organic compounds Acta Crystallographica Section E Data collection Structure Reports Online ISSN 1600-5368 (E)-1-(2,5-Dimethyl-3-thienyl)-3-(2,4,5trimethoxyphenyl)prop-2-en-1-one Abdullah M. Asiri,a,b Salman A. Khanb and M. Nawaz Tahirc* a The Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, bDepartment of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, and cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan Correspondence e-mail: dmntahir_uos@yahoo.com Received 12 July 2010; accepted 18 July 2010 In the title compound, C18H20O4S, the thiophene and benzene rings are oriented at a dihedral angle of 10.83 (11) . The central chain makes dihedral angles of 1.86 (13) and 9.25 (12) with the benzene and thiophene rings, respectively. In the crystal, molecules are linked through weak intermolecular C— H  O interactions. – interactions are also observed between the benzene rings with a centroid–centroid distance of 3.6832 (12) Å. The slippage between the benzene rings is 0.956 Å. Related literature For the biological activity of 1,3-diphenyl-2-propene-1-ones, see: Gökhan-Kelekçi et al. (2007); Ducki et al. (2009); dos Santos et al. (2008); Hussain et al. (2009); Dandia et al. (2006); Valla et al. (2006); Ye et al. (2004). For related structures, see: Asiri et al. (2009): Hussain et al. (2010): Fun et al. (2010). Experimental Crystal data Acta Cryst. (2010). E66, o2099 Z = 16 Mo K radiation  = 0.21 mm1 T = 296 K 0.26  0.18  0.16 mm Refinement R[F 2 > 2(F 2)] = 0.040 wR(F 2) = 0.113 S = 1.05 3106 reflections 213 parameters H-atom parameters constrained
max = 0.19 e Å3
min = 0.15 e Å3 Table 1 Hydrogen-bond geometry (Å,  ). D—H  A i C9—H9C  O3 C14—H14  O4ii D—H H  A D  A D—H  A 0.96 0.93 2.55 2.57 3.209 (3) 3.483 (3) 126 168 Symmetry codes: (i) y þ 14; x  14; z þ 34; (ii) y þ 14; x  14; z  14. Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.003 Å; R factor = 0.040; wR factor = 0.113; data-to-parameter ratio = 14.6. C18H20O4S Mr = 332.40 Tetragonal, I41 =a a = 19.5263 (5) Å c = 17.9952 (4) Å V = 6861.2 (3) Å3 25995 measured reflections 3106 independent reflections 2225 reflections with I > 2(I) Rint = 0.038 Bruker KAPPA APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005) Tmin = 0.966, Tmax = 0.975 Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON. The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia for providing research facilities and the Deanship of Scientific Research for the financial support of this work via grant No. (3–045/430). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2278). References Asiri, A. M., Khan, S. A. & Ng, S. W. (2009). Acta Cryst. E65, o1726. Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Dandia, A., Singh, R. & Khaturia, S. (2006). Bioorg. Med. Chem. 14, 1303– 1308. Ducki, S., Rennison, D., Woo, M., Kendall, A., Chabert, J. F. D., McGown, A. T. & Lawrence, N. J. (2009). Bioorg. Med. Chem. 17, 7698–7710. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. Fun, H.-K., Hemamalini, M., Asiri, A. M. & Khan, S. A. (2010). Acta Cryst. E66, o1656–o1657. Gökhan-Kelekçi, N., Yabanoglu, S., Küpeli, E., Salgin, U., Özgen, Ö., Uçar, G., Yesilada, E., Kendi, E., Yesilada, A. & Bilgin, A. A. (2007). Bioorg. Med. Chem. 15, 5775–5786. Hussain, T., Siddiqui, H. L., Zia-ur-Rehman, M., Yasinzai, M. M. & Parvez, M. (2009). Eur. J. Med. Chem. 44, 4654–4660. Hussain, A., Tahir, M. N., Tariq, M. I., Ahmad, S. & Asiri, A. M. (2010). Acta Cryst. E66, o1953. Santos, L. dos, Lima, L. A., Cechinel-Filho, V., Corréa, R., Buzzi, F. C. & Nunes, R. J. (2008). Bioorg. Med. Chem. 16, 8526–8534. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Spek, A. L. (2009). Acta Cryst. D65, 148–155. Valla, A., Valla, B., Cartier, D., Guillou, R. L., Labia, R., Florent, L., Charneau, S., Schrevel, J. & Potier, P. (2006). Eur. J. Med. Chem. 41, 142–146. Ye, C., Liu, J., Wei, D., Lu, Y. & Qian, F. (2004). Pharmacol. Res. 50, 505–510. doi:10.1107/S1600536810028709 Asiri et al. o2099 supplementary materials supplementary materials Acta Cryst. (2010). E66, o2099 [ doi:10.1107/S1600536810028709 ] (E)-1-(2,5-Dimethyl-3-thienyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one A. M. Asiri, S. A. Khan and M. N. Tahir Comment 1,3-Diphenyl-2-propene-1-one, are considered to be precursors of flavonoids when found as naturally occurring compounds, but it could be considered that their true importance is extended in two branches: The biological activity associated with them, including anti-inflammatory (Gökhan-Kelekçi et al., 2007), antimitotic (Ducki, et al., 2009), anti-leishmanial (dos Santos, et al., 2008), anti-invasive (Hussain, et al., 2009), anti-fungal (Dandia et al., 2006) antimalarial (Valla et al., 2006) and anti-tumor (Ye et al., 2004) properties; as well as their recognized synthetic utility in the preparation of pharmacologically interesting heterocyclic systems. On the bases of these aspects in this paper we are reporting the synthesis and crystal structure of the title compound (I), (Fig. 1). The crystal structures of (II) i.e., (2E,2'E)-1,1'-bis(2,5-dimethyl-3-thienyl)-3,3'-(p-phenylene) diprop-2-en-1-one (Asiri et al., 2009) has been published which contain the 2,5-dimethylthiophen-3-yl moiety. Similarly, the crystal structures of (III) 2,3-dimethyl-N-[(E)-2,4,5-trimethoxybenzylidene]aniline (Hussain et al., 2010) and (IV) 4-[(E)-(2,4,5trimethoxybenzylidene)amino]-1,5-dimethyl-2- phenyl-1H-pyrazol-3(2H)-one (Fun et al., 2010) have been published which contain the 2,4,5-trimethoxyphenyl moiety. In (I), the group A (C1—C6/O1/O2/O3) of 2,4,5-trimethoxyphenyl moiety, the central chain B (C10—C12/O4) and 2,5dimethylthiophen-3-yl C (C13—C18/S1) are planar with r. m. s. deviation of 0.0033, 0.0160 and 0.0031 Å, respectively. The dihedral angle between A/B, A/C and B/C is 1.80 (10), 10.65 (9) and 9.23 (12)°, respectively. Overall 2,4,5-trimethoxyphenyl group has a maximum deviation 0.0338 Å and in it the C9 deviates at maximum 0.0834 (20) Å. The molecules are interlinked through H-bondings of C—H···O type (Table 1, Fig. 2). There exist π—π interaction between the centroids of phenyl rings at a distance of 3.6832 (12) Å [symmetry: - x, - y, 1 - z]. Experimental A solution of 3-acetyl-2,5-dimethythiophene (0.38 g, 0.0025 mol) and 2,4,5-trimethoxy benzaldehyde (0.49 g, 0.0025 mol) in ethanolic solution of NaOH (3.0 g in 10 ml of methanol) was stirred for 16 h at room temperature. The solution was poured into ice cold water of pH = 2 (pH adjusted by HCl). The solid was separated and dissolved in CH2Cl2, washed with saturated solution of NaHCO3 and evaporated to dryness. The residual was recrystallized from methanol/chloroform to affoard yellow prisms. Yield: 72%; m. p. 380–381 K. IR (KBr) vmax cm-1: 3016 (Ar—H), 2924 (C—H), 1642 (C═O), 1572(C═ C). 1H NMR (DMSO-d6) (δ/p.p.m.): 8.01 (s, 1H, CHaromatic), 7.98 (s, CHaromatic), 7.20 (d, C═CH, J = 15.6 Hz), 7.08 (d, C═CH, J=15.0 Hz), 6.51 (s, 1H, C3, CHthiophene), 3.94 (s, OCH3), 3.73 (s, OCH3), 3.62 (s, OCH3),2.44 (s, 3H, –CH3), 2.17 (s, 3H, CH3). sup-1 supplementary materials Refinement The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for aryl H-atoms. Figures Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radii. Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules are interlinked through H-bondings. (E)-1-(2,5-Dimethyl-3-thienyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one Crystal data C18H20O4S Dx = 1.287 Mg m−3 Mr = 332.40 Mo Kα radiation, λ = 0.71073 Å Tetragonal, I41/a Cell parameters from 2225 reflections Hall symbol: -I 4ad θ = 2.1–25.2° a = 19.5263 (5) Å µ = 0.21 mm−1 T = 296 K c = 17.9952 (4) Å V = 6861.2 (3) Å3 Z = 16 F(000) = 2816 Prism, yellow 0.26 × 0.18 × 0.16 mm Data collection Bruker KAPPA APEXII CCD diffractometer Radiation source: fine-focus sealed tube graphite Detector resolution: 8.10 pixels mm-1 ω scans Absorption correction: multi-scan (SADABS; Bruker, 2005) Tmin = 0.966, Tmax = 0.975 25995 measured reflections sup-2 3106 independent reflections 2225 reflections with I > 2σ(I) Rint = 0.038 θmax = 25.2°, θmin = 2.1° h = −20→23 k = −23→23 l = −21→21 supplementary materials Refinement R[F2 > 2σ(F2)] = 0.040 Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites wR(F2) = 0.113 H-atom parameters constrained Refinement on F2 Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0466P)2 + 4.0141P] S = 1.05 where P = (Fo2 + 2Fc2)/3 3106 reflections (Δ/σ)max = 0.001 213 parameters Δρmax = 0.19 e Å−3 0 restraints Δρmin = −0.15 e Å−3 Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) S1 O1 O2 O3 O4 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 x y z Uiso*/Ueq 0.35094 (3) 0.12845 (9) −0.03254 (9) 0.00824 (9) 0.27754 (9) 0.12078 (10) 0.09748 (11) 0.04661 (11) 0.01787 (11) 0.04047 (11) 0.09028 (11) 0.10721 (14) −0.05983 (14) 0.03306 (14) 0.17351 (10) 0.20201 (11) 0.25438 (11) 0.28009 (11) 0.25098 (12) 0.20431 (3) 0.01126 (9) −0.15317 (9) −0.12701 (10) 0.14060 (9) −0.00807 (10) −0.02371 (11) −0.07194 (11) −0.10560 (11) −0.09097 (12) −0.04341 (11) −0.00049 (14) −0.16834 (16) −0.12099 (15) 0.04257 (11) 0.06423 (11) 0.11732 (11) 0.14298 (11) 0.12648 (12) 0.27680 (3) 0.64860 (7) 0.54859 (9) 0.41648 (8) 0.50556 (8) 0.52048 (10) 0.59198 (10) 0.60327 (11) 0.54363 (12) 0.47106 (11) 0.46095 (11) 0.72270 (11) 0.61946 (14) 0.34337 (12) 0.51010 (10) 0.44711 (11) 0.44709 (11) 0.37456 (10) 0.30381 (11) 0.0714 (2) 0.0807 (6) 0.0813 (6) 0.0862 (7) 0.0818 (6) 0.0514 (7) 0.0556 (7) 0.0600 (7) 0.0600 (8) 0.0604 (8) 0.0569 (7) 0.0754 (9) 0.0904 (11) 0.0829 (10) 0.0553 (7) 0.0581 (7) 0.0579 (7) 0.0536 (7) 0.0622 (8) sup-3 supplementary materials C15 C16 C17 C18 H3 H6 H7A H7B H7C H8A H8B H8C H9A H9B H9C H10 H11 H14 H16A H16B H16C H18A H18B H18C 0.28342 (12) 0.26802 (14) 0.33529 (11) 0.38074 (14) 0.03178 0.10480 0.05890 0.13148 0.11684 −0.02460 −0.09654 −0.07688 0.02961 0.00640 0.08010 0.18992 0.18819 0.21311 0.30512 0.26257 0.22655 0.35531 0.41902 0.39698 0.15590 (12) 0.14998 (15) 0.18552 (11) 0.21495 (14) −0.08165 −0.03382 0.00783 0.02983 −0.04708 −0.18752 −0.20070 −0.12709 −0.07418 −0.14950 −0.13520 0.06293 0.04507 0.09805 0.12692 0.19491 0.12433 0.24738 0.23751 0.17880 0.24581 (11) 0.16401 (12) 0.36833 (11) 0.42741 (13) 0.65123 0.41285 0.72682 0.75542 0.73613 0.65031 0.61437 0.64183 0.32751 0.31093 0.34178 0.55329 0.40224 0.29830 0.13955 0.14319 0.15719 0.45650 0.40458 0.45898 0.0636 (8) 0.0857 (10) 0.0577 (7) 0.0810 (10) 0.0720* 0.0683* 0.1132* 0.1132* 0.1132* 0.1355* 0.1355* 0.1355* 0.1242* 0.1242* 0.1242* 0.0664* 0.0697* 0.0747* 0.1286* 0.1286* 0.1286* 0.1215* 0.1215* 0.1215* Atomic displacement parameters (Å2) S1 O1 O2 O3 O4 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 sup-4 U11 0.0843 (4) 0.1053 (13) 0.0825 (11) 0.0853 (12) 0.0953 (12) 0.0545 (12) 0.0648 (13) 0.0685 (14) 0.0582 (13) 0.0594 (13) 0.0582 (12) 0.0982 (18) 0.093 (2) 0.0979 (19) 0.0624 (13) 0.0659 (13) 0.0644 (13) 0.0584 (12) 0.0656 (14) 0.0700 (14) U22 0.0798 (4) 0.0996 (12) 0.0952 (12) 0.1182 (14) 0.1074 (13) 0.0567 (12) 0.0599 (12) 0.0697 (14) 0.0642 (14) 0.0720 (14) 0.0691 (14) 0.0905 (17) 0.104 (2) 0.100 (2) 0.0620 (13) 0.0673 (14) 0.0685 (14) 0.0586 (12) 0.0786 (15) 0.0767 (15) U33 0.0502 (3) 0.0372 (7) 0.0662 (10) 0.0552 (9) 0.0426 (8) 0.0430 (10) 0.0421 (10) 0.0417 (10) 0.0575 (12) 0.0497 (12) 0.0434 (10) 0.0376 (11) 0.0743 (16) 0.0507 (13) 0.0416 (10) 0.0411 (10) 0.0408 (10) 0.0439 (10) 0.0425 (11) 0.0440 (11) U12 −0.0019 (3) −0.0388 (10) −0.0260 (10) −0.0282 (10) −0.0294 (10) 0.0055 (10) −0.0002 (11) −0.0026 (12) −0.0024 (11) 0.0016 (12) 0.0050 (11) −0.0146 (14) −0.0267 (17) −0.0002 (16) 0.0028 (10) −0.0020 (11) 0.0026 (11) 0.0069 (10) 0.0027 (11) 0.0121 (12) U13 0.0108 (3) −0.0040 (8) 0.0093 (8) 0.0079 (8) −0.0032 (8) −0.0006 (8) −0.0039 (9) 0.0018 (9) 0.0040 (10) 0.0015 (10) 0.0060 (9) −0.0026 (11) 0.0136 (14) −0.0021 (12) −0.0034 (9) −0.0016 (9) −0.0012 (9) 0.0009 (9) −0.0005 (10) 0.0002 (10) U23 0.0054 (3) −0.0007 (8) −0.0140 (9) −0.0337 (9) −0.0034 (8) −0.0037 (9) −0.0020 (9) 0.0004 (10) −0.0072 (10) −0.0171 (10) −0.0084 (9) 0.0011 (10) 0.0047 (14) −0.0240 (12) −0.0044 (9) −0.0048 (9) −0.0016 (9) 0.0003 (9) −0.0003 (10) −0.0011 (10) supplementary materials C16 C17 C18 0.0957 (19) 0.0666 (14) 0.0866 (18) 0.120 (2) 0.0611 (13) 0.0967 (19) 0.0414 (12) 0.0454 (11) 0.0597 (14) 0.0123 (16) 0.0065 (11) −0.0225 (15) −0.0012 (12) 0.0041 (9) 0.0038 (12) 0.0040 (12) −0.0021 (9) −0.0086 (13) Geometric parameters (Å, °) S1—C15 S1—C17 O1—C2 O1—C7 O2—C4 O2—C8 O3—C5 O3—C9 O4—C12 C1—C2 C1—C6 C1—C10 C2—C3 C3—C4 C4—C5 C5—C6 C10—C11 C11—C12 C12—C13 C13—C14 C13—C17 C14—C15 1.715 (2) 1.715 (2) 1.368 (2) 1.415 (2) 1.356 (3) 1.414 (3) 1.362 (3) 1.407 (3) 1.232 (3) 1.399 (3) 1.407 (3) 1.440 (3) 1.384 (3) 1.378 (3) 1.408 (3) 1.357 (3) 1.332 (3) 1.456 (3) 1.486 (3) 1.431 (3) 1.365 (3) 1.349 (3) C15—C16 C17—C18 C3—H3 C6—H6 C7—H7A C7—H7B C7—H7C C8—H8A C8—H8B C8—H8C C9—H9A C9—H9B C9—H9C C10—H10 C11—H11 C14—H14 C16—H16A C16—H16B C16—H16C C18—H18A C18—H18B C18—H18C 1.507 (3) 1.499 (3) 0.9300 0.9300 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 0.9300 0.9300 0.9300 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 O2···O3 2.559 (2) H6···C9 2.5300 i O2···C9 O3···O2 3.410 (3) H6···C11 2.7700 2.559 (2) H6···H9A 2.2700 O3···C9i O4···C18 3.209 (3) H6···H9C 2.4100 2.854 (3) H6···H11 2.2500 O1···H10 2.3200 H6···H10 O3···H9Ci O4···H10 2.5500 H7A···C3 2.4400 H7A···H3 O4···H18A 2.7300 H7A···H9A O4···H18C 2.5900 H7B···C16v 2.9300 O4···H8Cii 2.7600 H7B···H16Av 2.4700 O4···H9Aiii 2.8400 H7B···C1iii 2.9100 O4···H14iii 2.5700 H7B···C6iii 3.0400 C4···C6iv 3.596 (3) H7C···C3 2.8000 iv 3.596 (3) H7C···H3 C6···C4 viii 2.5900 2.7300 2.2800 iv 2.3700 2.3600 v ix C7···C16 3.464 (3) H7C···C15 C9···O3 vi 3.209 (3) H8A···C3 2.7800 C9···O2 vi 3.410 (3) H8A···H3 2.3400 2.8900 sup-5 supplementary materials C16···C7vii C18···O4 3.464 (3) H8C···C3 2.854 (3) H8C···H3 2.7300 2.3100 xiii viii C1···H7B 2.9100 H8C···O4 C2···H16Aix C3···H8C 2.9000 H9A···C6 2.7300 H9A···H6 2.7400 C3···H8A 2.7800 C3···H7A 2.7300 C3···H7C 2.8000 H9A···O4 H9C···C6 3.0400 H9C···H6 viii C6···H7B C6···H9C 2.8000 C6···H11 C6···H9A 2.7800 2.7400 C7···H3 2.5200 C8···H3 C9···H6 C11···H6 C11···H14 C12···H14iii C12···H18C iii C12···H16C iii C13···H16C C14···H11 2.2700 H9A···H7A H9C···O3 H10···O1 H10···O4 2.7600 iv 2.3700 viii 2.8400 2.8000 2.4100 vi 2.5500 2.3200 2.4400 2.5300 2.5300 2.7700 2.7700 H10···H6iii H11···C6 H11···C14 H11···H6 H11···H14 2.7800 2.6800 2.2500 2.1900 3.0200 H14···C11 2.7700 3.0400 H14···H11 2.1900 3.0600 3.0300 2.6800 H14···O4 2.5900 viii H14···C12 2.5700 viii H16A···C2 3.0200 x 2.9000 x 2.8900 H16A···H7B 2.4700 vii C16···H7B 2.9300 H16B···C17xi 3.0200 C17···H16Bxi 3.0200 H16C···C12viii 3.0600 C18···H18Bxii H3···C7 3.1000 3.0300 2.5200 H16C···C13viii H18A···O4 2.7300 2.5300 xiv 3.1000 C15···H7C H3···C8 H3···H7A 2.2800 H3···H7C 2.3600 H3···H8A H3···H8C C15—S1—C17 C2—O1—C7 C4—O2—C8 C5—O3—C9 C2—C1—C6 C2—C1—C10 C6—C1—C10 O1—C2—C1 O1—C2—C3 C1—C2—C3 C2—C3—C4 O2—C4—C3 O2—C4—C5 sup-6 vii H18B···C18 xiv 2.5000 xii 2.5000 H18B···H18B 2.3400 2.3100 H18B···H18B H18C···O4 H18C···C12 2.5900 3.0400 93.29 (10) 119.44 (18) 118.45 (19) 118.16 (19) 117.12 (18) 120.13 (17) 122.75 (17) 115.63 (18) 123.22 (17) 121.15 (18) 120.17 (19) 124.82 (19) 115.31 (19) O1—C7—H7A O1—C7—H7B O1—C7—H7C H7A—C7—H7B H7A—C7—H7C H7B—C7—H7C O2—C8—H8A O2—C8—H8B O2—C8—H8C H8A—C8—H8B H8A—C8—H8C H8B—C8—H8C O3—C9—H9A 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 supplementary materials C3—C4—C5 O3—C5—C4 O3—C5—C6 C4—C5—C6 C1—C6—C5 C1—C10—C11 C10—C11—C12 O4—C12—C11 O4—C12—C13 C11—C12—C13 C12—C13—C14 C12—C13—C17 C14—C13—C17 C13—C14—C15 S1—C15—C14 S1—C15—C16 C14—C15—C16 S1—C17—C13 S1—C17—C18 C13—C17—C18 C2—C3—H3 C4—C3—H3 C1—C6—H6 C5—C6—H6 119.9 (2) 114.78 (19) 126.01 (19) 119.20 (19) 122.49 (18) 128.86 (18) 121.32 (19) 121.34 (19) 120.12 (19) 118.53 (18) 124.86 (19) 122.97 (18) 112.18 (18) 114.0 (2) 110.12 (16) 120.88 (17) 129.0 (2) 110.47 (15) 119.58 (17) 129.96 (19) 120.00 120.00 119.00 119.00 O3—C9—H9B O3—C9—H9C H9A—C9—H9B H9A—C9—H9C H9B—C9—H9C C1—C10—H10 C11—C10—H10 C10—C11—H11 C12—C11—H11 C13—C14—H14 C15—C14—H14 C15—C16—H16A C15—C16—H16B C15—C16—H16C H16A—C16—H16B H16A—C16—H16C H16B—C16—H16C C17—C18—H18A C17—C18—H18B C17—C18—H18C H18A—C18—H18B H18A—C18—H18C H18B—C18—H18C 109.00 109.00 109.00 109.00 109.00 116.00 116.00 119.00 119.00 123.00 123.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 C17—S1—C15—C14 −0.40 (19) O2—C4—C5—O3 −0.1 (3) C17—S1—C15—C16 −179.6 (2) O2—C4—C5—C6 179.3 (2) C15—S1—C17—C13 0.38 (18) C3—C4—C5—O3 −179.7 (2) C15—S1—C17—C18 179.9 (2) C3—C4—C5—C6 −0.3 (3) C7—O1—C2—C1 178.9 (2) O3—C5—C6—C1 179.6 (2) C7—O1—C2—C3 −1.5 (3) C4—C5—C6—C1 0.3 (3) C8—O2—C4—C3 2.2 (3) C1—C10—C11—C12 178.9 (2) C8—O2—C4—C5 −177.3 (2) C10—C11—C12—O4 5.2 (3) C9—O3—C5—C4 −173.0 (2) C10—C11—C12—C13 −175.2 (2) C9—O3—C5—C6 7.6 (3) O4—C12—C13—C14 −171.4 (2) C6—C1—C2—O1 179.65 (19) O4—C12—C13—C17 8.8 (3) C6—C1—C2—C3 0.0 (3) C11—C12—C13—C14 9.0 (3) C10—C1—C2—O1 −0.7 (3) C11—C12—C13—C17 −170.8 (2) C10—C1—C2—C3 179.7 (2) C12—C13—C14—C15 −179.9 (2) C2—C1—C6—C5 −0.2 (3) C17—C13—C14—C15 0.0 (3) C10—C1—C6—C5 −179.8 (2) C12—C13—C17—S1 179.55 (17) C2—C1—C10—C11 −180.0 (2) C12—C13—C17—C18 0.2 (4) C6—C1—C10—C11 −0.3 (3) C14—C13—C17—S1 −0.3 (2) O1—C2—C3—C4 −179.6 (2) C14—C13—C17—C18 −179.7 (2) C1—C2—C3—C4 0.0 (3) C13—C14—C15—S1 0.3 (3) C2—C3—C4—O2 −179.4 (2) C13—C14—C15—C16 179.4 (2) C2—C3—C4—C5 0.2 (3) Symmetry codes: (i) −y−1/4, x−1/4, −z+3/4; (ii) −y+1/4, x+1/4, −z+5/4; (iii) y+1/4, −x+1/4, z+1/4; (iv) −x, −y, −z+1; (v) −y+1/4, x−1/4, z+3/4; (vi) y+1/4, −x−1/4, −z+3/4; (vii) y+1/4, −x+1/4, z−3/4; (viii) −y+1/4, x−1/4, z−1/4; (ix) −x+1/2, −y, z+1/2; (x) −x+1/2, −y, z−1/2; (xi) −x+1/2, −y+1/2, −z+1/2; (xii) −y+3/4, x−1/4, −z+3/4; (xiii) y−1/4, −x+1/4, −z+5/4; (xiv) y+1/4, −x+3/4, −z+3/4. sup-7 supplementary materials Hydrogen-bond geometry (Å, °) D—H···A D—H H···A D···A D—H···A 0.96 2.55 3.209 (3) 126 0.93 2.57 C14—H14···O4 Symmetry codes: (vi) y+1/4, −x−1/4, −z+3/4; (viii) −y+1/4, x−1/4, z−1/4. 3.483 (3) 168 C9—H9C···O3 vi viii sup-8 supplementary materials Fig. 1 sup-9 supplementary materials Fig. 2 sup-10