#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/03/2200385.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_2200385 loop_ _publ_author_name 'Pavkovic, Stephen F.' 'Zerkowski, Jonathan A.' 'Zeng, Qi' _publ_section_title ; Cyclo(alanine-4-hydroxyproline) ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o798 _journal_page_last o799 _journal_paper_doi 10.1107/S1600536801012636 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C8 H12 N2 O3' _chemical_formula_moiety 'C8 H12 N2 O3' _chemical_formula_sum 'C8 H12 N2 O3' _chemical_formula_weight 184.20 _chemical_name_common cyclo(analine-4-hydroxyproline) _chemical_name_systematic ; 2-hydroxy-6-methyl-1,2,3,5,6,7,8,8a-octahydro-7-azaindolizine-5,8-dione ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90.00 _cell_angle_beta 103.719(9) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 8.626(2) _cell_length_b 9.924(3) _cell_length_c 5.1790(10) _cell_measurement_reflns_used 16 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 13 _cell_measurement_theta_min 11 _cell_volume 430.70(18) _computing_cell_refinement 'Please provide' _computing_data_collection 'Please provide' _computing_data_reduction 'Please provide' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 21(2) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'MAKER? four-circle' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator none _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71070 _diffrn_reflns_av_R_equivalents .0353 _diffrn_reflns_av_sigmaI/netI .0738 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 2100 _diffrn_reflns_theta_full 28.01 _diffrn_reflns_theta_max 28.01 _diffrn_reflns_theta_min 2.43 _diffrn_standards_decay_% <1 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .110 _exptl_absorpt_correction_T_max .978 _exptl_absorpt_correction_T_min .952 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 196 _exptl_crystal_size_max .45 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .20 _refine_diff_density_max .199 _refine_diff_density_min -.175 _refine_ls_extinction_coef .074(13) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref .989 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 1099 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all .989 _refine_ls_R_factor_all .0562 _refine_ls_R_factor_gt .0400 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0264P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .0960 _reflns_number_gt 835 _reflns_number_total 1099 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6054.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2200385 _cod_database_fobs_code 2200385 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, 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 C1 .2467(3) .6102(3) .3226(5) .0347(6) Uani d . 1 . . C C2 -.0077(3) .4887(3) .2753(5) .0342(6) Uani d . 1 . . C H2 -.0731 .5261 .1098 .041 Uiso calc R 1 . . H C3 .0726(3) .3612(3) .2082(5) .0325(6) Uani d . 1 . . C C4 .2801(3) .5138(3) .1155(5) .0325(6) Uani d . 1 . . C H4 .2393 .5525 -.0617 .039 Uiso calc R 1 . . H C5 .4557(4) .4786(3) .1508(6) .0408(7) Uani d . 1 . . C H5A .5094 .4739 .3377 .049 Uiso calc R 1 . . H H5B .5092 .5449 .0648 .049 Uiso calc R 1 . . H C6 .4536(3) .3413(3) .0187(6) .0390(7) Uani d . 1 . . C H6 .5517 .2911 .0942 .047 Uiso calc R 1 . . H C7 .3088(4) .2714(3) .0811(7) .0444(7) Uani d . 1 . . C H7A .2542 .2162 -.0674 .053 Uiso calc R 1 . . H H7B .3406 .2149 .2375 .053 Uiso calc R 1 . . H C8 -.1152(4) .4593(3) .4595(8) .0524(8) Uani d . 1 . . C H8A -.1638 .5415 .4984 .079 Uiso calc R 1 . . H H8B -.0534 .4209 .6216 .079 Uiso calc R 1 . . H H8C -.1966 .3969 .3758 .079 Uiso calc R 1 . . H N1 .1110(3) .5890(2) .3947(4) .0350(5) Uani d . 1 . . N H1 .0918 .6379 .5206 .042 Uiso calc R 1 . . H N2 .2062(3) .3816(2) .1281(4) .0342(5) Uani d . 1 . . N O1 .3407(3) .7007(2) .4120(4) .0514(6) Uani d . 1 . . O O2 .0168(2) .24882(19) .2236(4) .0466(6) Uani d . 1 . . O O3 .4307(3) .3558(3) -.2594(4) .0625(7) Uani d . 1 . . O H3 .4828 .2984 -.3154 .075 Uiso calc R 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 C1 .0388(15) .0284(13) .0396(15) .0003(11) .0148(11) .0010(11) C2 .0323(14) .0318(14) .0383(14) .0023(11) .0076(11) -.0003(11) C3 .0348(14) .0324(14) .0303(13) -.0034(11) .0076(10) -.0002(11) C4 .0400(14) .0284(12) .0324(13) .0000(11) .0149(11) .0017(11) C5 .0385(15) .0388(15) .0511(16) -.0005(12) .0225(13) .0014(13) C6 .0381(15) .0413(16) .0395(15) .0094(12) .0130(12) .0044(12) C7 .0502(16) .0330(15) .0531(19) .0011(13) .0188(14) -.0092(13) C8 .0410(16) .0476(17) .077(2) -.0074(14) .0311(16) -.0152(17) N1 .0391(13) .0283(12) .0417(13) -.0034(10) .0179(10) -.0077(9) N2 .0375(12) .0265(11) .0412(13) -.0003(10) .0142(9) -.0061(10) O1 .0528(13) .0426(12) .0674(16) -.0181(10) .0313(11) -.0189(11) O2 .0511(12) .0339(11) .0607(15) -.0104(9) .0249(11) -.0040(9) O3 .0801(17) .0728(17) .0421(12) .0356(13) .0295(11) .0071(11) 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 _geom_angle_publ_flag O1 C1 N1 124.0(2) no O1 C1 C4 120.7(3) no N1 C1 C4 115.3(2) no N1 C2 C8 109.8(2) no N1 C2 C3 110.7(2) no C8 C2 C3 111.4(2) no N1 C2 H2 108.3 no C8 C2 H2 108.3 no C3 C2 H2 108.3 no O2 C3 N2 122.9(3) no O2 C3 C2 122.3(2) no N2 C3 C2 114.8(2) no N2 C4 C1 112.1(2) no N2 C4 C5 102.7(2) no C1 C4 C5 114.2(2) no N2 C4 H4 109.2 no C1 C4 H4 109.2 no C5 C4 H4 109.2 no C4 C5 C6 104.2(2) no C4 C5 H5A 110.9 no C6 C5 H5A 110.9 no C4 C5 H5B 110.9 no C6 C5 H5B 110.9 no H5A C5 H5B 108.9 no O3 C6 C5 110.5(2) no O3 C6 C7 109.7(2) no C5 C6 C7 103.5(2) no O3 C6 H6 110.9 no C5 C6 H6 110.9 no C7 C6 H6 110.9 no N2 C7 C6 104.7(2) no N2 C7 H7A 110.8 no C6 C7 H7A 110.8 no N2 C7 H7B 110.8 no C6 C7 H7B 110.8 no H7A C7 H7B 108.9 no C2 C8 H8A 109.5 no C2 C8 H8B 109.5 no H8A C8 H8B 109.5 no C2 C8 H8C 109.5 no H8A C8 H8C 109.5 no H8B C8 H8C 109.5 no C1 N1 C2 124.5(2) no C1 N1 H1 117.7 no C2 N1 H1 117.7 no C3 N2 C4 124.6(2) no C3 N2 C7 122.7(2) no C4 N2 C7 112.0(2) no C6 O3 H3 109.5 no 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 C1 O1 . 1.225(3) no C1 N1 . 1.327(3) no C1 C4 . 1.515(3) no C2 N1 . 1.456(3) no C2 C8 . 1.508(4) no C2 C3 . 1.522(4) no C2 H2 . .9800 no C3 O2 . 1.225(3) no C3 N2 . 1.330(3) no C4 N2 . 1.467(3) no C4 C5 . 1.523(4) no C4 H4 . .9800 no C5 C6 . 1.523(4) no C5 H5A . .9700 no C5 H5B . .9700 no C6 O3 . 1.414(4) no C6 C7 . 1.529(4) no C6 H6 . .9800 no C7 N2 . 1.463(4) no C7 H7A . .9700 no C7 H7B . .9700 no C8 H8A . .9600 no C8 H8B . .9600 no C8 H8C . .9600 no N1 H1 . .8600 no O3 H3 . .8200 no 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 _geom_hbond_publ_flag N1 H1 O2 2_556 .86 2.10 2.945(3) 165.2 yes O3 H3 O1 2_645 .82 1.97 2.761(3) 162.7 yes 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 _geom_torsion_publ_flag N1 C2 C3 O2 145.8(3) no C8 C2 C3 O2 23.3(4) no N1 C2 C3 N2 -35.2(3) no C8 C2 C3 N2 -157.7(2) no O1 C1 C4 N2 151.9(3) no N1 C1 C4 N2 -28.5(3) no O1 C1 C4 C5 35.6(4) no N1 C1 C4 C5 -144.7(2) no N2 C4 C5 C6 33.0(3) no C1 C4 C5 C6 154.5(2) no C4 C5 C6 O3 82.0(3) no C4 C5 C6 C7 -35.5(3) no O3 C6 C7 N2 -94.0(3) no C5 C6 C7 N2 23.9(3) no O1 C1 N1 C2 174.9(3) no C4 C1 N1 C2 -4.7(4) no C8 C2 N1 C1 160.8(2) no C3 C2 N1 C1 37.4(3) no O2 C3 N2 C4 -177.8(3) no C2 C3 N2 C4 3.2(4) no O2 C3 N2 C7 -7.4(4) no C2 C3 N2 C7 173.6(2) no C1 C4 N2 C3 29.7(4) no C5 C4 N2 C3 152.7(2) no C1 C4 N2 C7 -141.6(3) no C5 C4 N2 C7 -18.5(3) no C6 C7 N2 C3 -174.9(2) no C6 C7 N2 C4 -3.4(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 24215522 2 PubChem 45099895