Home Physical Sciences Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
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Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5

  • Fatin Nur Ain Abdul Rashid ORCID logo , Muhamad Zulfaqar Bacho , Alexandra M. Z. Slawin , Mohd Abdul Fatah Abdul Manan , Saiful Azmi Johari ORCID logo and Mohd Fazli Mohammat EMAIL logo
Published/Copyright: December 13, 2022

Abstract

C16H20N2O5, triclinic, P 1 (no. 2), a = 7.9179(7) Å, b = 10.1982(9) Å, c = 10.4144(8) Å, α = 76.184(7)°, β = 87.090 (7)°, γ = 73.500(8)°, V = 782.86(12) Å3, Z = 2, R gt (F) = 0.0458, wR ref (F 2) = 0.1333, T = 93 K.

CCDC no.: 2208835

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless prism
Size: 0.20 × 0.10 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.10 mm−1
Diffractometer, scan mode: Rigaku XtaLAB P200, ω
θ max, completeness: 26.4°, >99%
N(hkl) measuredN(hkl) uniqueR int: 7943, 3178, 0.038
Criterion for I obs, N(hkl) gt: I obs > 2 σ(I obs), 2979
N(param) refined: 218
Programs: CrysAlisPRO [1], SHELX [23], Mercury [4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
O2 0.11051 (12) 0.16554 (10) 0.41846 (9) 0.0256 (2)
O7 −0.05650 (12) −0.00798 (9) 0.74929 (9) 0.0252 (2)
O11 0.62501 (12) 0.08398 (9) 0.02766 (8) 0.0218 (2)
O15 0.37685 (11) 0.49239 (9) 0.62943 (9) 0.0227 (2)
O16 0.15173 (11) 0.51537 (9) 0.77205 (8) 0.0210 (2)
N1 −0.03381 (13) 0.26014 (11) 0.58643 (10) 0.0192 (2)
N3 0.36381 (13) 0.32308 (11) 0.44944 (10) 0.0210 (2)
C2 0.09672 (15) 0.23665 (12) 0.49985 (11) 0.0180 (3)
C3 0.22057 (15) 0.31601 (12) 0.52269 (11) 0.0168 (3)
C4 0.15872 (15) 0.37848 (12) 0.62344 (11) 0.0171 (3)
C5 −0.00996 (15) 0.34710 (12) 0.67152 (11) 0.0182 (3)
H5A 0.000488 0.295627 0.765591 0.022*
H5B −0.108557 0.434339 0.660656 0.022*
C6 −0.18845 (16) 0.21055 (14) 0.58967 (12) 0.0235 (3)
H6A −0.183048 0.162756 0.516621 0.028*
H6B −0.294674 0.292329 0.574819 0.028*
C7 −0.20545 (16) 0.10962 (13) 0.71960 (12) 0.0228 (3)
H7A −0.222266 0.159903 0.791731 0.027*
H7B −0.311069 0.077179 0.714958 0.027*
C8 0.42331 (15) 0.25494 (13) 0.34363 (12) 0.0183 (3)
C9 0.36126 (16) 0.32034 (13) 0.21533 (13) 0.0237 (3)
H9 0.271743 0.407427 0.198590 0.028*
C10 0.42897 (16) 0.25948 (13) 0.11218 (12) 0.0228 (3)
H10 0.385147 0.304037 0.024651 0.027*
C11 0.56138 (15) 0.13291 (12) 0.13611 (11) 0.0175 (3)
C12 0.62112 (15) 0.06565 (12) 0.26465 (12) 0.0176 (3)
H12 0.708970 −0.022341 0.281932 0.021*
C13 0.55152 (15) 0.12793 (12) 0.36767 (11) 0.0175 (3)
H13 0.592751 0.082492 0.455646 0.021*
C14 0.75390 (17) −0.05001 (13) 0.05126 (12) 0.0240 (3)
H14A 0.858124 −0.044962 0.094595 0.029*
H14B 0.787361 −0.076083 −0.033088 0.029*
H14C 0.704607 −0.120876 0.108448 0.029*
C15 0.24119 (15) 0.46570 (12) 0.67301 (11) 0.0178 (3)
C17 0.22268 (18) 0.60931 (14) 0.82359 (12) 0.0246 (3)
H17A 0.228085 0.691792 0.752255 0.029*
H17B 0.343285 0.559982 0.859765 0.029*
C18 0.10359 (18) 0.65577 (14) 0.93055 (13) 0.0257 (3)
H18A 0.100625 0.573518 1.001217 0.031*
H18B −0.015559 0.703724 0.893858 0.031*
H18C 0.147814 0.720445 0.966503 0.031*
H7 −0.058 (3) −0.0669 (17) 0.6883 (15) 0.047 (5)*
H3 0.431 (2) 0.3830 (15) 0.4679 (17) 0.037 (4)*

Source of materials

A mixture of 2,3-dioxopyrrolidine (2.00 g, 9.29 mmol), p-anisidine (1.37 g, 11.15 mmol) and formic acid (0.56 mL, 14.87 mmol) in ethanol was refluxed for 24 h. The solution was concentrated by distillation. The organic mixture was extracted with dichloromethane, washed with water and dried over MgSO4. The solvent was evaporated under reduced pressure and the crude was purified by column chromatography on silica gel (ethyl acetate:petroleum ether, 50:50) to afford 1 as brown solid product (2.34 g, 79%).

Experimental details

The data were indexed and processed using CrysAlisPRO [1]. A multi-scan absorption correction was performed. The structure was solved with SHELXT Version 2018/2 [2] solution program. The model was refined with SHELXL Version 2018/3 [3].

Comment

Pyrrolinones play an important role in organic synthesis and find vast applications in pharmaceutical fields due to their broad range of biological properties such as anti-inflammatory, antifungal, and antibacterial activities [56]. Owing to their notable pharmaceutical effects, they have received tremendous attention over the past few years [7]. Thus, in view of diversifying the structural motifs of these classes of compounds, we decided to prepare the analogue of N-substituted pyrrolinone via amination of 2,3-dioxopyrrolidine with p-anisidine [8]. The starting material, 2,3-dioxopyrrolidine was initially prepared according to the reported procedure [9], [10], [11]. This paper describes the crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate (1).

The crystal structure of 1 is similar to previously reported structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate [12]. All bond angles and lengths are within the normal ranges and comparable to the related structures [12], [13], [14], [15]. The 4-methoxyaniline (N3/C8–C13/O11/C–14) and hydroxyethyl (C6/C7/O7) moieties are observed slightly twisted at N3–C8 and C6–C7 bonds, respectively. The twisted angle of C3–N3–C8–C9 is found to be 87.97° while the twisted angle for N1–C6–C7–O7 is −57.11. The ethyl acetate (O15/O16/C15/C17/C18) and 4-methoxyaniline (N3/C8–C13/O11/C14) moieties are almost perpendicular to each other, subtending a dihedral angle of 86.00°. Meanwhile, the pyrrole ring (N1/C2–C5) forms a dihedral angle of 83.17° with the phenyl ring (C8–C13). In the molecule, an intramolecular N3–H3···O15 hydrogen bond is observed, forming a pseudo six-membered ring, which further stabilizes and lock its atoms in a nearly planar arrangement. A similar feature was observed in the reported structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate [16].


Corresponding author: Mohd Fazli Mohammat, Organic Synthesis Research Laboratory, Institute of Science, Universiti Teknologi MARA, 42300 Bandar Puncak Alam, Selangor, Malaysia, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Forest Research Institute Malaysia (FRIM) and Malaysian Government (MOHE) for the financial support (FRGS/1/2019/STG05/NRE/03/1).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2022-10-14
Accepted: 2022-11-25
Published Online: 2022-12-13
Published in Print: 2023-01-27

© 2022 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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