#------------------------------------------------------------------------------ #$Date: 2022-01-14 04:35:18 +0200 (Fri, 14 Jan 2022) $ #$Revision: 272038 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/02/25/2022512.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_2022512 loop_ _publ_author_name 'Akram, Sehrish' 'Mehmood, Arshad' 'Noureen, Sajida' 'Ahmed, Maqsood' _publ_section_title ; Thermal-induced transformation of glutamic acid to pyroglutamic acid and self-cocrystallization: a charge--density analysis ; _journal_coeditor_code EF3024 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C Structural Chemistry' _journal_paper_doi 10.1107/S2053229621013607 _journal_volume 78 _journal_year 2022 _chemical_absolute_configuration unk _chemical_formula_iupac 'C5 H7 N O3, C5 H9 N O4, H2 O' _chemical_formula_moiety 'C5 H7 N O3, C5 H9 N O4, H2 O' _chemical_formula_sum 'C10 H18 N2 O8' _chemical_formula_weight 294.263 _chemical_name_common ; Glutamic acid--pyroglutamic acid--water (1/1/1) ; _chemical_name_systematic ; 2-Aminopentanedioic acid--5-oxopyrrolidine-2-carboxylic acid--water (1/1/1) ; _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _cell_angle_alpha 90 _cell_angle_beta 96.817(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.1153(3) _cell_length_b 7.1849(4) _cell_length_c 18.4639(9) _cell_measurement_reflns_used 3695 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 25.31 _cell_measurement_theta_min 3.05 _cell_volume 673.80(6) _computing_cell_refinement ; SAINT (Bruker, 2016) ; _computing_data_reduction ; SAINT (Bruker, 2016) ; _computing_molecular_graphics ; OLEX2 (Dolomanov et al., 2009) ; _computing_publication_material ; OLEX2 (Dolomanov et al., 2009) ; _computing_structure_refinement ; olex2.refine (Bourhis et al., 2015) ; _computing_structure_solution ; SHELXT2018 (Sheldrick, 2015) ; _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.9970 _diffrn_measured_fraction_theta_max 0.9963 _diffrn_measurement_device_type ; Bruker D8 Venture ; _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_unetI/netI 0.0659 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 7139 _diffrn_reflns_theta_full 25.2417 _diffrn_reflns_theta_max 25.33 _diffrn_reflns_theta_min 2.22 _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.4873 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (SADABS; Bruker, 2016; Krause et al., 2015) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.450 _exptl_crystal_description plate-like _exptl_crystal_F_000 312.231 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.2705 _refine_diff_density_min -0.2724 _refine_ls_abs_structure_details ; Flack (1983) ; _refine_ls_abs_structure_Flack 0.0(19) _refine_ls_goodness_of_fit_ref 1.1218 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_constraints 23 _refine_ls_number_parameters 199 _refine_ls_number_reflns 2442 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.1218 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0505 _refine_ls_shift/su_max 0.0003 _refine_ls_shift/su_mean 0.0000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+0.2123P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1008 _refine_ls_wR_factor_ref 0.1157 _reflns_number_gt 1905 _reflns_number_total 2442 _reflns_threshold_expression I>=2u(I) _iucr_refine_instructions_details ; TITL mo_SA3_Sehrishakram_redone_2_0_a.res in P2(1) CELL 0.71073 5.1153 7.1849 18.4639 90 96.817 90 ZERR 2 0.0003 0.0004 0.0009 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O UNIT 20 36 4 16 L.S. 10 PLAN 20 SIZE 0.07 0.29 0.5 TEMP 0 CONF MORE -1 FMAP 2 ACTA BOND BOND $H HTAB LIST 6 MERG 2 WGHT 0.033143 0.212282 FVAR 1.507747 REM REM REM O2 4 -0.19415 -0.66340 -0.70646 11.00000 0.04545 0.05871 0.03428 = -0.00350 -0.00338 0.01477 O3 4 -0.54903 -0.51385 -0.67679 11.00000 0.04595 0.05905 0.03017 = -0.01119 0.00036 0.01063 O4 4 -0.30701 -0.47791 -0.54825 11.00000 0.03103 0.05945 0.02276 = -0.00818 0.00105 -0.00069 O5 4 -0.67432 -0.50195 -0.49491 11.00000 0.02347 0.03961 0.03861 = -0.00859 -0.00121 -0.00290 O6 4 -0.34157 -0.48784 -0.25593 11.00000 0.05200 0.05631 0.03686 = -0.00009 0.00727 0.00766 O7 4 0.03865 -0.56440 -0.19112 11.00000 0.05604 0.06534 0.02878 = 0.00385 -0.00212 -0.00687 O8 4 -0.14194 -0.46769 -0.07159 11.00000 0.11703 0.10181 0.04291 = -0.00082 0.01589 -0.02910 N1 3 -0.40108 -0.70273 -0.84719 11.00000 0.09875 0.02924 0.02832 = -0.00040 0.00901 0.01172 N2 3 -0.05954 -0.29848 -0.42950 11.00000 0.02831 0.02457 0.02569 = 0.00107 -0.00030 -0.00540 AFIX 137 H2a 2 0.01776 -0.26363 -0.38588 11.00000 -1.50000 H2b 2 0.05805 -0.35401 -0.45410 11.00000 -1.50000 H2c 2 -0.12423 -0.19885 -0.45407 11.00000 -1.50000 AFIX 0 O1 4 -0.21017 -0.67809 -0.95192 11.00000 0.13290 0.06672 0.04401 = 0.00217 0.03465 0.02427 C1 1 -0.33731 -0.61159 -0.90464 11.00000 0.07662 0.04143 0.03405 = 0.00329 0.00206 0.00435 C2 1 -0.44153 -0.42127 -0.90392 11.00000 0.14725 0.04897 0.05786 = 0.01546 0.03143 0.02860 AFIX 23 H2d 2 -0.30071 -0.33131 -0.90509 11.00000 -1.20000 H2e 2 -0.57111 -0.40070 -0.94593 11.00000 -1.20000 AFIX 0 C3 1 -0.56600 -0.40212 -0.83460 11.00000 0.07940 0.04552 0.04181 = 0.00386 -0.00470 0.02119 AFIX 23 H3a 2 -0.47143 -0.31163 -0.80245 11.00000 -1.20000 H3b 2 -0.74785 -0.36248 -0.84500 11.00000 -1.20000 AFIX 0 C4 1 -0.55009 -0.59533 -0.79956 11.00000 0.04861 0.03419 0.02898 = -0.00139 -0.00232 0.00293 AFIX 13 H4 2 -0.72721 -0.64767 -0.80005 11.00000 -1.20000 AFIX 0 C5 1 -0.40990 -0.59552 -0.72237 11.00000 0.03990 0.03122 0.02914 = -0.00006 0.00045 -0.00074 C6 1 -0.43341 -0.47120 -0.49441 11.00000 0.02875 0.02232 0.03103 = -0.00094 0.00177 0.00183 C7 1 -0.27729 -0.43053 -0.42022 11.00000 0.02500 0.02566 0.02289 = -0.00274 0.00433 -0.00442 AFIX 13 H7a 2 -0.39442 -0.37535 -0.38777 11.00000 -1.20000 AFIX 0 C8 1 -0.17292 -0.61645 -0.38876 11.00000 0.04019 0.02504 0.03079 = 0.00090 0.00501 -0.00180 AFIX 23 H8a 2 -0.32303 -0.69459 -0.38229 11.00000 -1.20000 H8b 2 -0.07819 -0.67631 -0.42487 11.00000 -1.20000 AFIX 0 C9 1 0.00672 -0.61305 -0.31693 11.00000 0.03995 0.03391 0.03019 = 0.00437 -0.00301 0.00586 AFIX 23 H9a 2 0.07347 -0.73779 -0.30658 11.00000 -1.20000 H9b 2 0.15623 -0.53350 -0.32252 11.00000 -1.20000 AFIX 0 C10 1 -0.12112 -0.54618 -0.25318 11.00000 0.04665 0.02949 0.03238 = 0.00672 0.00322 -0.00477 H7 2 -0.04225 -0.53568 -0.15233 11.00000 -1.50000 H1 2 -0.33943 -0.82727 -0.83246 11.00000 -1.50000 H3 2 -0.46664 -0.49694 -0.62787 11.00000 -1.50000 H8c 2 -0.12580 -0.55182 -0.03144 11.00000 0.14712 H8d 2 0.00950 -0.39516 -0.05831 11.00000 0.09588 HKLF 4 END Q1 1 -0.6 -0.625 -0.55 11 0.05 0.27 Q2 1 -0.533333 -0.541667 -0.283333 11 0.05 0.26 Q3 1 0.066667 -0.541667 -0.716667 11 0.05 0.24 Q4 1 -0.266667 -0.458333 -0.033333 11 0.05 0.24 REM The information below was added by Olex2. REM REM R1 = 0.0505 for 1905 Fo > 4sig(Fo) and 0.0744 for all 2442 data REM 199 parameters refined using 1 restraints REM Highest difference peak 0.2705, deepest hole -0.2724 REM Mean Shift 0.0000, Max Shift 0.0003. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0744 REM R1_gt = 0.0505 REM wR_ref = 0.1157 REM GOOF = 1.1218 REM Shift_max = 0.0003 REM Shift_mean = 0.0000 REM Reflections_all = 2442 REM Reflections_gt = 1905 REM Parameters = 199 REM Hole = -0.2724 REM Peak = 0.2705 REM Flack = 0.0(19) ; _cod_data_source_file ef3024sup1.cif _cod_data_source_block IAM_SHELX _cod_original_sg_symbol_Hall ' P 2yb' _cod_database_code 2022512 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,y+1/2,-z loop_ _atom_site_type_symbol _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_occupancy O O2 -0.1942(5) -0.6634(4) -0.70646(12) 0.0468(7) Uani 1.000000 O O3 -0.5490(5) -0.5139(4) -0.67679(12) 0.0454(7) Uani 1.000000 O O4 -0.3070(4) -0.4779(4) -0.54825(10) 0.0379(6) Uani 1.000000 O O5 -0.6743(4) -0.5020(3) -0.49491(11) 0.0343(6) Uani 1.000000 O O6 -0.3416(5) -0.4878(4) -0.25593(12) 0.0482(7) Uani 1.000000 O O7 0.0386(5) -0.5644(4) -0.19112(12) 0.0506(8) Uani 1.000000 O O8 -0.1419(9) -0.4677(7) -0.07159(18) 0.0867(12) Uani 1.000000 N N1 -0.4011(8) -0.7027(5) -0.84719(15) 0.0520(10) Uani 1.000000 N N2 -0.0595(5) -0.2985(4) -0.42950(13) 0.0265(6) Uani 1.000000 H H2a 0.018(3) -0.264(2) -0.38588(13) 0.0397(9) Uiso 1.000000 H H2b 0.058(2) -0.3540(9) -0.4541(9) 0.0397(9) Uiso 1.000000 H H2c -0.1242(7) -0.1988(13) -0.4541(10) 0.0397(9) Uiso 1.000000 O O1 -0.2102(7) -0.6781(4) -0.95192(14) 0.0793(11) Uani 1.000000 C C1 -0.3373(9) -0.6116(6) -0.9046(2) 0.0511(11) Uani 1.000000 C C2 -0.4415(13) -0.4213(7) -0.9039(3) 0.0831(18) Uani 1.000000 H H2d -0.3007(13) -0.3313(7) -0.9051(3) 0.100(2) Uiso 1.000000 H H2e -0.5711(13) -0.4007(7) -0.9459(3) 0.100(2) Uiso 1.000000 C C3 -0.5660(10) -0.4021(6) -0.8346(2) 0.0565(12) Uani 1.000000 H H3a -0.4714(10) -0.3116(6) -0.8025(2) 0.0678(14) Uiso 1.000000 H H3b -0.7479(10) -0.3625(6) -0.8450(2) 0.0678(14) Uiso 1.000000 C C4 -0.5501(7) -0.5953(5) -0.79956(16) 0.0378(9) Uani 1.000000 H H4 -0.7272(7) -0.6477(5) -0.80005(16) 0.0454(11) Uiso 1.000000 C C5 -0.4099(7) -0.5955(5) -0.72237(17) 0.0337(8) Uani 1.000000 C C6 -0.4334(6) -0.4712(5) -0.49441(16) 0.0275(7) Uani 1.000000 C C7 -0.2773(6) -0.4305(4) -0.42022(15) 0.0244(7) Uani 1.000000 H H7a -0.3944(6) -0.3754(4) -0.38777(15) 0.0293(9) Uiso 1.000000 C C8 -0.1729(7) -0.6164(5) -0.38876(16) 0.0319(8) Uani 1.000000 H H8a -0.3230(7) -0.6946(5) -0.38229(16) 0.0383(9) Uiso 1.000000 H H8b -0.0782(7) -0.6763(5) -0.42487(16) 0.0383(9) Uiso 1.000000 C C9 0.0067(7) -0.6130(5) -0.31693(15) 0.0353(8) Uani 1.000000 H H9a 0.0735(7) -0.7378(5) -0.30658(15) 0.0423(10) Uiso 1.000000 H H9b 0.1562(7) -0.5335(5) -0.32252(15) 0.0423(10) Uiso 1.000000 C C10 -0.1211(8) -0.5462(5) -0.25318(17) 0.0363(9) Uani 1.000000 H H7 -0.042(7) -0.536(6) -0.152(2) 0.0544(13) Uiso 1.000000 H H1 -0.339(7) -0.827(6) -0.832(2) 0.0544(13) Uiso 1.000000 H H3 -0.467(7) -0.497(7) -0.628(2) 0.0544(13) Uiso 1.000000 H H8c -0.126(12) -0.552(11) -0.031(4) 0.15(3) Uiso 1.000000 H H8d 0.010(12) -0.395(8) -0.058(3) 0.10(2) Uiso 1.000000 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 0.0454(16) 0.0587(18) 0.0343(13) 0.0148(14) -0.0034(12) -0.0035(13) O3 0.0459(14) 0.0590(18) 0.0302(12) 0.0106(15) 0.0004(11) -0.0112(13) O4 0.0310(12) 0.0594(17) 0.0228(10) -0.0007(13) 0.0010(9) -0.0082(12) O5 0.0235(12) 0.0396(15) 0.0386(12) -0.0029(12) -0.0012(9) -0.0086(12) O6 0.0520(16) 0.0563(18) 0.0369(13) 0.0077(16) 0.0073(11) -0.0001(14) O7 0.0560(17) 0.065(2) 0.0288(12) -0.0069(15) -0.0021(12) 0.0038(14) O8 0.117(3) 0.102(3) 0.0429(18) -0.029(3) 0.0159(18) -0.001(2) N1 0.099(3) 0.0292(19) 0.0283(16) 0.0117(19) 0.0090(17) -0.0004(15) N2 0.0283(14) 0.0246(14) 0.0257(13) -0.0054(12) -0.0003(11) 0.0011(12) O1 0.133(3) 0.067(2) 0.0440(16) 0.024(2) 0.0347(18) 0.0022(17) C1 0.077(3) 0.041(2) 0.0340(19) 0.004(2) 0.002(2) 0.003(2) C2 0.147(5) 0.049(3) 0.058(3) 0.029(3) 0.031(3) 0.015(2) C3 0.079(3) 0.046(3) 0.042(2) 0.021(2) -0.005(2) 0.004(2) C4 0.049(2) 0.034(2) 0.0290(16) 0.0029(18) -0.0023(16) -0.0014(17) C5 0.040(2) 0.0312(19) 0.0291(16) -0.0007(17) 0.0005(15) -0.0001(16) C6 0.0288(17) 0.0223(17) 0.0310(16) 0.0018(14) 0.0018(13) -0.0009(15) C7 0.0250(17) 0.0257(18) 0.0229(15) -0.0044(13) 0.0043(13) -0.0027(14) C8 0.040(2) 0.0250(18) 0.0308(17) -0.0018(16) 0.0050(14) 0.0009(16) C9 0.040(2) 0.034(2) 0.0302(16) 0.0059(17) -0.0030(15) 0.0044(16) C10 0.047(2) 0.029(2) 0.0324(18) -0.0048(17) 0.0032(16) 0.0067(16) loop_ _atom_type_symbol _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_dispersion_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236 57.79970 0.0030380000826 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' C 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870 51.65120 0.215599998832 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' O 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390 32.90890 0.250800013542 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' N 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750 0.58260 -11.5290002823 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' loop_ _diffrn_refln_index_h _diffrn_refln_index_k _diffrn_refln_index_l 1 0 0 -1 0 0 1 0 0 -1 0 0 2 0 0 2 0 0 -2 0 0 -2 0 0 3 0 0 -3 0 0 -4 0 0 4 0 0 4 0 0 -5 0 0 5 0 0 5 0 0 -6 0 0 0 -1 0 0 -1 0 0 -1 0 0 -1 0 0 1 0 0 1 0 0 1 0 1 -1 0 -1 -1 0 1 1 0 -1 1 0 2 -1 0 -2 -1 0 2 -1 0 2 1 0 -2 1 0 -2 1 0 2 1 0 3 -1 0 -3 -1 0 -3 -1 0 3 -1 0 -3 1 0 3 1 0 4 -1 0 -4 -1 0 4 -1 0 -4 1 0 5 -1 0 5 -1 0 -5 -1 0 -5 1 0 5 1 0 -6 -1 0 6 -1 0 -6 1 0 -1 -2 0 1 -2 0 -1 -2 0 1 -2 0 1 -2 0 -1 -2 0 -1 2 0 -1 2 0 1 2 0 -1 2 0 1 2 0 2 -2 0 -2 -2 0 2 -2 0 2 2 0 2 2 0 2 2 0 -2 2 0 -2 2 0 3 -2 0 -3 -2 0 3 -2 0 -3 2 0 3 2 0 4 -2 0 -4 -2 0 4 -2 0 -4 2 0 5 -2 0 5 -2 0 -5 -2 0 -5 2 0 5 2 0 0 -3 0 0 -3 0 0 -3 0 0 -3 0 0 3 0 0 3 0 0 3 0 -1 -3 0 1 -3 0 1 -3 0 -1 -3 0 -1 3 0 1 3 0 1 3 0 -1 3 0 1 3 0 2 -3 0 -2 -3 0 2 -3 0 -2 -3 0 2 3 0 2 3 0 -2 3 0 2 3 0 3 -3 0 3 -3 0 -3 -3 0 -3 3 0 3 3 0 3 3 0 4 -3 0 -4 -3 0 4 -3 0 -4 -3 0 4 3 0 -4 3 0 5 -3 0 -5 -3 0 5 -3 0 -5 3 0 5 3 0 0 -4 0 0 -4 0 0 4 0 1 -4 0 1 -4 0 -1 -4 0 1 4 0 -1 4 0 1 4 0 2 -4 0 -2 -4 0 2 -4 0 2 4 0 2 4 0 -2 4 0 3 -4 0 3 -4 0 3 4 0 -3 4 0 3 4 0 4 -4 0 4 -4 0 -4 -4 0 4 4 0 -4 4 0 -5 -4 0 5 -4 0 5 -4 0 5 4 0 -5 4 0 0 -5 0 0 -5 0 0 5 0 1 -5 0 1 -5 0 -1 -5 0 -1 -5 0 1 -5 0 -1 5 0 1 5 0 1 5 0 2 -5 0 2 -5 0 -2 -5 0 -2 -5 0 2 5 0 2 5 0 -2 5 0 -3 -5 0 3 -5 0 3 -5 0 3 5 0 -3 5 0 3 5 0 4 -5 0 4 -5 0 -4 5 0 4 5 0 0 -6 0 0 -6 0 0 6 0 -1 -6 0 1 -6 0 1 -6 0 1 -6 0 -1 -6 0 1 6 0 -1 6 0 2 -6 0 -2 -6 0 2 -6 0 -2 -6 0 -2 6 0 2 6 0 3 -6 0 -3 -6 0 3 -6 0 -3 6 0 3 6 0 3 6 0 4 -6 0 4 -6 0 -4 6 0 4 6 0 0 -7 0 0 -7 0 0 7 0 0 7 0 1 -7 0 -1 -7 0 1 7 0 -1 7 0 1 7 0 2 -7 0 2 -7 0 2 -7 0 -2 -7 0 -2 7 0 2 7 0 3 -7 0 3 -7 0 3 -7 0 3 7 0 3 7 0 -3 7 0 0 -8 0 0 8 0 0 8 0 1 -8 0 1 -8 0 -1 -8 0 2 -8 0 2 -8 0 2 -8 0 2 8 0 -2 8 0 -6 0 1 6 0 -1 -5 0 1 5 0 -1 4 0 -1 4 0 -1 -4 0 1 -3 0 1 3 0 -1 -2 0 1 2 0 -1 -2 0 1 2 0 -1 1 0 -1 -1 0 1 1 0 -1 -1 0 1 1 0 1 -1 0 -1 -1 0 -1 1 0 1 -1 0 -1 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-1 5 18 3 0 -19 -3 0 19 3 0 -19 -2 0 19 2 0 -19 2 0 -19 -2 0 19 -1 0 19 1 0 -19 1 0 -19 1 0 -19 -1 0 19 0 0 19 0 0 -19 0 0 -19 0 0 -19 -1 0 -19 1 0 19 -1 0 -19 -1 0 -19 2 0 19 -2 0 -19 3 -1 -19 -3 -1 19 3 -1 -19 -3 1 19 3 1 -19 3 1 -19 -2 -1 19 2 -1 -19 2 -1 -19 2 -1 -19 -2 -1 19 -2 1 19 2 1 -19 2 1 -19 1 -1 -19 1 -1 -19 -1 -1 19 1 1 -19 1 1 -19 -1 1 19 1 1 -19 0 -1 -19 0 -1 -19 0 -1 19 0 -1 -19 0 1 19 0 1 -19 0 1 -19 1 -1 19 -1 -1 -19 -1 1 -19 1 1 19 -1 1 -19 -2 -1 -19 -2 1 -19 2 1 19 3 -2 -19 -3 -2 19 3 2 -19 3 2 -19 2 -2 -19 2 -2 -19 -2 -2 19 2 -2 -19 2 2 -19 2 2 -19 -2 2 19 -1 -2 19 1 -2 -19 -1 -2 19 1 -2 -19 1 2 -19 -1 2 19 1 2 -19 1 2 -19 0 -2 -19 0 -2 19 0 -2 -19 0 2 -19 0 2 -19 0 2 -19 0 2 19 -1 -2 -19 1 -2 19 -1 2 -19 -1 2 -19 1 2 19 -2 -2 -19 -2 2 -19 -2 -3 19 2 -3 -19 2 -3 -19 2 3 -19 -2 3 19 1 -3 -19 -1 -3 19 1 -3 -19 -1 3 19 1 3 -19 1 3 -19 0 -3 -19 0 -3 -19 0 3 -19 0 3 19 0 3 -19 1 -3 19 -1 -3 -19 -1 3 -19 1 3 19 2 -4 -19 -2 -4 19 2 -4 -19 -2 4 19 2 4 -19 1 -4 -19 -1 -4 19 1 4 -19 -1 4 19 1 4 -19 0 -4 19 0 -4 -19 0 4 -19 0 4 -19 0 4 19 -3 0 20 3 0 -20 2 0 -20 2 0 -20 -2 0 20 2 0 -20 -1 0 20 1 0 -20 1 0 -20 -1 0 20 1 0 -20 0 0 -20 0 0 20 0 0 -20 0 0 -20 -1 0 -20 1 0 20 -1 0 -20 -2 0 -20 -3 -1 20 3 -1 -20 3 -1 -20 -3 1 20 3 1 -20 2 -1 -20 2 -1 -20 -2 -1 20 2 -1 -20 -2 1 20 2 1 -20 2 1 -20 -1 -1 20 1 -1 -20 1 -1 -20 -1 -1 20 1 -1 -20 -1 1 20 1 1 -20 1 1 -20 -1 1 20 1 1 -20 0 -1 20 0 -1 -20 0 -1 -20 0 1 -20 0 1 -20 0 1 -20 0 1 20 1 -1 20 -1 -1 -20 -1 1 -20 -1 1 -20 1 1 20 -2 -2 20 -2 -2 20 2 -2 -20 2 -2 -20 2 -2 -20 -2 2 20 2 2 -20 -1 -2 20 1 -2 -20 -1 -2 20 1 -2 -20 1 2 -20 1 2 -20 -1 2 20 0 -2 -20 0 -2 -20 0 -2 -20 0 2 -20 0 2 -20 0 2 20 -1 -2 -20 -1 2 -20 -1 2 -20 1 2 20 -2 -3 20 2 -3 -20 2 3 -20 -2 3 20 1 -3 -20 1 -3 -20 1 -3 -20 1 3 -20 1 3 -20 -1 3 20 0 -3 20 0 -3 -20 0 3 20 2 0 -21 2 0 -21 -2 0 21 -1 0 21 1 0 -21 1 0 -21 1 0 -21 0 0 -21 0 0 -21 0 0 21 0 0 -21 -1 0 -21 -2 -1 21 2 -1 -21 -2 -1 21 2 -1 -21 2 1 -21 2 1 -21 -2 1 21 1 -1 -21 -1 -1 21 1 -1 -21 1 1 -21 1 1 -21 -1 1 21 1 1 -21 0 -1 21 0 -1 -21 0 1 21 0 1 -21 0 1 -21 0 1 -21 -1 -1 -21 -1 1 -21 1 1 21 -1 1 -21 -2 -2 21 2 -2 -21 2 -2 -21 -2 2 21 1 -2 -21 1 -2 -21 1 -2 -21 1 2 -21 -1 2 21 1 2 -21 1 2 -21 0 -2 -21 0 -2 -21 0 2 -21 0 2 -21 0 2 21 1 0 -22 1 0 -22 -1 0 22 1 0 -22 0 0 22 0 0 -22 0 0 -22 1 -1 -22 1 -1 -22 -1 -1 22 1 -1 -22 1 1 -22 -1 1 22 1 1 -22 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C4 N1 C1 . . 114.9(3) ? O1 C1 N1 . . 125.0(4) ? C2 C1 N1 . . 109.3(4) ? C2 C1 O1 . . 125.8(4) ? C3 C2 C1 . . 106.5(4) ? C4 C3 C2 . . 105.7(3) ? C3 C4 N1 . . 103.4(3) ? C5 C4 N1 . . 110.2(3) ? C5 C4 C3 . . 113.2(3) ? O3 C5 O2 . . 125.2(3) ? C4 C5 O2 . . 122.9(3) ? C4 C5 O3 . . 111.9(3) ? O5 C6 O4 . . 126.1(3) ? C7 C6 O4 . . 117.1(3) ? C7 C6 O5 . . 116.7(3) ? C6 C7 N2 . . 109.7(2) ? C8 C7 N2 . . 111.6(2) ? C8 C7 C6 . . 107.2(2) ? C9 C8 C7 . . 117.7(3) ? C10 C9 C8 . . 114.6(3) ? O7 C10 O6 . . 123.3(3) ? C9 C10 O6 . . 125.3(3) ? C9 C10 O7 . . 111.4(3) ? 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 O2 C5 . 1.210(4) ? O3 C5 . 1.304(4) ? O4 C6 . 1.249(3) ? O5 C6 . 1.251(3) ? O6 C10 . 1.198(4) ? O7 C10 . 1.333(4) ? N1 C1 . 1.320(5) ? N1 C4 . 1.452(5) ? N2 C7 . 1.488(4) ? O1 C1 . 1.244(5) ? C1 C2 . 1.468(6) ? C2 C3 . 1.502(6) ? C3 C4 . 1.530(5) ? C4 C5 . 1.518(5) ? C6 C7 . 1.530(4) ? C7 C8 . 1.527(4) ? C8 C9 . 1.521(4) ? C9 C10 . 1.492(4) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 C5 C4 N1 . . . . 5.8(4) ? O2 C5 C4 C3 . . . . -109.3(4) ? O3 C5 C4 N1 . . . . -174.5(3) ? O3 C5 C4 C3 . . . . 70.3(3) ? O4 C6 C7 N2 . . . . 35.1(3) ? O4 C6 C7 C8 . . . . -86.2(3) ? O5 C6 C7 N2 . . . . -147.6(3) ? O5 C6 C7 C8 . . . . 91.0(3) ? O6 C10 C9 C8 . . . . -4.3(4) ? O7 C10 C9 C8 . . . . 173.7(3) ? N1 C1 C2 C3 . . . . 3.6(4) ? N1 C4 C3 C2 . . . . 4.7(4) ? N2 C7 C8 C9 . . . . 55.7(3) ? O1 C1 C2 C3 . . . . -176.8(6) ? C1 C2 C3 C4 . . . . -5.1(5) ? C2 C3 C4 C5 . . . . 123.8(4) ? C6 C7 C8 C9 . . . . 175.8(2) ? C7 C8 C9 C10 . . . . 64.9(3) ? _cod_database_fobs_code 2022512