# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Ibon Alkorta' 'Carmen Alvarez-Rua' 'R. M. Claramunt' 'Swapan Dey' 'Jose Elguero' 'Santiago Garcia-granda' 'Shyamaprosad Goswami' 'Nadine Jagerovic' 'M Dolores Santa Maria' 'Reshmi Mukherjee' 'Isabel Rozas' _publ_contact_author_name 'Dr Ibon Alkorta' _publ_contact_author_address ; I.Q.M CSIC Juan de la Cierva, 3 Madrid 28006 SPAIN ; _publ_contact_author_email IBON@IQM.CSIC.ES _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Multiple hydrogen bonds and tautomerism in naphthyridine derivatives ; # 4. text _publ_section_exptl_prep ; data collection was performed on a nonius kappaccd single crystal diffractometer. crystal-detector distance was fixed at 29 mm, and a total of 1315 images were collected using the oscillation method, with 1.2\% oscillation and 30 s exposure time per image. final mosaicity was 0.414(2)\%. all data completeness was 98.4%. intensity-error ratio for all reflections was 122.3 : 8.5. ; _publ_section_exptl_refinement ; crystal structure was solved by direct methods. all non-hydrogen atoms were anisotropically refined. hydrogen atoms were located in difference fourier maps. geometrical calculations made with parst97 (nardelli, 1995). all calculations were made at the university of oviedo on the x-ray group computers. ; _publ_section_references ; blessing, r. h. (1995). acta cryst. a51, 33-38. nardelli, m. (1995). j. appl. cryst. 28, 659. nonius bv, (1997-2000). collect. otwinowski, z. & minor, w. (1997). methods enzymol. 276, 307-326. sheldrick, g. m. (1990). acta cryst. a46, 467-473. sheldrick, g. m. (1997). shelxl-97. university of gottingen. a computer program for refinement of crystal structures. spek, a. l. (2001). platon. a multipurpose crystallographic tool, utrecht university, utrecht, the netherlands. ; #================================================================== #============ data_4a _database_code_depnum_ccdc_archive 'CCDC 236718' #================================================================== #============ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety '2(C12 H12 N4 O2), H2 O' _chemical_formula_sum 'C24 H26 N8 O5' _chemical_formula_weight 506.53 _chemical_compound_source synthesis loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 27.8630(5) _cell_length_b 11.4857(2) _cell_length_c 7.5182(1) _cell_angle_alpha 90.00 _cell_angle_beta 93.915(1) _cell_angle_gamma 90.00 _cell_volume 2400.41(7) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 18703 _cell_measurement_theta_min 1.767 _cell_measurement_theta_max 70.076 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.846 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sortav (Blessing, 1995) ' _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_T_max 0.955 _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26311 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.1038 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 69.85 _reflns_number_total 4481 _reflns_number_gt 2970 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4481 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1647 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1A N 0.19409(7) 0.65308(18) 0.3686(3) 0.0422(5) Uani 1 d . . . H11A H 0.1996(10) 0.582(2) 0.339(4) 0.046(8) Uiso 1 d . . . N2A N 0.27575(7) 0.65455(16) 0.3651(3) 0.0370(5) Uani 1 d . . . N3A N 0.35754(6) 0.64236(16) 0.3439(2) 0.0346(4) Uani 1 d . . . N4A N 0.43769(7) 0.61641(18) 0.3143(3) 0.0374(5) Uani 1 d . . . H44A H 0.4258(11) 0.541(3) 0.267(4) 0.071(9) Uiso 1 d . . . O1A O 0.13742(7) 0.79431(18) 0.3840(4) 0.0900(9) Uani 1 d . . . O2A O 0.50394(7) 0.73234(17) 0.3610(3) 0.0630(6) Uani 1 d . . . C1A C 0.11042(10) 0.6003(2) 0.3772(5) 0.0585(8) Uani 1 d . . . H1A H 0.1227 0.5278 0.3288 0.088 Uiso 1 calc R . . H1B H 0.0818 0.6254 0.3041 0.088 Uiso 1 calc R . . H1C H 0.1019 0.5873 0.5000 0.088 Uiso 1 calc R . . C2A C 0.14792(9) 0.6916(2) 0.3751(4) 0.0486(6) Uani 1 d . . . C3A C 0.23676(8) 0.7178(2) 0.3847(3) 0.0377(5) Uani 1 d . . . C4A C 0.23736(10) 0.8391(2) 0.4230(3) 0.0421(6) Uani 1 d . . . H4A H 0.2085(10) 0.875(2) 0.445(4) 0.061(9) Uiso 1 d . . . C5A C 0.28090(9) 0.8931(2) 0.4365(3) 0.0428(6) Uani 1 d . . . H5A H 0.2828(9) 0.977(2) 0.475(4) 0.052(8) Uiso 1 d . . . C6A C 0.32310(9) 0.8315(2) 0.4082(3) 0.0365(5) Uani 1 d . . . C7A C 0.36941(9) 0.8799(2) 0.4153(3) 0.0410(6) Uani 1 d . . . H7A H 0.3735(10) 0.963(2) 0.443(4) 0.056(8) Uiso 1 d . . . C8A C 0.40823(9) 0.8125(2) 0.3869(3) 0.0414(6) Uani 1 d . . . H8A H 0.4408(10) 0.843(2) 0.385(3) 0.047(7) Uiso 1 d . . . C9A C 0.40015(8) 0.6929(2) 0.3507(3) 0.0348(5) Uani 1 d . . . C10A C 0.31889(8) 0.71083(19) 0.3726(3) 0.0339(5) Uani 1 d . . . C11A C 0.48562(9) 0.6396(2) 0.3141(3) 0.0442(6) Uani 1 d . . . C12A C 0.51501(9) 0.5410(3) 0.2516(4) 0.0544(7) Uani 1 d . . . H12A H 0.4939 0.4751 0.2183 0.082 Uiso 1 calc R . . H12B H 0.5386 0.5172 0.3475 0.082 Uiso 1 calc R . . H12C H 0.5319 0.5658 0.1478 0.082 Uiso 1 calc R . . N1B N 0.07812(7) 0.50225(19) -0.1071(3) 0.0422(5) Uani 1 d . . . H11B H 0.0944(10) 0.571(3) -0.102(4) 0.061(9) Uiso 1 d . . . N2B N 0.14602(6) 0.44386(16) 0.0525(3) 0.0372(5) Uani 1 d . . . N3B N 0.21597(7) 0.40135(15) 0.2177(3) 0.0349(4) Uani 1 d . . . N4B N 0.28732(7) 0.37475(18) 0.3776(3) 0.0374(5) Uani 1 d . . . H44B H 0.2866(11) 0.460(3) 0.379(4) 0.076(10) Uiso 1 d . . . O1B O 0.01005(7) 0.41272(19) -0.2199(4) 0.0778(7) Uani 1 d . . . O2B O 0.32799(6) 0.21386(15) 0.4863(2) 0.0491(5) Uani 1 d . . . C1B C 0.01572(10) 0.6172(3) -0.2604(4) 0.0571(7) Uani 1 d . . . H1D H 0.0420 0.6739 -0.2467 0.086 Uiso 1 calc R . . H1E H -0.0108 0.6425 -0.1905 0.086 Uiso 1 calc R . . H1F H 0.0044 0.6117 -0.3864 0.086 Uiso 1 calc R . . C2B C 0.03335(9) 0.5008(2) -0.1956(4) 0.0494(6) Uani 1 d . . . C3B C 0.10445(8) 0.4106(2) -0.0278(3) 0.0371(5) Uani 1 d . . . C4B C 0.08792(8) 0.2938(2) -0.0343(3) 0.0399(5) Uani 1 d . . . H4B H 0.0549(11) 0.273(3) -0.089(4) 0.067(9) Uiso 1 d . . . C5B C 0.11817(9) 0.2107(2) 0.0393(3) 0.0413(6) Uani 1 d . . . H5B H 0.1065(9) 0.127(2) 0.040(4) 0.054(8) Uiso 1 d . . . C6B C 0.16360(8) 0.24095(19) 0.1198(3) 0.0350(5) Uani 1 d . . . C7B C 0.19812(9) 0.1619(2) 0.1938(3) 0.0398(5) Uani 1 d . . . H7B H 0.1907(9) 0.076(2) 0.190(4) 0.052(8) Uiso 1 d . . . C8B C 0.23990(9) 0.2019(2) 0.2745(3) 0.0399(5) Uani 1 d . . . H8B H 0.2635(9) 0.151(2) 0.326(4) 0.051(8) Uiso 1 d . . . C9B C 0.24717(8) 0.32407(19) 0.2865(3) 0.0351(5) Uani 1 d . . . C10B C 0.17496(8) 0.36066(19) 0.1290(3) 0.0339(5) Uani 1 d . . . C11B C 0.32374(8) 0.3202(2) 0.4765(3) 0.0395(5) Uani 1 d . . . C12B C 0.35897(10) 0.3994(2) 0.5736(4) 0.0509(7) Uani 1 d . . . H12D H 0.3457 0.4784 0.5748 0.076 Uiso 1 calc R . . H12E H 0.3891 0.3999 0.5134 0.076 Uiso 1 calc R . . H12F H 0.3653 0.3718 0.6963 0.076 Uiso 1 calc R . . O10 O 0.41465(7) 0.38014(16) 0.1663(3) 0.0594(6) Uani 1 d G . . H10A H 0.4369 0.3216 0.1690 0.072(10) Uiso 1 d G . . H10B H 0.3881 0.3487 0.1194 0.076(11) Uiso 1 d G . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1A 0.0358(11) 0.0338(11) 0.0566(13) -0.0082(9) 0.0004(9) 0.0037(9) N2A 0.0341(10) 0.0337(10) 0.0426(11) -0.0035(8) -0.0016(8) -0.0002(8) N3A 0.0312(10) 0.0349(10) 0.0371(10) -0.0030(8) -0.0018(8) -0.0027(8) N4A 0.0310(10) 0.0414(11) 0.0392(11) -0.0025(9) -0.0029(8) -0.0040(9) O1A 0.0411(12) 0.0479(12) 0.178(3) -0.0321(15) -0.0134(14) 0.0135(10) O2A 0.0423(11) 0.0553(12) 0.0906(16) -0.0128(11) -0.0003(10) -0.0143(9) C1A 0.0401(15) 0.0512(16) 0.086(2) -0.0112(15) 0.0145(14) 0.0008(12) C2A 0.0411(14) 0.0440(14) 0.0600(16) -0.0098(12) -0.0027(12) 0.0058(12) C3A 0.0406(13) 0.0340(12) 0.0379(12) -0.0035(9) -0.0029(10) 0.0021(10) C4A 0.0475(14) 0.0369(13) 0.0414(14) -0.0033(10) 0.0003(11) 0.0064(11) C5A 0.0516(15) 0.0308(12) 0.0459(14) -0.0058(10) 0.0022(11) -0.0005(10) C6A 0.0452(13) 0.0332(12) 0.0308(11) 0.0000(9) -0.0009(9) -0.0024(10) C7A 0.0503(15) 0.0320(12) 0.0405(13) -0.0010(10) 0.0012(10) -0.0079(11) C8A 0.0471(14) 0.0374(12) 0.0394(13) -0.0006(10) 0.0015(11) -0.0093(11) C9A 0.0351(12) 0.0379(12) 0.0307(11) 0.0006(9) -0.0018(9) -0.0039(10) C10A 0.0366(12) 0.0329(12) 0.0316(11) -0.0003(9) -0.0024(9) -0.0022(9) C11A 0.0366(13) 0.0485(14) 0.0466(14) 0.0003(11) -0.0039(11) -0.0094(11) C12A 0.0366(14) 0.0587(17) 0.0677(18) -0.0060(14) 0.0025(13) -0.0021(12) N1B 0.0301(11) 0.0401(11) 0.0553(13) 0.0024(9) -0.0045(9) -0.0016(9) N2B 0.0283(9) 0.0343(10) 0.0485(11) -0.0015(8) -0.0006(8) -0.0002(8) N3B 0.0308(10) 0.0311(10) 0.0425(11) 0.0011(8) 0.0003(8) -0.0011(8) N4B 0.0341(10) 0.0343(10) 0.0432(11) 0.0017(8) -0.0023(8) -0.0003(8) O1B 0.0498(13) 0.0578(13) 0.120(2) 0.0024(13) -0.0348(13) -0.0088(10) O2B 0.0468(10) 0.0390(10) 0.0594(11) 0.0053(8) -0.0109(8) 0.0040(8) C1B 0.0419(15) 0.0630(18) 0.0652(19) 0.0057(15) -0.0046(13) 0.0092(13) C2B 0.0321(13) 0.0524(15) 0.0629(17) -0.0020(13) -0.0026(12) 0.0007(11) C3B 0.0304(11) 0.0374(12) 0.0435(13) 0.0010(10) 0.0025(9) -0.0019(9) C4B 0.0313(12) 0.0426(13) 0.0454(13) -0.0023(10) -0.0012(10) -0.0082(10) C5B 0.0447(14) 0.0368(13) 0.0422(13) -0.0024(10) 0.0016(10) -0.0097(11) C6B 0.0386(12) 0.0307(11) 0.0359(11) -0.0018(9) 0.0031(9) -0.0052(9) C7B 0.0489(14) 0.0306(12) 0.0400(13) 0.0011(10) 0.0042(10) -0.0019(10) C8B 0.0465(14) 0.0310(12) 0.0416(13) 0.0019(10) -0.0006(11) 0.0022(11) C9B 0.0354(12) 0.0335(11) 0.0362(12) 0.0006(9) 0.0022(9) -0.0014(10) C10B 0.0299(11) 0.0314(11) 0.0409(12) -0.0013(9) 0.0057(9) -0.0018(9) C11B 0.0383(13) 0.0421(13) 0.0378(13) 0.0040(10) -0.0003(10) 0.0012(10) C12B 0.0504(16) 0.0480(15) 0.0520(16) 0.0073(12) -0.0138(12) -0.0071(12) O10 0.0382(10) 0.0421(10) 0.0957(16) -0.0108(10) -0.0104(10) 0.0028(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 N1A C2A 1.364(3) . ? N1A C3A 1.400(3) . ? N1A H11A 0.86(3) . ? N2A C3A 1.323(3) . ? N2A C10A 1.363(3) . ? N3A C9A 1.319(3) . ? N3A C10A 1.362(3) . ? N4A C11A 1.362(3) . ? N4A C9A 1.407(3) . ? N4A H44A 0.99(3) . ? O1A C2A 1.219(3) . ? O2A C11A 1.223(3) . ? C1A C2A 1.481(4) . ? C1A H1A 0.9800 . ? C1A H1B 0.9800 . ? C1A H1C 0.9800 . ? C3A C4A 1.423(3) . ? C4A C5A 1.360(4) . ? C4A H4A 0.93(3) . ? C5A C6A 1.401(3) . ? C5A H5A 1.01(3) . ? C6A C7A 1.403(3) . ? C6A C10A 1.415(3) . ? C7A C8A 1.359(4) . ? C7A H7A 0.98(3) . ? C8A C9A 1.416(3) . ? C8A H8A 0.97(3) . ? C11A C12A 1.493(4) . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C12A H12C 0.9800 . ? N1B C2B 1.373(3) . ? N1B C3B 1.394(3) . ? N1B H11B 0.91(3) . ? N2B C3B 1.325(3) . ? N2B C10B 1.353(3) . ? N3B C9B 1.323(3) . ? N3B C10B 1.365(3) . ? N4B C11B 1.368(3) . ? N4B C9B 1.398(3) . ? N4B H44B 0.98(3) . ? O1B C2B 1.209(3) . ? O2B C11B 1.228(3) . ? C1B C2B 1.495(4) . ? C1B H1D 0.9800 . ? C1B H1E 0.9800 . ? C1B H1F 0.9800 . ? C3B C4B 1.418(3) . ? C4B C5B 1.365(3) . ? C4B H4B 1.01(3) . ? C5B C6B 1.409(3) . ? C5B H5B 1.02(3) . ? C6B C7B 1.409(3) . ? C6B C10B 1.412(3) . ? C7B C8B 1.355(3) . ? C7B H7B 1.01(3) . ? C8B C9B 1.420(3) . ? C8B H8B 0.94(3) . ? C11B C12B 1.492(3) . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? O10 H10A 0.9142 . ? O10 H10B 0.8761 . ? 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 C2A N1A C3A 128.5(2) . . ? C2A N1A H11A 120.1(18) . . ? C3A N1A H11A 111.0(18) . . ? C3A N2A C10A 117.6(2) . . ? C9A N3A C10A 117.32(19) . . ? C11A N4A C9A 128.3(2) . . ? C11A N4A H44A 118.5(18) . . ? C9A N4A H44A 112.5(18) . . ? C2A C1A H1A 109.5 . . ? C2A C1A H1B 109.5 . . ? H1A C1A H1B 109.5 . . ? C2A C1A H1C 109.5 . . ? H1A C1A H1C 109.5 . . ? H1B C1A H1C 109.5 . . ? O1A C2A N1A 123.1(3) . . ? O1A C2A C1A 120.8(2) . . ? N1A C2A C1A 116.0(2) . . ? N2A C3A N1A 113.5(2) . . ? N2A C3A C4A 124.2(2) . . ? N1A C3A C4A 122.4(2) . . ? C5A C4A C3A 117.4(2) . . ? C5A C4A H4A 124.2(18) . . ? C3A C4A H4A 118.3(18) . . ? C4A C5A C6A 120.8(2) . . ? C4A C5A H5A 119.1(15) . . ? C6A C5A H5A 119.9(15) . . ? C5A C6A C7A 125.0(2) . . ? C5A C6A C10A 117.6(2) . . ? C7A C6A C10A 117.4(2) . . ? C8A C7A C6A 120.5(2) . . ? C8A C7A H7A 120.4(17) . . ? C6A C7A H7A 119.1(17) . . ? C7A C8A C9A 117.7(2) . . ? C7A C8A H8A 123.6(15) . . ? C9A C8A H8A 118.6(15) . . ? N3A C9A N4A 113.4(2) . . ? N3A C9A C8A 124.4(2) . . ? N4A C9A C8A 122.2(2) . . ? N3A C10A N2A 115.10(19) . . ? N3A C10A C6A 122.6(2) . . ? N2A C10A C6A 122.3(2) . . ? O2A C11A N4A 124.1(3) . . ? O2A C11A C12A 121.7(2) . . ? N4A C11A C12A 114.3(2) . . ? C11A C12A H12A 109.5 . . ? C11A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C11A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C2B N1B C3B 129.2(2) . . ? C2B N1B H11B 117.8(19) . . ? C3B N1B H11B 113.0(19) . . ? C3B N2B C10B 117.82(19) . . ? C9B N3B C10B 117.84(19) . . ? C11B N4B C9B 127.9(2) . . ? C11B N4B H44B 117.9(18) . . ? C9B N4B H44B 113.8(18) . . ? C2B C1B H1D 109.5 . . ? C2B C1B H1E 109.5 . . ? H1D C1B H1E 109.5 . . ? C2B C1B H1F 109.5 . . ? H1D C1B H1F 109.5 . . ? H1E C1B H1F 109.5 . . ? O1B C2B N1B 123.0(3) . . ? O1B C2B C1B 122.6(2) . . ? N1B C2B C1B 114.5(2) . . ? N2B C3B N1B 113.3(2) . . ? N2B C3B C4B 124.1(2) . . ? N1B C3B C4B 122.7(2) . . ? C5B C4B C3B 117.2(2) . . ? C5B C4B H4B 121.1(17) . . ? C3B C4B H4B 121.7(17) . . ? C4B C5B C6B 120.9(2) . . ? C4B C5B H5B 118.3(15) . . ? C6B C5B H5B 120.8(15) . . ? C7B C6B C5B 125.4(2) . . ? C7B C6B C10B 117.6(2) . . ? C5B C6B C10B 117.0(2) . . ? C8B C7B C6B 120.0(2) . . ? C8B C7B H7B 120.9(15) . . ? C6B C7B H7B 119.1(15) . . ? C7B C8B C9B 118.5(2) . . ? C7B C8B H8B 121.7(16) . . ? C9B C8B H8B 119.8(16) . . ? N3B C9B N4B 113.24(19) . . ? N3B C9B C8B 123.5(2) . . ? N4B C9B C8B 123.3(2) . . ? N2B C10B N3B 114.86(19) . . ? N2B C10B C6B 122.8(2) . . ? N3B C10B C6B 122.3(2) . . ? O2B C11B N4B 123.6(2) . . ? O2B C11B C12B 121.3(2) . . ? N4B C11B C12B 115.2(2) . . ? C11B C12B H12D 109.5 . . ? C11B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C11B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? H10A O10 H10B 105.0 . . ? 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 C3A N1A C2A O1A 5.5(5) . . . . ? C3A N1A C2A C1A -172.4(3) . . . . ? C10A N2A C3A N1A 177.8(2) . . . . ? C10A N2A C3A C4A -3.7(3) . . . . ? C2A N1A C3A N2A -177.4(2) . . . . ? C2A N1A C3A C4A 4.1(4) . . . . ? N2A C3A C4A C5A 1.4(4) . . . . ? N1A C3A C4A C5A 179.7(2) . . . . ? C3A C4A C5A C6A 1.9(4) . . . . ? C4A C5A C6A C7A 178.6(2) . . . . ? C4A C5A C6A C10A -2.5(3) . . . . ? C5A C6A C7A C8A 179.6(2) . . . . ? C10A C6A C7A C8A 0.7(3) . . . . ? C6A C7A C8A C9A -0.1(3) . . . . ? C10A N3A C9A N4A -178.21(18) . . . . ? C10A N3A C9A C8A 0.5(3) . . . . ? C11A N4A C9A N3A -178.4(2) . . . . ? C11A N4A C9A C8A 2.8(4) . . . . ? C7A C8A C9A N3A -0.5(3) . . . . ? C7A C8A C9A N4A 178.1(2) . . . . ? C9A N3A C10A N2A -179.70(19) . . . . ? C9A N3A C10A C6A 0.1(3) . . . . ? C3A N2A C10A N3A -177.3(2) . . . . ? C3A N2A C10A C6A 2.9(3) . . . . ? C5A C6A C10A N3A -179.7(2) . . . . ? C7A C6A C10A N3A -0.7(3) . . . . ? C5A C6A C10A N2A 0.1(3) . . . . ? C7A C6A C10A N2A 179.1(2) . . . . ? C9A N4A C11A O2A 6.1(4) . . . . ? C9A N4A C11A C12A -174.1(2) . . . . ? C3B N1B C2B O1B -1.5(5) . . . . ? C3B N1B C2B C1B 178.7(2) . . . . ? C10B N2B C3B N1B -178.0(2) . . . . ? C10B N2B C3B C4B 1.8(4) . . . . ? C2B N1B C3B N2B -177.6(3) . . . . ? C2B N1B C3B C4B 2.6(4) . . . . ? N2B C3B C4B C5B -3.6(4) . . . . ? N1B C3B C4B C5B 176.2(2) . . . . ? C3B C4B C5B C6B 0.8(4) . . . . ? C4B C5B C6B C7B -177.7(2) . . . . ? C4B C5B C6B C10B 3.3(4) . . . . ? C5B C6B C7B C8B -177.3(2) . . . . ? C10B C6B C7B C8B 1.7(4) . . . . ? C6B C7B C8B C9B 1.7(4) . . . . ? C10B N3B C9B N4B -178.7(2) . . . . ? C10B N3B C9B C8B -0.7(3) . . . . ? C11B N4B C9B N3B 173.7(2) . . . . ? C11B N4B C9B C8B -4.3(4) . . . . ? C7B C8B C9B N3B -2.4(4) . . . . ? C7B C8B C9B N4B 175.4(2) . . . . ? C3B N2B C10B N3B -176.6(2) . . . . ? C3B N2B C10B C6B 2.8(4) . . . . ? C9B N3B C10B N2B -176.1(2) . . . . ? C9B N3B C10B C6B 4.5(3) . . . . ? C7B C6B C10B N2B 175.6(2) . . . . ? C5B C6B C10B N2B -5.3(4) . . . . ? C7B C6B C10B N3B -5.0(4) . . . . ? C5B C6B C10B N3B 174.1(2) . . . . ? C9B N4B C11B O2B 6.5(4) . . . . ? C9B N4B C11B C12B -173.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1A H11A N3B 1_555 0.86(3) 2.32(3) 3.180(3) 171(2) yes N4A H44A O10 1_555 0.98(3) 2.01(3) 2.986(3) 169(3) yes N4B H44B N2A 1_555 0.98(3) 2.23(3) 3.231(3) 173(3) yes N1B H11B O1A 4_575 0.91(3) 1.97(3) 2.865(3) 170(2) yes O10 H10A O2A 2_645 0.914 1.967 2.852(3) 162.4(1) yes O10 H10B O2B 4_565 0.876 2.023 2.895(3) 173.6(1) yes C4A H4A O1A . 0.93(3) 2.21(3) 2.827(3) 124(2) yes C4B H4B O1B . 1.01(3) 2.22(3) 2.847(3) 119(3) yes C8A H8A O2A . 0.97(3) 2.19(3) 2.840(3) 123(2) yes C8B H8B O2B . 0.94(3) 2.22(3) 2.836(3) 123(2) yes _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 69.85 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.272 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.07 #==END #================================================================== #============ data_3a _database_code_depnum_ccdc_archive 'CCDC 236719' #================================================================== #============ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N4 O' _chemical_formula_sum 'C10 H10 N4 O' _chemical_formula_weight 202.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'F d d 2' _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,z 1/4-x,1/4+y,1/4+z 3/4+x,3/4-y,1/4+z x,1/2+y,1/2+z -x,1/2-y,1/2+z 1/4-x,3/4+y,3/4+z 3/4+x,1/4-y,3/4+z 1/2+x,y,1/2+z 1/2-x,-y,1/2+z 3/4-x,1/4+y,3/4+z 1/4+x,3/4-y,3/4+z 1/2+x,1/2+y,z 1/2-x,1/2-y,z 3/4-x,3/4+y,1/4+z 1/4+x,1/4-y,1/4+z _cell_length_a 19.001(3) _cell_length_b 25.829(8) _cell_length_c 7.844(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3849.7(17) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1432 _cell_measurement_theta_min 5.78 _cell_measurement_theta_max 68.14 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.790 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2690 _diffrn_reflns_av_R_equivalents 0.0712 _diffrn_reflns_av_sigmaI/netI 0.0974 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.78 _diffrn_reflns_theta_max 68.14 _reflns_number_total 1431 _reflns_number_gt 938 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0451P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(6) _refine_ls_number_reflns 1431 _refine_ls_number_parameters 142 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _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 N2 N 0.02441(19) 0.19096(12) 0.2541(4) 0.0514(10) Uani 1 1 d . . . C6 C -0.0010(4) 0.10878(11) 0.1213(6) 0.0558(8) Uani 1 1 d . . . C3 C 0.0498(3) 0.16476(18) 0.3879(5) 0.0525(13) Uani 1 1 d . . . N3 N -0.02820(18) 0.19240(13) -0.0096(4) 0.0513(11) Uani 1 1 d . . . N4 N -0.0795(2) 0.19521(18) -0.2761(5) 0.0689(12) Uani 1 1 d . . . C10 C -0.0018(4) 0.16337(11) 0.1208(6) 0.0501(8) Uani 1 1 d . . . C8 C -0.0562(3) 0.11198(19) -0.1527(6) 0.0694(15) Uani 1 1 d . . . H8 H -0.0754 0.0955 -0.2473 0.083 Uiso 1 1 calc R . . C4 C 0.0524(3) 0.11109(18) 0.3967(5) 0.0599(13) Uani 1 1 d . . . H4 H 0.0710 0.0945 0.4918 0.072 Uiso 1 1 calc R . . O1 O 0.11980(17) 0.13983(12) 0.7078(4) 0.0771(9) Uani 1 1 d . . . C5 C 0.0269(3) 0.08327(17) 0.2619(6) 0.0659(14) Uani 1 1 d . . . H5 H 0.0283 0.0473 0.2642 0.079 Uiso 1 1 calc R . . N1 N 0.0736(2) 0.19774(15) 0.5187(4) 0.0577(10) Uani 1 1 d . . . H1 H 0.0673 0.2304 0.5029 0.069 Uiso 1 1 calc R . . C7 C -0.0309(3) 0.08458(17) -0.0239(6) 0.0698(16) Uani 1 1 d . . . H7 H -0.0328 0.0486 -0.0288 0.084 Uiso 1 1 calc R . . C2 C 0.1054(3) 0.18394(19) 0.6673(5) 0.0629(13) Uani 1 1 d . . . C9 C -0.0537(3) 0.16743(17) -0.1445(5) 0.0547(13) Uani 1 1 d . . . C1 C 0.1247(2) 0.22980(16) 0.7785(5) 0.0693(12) Uani 1 1 d . . . H1A H 0.1091 0.2612 0.7249 0.104 Uiso 1 1 calc R . . H1B H 0.1748 0.2309 0.7935 0.104 Uiso 1 1 calc R . . H1C H 0.1023 0.2263 0.8877 0.104 Uiso 1 1 calc R . . H4B H -0.058(3) 0.229(2) -0.290(6) 0.104 Uiso 1 1 d . . . H4A H -0.099(4) 0.179(2) -0.366(7) 0.104 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N2 0.060(3) 0.047(2) 0.0470(18) 0.000(2) -0.0022(15) -0.0007(19) C6 0.063(2) 0.0476(18) 0.0568(19) -0.002(3) 0.0023(16) 0.000(3) C3 0.050(3) 0.057(3) 0.050(2) -0.001(2) 0.000(2) 0.004(2) N3 0.058(3) 0.050(2) 0.0463(19) -0.004(2) 0.0051(16) -0.0046(19) N4 0.088(3) 0.070(3) 0.0484(19) 0.000(2) -0.009(2) -0.010(3) C10 0.060(2) 0.0425(17) 0.0481(17) -0.002(3) 0.0025(15) -0.004(3) C8 0.086(4) 0.057(4) 0.065(3) -0.012(3) -0.008(3) -0.001(3) C4 0.071(4) 0.047(3) 0.063(3) 0.007(2) -0.005(2) 0.009(3) O1 0.097(2) 0.065(2) 0.0695(17) 0.0115(14) -0.0140(17) 0.014(2) C5 0.075(4) 0.048(3) 0.074(3) -0.009(3) 0.002(2) 0.004(2) N1 0.070(3) 0.052(2) 0.0509(18) 0.0056(18) -0.0100(18) 0.004(2) C7 0.088(5) 0.045(3) 0.076(3) -0.014(3) -0.003(3) -0.007(3) C2 0.066(3) 0.064(3) 0.060(3) 0.006(2) 0.002(2) 0.010(2) C9 0.061(4) 0.054(3) 0.049(3) -0.004(2) 0.009(2) -0.002(3) C1 0.079(3) 0.071(3) 0.058(2) 0.004(2) -0.010(2) -0.005(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 N2 C3 1.339(5) . ? N2 C10 1.360(5) . ? C6 C5 1.390(7) . ? C6 C10 1.410(4) . ? C6 C7 1.419(7) . ? C3 C4 1.389(6) . ? C3 N1 1.408(6) . ? N3 C9 1.330(5) . ? N3 C10 1.364(6) . ? N4 C9 1.350(6) . ? N4 H4B 0.98(5) . ? N4 H4A 0.89(6) . ? C8 C7 1.324(7) . ? C8 C9 1.434(6) . ? C8 H8 0.9300 . ? C4 C5 1.367(6) . ? C4 H4 0.9300 . ? O1 C2 1.214(5) . ? C5 H5 0.9300 . ? N1 C2 1.360(5) . ? N1 H1 0.8600 . ? C7 H7 0.9300 . ? C2 C1 1.516(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 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 C3 N2 C10 118.0(3) . . ? C5 C6 C10 118.7(4) . . ? C5 C6 C7 125.5(3) . . ? C10 C6 C7 115.7(5) . . ? N2 C3 C4 123.8(4) . . ? N2 C3 N1 112.4(4) . . ? C4 C3 N1 123.8(4) . . ? C9 N3 C10 117.7(3) . . ? C9 N4 H4B 114(3) . . ? C9 N4 H4A 121(4) . . ? H4B N4 H4A 120(4) . . ? N2 C10 N3 115.0(3) . . ? N2 C10 C6 121.2(5) . . ? N3 C10 C6 123.8(5) . . ? C7 C8 C9 119.2(5) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C5 C4 C3 118.3(4) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C4 C5 C6 120.0(4) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C2 N1 C3 127.5(4) . . ? C2 N1 H1 116.3 . . ? C3 N1 H1 116.3 . . ? C8 C7 C6 121.5(4) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? O1 C2 N1 124.8(4) . . ? O1 C2 C1 121.9(4) . . ? N1 C2 C1 113.3(4) . . ? N3 C9 N4 118.9(4) . . ? N3 C9 C8 122.1(4) . . ? N4 C9 C8 119.0(4) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 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 C10 N2 C3 C4 1.6(7) . . . . ? C10 N2 C3 N1 -178.5(4) . . . . ? C3 N2 C10 N3 178.6(4) . . . . ? C3 N2 C10 C6 -1.4(8) . . . . ? C9 N3 C10 N2 179.1(4) . . . . ? C9 N3 C10 C6 -0.9(8) . . . . ? C5 C6 C10 N2 0.4(9) . . . . ? C7 C6 C10 N2 179.0(5) . . . . ? C5 C6 C10 N3 -179.6(5) . . . . ? C7 C6 C10 N3 -1.0(10) . . . . ? N2 C3 C4 C5 -0.7(8) . . . . ? N1 C3 C4 C5 179.3(4) . . . . ? C3 C4 C5 C6 -0.4(8) . . . . ? C10 C6 C5 C4 0.5(9) . . . . ? C7 C6 C5 C4 -178.0(5) . . . . ? N2 C3 N1 C2 -176.5(4) . . . . ? C4 C3 N1 C2 3.5(7) . . . . ? C9 C8 C7 C6 -0.4(9) . . . . ? C5 C6 C7 C8 -179.8(5) . . . . ? C10 C6 C7 C8 1.6(9) . . . . ? C3 N1 C2 O1 2.0(7) . . . . ? C3 N1 C2 C1 179.5(4) . . . . ? C10 N3 C9 N4 -179.4(5) . . . . ? C10 N3 C9 C8 2.3(7) . . . . ? C7 C8 C9 N3 -1.7(8) . . . . ? C7 C8 C9 N4 -180.0(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N1 H1 N3 0.8600 2.1300 2.974(5) 166.00 6_555 yes N4 H4A O1 0.90(6) 2.33(6) 3.180(5) 158(5) 8_453 yes N4 H4B N2 0.97(5) 2.19(5) 3.130(6) 163(4) 6_554 yes C4 H4 O1 0.9300 2.2600 2.854(5) 121.00 . yes C8 H8 O1 0.9300 2.5700 3.364(6) 144.00 8_453 yes _diffrn_measured_fraction_theta_max 0.834 _diffrn_reflns_theta_full 68.14 _diffrn_measured_fraction_theta_full 0.833 _refine_diff_density_max 0.189 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.068 #===END