#------------------------------------------------------------------------------ #$Date: 2025-08-19 20:21:09 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301810 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/00/3500024.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_3500024 loop_ _publ_author_name 'Thierry Maris' _publ_section_title ; 4-Acetamidophenyl 2-hydroxybenzoate ; _journal_name_full 'Personal communication to COD' _journal_year 2015 _chemical_absolute_configuration ad _chemical_formula_moiety 'C15 H13 N O4' _chemical_formula_sum 'C15 H13 N O4' _chemical_formula_weight 271.26 _chemical_name_common '4-Acetamidophenyl salicylate' _chemical_name_systematic ; 4-Acetamidophenyl 2-hydroxybenzoate ; _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2013-01-18 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _cell_angle_alpha 90.00 _cell_angle_beta 100.040(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.7567(2) _cell_length_b 25.8548(11) _cell_length_c 8.7938(4) _cell_measurement_reflns_used 8180 _cell_measurement_temperature 150 _cell_measurement_theta_max 73.189 _cell_measurement_theta_min 3.419 _cell_volume 1288.81(9) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _diffrn_ambient_temperature 150 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator 'Montel 200 Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_unetI/netI 0.0282 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 9191 _diffrn_reflns_theta_full 73.31 _diffrn_reflns_theta_max 73.31 _diffrn_reflns_theta_min 3.42 _diffrn_source 'FR591 Rotating Anode' _diffrn_source_target Cu _exptl_absorpt_coefficient_mu 0.852 _exptl_absorpt_correction_T_max 0.7638 _exptl_absorpt_correction_T_min 0.6335 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; ? was used for absorption correction. wR2(int) was 0.1249 before and 0.0516 after correction. The Ratio of minimum to maximum transmission is 0.8294. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 568 _exptl_crystal_preparation Commercial _exptl_crystal_recrystallization_method 'Recrystallized from EtOAc' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_special_details ; ? ; _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; _refine_diff_density_max 0.191 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.073 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(18) _refine_ls_extinction_coef 0.0393(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 185 _refine_ls_number_reflns 2285 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.135 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0411 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.1496P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0954 _refine_ls_wR_factor_ref 0.0954 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_gt 2278 _reflns_number_total 2285 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL salophen in Cc #9 CELL 1.54178 5.7567 25.8548 8.7938 90 100.04 90 ZERR 4 0.0002 0.0011 0.0004 0 0.002 0 LATT -7 SYMM +X,-Y,0.5+Z SFAC C H N O UNIT 60 52 4 16 EQIV $1 0.5+X,0.5-Y,0.5+Z EQIV $2 +X,1-Y,-0.5+Z L.S. 12 PLAN 3 SIZE 0.18 0.18 0.32 TEMP -123.15 HTAB O1 O2 HTAB N1 O4_$1 HTAB O1 O3_$2 REM reset to Cc #9 BOND $H more -3 fmap 2 acta HTAB conf TWIN -1 0 0 0 -1 0 0 0 -1 2 REM E:/PROJETS/SALOPHEN/STRUCTURE/PHEN1/OLEX2/salophen.hkl WGHT 0.067600 0.149600 EXTI 0.039260 BASF 0.07621 FVAR 1.34068 O1 4 -0.036866 0.601251 0.218378 11.00000 0.05438 0.03081 = 0.03958 0.00802 0.01876 0.01099 AFIX 147 H1 2 0.040999 0.575527 0.197517 11.00000 -1.50000 AFIX 0 O2 4 0.129341 0.506442 0.253630 11.00000 0.03314 0.02977 = 0.03642 0.00153 0.01170 0.00343 O3 4 -0.021633 0.452706 0.412754 11.00000 0.04100 0.02295 = 0.03654 0.00080 0.01482 0.00484 O4 4 0.339154 0.257975 0.042406 11.00000 0.04325 0.03709 = 0.03353 -0.00944 -0.00351 0.00616 N1 3 0.531365 0.287028 0.275722 11.00000 0.02860 0.02694 = 0.02412 -0.00011 0.00161 0.00309 AFIX 43 H1A 2 0.653944 0.280747 0.348275 11.00000 -1.20000 AFIX 0 C1 1 -0.178285 0.587094 0.318731 11.00000 0.03409 0.03028 = 0.02524 -0.00052 0.00088 0.00474 C2 1 -0.339203 0.623881 0.355165 11.00000 0.04331 0.03127 = 0.02898 -0.00232 0.00073 0.01065 AFIX 43 H2 2 -0.342815 0.657547 0.311539 11.00000 -1.20000 AFIX 0 C3 1 -0.491589 0.611434 0.453658 11.00000 0.03384 0.04034 = 0.03132 -0.00907 -0.00091 0.01043 AFIX 43 H3 2 -0.601651 0.636486 0.475907 11.00000 -1.20000 AFIX 0 C4 1 -0.487203 0.562434 0.521707 11.00000 0.02919 0.04344 = 0.03328 -0.00934 0.00617 -0.00086 AFIX 43 H4 2 -0.592022 0.554284 0.590560 11.00000 -1.20000 AFIX 0 C5 1 -0.328465 0.526136 0.487360 11.00000 0.02835 0.03042 = 0.03287 -0.00447 0.00306 -0.00290 AFIX 43 H5 2 -0.324385 0.492840 0.533436 11.00000 -1.20000 AFIX 0 C6 1 -0.172463 0.537558 0.385271 11.00000 0.02789 0.02660 = 0.02584 -0.00401 0.00144 0.00237 C7 1 -0.006005 0.498774 0.342969 11.00000 0.02835 0.02492 = 0.02612 -0.00264 0.00068 -0.00019 C8 1 0.121652 0.412080 0.373753 11.00000 0.03613 0.02000 = 0.03185 0.00212 0.01303 0.00196 C9 1 0.344551 0.404855 0.457338 11.00000 0.03328 0.02504 = 0.02832 -0.00449 0.00706 -0.00782 AFIX 43 H9 2 0.406067 0.427891 0.538594 11.00000 -1.20000 AFIX 0 C10 1 0.478622 0.363288 0.421087 11.00000 0.02773 0.02706 = 0.02512 -0.00014 0.00434 -0.00308 AFIX 43 H10 2 0.633827 0.358277 0.476804 11.00000 -1.20000 AFIX 0 C11 1 0.386768 0.328941 0.303564 11.00000 0.02826 0.02145 = 0.02391 0.00184 0.00589 -0.00063 C12 1 0.158633 0.336452 0.221721 11.00000 0.03014 0.02565 = 0.02805 -0.00378 0.00279 -0.00105 AFIX 43 H12 2 0.093846 0.312985 0.142452 11.00000 -1.20000 AFIX 0 C13 1 0.027012 0.378439 0.256908 11.00000 0.02929 0.03085 = 0.02986 -0.00041 0.00150 0.00316 AFIX 43 H13 2 -0.127554 0.384033 0.200888 11.00000 -1.20000 AFIX 0 C14 1 0.504648 0.255282 0.151053 11.00000 0.03195 0.02225 = 0.02829 -0.00063 0.00574 -0.00031 C15 1 0.699808 0.216420 0.153092 11.00000 0.04283 0.03014 = 0.04212 -0.00330 0.00818 0.00882 AFIX 137 H15A 2 0.794849 0.225793 0.075019 11.00000 -1.50000 H15B 2 0.631695 0.181962 0.130227 11.00000 -1.50000 H15C 2 0.799960 0.216200 0.255358 11.00000 -1.50000 HKLF 4 REM salophen in Cc #9 REM R1 = 0.0411 for 2278 Fo > 4sig(Fo) and 0.0411 for all 2285 data REM 185 parameters refined using 2 restraints END WGHT 0.0676 0.1496 REM Highest difference peak 0.191, deepest hole -0.283, 1-sigma level 0.073 Q1 1 -0.8757 0.5581 0.5838 11.00000 0.05 0.19 Q2 1 -0.5059 0.4782 0.3142 11.00000 0.05 0.19 Q3 1 0.9687 0.3118 0.3978 11.00000 0.05 0.19 REM The information below was added by Olex2. REM REM R1 = 0.0411 for 2278 Fo > 4sig(Fo) and n/a for all 9309 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.19, deepest hole -0.28 REM Mean Shift 0, Max Shift 0. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = n/a REM R1_gt = 0.0411 REM wR_ref = 0.0954 REM GOOF = 1.135 REM Shift_max = 0 REM Shift_mean = 0 REM Reflections_all = 9309 REM Reflections_gt = 2278 REM Parameters = n/a REM Hole = 0.19 REM Peak = -0.28 REM Flack = 0.08(16) ; _cod_data_source_file salophen.cif _cod_data_source_block salophen _cod_depositor_comments ; The following automatic conversions were performed: '_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according to the built-in table from CIF Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius ; _cod_database_code 3500024 _cod_database_fobs_code 3500024 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H2 of C2, H3 of C3, H4 of C4, H5 of C5, H9 of C9, H10 of C10, H1A of N1, H13 of C13, H12 of C12 At 1.5 times of: {H15A,H15B,H15C} of C15, H1 of O1 2.a Aromatic/amide H refined with riding coordinates: N1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13) 2.b Idealised Me refined as rotating group: C15(H15A,H15B,H15C) 2.c Idealised tetrahedral OH refined as rotating group: O1(H1) ; loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 'x, -y, z+1/2' 3 'x+1/2, y+1/2, z' 4 'x+1/2, -y+1/2, z+1/2' loop_ _atom_site_label _atom_site_type_symbol _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 _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0369(2) 0.60125(5) 0.21838(15) 0.0403(3) Uani 1 1 d . . . H1 H 0.0410 0.5755 0.1975 0.060 Uiso 1 1 calc R . . O2 O 0.1293(2) 0.50644(4) 0.25363(14) 0.0324(3) Uani 1 1 d . . . O3 O -0.0216(2) 0.45271(4) 0.41275(14) 0.0325(3) Uani 1 1 d . . . O4 O 0.3392(2) 0.25798(5) 0.04241(16) 0.0392(3) Uani 1 1 d . . . N1 N 0.5314(2) 0.28703(5) 0.27572(15) 0.0269(3) Uani 1 1 d . . . H1A H 0.6539 0.2807 0.3483 0.032 Uiso 1 1 calc R . . C1 C -0.1783(3) 0.58709(6) 0.31873(19) 0.0304(4) Uani 1 1 d . . . C2 C -0.3392(3) 0.62388(7) 0.35517(19) 0.0352(4) Uani 1 1 d . . . H2 H -0.3428 0.6575 0.3115 0.042 Uiso 1 1 calc R . . C3 C -0.4916(3) 0.61143(7) 0.4537(2) 0.0360(4) Uani 1 1 d . . . H3 H -0.6017 0.6365 0.4759 0.043 Uiso 1 1 calc R . . C4 C -0.4872(3) 0.56243(7) 0.5217(2) 0.0352(4) Uani 1 1 d . . . H4 H -0.5920 0.5543 0.5906 0.042 Uiso 1 1 calc R . . C5 C -0.3285(3) 0.52614(6) 0.4874(2) 0.0308(3) Uani 1 1 d . . . H5 H -0.3244 0.4928 0.5334 0.037 Uiso 1 1 calc R . . C6 C -0.1725(3) 0.53756(6) 0.38527(19) 0.0272(3) Uani 1 1 d . . . C7 C -0.0060(3) 0.49877(6) 0.34297(18) 0.0270(3) Uani 1 1 d . . . C8 C 0.1217(3) 0.41208(6) 0.37375(19) 0.0285(4) Uani 1 1 d . . . C9 C 0.3446(3) 0.40485(6) 0.45734(19) 0.0287(3) Uani 1 1 d . . . H9 H 0.4061 0.4279 0.5386 0.034 Uiso 1 1 calc R . . C10 C 0.4786(3) 0.36329(6) 0.42109(19) 0.0267(3) Uani 1 1 d . . . H10 H 0.6338 0.3583 0.4768 0.032 Uiso 1 1 calc R . . C11 C 0.3868(2) 0.32894(6) 0.30356(17) 0.0244(3) Uani 1 1 d . . . C12 C 0.1586(3) 0.33645(6) 0.22172(19) 0.0282(3) Uani 1 1 d . . . H12 H 0.0938 0.3130 0.1425 0.034 Uiso 1 1 calc R . . C13 C 0.0270(3) 0.37844(6) 0.25691(19) 0.0304(4) Uani 1 1 d . . . H13 H -0.1276 0.3840 0.2009 0.037 Uiso 1 1 calc R . . C14 C 0.5046(3) 0.25528(6) 0.15105(19) 0.0274(3) Uani 1 1 d . . . C15 C 0.6998(3) 0.21642(7) 0.1531(2) 0.0383(4) Uani 1 1 d . . . H15A H 0.7948 0.2258 0.0750 0.057 Uiso 1 1 calc R . . H15B H 0.6317 0.1820 0.1302 0.057 Uiso 1 1 calc R . . H15C H 0.8000 0.2162 0.2554 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0544(8) 0.0308(6) 0.0396(7) 0.0080(5) 0.0188(6) 0.0110(5) O2 0.0331(6) 0.0298(6) 0.0364(7) 0.0015(5) 0.0117(5) 0.0034(4) O3 0.0410(6) 0.0229(5) 0.0365(6) 0.0008(5) 0.0148(5) 0.0048(5) O4 0.0432(7) 0.0371(6) 0.0335(7) -0.0094(5) -0.0035(6) 0.0062(5) N1 0.0286(6) 0.0269(6) 0.0241(6) -0.0001(5) 0.0016(5) 0.0031(5) C1 0.0341(8) 0.0303(8) 0.0252(8) -0.0005(6) 0.0009(6) 0.0047(6) C2 0.0433(9) 0.0313(8) 0.0290(8) -0.0023(6) 0.0007(7) 0.0107(7) C3 0.0338(8) 0.0403(9) 0.0313(9) -0.0091(7) -0.0009(7) 0.0104(7) C4 0.0292(8) 0.0434(10) 0.0333(9) -0.0093(7) 0.0062(7) -0.0009(7) C5 0.0284(7) 0.0304(8) 0.0329(9) -0.0045(6) 0.0031(6) -0.0029(6) C6 0.0279(7) 0.0266(7) 0.0258(8) -0.0040(6) 0.0014(6) 0.0024(5) C7 0.0283(7) 0.0249(7) 0.0261(8) -0.0026(6) 0.0007(6) -0.0002(6) C8 0.0361(9) 0.0200(7) 0.0318(9) 0.0021(6) 0.0130(7) 0.0020(6) C9 0.0333(8) 0.0250(7) 0.0283(8) -0.0045(6) 0.0071(6) -0.0078(6) C10 0.0277(7) 0.0271(7) 0.0251(7) -0.0001(6) 0.0043(6) -0.0031(6) C11 0.0283(8) 0.0214(6) 0.0239(7) 0.0018(5) 0.0059(6) -0.0006(5) C12 0.0301(8) 0.0257(7) 0.0281(8) -0.0038(6) 0.0028(6) -0.0011(6) C13 0.0293(8) 0.0308(8) 0.0299(9) -0.0004(6) 0.0015(6) 0.0032(6) C14 0.0320(8) 0.0222(7) 0.0283(8) -0.0006(6) 0.0057(6) -0.0003(6) C15 0.0428(9) 0.0301(8) 0.0421(9) -0.0033(7) 0.0082(8) 0.0088(7) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C1 O1 H1 109.5 . . C7 O3 C8 117.20(12) . . C11 N1 H1A 116.0 . . C14 N1 H1A 116.0 . . C14 N1 C11 128.06(13) . . O1 C1 C2 117.54(14) . . O1 C1 C6 123.03(14) . . C2 C1 C6 119.42(15) . . C1 C2 H2 119.8 . . C3 C2 C1 120.31(16) . . C3 C2 H2 119.8 . . C2 C3 H3 119.5 . . C2 C3 C4 121.04(15) . . C4 C3 H3 119.5 . . C3 C4 H4 120.5 . . C5 C4 C3 119.04(15) . . C5 C4 H4 120.5 . . C4 C5 H5 119.4 . . C4 C5 C6 121.17(15) . . C6 C5 H5 119.4 . . C1 C6 C5 119.01(14) . . C1 C6 C7 118.85(14) . . C5 C6 C7 122.12(14) . . O2 C7 O3 122.60(14) . . O2 C7 C6 124.65(14) . . O3 C7 C6 112.74(13) . . C9 C8 O3 120.03(14) . . C9 C8 C13 121.42(14) . . C13 C8 O3 118.44(15) . . C8 C9 H9 120.5 . . C8 C9 C10 119.02(14) . . C10 C9 H9 120.5 . . C9 C10 H10 119.8 . . C9 C10 C11 120.49(15) . . C11 C10 H10 119.8 . . C10 C11 N1 117.24(13) . . C10 C11 C12 119.62(14) . . C12 C11 N1 123.13(14) . . C11 C12 H12 120.2 . . C13 C12 C11 119.62(14) . . C13 C12 H12 120.2 . . C8 C13 C12 119.82(15) . . C8 C13 H13 120.1 . . C12 C13 H13 120.1 . . O4 C14 N1 123.90(15) . . O4 C14 C15 121.56(15) . . N1 C14 C15 114.52(15) . . C14 C15 H15A 109.5 . . C14 C15 H15B 109.5 . . C14 C15 H15C 109.5 . . H15A C15 H15B 109.5 . . H15A C15 H15C 109.5 . . H15B C15 H15C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 H1 0.8400 . O1 C1 1.351(2) . O2 C7 1.215(2) . O3 C7 1.3500(19) . O3 C8 1.4142(18) . O4 C14 1.228(2) . N1 H1A 0.8800 . N1 C11 1.4136(18) . N1 C14 1.357(2) . C1 C2 1.403(2) . C1 C6 1.406(2) . C2 H2 0.9500 . C2 C3 1.374(3) . C3 H3 0.9500 . C3 C4 1.399(3) . C4 H4 0.9500 . C4 C5 1.380(2) . C5 H5 0.9500 . C5 C6 1.407(2) . C6 C7 1.479(2) . C8 C9 1.376(2) . C8 C13 1.383(2) . C9 H9 0.9500 . C9 C10 1.392(2) . C10 H10 0.9500 . C10 C11 1.395(2) . C11 C12 1.397(2) . C12 H12 0.9500 . C12 C13 1.389(2) . C13 H13 0.9500 . C14 C15 1.505(2) . C15 H15A 0.9800 . C15 H15B 0.9800 . C15 H15C 0.9800 . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.84 1.90 2.6300(15) 144.8 . O1 H1 O3 0.84 2.57 3.0429(17) 116.6 2_564 N1 H1A O4 0.88 2.10 2.9231(19) 154.9 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O1 C1 C2 C3 178.47(16) . . . . O1 C1 C6 C5 -179.28(15) . . . . O1 C1 C6 C7 -0.6(2) . . . . O3 C8 C9 C10 177.28(13) . . . . O3 C8 C13 C12 -176.40(14) . . . . N1 C11 C12 C13 179.49(14) . . . . C1 C2 C3 C4 1.2(3) . . . . C1 C6 C7 O2 0.1(2) . . . . C1 C6 C7 O3 -178.86(14) . . . . C2 C1 C6 C5 -0.1(2) . . . . C2 C1 C6 C7 178.55(14) . . . . C2 C3 C4 C5 -0.7(3) . . . . C3 C4 C5 C6 -0.2(2) . . . . C4 C5 C6 C1 0.6(2) . . . . C4 C5 C6 C7 -178.05(14) . . . . C5 C6 C7 O2 178.77(15) . . . . C5 C6 C7 O3 -0.2(2) . . . . C6 C1 C2 C3 -0.7(2) . . . . C7 O3 C8 C9 90.30(18) . . . . C7 O3 C8 C13 -93.53(18) . . . . C8 O3 C7 O2 -2.2(2) . . . . C8 O3 C7 C6 176.79(14) . . . . C8 C9 C10 C11 -1.1(2) . . . . C9 C8 C13 C12 -0.3(2) . . . . C9 C10 C11 N1 -178.63(13) . . . . C9 C10 C11 C12 0.1(2) . . . . C10 C11 C12 C13 0.9(2) . . . . C11 N1 C14 O4 -2.3(2) . . . . C11 N1 C14 C15 176.20(14) . . . . C11 C12 C13 C8 -0.8(2) . . . . C13 C8 C9 C10 1.2(2) . . . . C14 N1 C11 C10 -165.15(15) . . . . C14 N1 C11 C12 16.2(2) . . . . loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 1984