# 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 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'P Cox' _publ_contact_author_email P.J.COX@RGU.AC.UK _publ_section_title ; Supramolecular structures of some adenine-carboxylic acid complexes ; loop_ _publ_author_name 'P Cox' 'Maureen Byres' 'Graeme Kay' 'Elaine Nixon' # Attachment 'accallcifs.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-02-12 at 14:48:53 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\cifdoc.dat # CIF files read : 2d4d info struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_adba _database_code_depnum_ccdc_archive 'CCDC 686683' _audit_creation_date 2008-02-12T16:18:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Adenine - benzoic acid (1:2) co-crystal ; _chemical_formula_moiety ; C5 H5 N5, 2(C7 H6 O2) ; _chemical_formula_sum 'C19 H17 N5 O4' _chemical_formula_weight 379.38 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9422(2) _cell_length_b 10.1547(4) _cell_length_c 14.1896(5) _cell_angle_alpha 81.003(2) _cell_angle_beta 76.327(2) _cell_angle_gamma 70.344(2) _cell_volume 912.09(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4094 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.48 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.1 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.8606 _exptl_absorpt_correction_T_max 0.9881 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type ; Bruker-Nonius KappaCCD Area Detector ; _diffrn_measurement_method ; \f and \w scans ; _diffrn_standards_number 0 _diffrn_standards_decay_% negligible _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_unetI/netI 0.0326 _diffrn_reflns_number 19200 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.2 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 4139 _reflns_number_gt 3362 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998) ; _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek,2002) ; _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0433P)^2^+0.2515P] 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_number_reflns 4139 _refine_ls_number_parameters 288 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.252 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.04 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 N1A N 0.6078(2) 0.77093(13) -0.02817(10) 0.0241(3) Uani 0.907(3) 1 d PD A 1 N2A N 0.8606(2) 0.88840(14) -0.03692(11) 0.0226(3) Uani 0.907(3) 1 d PD A 1 N3A N 0.53323(19) 0.93323(15) 0.19995(9) 0.0244(3) Uani 0.907(3) 1 d PD A 1 N4A N 0.8095(2) 0.99364(16) 0.11381(10) 0.0233(3) Uani 0.907(3) 1 d PD A 1 H4A H 0.911 1.0314 0.0992 0.028 Uiso 0.907(3) 1 calc PR A 1 N5A N 0.3375(3) 0.7678(3) 0.1037(2) 0.0257(5) Uani 0.907(3) 1 d PD A 1 H5A H 0.2931 0.7205 0.0713 0.031 Uiso 0.907(3) 1 calc PR A 1 H5B H 0.2704 0.7899 0.1628 0.031 Uiso 0.907(3) 1 calc PR A 1 C1A C 0.7731(2) 0.81316(15) -0.07136(12) 0.0244(3) Uani 0.907(3) 1 d PD A 1 H1A H 0.8363 0.7855 -0.1353 0.029 Uiso 0.907(3) 1 calc PR A 1 C2A C 0.7618(2) 0.91900(17) 0.05530(11) 0.0206(3) Uani 0.907(3) 1 d PD A 1 C3A C 0.5906(2) 0.88216(14) 0.10872(10) 0.0221(3) Uani 0.907(3) 1 d PD A 1 C4A C 0.5064(2) 0.80620(14) 0.06338(11) 0.0220(3) Uani 0.907(3) 1 d PD A 1 C5A C 0.6694(2) 0.99790(18) 0.19867(10) 0.0250(3) Uani 0.907(3) 1 d PD A 1 H5C H 0.6693 1.0434 0.2523 0.03 Uiso 0.907(3) 1 calc PR A 1 N1B N 0.492(2) 0.1165(14) -0.1920(9) 0.023(2) Uiso 0.093(3) 1 d PD A 2 N2B N 0.197(3) 0.0449(18) -0.1016(11) 0.023(2) Uiso 0.093(3) 1 d PD A 2 N3B N 0.331(2) 0.2135(14) 0.0617(9) 0.023(2) Uiso 0.093(3) 1 d PD A 2 N4B N 0.092(2) 0.1017(16) 0.0684(10) 0.023(2) Uiso 0.093(3) 1 d PD A 2 H4B H -0.0104 0.0656 0.0918 0.027 Uiso 0.093(3) 1 calc PR A 2 N5B N 0.677(4) 0.209(3) -0.114(2) 0.023(2) Uiso 0.093(3) 1 d PD A 2 H5X H 0.779 0.1953 -0.1658 0.027 Uiso 0.093(3) 1 calc PR A 2 H5Y H 0.6864 0.2449 -0.064 0.027 Uiso 0.093(3) 1 calc PR A 2 C1B C 0.343(2) 0.0579(15) -0.1830(9) 0.0157(19) Uiso 0.093(3) 1 d PD A 2 H1X H 0.3368 0.0212 -0.2394 0.019 Uiso 0.093(3) 1 calc PR A 2 C2B C 0.207(2) 0.1023(18) -0.0236(12) 0.0157(19) Uiso 0.093(3) 1 d PD A 2 C3B C 0.3553(16) 0.1708(12) -0.0271(7) 0.0157(19) Uiso 0.093(3) 1 d PD A 2 C4B C 0.5048(17) 0.1730(13) -0.1130(8) 0.0157(19) Uiso 0.093(3) 1 d PD A 2 C5B C 0.1759(19) 0.1726(13) 0.1162(10) 0.0157(19) Uiso 0.093(3) 1 d PD A 2 H5Z H 0.1254 0.19 0.1828 0.019 Uiso 0.093(3) 1 calc PR A 2 O1 O 0.49125(15) 0.36228(11) 0.14553(7) 0.0348(2) Uani 1 1 d . . . H1 H 0.4666 0.325 0.1028 0.042 Uiso 1 1 calc R . . O2 O 0.74443(15) 0.39878(11) 0.02403(7) 0.0333(2) Uani 1 1 d . . . C6 C 0.7094(2) 0.47533(13) 0.17919(9) 0.0253(3) Uani 1 1 d . . . C7 C 0.5867(2) 0.49898(14) 0.27201(10) 0.0305(3) Uani 1 1 d . . . H7 H 0.4623 0.4737 0.291 0.037 Uiso 1 1 calc R . . C8 C 0.6474(2) 0.55972(15) 0.33658(11) 0.0388(3) Uani 1 1 d . . . H8 H 0.5638 0.5766 0.3996 0.047 Uiso 1 1 calc R . . C9 C 0.8291(3) 0.59563(16) 0.30914(12) 0.0427(4) Uani 1 1 d . . . H9 H 0.8708 0.6361 0.3538 0.051 Uiso 1 1 calc R . . C10 C 0.9505(2) 0.57308(15) 0.21736(11) 0.0380(3) Uani 1 1 d . . . H10 H 1.075 0.5983 0.1989 0.046 Uiso 1 1 calc R . . C11 C 0.8908(2) 0.51366(14) 0.15201(10) 0.0303(3) Uani 1 1 d . . . H11 H 0.9737 0.4991 0.0886 0.036 Uiso 1 1 calc R . . C12 C 0.65076(19) 0.40923(13) 0.10822(9) 0.0254(3) Uani 1 1 d . . . O3 O -0.30044(13) 0.12710(10) 0.63054(6) 0.0282(2) Uani 1 1 d . . . H3 H -0.3649 0.1113 0.687 0.034 Uiso 1 1 calc R . . O4 O -0.05518(15) 0.11742(12) 0.71092(7) 0.0395(3) Uani 1 1 d . . . C13 C 0.00999(19) 0.16268(13) 0.53844(9) 0.0231(3) Uani 1 1 d . . . C14 C 0.2187(2) 0.14953(15) 0.53057(10) 0.0302(3) Uani 1 1 d . . . H14 H 0.2814 0.1184 0.5861 0.036 Uiso 1 1 calc R . . C15 C 0.3355(2) 0.18166(16) 0.44207(11) 0.0368(3) Uani 1 1 d . . . H15 H 0.4785 0.1719 0.437 0.044 Uiso 1 1 calc R . . C16 C 0.2456(2) 0.22787(15) 0.36084(10) 0.0357(3) Uani 1 1 d . . . H16 H 0.326 0.2512 0.3004 0.043 Uiso 1 1 calc R . . C17 C 0.0385(2) 0.23997(15) 0.36795(10) 0.0344(3) Uani 1 1 d . . . H17 H -0.0233 0.2707 0.3121 0.041 Uiso 1 1 calc R . . C18 C -0.0792(2) 0.20741(14) 0.45617(9) 0.0284(3) Uani 1 1 d . . . H18 H -0.2214 0.2156 0.4607 0.034 Uiso 1 1 calc R . . C19 C -0.11665(19) 0.13293(13) 0.63489(9) 0.0251(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 N1A 0.0235(7) 0.0259(7) 0.0236(7) -0.0013(5) -0.0035(5) -0.0099(5) N2A 0.0194(7) 0.0285(7) 0.0203(8) -0.0017(6) -0.0024(6) -0.0091(5) N3A 0.0231(7) 0.0323(8) 0.0184(6) 0.0006(5) -0.0036(5) -0.0110(6) N4A 0.0201(6) 0.0328(9) 0.0199(6) -0.0016(5) -0.0039(5) -0.0122(6) N5A 0.0251(7) 0.0298(14) 0.0259(11) -0.0026(7) -0.0014(6) -0.0156(9) C1A 0.0236(8) 0.0278(8) 0.0206(8) -0.0029(6) -0.0021(6) -0.0075(6) C2A 0.0177(7) 0.0239(8) 0.0199(8) 0.0008(6) -0.0049(6) -0.0066(6) C3A 0.0200(7) 0.0251(7) 0.0207(7) 0.0024(5) -0.0053(5) -0.0074(5) C4A 0.0219(7) 0.0208(7) 0.0223(7) 0.0032(6) -0.0061(6) -0.0062(5) C5A 0.0228(7) 0.0337(9) 0.0200(7) -0.0002(6) -0.0045(5) -0.0115(6) O1 0.0398(6) 0.0498(6) 0.0246(5) -0.0054(4) -0.0032(4) -0.0280(5) O2 0.0328(5) 0.0446(6) 0.0239(5) -0.0044(4) -0.0017(4) -0.0160(4) C6 0.0279(7) 0.0215(6) 0.0260(7) 0.0013(5) -0.0076(5) -0.0068(5) C7 0.0298(7) 0.0296(7) 0.0305(7) -0.0033(6) -0.0048(6) -0.0079(6) C8 0.0455(9) 0.0348(8) 0.0335(8) -0.0130(6) -0.0056(6) -0.0059(7) C9 0.0576(10) 0.0335(8) 0.0464(9) -0.0090(7) -0.0182(8) -0.0187(7) C10 0.0440(8) 0.0320(8) 0.0460(9) 0.0035(6) -0.0147(7) -0.0211(7) C11 0.0342(7) 0.0267(7) 0.0301(7) 0.0038(5) -0.0063(6) -0.0124(6) C12 0.0255(6) 0.0250(7) 0.0241(7) 0.0019(5) -0.0054(5) -0.0071(5) O3 0.0243(5) 0.0434(6) 0.0181(4) 0.0003(4) -0.0014(3) -0.0153(4) O4 0.0342(5) 0.0674(7) 0.0216(5) -0.0019(5) -0.0089(4) -0.0204(5) C13 0.0256(6) 0.0223(6) 0.0234(6) -0.0042(5) -0.0037(5) -0.0096(5) C14 0.0271(7) 0.0386(8) 0.0288(7) -0.0082(6) -0.0058(5) -0.0125(6) C15 0.0273(7) 0.0467(9) 0.0406(8) -0.0115(7) 0.0014(6) -0.0189(6) C16 0.0381(8) 0.0358(8) 0.0304(7) -0.0032(6) 0.0071(6) -0.0173(6) C17 0.0358(8) 0.0374(8) 0.0248(7) 0.0040(6) -0.0038(6) -0.0094(6) C18 0.0250(6) 0.0329(7) 0.0265(7) 0.0009(5) -0.0043(5) -0.0100(5) C19 0.0245(6) 0.0287(7) 0.0231(6) -0.0036(5) -0.0052(5) -0.0087(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1A C1A 1.339(2) . ? N1A C4A 1.362(2) . ? N2A C1A 1.3268(19) . ? N2A C2A 1.3560(19) . ? N3A C5A 1.315(2) . ? N3A C3A 1.3895(19) . ? N4A C5A 1.3536(19) . ? N4A C2A 1.367(2) . ? N4A H4A 0.88 . ? N5A C4A 1.332(2) . ? N5A H5A 0.88 . ? N5A H5B 0.88 . ? C1A H1A 0.95 . ? C2A C3A 1.3828(19) . ? C3A C4A 1.409(2) . ? C5A H5C 0.95 . ? N1B C1B 1.329(14) . ? N1B C4B 1.370(14) . ? N2B C2B 1.353(14) . ? N2B C1B 1.364(15) . ? N3B C5B 1.317(14) . ? N3B C3B 1.352(13) . ? N4B C2B 1.361(14) . ? N4B C5B 1.393(14) . ? N4B H4B 0.88 . ? N5B C4B 1.354(16) . ? N5B H5X 0.88 . ? N5B H5Y 0.88 . ? C1B H1X 0.95 . ? C2B C3B 1.410(14) . ? C3B C4B 1.404(12) . ? C5B H5Z 0.95 . ? O1 C12 1.3163(15) . ? O1 H1 0.84 . ? O2 C12 1.2195(15) . ? C6 C11 1.3924(18) . ? C6 C7 1.3960(18) . ? C6 C12 1.4900(18) . ? C7 C8 1.389(2) . ? C7 H7 0.95 . ? C8 C9 1.382(2) . ? C8 H8 0.95 . ? C9 C10 1.379(2) . ? C9 H9 0.95 . ? C10 C11 1.386(2) . ? C10 H10 0.95 . ? C11 H11 0.95 . ? O3 C19 1.3131(15) . ? O3 H3 0.84 . ? O4 C19 1.2207(15) . ? C13 C14 1.3887(17) . ? C13 C18 1.3923(17) . ? C13 C19 1.4892(17) . ? C14 C15 1.382(2) . ? C14 H14 0.95 . ? C15 C16 1.383(2) . ? C15 H15 0.95 . ? C16 C17 1.382(2) . ? C16 H16 0.95 . ? C17 C18 1.3828(18) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? 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 C1A N1A C4A 119.79(12) . . ? C1A N2A C2A 110.71(14) . . ? C5A N3A C3A 103.93(12) . . ? C5A N4A C2A 106.30(12) . . ? C5A N4A H4A 126.9 . . ? C2A N4A H4A 126.9 . . ? C4A N5A H5A 120 . . ? C4A N5A H5B 120 . . ? H5A N5A H5B 120 . . ? N2A C1A N1A 128.75(14) . . ? N2A C1A H1A 115.6 . . ? N1A C1A H1A 115.6 . . ? N2A C2A N4A 127.10(13) . . ? N2A C2A C3A 126.77(15) . . ? N4A C2A C3A 106.12(14) . . ? C2A C3A N3A 109.90(13) . . ? C2A C3A C4A 117.50(13) . . ? N3A C3A C4A 132.59(13) . . ? N5A C4A N1A 118.94(15) . . ? N5A C4A C3A 124.65(16) . . ? N1A C4A C3A 116.41(12) . . ? N3A C5A N4A 113.75(14) . . ? N3A C5A H5C 123.1 . . ? N4A C5A H5C 123.1 . . ? C1B N1B C4B 118.6(11) . . ? C2B N2B C1B 114.6(13) . . ? C5B N3B C3B 105.1(12) . . ? C2B N4B C5B 102.7(11) . . ? C2B N4B H4B 128.7 . . ? C5B N4B H4B 128.7 . . ? C4B N5B H5X 120 . . ? C4B N5B H5Y 120 . . ? H5X N5B H5Y 120 . . ? N1B C1B N2B 127.2(13) . . ? N1B C1B H1X 116.4 . . ? N2B C1B H1X 116.4 . . ? N2B C2B N4B 129.0(13) . . ? N2B C2B C3B 122.4(13) . . ? N4B C2B C3B 108.6(11) . . ? N3B C3B C4B 132.1(11) . . ? N3B C3B C2B 108.9(11) . . ? C4B C3B C2B 118.7(10) . . ? N5B C4B N1B 119.4(15) . . ? N5B C4B C3B 121.3(16) . . ? N1B C4B C3B 118.4(10) . . ? N3B C5B N4B 114.7(12) . . ? N3B C5B H5Z 122.6 . . ? N4B C5B H5Z 122.6 . . ? C12 O1 H1 109.5 . . ? C11 C6 C7 119.64(12) . . ? C11 C6 C12 119.03(12) . . ? C7 C6 C12 121.33(11) . . ? C8 C7 C6 119.73(13) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 120.06(14) . . ? C9 C8 H8 120 . . ? C7 C8 H8 120 . . ? C10 C9 C8 120.45(14) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.04(14) . . ? C9 C10 H10 120 . . ? C11 C10 H10 120 . . ? C10 C11 C6 120.07(13) . . ? C10 C11 H11 120 . . ? C6 C11 H11 120 . . ? O2 C12 O1 123.77(12) . . ? O2 C12 C6 122.62(11) . . ? O1 C12 C6 113.60(11) . . ? C19 O3 H3 109.5 . . ? C14 C13 C18 119.26(12) . . ? C14 C13 C19 119.73(11) . . ? C18 C13 C19 120.98(11) . . ? C15 C14 C13 120.13(13) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.42(13) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 119.76(13) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.15(13) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 120.28(12) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? O4 C19 O3 123.41(12) . . ? O4 C19 C13 122.67(11) . . ? O3 C19 C13 113.91(10) . . ? 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 C2A N2A C1A N1A 1.6(2) . . . . ? C4A N1A C1A N2A 0.3(2) . . . . ? C1A N2A C2A N4A 179.55(15) . . . . ? C1A N2A C2A C3A -1.3(2) . . . . ? C5A N4A C2A N2A 179.80(15) . . . . ? C5A N4A C2A C3A 0.47(17) . . . . ? N2A C2A C3A N3A -179.58(14) . . . . ? N4A C2A C3A N3A -0.26(16) . . . . ? N2A C2A C3A C4A -0.8(2) . . . . ? N4A C2A C3A C4A 178.56(13) . . . . ? C5A N3A C3A C2A -0.07(16) . . . . ? C5A N3A C3A C4A -178.64(15) . . . . ? C1A N1A C4A N5A 177.5(2) . . . . ? C1A N1A C4A C3A -2.48(19) . . . . ? C2A C3A C4A N5A -177.3(2) . . . . ? N3A C3A C4A N5A 1.2(3) . . . . ? C2A C3A C4A N1A 2.63(19) . . . . ? N3A C3A C4A N1A -178.88(14) . . . . ? C3A N3A C5A N4A 0.39(17) . . . . ? C2A N4A C5A N3A -0.56(19) . . . . ? C4B N1B C1B N2B -1(2) . . . . ? C2B N2B C1B N1B 2(3) . . . . ? C1B N2B C2B N4B -176.9(18) . . . . ? C1B N2B C2B C3B 0(3) . . . . ? C5B N4B C2B N2B 178.3(19) . . . . ? C5B N4B C2B C3B 0.7(19) . . . . ? C5B N3B C3B C4B -173.9(14) . . . . ? C5B N3B C3B C2B 0.1(16) . . . . ? N2B C2B C3B N3B -178.3(17) . . . . ? N4B C2B C3B N3B -0.5(19) . . . . ? N2B C2B C3B C4B -3(2) . . . . ? N4B C2B C3B C4B 174.3(13) . . . . ? C1B N1B C4B N5B 167(2) . . . . ? C1B N1B C4B C3B -2.2(19) . . . . ? N3B C3B C4B N5B 8(3) . . . . ? C2B C3B C4B N5B -165(2) . . . . ? N3B C3B C4B N1B 177.7(14) . . . . ? C2B C3B C4B N1B 4.3(19) . . . . ? C3B N3B C5B N4B 0.4(17) . . . . ? C2B N4B C5B N3B -0.7(19) . . . . ? C11 C6 C7 C8 -0.4(2) . . . . ? C12 C6 C7 C8 179.42(12) . . . . ? C6 C7 C8 C9 -0.4(2) . . . . ? C7 C8 C9 C10 0.7(2) . . . . ? C8 C9 C10 C11 -0.2(2) . . . . ? C9 C10 C11 C6 -0.6(2) . . . . ? C7 C6 C11 C10 0.94(19) . . . . ? C12 C6 C11 C10 -178.88(12) . . . . ? C11 C6 C12 O2 -6.91(19) . . . . ? C7 C6 C12 O2 173.28(12) . . . . ? C11 C6 C12 O1 172.29(11) . . . . ? C7 C6 C12 O1 -7.53(17) . . . . ? C18 C13 C14 C15 0.5(2) . . . . ? C19 C13 C14 C15 -177.73(12) . . . . ? C13 C14 C15 C16 0.4(2) . . . . ? C14 C15 C16 C17 -1.0(2) . . . . ? C15 C16 C17 C18 0.7(2) . . . . ? C16 C17 C18 C13 0.2(2) . . . . ? C14 C13 C18 C17 -0.8(2) . . . . ? C19 C13 C18 C17 177.42(12) . . . . ? C14 C13 C19 O4 11.2(2) . . . . ? C18 C13 C19 O4 -166.95(13) . . . . ? C14 C13 C19 O3 -169.72(11) . . . . ? C18 C13 C19 O3 12.09(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1A 0.84 1.8 2.6357(15) 170.2 2_665 O1 H1 N3B 0.84 1.92 2.694(14) 152.3 . O3 H3 N3A 0.84 1.84 2.6721(15) 170.2 2_566 O3 H3 N1B 0.84 1.77 2.596(12) 167.7 1_456 N5A H5B O4 0.88 2.15 3.017(2) 166.3 2_566 N5A H5A O2 0.88 2.06 2.927(2) 167.1 2_665 N4A H4A N2A 0.88 1.98 2.8506(17) 167.6 2_775 N5B H5X O4 0.88 1.97 2.80(3) 156.7 1_654 N5B H5Y O2 0.88 2.33 3.17(2) 159.2 . N4B H4B N2B 0.88 1.95 2.796(19) 160.1 2 #-----------------------END OF CIF 1 OF 6--------------------------------- data_addip _database_code_depnum_ccdc_archive 'CCDC 686684' _audit_creation_date 2008-02-12T13:03:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Adenine - adipic acid (2:1) dimethanolate ; _chemical_formula_moiety ; 2(C5 H5 N5), C6 H10 O4, 2(C1 H4 O1) ; _chemical_formula_sum 'C18 H28 N10 O6' _chemical_formula_weight 480.5 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9781(5) _cell_length_b 9.9334(5) _cell_length_c 14.2815(7) _cell_angle_alpha 74.908(3) _cell_angle_beta 85.357(3) _cell_angle_gamma 66.786(3) _cell_volume 1129.84(10) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5020 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.6436 _exptl_absorpt_correction_T_max 0.9935 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type ; Bruker-Nonius KappaCCD Area Detector ; _diffrn_measurement_method ; \f and \w scans ; _diffrn_standards_number 0 _diffrn_standards_decay_% negligible _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_unetI/netI 0.0471 _diffrn_reflns_number 22714 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 5137 _reflns_number_gt 3644 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998) ; _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek,2002) ; _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0539P)^2^+0.2864P] 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_number_reflns 5137 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.25 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.054 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.81696(16) -0.10103(15) 0.02250(8) 0.0287(3) Uani 1 1 d . . . H1 H 0.7421 -0.1263 0.0121 0.034 Uiso 1 1 calc R . . O2 O 0.72167(16) -0.13095(14) 0.17253(9) 0.0296(3) Uani 1 1 d . . . O3 O 1.07342(16) 0.20006(14) 0.46546(8) 0.0273(3) Uani 1 1 d . . . H3 H 1.1147 0.2597 0.4721 0.033 Uiso 1 1 calc R . . O4 O 1.17570(16) 0.23689(14) 0.31762(9) 0.0292(3) Uani 1 1 d . . . C1 C 0.8157(2) -0.09603(18) 0.11400(12) 0.0215(4) Uani 1 1 d . . . C2 C 0.9392(2) -0.04260(19) 0.13745(12) 0.0230(4) Uani 1 1 d . . . H2A H 0.9259 0.0543 0.0902 0.028 Uiso 1 1 calc R . . H2B H 1.0487 -0.1172 0.1294 0.028 Uiso 1 1 calc R . . C3 C 0.9290(2) -0.0200(2) 0.23913(12) 0.0248(4) Uani 1 1 d . . . H3A H 0.9605 -0.1197 0.2865 0.03 Uiso 1 1 calc R . . H3B H 0.8152 0.0415 0.2512 0.03 Uiso 1 1 calc R . . C4 C 1.0371(2) 0.05795(19) 0.25571(12) 0.0226(4) Uani 1 1 d . . . H4X H 1.1521 -0.007 0.2493 0.027 Uiso 1 1 calc R . . H4Y H 1.0114 0.1547 0.2058 0.027 Uiso 1 1 calc R . . C5 C 1.0121(2) 0.0883(2) 0.35602(12) 0.0240(4) Uani 1 1 d . . . H5C H 0.8944 0.1402 0.3646 0.029 Uiso 1 1 calc R . . H5D H 1.0499 -0.0101 0.405 0.029 Uiso 1 1 calc R . . C6 C 1.0965(2) 0.18148(18) 0.37634(12) 0.0209(4) Uani 1 1 d . . . N1A N 0.69115(18) 0.33731(16) -0.10302(10) 0.0242(3) Uani 1 1 d . . . N2A N 0.67769(18) 0.35362(16) 0.06348(10) 0.0238(3) Uani 1 1 d . . . N3A N 0.39550(18) 0.19121(16) 0.03706(10) 0.0246(3) Uani 1 1 d . . . N4A N 0.48258(18) 0.25774(16) 0.15344(10) 0.0236(3) Uani 1 1 d . . . H4A H 0.4913 0.2719 0.2107 0.028 Uiso 1 1 calc R . . N5A N 0.54444(18) 0.23177(16) -0.16597(10) 0.0252(3) Uani 1 1 d . . . H5A H 0.5914 0.248 -0.222 0.03 Uiso 1 1 calc R . . H5B H 0.4735 0.1893 -0.1593 0.03 Uiso 1 1 calc R . . C1A C 0.7315(2) 0.37229(19) -0.02717(12) 0.0254(4) Uani 1 1 d . . . H1A H 0.8096 0.4168 -0.0394 0.031 Uiso 1 1 calc R . . C2A C 0.5662(2) 0.29108(18) 0.07267(12) 0.0209(4) Uani 1 1 d . . . C3A C 0.5112(2) 0.24995(18) 0.00074(12) 0.0219(4) Uani 1 1 d . . . C4A C 0.5809(2) 0.27163(18) -0.09122(12) 0.0223(4) Uani 1 1 d . . . C5A C 0.3831(2) 0.1984(2) 0.12828(12) 0.0254(4) Uani 1 1 d . . . H5Z H 0.3119 0.1654 0.1722 0.03 Uiso 1 1 calc R . . N1B N 0.31230(18) 0.67665(16) 0.35973(10) 0.0247(3) Uani 1 1 d . . . N2B N 0.33385(18) 0.66227(16) 0.52952(10) 0.0250(3) Uani 1 1 d . . . N3B N 0.20036(19) 0.37091(16) 0.51917(10) 0.0256(3) Uani 1 1 d . . . N4B N 0.25561(18) 0.46426(16) 0.63270(10) 0.0252(3) Uani 1 1 d . . . H4B H 0.2677 0.4749 0.6905 0.03 Uiso 1 1 calc R . . N5B N 0.22308(18) 0.52150(16) 0.30273(10) 0.0255(3) Uani 1 1 d . . . H5X H 0.2325 0.5703 0.243 0.031 Uiso 1 1 calc R . . H5Y H 0.1893 0.447 0.313 0.031 Uiso 1 1 calc R . . C1B C 0.3450(2) 0.7177(2) 0.43474(13) 0.0262(4) Uani 1 1 d . . . H1B H 0.3816 0.7983 0.4183 0.031 Uiso 1 1 calc R . . C2B C 0.2817(2) 0.54815(19) 0.54559(12) 0.0225(4) Uani 1 1 d . . . C3B C 0.2463(2) 0.49071(19) 0.47539(12) 0.0223(4) Uani 1 1 d . . . C4B C 0.2601(2) 0.56042(19) 0.37771(12) 0.0228(4) Uani 1 1 d . . . C5B C 0.2074(2) 0.3610(2) 0.61245(13) 0.0278(4) Uani 1 1 d . . . H5E H 0.1812 0.2886 0.6611 0.033 Uiso 1 1 calc R . . O5 O 0.79813(16) 0.45337(15) 0.19517(9) 0.0319(3) Uani 1 1 d . . . H5 H 0.7491 0.4257 0.1611 0.038 Uiso 1 1 calc R . . C7 C 0.9176(2) 0.4960(2) 0.13904(13) 0.0311(4) Uani 1 1 d . . . H7A H 0.8665 0.574 0.0802 0.037 Uiso 1 1 calc R . . H7B H 1.0001 0.4075 0.1211 0.037 Uiso 1 1 calc R . . H7C H 0.9687 0.5361 0.1771 0.037 Uiso 1 1 calc R . . O6 O 0.56911(17) 0.22931(14) 0.33651(8) 0.0304(3) Uani 1 1 d . . . H6 H 0.5923 0.2769 0.3699 0.037 Uiso 1 1 calc R . . C8 C 0.5606(3) 0.0955(2) 0.39778(14) 0.0356(5) Uani 1 1 d . . . H8A H 0.6622 0.0365 0.4356 0.043 Uiso 1 1 calc R . . H8B H 0.5436 0.0353 0.3583 0.043 Uiso 1 1 calc R . . H8C H 0.4703 0.1219 0.4419 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 0.0362(8) 0.0410(7) 0.0200(6) -0.0086(6) 0.0041(5) -0.0264(6) O2 0.0366(8) 0.0396(7) 0.0211(6) -0.0052(6) 0.0041(5) -0.0257(6) O3 0.0385(8) 0.0334(7) 0.0209(6) -0.0088(5) 0.0054(5) -0.0247(6) O4 0.0379(8) 0.0370(7) 0.0231(7) -0.0084(6) 0.0083(6) -0.0262(6) C1 0.0260(9) 0.0184(8) 0.0182(8) -0.0027(7) 0.0012(7) -0.0080(7) C2 0.0257(9) 0.0237(8) 0.0230(9) -0.0066(7) 0.0036(7) -0.0131(7) C3 0.0290(10) 0.0287(9) 0.0215(9) -0.0064(7) 0.0025(7) -0.0166(8) C4 0.0271(9) 0.0229(8) 0.0211(9) -0.0041(7) 0.0013(7) -0.0141(8) C5 0.0280(10) 0.0267(9) 0.0213(9) -0.0051(7) 0.0036(7) -0.0159(8) C6 0.0228(9) 0.0213(8) 0.0174(8) -0.0023(7) 0.0008(7) -0.0089(7) N1A 0.0282(8) 0.0250(7) 0.0207(8) -0.0039(6) 0.0047(6) -0.0134(7) N2A 0.0293(8) 0.0245(7) 0.0188(8) -0.0040(6) 0.0023(6) -0.0131(7) N3A 0.0270(8) 0.0286(8) 0.0205(8) -0.0038(6) 0.0022(6) -0.0150(7) N4A 0.0298(8) 0.0273(8) 0.0168(7) -0.0046(6) 0.0007(6) -0.0148(7) N5A 0.0321(9) 0.0336(8) 0.0163(7) -0.0079(6) 0.0060(6) -0.0194(7) C1A 0.0284(10) 0.0242(9) 0.0252(9) -0.0038(7) 0.0033(7) -0.0137(8) C2A 0.0238(9) 0.0186(8) 0.0194(8) -0.0043(7) 0.0005(7) -0.0074(7) C3A 0.0247(9) 0.0214(8) 0.0198(9) -0.0030(7) 0.0005(7) -0.0106(7) C4A 0.0238(9) 0.0209(8) 0.0204(9) -0.0025(7) 0.0009(7) -0.0084(7) C5A 0.0283(10) 0.0293(9) 0.0205(9) -0.0040(7) 0.0014(7) -0.0147(8) N1B 0.0285(8) 0.0269(8) 0.0197(8) -0.0037(6) 0.0031(6) -0.0136(7) N2B 0.0273(8) 0.0284(8) 0.0191(8) -0.0047(6) 0.0030(6) -0.0119(7) N3B 0.0323(9) 0.0268(8) 0.0207(8) -0.0040(6) 0.0027(6) -0.0162(7) N4B 0.0319(9) 0.0313(8) 0.0171(7) -0.0069(6) 0.0015(6) -0.0167(7) N5B 0.0365(9) 0.0293(8) 0.0159(7) -0.0035(6) 0.0016(6) -0.0196(7) C1B 0.0276(10) 0.0263(9) 0.0259(10) -0.0052(7) 0.0026(8) -0.0130(8) C2B 0.0221(9) 0.0261(9) 0.0192(9) -0.0061(7) 0.0016(7) -0.0092(7) C3B 0.0234(9) 0.0231(8) 0.0215(9) -0.0047(7) 0.0025(7) -0.0112(7) C4B 0.0219(9) 0.0241(9) 0.0211(9) -0.0054(7) 0.0032(7) -0.0081(7) C5B 0.0359(11) 0.0319(10) 0.0209(9) -0.0054(7) 0.0023(8) -0.0198(9) O5 0.0356(8) 0.0446(8) 0.0277(7) -0.0169(6) 0.0074(6) -0.0244(6) C7 0.0348(11) 0.0317(10) 0.0285(10) -0.0026(8) 0.0010(8) -0.0179(9) O6 0.0452(8) 0.0324(7) 0.0194(6) -0.0028(5) -0.0022(6) -0.0226(6) C8 0.0387(12) 0.0366(11) 0.0325(11) 0.0017(9) -0.0006(9) -0.0217(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.320(2) . ? O1 H1 0.84 . ? O2 C1 1.223(2) . ? O3 C6 1.322(2) . ? O3 H3 0.84 . ? O4 C6 1.218(2) . ? C1 C2 1.497(2) . ? C2 C3 1.517(2) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.524(2) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C5 1.521(2) . ? C4 H4X 0.99 . ? C4 H4Y 0.99 . ? C5 C6 1.498(2) . ? C5 H5C 0.99 . ? C5 H5D 0.99 . ? N1A C1A 1.336(2) . ? N1A C4A 1.363(2) . ? N2A C1A 1.337(2) . ? N2A C2A 1.354(2) . ? N3A C5A 1.316(2) . ? N3A C3A 1.386(2) . ? N4A C5A 1.361(2) . ? N4A C2A 1.364(2) . ? N4A H4A 0.88 . ? N5A C4A 1.335(2) . ? N5A H5A 0.88 . ? N5A H5B 0.88 . ? C1A H1A 0.95 . ? C2A C3A 1.388(2) . ? C3A C4A 1.410(2) . ? C5A H5Z 0.95 . ? N1B C1B 1.331(2) . ? N1B C4B 1.368(2) . ? N2B C1B 1.334(2) . ? N2B C2B 1.350(2) . ? N3B C5B 1.315(2) . ? N3B C3B 1.391(2) . ? N4B C5B 1.359(2) . ? N4B C2B 1.365(2) . ? N4B H4B 0.88 . ? N5B C4B 1.334(2) . ? N5B H5X 0.88 . ? N5B H5Y 0.88 . ? C1B H1B 0.95 . ? C2B C3B 1.387(2) . ? C3B C4B 1.406(2) . ? C5B H5E 0.95 . ? O5 C7 1.420(2) . ? O5 H5 0.84 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? O6 C8 1.415(2) . ? O6 H6 0.84 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? 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 O1 H1 109.5 . . ? C6 O3 H3 109.5 . . ? O2 C1 O1 122.72(16) . . ? O2 C1 C2 124.26(15) . . ? O1 C1 C2 113.02(14) . . ? C1 C2 C3 114.22(14) . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C2 C3 C4 113.07(14) . . ? C2 C3 H3A 109 . . ? C4 C3 H3A 109 . . ? C2 C3 H3B 109 . . ? C4 C3 H3B 109 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 110.65(14) . . ? C5 C4 H4X 109.5 . . ? C3 C4 H4X 109.5 . . ? C5 C4 H4Y 109.5 . . ? C3 C4 H4Y 109.5 . . ? H4X C4 H4Y 108.1 . . ? C6 C5 C4 115.58(14) . . ? C6 C5 H5C 108.4 . . ? C4 C5 H5C 108.4 . . ? C6 C5 H5D 108.4 . . ? C4 C5 H5D 108.4 . . ? H5C C5 H5D 107.4 . . ? O4 C6 O3 123.01(15) . . ? O4 C6 C5 124.51(15) . . ? O3 C6 C5 112.47(14) . . ? C1A N1A C4A 118.97(14) . . ? C1A N2A C2A 110.51(14) . . ? C5A N3A C3A 104.06(14) . . ? C5A N4A C2A 106.72(14) . . ? C5A N4A H4A 126.6 . . ? C2A N4A H4A 126.6 . . ? C4A N5A H5A 120 . . ? C4A N5A H5B 120 . . ? H5A N5A H5B 120 . . ? N1A C1A N2A 129.29(16) . . ? N1A C1A H1A 115.4 . . ? N2A C1A H1A 115.4 . . ? N2A C2A N4A 127.49(15) . . ? N2A C2A C3A 126.82(15) . . ? N4A C2A C3A 105.68(14) . . ? N3A C3A C2A 110.25(14) . . ? N3A C3A C4A 132.64(15) . . ? C2A C3A C4A 117.10(15) . . ? N5A C4A N1A 119.15(15) . . ? N5A C4A C3A 123.60(15) . . ? N1A C4A C3A 117.25(15) . . ? N3A C5A N4A 113.28(15) . . ? N3A C5A H5Z 123.4 . . ? N4A C5A H5Z 123.4 . . ? C1B N1B C4B 118.57(14) . . ? C1B N2B C2B 110.88(15) . . ? C5B N3B C3B 103.94(14) . . ? C5B N4B C2B 106.45(14) . . ? C5B N4B H4B 126.8 . . ? C2B N4B H4B 126.8 . . ? C4B N5B H5X 120 . . ? C4B N5B H5Y 120 . . ? H5X N5B H5Y 120 . . ? N1B C1B N2B 129.55(16) . . ? N1B C1B H1B 115.2 . . ? N2B C1B H1B 115.2 . . ? N2B C2B N4B 127.80(15) . . ? N2B C2B C3B 126.23(15) . . ? N4B C2B C3B 105.97(14) . . ? C2B C3B N3B 110.00(15) . . ? C2B C3B C4B 117.55(15) . . ? N3B C3B C4B 132.45(16) . . ? N5B C4B N1B 118.80(15) . . ? N5B C4B C3B 124.01(15) . . ? N1B C4B C3B 117.18(15) . . ? N3B C5B N4B 113.64(16) . . ? N3B C5B H5E 123.2 . . ? N4B C5B H5E 123.2 . . ? C7 O5 H5 109.5 . . ? O5 C7 H7A 109.5 . . ? O5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8 O6 H6 109.5 . . ? O6 C8 H8A 109.5 . . ? O6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 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 O2 C1 C2 C3 -5.6(2) . . . . ? O1 C1 C2 C3 173.92(14) . . . . ? C1 C2 C3 C4 -170.77(14) . . . . ? C2 C3 C4 C5 175.69(15) . . . . ? C3 C4 C5 C6 -172.78(15) . . . . ? C4 C5 C6 O4 2.9(3) . . . . ? C4 C5 C6 O3 -178.27(15) . . . . ? C4A N1A C1A N2A -0.6(3) . . . . ? C2A N2A C1A N1A -0.6(3) . . . . ? C1A N2A C2A N4A -178.74(16) . . . . ? C1A N2A C2A C3A 0.0(2) . . . . ? C5A N4A C2A N2A 179.30(16) . . . . ? C5A N4A C2A C3A 0.31(18) . . . . ? C5A N3A C3A C2A 0.15(19) . . . . ? C5A N3A C3A C4A 178.94(18) . . . . ? N2A C2A C3A N3A -179.28(16) . . . . ? N4A C2A C3A N3A -0.29(18) . . . . ? N2A C2A C3A C4A 1.7(3) . . . . ? N4A C2A C3A C4A -179.30(15) . . . . ? C1A N1A C4A N5A -177.73(15) . . . . ? C1A N1A C4A C3A 2.4(2) . . . . ? N3A C3A C4A N5A -1.5(3) . . . . ? C2A C3A C4A N5A 177.28(16) . . . . ? N3A C3A C4A N1A 178.42(17) . . . . ? C2A C3A C4A N1A -2.8(2) . . . . ? C3A N3A C5A N4A 0.1(2) . . . . ? C2A N4A C5A N3A -0.2(2) . . . . ? C4B N1B C1B N2B -0.5(3) . . . . ? C2B N2B C1B N1B 0.3(3) . . . . ? C1B N2B C2B N4B 180.00(17) . . . . ? C1B N2B C2B C3B 1.2(2) . . . . ? C5B N4B C2B N2B -178.64(17) . . . . ? C5B N4B C2B C3B 0.31(19) . . . . ? N2B C2B C3B N3B 178.33(16) . . . . ? N4B C2B C3B N3B -0.65(19) . . . . ? N2B C2B C3B C4B -2.4(3) . . . . ? N4B C2B C3B C4B 178.61(15) . . . . ? C5B N3B C3B C2B 0.7(2) . . . . ? C5B N3B C3B C4B -178.39(19) . . . . ? C1B N1B C4B N5B 178.26(16) . . . . ? C1B N1B C4B C3B -0.7(2) . . . . ? C2B C3B C4B N5B -176.93(16) . . . . ? N3B C3B C4B N5B 2.1(3) . . . . ? C2B C3B C4B N1B 2.0(2) . . . . ? N3B C3B C4B N1B -178.95(17) . . . . ? C3B N3B C5B N4B -0.5(2) . . . . ? C2B N4B C5B N3B 0.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N3A 0.84 1.85 2.6779(18) 166.4 2_655 O3 H3 N3B 0.84 1.84 2.6668(18) 165.7 1_655 N4A H4A O6 0.88 1.86 2.7001(18) 158.4 . N5A H5A N1B 0.88 2.16 3.029(2) 171.4 2_665 N5A H5B O2 0.88 2.09 2.9481(19) 166.1 2_655 N4B H4B O5 0.88 1.91 2.7366(18) 156.4 2_666 N5B H5X N1A 0.88 2.15 3.018(2) 168 2_665 N5B H5Y O4 0.88 2.12 2.9731(18) 162.5 1_455 O5 H5 N2A 0.84 1.97 2.7988(18) 167.2 . O6 H6 N2B 0.84 1.95 2.7680(19) 165.6 2_666 #---------------------------END OF CIF 2 OF 6----------------------------------- data_ad26 _database_code_depnum_ccdc_archive 'CCDC 686685' _audit_creation_date 2008-02-12T13:46:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Adenine 2,6-dihydroxybenzoate ; _chemical_formula_moiety ; C5 H6 N5 1+, C7 H5 O4 1- ; _chemical_formula_sum 'C12 H11 N5 O4' _chemical_formula_weight 289.26 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 7.0966(3) _cell_length_b 7.2069(3) _cell_length_c 23.5630(11) _cell_angle_alpha 90 _cell_angle_beta 93.978(3) _cell_angle_gamma 90 _cell_volume 1202.21(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6301 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.7409 _exptl_absorpt_correction_T_max 0.9975 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type ; Bruker-Nonius KappaCCD Area Detector ; _diffrn_measurement_method ; \f and \w scans ; _diffrn_standards_number 0 _diffrn_standards_decay_% negligible _diffrn_reflns_av_R_equivalents 0.0711 _diffrn_reflns_av_unetI/netI 0.0615 _diffrn_reflns_number 13251 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 2738 _reflns_number_gt 1862 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998) ; _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek,2002) ; _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0488P)^2^+0.5699P] 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_number_reflns 2738 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.254 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.066 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.8109(2) 0.3844(2) 0.06569(6) 0.0229(4) Uani 1 1 d . . . O2 O 1.0539(2) 0.3518(2) 0.13030(6) 0.0213(4) Uani 1 1 d . . . O3 O 0.4944(2) 0.5017(2) 0.09277(6) 0.0234(4) Uani 1 1 d . . . H3 H 0.5749 0.4595 0.0717 0.028 Uiso 1 1 calc R . . O4 O 1.02687(19) 0.4790(2) 0.23116(6) 0.0228(4) Uani 1 1 d . . . H4 H 1.0774 0.4305 0.2036 0.027 Uiso 1 1 calc R . . C6 C 0.8863(3) 0.4012(3) 0.11654(9) 0.0167(5) Uani 1 1 d . . . C7 C 0.7678(3) 0.4827(3) 0.15962(8) 0.0156(4) Uani 1 1 d . . . C8 C 0.5770(3) 0.5328(3) 0.14554(9) 0.0166(4) Uani 1 1 d . . . C9 C 0.4691(3) 0.6179(3) 0.18525(9) 0.0189(5) Uani 1 1 d . . . H9 H 0.3416 0.6516 0.1754 0.023 Uiso 1 1 calc R . . C10 C 0.5502(3) 0.6528(3) 0.23932(9) 0.0188(5) Uani 1 1 d . . . H10 H 0.4773 0.7128 0.2662 0.023 Uiso 1 1 calc R . . C11 C 0.7348(3) 0.6028(3) 0.25534(9) 0.0185(5) Uani 1 1 d . . . H11 H 0.7864 0.6251 0.293 0.022 Uiso 1 1 calc R . . C12 C 0.8435(3) 0.5195(3) 0.21564(9) 0.0165(5) Uani 1 1 d . . . N1 N 1.0206(2) 0.7587(2) 0.02036(7) 0.0174(4) Uani 1 1 d . . . H1A H 1.0702 0.7103 -0.0095 0.021 Uiso 1 1 calc R . . N2 N 1.0735(2) 0.8292(2) 0.11871(7) 0.0193(4) Uani 1 1 d . . . N3 N 0.6004(2) 0.9739(2) 0.07495(8) 0.0198(4) Uani 1 1 d . . . N4 N 0.7928(2) 0.9668(2) 0.15459(7) 0.0180(4) Uani 1 1 d . . . H4A H 0.8314 0.9821 0.1906 0.022 Uiso 1 1 calc R . . N5 N 0.7460(2) 0.8166(3) -0.03635(7) 0.0208(4) Uani 1 1 d . . . H5A H 0.7991 0.7671 -0.0654 0.025 Uiso 1 1 calc R . . H5B H 0.6299 0.8598 -0.0407 0.025 Uiso 1 1 calc R . . C1 C 1.1272(3) 0.7626(3) 0.07062(9) 0.0195(5) Uani 1 1 d . . . H1 H 1.2512 0.7128 0.0709 0.023 Uiso 1 1 calc R . . C2 C 0.8945(3) 0.8956(3) 0.11291(9) 0.0158(4) Uani 1 1 d . . . C3 C 0.7745(3) 0.9004(3) 0.06365(9) 0.0155(4) Uani 1 1 d . . . C4 C 0.8405(3) 0.8260(3) 0.01385(9) 0.0167(5) Uani 1 1 d . . . C5 C 0.6196(3) 1.0096(3) 0.12965(9) 0.0208(5) Uani 1 1 d . . . H5 H 0.5212 1.0608 0.1501 0.025 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(8) 0.0304(9) 0.0148(8) -0.0058(7) 0.0001(6) 0.0040(7) O2 0.0187(8) 0.0267(9) 0.0185(8) -0.0006(6) 0.0023(6) 0.0054(6) O3 0.0189(8) 0.0353(10) 0.0159(8) -0.0071(7) -0.0004(6) 0.0039(7) O4 0.0173(8) 0.0345(9) 0.0165(8) -0.0011(7) -0.0004(6) 0.0059(7) C6 0.0197(11) 0.0135(10) 0.0173(11) -0.0005(9) 0.0034(9) -0.0011(9) C7 0.0165(11) 0.0151(10) 0.0151(11) -0.0002(8) 0.0013(8) -0.0001(8) C8 0.0174(11) 0.0176(10) 0.0147(11) -0.0005(9) -0.0003(8) -0.0001(9) C9 0.0172(11) 0.0200(11) 0.0197(12) 0.0020(9) 0.0026(9) 0.0021(9) C10 0.0226(11) 0.0186(11) 0.0161(11) 0.0001(9) 0.0075(8) 0.0022(9) C11 0.0235(12) 0.0207(11) 0.0112(10) 0.0004(9) 0.0006(8) -0.0008(9) C12 0.0158(11) 0.0173(11) 0.0162(11) 0.0032(9) 0.0007(8) -0.0016(8) N1 0.0200(9) 0.0194(9) 0.0129(9) -0.0025(7) 0.0019(7) 0.0027(7) N2 0.0187(9) 0.0218(10) 0.0175(10) 0.0022(8) 0.0017(7) 0.0012(8) N3 0.0201(10) 0.0223(10) 0.0171(10) -0.0012(8) 0.0025(7) 0.0022(8) N4 0.0205(10) 0.0214(10) 0.0120(9) -0.0008(7) 0.0009(7) 0.0018(8) N5 0.0199(9) 0.0278(10) 0.0145(10) -0.0046(8) 0.0007(7) 0.0031(8) C1 0.0180(11) 0.0226(12) 0.0177(12) 0.0022(9) 0.0015(9) 0.0035(9) C2 0.0189(11) 0.0144(10) 0.0140(11) 0.0007(8) 0.0011(8) -0.0010(8) C3 0.0173(11) 0.0142(10) 0.0151(11) 0.0011(8) 0.0018(8) -0.0004(8) C4 0.0176(11) 0.0140(10) 0.0187(11) 0.0009(9) 0.0021(8) 0.0003(8) C5 0.0201(11) 0.0243(12) 0.0183(12) -0.0023(9) 0.0026(9) 0.0027(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.283(2) . ? O2 C6 1.262(2) . ? O3 C8 1.356(2) . ? O3 H3 0.84 . ? O4 C12 1.359(2) . ? O4 H4 0.84 . ? C6 C7 1.484(3) . ? C7 C12 1.415(3) . ? C7 C8 1.418(3) . ? C8 C9 1.392(3) . ? C9 C10 1.384(3) . ? C9 H9 0.95 . ? C10 C11 1.385(3) . ? C10 H10 0.95 . ? C11 C12 1.389(3) . ? C11 H11 0.95 . ? N1 C1 1.361(3) . ? N1 C4 1.366(3) . ? N1 H1A 0.88 . ? N2 C1 1.311(3) . ? N2 C2 1.355(3) . ? N3 C5 1.312(3) . ? N3 C3 1.387(3) . ? N4 C2 1.359(3) . ? N4 C5 1.360(3) . ? N4 H4A 0.88 . ? N5 C4 1.320(3) . ? N5 H5A 0.88 . ? N5 H5B 0.88 . ? C1 H1 0.95 . ? C2 C3 1.392(3) . ? C3 C4 1.400(3) . ? C5 H5 0.95 . ? 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 C8 O3 H3 109.5 . . ? C12 O4 H4 109.5 . . ? O2 C6 O1 122.52(19) . . ? O2 C6 C7 120.30(18) . . ? O1 C6 C7 117.18(18) . . ? C12 C7 C8 117.70(19) . . ? C12 C7 C6 121.07(18) . . ? C8 C7 C6 121.19(18) . . ? O3 C8 C9 117.77(18) . . ? O3 C8 C7 121.18(18) . . ? C9 C8 C7 121.05(18) . . ? C10 C9 C8 119.05(19) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 121.91(19) . . ? C9 C10 H10 119 . . ? C11 C10 H10 119 . . ? C10 C11 C12 119.16(19) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? O4 C12 C11 118.52(18) . . ? O4 C12 C7 120.34(18) . . ? C11 C12 C7 121.11(19) . . ? C1 N1 C4 123.37(18) . . ? C1 N1 H1A 118.3 . . ? C4 N1 H1A 118.3 . . ? C1 N2 C2 111.64(18) . . ? C5 N3 C3 103.32(17) . . ? C2 N4 C5 106.40(17) . . ? C2 N4 H4A 126.8 . . ? C5 N4 H4A 126.8 . . ? C4 N5 H5A 120 . . ? C4 N5 H5B 120 . . ? H5A N5 H5B 120 . . ? N2 C1 N1 125.6(2) . . ? N2 C1 H1 117.2 . . ? N1 C1 H1 117.2 . . ? N2 C2 N4 126.96(18) . . ? N2 C2 C3 127.44(19) . . ? N4 C2 C3 105.58(18) . . ? N3 C3 C2 110.55(18) . . ? N3 C3 C4 131.42(19) . . ? C2 C3 C4 117.94(19) . . ? N5 C4 N1 119.70(19) . . ? N5 C4 C3 126.30(19) . . ? N1 C4 C3 114.00(18) . . ? N3 C5 N4 114.14(19) . . ? N3 C5 H5 122.9 . . ? N4 C5 H5 122.9 . . ? 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 O2 C6 C7 C12 4.7(3) . . . . ? O1 C6 C7 C12 -175.13(18) . . . . ? O2 C6 C7 C8 -177.67(19) . . . . ? O1 C6 C7 C8 2.5(3) . . . . ? C12 C7 C8 O3 -179.90(18) . . . . ? C6 C7 C8 O3 2.4(3) . . . . ? C12 C7 C8 C9 1.0(3) . . . . ? C6 C7 C8 C9 -176.72(19) . . . . ? O3 C8 C9 C10 -179.46(19) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? C8 C9 C10 C11 -1.1(3) . . . . ? C9 C10 C11 C12 1.7(3) . . . . ? C10 C11 C12 O4 177.00(18) . . . . ? C10 C11 C12 C7 -1.0(3) . . . . ? C8 C7 C12 O4 -178.28(18) . . . . ? C6 C7 C12 O4 -0.6(3) . . . . ? C8 C7 C12 C11 -0.3(3) . . . . ? C6 C7 C12 C11 177.39(19) . . . . ? C2 N2 C1 N1 0.1(3) . . . . ? C4 N1 C1 N2 0.2(3) . . . . ? C1 N2 C2 N4 177.0(2) . . . . ? C1 N2 C2 C3 -0.9(3) . . . . ? C5 N4 C2 N2 -177.9(2) . . . . ? C5 N4 C2 C3 0.3(2) . . . . ? C5 N3 C3 C2 -0.4(2) . . . . ? C5 N3 C3 C4 176.1(2) . . . . ? N2 C2 C3 N3 178.27(19) . . . . ? N4 C2 C3 N3 0.0(2) . . . . ? N2 C2 C3 C4 1.3(3) . . . . ? N4 C2 C3 C4 -176.95(18) . . . . ? C1 N1 C4 N5 -179.78(19) . . . . ? C1 N1 C4 C3 0.2(3) . . . . ? N3 C3 C4 N5 2.9(4) . . . . ? C2 C3 C4 N5 179.1(2) . . . . ? N3 C3 C4 N1 -177.0(2) . . . . ? C2 C3 C4 N1 -0.8(3) . . . . ? C3 N3 C5 N4 0.6(2) . . . . ? C2 N4 C5 N3 -0.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4A O4 0.88 2.04 2.901(2) 166.3 2_755 N5 H5A O2 0.88 2.09 2.971(2) 175.3 3_765 N5 H5B N3 0.88 2.14 2.974(2) 158 3_675 N1 H1A O1 0.88 1.76 2.635(2) 174.9 3_765 O3 H3 O1 0.84 1.77 2.523(2) 147.4 . O4 H4 O2 0.84 1.81 2.567(2) 148.3 . #--------------------END OF CIF 3 OF 6--------------------------------------- data_ad26h _database_code_depnum_ccdc_archive 'CCDC 686686' _audit_creation_date 2008-02-12T14:29:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Adenine 2,6-dihydroxybenzoate hydrate ; _chemical_formula_moiety ; C7 H5 O4 1-, C5 H6 N5 1+, H2 O1 ; _chemical_formula_sum 'C12 H13 N5 O5' _chemical_formula_weight 307.27 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.9541(2) _cell_length_b 15.2160(6) _cell_length_c 7.0195(3) _cell_angle_alpha 90 _cell_angle_beta 118.59 _cell_angle_gamma 90 _cell_volume 652.20(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8129 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.7715 _exptl_absorpt_correction_T_max 0.9755 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type ; Bruker-Nonius KappaCCD Area Detector ; _diffrn_measurement_method ; \f and \w scans ; _diffrn_standards_number 0 _diffrn_standards_decay_% negligible _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_unetI/netI 0.0251 _diffrn_reflns_number 8951 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 1538 _reflns_number_gt 1468 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998) ; _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek,2002) ; _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0434P)^2^+2.1292P] 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_number_reflns 1538 _refine_ls_number_parameters 205 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1598 _refine_ls_wR_factor_gt 0.1583 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.115 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(3) _refine_diff_density_max 0.381 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.087 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 -0.3392(6) 0.7250(3) 0.7152(6) 0.0198(8) Uani 1 1 d . . . O2 O -0.0982(6) 0.7229(3) 1.0698(6) 0.0219(9) Uani 1 1 d . . . O3 O -0.2536(6) 0.8061(3) 0.4474(6) 0.0201(8) Uani 1 1 d . . . H3 H -0.3396 0.7924 0.4952 0.024 Uiso 1 1 d R . . O4 O 0.2829(7) 0.7849(3) 1.2033(6) 0.0224(9) Uani 1 1 d . . . H4 H 0.175 0.7636 1.2102 0.027 Uiso 1 1 d R . . O5 O 0.5296(6) 0.9769(3) 0.3995(6) 0.0208(8) Uani 1 1 d D . . H5X H 0.626(8) 0.993(3) 0.525(6) 0.02 Uiso 1 1 d D . . H5Y H 0.557(10) 0.9225(17) 0.392(9) 0.02 Uiso 1 1 d D . . N1 N 0.3496(7) 0.6411(3) 0.7753(7) 0.0169(9) Uani 1 1 d . . . H1A H 0.449 0.6698 0.7563 0.02 Uiso 1 1 calc R . . N2 N -0.0157(8) 0.5892(3) 0.5999(7) 0.0173(9) Uani 1 1 d . . . N3 N 0.2192(8) 0.5356(3) 1.1679(7) 0.0180(9) Uani 1 1 d . . . N4 N -0.1054(8) 0.5203(3) 0.8634(7) 0.0171(9) Uani 1 1 d . . . H4A H -0.2424 0.5049 0.7785 0.02 Uiso 1 1 d R . . N5 N 0.6039(7) 0.6262(3) 1.1414(7) 0.0201(10) Uani 1 1 d . . . H5A H 0.7014 0.6545 1.1186 0.024 Uiso 1 1 calc R . . H5B H 0.6386 0.6073 1.2724 0.024 Uiso 1 1 calc R . . C1 C 0.1529(9) 0.6285(4) 0.6019(9) 0.0177(10) Uani 1 1 d . . . H1 H 0.1338 0.6503 0.4671 0.021 Uiso 1 1 calc R . . C2 C 0.0333(8) 0.5609(3) 0.8019(8) 0.0154(10) Uani 1 1 d . . . C3 C 0.2321(9) 0.5699(4) 0.9918(8) 0.0163(10) Uani 1 1 d . . . C4 C 0.4058(9) 0.6122(3) 0.9792(9) 0.0171(10) Uani 1 1 d . . . C5 C 0.0132(9) 0.5081(4) 1.0814(9) 0.0175(10) Uani 1 1 d . . . H5C H -0.0464 0.4822 1.1649 0.021 Uiso 1 1 calc R . . C6 C -0.1538(8) 0.7437(4) 0.8734(8) 0.0158(10) Uani 1 1 d . . . C7 C 0.0066(8) 0.7910(3) 0.8271(8) 0.0152(10) Uani 1 1 d . . . C8 C -0.0475(8) 0.8186(3) 0.6168(8) 0.0144(10) Uani 1 1 d . . . C9 C 0.1046(9) 0.8598(4) 0.5716(9) 0.0175(10) Uani 1 1 d . . . H9 H 0.0649 0.878 0.4281 0.021 Uiso 1 1 calc R . . C10 C 0.3147(9) 0.8740(4) 0.7388(9) 0.0182(11) Uani 1 1 d . . . H10 H 0.4187 0.9021 0.708 0.022 Uiso 1 1 calc R . . C11 C 0.3772(9) 0.8484(4) 0.9494(9) 0.0193(11) Uani 1 1 d . . . H11 H 0.5225 0.8583 1.0615 0.023 Uiso 1 1 calc R . . C12 C 0.2225(8) 0.8073(4) 0.9959(8) 0.0156(10) 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 0.0179(18) 0.022(2) 0.0204(18) -0.0003(16) 0.0099(15) -0.0020(16) O2 0.0195(19) 0.028(2) 0.0192(18) 0.0034(16) 0.0101(16) -0.0043(17) O3 0.0135(17) 0.027(2) 0.0166(17) 0.0011(16) 0.0043(15) -0.0024(16) O4 0.0203(19) 0.030(2) 0.0142(17) 0.0028(16) 0.0065(15) -0.0022(17) O5 0.0201(18) 0.0187(18) 0.0187(18) -0.0014(16) 0.0053(14) 0.0026(16) N1 0.017(2) 0.014(2) 0.024(2) 0.0007(18) 0.0135(19) 0.0012(17) N2 0.019(2) 0.018(2) 0.019(2) -0.0009(17) 0.0126(18) -0.0017(17) N3 0.020(2) 0.019(2) 0.016(2) 0.0063(17) 0.0095(18) -0.0008(18) N4 0.017(2) 0.014(2) 0.015(2) 0.0017(17) 0.0038(17) -0.0018(17) N5 0.014(2) 0.026(2) 0.019(2) 0.005(2) 0.0072(18) 0.0002(19) C1 0.023(3) 0.014(2) 0.019(2) -0.001(2) 0.013(2) -0.001(2) C2 0.017(2) 0.011(2) 0.019(2) -0.0031(19) 0.009(2) -0.0016(19) C3 0.019(2) 0.012(2) 0.017(2) 0.0021(19) 0.009(2) 0.000(2) C4 0.017(2) 0.013(2) 0.022(3) -0.003(2) 0.011(2) -0.0012(19) C5 0.020(3) 0.014(2) 0.020(2) 0.003(2) 0.010(2) -0.001(2) C6 0.015(2) 0.014(2) 0.019(2) 0.0025(19) 0.008(2) 0.0023(19) C7 0.016(2) 0.012(2) 0.019(2) -0.0026(19) 0.0094(19) 0.0009(19) C8 0.014(2) 0.013(2) 0.015(2) -0.0026(19) 0.0068(19) 0.0013(19) C9 0.022(2) 0.015(2) 0.017(2) 0.0011(19) 0.010(2) 0.001(2) C10 0.022(3) 0.018(3) 0.024(3) -0.003(2) 0.018(2) -0.003(2) C11 0.015(2) 0.020(3) 0.021(3) -0.001(2) 0.008(2) -0.001(2) C12 0.017(2) 0.017(3) 0.013(2) -0.0010(19) 0.0075(19) 0.002(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.267(6) . ? O2 C6 1.281(6) . ? O3 C8 1.368(6) . ? O3 H3 0.84 . ? O4 C12 1.351(6) . ? O4 H4 0.8401 . ? O5 H5X 0.85(2) . ? O5 H5Y 0.86(2) . ? N1 C1 1.340(7) . ? N1 C4 1.364(7) . ? N1 H1A 0.88 . ? N2 C1 1.310(7) . ? N2 C2 1.360(7) . ? N3 C5 1.328(7) . ? N3 C3 1.384(7) . ? N4 C5 1.360(7) . ? N4 C2 1.377(7) . ? N4 H4A 0.88 . ? N5 C4 1.318(7) . ? N5 H5A 0.88 . ? N5 H5B 0.88 . ? C1 H1 0.95 . ? C2 C3 1.394(7) . ? C3 C4 1.408(8) . ? C5 H5C 0.95 . ? C6 C7 1.489(7) . ? C7 C8 1.402(7) . ? C7 C12 1.420(7) . ? C8 C9 1.391(8) . ? C9 C10 1.385(8) . ? C9 H9 0.95 . ? C10 C11 1.383(8) . ? C10 H10 0.95 . ? C11 C12 1.411(7) . ? C11 H11 0.95 . ? 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 C8 O3 H3 109.7 . . ? C12 O4 H4 109.5 . . ? H5X O5 H5Y 104(3) . . ? C1 N1 C4 124.2(5) . . ? C1 N1 H1A 117.9 . . ? C4 N1 H1A 117.9 . . ? C1 N2 C2 110.9(5) . . ? C5 N3 C3 103.1(4) . . ? C5 N4 C2 106.0(5) . . ? C5 N4 H4A 127 . . ? C2 N4 H4A 127 . . ? C4 N5 H5A 120 . . ? C4 N5 H5B 120 . . ? H5A N5 H5B 120 . . ? N2 C1 N1 126.4(5) . . ? N2 C1 H1 116.8 . . ? N1 C1 H1 116.8 . . ? N2 C2 N4 127.3(5) . . ? N2 C2 C3 127.2(5) . . ? N4 C2 C3 105.5(5) . . ? N3 C3 C2 111.0(5) . . ? N3 C3 C4 130.7(5) . . ? C2 C3 C4 118.2(5) . . ? N5 C4 N1 120.7(5) . . ? N5 C4 C3 126.4(5) . . ? N1 C4 C3 112.9(5) . . ? N3 C5 N4 114.3(5) . . ? N3 C5 H5C 122.8 . . ? N4 C5 H5C 122.8 . . ? O1 C6 O2 123.0(5) . . ? O1 C6 C7 118.1(5) . . ? O2 C6 C7 118.9(5) . . ? C8 C7 C12 118.1(5) . . ? C8 C7 C6 121.5(5) . . ? C12 C7 C6 120.3(5) . . ? O3 C8 C9 117.4(5) . . ? O3 C8 C7 121.0(5) . . ? C9 C8 C7 121.6(5) . . ? C10 C9 C8 119.1(5) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C11 C10 C9 121.7(5) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C10 C11 C12 119.2(5) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? O4 C12 C11 118.8(5) . . ? O4 C12 C7 121.0(5) . . ? C11 C12 C7 120.2(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 C2 N2 C1 N1 -0.3(8) . . . . ? C4 N1 C1 N2 1.6(9) . . . . ? C1 N2 C2 N4 177.1(5) . . . . ? C1 N2 C2 C3 -0.2(8) . . . . ? C5 N4 C2 N2 -177.1(5) . . . . ? C5 N4 C2 C3 0.6(6) . . . . ? C5 N3 C3 C2 -1.0(6) . . . . ? C5 N3 C3 C4 177.2(6) . . . . ? N2 C2 C3 N3 178.0(5) . . . . ? N4 C2 C3 N3 0.2(6) . . . . ? N2 C2 C3 C4 -0.5(9) . . . . ? N4 C2 C3 C4 -178.2(5) . . . . ? C1 N1 C4 N5 179.2(5) . . . . ? C1 N1 C4 C3 -2.1(8) . . . . ? N3 C3 C4 N5 2.1(10) . . . . ? C2 C3 C4 N5 -179.9(5) . . . . ? N3 C3 C4 N1 -176.6(5) . . . . ? C2 C3 C4 N1 1.5(7) . . . . ? C3 N3 C5 N4 1.4(6) . . . . ? C2 N4 C5 N3 -1.3(6) . . . . ? O1 C6 C7 C8 3.3(7) . . . . ? O2 C6 C7 C8 -177.5(5) . . . . ? O1 C6 C7 C12 -174.9(5) . . . . ? O2 C6 C7 C12 4.3(7) . . . . ? C12 C7 C8 O3 -179.1(5) . . . . ? C6 C7 C8 O3 2.7(7) . . . . ? C12 C7 C8 C9 0.8(8) . . . . ? C6 C7 C8 C9 -177.5(5) . . . . ? O3 C8 C9 C10 179.8(5) . . . . ? C7 C8 C9 C10 0.0(8) . . . . ? C8 C9 C10 C11 -0.1(8) . . . . ? C9 C10 C11 C12 -0.5(8) . . . . ? C10 C11 C12 O4 -178.0(5) . . . . ? C10 C11 C12 C7 1.2(8) . . . . ? C8 C7 C12 O4 177.8(5) . . . . ? C6 C7 C12 O4 -3.9(8) . . . . ? C8 C7 C12 C11 -1.3(8) . . . . ? C6 C7 C12 C11 176.9(5) . . . . ? 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 O3 H3 O1 0.84 1.85 2.546(5) 138.8 . O3 H3 O4 0.84 2.44 2.854(5) 111.2 1_454 O4 H4 O2 0.84 1.78 2.533(6) 148 . N4 H4A O5 0.88 1.83 2.708(6) 178 2_546 N5 H5A O2 0.88 1.9 2.776(6) 176 1_655 N5 H5B N2 0.88 2.42 3.086(6) 132.9 1_656 N1 H1A O1 0.88 1.83 2.714(6) 177.4 1_655 O5 H5X N3 0.85(2) 2.00(3) 2.827(6) 164(6) 2_657 O5 H5Y O3 0.86(2) 2.13(3) 2.942(6) 158(5) 1_655 #--------------------------END OF CIF 4 OF 6------------------------------- data_adsal _database_code_depnum_ccdc_archive 'CCDC 686687' _audit_creation_date 2008-02-12T14:36:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Adenine 2-hydroxybenzoate methanolate ; _chemical_formula_moiety ; C7 H5 O3 1-, C5 H6 N5 1+, C1 H4 O1 ; _chemical_formula_sum 'C13 H15 N5 O4' _chemical_formula_weight 305.3 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.1636(2) _cell_length_b 7.9486(3) _cell_length_c 24.7336(9) _cell_angle_alpha 90 _cell_angle_beta 91.248(2) _cell_angle_gamma 90 _cell_volume 1408.01(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3278 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.49 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.44 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.11 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.7372 _exptl_absorpt_correction_T_max 0.9784 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type ; Bruker-Nonius KappaCCD Area Detector ; _diffrn_measurement_method ; \f and \w scans ; _diffrn_standards_number 0 _diffrn_standards_decay_% negligible _diffrn_reflns_av_R_equivalents 0.0575 _diffrn_reflns_av_unetI/netI 0.0403 _diffrn_reflns_number 13944 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 3195 _reflns_number_gt 2449 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998) ; _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek,2002) ; _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0501P)^2^+0.6703P] 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_number_reflns 3195 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.239 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.48681(16) 0.51833(15) 0.39528(5) 0.0312(3) Uani 1 1 d . A . O2 O 0.19373(16) 0.57236(16) 0.41910(5) 0.0338(3) Uani 1 1 d . A . O3 O 0.5464(2) 0.3186(2) 0.31702(6) 0.0311(5) Uani 0.772(3) 1 d P A 1 H3 H 0.5718 0.382 0.3433 0.037 Uiso 0.772(3) 1 calc PR A 1 O4 O 0.18318(15) 0.09546(17) 0.62256(5) 0.0347(3) Uani 1 1 d . . . H4 H 0.282 0.0514 0.6116 0.042 Uiso 1 1 calc R . . N1 N 0.36457(18) 0.31038(17) 0.52030(5) 0.0247(3) Uani 1 1 d . . . H1 H 0.4103 0.3767 0.5458 0.03 Uiso 1 1 calc R . . N2 N 0.08719(18) 0.19952(18) 0.48015(6) 0.0266(3) Uani 1 1 d . . . N3 N 0.47376(18) 0.02351(17) 0.40929(5) 0.0255(3) Uani 1 1 d . . . N4 N 0.16116(18) 0.00779(17) 0.40694(5) 0.0253(3) Uani 1 1 d . . . H4A H 0.0481 -0.0235 0.3966 0.03 Uiso 1 1 calc R . . N5 N 0.66852(18) 0.25377(17) 0.49425(6) 0.0259(3) Uani 1 1 d . . . H5A H 0.71 0.3212 0.5201 0.031 Uiso 1 1 calc R . . H5B H 0.7478 0.2024 0.4732 0.031 Uiso 1 1 calc R . . C1 C 0.1760(2) 0.2931(2) 0.51574(7) 0.0270(4) Uani 1 1 d . . . H1A H 0.1026 0.3543 0.5405 0.032 Uiso 1 1 calc R . . C2 C 0.2063(2) 0.1178(2) 0.44726(6) 0.0235(3) Uani 1 1 d . . . C3 C 0.4004(2) 0.1262(2) 0.44826(6) 0.0232(3) Uani 1 1 d . . . C4 C 0.4874(2) 0.2297(2) 0.48718(6) 0.0233(3) Uani 1 1 d . . . C5 C 0.3249(2) -0.0443(2) 0.38575(7) 0.0269(4) Uani 1 1 d . . . H5C H 0.3315 -0.1223 0.3567 0.032 Uiso 1 1 calc R . . C6 C 0.2395(2) 0.3889(2) 0.34516(6) 0.0255(3) Uani 1 1 d . A . C7 C 0.3623(2) 0.3017(2) 0.31182(7) 0.0291(4) Uani 1 1 d . . . H7 H 0.4933 0.3153 0.3169 0.035 Uiso 0.228(3) 1 calc PR A 2 C8 C 0.2931(3) 0.1953(2) 0.27129(7) 0.0353(4) Uani 1 1 d . A . H8 H 0.3769 0.1357 0.249 0.042 Uiso 1 1 calc R . . C9 C 0.1035(3) 0.1767(2) 0.26360(7) 0.0375(4) Uani 1 1 d . . . H9 H 0.057 0.1054 0.2356 0.045 Uiso 1 1 calc R A . C10 C -0.0210(3) 0.2610(2) 0.29639(8) 0.0364(4) Uani 1 1 d . A . H10 H -0.1518 0.2467 0.2911 0.044 Uiso 1 1 calc R . . C11 C 0.0472(2) 0.3658(2) 0.33671(7) 0.0301(4) Uani 1 1 d . . . H11 H -0.0378 0.4233 0.3592 0.036 Uiso 0.772(3) 1 calc PR A 1 C12 C 0.3097(2) 0.5011(2) 0.38958(7) 0.0269(4) Uani 1 1 d . . . C13 C 0.2139(3) 0.1599(3) 0.67547(8) 0.0490(6) Uani 1 1 d . . . H13A H 0.2823 0.2664 0.6735 0.059 Uiso 1 1 calc R . . H13B H 0.2872 0.0788 0.6969 0.059 Uiso 1 1 calc R . . H13C H 0.0936 0.1789 0.6926 0.059 Uiso 1 1 calc R . . O31 O -0.0669(10) 0.4366(10) 0.3650(3) 0.059 Uiso 0.228(3) 1 d P A 2 H31 H -0.0106 0.4922 0.3892 0.059 Uiso 0.228(3) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0292(6) 0.0319(7) 0.0323(6) -0.0028(5) -0.0008(5) -0.0040(5) O2 0.0308(6) 0.0345(7) 0.0361(7) -0.0095(6) 0.0005(5) -0.0008(5) O3 0.0255(8) 0.0353(10) 0.0327(9) -0.0038(7) 0.0015(6) -0.0011(6) O4 0.0220(6) 0.0483(8) 0.0337(7) -0.0086(6) 0.0004(5) -0.0006(5) N1 0.0266(7) 0.0216(7) 0.0257(7) -0.0006(5) -0.0025(5) -0.0020(5) N2 0.0243(7) 0.0252(7) 0.0302(7) 0.0019(6) 0.0006(6) -0.0011(6) N3 0.0260(7) 0.0246(7) 0.0259(7) 0.0014(6) 0.0007(5) 0.0001(6) N4 0.0226(7) 0.0253(7) 0.0278(7) 0.0015(6) -0.0025(5) -0.0024(5) N5 0.0220(7) 0.0256(7) 0.0300(7) -0.0012(6) -0.0018(6) -0.0017(6) C1 0.0262(8) 0.0261(8) 0.0288(9) 0.0012(7) 0.0012(6) 0.0007(7) C2 0.0223(7) 0.0216(8) 0.0264(8) 0.0060(6) -0.0015(6) -0.0012(6) C3 0.0234(8) 0.0213(8) 0.0250(8) 0.0030(6) -0.0002(6) -0.0006(6) C4 0.0236(8) 0.0200(8) 0.0262(8) 0.0050(6) -0.0006(6) -0.0001(6) C5 0.0269(8) 0.0254(8) 0.0283(9) 0.0014(7) -0.0001(6) -0.0009(7) C6 0.0319(8) 0.0208(8) 0.0237(8) 0.0026(6) -0.0011(6) -0.0021(7) C7 0.0330(9) 0.0251(9) 0.0291(9) 0.0047(7) -0.0002(7) -0.0001(7) C8 0.0442(11) 0.0304(10) 0.0313(9) -0.0026(8) -0.0001(8) 0.0045(8) C9 0.0491(11) 0.0329(10) 0.0301(10) -0.0057(8) -0.0101(8) 0.0000(8) C10 0.0354(10) 0.0348(10) 0.0387(10) -0.0002(8) -0.0106(8) -0.0002(8) C11 0.0322(9) 0.0281(9) 0.0297(9) 0.0003(7) -0.0020(7) 0.0033(7) C12 0.0317(9) 0.0222(8) 0.0266(8) 0.0042(7) -0.0013(7) -0.0034(7) C13 0.0429(11) 0.0611(14) 0.0433(12) -0.0204(11) 0.0058(9) -0.0122(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C12 1.281(2) . ? O2 C12 1.253(2) . ? O3 C7 1.329(2) . ? O3 H3 0.84 . ? O4 C13 1.418(2) . ? O4 H4 0.84 . ? N1 C1 1.360(2) . ? N1 C4 1.374(2) . ? N1 H1 0.88 . ? N2 C1 1.307(2) . ? N2 C2 1.357(2) . ? N3 C5 1.319(2) . ? N3 C3 1.376(2) . ? N4 C5 1.360(2) . ? N4 C2 1.360(2) . ? N4 H4A 0.88 . ? N5 C4 1.319(2) . ? N5 H5A 0.88 . ? N5 H5B 0.88 . ? C1 H1A 0.95 . ? C2 C3 1.392(2) . ? C3 C4 1.402(2) . ? C5 H5C 0.95 . ? C6 C11 1.400(2) . ? C6 C7 1.402(2) . ? C6 C12 1.494(2) . ? C7 C8 1.394(2) . ? C7 H7 0.95 . ? C8 C9 1.376(3) . ? C8 H8 0.95 . ? C9 C10 1.391(3) . ? C9 H9 0.95 . ? C10 C11 1.381(3) . ? C10 H10 0.95 . ? C11 O31 1.225(7) . ? C11 H11 0.95 . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? O31 H31 0.84 . ? 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 H3 109.5 . . ? C13 O4 H4 109.5 . . ? C1 N1 C4 123.46(14) . . ? C1 N1 H1 118.3 . . ? C4 N1 H1 118.3 . . ? C1 N2 C2 111.90(13) . . ? C5 N3 C3 103.55(13) . . ? C5 N4 C2 106.58(13) . . ? C5 N4 H4A 126.7 . . ? C2 N4 H4A 126.7 . . ? C4 N5 H5A 120 . . ? C4 N5 H5B 120 . . ? H5A N5 H5B 120 . . ? N2 C1 N1 125.55(16) . . ? N2 C1 H1A 117.2 . . ? N1 C1 H1A 117.2 . . ? N2 C2 N4 127.24(14) . . ? N2 C2 C3 127.38(15) . . ? N4 C2 C3 105.37(14) . . ? N3 C3 C2 110.85(14) . . ? N3 C3 C4 131.15(14) . . ? C2 C3 C4 117.99(14) . . ? N5 C4 N1 119.60(14) . . ? N5 C4 C3 126.68(15) . . ? N1 C4 C3 113.71(13) . . ? N3 C5 N4 113.65(15) . . ? N3 C5 H5C 123.2 . . ? N4 C5 H5C 123.2 . . ? C11 C6 C7 118.37(15) . . ? C11 C6 C12 120.16(15) . . ? C7 C6 C12 121.46(15) . . ? O3 C7 C8 117.83(16) . . ? O3 C7 C6 121.84(16) . . ? C8 C7 C6 120.33(16) . . ? O3 C7 H7 2.1 . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C9 C8 C7 119.92(17) . . ? C9 C8 H8 120 . . ? C7 C8 H8 120 . . ? C8 C9 C10 120.78(17) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 119.37(17) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? O31 C11 C10 117.4(4) . . ? O31 C11 C6 121.4(4) . . ? C10 C11 C6 121.24(16) . . ? O31 C11 H11 2 . . ? C10 C11 H11 119.4 . . ? C6 C11 H11 119.4 . . ? O2 C12 O1 123.74(15) . . ? O2 C12 C6 118.77(14) . . ? O1 C12 C6 117.49(15) . . ? O4 C13 H13A 109.5 . . ? O4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 O31 H31 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 C2 N2 C1 N1 0.3(2) . . . . ? C4 N1 C1 N2 0.1(3) . . . . ? C1 N2 C2 N4 178.29(15) . . . . ? C1 N2 C2 C3 -0.4(2) . . . . ? C5 N4 C2 N2 -178.95(15) . . . . ? C5 N4 C2 C3 -0.05(17) . . . . ? C5 N3 C3 C2 -0.05(17) . . . . ? C5 N3 C3 C4 178.75(17) . . . . ? N2 C2 C3 N3 178.97(15) . . . . ? N4 C2 C3 N3 0.06(17) . . . . ? N2 C2 C3 C4 0.0(2) . . . . ? N4 C2 C3 C4 -178.92(14) . . . . ? C1 N1 C4 N5 179.81(15) . . . . ? C1 N1 C4 C3 -0.5(2) . . . . ? N3 C3 C4 N5 1.4(3) . . . . ? C2 C3 C4 N5 -179.89(15) . . . . ? N3 C3 C4 N1 -178.30(15) . . . . ? C2 C3 C4 N1 0.4(2) . . . . ? C3 N3 C5 N4 0.02(18) . . . . ? C2 N4 C5 N3 0.02(19) . . . . ? C11 C6 C7 O3 179.30(16) . . . . ? C12 C6 C7 O3 -2.0(3) . . . . ? C11 C6 C7 C8 0.1(2) . . . . ? C12 C6 C7 C8 178.80(15) . . . . ? O3 C7 C8 C9 -178.60(17) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C7 C8 C9 C10 -1.0(3) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C9 C10 C11 O31 -179.4(4) . . . . ? C9 C10 C11 C6 0.1(3) . . . . ? C7 C6 C11 O31 179.0(4) . . . . ? C12 C6 C11 O31 0.3(5) . . . . ? C7 C6 C11 C10 -0.5(3) . . . . ? C12 C6 C11 C10 -179.16(16) . . . . ? C11 C6 C12 O2 0.6(2) . . . . ? C7 C6 C12 O2 -178.05(15) . . . . ? C11 C6 C12 O1 -179.65(15) . . . . ? C7 C6 C12 O1 1.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O1 0.84 1.8 2.547(2) 147.6 . O31 H31 O2 0.84 1.75 2.516(7) 151.5 . O4 H4 N3 0.84 1.93 2.7638(17) 172.1 3_656 N1 H1 O1 0.88 1.82 2.6927(18) 170.4 3_666 N5 H5A O2 0.88 1.85 2.7174(18) 169.8 3_666 N5 H5B N2 0.88 2.43 3.0575(19) 128.3 1_655 N4 H4A O4 0.88 1.81 2.6855(17) 177.5 3_556 #--------------------------END OF CIF 5 OF 6----------------------------- data_ad35 _database_code_depnum_ccdc_archive 'CCDC 686688' _audit_creation_date 2008-02-12T11:15:43-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; [Adenine hydroxide] [3,5-dihydroxybenzoic acid hydrate] ; _chemical_formula_moiety ; C7 H5 O4 1-, C5 H6 N5 1+, H3 O1 1+, H1 O1 1-' ; _chemical_formula_sum 'C12 H15 N5 O6' _chemical_formula_weight 325.29 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 c 1' _symmetry_space_group_name_Hall 'C -2yc' _symmetry_Int_Tables_number 9 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 11.6347(5) _cell_length_b 14.9993(8) _cell_length_c 7.9794(4) _cell_angle_alpha 90 _cell_angle_beta 91.496(3) _cell_angle_gamma 90 _cell_volume 1392.03(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1607 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.8668 _exptl_absorpt_correction_T_max 0.9924 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type ; Bruker-Nonius KappaCCD Area Detector ; _diffrn_measurement_method ; \f and \w scans ; _diffrn_standards_number 0 _diffrn_standards_decay_% negligible _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_unetI/netI 0.0609 _diffrn_reflns_number 6421 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 27.57 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 1599 _reflns_number_gt 1403 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998) ; _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek,2002) ; _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0328P)^2^+3.9257P] 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_number_reflns 1599 _refine_ls_number_parameters 223 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.069 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1166 _refine_ls_goodness_of_fit_ref 1.08 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(2) _refine_diff_density_max 0.326 _refine_diff_density_min -0.38 _refine_diff_density_rms 0.09 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.2331(3) 0.5445(2) 0.5558(4) 0.0228(7) Uani 1 1 d . . . O2 O 0.0751(3) 0.5109(2) 0.6924(4) 0.0251(8) Uani 1 1 d . . . O3 O 0.0610(3) 0.1768(2) 0.7177(5) 0.0260(8) Uani 1 1 d . . . H3 H 0.0124 0.2029 0.7763 0.031 Uiso 1 1 calc R . . O4 O 0.3782(3) 0.2407(2) 0.3719(4) 0.0228(7) Uani 1 1 d . . . H4 H 0.3752 0.185 0.361 0.027 Uiso 1 1 calc R . . C6 C 0.1632(4) 0.4887(3) 0.6124(6) 0.0177(10) Uani 1 1 d . . . C7 C 0.1850(4) 0.3902(3) 0.5878(6) 0.0180(9) Uani 1 1 d . . . C8 C 0.1132(4) 0.3296(3) 0.6655(6) 0.0181(9) Uani 1 1 d . . . H8 H 0.0533 0.3504 0.7342 0.022 Uiso 1 1 calc R . . C9 C 0.1290(4) 0.2386(3) 0.6427(6) 0.0188(10) Uani 1 1 d . . . C10 C 0.2181(4) 0.2073(3) 0.5449(5) 0.0166(9) Uani 1 1 d . . . H10 H 0.2307 0.1451 0.5315 0.02 Uiso 1 1 calc R . . C11 C 0.2879(4) 0.2691(3) 0.4677(6) 0.0180(9) Uani 1 1 d . . . C12 C 0.2721(4) 0.3600(3) 0.4871(6) 0.0172(9) Uani 1 1 d . . . H12 H 0.3204 0.4012 0.4321 0.021 Uiso 1 1 calc R . . N1 N 0.0187(3) 0.3214(3) 0.2433(5) 0.0200(9) Uani 1 1 d . . . H1 H 0.0417 0.3757 0.2193 0.024 Uiso 1 1 calc R . . N2 N -0.1151(3) 0.2370(3) 0.3973(5) 0.0183(8) Uani 1 1 d . . . N3 N 0.0570(3) 0.0822(3) 0.1695(5) 0.0227(9) Uani 1 1 d . . . N4 N -0.0870(3) 0.0781(3) 0.3494(5) 0.0203(9) Uani 1 1 d . . . H4A H -0.1406 0.0561 0.4132 0.024 Uiso 1 1 calc R . . N5 N 0.1619(3) 0.2670(3) 0.0766(5) 0.0233(9) Uani 1 1 d . . . H5A H 0.1844 0.3221 0.0593 0.028 Uiso 1 1 calc R . . H5B H 0.1983 0.2223 0.0299 0.028 Uiso 1 1 calc R . . C1 C -0.0697(4) 0.3121(3) 0.3488(6) 0.0201(10) Uani 1 1 d . . . H1A H -0.1019 0.3653 0.3919 0.024 Uiso 1 1 calc R . . C2 C -0.0623(4) 0.1659(3) 0.3270(5) 0.0181(10) Uani 1 1 d . . . C3 C 0.0273(4) 0.1676(3) 0.2155(6) 0.0176(9) Uani 1 1 d . . . C4 C 0.0741(4) 0.2513(3) 0.1719(6) 0.0169(9) Uani 1 1 d . . . C5 C -0.0127(5) 0.0307(3) 0.2541(6) 0.0249(10) Uani 1 1 d . . . H5C H -0.0115 -0.0326 0.2493 0.03 Uiso 1 1 calc R . . O6 O 0.2720(4) 0.0481(3) 0.0368(5) 0.0374(10) Uani 1 1 d D . . H6A H 0.302(4) 0.054(4) 0.137(4) 0.045 Uiso 1 1 d D . . H6B H 0.1991(17) 0.041(4) 0.047(6) 0.045 Uiso 1 1 d D . . H6C H 0.303(4) 0.006(3) -0.016(6) 0.045 Uiso 1 1 d D . . O5 O 0.3876(3) 0.0632(3) 0.3411(5) 0.0352(10) Uani 1 1 d D . . H5X H 0.454(3) 0.043(4) 0.314(8) 0.042 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0263(17) 0.0134(16) 0.0292(18) 0.0013(13) 0.0095(14) 0.0023(14) O2 0.0256(18) 0.0155(17) 0.035(2) 0.0009(14) 0.0141(16) 0.0021(15) O3 0.0298(19) 0.0126(17) 0.036(2) 0.0011(14) 0.0165(16) -0.0008(14) O4 0.0230(16) 0.0141(16) 0.0319(18) -0.0016(14) 0.0126(14) 0.0038(14) C6 0.014(2) 0.018(3) 0.021(2) 0.0016(17) -0.0013(17) 0.0029(17) C7 0.020(2) 0.014(2) 0.020(2) -0.0020(18) 0.0032(18) 0.0007(17) C8 0.0155(19) 0.015(2) 0.024(2) 0.0023(18) 0.0062(18) 0.0021(17) C9 0.019(2) 0.016(2) 0.022(2) -0.0029(19) 0.0067(18) -0.0067(19) C10 0.019(2) 0.013(2) 0.018(2) -0.0017(17) 0.0011(17) -0.0005(18) C11 0.017(2) 0.020(2) 0.018(2) 0.0007(17) 0.0040(17) 0.0025(18) C12 0.013(2) 0.020(2) 0.018(2) 0.0013(17) 0.0008(17) -0.0008(17) N1 0.022(2) 0.016(2) 0.022(2) -0.0035(15) 0.0047(16) -0.0024(15) N2 0.0202(19) 0.0119(19) 0.023(2) -0.0010(15) 0.0021(16) -0.0017(15) N3 0.025(2) 0.0133(19) 0.030(2) -0.0010(16) 0.0089(17) -0.0002(16) N4 0.024(2) 0.012(2) 0.025(2) 0.0015(16) 0.0066(16) -0.0027(16) N5 0.021(2) 0.023(2) 0.026(2) 0.0016(17) 0.0071(17) -0.0019(17) C1 0.022(2) 0.015(2) 0.023(2) -0.0026(18) 0.0075(19) -0.0023(19) C2 0.019(2) 0.020(2) 0.015(2) -0.0013(17) -0.0025(17) 0.0000(19) C3 0.016(2) 0.018(2) 0.019(2) -0.0021(17) 0.0032(17) 0.0006(17) C4 0.018(2) 0.013(2) 0.019(2) -0.0004(17) 0.0017(18) 0.0032(18) C5 0.025(2) 0.021(2) 0.029(3) 0.002(2) 0.007(2) 0.004(2) O6 0.033(2) 0.038(2) 0.042(2) -0.0065(18) 0.0204(18) -0.0009(19) O5 0.0312(19) 0.0207(19) 0.055(3) -0.0049(17) 0.0222(19) 0.0034(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.259(6) . ? O2 C6 1.266(5) . ? O3 C9 1.367(5) . ? O3 H3 0.84 . ? O4 C11 1.383(5) . ? O4 H4 0.84 . ? C6 C7 1.512(7) . ? C7 C12 1.386(6) . ? C7 C8 1.391(6) . ? C8 C9 1.390(6) . ? C8 H8 0.95 . ? C9 C10 1.395(7) . ? C10 C11 1.388(6) . ? C10 H10 0.95 . ? C11 C12 1.385(7) . ? C12 H12 0.95 . ? N1 C1 1.354(6) . ? N1 C4 1.366(6) . ? N1 H1 0.88 . ? N2 C1 1.307(6) . ? N2 C2 1.359(6) . ? N3 C5 1.319(6) . ? N3 C3 1.379(6) . ? N4 C2 1.360(6) . ? N4 C5 1.365(6) . ? N4 H4A 0.88 . ? N5 C4 1.310(6) . ? N5 H5A 0.88 . ? N5 H5B 0.88 . ? C1 H1A 0.95 . ? C2 C3 1.388(6) . ? C3 C4 1.416(6) . ? C5 H5C 0.95 . ? O6 H6A 0.869(19) . ? O6 H6B 0.861(19) . ? O6 H6C 0.843(19) . ? O5 H5X 0.86(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O3 H3 109.5 . . ? C11 O4 H4 109.5 . . ? O1 C6 O2 123.0(4) . . ? O1 C6 C7 119.4(4) . . ? O2 C6 C7 117.5(4) . . ? C12 C7 C8 120.1(4) . . ? C12 C7 C6 121.4(4) . . ? C8 C7 C6 118.4(4) . . ? C9 C8 C7 120.0(4) . . ? C9 C8 H8 120 . . ? C7 C8 H8 120 . . ? O3 C9 C8 121.9(4) . . ? O3 C9 C10 117.6(4) . . ? C8 C9 C10 120.5(4) . . ? C11 C10 C9 118.4(4) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? O4 C11 C12 118.1(4) . . ? O4 C11 C10 120.1(4) . . ? C12 C11 C10 121.8(4) . . ? C11 C12 C7 119.2(4) . . ? C11 C12 H12 120.4 . . ? C7 C12 H12 120.4 . . ? C1 N1 C4 123.7(4) . . ? C1 N1 H1 118.2 . . ? C4 N1 H1 118.2 . . ? C1 N2 C2 111.3(4) . . ? C5 N3 C3 104.2(4) . . ? C2 N4 C5 107.0(4) . . ? C2 N4 H4A 126.5 . . ? C5 N4 H4A 126.5 . . ? C4 N5 H5A 120 . . ? C4 N5 H5B 120 . . ? H5A N5 H5B 120 . . ? N2 C1 N1 126.4(5) . . ? N2 C1 H1A 116.8 . . ? N1 C1 H1A 116.8 . . ? N2 C2 N4 127.3(4) . . ? N2 C2 C3 127.3(5) . . ? N4 C2 C3 105.4(4) . . ? N3 C3 C2 110.6(4) . . ? N3 C3 C4 131.1(4) . . ? C2 C3 C4 118.3(4) . . ? N5 C4 N1 119.2(4) . . ? N5 C4 C3 127.8(4) . . ? N1 C4 C3 113.1(4) . . ? N3 C5 N4 112.7(4) . . ? N3 C5 H5C 123.6 . . ? N4 C5 H5C 123.6 . . ? H6A O6 H6B 107(3) . . ? H6A O6 H6C 112(3) . . ? H6B O6 H6C 113(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 O1 C6 C7 C12 -8.0(7) . . . . ? O2 C6 C7 C12 173.1(4) . . . . ? O1 C6 C7 C8 173.7(5) . . . . ? O2 C6 C7 C8 -5.2(6) . . . . ? C12 C7 C8 C9 0.2(7) . . . . ? C6 C7 C8 C9 178.6(5) . . . . ? C7 C8 C9 O3 179.5(5) . . . . ? C7 C8 C9 C10 1.3(8) . . . . ? O3 C9 C10 C11 179.9(4) . . . . ? C8 C9 C10 C11 -1.8(8) . . . . ? C9 C10 C11 O4 179.0(4) . . . . ? C9 C10 C11 C12 0.8(7) . . . . ? O4 C11 C12 C7 -177.5(4) . . . . ? C10 C11 C12 C7 0.7(7) . . . . ? C8 C7 C12 C11 -1.2(7) . . . . ? C6 C7 C12 C11 -179.5(5) . . . . ? C2 N2 C1 N1 -0.3(7) . . . . ? C4 N1 C1 N2 -0.3(8) . . . . ? C1 N2 C2 N4 180.0(5) . . . . ? C1 N2 C2 C3 -0.9(6) . . . . ? C5 N4 C2 N2 179.7(5) . . . . ? C5 N4 C2 C3 0.5(5) . . . . ? C5 N3 C3 C2 -0.8(6) . . . . ? C5 N3 C3 C4 177.3(5) . . . . ? N2 C2 C3 N3 -179.1(4) . . . . ? N4 C2 C3 N3 0.2(5) . . . . ? N2 C2 C3 C4 2.6(7) . . . . ? N4 C2 C3 C4 -178.2(4) . . . . ? C1 N1 C4 N5 -177.2(5) . . . . ? C1 N1 C4 C3 1.8(6) . . . . ? N3 C3 C4 N5 -1.8(8) . . . . ? C2 C3 C4 N5 176.2(5) . . . . ? N3 C3 C4 N1 179.3(5) . . . . ? C2 C3 C4 N1 -2.8(6) . . . . ? C3 N3 C5 N4 1.1(6) . . . . ? C2 N4 C5 N3 -1.0(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 O3 H3 O4 0.84 1.95 2.776(5) 168.1 4_455 O4 H4 O5 0.84 1.84 2.675(5) 173 . N1 H1 O2 0.88 1.76 2.634(5) 172.2 2_564 N4 H4A O1 0.88 1.89 2.744(5) 163.1 3_445 N5 H5A O1 0.88 2.08 2.952(5) 171.5 2_564 N5 H5B N2 0.88 2.52 2.996(5) 115.1 4_554 O6 H6A O5 0.869(19) 1.89(2) 2.754(6) 172(5) . O6 H6B N3 0.861(19) 2.04(3) 2.789(5) 145(5) . O6 H6C O5 0.843(19) 1.85(2) 2.673(5) 167(6) 2_554 O5 H5X O2 0.86(2) 1.92(3) 2.745(5) 162(6) 4_554 #------------------------END OF CIF 6 OF 6------------------------------