#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/04/2200452.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_2200452 loop_ _publ_author_name 'Howie, R. Alan' 'Skakle, Janet M. S.' _publ_section_title ; 3-Azabicyclo[3.3.1]nonane-2,4-dione: CSP2001 structure prediction test case No. 1 ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o822 _journal_page_last o824 _journal_paper_doi 10.1107/S1600536801012818 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C8 H11 N O2' _chemical_formula_moiety 'C8 H11 N O2' _chemical_formula_sum 'C8 H11 N O2' _chemical_formula_weight 153.18 _chemical_name_systematic ; 3-Aza-bicyclo[3.3.1]nonane-2,4-dione ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 95.033(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.7046(5) _cell_length_b 10.6062(7) _cell_length_c 9.3384(6) _cell_measurement_reflns_used 2072 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 30.250 _cell_measurement_theta_min 2.189 _cell_volume 760.16(9) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 297(2) _diffrn_measured_fraction_theta_full .99 _diffrn_measured_fraction_theta_max .99 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \f-\w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .026 _diffrn_reflns_av_sigmaI/netI .034 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7616 _diffrn_reflns_theta_full 32.48 _diffrn_reflns_theta_max 32.48 _diffrn_reflns_theta_min 2.91 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .097 _exptl_absorpt_correction_T_max .9810 _exptl_absorpt_correction_T_min .9716 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1999)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 328 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .20 _refine_diff_density_max .24 _refine_diff_density_min -.20 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .90 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 144 _refine_ls_number_reflns 2736 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .90 _refine_ls_R_factor_all .083 _refine_ls_R_factor_gt .044 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0713P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .123 _reflns_number_gt 1584 _reflns_number_total 2736 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6050.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2200452 _cod_database_fobs_code 2200452 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z' '-x, -y, -z' '-x-1/2, y-1/2, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 .47604(11) .41167(9) .19143(11) .0385(2) Uani d . 1 . . N H1 .5638(18) .3594(15) .1944(14) .050(4) Uiso d . 1 . . H C1 .31183(13) .35911(11) .19361(12) .0382(3) Uani d . 1 . . C O1 .29710(11) .24477(8) .19994(12) .0609(3) Uani d . 1 . . O C2 .15972(13) .44791(11) .19189(13) .0385(3) Uani d . 1 . . C H2 .0576(18) .4025(14) .1402(15) .053(4) Uiso d . 1 . . H C3 .19984(16) .57024(13) .11776(14) .0444(3) Uani d . 1 . . C H3A .1010(18) .6311(14) .1206(15) .055(4) Uiso d . 1 . . H H3B .2158(19) .5561(13) .0134(16) .054(4) Uiso d . 1 . . H C4 .36180(16) .62782(11) .19735(14) .0422(3) Uani d . 1 . . C H4 .396(2) .7013(16) .1533(16) .065(5) Uiso d . 1 . . H C5 .51396(14) .53949(10) .19270(12) .0366(2) Uani d . 1 . . C O2 .66431(11) .57333(9) .19198(11) .0541(3) Uani d . 1 . . O C6 .32967(17) .65664(13) .35390(15) .0496(3) Uani d . 1 . . C H6A .235(2) .7262(16) .3468(17) .068(5) Uiso d . 1 . . H H6B .440(2) .6914(14) .4008(15) .060(4) Uiso d . 1 . . H C7 .26614(16) .54282(15) .43251(14) .0501(3) Uani d . 1 . . C H7A .362(2) .4814(14) .4494(14) .052(4) Uiso d . 1 . . H H7B .229(2) .5673(16) .523(2) .075(5) Uiso d . 1 . . H C8 .11724(14) .47485(14) .34682(14) .0458(3) Uani d . 1 . . C H8A .0860(18) .3940(16) .3915(15) .053(4) Uiso d . 1 . . H H8B .0121(19) .5233(14) .3405(14) .049(4) Uiso d . 1 . . H 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 N1 .0256(4) .0312(5) .0591(6) .0018(3) .0054(4) -.0022(4) C1 .0283(5) .0336(6) .0526(7) -.0021(4) .0025(4) -.0024(5) O1 .0378(4) .0326(5) .1127(9) -.0042(4) .0093(5) -.0038(5) C2 .0246(4) .0417(6) .0484(6) .0014(4) -.0018(4) -.0027(5) C3 .0409(6) .0468(7) .0450(7) .0114(5) .0009(5) .0063(5) C4 .0433(6) .0280(5) .0561(7) .0028(5) .0092(5) .0061(5) C5 .0356(5) .0326(6) .0424(6) -.0027(4) .0084(4) -.0008(4) O2 .0377(4) .0472(5) .0791(6) -.0119(4) .0157(4) -.0063(5) C6 .0410(6) .0452(7) .0628(8) .0027(5) .0061(6) -.0172(6) C7 .0386(6) .0710(10) .0411(7) .0028(6) .0063(5) -.0051(6) C8 .0294(5) .0553(7) .0539(7) .0011(5) .0103(5) .0038(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 '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 C1 N1 C5 125.86(9) C1 N1 H1 116.8(10) C5 N1 H1 117.3(10) O1 C1 N1 119.35(10) O1 C1 C2 123.22(10) N1 C1 C2 117.41(10) C1 C2 C3 110.58(9) C1 C2 C8 109.67(9) C3 C2 C8 109.85(10) C1 C2 H2 106.3(8) C3 C2 H2 111.8(8) C8 C2 H2 108.5(8) C2 C3 C4 108.16(10) C2 C3 H3A 110.8(8) C4 C3 H3A 108.7(8) C2 C3 H3B 111.3(8) C4 C3 H3B 111.6(8) H3A C3 H3B 106.3(12) C5 C4 C3 110.09(10) C5 C4 C6 110.05(10) C3 C4 C6 110.55(10) C5 C4 H4 105.1(10) C3 C4 H4 111.7(9) C6 C4 H4 109.2(10) O2 C5 N1 119.32(10) O2 C5 C4 124.25(11) N1 C5 C4 116.42(9) C7 C6 C4 112.86(10) C7 C6 H6A 109.9(9) C4 C6 H6A 104.7(9) C7 C6 H6B 112.5(9) C4 C6 H6B 107.0(9) H6A C6 H6B 109.7(12) C6 C7 C8 112.53(11) C6 C7 H7A 109.3(8) C8 C7 H7A 107.0(8) C6 C7 H7B 110.3(10) C8 C7 H7B 109.2(10) H7A C7 H7B 108.4(12) C7 C8 C2 111.71(9) C7 C8 H8A 112.8(8) C2 C8 H8A 108.3(8) C7 C8 H8B 111.9(9) C2 C8 H8B 106.9(8) H8A C8 H8B 104.7(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 . 1.3843(13) ? N1 C5 . 1.3866(14) ? N1 H1 . .873(15) ? C1 O1 . 1.2199(14) ? C1 C2 . 1.5025(15) ? C2 C3 . 1.5151(18) ? C2 C8 . 1.5379(17) ? C2 H2 . 1.009(14) ? C3 C4 . 1.5231(18) ? C3 H3A . 1.001(14) ? C3 H3B . 1.004(14) ? C4 C5 . 1.5042(16) ? C4 C6 . 1.5348(19) ? C4 H4 . .929(17) ? C5 O2 . 1.2133(13) ? C6 C7 . 1.516(2) ? C6 H6A . 1.038(16) ? C6 H6B . .992(15) ? C7 C8 . 1.5215(18) ? C7 H7A . .990(15) ? C7 H7B . .952(18) ? C8 H8A . .993(16) ? C8 H8B . .957(15) ? 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 N1 H1 O1 2 .873(15) 2.107(15) 2.9739(12) 172.2(14) C3 H3B O2 3_665 1.004(14) 2.594(15) 3.5088(16) 151.5(11) C6 H6A O2 2_465 1.038(16) 2.601(17) 3.4313(17) 136.7(11) 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 C5 N1 C1 O1 -176.09(11) C5 N1 C1 C2 2.33(16) O1 C1 C2 C3 -154.08(12) N1 C1 C2 C3 27.57(14) O1 C1 C2 C8 84.64(14) N1 C1 C2 C8 -93.72(12) C1 C2 C3 C4 -58.23(13) C8 C2 C3 C4 62.95(12) C2 C3 C4 C5 60.72(13) C2 C3 C4 C6 -61.07(13) C1 N1 C5 O2 179.25(11) C1 N1 C5 C4 .21(16) C3 C4 C5 O2 148.85(12) C6 C4 C5 O2 -89.06(14) C3 C4 C5 N1 -32.16(14) C6 C4 C5 N1 89.93(12) C5 C4 C6 C7 -67.62(13) C3 C4 C6 C7 54.19(14) C4 C6 C7 C8 -48.23(15) C6 C7 C8 C2 49.82(15) C1 C2 C8 C7 63.92(14) C3 C2 C8 C7 -57.80(14) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4425336 2 PubChem 92965868