#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/65/2006545.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2006545 loop_ _publ_author_name 'Piacenza, Guy' 'Beguet, Christelle' 'Wimmer, Eric' 'Gallo, Roger' 'Giorgi, Michel' _publ_section_title ; 2,4,6,8-Tetraazabicyclo[3.3.1]nonane-3,7-dione and 2,4,6,8-Tetraacetyl-2,4,6,8-tetraazabicyclo[3.3.1]nonane-3,7-dione ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1459 _journal_page_last 1462 _journal_paper_doi 10.1107/S0108270197006495 _journal_volume 53 _journal_year 1997 _chemical_formula_sum 'C5 H8 N4 O2' _chemical_formula_weight 156.15 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _atom_type_scat_source IntTabIV _cell_angle_alpha 90.00(3) _cell_angle_beta 90.00(3) _cell_angle_gamma 90.000(10) _cell_formula_units_Z 8 _cell_length_a 11.388(2) _cell_length_b 10.171(2) _cell_length_c 11.767(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294 _cell_measurement_theta_max 18 _cell_measurement_theta_min 15 _cell_volume 1362.9(7) _computing_cell_refinement 'CAD4 Software' _computing_data_collection 'CAD4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'BEGIN SDP (Frenz, 1985)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'CIF VAX in MolEN (Fair, 1990)' _computing_structure_refinement 'LSFM SDP (Frenz, 1985)' _computing_structure_solution 'direct methods (MULTAN80; Main et al., 1980)' _diffrn_ambient_temperature 294 _diffrn_measurement_device Enraf_Nonius_CAD4 _diffrn_measurement_method \w/2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2655 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 3 _diffrn_standards_decay_% 0.28 _diffrn_standards_interval_time 60 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.52 _exptl_crystal_density_meas 1.500 _exptl_crystal_density_method 'flotation in chloroform' _exptl_crystal_description prism _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _refine_diff_density_max 0.257 _refine_diff_density_min -0.291 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.835 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 1005 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.049 _refine_ls_R_factor_obs .039 _refine_ls_shift/esd_max 0.007 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0016Fo^4^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs .052 _reflns_number_observed 1005 _reflns_number_total 1192 _reflns_observed_criterion >3.0\s(I) _cod_data_source_file ab1467.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '4Fo^2^/[\s^2^(Fo^2^) + 0.0016Fo^4^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0016Fo^4^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1363.0(10) _cod_database_code 2006545 _cod_database_fobs_code 2006545 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O2 .0303(5) .0571(6) .0323(4) -.0037(5) -.0066(4) .0099(5) O5 .0319(5) .0564(6) .0362(5) -.0074(5) -.0036(4) -.0105(6) N3 .0279(5) .0380(6) .0285(5) .0000(5) .0013(5) .0015(5) N6 .0277(5) .0461(7) .0295(6) -.0015(5) .0030(5) -.0017(5) N4 .0301(5) .0406(6) .0286(5) -.0030(5) .0030(5) -.0028(5) N1 .0312(5) .0471(6) .0261(5) .0022(6) .0027(5) -.0007(6) C7 .0343(7) .0349(7) .0328(6) .0072(6) .0020(6) -.0057(6) C2 .0268(5) .0344(7) .0260(6) -.0053(6) -.0038(5) -.0030(6) C5 .0272(6) .0359(6) .0247(5) .0022(6) -.0036(5) .0023(6) C8 .0324(6) .0300(6) .0307(6) -.0043(6) .0026(5) .0037(6) C9 .0460(8) .0272(7) .0446(8) .0021(6) -.0001(6) .0009(7) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag O2 .64121(8) .21990(10) .69705(8) .0399(3) Uani ? O5 .92566(8) .26890(10) 1.06035(9) .0415(3) Uani ? N3 .64081(9) .11390(10) .86560(10) .0315(3) Uani ? N6 .93111(9) .12940(10) .91055(9) .0344(3) Uani ? N4 .76949(9) .13660(10) 1.02840(10) .0331(3) Uani ? N1 .80370(10) .10620(10) .74780(10) .0348(3) Uani ? C7 .87240(10) .03820(10) .83380(10) .0340(3) Uani ? C2 .69330(10) .14990(10) .76750(10) .0290(3) Uani ? C5 .87740(10) .18190(10) 1.00180(10) .0292(3) Uani ? C8 .70440(10) .04670(10) .95660(10) .0310(3) Uani ? C9 .79040(10) -.04720(10) .90240(10) .0392(4) Uani ? H1 .643 .005 1.005 .0348 Uiso calc H2 .746 -.105 .858 .0447 Uiso calc H3 .937 -.014 .793 .0381 Uiso calc H5 .837 -.096 .961 .0447 Uiso calc H4 .573 .159 .882 .0343 Uiso calc H6 .733 .180 1.084 .0363 Uiso calc H7 .999 .170 .887 .0386 Uiso calc H8 .836 .144 .692 .0388 Uiso calc loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 N3 C8 122.20(10) no C7 N6 C5 122.60(10) no C5 N4 C8 123.10(10) no C7 N1 C2 122.50(10) yes N6 C7 N1 112.10(10) yes N6 C7 C9 108.60(10) no N1 C7 C9 108.30(10) yes O2 C2 N3 120.90(10) no O2 C2 N1 121.20(10) yes N3 C2 N1 117.90(10) yes O5 C5 N6 121.40(10) no O5 C5 N4 121.00(10) no N6 C5 N4 117.60(10) no N3 C8 N4 112.70(10) no N3 C8 C9 107.90(10) no N4 C8 C9 108.30(10) no C7 C9 C8 105.20(10) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O2 C2 1.243(2) yes O5 C5 1.249(2) no N3 C2 1.351(2) no N3 C8 1.463(2) no N6 C7 1.456(2) no N6 C5 1.346(2) no N4 C5 1.349(2) no N4 C8 1.449(2) no N1 C7 1.454(2) yes N1 C2 1.352(2) yes C7 C9 1.509(2) yes C8 C9 1.509(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 5150075