# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'William Jones' _publ_contact_author_email WJ10@CAM.AC.UK _publ_section_title ; Control and interconversion of cocrystal stoichiometry in grinding: stepwise mechanism for the formation of a hydrogen-bonded cocrystal ; loop_ _publ_author_name 'William Jones' 'Tomislav Friscic' 'Shyam Karki' # Attachment 'deposit_revised.cif' data_(na)2.(mal) _database_code_depnum_ccdc_archive 'CCDC 695329' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nicotinamide:malonic acid 2/1 ; _chemical_name_common 'nicotinamide:malonic acid 2/1' _chemical_melting_point ? _chemical_formula_moiety '2(C6 H6 N2 O), C3 H4 O4' _chemical_formula_sum 'C15 H16 N4 O6' _chemical_formula_weight 348.32 _chemical_absolute_configuration ; 1473 Friedel pairs were averaged for the refinement. ; 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 Pna2(1) 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' _cell_length_a 32.9054(6) _cell_length_b 4.0078(1) _cell_length_c 12.3689(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1631.19(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 11834 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.918 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atoms were located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 8534 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 27.86 _reflns_number_total 1983 _reflns_number_gt 1780 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.2847P] 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 1983 _refine_ls_number_parameters 232 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0878 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.07251(5) 0.1344(5) 0.41728(13) 0.0423(4) Uani 1 1 d . . . O2 O 0.32014(5) -0.0976(4) -0.10065(13) 0.0406(4) Uani 1 1 d . . . O3 O 0.31892(5) 0.2583(5) 0.42063(14) 0.0358(4) Uani 1 1 d . . . H3A H 0.2996(9) 0.120(7) 0.477(2) 0.043 Uiso 1 1 d . . . O4 O 0.35649(6) 0.3646(5) 0.56534(14) 0.0480(5) Uani 1 1 d . . . O5 O 0.39507(6) 0.2974(5) 0.23603(14) 0.0465(4) Uani 1 1 d . . . O6 O 0.43553(5) 0.2770(4) 0.37990(13) 0.0348(4) Uani 1 1 d . . . H6A H 0.4519(9) 0.134(7) 0.332(2) 0.042 Uiso 1 1 d . . . N1 N -0.01705(6) -0.4073(5) 0.26547(15) 0.0338(4) Uani 1 1 d . . . N2 N 0.11471(6) 0.0964(6) 0.27426(17) 0.0437(5) Uani 1 1 d . . . H2A H 0.1350 0.1893 0.3096 0.052 Uiso 1 1 calc R . . H2B H 0.1180 0.0332 0.2067 0.052 Uiso 1 1 calc R . . N3 N 0.22956(6) 0.4424(5) 0.04466(14) 0.0318(4) Uani 1 1 d . . . N4 N 0.36360(6) -0.0186(6) 0.03800(16) 0.0455(5) Uani 1 1 d . . . H4A H 0.3838 -0.1169 0.0040 0.055 Uiso 1 1 calc R . . H4B H 0.3673 0.0618 0.1035 0.055 Uiso 1 1 calc R . . C1 C 0.04583(7) -0.1052(5) 0.25842(17) 0.0289(4) Uani 1 1 d . . . C2 C 0.04215(7) -0.0832(6) 0.14630(18) 0.0339(5) Uani 1 1 d . . . H2 H 0.0629 0.0211 0.1048 0.041 Uiso 1 1 calc R . . C3 C 0.00824(7) -0.2141(6) 0.0960(2) 0.0370(5) Uani 1 1 d . . . H3 H 0.0049 -0.1939 0.0200 0.044 Uiso 1 1 calc R . . C4 C -0.02076(7) -0.3746(6) 0.15781(19) 0.0348(5) Uani 1 1 d . . . H4 H -0.0440 -0.4648 0.1231 0.042 Uiso 1 1 calc R . . C5 C 0.01518(7) -0.2713(5) 0.31405(18) 0.0294(5) Uani 1 1 d . . . H5 H 0.0173 -0.2890 0.3904 0.035 Uiso 1 1 calc R . . C6 C 0.07921(7) 0.0517(6) 0.32279(18) 0.0321(5) Uani 1 1 d . . . C7 C 0.29401(6) 0.1704(5) 0.05483(16) 0.0273(4) Uani 1 1 d . . . C8 C 0.29212(7) 0.1802(6) 0.16672(18) 0.0351(5) Uani 1 1 d . . . H8 H 0.3140 0.0967 0.2091 0.042 Uiso 1 1 calc R . . C9 C 0.25781(7) 0.3139(6) 0.21610(19) 0.0363(5) Uani 1 1 d . . . H9 H 0.2556 0.3159 0.2927 0.044 Uiso 1 1 calc R . . C10 C 0.22724(7) 0.4430(6) 0.15315(19) 0.0342(5) Uani 1 1 d . . . H10 H 0.2039 0.5348 0.1871 0.041 Uiso 1 1 calc R . . C11 C 0.26194(7) 0.3070(6) -0.00276(18) 0.0299(5) Uani 1 1 d . . . H11 H 0.2631 0.3038 -0.0795 0.036 Uiso 1 1 calc R . . C12 C 0.32768(7) 0.0082(6) -0.00941(17) 0.0312(5) Uani 1 1 d . . . C13 C 0.34946(6) 0.3984(5) 0.46960(18) 0.0285(4) Uani 1 1 d . . . C14 C 0.37621(8) 0.6026(5) 0.3957(2) 0.0343(5) Uani 1 1 d . . . H14A H 0.3934 0.7541 0.4394 0.041 Uiso 1 1 calc R . . H14B H 0.3590 0.7409 0.3476 0.041 Uiso 1 1 calc R . . C15 C 0.40311(6) 0.3783(5) 0.32776(17) 0.0292(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 O1 0.0344(8) 0.0632(11) 0.0293(8) -0.0147(8) 0.0032(7) -0.0080(8) O2 0.0307(8) 0.0593(11) 0.0320(9) -0.0143(8) -0.0027(7) 0.0078(7) O3 0.0282(8) 0.0505(9) 0.0288(8) -0.0026(7) -0.0010(7) -0.0084(7) O4 0.0432(10) 0.0709(13) 0.0300(9) -0.0025(8) -0.0071(8) -0.0139(9) O5 0.0387(10) 0.0667(12) 0.0339(9) -0.0061(9) -0.0074(8) 0.0036(9) O6 0.0278(8) 0.0457(9) 0.0310(8) -0.0009(7) -0.0012(7) 0.0034(6) N1 0.0283(9) 0.0365(10) 0.0365(10) -0.0038(8) 0.0039(8) -0.0012(8) N2 0.0280(10) 0.0677(14) 0.0354(10) -0.0189(10) 0.0047(8) -0.0106(9) N3 0.0266(9) 0.0365(10) 0.0322(9) -0.0037(8) -0.0022(7) 0.0032(7) N4 0.0294(10) 0.0727(14) 0.0342(10) -0.0193(11) -0.0043(8) 0.0128(9) C1 0.0263(10) 0.0307(10) 0.0298(11) -0.0045(8) 0.0005(8) 0.0024(8) C2 0.0307(11) 0.0413(12) 0.0296(10) 0.0000(10) 0.0042(9) -0.0016(9) C3 0.0348(13) 0.0470(13) 0.0291(11) -0.0024(10) -0.0030(10) 0.0000(9) C4 0.0259(10) 0.0424(12) 0.0360(11) -0.0068(10) -0.0023(9) -0.0009(9) C5 0.0287(10) 0.0332(11) 0.0262(10) -0.0030(9) 0.0017(9) 0.0010(8) C6 0.0286(10) 0.0378(11) 0.0297(10) -0.0042(9) 0.0010(9) -0.0022(9) C7 0.0235(9) 0.0319(10) 0.0264(10) -0.0048(8) -0.0001(8) 0.0002(8) C8 0.0346(12) 0.0424(13) 0.0281(11) -0.0004(9) -0.0037(9) 0.0061(10) C9 0.0358(13) 0.0479(13) 0.0252(10) -0.0022(10) 0.0011(9) 0.0049(10) C10 0.0284(11) 0.0408(13) 0.0334(11) -0.0039(9) 0.0050(9) 0.0027(9) C11 0.0275(11) 0.0374(11) 0.0249(10) -0.0039(9) -0.0015(8) 0.0000(9) C12 0.0266(10) 0.0369(11) 0.0301(11) -0.0041(9) -0.0016(8) 0.0022(9) C13 0.0234(10) 0.0311(11) 0.0310(10) -0.0051(8) -0.0013(8) 0.0044(8) C14 0.0335(10) 0.0255(9) 0.0438(12) 0.0003(10) 0.0000(9) -0.0020(9) C15 0.0259(10) 0.0305(10) 0.0312(11) 0.0045(9) 0.0009(8) -0.0050(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.235(3) . ? O2 C12 1.231(3) . ? O3 C13 1.301(3) . ? O3 H3A 1.10(3) . ? O4 C13 1.214(3) . ? O5 C15 1.209(3) . ? O6 C15 1.311(3) . ? O6 H6A 0.99(3) . ? N1 C5 1.335(3) . ? N1 C4 1.344(3) . ? N2 C6 1.326(3) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 C11 1.332(3) . ? N3 C10 1.344(3) . ? N4 C12 1.324(3) . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? C1 C5 1.391(3) . ? C1 C2 1.395(3) . ? C1 C6 1.495(3) . ? C2 C3 1.381(3) . ? C2 H2 0.9500 . ? C3 C4 1.382(3) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C7 C11 1.386(3) . ? C7 C8 1.386(3) . ? C7 C12 1.510(3) . ? C8 C9 1.391(3) . ? C8 H8 0.9500 . ? C9 C10 1.373(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C13 C14 1.510(3) . ? C14 C15 1.516(3) . ? C14 H14A 0.9900 . ? C14 H14B 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 C13 O3 H3A 111.6(15) . . ? C15 O6 H6A 109.1(17) . . ? C5 N1 C4 118.6(2) . . ? C6 N2 H2A 120.0 . . ? C6 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C11 N3 C10 119.1(2) . . ? C12 N4 H4A 120.0 . . ? C12 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C5 C1 C2 117.3(2) . . ? C5 C1 C6 118.07(19) . . ? C2 C1 C6 124.5(2) . . ? C3 C2 C1 119.6(2) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 119.1(2) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? N1 C4 C3 122.1(2) . . ? N1 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? N1 C5 C1 123.3(2) . . ? N1 C5 H5 118.4 . . ? C1 C5 H5 118.4 . . ? O1 C6 N2 123.3(2) . . ? O1 C6 C1 119.1(2) . . ? N2 C6 C1 117.6(2) . . ? C11 C7 C8 117.9(2) . . ? C11 C7 C12 117.27(19) . . ? C8 C7 C12 124.8(2) . . ? C7 C8 C9 119.1(2) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C10 C9 C8 119.4(2) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? N3 C10 C9 121.6(2) . . ? N3 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? N3 C11 C7 122.9(2) . . ? N3 C11 H11 118.5 . . ? C7 C11 H11 118.5 . . ? O2 C12 N4 123.9(2) . . ? O2 C12 C7 118.9(2) . . ? N4 C12 C7 117.19(19) . . ? O4 C13 O3 123.6(2) . . ? O4 C13 C14 122.7(2) . . ? O3 C13 C14 113.7(2) . . ? C13 C14 C15 110.78(16) . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? O5 C15 O6 123.8(2) . . ? O5 C15 C14 123.4(2) . . ? O6 C15 C14 112.74(19) . . ? 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 C5 C1 C2 C3 2.2(3) . . . . ? C6 C1 C2 C3 -174.6(2) . . . . ? C1 C2 C3 C4 -2.2(4) . . . . ? C5 N1 C4 C3 1.9(3) . . . . ? C2 C3 C4 N1 0.1(4) . . . . ? C4 N1 C5 C1 -1.9(3) . . . . ? C2 C1 C5 N1 -0.2(3) . . . . ? C6 C1 C5 N1 176.8(2) . . . . ? C5 C1 C6 O1 -25.2(3) . . . . ? C2 C1 C6 O1 151.6(2) . . . . ? C5 C1 C6 N2 155.2(2) . . . . ? C2 C1 C6 N2 -28.0(3) . . . . ? C11 C7 C8 C9 2.4(4) . . . . ? C12 C7 C8 C9 -174.9(2) . . . . ? C7 C8 C9 C10 -2.1(4) . . . . ? C11 N3 C10 C9 1.4(4) . . . . ? C8 C9 C10 N3 0.2(4) . . . . ? C10 N3 C11 C7 -1.2(3) . . . . ? C8 C7 C11 N3 -0.7(3) . . . . ? C12 C7 C11 N3 176.7(2) . . . . ? C11 C7 C12 O2 -24.3(3) . . . . ? C8 C7 C12 O2 153.0(2) . . . . ? C11 C7 C12 N4 157.5(2) . . . . ? C8 C7 C12 N4 -25.3(4) . . . . ? O4 C13 C14 C15 102.6(3) . . . . ? O3 C13 C14 C15 -76.1(3) . . . . ? C13 C14 C15 O5 97.4(3) . . . . ? C13 C14 C15 O6 -81.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.163 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.037 data_(na).(fum) _database_code_depnum_ccdc_archive 'CCDC 695330' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nictinamide:fumaric acid 1:1 ; _chemical_name_common 'nictinamide:fumaric acid 1:1' _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N2 O, C4 H4 O4' _chemical_formula_sum 'C10 H10 N2 O5' _chemical_formula_weight 238.20 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 5.53140(10) _cell_length_b 13.7844(4) _cell_length_c 14.2056(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.5900(10) _cell_angle_gamma 90.00 _cell_volume 1082.03(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 10762 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 34.97 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.873 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atoms were located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 16034 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 35.03 _reflns_number_total 4712 _reflns_number_gt 2963 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.1671P] 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 4712 _refine_ls_number_parameters 160 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.81471(15) 0.35939(6) 0.80960(7) 0.0312(2) Uani 1 1 d . . . O2 O 1.32228(15) 0.39918(7) 0.95064(7) 0.0361(2) Uani 1 1 d . . . O3 O 1.16741(15) 0.26024(7) 0.89169(7) 0.0347(2) Uani 1 1 d D . . H3A H 1.043(3) 0.3008(12) 0.8606(11) 0.042 Uiso 1 1 d D . . O4 O 2.06945(15) 0.27379(7) 1.12756(7) 0.0334(2) Uani 1 1 d . . . O5 O 1.88068(15) 0.13897(7) 1.07628(7) 0.0325(2) Uani 1 1 d D . . H5A H 2.020(2) 0.1021(12) 1.1075(11) 0.039 Uiso 1 1 d D . . N1 N 0.21648(17) 0.46402(8) 0.65968(7) 0.0280(2) Uani 1 1 d . . . N2 N 0.92361(18) 0.50653(8) 0.86583(8) 0.0318(2) Uani 1 1 d . . . H2A H 1.0501 0.4826 0.8977 0.038 Uiso 1 1 calc R . . H2B H 0.8930 0.5691 0.8679 0.038 Uiso 1 1 calc R . . C1 C 0.40842(19) 0.43090(8) 0.71104(8) 0.0255(2) Uani 1 1 d . . . H1 H 0.4362 0.3629 0.7140 0.031 Uiso 1 1 calc R . . C2 C 0.56854(18) 0.49256(8) 0.76024(8) 0.0226(2) Uani 1 1 d . . . C3 C 0.5255(2) 0.59159(9) 0.75584(9) 0.0286(2) Uani 1 1 d . . . H3 H 0.6317 0.6356 0.7885 0.034 Uiso 1 1 calc R . . C4 C 0.3254(2) 0.62591(9) 0.70323(10) 0.0312(3) Uani 1 1 d . . . H4 H 0.2920 0.6934 0.6997 0.037 Uiso 1 1 calc R . . C5 C 0.1762(2) 0.55977(9) 0.65625(9) 0.0291(2) Uani 1 1 d . . . H5 H 0.0397 0.5831 0.6201 0.035 Uiso 1 1 calc R . . C6 C 0.77935(18) 0.44829(8) 0.81478(8) 0.0234(2) Uani 1 1 d . . . C7 C 1.32592(18) 0.31144(9) 0.94354(8) 0.0258(2) Uani 1 1 d . . . C8 C 1.51196(18) 0.24939(9) 0.99268(9) 0.0265(2) Uani 1 1 d . . . H8 H 1.4947 0.1808 0.9918 0.032 Uiso 1 1 calc R . . C9 C 1.70150(19) 0.28954(9) 1.03758(9) 0.0277(2) Uani 1 1 d . . . H9 H 1.7111 0.3583 1.0394 0.033 Uiso 1 1 calc R . . C10 C 1.90041(18) 0.23274(9) 1.08530(8) 0.0254(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0297(4) 0.0188(4) 0.0438(5) 0.0006(4) -0.0145(3) 0.0016(3) O2 0.0314(4) 0.0250(5) 0.0504(6) -0.0004(4) -0.0161(4) 0.0024(3) O3 0.0309(4) 0.0251(5) 0.0461(5) -0.0012(4) -0.0191(4) 0.0018(3) O4 0.0269(4) 0.0266(4) 0.0452(5) -0.0005(4) -0.0142(3) -0.0028(3) O5 0.0303(4) 0.0219(4) 0.0437(5) 0.0019(4) -0.0170(3) -0.0001(3) N1 0.0259(4) 0.0229(5) 0.0341(5) 0.0002(4) -0.0104(3) -0.0006(3) N2 0.0280(5) 0.0218(5) 0.0439(6) -0.0045(4) -0.0161(4) 0.0035(3) C1 0.0249(5) 0.0189(5) 0.0317(6) -0.0006(4) -0.0073(4) 0.0004(4) C2 0.0217(4) 0.0184(5) 0.0272(5) 0.0002(4) -0.0052(4) -0.0001(3) C3 0.0285(5) 0.0186(5) 0.0378(6) -0.0001(5) -0.0100(4) -0.0018(4) C4 0.0315(5) 0.0185(5) 0.0424(7) 0.0038(5) -0.0107(5) 0.0008(4) C5 0.0273(5) 0.0241(6) 0.0349(6) 0.0041(5) -0.0102(4) 0.0006(4) C6 0.0215(4) 0.0202(5) 0.0279(5) 0.0005(4) -0.0054(4) 0.0003(3) C7 0.0210(4) 0.0256(6) 0.0301(6) 0.0013(4) -0.0057(4) 0.0004(4) C8 0.0226(5) 0.0243(5) 0.0320(6) 0.0016(4) -0.0060(4) 0.0020(4) C9 0.0238(5) 0.0238(5) 0.0347(6) 0.0022(5) -0.0076(4) 0.0015(4) C10 0.0229(4) 0.0232(5) 0.0293(6) 0.0012(4) -0.0062(4) -0.0017(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.2436(14) . ? O2 C7 1.2139(15) . ? O3 C7 1.3233(14) . ? O3 H3A 0.976(13) . ? O4 C10 1.2264(13) . ? O5 C10 1.3031(15) . ? O5 H5A 1.009(13) . ? N1 C5 1.3389(16) . ? N1 C1 1.3409(13) . ? N2 C6 1.3247(14) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? C1 C2 1.3926(15) . ? C1 H1 0.9500 . ? C2 C3 1.3867(16) . ? C2 C6 1.5002(14) . ? C3 C4 1.3900(15) . ? C3 H3 0.9500 . ? C4 C5 1.3813(16) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C7 C8 1.4875(15) . ? C8 C9 1.3236(15) . ? C8 H8 0.9500 . ? C9 C10 1.4886(15) . ? C9 H9 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 C7 O3 H3A 112.5(11) . . ? C10 O5 H5A 113.4(10) . . ? C5 N1 C1 118.80(10) . . ? C6 N2 H2A 120.0 . . ? C6 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? N1 C1 C2 122.36(10) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 118.31(9) . . ? C3 C2 C6 123.47(9) . . ? C1 C2 C6 118.22(10) . . ? C2 C3 C4 119.35(10) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 118.62(11) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 122.56(10) . . ? N1 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? O1 C6 N2 122.48(9) . . ? O1 C6 C2 119.40(9) . . ? N2 C6 C2 118.11(10) . . ? O2 C7 O3 124.37(10) . . ? O2 C7 C8 123.21(10) . . ? O3 C7 C8 112.43(10) . . ? C9 C8 C7 120.12(11) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 123.55(11) . . ? C8 C9 H9 118.2 . . ? C10 C9 H9 118.2 . . ? O4 C10 O5 124.36(10) . . ? O4 C10 C9 120.78(11) . . ? O5 C10 C9 114.84(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 C5 N1 C1 C2 -0.59(18) . . . . ? N1 C1 C2 C3 0.33(18) . . . . ? N1 C1 C2 C6 -179.33(11) . . . . ? C1 C2 C3 C4 0.21(19) . . . . ? C6 C2 C3 C4 179.85(12) . . . . ? C2 C3 C4 C5 -0.5(2) . . . . ? C1 N1 C5 C4 0.3(2) . . . . ? C3 C4 C5 N1 0.2(2) . . . . ? C3 C2 C6 O1 -174.84(12) . . . . ? C1 C2 C6 O1 4.80(17) . . . . ? C3 C2 C6 N2 4.12(18) . . . . ? C1 C2 C6 N2 -176.23(11) . . . . ? O2 C7 C8 C9 -8.6(2) . . . . ? O3 C7 C8 C9 171.27(12) . . . . ? C7 C8 C9 C10 -177.55(11) . . . . ? C8 C9 C10 O4 -178.49(13) . . . . ? C8 C9 C10 O5 2.93(19) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 35.03 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.336 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.053 data_(na).(glu) _database_code_depnum_ccdc_archive 'CCDC 695331' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nicotinamide:glutaric acid 1:1 ; _chemical_name_common 'nicotinamide:glutaric acid 1:1' _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N2 O, C5 H8 O4' _chemical_formula_sum 'C11 H14 N2 O5' _chemical_formula_weight 254.24 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 5.4556(5) _cell_length_b 7.3692(6) _cell_length_c 15.1945(13) _cell_angle_alpha 99.413(5) _cell_angle_beta 94.592(5) _cell_angle_gamma 104.775(3) _cell_volume 577.95(9) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 10439 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.909 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atoms were located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 4270 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0598 _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 -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 24.93 _reflns_number_total 1964 _reflns_number_gt 1467 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+0.2989P] 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 1964 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1335 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 O2 O 1.2613(3) -0.0662(2) 0.35623(11) 0.0367(5) Uani 1 1 d . . . O3 O 0.8604(3) -0.2499(3) 0.32587(12) 0.0359(5) Uani 1 1 d . . . H3A H 0.874(6) -0.261(4) 0.386(2) 0.043 Uiso 1 1 d . . . O4 O 0.3437(3) -0.3282(3) 0.01925(12) 0.0381(5) Uani 1 1 d . . . O5 O 0.5639(4) -0.1904(3) -0.08175(12) 0.0388(5) Uani 1 1 d . . . H5A H 0.423(6) -0.234(4) -0.116(2) 0.047 Uiso 1 1 d . . . C7 C 1.0683(5) -0.1435(3) 0.30295(15) 0.0268(6) Uani 1 1 d . . . C8 C 1.0512(4) -0.1251(3) 0.20648(15) 0.0268(6) Uani 1 1 d . . . H8A H 1.1703 -0.1895 0.1772 0.032 Uiso 1 1 calc R . . H8B H 1.1111 0.0122 0.2037 0.032 Uiso 1 1 calc R . . C9 C 0.7863(4) -0.2071(3) 0.15184(15) 0.0271(6) Uani 1 1 d . . . H9A H 0.7284 -0.3466 0.1498 0.032 Uiso 1 1 calc R . . H9B H 0.6626 -0.1478 0.1813 0.032 Uiso 1 1 calc R . . C10 C 0.7938(5) -0.1689(4) 0.05715(15) 0.0294(6) Uani 1 1 d . . . H10A H 0.8586 -0.0294 0.0604 0.035 Uiso 1 1 calc R . . H10B H 0.9169 -0.2300 0.0285 0.035 Uiso 1 1 calc R . . C11 C 0.5412(5) -0.2397(3) -0.00161(15) 0.0276(6) Uani 1 1 d . . . O1 O 1.1481(3) -0.6780(3) 0.51342(11) 0.0383(5) Uani 1 1 d . . . N1 N 0.8477(4) -0.6943(3) 0.20825(13) 0.0312(5) Uani 1 1 d . . . C1 C 0.8140(5) -0.7393(3) 0.28926(16) 0.0305(6) Uani 1 1 d . . . H1 H 0.6498 -0.8121 0.2976 0.037 Uiso 1 1 calc R . . N2 N 0.7463(4) -0.8466(3) 0.46206(15) 0.0482(7) Uani 1 1 d . . . H2A H 0.7211 -0.8792 0.5145 0.058 Uiso 1 1 calc R . . H2B H 0.6223 -0.8870 0.4168 0.058 Uiso 1 1 calc R . . C2 C 1.0066(5) -0.6850(3) 0.36154(15) 0.0266(6) Uani 1 1 d . . . C3 C 1.2456(5) -0.5775(3) 0.34849(16) 0.0315(6) Uani 1 1 d . . . H3 H 1.3818 -0.5358 0.3965 0.038 Uiso 1 1 calc R . . C4 C 1.2834(5) -0.5318(4) 0.26546(17) 0.0331(6) Uani 1 1 d . . . H4 H 1.4460 -0.4599 0.2551 0.040 Uiso 1 1 calc R . . C5 C 1.0790(5) -0.5931(4) 0.19714(16) 0.0312(6) Uani 1 1 d . . . H5 H 1.1055 -0.5613 0.1399 0.037 Uiso 1 1 calc R . . C6 C 0.9688(5) -0.7377(3) 0.45133(16) 0.0297(6) 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 O2 0.0291(10) 0.0412(11) 0.0284(10) 0.0077(8) -0.0088(8) -0.0077(8) O3 0.0272(10) 0.0470(12) 0.0245(10) 0.0103(8) -0.0017(8) -0.0069(8) O4 0.0250(10) 0.0480(12) 0.0356(11) 0.0093(8) -0.0005(8) 0.0004(9) O5 0.0295(10) 0.0560(13) 0.0244(10) 0.0114(8) -0.0071(8) 0.0011(9) C7 0.0281(13) 0.0261(13) 0.0236(13) 0.0037(10) -0.0030(11) 0.0053(11) C8 0.0223(13) 0.0281(13) 0.0261(13) 0.0054(10) -0.0001(10) 0.0008(10) C9 0.0232(13) 0.0298(13) 0.0246(12) 0.0053(10) 0.0000(10) 0.0017(10) C10 0.0241(13) 0.0334(14) 0.0264(13) 0.0068(10) -0.0008(10) 0.0004(11) C11 0.0295(14) 0.0287(14) 0.0218(13) 0.0027(10) -0.0007(11) 0.0057(11) O1 0.0309(10) 0.0489(12) 0.0265(10) 0.0088(8) -0.0049(8) -0.0027(9) N1 0.0326(12) 0.0329(12) 0.0254(11) 0.0050(9) -0.0013(9) 0.0061(10) C1 0.0279(14) 0.0310(14) 0.0282(14) 0.0036(10) 0.0000(11) 0.0027(11) N2 0.0364(14) 0.0647(17) 0.0280(12) 0.0185(11) -0.0098(10) -0.0154(12) C2 0.0269(13) 0.0254(13) 0.0248(13) 0.0017(9) 0.0000(10) 0.0053(10) C3 0.0258(13) 0.0338(15) 0.0307(14) 0.0056(11) -0.0017(11) 0.0027(11) C4 0.0284(14) 0.0328(14) 0.0338(15) 0.0066(11) 0.0036(11) 0.0009(11) C5 0.0362(15) 0.0309(14) 0.0267(13) 0.0077(11) 0.0046(11) 0.0081(12) C6 0.0282(14) 0.0286(14) 0.0273(13) 0.0034(10) -0.0026(11) 0.0016(11) _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 O2 C7 1.223(3) . ? O3 C7 1.312(3) . ? O3 H3A 0.93(3) . ? O4 C11 1.205(3) . ? O5 C11 1.333(3) . ? O5 H5A 0.85(3) . ? C7 C8 1.492(3) . ? C8 C9 1.530(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.512(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.501(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? O1 C6 1.240(3) . ? N1 C5 1.331(3) . ? N1 C1 1.341(3) . ? C1 C2 1.388(3) . ? C1 H1 0.9500 . ? N2 C6 1.313(3) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? C2 C3 1.390(3) . ? C2 C6 1.494(3) . ? C3 C4 1.376(3) . ? C3 H3 0.9500 . ? C4 C5 1.389(3) . ? C4 H4 0.9500 . ? C5 H5 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 C7 O3 H3A 113.8(18) . . ? C11 O5 H5A 111(2) . . ? O2 C7 O3 122.8(2) . . ? O2 C7 C8 122.6(2) . . ? O3 C7 C8 114.67(19) . . ? C7 C8 C9 116.1(2) . . ? C7 C8 H8A 108.3 . . ? C9 C8 H8A 108.3 . . ? C7 C8 H8B 108.3 . . ? C9 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C10 C9 C8 110.42(19) . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9B 109.6 . . ? C8 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 114.7(2) . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? O4 C11 O5 123.8(2) . . ? O4 C11 C10 125.9(2) . . ? O5 C11 C10 110.3(2) . . ? C5 N1 C1 117.8(2) . . ? N1 C1 C2 123.4(2) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C6 N2 H2A 120.0 . . ? C6 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C1 C2 C3 117.7(2) . . ? C1 C2 C6 123.2(2) . . ? C3 C2 C6 119.1(2) . . ? C4 C3 C2 119.5(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 118.6(2) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? N1 C5 C4 123.0(2) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? O1 C6 N2 121.9(2) . . ? O1 C6 C2 119.2(2) . . ? N2 C6 C2 118.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C7 C8 C9 -171.9(2) . . . . ? O3 C7 C8 C9 8.5(3) . . . . ? C7 C8 C9 C10 176.8(2) . . . . ? C8 C9 C10 C11 -178.6(2) . . . . ? C9 C10 C11 O4 -3.3(4) . . . . ? C9 C10 C11 O5 176.6(2) . . . . ? C5 N1 C1 C2 0.3(4) . . . . ? N1 C1 C2 C3 0.4(4) . . . . ? N1 C1 C2 C6 -179.2(2) . . . . ? C1 C2 C3 C4 -1.0(4) . . . . ? C6 C2 C3 C4 178.6(2) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C1 N1 C5 C4 -0.5(4) . . . . ? C3 C4 C5 N1 -0.1(4) . . . . ? C1 C2 C6 O1 -177.5(2) . . . . ? C3 C2 C6 O1 2.9(4) . . . . ? C1 C2 C6 N2 2.7(4) . . . . ? C3 C2 C6 N2 -176.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 24.93 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.208 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.059 data_(na).(adi) _database_code_depnum_ccdc_archive 'CCDC 695332' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nicotinamide:adipic acid 1:1 ; _chemical_name_common 'nicotinamide:adipic acid 1:1' _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 O4, C6 H6 N2 O' _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 5.0110(1) _cell_length_b 5.3379(1) _cell_length_c 24.0348(6) _cell_angle_alpha 93.036(1) _cell_angle_beta 92.753(1) _cell_angle_gamma 92.189(1) _cell_volume 640.71(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 11039 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 29.13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.921 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atoms were located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 8840 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 29.10 _reflns_number_total 3376 _reflns_number_gt 2703 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.1834P] 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 3376 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.12964(17) 0.57741(17) 0.30422(4) 0.0342(2) Uani 1 1 d . . . O2 O 0.5906(2) 0.08361(17) 0.08203(4) 0.0347(2) Uani 1 1 d . . . H2A H 0.711(3) 0.089(3) 0.1129(8) 0.042 Uiso 1 1 d . . . O3 O 0.4588(2) 0.44511(18) 0.12069(4) 0.0386(3) Uani 1 1 d . . . O4 O -0.2209(2) -0.0087(2) 0.36201(5) 0.0451(3) Uani 1 1 d . . . H4A H -0.162(4) -0.145(4) 0.3442(8) 0.054 Uiso 1 1 d . . . O5 O 0.1630(2) -0.03268(19) 0.41150(4) 0.0415(3) Uani 1 1 d . . . N1 N -0.0475(2) 0.0816(2) 0.16829(5) 0.0302(2) Uani 1 1 d . . . N2 N 0.3036(2) 0.5545(2) 0.33207(5) 0.0312(3) Uani 1 1 d . . . H2N1 H 0.2906 0.6744 0.3582 0.037 Uiso 1 1 calc R . . H2N2 H 0.4573 0.4833 0.3277 0.037 Uiso 1 1 calc R . . C1 C 0.1229(2) 0.2779(2) 0.25538(5) 0.0249(2) Uani 1 1 d . . . C2 C 0.3216(2) 0.1036(2) 0.25886(5) 0.0286(3) Uani 1 1 d . . . H2 H 0.4480 0.1111 0.2897 0.034 Uiso 1 1 calc R . . C3 C 0.3313(3) -0.0813(2) 0.21631(6) 0.0311(3) Uani 1 1 d . . . H3 H 0.4651 -0.2026 0.2174 0.037 Uiso 1 1 calc R . . C4 C 0.1432(3) -0.0864(2) 0.17222(6) 0.0302(3) Uani 1 1 d . . . H4 H 0.1495 -0.2148 0.1434 0.036 Uiso 1 1 calc R . . C5 C -0.0559(2) 0.2604(2) 0.20933(5) 0.0274(3) Uani 1 1 d . . . H5 H -0.1903 0.3806 0.2068 0.033 Uiso 1 1 calc R . . C6 C 0.0921(2) 0.4811(2) 0.29932(5) 0.0253(2) Uani 1 1 d . . . C7 C 0.4381(2) 0.2814(2) 0.08359(5) 0.0271(3) Uani 1 1 d . . . C8 C 0.2385(3) 0.2716(2) 0.03474(5) 0.0294(3) Uani 1 1 d . . . H8A H 0.1074 0.1312 0.0389 0.035 Uiso 1 1 calc R . . H8B H 0.3336 0.2331 0.0004 0.035 Uiso 1 1 calc R . . C9 C 0.0863(2) 0.5091(2) 0.02711(5) 0.0284(3) Uani 1 1 d . . . H9A H 0.2150 0.6544 0.0268 0.034 Uiso 1 1 calc R . . H9B H -0.0289 0.5376 0.0590 0.034 Uiso 1 1 calc R . . C10 C -0.0486(3) 0.0642(2) 0.40374(5) 0.0307(3) Uani 1 1 d . . . C11 C -0.1486(3) 0.2748(3) 0.43996(6) 0.0377(3) Uani 1 1 d . . . H11A H -0.2985 0.2086 0.4610 0.045 Uiso 1 1 calc R . . H11B H -0.2199 0.4033 0.4157 0.045 Uiso 1 1 calc R . . C12 C 0.0599(3) 0.4001(2) 0.48100(5) 0.0326(3) Uani 1 1 d . . . H12A H 0.2040 0.4788 0.4603 0.039 Uiso 1 1 calc R . . H12B H 0.1401 0.2715 0.5041 0.039 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 O1 0.0231(4) 0.0364(5) 0.0414(5) -0.0148(4) 0.0006(4) 0.0046(4) O2 0.0384(5) 0.0337(5) 0.0310(5) -0.0088(4) -0.0080(4) 0.0154(4) O3 0.0442(6) 0.0341(5) 0.0355(5) -0.0129(4) -0.0103(4) 0.0121(4) O4 0.0410(6) 0.0471(6) 0.0443(6) -0.0229(5) -0.0117(5) 0.0173(5) O5 0.0365(5) 0.0439(6) 0.0424(6) -0.0163(4) -0.0050(4) 0.0122(4) N1 0.0303(5) 0.0315(5) 0.0282(5) -0.0052(4) -0.0024(4) 0.0055(4) N2 0.0253(5) 0.0354(6) 0.0317(6) -0.0102(4) -0.0027(4) 0.0055(4) C1 0.0219(5) 0.0251(5) 0.0275(6) -0.0025(4) 0.0025(4) 0.0022(4) C2 0.0260(6) 0.0299(6) 0.0297(6) 0.0000(5) -0.0015(5) 0.0052(5) C3 0.0298(6) 0.0280(6) 0.0361(7) -0.0009(5) 0.0030(5) 0.0092(5) C4 0.0337(7) 0.0267(6) 0.0301(6) -0.0042(5) 0.0039(5) 0.0055(5) C5 0.0253(6) 0.0272(6) 0.0293(6) -0.0039(5) -0.0006(5) 0.0056(4) C6 0.0234(5) 0.0261(5) 0.0264(6) -0.0017(4) 0.0026(4) 0.0021(4) C7 0.0267(6) 0.0268(6) 0.0277(6) -0.0020(4) 0.0008(5) 0.0046(4) C8 0.0302(6) 0.0279(6) 0.0291(6) -0.0064(5) -0.0030(5) 0.0054(5) C9 0.0279(6) 0.0273(6) 0.0291(6) -0.0043(5) -0.0020(5) 0.0043(5) C10 0.0328(6) 0.0310(6) 0.0279(6) -0.0052(5) 0.0014(5) 0.0045(5) C11 0.0386(7) 0.0382(7) 0.0352(7) -0.0118(6) -0.0015(6) 0.0118(6) C12 0.0381(7) 0.0319(6) 0.0274(6) -0.0062(5) 0.0017(5) 0.0075(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.2498(14) . ? O2 C7 1.3263(14) . ? O2 H2A 0.933(19) . ? O3 C7 1.2131(15) . ? O4 C10 1.3238(17) . ? O4 H4A 0.89(2) . ? O5 C10 1.2085(16) . ? N1 C5 1.3389(16) . ? N1 C4 1.3390(16) . ? N2 C6 1.3237(16) . ? N2 H2N1 0.8800 . ? N2 H2N2 0.8800 . ? C1 C5 1.3872(17) . ? C1 C2 1.3912(16) . ? C1 C6 1.4910(16) . ? C2 C3 1.3871(18) . ? C2 H2 0.9500 . ? C3 C4 1.3826(19) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C7 C8 1.5029(17) . ? C8 C9 1.5186(17) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C9 1.526(2) 2_565 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5013(17) . ? C11 C12 1.5130(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C12 1.526(2) 2_566 ? C12 H12A 0.9900 . ? C12 H12B 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 C7 O2 H2A 111.0(10) . . ? C10 O4 H4A 109.1(12) . . ? C5 N1 C4 118.02(11) . . ? C6 N2 H2N1 120.0 . . ? C6 N2 H2N2 120.0 . . ? H2N1 N2 H2N2 120.0 . . ? C5 C1 C2 118.59(11) . . ? C5 C1 C6 118.58(10) . . ? C2 C1 C6 122.82(11) . . ? C3 C2 C1 118.59(12) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C4 C3 C2 118.96(11) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? N1 C4 C3 122.89(11) . . ? N1 C4 H4 118.6 . . ? C3 C4 H4 118.6 . . ? N1 C5 C1 122.94(11) . . ? N1 C5 H5 118.5 . . ? C1 C5 H5 118.5 . . ? O1 C6 N2 121.97(11) . . ? O1 C6 C1 119.73(11) . . ? N2 C6 C1 118.29(10) . . ? O3 C7 O2 123.13(12) . . ? O3 C7 C8 125.43(11) . . ? O2 C7 C8 111.44(10) . . ? C7 C8 C9 115.58(10) . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8A 108.4 . . ? C7 C8 H8B 108.4 . . ? C9 C8 H8B 108.4 . . ? H8A C8 H8B 107.4 . . ? C8 C9 C9 111.42(12) . 2_565 ? C8 C9 H9A 109.3 . . ? C9 C9 H9A 109.3 2_565 . ? C8 C9 H9B 109.3 . . ? C9 C9 H9B 109.3 2_565 . ? H9A C9 H9B 108.0 . . ? O5 C10 O4 122.83(12) . . ? O5 C10 C11 124.70(12) . . ? O4 C10 C11 112.46(11) . . ? C10 C11 C12 114.60(11) . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C11 C12 C12 111.70(14) . 2_566 ? C11 C12 H12A 109.3 . . ? C12 C12 H12A 109.3 2_566 . ? C11 C12 H12B 109.3 . . ? C12 C12 H12B 109.3 2_566 . ? H12A C12 H12B 107.9 . . ? 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 C5 C1 C2 C3 -0.45(18) . . . . ? C6 C1 C2 C3 178.89(12) . . . . ? C1 C2 C3 C4 -0.24(19) . . . . ? C5 N1 C4 C3 -0.57(19) . . . . ? C2 C3 C4 N1 0.8(2) . . . . ? C4 N1 C5 C1 -0.17(19) . . . . ? C2 C1 C5 N1 0.68(19) . . . . ? C6 C1 C5 N1 -178.69(11) . . . . ? C5 C1 C6 O1 22.78(18) . . . . ? C2 C1 C6 O1 -156.56(12) . . . . ? C5 C1 C6 N2 -157.02(12) . . . . ? C2 C1 C6 N2 23.64(18) . . . . ? O3 C7 C8 C9 10.98(19) . . . . ? O2 C7 C8 C9 -170.03(11) . . . . ? C7 C8 C9 C9 173.36(13) . . . 2_565 ? O5 C10 C11 C12 12.6(2) . . . . ? O4 C10 C11 C12 -168.33(13) . . . . ? C10 C11 C12 C12 -176.14(14) . . . 2_566 ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 29.10 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.259 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.043 data_(na)2.(adi) _database_code_depnum_ccdc_archive 'CCDC 695333' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nicotinamide:adipic acid 2:1 ; _chemical_name_common 'nicotinamide:adipic acid 2:1' _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 O4, 2(C6 H6 N2 O)' _chemical_formula_sum 'C18 H22 N4 O6' _chemical_formula_weight 390.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.0302(3) _cell_length_b 5.4600(3) _cell_length_c 16.9903(9) _cell_angle_alpha 82.380(4) _cell_angle_beta 89.395(4) _cell_angle_gamma 90.006(2) _cell_volume 462.49(4) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3300 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 206 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.936 _exptl_absorpt_correction_T_max 1.008 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -OH hydrogen atom was located and its position was refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 4351 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 27.86 _reflns_number_total 2176 _reflns_number_gt 1549 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.1635P] 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 2176 _refine_ls_number_parameters 130 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0782 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1130 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8087(2) 0.8271(3) 0.43195(8) 0.0376(4) Uani 1 1 d . . . O2 O 0.4281(3) 0.8420(3) 0.17017(8) 0.0449(4) Uani 1 1 d . . . O3 O 0.5773(3) 0.5181(3) 0.11603(7) 0.0403(4) Uani 1 1 d D . . H3A H 0.697(4) 0.499(4) 0.1612(11) 0.048 Uiso 1 1 d D . . N1 N 0.9172(3) 0.4451(3) 0.23803(9) 0.0349(4) Uani 1 1 d . . . N2 N 1.2428(3) 0.7905(3) 0.46255(8) 0.0328(4) Uani 1 1 d . . . H2A H 1.2260 0.8871 0.4998 0.039 Uiso 1 1 calc R . . H2B H 1.3986 0.7267 0.4531 0.039 Uiso 1 1 calc R . . C1 C 1.1093(4) 0.2760(4) 0.24253(11) 0.0353(4) Uani 1 1 d . . . H1 H 1.1209 0.1710 0.2023 0.042 Uiso 1 1 calc R . . C2 C 1.2930(4) 0.2464(4) 0.30331(11) 0.0349(4) Uani 1 1 d . . . H2 H 1.4283 0.1247 0.3045 0.042 Uiso 1 1 calc R . . C3 C 1.2747(4) 0.3985(3) 0.36231(10) 0.0323(4) Uani 1 1 d . . . H3 H 1.3989 0.3836 0.4044 0.039 Uiso 1 1 calc R . . C4 C 1.0734(3) 0.5723(3) 0.35916(9) 0.0276(4) Uani 1 1 d . . . C5 C 0.9006(4) 0.5901(3) 0.29531(10) 0.0318(4) Uani 1 1 d . . . H5 H 0.7642 0.7113 0.2923 0.038 Uiso 1 1 calc R . . C6 C 1.0328(3) 0.7410(3) 0.42059(10) 0.0287(4) Uani 1 1 d . . . C7 C 0.4214(4) 0.7127(3) 0.11785(10) 0.0319(4) Uani 1 1 d . . . C8 C 0.2361(4) 0.7458(4) 0.04855(10) 0.0349(4) Uani 1 1 d . . . H8A H 0.1092 0.6058 0.0544 0.042 Uiso 1 1 calc R . . H8B H 0.3413 0.7372 -0.0006 0.042 Uiso 1 1 calc R . . C9 C 0.0791(4) 0.9842(3) 0.03843(10) 0.0331(4) Uani 1 1 d . . . H9A H 0.2027 1.1254 0.0382 0.040 Uiso 1 1 calc R . . H9B H -0.0446 0.9852 0.0841 0.040 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 O1 0.0244(7) 0.0487(9) 0.0442(7) -0.0231(6) -0.0004(5) 0.0033(6) O2 0.0512(9) 0.0470(9) 0.0410(8) -0.0217(6) -0.0135(6) 0.0155(7) O3 0.0446(8) 0.0453(9) 0.0344(7) -0.0169(6) -0.0116(6) 0.0193(7) N1 0.0360(9) 0.0384(9) 0.0322(8) -0.0120(6) -0.0039(6) 0.0066(7) N2 0.0257(8) 0.0414(9) 0.0343(8) -0.0157(7) -0.0026(6) 0.0057(7) C1 0.0399(11) 0.0353(10) 0.0326(9) -0.0117(7) 0.0023(7) 0.0037(8) C2 0.0360(10) 0.0330(10) 0.0366(10) -0.0081(8) 0.0013(7) 0.0093(8) C3 0.0324(10) 0.0356(10) 0.0292(9) -0.0052(7) -0.0021(7) 0.0041(8) C4 0.0246(8) 0.0310(10) 0.0281(8) -0.0068(7) 0.0015(6) 0.0013(7) C5 0.0285(9) 0.0350(10) 0.0334(9) -0.0100(7) -0.0013(7) 0.0061(8) C6 0.0246(9) 0.0332(10) 0.0292(9) -0.0076(7) 0.0012(6) 0.0004(7) C7 0.0318(10) 0.0343(10) 0.0309(9) -0.0089(7) -0.0010(7) 0.0035(8) C8 0.0356(10) 0.0385(11) 0.0329(9) -0.0124(8) -0.0065(7) 0.0055(8) C9 0.0329(10) 0.0361(10) 0.0321(9) -0.0107(8) -0.0040(7) 0.0040(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.244(2) . ? O2 C7 1.207(2) . ? O3 C7 1.324(2) . ? O3 H3A 0.975(15) . ? N1 C1 1.333(2) . ? N1 C5 1.336(2) . ? N2 C6 1.328(2) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? C1 C2 1.386(3) . ? C1 H1 0.9500 . ? C2 C3 1.386(2) . ? C2 H2 0.9500 . ? C3 C4 1.385(2) . ? C3 H3 0.9500 . ? C4 C5 1.391(2) . ? C4 C6 1.493(2) . ? C5 H5 0.9500 . ? C7 C8 1.502(2) . ? C8 C9 1.514(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C9 1.527(3) 2_575 ? C9 H9A 0.9900 . ? C9 H9B 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 C7 O3 H3A 110.7(13) . . ? C1 N1 C5 118.13(15) . . ? C6 N2 H2A 120.0 . . ? C6 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? N1 C1 C2 122.92(16) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 118.50(17) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C4 C3 C2 119.23(16) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 118.07(15) . . ? C3 C4 C6 123.43(15) . . ? C5 C4 C6 118.50(15) . . ? N1 C5 C4 123.14(16) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? O1 C6 N2 122.21(15) . . ? O1 C6 C4 120.41(15) . . ? N2 C6 C4 117.37(15) . . ? O2 C7 O3 123.09(16) . . ? O2 C7 C8 125.33(17) . . ? O3 C7 C8 111.57(14) . . ? C7 C8 C9 115.50(15) . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8A 108.4 . . ? C7 C8 H8B 108.4 . . ? C9 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C8 C9 C9 111.86(18) . 2_575 ? C8 C9 H9A 109.2 . . ? C9 C9 H9A 109.2 2_575 . ? C8 C9 H9B 109.2 . . ? C9 C9 H9B 109.2 2_575 . ? H9A C9 H9B 107.9 . . ? 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 C5 N1 C1 C2 -0.7(3) . . . . ? N1 C1 C2 C3 0.5(3) . . . . ? C1 C2 C3 C4 0.6(3) . . . . ? C2 C3 C4 C5 -1.4(3) . . . . ? C2 C3 C4 C6 178.64(16) . . . . ? C1 N1 C5 C4 -0.2(3) . . . . ? C3 C4 C5 N1 1.2(3) . . . . ? C6 C4 C5 N1 -178.84(16) . . . . ? C3 C4 C6 O1 -154.23(18) . . . . ? C5 C4 C6 O1 25.8(3) . . . . ? C3 C4 C6 N2 24.7(3) . . . . ? C5 C4 C6 N2 -155.19(17) . . . . ? O2 C7 C8 C9 10.1(3) . . . . ? O3 C7 C8 C9 -171.14(16) . . . . ? C7 C8 C9 C9 173.42(19) . . . 2_575 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.247 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.047 data_(na).(pim) _database_code_depnum_ccdc_archive 'CCDC 695334' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nicotinamide:pimelic acid 1:1 ; _chemical_name_common 'nicotinamide:pimelic acid 1:1' _chemical_melting_point ? _chemical_formula_moiety 'C7 H12 O4, C6 H6 N2 O' _chemical_formula_sum 'C13 H18 N2 O5' _chemical_formula_weight 282.29 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 5.4425(1) _cell_length_b 7.3981(2) _cell_length_c 17.9304(6) _cell_angle_alpha 99.568(2) _cell_angle_beta 94.075(2) _cell_angle_gamma 104.177(2) _cell_volume 685.49(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4820 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.931 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atoms were located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 6741 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0294 _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 21 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2390 _reflns_number_gt 2156 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+0.1547P] 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 2390 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.84889(17) 0.67931(13) -0.01703(5) 0.0352(2) Uani 1 1 d . . . O2 O 0.12418(17) 0.24623(13) 0.15366(5) 0.0347(2) Uani 1 1 d . . . H21 H 0.116(3) 0.257(2) 0.1048(10) 0.042 Uiso 1 1 d . . . O3 O -0.27450(17) 0.06694(13) 0.12325(5) 0.0356(2) Uani 1 1 d . . . O4 O 0.76909(17) 0.31321(15) 0.56772(5) 0.0405(3) Uani 1 1 d . . . O5 O 0.47908(19) 0.21731(15) 0.64443(5) 0.0398(3) Uani 1 1 d . . . H51 H 0.616(3) 0.243(2) 0.6788(11) 0.048 Uiso 1 1 d . . . N1 N 1.1312(2) 0.70168(15) 0.24309(6) 0.0289(3) Uani 1 1 d . . . N2 N 1.2447(2) 0.85115(19) 0.02929(7) 0.0474(4) Uani 1 1 d . . . H2A H 1.2737 0.8840 -0.0149 0.057 Uiso 1 1 calc R . . H2B H 1.3643 0.8924 0.0683 0.057 Uiso 1 1 calc R . . C1 C 0.8990(2) 0.60365(17) 0.25303(7) 0.0295(3) Uani 1 1 d . . . H1 H 0.8700 0.5759 0.3020 0.035 Uiso 1 1 calc R . . C2 C 0.6984(2) 0.54065(18) 0.19505(7) 0.0311(3) Uani 1 1 d . . . H2 H 0.5361 0.4697 0.2040 0.037 Uiso 1 1 calc R . . C3 C 0.7390(2) 0.58307(17) 0.12385(7) 0.0290(3) Uani 1 1 d . . . H3 H 0.6051 0.5406 0.0830 0.035 Uiso 1 1 calc R . . C4 C 0.9784(2) 0.68865(16) 0.11294(7) 0.0252(3) Uani 1 1 d . . . C5 C 1.1685(2) 0.74357(17) 0.17427(7) 0.0274(3) Uani 1 1 d . . . H5 H 1.3331 0.8143 0.1670 0.033 Uiso 1 1 calc R . . C6 C 1.0223(2) 0.74026(17) 0.03694(7) 0.0275(3) Uani 1 1 d . . . C7 C -0.0893(2) 0.14259(16) 0.17048(7) 0.0257(3) Uani 1 1 d . . . C8 C -0.0899(2) 0.12502(17) 0.25275(7) 0.0278(3) Uani 1 1 d . . . H8A H -0.1562 -0.0110 0.2548 0.033 Uiso 1 1 calc R . . H8B H -0.2119 0.1923 0.2749 0.033 Uiso 1 1 calc R . . C9 C 0.1639(2) 0.20010(17) 0.30329(7) 0.0281(3) Uani 1 1 d . . . H9A H 0.2301 0.3376 0.3040 0.034 Uiso 1 1 calc R . . H9B H 0.2893 0.1348 0.2821 0.034 Uiso 1 1 calc R . . C10 C 0.1331(2) 0.16784(19) 0.38427(7) 0.0313(3) Uani 1 1 d . . . H10A H 0.0109 0.2366 0.4052 0.038 Uiso 1 1 calc R . . H10B H 0.0580 0.0308 0.3824 0.038 Uiso 1 1 calc R . . C11 C 0.3788(2) 0.23131(18) 0.43826(7) 0.0285(3) Uani 1 1 d . . . H11A H 0.4566 0.3683 0.4408 0.034 Uiso 1 1 calc R . . H11B H 0.5013 0.1605 0.4191 0.034 Uiso 1 1 calc R . . C12 C 0.3244(2) 0.19551(19) 0.51739(7) 0.0306(3) Uani 1 1 d . . . H12A H 0.2000 0.2661 0.5350 0.037 Uiso 1 1 calc R . . H12B H 0.2419 0.0586 0.5132 0.037 Uiso 1 1 calc R . . C13 C 0.5502(2) 0.24979(17) 0.57715(7) 0.0267(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0295(5) 0.0466(5) 0.0231(5) 0.0096(4) -0.0041(4) -0.0023(4) O2 0.0275(5) 0.0471(6) 0.0223(5) 0.0096(4) -0.0022(4) -0.0039(4) O3 0.0301(5) 0.0433(5) 0.0258(5) 0.0094(4) -0.0058(4) -0.0039(4) O4 0.0272(5) 0.0602(6) 0.0319(5) 0.0127(4) 0.0002(4) 0.0056(4) O5 0.0292(5) 0.0657(7) 0.0208(5) 0.0103(4) -0.0019(4) 0.0054(5) N1 0.0293(6) 0.0336(6) 0.0230(5) 0.0053(4) -0.0005(4) 0.0075(4) N2 0.0350(7) 0.0673(8) 0.0265(6) 0.0195(6) -0.0074(5) -0.0157(6) C1 0.0340(7) 0.0322(6) 0.0240(6) 0.0074(5) 0.0046(5) 0.0102(5) C2 0.0269(6) 0.0349(7) 0.0305(7) 0.0086(5) 0.0040(5) 0.0044(5) C3 0.0263(6) 0.0318(6) 0.0261(6) 0.0048(5) -0.0021(5) 0.0045(5) C4 0.0267(6) 0.0254(6) 0.0228(6) 0.0038(5) 0.0007(5) 0.0066(5) C5 0.0255(6) 0.0314(6) 0.0241(6) 0.0059(5) 0.0003(5) 0.0053(5) C6 0.0266(6) 0.0299(6) 0.0230(6) 0.0047(5) -0.0025(5) 0.0036(5) C7 0.0253(6) 0.0259(6) 0.0243(6) 0.0051(5) -0.0010(5) 0.0047(5) C8 0.0271(6) 0.0310(6) 0.0242(6) 0.0075(5) 0.0014(5) 0.0046(5) C9 0.0276(6) 0.0315(6) 0.0233(6) 0.0069(5) -0.0004(5) 0.0040(5) C10 0.0283(7) 0.0395(7) 0.0245(7) 0.0087(5) 0.0006(5) 0.0047(5) C11 0.0289(7) 0.0325(7) 0.0237(6) 0.0068(5) 0.0009(5) 0.0065(5) C12 0.0266(6) 0.0402(7) 0.0235(6) 0.0059(5) 0.0000(5) 0.0065(5) C13 0.0287(7) 0.0290(6) 0.0231(6) 0.0041(5) 0.0018(5) 0.0094(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.2438(15) . ? O2 C7 1.3110(15) . ? O2 H21 0.893(18) . ? O3 C7 1.2213(15) . ? O4 C13 1.2040(15) . ? O5 C13 1.3341(15) . ? O5 H51 0.891(19) . ? N1 C1 1.3347(16) . ? N1 C5 1.3385(16) . ? N2 C6 1.3157(17) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? C1 C2 1.3849(18) . ? C1 H1 0.9500 . ? C2 C3 1.3844(18) . ? C2 H2 0.9500 . ? C3 C4 1.3910(17) . ? C3 H3 0.9500 . ? C4 C5 1.3888(17) . ? C4 C6 1.4948(17) . ? C5 H5 0.9500 . ? C7 C8 1.5023(16) . ? C8 C9 1.5222(17) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5244(17) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5176(17) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5222(17) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.4989(17) . ? C12 H12A 0.9900 . ? C12 H12B 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 C7 O2 H21 112.6(10) . . ? C13 O5 H51 110.2(11) . . ? C1 N1 C5 118.08(11) . . ? C6 N2 H2A 120.0 . . ? C6 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? N1 C1 C2 122.86(11) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 118.73(12) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.13(11) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 117.97(11) . . ? C5 C4 C6 122.43(11) . . ? C3 C4 C6 119.60(11) . . ? N1 C5 C4 123.21(11) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? O1 C6 N2 121.72(11) . . ? O1 C6 C4 119.66(11) . . ? N2 C6 C4 118.62(11) . . ? O3 C7 O2 122.83(11) . . ? O3 C7 C8 122.32(11) . . ? O2 C7 C8 114.85(10) . . ? C7 C8 C9 117.13(10) . . ? C7 C8 H8A 108.0 . . ? C9 C8 H8A 108.0 . . ? C7 C8 H8B 108.0 . . ? C9 C8 H8B 108.0 . . ? H8A C8 H8B 107.3 . . ? C8 C9 C10 110.84(10) . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 114.67(10) . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 110.04(10) . . ? C10 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? C10 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C13 C12 C11 116.28(11) . . ? C13 C12 H12A 108.2 . . ? C11 C12 H12A 108.2 . . ? C13 C12 H12B 108.2 . . ? C11 C12 H12B 108.2 . . ? H12A C12 H12B 107.4 . . ? O4 C13 O5 122.82(12) . . ? O4 C13 C12 126.14(11) . . ? O5 C13 C12 111.03(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 1.42(18) . . . . ? N1 C1 C2 C3 -0.87(19) . . . . ? C1 C2 C3 C4 -0.54(18) . . . . ? C2 C3 C4 C5 1.31(17) . . . . ? C2 C3 C4 C6 -178.18(11) . . . . ? C1 N1 C5 C4 -0.57(18) . . . . ? C3 C4 C5 N1 -0.79(18) . . . . ? C6 C4 C5 N1 178.69(11) . . . . ? C5 C4 C6 O1 176.45(11) . . . . ? C3 C4 C6 O1 -4.09(18) . . . . ? C5 C4 C6 N2 -4.11(18) . . . . ? C3 C4 C6 N2 175.36(12) . . . . ? O3 C7 C8 C9 170.95(11) . . . . ? O2 C7 C8 C9 -9.54(16) . . . . ? C7 C8 C9 C10 -178.65(10) . . . . ? C8 C9 C10 C11 177.71(10) . . . . ? C9 C10 C11 C12 179.02(10) . . . . ? C10 C11 C12 C13 179.52(10) . . . . ? C11 C12 C13 O4 -2.34(19) . . . . ? C11 C12 C13 O5 178.20(10) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.197 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.035 data_(na).(sub) _database_code_depnum_ccdc_archive 'CCDC 695335' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nicotinamide:suberic acid 1:1 ; _chemical_name_common 'nicotinamide:suberic acid 1:1' _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N2 O, C8 H14 O4' _chemical_formula_sum 'C14 H20 N2 O5' _chemical_formula_weight 296.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 4.95370(10) _cell_length_b 35.2893(6) _cell_length_c 8.7180(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.8320(10) _cell_angle_gamma 90.00 _cell_volume 1518.60(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 16782 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 17.68 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.919 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Poor (weakly diffracting) crystals: theta(max)=17.68deg. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 4592 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 17.68 _reflns_number_total 982 _reflns_number_gt 898 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0446P)^2^+0.3752P] 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 982 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0734 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8745(4) 0.30154(4) 0.5036(2) 0.0333(5) Uani 1 1 d . . . O2 O 1.1089(3) 0.33107(6) 0.8417(2) 0.0383(6) Uani 1 1 d . . . O3 O 0.8785(4) 0.36826(5) 0.9903(2) 0.0427(6) Uani 1 1 d . . . H3A H 0.796(5) 0.3439(8) 1.024(3) 0.051 Uiso 1 1 d . . . O4 O 0.9483(4) 0.63639(7) 0.6097(2) 0.0468(6) Uani 1 1 d . . . H4A H 1.019(5) 0.6576(8) 0.563(3) 0.056 Uiso 1 1 d . . . O5 O 1.2895(4) 0.60294(5) 0.5314(2) 0.0541(7) Uani 1 1 d . . . N1 N 0.6526(5) 0.19219(8) 0.5935(3) 0.0291(6) Uani 1 1 d . . . N2 N 0.5293(4) 0.32696(7) 0.6187(2) 0.0344(6) Uani 1 1 d . . . H2A H 0.5740 0.3500 0.5915 0.041 Uiso 1 1 calc R . . H2B H 0.3884 0.3235 0.6722 0.041 Uiso 1 1 calc R . . C1 C 0.4559(7) 0.18632(8) 0.6866(4) 0.0309(8) Uani 1 1 d . . . H1 H 0.4096 0.1609 0.7095 0.037 Uiso 1 1 calc R . . C2 C 0.3175(5) 0.21516(11) 0.7510(3) 0.0291(7) Uani 1 1 d . . . H2 H 0.1782 0.2098 0.8162 0.035 Uiso 1 1 calc R . . C3 C 0.3840(6) 0.25192(10) 0.7193(3) 0.0272(7) Uani 1 1 d . . . H3 H 0.2906 0.2723 0.7623 0.033 Uiso 1 1 calc R . . C4 C 0.5887(6) 0.25907(9) 0.6239(3) 0.0220(7) Uani 1 1 d . . . C5 C 0.7155(5) 0.22805(12) 0.5635(3) 0.0274(7) Uani 1 1 d . . . H5 H 0.8547 0.2326 0.4972 0.033 Uiso 1 1 calc R . . C6 C 0.6733(6) 0.29770(9) 0.5794(3) 0.0255(7) Uani 1 1 d . . . C7 C 1.0551(6) 0.36262(10) 0.8883(4) 0.0311(8) Uani 1 1 d . . . C8 C 1.1882(5) 0.39811(8) 0.8376(3) 0.0415(8) Uani 1 1 d . . . H8A H 1.2537 0.3934 0.7351 0.050 Uiso 1 1 calc R . . H8B H 1.3491 0.4031 0.9100 0.050 Uiso 1 1 calc R . . C9 C 1.0147(5) 0.43351(7) 0.8273(3) 0.0371(8) Uani 1 1 d . . . H9A H 0.9519 0.4389 0.9299 0.044 Uiso 1 1 calc R . . H9B H 0.8526 0.4288 0.7554 0.044 Uiso 1 1 calc R . . C10 C 1.1632(5) 0.46801(8) 0.7729(3) 0.0428(8) Uani 1 1 d . . . H10A H 1.3207 0.4733 0.8475 0.051 Uiso 1 1 calc R . . H10B H 1.2335 0.4621 0.6727 0.051 Uiso 1 1 calc R . . C11 C 0.9904(5) 0.50336(7) 0.7549(3) 0.0401(8) Uani 1 1 d . . . H11A H 0.9286 0.5102 0.8564 0.048 Uiso 1 1 calc R . . H11B H 0.8277 0.4977 0.6848 0.048 Uiso 1 1 calc R . . C12 C 1.1358(5) 0.53713(7) 0.6923(3) 0.0407(8) Uani 1 1 d . . . H12A H 1.3002 0.5426 0.7613 0.049 Uiso 1 1 calc R . . H12B H 1.1945 0.5306 0.5898 0.049 Uiso 1 1 calc R . . C13 C 0.9616(5) 0.57240(8) 0.6776(3) 0.0381(8) Uani 1 1 d . . . H13A H 0.7877 0.5660 0.6191 0.046 Uiso 1 1 calc R . . H13B H 0.9205 0.5805 0.7819 0.046 Uiso 1 1 calc R . . C14 C 1.0868(8) 0.60482(9) 0.6002(3) 0.0331(8) 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 O1 0.0322(12) 0.0268(12) 0.0443(12) 0.0021(9) 0.0230(11) 0.0009(10) O2 0.0436(12) 0.0233(14) 0.0503(13) -0.0030(10) 0.0173(9) 0.0024(10) O3 0.0559(13) 0.0221(13) 0.0554(14) 0.0024(10) 0.0356(12) -0.0027(10) O4 0.0524(13) 0.0204(15) 0.0719(15) 0.0134(10) 0.0300(11) 0.0043(12) O5 0.0510(15) 0.0338(14) 0.0827(17) 0.0127(10) 0.0364(14) 0.0066(11) N1 0.0323(16) 0.021(2) 0.0356(16) 0.0015(12) 0.0122(14) -0.0006(12) N2 0.0335(14) 0.0226(16) 0.0504(16) 0.0047(11) 0.0222(12) 0.0005(13) C1 0.0325(19) 0.024(2) 0.0362(19) 0.0038(17) 0.0056(17) -0.0029(18) C2 0.0286(18) 0.028(2) 0.0321(18) 0.0039(18) 0.0116(15) 0.001(2) C3 0.028(2) 0.025(3) 0.0291(18) -0.0014(15) 0.0078(17) 0.0051(15) C4 0.0218(19) 0.020(3) 0.0245(18) 0.0036(17) 0.0051(17) 0.0000(19) C5 0.0262(17) 0.028(2) 0.0293(19) 0.0032(18) 0.0082(14) 0.001(2) C6 0.0253(19) 0.023(2) 0.0286(18) -0.0013(17) 0.0060(16) 0.008(2) C7 0.0301(19) 0.030(3) 0.034(2) 0.0051(18) 0.0081(17) -0.0006(18) C8 0.0440(19) 0.027(2) 0.056(2) 0.0075(15) 0.0228(16) 0.0014(18) C9 0.0423(18) 0.0248(19) 0.0458(19) 0.0034(15) 0.0132(15) 0.0058(17) C10 0.0518(19) 0.025(2) 0.054(2) 0.0069(14) 0.0171(16) -0.0044(18) C11 0.0504(19) 0.021(2) 0.051(2) 0.0050(14) 0.0162(16) 0.0017(18) C12 0.0492(19) 0.021(2) 0.053(2) 0.0090(15) 0.0124(16) -0.0014(17) C13 0.0499(19) 0.019(2) 0.0469(19) 0.0052(15) 0.0138(16) -0.0015(18) C14 0.043(2) 0.018(2) 0.039(2) 0.0024(17) 0.0051(18) 0.003(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 O1 C6 1.249(3) . ? O2 C7 1.222(3) . ? O3 C7 1.314(3) . ? O3 H3A 1.01(3) . ? O4 C14 1.315(3) . ? O4 H4A 0.93(3) . ? O5 C14 1.214(3) . ? N1 C5 1.334(3) . ? N1 C1 1.336(3) . ? N2 C6 1.317(3) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? C1 C2 1.373(3) . ? C1 H1 0.9500 . ? C2 C3 1.372(3) . ? C2 H2 0.9500 . ? C3 C4 1.388(3) . ? C3 H3 0.9500 . ? C4 C5 1.388(3) . ? C4 C6 1.487(4) . ? C5 H5 0.9500 . ? C7 C8 1.499(4) . ? C8 C9 1.515(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.519(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.513(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.518(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.514(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.490(4) . ? C13 H13A 0.9900 . ? C13 H13B 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 C7 O3 H3A 112.2(14) . . ? C14 O4 H4A 115.7(17) . . ? C5 N1 C1 117.4(2) . . ? C6 N2 H2A 120.0 . . ? C6 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? N1 C1 C2 123.2(2) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C3 C2 C1 118.8(2) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.5(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 117.5(2) . . ? C3 C4 C6 124.0(3) . . ? C5 C4 C6 118.5(3) . . ? N1 C5 C4 123.6(2) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? O1 C6 N2 121.8(3) . . ? O1 C6 C4 119.5(3) . . ? N2 C6 C4 118.7(3) . . ? O2 C7 O3 122.6(3) . . ? O2 C7 C8 123.3(3) . . ? O3 C7 C8 114.0(3) . . ? C7 C8 C9 116.4(2) . . ? C7 C8 H8A 108.2 . . ? C9 C8 H8A 108.2 . . ? C7 C8 H8B 108.2 . . ? C9 C8 H8B 108.2 . . ? H8A C8 H8B 107.3 . . ? C8 C9 C10 113.1(2) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 114.1(2) . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 113.8(2) . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 113.0(2) . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? C11 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 114.4(2) . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13B 108.7 . . ? C12 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? O5 C14 O4 122.4(3) . . ? O5 C14 C13 125.1(3) . . ? O4 C14 C13 112.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.3(3) . . . . ? N1 C1 C2 C3 -0.3(3) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C2 C3 C4 C6 178.7(2) . . . . ? C1 N1 C5 C4 0.2(3) . . . . ? C3 C4 C5 N1 -0.7(3) . . . . ? C6 C4 C5 N1 -178.8(2) . . . . ? C3 C4 C6 O1 174.0(2) . . . . ? C5 C4 C6 O1 -7.9(3) . . . . ? C3 C4 C6 N2 -7.4(3) . . . . ? C5 C4 C6 N2 170.7(2) . . . . ? O2 C7 C8 C9 146.7(2) . . . . ? O3 C7 C8 C9 -34.6(3) . . . . ? C7 C8 C9 C10 -179.1(2) . . . . ? C8 C9 C10 C11 177.4(2) . . . . ? C9 C10 C11 C12 -176.9(2) . . . . ? C10 C11 C12 C13 -179.0(2) . . . . ? C11 C12 C13 C14 -173.4(2) . . . . ? C12 C13 C14 O5 11.3(4) . . . . ? C12 C13 C14 O4 -170.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 17.68 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.118 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.026 data_(na)2.(sub) _database_code_depnum_ccdc_archive 'CCDC 695336' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nicotinamide:suberic acid 2:1 ; _chemical_name_common 'nicotinamide:suberic acid 2:1' _chemical_melting_point ? _chemical_formula_moiety 'C8 H14 O4, 2(C6 H6 N2 O)' _chemical_formula_sum 'C20 H26 N4 O6' _chemical_formula_weight 418.45 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 5.0288(3) _cell_length_b 5.4403(3) _cell_length_c 18.7537(11) _cell_angle_alpha 93.062(3) _cell_angle_beta 94.810(3) _cell_angle_gamma 90.740(2) _cell_volume 510.45(5) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7216 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 30.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 222 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.937 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atom was located and its position was refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 6237 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.1063 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 29.90 _reflns_number_total 2848 _reflns_number_gt 1495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+0.4980P] 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 2848 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1719 _refine_ls_R_factor_gt 0.0800 _refine_ls_wR_factor_ref 0.1764 _refine_ls_wR_factor_gt 0.1370 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3238(4) 0.8094(4) 0.06122(10) 0.0346(5) Uani 1 1 d . . . N1 N 0.4762(5) 0.3822(4) 0.23700(12) 0.0338(6) Uani 1 1 d . . . C1 C 0.6664(6) 0.2140(5) 0.23297(15) 0.0339(7) Uani 1 1 d . . . H1 H 0.6875 0.0996 0.2695 0.041 Uiso 1 1 calc R . . O2 O 0.1720(4) 0.4321(4) 0.34786(11) 0.0402(6) Uani 1 1 d . . . H2C H 0.268(7) 0.414(6) 0.3054(18) 0.048 Uiso 1 1 d . . . N2 N 0.7489(4) 0.7813(4) 0.03355(12) 0.0319(6) Uani 1 1 d . . . H2A H 0.7240 0.8878 0.0000 0.038 Uiso 1 1 calc R . . H2B H 0.9065 0.7152 0.0420 0.038 Uiso 1 1 calc R . . C2 C 0.8330(6) 0.1991(5) 0.17841(15) 0.0320(7) Uani 1 1 d . . . H2 H 0.9673 0.0780 0.1776 0.038 Uiso 1 1 calc R . . O3 O 0.0027(4) 0.7642(4) 0.29671(11) 0.0427(6) Uani 1 1 d . . . C3 C 0.8015(5) 0.3630(5) 0.12484(14) 0.0288(6) Uani 1 1 d . . . H3 H 0.9141 0.3560 0.0866 0.035 Uiso 1 1 calc R . . C4 C 0.6037(5) 0.5382(5) 0.12731(14) 0.0252(6) Uani 1 1 d . . . C5 C 0.4468(5) 0.5417(5) 0.18487(14) 0.0303(6) Uani 1 1 d . . . H5 H 0.3127 0.6625 0.1875 0.036 Uiso 1 1 calc R . . C6 C 0.5484(5) 0.7202(5) 0.07154(14) 0.0277(6) Uani 1 1 d . . . C7 C 0.0131(6) 0.6239(5) 0.34517(15) 0.0323(7) Uani 1 1 d . . . C8 C -0.1492(6) 0.6428(6) 0.40875(16) 0.0381(7) Uani 1 1 d . . . H8A H -0.0287 0.6184 0.4522 0.046 Uiso 1 1 calc R . . H8B H -0.2815 0.5053 0.4039 0.046 Uiso 1 1 calc R . . C9 C -0.2966(6) 0.8793(5) 0.42075(15) 0.0345(7) Uani 1 1 d . . . H9A H -0.4348 0.8969 0.3806 0.041 Uiso 1 1 calc R . . H9B H -0.1702 1.0207 0.4218 0.041 Uiso 1 1 calc R . . C10 C -0.4284(6) 0.8815(5) 0.49129(16) 0.0361(7) Uani 1 1 d . . . H10A H -0.5583 0.7424 0.4891 0.043 Uiso 1 1 calc R . . H10B H -0.2899 0.8548 0.5307 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 O1 0.0226(10) 0.0410(12) 0.0417(12) 0.0173(9) 0.0018(9) 0.0054(8) N1 0.0342(14) 0.0340(14) 0.0348(14) 0.0106(11) 0.0057(11) 0.0066(11) C1 0.0369(17) 0.0323(16) 0.0329(16) 0.0095(12) -0.0012(13) 0.0056(13) O2 0.0465(14) 0.0436(13) 0.0341(12) 0.0135(10) 0.0139(10) 0.0188(10) N2 0.0238(12) 0.0385(14) 0.0351(13) 0.0133(11) 0.0052(10) 0.0041(10) C2 0.0337(16) 0.0271(15) 0.0354(16) 0.0058(12) 0.0009(13) 0.0086(12) O3 0.0532(15) 0.0418(13) 0.0369(12) 0.0162(10) 0.0146(10) 0.0132(10) C3 0.0274(15) 0.0315(16) 0.0280(15) 0.0019(12) 0.0040(11) 0.0048(12) C4 0.0205(13) 0.0270(15) 0.0279(14) 0.0031(11) 0.0009(11) -0.0006(11) C5 0.0287(15) 0.0288(15) 0.0343(16) 0.0070(12) 0.0039(12) 0.0053(12) C6 0.0228(14) 0.0271(15) 0.0333(15) 0.0047(12) 0.0005(11) 0.0000(11) C7 0.0334(16) 0.0336(16) 0.0308(15) 0.0060(13) 0.0047(12) 0.0052(13) C8 0.0446(19) 0.0398(18) 0.0327(16) 0.0126(13) 0.0113(14) 0.0082(14) C9 0.0380(17) 0.0349(17) 0.0321(15) 0.0061(12) 0.0090(13) 0.0026(13) C10 0.0387(18) 0.0355(17) 0.0356(16) 0.0080(13) 0.0085(13) 0.0025(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.239(3) . ? N1 C1 1.336(4) . ? N1 C5 1.342(3) . ? C1 C2 1.375(4) . ? C1 H1 0.9500 . ? O2 C7 1.323(3) . ? O2 H2C 0.97(3) . ? N2 C6 1.331(3) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? C2 C3 1.379(4) . ? C2 H2 0.9500 . ? O3 C7 1.216(3) . ? C3 C4 1.389(4) . ? C3 H3 0.9500 . ? C4 C5 1.389(4) . ? C4 C6 1.490(4) . ? C5 H5 0.9500 . ? C7 C8 1.500(4) . ? C8 C9 1.509(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.528(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C10 1.518(6) 2_476 ? C10 H10A 0.9900 . ? C10 H10B 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 C1 N1 C5 118.0(2) . . ? N1 C1 C2 123.0(3) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C7 O2 H2C 111.3(19) . . ? C6 N2 H2A 120.0 . . ? C6 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C1 C2 C3 118.8(3) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C2 C3 C4 119.4(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 117.8(2) . . ? C3 C4 C6 123.9(2) . . ? C5 C4 C6 118.3(2) . . ? N1 C5 C4 122.9(3) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? O1 C6 N2 121.8(2) . . ? O1 C6 C4 120.8(2) . . ? N2 C6 C4 117.3(2) . . ? O3 C7 O2 123.4(3) . . ? O3 C7 C8 125.3(3) . . ? O2 C7 C8 111.3(2) . . ? C7 C8 C9 117.0(2) . . ? C7 C8 H8A 108.1 . . ? C9 C8 H8A 108.1 . . ? C7 C8 H8B 108.1 . . ? C9 C8 H8B 108.1 . . ? H8A C8 H8B 107.3 . . ? C8 C9 C10 110.8(2) . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C10 C10 C9 114.0(3) 2_476 . ? C10 C10 H10A 108.8 2_476 . ? C9 C10 H10A 108.8 . . ? C10 C10 H10B 108.8 2_476 . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? 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 C5 N1 C1 C2 0.5(4) . . . . ? N1 C1 C2 C3 -0.7(4) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C5 0.7(4) . . . . ? C2 C3 C4 C6 -178.6(3) . . . . ? C1 N1 C5 C4 0.3(4) . . . . ? C3 C4 C5 N1 -0.9(4) . . . . ? C6 C4 C5 N1 178.4(2) . . . . ? C3 C4 C6 O1 154.0(3) . . . . ? C5 C4 C6 O1 -25.3(4) . . . . ? C3 C4 C6 N2 -25.8(4) . . . . ? C5 C4 C6 N2 154.9(3) . . . . ? O3 C7 C8 C9 -12.3(5) . . . . ? O2 C7 C8 C9 167.9(3) . . . . ? C7 C8 C9 C10 -174.1(3) . . . . ? C8 C9 C10 C10 177.6(3) . . . 2_476 ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 29.90 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.266 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.067 data_(na).(aze) _database_code_depnum_ccdc_archive 'CCDC 695337' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nicotinamide:azelaic acid 2:1 ; _chemical_name_common 'nicotinamide:azelaic acid 2:1' _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N2 O, C9 H16 O4' _chemical_formula_sum 'C15 H22 N2 O5' _chemical_formula_weight 310.35 _chemical_absolute_configuration ; 1133 Friedel pairs were averaged for the refinement. ; 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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 8.64550(10) _cell_length_b 36.5695(6) _cell_length_c 5.20210(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1644.70(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 23872 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.937 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atoms were located and their positions were refinede satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 10952 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -47 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2082 _reflns_number_gt 1620 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.3144P] 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 2082 _refine_ls_number_parameters 205 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5529(2) 0.29892(4) 1.7504(4) 0.0482(5) Uani 1 1 d . . . O2 O 0.8911(2) 0.32755(5) 0.9865(4) 0.0569(5) Uani 1 1 d . . . O3 O 1.0730(2) 0.36331(5) 0.8246(4) 0.0591(6) Uani 1 1 d . . . H3A H 1.099(3) 0.3397(8) 0.699(8) 0.071 Uiso 1 1 d . . . O4 O 0.5358(2) 0.63839(5) 1.4411(4) 0.0567(6) Uani 1 1 d . . . H4A H 0.501(3) 0.6583(8) 1.365(7) 0.068 Uiso 1 1 d . . . O5 O 0.4916(3) 0.61078(5) 1.0708(5) 0.0814(8) Uani 1 1 d . . . N1 N 0.6523(2) 0.19274(5) 1.5445(4) 0.0427(5) Uani 1 1 d . . . N2 N 0.6582(3) 0.32234(6) 1.3924(5) 0.0508(6) Uani 1 1 d . . . H2A H 0.6297 0.3446 1.4347 0.061 Uiso 1 1 calc R . . H2B H 0.7091 0.3185 1.2484 0.061 Uiso 1 1 calc R . . C1 C 0.6173(3) 0.22752(6) 1.6029(5) 0.0402(6) Uani 1 1 d . . . H1 H 0.5520 0.2320 1.7463 0.048 Uiso 1 1 calc R . . C2 C 0.6717(2) 0.25702(6) 1.4645(5) 0.0354(5) Uani 1 1 d . . . C3 C 0.7644(3) 0.25031(7) 1.2537(6) 0.0427(6) Uani 1 1 d . . . H3 H 0.8025 0.2700 1.1524 0.051 Uiso 1 1 calc R . . C4 C 0.8013(3) 0.21440(7) 1.1918(6) 0.0471(7) Uani 1 1 d . . . H4 H 0.8653 0.2091 1.0482 0.057 Uiso 1 1 calc R . . C5 C 0.7436(3) 0.18687(7) 1.3421(5) 0.0446(6) Uani 1 1 d . . . H5 H 0.7699 0.1624 1.3001 0.053 Uiso 1 1 calc R . . C6 C 0.6248(3) 0.29467(6) 1.5448(5) 0.0397(6) Uani 1 1 d . . . C7 C 0.9621(3) 0.35611(7) 0.9877(6) 0.0484(7) Uani 1 1 d . . . C8 C 0.9335(4) 0.38615(7) 1.1786(7) 0.0622(9) Uani 1 1 d . . . H8A H 1.0316 0.3919 1.2681 0.075 Uiso 1 1 calc R . . H8B H 0.8588 0.3774 1.3091 0.075 Uiso 1 1 calc R . . C9 C 0.8717(3) 0.42045(7) 1.0568(7) 0.0595(8) Uani 1 1 d . . . H9A H 0.7771 0.4145 0.9584 0.071 Uiso 1 1 calc R . . H9B H 0.9493 0.4301 0.9345 0.071 Uiso 1 1 calc R . . C10 C 0.8338(3) 0.44995(7) 1.2552(7) 0.0571(8) Uani 1 1 d . . . H10A H 0.7563 0.4402 1.3773 0.068 Uiso 1 1 calc R . . H10B H 0.9285 0.4557 1.3540 0.068 Uiso 1 1 calc R . . C11 C 0.7717(4) 0.48484(7) 1.1384(7) 0.0646(9) Uani 1 1 d . . . H11A H 0.6792 0.4789 1.0345 0.078 Uiso 1 1 calc R . . H11B H 0.8507 0.4950 1.0206 0.078 Uiso 1 1 calc R . . C12 C 0.7284(3) 0.51397(6) 1.3327(7) 0.0528(7) Uani 1 1 d . . . H12A H 0.6533 0.5035 1.4561 0.063 Uiso 1 1 calc R . . H12B H 0.8221 0.5210 1.4305 0.063 Uiso 1 1 calc R . . C13 C 0.6590(4) 0.54794(7) 1.2139(7) 0.0567(8) Uani 1 1 d . . . H13A H 0.7332 0.5580 1.0871 0.068 Uiso 1 1 calc R . . H13B H 0.5641 0.5410 1.1196 0.068 Uiso 1 1 calc R . . C14 C 0.6189(3) 0.57764(6) 1.4039(6) 0.0474(7) Uani 1 1 d . . . H14A H 0.5490 0.5673 1.5361 0.057 Uiso 1 1 calc R . . H14B H 0.7147 0.5856 1.4916 0.057 Uiso 1 1 calc R . . C15 C 0.5428(3) 0.61031(6) 1.2854(6) 0.0449(6) 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 O1 0.0627(11) 0.0356(8) 0.0464(11) 0.0022(8) 0.0257(10) 0.0063(8) O2 0.0687(12) 0.0429(9) 0.0590(13) -0.0057(10) 0.0277(11) -0.0109(8) O3 0.0735(12) 0.0374(9) 0.0665(14) -0.0075(10) 0.0320(12) -0.0113(9) O4 0.0858(14) 0.0334(9) 0.0510(12) -0.0070(9) -0.0228(12) 0.0144(9) O5 0.139(2) 0.0442(11) 0.0609(15) -0.0129(11) -0.0444(17) 0.0257(12) N1 0.0482(11) 0.0366(10) 0.0432(13) -0.0005(10) 0.0116(12) 0.0023(9) N2 0.0699(14) 0.0347(10) 0.0479(14) 0.0047(10) 0.0275(13) 0.0087(10) C1 0.0430(13) 0.0388(12) 0.0388(14) -0.0004(11) 0.0102(12) 0.0057(10) C2 0.0365(11) 0.0362(11) 0.0335(12) 0.0002(11) 0.0043(12) 0.0029(9) C3 0.0465(13) 0.0402(12) 0.0415(14) 0.0035(12) 0.0122(13) 0.0015(10) C4 0.0528(15) 0.0452(13) 0.0434(16) -0.0026(13) 0.0166(14) 0.0072(12) C5 0.0492(14) 0.0390(12) 0.0455(16) -0.0046(12) 0.0104(14) 0.0034(11) C6 0.0416(12) 0.0394(12) 0.0383(14) 0.0026(12) 0.0102(12) 0.0037(10) C7 0.0604(16) 0.0355(12) 0.0493(17) 0.0035(13) 0.0157(15) 0.0026(12) C8 0.087(2) 0.0388(13) 0.061(2) -0.0037(14) 0.0214(19) 0.0032(13) C9 0.0656(17) 0.0444(14) 0.069(2) -0.0082(16) 0.0019(18) 0.0088(13) C10 0.0612(16) 0.0371(13) 0.073(2) -0.0076(15) 0.0060(18) 0.0060(12) C11 0.078(2) 0.0410(15) 0.075(2) -0.0082(16) -0.0012(19) 0.0125(14) C12 0.0589(15) 0.0346(13) 0.065(2) -0.0055(14) -0.0039(17) 0.0035(11) C13 0.0718(18) 0.0390(13) 0.0595(19) -0.0064(14) -0.0062(18) 0.0098(13) C14 0.0565(15) 0.0317(11) 0.0540(17) -0.0023(12) -0.0124(15) 0.0022(11) C15 0.0542(14) 0.0341(13) 0.0463(17) -0.0046(13) -0.0110(15) 0.0014(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.246(3) . ? O2 C7 1.211(3) . ? O3 C7 1.307(3) . ? O3 H3A 1.11(3) . ? O4 C15 1.309(3) . ? O4 H4A 0.88(3) . ? O5 C15 1.201(4) . ? N1 C5 1.334(3) . ? N1 C1 1.342(3) . ? N2 C6 1.317(3) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? C1 C2 1.380(3) . ? C1 H1 0.9500 . ? C2 C3 1.380(4) . ? C2 C6 1.495(3) . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C5 1.369(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C7 C8 1.501(4) . ? C8 C9 1.503(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.529(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.512(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.515(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.512(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.509(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.496(3) . ? C14 H14A 0.9900 . ? C14 H14B 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 C7 O3 H3A 112.0(16) . . ? C15 O4 H4A 113(2) . . ? C5 N1 C1 117.7(2) . . ? C6 N2 H2A 120.0 . . ? C6 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? N1 C1 C2 123.1(2) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 118.3(2) . . ? C1 C2 C6 118.8(2) . . ? C3 C2 C6 122.9(2) . . ? C2 C3 C4 119.0(2) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 118.6(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 123.3(2) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? O1 C6 N2 122.0(2) . . ? O1 C6 C2 119.3(2) . . ? N2 C6 C2 118.7(2) . . ? O2 C7 O3 122.8(3) . . ? O2 C7 C8 123.4(3) . . ? O3 C7 C8 113.7(2) . . ? C7 C8 C9 113.0(3) . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 C10 112.4(3) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 113.6(3) . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C11 C12 114.4(3) . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C13 C12 C11 113.8(3) . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 114.5(3) . . ? C14 C13 H13A 108.6 . . ? C12 C13 H13A 108.6 . . ? C14 C13 H13B 108.6 . . ? C12 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C13 113.9(3) . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? O5 C15 O4 123.1(2) . . ? O5 C15 C14 123.8(2) . . ? O4 C15 C14 113.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -0.3(4) . . . . ? N1 C1 C2 C3 1.1(4) . . . . ? N1 C1 C2 C6 179.6(2) . . . . ? C1 C2 C3 C4 -1.0(4) . . . . ? C6 C2 C3 C4 -179.5(3) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C1 N1 C5 C4 -0.6(4) . . . . ? C3 C4 C5 N1 0.6(4) . . . . ? C1 C2 C6 O1 8.2(4) . . . . ? C3 C2 C6 O1 -173.4(2) . . . . ? C1 C2 C6 N2 -170.5(2) . . . . ? C3 C2 C6 N2 8.0(4) . . . . ? O2 C7 C8 C9 -114.7(3) . . . . ? O3 C7 C8 C9 66.3(4) . . . . ? C7 C8 C9 C10 176.4(2) . . . . ? C8 C9 C10 C11 179.8(3) . . . . ? C9 C10 C11 C12 178.1(3) . . . . ? C10 C11 C12 C13 -177.1(3) . . . . ? C11 C12 C13 C14 -178.6(3) . . . . ? C12 C13 C14 C15 -177.0(2) . . . . ? C13 C14 C15 O5 13.2(4) . . . . ? C13 C14 C15 O4 -167.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.196 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.034 data_(na)2.(seb) _database_code_depnum_ccdc_archive 'CCDC 695338' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nicotinamide:sebacic acid 2:1 ; _chemical_name_common 'nicotinamide:sebacic acid 2:1' _chemical_melting_point ? _chemical_formula_moiety 'C10 H18 O4, 2(C6 H6 O2 N)' _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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.0365(2) _cell_length_b 5.4470(2) _cell_length_c 20.5004(9) _cell_angle_alpha 89.354(2) _cell_angle_beta 84.241(2) _cell_angle_gamma 89.872(2) _cell_volume 559.53(4) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7012 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 238 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.909 _exptl_absorpt_correction_T_max 1.018 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -OH hydrogen atom was located and its position was refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5593 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 27.53 _reflns_number_total 2529 _reflns_number_gt 1906 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.2549P] 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 2529 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1267 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7843(2) 0.7969(2) 0.05643(6) 0.0391(3) Uani 1 1 d . . . O2 O 0.4426(3) 0.3510(3) 0.31871(6) 0.0462(4) Uani 1 1 d . . . H2C H 0.577(5) 0.351(4) 0.2820(11) 0.055 Uiso 1 1 d . . . O3 O 0.3062(3) 0.6954(3) 0.27232(6) 0.0488(4) Uani 1 1 d . . . N1 N 0.8225(3) 0.3287(3) 0.21691(7) 0.0382(4) Uani 1 1 d . . . N2 N 1.2293(3) 0.7742(3) 0.03105(7) 0.0345(3) Uani 1 1 d . . . H2A H 1.2262 0.8880 0.0003 0.041 Uiso 1 1 calc R . . H2B H 1.3816 0.7058 0.0388 0.041 Uiso 1 1 calc R . . C1 C 1.0181(4) 0.1607(3) 0.21321(9) 0.0375(4) Uani 1 1 d . . . H1 H 1.0160 0.0379 0.2465 0.045 Uiso 1 1 calc R . . C2 C 1.2221(4) 0.1587(3) 0.16308(9) 0.0371(4) Uani 1 1 d . . . H2 H 1.3585 0.0377 0.1622 0.044 Uiso 1 1 calc R . . C3 C 1.2252(3) 0.3359(3) 0.11405(8) 0.0338(4) Uani 1 1 d . . . H3 H 1.3640 0.3386 0.0791 0.041 Uiso 1 1 calc R . . C4 C 1.0220(3) 0.5099(3) 0.11678(8) 0.0290(4) Uani 1 1 d . . . C5 C 0.8266(3) 0.4988(3) 0.16937(8) 0.0341(4) Uani 1 1 d . . . H5 H 0.6884 0.6183 0.1717 0.041 Uiso 1 1 calc R . . C6 C 1.0031(3) 0.7052(3) 0.06582(8) 0.0296(4) Uani 1 1 d . . . C7 C 0.2848(4) 0.5456(3) 0.31641(8) 0.0350(4) Uani 1 1 d . . . C8 C 0.0770(4) 0.5505(3) 0.37427(9) 0.0416(5) Uani 1 1 d . . . H8A H 0.1656 0.5125 0.4142 0.050 Uiso 1 1 calc R . . H8B H -0.0523 0.4172 0.3691 0.050 Uiso 1 1 calc R . . C9 C -0.0776(4) 0.7878(3) 0.38554(9) 0.0376(4) Uani 1 1 d . . . H9A H -0.1879 0.8172 0.3489 0.045 Uiso 1 1 calc R . . H9B H 0.0489 0.9263 0.3865 0.045 Uiso 1 1 calc R . . C10 C -0.2569(4) 0.7774(3) 0.44985(9) 0.0409(4) Uani 1 1 d . . . H10A H -0.3855 0.6413 0.4476 0.049 Uiso 1 1 calc R . . H10B H -0.1451 0.7373 0.4856 0.049 Uiso 1 1 calc R . . C11 C -0.4120(4) 1.0098(3) 0.46770(8) 0.0396(4) Uani 1 1 d . . . H11A H -0.5253 1.0505 0.4323 0.047 Uiso 1 1 calc R . . H11B H -0.2845 1.1466 0.4704 0.047 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 O1 0.0252(6) 0.0467(7) 0.0452(7) 0.0177(6) -0.0047(5) 0.0028(5) O2 0.0488(8) 0.0493(8) 0.0374(7) 0.0138(6) 0.0098(6) 0.0191(6) O3 0.0551(9) 0.0462(8) 0.0417(7) 0.0167(6) 0.0100(6) 0.0139(6) N1 0.0382(8) 0.0398(9) 0.0354(8) 0.0096(6) 0.0010(6) 0.0064(6) N2 0.0266(7) 0.0398(8) 0.0365(8) 0.0119(6) -0.0019(6) 0.0036(6) C1 0.0425(10) 0.0350(9) 0.0349(9) 0.0096(7) -0.0045(7) 0.0048(8) C2 0.0384(10) 0.0327(9) 0.0402(10) 0.0025(7) -0.0053(7) 0.0099(7) C3 0.0312(9) 0.0376(9) 0.0318(8) 0.0022(7) 0.0001(7) 0.0059(7) C4 0.0266(8) 0.0311(8) 0.0298(8) 0.0032(6) -0.0050(6) 0.0012(6) C5 0.0309(9) 0.0352(9) 0.0357(9) 0.0065(7) -0.0010(7) 0.0066(7) C6 0.0270(8) 0.0327(8) 0.0293(8) 0.0030(6) -0.0043(6) 0.0003(6) C7 0.0355(9) 0.0358(9) 0.0331(9) 0.0050(7) -0.0010(7) 0.0043(7) C8 0.0444(11) 0.0409(10) 0.0370(10) 0.0094(8) 0.0070(8) 0.0069(8) C9 0.0381(10) 0.0389(10) 0.0342(9) 0.0067(7) 0.0029(7) 0.0035(8) C10 0.0451(11) 0.0415(10) 0.0341(9) 0.0072(7) 0.0056(8) 0.0049(8) C11 0.0425(10) 0.0402(10) 0.0342(9) 0.0060(7) 0.0044(8) 0.0029(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.2406(19) . ? O2 C7 1.327(2) . ? O2 H2C 0.96(2) . ? O3 C7 1.208(2) . ? N1 C5 1.336(2) . ? N1 C1 1.340(2) . ? N2 C6 1.334(2) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? C1 C2 1.379(3) . ? C1 H1 0.9500 . ? C2 C3 1.385(2) . ? C2 H2 0.9500 . ? C3 C4 1.391(2) . ? C3 H3 0.9500 . ? C4 C5 1.386(2) . ? C4 C6 1.492(2) . ? C5 H5 0.9500 . ? C7 C8 1.502(2) . ? C8 C9 1.515(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.522(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.515(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C11 1.520(3) 2_476 ? C11 H11A 0.9900 . ? C11 H11B 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 C7 O2 H2C 110.9(13) . . ? C5 N1 C1 117.95(15) . . ? C6 N2 H2A 120.0 . . ? C6 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? N1 C1 C2 122.75(15) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 118.96(16) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 119.00(15) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 117.95(15) . . ? C5 C4 C6 118.69(14) . . ? C3 C4 C6 123.35(14) . . ? N1 C5 C4 123.38(15) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? O1 C6 N2 122.06(15) . . ? O1 C6 C4 120.65(14) . . ? N2 C6 C4 117.29(14) . . ? O3 C7 O2 123.37(16) . . ? O3 C7 C8 125.24(16) . . ? O2 C7 C8 111.37(14) . . ? C7 C8 C9 116.66(15) . . ? C7 C8 H8A 108.1 . . ? C9 C8 H8A 108.1 . . ? C7 C8 H8B 108.1 . . ? C9 C8 H8B 108.1 . . ? H8A C8 H8B 107.3 . . ? C8 C9 C10 111.00(14) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 115.57(15) . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? C9 C10 H10B 108.4 . . ? H10A C10 H10B 107.4 . . ? C10 C11 C11 113.56(18) . 2_476 ? C10 C11 H11A 108.9 . . ? C11 C11 H11A 108.9 2_476 . ? C10 C11 H11B 108.9 . . ? C11 C11 H11B 108.9 2_476 . ? H11A C11 H11B 107.7 . . ? 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 C5 N1 C1 C2 0.7(3) . . . . ? N1 C1 C2 C3 -0.6(3) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 0.8(3) . . . . ? C2 C3 C4 C6 -178.66(16) . . . . ? C1 N1 C5 C4 0.0(3) . . . . ? C3 C4 C5 N1 -0.7(3) . . . . ? C6 C4 C5 N1 178.77(17) . . . . ? C5 C4 C6 O1 -25.3(2) . . . . ? C3 C4 C6 O1 154.08(18) . . . . ? C5 C4 C6 N2 155.14(16) . . . . ? C3 C4 C6 N2 -25.5(2) . . . . ? O3 C7 C8 C9 -13.9(3) . . . . ? O2 C7 C8 C9 167.34(17) . . . . ? C7 C8 C9 C10 -173.31(17) . . . . ? C8 C9 C10 C11 177.35(18) . . . . ? C9 C10 C11 C11 180.0(2) . . . 2_476 ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.202 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.044