# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'C. Aakeroy' 'John Desper' 'Curtis Moore' 'Nate Schultheiss' _publ_contact_author_name 'C. Aakeroy' _publ_contact_author_address ; Department of Chemistry Kansas State University Manhattan Kansas 66506-3701 UNITED STATES OF AMERICA ; _publ_contact_author_email AAKEROY@KSU.EDU _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Balancing intermolecular hydrogen-bond interactions for the directed assembly of binary 1:1 co-crystals ; data_1a _database_code_depnum_ccdc_archive 'CCDC 614724' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-amino-4-methyl-6-(3-pyridyl)pyrimidine,4-nitrobenzoic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C10 H10 N4) (C7 H5 N O4) ; _chemical_formula_sum 'C17 H15 N5 O4' _chemical_formula_weight 353.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8245(5) _cell_length_b 9.5538(7) _cell_length_c 12.6278(9) _cell_angle_alpha 77.174(4) _cell_angle_beta 84.400(4) _cell_angle_gamma 82.637(4) _cell_volume 794.13(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1873 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 28.20 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5974 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.0668 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3581 _reflns_number_gt 2272 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3581 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1485 _refine_ls_wR_factor_gt 0.1267 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.5172(2) 0.29843(16) 0.54855(12) 0.0266(4) Uani 1 1 d . . . C12 C 0.3476(3) 0.23603(19) 0.56286(14) 0.0267(4) Uani 1 1 d . . . N12 N 0.2263(3) 0.25143(19) 0.64977(14) 0.0336(4) Uani 1 1 d . . . H12A H 0.130(3) 0.197(2) 0.6691(17) 0.040 Uiso 1 1 d . . . H12B H 0.265(3) 0.303(2) 0.6948(17) 0.040 Uiso 1 1 d . . . N13 N 0.2929(2) 0.16060(15) 0.49469(12) 0.0270(4) Uani 1 1 d . . . C14 C 0.4165(3) 0.14806(18) 0.40834(14) 0.0266(4) Uani 1 1 d . . . C15 C 0.5942(3) 0.20765(19) 0.38926(15) 0.0294(4) Uani 1 1 d . . . H15 H 0.6808 0.1966 0.3273 0.035 Uiso 1 1 calc R . . C16 C 0.6426(3) 0.28314(19) 0.46189(15) 0.0272(4) Uani 1 1 d . . . C17 C 0.8300(3) 0.3512(2) 0.44944(16) 0.0335(5) Uani 1 1 d . . . H17A H 0.9006 0.3166 0.5159 0.050 Uiso 1 1 calc R . . H17B H 0.7996 0.4564 0.4368 0.050 Uiso 1 1 calc R . . H17C H 0.9132 0.3253 0.3874 0.050 Uiso 1 1 calc R . . N21 N 0.0980(3) -0.05579(18) 0.28499(14) 0.0392(4) Uani 1 1 d . . . C22 C 0.1659(3) 0.0187(2) 0.34861(16) 0.0324(5) Uani 1 1 d . . . H22 H 0.0809 0.0414 0.4081 0.039 Uiso 1 1 calc R . . C23 C 0.3533(3) 0.06493(18) 0.33330(14) 0.0278(4) Uani 1 1 d . . . C24 C 0.4756(3) 0.0301(2) 0.24741(15) 0.0337(5) Uani 1 1 d . . . H24 H 0.6054 0.0590 0.2339 0.040 Uiso 1 1 calc R . . C25 C 0.4072(3) -0.0471(2) 0.18126(17) 0.0390(5) Uani 1 1 d . . . H25 H 0.4895 -0.0723 0.1217 0.047 Uiso 1 1 calc R . . C26 C 0.2200(3) -0.0872(2) 0.20221(16) 0.0392(5) Uani 1 1 d . . . H26 H 0.1744 -0.1399 0.1557 0.047 Uiso 1 1 calc R . . C31 C 0.6618(3) 0.53965(19) 0.81831(14) 0.0274(4) Uani 1 1 d . . . C37 C 0.5544(3) 0.46286(19) 0.75399(15) 0.0280(4) Uani 1 1 d . . . O31 O 0.6614(2) 0.42543(16) 0.67347(11) 0.0392(4) Uani 1 1 d . . . H31 H 0.587(3) 0.366(2) 0.6189(16) 0.047 Uiso 1 1 d . . . O32 O 0.3820(2) 0.44042(15) 0.77924(11) 0.0381(4) Uani 1 1 d . . . C32 C 0.5565(3) 0.6136(2) 0.89162(15) 0.0317(4) Uani 1 1 d . . . H32 H 0.4167 0.6135 0.9022 0.038 Uiso 1 1 calc R . . C33 C 0.6522(3) 0.6878(2) 0.95002(15) 0.0332(5) Uani 1 1 d . . . H33 H 0.5802 0.7388 1.0006 0.040 Uiso 1 1 calc R . . C34 C 0.8533(3) 0.6856(2) 0.93257(15) 0.0318(4) Uani 1 1 d . . . N34 N 0.9558(3) 0.76550(19) 0.99302(14) 0.0410(5) Uani 1 1 d . . . O33 O 1.1344(2) 0.7665(2) 0.97498(15) 0.0652(6) Uani 1 1 d . . . O34 O 0.8590(2) 0.8274(2) 1.05825(14) 0.0578(5) Uani 1 1 d . . . C35 C 0.9634(3) 0.6123(2) 0.86109(16) 0.0378(5) Uani 1 1 d . . . H35 H 1.1032 0.6123 0.8512 0.045 Uiso 1 1 calc R . . C36 C 0.8649(3) 0.5384(2) 0.80369(16) 0.0349(5) Uani 1 1 d . . . H36 H 0.9377 0.4864 0.7539 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0238(8) 0.0289(8) 0.0291(8) -0.0079(6) -0.0058(6) -0.0041(6) C12 0.0247(10) 0.0271(9) 0.0301(10) -0.0072(8) -0.0072(8) -0.0032(7) N12 0.0289(9) 0.0417(10) 0.0371(10) -0.0190(8) -0.0003(7) -0.0128(8) N13 0.0254(8) 0.0275(8) 0.0311(9) -0.0096(6) -0.0064(7) -0.0043(6) C14 0.0303(10) 0.0226(9) 0.0286(10) -0.0055(7) -0.0092(8) -0.0032(7) C15 0.0304(10) 0.0315(10) 0.0284(10) -0.0086(8) -0.0036(8) -0.0064(8) C16 0.0264(10) 0.0245(9) 0.0310(10) -0.0041(7) -0.0076(8) -0.0025(7) C17 0.0301(11) 0.0387(11) 0.0348(11) -0.0096(9) -0.0029(8) -0.0119(9) N21 0.0382(10) 0.0454(10) 0.0419(10) -0.0186(8) -0.0067(8) -0.0151(8) C22 0.0336(11) 0.0357(10) 0.0325(11) -0.0135(8) -0.0033(8) -0.0093(9) C23 0.0324(11) 0.0244(9) 0.0280(10) -0.0047(7) -0.0083(8) -0.0046(8) C24 0.0336(11) 0.0357(11) 0.0347(11) -0.0109(8) -0.0011(9) -0.0092(9) C25 0.0449(13) 0.0414(12) 0.0351(11) -0.0152(9) 0.0011(9) -0.0115(10) C26 0.0487(14) 0.0419(12) 0.0341(11) -0.0170(9) -0.0063(10) -0.0127(10) C31 0.0295(10) 0.0297(9) 0.0239(10) -0.0027(7) -0.0057(8) -0.0089(8) C37 0.0295(11) 0.0279(9) 0.0292(10) -0.0075(8) -0.0063(8) -0.0062(8) O31 0.0325(8) 0.0541(9) 0.0404(8) -0.0256(7) 0.0008(6) -0.0154(7) O32 0.0310(8) 0.0495(9) 0.0396(8) -0.0163(7) -0.0007(6) -0.0158(7) C32 0.0248(10) 0.0411(11) 0.0312(11) -0.0102(8) -0.0025(8) -0.0067(8) C33 0.0318(11) 0.0396(11) 0.0316(11) -0.0137(9) -0.0019(8) -0.0060(9) C34 0.0333(11) 0.0364(10) 0.0298(10) -0.0100(8) -0.0089(8) -0.0093(9) N34 0.0348(11) 0.0529(11) 0.0443(11) -0.0237(9) -0.0078(8) -0.0107(8) O33 0.0313(9) 0.0973(14) 0.0896(14) -0.0610(12) -0.0068(9) -0.0167(9) O34 0.0450(10) 0.0824(12) 0.0637(11) -0.0499(10) -0.0016(8) -0.0139(9) C35 0.0240(10) 0.0537(13) 0.0420(12) -0.0198(10) -0.0027(9) -0.0098(9) C36 0.0299(11) 0.0439(11) 0.0357(11) -0.0169(9) -0.0001(8) -0.0084(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.344(2) . ? N11 C12 1.348(2) . ? N11 H31 1.36(2) . ? C12 N12 1.332(2) . ? C12 N13 1.344(2) . ? N12 H12A 0.87(2) . ? N12 H12B 0.90(2) . ? N13 C14 1.330(2) . ? C14 C15 1.383(3) . ? C14 C23 1.489(2) . ? C15 C16 1.373(2) . ? C15 H15 0.9500 . ? C16 C17 1.487(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N21 C22 1.333(2) . ? N21 C26 1.335(3) . ? C22 C23 1.388(3) . ? C22 H22 0.9500 . ? C23 C24 1.377(3) . ? C24 C25 1.378(3) . ? C24 H24 0.9500 . ? C25 C26 1.365(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C36 1.379(3) . ? C31 C32 1.379(2) . ? C31 C37 1.501(2) . ? C37 O32 1.222(2) . ? C37 O31 1.282(2) . ? O31 H31 1.17(2) . ? C32 C33 1.385(3) . ? C32 H32 0.9500 . ? C33 C34 1.367(3) . ? C33 H33 0.9500 . ? C34 C35 1.372(3) . ? C34 N34 1.468(2) . ? N34 O34 1.215(2) . ? N34 O33 1.219(2) . ? C35 C36 1.386(3) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 118.60(14) . . ? C16 N11 H31 114.5(9) . . ? C12 N11 H31 126.6(9) . . ? N12 C12 N13 118.21(16) . . ? N12 C12 N11 117.62(15) . . ? N13 C12 N11 124.16(16) . . ? C12 N12 H12A 119.4(13) . . ? C12 N12 H12B 117.3(14) . . ? H12A N12 H12B 121.7(19) . . ? C14 N13 C12 116.73(16) . . ? N13 C14 C15 122.23(15) . . ? N13 C14 C23 116.09(16) . . ? C15 C14 C23 121.68(17) . . ? C16 C15 C14 118.46(17) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? N11 C16 C15 119.80(17) . . ? N11 C16 C17 117.28(15) . . ? C15 C16 C17 122.92(17) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C22 N21 C26 117.07(18) . . ? N21 C22 C23 124.00(18) . . ? N21 C22 H22 118.0 . . ? C23 C22 H22 118.0 . . ? C24 C23 C22 117.40(16) . . ? C24 C23 C14 122.28(17) . . ? C22 C23 C14 120.32(17) . . ? C23 C24 C25 119.13(19) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C26 C25 C24 119.33(19) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? N21 C26 C25 123.07(17) . . ? N21 C26 H26 118.5 . . ? C25 C26 H26 118.5 . . ? C36 C31 C32 119.70(17) . . ? C36 C31 C37 120.47(16) . . ? C32 C31 C37 119.82(17) . . ? O32 C37 O31 125.52(16) . . ? O32 C37 C31 121.13(16) . . ? O31 C37 C31 113.35(16) . . ? C37 O31 H31 117.3(10) . . ? C31 C32 C33 120.75(18) . . ? C31 C32 H32 119.6 . . ? C33 C32 H32 119.6 . . ? C34 C33 C32 117.98(17) . . ? C34 C33 H33 121.0 . . ? C32 C33 H33 121.0 . . ? C33 C34 C35 122.99(17) . . ? C33 C34 N34 118.39(16) . . ? C35 C34 N34 118.63(18) . . ? O34 N34 O33 123.24(17) . . ? O34 N34 C34 118.61(17) . . ? O33 N34 C34 118.15(16) . . ? C34 C35 C36 118.13(18) . . ? C34 C35 H35 120.9 . . ? C36 C35 H35 120.9 . . ? C31 C36 C35 120.45(17) . . ? C31 C36 H36 119.8 . . ? C35 C36 H36 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 179.42(17) . . . . ? C16 N11 C12 N13 -1.1(3) . . . . ? N12 C12 N13 C14 179.54(17) . . . . ? N11 C12 N13 C14 0.1(3) . . . . ? C12 N13 C14 C15 0.7(3) . . . . ? C12 N13 C14 C23 -179.67(15) . . . . ? N13 C14 C15 C16 -0.5(3) . . . . ? C23 C14 C15 C16 179.89(17) . . . . ? C12 N11 C16 C15 1.3(3) . . . . ? C12 N11 C16 C17 -179.00(17) . . . . ? C14 C15 C16 N11 -0.5(3) . . . . ? C14 C15 C16 C17 179.81(17) . . . . ? C26 N21 C22 C23 0.3(3) . . . . ? N21 C22 C23 C24 -0.5(3) . . . . ? N21 C22 C23 C14 179.81(18) . . . . ? N13 C14 C23 C24 -172.83(17) . . . . ? C15 C14 C23 C24 6.8(3) . . . . ? N13 C14 C23 C22 6.8(3) . . . . ? C15 C14 C23 C22 -173.62(18) . . . . ? C22 C23 C24 C25 0.4(3) . . . . ? C14 C23 C24 C25 179.99(18) . . . . ? C23 C24 C25 C26 0.1(3) . . . . ? C22 N21 C26 C25 0.2(3) . . . . ? C24 C25 C26 N21 -0.4(3) . . . . ? C36 C31 C37 O32 166.55(19) . . . . ? C32 C31 C37 O32 -14.2(3) . . . . ? C36 C31 C37 O31 -13.3(3) . . . . ? C32 C31 C37 O31 165.92(17) . . . . ? C36 C31 C32 C33 0.7(3) . . . . ? C37 C31 C32 C33 -178.55(18) . . . . ? C31 C32 C33 C34 0.1(3) . . . . ? C32 C33 C34 C35 -0.6(3) . . . . ? C32 C33 C34 N34 179.22(18) . . . . ? C33 C34 N34 O34 1.9(3) . . . . ? C35 C34 N34 O34 -178.2(2) . . . . ? C33 C34 N34 O33 -178.0(2) . . . . ? C35 C34 N34 O33 1.9(3) . . . . ? C33 C34 C35 C36 0.5(3) . . . . ? N34 C34 C35 C36 -179.41(19) . . . . ? C32 C31 C36 C35 -0.9(3) . . . . ? C37 C31 C36 C35 178.36(19) . . . . ? C34 C35 C36 C31 0.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N12 H12B O32 0.90(2) 2.14(2) 3.034(2) 170.9(19) . N12 H12A N21 0.87(2) 2.14(2) 3.015(2) 177.4(19) 2_556 O31 H31 N11 1.17(2) 1.36(2) 2.5274(18) 174.4(19) . _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.909 _refine_diff_density_max 0.278 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.065 #END data_1b _database_code_depnum_ccdc_archive 'CCDC 614725' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-amino-4-(3-pyridyl)-6-methylpyrimidine, Me5-PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C10 H10 N4) (C12 H16 O2) ; _chemical_formula_sum 'C22 H26 N4 O2' _chemical_formula_weight 378.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2088(7) _cell_length_b 8.7891(6) _cell_length_c 15.3371(12) _cell_angle_alpha 92.767(5) _cell_angle_beta 105.536(4) _cell_angle_gamma 115.332(4) _cell_volume 946.59(13) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3157 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.65 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6992 _diffrn_reflns_av_R_equivalents 0.0957 _diffrn_reflns_av_sigmaI/netI 0.0769 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 27.90 _reflns_number_total 4181 _reflns_number_gt 3038 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.040(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4181 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0738 _refine_ls_wR_factor_ref 0.2100 _refine_ls_wR_factor_gt 0.1959 _refine_ls_goodness_of_fit_ref 1.325 _refine_ls_restrained_S_all 1.325 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.1476(2) 0.0820(2) 0.32892(12) 0.0243(4) Uani 1 1 d . . . C12 C 0.2724(3) 0.1108(3) 0.41264(14) 0.0247(5) Uani 1 1 d . . . N12 N 0.4407(3) 0.2506(2) 0.43432(15) 0.0335(5) Uani 1 1 d . . . H12A H 0.451(4) 0.309(3) 0.390(2) 0.040 Uiso 1 1 d . . . H12B H 0.521(4) 0.272(3) 0.489(2) 0.040 Uiso 1 1 d . . . N13 N 0.2410(2) 0.0092(2) 0.47577(12) 0.0256(4) Uani 1 1 d . . . C14 C 0.0727(3) -0.1317(2) 0.45091(14) 0.0237(4) Uani 1 1 d . . . C15 C -0.0617(3) -0.1729(3) 0.36498(14) 0.0256(5) Uani 1 1 d . . . H15 H -0.1786 -0.2752 0.3477 0.031 Uiso 1 1 calc R . . C16 C -0.0191(3) -0.0592(3) 0.30507(14) 0.0243(5) Uani 1 1 d . . . C17 C -0.1564(3) -0.0868(3) 0.21294(15) 0.0322(5) Uani 1 1 d . . . H17A H -0.0910 -0.0682 0.1666 0.048 Uiso 1 1 calc R . . H17B H -0.2094 -0.0059 0.2138 0.048 Uiso 1 1 calc R . . H17C H -0.2595 -0.2043 0.1976 0.048 Uiso 1 1 calc R . . N21 N -0.1715(3) -0.4792(2) 0.57218(13) 0.0316(5) Uani 1 1 d . . . C22 C -0.1368(3) -0.3740(3) 0.51185(15) 0.0275(5) Uani 1 1 d . . . H22 H -0.2403 -0.3909 0.4596 0.033 Uiso 1 1 calc R . . C23 C 0.0409(3) -0.2419(2) 0.52095(14) 0.0240(5) Uani 1 1 d . . . C24 C -0.0247(3) -0.4524(3) 0.64523(15) 0.0300(5) Uani 1 1 d . . . H24A H -0.0468 -0.5252 0.6891 0.036 Uiso 1 1 calc R . . C25 C 0.1575(3) -0.3252(3) 0.66078(15) 0.0310(5) Uani 1 1 d . . . H25 H 0.2583 -0.3113 0.7137 0.037 Uiso 1 1 calc R . . C26 C 0.1903(3) -0.2181(3) 0.59754(15) 0.0288(5) Uani 1 1 d . . . H26 H 0.3145 -0.1289 0.6066 0.035 Uiso 1 1 calc R . . C31 C 0.3270(3) 0.5442(2) 0.15974(14) 0.0235(5) Uani 1 1 d . . . C32 C 0.3530(3) 0.7051(2) 0.19548(14) 0.0241(5) Uani 1 1 d . . . C33 C 0.3291(3) 0.8133(3) 0.13465(15) 0.0255(5) Uani 1 1 d . . . C34 C 0.2756(3) 0.7574(3) 0.03965(15) 0.0264(5) Uani 1 1 d . A . C35 C 0.2540(3) 0.5972(3) 0.00514(14) 0.0269(5) Uani 1 1 d . . . C36 C 0.2805(3) 0.4897(3) 0.06568(14) 0.0248(5) Uani 1 1 d . A . C41 C 0.3430(3) 0.4252(3) 0.22508(14) 0.0250(5) Uani 1 1 d . . . O41 O 0.1778(2) 0.29712(18) 0.21647(10) 0.0298(4) Uani 1 1 d . . . H41 H 0.191(4) 0.236(3) 0.2606(19) 0.036 Uiso 1 1 d . . . O42 O 0.4916(2) 0.4468(2) 0.27978(11) 0.0368(4) Uani 1 1 d . . . C42 C 0.4084(3) 0.7618(3) 0.29813(15) 0.0320(5) Uani 1 1 d . . . H42A H 0.3849 0.6620 0.3282 0.048 Uiso 1 1 calc R . . H42B H 0.3326 0.8161 0.3106 0.048 Uiso 1 1 calc R . . H42C H 0.5438 0.8440 0.3223 0.048 Uiso 1 1 calc R . . C43 C 0.3603(4) 0.9885(3) 0.17156(17) 0.0356(6) Uani 1 1 d . . . H43A H 0.4432 1.0736 0.1435 0.053 Uiso 1 1 calc R . . H43B H 0.4204 1.0152 0.2386 0.053 Uiso 1 1 calc R . . H43C H 0.2377 0.9908 0.1567 0.053 Uiso 1 1 calc R . . C44 C 0.2404(3) 0.8696(3) -0.02666(17) 0.0362(6) Uani 1 1 d . . . H44A H 0.3429 0.9134 -0.0541 0.054 Uiso 1 1 calc R A . H44B H 0.2371 0.9659 0.0064 0.054 Uiso 1 1 calc R . . H44C H 0.1185 0.8024 -0.0754 0.054 Uiso 1 1 calc R . . C45A C 0.1976(4) 0.5370(3) -0.09679(15) 0.0362(6) Uani 0.51(3) 1 d P A 1 H45A H 0.0936 0.4197 -0.1145 0.054 Uiso 0.51(3) 1 calc PR A 1 H45B H 0.3070 0.5394 -0.1122 0.054 Uiso 0.51(3) 1 calc PR A 1 H45C H 0.1553 0.6127 -0.1302 0.054 Uiso 0.51(3) 1 calc PR A 1 C45B C 0.1976(4) 0.5370(3) -0.09679(15) 0.0362(6) Uani 0.49(3) 1 d P A 2 H45D H 0.0626 0.5052 -0.1254 0.054 Uiso 0.49(3) 1 calc PR A 2 H45E H 0.2189 0.4372 -0.1076 0.054 Uiso 0.49(3) 1 calc PR A 2 H45F H 0.2744 0.6293 -0.1237 0.054 Uiso 0.49(3) 1 calc PR A 2 C46 C 0.2629(3) 0.3191(3) 0.02917(16) 0.0333(5) Uani 1 1 d . . . H46A H 0.3486 0.3364 -0.0074 0.050 Uiso 1 1 calc R A . H46B H 0.1315 0.2446 -0.0096 0.050 Uiso 1 1 calc R . . H46C H 0.2974 0.2654 0.0808 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0254(9) 0.0238(8) 0.0230(9) 0.0064(7) 0.0095(7) 0.0096(7) C12 0.0224(10) 0.0273(10) 0.0242(10) 0.0059(8) 0.0089(8) 0.0102(8) N12 0.0250(10) 0.0342(10) 0.0301(10) 0.0129(8) 0.0039(8) 0.0056(8) N13 0.0260(9) 0.0250(9) 0.0235(9) 0.0064(7) 0.0078(7) 0.0094(7) C14 0.0255(10) 0.0237(10) 0.0243(10) 0.0052(8) 0.0105(8) 0.0121(8) C15 0.0268(11) 0.0233(10) 0.0235(10) 0.0055(8) 0.0083(9) 0.0084(8) C16 0.0272(11) 0.0247(10) 0.0222(10) 0.0044(8) 0.0099(8) 0.0117(8) C17 0.0303(12) 0.0300(11) 0.0258(11) 0.0075(9) 0.0049(9) 0.0066(9) N21 0.0321(10) 0.0326(10) 0.0275(10) 0.0118(8) 0.0101(8) 0.0114(8) C22 0.0273(11) 0.0292(10) 0.0235(11) 0.0073(8) 0.0073(9) 0.0111(9) C23 0.0289(11) 0.0231(10) 0.0222(10) 0.0042(8) 0.0102(9) 0.0127(9) C24 0.0380(13) 0.0292(11) 0.0241(11) 0.0093(8) 0.0126(9) 0.0145(10) C25 0.0328(12) 0.0318(11) 0.0256(11) 0.0065(9) 0.0054(9) 0.0146(10) C26 0.0278(11) 0.0293(10) 0.0274(11) 0.0058(9) 0.0088(9) 0.0114(9) C31 0.0205(10) 0.0231(9) 0.0240(10) 0.0067(8) 0.0055(8) 0.0080(8) C32 0.0202(10) 0.0256(10) 0.0231(10) 0.0065(8) 0.0073(8) 0.0070(8) C33 0.0221(10) 0.0233(10) 0.0297(11) 0.0088(8) 0.0079(8) 0.0091(8) C34 0.0207(10) 0.0293(11) 0.0266(11) 0.0114(9) 0.0058(8) 0.0096(8) C35 0.0232(10) 0.0308(11) 0.0229(10) 0.0086(8) 0.0068(8) 0.0088(9) C36 0.0230(10) 0.0247(10) 0.0250(10) 0.0065(8) 0.0087(8) 0.0088(8) C41 0.0268(11) 0.0243(10) 0.0230(10) 0.0063(8) 0.0093(8) 0.0098(8) O41 0.0267(8) 0.0274(8) 0.0280(8) 0.0123(6) 0.0062(6) 0.0066(6) O42 0.0251(8) 0.0371(9) 0.0396(10) 0.0188(7) 0.0035(7) 0.0096(7) C42 0.0390(13) 0.0276(11) 0.0263(11) 0.0062(9) 0.0096(10) 0.0128(10) C43 0.0432(14) 0.0275(11) 0.0382(13) 0.0089(10) 0.0151(11) 0.0165(10) C44 0.0341(13) 0.0370(12) 0.0379(13) 0.0187(10) 0.0089(10) 0.0170(10) C45A 0.0422(14) 0.0396(12) 0.0222(11) 0.0080(9) 0.0084(10) 0.0156(11) C45B 0.0422(14) 0.0396(12) 0.0222(11) 0.0080(9) 0.0084(10) 0.0156(11) C46 0.0416(13) 0.0305(11) 0.0302(12) 0.0060(9) 0.0147(10) 0.0167(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.335(3) . ? N11 C12 1.343(3) . ? C12 N12 1.338(3) . ? C12 N13 1.350(2) . ? N12 H12A 0.87(3) . ? N12 H12B 0.88(3) . ? N13 C14 1.340(3) . ? C14 C15 1.385(3) . ? C14 C23 1.482(3) . ? C15 C16 1.388(3) . ? C15 H15 0.9500 . ? C16 C17 1.485(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N21 C24 1.331(3) . ? N21 C22 1.338(3) . ? C22 C23 1.386(3) . ? C22 H22 0.9500 . ? C23 C26 1.383(3) . ? C24 C25 1.377(3) . ? C24 H24A 0.9500 . ? C25 C26 1.382(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C36 1.392(3) . ? C31 C32 1.397(3) . ? C31 C41 1.505(3) . ? C32 C33 1.400(3) . ? C32 C42 1.510(3) . ? C33 C34 1.400(3) . ? C33 C43 1.503(3) . ? C34 C35 1.399(3) . ? C34 C44 1.508(3) . ? C35 C36 1.398(3) . ? C35 C45A 1.504(3) . ? C36 C46 1.508(3) . ? C41 O42 1.211(3) . ? C41 O41 1.306(2) . ? O41 H41 0.90(3) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45A H45A 0.9800 . ? C45A H45B 0.9800 . ? C45A H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 117.98(16) . . ? N12 C12 N11 117.10(17) . . ? N12 C12 N13 117.95(19) . . ? N11 C12 N13 124.96(18) . . ? C12 N12 H12A 112.7(18) . . ? C12 N12 H12B 117.6(18) . . ? H12A N12 H12B 130(3) . . ? C14 N13 C12 116.33(18) . . ? N13 C14 C15 122.26(17) . . ? N13 C14 C23 115.59(18) . . ? C15 C14 C23 122.15(18) . . ? C14 C15 C16 117.52(19) . . ? C14 C15 H15 121.2 . . ? C16 C15 H15 121.2 . . ? N11 C16 C15 120.92(19) . . ? N11 C16 C17 117.07(16) . . ? C15 C16 C17 122.00(19) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C24 N21 C22 116.95(18) . . ? N21 C22 C23 124.0(2) . . ? N21 C22 H22 118.0 . . ? C23 C22 H22 118.0 . . ? C26 C23 C22 117.46(18) . . ? C26 C23 C14 120.63(18) . . ? C22 C23 C14 121.90(19) . . ? N21 C24 C25 123.69(19) . . ? N21 C24 H24A 118.2 . . ? C25 C24 H24A 118.2 . . ? C24 C25 C26 118.4(2) . . ? C24 C25 H25 120.8 . . ? C26 C25 H25 120.8 . . ? C25 C26 C23 119.5(2) . . ? C25 C26 H26 120.3 . . ? C23 C26 H26 120.3 . . ? C36 C31 C32 121.83(18) . . ? C36 C31 C41 119.61(18) . . ? C32 C31 C41 118.52(18) . . ? C31 C32 C33 118.85(19) . . ? C31 C32 C42 120.37(17) . . ? C33 C32 C42 120.77(19) . . ? C32 C33 C34 119.80(19) . . ? C32 C33 C43 119.87(19) . . ? C34 C33 C43 120.33(18) . . ? C35 C34 C33 120.56(18) . . ? C35 C34 C44 119.3(2) . . ? C33 C34 C44 120.2(2) . . ? C36 C35 C34 119.83(19) . . ? C36 C35 C45A 119.4(2) . . ? C34 C35 C45A 120.75(18) . . ? C31 C36 C35 119.05(19) . . ? C31 C36 C46 120.84(18) . . ? C35 C36 C46 120.09(19) . . ? O42 C41 O41 124.09(18) . . ? O42 C41 C31 123.80(17) . . ? O41 C41 C31 112.11(17) . . ? C41 O41 H41 109.6(17) . . ? C32 C42 H42A 109.5 . . ? C32 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C32 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C33 C43 H43A 109.5 . . ? C33 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C33 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C34 C44 H44A 109.5 . . ? C34 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C34 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C35 C45A H45A 109.5 . . ? C35 C45A H45B 109.5 . . ? C35 C45A H45C 109.5 . . ? C36 C46 H46A 109.5 . . ? C36 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C36 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 178.2(2) . . . . ? C16 N11 C12 N13 -1.4(3) . . . . ? N12 C12 N13 C14 -178.50(19) . . . . ? N11 C12 N13 C14 1.1(3) . . . . ? C12 N13 C14 C15 0.7(3) . . . . ? C12 N13 C14 C23 179.84(18) . . . . ? N13 C14 C15 C16 -2.1(3) . . . . ? C23 C14 C15 C16 178.82(19) . . . . ? C12 N11 C16 C15 -0.1(3) . . . . ? C12 N11 C16 C17 178.8(2) . . . . ? C14 C15 C16 N11 1.8(3) . . . . ? C14 C15 C16 C17 -177.2(2) . . . . ? C24 N21 C22 C23 0.5(3) . . . . ? N21 C22 C23 C26 -0.3(3) . . . . ? N21 C22 C23 C14 178.4(2) . . . . ? N13 C14 C23 C26 -13.0(3) . . . . ? C15 C14 C23 C26 166.1(2) . . . . ? N13 C14 C23 C22 168.31(19) . . . . ? C15 C14 C23 C22 -12.5(3) . . . . ? C22 N21 C24 C25 -0.6(3) . . . . ? N21 C24 C25 C26 0.5(4) . . . . ? C24 C25 C26 C23 -0.2(3) . . . . ? C22 C23 C26 C25 0.1(3) . . . . ? C14 C23 C26 C25 -178.6(2) . . . . ? C36 C31 C32 C33 0.8(3) . . . . ? C41 C31 C32 C33 -176.90(17) . . . . ? C36 C31 C32 C42 -178.40(19) . . . . ? C41 C31 C32 C42 3.9(3) . . . . ? C31 C32 C33 C34 1.5(3) . . . . ? C42 C32 C33 C34 -179.30(18) . . . . ? C31 C32 C33 C43 -178.70(18) . . . . ? C42 C32 C33 C43 0.5(3) . . . . ? C32 C33 C34 C35 -2.9(3) . . . . ? C43 C33 C34 C35 177.38(19) . . . . ? C32 C33 C34 C44 177.05(18) . . . . ? C43 C33 C34 C44 -2.7(3) . . . . ? C33 C34 C35 C36 1.9(3) . . . . ? C44 C34 C35 C36 -178.04(19) . . . . ? C33 C34 C35 C45A -179.68(19) . . . . ? C44 C34 C35 C45A 0.4(3) . . . . ? C32 C31 C36 C35 -1.7(3) . . . . ? C41 C31 C36 C35 175.89(18) . . . . ? C32 C31 C36 C46 176.88(19) . . . . ? C41 C31 C36 C46 -5.5(3) . . . . ? C34 C35 C36 C31 0.4(3) . . . . ? C45A C35 C36 C31 -178.06(18) . . . . ? C34 C35 C36 C46 -178.22(18) . . . . ? C45A C35 C36 C46 3.3(3) . . . . ? C36 C31 C41 O42 110.8(3) . . . . ? C32 C31 C41 O42 -71.4(3) . . . . ? C36 C31 C41 O41 -69.8(3) . . . . ? C32 C31 C41 O41 107.9(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 O41 H41 N11 0.90(3) 1.72(3) 2.599(2) 164(3) . N12 H12A O42 0.87(3) 2.15(3) 3.013(2) 176(3) . N12 H12B N21 0.88(3) 2.46(3) 3.112(3) 132(2) 1_665 _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.471 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.106 #END data_1c _database_code_depnum_ccdc_archive 'CCDC 614726' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-amino-4-(3-pyridyl)-6-methylpyrimidine, 4-hydroxybenzoic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C10 H10 N4) (C7 H6 O3) ; _chemical_formula_sum 'C17 H16 N4 O3' _chemical_formula_weight 324.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3089(6) _cell_length_b 8.9991(7) _cell_length_c 11.1671(7) _cell_angle_alpha 85.733(4) _cell_angle_beta 69.174(4) _cell_angle_gamma 77.699(5) _cell_volume 762.52(9) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4887 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 25.00 _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.370 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.220 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22047 _diffrn_reflns_av_R_equivalents 0.1494 _diffrn_reflns_av_sigmaI/netI 0.0907 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 26.43 _reflns_number_total 3129 _reflns_number_gt 1979 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3129 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1129 _refine_ls_R_factor_gt 0.0863 _refine_ls_wR_factor_ref 0.2161 _refine_ls_wR_factor_gt 0.2031 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.1821(3) 0.5487(3) 0.3462(2) 0.0185(6) Uani 1 1 d . . . C12 C 0.2380(4) 0.4834(3) 0.2296(3) 0.0198(7) Uani 1 1 d . . . N12 N 0.3457(4) 0.3453(3) 0.2146(3) 0.0248(7) Uani 1 1 d . . . H12A H 0.368(4) 0.305(4) 0.278(3) 0.030 Uiso 1 1 d . . . H12B H 0.388(4) 0.299(4) 0.135(3) 0.030 Uiso 1 1 d . . . N13 N 0.1969(3) 0.5436(3) 0.1283(2) 0.0211(6) Uani 1 1 d . . . C14 C 0.0841(4) 0.6777(3) 0.1474(3) 0.0200(7) Uani 1 1 d . . . C15 C 0.0146(4) 0.7514(3) 0.2651(3) 0.0207(7) Uani 1 1 d . . . H15 H -0.0683 0.8448 0.2780 0.025 Uiso 1 1 calc R . . C16 C 0.0699(4) 0.6843(3) 0.3630(3) 0.0193(7) Uani 1 1 d . . . C17 C 0.0146(4) 0.7594(3) 0.4903(3) 0.0247(7) Uani 1 1 d . . . H17A H -0.0749 0.8515 0.4946 0.037 Uiso 1 1 calc R . . H17B H 0.1166 0.7867 0.5012 0.037 Uiso 1 1 calc R . . H17C H -0.0342 0.6893 0.5585 0.037 Uiso 1 1 calc R . . N21 N -0.1526(3) 0.9043(3) -0.0588(2) 0.0223(6) Uani 1 1 d . . . C22 C -0.1120(4) 0.8435(3) 0.0425(3) 0.0195(7) Uani 1 1 d . . . H22 H -0.1960 0.8685 0.1256 0.023 Uiso 1 1 calc R . . C23 C 0.0458(4) 0.7462(3) 0.0329(3) 0.0185(7) Uani 1 1 d . . . C24 C 0.1707(4) 0.7143(3) -0.0893(3) 0.0248(7) Uani 1 1 d . . . H24 H 0.2818 0.6505 -0.0999 0.030 Uiso 1 1 calc R . . C25 C 0.1309(4) 0.7767(4) -0.1947(3) 0.0289(8) Uani 1 1 d . . . H25 H 0.2137 0.7565 -0.2789 0.035 Uiso 1 1 calc R . . C26 C -0.0314(4) 0.8686(3) -0.1749(3) 0.0238(7) Uani 1 1 d . . . H26 H -0.0590 0.9092 -0.2478 0.029 Uiso 1 1 calc R . . C31 C 0.4479(4) 0.2715(3) 0.6429(3) 0.0192(7) Uani 1 1 d . . . C37 C 0.3994(4) 0.3196(3) 0.5281(3) 0.0205(7) Uani 1 1 d . . . O31 O 0.3018(3) 0.4567(2) 0.5361(2) 0.0250(6) Uani 1 1 d . . . H31 H 0.267(4) 0.483(4) 0.467(3) 0.030 Uiso 1 1 d . . . O32 O 0.4449(3) 0.2352(2) 0.4350(2) 0.0321(6) Uani 1 1 d . . . C32 C 0.5370(4) 0.1253(3) 0.6530(3) 0.0211(7) Uani 1 1 d . . . H32 H 0.5682 0.0548 0.5854 0.025 Uiso 1 1 calc R . . C33 C 0.5814(4) 0.0806(3) 0.7602(3) 0.0214(7) Uani 1 1 d . . . H33 H 0.6395 -0.0209 0.7672 0.026 Uiso 1 1 calc R . . C34 C 0.5405(4) 0.1852(3) 0.8584(3) 0.0184(7) Uani 1 1 d . . . O34 O 0.5800(3) 0.1495(2) 0.96648(18) 0.0223(5) Uani 1 1 d . . . H34 H 0.661(4) 0.059(4) 0.962(3) 0.027 Uiso 1 1 d . . . C35 C 0.4492(4) 0.3309(3) 0.8494(3) 0.0218(7) Uani 1 1 d . . . H35 H 0.4183 0.4017 0.9168 0.026 Uiso 1 1 calc R . . C36 C 0.4027(4) 0.3740(3) 0.7428(3) 0.0226(7) Uani 1 1 d . . . H36 H 0.3396 0.4741 0.7376 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0206(13) 0.0171(13) 0.0180(13) 0.0019(10) -0.0092(10) -0.0009(11) C12 0.0195(16) 0.0187(16) 0.0218(16) 0.0032(12) -0.0086(13) -0.0037(13) N12 0.0318(16) 0.0201(15) 0.0201(14) -0.0005(11) -0.0131(12) 0.0070(12) N13 0.0251(14) 0.0173(14) 0.0204(13) 0.0016(10) -0.0108(11) 0.0012(11) C14 0.0188(16) 0.0206(16) 0.0217(16) 0.0030(12) -0.0098(13) -0.0024(13) C15 0.0215(16) 0.0179(16) 0.0208(15) 0.0011(12) -0.0093(13) 0.0034(13) C16 0.0165(15) 0.0210(16) 0.0194(15) 0.0026(12) -0.0059(12) -0.0033(12) C17 0.0286(18) 0.0238(17) 0.0196(16) 0.0002(13) -0.0094(13) 0.0005(14) N21 0.0213(14) 0.0234(14) 0.0225(14) 0.0031(11) -0.0112(11) -0.0002(11) C22 0.0187(16) 0.0209(16) 0.0191(15) 0.0024(12) -0.0080(12) -0.0030(13) C23 0.0202(16) 0.0160(15) 0.0189(15) 0.0011(12) -0.0083(12) -0.0006(12) C24 0.0247(17) 0.0232(17) 0.0233(17) -0.0022(13) -0.0106(13) 0.0065(13) C25 0.0349(19) 0.0291(19) 0.0176(16) -0.0011(13) -0.0101(14) 0.0062(15) C26 0.0288(18) 0.0246(17) 0.0188(16) 0.0029(13) -0.0136(14) 0.0012(14) C31 0.0178(15) 0.0222(16) 0.0176(15) 0.0008(12) -0.0082(12) -0.0009(13) C37 0.0190(16) 0.0187(16) 0.0228(16) 0.0019(13) -0.0085(13) 0.0002(13) O31 0.0307(13) 0.0230(12) 0.0215(11) 0.0004(9) -0.0158(10) 0.0057(10) O32 0.0442(15) 0.0279(13) 0.0244(12) -0.0053(10) -0.0196(11) 0.0076(11) C32 0.0198(16) 0.0198(16) 0.0229(16) -0.0016(13) -0.0089(13) 0.0006(13) C33 0.0193(16) 0.0192(16) 0.0241(16) -0.0002(12) -0.0099(13) 0.0038(13) C34 0.0160(15) 0.0227(16) 0.0174(15) 0.0033(12) -0.0093(12) -0.0009(12) O34 0.0251(12) 0.0228(12) 0.0187(11) 0.0015(9) -0.0127(9) 0.0043(10) C35 0.0238(17) 0.0232(17) 0.0181(15) -0.0031(12) -0.0090(13) -0.0002(13) C36 0.0230(16) 0.0198(16) 0.0229(16) 0.0023(13) -0.0096(13) 0.0018(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.348(4) . ? N11 C12 1.351(4) . ? C12 N13 1.339(4) . ? C12 N12 1.351(4) . ? N12 H12A 0.83(4) . ? N12 H12B 0.93(3) . ? N13 C14 1.340(4) . ? C14 C15 1.389(4) . ? C14 C23 1.484(4) . ? C15 C16 1.383(4) . ? C15 H15 0.9500 . ? C16 C17 1.495(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N21 C26 1.339(4) . ? N21 C22 1.340(4) . ? C22 C23 1.387(4) . ? C22 H22 0.9500 . ? C23 C24 1.394(4) . ? C24 C25 1.382(4) . ? C24 H24 0.9500 . ? C25 C26 1.375(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C32 1.384(4) . ? C31 C36 1.395(4) . ? C31 C37 1.484(4) . ? C37 O32 1.231(3) . ? C37 O31 1.313(3) . ? O31 H31 0.91(4) . ? C32 C33 1.382(4) . ? C32 H32 0.9500 . ? C33 C34 1.398(4) . ? C33 H33 0.9500 . ? C34 O34 1.359(3) . ? C34 C35 1.384(4) . ? O34 H34 0.93(3) . ? C35 C36 1.382(4) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 116.8(2) . . ? N13 C12 N12 117.6(3) . . ? N13 C12 N11 125.9(3) . . ? N12 C12 N11 116.5(3) . . ? C12 N12 H12A 118(2) . . ? C12 N12 H12B 118(2) . . ? H12A N12 H12B 124(3) . . ? C12 N13 C14 116.3(2) . . ? N13 C14 C15 122.0(3) . . ? N13 C14 C23 115.7(3) . . ? C15 C14 C23 122.2(3) . . ? C16 C15 C14 117.8(3) . . ? C16 C15 H15 121.1 . . ? C14 C15 H15 121.1 . . ? N11 C16 C15 121.1(3) . . ? N11 C16 C17 116.6(3) . . ? C15 C16 C17 122.3(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C26 N21 C22 117.0(2) . . ? N21 C22 C23 123.7(3) . . ? N21 C22 H22 118.2 . . ? C23 C22 H22 118.2 . . ? C22 C23 C24 117.7(3) . . ? C22 C23 C14 122.1(3) . . ? C24 C23 C14 120.2(3) . . ? C25 C24 C23 119.2(3) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C26 C25 C24 118.5(3) . . ? C26 C25 H25 120.8 . . ? C24 C25 H25 120.8 . . ? N21 C26 C25 123.8(3) . . ? N21 C26 H26 118.1 . . ? C25 C26 H26 118.1 . . ? C32 C31 C36 119.0(3) . . ? C32 C31 C37 121.0(3) . . ? C36 C31 C37 120.0(3) . . ? O32 C37 O31 123.6(3) . . ? O32 C37 C31 121.9(3) . . ? O31 C37 C31 114.5(3) . . ? C37 O31 H31 114(2) . . ? C33 C32 C31 120.9(3) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C32 C33 C34 119.8(3) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? O34 C34 C35 117.4(3) . . ? O34 C34 C33 123.1(3) . . ? C35 C34 C33 119.4(3) . . ? C34 O34 H34 115(2) . . ? C36 C35 C34 120.3(3) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C35 C36 C31 120.4(3) . . ? C35 C36 H36 119.8 . . ? C31 C36 H36 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N13 2.6(4) . . . . ? C16 N11 C12 N12 -177.9(3) . . . . ? N12 C12 N13 C14 177.3(3) . . . . ? N11 C12 N13 C14 -3.1(4) . . . . ? C12 N13 C14 C15 0.6(4) . . . . ? C12 N13 C14 C23 177.5(2) . . . . ? N13 C14 C15 C16 2.2(4) . . . . ? C23 C14 C15 C16 -174.5(3) . . . . ? C12 N11 C16 C15 0.5(4) . . . . ? C12 N11 C16 C17 -177.4(3) . . . . ? C14 C15 C16 N11 -2.7(4) . . . . ? C14 C15 C16 C17 175.1(3) . . . . ? C26 N21 C22 C23 -0.7(4) . . . . ? N21 C22 C23 C24 2.2(5) . . . . ? N21 C22 C23 C14 -178.3(3) . . . . ? N13 C14 C23 C22 152.5(3) . . . . ? C15 C14 C23 C22 -30.7(4) . . . . ? N13 C14 C23 C24 -28.0(4) . . . . ? C15 C14 C23 C24 148.9(3) . . . . ? C22 C23 C24 C25 -1.8(5) . . . . ? C14 C23 C24 C25 178.6(3) . . . . ? C23 C24 C25 C26 0.1(5) . . . . ? C22 N21 C26 C25 -1.2(5) . . . . ? C24 C25 C26 N21 1.5(5) . . . . ? C32 C31 C37 O32 -4.2(4) . . . . ? C36 C31 C37 O32 176.1(3) . . . . ? C32 C31 C37 O31 174.3(3) . . . . ? C36 C31 C37 O31 -5.4(4) . . . . ? C36 C31 C32 C33 0.0(4) . . . . ? C37 C31 C32 C33 -179.7(3) . . . . ? C31 C32 C33 C34 -1.9(4) . . . . ? C32 C33 C34 O34 -180.0(3) . . . . ? C32 C33 C34 C35 2.7(4) . . . . ? O34 C34 C35 C36 -179.1(3) . . . . ? C33 C34 C35 C36 -1.7(4) . . . . ? C34 C35 C36 C31 -0.3(4) . . . . ? C32 C31 C36 C35 1.1(4) . . . . ? C37 C31 C36 C35 -179.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N12 H12A O32 0.83(4) 2.08(4) 2.906(3) 170(3) . N12 H12B O34 0.93(3) 2.28(4) 3.163(3) 157(3) 1_554 O31 H31 N11 0.91(4) 1.75(4) 2.656(3) 173(3) . O34 H34 N21 0.93(3) 1.80(4) 2.728(3) 169(3) 1_646 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.590 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.174 #END data_2a _database_code_depnum_ccdc_archive 'CCDC 614727' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-amino-4-(6-methoxy-3-pyridyl)-6-methylpyrimidine, 4-(Me2N)-PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C11 H12 N4 O) (C9 H11 N O2) ; _chemical_formula_sum 'C20 H23 N5 O3' _chemical_formula_weight 381.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8442(12) _cell_length_b 8.8879(14) _cell_length_c 14.216(2) _cell_angle_alpha 101.607(2) _cell_angle_beta 90.830(2) _cell_angle_gamma 106.753(2) _cell_volume 926.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4307 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 28.25 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8262 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4281 _reflns_number_gt 3502 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4281 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1318 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.42238(14) 0.12732(12) 0.58482(7) 0.0158(2) Uani 1 1 d . . . C12 C 0.36051(16) 0.14813(15) 0.50048(9) 0.0155(3) Uani 1 1 d . . . N12 N 0.44299(15) 0.28617(13) 0.47346(8) 0.0181(2) Uani 1 1 d . . . H12A H 0.524(2) 0.3614(19) 0.5161(11) 0.022 Uiso 1 1 d . . . H12B H 0.388(2) 0.3135(19) 0.4298(12) 0.022 Uiso 1 1 d . . . N13 N 0.22700(14) 0.04061(12) 0.44035(7) 0.0161(2) Uani 1 1 d . . . C14 C 0.15049(16) -0.09867(15) 0.46628(9) 0.0153(3) Uani 1 1 d . . . C15 C 0.20431(17) -0.12992(15) 0.55274(9) 0.0171(3) Uani 1 1 d . . . H15 H 0.1476 -0.2282 0.5713 0.020 Uiso 1 1 calc R . . C16 C 0.34302(17) -0.01278(15) 0.61044(9) 0.0165(3) Uani 1 1 d . . . C17 C 0.41644(18) -0.03350(15) 0.70318(9) 0.0197(3) Uani 1 1 d . . . H17A H 0.3432 -0.1341 0.7183 0.030 Uiso 1 1 calc R . . H17B H 0.4147 0.0571 0.7550 0.030 Uiso 1 1 calc R . . H17C H 0.5395 -0.0371 0.6969 0.030 Uiso 1 1 calc R . . N21 N -0.15470(15) -0.28647(13) 0.24089(8) 0.0191(2) Uani 1 1 d . . . C22 C -0.02900(17) -0.18637(15) 0.30872(9) 0.0178(3) Uani 1 1 d . . . H22 H 0.0396 -0.0874 0.2949 0.021 Uiso 1 1 calc R . . C23 C 0.00733(17) -0.21787(15) 0.39758(9) 0.0156(3) Uani 1 1 d . . . C24 C -0.09508(17) -0.36445(15) 0.41707(9) 0.0178(3) Uani 1 1 d . . . H24 H -0.0755 -0.3912 0.4769 0.021 Uiso 1 1 calc R . . C25 C -0.22379(18) -0.46908(15) 0.34908(9) 0.0191(3) Uani 1 1 d . . . H25 H -0.2944 -0.5691 0.3607 0.023 Uiso 1 1 calc R . . C26 C -0.24779(17) -0.42384(15) 0.26201(9) 0.0176(3) Uani 1 1 d . . . O26 O -0.37651(13) -0.52974(11) 0.19709(7) 0.0222(2) Uani 1 1 d . . . C27 C -0.4072(2) -0.48007(17) 0.11040(10) 0.0258(3) Uani 1 1 d . . . H27A H -0.4385 -0.3793 0.1264 0.039 Uiso 1 1 calc R . . H27B H -0.5055 -0.5634 0.0699 0.039 Uiso 1 1 calc R . . H27C H -0.2988 -0.4635 0.0755 0.039 Uiso 1 1 calc R . . C31 C 0.85476(17) 0.59744(15) 0.77728(9) 0.0175(3) Uani 1 1 d . . . C37 C 0.73317(17) 0.48082(15) 0.69820(9) 0.0175(3) Uani 1 1 d . . . O31 O 0.65792(13) 0.33820(11) 0.71663(7) 0.0202(2) Uani 1 1 d . . . H31 H 0.580(2) 0.2675(19) 0.6638(11) 0.024 Uiso 1 1 d . . . O32 O 0.70584(13) 0.51508(11) 0.62062(7) 0.0237(2) Uani 1 1 d . . . C32 C 0.93250(18) 0.75660(16) 0.76885(9) 0.0187(3) Uani 1 1 d . . . H32 H 0.9063 0.7886 0.7118 0.022 Uiso 1 1 calc R . . C33 C 1.04641(18) 0.86788(15) 0.84174(9) 0.0193(3) Uani 1 1 d . . . H33 H 1.0972 0.9751 0.8342 0.023 Uiso 1 1 calc R . . C34 C 1.08863(18) 0.82451(15) 0.92749(9) 0.0198(3) Uani 1 1 d . . . N34 N 1.19760(18) 0.93360(14) 1.00186(8) 0.0270(3) Uani 1 1 d . . . C38 C 1.2963(2) 1.09336(16) 0.99025(10) 0.0264(3) Uani 1 1 d . . . H38A H 1.3700 1.0845 0.9355 0.040 Uiso 1 1 calc R . . H38B H 1.3731 1.1518 1.0490 0.040 Uiso 1 1 calc R . . H38C H 1.2123 1.1517 0.9784 0.040 Uiso 1 1 calc R . . C39 C 1.2315(2) 0.88689(17) 1.09071(10) 0.0247(3) Uani 1 1 d . . . H39A H 1.1178 0.8342 1.1144 0.037 Uiso 1 1 calc R . . H39B H 1.2964 0.9827 1.1390 0.037 Uiso 1 1 calc R . . H39C H 1.3034 0.8122 1.0787 0.037 Uiso 1 1 calc R . . C35 C 1.01044(19) 0.66332(16) 0.93508(9) 0.0213(3) Uani 1 1 d . . . H35 H 1.0367 0.6300 0.9916 0.026 Uiso 1 1 calc R . . C36 C 0.89639(19) 0.55350(16) 0.86142(10) 0.0206(3) Uani 1 1 d . . . H36 H 0.8453 0.4459 0.8683 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 N11 0.0162(5) 0.0153(5) 0.0153(5) 0.0021(4) -0.0001(4) 0.0047(4) C12 0.0152(6) 0.0158(6) 0.0161(6) 0.0021(4) 0.0021(5) 0.0064(5) N12 0.0189(6) 0.0154(5) 0.0183(5) 0.0048(4) -0.0035(4) 0.0018(4) N13 0.0159(5) 0.0148(5) 0.0170(5) 0.0032(4) 0.0008(4) 0.0040(4) C14 0.0142(6) 0.0169(6) 0.0149(6) 0.0018(5) 0.0022(5) 0.0056(5) C15 0.0178(6) 0.0154(6) 0.0172(6) 0.0044(5) 0.0013(5) 0.0029(5) C16 0.0163(6) 0.0177(6) 0.0157(6) 0.0026(5) 0.0029(5) 0.0062(5) C17 0.0218(7) 0.0198(6) 0.0162(6) 0.0048(5) 0.0001(5) 0.0035(5) N21 0.0209(6) 0.0168(5) 0.0169(5) 0.0031(4) -0.0012(4) 0.0019(4) C22 0.0186(7) 0.0146(6) 0.0171(6) 0.0026(5) -0.0004(5) 0.0008(5) C23 0.0159(6) 0.0149(6) 0.0157(6) 0.0018(5) 0.0010(5) 0.0054(5) C24 0.0187(6) 0.0184(6) 0.0169(6) 0.0053(5) 0.0006(5) 0.0057(5) C25 0.0201(7) 0.0149(6) 0.0213(6) 0.0042(5) 0.0017(5) 0.0032(5) C26 0.0165(6) 0.0162(6) 0.0177(6) 0.0002(5) -0.0003(5) 0.0035(5) O26 0.0242(5) 0.0172(5) 0.0193(5) 0.0023(4) -0.0053(4) -0.0017(4) C27 0.0280(8) 0.0237(7) 0.0192(7) 0.0042(5) -0.0067(5) -0.0016(6) C31 0.0170(6) 0.0172(6) 0.0182(6) 0.0040(5) 0.0008(5) 0.0049(5) C37 0.0175(6) 0.0165(6) 0.0196(6) 0.0048(5) 0.0011(5) 0.0061(5) O31 0.0232(5) 0.0146(4) 0.0196(5) 0.0041(4) -0.0037(4) 0.0007(4) O32 0.0277(6) 0.0200(5) 0.0212(5) 0.0074(4) -0.0058(4) 0.0022(4) C32 0.0189(7) 0.0192(6) 0.0187(6) 0.0072(5) 0.0017(5) 0.0047(5) C33 0.0208(7) 0.0158(6) 0.0213(7) 0.0062(5) 0.0030(5) 0.0038(5) C34 0.0211(7) 0.0170(6) 0.0198(6) 0.0032(5) -0.0003(5) 0.0041(5) N34 0.0365(7) 0.0161(6) 0.0214(6) 0.0034(4) -0.0074(5) -0.0020(5) C38 0.0286(8) 0.0185(7) 0.0254(7) 0.0038(5) -0.0015(6) -0.0024(6) C39 0.0284(8) 0.0197(7) 0.0220(7) 0.0032(5) -0.0069(5) 0.0020(6) C35 0.0265(7) 0.0168(6) 0.0194(6) 0.0059(5) -0.0039(5) 0.0034(5) C36 0.0240(7) 0.0143(6) 0.0224(7) 0.0056(5) -0.0017(5) 0.0029(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.3464(16) . ? N11 C12 1.3533(15) . ? C12 N13 1.3451(16) . ? C12 N12 1.3456(16) . ? N12 H12A 0.894(17) . ? N12 H12B 0.862(16) . ? N13 C14 1.3380(16) . ? C14 C15 1.3986(17) . ? C14 C23 1.4843(17) . ? C15 C16 1.3849(17) . ? C15 H15 0.9500 . ? C16 C17 1.4968(17) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N21 C26 1.3244(17) . ? N21 C22 1.3472(16) . ? C22 C23 1.3905(17) . ? C22 H22 0.9500 . ? C23 C24 1.4027(17) . ? C24 C25 1.3737(18) . ? C24 H24 0.9500 . ? C25 C26 1.4023(18) . ? C25 H25 0.9500 . ? C26 O26 1.3538(15) . ? O26 C27 1.4295(15) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C31 C36 1.3928(17) . ? C31 C32 1.4001(17) . ? C31 C37 1.4759(17) . ? C37 O32 1.2332(15) . ? C37 O31 1.3155(15) . ? O31 H31 0.951(17) . ? C32 C33 1.3789(18) . ? C32 H32 0.9500 . ? C33 C34 1.4125(17) . ? C33 H33 0.9500 . ? C34 N34 1.3683(17) . ? C34 C35 1.4135(18) . ? N34 C39 1.4504(17) . ? N34 C38 1.4515(17) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C35 C36 1.3812(18) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 117.03(11) . . ? N13 C12 N12 117.43(11) . . ? N13 C12 N11 125.44(11) . . ? N12 C12 N11 117.10(11) . . ? C12 N12 H12A 117.1(10) . . ? C12 N12 H12B 117.8(11) . . ? H12A N12 H12B 120.1(15) . . ? C14 N13 C12 116.88(10) . . ? N13 C14 C15 121.63(11) . . ? N13 C14 C23 116.12(11) . . ? C15 C14 C23 122.25(11) . . ? C16 C15 C14 117.78(11) . . ? C16 C15 H15 121.1 . . ? C14 C15 H15 121.1 . . ? N11 C16 C15 121.23(11) . . ? N11 C16 C17 115.80(11) . . ? C15 C16 C17 122.96(11) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C26 N21 C22 116.40(11) . . ? N21 C22 C23 124.56(12) . . ? N21 C22 H22 117.7 . . ? C23 C22 H22 117.7 . . ? C22 C23 C24 117.09(11) . . ? C22 C23 C14 119.68(11) . . ? C24 C23 C14 123.23(11) . . ? C25 C24 C23 119.60(12) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 118.02(12) . . ? C24 C25 H25 121.0 . . ? C26 C25 H25 121.0 . . ? N21 C26 O26 119.42(11) . . ? N21 C26 C25 124.33(12) . . ? O26 C26 C25 116.25(11) . . ? C26 O26 C27 116.24(10) . . ? O26 C27 H27A 109.5 . . ? O26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C36 C31 C32 118.18(12) . . ? C36 C31 C37 121.64(11) . . ? C32 C31 C37 120.18(11) . . ? O32 C37 O31 122.88(12) . . ? O32 C37 C31 122.15(11) . . ? O31 C37 C31 114.96(11) . . ? C37 O31 H31 111.9(9) . . ? C33 C32 C31 121.30(12) . . ? C33 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C32 C33 C34 120.88(12) . . ? C32 C33 H33 119.6 . . ? C34 C33 H33 119.6 . . ? N34 C34 C33 122.02(12) . . ? N34 C34 C35 120.55(12) . . ? C33 C34 C35 117.42(12) . . ? C34 N34 C39 120.61(11) . . ? C34 N34 C38 120.83(11) . . ? C39 N34 C38 118.25(11) . . ? N34 C38 H38A 109.5 . . ? N34 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? N34 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N34 C39 H39A 109.5 . . ? N34 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? N34 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C36 C35 C34 120.93(12) . . ? C36 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C35 C36 C31 121.29(12) . . ? C35 C36 H36 119.4 . . ? C31 C36 H36 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N13 -0.12(18) . . . . ? C16 N11 C12 N12 -178.18(11) . . . . ? N12 C12 N13 C14 177.57(11) . . . . ? N11 C12 N13 C14 -0.48(18) . . . . ? C12 N13 C14 C15 1.21(17) . . . . ? C12 N13 C14 C23 -178.13(10) . . . . ? N13 C14 C15 C16 -1.33(18) . . . . ? C23 C14 C15 C16 177.97(11) . . . . ? C12 N11 C16 C15 0.00(18) . . . . ? C12 N11 C16 C17 178.96(10) . . . . ? C14 C15 C16 N11 0.69(18) . . . . ? C14 C15 C16 C17 -178.19(11) . . . . ? C26 N21 C22 C23 -0.24(19) . . . . ? N21 C22 C23 C24 -0.05(19) . . . . ? N21 C22 C23 C14 179.47(11) . . . . ? N13 C14 C23 C22 5.40(17) . . . . ? C15 C14 C23 C22 -173.93(11) . . . . ? N13 C14 C23 C24 -175.10(11) . . . . ? C15 C14 C23 C24 5.56(19) . . . . ? C22 C23 C24 C25 0.26(18) . . . . ? C14 C23 C24 C25 -179.25(11) . . . . ? C23 C24 C25 C26 -0.18(19) . . . . ? C22 N21 C26 O26 179.84(11) . . . . ? C22 N21 C26 C25 0.33(19) . . . . ? C24 C25 C26 N21 -0.1(2) . . . . ? C24 C25 C26 O26 -179.65(11) . . . . ? N21 C26 O26 C27 -2.65(18) . . . . ? C25 C26 O26 C27 176.89(11) . . . . ? C36 C31 C37 O32 -174.46(12) . . . . ? C32 C31 C37 O32 5.17(19) . . . . ? C36 C31 C37 O31 5.05(18) . . . . ? C32 C31 C37 O31 -175.32(11) . . . . ? C36 C31 C32 C33 -0.4(2) . . . . ? C37 C31 C32 C33 179.95(12) . . . . ? C31 C32 C33 C34 0.1(2) . . . . ? C32 C33 C34 N34 -178.29(13) . . . . ? C32 C33 C34 C35 0.3(2) . . . . ? C33 C34 N34 C39 177.08(12) . . . . ? C35 C34 N34 C39 -1.5(2) . . . . ? C33 C34 N34 C38 -9.4(2) . . . . ? C35 C34 N34 C38 172.09(13) . . . . ? N34 C34 C35 C36 178.20(13) . . . . ? C33 C34 C35 C36 -0.4(2) . . . . ? C34 C35 C36 C31 0.1(2) . . . . ? C32 C31 C36 C35 0.3(2) . . . . ? C37 C31 C36 C35 179.94(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O31 H31 N11 0.951(17) 1.690(17) 2.6321(14) 170.0(15) . N12 H12A O32 0.894(17) 2.026(17) 2.9173(15) 174.3(14) . N12 H12B O32 0.862(16) 2.110(16) 2.8925(15) 150.8(14) 2_666 _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.401 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.057 #END data_2b _database_code_depnum_ccdc_archive 'CCDC 614728' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-amino-4-(6-methoxy-3-pyridyl)-6-methylpyrimidine), (2,4-difluorobenzoic acid) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C11 H12 N4 O), (C7 H4 F2 O2)' _chemical_formula_sum 'C18 H16 F2 N4 O3' _chemical_formula_weight 374.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.158(4) _cell_length_b 7.3848(7) _cell_length_c 14.1634(16) _cell_angle_alpha 90.00 _cell_angle_beta 106.439(6) _cell_angle_gamma 90.00 _cell_volume 3326.4(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1729 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 28.45 _exptl_crystal_description Plate _exptl_crystal_colour lustrous _exptl_crystal_size_max 0.310 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 68430 _diffrn_reflns_av_R_equivalents 0.2039 _diffrn_reflns_av_sigmaI/netI 0.1172 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.18 _reflns_number_total 3690 _reflns_number_gt 1598 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3690 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1522 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1514 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 0.876 _refine_ls_restrained_S_all 0.876 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.54075(6) 0.1207(3) 0.38589(15) 0.0247(5) Uani 1 1 d . . . C12 C 0.50678(8) 0.1907(3) 0.40644(19) 0.0236(6) Uani 1 1 d . . . N12 N 0.47152(7) 0.2144(3) 0.33274(18) 0.0299(6) Uani 1 1 d . . . H12A H 0.4476(8) 0.249(3) 0.3479(19) 0.036 Uiso 1 1 d . . . H12B H 0.4697(8) 0.178(3) 0.268(2) 0.036 Uiso 1 1 d . . . N13 N 0.50513(6) 0.2412(3) 0.49760(15) 0.0243(5) Uani 1 1 d . . . C14 C 0.57549(8) 0.0980(3) 0.46216(18) 0.0227(6) Uani 1 1 d . . . C15 C 0.57572(8) 0.1459(3) 0.55686(19) 0.0280(7) Uani 1 1 d . . . H15 H 0.5997 0.1286 0.6093 0.034 Uiso 1 1 calc R . . C16 C 0.53987(8) 0.2198(3) 0.57226(19) 0.0258(7) Uani 1 1 d . . . C17 C 0.53749(8) 0.2772(4) 0.67137(19) 0.0347(8) Uani 1 1 d . . . H17A H 0.5651 0.2734 0.7171 0.052 Uiso 1 1 calc R . . H17B H 0.5192 0.1968 0.6931 0.052 Uiso 1 1 calc R . . H17C H 0.5267 0.3984 0.6677 0.052 Uiso 1 1 calc R . . N21 N 0.64744(7) -0.0690(3) 0.31729(15) 0.0291(6) Uani 1 1 d . . . C22 C 0.61415(8) -0.0062(3) 0.34421(19) 0.0278(7) Uani 1 1 d . . . H22 H 0.5898 0.0188 0.2942 0.033 Uiso 1 1 calc R . . C23 C 0.61313(8) 0.0243(3) 0.44038(18) 0.0235(6) Uani 1 1 d . . . C24 C 0.65044(8) -0.0148(3) 0.51371(19) 0.0283(7) Uani 1 1 d . . . H24 H 0.6518 0.0018 0.5796 0.034 Uiso 1 1 calc R . . C25 C 0.68491(8) -0.0772(4) 0.48867(19) 0.0298(7) Uani 1 1 d . . . H25 H 0.7098 -0.1024 0.5371 0.036 Uiso 1 1 calc R . . C26 C 0.68222(8) -0.1023(3) 0.3905(2) 0.0268(7) Uani 1 1 d . . . O26 O 0.71678(5) -0.1654(3) 0.36888(13) 0.0336(5) Uani 1 1 d . . . C27 C 0.71459(9) -0.1852(4) 0.2670(2) 0.0492(9) Uani 1 1 d . . . H27A H 0.7408 -0.2327 0.2613 0.074 Uiso 1 1 calc R . . H27B H 0.7094 -0.0693 0.2352 0.074 Uiso 1 1 calc R . . H27C H 0.6922 -0.2669 0.2363 0.074 Uiso 1 1 calc R . . C31 C 0.37327(8) 0.4754(3) 0.52154(18) 0.0244(6) Uani 1 1 d . . . C37 C 0.40705(8) 0.4017(3) 0.4830(2) 0.0256(7) Uani 1 1 d . A . O31 O 0.44315(6) 0.3869(3) 0.54963(13) 0.0365(5) Uani 1 1 d . . . H31 H 0.4636(8) 0.336(4) 0.5273(19) 0.044 Uiso 1 1 d . . . O32 O 0.40136(6) 0.3574(3) 0.39703(14) 0.0398(5) Uani 1 1 d . . . C32A C 0.33209(8) 0.4959(4) 0.46434(19) 0.0280(7) Uani 0.893(4) 1 d P A 1 F32 F 0.32074(5) 0.4456(2) 0.36897(12) 0.0423(7) Uani 0.893(4) 1 d P A 1 C32B C 0.33209(8) 0.4959(4) 0.46434(19) 0.0280(7) Uani 0.107(4) 1 d P A 2 H32 H 0.3255 0.4631 0.3983 0.034 Uiso 0.107(4) 1 calc PR A 2 C33 C 0.30049(8) 0.5620(4) 0.5000(2) 0.0328(7) Uani 1 1 d . . . H33 H 0.2732 0.5757 0.4592 0.039 Uiso 1 1 calc R A 1 C34 C 0.31058(9) 0.6064(4) 0.5968(2) 0.0310(7) Uani 1 1 d . A . F34 F 0.27993(5) 0.6705(2) 0.63368(12) 0.0490(5) Uani 1 1 d . . . C35 C 0.35046(9) 0.5889(4) 0.6600(2) 0.0316(7) Uani 1 1 d . . . H35 H 0.3564 0.6190 0.7263 0.038 Uiso 1 1 calc R A 1 C36A C 0.38115(9) 0.5245(3) 0.62034(19) 0.0286(7) Uani 0.893(4) 1 d P A 1 H36 H 0.4084 0.5133 0.6613 0.034 Uiso 0.893(4) 1 calc PR A 1 C36B C 0.38115(9) 0.5245(3) 0.62034(19) 0.0286(7) Uani 0.107(4) 1 d P A 2 F36 F 0.4159(5) 0.5440(19) 0.6789(10) 0.039(6) Uiso 0.107(4) 1 d P 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 N11 0.0243(13) 0.0251(14) 0.0253(13) -0.0005(10) 0.0082(11) 0.0012(10) C12 0.0240(16) 0.0193(16) 0.0273(16) -0.0012(12) 0.0071(14) -0.0042(12) N12 0.0259(14) 0.0392(16) 0.0262(14) -0.0038(11) 0.0101(13) 0.0043(11) N13 0.0258(13) 0.0258(13) 0.0211(13) -0.0035(10) 0.0061(11) 0.0005(10) C14 0.0253(15) 0.0197(16) 0.0246(16) 0.0012(12) 0.0094(13) -0.0025(12) C15 0.0276(16) 0.0282(17) 0.0272(17) 0.0019(13) 0.0064(13) 0.0007(13) C16 0.0307(17) 0.0234(17) 0.0245(16) 0.0001(12) 0.0097(14) -0.0018(13) C17 0.0360(18) 0.0387(19) 0.0284(17) -0.0052(13) 0.0074(14) 0.0052(14) N21 0.0273(14) 0.0316(15) 0.0292(14) -0.0007(11) 0.0092(12) 0.0057(11) C22 0.0229(15) 0.0272(17) 0.0296(17) -0.0042(13) 0.0013(13) 0.0025(13) C23 0.0246(16) 0.0206(16) 0.0249(16) -0.0021(12) 0.0061(13) -0.0043(12) C24 0.0305(17) 0.0309(18) 0.0254(16) -0.0018(12) 0.0109(14) -0.0010(13) C25 0.0246(16) 0.0294(18) 0.0321(18) 0.0028(13) 0.0026(13) -0.0003(13) C26 0.0257(16) 0.0241(17) 0.0329(17) -0.0015(13) 0.0121(14) -0.0002(12) O26 0.0266(11) 0.0427(13) 0.0346(12) -0.0004(9) 0.0140(9) 0.0050(9) C27 0.041(2) 0.069(3) 0.043(2) -0.0055(17) 0.0200(17) 0.0124(17) C31 0.0260(16) 0.0186(16) 0.0288(16) 0.0022(12) 0.0081(13) -0.0014(12) C37 0.0258(17) 0.0219(17) 0.0287(17) 0.0040(13) 0.0072(14) 0.0013(12) O31 0.0264(12) 0.0509(15) 0.0321(13) -0.0052(10) 0.0083(10) 0.0103(10) O32 0.0367(12) 0.0555(15) 0.0272(12) -0.0057(10) 0.0089(10) 0.0091(10) C32A 0.0331(18) 0.0297(17) 0.0209(16) 0.0011(12) 0.0072(14) 0.0008(13) F32 0.0361(12) 0.0613(15) 0.0270(12) -0.0021(9) 0.0047(9) 0.0082(9) C32B 0.0331(18) 0.0297(17) 0.0209(16) 0.0011(12) 0.0072(14) 0.0008(13) C33 0.0244(16) 0.036(2) 0.0366(19) 0.0062(14) 0.0065(14) 0.0032(13) C34 0.0308(17) 0.0284(18) 0.0397(19) 0.0009(13) 0.0194(15) 0.0028(13) F34 0.0417(11) 0.0622(13) 0.0510(11) -0.0004(9) 0.0261(9) 0.0128(9) C35 0.0415(19) 0.0282(18) 0.0283(17) -0.0026(13) 0.0149(15) -0.0004(14) C36A 0.0303(17) 0.0265(18) 0.0287(17) 0.0028(13) 0.0076(14) -0.0020(13) C36B 0.0303(17) 0.0265(18) 0.0287(17) 0.0028(13) 0.0076(14) -0.0020(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.344(3) . ? N11 C14 1.348(3) . ? C12 N12 1.340(3) . ? C12 N13 1.360(3) . ? N12 H12A 0.92(3) . ? N12 H12B 0.94(3) . ? N13 C16 1.335(3) . ? C14 C15 1.385(3) . ? C14 C23 1.472(3) . ? C15 C16 1.380(3) . ? C15 H15 0.9300 . ? C16 C17 1.490(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? N21 C26 1.337(3) . ? N21 C22 1.348(3) . ? C22 C23 1.390(3) . ? C22 H22 0.9300 . ? C23 C24 1.402(3) . ? C24 C25 1.369(3) . ? C24 H24 0.9300 . ? C25 C26 1.381(3) . ? C25 H25 0.9300 . ? C26 O26 1.350(3) . ? O26 C27 1.432(3) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C31 C32A 1.385(4) . ? C31 C36A 1.397(3) . ? C31 C37 1.481(3) . ? C37 O32 1.223(3) . ? C37 O31 1.302(3) . ? O31 H31 0.91(3) . ? C32A F32 1.348(3) . ? C32A C33 1.375(3) . ? C33 C34 1.356(4) . ? C33 H33 0.9300 . ? C34 F34 1.353(3) . ? C34 C35 1.377(4) . ? C35 C36A 1.379(3) . ? C35 H35 0.9300 . ? C36A H36 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C14 116.9(2) . . ? N12 C12 N11 118.8(2) . . ? N12 C12 N13 116.3(2) . . ? N11 C12 N13 124.9(2) . . ? C12 N12 H12A 118.5(16) . . ? C12 N12 H12B 121.4(16) . . ? H12A N12 H12B 119(2) . . ? C16 N13 C12 117.5(2) . . ? N11 C14 C15 120.9(2) . . ? N11 C14 C23 117.4(2) . . ? C15 C14 C23 121.6(2) . . ? C16 C15 C14 119.0(2) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? N13 C16 C15 120.7(2) . . ? N13 C16 C17 116.7(2) . . ? C15 C16 C17 122.6(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C26 N21 C22 116.1(2) . . ? N21 C22 C23 125.6(2) . . ? N21 C22 H22 117.2 . . ? C23 C22 H22 117.2 . . ? C22 C23 C24 115.6(2) . . ? C22 C23 C14 121.5(2) . . ? C24 C23 C14 122.9(2) . . ? C25 C24 C23 120.3(2) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 119.0(3) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? N21 C26 O26 119.3(2) . . ? N21 C26 C25 123.5(2) . . ? O26 C26 C25 117.2(2) . . ? C26 O26 C27 117.4(2) . . ? O26 C27 H27A 109.5 . . ? O26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C32A C31 C36A 115.6(2) . . ? C32A C31 C37 123.2(2) . . ? C36A C31 C37 121.2(2) . . ? O32 C37 O31 123.4(2) . . ? O32 C37 C31 123.0(2) . . ? O31 C37 C31 113.6(2) . . ? C37 O31 H31 114.1(17) . . ? F32 C32A C33 116.1(2) . . ? F32 C32A C31 120.4(2) . . ? C33 C32A C31 123.5(3) . . ? C34 C33 C32A 117.5(3) . . ? C34 C33 H33 121.3 . . ? C32A C33 H33 121.3 . . ? F34 C34 C33 118.5(3) . . ? F34 C34 C35 118.0(2) . . ? C33 C34 C35 123.5(2) . . ? C34 C35 C36A 116.8(3) . . ? C34 C35 H35 121.6 . . ? C36A C35 H35 121.6 . . ? C35 C36A C31 123.2(3) . . ? C35 C36A H36 118.4 . . ? C31 C36A H36 118.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 N11 C12 N12 -179.6(2) . . . . ? C14 N11 C12 N13 0.7(4) . . . . ? N12 C12 N13 C16 -179.7(2) . . . . ? N11 C12 N13 C16 0.0(4) . . . . ? C12 N11 C14 C15 -0.3(3) . . . . ? C12 N11 C14 C23 -179.0(2) . . . . ? N11 C14 C15 C16 -0.7(4) . . . . ? C23 C14 C15 C16 177.9(2) . . . . ? C12 N13 C16 C15 -1.1(4) . . . . ? C12 N13 C16 C17 179.6(2) . . . . ? C14 C15 C16 N13 1.5(4) . . . . ? C14 C15 C16 C17 -179.3(2) . . . . ? C26 N21 C22 C23 -0.6(4) . . . . ? N21 C22 C23 C24 0.1(4) . . . . ? N21 C22 C23 C14 178.3(2) . . . . ? N11 C14 C23 C22 5.4(4) . . . . ? C15 C14 C23 C22 -173.3(2) . . . . ? N11 C14 C23 C24 -176.5(2) . . . . ? C15 C14 C23 C24 4.8(4) . . . . ? C22 C23 C24 C25 0.5(4) . . . . ? C14 C23 C24 C25 -177.7(2) . . . . ? C23 C24 C25 C26 -0.5(4) . . . . ? C22 N21 C26 O26 -180.0(2) . . . . ? C22 N21 C26 C25 0.6(4) . . . . ? C24 C25 C26 N21 -0.1(4) . . . . ? C24 C25 C26 O26 -179.5(2) . . . . ? N21 C26 O26 C27 2.9(3) . . . . ? C25 C26 O26 C27 -177.7(2) . . . . ? C32A C31 C37 O32 1.9(4) . . . . ? C36A C31 C37 O32 -179.9(2) . . . . ? C32A C31 C37 O31 -177.4(2) . . . . ? C36A C31 C37 O31 0.7(3) . . . . ? C36A C31 C32A F32 -177.3(2) . . . . ? C37 C31 C32A F32 0.9(4) . . . . ? C36A C31 C32A C33 0.8(4) . . . . ? C37 C31 C32A C33 179.1(2) . . . . ? F32 C32A C33 C34 177.2(2) . . . . ? C31 C32A C33 C34 -1.0(4) . . . . ? C32A C33 C34 F34 -179.5(2) . . . . ? C32A C33 C34 C35 0.1(4) . . . . ? F34 C34 C35 C36A -179.5(2) . . . . ? C33 C34 C35 C36A 0.8(4) . . . . ? C34 C35 C36A C31 -1.0(4) . . . . ? C32A C31 C36A C35 0.2(4) . . . . ? C37 C31 C36A C35 -178.1(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 N12 H12A O32 0.92(3) 2.02(3) 2.925(3) 170(2) . N12 H12B N11 0.94(3) 2.16(3) 3.085(3) 172(2) 2_655 O31 H31 N13 0.91(3) 1.70(3) 2.604(3) 174(3) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.18 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.259 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.065 #END data_2c _database_code_depnum_ccdc_archive 'CCDC 614729' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-amino-4-(6-methoxy-3-pyridyl)-6-methylpyrimidine), Me5-PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C11 H12 N4 O) (C12 H16 O2) ; _chemical_formula_sum 'C23 H28 N4 O3' _chemical_formula_weight 408.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.3534(5) _cell_length_b 12.6941(12) _cell_length_c 15.1880(14) _cell_angle_alpha 87.7550(10) _cell_angle_beta 82.9210(10) _cell_angle_gamma 87.542(2) _cell_volume 1022.72(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3802 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 28.20 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8494 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4648 _reflns_number_gt 3490 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4648 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1483 _refine_ls_wR_factor_gt 0.1352 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.0490(3) 0.67626(11) 0.58552(9) 0.0149(3) Uani 1 1 d . . . C12 C 0.2026(3) 0.75967(13) 0.58066(10) 0.0145(3) Uani 1 1 d . . . N12 N 0.3550(3) 0.76195(12) 0.64382(10) 0.0178(3) Uani 1 1 d . . . H12A H 0.345(4) 0.7104(17) 0.6870(13) 0.021 Uiso 1 1 d . . . H12B H 0.452(4) 0.8130(17) 0.6453(13) 0.021 Uiso 1 1 d . . . N13 N 0.2133(3) 0.83735(11) 0.51766(9) 0.0147(3) Uani 1 1 d . . . C14 C 0.0496(3) 0.83420(13) 0.45798(11) 0.0146(3) Uani 1 1 d . . . C15 C -0.1195(3) 0.75362(14) 0.45972(11) 0.0182(4) Uani 1 1 d . . . H15 H -0.2360 0.7529 0.4174 0.022 Uiso 1 1 calc R . . C16 C -0.1130(3) 0.67476(13) 0.52488(11) 0.0161(3) Uani 1 1 d . . . C18 C -0.2841(3) 0.58385(14) 0.53029(12) 0.0207(4) Uani 1 1 d . . . H18A H -0.4295 0.6031 0.4988 0.031 Uiso 1 1 calc R . . H18B H -0.3423 0.5664 0.5927 0.031 Uiso 1 1 calc R . . H18C H -0.1925 0.5226 0.5030 0.031 Uiso 1 1 calc R . . N21 N 0.2524(3) 1.07818(11) 0.32329(9) 0.0157(3) Uani 1 1 d . . . C22 C 0.2332(3) 0.99854(13) 0.38499(11) 0.0152(3) Uani 1 1 d . . . H22 H 0.3468 0.9957 0.4285 0.018 Uiso 1 1 calc R . . C23 C 0.0580(3) 0.92056(13) 0.38884(10) 0.0146(3) Uani 1 1 d . . . C24 C -0.1108(3) 0.92752(14) 0.32479(11) 0.0188(4) Uani 1 1 d . . . H24 H -0.2358 0.8765 0.3253 0.023 Uiso 1 1 calc R . . C25 C -0.0952(3) 1.00758(14) 0.26186(12) 0.0205(4) Uani 1 1 d . . . H25 H -0.2081 1.0132 0.2182 0.025 Uiso 1 1 calc R . . C26 C 0.0914(3) 1.08094(13) 0.26346(10) 0.0158(3) Uani 1 1 d . . . O26 O 0.1016(2) 1.15701(10) 0.19873(8) 0.0200(3) Uani 1 1 d . . . C27 C 0.2880(4) 1.23489(14) 0.19758(12) 0.0218(4) Uani 1 1 d . . . H27A H 0.2860 1.2805 0.1441 0.033 Uiso 1 1 calc R . . H27B H 0.4548 1.1998 0.1976 0.033 Uiso 1 1 calc R . . H27C H 0.2509 1.2776 0.2503 0.033 Uiso 1 1 calc R . . C31 C 0.1903(3) 0.40574(13) 0.81322(10) 0.0155(3) Uani 1 1 d . . . C32 C 0.0020(3) 0.39608(13) 0.88549(11) 0.0158(3) Uani 1 1 d . . . C33 C 0.0023(3) 0.30483(14) 0.94025(11) 0.0167(4) Uani 1 1 d . . . C34 C 0.1857(3) 0.22371(13) 0.92142(11) 0.0169(4) Uani 1 1 d . . . C35 C 0.3757(3) 0.23558(13) 0.84908(11) 0.0163(3) Uani 1 1 d . . . C36 C 0.3762(3) 0.32657(13) 0.79389(11) 0.0156(3) Uani 1 1 d . . . C41 C 0.1977(3) 0.50602(14) 0.75671(11) 0.0171(4) Uani 1 1 d . . . O41 O 0.0704(3) 0.50305(10) 0.68814(8) 0.0237(3) Uani 1 1 d . . . H41 H 0.081(4) 0.5659(18) 0.6582(14) 0.028 Uiso 1 1 d . . . O42 O 0.3112(3) 0.58228(10) 0.77346(9) 0.0276(3) Uani 1 1 d . . . C42 C -0.2000(3) 0.48226(15) 0.90273(12) 0.0215(4) Uani 1 1 d . . . H42A H -0.1825 0.5151 0.9589 0.032 Uiso 1 1 calc R . . H42B H -0.3663 0.4519 0.9063 0.032 Uiso 1 1 calc R . . H42C H -0.1820 0.5356 0.8542 0.032 Uiso 1 1 calc R . . C43 C -0.2006(3) 0.29478(15) 1.01877(11) 0.0225(4) Uani 1 1 d . . . H43A H -0.2429 0.3644 1.0434 0.034 Uiso 1 1 calc R . . H43B H -0.1389 0.2472 1.0644 0.034 Uiso 1 1 calc R . . H43C H -0.3510 0.2662 0.9993 0.034 Uiso 1 1 calc R . . C44 C 0.1791(4) 0.12193(15) 0.97697(12) 0.0256(4) Uani 1 1 d . . . H44A H 0.2031 0.0618 0.9378 0.038 Uiso 1 1 calc R . . H44B H 0.0159 0.1179 1.0138 0.038 Uiso 1 1 calc R . . H44C H 0.3141 0.1202 1.0152 0.038 Uiso 1 1 calc R . . C45 C 0.5832(3) 0.15226(15) 0.83066(12) 0.0223(4) Uani 1 1 d . . . H45A H 0.5622 0.1171 0.7759 0.033 Uiso 1 1 calc R . . H45B H 0.5753 0.1002 0.8802 0.033 Uiso 1 1 calc R . . H45C H 0.7468 0.1854 0.8239 0.033 Uiso 1 1 calc R . . C46 C 0.5763(3) 0.33895(15) 0.71520(11) 0.0215(4) Uani 1 1 d . . . H46A H 0.5351 0.4018 0.6794 0.032 Uiso 1 1 calc R . . H46B H 0.5835 0.2765 0.6789 0.032 Uiso 1 1 calc R . . H46C H 0.7402 0.3467 0.7363 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0139(7) 0.0130(7) 0.0175(7) 0.0007(5) -0.0008(5) -0.0026(5) C12 0.0132(8) 0.0134(8) 0.0163(8) -0.0018(6) 0.0012(6) -0.0008(6) N12 0.0198(8) 0.0149(7) 0.0199(7) 0.0036(6) -0.0068(6) -0.0069(6) N13 0.0130(7) 0.0144(7) 0.0168(7) 0.0006(5) -0.0020(5) -0.0020(5) C14 0.0120(8) 0.0145(8) 0.0169(8) -0.0016(6) 0.0002(6) 0.0000(6) C15 0.0160(8) 0.0190(9) 0.0202(8) 0.0024(7) -0.0043(6) -0.0050(7) C16 0.0133(8) 0.0153(8) 0.0193(8) -0.0015(6) 0.0005(6) -0.0033(7) C18 0.0187(9) 0.0177(9) 0.0265(9) 0.0022(7) -0.0047(7) -0.0067(7) N21 0.0152(7) 0.0160(7) 0.0158(7) -0.0006(5) -0.0009(5) -0.0023(6) C22 0.0146(8) 0.0159(8) 0.0153(8) 0.0003(6) -0.0025(6) -0.0016(7) C23 0.0131(8) 0.0130(8) 0.0174(8) -0.0013(6) 0.0002(6) -0.0003(6) C24 0.0145(8) 0.0192(9) 0.0237(9) 0.0011(7) -0.0051(7) -0.0045(7) C25 0.0170(8) 0.0230(10) 0.0223(9) 0.0021(7) -0.0065(7) -0.0018(7) C26 0.0158(8) 0.0155(8) 0.0154(8) 0.0000(6) -0.0001(6) 0.0009(7) O26 0.0220(6) 0.0195(6) 0.0190(6) 0.0062(5) -0.0050(5) -0.0066(5) C27 0.0254(9) 0.0196(9) 0.0209(8) 0.0040(7) -0.0038(7) -0.0064(8) C31 0.0168(8) 0.0152(8) 0.0151(8) 0.0009(6) -0.0039(6) -0.0047(7) C32 0.0142(8) 0.0169(8) 0.0168(8) -0.0022(6) -0.0032(6) -0.0029(7) C33 0.0159(8) 0.0193(9) 0.0155(8) -0.0016(6) -0.0020(6) -0.0072(7) C34 0.0195(8) 0.0154(8) 0.0167(8) -0.0001(6) -0.0042(6) -0.0059(7) C35 0.0161(8) 0.0162(8) 0.0175(8) -0.0030(6) -0.0047(6) -0.0022(7) C36 0.0134(8) 0.0180(9) 0.0163(8) -0.0013(6) -0.0023(6) -0.0064(7) C41 0.0162(8) 0.0182(9) 0.0170(8) 0.0005(6) -0.0016(6) -0.0032(7) O41 0.0314(7) 0.0184(7) 0.0235(6) 0.0075(5) -0.0114(6) -0.0096(6) O42 0.0384(8) 0.0190(7) 0.0284(7) 0.0050(5) -0.0144(6) -0.0121(6) C42 0.0191(9) 0.0232(10) 0.0219(9) -0.0024(7) -0.0014(7) 0.0009(7) C43 0.0210(9) 0.0270(10) 0.0190(8) 0.0018(7) 0.0005(7) -0.0048(8) C44 0.0350(11) 0.0189(9) 0.0224(9) 0.0037(7) -0.0013(8) -0.0039(8) C45 0.0222(9) 0.0211(9) 0.0240(9) -0.0029(7) -0.0051(7) 0.0028(7) C46 0.0183(9) 0.0254(10) 0.0202(9) -0.0012(7) 0.0014(7) -0.0047(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.342(2) . ? N11 C12 1.363(2) . ? C12 N12 1.336(2) . ? C12 N13 1.345(2) . ? N12 H12A 0.91(2) . ? N12 H12B 0.85(2) . ? N13 C14 1.339(2) . ? C14 C15 1.392(2) . ? C14 C23 1.486(2) . ? C15 C16 1.382(2) . ? C15 H15 0.9500 . ? C16 C18 1.497(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? N21 C26 1.326(2) . ? N21 C22 1.350(2) . ? C22 C23 1.387(2) . ? C22 H22 0.9500 . ? C23 C24 1.405(2) . ? C24 C25 1.366(2) . ? C24 H24 0.9500 . ? C25 C26 1.397(2) . ? C25 H25 0.9500 . ? C26 O26 1.3487(19) . ? O26 C27 1.433(2) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C31 C36 1.397(2) . ? C31 C32 1.401(2) . ? C31 C41 1.506(2) . ? C32 C33 1.399(2) . ? C32 C42 1.512(2) . ? C33 C34 1.405(2) . ? C33 C43 1.516(2) . ? C34 C35 1.410(2) . ? C34 C44 1.514(2) . ? C35 C36 1.400(2) . ? C35 C45 1.509(2) . ? C36 C46 1.512(2) . ? C41 O42 1.216(2) . ? C41 O41 1.316(2) . ? O41 H41 0.90(2) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 116.97(14) . . ? N12 C12 N13 118.65(15) . . ? N12 C12 N11 116.03(15) . . ? N13 C12 N11 125.32(15) . . ? C12 N12 H12A 118.7(13) . . ? C12 N12 H12B 120.5(14) . . ? H12A N12 H12B 120.7(19) . . ? C14 N13 C12 116.51(14) . . ? N13 C14 C15 121.89(15) . . ? N13 C14 C23 116.82(15) . . ? C15 C14 C23 121.28(15) . . ? C16 C15 C14 118.07(16) . . ? C16 C15 H15 121.0 . . ? C14 C15 H15 121.0 . . ? N11 C16 C15 121.16(16) . . ? N11 C16 C18 117.28(15) . . ? C15 C16 C18 121.56(15) . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C26 N21 C22 116.97(15) . . ? N21 C22 C23 124.09(15) . . ? N21 C22 H22 118.0 . . ? C23 C22 H22 118.0 . . ? C22 C23 C24 116.90(15) . . ? C22 C23 C14 121.27(15) . . ? C24 C23 C14 121.83(15) . . ? C25 C24 C23 120.00(17) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 118.22(16) . . ? C24 C25 H25 120.9 . . ? C26 C25 H25 120.9 . . ? N21 C26 O26 120.48(15) . . ? N21 C26 C25 123.81(15) . . ? O26 C26 C25 115.71(15) . . ? C26 O26 C27 118.10(13) . . ? O26 C27 H27A 109.5 . . ? O26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C36 C31 C32 121.90(15) . . ? C36 C31 C41 119.07(14) . . ? C32 C31 C41 118.99(15) . . ? C33 C32 C31 118.87(15) . . ? C33 C32 C42 120.84(15) . . ? C31 C32 C42 120.29(15) . . ? C32 C33 C34 120.16(15) . . ? C32 C33 C43 118.81(15) . . ? C34 C33 C43 121.02(15) . . ? C33 C34 C35 120.07(15) . . ? C33 C34 C44 120.68(15) . . ? C35 C34 C44 119.24(16) . . ? C36 C35 C34 120.03(15) . . ? C36 C35 C45 118.93(15) . . ? C34 C35 C45 121.03(15) . . ? C31 C36 C35 118.91(15) . . ? C31 C36 C46 120.74(15) . . ? C35 C36 C46 120.34(15) . . ? O42 C41 O41 123.54(16) . . ? O42 C41 C31 122.73(15) . . ? O41 C41 C31 113.73(15) . . ? C41 O41 H41 108.7(14) . . ? C32 C42 H42A 109.5 . . ? C32 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C32 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C33 C43 H43A 109.5 . . ? C33 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C33 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C34 C44 H44A 109.5 . . ? C34 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C34 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C35 C45 H45A 109.5 . . ? C35 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C35 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C36 C46 H46A 109.5 . . ? C36 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C36 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 177.30(15) . . . . ? C16 N11 C12 N13 -3.5(2) . . . . ? N12 C12 N13 C14 -177.23(15) . . . . ? N11 C12 N13 C14 3.6(2) . . . . ? C12 N13 C14 C15 -1.3(2) . . . . ? C12 N13 C14 C23 179.22(14) . . . . ? N13 C14 C15 C16 -0.7(3) . . . . ? C23 C14 C15 C16 178.68(15) . . . . ? C12 N11 C16 C15 1.1(2) . . . . ? C12 N11 C16 C18 -179.46(14) . . . . ? C14 C15 C16 N11 0.9(3) . . . . ? C14 C15 C16 C18 -178.56(15) . . . . ? C26 N21 C22 C23 0.3(2) . . . . ? N21 C22 C23 C24 -1.1(3) . . . . ? N21 C22 C23 C14 179.18(15) . . . . ? N13 C14 C23 C22 2.0(2) . . . . ? C15 C14 C23 C22 -177.41(16) . . . . ? N13 C14 C23 C24 -177.64(16) . . . . ? C15 C14 C23 C24 2.9(2) . . . . ? C22 C23 C24 C25 0.9(3) . . . . ? C14 C23 C24 C25 -179.38(15) . . . . ? C23 C24 C25 C26 0.0(3) . . . . ? C22 N21 C26 O26 -178.82(14) . . . . ? C22 N21 C26 C25 0.7(3) . . . . ? C24 C25 C26 N21 -0.9(3) . . . . ? C24 C25 C26 O26 178.68(15) . . . . ? N21 C26 O26 C27 -0.9(2) . . . . ? C25 C26 O26 C27 179.50(15) . . . . ? C36 C31 C32 C33 0.6(2) . . . . ? C41 C31 C32 C33 -177.15(15) . . . . ? C36 C31 C32 C42 -178.35(16) . . . . ? C41 C31 C32 C42 3.9(2) . . . . ? C31 C32 C33 C34 -1.4(2) . . . . ? C42 C32 C33 C34 177.61(16) . . . . ? C31 C32 C33 C43 179.63(16) . . . . ? C42 C32 C33 C43 -1.4(2) . . . . ? C32 C33 C34 C35 2.3(2) . . . . ? C43 C33 C34 C35 -178.75(16) . . . . ? C32 C33 C34 C44 -176.43(16) . . . . ? C43 C33 C34 C44 2.6(3) . . . . ? C33 C34 C35 C36 -2.4(2) . . . . ? C44 C34 C35 C36 176.30(16) . . . . ? C33 C34 C35 C45 176.50(16) . . . . ? C44 C34 C35 C45 -4.8(2) . . . . ? C32 C31 C36 C35 -0.8(2) . . . . ? C41 C31 C36 C35 177.00(15) . . . . ? C32 C31 C36 C46 179.73(16) . . . . ? C41 C31 C36 C46 -2.5(2) . . . . ? C34 C35 C36 C31 1.6(2) . . . . ? C45 C35 C36 C31 -177.28(16) . . . . ? C34 C35 C36 C46 -178.85(16) . . . . ? C45 C35 C36 C46 2.2(2) . . . . ? C36 C31 C41 O42 -89.7(2) . . . . ? C32 C31 C41 O42 88.1(2) . . . . ? C36 C31 C41 O41 90.37(19) . . . . ? C32 C31 C41 O41 -91.80(19) . . . . ? 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 N12 H12A O42 0.91(2) 2.05(2) 2.9519(19) 173.1(19) . N12 H12B N21 0.85(2) 2.25(2) 3.080(2) 165.3(19) 2_676 O41 H41 N11 0.90(2) 1.77(2) 2.6515(18) 167(2) . _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.914 _refine_diff_density_max 0.397 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.059 #END data_3a _database_code_depnum_ccdc_archive 'CCDC 614730' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(3-methoxy-5-pyridyl)-2-(2-amino-6-methyl-4-pyrimidyl)ethyne, (NO2)2PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C13 H12 N4 O) (C7 H4 N2 O6)' _chemical_formula_sum 'C20 H16 N6 O7' _chemical_formula_weight 452.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.374(11) _cell_length_b 8.385(13) _cell_length_c 17.56(3) _cell_angle_alpha 93.51(10) _cell_angle_beta 96.29(7) _cell_angle_gamma 104.50(11) _cell_volume 1040(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.25 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7011 _diffrn_reflns_av_R_equivalents 0.2098 _diffrn_reflns_av_sigmaI/netI 0.3545 _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 -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.14 _reflns_number_total 4228 _reflns_number_gt 1209 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.057(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4228 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2841 _refine_ls_R_factor_gt 0.1139 _refine_ls_wR_factor_ref 0.3299 _refine_ls_wR_factor_gt 0.2495 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.5396(10) 0.2350(6) 0.5225(4) 0.0393(19) Uani 1 1 d . . . C12 C 0.7118(13) 0.3324(8) 0.5157(4) 0.036(2) Uani 1 1 d . . . N12 N 0.8613(10) 0.3367(7) 0.5691(3) 0.046(2) Uani 1 1 d . . . H12A H 0.8459 0.2759 0.6081 0.055 Uiso 1 1 calc R . . H12B H 0.9735 0.4003 0.5646 0.055 Uiso 1 1 calc R . . N13 N 0.7508(10) 0.4319(6) 0.4559(3) 0.0364(18) Uani 1 1 d . . . C14 C 0.5940(13) 0.4306(8) 0.4048(4) 0.039(2) Uani 1 1 d . . . C15 C 0.4124(13) 0.3361(8) 0.4095(4) 0.042(2) Uani 1 1 d . . . H15 H 0.3085 0.3383 0.3729 0.050 Uiso 1 1 calc R . . C16 C 0.3906(11) 0.2392(8) 0.4700(4) 0.0289(19) Uani 1 1 d . . . C17 C 0.2007(12) 0.1326(9) 0.4812(4) 0.042(2) Uani 1 1 d . . . H17A H 0.2059 0.0169 0.4810 0.064 Uiso 1 1 calc R . . H17B H 0.1061 0.1431 0.4393 0.064 Uiso 1 1 calc R . . H17C H 0.1660 0.1682 0.5305 0.064 Uiso 1 1 calc R . . C18 C 0.6271(12) 0.5340(8) 0.3417(4) 0.034(2) Uani 1 1 d . . . N21 N 0.8641(11) 0.9107(7) 0.1564(4) 0.049(2) Uani 1 1 d . . . C22 C 0.7085(13) 0.9064(9) 0.1055(4) 0.041(2) Uani 1 1 d . . . H22 H 0.7267 0.9750 0.0644 0.049 Uiso 1 1 calc R . . C23 C 0.5270(13) 0.8113(9) 0.1082(4) 0.044(3) Uani 1 1 d . . . O23 O 0.3904(9) 0.8272(6) 0.0506(3) 0.0469(17) Uani 1 1 d . . . C24 C 0.4972(12) 0.7121(8) 0.1675(4) 0.036(2) Uani 1 1 d . . . H24 H 0.3751 0.6450 0.1722 0.043 Uiso 1 1 calc R . . C25 C 0.6579(14) 0.7136(9) 0.2219(5) 0.046(3) Uani 1 1 d . . . C26 C 0.8272(15) 0.8126(9) 0.2161(4) 0.048(3) Uani 1 1 d . . . H26 H 0.9281 0.8158 0.2553 0.057 Uiso 1 1 calc R . . C27 C 0.1953(14) 0.7346(10) 0.0546(5) 0.062(3) Uani 1 1 d . . . H27A H 0.1133 0.7519 0.0098 0.093 Uiso 1 1 calc R . . H27B H 0.1534 0.7735 0.1018 0.093 Uiso 1 1 calc R . . H27C H 0.1888 0.6165 0.0551 0.093 Uiso 1 1 calc R . . C28 C 0.6367(12) 0.6170(8) 0.2883(4) 0.034(2) Uani 1 1 d . . . C31 C 0.4979(14) -0.0932(8) 0.7434(4) 0.040(2) Uani 1 1 d . . . C37 C 0.5727(14) 0.0249(9) 0.6843(4) 0.043(2) Uani 1 1 d . . . O31 O 0.4393(8) 0.0320(5) 0.6280(3) 0.0431(16) Uani 1 1 d . . . H31 H 0.4771 0.1162 0.6047 0.052 Uiso 1 1 calc R . . O32 O 0.7358(9) 0.1020(7) 0.6904(3) 0.0518(18) Uani 1 1 d . . . C32 C 0.6299(12) -0.1195(8) 0.8033(4) 0.034(2) Uani 1 1 d . . . H32 H 0.7608 -0.0664 0.8066 0.041 Uiso 1 1 calc R . . C33 C 0.5593(14) -0.2266(9) 0.8572(4) 0.045(3) Uani 1 1 d . . . N33 N 0.6947(11) -0.2582(8) 0.9209(4) 0.0413(19) Uani 1 1 d . . . O33 O 0.8547(10) -0.1624(8) 0.9318(3) 0.067(2) Uani 1 1 d . . . O34 O 0.6459(9) -0.3732(6) 0.9582(3) 0.0495(18) Uani 1 1 d . . . C34 C 0.3708(13) -0.3069(8) 0.8537(4) 0.036(2) Uani 1 1 d . . . H34 H 0.3274 -0.3808 0.8907 0.044 Uiso 1 1 calc R . . C35 C 0.2448(14) -0.2763(9) 0.7938(4) 0.042(2) Uani 1 1 d . . . N35 N 0.0413(12) -0.3569(8) 0.7885(4) 0.057(2) Uani 1 1 d . . . O35 O -0.0139(10) -0.4490(8) 0.8387(4) 0.075(2) Uani 1 1 d . . . O36 O -0.0678(9) -0.3297(8) 0.7350(4) 0.070(2) Uani 1 1 d . . . C36 C 0.3063(13) -0.1714(9) 0.7378(4) 0.040(2) Uani 1 1 d . . . H36 H 0.2196 -0.1539 0.6971 0.048 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.039(5) 0.023(3) 0.050(4) -0.005(3) -0.022(4) 0.010(3) C12 0.046(6) 0.023(4) 0.034(4) -0.013(3) -0.020(4) 0.015(4) N12 0.053(5) 0.044(4) 0.037(4) 0.013(3) -0.015(4) 0.014(4) N13 0.051(5) 0.024(3) 0.034(4) 0.002(3) -0.009(3) 0.017(3) C14 0.053(7) 0.027(4) 0.034(4) -0.010(3) -0.017(4) 0.018(4) C15 0.056(7) 0.033(4) 0.034(4) -0.005(3) -0.027(4) 0.022(5) C16 0.025(5) 0.026(4) 0.033(4) -0.001(3) -0.004(4) 0.004(4) C17 0.040(6) 0.047(5) 0.038(5) -0.005(4) -0.014(4) 0.019(5) C18 0.043(6) 0.028(4) 0.032(4) 0.006(3) -0.005(4) 0.016(4) N21 0.057(6) 0.039(4) 0.048(4) 0.007(3) -0.007(4) 0.013(4) C22 0.050(7) 0.036(4) 0.033(4) 0.004(3) -0.007(4) 0.009(4) C23 0.051(7) 0.031(4) 0.044(5) -0.005(4) -0.032(5) 0.017(4) O23 0.056(5) 0.049(3) 0.036(3) 0.009(3) -0.012(3) 0.020(3) C24 0.040(6) 0.025(4) 0.041(5) -0.003(3) -0.014(4) 0.014(4) C25 0.054(7) 0.026(4) 0.049(5) -0.003(4) -0.025(5) 0.012(4) C26 0.066(7) 0.038(4) 0.034(5) 0.000(4) -0.024(5) 0.018(5) C27 0.060(8) 0.048(5) 0.066(6) -0.003(4) -0.036(6) 0.015(5) C28 0.035(6) 0.025(4) 0.038(4) -0.002(3) -0.010(4) 0.010(4) C31 0.071(8) 0.030(4) 0.020(4) -0.001(3) -0.016(4) 0.026(5) C37 0.035(6) 0.041(5) 0.047(5) -0.009(4) -0.026(5) 0.015(5) O31 0.052(4) 0.035(3) 0.041(3) 0.008(2) -0.009(3) 0.013(3) O32 0.049(5) 0.061(4) 0.038(3) 0.023(3) -0.013(3) 0.005(3) C32 0.051(6) 0.027(4) 0.027(4) 0.003(3) -0.002(4) 0.018(4) C33 0.067(8) 0.031(4) 0.033(5) -0.004(4) -0.022(5) 0.023(5) N33 0.040(5) 0.043(4) 0.040(4) 0.006(3) -0.011(4) 0.016(4) O33 0.043(5) 0.093(5) 0.057(4) 0.040(3) -0.010(3) 0.001(4) O34 0.078(5) 0.038(3) 0.038(3) 0.021(3) 0.004(3) 0.023(3) C34 0.048(7) 0.030(4) 0.028(4) -0.009(3) -0.006(4) 0.011(4) C35 0.056(7) 0.037(4) 0.032(4) -0.003(3) -0.012(4) 0.018(4) N35 0.055(6) 0.056(4) 0.055(5) 0.008(4) -0.021(4) 0.018(4) O35 0.061(5) 0.085(4) 0.069(4) 0.042(4) -0.012(4) 0.002(4) O36 0.037(4) 0.097(5) 0.065(4) 0.028(4) -0.010(4) -0.001(4) C36 0.048(6) 0.041(4) 0.034(5) -0.007(4) -0.015(4) 0.029(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.349(11) . ? N11 C16 1.363(9) . ? C12 N12 1.357(9) . ? C12 N13 1.390(10) . ? N12 H12A 0.8800 . ? N12 H12B 0.8800 . ? N13 C14 1.382(9) . ? C14 C15 1.389(12) . ? C14 C18 1.452(11) . ? C15 C16 1.375(10) . ? C15 H15 0.9500 . ? C16 C17 1.501(11) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C28 1.199(9) . ? N21 C22 1.367(9) . ? N21 C26 1.381(10) . ? C22 C23 1.383(12) . ? C22 H22 0.9500 . ? C23 C24 1.374(11) . ? C23 O23 1.384(8) . ? O23 C27 1.465(11) . ? C24 C25 1.435(10) . ? C24 H24 0.9500 . ? C25 C26 1.333(13) . ? C25 C28 1.461(11) . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C31 C36 1.391(13) . ? C31 C32 1.419(9) . ? C31 C37 1.528(12) . ? C37 O32 1.204(10) . ? C37 O31 1.332(8) . ? O31 H31 0.8400 . ? C32 C33 1.397(11) . ? C32 H32 0.9500 . ? C33 C34 1.377(12) . ? C33 N33 1.496(9) . ? N33 O34 1.201(8) . ? N33 O33 1.238(9) . ? C34 C35 1.405(10) . ? C34 H34 0.9500 . ? C35 C36 1.396(12) . ? C35 N35 1.473(12) . ? N35 O36 1.238(8) . ? N35 O35 1.242(10) . ? C36 H36 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C16 118.7(6) . . ? N11 C12 N12 120.1(7) . . ? N11 C12 N13 124.2(7) . . ? N12 C12 N13 115.7(8) . . ? C12 N12 H12A 120.0 . . ? C12 N12 H12B 120.0 . . ? H12A N12 H12B 120.0 . . ? C14 N13 C12 114.1(8) . . ? N13 C14 C15 124.4(7) . . ? N13 C14 C18 116.2(8) . . ? C15 C14 C18 119.4(7) . . ? C16 C15 C14 116.6(7) . . ? C16 C15 H15 121.7 . . ? C14 C15 H15 121.7 . . ? N11 C16 C15 121.8(8) . . ? N11 C16 C17 116.9(6) . . ? C15 C16 C17 121.3(7) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C28 C18 C14 173.9(9) . . ? C22 N21 C26 114.1(8) . . ? N21 C22 C23 126.1(7) . . ? N21 C22 H22 117.0 . . ? C23 C22 H22 117.0 . . ? C24 C23 C22 118.0(7) . . ? C24 C23 O23 125.9(9) . . ? C22 C23 O23 116.2(7) . . ? C23 O23 C27 117.2(7) . . ? C23 C24 C25 117.4(8) . . ? C23 C24 H24 121.3 . . ? C25 C24 H24 121.3 . . ? C26 C25 C24 120.7(8) . . ? C26 C25 C28 118.3(7) . . ? C24 C25 C28 120.7(9) . . ? C25 C26 N21 123.6(7) . . ? C25 C26 H26 118.2 . . ? N21 C26 H26 118.2 . . ? O23 C27 H27A 109.5 . . ? O23 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O23 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C18 C28 C25 176.3(9) . . ? C36 C31 C32 121.7(8) . . ? C36 C31 C37 120.5(6) . . ? C32 C31 C37 117.8(8) . . ? O32 C37 O31 125.3(8) . . ? O32 C37 C31 121.9(7) . . ? O31 C37 C31 112.8(8) . . ? C37 O31 H31 109.5 . . ? C33 C32 C31 117.2(8) . . ? C33 C32 H32 121.4 . . ? C31 C32 H32 121.4 . . ? C34 C33 C32 122.9(7) . . ? C34 C33 N33 118.4(8) . . ? C32 C33 N33 118.7(9) . . ? O34 N33 O33 123.2(7) . . ? O34 N33 C33 119.9(8) . . ? O33 N33 C33 117.0(7) . . ? C33 C34 C35 117.9(8) . . ? C33 C34 H34 121.0 . . ? C35 C34 H34 121.0 . . ? C36 C35 C34 122.0(9) . . ? C36 C35 N35 118.1(7) . . ? C34 C35 N35 120.0(8) . . ? O36 N35 O35 122.6(9) . . ? O36 N35 C35 119.2(8) . . ? O35 N35 C35 118.2(7) . . ? C31 C36 C35 118.2(7) . . ? C31 C36 H36 120.9 . . ? C35 C36 H36 120.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 177.0(6) . . . . ? C16 N11 C12 N13 -3.5(11) . . . . ? N11 C12 N13 C14 3.4(10) . . . . ? N12 C12 N13 C14 -177.1(6) . . . . ? C12 N13 C14 C15 -1.8(10) . . . . ? C12 N13 C14 C18 179.4(6) . . . . ? N13 C14 C15 C16 0.4(11) . . . . ? C18 C14 C15 C16 179.2(6) . . . . ? C12 N11 C16 C15 1.9(10) . . . . ? C12 N11 C16 C17 -178.2(6) . . . . ? C14 C15 C16 N11 -0.4(11) . . . . ? C14 C15 C16 C17 179.7(7) . . . . ? N13 C14 C18 C28 -167(7) . . . . ? C15 C14 C18 C28 14(7) . . . . ? C26 N21 C22 C23 -2.1(11) . . . . ? N21 C22 C23 C24 0.5(12) . . . . ? N21 C22 C23 O23 179.7(7) . . . . ? C24 C23 O23 C27 2.4(11) . . . . ? C22 C23 O23 C27 -176.8(7) . . . . ? C22 C23 C24 C25 -0.5(11) . . . . ? O23 C23 C24 C25 -179.7(7) . . . . ? C23 C24 C25 C26 2.4(11) . . . . ? C23 C24 C25 C28 177.4(7) . . . . ? C24 C25 C26 N21 -4.4(13) . . . . ? C28 C25 C26 N21 -179.5(7) . . . . ? C22 N21 C26 C25 4.0(12) . . . . ? C14 C18 C28 C25 -140(11) . . . . ? C26 C25 C28 C18 -57(12) . . . . ? C24 C25 C28 C18 128(12) . . . . ? C36 C31 C37 O32 175.4(8) . . . . ? C32 C31 C37 O32 -4.6(11) . . . . ? C36 C31 C37 O31 -4.2(10) . . . . ? C32 C31 C37 O31 175.9(6) . . . . ? C36 C31 C32 C33 -0.5(10) . . . . ? C37 C31 C32 C33 179.5(6) . . . . ? C31 C32 C33 C34 0.7(11) . . . . ? C31 C32 C33 N33 179.5(6) . . . . ? C34 C33 N33 O34 14.1(10) . . . . ? C32 C33 N33 O34 -164.7(7) . . . . ? C34 C33 N33 O33 -166.4(7) . . . . ? C32 C33 N33 O33 14.7(10) . . . . ? C32 C33 C34 C35 -1.3(11) . . . . ? N33 C33 C34 C35 179.9(6) . . . . ? C33 C34 C35 C36 1.6(11) . . . . ? C33 C34 C35 N35 -178.9(7) . . . . ? C36 C35 N35 O36 0.1(11) . . . . ? C34 C35 N35 O36 -179.5(7) . . . . ? C36 C35 N35 O35 -179.3(7) . . . . ? C34 C35 N35 O35 1.1(11) . . . . ? C32 C31 C36 C35 0.8(11) . . . . ? C37 C31 C36 C35 -179.1(7) . . . . ? C34 C35 C36 C31 -1.4(11) . . . . ? N35 C35 C36 C31 179.1(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N12 H12A O32 0.88 2.19 3.049(9) 165.6 . N12 H12B N13 0.88 2.24 3.121(12) 175.3 2_766 O31 H31 N11 0.84 1.84 2.633(9) 157.2 . _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.917 _refine_diff_density_max 0.607 _refine_diff_density_min -0.723 _refine_diff_density_rms 0.125 #END data_3b _database_code_depnum_ccdc_archive 'CCDC 614731' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [1-(3-OMe-5-pyridyl)-2-(2-amino-4-methyl-6-pyrimidyl)-ethyne], NO2PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C13 H12 N4 O) (C7 H5 N O4) ; _chemical_formula_sum 'C20 H17 N5 O5' _chemical_formula_weight 407.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9157(12) _cell_length_b 6.9405(12) _cell_length_c 19.854(4) _cell_angle_alpha 87.646(3) _cell_angle_beta 80.636(3) _cell_angle_gamma 81.138(3) _cell_volume 928.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1448 _cell_measurement_theta_min 4.95 _cell_measurement_theta_max 25.95 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4809 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0667 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3438 _reflns_number_gt 2099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.1500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3438 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1084 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1382 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.2547(3) 0.4953(3) 0.51616(11) 0.0176(5) Uani 1 1 d . . . C12 C 0.3334(4) 0.3048(4) 0.51252(14) 0.0181(6) Uani 1 1 d . . . N12 N 0.3537(4) 0.2074(4) 0.57121(13) 0.0211(6) Uani 1 1 d . . . H12A H 0.318(4) 0.273(4) 0.6108(15) 0.025 Uiso 1 1 d . . . H12B H 0.419(4) 0.084(4) 0.5705(14) 0.025 Uiso 1 1 d . . . N13 N 0.3919(3) 0.2031(3) 0.45413(11) 0.0181(5) Uani 1 1 d . . . C14 C 0.3619(4) 0.3040(4) 0.39638(14) 0.0185(6) Uani 1 1 d . . . C15 C 0.2817(4) 0.4997(4) 0.39547(14) 0.0218(7) Uani 1 1 d . . . H15 H 0.2628 0.5674 0.3539 0.026 Uiso 1 1 calc R . . C16 C 0.2302(4) 0.5924(4) 0.45769(14) 0.0187(6) Uani 1 1 d . . . C17 C 0.4156(4) 0.2010(4) 0.33326(14) 0.0194(6) Uani 1 1 d . . . C18 C 0.1449(4) 0.8039(4) 0.46314(15) 0.0252(7) Uani 1 1 d . . . H18A H 0.1406 0.8607 0.4173 0.038 Uiso 1 1 calc R . . H18B H 0.2280 0.8721 0.4866 0.038 Uiso 1 1 calc R . . H18C H 0.0104 0.8174 0.4890 0.038 Uiso 1 1 calc R . . N21 N 0.5123(4) 0.1335(3) 0.09003(12) 0.0255(6) Uani 1 1 d . . . C22 C 0.4727(4) 0.1873(4) 0.15497(14) 0.0227(7) Uani 1 1 d . . . H22 H 0.4248 0.3206 0.1648 0.027 Uiso 1 1 calc R . . C23 C 0.4982(4) 0.0568(4) 0.20952(14) 0.0185(6) Uani 1 1 d . . . C24 C 0.5673(4) -0.1377(4) 0.19556(14) 0.0200(6) Uani 1 1 d . . . H24 H 0.5857 -0.2300 0.2315 0.024 Uiso 1 1 calc R . . C25 C 0.6090(4) -0.1945(4) 0.12829(14) 0.0186(6) Uani 1 1 d . . . O25 O 0.6776(3) -0.3868(3) 0.11655(10) 0.0272(5) Uani 1 1 d . . . C28 C 0.7193(5) -0.4455(4) 0.04599(14) 0.0301(8) Uani 1 1 d . . . H28A H 0.7495 -0.5880 0.0439 0.045 Uiso 1 1 calc R . . H28B H 0.8333 -0.3882 0.0224 0.045 Uiso 1 1 calc R . . H28C H 0.6035 -0.4002 0.0238 0.045 Uiso 1 1 calc R . . C26 C 0.5822(4) -0.0554(4) 0.07728(15) 0.0233(7) Uani 1 1 d . . . H26 H 0.6146 -0.0953 0.0311 0.028 Uiso 1 1 calc R . . C27 C 0.4535(4) 0.1297(4) 0.27775(14) 0.0208(7) Uani 1 1 d . . . C31 C 0.0709(4) 0.7987(4) 0.73916(14) 0.0185(6) Uani 1 1 d . . . C37 C 0.1397(4) 0.6528(4) 0.68331(15) 0.0209(7) Uani 1 1 d . . . O31 O 0.1394(3) 0.7304(3) 0.62178(10) 0.0249(5) Uani 1 1 d . . . H31 H 0.178(4) 0.634(4) 0.5849(15) 0.030 Uiso 1 1 d . . . O32 O 0.1912(3) 0.4797(3) 0.69457(10) 0.0289(5) Uani 1 1 d . . . C32 C 0.0549(4) 0.7363(4) 0.80635(14) 0.0230(7) Uani 1 1 d . . . H32 H 0.0866 0.6015 0.8169 0.028 Uiso 1 1 calc R . . C33 C -0.0072(4) 0.8694(4) 0.85889(14) 0.0222(7) Uani 1 1 d . . . H33 H -0.0179 0.8276 0.9053 0.027 Uiso 1 1 calc R . . C34 C -0.0527(4) 1.0635(4) 0.84170(14) 0.0192(6) Uani 1 1 d . . . N34 N -0.1168(3) 1.2049(4) 0.89715(13) 0.0239(6) Uani 1 1 d . . . O33 O -0.1092(3) 1.1460(3) 0.95586(10) 0.0351(6) Uani 1 1 d . . . O34 O -0.1747(3) 1.3751(3) 0.88219(11) 0.0333(6) Uani 1 1 d . . . C35 C -0.0380(4) 1.1306(4) 0.77532(14) 0.0212(7) Uani 1 1 d . . . H35 H -0.0703 1.2655 0.7652 0.025 Uiso 1 1 calc R . . C36 C 0.0251(4) 0.9969(4) 0.72348(15) 0.0198(6) Uani 1 1 d . . . H36 H 0.0372 1.0401 0.6772 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0173(12) 0.0121(12) 0.0228(13) -0.0033(10) -0.0030(10) 0.0002(10) C12 0.0149(14) 0.0183(15) 0.0211(16) -0.0047(12) -0.0016(12) -0.0023(12) N12 0.0259(14) 0.0157(13) 0.0199(14) -0.0018(10) -0.0014(11) 0.0003(11) N13 0.0179(12) 0.0142(12) 0.0218(13) -0.0031(10) -0.0029(10) -0.0007(10) C14 0.0167(15) 0.0176(15) 0.0208(15) -0.0049(12) -0.0006(12) -0.0025(12) C15 0.0217(15) 0.0214(16) 0.0216(16) -0.0014(12) -0.0030(12) -0.0005(13) C16 0.0146(14) 0.0162(14) 0.0255(17) -0.0012(12) -0.0030(12) -0.0026(12) C17 0.0189(15) 0.0151(15) 0.0225(16) -0.0003(12) -0.0017(12) 0.0016(12) C18 0.0260(16) 0.0170(15) 0.0323(18) -0.0035(13) -0.0089(13) 0.0034(13) N21 0.0290(15) 0.0220(14) 0.0241(14) -0.0013(11) -0.0050(11) 0.0021(11) C22 0.0261(16) 0.0175(15) 0.0236(17) -0.0023(12) -0.0052(13) 0.0010(13) C23 0.0146(14) 0.0212(15) 0.0186(15) -0.0028(12) 0.0001(11) -0.0011(12) C24 0.0168(14) 0.0229(16) 0.0197(16) -0.0005(12) -0.0030(12) -0.0015(12) C25 0.0164(15) 0.0144(15) 0.0253(17) -0.0019(12) -0.0033(12) -0.0025(12) O25 0.0403(13) 0.0157(11) 0.0234(12) -0.0047(8) -0.0057(9) 0.0046(9) C28 0.0392(19) 0.0259(17) 0.0236(17) -0.0109(14) -0.0021(14) 0.0000(15) C26 0.0224(16) 0.0250(16) 0.0225(16) -0.0043(13) -0.0040(13) -0.0015(13) C27 0.0185(15) 0.0181(15) 0.0261(17) -0.0002(13) -0.0058(12) -0.0014(12) C31 0.0136(14) 0.0166(15) 0.0251(16) -0.0022(12) -0.0019(12) -0.0023(12) C37 0.0137(15) 0.0224(17) 0.0258(17) -0.0040(13) 0.0008(12) -0.0030(12) O31 0.0335(12) 0.0186(11) 0.0212(12) -0.0045(9) -0.0039(9) 0.0006(9) O32 0.0377(13) 0.0164(11) 0.0299(12) -0.0032(9) -0.0016(10) 0.0010(10) C32 0.0250(16) 0.0159(15) 0.0257(17) 0.0006(12) -0.0003(13) 0.0001(12) C33 0.0239(16) 0.0226(16) 0.0182(15) 0.0023(12) -0.0013(12) -0.0008(13) C34 0.0131(14) 0.0213(16) 0.0230(16) -0.0059(12) -0.0013(12) -0.0023(12) N34 0.0220(14) 0.0249(15) 0.0243(15) -0.0074(11) -0.0008(11) -0.0034(11) O33 0.0493(15) 0.0307(13) 0.0225(13) -0.0047(10) -0.0030(11) 0.0008(11) O34 0.0438(14) 0.0154(11) 0.0370(14) -0.0051(9) -0.0025(11) 0.0038(10) C35 0.0221(15) 0.0172(15) 0.0242(17) -0.0030(12) -0.0029(12) -0.0024(12) C36 0.0176(15) 0.0198(15) 0.0225(16) 0.0002(12) -0.0053(12) -0.0018(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.340(3) . ? N11 C12 1.350(3) . ? C12 N12 1.339(4) . ? C12 N13 1.354(3) . ? N12 H12A 0.91(3) . ? N12 H12B 0.90(3) . ? N13 C14 1.347(3) . ? C14 C15 1.387(4) . ? C14 C17 1.435(4) . ? C15 C16 1.385(4) . ? C15 H15 0.9500 . ? C16 C18 1.497(4) . ? C17 C27 1.200(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? N21 C22 1.330(4) . ? N21 C26 1.345(4) . ? C22 C23 1.399(4) . ? C22 H22 0.9500 . ? C23 C24 1.384(4) . ? C23 C27 1.435(4) . ? C24 C25 1.380(4) . ? C24 H24 0.9500 . ? C25 O25 1.362(3) . ? C25 C26 1.385(4) . ? O25 C28 1.446(3) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C26 H26 0.9500 . ? C31 C32 1.378(4) . ? C31 C36 1.398(4) . ? C31 C37 1.501(4) . ? C37 O32 1.221(3) . ? C37 O31 1.315(3) . ? O31 H31 0.99(3) . ? C32 C33 1.392(4) . ? C32 H32 0.9500 . ? C33 C34 1.377(4) . ? C33 H33 0.9500 . ? C34 C35 1.373(4) . ? C34 N34 1.472(3) . ? N34 O33 1.226(3) . ? N34 O34 1.228(3) . ? C35 C36 1.385(4) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 118.0(2) . . ? N12 C12 N11 117.7(2) . . ? N12 C12 N13 117.1(3) . . ? N11 C12 N13 125.2(3) . . ? C12 N12 H12A 118.5(18) . . ? C12 N12 H12B 119.9(18) . . ? H12A N12 H12B 121(3) . . ? C14 N13 C12 115.3(2) . . ? N13 C14 C15 123.2(2) . . ? N13 C14 C17 117.5(2) . . ? C15 C14 C17 119.3(3) . . ? C16 C15 C14 117.2(3) . . ? C16 C15 H15 121.4 . . ? C14 C15 H15 121.4 . . ? N11 C16 C15 121.0(3) . . ? N11 C16 C18 116.9(2) . . ? C15 C16 C18 122.1(3) . . ? C27 C17 C14 174.2(3) . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C22 N21 C26 117.5(3) . . ? N21 C22 C23 123.1(3) . . ? N21 C22 H22 118.5 . . ? C23 C22 H22 118.5 . . ? C24 C23 C22 118.7(3) . . ? C24 C23 C27 122.5(3) . . ? C22 C23 C27 118.8(3) . . ? C25 C24 C23 118.6(3) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? O25 C25 C24 116.9(3) . . ? O25 C25 C26 124.1(2) . . ? C24 C25 C26 119.0(3) . . ? C25 O25 C28 116.5(2) . . ? O25 C28 H28A 109.5 . . ? O25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N21 C26 C25 123.1(3) . . ? N21 C26 H26 118.4 . . ? C25 C26 H26 118.4 . . ? C17 C27 C23 176.3(3) . . ? C32 C31 C36 119.9(3) . . ? C32 C31 C37 119.6(2) . . ? C36 C31 C37 120.5(3) . . ? O32 C37 O31 123.9(3) . . ? O32 C37 C31 122.8(3) . . ? O31 C37 C31 113.3(2) . . ? C37 O31 H31 113.7(17) . . ? C31 C32 C33 120.4(3) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C34 C33 C32 118.2(3) . . ? C34 C33 H33 120.9 . . ? C32 C33 H33 120.9 . . ? C35 C34 C33 122.8(3) . . ? C35 C34 N34 118.8(2) . . ? C33 C34 N34 118.3(3) . . ? O33 N34 O34 123.5(2) . . ? O33 N34 C34 118.1(2) . . ? O34 N34 C34 118.4(2) . . ? C34 C35 C36 118.5(3) . . ? C34 C35 H35 120.8 . . ? C36 C35 H35 120.8 . . ? C35 C36 C31 120.1(3) . . ? C35 C36 H36 119.9 . . ? C31 C36 H36 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 -178.6(2) . . . . ? C16 N11 C12 N13 0.7(4) . . . . ? N12 C12 N13 C14 177.5(2) . . . . ? N11 C12 N13 C14 -1.9(4) . . . . ? C12 N13 C14 C15 1.7(4) . . . . ? C12 N13 C14 C17 -178.1(2) . . . . ? N13 C14 C15 C16 -0.4(4) . . . . ? C17 C14 C15 C16 179.3(3) . . . . ? C12 N11 C16 C15 0.8(4) . . . . ? C12 N11 C16 C18 -179.3(2) . . . . ? C14 C15 C16 N11 -0.9(4) . . . . ? C14 C15 C16 C18 179.2(3) . . . . ? c26 N21 C22 C23 -0.8(4) . . . . ? N21 C22 C23 C24 -0.2(4) . . . . ? N21 C22 C23 C27 179.2(3) . . . . ? C22 C23 C24 C25 0.3(4) . . . . ? C27 C23 C24 C25 -179.1(3) . . . . ? C23 C24 C25 O25 179.7(2) . . . . ? C23 C24 C25 C26 0.6(4) . . . . ? C24 C25 O25 C28 179.5(2) . . . . ? C26 C25 O25 C28 -1.4(4) . . . . ? C22 N21 C26 C25 1.7(4) . . . . ? O25 C25 C26 N21 179.3(3) . . . . ? C24 C25 C26 N21 -1.7(4) . . . . ? C32 C31 C37 O32 -3.2(4) . . . . ? C36 C31 C37 O32 176.1(3) . . . . ? C32 C31 C37 O31 177.0(2) . . . . ? C36 C31 C37 O31 -3.7(4) . . . . ? C36 C31 C32 C33 0.2(4) . . . . ? C37 C31 C32 C33 179.5(3) . . . . ? C31 C32 C33 C34 0.3(4) . . . . ? C32 C33 C34 C35 -0.5(4) . . . . ? C32 C33 C34 N34 -179.5(2) . . . . ? C35 C34 N34 O33 -172.4(3) . . . . ? C33 C34 N34 O33 6.6(4) . . . . ? C35 C34 N34 O34 7.5(4) . . . . ? C33 C34 N34 O34 -173.4(3) . . . . ? C33 C34 C35 C36 0.1(4) . . . . ? N34 C34 C35 C36 179.1(2) . . . . ? C34 C35 C36 C31 0.4(4) . . . . ? C32 C31 C36 C35 -0.6(4) . . . . ? C37 C31 C36 C35 -179.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N12 H12A O32 0.91(3) 2.22(3) 3.109(3) 168(2) . O31 H31 N11 0.99(3) 1.67(3) 2.652(3) 173(3) . N12 H12B N13 0.90(3) 2.24(3) 3.122(3) 168(2) 2_656 _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.307 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.056 #END data_3c _database_code_depnum_ccdc_archive 'CCDC 614732' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [1-(3-OMe-5-pyridyl)-2-(2-amino-4-methyl-6-pyrimidyl)-ethyne], 3-Me2N-PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C13 H12 N4 O) (C9 H11 N O2) ; _chemical_formula_sum 'C22 H23 N5 O3' _chemical_formula_weight 405.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5742(19) _cell_length_b 14.599(3) _cell_length_c 13.519(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.453(11) _cell_angle_gamma 90.00 _cell_volume 2037.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1097 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 18.75 _exptl_crystal_description Block _exptl_crystal_colour lustrous _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44586 _diffrn_reflns_av_R_equivalents 0.1870 _diffrn_reflns_av_sigmaI/netI 0.1380 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.22 _reflns_number_total 4534 _reflns_number_gt 2037 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4534 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1809 _refine_ls_R_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.2304 _refine_ls_wR_factor_gt 0.1753 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.2921(2) 0.69559(17) 0.64765(17) 0.0295(7) Uani 1 1 d . . . C12 C 0.2330(3) 0.6937(2) 0.5481(2) 0.0293(8) Uani 1 1 d . . . N12 N 0.2162(3) 0.61190(19) 0.5023(2) 0.0384(8) Uani 1 1 d . . . H12A H 0.242(3) 0.559(2) 0.548(2) 0.046 Uiso 1 1 d . . . H12B H 0.164(3) 0.610(2) 0.436(3) 0.046 Uiso 1 1 d . . . N13 N 0.1904(2) 0.76792(17) 0.49159(18) 0.0300(7) Uani 1 1 d . . . C14 C 0.2122(3) 0.8490(2) 0.5383(2) 0.0291(8) Uani 1 1 d . . . C15 C 0.2752(3) 0.8567(2) 0.6393(2) 0.0290(8) Uani 1 1 d . . . H15 H 0.2914 0.9137 0.6701 0.035 Uiso 1 1 calc R . . C16 C 0.3129(3) 0.7773(2) 0.6924(2) 0.0283(8) Uani 1 1 d . . . C17 C 0.1642(3) 0.9279(2) 0.4789(2) 0.0300(8) Uani 1 1 d . . . C18 C 0.3758(3) 0.7776(2) 0.8027(2) 0.0384(9) Uani 1 1 d . . . H18A H 0.4544 0.7425 0.8134 0.058 Uiso 1 1 calc R . . H18B H 0.3181 0.7509 0.8406 0.058 Uiso 1 1 calc R . . H18C H 0.3954 0.8394 0.8249 0.058 Uiso 1 1 calc R . . N21 N -0.0386(2) 1.12485(18) 0.20490(18) 0.0342(7) Uani 1 1 d . . . C22 C 0.0107(3) 1.0565(2) 0.2666(2) 0.0316(8) Uani 1 1 d . . . H22 H 0.0038 0.9971 0.2411 0.038 Uiso 1 1 calc R . . C23 C 0.0721(3) 1.0699(2) 0.3676(2) 0.0296(8) Uani 1 1 d . . . C24 C 0.0836(3) 1.1588(2) 0.4055(2) 0.0291(8) Uani 1 1 d . . . H24 H 0.1241 1.1701 0.4726 0.035 Uiso 1 1 calc R . . C25 C 0.0338(3) 1.2296(2) 0.3415(2) 0.0291(7) Uani 1 1 d . . . O25 O 0.0360(2) 1.31985(15) 0.36726(16) 0.0412(6) Uani 1 1 d . . . C26 C -0.0272(3) 1.2089(2) 0.2419(2) 0.0316(8) Uani 1 1 d . . . H26 H -0.0618 1.2568 0.1993 0.038 Uiso 1 1 calc R . . C27 C 0.1224(3) 0.9933(2) 0.4292(2) 0.0314(8) Uani 1 1 d . . . C28 C 0.0985(3) 1.3440(2) 0.4688(2) 0.0434(9) Uani 1 1 d . . . H28A H 0.1903 1.3359 0.4776 0.065 Uiso 1 1 calc R . . H28B H 0.0669 1.3055 0.5157 0.065 Uiso 1 1 calc R . . H28C H 0.0801 1.4069 0.4812 0.065 Uiso 1 1 calc R . . C31 C 0.3620(3) 0.3970(2) 0.8046(2) 0.0307(8) Uani 1 1 d . . . C37 C 0.3297(3) 0.4712(2) 0.7288(2) 0.0324(8) Uani 1 1 d . . . O31 O 0.3536(2) 0.55371(16) 0.76764(16) 0.0426(7) Uani 1 1 d . . . H31 H 0.337(3) 0.603(2) 0.719(3) 0.051 Uiso 1 1 d . . . O32 O 0.2858(2) 0.45727(15) 0.63879(16) 0.0469(7) Uani 1 1 d . . . C32 C 0.3351(3) 0.3073(2) 0.7727(2) 0.0343(8) Uani 1 1 d . . . H32 H 0.2960 0.2959 0.7054 0.041 Uiso 1 1 calc R . . C33 C 0.3661(3) 0.2337(2) 0.8403(3) 0.0389(9) Uani 1 1 d . . . N33 N 0.3374(4) 0.1451(2) 0.8093(2) 0.0677(10) Uani 1 1 d . . . C34 C 0.4275(3) 0.2552(2) 0.9399(2) 0.0395(9) Uani 1 1 d . . . H34 H 0.4516 0.2080 0.9865 0.047 Uiso 1 1 calc R . . C35 C 0.4528(3) 0.3435(2) 0.9704(2) 0.0393(9) Uani 1 1 d . . . H35 H 0.4933 0.3553 1.0373 0.047 Uiso 1 1 calc R . . C36 C 0.4198(3) 0.4155(2) 0.9043(2) 0.0357(8) Uani 1 1 d . . . H36 H 0.4362 0.4756 0.9263 0.043 Uiso 1 1 calc R . . C38 C 0.2652(4) 0.1253(3) 0.7099(3) 0.0612(12) Uani 1 1 d . . . H38A H 0.2138 0.0714 0.7118 0.092 Uiso 1 1 calc R . . H38B H 0.3236 0.1152 0.6656 0.092 Uiso 1 1 calc R . . H38C H 0.2095 0.1761 0.6854 0.092 Uiso 1 1 calc R . . C39 C 0.3874(4) 0.0688(2) 0.8745(3) 0.0639(12) Uani 1 1 d . . . H39A H 0.3454 0.0669 0.9307 0.096 Uiso 1 1 calc R . . H39B H 0.4790 0.0761 0.8992 0.096 Uiso 1 1 calc R . . H39C H 0.3710 0.0127 0.8369 0.096 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0326(16) 0.0303(16) 0.0246(14) -0.0003(12) 0.0040(12) 0.0012(12) C12 0.0318(18) 0.031(2) 0.0248(17) 0.0002(15) 0.0061(14) 0.0012(15) N12 0.059(2) 0.0287(17) 0.0225(14) -0.0019(13) -0.0028(13) 0.0067(15) N13 0.0382(17) 0.0236(16) 0.0276(14) 0.0037(12) 0.0057(12) 0.0026(13) C14 0.0303(18) 0.0271(19) 0.0305(17) 0.0057(15) 0.0079(15) 0.0033(15) C15 0.0322(19) 0.0260(18) 0.0282(17) -0.0021(14) 0.0052(14) -0.0007(15) C16 0.0287(18) 0.0284(19) 0.0273(17) 0.0001(14) 0.0049(14) -0.0005(15) C17 0.0366(19) 0.0294(19) 0.0233(16) -0.0004(15) 0.0046(14) 0.0010(16) C18 0.053(2) 0.031(2) 0.0267(18) -0.0009(14) -0.0017(16) -0.0002(17) N21 0.0412(17) 0.0321(16) 0.0277(14) 0.0043(13) 0.0036(12) 0.0031(14) C22 0.0336(19) 0.0322(19) 0.0276(17) 0.0015(15) 0.0034(14) 0.0005(16) C23 0.0305(18) 0.031(2) 0.0282(17) 0.0041(14) 0.0074(14) -0.0029(15) C24 0.0305(18) 0.034(2) 0.0219(16) 0.0019(14) 0.0033(14) -0.0032(15) C25 0.0302(18) 0.0289(19) 0.0274(17) -0.0028(14) 0.0048(14) -0.0025(15) O25 0.0557(15) 0.0275(13) 0.0370(13) -0.0037(11) 0.0026(11) -0.0043(12) C26 0.0347(19) 0.031(2) 0.0267(17) 0.0061(14) 0.0020(14) 0.0006(16) C27 0.035(2) 0.0323(19) 0.0272(16) 0.0016(16) 0.0082(15) 0.0016(16) C28 0.053(2) 0.039(2) 0.035(2) -0.0136(16) 0.0000(17) -0.0038(18) C31 0.0317(19) 0.0301(19) 0.0313(18) 0.0013(15) 0.0089(15) 0.0023(15) C37 0.038(2) 0.0242(19) 0.0346(19) 0.0022(16) 0.0074(16) -0.0014(16) O31 0.0664(18) 0.0276(14) 0.0290(13) 0.0041(11) -0.0002(12) -0.0007(13) O32 0.0708(18) 0.0363(14) 0.0276(13) 0.0035(11) -0.0028(12) -0.0019(12) C32 0.039(2) 0.032(2) 0.0299(17) -0.0001(16) 0.0036(15) 0.0011(16) C33 0.048(2) 0.028(2) 0.041(2) 0.0023(16) 0.0120(18) 0.0090(17) N33 0.104(3) 0.031(2) 0.059(2) -0.0011(17) -0.002(2) 0.0059(19) C34 0.046(2) 0.037(2) 0.033(2) 0.0135(16) 0.0033(17) 0.0080(17) C35 0.044(2) 0.038(2) 0.0330(19) 0.0034(16) 0.0013(16) 0.0042(17) C36 0.040(2) 0.0290(19) 0.0347(18) 0.0035(15) 0.0007(16) -0.0009(16) C38 0.086(3) 0.035(2) 0.061(3) -0.014(2) 0.014(2) -0.011(2) C39 0.095(3) 0.029(2) 0.070(3) 0.006(2) 0.022(3) 0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.335(4) . ? N11 C12 1.357(4) . ? C12 N12 1.339(4) . ? C12 N13 1.346(4) . ? N12 H12A 0.99(3) . ? N12 H12B 0.95(3) . ? N13 C14 1.338(4) . ? C14 C15 1.389(4) . ? C14 C17 1.434(4) . ? C15 C16 1.376(4) . ? C15 H15 0.9300 . ? C16 C18 1.496(4) . ? C17 C27 1.196(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N21 C26 1.321(4) . ? N21 C22 1.333(4) . ? C22 C23 1.393(4) . ? C22 H22 0.9300 . ? C23 C24 1.390(4) . ? C23 C27 1.427(4) . ? C24 C25 1.379(4) . ? C24 H24 0.9300 . ? C25 O25 1.361(4) . ? C25 C26 1.395(4) . ? O25 C28 1.434(4) . ? C26 H26 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C31 C36 1.382(4) . ? C31 C32 1.388(4) . ? C31 C37 1.479(4) . ? C37 O32 1.223(3) . ? C37 O31 1.316(4) . ? O31 H31 0.96(4) . ? C32 C33 1.403(4) . ? C32 H32 0.9300 . ? C33 N33 1.374(4) . ? C33 C34 1.398(5) . ? N33 C38 1.424(5) . ? N33 C39 1.449(4) . ? C34 C35 1.362(4) . ? C34 H34 0.9300 . ? C35 C36 1.376(4) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 117.6(3) . . ? N12 C12 N13 117.5(3) . . ? N12 C12 N11 117.6(3) . . ? N13 C12 N11 125.0(3) . . ? C12 N12 H12A 114.6(18) . . ? C12 N12 H12B 117(2) . . ? H12A N12 H12B 126(3) . . ? C14 N13 C12 116.2(2) . . ? N13 C14 C15 122.2(3) . . ? N13 C14 C17 116.3(3) . . ? C15 C14 C17 121.5(3) . . ? C16 C15 C14 117.9(3) . . ? C16 C15 H15 121.0 . . ? C14 C15 H15 121.0 . . ? N11 C16 C15 121.0(3) . . ? N11 C16 C18 116.7(3) . . ? C15 C16 C18 122.3(3) . . ? C27 C17 C14 179.0(3) . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C26 N21 C22 117.8(3) . . ? N21 C22 C23 123.0(3) . . ? N21 C22 H22 118.5 . . ? C23 C22 H22 118.5 . . ? C24 C23 C22 118.5(3) . . ? C24 C23 C27 121.6(3) . . ? C22 C23 C27 119.8(3) . . ? C25 C24 C23 118.5(3) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? O25 C25 C24 125.6(3) . . ? O25 C25 C26 115.8(3) . . ? C24 C25 C26 118.5(3) . . ? C25 O25 C28 117.5(2) . . ? N21 C26 C25 123.6(3) . . ? N21 C26 H26 118.2 . . ? C25 C26 H26 118.2 . . ? C17 C27 C23 178.6(3) . . ? O25 C28 H28A 109.5 . . ? O25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C36 C31 C32 120.3(3) . . ? C36 C31 C37 121.3(3) . . ? C32 C31 C37 118.4(3) . . ? O32 C37 O31 123.3(3) . . ? O32 C37 C31 123.2(3) . . ? O31 C37 C31 113.5(3) . . ? C37 O31 H31 115.1(19) . . ? C31 C32 C33 121.1(3) . . ? C31 C32 H32 119.4 . . ? C33 C32 H32 119.4 . . ? N33 C33 C34 122.1(3) . . ? N33 C33 C32 121.1(3) . . ? C34 C33 C32 116.8(3) . . ? C33 N33 C38 121.1(3) . . ? C33 N33 C39 120.7(3) . . ? C38 N33 C39 118.0(3) . . ? C35 C34 C33 121.5(3) . . ? C35 C34 H34 119.2 . . ? C33 C34 H34 119.2 . . ? C34 C35 C36 121.4(3) . . ? C34 C35 H35 119.3 . . ? C36 C35 H35 119.3 . . ? C35 C36 C31 118.8(3) . . ? C35 C36 H36 120.6 . . ? C31 C36 H36 120.6 . . ? N33 C38 H38A 109.5 . . ? N33 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? N33 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N33 C39 H39A 109.5 . . ? N33 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? N33 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 177.7(3) . . . . ? C16 N11 C12 N13 -2.0(4) . . . . ? N12 C12 N13 C14 -177.9(3) . . . . ? N11 C12 N13 C14 1.8(4) . . . . ? C12 N13 C14 C15 0.1(4) . . . . ? C12 N13 C14 C17 -178.6(3) . . . . ? N13 C14 C15 C16 -1.6(4) . . . . ? C17 C14 C15 C16 177.0(3) . . . . ? C12 N11 C16 C15 0.2(4) . . . . ? C12 N11 C16 C18 178.8(3) . . . . ? C14 C15 C16 N11 1.4(4) . . . . ? C14 C15 C16 C18 -177.1(3) . . . . ? C26 N21 C22 C23 0.5(4) . . . . ? N21 C22 C23 C24 -0.7(5) . . . . ? N21 C22 C23 C27 179.9(3) . . . . ? C22 C23 C24 C25 0.0(4) . . . . ? C27 C23 C24 C25 179.4(3) . . . . ? C23 C24 C25 O25 179.2(3) . . . . ? C23 C24 C25 C26 0.7(4) . . . . ? C24 C25 O25 C28 1.8(4) . . . . ? C26 C25 O25 C28 -179.7(3) . . . . ? C22 N21 C26 C25 0.3(5) . . . . ? O25 C25 C26 N21 -179.5(3) . . . . ? C24 C25 C26 N21 -0.9(5) . . . . ? C36 C31 C37 O32 175.4(3) . . . . ? C32 C31 C37 O32 -3.3(5) . . . . ? C36 C31 C37 O31 -4.1(4) . . . . ? C32 C31 C37 O31 177.2(3) . . . . ? C36 C31 C32 C33 -0.2(5) . . . . ? C37 C31 C32 C33 178.5(3) . . . . ? C31 C32 C33 N33 178.8(3) . . . . ? C31 C32 C33 C34 -1.4(5) . . . . ? C34 C33 N33 C38 174.6(4) . . . . ? C32 C33 N33 C38 -5.6(6) . . . . ? C34 C33 N33 C39 -9.7(6) . . . . ? C32 C33 N33 C39 170.2(3) . . . . ? N33 C33 C34 C35 -178.5(3) . . . . ? C32 C33 C34 C35 1.7(5) . . . . ? C33 C34 C35 C36 -0.4(5) . . . . ? C34 C35 C36 C31 -1.2(5) . . . . ? C32 C31 C36 C35 1.5(5) . . . . ? C37 C31 C36 C35 -177.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O31 H31 N11 0.96(4) 1.67(4) 2.625(3) 170(3) . N12 H12A O32 0.99(3) 1.92(3) 2.908(4) 177(3) . N12 H12B N21 0.95(3) 2.09(3) 3.023(4) 171(3) 2_545 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.22 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.268 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.085 #END