Home The crystal structure of 3-(2,5-dimethylanilino)-1-(2,5-dimethylphenyl)-4-methyl-1H-pyrrole-2,5-dione, C21H22N2O2
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The crystal structure of 3-(2,5-dimethylanilino)-1-(2,5-dimethylphenyl)-4-methyl-1H-pyrrole-2,5-dione, C21H22N2O2

  • Ramakwala Christinah Chokwe ORCID logo and Mark G. Smith ORCID logo EMAIL logo
Published/Copyright: October 16, 2024

Abstract

C21H22N2O2, monoclinic, C2/c (no. 15), a = 15.4261(9) Å, b = 10.0885(6) Å, c = 23.9311(13) Å, β = 106.875(2)°, V = 3563.9(4) Å3, Z = 8, R gt (F) = 0.0457, wR ref (F 2) = 0.1196, T = 173 K.

CCDC no.: 2380168

1 Source of materials

4-aminoantipyrine, diflunisal, salicylaldehyde and chloroform were commercially sourced and not purified any further. 0.0948 g (0.4664 mmol) of 4-aminoantipyrine and 0.1162 g (0.4644 mmol) of diflunisal were dissolved in a mixture of 1 mL of salicylaldehyde and 3 mL of chloroform while stirring with a magnetic stirrer bar at 40 °C in a polytop vial for 6 h. The solution was left to evaporate at room temperature, with the cap being left slightly open. Yellow plate crystals formed after 24 h. The data collection and handling details as well as the fractional atomic coordinates and isotropic displacement parameters are given in Tables 1 and 2.

Table 1:

Data collection and handling.

Crystal: Yellow plate
Size: 0.29 × 0.09 × 0.04 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Bruker D8 Venture Photon, ω
θ max, completeness: 25.8°, >99 %
N(hkl)measured, N(hkl)unique, R int: 26363, 3427, 0.045
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2,617
N(param)refined: 234
Programs: Bruker 1 , SHELX 2 , 3 , WinGX/ORTEP 4 , 5 , PLATON 6
Table 2:

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

Atom x y z U iso*/U eq
C1 0.13284 (11) 0.33272 (17) 0.33205 (7) 0.0265 (4)
C2 0.07246 (11) 0.33849 (17) 0.37118 (7) 0.0253 (4)
C3 0.12266 (11) 0.37026 (17) 0.42589 (7) 0.0271 (4)
C4 0.21640 (12) 0.38264 (17) 0.42471 (7) 0.0271 (4)
C5 0.09857 (13) 0.3976 (2) 0.48091 (8) 0.0368 (5)
H5A 0.032532 0.401760 0.472361 0.055*
H5B 0.125076 0.482346 0.497360 0.055*
H5C 0.122300 0.326464 0.509113 0.055*
C6 0.29670 (11) 0.37232 (18) 0.34576 (7) 0.0278 (4)
C7 0.30305 (12) 0.47629 (19) 0.30869 (7) 0.0343 (4)
C8 0.38101 (14) 0.4791 (2) 0.29047 (8) 0.0462 (6)
H8 0.387995 0.547305 0.264750 0.055*
C9 0.44806 (14) 0.3855 (2) 0.30883 (9) 0.0479 (6)
H9 0.500065 0.390549 0.295268 0.058*
C10 0.44199 (12) 0.2841 (2) 0.34649 (9) 0.0414 (5)
C11 0.36423 (12) 0.27879 (19) 0.36419 (8) 0.0337 (4)
H11 0.357251 0.209545 0.389437 0.040*
C12 0.23238 (14) 0.5824 (2) 0.29125 (9) 0.0451 (5)
H12A 0.175546 0.543726 0.267135 0.068*
H12B 0.252751 0.650943 0.268894 0.068*
H12C 0.222610 0.622064 0.326325 0.068*
C13 0.51684 (16) 0.1841 (3) 0.36801 (14) 0.0698 (8)
H13A 0.529389 0.140664 0.334547 0.105*
H13B 0.498154 0.117401 0.391984 0.105*
H13C 0.571637 0.229031 0.391494 0.105*
C14 −0.08314 (11) 0.30577 (17) 0.37637 (7) 0.0266 (4)
C15 −0.07894 (12) 0.20627 (18) 0.41757 (7) 0.0299 (4)
C16 −0.14671 (13) 0.2058 (2) 0.44533 (8) 0.0357 (4)
H16 −0.145492 0.140030 0.473959 0.043*
C17 −0.21545 (12) 0.2980 (2) 0.43242 (8) 0.0358 (4)
H17 −0.260220 0.294884 0.452534 0.043*
C18 −0.22065 (11) 0.39530 (19) 0.39067 (8) 0.0315 (4)
C19 −0.15340 (11) 0.39749 (18) 0.36291 (7) 0.0289 (4)
H19 −0.155330 0.463035 0.334069 0.035*
C20 −0.00690 (13) 0.1012 (2) 0.43089 (9) 0.0401 (5)
H20A 0.044203 0.130121 0.463571 0.060*
H20B 0.013918 0.086192 0.396422 0.060*
H20C −0.031820 0.018619 0.441385 0.060*
C21 −0.29552 (13) 0.4960 (2) 0.37738 (9) 0.0438 (5)
H21A −0.291190 0.549330 0.412304 0.066*
H21B −0.354156 0.450473 0.365500 0.066*
H21C −0.290081 0.553796 0.345670 0.066*
N1 0.21833 (9) 0.36199 (15) 0.36606 (6) 0.0283 (3)
N2 −0.01629 (9) 0.31343 (15) 0.34596 (6) 0.0291 (4)
O1 0.11033 (8) 0.30613 (14) 0.28042 (5) 0.0356 (3)
O2 0.28346 (8) 0.40655 (13) 0.46438 (5) 0.0361 (3)
H2 −0.0327 (14) 0.311 (2) 0.3081 (10) 0.043*

2 Experimental details

The C-bound hydrogen atoms were located in the difference map, then positioned geometrically. They were then allowed to ride on their respective parent atoms with thermal displacement parameters 1.2 times of the parent C atom. The coordinates and isotropic displacement parameters of the N-bound H atom, namely H2, was allowed to refine freely. Diagrams and publication material were generated using ORTEP-3, 4 WinGX 5 and PLATON. 6

3 Discussion

Antipyrine and 4-(N,N-dimethyl)-antipyrine are known for their analgesic, antipyretic and anti-inflammatory propertes. However, the use of pyrazolones has been associated with agranulocytosis. 7 The use of 4-aminoantipyrine has mainly been discontinued due to dangerous side effects. 8 The covalent modification of antipyrines results in new structures that can be tested for the desired therapeutic activity and cytotoxicity.

The asymmetric unit of the crystal contains one molecule of 3-(2,5-dimethylanilino)-1-(2,5-dimethylphenyl)-4-methyl-1H-pyrrole-2,5-dione, and crystallizes in the monoclinic C2/c space group. The unit cell (Z = 8) contains four dimers of the molecule held together by hydrogen bonds. The bonding between each of these dimers occurs between the secondary amine hydrogen donor (N2–H2) of one molecule and a carbonyl hydrogen bond acceptor (C1–O1) of an adjacent molecule via a N2–H2⋯O1 synthon. Bond lengths are in the expected ranges 9 .


Corresponding author: Mark G. Smith, Chemistry Department, University of South Africa, Unisa Science Campus, 28 Pioneer Avenue, Florida, Roodepoort, Gauteng, South Africa, 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: This work was supported by the National Research Foundation (NRF) “Competitive Support for Unrated Researchers” grant Number CSUR23042597072 (Dr MG Smith) as well as the University of South Africa.

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

References

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Received: 2024-08-28
Accepted: 2024-10-04
Published Online: 2024-10-16
Published in Print: 2024-12-17

© 2024 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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