#------------------------------------------------------------------------------ #$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301806 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239066.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_2239066 loop_ _publ_author_name 'Al-Omary, Fatmah A. M.' 'Ghabbour, Hazem A.' 'El-Emam, Ali A.' 'Chidan Kumar, C. S.' 'Fun, Hoong-Kun' _publ_section_title ; 5-Propyl-6-(p-tolylsulfanyl)pyrimidine-2,4(1H,3H)-dione ; _journal_coeditor_code SJ5382 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o179 _journal_page_last o180 _journal_paper_doi 10.1107/S1600536814000749 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac 'C14 H16 N2 O2 S' _chemical_formula_moiety 'C14 H16 N2 O2 S' _chemical_formula_sum 'C14 H16 N2 O2 S' _chemical_formula_weight 276.35 _chemical_name_systematic ; 5-Propyl-6-(p-tolylsulfanyl)pyrimidine-2,4(1H,3H)-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 119.850(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.8356(3) _cell_length_b 10.3040(2) _cell_length_c 13.3999(3) _cell_measurement_reflns_used 5622 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 69.54 _cell_measurement_theta_min 3.80 _cell_volume 1417.37(6) _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material ; SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009) ; _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 9643 _diffrn_reflns_theta_full 69.93 _diffrn_reflns_theta_max 69.93 _diffrn_reflns_theta_min 4.31 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.030 _exptl_absorpt_correction_T_max 0.8545 _exptl_absorpt_correction_T_min 0.2868 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 584 _exptl_crystal_size_max 0.82 _exptl_crystal_size_mid 0.71 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.331 _refine_diff_density_min -0.394 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 180 _refine_ls_number_reflns 2658 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0436 _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^)+(0.0707P)^2^+0.4390P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1233 _refine_ls_wR_factor_ref 0.1259 _reflns_number_gt 2450 _reflns_number_total 2658 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL PY32 R: P21/c CELL 1.54178 11.8356 10.3040 13.3999 90.000 119.850 90.000 ZERR 4 0.0003 0.0002 0.0003 0.000 0.002 0.000 LATT 1 SYMM - X , 0.50000 + Y , 0.50000 - Z SFAC C H N O S UNIT 56 64 8 8 4 L.S. 10 FMAP 2 PLAN 25 ACTA BOND $H EQIV $1 x,1/2-y,1/2+z HTAB N1 O2_$1 CONF size 0.08 0.71 0.82 WGHT 0.070700 0.439000 FVAR 0.70633 S1 5 0.284970 0.530217 0.479497 11.00000 0.08790 0.04443 = 0.07010 0.01034 0.05410 0.01832 O1 4 0.452169 0.079796 0.583199 11.00000 0.09771 0.04984 = 0.04941 0.01345 0.05070 0.02484 N1 3 0.381706 0.286143 0.530861 11.00000 0.05880 0.04468 = 0.03563 0.00270 0.03033 0.01012 C1 1 0.350876 0.388027 0.454988 11.00000 0.04834 0.04113 = 0.03986 0.00131 0.02310 0.00353 O2 4 0.447409 0.243683 0.268886 11.00000 0.08883 0.05791 = 0.04869 0.00402 0.04945 0.00580 N2 3 0.454774 0.167697 0.429135 11.00000 0.06090 0.04207 = 0.03915 0.00289 0.03229 0.00915 C2 1 0.431325 0.171955 0.518500 11.00000 0.05234 0.04338 = 0.03352 0.00178 0.02430 0.00808 C3 1 0.426693 0.263742 0.348057 11.00000 0.05450 0.04609 = 0.03672 0.00085 0.02711 -0.00019 C4 1 0.372902 0.382875 0.365415 11.00000 0.05601 0.04429 = 0.04139 0.00261 0.02702 0.00186 C5 1 0.344604 0.492336 0.281373 11.00000 0.06775 0.04645 = 0.05137 0.00330 0.03482 -0.00211 AFIX 23 H5A 2 0.414986 0.497960 0.264209 11.00000 -1.20000 H5B 2 0.342388 0.573326 0.317260 11.00000 -1.20000 AFIX 0 C6 1 0.217565 0.476341 0.170210 11.00000 0.07046 0.05369 = 0.05908 0.00759 0.02907 0.00462 AFIX 23 H6A 2 0.147772 0.462841 0.187210 11.00000 -1.20000 H6B 2 0.222528 0.400166 0.130029 11.00000 -1.20000 AFIX 0 C7 1 0.186538 0.594900 0.092658 11.00000 0.10782 0.07112 = 0.06689 0.02611 0.02717 0.01748 AFIX 33 H7A 2 0.105356 0.581553 0.022917 11.00000 -1.50000 H7B 2 0.254705 0.607564 0.074556 11.00000 -1.50000 H7C 2 0.180028 0.670192 0.131698 11.00000 -1.50000 AFIX 0 C8 1 0.225228 0.479588 0.571422 11.00000 0.05571 0.04595 = 0.04979 0.00310 0.02993 0.01449 C9 1 0.127040 0.388063 0.536924 11.00000 0.06044 0.05511 = 0.06004 -0.00518 0.02980 0.00974 AFIX 43 H9A 2 0.093730 0.347668 0.465704 11.00000 -1.20000 AFIX 0 C10 1 0.079091 0.357325 0.608976 11.00000 0.06029 0.06158 = 0.08598 0.00960 0.04171 0.01097 AFIX 43 H10A 2 0.014898 0.294086 0.586571 11.00000 -1.20000 AFIX 0 C11 1 0.124448 0.418541 0.713769 11.00000 0.06246 0.08849 = 0.06802 0.02098 0.04066 0.02754 C12 1 0.219195 0.512252 0.744542 11.00000 0.07522 0.09369 = 0.04851 -0.00295 0.03179 0.02159 AFIX 43 H12A 2 0.248545 0.556467 0.813618 11.00000 -1.20000 AFIX 0 C13 1 0.271831 0.542348 0.675527 11.00000 0.05963 0.06228 = 0.05443 -0.00538 0.02848 0.00898 AFIX 43 H13A 2 0.337642 0.603963 0.698958 11.00000 -1.20000 AFIX 0 C14 1 0.073399 0.381684 0.792948 11.00000 0.09937 0.16674 = 0.10167 0.04442 0.07315 0.03827 AFIX 33 H14A 2 0.008636 0.315080 0.757541 11.00000 -1.50000 H14B 2 0.035261 0.456433 0.807409 11.00000 -1.50000 H14C 2 0.143795 0.350070 0.864311 11.00000 -1.50000 AFIX 0 H2N2 2 0.483386 0.096350 0.420586 11.00000 0.05538 H1N1 2 0.379066 0.291437 0.588299 11.00000 0.04629 HKLF 4 1 1.0000 0.0000 0.0000 0.0000 -1.0000 0.0000 -1.0000 0.0000 -1.0000 REM PY32 R: P21/c REM R1 = 0.0436 for 2450 Fo > 4sig(Fo) and 0.0462 for all 2658 data REM 180 parameters refined using 0 restraints END WGHT 0.0714 0.4284 REM Highest difference peak 0.331, deepest hole -0.394, 1-sigma level 0.056 Q1 1 0.2145 0.4850 0.4337 11.00000 0.05 0.33 Q2 1 0.2554 0.4400 0.2457 11.00000 0.05 0.24 Q3 1 -0.0290 0.3983 0.7553 11.00000 0.05 0.22 Q4 1 0.5183 0.1120 0.6010 11.00000 0.05 0.18 Q5 1 0.2612 0.6523 0.1175 11.00000 0.05 0.17 Q6 1 0.3018 0.3429 0.3307 11.00000 0.05 0.17 Q7 1 0.1336 0.4230 0.8905 11.00000 0.05 0.17 Q8 1 0.3199 0.5690 0.2189 11.00000 0.05 0.16 Q9 1 0.2676 0.5028 0.5379 11.00000 0.05 0.15 Q10 1 -0.1220 0.4068 0.6965 11.00000 0.05 0.14 Q11 1 0.1399 0.5760 0.0056 11.00000 0.05 0.14 Q12 1 0.4021 0.4041 0.4292 11.00000 0.05 0.13 Q13 1 0.2778 0.3111 0.8760 11.00000 0.05 0.13 Q14 1 0.0972 0.5328 0.3940 11.00000 0.05 0.13 Q15 1 0.0045 0.4927 0.6353 11.00000 0.05 0.12 Q16 1 0.1410 0.4467 0.2525 11.00000 0.05 0.12 Q17 1 0.2577 0.2472 0.5244 11.00000 0.05 0.12 Q18 1 -0.1310 0.3419 0.7453 11.00000 0.05 0.12 Q19 1 0.1424 0.4169 0.1618 11.00000 0.05 0.11 Q20 1 -0.0355 0.3305 0.5503 11.00000 0.05 0.11 Q21 1 0.5618 0.4446 0.3468 11.00000 0.05 0.11 Q22 1 -0.1187 0.2823 0.5753 11.00000 0.05 0.11 Q23 1 0.5785 0.2714 0.2978 11.00000 0.05 0.11 Q24 1 0.0615 0.6126 0.0716 11.00000 0.05 0.11 Q25 1 0.0443 0.4214 0.4294 11.00000 0.05 0.11 ; _cod_data_source_file sj5382sup1.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2239066 _cod_database_fobs_code 2239066 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 S S1 0.28497(6) 0.53022(5) 0.47950(5) 0.0610(2) Uani d . 1 1 O O1 0.45217(15) 0.07980(13) 0.58320(11) 0.0594(4) Uani d . 1 1 N N1 0.38171(14) 0.28614(14) 0.53086(12) 0.0434(3) Uani d . 1 1 C C1 0.35088(16) 0.38803(16) 0.45499(14) 0.0426(4) Uani d . 1 1 O O2 0.44741(15) 0.24368(14) 0.26889(11) 0.0584(4) Uani d . 1 1 N N2 0.45477(15) 0.16770(15) 0.42914(12) 0.0441(3) Uani d . 1 1 C C2 0.43133(16) 0.17195(16) 0.51850(13) 0.0418(4) Uani d . 1 1 C C3 0.42669(17) 0.26374(17) 0.34806(14) 0.0438(4) Uani d . 1 1 C C4 0.37290(17) 0.38287(17) 0.36542(14) 0.0460(4) Uani d . 1 1 C C5 0.3446(2) 0.49234(19) 0.28137(16) 0.0529(4) Uani d . 1 1 H H5A 0.4150 0.4980 0.2642 0.063 Uiso calc R 1 1 H H5B 0.3424 0.5733 0.3173 0.063 Uiso calc R 1 1 C C6 0.2176(2) 0.4763(2) 0.17021(19) 0.0625(5) Uani d . 1 1 H H6A 0.1478 0.4628 0.1872 0.075 Uiso calc R 1 1 H H6B 0.2225 0.4002 0.1300 0.075 Uiso calc R 1 1 C C7 0.1865(3) 0.5949(3) 0.0927(2) 0.0891(8) Uani d . 1 1 H H7A 0.1054 0.5816 0.0229 0.134 Uiso calc R 1 1 H H7B 0.2547 0.6076 0.0746 0.134 Uiso calc R 1 1 H H7C 0.1800 0.6702 0.1317 0.134 Uiso calc R 1 1 C C8 0.22523(18) 0.47959(18) 0.57142(16) 0.0489(4) Uani d . 1 1 C C9 0.1270(2) 0.3881(2) 0.53692(18) 0.0586(5) Uani d . 1 1 H H9A 0.0937 0.3477 0.4657 0.070 Uiso calc R 1 1 C C10 0.0791(2) 0.3573(2) 0.6090(2) 0.0669(6) Uani d . 1 1 H H10A 0.0149 0.2941 0.5866 0.080 Uiso calc R 1 1 C C11 0.1244(2) 0.4185(3) 0.7138(2) 0.0694(6) Uani d . 1 1 C C12 0.2192(2) 0.5123(3) 0.74454(19) 0.0720(6) Uani d . 1 1 H H12A 0.2485 0.5565 0.8136 0.086 Uiso calc R 1 1 C C13 0.2718(2) 0.5423(2) 0.67553(18) 0.0587(5) Uani d . 1 1 H H13A 0.3376 0.6040 0.6990 0.070 Uiso calc R 1 1 C C14 0.0734(3) 0.3817(4) 0.7929(3) 0.1124(13) Uani d . 1 1 H H14A 0.0086 0.3151 0.7575 0.169 Uiso calc R 1 1 H H14B 0.0353 0.4564 0.8074 0.169 Uiso calc R 1 1 H H14C 0.1438 0.3501 0.8643 0.169 Uiso calc R 1 1 H H2N2 0.483(2) 0.096(2) 0.4206(19) 0.055(6) Uiso d . 1 1 H H1N1 0.3791(19) 0.291(2) 0.5883(19) 0.046(5) Uiso d . 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 S1 0.0879(4) 0.0444(3) 0.0701(4) 0.0183(2) 0.0541(3) 0.0103(2) O1 0.0977(10) 0.0498(7) 0.0494(7) 0.0248(7) 0.0507(7) 0.0134(6) N1 0.0588(8) 0.0447(8) 0.0356(7) 0.0101(6) 0.0303(6) 0.0027(6) C1 0.0483(8) 0.0411(9) 0.0399(8) 0.0035(7) 0.0231(7) 0.0013(7) O2 0.0888(9) 0.0579(8) 0.0487(7) 0.0058(7) 0.0494(7) 0.0040(6) N2 0.0609(8) 0.0421(8) 0.0392(7) 0.0091(6) 0.0323(7) 0.0029(6) C2 0.0523(8) 0.0434(9) 0.0335(7) 0.0081(7) 0.0243(7) 0.0018(7) C3 0.0545(9) 0.0461(9) 0.0367(8) -0.0002(7) 0.0271(7) 0.0009(7) C4 0.0560(9) 0.0443(9) 0.0414(8) 0.0019(7) 0.0270(7) 0.0026(7) C5 0.0677(11) 0.0465(9) 0.0514(10) -0.0021(8) 0.0348(9) 0.0033(8) C6 0.0705(12) 0.0537(11) 0.0591(12) 0.0046(9) 0.0291(10) 0.0076(9) C7 0.108(2) 0.0711(16) 0.0669(14) 0.0175(14) 0.0272(14) 0.0261(12) C8 0.0557(10) 0.0460(10) 0.0498(10) 0.0145(7) 0.0299(8) 0.0031(7) C9 0.0604(11) 0.0551(11) 0.0600(11) 0.0097(9) 0.0298(9) -0.0052(9) C10 0.0603(11) 0.0616(12) 0.0860(15) 0.0110(9) 0.0417(11) 0.0096(11) C11 0.0625(12) 0.0885(16) 0.0680(13) 0.0275(12) 0.0407(11) 0.0210(12) C12 0.0752(14) 0.0937(17) 0.0485(11) 0.0216(13) 0.0318(10) -0.0030(11) C13 0.0596(11) 0.0623(12) 0.0544(11) 0.0090(9) 0.0285(9) -0.0054(9) C14 0.099(2) 0.167(4) 0.102(2) 0.038(2) 0.0731(19) 0.044(2) 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' S S 0.3331 0.5567 '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 S1 C8 104.50(8) C2 N1 C1 122.71(14) C2 N1 H1N1 114.1(16) C1 N1 H1N1 122.9(16) C4 C1 N1 121.90(15) C4 C1 S1 119.78(13) N1 C1 S1 118.30(12) C2 N2 C3 126.53(15) C2 N2 H2N2 114.9(16) C3 N2 H2N2 118.3(16) O1 C2 N2 122.78(15) O1 C2 N1 122.06(14) N2 C2 N1 115.16(14) O2 C3 N2 119.25(16) O2 C3 C4 125.16(16) N2 C3 C4 115.59(14) C1 C4 C3 117.98(15) C1 C4 C5 124.38(16) C3 C4 C5 117.64(15) C4 C5 C6 113.39(16) C4 C5 H5A 108.9 C6 C5 H5A 108.9 C4 C5 H5B 108.9 C6 C5 H5B 108.9 H5A C5 H5B 107.7 C5 C6 C7 111.6(2) C5 C6 H6A 109.3 C7 C6 H6A 109.3 C5 C6 H6B 109.3 C7 C6 H6B 109.3 H6A C6 H6B 108.0 C6 C7 H7A 109.5 C6 C7 H7B 109.5 H7A C7 H7B 109.5 C6 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 C13 C8 C9 120.23(19) C13 C8 S1 117.82(16) C9 C8 S1 121.72(15) C10 C9 C8 119.5(2) C10 C9 H9A 120.3 C8 C9 H9A 120.3 C9 C10 C11 121.3(2) C9 C10 H10A 119.3 C11 C10 H10A 119.3 C12 C11 C10 118.1(2) C12 C11 C14 121.2(3) C10 C11 C14 120.8(3) C11 C12 C13 121.8(2) C11 C12 H12A 119.1 C13 C12 H12A 119.1 C8 C13 C12 119.0(2) C8 C13 H13A 120.5 C12 C13 H13A 120.5 C11 C14 H14A 109.5 C11 C14 H14B 109.5 H14A C14 H14B 109.5 C11 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.7658(17) S1 C8 1.7766(19) O1 C2 1.225(2) N1 C2 1.361(2) N1 C1 1.378(2) N1 H1N1 0.79(2) C1 C4 1.350(2) O2 C3 1.220(2) N2 C2 1.358(2) N2 C3 1.382(2) N2 H2N2 0.84(3) C3 C4 1.454(2) C4 C5 1.509(2) C5 C6 1.509(3) C5 H5A 0.9700 C5 H5B 0.9700 C6 C7 1.526(3) C6 H6A 0.9700 C6 H6B 0.9700 C7 H7A 0.9600 C7 H7B 0.9600 C7 H7C 0.9600 C8 C13 1.379(3) C8 C9 1.385(3) C9 C10 1.378(3) C9 H9A 0.9300 C10 C11 1.381(4) C10 H10A 0.9300 C11 C12 1.378(4) C11 C14 1.508(3) C12 C13 1.383(3) C12 H12A 0.9300 C13 H13A 0.9300 C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 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 _geom_hbond_publ_flag N2 H2N2 O1 3_656 0.84(2) 1.98(2) 2.815(2) 173(2) yes N1 H1N1 O2 4_566 0.79(2) 2.17(2) 2.8988(18) 155(2) 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 C2 N1 C1 C4 -2.7(3) C2 N1 C1 S1 179.11(13) C8 S1 C1 C4 162.19(15) C8 S1 C1 N1 -19.57(16) C3 N2 C2 O1 175.69(18) C3 N2 C2 N1 -3.8(3) C1 N1 C2 O1 -176.24(17) C1 N1 C2 N2 3.3(2) C2 N2 C3 O2 -176.34(17) C2 N2 C3 C4 3.4(3) N1 C1 C4 C3 2.1(3) S1 C1 C4 C3 -179.72(13) N1 C1 C4 C5 -178.32(17) S1 C1 C4 C5 -0.1(2) O2 C3 C4 C1 177.39(17) N2 C3 C4 C1 -2.3(2) O2 C3 C4 C5 -2.2(3) N2 C3 C4 C5 178.08(16) C1 C4 C5 C6 -99.1(2) C3 C4 C5 C6 80.5(2) C4 C5 C6 C7 174.6(2) C1 S1 C8 C13 123.21(15) C1 S1 C8 C9 -62.23(17) C13 C8 C9 C10 -2.0(3) S1 C8 C9 C10 -176.42(15) C8 C9 C10 C11 1.8(3) C9 C10 C11 C12 0.3(3) C9 C10 C11 C14 -178.5(2) C10 C11 C12 C13 -2.2(3) C14 C11 C12 C13 176.6(2) C9 C8 C13 C12 0.1(3) S1 C8 C13 C12 174.76(16) C11 C12 C13 C8 2.0(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139086337