organic compounds
1-[(1-Butyl-1H-1,2,3-triazol-5-yl)methyl]-3-methylquinoxalin-2(1H)-one
aLaboratoire de Chimie Organique Hétérocyclique, Centre de Recherche des Sciences des Médicaments, URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, bLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, and cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: nadeemabad2018@gmail.com
In the title compound, C16H19N5O, the quinoxaline and triazole rings are almost orthogonal, inclined to one another at an angle of 79.8 (3)°. A weak intramolecular C—H⋯O interaction locks the conformation of the molecule. The crystal packing features weak intermolecular C—H⋯O and C—H⋯N interactions, which form chains along the b-axis direction. In addition, weak C—H⋯π intermolecular interactions further influence the crystal packing.
CCDC reference: 1832277
Structure description
The quinoxaline moiety is present in a variety of physiologically active compounds, with applications varying from medicinal to agricultural (Ramli et al., 2014). Quinoxaline derivatives possess diverse biological activities showing insecticidal, fungicidal, herbicidal, anthelmintic and antiviral properties (Ramli & Essassi, 2015). As a continuation of our work on the synthesis of 3-methyl quinoxalin-2-one derivatives in order to evaluate their pharmacological activities (Ramli et al., 2010a,b, 2011, 2013, 2017; Caleb et al., 2016; Missioui et al., 2017), the title compound (Fig. 1) was synthesized and its is reported here. This compound is built up from the two fused six-membered rings of a quinoxalinone ring system linked through a methylene bridge to a 1,2,3-triazole ring, which in turn carries a n-butyl substituent on N3 (Sebbar et al., 2016, Ellouz et al., 2015).
The title compound crystallizes with one independent molecule in the B⋯O1 interaction locks the conformation of the molecule (Fig. 2, Table 1).
The quinoxaline ring system is essentially planar with atom N4 showing a maximum deviation of 0.035 (9) Å from the mean plane of the ten-membered ring system. In addition, the quinoxaline ring system occupies an anti-clinal [C1—C2⋯C13—C14 = −119.8 (2)°] orientation with respect to the mean plane of the triazole ring and is twisted with a dihedral angle of 79.8 (3)° between this ring and the quinoxalinone ring system. The butyl moiety on the other hand is in a syn-clinal orientation [N2—N3—C12—C13 = 85.6 (2)] with respect to the triazole ring. A weak intramolecular C12—H12The crystal packing features weak C—H⋯O and C—H⋯N intermolecular interactions forming chains along the b-axis direction (Fig. 2, Table 1). In addition, weak C3—H3B⋯π(Cg1), C13—H13B⋯π(Cg2) and C14—H14A⋯π(Cg3) intermolecular interactions, Table 1, further influence the crystal packing. No classical hydrogen bonds are observed.
Synthesis and crystallization
To a solution of 3-methyl-1-(prop-2-ynyl)-3,4-dihydroquinoxalin-2(1H)-one (0.68 mmol) in ethanol (15 ml) was added 1-azidobutane (1.03 mmol). The reaction mixture was stirred under reflux for 72 h. After completion of the reaction (monitored by TLC), the solution was concentrated and the residue was purified by on silica gel by using as the mixture (hexane/ethyl acetate 8:2). The solid product obtained was crystallized from ethanol to afford colourless crystals in 16% yield.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 1832277
https://doi.org/10.1107/S2414314618004820/sj4170sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004820/sj4170Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618004820/sj4170Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314618004820/sj4170Isup4.cml
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C16H19N5O | F(000) = 632 |
Mr = 297.36 | Dx = 1.288 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 15.8299 (8) Å | Cell parameters from 2219 reflections |
b = 10.6270 (4) Å | θ = 5.0–71.3° |
c = 9.2041 (3) Å | µ = 0.68 mm−1 |
β = 98.084 (4)° | T = 293 K |
V = 1532.97 (11) Å3 | Plate, colourless |
Z = 4 | 0.24 × 0.22 × 0.04 mm |
Rigaku OD Xcalibur Eos Gemini diffractometer | 2887 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source | 2257 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 71.4°, θmin = 5.0° |
ω scans | h = −19→18 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −12→9 |
Tmin = 0.794, Tmax = 1.000 | l = −11→9 |
5580 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.0798P)2 + 0.4446P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
2887 reflections | Δρmax = 0.24 e Å−3 |
201 parameters | Δρmin = −0.21 e Å−3 |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.74544 (10) | 0.55020 (16) | 0.66870 (14) | 0.0596 (4) | |
N1 | 0.48881 (13) | 0.3093 (2) | 0.2446 (2) | 0.0697 (6) | |
N2 | 0.54195 (14) | 0.2443 (2) | 0.3387 (2) | 0.0693 (6) | |
N3 | 0.59408 (11) | 0.32718 (18) | 0.41696 (19) | 0.0546 (5) | |
N4 | 0.70864 (9) | 0.57241 (14) | 0.42118 (16) | 0.0392 (4) | |
N5 | 0.88308 (10) | 0.58729 (16) | 0.39979 (17) | 0.0463 (4) | |
C1 | 0.50794 (14) | 0.4318 (2) | 0.2624 (3) | 0.0588 (6) | |
H1 | 0.479662 | 0.497079 | 0.208530 | 0.071* | |
C2 | 0.57542 (12) | 0.4464 (2) | 0.3720 (2) | 0.0482 (5) | |
C3 | 0.61758 (12) | 0.56295 (19) | 0.4363 (2) | 0.0470 (5) | |
H3A | 0.588035 | 0.635325 | 0.389280 | 0.056* | |
H3B | 0.611719 | 0.566253 | 0.539760 | 0.056* | |
C4 | 0.76751 (12) | 0.56566 (18) | 0.54693 (19) | 0.0424 (4) | |
C5 | 0.85801 (12) | 0.57422 (18) | 0.5260 (2) | 0.0440 (4) | |
C6 | 0.82194 (12) | 0.59686 (17) | 0.27565 (19) | 0.0410 (4) | |
C7 | 0.85021 (14) | 0.6119 (2) | 0.1395 (2) | 0.0510 (5) | |
H7 | 0.908390 | 0.615156 | 0.134056 | 0.061* | |
C8 | 0.79259 (16) | 0.6219 (2) | 0.0140 (2) | 0.0562 (5) | |
H8 | 0.811729 | 0.630647 | −0.076527 | 0.067* | |
C9 | 0.70609 (15) | 0.6191 (2) | 0.0220 (2) | 0.0550 (5) | |
H9 | 0.667359 | 0.626632 | −0.063395 | 0.066* | |
C10 | 0.67642 (13) | 0.60513 (19) | 0.1549 (2) | 0.0468 (5) | |
H10 | 0.618071 | 0.604692 | 0.159195 | 0.056* | |
C11 | 0.73449 (12) | 0.59165 (16) | 0.28335 (19) | 0.0385 (4) | |
C12 | 0.66329 (15) | 0.2808 (2) | 0.5264 (2) | 0.0588 (6) | |
H12A | 0.644317 | 0.205872 | 0.572596 | 0.071* | |
H12B | 0.676992 | 0.344162 | 0.601957 | 0.071* | |
C13 | 0.74284 (15) | 0.2501 (2) | 0.4584 (2) | 0.0566 (5) | |
H13A | 0.731888 | 0.176846 | 0.395742 | 0.068* | |
H13B | 0.755878 | 0.320089 | 0.397712 | 0.068* | |
C14 | 0.81893 (16) | 0.2243 (2) | 0.5732 (3) | 0.0644 (6) | |
H14A | 0.807379 | 0.150401 | 0.629041 | 0.077* | |
H14B | 0.826964 | 0.294931 | 0.640492 | 0.077* | |
C15 | 0.90023 (18) | 0.2033 (3) | 0.5077 (3) | 0.0875 (9) | |
H15A | 0.911247 | 0.275242 | 0.450146 | 0.131* | |
H15B | 0.894122 | 0.129902 | 0.446367 | 0.131* | |
H15C | 0.946930 | 0.191470 | 0.585121 | 0.131* | |
C16 | 0.92225 (14) | 0.5652 (2) | 0.6610 (2) | 0.0594 (6) | |
H16A | 0.912318 | 0.489923 | 0.713739 | 0.089* | |
H16B | 0.917122 | 0.637133 | 0.722238 | 0.089* | |
H16C | 0.978585 | 0.562721 | 0.633781 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0602 (9) | 0.0843 (11) | 0.0344 (7) | −0.0058 (8) | 0.0071 (6) | −0.0005 (7) |
N1 | 0.0594 (11) | 0.0780 (14) | 0.0691 (12) | −0.0220 (11) | −0.0001 (9) | −0.0034 (11) |
N2 | 0.0713 (13) | 0.0620 (12) | 0.0736 (13) | −0.0227 (10) | 0.0067 (10) | −0.0045 (10) |
N3 | 0.0539 (10) | 0.0579 (10) | 0.0521 (10) | −0.0120 (8) | 0.0080 (8) | −0.0005 (8) |
N4 | 0.0398 (8) | 0.0417 (8) | 0.0353 (7) | −0.0011 (6) | 0.0023 (6) | −0.0029 (6) |
N5 | 0.0421 (8) | 0.0525 (9) | 0.0439 (9) | 0.0014 (7) | 0.0046 (7) | −0.0046 (7) |
C1 | 0.0438 (10) | 0.0697 (14) | 0.0614 (13) | −0.0123 (10) | 0.0018 (9) | −0.0015 (11) |
C2 | 0.0405 (9) | 0.0574 (12) | 0.0480 (10) | −0.0045 (9) | 0.0103 (8) | 0.0004 (9) |
C3 | 0.0435 (10) | 0.0525 (11) | 0.0455 (10) | −0.0004 (9) | 0.0078 (8) | −0.0040 (8) |
C4 | 0.0471 (10) | 0.0445 (10) | 0.0347 (9) | −0.0004 (8) | 0.0022 (7) | −0.0034 (7) |
C5 | 0.0449 (10) | 0.0443 (10) | 0.0409 (9) | 0.0020 (8) | −0.0005 (8) | −0.0039 (8) |
C6 | 0.0464 (10) | 0.0381 (9) | 0.0382 (9) | −0.0005 (8) | 0.0049 (7) | −0.0032 (7) |
C7 | 0.0557 (11) | 0.0526 (11) | 0.0472 (10) | −0.0012 (9) | 0.0157 (9) | −0.0019 (9) |
C8 | 0.0788 (15) | 0.0545 (12) | 0.0367 (9) | −0.0053 (11) | 0.0124 (9) | 0.0018 (9) |
C9 | 0.0744 (14) | 0.0495 (11) | 0.0372 (9) | −0.0046 (10) | −0.0060 (9) | 0.0050 (8) |
C10 | 0.0482 (10) | 0.0472 (10) | 0.0429 (10) | −0.0026 (8) | −0.0012 (8) | 0.0029 (8) |
C11 | 0.0469 (10) | 0.0334 (8) | 0.0346 (8) | −0.0007 (7) | 0.0033 (7) | −0.0015 (6) |
C12 | 0.0709 (14) | 0.0569 (12) | 0.0488 (11) | −0.0055 (11) | 0.0087 (10) | 0.0092 (9) |
C13 | 0.0723 (14) | 0.0498 (11) | 0.0465 (11) | 0.0008 (10) | 0.0039 (10) | 0.0035 (9) |
C14 | 0.0789 (16) | 0.0565 (13) | 0.0548 (12) | 0.0086 (11) | −0.0009 (11) | 0.0046 (10) |
C15 | 0.0768 (18) | 0.096 (2) | 0.0858 (19) | 0.0122 (16) | −0.0010 (15) | 0.0102 (17) |
C16 | 0.0489 (11) | 0.0771 (15) | 0.0488 (11) | 0.0032 (11) | −0.0049 (9) | −0.0002 (10) |
O1—C4 | 1.231 (2) | C8—H8 | 0.9300 |
N1—N2 | 1.316 (3) | C8—C9 | 1.382 (3) |
N1—C1 | 1.342 (3) | C9—H9 | 0.9300 |
N2—N3 | 1.345 (3) | C9—C10 | 1.379 (3) |
N3—C2 | 1.353 (3) | C10—H10 | 0.9300 |
N3—C12 | 1.466 (3) | C10—C11 | 1.399 (3) |
N4—C3 | 1.471 (2) | C12—H12A | 0.9700 |
N4—C4 | 1.382 (2) | C12—H12B | 0.9700 |
N4—C11 | 1.402 (2) | C12—C13 | 1.518 (3) |
N5—C5 | 1.287 (2) | C13—H13A | 0.9700 |
N5—C6 | 1.393 (2) | C13—H13B | 0.9700 |
C1—H1 | 0.9300 | C13—C14 | 1.511 (3) |
C1—C2 | 1.371 (3) | C14—H14A | 0.9700 |
C2—C3 | 1.489 (3) | C14—H14B | 0.9700 |
C3—H3A | 0.9700 | C14—C15 | 1.512 (4) |
C3—H3B | 0.9700 | C15—H15A | 0.9600 |
C4—C5 | 1.475 (3) | C15—H15B | 0.9600 |
C5—C16 | 1.494 (3) | C15—H15C | 0.9600 |
C6—C7 | 1.397 (3) | C16—H16A | 0.9600 |
C6—C11 | 1.397 (3) | C16—H16B | 0.9600 |
C7—H7 | 0.9300 | C16—H16C | 0.9600 |
C7—C8 | 1.372 (3) | ||
N2—N1—C1 | 108.45 (19) | C10—C9—H9 | 119.5 |
N1—N2—N3 | 107.2 (2) | C9—C10—H10 | 120.2 |
N2—N3—C2 | 111.02 (19) | C9—C10—C11 | 119.69 (19) |
N2—N3—C12 | 119.4 (2) | C11—C10—H10 | 120.2 |
C2—N3—C12 | 129.44 (19) | C6—C11—N4 | 117.98 (15) |
C4—N4—C3 | 118.12 (15) | C6—C11—C10 | 119.42 (17) |
C4—N4—C11 | 121.15 (15) | C10—C11—N4 | 122.60 (17) |
C11—N4—C3 | 120.70 (15) | N3—C12—H12A | 109.2 |
C5—N5—C6 | 118.76 (16) | N3—C12—H12B | 109.2 |
N1—C1—H1 | 125.1 | N3—C12—C13 | 111.84 (17) |
N1—C1—C2 | 109.8 (2) | H12A—C12—H12B | 107.9 |
C2—C1—H1 | 125.1 | C13—C12—H12A | 109.2 |
N3—C2—C1 | 103.48 (19) | C13—C12—H12B | 109.2 |
N3—C2—C3 | 126.22 (18) | C12—C13—H13A | 109.2 |
C1—C2—C3 | 130.2 (2) | C12—C13—H13B | 109.2 |
N4—C3—C2 | 114.17 (15) | H13A—C13—H13B | 107.9 |
N4—C3—H3A | 108.7 | C14—C13—C12 | 112.13 (18) |
N4—C3—H3B | 108.7 | C14—C13—H13A | 109.2 |
C2—C3—H3A | 108.7 | C14—C13—H13B | 109.2 |
C2—C3—H3B | 108.7 | C13—C14—H14A | 109.0 |
H3A—C3—H3B | 107.6 | C13—C14—H14B | 109.0 |
O1—C4—N4 | 121.69 (17) | C13—C14—C15 | 112.8 (2) |
O1—C4—C5 | 122.16 (17) | H14A—C14—H14B | 107.8 |
N4—C4—C5 | 116.12 (15) | C15—C14—H14A | 109.0 |
N5—C5—C4 | 123.58 (16) | C15—C14—H14B | 109.0 |
N5—C5—C16 | 119.83 (18) | C14—C15—H15A | 109.5 |
C4—C5—C16 | 116.58 (17) | C14—C15—H15B | 109.5 |
N5—C6—C7 | 118.05 (17) | C14—C15—H15C | 109.5 |
N5—C6—C11 | 122.31 (16) | H15A—C15—H15B | 109.5 |
C11—C6—C7 | 119.64 (17) | H15A—C15—H15C | 109.5 |
C6—C7—H7 | 119.8 | H15B—C15—H15C | 109.5 |
C8—C7—C6 | 120.3 (2) | C5—C16—H16A | 109.5 |
C8—C7—H7 | 119.8 | C5—C16—H16B | 109.5 |
C7—C8—H8 | 120.0 | C5—C16—H16C | 109.5 |
C7—C8—C9 | 119.95 (18) | H16A—C16—H16B | 109.5 |
C9—C8—H8 | 120.0 | H16A—C16—H16C | 109.5 |
C8—C9—H9 | 119.5 | H16B—C16—H16C | 109.5 |
C10—C9—C8 | 120.92 (19) | ||
O1—C4—C5—N5 | 178.3 (2) | C3—N4—C11—C10 | 1.2 (3) |
O1—C4—C5—C16 | −0.9 (3) | C4—N4—C3—C2 | −112.54 (19) |
N1—N2—N3—C2 | −0.8 (2) | C4—N4—C11—C6 | 3.5 (2) |
N1—N2—N3—C12 | −176.99 (18) | C4—N4—C11—C10 | −176.77 (17) |
N1—C1—C2—N3 | −0.3 (2) | C5—N5—C6—C7 | 179.55 (18) |
N1—C1—C2—C3 | −177.2 (2) | C5—N5—C6—C11 | −0.6 (3) |
N2—N1—C1—C2 | −0.2 (3) | C6—N5—C5—C4 | 1.5 (3) |
N2—N3—C2—C1 | 0.7 (2) | C6—N5—C5—C16 | −179.32 (18) |
N2—N3—C2—C3 | 177.76 (18) | C6—C7—C8—C9 | 1.0 (3) |
N2—N3—C12—C13 | 85.6 (2) | C7—C6—C11—N4 | 177.98 (17) |
N3—C2—C3—N4 | 63.9 (3) | C7—C6—C11—C10 | −1.8 (3) |
N3—C12—C13—C14 | 169.95 (19) | C7—C8—C9—C10 | −0.6 (3) |
N4—C4—C5—N5 | 0.0 (3) | C8—C9—C10—C11 | −1.0 (3) |
N4—C4—C5—C16 | −179.16 (18) | C9—C10—C11—N4 | −177.55 (17) |
N5—C6—C7—C8 | −179.93 (19) | C9—C10—C11—C6 | 2.2 (3) |
N5—C6—C11—N4 | −1.9 (3) | C11—N4—C3—C2 | 69.4 (2) |
N5—C6—C11—C10 | 178.35 (17) | C11—N4—C4—O1 | 179.18 (17) |
C1—N1—N2—N3 | 0.6 (3) | C11—N4—C4—C5 | −2.6 (2) |
C1—C2—C3—N4 | −119.8 (2) | C11—C6—C7—C8 | 0.2 (3) |
C2—N3—C12—C13 | −89.8 (3) | C12—N3—C2—C1 | 176.3 (2) |
C3—N4—C4—O1 | 1.1 (3) | C12—N3—C2—C3 | −6.6 (3) |
C3—N4—C4—C5 | 179.36 (15) | C12—C13—C14—C15 | −175.6 (2) |
C3—N4—C11—C6 | −178.52 (15) |
Cg1, Cg2 and Cg3 are the centroids of the N1–N3/C1/C2, N4/N5/C4–C6/C11 and C6–C11 rings respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12B···O1 | 0.97 | 2.48 | 3.335 (3) | 147 |
C3—H3A···N1i | 0.97 | 2.45 | 3.416 (3) | 176 |
C8—H8···O1ii | 0.93 | 2.58 | 3.251 (2) | 130 |
C3—H3B···Cg1iii | 0.97 | 3.00 | 3.670 (2) | 127 |
C13—H13B···Cg2 | 0.97 | 2.85 | 3.661 (2) | 142 |
C14—H14A···Cg3iv | 0.97 | 2.84 | 3.724 (2) | 152 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x, −y−1/2, z−1/2. |
Funding information
JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
References
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