0.2737(3) 1.05323(18) 0.0266(5) Uani 1 1 d . . . H24A H -0.3871 0.3684 1.0989 0.032 Uiso 1 1 calc R . . H24B H -0.5315 0.2775 1.0425 0.032 Uiso 1 1 calc R . . C25 C -0.3688(2) 0.0968(3) 1.12332(19) 0.0231(5) Uani 1 1 d . . . O25 O -0.3288(2) -0.03367(19) 1.06245(13) 0.0300(4) Uani 1 1 d . . . H25 H -0.309(3) -0.140(3) 1.114(2) 0.036 Uiso 1 1 d . . . O26 O -0.3834(2) 0.0794(2) 1.22784(15) 0.0380(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 0.0243(9) 0.0260(8) 0.0214(11) -0.0021(7) -0.0026(7) -0.0017(6) C12 0.0285(10) 0.0296(10) 0.0256(13) -0.0018(8) -0.0116(8) 0.0058(8) C13 0.0225(10) 0.0326(10) 0.0258(13) -0.0014(8) -0.0097(8) 0.0034(8) C14 0.0207(9) 0.0259(9) 0.0209(12) -0.0051(7) -0.0057(7) 0.0021(7) N14 0.0195(8) 0.0308(9) 0.0218(11) 0.0010(7) -0.0083(7) 0.0026(6) C15 0.0210(9) 0.0272(10) 0.0243(13) -0.0052(8) -0.0086(8) 0.0043(7) C16 0.0189(9) 0.0286(10) 0.0283(13) -0.0085(8) -0.0067(8) 0.0022(7) C17 0.0209(9) 0.0305(10) 0.0270(13) -0.0048(8) -0.0051(8) 0.0028(7) O17 0.0208(7) 0.0497(10) 0.0473(12) 0.0081(8) -0.0135(7) -0.0008(6) C18 0.0252(10) 0.0394(12) 0.0302(14) -0.0031(9) -0.0020(8) 0.0011(8) C21 0.0231(9) 0.0235(9) 0.0286(13) -0.0019(8) -0.0058(8) 0.0016(7) O21 0.0218(7) 0.0289(7) 0.0334(10) 0.0061(6) -0.0067(6) 0.0011(5) O22 0.0276(8) 0.0416(9) 0.0347(10) 0.0142(7) -0.0050(6) 0.0047(6) C22 0.0252(10) 0.0267(10) 0.0264(13) 0.0020(8) -0.0077(8) 0.0014(7) C23 0.0243(10) 0.0253(10) 0.0228(13) 0.0025(8) -0.0062(8) 0.0050(7) C24 0.0245(10) 0.0276(10) 0.0254(13) -0.0022(8) -0.0042(8) 0.0061(7) C25 0.0133(8) 0.0308(10) 0.0229(14) 0.0004(8) -0.0036(7) 0.0017(7) O25 0.0372(8) 0.0272(8) 0.0250(10) 0.0005(6) -0.0106(6) 0.0060(6) O26 0.0471(10) 0.0454(10) 0.0212(11) -0.0024(7) -0.0120(7) 0.0138(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 C16 1.337(3) . ? N11 C12 1.340(3) . ? N11 H11 0.88(3) . ? C12 C13 1.364(3) . ? C12 H12 0.9500 . ? C13 C14 1.386(3) . ? C13 H13 0.9500 . ? C14 N14 1.376(3) . ? C14 C15 1.404(2) . ? N14 C17 1.376(2) . ? N14 H14 0.86(2) . ? C15 C16 1.359(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.206(2) . ? C17 C18 1.499(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C21 O22 1.214(2) . ? C21 O21 1.293(2) . ? C21 C22 1.525(3) . ? C22 C23 1.513(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.531(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.500(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 O26 1.210(3) . ? C25 O25 1.308(3) . ? O25 H25 0.96(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 121.08(18) . . ? C16 N11 H11 119.5(15) . . ? C12 N11 H11 119.3(15) . . ? N11 C12 C13 121.06(19) . . ? N11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C12 C13 C14 119.28(17) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? N14 C14 C13 124.70(17) . . ? N14 C14 C15 116.87(18) . . ? C13 C14 C15 118.42(18) . . ? C17 N14 C14 127.65(17) . . ? C17 N14 H14 116.5(15) . . ? C14 N14 H14 115.8(15) . . ? C16 C15 C14 119.49(19) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? N11 C16 C15 120.66(17) . . ? N11 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? O17 C17 N14 123.07(18) . . ? O17 C17 C18 123.14(18) . . ? N14 C17 C18 113.79(17) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O22 C21 O21 123.78(19) . . ? O22 C21 C22 120.92(17) . . ? O21 C21 C22 115.26(17) . . ? C23 C22 C21 114.77(17) . . ? C23 C22 H22A 108.6 . . ? C21 C22 H22A 108.6 . . ? C23 C22 H22B 108.6 . . ? C21 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C22 C23 C24 112.82(16) . . ? C22 C23 H23A 109.0 . . ? C24 C23 H23A 109.0 . . ? C22 C23 H23B 109.0 . . ? C24 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C25 C24 C23 114.88(16) . . ? C25 C24 H24A 108.5 . . ? C23 C24 H24A 108.5 . . ? C25 C24 H24B 108.5 . . ? C23 C24 H24B 108.5 . . ? H24A C24 H24B 107.5 . . ? O26 C25 O25 123.90(19) . . ? O26 C25 C24 121.53(18) . . ? O25 C25 C24 114.56(19) . . ? C25 O25 H25 108.8(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 0.6(3) . . . . ? N11 C12 C13 C14 -0.6(3) . . . . ? C12 C13 C14 N14 -179.37(19) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C13 C14 N14 C17 -6.6(3) . . . . ? C15 C14 N14 C17 174.17(18) . . . . ? N14 C14 C15 C16 -179.73(17) . . . . ? C13 C14 C15 C16 1.0(3) . . . . ? C12 N11 C16 C15 0.3(3) . . . . ? C14 C15 C16 N11 -1.1(3) . . . . ? C14 N14 C17 O17 1.2(3) . . . . ? C14 N14 C17 C18 -178.35(18) . . . . ? O22 C21 C22 C23 14.5(3) . . . . ? O21 C21 C22 C23 -167.77(16) . . . . ? C21 C22 C23 C24 -164.60(16) . . . . ? C22 C23 C24 C25 -51.9(2) . . . . ? C23 C24 C25 O26 140.06(19) . . . . ? C23 C24 C25 O25 -40.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O21 0.88(3) 1.79(3) 2.677(2) 177(2) . O25 H25 O21 0.96(3) 1.58(3) 2.5309(19) 170(2) 2_557 N14 H14 O26 0.86(2) 1.97(2) 2.824(2) 177(2) 1_664 _diffrn_measured_fraction_theta_max 0.873 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.873 _refine_diff_density_max 0.442 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.073 #END