#------------------------------------------------------------------------------ #$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301806 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238921.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_2238921 loop_ _publ_author_name 'Qachchachi, Fatima-Zahrae' 'Kandri Rodi, Youssef' 'Essassi, El Mokhtar' 'Kunz, Werner' 'El Ammari, Lahcen' _publ_contact_author ; Fatima-Zahrae Qachchachi Laboratoire de Chimie Organique Appliqu\'ee Universit\'e Sidi Mohamed Ben Abdallah Facult\'e des Sciences et Techniques Route d'Immouzzer BP 2202 F\`es Morocco ; _publ_section_title ; 1-Octylindoline-2,3-dione ; _journal_coeditor_code RZ5095 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1801 _journal_paper_doi 10.1107/S1600536813031383 _journal_volume 69 _journal_year 2013 _chemical_formula_iupac 'C16 H21 N O2' _chemical_formula_moiety 'C16 H21 N O2' _chemical_formula_sum 'C16 H21 N O2' _chemical_formula_weight 259.34 _chemical_melting_point 317 _chemical_name_systematic ; 1-Octylindoline-2,3-dione ; _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 108.941(18) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 20.266(4) _cell_length_b 4.69250(10) _cell_length_c 15.7807(11) _cell_measurement_reflns_used 5321 _cell_measurement_temperature 123.00(18) _cell_measurement_theta_max 73.5259 _cell_measurement_theta_min 2.9581 _cell_volume 1419.5(3) _computing_cell_refinement 'CrysAlis PRO (Oxford Diffraction, 2012)' _computing_data_collection 'CrysAlis PRO (Oxford Diffraction, 2012)' _computing_data_reduction 'CrysAlis PRO (Oxford Diffraction, 2012)' _computing_molecular_graphics 'WinGX (Farrugia, 2012)' _computing_publication_material 'WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 123.00(18) _diffrn_detector_area_resol_mean 20.7092 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova (single source at offset, Atlas)' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 13541 _diffrn_reflns_theta_full 73.69 _diffrn_reflns_theta_max 73.69 _diffrn_reflns_theta_min 4.61 _exptl_absorpt_coefficient_mu 0.630 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_correction_T_min 0.899 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; [CrysAlis PRO (Oxford Diffraction, 2012); analytical numeric absorption correction using a multi-faceted crystal model (Clark & Reid, 1995)] ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.3120 _exptl_crystal_size_mid 0.0658 _exptl_crystal_size_min 0.0399 _refine_diff_density_max 0.491 _refine_diff_density_min -0.224 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2811 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.180 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0568 _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^)+(0.0633P)^2^+1.1901P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1607 _refine_ls_wR_factor_ref 0.1673 _reflns_number_gt 2462 _reflns_number_total 2811 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL FZ2 in P21/c CELL 1.54184 20.2660 4.6925 15.7807 90.000 108.941 90.000 ZERR 4.00 0.0042 0.0001 0.0011 0.000 0.018 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 64 84 4 8 MERG 2 OMIT 0 0 6 OMIT -3 1 6 OMIT -6 0 12 shel 40 0.8 HTAB C6 O1_$1 HTAB C6 O2_$2 HTAB C7 O1_$1 HTAB C4 O2_$3 eqiv $1 x, 3/2-y, 1/2+z eqiv $2 x, 5/2-y, 1/2+z eqiv $3 1-x, 3-y, 1-z FMAP 2 PLAN 10 conf ACTA BOND BOND $H L.S. 10 WGHT 0.063300 1.190100 FVAR 7.31288 O1 4 0.333542 0.766731 0.346566 11.00000 0.03964 0.04937 = 0.02932 -0.00513 0.01017 0.00807 O2 4 0.445108 1.190030 0.424543 11.00000 0.03031 0.05593 = 0.03346 0.01319 0.01604 0.00400 N1 3 0.325743 0.783567 0.489388 11.00000 0.02220 0.03137 = 0.02715 -0.00280 0.00668 0.00004 C1 1 0.352209 0.857358 0.423189 11.00000 0.02650 0.03719 = 0.02618 0.00139 0.00872 0.00981 C2 1 0.409992 1.083531 0.464681 11.00000 0.02245 0.03494 = 0.02973 0.00857 0.00925 0.00882 C3 1 0.407977 1.129485 0.555426 11.00000 0.02253 0.02849 = 0.02749 0.00720 0.00961 0.00502 C4 1 0.445089 1.312374 0.622814 11.00000 0.02072 0.03071 = 0.03641 0.00486 0.00776 -0.00076 AFIX 43 H4 2 0.479093 1.432516 0.614837 11.00000 -1.20000 AFIX 0 C5 1 0.430149 1.311591 0.702750 11.00000 0.02673 0.03191 = 0.03119 -0.00133 0.00587 0.00003 AFIX 43 H5 2 0.453981 1.434258 0.748804 11.00000 -1.20000 AFIX 0 C6 1 0.379916 1.129004 0.714284 11.00000 0.02751 0.03526 = 0.02433 0.00260 0.00835 0.00471 AFIX 43 H6 2 0.370985 1.130998 0.768484 11.00000 -1.20000 AFIX 0 C7 1 0.342296 0.942038 0.646915 11.00000 0.02402 0.03060 = 0.02863 0.00313 0.01068 0.00006 AFIX 43 H7 2 0.308870 0.819601 0.655318 11.00000 -1.20000 AFIX 0 C8 1 0.356851 0.947099 0.567864 11.00000 0.01882 0.02571 = 0.02627 0.00108 0.00529 0.00401 C9 1 0.266517 0.592996 0.475807 11.00000 0.02496 0.02841 = 0.03497 -0.00306 0.00640 -0.00120 AFIX 23 H9A 2 0.273152 0.481861 0.529770 11.00000 -1.20000 H9B 2 0.264477 0.461827 0.427514 11.00000 -1.20000 AFIX 0 C10 1 0.197681 0.754169 0.453151 11.00000 0.02471 0.02990 = 0.03398 -0.00140 0.00737 0.00144 AFIX 23 H10A 2 0.193977 0.883690 0.403913 11.00000 -1.20000 H10B 2 0.197588 0.867433 0.504531 11.00000 -1.20000 AFIX 0 C11 1 0.134370 0.557154 0.427305 11.00000 0.02376 0.03109 = 0.03446 -0.00264 0.00631 0.00038 AFIX 23 H11A 2 0.138233 0.426236 0.476252 11.00000 -1.20000 H11B 2 0.134059 0.445508 0.375446 11.00000 -1.20000 AFIX 0 C12 1 0.065654 0.720677 0.405745 11.00000 0.02363 0.03242 = 0.03526 -0.00130 0.00669 0.00112 AFIX 23 H12A 2 0.065051 0.822974 0.458901 11.00000 -1.20000 H12B 2 0.063514 0.860507 0.359657 11.00000 -1.20000 AFIX 0 C13 1 0.001065 0.531439 0.373937 11.00000 0.02526 0.03374 = 0.03470 -0.00235 0.00786 -0.00002 AFIX 23 H13A 2 0.001382 0.429795 0.320547 11.00000 -1.20000 H13B 2 0.003096 0.391249 0.419887 11.00000 -1.20000 AFIX 0 C14 1 -0.066899 0.697965 0.353102 11.00000 0.02557 0.03654 = 0.03439 -0.00054 0.00753 0.00043 AFIX 23 H14A 2 -0.068293 0.841214 0.308239 11.00000 -1.20000 H14B 2 -0.067546 0.796222 0.406907 11.00000 -1.20000 AFIX 0 C15 1 -0.131895 0.512344 0.319229 11.00000 0.02710 0.04044 = 0.03875 -0.00388 0.00921 -0.00135 AFIX 23 H15A 2 -0.130582 0.368291 0.363831 11.00000 -1.20000 H15B 2 -0.131694 0.415413 0.265022 11.00000 -1.20000 AFIX 0 C16 1 -0.199291 0.683763 0.299522 11.00000 0.02442 0.05460 = 0.04624 -0.00031 0.00694 -0.00059 AFIX 33 H16A 2 -0.238594 0.557827 0.278766 11.00000 -1.50000 H16B 2 -0.201488 0.823408 0.254228 11.00000 -1.50000 H16C 2 -0.200144 0.777780 0.353186 11.00000 -1.50000 HKLF 4 REM FZ2 in P21/c REM R1 = 0.0568 for 2462 Fo > 4sig(Fo) and 0.0640 for all 2811 data REM 172 parameters refined using 0 restraints END WGHT 0.0633 1.1903 REM Highest difference peak 0.491, deepest hole -0.224, 1-sigma level 0.061 Q1 1 0.3327 0.7467 0.6775 11.00000 0.05 0.49 Q2 1 0.3396 0.7840 0.5239 11.00000 0.05 0.31 Q3 1 -0.2009 0.2462 0.3736 11.00000 0.05 0.25 Q4 1 -0.1975 0.2479 0.2062 11.00000 0.05 0.25 Q5 1 0.4136 1.1411 0.5192 11.00000 0.05 0.25 Q6 1 0.4199 1.1475 0.7150 11.00000 0.05 0.25 Q7 1 0.3461 0.7080 0.4681 11.00000 0.05 0.24 Q8 1 -0.0649 0.2469 0.2638 11.00000 0.05 0.23 Q9 1 -0.1379 0.4707 0.2240 11.00000 0.05 0.23 Q10 1 0.3452 0.9324 0.3131 11.00000 0.05 0.23 ; _cod_data_source_file rz5095.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2238921 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_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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity O O1 0.33354(9) 0.7667(4) 0.34657(10) 0.0397(4) Uani d . 1 1 O O2 0.44511(8) 1.1900(4) 0.42454(10) 0.0385(4) Uani d . 1 1 N N1 0.32574(9) 0.7836(4) 0.48939(11) 0.0272(4) Uani d . 1 1 C C1 0.35221(11) 0.8574(5) 0.42319(14) 0.0299(5) Uani d . 1 1 C C2 0.40999(10) 1.0835(5) 0.46468(14) 0.0288(5) Uani d . 1 1 C C3 0.40798(10) 1.1295(4) 0.55543(13) 0.0258(4) Uani d . 1 1 C C4 0.44509(10) 1.3124(5) 0.62281(15) 0.0296(5) Uani d . 1 1 H H4 0.4791 1.4325 0.6148 0.036 Uiso calc R 1 1 C C5 0.43015(11) 1.3116(5) 0.70275(14) 0.0308(5) Uani d . 1 1 H H5 0.4540 1.4343 0.7488 0.037 Uiso calc R 1 1 C C6 0.37992(11) 1.1290(5) 0.71428(13) 0.0290(5) Uani d . 1 1 H H6 0.3710 1.1310 0.7685 0.035 Uiso calc R 1 1 C C7 0.34230(10) 0.9420(5) 0.64691(13) 0.0272(4) Uani d . 1 1 H H7 0.3089 0.8196 0.6553 0.033 Uiso calc R 1 1 C C8 0.35685(9) 0.9471(4) 0.56786(13) 0.0241(4) Uani d . 1 1 C C9 0.26652(10) 0.5930(5) 0.47581(15) 0.0303(5) Uani d . 1 1 H H9A 0.2732 0.4819 0.5298 0.036 Uiso calc R 1 1 H H9B 0.2645 0.4618 0.4275 0.036 Uiso calc R 1 1 C C10 0.19768(10) 0.7542(5) 0.45315(15) 0.0300(5) Uani d . 1 1 H H10A 0.1940 0.8837 0.4039 0.036 Uiso calc R 1 1 H H10B 0.1976 0.8674 0.5045 0.036 Uiso calc R 1 1 C C11 0.13437(10) 0.5572(5) 0.42731(15) 0.0305(5) Uani d . 1 1 H H11A 0.1382 0.4262 0.4763 0.037 Uiso calc R 1 1 H H11B 0.1341 0.4455 0.3754 0.037 Uiso calc R 1 1 C C12 0.06565(10) 0.7207(5) 0.40574(15) 0.0311(5) Uani d . 1 1 H H12A 0.0651 0.8230 0.4589 0.037 Uiso calc R 1 1 H H12B 0.0635 0.8605 0.3597 0.037 Uiso calc R 1 1 C C13 0.00107(10) 0.5314(5) 0.37394(15) 0.0317(5) Uani d . 1 1 H H13A 0.0014 0.4298 0.3205 0.038 Uiso calc R 1 1 H H13B 0.0031 0.3912 0.4199 0.038 Uiso calc R 1 1 C C14 -0.06690(11) 0.6980(5) 0.35310(15) 0.0327(5) Uani d . 1 1 H H14A -0.0683 0.8412 0.3082 0.039 Uiso calc R 1 1 H H14B -0.0675 0.7962 0.4069 0.039 Uiso calc R 1 1 C C15 -0.13189(11) 0.5123(5) 0.31923(16) 0.0358(5) Uani d . 1 1 H H15A -0.1306 0.3683 0.3638 0.043 Uiso calc R 1 1 H H15B -0.1317 0.4154 0.2650 0.043 Uiso calc R 1 1 C C16 -0.19929(12) 0.6838(6) 0.29952(18) 0.0429(6) Uani d . 1 1 H H16A -0.2386 0.5578 0.2788 0.064 Uiso calc R 1 1 H H16B -0.2015 0.8234 0.2542 0.064 Uiso calc R 1 1 H H16C -0.2001 0.7778 0.3532 0.064 Uiso calc R 1 1 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 O1 0.0396(9) 0.0494(10) 0.0293(8) 0.0081(7) 0.0102(7) -0.0051(7) O2 0.0303(8) 0.0559(11) 0.0335(8) 0.0040(7) 0.0160(7) 0.0132(7) N1 0.0222(8) 0.0314(9) 0.0271(9) 0.0000(7) 0.0067(7) -0.0028(7) C1 0.0265(10) 0.0372(12) 0.0262(10) 0.0098(8) 0.0087(8) 0.0014(8) C2 0.0224(9) 0.0349(11) 0.0297(10) 0.0088(8) 0.0092(8) 0.0086(9) C3 0.0225(9) 0.0285(10) 0.0275(10) 0.0050(7) 0.0096(8) 0.0072(8) C4 0.0207(9) 0.0307(11) 0.0364(11) -0.0008(8) 0.0078(8) 0.0049(9) C5 0.0267(10) 0.0319(11) 0.0312(11) 0.0000(8) 0.0059(8) -0.0013(8) C6 0.0275(10) 0.0353(11) 0.0243(10) 0.0047(8) 0.0084(8) 0.0026(8) C7 0.0240(9) 0.0306(11) 0.0286(10) 0.0001(8) 0.0107(8) 0.0031(8) C8 0.0188(9) 0.0257(10) 0.0263(9) 0.0040(7) 0.0053(7) 0.0011(8) C9 0.0250(10) 0.0284(11) 0.0350(11) -0.0012(8) 0.0064(8) -0.0031(8) C10 0.0247(10) 0.0299(11) 0.0340(11) 0.0014(8) 0.0074(8) -0.0014(8) C11 0.0238(10) 0.0311(11) 0.0345(11) 0.0004(8) 0.0063(8) -0.0026(9) C12 0.0236(10) 0.0324(11) 0.0353(11) 0.0011(8) 0.0067(8) -0.0013(9) C13 0.0253(10) 0.0337(12) 0.0347(11) 0.0000(8) 0.0079(8) -0.0023(9) C14 0.0256(11) 0.0365(12) 0.0344(11) 0.0004(9) 0.0075(9) -0.0005(9) C15 0.0271(11) 0.0404(13) 0.0388(12) -0.0014(9) 0.0092(9) -0.0039(10) C16 0.0244(11) 0.0546(15) 0.0462(14) -0.0006(10) 0.0069(10) -0.0003(12) 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 C1 N1 C8 110.93(17) C1 N1 C9 123.59(18) C8 N1 C9 124.91(17) O1 C1 N1 126.7(2) O1 C1 C2 127.1(2) N1 C1 C2 106.24(17) O2 C2 C3 131.6(2) O2 C2 C1 123.6(2) C3 C2 C1 104.83(16) C4 C3 C8 120.78(18) C4 C3 C2 131.56(19) C8 C3 C2 107.65(18) C3 C4 C5 118.16(19) C3 C4 H4 120.9 C5 C4 H4 120.9 C6 C5 C4 120.4(2) C6 C5 H5 119.8 C4 C5 H5 119.8 C5 C6 C7 122.01(19) C5 C6 H6 119.0 C7 C6 H6 119.0 C8 C7 C6 117.09(19) C8 C7 H7 121.5 C6 C7 H7 121.5 C7 C8 C3 121.54(19) C7 C8 N1 128.20(18) C3 C8 N1 110.25(17) N1 C9 C10 112.20(17) N1 C9 H9A 109.2 C10 C9 H9A 109.2 N1 C9 H9B 109.2 C10 C9 H9B 109.2 H9A C9 H9B 107.9 C9 C10 C11 112.85(17) C9 C10 H10A 109.0 C11 C10 H10A 109.0 C9 C10 H10B 109.0 C11 C10 H10B 109.0 H10A C10 H10B 107.8 C10 C11 C12 112.44(18) C10 C11 H11A 109.1 C12 C11 H11A 109.1 C10 C11 H11B 109.1 C12 C11 H11B 109.1 H11A C11 H11B 107.8 C13 C12 C11 113.79(18) C13 C12 H12A 108.8 C11 C12 H12A 108.8 C13 C12 H12B 108.8 C11 C12 H12B 108.8 H12A C12 H12B 107.7 C14 C13 C12 113.04(18) C14 C13 H13A 109.0 C12 C13 H13A 109.0 C14 C13 H13B 109.0 C12 C13 H13B 109.0 H13A C13 H13B 107.8 C13 C14 C15 113.60(19) C13 C14 H14A 108.8 C15 C14 H14A 108.8 C13 C14 H14B 108.8 C15 C14 H14B 108.8 H14A C14 H14B 107.7 C14 C15 C16 112.6(2) C14 C15 H15A 109.1 C16 C15 H15A 109.1 C14 C15 H15B 109.1 C16 C15 H15B 109.1 H15A C15 H15B 107.8 C15 C16 H16A 109.5 C15 C16 H16B 109.5 H16A C16 H16B 109.5 C15 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.220(3) O2 C2 1.204(3) N1 C1 1.365(3) N1 C8 1.419(3) N1 C9 1.456(3) C1 C2 1.558(3) C2 C3 1.462(3) C3 C4 1.383(3) C3 C8 1.406(3) C4 C5 1.390(3) C4 H4 0.9300 C5 C6 1.387(3) C5 H5 0.9300 C6 C7 1.398(3) C6 H6 0.9300 C7 C8 1.372(3) C7 H7 0.9300 C9 C10 1.524(3) C9 H9A 0.9700 C9 H9B 0.9700 C10 C11 1.526(3) C10 H10A 0.9700 C10 H10B 0.9700 C11 C12 1.528(3) C11 H11A 0.9700 C11 H11B 0.9700 C12 C13 1.526(3) C12 H12A 0.9700 C12 H12B 0.9700 C13 C14 1.524(3) C13 H13A 0.9700 C13 H13B 0.9700 C14 C15 1.524(3) C14 H14A 0.9700 C14 H14B 0.9700 C15 C16 1.528(3) C15 H15A 0.9700 C15 H15B 0.9700 C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 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 C6 H6 O1 4_576 0.93 2.49 3.156(3) 129.0 C6 H6 O2 4_586 0.93 2.57 3.260(3) 131.0 C4 H4 O2 3_686 0.93 2.55 3.470(3) 170.2 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 N1 C1 O1 -175.8(2) C9 N1 C1 O1 -4.1(3) C8 N1 C1 C2 3.3(2) C9 N1 C1 C2 174.96(17) O1 C1 C2 O2 -2.5(3) N1 C1 C2 O2 178.42(19) O1 C1 C2 C3 176.1(2) N1 C1 C2 C3 -3.0(2) O2 C2 C3 C4 1.1(4) C1 C2 C3 C4 -177.4(2) O2 C2 C3 C8 -180.0(2) C1 C2 C3 C8 1.6(2) C8 C3 C4 C5 -0.3(3) C2 C3 C4 C5 178.5(2) C3 C4 C5 C6 0.8(3) C4 C5 C6 C7 -0.5(3) C5 C6 C7 C8 -0.3(3) C6 C7 C8 C3 0.8(3) C6 C7 C8 N1 -179.05(19) C4 C3 C8 C7 -0.5(3) C2 C3 C8 C7 -179.61(18) C4 C3 C8 N1 179.39(18) C2 C3 C8 N1 0.3(2) C1 N1 C8 C7 177.49(19) C9 N1 C8 C7 5.9(3) C1 N1 C8 C3 -2.4(2) C9 N1 C8 C3 -173.93(18) C1 N1 C9 C10 -93.2(2) C8 N1 C9 C10 77.3(2) N1 C9 C10 C11 172.83(17) C9 C10 C11 C12 179.35(18) C10 C11 C12 C13 176.35(18) C11 C12 C13 C14 179.79(18) C12 C13 C14 C15 178.69(18) C13 C14 C15 C16 179.56(19) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 43129604