#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/61/1506182.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1506182 loop_ _publ_author_name 'Nowak, Ireneusz' 'Cannon, John F.' 'Robins, Morris J.' _publ_section_title ; N-oxides of adenosine-type nucleosides undergo pyrimidine ring opening and closure to give 5-amino-4-(1,2,4-oxadiazol-3-yl)imidazole derivatives. ; _journal_issue 20 _journal_name_full 'Organic letters' _journal_page_first 4565 _journal_page_last 4568 _journal_paper_doi 10.1021/ol061715v _journal_volume 8 _journal_year 2006 _chemical_absolute_configuration ad _chemical_formula_sum 'C11 H15 N5 O5' _chemical_formula_weight 297.28 _chemical_name_systematic ; ? ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.1879(6) _cell_length_b 6.6386(6) _cell_length_c 30.879(3) _cell_measurement_reflns_used 3825 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 50.28 _cell_measurement_theta_min 7.26 _cell_volume 1268.5(2) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.964 _diffrn_measured_fraction_theta_max 0.964 _diffrn_measurement_device_type 'Bruker Nonius Apex II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator 'Montel 200 mirrors' _diffrn_radiation_source 'Bruker Nonius FR591 rotating anode' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 4454 _diffrn_reflns_theta_full 50.27 _diffrn_reflns_theta_max 50.27 _diffrn_reflns_theta_min 7.26 _exptl_absorpt_coefficient_mu 1.067 _exptl_absorpt_correction_T_max 0.7264 _exptl_absorpt_correction_T_min 0.6810 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS; Sheldrick, 2003' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_description BLOCK _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _refine_diff_density_max 0.131 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.034 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 1245 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.099 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0312 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.1436P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0806 _refine_ls_wR_factor_ref 0.0812 _reflns_number_gt 1211 _reflns_number_total 1245 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ol061715vsi20060713_102004.cif _cod_data_source_block XL904 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M P2(1)2(1)2(1) _cod_database_code 1506182 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 C4 C 0.5604(4) 0.5342(4) 0.90582(8) 0.0368(7) Uani 1 1 d . A 4 C5 C 0.7601(4) 0.4581(4) 0.89656(8) 0.0338(7) Uani 1 1 d . A 4 C2" C 0.9141(4) -0.0239(4) 0.85236(9) 0.0407(7) Uani 1 1 d . A 4 H2"A H 0.8553 -0.0582 0.8809 0.049 Uiso 1 1 calc R A 4 C2 C 0.5062(4) 0.2974(5) 0.86041(9) 0.0473(8) Uani 1 1 d . A 4 H2 H 0.4395 0.2060 0.8419 0.057 Uiso 1 1 calc R A 4 C3' C 0.5154(4) 0.7075(4) 0.93239(8) 0.0364(7) Uani 1 1 d . A 4 C1" C 0.8896(4) 0.1990(4) 0.84209(8) 0.0379(7) Uani 1 1 d . A 4 H1" H 1.0292 0.2655 0.8466 0.045 Uiso 1 1 calc R A 4 C5' C 0.3518(5) 0.9521(5) 0.96049(9) 0.0424(7) Uani 1 1 d . A 4 C6' C 0.2018(6) 1.1119(5) 0.97481(10) 0.0627(9) Uani 1 1 d . A 4 H1A H 0.0555 1.0681 0.9705 0.094 Uiso 1 1 calc R A 4 H6'B H 0.2273 1.2319 0.9582 0.094 Uiso 1 1 calc R A 4 H6'C H 0.2251 1.1396 1.0050 0.094 Uiso 1 1 calc R A 4 C3" C 0.7875(5) -0.1219(4) 0.81579(9) 0.0413(7) Uani 1 1 d . A 4 H3"A H 0.6328 -0.1171 0.8225 0.050 Uiso 1 1 calc R A 4 O5" O 0.8326(3) 0.2144(3) 0.79722(5) 0.0446(5) Uani 1 1 d . A 4 O2" O 1.1354(3) -0.0760(3) 0.84858(6) 0.0522(6) Uani 1 1 d . A 4 H2"B H 1.1707 -0.1469 0.8691 0.078 Uiso 1 1 calc R A 4 O3" O 0.8500(4) -0.3240(3) 0.80839(7) 0.0574(6) Uani 1 1 d . A 4 H3"B H 0.7470 -0.3874 0.7987 0.086 Uiso 1 1 calc R A 4 O1' O 0.5539(3) 0.9594(3) 0.97510(6) 0.0542(6) Uani 1 1 d . A 4 N1 N 0.7254(3) 0.3058(3) 0.86687(7) 0.0367(6) Uani 1 1 d . A 4 N5 N 0.9556(3) 0.5077(4) 0.91206(7) 0.0499(7) Uani 1 1 d . A 4 H5A H 0.9677 0.6018 0.9310 0.060 Uiso 1 1 calc R A 4 H5B H 1.0688 0.4454 0.9030 0.060 Uiso 1 1 calc R A 4 N2' N 0.6648(4) 0.7934(4) 0.95640(8) 0.0531(7) Uani 1 1 d . A 4 N4' N 0.3186(4) 0.8033(4) 0.93436(7) 0.0446(6) Uani 1 1 d . A 4 N3 N 0.4019(4) 0.4308(4) 0.88290(8) 0.0483(7) Uani 1 1 d . A 4 C4"A C 0.8346(6) 0.0169(4) 0.77818(10) 0.0402(7) Uani 0.669(7) 1 d P A 1 C5"A C 0.681(2) 0.0087(12) 0.7422(5) 0.061(6) Uani 0.669(7) 1 d P A 1 H5"A H 0.7237 0.1108 0.7214 0.073 Uiso 0.669(7) 1 calc PR A 1 H5"B H 0.6988 -0.1208 0.7281 0.073 Uiso 0.669(7) 1 calc PR A 1 O5"A O 0.4754(6) 0.0327(6) 0.74983(13) 0.0717(15) Uani 0.669(7) 1 d P A 1 H5"1 H 0.4400 -0.0373 0.7705 0.108 Uiso 0.669(7) 1 calc PR A 1 C4"B C 0.8346(6) 0.0169(4) 0.77818(10) 0.0402(7) Uani 0.331(7) 1 d P A 2 O5"B O 0.6619(12) 0.1610(11) 0.7148(3) 0.063(3) Uani 0.331(7) 1 d P A 2 H5"2 H 0.7791 0.2185 0.7141 0.095 Uiso 0.331(7) 1 calc PR A 2 C5"B C 0.675(6) 0.009(5) 0.7393(10) 0.093(18) Uani 0.331(7) 1 d P A 2 H5"C H 0.7133 -0.1058 0.7216 0.111 Uiso 0.331(7) 1 calc PR A 2 H5"D H 0.5314 -0.0166 0.7508 0.111 Uiso 0.331(7) 1 calc PR A 2 H4" H 0.972(5) 0.002(4) 0.7698(8) 0.041(8) 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 C4 0.0278(15) 0.0411(17) 0.0414(15) -0.0084(14) -0.0014(13) -0.0015(14) C5 0.0282(16) 0.0355(15) 0.0376(15) -0.0071(14) -0.0044(12) -0.0001(13) C2" 0.0377(16) 0.0456(18) 0.0386(15) -0.0024(14) -0.0017(13) 0.0036(15) C2 0.0292(17) 0.056(2) 0.0572(18) -0.0212(17) -0.0016(13) -0.0032(16) C3' 0.0272(16) 0.0420(17) 0.0401(15) -0.0019(15) -0.0022(13) 0.0014(15) C1" 0.0327(15) 0.0406(16) 0.0404(15) -0.0084(14) -0.0013(13) -0.0013(14) C5' 0.0402(18) 0.0421(18) 0.0449(16) -0.0054(16) 0.0013(15) 0.0019(15) C6' 0.067(2) 0.0525(18) 0.069(2) -0.0154(16) -0.0044(18) 0.017(2) C3" 0.0444(17) 0.0337(16) 0.0458(17) -0.0015(13) -0.0040(13) -0.0007(15) O5" 0.0646(12) 0.0316(10) 0.0376(10) -0.0039(9) -0.0024(10) 0.0003(10) O2" 0.0419(12) 0.0575(14) 0.0572(12) -0.0012(10) -0.0136(10) 0.0095(11) O3" 0.0787(15) 0.0312(12) 0.0622(13) -0.0053(10) -0.0152(12) -0.0026(11) O1' 0.0460(12) 0.0537(14) 0.0630(13) -0.0234(11) -0.0058(11) 0.0023(11) N1 0.0261(12) 0.0393(12) 0.0445(13) -0.0122(11) 0.0006(10) -0.0010(11) N5 0.0295(13) 0.0565(16) 0.0638(15) -0.0267(14) -0.0049(12) 0.0030(12) N2' 0.0394(14) 0.0544(15) 0.0653(15) -0.0273(14) -0.0061(13) 0.0076(14) N4' 0.0377(15) 0.0481(14) 0.0479(14) -0.0140(13) -0.0040(11) 0.0027(13) N3 0.0313(13) 0.0553(15) 0.0582(14) -0.0216(14) -0.0015(12) -0.0012(13) C4"A 0.0419(19) 0.0352(17) 0.0436(19) -0.0034(15) -0.0025(19) 0.0031(15) C5"A 0.086(13) 0.014(3) 0.082(12) -0.007(4) -0.025(9) 0.009(5) O5"A 0.060(3) 0.072(3) 0.083(3) 0.022(2) -0.018(2) 0.005(2) C4"B 0.0419(19) 0.0352(17) 0.0436(19) -0.0034(15) -0.0025(19) 0.0031(15) O5"B 0.093(5) 0.056(5) 0.041(5) 0.013(4) -0.018(4) -0.021(4) C5"B 0.08(3) 0.18(4) 0.019(12) -0.006(13) -0.026(14) 0.010(17) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C5 C4 N3 110.4(2) C5 C4 C3' 126.1(2) N3 C4 C3' 123.2(2) N5 C5 C4 130.6(2) N5 C5 N1 123.8(2) C4 C5 N1 105.6(2) O2" C2" C3" 109.4(2) O2" C2" C1" 108.4(2) C3" C2" C1" 102.1(2) O2" C2" H2"A 112.1 C3" C2" H2"A 112.1 C1" C2" H2"A 112.1 N3 C2 N1 112.7(2) N3 C2 H2 123.6 N1 C2 H2 123.6 N2' C3' N4' 113.4(2) N2' C3' C4 122.1(2) N4' C3' C4 124.5(2) O5" C1" N1 107.5(2) O5" C1" C2" 107.2(2) N1 C1" C2" 115.7(2) O5" C1" H1" 108.7 N1 C1" H1" 108.7 C2" C1" H1" 108.7 N4' C5' O1' 112.9(2) N4' C5' C6' 129.5(3) O1' C5' C6' 117.6(3) O3" C3" C4"A 113.7(2) O3" C3" C2" 112.6(2) C4"A C3" C2" 102.1(2) O3" C3" H3"A 109.4 C4"A C3" H3"A 109.4 C2" C3" H3"A 109.4 C1" O5" C4"A 109.2(2) C5' O1' N2' 106.7(2) C2 N1 C5 106.2(2) C2 N1 C1" 126.4(2) C5 N1 C1" 126.6(2) C5 N5 H5A 120.0 C5 N5 H5B 120.0 H5A N5 H5B 120.0 C3' N2' O1' 103.1(2) C5' N4' C3' 103.9(2) C2 N3 C4 105.0(2) O5" C4"A C5"A 109.8(4) O5" C4"A C3" 103.9(2) C5"A C4"A C3" 115.9(6) O5" C4"A H4" 103.0(19) C5"A C4"A H4" 113.1(18) C3" C4"A H4" 110.0(17) O5"A C5"A C4"A 119.4(10) O5"A C5"A H5"A 107.5 C4"A C5"A H5"A 107.5 O5"A C5"A H5"B 107.5 C4"A C5"A H5"B 107.5 H5"A C5"A H5"B 107.0 C5"B O5"B H5"2 109.5 O5"B C5"B H5"C 107.7 O5"B C5"B H5"D 107.7 H5"C C5"B H5"D 107.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C4 C5 1.365(4) C4 N3 1.391(3) C4 C3' 1.440(4) C5 N5 1.342(3) C5 N1 1.381(3) C2" O2" 1.417(3) C2" C3" 1.521(4) C2" C1" 1.521(4) C2" H2"A 0.9800 C2 N3 1.297(4) C2 N1 1.372(3) C2 H2 0.9300 C3' N2' 1.315(4) C3' N4' 1.375(4) C1" O5" 1.434(3) C1" N1 1.456(3) C1" H1" 0.9800 C5' N4' 1.292(4) C5' O1' 1.330(3) C5' C6' 1.478(4) C6' H1A 0.9600 C6' H6'B 0.9600 C6' H6'C 0.9600 C3" O3" 1.415(3) C3" C4"A 1.511(4) C3" H3"A 0.9800 O5" C4"A 1.437(3) O2" H2"B 0.8200 O3" H3"B 0.8200 O1' N2' 1.421(3) N5 H5A 0.8600 N5 H5B 0.8600 C4"A C5"A 1.464(15) C4"A H4" 0.89(3) C5"A O5"A 1.304(14) C5"A H5"A 0.9700 C5"A H5"B 0.9700 O5"A H5"1 0.8200 O5"B C5"B 1.26(3) O5"B H5"2 0.8200 C5"B H5"C 0.9700 C5"B H5"D 0.9700 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 N5 H5B N3 0.86 2.16 2.949(3) 153.4 1_655 N5 H5A N4' 0.86 2.55 3.061(3) 118.8 1_655 O2" H2"B N4' 0.82 2.24 2.991(3) 153.0 1_645 O3" H3"B O5"A 0.82 2.10 2.862(4) 153.9 3_646 O5"A H5"1 O5"B 0.82 2.15 2.829(8) 140.5 3_646 O5"B H5"2 O2" 0.82 2.43 2.908(9) 118.5 3_756