#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/31/2203198.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_2203198 loop_ _publ_author_name 'Argay, Gyula' 'F\'abi\'an, L\'aszl\'o' 'K\'alm\'an, Alajos' 'Bern\'ath, G\'abor' 'Cs. Gyarmati, Zsuzsanna' _publ_section_title ; cis-7-Azabicyclo[4.2.0]octan-8-one ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o170 _journal_page_last o172 _journal_paper_doi 10.1107/S1600536803027958 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C7 H11 N O' _chemical_formula_moiety 'C7 H11 N O' _chemical_formula_sum 'C7 H11 N O' _chemical_formula_weight 125.17 _chemical_melting_point 329.5(5) _chemical_name_systematic ; cis-7-azabicyclo[4.2.0]octan-8-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _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 112.000(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.3330(10) _cell_length_b 6.4740(10) _cell_length_c 10.1810(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 32.34 _cell_measurement_theta_min 29.31 _cell_volume 692.59(15) _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, 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 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _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 0.0103 _diffrn_reflns_av_sigmaI/netI 0.0089 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 1554 _diffrn_reflns_theta_full 75.55 _diffrn_reflns_theta_max 75.55 _diffrn_reflns_theta_min 4.21 _diffrn_standards_decay_% 8 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.643 _exptl_absorpt_correction_T_max 0.8218 _exptl_absorpt_correction_T_min 0.7657 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 272 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.228 _refine_diff_density_min -0.146 _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.304 _refine_ls_hydrogen_treatment riding _refine_ls_matrix_type full _refine_ls_number_parameters 108 _refine_ls_number_reflns 1433 _refine_ls_number_restraints 188 _refine_ls_restrained_S_all 1.236 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0521 _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^)+(0.101P)^2^+0.05P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1824 _refine_ls_wR_factor_ref 0.1853 _reflns_number_gt 1256 _reflns_number_total 1433 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lh6150.cif _cod_data_source_block 2 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '329-330' was changed to '329.5(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 '329-330' was changed to '329.5(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_original_cell_volume 692.59(14) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2203198 _cod_database_fobs_code 2203198 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' 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 C1 0.29462(14) 0.4259(2) 0.41635(14) 0.0589(4) Uani d DU 1 . . C H1A 0.3219 0.5110 0.3532 0.077 Uiso calc PR 0.769(7) A 1 H H1B 0.3234 0.5103 0.3542 0.077 Uiso calc PR 0.231(7) A 2 H C2A 0.1508(3) 0.4204(8) 0.3717(6) 0.0667(10) Uani d PDU 0.769(7) A 1 C H2A1 0.1201 0.5590 0.3764 0.087 Uiso calc PR 0.769(7) A 1 H H2A2 0.1128 0.3738 0.2743 0.087 Uiso calc PR 0.769(7) A 1 H C3A 0.1094(3) 0.2785(4) 0.4650(4) 0.0745(7) Uani d PDU 0.769(7) A 1 C H3A1 0.0175 0.2661 0.4250 0.097 Uiso calc PR 0.769(7) A 1 H H3A2 0.1331 0.3406 0.5580 0.097 Uiso calc PR 0.769(7) A 1 H C4A 0.1676(3) 0.0642(5) 0.4810(4) 0.0745(7) Uani d PDU 0.769(7) A 1 C H4A1 0.0988 -0.0342 0.4407 0.097 Uiso calc PR 0.769(7) A 1 H H4A2 0.2072 0.0342 0.5814 0.097 Uiso calc PR 0.769(7) A 1 H C5A 0.2654(4) 0.0250(7) 0.4148(6) 0.0622(8) Uani d PDU 0.769(7) A 1 C H5A1 0.3134 -0.0988 0.4555 0.081 Uiso calc PR 0.769(7) A 1 H H5A2 0.2224 0.0032 0.3138 0.081 Uiso calc PR 0.769(7) A 1 H C2B 0.1574(9) 0.470(2) 0.394(3) 0.072(4) Uani d PDU 0.231(7) A 2 C H2B1 0.1540 0.5391 0.4774 0.094 Uiso calc PR 0.231(7) A 2 H H2B2 0.1207 0.5616 0.3139 0.094 Uiso calc PR 0.231(7) A 2 H C3B 0.0810(9) 0.2735(17) 0.3687(19) 0.103(3) Uani d PDU 0.231(7) A 2 C H3B1 0.0691 0.2220 0.2751 0.134 Uiso calc PR 0.231(7) A 2 H H3B2 -0.0025 0.3051 0.3693 0.134 Uiso calc PR 0.231(7) A 2 H C4B 0.1404(11) 0.104(3) 0.476(2) 0.103(3) Uani d PDU 0.231(7) A 2 C H4B1 0.0841 -0.0137 0.4612 0.134 Uiso calc PR 0.231(7) A 2 H H4B2 0.1641 0.1539 0.5723 0.134 Uiso calc PR 0.231(7) A 2 H C5B 0.2567(16) 0.053(2) 0.442(2) 0.084(5) Uani d PDU 0.231(7) A 2 C H5B1 0.3020 -0.0546 0.5073 0.109 Uiso calc PR 0.231(7) A 2 H H5B2 0.2246 -0.0097 0.3482 0.109 Uiso calc PR 0.231(7) A 2 H C6 0.35598(15) 0.2074(3) 0.44054(16) 0.0610(5) Uani d DU 1 A . C H6A 0.4135 0.1907 0.3895 0.079 Uiso calc PR 0.769(7) A 1 H H6B 0.4071 0.1713 0.3847 0.079 Uiso calc PR 0.231(7) A 2 H N7 0.42568(13) 0.2716(2) 0.58807(14) 0.0661(4) Uani d U 1 . . N H7 0.4799 0.2087 0.6598 0.086 Uiso calc R 1 A . H C8 0.37583(14) 0.4609(2) 0.57222(15) 0.0589(4) Uani d U 1 A . C O1 0.38991(13) 0.60397(19) 0.65522(12) 0.0788(5) 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 0.0662(9) 0.0549(8) 0.0517(8) -0.0100(6) 0.0175(6) 0.0072(6) C2A 0.0619(16) 0.059(2) 0.0662(19) 0.0025(11) 0.0095(12) -0.0031(18) C3A 0.0711(12) 0.0739(13) 0.0868(14) -0.0113(8) 0.0392(11) -0.0019(9) C4A 0.0711(12) 0.0739(13) 0.0868(14) -0.0113(8) 0.0392(11) -0.0019(9) C5A 0.0791(16) 0.0479(17) 0.065(2) -0.0039(12) 0.0328(12) -0.0103(14) C2B 0.067(5) 0.049(6) 0.082(9) -0.009(4) 0.007(4) -0.009(5) C3B 0.064(4) 0.094(6) 0.149(8) -0.009(3) 0.038(4) 0.019(5) C4B 0.064(4) 0.094(6) 0.149(8) -0.009(3) 0.038(4) 0.019(5) C5B 0.140(11) 0.044(5) 0.074(8) 0.008(5) 0.047(6) -0.022(4) C6 0.0633(9) 0.0638(9) 0.0589(8) -0.0011(6) 0.0263(7) -0.0006(6) N7 0.0622(8) 0.0669(8) 0.0588(8) 0.0041(6) 0.0107(6) 0.0050(6) C8 0.0591(8) 0.0573(8) 0.0544(8) -0.0117(6) 0.0144(6) 0.0031(6) O1 0.0929(9) 0.0622(8) 0.0672(7) -0.0139(6) 0.0137(6) -0.0088(5) 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 C2B C1 C8 108.2(9) C2A C1 C8 118.5(2) C2B C1 C6 124.7(5) C2A C1 C6 113.1(2) C8 C1 C6 84.87(11) C2A C1 H1A 112.5 C8 C1 H1A 112.5 C6 C1 H1A 112.5 C2B C1 H1B 111.8 C8 C1 H1B 111.8 C6 C1 H1B 111.8 C3A C2A C1 112.1(3) C3A C2A H2A1 109.2 C1 C2A H2A1 109.2 C3A C2A H2A2 109.2 C1 C2A H2A2 109.2 H2A1 C2A H2A2 107.9 C2A C3A C4A 113.4(3) C2A C3A H3A1 108.9 C4A C3A H3A1 108.9 C2A C3A H3A2 108.9 C4A C3A H3A2 108.9 H3A1 C3A H3A2 107.7 C3A C4A C5A 117.7(3) C3A C4A H4A1 107.9 C5A C4A H4A1 107.9 C3A C4A H4A2 107.9 C5A C4A H4A2 107.9 H4A1 C4A H4A2 107.2 C6 C5A C4A 110.6(3) C6 C5A H5A1 109.5 C4A C5A H5A1 109.5 C6 C5A H5A2 109.5 C4A C5A H5A2 109.5 H5A1 C5A H5A2 108.1 C3B C2B C1 111.0(8) C3B C2B H2B1 109.4 C1 C2B H2B1 109.4 C3B C2B H2B2 109.4 C1 C2B H2B2 109.4 H2B1 C2B H2B2 108.0 C2B C3B C4B 114.5(15) C2B C3B H3B1 108.6 C4B C3B H3B1 108.6 C2B C3B H3B2 108.6 C4B C3B H3B2 108.6 H3B1 C3B H3B2 107.6 C3B C4B C5B 100.5(14) C3B C4B H4B1 111.7 C5B C4B H4B1 111.7 C3B C4B H4B2 111.7 C5B C4B H4B2 111.7 H4B1 C4B H4B2 109.4 C6 C5B C4B 124.8(11) C6 C5B H5B1 106.1 C4B C5B H5B1 106.1 C6 C5B H5B2 106.1 C4B C5B H5B2 106.1 H5B1 C5B H5B2 106.3 N7 C6 C5B 107.3(8) N7 C6 C5A 117.7(2) N7 C6 C1 86.67(11) C5B C6 C1 108.2(7) C5A C6 C1 116.5(2) N7 C6 H6A 111.3 C5A C6 H6A 111.3 C1 C6 H6A 111.3 N7 C6 H6B 116.8 C5B C6 H6B 116.8 C1 C6 H6B 116.8 C8 N7 C6 95.45(12) C8 N7 H7 132.3 C6 N7 H7 132.3 O1 C8 N7 132.26(14) O1 C8 C1 134.71(15) N7 C8 C1 93.01(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2B 1.513(8) ? C1 C2A 1.519(4) yes C1 C8 1.524(2) yes C1 C6 1.555(2) yes C1 H1A 0.9800 ? C1 H1B 0.9800 ? C2A C3A 1.516(5) yes C2A H2A1 0.9700 ? C2A H2A2 0.9700 ? C3A C4A 1.519(4) yes C3A H3A1 0.9700 ? C3A H3A2 0.9700 ? C4A C5A 1.519(4) yes C4A H4A1 0.9700 ? C4A H4A2 0.9700 ? C5A C6 1.521(4) yes C5A H5A1 0.9700 ? C5A H5A2 0.9700 ? C2B C3B 1.506(8) ? C2B H2B1 0.9700 ? C2B H2B2 0.9700 ? C3B C4B 1.514(8) ? C3B H3B1 0.9700 ? C3B H3B2 0.9700 ? C4B C5B 1.521(8) ? C4B H4B1 0.9700 ? C4B H4B2 0.9700 ? C5B C6 1.507(12) ? C5B H5B1 0.9700 ? C5B H5B2 0.9700 ? C6 N7 1.4710(19) yes C6 H6A 0.9800 ? C6 H6B 0.9800 ? N7 C8 1.334(2) yes N7 H7 0.8600 ? C8 O1 1.2232(19) 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 N7 H7 O1 4_657 0.86 2.03 2.8781(17) 171 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 C8 C1 C2A C3A -49.1(4) C6 C1 C2A C3A 47.8(4) C1 C2A C3A C4A -51.1(5) C2A C3A C4A C5A 5.1(5) C3A C4A C5A C6 41.9(5) C8 C1 C2B C3B -108.3(16) C6 C1 C2B C3B -12(2) C1 C2B C3B C4B 50(2) C2B C3B C4B C5B -67(2) C3B C4B C5B C6 56(2) C4B C5B C6 N7 69(2) C4B C5B C6 C1 -24(2) C4A C5A C6 N7 56.2(5) C4A C5A C6 C1 -44.6(5) C2B C1 C6 N7 -108.4(11) C2A C1 C6 N7 -118.6(3) C8 C1 C6 N7 0.16(10) C2B C1 C6 C5B -1.3(14) C8 C1 C6 C5B 107.3(9) C2A C1 C6 C5A 0.8(3) C8 C1 C6 C5A 119.6(2) C5B C6 N7 C8 -108.3(7) C5A C6 N7 C8 -118.5(2) C1 C6 N7 C8 -0.18(12) C6 N7 C8 O1 178.67(17) C6 N7 C8 C1 0.19(12) C2B C1 C8 O1 -53.7(7) C2A C1 C8 O1 -65.1(3) C6 C1 C8 O1 -178.60(18) C2B C1 C8 N7 124.7(6) C2A C1 C8 N7 113.3(3) C6 C1 C8 N7 -0.18(12) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 7010078