Synthesis and crystal structure of 3-(2-{3-[2-(2-oxooxazolidin-3-yl)eth­oxy]quinoxalin-2-yl­oxy}eth­yl)oxazolidin-2-one

Fatima Ezzahra Aboutofil; Nour El Hoda Mustaphi; Olivier Blacque; Tuncer Hökelek; Ahmed Mazzah; Lhoussaine El Ghayati; Nada Kheira Sebbar

doi:10.1107/S2056989025003755

. 2025 May 2;81(Pt 6):469–472. doi: 10.1107/S2056989025003755

Synthesis and crystal structure of 3-(2-{3-[2-(2-oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one

Fatima Ezzahra Aboutofil ^a, Nour El Hoda Mustaphi ^a,^*, Olivier Blacque ^b, Tuncer Hökelek ^c, Ahmed Mazzah ^d, Lhoussaine El Ghayati ^a, Nada Kheira Sebbar ^e,^f

Editor: W T A Harrison^g

PMCID: PMC12142413 PMID: 40487685

In the title compound, one of the oxazolidine rings adopts a twisted conformation and the other is a shallow envelope. In the crystal, weak C—H⋯O hydrogen bonds and π–π stacking interactions help to consolidate a three-dimensional architecture.

Keywords: crystal structure, hydrogen bond, π-stacking, quinoxaline

Abstract

In the title compound, C₁₈H₂₀N₄O₆, one of the oxazolidine rings adopts a twisted conformation and the other is a shallow envelope. In the crystal, weak C—H⋯O hydrogen bonds and π–π stacking interactions help to consolidate a three-dimensional architecture. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (48.4%) and H⋯O/O⋯H (29.1%) contacts.

1. Chemical context

Quinoxaline and its derivatives are widely used in various fields, including medicine (Kaushal et al., 2019 ▸; Montana et al., 2019 ▸), pharmacology, molecular biology, neuroscience, immunology, microbiology, agriculture, chemistry, toxicology, materials science, and biochemistry (Balderas-Renteria et al., 2012 ▸; Pereira et al., 2015 ▸; Zeb et al., 2014 ▸; Tangherlini et al., 2019 ▸; Vieira et al., 2014 ▸; Zheng et al., 2002 ▸).

The quinoxaline molecule has been utilized as a precursor for synthesizing bioactive derivatives, with several research teams emphasizing its potential applications in the pharmaceutical and therapeutic fields (Raoa et al., 2010 ▸; Yousra et al., 2023 ▸). Different synthesis methodologies have been detailed in the literature, reflecting extensive research efforts to elucidate these compounds’ properties and applications (e.g., Gu et al., 2017 ▸). Building on our previous research into the synthesis of quinoxaline derivatives (Yousra et al., 2023 ▸), we have synthesized the title compound, C₁₈H₂₀N₄O₆ (I), and we now describe its synthesis, crystal structure and Hirshfeld surface.

2. Structural commentary

Compound (I) contains an almost planar quinoxaline fused ring and two oxazolidine rings (Fig. 1 ▸), where the oxazolidine (C, N3/O3/C13–C15) and (D, N4/O5/C16–C18) rings are in half-chair [with a puckering parameter value of φ = 305.0 (4)°] and shallow envelope conformations, respectively. In ring D, atom N4 is at the flap position and is 0.0849 (11) Å away from the best least-squares plane of the other four atoms. The almost planar A (N1/N2/C3–C6) and B (C5–C10) rings are oriented at a dihedral angle of 1.46 (4)°. Atoms O1, O2 and C11 are −0.094 (1), 0.059 (1) and 0.070 (1) Å, respectively, away from the best least-squares plane of ring A. The side chains both have anti–gauche conformations as indicated by the following torsion angles: C3—O1—C2—C1 = −162.00 (10), O1—C2—C1—N3 = −55.36 (14), C4—O2—C11—C12 = −174.35 (9) and O2—C11—C12—N4 = −57.76 (13)°. The dihedral angles between the quinoxaline ring and the pendant oxazolidine C and D rings (all atoms) are 85.72 (6) and 56.91 (7)°, respectively; the equivalent angle between the oxazolidine rings is 89.98 (9)°.

The molecular structure of the title molecule with 50% probability ellipsoids.

3. Supramolecular features

In the crystal structure of (I), the molecules are linked by C—H⋯O hydrogen bonds (Table 1 ▸ and Fig. 2 ▸). Aromatic π–π stacking interactions between the quinoxaline A and B rings of adjacent molecules with a shortest intercentroid distance of 3.5155 (7) Å may help to consolidate the packing. No C—H⋯π interactions could be identified.

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O6ⁱ	0.99	2.37	3.189 (2)	140
C10—H10⋯O5ⁱⁱ	0.95	2.56	3.4935 (18)	168

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Symmetry codes: (i) Inline graphic ; (ii) .

A partial packing diagram viewed down the a-axis direction. Intermolecular C—H⋯O hydrogen bonds are shown as dashed lines. H atoms not involved in these interactions are omitted for clarity.

4. Hirshfeld surface analysis

A Hirshfeld surface (HS) analysis was carried out using Crystal Explorer 17.5 (Spackman et al., 2021 ▸) to investigate the intermolecular interactions in the crystal of (I). The HS is shown in Fig. 3 ▸, where the bright-red spots correspond to the respective donors and/or acceptors. According to the two-dimensional fingerprint plots (McKinnon et al., 2007 ▸), the intermolecular H⋯H and H⋯O/O⋯H contacts make the most important contributions to the HS of 48.4% and 29.1%, respectively (Fig. 4 ▸). All other contact types contribute 5% or less to the surface.

View of the three-dimensional Hirshfeld surface of the title compound plotted over d_norm.

The full two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) H⋯O/O⋯H, (d) C⋯C, (e) H⋯C/C⋯H, (f) H⋯N/N⋯H, (g) C⋯N/N⋯C, (h) C⋯O/O⋯C, (i) N⋯N, (j) N⋯O/O⋯N and (k) O⋯O interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

5. Database survey

A search of the Cambridge Structural Database (CSD) (Groom et al., 2016 ▸; updated to January 2024) using the search fragment (II) yielded 25 hits of which those most similar to the title molecule have the formula (III) with R = Me and R′ = CH₂CO₂H (CSD refcode DEZJAW; Missioui et al., 2018 ▸) or benzyl (DUSHUV; Ramli et al., 2010 ▸) with R = CF₃ and R′ = i-Bu (DUBPUO; Wei et al., 2019 ▸), with R = Ph and R′ = CH₂ (cyclo-CHCH₂O) and R′ = benzyl (PUGGII; Benzeid et al., 2009 ▸). As expected, in all these hits, the dihydroquinoxaline ring system is essentially planar with the dihedral angle between the constituent rings being less than 1° or having the nitrogen atom bearing the exocyclic substituent less than 0.03 Å from the mean plane of the remaining nine atoms.

6. Synthesis and crystallization

A solution of quinoxaline-2,3-dione (0.29 g, 1.00 mmol) in dimethylformamide (15 ml) was prepared. To this solution, tetra-n-butylammonium bromide (0.1 mmol), 2.2 equivalents of bis(2-chloroethyl)amine hydrochloride, and 2.00 equivalents of potassium carbonate were added. The mixture was stirred at 353 K for 6 h. After stirring, the salts were removed by filtration, and the solution was evaporated under reduced pressure. The resulting residue was dissolved in dichloromethane. The remaining salts were extracted with distilled water. The mixture obtained was then chromatographed on a silica gel column using an eluent of ethyl acetate and hexane in a 4:1 ratio. The solid isolate was recrystallized from an ethanol solution, resulting in crystals of (I) with a yield of 56%.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The C-bound hydrogen-atom positions were calculated geometrically at distances of 0.95 Å (for aromatic CH) and 0.99 Å (for CH₂) and they were refined using a riding model by applying the constraint U_iso(H) = 1.2U_eq(C).

Table 2. Experimental details.

Crystal data
Chemical formula	C₁₈H₂₀N₄O₆
M _r	388.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	160
a, b, c (Å)	6.6576 (1), 17.1463 (2), 15.8105 (2)
β (°)	98.935 (1)
V (Å³)	1782.92 (4)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.93
Crystal size (mm)	0.25 × 0.21 × 0.10

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Analytical (CrysAlis PRO; Rigaku OD, 2024 ▸)
T_min, T_max	0.845, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	23056, 3781, 3577
R _int	0.027
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.099, 1.06
No. of reflections	3781
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.29

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Computer programs: CrysAlis PRO (Rigaku OD, 2024 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL2019/3 (Sheldrick, 2015b ▸) and OLEX2 (Dolomanov et al., 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989025003755/hb8134sup1.cif

e-81-00469-sup1.cif^{(790.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025003755/hb8134Isup2.hkl

e-81-00469-Isup2.hkl^{(301.6KB, hkl)}

e-81-00469-Isup3.cdx^{(3.6KB, cdx)}

Supporting information file. DOI: 10.1107/S2056989025003755/hb8134Isup3.cdx

e-81-00469-Isup4.cml^{(7.5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989025003755/hb8134Isup4.cml

CCDC reference: 2447382

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

supplementary crystallographic information

3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Crystal data

C₁₈H₂₀N₄O₆	F(000) = 816
M_r = 388.38	D_x = 1.447 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 6.6576 (1) Å	Cell parameters from 17516 reflections
b = 17.1463 (2) Å	θ = 3.8–79.5°
c = 15.8105 (2) Å	µ = 0.93 mm⁻¹
β = 98.935 (1)°	T = 160 K
V = 1782.92 (4) Å³	Plate, colourless
Z = 4	0.25 × 0.21 × 0.10 mm

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3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Data collection

XtaLAB Synergy, Dualflex, HyPix diffractometer	3781 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	3577 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 10.0000 pixels mm^-1	θ_max = 77.4°, θ_min = 3.8°
ω scans	h = −8→8
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2024)	k = −21→21
T_min = 0.845, T_max = 0.932	l = −17→19
23056 measured reflections

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3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Refinement

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.038	w = 1/[σ²(F_o²) + (0.0447P)² + 0.6483P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.099	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.35 e Å⁻³
3781 reflections	Δρ_min = −0.29 e Å⁻³
254 parameters	Extinction correction: SHELXL2019/3 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0023 (2)
Primary atom site location: dual

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3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq
O1	0.34531 (13)	0.47199 (5)	0.72202 (5)	0.02841 (19)
O2	0.29395 (12)	0.35049 (4)	0.62370 (5)	0.02608 (19)
O3	0.35795 (16)	0.33324 (6)	0.96229 (7)	0.0444 (3)
O4	0.66392 (15)	0.37070 (6)	0.93404 (7)	0.0451 (3)
O5	0.74284 (18)	0.16514 (7)	0.76528 (7)	0.0527 (3)
O6	0.62002 (19)	0.11202 (8)	0.63787 (7)	0.0587 (3)
N1	0.28423 (15)	0.55758 (6)	0.60819 (6)	0.0269 (2)
N2	0.25336 (14)	0.42434 (6)	0.50000 (6)	0.0253 (2)
N3	0.37902 (16)	0.44689 (6)	0.89855 (7)	0.0322 (2)
N4	0.44993 (17)	0.20867 (6)	0.69704 (7)	0.0331 (2)
C1	0.4760 (2)	0.51244 (7)	0.86354 (8)	0.0342 (3)
H1A	0.616539	0.497667	0.857060	0.041*
H1B	0.484189	0.556502	0.904393	0.041*
C2	0.3645 (2)	0.53887 (7)	0.77796 (8)	0.0328 (3)
H2A	0.228380	0.559210	0.784233	0.039*
H2B	0.441442	0.580793	0.754216	0.039*
C3	0.30273 (16)	0.48736 (7)	0.63769 (7)	0.0252 (2)
C4	0.28227 (16)	0.41917 (6)	0.58255 (7)	0.0241 (2)
C5	0.23938 (16)	0.49903 (7)	0.46633 (8)	0.0261 (2)
C6	0.25158 (16)	0.56504 (7)	0.51985 (8)	0.0266 (2)
C7	0.23349 (18)	0.64004 (7)	0.48354 (9)	0.0316 (3)
H7	0.240283	0.684707	0.519426	0.038*
C8	0.20594 (18)	0.64869 (8)	0.39597 (9)	0.0354 (3)
H8	0.193559	0.699445	0.371627	0.043*
C9	0.19602 (19)	0.58335 (8)	0.34250 (9)	0.0358 (3)
H9	0.178341	0.590080	0.282161	0.043*
C10	0.21172 (18)	0.50923 (8)	0.37678 (8)	0.0314 (3)
H10	0.203901	0.465090	0.340091	0.038*
C11	0.27737 (18)	0.28136 (6)	0.57133 (7)	0.0266 (2)
H11A	0.395000	0.277258	0.540209	0.032*
H11B	0.151217	0.282899	0.528962	0.032*
C12	0.27329 (19)	0.21297 (7)	0.63101 (8)	0.0298 (3)
H12A	0.149795	0.216567	0.658525	0.036*
H12B	0.263947	0.164211	0.597081	0.036*
C13	0.4844 (2)	0.38405 (7)	0.93076 (8)	0.0335 (3)
C14	0.1517 (2)	0.36156 (10)	0.94072 (11)	0.0483 (4)
H14A	0.077858	0.356549	0.990193	0.058*
H14B	0.077252	0.332043	0.891836	0.058*
C15	0.1730 (2)	0.44643 (9)	0.91721 (10)	0.0429 (3)
H15A	0.073565	0.461243	0.866518	0.051*
H15B	0.157556	0.481479	0.965547	0.051*
C16	0.6022 (2)	0.15857 (8)	0.69375 (8)	0.0366 (3)
C17	0.6778 (4)	0.22219 (12)	0.82074 (12)	0.0720 (6)
H17A	0.773792	0.266660	0.828125	0.086*
H17B	0.670734	0.199276	0.877681	0.086*
C18	0.4690 (3)	0.24899 (9)	0.77867 (9)	0.0520 (4)
H18A	0.361999	0.232637	0.811984	0.062*
H18B	0.463720	0.306297	0.771004	0.062*

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3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0383 (5)	0.0205 (4)	0.0264 (4)	0.0002 (3)	0.0047 (3)	−0.0015 (3)
O2	0.0325 (4)	0.0185 (4)	0.0268 (4)	0.0001 (3)	0.0032 (3)	0.0000 (3)
O3	0.0531 (6)	0.0357 (5)	0.0436 (5)	−0.0012 (4)	0.0054 (4)	0.0096 (4)
O4	0.0414 (6)	0.0437 (6)	0.0480 (6)	0.0111 (4)	−0.0001 (4)	0.0032 (5)
O5	0.0546 (7)	0.0533 (6)	0.0442 (6)	0.0125 (5)	−0.0111 (5)	0.0030 (5)
O6	0.0615 (7)	0.0665 (8)	0.0468 (6)	0.0281 (6)	0.0044 (5)	−0.0123 (6)
N1	0.0261 (5)	0.0223 (5)	0.0326 (5)	0.0002 (4)	0.0051 (4)	0.0015 (4)
N2	0.0236 (5)	0.0241 (5)	0.0280 (5)	0.0001 (3)	0.0028 (4)	0.0012 (4)
N3	0.0364 (6)	0.0299 (5)	0.0304 (5)	0.0043 (4)	0.0053 (4)	0.0020 (4)
N4	0.0451 (6)	0.0238 (5)	0.0285 (5)	0.0043 (4)	−0.0010 (4)	−0.0016 (4)
C1	0.0425 (7)	0.0263 (6)	0.0330 (6)	−0.0020 (5)	0.0034 (5)	−0.0029 (5)
C2	0.0464 (7)	0.0216 (5)	0.0300 (6)	0.0009 (5)	0.0051 (5)	−0.0039 (5)
C3	0.0233 (5)	0.0232 (5)	0.0295 (6)	0.0001 (4)	0.0054 (4)	0.0003 (4)
C4	0.0220 (5)	0.0207 (5)	0.0297 (6)	0.0002 (4)	0.0047 (4)	0.0011 (4)
C5	0.0202 (5)	0.0262 (6)	0.0318 (6)	−0.0001 (4)	0.0042 (4)	0.0044 (4)
C6	0.0204 (5)	0.0255 (6)	0.0342 (6)	0.0005 (4)	0.0053 (4)	0.0042 (4)
C7	0.0263 (6)	0.0252 (6)	0.0436 (7)	0.0005 (4)	0.0061 (5)	0.0059 (5)
C8	0.0275 (6)	0.0324 (6)	0.0464 (7)	0.0019 (5)	0.0057 (5)	0.0153 (5)
C9	0.0300 (6)	0.0417 (7)	0.0354 (6)	0.0012 (5)	0.0042 (5)	0.0130 (5)
C10	0.0281 (6)	0.0348 (6)	0.0310 (6)	−0.0006 (5)	0.0032 (5)	0.0040 (5)
C11	0.0305 (6)	0.0205 (5)	0.0280 (5)	−0.0003 (4)	0.0024 (4)	−0.0025 (4)
C12	0.0343 (6)	0.0217 (5)	0.0328 (6)	−0.0017 (4)	0.0032 (5)	−0.0002 (4)
C13	0.0436 (7)	0.0298 (6)	0.0257 (6)	0.0017 (5)	0.0007 (5)	−0.0019 (5)
C14	0.0453 (8)	0.0538 (9)	0.0464 (8)	−0.0081 (7)	0.0084 (6)	0.0063 (7)
C15	0.0377 (7)	0.0479 (8)	0.0438 (8)	0.0052 (6)	0.0090 (6)	0.0029 (6)
C16	0.0415 (7)	0.0344 (7)	0.0331 (6)	0.0043 (5)	0.0033 (5)	0.0041 (5)
C17	0.1003 (15)	0.0538 (10)	0.0487 (9)	0.0250 (10)	−0.0297 (10)	−0.0142 (8)
C18	0.0775 (11)	0.0436 (8)	0.0309 (7)	0.0155 (8)	−0.0045 (7)	−0.0085 (6)

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3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Geometric parameters (Å, º)

O1—C2	1.4416 (14)	C5—C6	1.4079 (17)
O1—C3	1.3454 (14)	C5—C10	1.4100 (17)
O2—C4	1.3418 (13)	C6—C7	1.4057 (16)
O2—C11	1.4403 (13)	C7—H7	0.9500
O3—C13	1.3589 (17)	C7—C8	1.3762 (19)
O3—C14	1.447 (2)	C8—H8	0.9500
O4—C13	1.2101 (17)	C8—C9	1.399 (2)
O5—C16	1.3563 (17)	C9—H9	0.9500
O5—C17	1.425 (2)	C9—C10	1.3792 (18)
O6—C16	1.2100 (18)	C10—H10	0.9500
N1—C3	1.2901 (15)	C11—H11A	0.9900
N1—C6	1.3857 (16)	C11—H11B	0.9900
N2—C4	1.2924 (15)	C11—C12	1.5080 (16)
N2—C5	1.3846 (15)	C12—H12A	0.9900
N3—C1	1.4483 (17)	C12—H12B	0.9900
N3—C13	1.3421 (16)	C14—H14A	0.9900
N3—C15	1.4474 (18)	C14—H14B	0.9900
N4—C12	1.4480 (16)	C14—C15	1.514 (2)
N4—C16	1.3359 (17)	C15—H15A	0.9900
N4—C18	1.4522 (17)	C15—H15B	0.9900
C1—H1A	0.9900	C17—H17A	0.9900
C1—H1B	0.9900	C17—H17B	0.9900
C1—C2	1.5084 (18)	C17—C18	1.516 (3)
C2—H2A	0.9900	C18—H18A	0.9900
C2—H2B	0.9900	C18—H18B	0.9900
C3—C4	1.4521 (15)

C3—O1—C2	115.92 (9)	C5—C10—H10	120.0
C4—O2—C11	116.75 (9)	C9—C10—C5	119.93 (12)
C13—O3—C14	108.53 (11)	C9—C10—H10	120.0
C16—O5—C17	109.50 (12)	O2—C11—H11A	110.4
C3—N1—C6	116.22 (10)	O2—C11—H11B	110.4
C4—N2—C5	116.25 (10)	O2—C11—C12	106.71 (9)
C13—N3—C1	122.03 (11)	H11A—C11—H11B	108.6
C13—N3—C15	111.99 (11)	C12—C11—H11A	110.4
C15—N3—C1	125.10 (11)	C12—C11—H11B	110.4
C12—N4—C18	124.44 (11)	N4—C12—C11	113.52 (10)
C16—N4—C12	122.74 (11)	N4—C12—H12A	108.9
C16—N4—C18	112.25 (11)	N4—C12—H12B	108.9
N3—C1—H1A	109.0	C11—C12—H12A	108.9
N3—C1—H1B	109.0	C11—C12—H12B	108.9
N3—C1—C2	112.93 (11)	H12A—C12—H12B	107.7
H1A—C1—H1B	107.8	O4—C13—O3	121.80 (12)
C2—C1—H1A	109.0	O4—C13—N3	128.51 (13)
C2—C1—H1B	109.0	N3—C13—O3	109.68 (12)
O1—C2—C1	107.19 (10)	O3—C14—H14A	110.7
O1—C2—H2A	110.3	O3—C14—H14B	110.7
O1—C2—H2B	110.3	O3—C14—C15	105.00 (12)
C1—C2—H2A	110.3	H14A—C14—H14B	108.8
C1—C2—H2B	110.3	C15—C14—H14A	110.7
H2A—C2—H2B	108.5	C15—C14—H14B	110.7
O1—C3—C4	115.02 (10)	N3—C15—C14	100.55 (11)
N1—C3—O1	122.32 (10)	N3—C15—H15A	111.7
N1—C3—C4	122.65 (11)	N3—C15—H15B	111.7
O2—C4—C3	115.00 (10)	C14—C15—H15A	111.7
N2—C4—O2	122.56 (10)	C14—C15—H15B	111.7
N2—C4—C3	122.44 (10)	H15A—C15—H15B	109.4
N2—C5—C6	121.22 (10)	O6—C16—O5	122.03 (13)
N2—C5—C10	119.43 (11)	O6—C16—N4	127.85 (13)
C6—C5—C10	119.35 (11)	N4—C16—O5	110.11 (12)
N1—C6—C5	121.12 (10)	O5—C17—H17A	110.4
N1—C6—C7	119.09 (11)	O5—C17—H17B	110.4
C7—C6—C5	119.78 (11)	O5—C17—C18	106.47 (13)
C6—C7—H7	120.0	H17A—C17—H17B	108.6
C8—C7—C6	119.93 (12)	C18—C17—H17A	110.4
C8—C7—H7	120.0	C18—C17—H17B	110.4
C7—C8—H8	119.7	N4—C18—C17	101.14 (13)
C7—C8—C9	120.54 (11)	N4—C18—H18A	111.5
C9—C8—H8	119.7	N4—C18—H18B	111.5
C8—C9—H9	119.8	C17—C18—H18A	111.5
C10—C9—C8	120.46 (12)	C17—C18—H18B	111.5
C10—C9—H9	119.8	H18A—C18—H18B	109.4

O1—C3—C4—O2	4.66 (14)	C6—C5—C10—C9	−0.28 (17)
O1—C3—C4—N2	−175.86 (10)	C6—C7—C8—C9	−0.10 (18)
O2—C11—C12—N4	−57.76 (13)	C7—C8—C9—C10	0.64 (19)
O3—C14—C15—N3	19.93 (15)	C8—C9—C10—C5	−0.44 (19)
O5—C17—C18—N4	−6.2 (2)	C10—C5—C6—N1	−178.23 (10)
N1—C3—C4—O2	−176.22 (10)	C10—C5—C6—C7	0.82 (16)
N1—C3—C4—N2	3.25 (18)	C11—O2—C4—N2	1.41 (15)
N1—C6—C7—C8	178.43 (10)	C11—O2—C4—C3	−179.12 (9)
N2—C5—C6—N1	1.99 (16)	C12—N4—C16—O5	−177.58 (11)
N2—C5—C6—C7	−178.96 (10)	C12—N4—C16—O6	1.4 (2)
N2—C5—C10—C9	179.50 (11)	C12—N4—C18—C17	178.95 (14)
N3—C1—C2—O1	−55.36 (14)	C13—O3—C14—C15	−17.07 (15)
C1—N3—C13—O3	177.45 (11)	C13—N3—C1—C2	132.78 (12)
C1—N3—C13—O4	−2.1 (2)	C13—N3—C15—C14	−17.38 (15)
C1—N3—C15—C14	173.26 (12)	C14—O3—C13—O4	−173.94 (13)
C2—O1—C3—N1	1.41 (16)	C14—O3—C13—N3	6.47 (15)
C2—O1—C3—C4	−179.46 (10)	C15—N3—C1—C2	−58.87 (16)
C3—O1—C2—C1	−162.00 (10)	C15—N3—C13—O3	7.71 (15)
C3—N1—C6—C5	0.10 (16)	C15—N3—C13—O4	−171.84 (14)
C3—N1—C6—C7	−178.95 (10)	C16—O5—C17—C18	3.4 (2)
C4—O2—C11—C12	−174.35 (9)	C16—N4—C12—C11	−102.91 (14)
C4—N2—C5—C6	−1.41 (16)	C16—N4—C18—C17	7.40 (18)
C4—N2—C5—C10	178.81 (10)	C17—O5—C16—O6	−177.74 (17)
C5—N2—C4—O2	178.41 (9)	C17—O5—C16—N4	1.34 (19)
C5—N2—C4—C3	−1.03 (16)	C18—N4—C12—C11	86.40 (16)
C5—C6—C7—C8	−0.63 (17)	C18—N4—C16—O5	−5.86 (17)
C6—N1—C3—O1	176.48 (9)	C18—N4—C16—O6	173.16 (16)
C6—N1—C3—C4	−2.57 (16)

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3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O6ⁱ	0.99	2.37	3.189 (2)	140
C10—H10···O5ⁱⁱ	0.95	2.56	3.4935 (18)	168

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Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2.

References

Balderas-Renteria, I., Gonzalez-Barranco, P., Garcia, A., Banik, B. K. & Rivera, G. (2012). Curr. Med. Chem.19, 4377–4398. [DOI] [PubMed]
Benzeid, H., Saffon, N., Garrigues, B., Essassi, E. M. & Ng, S. W. (2009). Acta Cryst. E65, o2685. [DOI] [PMC free article] [PubMed]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst.42, 339–341.
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]
Gu, W., Wang, S., Jin, X., Zhang, Y., Hua, D., Miao, T., Tao, X. & Wang, S. (2017). Molecules, 22, 1154. [DOI] [PMC free article] [PubMed]
Kaushal, T., Srivastava, G., Sharma, A. & Singh Negi, A. (2019). Bioorg. Med. Chem.27, 16–35. [DOI] [PubMed]
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. [DOI] [PubMed]
Missioui, M., El Fal, M., Taoufik, J., Essassi, E. M., Mague, J. T. & Ramli, Y. (2018). IUCrData3, x180882.
Montana, M., Mathias, F., Terme, T. & Vanelle, P. (2019). Eur. J. Med. Chem.163, 136–147. [DOI] [PubMed]
Pereira, J. A., Pessoa, A. M., Cordeiro, M. N. D. S., Fernandes, R., Prudêncio, C., Noronha, J. P. & Vieira, M. (2015). Eur. J. Med. Chem.97, 664–672. [DOI] [PubMed]
Ramli, Y., Moussaif, A., Zouihri, H., Lazar, S. & Essassi, E. M. (2010). Acta Cryst. E66, o1922. [DOI] [PMC free article] [PubMed]
Raoa, G. K., Kotnal, R. B. & Sanjay Paib, P. N. (2010). J. Chem. Pharm. Res. 2, 368–373.
Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst.54, 1006–1011. [DOI] [PMC free article] [PubMed]
Tangherlini, G., Kalinin, D. V., Schepmann, D., Che, T., Mykicki, N., Ständer, S., Loser, K. & Wünsch, B. (2019). J. Med. Chem.62, 893–907. [DOI] [PubMed]
Vieira, M., Pinheiro, C., Fernandes, R., Noronha, J. P. & Prudêncio, C. (2014). Microbiol. Res.169, 287–293. [DOI] [PubMed]
Wei, Z., Qi, S., Xu, Y., Liu, H., Wu, J., Li, H., Xia, C. & Duan, G. (2019). Adv. Synth. Catal.361, 5490–5498.
Yousra, S., El Ghayati, L., Hökelek, T., Ouazzani Chahdi, F., Mague, J. T., Kandri Rodi, Y. & Sebbar, N. K. (2023). Acta Cryst. E79, 895–898. [DOI] [PMC free article] [PubMed]
Zeb, A., Hameed, A., Khan, L., Khan, I. K., Dalvandi, K., Choudhary, M. I. & Basha, F. Z. (2014). Med. Chem.10, 724–729. [DOI] [PubMed]
Zheng, H., Jiang, C., Chiu, M. H., Covey, J. M. & Chan, K. K. (2002). Drug Metab. Dispos.30, 344–348. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989025003755/hb8134sup1.cif

e-81-00469-sup1.cif^{(790.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025003755/hb8134Isup2.hkl

e-81-00469-Isup2.hkl^{(301.6KB, hkl)}

e-81-00469-Isup3.cdx^{(3.6KB, cdx)}

Supporting information file. DOI: 10.1107/S2056989025003755/hb8134Isup3.cdx

e-81-00469-Isup4.cml^{(7.5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989025003755/hb8134Isup4.cml

CCDC reference: 2447382

Additional supporting information: crystallographic information; 3D view; checkCIF report

[bb1] Balderas-Renteria, I., Gonzalez-Barranco, P., Garcia, A., Banik, B. K. & Rivera, G. (2012). Curr. Med. Chem.19, 4377–4398. [DOI] [PubMed]

[bb2] Benzeid, H., Saffon, N., Garrigues, B., Essassi, E. M. & Ng, S. W. (2009). Acta Cryst. E65, o2685. [DOI] [PMC free article] [PubMed]

[bb3] Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst.42, 339–341.

[bb4] Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]

[bb5] Gu, W., Wang, S., Jin, X., Zhang, Y., Hua, D., Miao, T., Tao, X. & Wang, S. (2017). Molecules, 22, 1154. [DOI] [PMC free article] [PubMed]

[bb6] Kaushal, T., Srivastava, G., Sharma, A. & Singh Negi, A. (2019). Bioorg. Med. Chem.27, 16–35. [DOI] [PubMed]

[bb7] McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. [DOI] [PubMed]

[bb8] Missioui, M., El Fal, M., Taoufik, J., Essassi, E. M., Mague, J. T. & Ramli, Y. (2018). IUCrData3, x180882.

[bb9] Montana, M., Mathias, F., Terme, T. & Vanelle, P. (2019). Eur. J. Med. Chem.163, 136–147. [DOI] [PubMed]

[bb10] Pereira, J. A., Pessoa, A. M., Cordeiro, M. N. D. S., Fernandes, R., Prudêncio, C., Noronha, J. P. & Vieira, M. (2015). Eur. J. Med. Chem.97, 664–672. [DOI] [PubMed]

[bb11] Ramli, Y., Moussaif, A., Zouihri, H., Lazar, S. & Essassi, E. M. (2010). Acta Cryst. E66, o1922. [DOI] [PMC free article] [PubMed]

[bb12] Raoa, G. K., Kotnal, R. B. & Sanjay Paib, P. N. (2010). J. Chem. Pharm. Res. 2, 368–373.

[bb13] Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.

[bb14] Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.

[bb15] Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.

[bb16] Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst.54, 1006–1011. [DOI] [PMC free article] [PubMed]

[bb17] Tangherlini, G., Kalinin, D. V., Schepmann, D., Che, T., Mykicki, N., Ständer, S., Loser, K. & Wünsch, B. (2019). J. Med. Chem.62, 893–907. [DOI] [PubMed]

[bb18] Vieira, M., Pinheiro, C., Fernandes, R., Noronha, J. P. & Prudêncio, C. (2014). Microbiol. Res.169, 287–293. [DOI] [PubMed]

[bb19] Wei, Z., Qi, S., Xu, Y., Liu, H., Wu, J., Li, H., Xia, C. & Duan, G. (2019). Adv. Synth. Catal.361, 5490–5498.

[bb20] Yousra, S., El Ghayati, L., Hökelek, T., Ouazzani Chahdi, F., Mague, J. T., Kandri Rodi, Y. & Sebbar, N. K. (2023). Acta Cryst. E79, 895–898. [DOI] [PMC free article] [PubMed]

[bb21] Zeb, A., Hameed, A., Khan, L., Khan, I. K., Dalvandi, K., Choudhary, M. I. & Basha, F. Z. (2014). Med. Chem.10, 724–729. [DOI] [PubMed]

[bb22] Zheng, H., Jiang, C., Chiu, M. H., Covey, J. M. & Chan, K. K. (2002). Drug Metab. Dispos.30, 344–348. [DOI] [PubMed]

PERMALINK

Synthesis and crystal structure of 3-(2-{3-[2-(2-oxooxazolidin-3-yl)eth­oxy]quinoxalin-2-yl­oxy}eth­yl)oxazolidin-2-one

Fatima Ezzahra Aboutofil

Nour El Hoda Mustaphi

Olivier Blacque

Tuncer Hökelek

Ahmed Mazzah

Lhoussaine El Ghayati

Nada Kheira Sebbar

Roles

Abstract

1. Chemical context

2. Structural commentary

Figure 1.

3. Supra­molecular features

Table 1. Hydrogen-bond geometry (Å, °).

Figure 2.

4. Hirshfeld surface analysis

Figure 3.

Figure 4.

5. Database survey

6. Synthesis and crystallization

7. Refinement

Table 2. Experimental details.

Supplementary Material

Acknowledgments

supplementary crystallographic information

3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Crystal data

3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Data collection

3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Refinement

3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Special details

3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Atomic displacement parameters (Å2)

3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Geometric parameters (Å, º)

3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Hydrogen-bond geometry (Å, º)

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

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Synthesis and crystal structure of 3-(2-{3-[2-(2-oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one

3. Supramolecular features

3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

3-(2-{3-[2-(2-Oxooxazolidin-3-yl)ethoxy]quinoxalin-2-yloxy}ethyl)oxazolidin-2-one. Atomic displacement parameters (Å²)