Crystal structure of (2E)-1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one European Journal of Chemistry 9 (2) (2018) 147-150 European Journal of Chemistry View Journal Online View Article Online Crystal structure of (2E)-1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2- en-1-one Fatma Yesilyurt 1, Abdullah Aydin 2,*, Halise Inci Gul 1, Mehmet Akkurt 3 and Nefise Dilek Ozcelik 4 1 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, 25240 Erzurum, Turkey fatmayesilyurttt@gmail.com (F.Y.), incigul1967@yahoo.com (H.I.G.) 2 Department of Mathematics and Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey aaydin@kastamonu.edu.tr (A.A.) 3 Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey akkurt@erciyes.edu.tr (M.A.) 4 Department of Physics, Arts and Sciences Faculty, Aksaray University, 68100 Aksaray, Turkey nefised@gmail.com (N.D.O.) * Corresponding author at: Department of Mathematics and Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey. Tel: +90.366.2803310 Fax: +90.366.2123353 e-mail: aaydin@kastamonu.edu.tr (A. Aydin). 10.5155/eurjchem.9.2.147-150.1733 Received: 11 May 2018 Received in revised form: 25 May 2018 Accepted: 25 May 2018 Published online: 30 June 2018 Printed: 30 June 2018 The compound, C16H14O3, (except H atoms) is almost planar [r.m.s. deviations for all non-H atoms = 0.001 Å] and the dihedral angle between the aromatic rings is 9.35 (7)°. In the crystal, molecules are linked by intermolecular O—H···O and C—H···O hydrogen bonds, forming a three-dimensional network structure. Furthermore, a weak π-π stacking interactions [centroid-to-centroid distance = 3.7055 (9) Å] contributes to the stabilization of the molecular packing. Crystal Data for C16H14O3 (M = 254.27 g/mol): Orthorhombic, space group Pbca (no. 61), a = 13.4563(16) Å, b = 11.4986(14) Å, c = 16.720(2) Å, V = 2587.1(5) Å3, Z = 8, T = 296(2) K, μ(MoKα) = 0.090 mm-1, Dcalc = 1.306 g/cm3, 61402 reflections measured (4.88° ≤ 2Θ ≤ 56.76°), 3240 unique (Rint = 0.0334, Rsigma = 0.0120) which were used in all calculations. The final R1 was 0.0438 (I≥2σ(I)) and wR2 was 0.1228 (all data). Chalcones π-π Stacking Aromatic ring Methoxyphenyl Crystal structure Geometric parameter Cite this: Eur. J. Chem. 2018, 9(2), 147-150 Journal website: www.eurjchem.com 1. Introduction Chalcones, 1,3-diaryl-2-propene-1-ones, are major component of many natural products as well as important precursors for many synthetic manipulations [1-3]. Chalcones as well as their synthetic analogues display enormous number of biological activities such as anticancer, antimalarial, antibacterial, anti-inflammatory, antifungal, antioxidant, anti- HIV, antiprotozoal and carbonic anhydrase inhibiting activities [1-8]. The presence of double bond in conjugation with carbonyl functionality is believed to be responsible for the biological activities of chalcones, as removal of this functionality make them inactive [1,3,5,7]. They have the tendency to exist both in cis- and trans-forms, and can easily be cyclized to form flavanones via Michael addition. A number of synthetic routes have been reported for synthesis of chalcones while their general synthesis involves Claisen-Schmidt condensation under homogeneous conditions in the presence of acid or base [1-8]. In this paper, we are reporting the synthesis and structural characterization of (2E)-1-(4-hydroxyphenyl)-3-(4-methoxy- phenyl)prop-2-en-1-one (I) (Scheme 1). 2. Experimental 2.1. Synthesis and crystallization An aqueous solution of sodium hydroxide (10% w:v, 10 mL) was added into the mixture of 4-methoxybenzaldehyde (0.02 mol) and 4-hydroxyacetophenone (0.02 mol) in ethanole (6 mL). After stirring it at room temperature overnight, it was poured into the water in a beaker (100 mL). This mixture was neutralised with HCl (10%) and the precipitate formed was filtered, washed with cold water and dried. ABSTRACT RESEARCH ARTICLE KEYWORDS European Journal of Chemistry ISSN 2153-2249 (Print) / ISSN 2153-2257 (Online) – Copyright © 2018 The Authors – Atlanta Publishing House LLC – Printed in the USA. This work is published and licensed by Atlanta Publishing House LLC – CC BY NC – Some Rights Reserved. http://dx.doi.org/10.5155/eurjchem.9.2.147-150.1733 http://dx.doi.org/10.5155/eurjchem.9.2.147-150.1733 https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.9.2.147-150.1733&domain=pdf&date_stamp=2018-06-30 http://www.eurjchem.com/ http://dx.doi.org/10.5155/eurjchem.9.2.147-150.1733 mailto:fatmayesilyurttt@gmail.com mailto:incigul1967@yahoo.com mailto:aaydin@kastamonu.edu.tr mailto:akkurt@erciyes.edu.tr mailto:nefised@gmail.com mailto:aaydin@kastamonu.edu.tr http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.9.2.147-150.1733&domain=pdf&date_stamp=2018-06-30� 148 Yesilyurt et al. / European Journal of Chemistry 9 (2) (2018) 147-150 Table 1. Crystal data and structure refinement for the title compound. CCDC no 1842374 Empirical formula C16H14O3 Formula weight 254.27 Temperature (K) 296(2) Crystal system Orthorhombic Space group Pbca a (Å) 13.4563(16) b (Å) 11.4986(14) c (Å) 16.720(2) Volume (Å3) 2587.1(5) Z 8 ρcalc (g/cm3) 1.306 μ (mm-1) 0.090 F(000) 1072.0 Crystal size (mm3) 0.668 × 0.380 × 0.158 Radiation MoKα (λ = 0.71073) 2Θ range for data collection (°) 4.88 to 56.76 Index ranges -17 ≤ h ≤ 17, -15 ≤ k ≤ 15, -22 ≤ l ≤ 22 Reflections collected 61402 Independent reflections 3240 [Rint = 0.0334, Rsigma = 0.0120] Data/restraints/parameters 3240/0/174 Goodness-of-fit on F2 1.041 Final R indexes [I≥2σ (I)] R1 = 0.0438, wR2 = 0.1104 Final R indexes [all data] R1 = 0.0590, wR2 = 0.1228 Largest diff. peak/hole (e.Å-3) 0.23/-0.16 Table 2. Hydrogen-bond parameters (Å, °) for compound I. D—H···A D—H H···A D···A D—H···A O3—H3···O2 i 0.82 1.88 2.6926 (17) 169 C8—H8···O1 ii 0.93 2.54 3.4383 (18) 161 Symmetry codes: (i) x+1/2, −y−1/2, −z+1; (ii) −x+1, y−1/2, −z+3/2. Figure 1. View of the molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. The solid was crystallized from ethanol-water. M.p.: 182- 184 °C, Yield: 86% [2-5,7,9,10]. OHH3CO O Scheme 1 2.2. X-ray crystallography Data collection and cell refinement for compound I were carried out using a diffractometer Bruker APEX-II CCD [11] with graphite monochromated MoKα radiation at 296 K and Bruker SAINT [11], respectively. The absorption correction was applied using multi-scan SADABS [12]. The structure was solved by using SHELXS-2014 [13] and refined by using SHELXL-2014 [13]. The structure was drawn with ORTEP-3 for Windows [14] and Software used to prepare material for publication with PLATON [15]. The crystal data, conditions of data collection and refinement are reported in Table 1. 2.3. Refinement All H-atoms were positioned geometrically (C—H = 0.93 Å for aromatic H, C—H = 0.96 Å for methyl H, O—H = 0.82 Å), and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2 Ueq(C) for aromatic H atoms, and Uiso(H) = 1.5 Ueq(C, O) for methyl and hydroxyl H atoms. 3. Result and discussion 3.1. Description of crystal structure of compound I As shown in Figure 1, whole molecule (except H atoms) of the title compound is almost planar [r.m.s. deviations for all non-H atoms = 0.001 Å]. The aromatic rings (C2–C7 and C11– C16) makes a dihedral angle of 9.35 (7)° with each other. The values of the geometric parameters are normal and comparable with those previously reported for the related structures in literature [16-18]. Intermolecular O—H···O and C—H···O hydrogen bonds link the adjacent molecules, forming a three-dimensional network structure (Table 2, Figures 2-4). In addition, π-π stacking interactions [Cg2···Cg2 (2−x, −y, 1−z) = 3.7055 (9) Å; where Cg2 is a centroid of the C11–C16 benzene ring] also contribute to the stabilization of the crystal structure. 2018 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.9.2.147-150.1733 Yesilyurt et al. / European Journal of Chemistry 9 (2) (2018) 147-150 149 Table 3. Atomic coordinates and equivalent isotropic thermal displacement parameters for non-hydrogen atoms (Å2; ( )* eq *(1/ 3)= ∑ ∑ j ij i j i ji U a a a aU ). Atom x y z Ueq O1 0.56044 (8) 0.43745 (10) 0.86953 (7) 0.0606 (4) O2 0.70623 (7) -0.13924 (10) 0.58111 (7) 0.0577 (4) O3 1.17050 (7) -0.17719 (10) 0.51465 (7) 0.0577 (4) C1 0.63246 (14) 0.50062 (15) 0.91428 (13) 0.0709 (6) C2 0.59188 (10) 0.34586 (12) 0.82428 (8) 0.0430 (4) C3 0.51834 (10) 0.28209 (13) 0.78629 (9) 0.0499 (4) C4 0.54337 (10) 0.18849 (12) 0.73899 (9) 0.0457 (4) C5 0.64222 (10) 0.15542 (11) 0.72790 (8) 0.0404 (4) C6 0.71418 (10) 0.22069 (13) 0.76745 (9) 0.0507 (5) C7 0.69045 (10) 0.31462 (13) 0.81497 (9) 0.0502 (5) C8 0.66677 (10) 0.05684 (12) 0.67640 (8) 0.0433 (4) C9 0.75684 (11) 0.02032 (14) 0.65808 (9) 0.0511 (4) C10 0.77635 (10) -0.08013 (12) 0.60571 (8) 0.0431 (4) C11 0.88015 (9) -0.10679 (11) 0.58359 (8) 0.0387 (3) C12 0.90093 (10) -0.19947 (12) 0.53215 (9) 0.0450 (4) C13 0.99669 (10) -0.22530 (12) 0.50884 (9) 0.0439 (4) C14 1.07523 (9) -0.15835 (11) 0.53666 (8) 0.0410 (4) C15 1.05667 (10) -0.06654 (12) 0.58833 (9) 0.0469 (4) C16 0.96075 (10) -0.04144 (12) 0.61111 (8) 0.0441 (4) Table 4. Selected geometric parameters (Å, °) for compound I. O1—C1 1.424 (2) O2—C10 1.234 (2) C6—C7 1.378 (2) C14—C15 1.387 (2) C1—O1—C2 118.32 (12) C5—C6—C7 122.35 (13) O3—C14—C13 122.84 (12) C1—O1—C2—C3 175.62 (14) O2—C10—C11—C16 -179.63 (13) C16—C11—C12—C13 -0.5 (2) Figure 2. The molecular packing and hydrogen bonding viewing down a- axis. H atoms not involved in hydrogen bonding have been omitted for clarity. Figure 3. The molecular packing and hydrogen bonding viewing down b- axis. H atoms not involved in hydrogen bonding have been omitted for clarity. The atomic coordinates of the non-hydrogen atoms with their equivalent temperature factors are presented in Table 3. The experimental geometric parameters of the title molecule are listed in Table 4. The values of the geometric parameters are normal and comparable with those previously reported for the related structures in literature [16-18]. Figure 4. The molecular packing and hydrogen bonding viewing down c- axis. H atoms not involved in hydrogen bonding have been omitted for clarity. 4. Conclusions In this study, we have determined the crystal structure of (2E)-1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1- one using single crystal X-ray diffraction analysis. In the crystal, molecules are linked by intermolecular O—H···O and C—H···O hydrogen bonds, forming a three-dimensional 2018 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.9.2.147-150.1733 150 Yesilyurt et al. / European Journal of Chemistry 9 (2) (2018) 147-150 network structure. Furthermore, a weak π-π stacking interactions [centroid-to-centroid distance = 3.7055(9) Å] contributes to the stabilization of the molecular packing. Acknowledgements The authors acknowledge the Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (Grant No. 2010K120480 of the State of Planning Organization). Supplementary information CCDC-1842374 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via https://www.ccdc.cam.ac.uk/ structures/, or by e-mailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223- 336033. Disclosure statement Conflict of interests: The authors declare that they have no conflict of interest. Author contributions: All authors contributed equally to this work. Ethical approval: All ethical guidelines have been adhered. Sample availability: Samples of the compounds are available from the author. ORCID Fatma Yesilyurt http://orcid.org/0000-0002-1336-6322 Abdullah Aydin http://orcid.org/0000-0003-2805-9314 Halise Inci Gul http://orcid.org/0000-0001-6164-9602 Mehmet Akkurt http://orcid.org/0000-0003-2421-0929 Nefise Dilek Ozcelik http://orcid.org/0000-0002-6972-1071 References [1]. Das, U.; Gul, H. I.; Alcorn, J.; Shrivastav, A.; George, T.; Sharma, R. K.; Nienaber, K. H.; Clercq, E. D.; Balzarini, J.; Kawase, M.; Kan, N.; Tanaka, T.; Tani, S.; Werbovetz, K. A.; Yakovich, A. J.; Manavathu, E. K.; Stables, J. P.; Dimmock, J. R. Eur. J. Med. Chem. 2006, 41, 577-585. [2]. Yerdelen, K. O.; Gul, H. I.; Sakagami, H.; Umemura, N.; Sukuroglu, M. Lett. Drug Des. Discov. 2015, 12, 643-649. [3]. Gul, H. I.; Cizmecioglu, M.; Zencir, S.; Gul, M.; Canturk, P.; Atalay M.; Topcu, Z. J. Enzyme Inh. Med. Chem. 2009, 24, 804-807. [4]. Gul, H. I.; Yerdelen, K. O.; Gul, M.; Das, U.; Pandit, B.; Li, P-K.; Secen H.; Sahin, F. Arch. Der Pharm. 2007, 340, 195-201. [5]. Bilginer, S.; Gul, H. I.; Mete, E.; Das, U.; Sakagami, H.; Umemura, N.; Dimmock, J. R. J. Enzyme Inh. Med. Chem. 2013, 28, 974-980. [6]. Bilginer, S.; Unluer, E.; Gul, H. I.; Mete, E.; Isik, S.; Vullo, D.; Ozensoy- Guler, O.; Beyaztas, S.; Capasso, C.; Supuran, C. T. J. Enzyme Inh. Med. Chem. 2014, 29, 495-499. [7]. Yamali, C.; Tugrak, M.; Gul, H. I.; Tanc, M.; Supuran, C. T. J. Enzyme Inh. Med. Chem. 2016, 31, 1678-1681. [8]. Singh, P.; Anand, A.; Kumar, V. Eur. J. Med. Chem. 2014, 85, 758-777. [9]. Yerdelen, K. O. Synthesis and evaluation of the cytotoxic activities of the compounds 3-aryl-1-(4-hydroxyphenyl)-2-propen-1 ones and 1,5-diaryl-penta-1,4-dien-3-ones and their aminomethyl derivatives. PhD thesis, Institute of Medical Sciences, Ataturk University, Erzurum, Turkey, 2009. [10]. Dimmock, J. R.; Kandepu, N. M.; Hetherington, M.; Quail, J. W.; Pugazhenthi, U.; Sudom, A. M.; Chamankhah, M.; Rose, P.; Pass, E.; Allen, T. M.; Halleran, S.; Szydlowski, J.; Mutus, B.; Tannous, M.; Manavathu, E. K.; Myers, T. G.; Clercq, E. D.; Balzarini, J. J. Med. Chem. 1998, 41, 1014-1026. [11]. Bruker. APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA, 2007. [12]. Bruker. SADABS. Bruker AXS Inc., Madison, Wisconsin, USA, 2012. [13]. Sheldrick, G. M. Acta Cryst. A 2008, 64, 112-122. [14]. Farrugia, L. J. J. Appl. Cryst. 2012, 45, 849-854. [15]. Spek, A. L. Acta Cryst. D 2009, 65, 148-155. [16]. Sarojini, B. K.; Yathirajan, H. S.; Mustafa, K.; Sarfraz, H.; Bolte, M. Acta Cryst. E 2007, 63, o4477-o4477. [17]. Sathya, S.; Reuben Jonathan, D.; Prathebha, K.; Jovita, J.; Usha, G. Acta Cryst. E 2014, 70, o1158-o1159. [18]. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc. Perkin Trans. 1987, 2, S1-19. Copyright © 2018 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. 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Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry). 2018 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.9.2.147-150.1733 https://www.ccdc.cam.ac.uk/%20structures/ https://www.ccdc.cam.ac.uk/%20structures/ mailto:data_request@ccdc.cam.ac.uk http://orcid.org/0000-0002-1336-6322 http://orcid.org/0000-0003-2805-9314 http://orcid.org/0000-0001-6164-9602 http://orcid.org/0000-0003-2421-0929 http://orcid.org/0000-0002-6972-1071 http://www.eurjchem.com/index.php/eurjchem/pages/view/terms http://creativecommons.org/licenses/by-nc/4.0 http://www.eurjchem.com/index.php/eurjchem/pages/view/terms 1. Introduction 2. Experimental 2.1. Synthesis and crystallization 2.2. X-ray crystallography 2.3. Refinement 3. Result and discussion 3.1. Description of crystal structure of compound I 4. Conclusions Supplementary information Disclosure statement ORCID References PrintField10: PrintField11: PrintField12: PrintField13: PrintField20: PrintField21: PrintField22: PrintField23: