# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Thompson, Laura' 'Voguri, Raja' 'Male, Louise' 'Tremayne, Maryjane' _publ_contact_author_name 'Tremayne, Maryjane' _publ_contact_author_email m.tremayne@bham.ac.uk _publ_section_title ; The Crystal Structures and Melting Point Properties of Isonicotinamide Cocrystals with Alkanediacids HO2C(CH2)n-2CO2H n=7-9 ; # Attachment '- isonicotinamide_azelaic.cif' data_2010src0565r _database_code_depnum_ccdc_archive 'CCDC 810990' #TrackingRef '- isonicotinamide_azelaic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Isonicotinamide:azelaic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H16 O4, C6 H6 N2 O' _chemical_formula_sum 'C15 H22 N2 O5' _chemical_formula_weight 310.35 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 'P 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 8.2118(11) _cell_length_b 5.0680(7) _cell_length_c 38.683(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.264(6) _cell_angle_gamma 90.00 _cell_volume 1607.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 35938 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9876 _exptl_absorpt_correction_T_max 0.9961 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 10359 reflections reduced R(int) from 0.1925 to 0.0793 Ratio of minimum to maximum apparent transmission: 0.864805 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11278 _diffrn_reflns_av_R_equivalents 0.0748 _diffrn_reflns_av_sigmaI/netI 0.0635 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2761 _reflns_number_gt 2049 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0519P)^2^+4.3636P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2761 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1217 _refine_ls_R_factor_gt 0.0880 _refine_ls_wR_factor_ref 0.2250 _refine_ls_wR_factor_gt 0.1995 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _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 C2 C 0.6162(5) 0.2604(9) 0.97457(10) 0.0332(10) Uani 1 1 d . . . H2 H 0.5474 0.1101 0.9721 0.040 Uiso 1 1 calc R . . C3 C 0.6852(6) 0.3178(9) 1.00704(11) 0.0371(11) Uani 1 1 d . . . H3 H 0.6647 0.2087 1.0263 0.044 Uiso 1 1 calc R . . C4 C 0.7855(5) 0.5385(8) 1.01112(10) 0.0302(10) Uani 1 1 d . . . C5 C 0.8120(5) 0.6902(9) 0.98189(10) 0.0331(10) Uani 1 1 d . . . H5 H 0.8802 0.8416 0.9836 0.040 Uiso 1 1 calc R . . C6 C 0.7374(5) 0.6166(9) 0.95048(11) 0.0355(11) Uani 1 1 d . . . H6 H 0.7557 0.7216 0.9307 0.043 Uiso 1 1 calc R . . C7 C 0.8655(5) 0.6190(9) 1.04536(10) 0.0310(10) Uani 1 1 d . . . N1 N 0.6409(4) 0.4053(7) 0.94641(8) 0.0342(9) Uani 1 1 d . . . N7 N 0.8424(4) 0.4696(7) 1.07265(8) 0.0360(9) Uani 1 1 d . . . H7A H 0.8900 0.5104 1.0929 0.043 Uiso 1 1 calc R . . H7B H 0.7794 0.3294 1.0706 0.043 Uiso 1 1 calc R . . O7 O 0.9534(4) 0.8200(6) 1.04678(7) 0.0340(8) Uani 1 1 d . . . C8 C 0.0796(5) 0.1185(9) 0.63278(10) 0.0320(10) Uani 1 1 d . . . C9 C 0.1545(6) -0.0274(10) 0.66283(10) 0.0375(11) Uani 1 1 d . . . H9A H 0.2626 -0.0929 0.6567 0.045 Uiso 1 1 calc R . . H9B H 0.0858 -0.1832 0.6672 0.045 Uiso 1 1 calc R . . C10 C 0.1764(6) 0.1306(10) 0.69621(10) 0.0368(11) Uani 1 1 d . . . H10A H 0.0733 0.2236 0.7004 0.044 Uiso 1 1 calc R . . H10B H 0.2620 0.2655 0.6936 0.044 Uiso 1 1 calc R . . C11 C 0.2238(6) -0.0420(10) 0.72740(10) 0.0387(11) Uani 1 1 d . . . H11A H 0.3220 -0.1455 0.7224 0.046 Uiso 1 1 calc R . . H11B H 0.1343 -0.1682 0.7310 0.046 Uiso 1 1 calc R . . C12 C 0.2588(6) 0.1151(10) 0.76066(10) 0.0399(12) Uani 1 1 d . . . H12A H 0.3564 0.2263 0.7581 0.048 Uiso 1 1 calc R . . H12B H 0.1655 0.2338 0.7643 0.048 Uiso 1 1 calc R . . C13 C 0.2872(6) -0.0606(10) 0.79237(10) 0.0398(12) Uani 1 1 d . . . H13A H 0.1856 -0.1585 0.7963 0.048 Uiso 1 1 calc R . . H13B H 0.3727 -0.1916 0.7877 0.048 Uiso 1 1 calc R . . C14 C 0.3388(6) 0.0915(10) 0.82505(10) 0.0369(11) Uani 1 1 d . . . H14A H 0.2566 0.2294 0.8291 0.044 Uiso 1 1 calc R . . H14B H 0.4441 0.1805 0.8218 0.044 Uiso 1 1 calc R . . C15 C 0.3568(6) -0.0863(10) 0.85671(11) 0.0385(11) Uani 1 1 d . . . H15A H 0.2491 -0.1655 0.8605 0.046 Uiso 1 1 calc R . . H15B H 0.4318 -0.2322 0.8515 0.046 Uiso 1 1 calc R . . C16 C 0.4191(5) 0.0423(9) 0.88998(11) 0.0335(10) Uani 1 1 d . . . O8 O 0.0832(4) -0.0153(6) 0.60363(7) 0.0426(9) Uani 1 1 d . . . H8 H 0.0371 0.0725 0.5875 0.064 Uiso 1 1 calc R . . O9 O 0.0187(4) 0.3364(7) 0.63456(8) 0.0460(9) Uani 1 1 d . . . O16 O 0.5188(4) 0.2411(6) 0.88598(7) 0.0393(8) Uani 1 1 d . . . H16 H 0.5605 0.2870 0.9054 0.059 Uiso 1 1 calc R . . O17 O 0.3818(4) -0.0348(6) 0.91839(7) 0.0400(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 C2 0.039(3) 0.030(2) 0.030(2) 0.000(2) -0.0044(18) -0.008(2) C3 0.048(3) 0.034(3) 0.030(2) 0.005(2) 0.003(2) -0.006(2) C4 0.032(2) 0.026(2) 0.032(2) -0.0012(19) 0.0004(18) 0.001(2) C5 0.036(2) 0.029(2) 0.034(2) 0.003(2) -0.0002(18) -0.007(2) C6 0.043(3) 0.037(3) 0.027(2) 0.003(2) 0.0000(19) -0.006(2) C7 0.034(2) 0.031(3) 0.028(2) 0.0000(19) 0.0002(17) 0.005(2) N1 0.037(2) 0.036(2) 0.0297(19) 0.0006(17) -0.0032(15) -0.0044(18) N7 0.046(2) 0.034(2) 0.0270(19) -0.0002(17) -0.0039(16) -0.0086(18) O7 0.0433(18) 0.0282(17) 0.0301(16) 0.0001(13) -0.0005(13) -0.0102(15) C8 0.036(2) 0.035(3) 0.026(2) 0.000(2) 0.0004(17) 0.000(2) C9 0.047(3) 0.037(3) 0.029(2) 0.000(2) -0.0001(19) 0.005(2) C10 0.041(3) 0.044(3) 0.025(2) 0.000(2) -0.0057(18) 0.002(2) C11 0.041(3) 0.047(3) 0.028(2) 0.002(2) -0.0010(18) 0.003(2) C12 0.043(3) 0.049(3) 0.027(2) 0.000(2) -0.0015(19) -0.002(2) C13 0.047(3) 0.042(3) 0.030(2) 0.000(2) -0.003(2) -0.001(2) C14 0.041(3) 0.044(3) 0.026(2) 0.001(2) -0.0029(18) -0.004(2) C15 0.043(3) 0.040(3) 0.032(2) -0.002(2) -0.0030(19) -0.006(2) C16 0.037(2) 0.032(3) 0.031(2) 0.002(2) -0.0046(19) 0.002(2) O8 0.064(2) 0.0385(19) 0.0249(15) -0.0032(14) -0.0056(14) 0.0143(17) O9 0.066(2) 0.041(2) 0.0307(17) -0.0018(15) -0.0063(15) 0.0158(18) O16 0.0463(19) 0.044(2) 0.0274(15) 0.0019(15) -0.0021(13) -0.0170(16) O17 0.053(2) 0.0410(19) 0.0260(16) 0.0024(14) -0.0004(13) -0.0108(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 N1 1.339(5) . ? C2 C3 1.379(6) . ? C2 H2 0.9500 . ? C3 C4 1.393(6) . ? C3 H3 0.9500 . ? C4 C5 1.394(6) . ? C4 C7 1.501(6) . ? C5 C6 1.381(6) . ? C5 H5 0.9500 . ? C6 N1 1.336(6) . ? C6 H6 0.9500 . ? C7 O7 1.248(5) . ? C7 N7 1.322(5) . ? N7 H7A 0.8800 . ? N7 H7B 0.8800 . ? C8 O9 1.216(5) . ? C8 O8 1.318(5) . ? C8 C9 1.481(6) . ? C9 C10 1.521(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.523(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.526(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.523(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.520(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.521(6) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.506(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O17 1.222(5) . ? C16 O16 1.313(5) . ? O8 H8 0.8400 . ? O16 H16 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 123.5(4) . . ? N1 C2 H2 118.3 . . ? C3 C2 H2 118.3 . . ? C2 C3 C4 118.9(4) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C3 C4 C5 118.0(4) . . ? C3 C4 C7 123.0(4) . . ? C5 C4 C7 119.0(4) . . ? C6 C5 C4 118.9(4) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? N1 C6 C5 123.4(4) . . ? N1 C6 H6 118.3 . . ? C5 C6 H6 118.3 . . ? O7 C7 N7 122.8(4) . . ? O7 C7 C4 118.9(4) . . ? N7 C7 C4 118.3(4) . . ? C6 N1 C2 117.4(4) . . ? C7 N7 H7A 120.0 . . ? C7 N7 H7B 120.0 . . ? H7A N7 H7B 120.0 . . ? O9 C8 O8 123.1(4) . . ? O9 C8 C9 124.2(4) . . ? O8 C8 C9 112.7(4) . . ? C8 C9 C10 115.3(4) . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C9 C10 C11 112.5(4) . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 113.3(4) . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 112.7(4) . . ? 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 113.3(4) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C13 C14 C15 112.3(4) . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 116.4(4) . . ? C16 C15 H15A 108.2 . . ? C14 C15 H15A 108.2 . . ? C16 C15 H15B 108.2 . . ? C14 C15 H15B 108.2 . . ? H15A C15 H15B 107.3 . . ? O17 C16 O16 122.8(4) . . ? O17 C16 C15 122.7(4) . . ? O16 C16 C15 114.5(4) . . ? C8 O8 H8 109.5 . . ? C16 O16 H16 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 0.4(7) . . . . ? C2 C3 C4 C5 -0.4(6) . . . . ? C2 C3 C4 C7 179.6(4) . . . . ? C3 C4 C5 C6 0.4(6) . . . . ? C7 C4 C5 C6 -179.6(4) . . . . ? C4 C5 C6 N1 -0.3(7) . . . . ? C3 C4 C7 O7 -179.9(4) . . . . ? C5 C4 C7 O7 0.1(6) . . . . ? C3 C4 C7 N7 1.6(6) . . . . ? C5 C4 C7 N7 -178.4(4) . . . . ? C5 C6 N1 C2 0.2(7) . . . . ? C3 C2 N1 C6 -0.3(7) . . . . ? O9 C8 C9 C10 -9.5(7) . . . . ? O8 C8 C9 C10 171.5(4) . . . . ? C8 C9 C10 C11 169.3(4) . . . . ? C9 C10 C11 C12 175.7(4) . . . . ? C10 C11 C12 C13 173.5(4) . . . . ? C11 C12 C13 C14 174.2(4) . . . . ? C12 C13 C14 C15 176.7(4) . . . . ? C13 C14 C15 C16 175.8(4) . . . . ? C14 C15 C16 O17 150.4(4) . . . . ? C14 C15 C16 O16 -30.6(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7A O9 0.88 2.03 2.899(5) 168.9 4_666 N7 H7B O17 0.88 2.06 2.905(5) 161.7 3_657 O8 H8 O7 0.84 1.77 2.586(4) 164.2 4_465 O16 H16 N1 0.84 1.79 2.626(4) 176.0 . _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.391 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.072 # Attachment '- isonicotinamide_pimelic.cif' data_2010src0399 _database_code_depnum_ccdc_archive 'CCDC 810991' #TrackingRef '- isonicotinamide_pimelic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Isonicotinamide:pimelic acid ; _chemical_name_common ? _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 Monoclinic _symmetry_space_group_name_H-M 'P 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 8.2223(5) _cell_length_b 5.1437(3) _cell_length_c 33.389(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.873(3) _cell_angle_gamma 90.00 _cell_volume 1408.90(15) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 15181 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9898 _exptl_absorpt_correction_T_max 0.9949 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission from SADABS: 0.6531 and 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13904 _diffrn_reflns_av_R_equivalents 0.0742 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2480 _reflns_number_gt 1772 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0541P)^2^+0.5667P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2480 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 C2 C 0.7724(3) 0.1102(5) 0.55838(7) 0.0281(6) Uani 1 1 d . . . H2 H 0.7571 0.2137 0.5814 0.034 Uiso 1 1 calc R . . C3 C 0.6946(3) 0.1839(5) 0.52187(7) 0.0265(6) Uani 1 1 d . . . H3 H 0.6278 0.3348 0.5202 0.032 Uiso 1 1 calc R . . C4 C 0.7155(3) 0.0353(4) 0.48809(6) 0.0219(5) Uani 1 1 d . . . C5 C 0.8129(3) -0.1838(5) 0.49244(7) 0.0275(6) Uani 1 1 d . . . H5 H 0.8289 -0.2923 0.4700 0.033 Uiso 1 1 calc R . . C6 C 0.8865(3) -0.2429(5) 0.52972(7) 0.0285(6) Uani 1 1 d . . . H6 H 0.9540 -0.3927 0.5322 0.034 Uiso 1 1 calc R . . C7 C 0.6307(3) 0.1164(5) 0.44875(7) 0.0223(6) Uani 1 1 d . . . N1 N 0.8674(2) -0.0994(4) 0.56251(5) 0.0245(5) Uani 1 1 d . . . N7 N 0.6493(2) -0.0290(4) 0.41674(5) 0.0292(5) Uani 1 1 d . . . H7A H 0.5996 0.0136 0.3935 0.035 Uiso 1 1 calc R . . H7B H 0.7113 -0.1685 0.4187 0.035 Uiso 1 1 calc R . . O7 O 0.5444(2) 0.3157(3) 0.44773(4) 0.0282(4) Uani 1 1 d . . . C8 C 0.4050(3) 0.3819(5) 0.34881(7) 0.0255(6) Uani 1 1 d . . . C9 C 0.3299(3) 0.5361(5) 0.31418(6) 0.0293(6) Uani 1 1 d . . . H9A H 0.4054 0.6784 0.3081 0.035 Uiso 1 1 calc R . . H9B H 0.2281 0.6169 0.3225 0.035 Uiso 1 1 calc R . . C10 C 0.2903(3) 0.3811(5) 0.27608(7) 0.0297(6) Uani 1 1 d . . . H10A H 0.1996 0.2601 0.2804 0.036 Uiso 1 1 calc R . . H10B H 0.3865 0.2759 0.2701 0.036 Uiso 1 1 calc R . . C11 C 0.2429(3) 0.5545(5) 0.24035(6) 0.0290(6) Uani 1 1 d . . . H11A H 0.3367 0.6671 0.2350 0.035 Uiso 1 1 calc R . . H11B H 0.1521 0.6689 0.2473 0.035 Uiso 1 1 calc R . . C12 C 0.1909(3) 0.4059(5) 0.20217(6) 0.0288(6) Uani 1 1 d . . . H12A H 0.2775 0.2805 0.1963 0.035 Uiso 1 1 calc R . . H12B H 0.0907 0.3060 0.2065 0.035 Uiso 1 1 calc R . . C13 C 0.1590(3) 0.5859(5) 0.16631(7) 0.0306(6) Uani 1 1 d . . . H13A H 0.0799 0.7201 0.1736 0.037 Uiso 1 1 calc R . . H13B H 0.2621 0.6761 0.1614 0.037 Uiso 1 1 calc R . . C14 C 0.0949(3) 0.4602(5) 0.12760(7) 0.0262(6) Uani 1 1 d . . . O8 O 0.4114(2) 0.5174(3) 0.38253(5) 0.0372(5) Uani 1 1 d . . . H8 H 0.4565 0.4280 0.4012 0.056 Uiso 1 1 calc R . . O9 O 0.4577(2) 0.1636(3) 0.34620(5) 0.0378(5) Uani 1 1 d . . . O14 O -0.0053(2) 0.2648(3) 0.13243(5) 0.0355(5) Uani 1 1 d . . . H14 H -0.0398 0.2077 0.1099 0.053 Uiso 1 1 calc R . . O15 O 0.1285(2) 0.5368(3) 0.09472(5) 0.0341(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0329(14) 0.0299(14) 0.0211(13) -0.0055(11) -0.0010(10) 0.0055(12) C3 0.0285(14) 0.0263(14) 0.0242(13) -0.0006(11) -0.0016(10) 0.0047(11) C4 0.0234(13) 0.0241(13) 0.0183(12) 0.0008(10) 0.0021(10) -0.0015(11) C5 0.0344(14) 0.0292(14) 0.0185(13) -0.0043(11) -0.0008(10) 0.0073(12) C6 0.0319(14) 0.0292(14) 0.0241(14) -0.0015(11) -0.0012(11) 0.0082(12) C7 0.0250(13) 0.0215(14) 0.0203(13) 0.0000(10) 0.0016(10) -0.0011(11) N1 0.0277(11) 0.0252(11) 0.0202(11) 0.0001(9) -0.0007(8) 0.0025(10) N7 0.0385(12) 0.0279(12) 0.0202(11) -0.0008(9) -0.0050(9) 0.0123(10) O7 0.0365(10) 0.0262(10) 0.0216(9) -0.0011(7) -0.0006(7) 0.0085(8) C8 0.0259(13) 0.0320(15) 0.0183(13) -0.0030(11) -0.0002(10) -0.0017(12) C9 0.0333(14) 0.0342(15) 0.0202(13) 0.0003(11) -0.0005(10) 0.0056(12) C10 0.0326(14) 0.0361(15) 0.0199(13) -0.0019(11) -0.0020(10) -0.0012(12) C11 0.0289(14) 0.0383(15) 0.0195(13) -0.0025(11) -0.0014(10) 0.0001(12) C12 0.0304(14) 0.0369(15) 0.0187(13) 0.0011(11) -0.0008(10) -0.0043(12) C13 0.0353(15) 0.0359(15) 0.0198(13) 0.0000(11) -0.0033(11) -0.0071(12) C14 0.0259(13) 0.0290(14) 0.0232(13) 0.0025(11) -0.0024(10) -0.0022(12) O8 0.0556(12) 0.0355(11) 0.0192(9) -0.0023(8) -0.0078(8) 0.0152(9) O9 0.0564(12) 0.0321(11) 0.0237(10) -0.0050(8) -0.0066(8) 0.0136(9) O14 0.0426(11) 0.0453(12) 0.0179(9) 0.0026(8) -0.0034(8) -0.0197(9) O15 0.0447(11) 0.0389(11) 0.0182(9) 0.0039(8) -0.0012(8) -0.0127(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 N1 1.333(3) . ? C2 C3 1.390(3) . ? C2 H2 0.9500 . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.385(3) . ? C4 C7 1.504(3) . ? C5 C6 1.380(3) . ? C5 H5 0.9500 . ? C6 N1 1.338(3) . ? C6 H6 0.9500 . ? C7 O7 1.246(3) . ? C7 N7 1.322(3) . ? N7 H7A 0.8800 . ? N7 H7B 0.8800 . ? C8 O9 1.209(3) . ? C8 O8 1.322(3) . ? C8 C9 1.500(3) . ? C9 C10 1.518(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.520(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.522(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.522(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.508(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O15 1.216(3) . ? C14 O14 1.316(3) . ? O8 H8 0.8400 . ? O14 H14 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 122.9(2) . . ? N1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C4 C3 C2 119.3(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 117.9(2) . . ? C3 C4 C7 118.9(2) . . ? C5 C4 C7 123.2(2) . . ? C6 C5 C4 119.3(2) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? N1 C6 C5 123.2(2) . . ? N1 C6 H6 118.4 . . ? C5 C6 H6 118.4 . . ? O7 C7 N7 122.7(2) . . ? O7 C7 C4 118.8(2) . . ? N7 C7 C4 118.5(2) . . ? C2 N1 C6 117.5(2) . . ? C7 N7 H7A 120.0 . . ? C7 N7 H7B 120.0 . . ? H7A N7 H7B 120.0 . . ? O9 C8 O8 123.8(2) . . ? O9 C8 C9 124.5(2) . . ? O8 C8 C9 111.6(2) . . ? C8 C9 C10 114.9(2) . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C9 C10 C11 112.2(2) . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C10 C11 C12 113.9(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 112.1(2) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 116.4(2) . . ? C14 C13 H13A 108.2 . . ? C12 C13 H13A 108.2 . . ? C14 C13 H13B 108.2 . . ? C12 C13 H13B 108.2 . . ? H13A C13 H13B 107.3 . . ? O15 C14 O14 122.7(2) . . ? O15 C14 C13 123.2(2) . . ? O14 C14 C13 114.1(2) . . ? C8 O8 H8 109.5 . . ? C14 O14 H14 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 0.0(4) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C2 C3 C4 C7 179.9(2) . . . . ? C3 C4 C5 C6 -0.9(3) . . . . ? C7 C4 C5 C6 179.8(2) . . . . ? C4 C5 C6 N1 0.7(4) . . . . ? C3 C4 C7 O7 0.2(3) . . . . ? C5 C4 C7 O7 179.5(2) . . . . ? C3 C4 C7 N7 -178.9(2) . . . . ? C5 C4 C7 N7 0.3(3) . . . . ? C3 C2 N1 C6 -0.3(4) . . . . ? C5 C6 N1 C2 0.0(4) . . . . ? O9 C8 C9 C10 12.4(4) . . . . ? O8 C8 C9 C10 -169.6(2) . . . . ? C8 C9 C10 C11 -169.9(2) . . . . ? C9 C10 C11 C12 -176.0(2) . . . . ? C10 C11 C12 C13 -174.9(2) . . . . ? C11 C12 C13 C14 -175.6(2) . . . . ? C12 C13 C14 O15 -146.7(2) . . . . ? C12 C13 C14 O14 35.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7A O9 0.88 2.05 2.917(2) 168.4 . N7 H7B O15 0.88 2.08 2.927(3) 162.2 2_645 O8 H8 O7 0.84 1.77 2.586(2) 164.9 . O14 H14 N1 0.84 1.80 2.634(2) 174.4 4_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.311 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.101 # Attachment '- isonicotinamide_suberic.cif' data_2010src0398 _database_code_depnum_ccdc_archive 'CCDC 810992' #TrackingRef '- isonicotinamide_suberic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Isonicotinamide:suberic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H14 O4, C6 H6 N2 O' _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' 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 8.9413(15) _cell_length_b 9.5366(13) _cell_length_c 10.1347(17) _cell_angle_alpha 86.653(11) _cell_angle_beta 66.031(7) _cell_angle_gamma 66.571(10) _cell_volume 719.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 48454 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description 'Cut plate' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9794 _exptl_absorpt_correction_T_max 0.9969 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 8940 reflections reduced R(int) from 0.2407 to 0.0750 Ratio of minimum to maximum apparent transmission: 0.581982 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9503 _diffrn_reflns_av_R_equivalents 0.0719 _diffrn_reflns_av_sigmaI/netI 0.0608 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2516 _reflns_number_gt 1855 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0541P)^2^+1.1400P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2516 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1055 _refine_ls_R_factor_gt 0.0724 _refine_ls_wR_factor_ref 0.1837 _refine_ls_wR_factor_gt 0.1604 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 C2 C 0.7646(5) 0.9997(4) 0.7047(4) 0.0358(8) Uani 1 1 d . . . H2 H 0.6887 1.0898 0.7730 0.043 Uiso 1 1 calc R . . C3 C 0.6881(5) 0.9395(4) 0.6422(4) 0.0348(8) Uani 1 1 d . . . H3 H 0.5625 0.9855 0.6687 0.042 Uiso 1 1 calc R . . C4 C 0.7989(4) 0.8102(4) 0.5400(3) 0.0306(8) Uani 1 1 d . . . C5 C 0.9803(5) 0.7471(4) 0.5062(4) 0.0355(8) Uani 1 1 d . . . H5 H 1.0598 0.6590 0.4358 0.043 Uiso 1 1 calc R . . C6 C 1.0446(5) 0.8133(4) 0.5757(4) 0.0341(8) Uani 1 1 d . . . H6 H 1.1694 0.7683 0.5526 0.041 Uiso 1 1 calc R . . C7 C 0.7311(4) 0.7342(4) 0.4653(3) 0.0320(8) Uani 1 1 d . . . N1 N 0.9389(4) 0.9384(3) 0.6745(3) 0.0341(7) Uani 1 1 d . . . N7 N 0.5555(4) 0.7827(3) 0.5090(3) 0.0344(7) Uani 1 1 d . . . H7A H 0.5133 0.7382 0.4677 0.041 Uiso 1 1 calc R . . H7B H 0.4811 0.8593 0.5794 0.041 Uiso 1 1 calc R . . O7 O 0.8406(3) 0.6265(3) 0.3664(3) 0.0396(6) Uani 1 1 d . . . C8 C 0.5979(5) 0.4913(4) 0.2605(4) 0.0322(8) Uani 1 1 d . . . C9 C 0.5879(5) 0.3816(4) 0.1678(4) 0.0326(8) Uani 1 1 d . . . H9A H 0.6364 0.2771 0.1951 0.039 Uiso 1 1 calc R . . H9B H 0.6678 0.3800 0.0653 0.039 Uiso 1 1 calc R . . C10 C 0.4050(4) 0.4143(4) 0.1758(4) 0.0315(8) Uani 1 1 d . . . H10A H 0.3510 0.5205 0.1539 0.038 Uiso 1 1 calc R . . H10B H 0.3259 0.4061 0.2755 0.038 Uiso 1 1 calc R . . C11 C 0.4197(4) 0.2998(4) 0.0670(4) 0.0325(8) Uani 1 1 d . . . H11A H 0.4976 0.3108 -0.0320 0.039 Uiso 1 1 calc R . . H11B H 0.4799 0.1943 0.0873 0.039 Uiso 1 1 calc R . . C12 C 0.2434(4) 0.3167(4) 0.0675(4) 0.0320(8) Uani 1 1 d . . . H12A H 0.1811 0.4223 0.0483 0.038 Uiso 1 1 calc R . . H12B H 0.1658 0.3023 0.1650 0.038 Uiso 1 1 calc R . . C13 C 0.2707(4) 0.2009(4) -0.0461(4) 0.0310(8) Uani 1 1 d . . . H13A H 0.3460 0.2172 -0.1437 0.037 Uiso 1 1 calc R . . H13B H 0.3359 0.0956 -0.0283 0.037 Uiso 1 1 calc R . . C14 C 0.0955(4) 0.2135(4) -0.0446(4) 0.0333(8) Uani 1 1 d . . . H14A H 0.0208 0.1971 0.0532 0.040 Uiso 1 1 calc R . . H14B H 0.0302 0.3195 -0.0611 0.040 Uiso 1 1 calc R . . C15 C 0.1164(4) 0.1019(4) -0.1558(4) 0.0307(8) Uani 1 1 d . . . O8 O 0.7644(3) 0.4492(3) 0.2452(3) 0.0419(7) Uani 1 1 d . . . H8 H 0.7687 0.5156 0.2928 0.063 Uiso 1 1 calc R . . O9 O 0.4728(3) 0.6055(3) 0.3381(3) 0.0412(7) Uani 1 1 d . . . O15 O -0.0381(3) 0.1116(3) -0.1458(3) 0.0427(7) Uani 1 1 d . . . H15 H -0.0207 0.0475 -0.2097 0.064 Uiso 1 1 calc R . . O16 O 0.2593(3) 0.0119(3) -0.2462(2) 0.0379(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 C2 0.0311(19) 0.0323(18) 0.0324(19) -0.0050(15) -0.0058(15) -0.0083(15) C3 0.0270(18) 0.0382(19) 0.0323(19) -0.0019(15) -0.0088(15) -0.0097(15) C4 0.0313(18) 0.0285(17) 0.0264(17) 0.0004(14) -0.0090(15) -0.0096(14) C5 0.0322(19) 0.0361(19) 0.0302(18) -0.0013(15) -0.0086(15) -0.0104(16) C6 0.0300(18) 0.0340(19) 0.0299(18) -0.0018(15) -0.0081(15) -0.0087(16) C7 0.0288(18) 0.0366(19) 0.0259(17) 0.0026(15) -0.0087(15) -0.0117(16) N1 0.0319(16) 0.0369(16) 0.0334(16) 0.0020(13) -0.0116(13) -0.0158(13) N7 0.0299(16) 0.0373(16) 0.0312(15) -0.0082(13) -0.0095(13) -0.0108(13) O7 0.0306(13) 0.0384(14) 0.0381(14) -0.0130(11) -0.0077(11) -0.0077(11) C8 0.0306(18) 0.0346(19) 0.0287(18) 0.0029(15) -0.0109(15) -0.0121(16) C9 0.0331(18) 0.0333(18) 0.0247(17) -0.0006(14) -0.0076(15) -0.0114(15) C10 0.0297(18) 0.0305(17) 0.0304(17) -0.0008(14) -0.0098(14) -0.0109(14) C11 0.0318(18) 0.0297(18) 0.0312(18) -0.0009(14) -0.0095(15) -0.0111(15) C12 0.0292(18) 0.0302(18) 0.0296(18) -0.0007(14) -0.0078(15) -0.0095(15) C13 0.0270(17) 0.0300(17) 0.0291(18) -0.0015(14) -0.0083(14) -0.0081(14) C14 0.0288(18) 0.0304(18) 0.0323(18) -0.0041(14) -0.0071(15) -0.0087(15) C15 0.0253(18) 0.0331(18) 0.0287(18) 0.0030(14) -0.0086(15) -0.0098(15) O8 0.0320(14) 0.0408(15) 0.0475(16) -0.0134(12) -0.0165(12) -0.0074(11) O9 0.0310(14) 0.0409(15) 0.0418(15) -0.0139(12) -0.0114(12) -0.0068(12) O15 0.0298(13) 0.0504(16) 0.0415(15) -0.0162(12) -0.0100(11) -0.0123(12) O16 0.0289(13) 0.0398(14) 0.0337(13) -0.0108(11) -0.0063(11) -0.0082(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 N1 1.332(4) . ? C2 C3 1.381(5) . ? C2 H2 0.9500 . ? C3 C4 1.385(5) . ? C3 H3 0.9500 . ? C4 C5 1.381(5) . ? C4 C7 1.500(5) . ? C5 C6 1.377(5) . ? C5 H5 0.9500 . ? C6 N1 1.339(4) . ? C6 H6 0.9500 . ? C7 O7 1.241(4) . ? C7 N7 1.326(4) . ? N7 H7A 0.8800 . ? N7 H7B 0.8800 . ? C8 O9 1.214(4) . ? C8 O8 1.321(4) . ? C8 C9 1.497(5) . ? C9 C10 1.506(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.528(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.517(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.520(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.516(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.500(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O16 1.215(4) . ? C15 O15 1.309(4) . ? O8 H8 0.8400 . ? O15 H15 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 123.6(3) . . ? N1 C2 H2 118.2 . . ? C3 C2 H2 118.2 . . ? C2 C3 C4 118.4(3) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 118.5(3) . . ? C5 C4 C7 118.3(3) . . ? C3 C4 C7 123.2(3) . . ? C6 C5 C4 119.2(3) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? N1 C6 C5 122.9(3) . . ? N1 C6 H6 118.6 . . ? C5 C6 H6 118.6 . . ? O7 C7 N7 122.0(3) . . ? O7 C7 C4 119.2(3) . . ? N7 C7 C4 118.7(3) . . ? C2 N1 C6 117.4(3) . . ? C7 N7 H7A 120.0 . . ? C7 N7 H7B 120.0 . . ? H7A N7 H7B 120.0 . . ? O9 C8 O8 123.4(3) . . ? O9 C8 C9 125.8(3) . . ? O8 C8 C9 110.8(3) . . ? C8 C9 C10 116.7(3) . . ? C8 C9 H9A 108.1 . . ? C10 C9 H9A 108.1 . . ? C8 C9 H9B 108.1 . . ? C10 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? C9 C10 C11 110.2(3) . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 115.5(3) . . ? C12 C11 H11A 108.4 . . ? C10 C11 H11A 108.4 . . ? C12 C11 H11B 108.4 . . ? C10 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C11 C12 C13 112.0(3) . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 112.8(3) . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C13 114.5(3) . . ? C15 C14 H14A 108.6 . . ? C13 C14 H14A 108.6 . . ? C15 C14 H14B 108.6 . . ? C13 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? O16 C15 O15 122.8(3) . . ? O16 C15 C14 124.8(3) . . ? O15 C15 C14 112.4(3) . . ? C8 O8 H8 109.5 . . ? C15 O15 H15 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 -1.5(5) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? C2 C3 C4 C7 179.8(3) . . . . ? C3 C4 C5 C6 0.6(5) . . . . ? C7 C4 C5 C6 -178.7(3) . . . . ? C4 C5 C6 N1 -0.8(5) . . . . ? C5 C4 C7 O7 -6.5(5) . . . . ? C3 C4 C7 O7 174.1(3) . . . . ? C5 C4 C7 N7 172.2(3) . . . . ? C3 C4 C7 N7 -7.1(5) . . . . ? C3 C2 N1 C6 1.4(5) . . . . ? C5 C6 N1 C2 -0.2(5) . . . . ? O9 C8 C9 C10 -2.0(5) . . . . ? O8 C8 C9 C10 179.2(3) . . . . ? C8 C9 C10 C11 175.7(3) . . . . ? C9 C10 C11 C12 178.0(3) . . . . ? C10 C11 C12 C13 178.7(3) . . . . ? C11 C12 C13 C14 178.6(3) . . . . ? C12 C13 C14 C15 179.6(3) . . . . ? C13 C14 C15 O16 -3.4(5) . . . . ? C13 C14 C15 O15 176.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7A O9 0.88 2.10 2.963(4) 167.3 . N7 H7B O16 0.88 2.08 2.939(4) 164.6 1_566 O8 H8 O7 0.84 1.76 2.583(3) 164.5 . O15 H15 N1 0.84 1.84 2.648(4) 161.6 1_444 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.281 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.062