Synthesis, spectroscopic and X-ray crystallographic analysis of N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide European Journal of Chemistry 10 (3) (2019) 234-238 European Journal of Chemistry View Journal Online View Article Online Synthesis, spectroscopic and X-ray crystallographic analysis of N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide Fares Hezam Al-Ostoot 1,2, Jigmat Stondus 3, Sumati Anthal 3, Geetha Doddenahally Venkatesh 4, Yasser Hussein Eissa Mohammed 1,5, Mandayam Anandalwar Sridhar 4, Shaukath Ara Khanum 1 and Rajni Kant 3,* 1 Department of Chemistry, Yuvaraja’s College, University of Mysore, Mysuru, 570005, India faresalostoot@gmail.com (F.H.A.), issayasser16@gmail.com (Y.H.E.M.), shaukathara@yahoo.co.in (S.A.K.) 2 Department of Biochemistry, Faculty of Education and Science, Albaydaa University, Al bayda, 00967, Yemen 3 X-ray Crystallography Laboratory, Department of Physics, University of Jammu, Jammu, 180006, India jstondus@gmail.com (J.S.), sumatianthal@gmail.com (S.A.), rkant.ju@gmail.com (R.K.) 4 Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru, 570005, India geetha@uomphysics.net (G.D.V.), mas@physics.uni-mysore.ac.in (M.A.S.) 5 Department of Biochemistry, Faculty of Applied Science, University of Hajjah, Hajjah, 00967, Yemen * Corresponding author at: Department of Physics, University of Jammu, Jammu, 180006, India. Tel: +91.9419194375 Fax: +91.191.2432051 e-mail: rkant.ju@gmail.com (R. Kant). 10.5155/eurjchem.10.3.234-238.1874 Received: 13 April 2019 Received in revised form: 23 May 2019 Accepted: 28 May 2019 Published online: 30 September 2019 Printed: 30 September 2019 Medicinal chemistry of indole analogs constitutes important therapeutic agents with anti- oxidant, anti-HIV and anti-cancer activities. Indole nucleus is frequently found in synthetic and natural products, pharmaceuticals, functional materials, agrochemicals, etc. The title compound, N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide (5), has been synthesized in good yield by stirring the compound N-(2-aminophenyl)-2-(4- chlorophenoxy)acetamide (3) with 1H-indole-2-carboxylic acid (4), in dry dichloromethane followed by the addition of 2,6-lutidine, and o-(benzotriazol-1-yl)-N,N,N',N'-tetramethyl uraniumtetrafluoroborate in cooled condition. Compound 5 was synthesized and characterized by the conventional spectroscopic techniques (1H NMR, 13C NMR and LC-MS) and the three-dimensional structure was elucidated by using single crystal X-ray diffraction methods. It crystallizes in the monoclinic crystal system with space group P21/c. The structure was solved by direct methods and refined by full matrix least square procedure to a final R value of 0.043 for 2490 observed reflections. Three intra-molecular interactions of the type N-H···N and C-H···N were observed. The packing of molecules in the unit cell is governed by N-H···O and C-H···O intermolecular H-boned interactions which leads to the formation of infinite staking chain along [001] direction. In addition, two weak C-H···π interactions also contribute to molecular packing. Amide Single crystal X-ray diffraction Indole analogues H-bonded interactions Spectroscopic analysis Cite this: Eur. J. Chem. 2019, 10(3), 234-238 Journal website: www.eurjchem.com 1. Introduction In drug discovery, medicinal chemists use the privileged structures to synthesize a novel compounds based on a central scaffold and to screen them against different receptors involved in various pathways, in other cases producing biologically active compounds. Indole nucleus is often found in medicinal chemistry world with unique properties due to the presence of a rich-in-electron at pyrrole moiety [1] that can use non-covalent interactions with other molecules by formation of hydrogen bonding in the NH moiety by π-π system [2] and is considered as privileged structures [3,4]. Due to this unique property, indole and its derivatives are used broadly for new drugs therapy development [5]. Therefore, due and considerable attention has been given to the development of synthetic methods for the preparation of such materials and their structure elucidation for its possible pharmaceutical properties, viz. anti-histaminic, anti- inflammatory [6,7], anti-oxidant [8], anti-rheumatoid, anti-HIV [9,10] and anti-cancer activity [11-14]. Indole and its derivatives have also played a vital role in the field of immunology [15,16]. Furthermore, it is considered as the most potent scavenger of free radicals [17]. Different studies involving in vitro and in vivo inhibition activity have shown that compounds with indole moiety can effectively inhibit the diabetic activity [18,19]. The design and selective functioning of indoles have been the center of the current investigation over the years [20-24]. In view of their broad spectrum of biological properties and as a part of our ongoing work on synthesis and characterization of indole derivatives [25,26], the synthesis, spectroscopic and X-ray crystallographic analy- ABSTRACT RESEARCH ARTICLE KEYWORDS European Journal of Chemistry ISSN 2153-2249 (Print) / ISSN 2153-2257 (Online) – Copyright © 2019 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.10.3.234-238.1874 http://dx.doi.org/10.5155/eurjchem.10.3.234-238.1874 https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.10.3.234-238.1874&domain=pdf&date_stamp=2019-09-30 http://www.eurjchem.com/ http://dx.doi.org/10.5155/eurjchem.10.3.234-238.1874 mailto:faresalostoot@gmail.com mailto:issayasser16@gmail.com mailto:shaukathara@yahoo.co.in mailto:jstondus@gmail.com mailto:sumatianthal@gmail.com mailto:rkant.ju@gmail.com mailto:geetha@uomphysics.net mailto:mas@physics.uni-mysore.ac.in mailto:rkant.ju@gmail.com http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.10.3.234-238.1874&domain=pdf&date_stamp=2019-09-30� Al-Ostoot et al. / European Journal of Chemistry 10 (3) (2019) 234-238 235 N H HO O O O OH Cl NH2 NH2 O O H N NH2 Cl NH O HN NH O O Cl TBTU/Lutidine DCM (1) (4) (5) TBTU/Lutidine DCM (2) (3) + O O H N NH2 Cl (3) + Scheme 1. Reaction pathway for the synthesis of compound 5. sis of N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H- indole-2-carboxamide is reported in this paper. 2. Experimental 2.1. Materials and instrumentations Chemicals, solvents and agents were purchased from Sigma Aldrich. Analytical thin layer chromatography (TLC) was performed on 0.25 mm silica gel plates (Merck 60 F254) by using solvent system using hexane: ethyl acetate (9:3, v:v). Melting point was determination using the Chemi Line CL725 Micro Controller Based melting point apparatus with a digital thermometer. The NMR spectrum (1H NMR and 13C NMR) was recorded on a VNMRS-400 MHz Agilent-NMR spectrophoto- meter in DMSO-d6. Mass spectra was obtained with a VG70- 70H spectrometer. Elemental analysis (Elementar Vario EL III elemental analyzer) results are within 0.5% range of the calculated values. The three dimensional molecular structure of the compound was confirmed by single crystal X-ray diffraction technique. 2.2. Synthesis of N-(2-aminophenyl)-2-(4-chlorophenoxy) acetamide (3) The title compound N-(2-aminophenyl)-2-(4-chloro phenoxy)acetamide (3) was obtained by the synthetic proce- dure as shown in Scheme 1. To compound 1 (0.8 g, 0.009 mol), in dry DCM (10 mL), 2,6-lutidine (1.3 vol.) was added at 25-30 °C, followed by the addition of 1,2-diaminobenzene 2 (1.5 g, 0.009 mol), the reaction mixture was stirred at 25-30 °C for 25 min. The reaction was cooled to 0-5 °C and 2-(1H-benzo- triazole-1-yl)-1, 1, 3, 3-tetramethylaminium tetrafluoro borate (TBTU) (4.5 g, 0.02 mol) was added over a period of 30 minutes while maintaining the temperature below 5 °C. The reaction was stirred overnight and monitored by TLC using mobile phase system (hexane: ethyl acetate, 9:3, v:v). The reaction mixture was diluted with 25 mL of DCM and treated with 2.0 N HCl solution (20 mL). The organic layer was washed with water (3 × 25 mL) and brine (3 × 25 mL). Finally, the organic layer was dried over anhydrous sodium sulfate and concentrated to afford compound 3 [27,28]. 2.3. Synthesis of N-(2-(2-(4-chlorophenoxy)acetamido) phenyl)-1H-indole-2-carboxamide (5) To the compound of N-(2-aminophenyl)-2-(4-chloro phenoxy)acetamide 3 (0.5 g, 0.002 mol), in dry DCM (10 mL), 1H-indole-2-carboxylic acid 4 (0.3 g, 0.002 mol), was added at 25-30 °C, followed by the addition of 2,6-lutidine (0.001 mol). The reaction mixture was stirred at 25-30 °C for 30 minutes. The reaction was cooled to 0-5 °C, TBTU (0.9 g, 0.003 mol) was added over a period of 30 min while maintaining the temperature below 5 °C. The reaction was stirred overnight and monitored by TLC mobile phase system (hexane: ethyl acetate, 9:3, v:v). The reaction mixture was diluted with (25 mL) of DCM and treated with 10% of sodium bicarbonate solution (3×25 mL). The organic layer was washed with water (3×25 mL), dried over anhydrous sodium sulfate and concentrated to yield compound 5 [29,30]. The crude product upon re-crystallization with ethanol afforded the title compound 5 as colorless rectangular block shape crystals and then confirmed by 1H NMR, 13C NMR, LC-MS spectra. The schematic diagram of the synthesized compound is shown in Scheme 1. N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole- 2-carboxamide (5): Color: White. Yield: 85%. M.p.: 205-207 ᵒC. FT-IR (KBr, νmax, cm-1): 1633 (amide, C=O), 3210-3320 (amide CO-NH). 1H NMR (400 MHz, DMSO-d6 , δ, ppm): 4.71 (s, 2H, OCH2), 6.89-7.77 (s, 13H, Ar-H), 9.65 (s, 1H, NH), 10.18 (s, 1H, NH), 11.83 (s, 1H, NH indole). 13C NMR (100 MHz, DMSO-d6 , δ, ppm): 166.96, 160.65, 156.44, 137.40, 131.51, 131.10, 130.10, 129.67, 129.48, 127.49, 126.43, 126.37, 125.83, 125.55, 124.44, 122.25, 120.48, 116.87, 116.63, 112.90, 104.70, 67.76. LC-MS (m/z): 420 [M+], 422 [M+2]. 2.4. X-ray intensity data collection, structure solution and refinement A block-shaped single crystal with good surface morphology was chosen for intensity data collection. The data were collected on Bruker Kappa APEX-II four circle-CCD diffractrometer [31] using graphite monochromated MoKα radiation (λ = 0.71071 Å). A total of 26028 reflections were collected at 296 K out of which 4086 reflections were found unique. The structure solution was carried out by Direct Methods using SHELXS [32] and the non-H atoms were located in the best E-map. Full matrix least square refinement procedure resulted the structure to converge to a final R-value of 0.043 for 2490 observed reflections (I>2σ(I)) using SHELXL [33]. 2019 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.10.3.234-238.1874 236 Al-Ostoot et al. / European Journal of Chemistry 10 (3) (2019) 234-238 Table 1. Crystal data and experimental details: Crystal data Chemical formula C 23H18ClN3O3 M r 419.85 Crystal system, space group Monoclinic, P21/c Temperature (K) 296 a, b, c (Å) 11.171 (2), 21.929 (5), 9.307 (2) β (°) 114.257 (14) V (Å3) 2078.7 (9) Z 4 Radiation type Mo Kα µ (mm−1) 0.21 Crystal size (mm) 0.30 × 0.25 × 0.20 Data collection Diffractometer Bruker APEX-II CCD Absorption correction Multi-scan SADABS (Sheldrick, 1996) Tmin, Tmax 0.885, 0.959 No. of measured, independent and observed [I> 2σ(I)] reflections 26028, 4086, 2490 R int 0.050 (sin θ/λ)max (Å−1) 0.617 Refinement R[F2> 2σ(F2)], wR(F2), S 0.043, 0.118, 1.00 No. of reflections 4086 No. of parameters 271 H-atom treatment H-atom parameters constrained Δρmax , Δρmin (e Å−3) 0.16, −0.28 Figure 1. ORTEP view of the molecule with the ellipsoid probability at 40% (dashed lines represents intra-molecular H-bonded interactions). All the hydrogen atoms were fixed geometrically and allowed to ride on their corresponding non-H atoms with U iso(H) = 1.2 Ueq(N) and 1.2 Ueq(C) (N-H= 0.86 Å, C-H= 0.93 Å). The atomic scattering factors were taken from International Tables for X-ray Crystallography (1992, Vol C, Tables 4.2.6.8 and 6.1.1.4). The publication materials of the structure of the compound have been prepared using WingX [34], PLATON [35] and PARST [36] software programs. 3. Results and discussion A precise description of the crystallographic data of the X-ray structure is given in Table 1. The molecule consists of three benzene rings [A(C1-C6), C(C10-C15) and D(C18-C23)] and a pyrrolidine ring B(C1/C6/C7/C8/N1) (Figure 1) (Mercury) [37]. Ring A and B are fused together forming indole ring system which is connected with ring C through acetamide group. Furthermore, the Ring C and D are connected through hydroxyacetamide group. The structural parameters including bond distances, bond angles and torsion angles are listed in Table 2. The bond distances of C9=O1 and C16=O2 are 1.244(3) Å and 1.234(3) Å, respectively, indicate a typical C=O double bond character. All the bond distances fall in the normal range [38], except for C18-C23 = 1.358(4) Å which is slightly shortened. This could possibly be due to the presence of oxygen atom at C18 and its involvement in hydrogen bond formation. The indole ring system is approximately planar with maximum deviation of 0.0293 Å obtained for N1 atom and the benzene rings C and D are also planar (with maximum deviation of -0.0110 Å for C11). The least square plane of indole ring (C1/C2/C3/C4/C5/C6/C7/C8/N1) makes a dihedral angle of 47.49 and 85.21ᵒ, respectively, with the least square planes of the ring C and ring D. Similarly, the least square planes of ring C and ring D make a dihedral angle of 40.83ᵒ. The N-H···O (N3-H3A···O1, N3-H3A···O3) and C-H···O (C14-H14···O2) intra-molecular hydrogen interactions result in the formation of three virtual rings with S(7), S(6) and S(5) graph-set motif [39] as shown in the ORTEP plot (Figure 1). In the crystal structure, the adjacent molecules are linked by N- H···O (N1-H1···O1, N2-H2A···O2) and C-H···O (C19-H19···O1) intermolecular hydrogen bonded interactions forming one dimensional stacking chain along [001] direction (Figure 2) (Mercury 3.10.2) [37]. In addition, the crystal structure is also stabilized by two weak C-H···π (C23-H23···Cg2 and C23- H23···Cg5) interactions (Table 3). 4. Conclusion The compound N-(2-(2-(4-chlorophenoxy)acetamido) phenyl)-1H-indole-2-carboxamide was synthesized and characterized by 1H NMR, 13C NMR and LC MS spectroscopic techniques. The molecular structure of the compound was finally confirmed by single crystal XRD technique. 2019 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.10.3.234-238.1874 Al-Ostoot et al. / European Journal of Chemistry 10 (3) (2019) 234-238 237 Table 2. Selected bond distances, bond angles and torsion angles. Bond distance (Å) C1-N1 1.368 (3) C10-N2 1.421 (3) C6-C7 1.424 (3) C14-C15 1.396 (3) C7-C8 1.358 (3) C15-N3 1.415 (3) C8-N1 1.373 (3) C16-O2 1.234 (3) C8-C9 1.468 (3) C16-N3 1.342 (3) C9-O1 1.244 (3) C16-C17 1.504 (3) C9-N2 1.346 (3) C17-O3 1.424 (3) C10-C11 1.381 (3) C18-O3 1.371 (3) C10-C15 1.396 (3) C21-Cl1 1.742 (3) Bond angle (ᵒ) N1-C1-C2 130.6 (2) C14-C15-N3 120.8 (2) N1-C1-C6 107.5 (2) C10-C15-N3 119.9 (2) C2-C1-C6 121.8 (2) O2-C16-N3 125.6 (2) C5-C6-C1 118.6 (2) O2-C16-C17 119.3 (2) C5-C6-C7 134.7 (2) N3-C16-C17 115.1 (2) C1-C6-C7 106.7 (2) O3-C17-C16 109.1 (2) C8-C7-C6 107.3 (2) C23-C18-O3 124.4 (2) C7-C8-N1 109.2 (2) C23-C18-C19 120.5 (2) C7-C8-C9 132.1 (2) O3-C18-C19 115.0 (2) N1-C8-C9 118.5 (2) C22-C21-Cl1 119.6 (2) O1-C9-N2 122.2 (2) C20-C21-Cl1 119.5 (2) O1-C9-C8 120.92 (19) C18-C23-C22 118.9 (3) N2-C9-C8 116.8 (2) C1-N1-C8 109.19 (19) C11-C10-C15 118.9 (2) C9-N2-C10 127.11 (19) C11-C10-N2 118.6 (2) C16-N3-C15 126.78 (19) C15-C10-N2 122.3 (2) C18-O3-C17 119.53 (19) Torsion angle (ᵒ) C6-C7-C8-C9 175.1 (2) C8-C9-N2-C10 −175.0 (2) C7-C8-C9-O1 177.9 (2) C11-C10-N2-C9 −131.8 (3) N1-C8-C9-O1 −7.0 (3) N3-C16-C17-O3 −7.9 (3) C7-C8-C9-N2 −5.0 (4) C14-C15-N3-C16 −39.9 (3) N1-C8-C9-N2 170.1 (2) C10-C15-N3-C16 140.0 (2) N2-C10-C11-C12 −172.3 (2) C23-C18-O3-C17 10.3 (4) N2-C10-C15-C14 173.5 (2) C19-C18-O3-C17 −172.1 (2) N2-C10-C15-N3 −6.4 (3) C16-C17-O3-C18 168.5 (2) O2-C16-C17-O3 174.1 (2) C2-C1-N1-C8 176.8 (3) C15-C10-N2-C9 54.3 (3) Table 3. List of D-H···A and D-H···π H-bonded interactions *. No D-H....A D – H (Å) H···A (Å) D···A (Å) D - H···A (ᵒ) 1 N3-H3A···O1 0.86 2.06 2.7897(6) 142 2 N3-H3A···O3 0.86 2.09 2.5479(6) 113 3 C14-H14···O2 0.93 2.58 2.9874(7) 107 4 N1-H1···O1(i) 0.86 2.20 2.9702(7) 150 5 N2 -H2A···O2(ii) 0.86 2.06 2.8530(7) 153 6 C19-H19···O1(ii) 0.93 2.56 3.3155(8) 139 7 C23-H23···Cg1(iii) 0.93 2.78 3.6149(8) 150 8 C23-H23···Cg2(iii) 0.93 2.93 3.8418(9) 169 * Symmetry codes: (i) –x, -y, 1-z, (ii) 1-x,-y,1-z, (iii) x,y,-1+z; Cg1 represents centre of gravity of ring A and Cg2 represents centre of gravity of Indole ring system (fused structure of ring A and B). Figure 2. A fraction of molecular packing showing N-H···O and C-H···O H-bonded interaction. 2019 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.10.3.234-238.1874 238 Al-Ostoot et al. / European Journal of Chemistry 10 (3) (2019) 234-238 The compound crystallizes in the monoclinic crystal system with space group P21/c. Crystallographic analysis of the compound reveals the existence of three intra-molecular hydrogen bonds (of the type N-H···O and C-H···O), three inter- molecular H-bonded interactions (of the type N-H···O and C- H···O) and two weak C-H···π interactions, that contributes in the stability of the crystal structure. Acknowledgements Rajni Kant is thankful to the Department of Science and Technology (Project No, EMR/2014/000467) for research funding. Supporting information CCDC-1893314 contains the supplementary crystallo- graphic 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. Funding Department of Science and Technology http://dx.doi.org/10.13039/501100010218 ORCID Jigmat Stondus http://orcid.org/0000-0002-6924-0454 Sumati Anthal http://orcid.org/0000-0001-7947-7335 Fares Hezam Al-Ostoot http://orcid.org/0000-0003-4571-6419 Geetha Doddenahally Venkatesh http://orcid.org/0000-0001-8628-8794 YasserHussein Eissa Mohammed http://orcid.org/0000-0003-1086-7292 Mandayam Anandalwar Sridhar http://orcid.org/0000-0002-3065-3630 Shaukath Ara Khanum http://orcid.org/0000-0003-1713-4489 Rajni Kant http://orcid.org/0000-0001-8043-2329 References [1]. Lal, S.; Snape, T. J. Curr. Med. Chem. 2012, 19, 4828-4837. [2]. Shimazaki, Y.; Yajima, T.; Takani, M.; Yamauchi, O. Coordin. Chem. Rev. 2009, 253, 479-492. [3]. Sundberg, R. J. Indoles, Academic Press, San Diego, 1996. [4]. Denhart, D. J.; Deskus, J. A.; Ditta, J. L.; Gao, Q.; King, H. 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Ed. Engl. 1995, 34, 1555-1573. Copyright © 2019 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. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. 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). 2019 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.10.3.234-238.1874 https://www.ccdc.cam.ac.uk/structures/ mailto:data_request@ccdc.cam.ac.uk http://dx.doi.org/10.13039/501100010218 http://orcid.org/0000-0002-6924-0454 http://orcid.org/0000-0001-7947-7335 http://orcid.org/0000-0003-4571-6419 http://orcid.org/0000-0001-8628-8794 http://orcid.org/0000-0003-1086-7292 http://orcid.org/0000-0002-3065-3630 http://orcid.org/0000-0003-1713-4489 http://orcid.org/0000-0001-8043-2329 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. Materials and instrumentations 2.2. Synthesis of N-(2-aminophenyl)-2-(4-chlorophenoxy) acetamide (3) 2.3. Synthesis of N-(2-(2-(4-chlorophenoxy)acetamido) phenyl)-1H-indole-2-carboxamide (5) 2.4. X-ray intensity data collection, structure solution and refinement 3. Results and discussion 4. Conclusion Acknowledgements Supporting information Disclosure statement Funding ORCID References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: