#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/31/2203199.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_2203199 loop_ _publ_author_name 'Argay, Gyula' 'K\'alm\'an, Alajos' 'Bern\'ath, G\'abor' 'Cs. Gyarmati, Zsuzsanna' _publ_section_title ; cis-8-Azabicyclo[5.2.0]nonan-9-one ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o173 _journal_page_last o175 _journal_paper_doi 10.1107/S160053680302796X _journal_volume 60 _journal_year 2004 _chemical_formula_moiety 'C8 H13 N O' _chemical_formula_sum 'C8 H13 N O' _chemical_formula_weight 139.19 _chemical_melting_point 328.5(5) _chemical_name_systematic ; cis-8-azabicyclo[5.2.0]nonan-9-one ; _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 6.6830(10) _cell_length_b 9.1660(10) _cell_length_c 12.696(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.54 _cell_measurement_theta_min 24.34 _cell_volume 777.71(19) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1992)' _computing_data_reduction 'XCAD4 (Harms 1996)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and RPluto in CSD (Allen, F. H. (2002)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w-\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'CU k\a' _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 1863 _diffrn_reflns_theta_full 74.85 _diffrn_reflns_theta_max 74.85 _diffrn_reflns_theta_min 5.95 _diffrn_standards_decay_% 16 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.620 _exptl_absorpt_correction_T_max 0.9099 _exptl_absorpt_correction_T_min 0.8920 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 304 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.225 _refine_diff_density_min -0.275 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.979 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 91 _refine_ls_number_reflns 941 _refine_ls_number_restraints 86 _refine_ls_restrained_S_all 1.889 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0660 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2144 _refine_ls_wR_factor_ref 0.2270 _reflns_number_gt 842 _reflns_number_total 941 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lh6151.cif _cod_data_source_block 3 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '328-329' was changed to '328.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '328-329' was changed to '328.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2203199 _cod_database_fobs_code 2203199 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_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_type_symbol C1 0.4015(4) 0.4291(4) 0.2136(2) 0.0546(7) Uani d U 1 C H1 0.3830 0.5342 0.2033 0.071 Uiso calc R 1 H C2 0.4753(4) 0.3970(4) 0.3239(2) 0.0539(7) Uani d U 1 C H2A 0.5070 0.2940 0.3290 0.070 Uiso calc R 1 H H2B 0.5976 0.4513 0.3361 0.070 Uiso calc R 1 H C3 0.3248(5) 0.4357(4) 0.4092(2) 0.0624(9) Uani d U 1 C H3A 0.3963 0.4493 0.4750 0.081 Uiso calc R 1 H H3B 0.2630 0.5282 0.3912 0.081 Uiso calc R 1 H C4 0.1599(6) 0.3236(5) 0.4268(3) 0.0734(10) Uani d U 1 C H4A 0.0787 0.3558 0.4857 0.095 Uiso calc R 1 H H4B 0.2221 0.2322 0.4471 0.095 Uiso calc R 1 H C5 0.0210(5) 0.2938(5) 0.3335(3) 0.0715(10) Uani d U 1 C H5A -0.0425 0.3847 0.3130 0.093 Uiso calc R 1 H H5B -0.0837 0.2275 0.3561 0.093 Uiso calc R 1 H C6 0.1239(5) 0.2294(4) 0.2382(3) 0.0657(9) Uani d U 1 C H6A 0.2252 0.1609 0.2617 0.085 Uiso calc R 1 H H6B 0.0265 0.1755 0.1970 0.085 Uiso calc R 1 H C7 0.2206(5) 0.3426(4) 0.1692(2) 0.0609(8) Uani d U 1 C H7 0.1206 0.4083 0.1386 0.079 Uiso calc R 1 H N8 0.3600(5) 0.2879(4) 0.0878(2) 0.0723(9) Uani d U 1 N H8 0.3438 0.2285 0.0361 0.094 Uiso calc R 1 H C9 0.5201(5) 0.3623(4) 0.1218(2) 0.0630(8) Uani d U 1 C O1 0.6909(4) 0.3724(4) 0.0909(2) 0.0895(10) Uani d U 1 O 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 C1 0.0524(15) 0.0613(15) 0.0499(14) 0.0004(13) 0.0036(11) -0.0037(11) C2 0.0428(13) 0.0676(16) 0.0511(14) 0.0004(12) -0.0005(11) -0.0063(12) C3 0.0613(19) 0.0773(19) 0.0488(13) 0.0043(15) 0.0045(14) -0.0116(14) C4 0.0635(19) 0.097(2) 0.0593(17) -0.0014(19) 0.0131(14) 0.0051(16) C5 0.0472(15) 0.087(2) 0.080(2) -0.0049(16) 0.0019(15) 0.0166(18) C6 0.0565(15) 0.0700(17) 0.0705(18) -0.0115(15) -0.0135(14) 0.0045(15) C7 0.0574(16) 0.0743(18) 0.0511(14) 0.0031(15) -0.0125(12) 0.0026(14) N8 0.0811(18) 0.0895(19) 0.0464(12) 0.0014(16) -0.0085(13) -0.0136(13) C9 0.0664(17) 0.0780(18) 0.0447(13) 0.0035(16) 0.0049(12) -0.0052(13) O1 0.0736(17) 0.125(2) 0.0703(15) -0.0044(17) 0.0238(14) -0.0227(16) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0000 '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 C2 C1 C7 119.4(3) C2 C1 C9 117.1(2) C7 C1 C9 85.6(2) C2 C1 H1 110.8 C7 C1 H1 110.8 C9 C1 H1 110.8 C3 C2 C1 113.5(2) C3 C2 H2A 108.9 C1 C2 H2A 108.9 C3 C2 H2B 108.9 C1 C2 H2B 108.9 H2A C2 H2B 107.7 C4 C3 C2 115.2(3) C4 C3 H3A 108.5 C2 C3 H3A 108.5 C4 C3 H3B 108.5 C2 C3 H3B 108.5 H3A C3 H3B 107.5 C3 C4 C5 116.4(3) C3 C4 H4A 108.2 C5 C4 H4A 108.2 C3 C4 H4B 108.2 C5 C4 H4B 108.2 H4A C4 H4B 107.3 C4 C5 C6 114.4(3) C4 C5 H5A 108.7 C6 C5 H5A 108.7 C4 C5 H5B 108.7 C6 C5 H5B 108.7 H5A C5 H5B 107.6 C7 C6 C5 113.1(3) C7 C6 H6A 109.0 C5 C6 H6A 109.0 C7 C6 H6B 109.0 C5 C6 H6B 109.0 H6A C6 H6B 107.8 N8 C7 C6 116.4(3) N8 C7 C1 86.3(2) C6 C7 C1 118.4(2) N8 C7 H7 111.2 C6 C7 H7 111.2 C1 C7 H7 111.2 C9 N8 C7 96.1(2) C9 N8 H8 132.0 C7 N8 H8 132.0 O1 C9 N8 133.4(3) O1 C9 C1 134.6(3) N8 C9 C1 92.0(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.513(4) yes C1 C7 1.552(4) yes C1 C9 1.537(4) yes C1 H1 0.9800 ? C2 C3 1.521(4) yes C2 H2A 0.9700 ? C2 H2B 0.9700 ? C3 C4 1.524(5) yes C3 H3A 0.9700 ? C3 H3B 0.9700 ? C4 C5 1.530(5) yes C4 H4A 0.9700 ? C4 H4B 0.9700 ? C5 C6 1.511(5) yes C5 H5A 0.9700 ? C5 H5B 0.9700 ? C6 C7 1.505(5) yes C6 H6A 0.9700 ? C6 H6B 0.9700 ? C7 N8 1.478(4) yes C7 H7 0.9800 ? N8 C9 1.340(5) yes N8 H8 0.8600 ? C9 O1 1.210(4) yes 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 N8 H8 O1 4_455 0.86 2.12 2.929(4) 156.5 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 C7 C1 C2 C3 -65.4(4) C9 C1 C2 C3 -166.3(3) C1 C2 C3 C4 80.4(4) C2 C3 C4 C5 -61.9(4) C3 C4 C5 C6 63.3(4) C4 C5 C6 C7 -83.5(4) C5 C6 C7 N8 167.3(3) C5 C6 C7 C1 66.5(4) C2 C1 C7 N8 -117.9(3) C9 C1 C7 N8 0.9(2) C2 C1 C7 C6 0.3(4) C9 C1 C7 C6 119.0(3) C6 C7 N8 C9 -121.0(3) C1 C7 N8 C9 -1.0(3) C7 N8 C9 O1 -178.6(5) C7 N8 C9 C1 1.0(3) C2 C1 C9 O1 -60.5(6) C7 C1 C9 O1 178.7(5) C2 C1 C9 N8 119.9(3) C7 C1 C9 N8 -1.0(3)