The title compound was synthesized using the acid catalyst NH4HF2 in a water/methanol solution. The extended structure features offset stacked quinoxalines along the [100] direction.
Keywords: crystal structure, quinoxaline
Abstract
The title compound, C15H10Cl2N2, was synthesized using the acid catalyst NH4HF2 in a water/methanol solution. The dihedral angle between the phenyl ring and the quinoxaline unit is 39.80 (5)°. There is an intermolecular hydrogen-bonding-like interaction with a neighboring chlorine atom at a distance of 2.76 Å. The extended structure features offset-stacked quinoxaline units along the [100] direction.
Structure description
In general, quinoxalines are of interest as potential antibacterial (Parhi et al., 2013 ▸), antimicrobial (Singh et al., 2010 ▸), and antifungal medicines (Tang et al., 2022 ▸) and therefore exploring their synthesis and structures are of interest. The title compound was synthesized via a condensation reaction of a diamine and diketone using a water/methanol solution containing the NH4HF2 catalyst (Lassagne et al., 2015 ▸).
The molecular structure is shown in Fig. 1 ▸. The quinoxaline ring system is essentially planar. The r.m.s. deviation of the dichloroquinoxaline unit (using atoms C1–C9, N1, N2, Cl1, and Cl2) is only 0.0604 Å. The quinoxaline moiety makes an angle of 39.80 (5)° with respect to the phenyl ring. There is a hydrogen-bonding-like interaction between a carbon hydrogen and a neighboring chlorine atom (Table 1 ▸). Molecules stack along the [100] direction of the unit cell (Fig. 2 ▸). Analysis of ring interactions using PLATON (Spek, 2009 ▸) indicats that the quinoxaline ring system (C1–C6,C8,C9,N1,N2) exhibits π⋯π stacking with interplanar spacings of 3.5039 (7) Å [for neighbor at (1 − x, −y, z)], 3.4022 (7) Å [for neighbor at (
− x, y, −
+ z)], and 3.3845 (7) Å [for neighbor at (
− x, y, 1/2 + z)] with slippages of 1.515, 3.582, and 3.565Å, respectively..
Figure 1.

A view of the title molecule. Hydrogen atoms are omitted and displacement ellipsoids are drawn at the 50% probability level.
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C2—H2⋯Cl2i | 0.95 | 2.76 | 3.704 (3) | 175 |
Symmetry code: (i)
.
Figure 2.

A view of the unit-cell packing along the [100] direction.
Synthesis and crystallization
In a 50 mL Erlenmeyer flask, 1.49 g of 1-phenyl-1,2-propanedione (10.0 mmol) were added to 2 mL of H2O and 20 mL of a 2.5 x 10−3M methanol solution of NH4HF2 (Lassagne et al., 2015 ▸). To this mixture 1.78 g of 4,5-dichloro-1,2-phenylenediamine (10.0 mmol) were added. The solution was stirred for 24 h during which the product precipitated as a pale light-tan product. 2.65 g of crude product were isolated and recrysallized from methanol solution yielding 1.92 g of purified product (66%). Crystals for the diffraction study were isolated by the slow evaporation of 50/50 hexane/ethyl acetate solutions. M.p: 426 K; 1H NMR (CDCl3, 300 MHz): δ = 2.78 (s, 3H), 7.55 (m, 3H), 7.64 (m, 2H), 8.17 (s, 1H), 8.22 (s, 1H); 13C NMR (CDCl3, 300 MHz): δ = 24.51, 128.85, 128.91, 129.16, 129.43, 129.84, 133.65, 134.12, 138.31, 139.77, 139.86, 153.98, 155.89.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C15H10Cl2N2 |
| M r | 289.15 |
| Crystal system, space group | Orthorhombic, Aea2 |
| Temperature (K) | 150 |
| a, b, c (Å) | 13.7569 (4), 26.2508 (8), 7.1470 (2) |
| V (Å3) | 2580.99 (13) |
| Z | 8 |
| Radiation type | Cu Kα |
| μ (mm−1) | 4.40 |
| Crystal size (mm) | 0.21 × 0.11 × 0.06 |
| Data collection | |
| Diffractometer | Bruker AXS D8 Quest |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| Tmin, Tmax | 0.500, 0.754 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 35150, 2788, 2646 |
| R int | 0.064 |
| (sin θ/λ)max (Å−1) | 0.640 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.078, 1.11 |
| No. of reflections | 2788 |
| No. of parameters | 173 |
| No. of restraints | 1 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.23, −0.28 |
| Absolute structure | Flack x determined using 1146 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013 ▸) |
| Absolute structure parameter | 0.004 (7) |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314626008928/zl4103sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314626008928/zl4103Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314626008928/zl4103Isup3.cml
CCDC reference: 2583897
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
This work was supported by a CCSU-AAUP grant. All data were collected at Purdue University by Dr Matthias Zeller as part of the American Crystallographic Association Summer Course (2026). Dr Zeller also assisted with the refinement.
full crystallographic data
6,7-Dichloro-2-methyl-3-phenylquinoxaline. Crystal data
| C15H10Cl2N2 | Dx = 1.488 Mg m−3 |
| Mr = 289.15 | Melting point: 426 K |
| Orthorhombic, Aea2 | Cu Kα radiation, λ = 1.54178 Å |
| a = 13.7569 (4) Å | Cell parameters from 9889 reflections |
| b = 26.2508 (8) Å | θ = 3.4–80.1° |
| c = 7.1470 (2) Å | µ = 4.40 mm−1 |
| V = 2580.99 (13) Å3 | T = 150 K |
| Z = 8 | Plate, clear colourless |
| F(000) = 1184 | 0.21 × 0.11 × 0.06 mm |
6,7-Dichloro-2-methyl-3-phenylquinoxaline. Data collection
| Bruker AXS D8 Quest diffractometer | 2788 independent reflections |
| Radiation source: I-mu-S 3.0 microsource X-ray tube | 2646 reflections with I > 2σ(I) |
| HELIOS multilayer Montel optics monochromator | Rint = 0.064 |
| Detector resolution: 7.4074 pixels mm-1 | θmax = 80.6°, θmin = 3.4° |
| ω and phi scans | h = −17→17 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −33→33 |
| Tmin = 0.500, Tmax = 0.754 | l = −8→9 |
| 35150 measured reflections |
6,7-Dichloro-2-methyl-3-phenylquinoxaline. Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
| wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0438P)2 + 0.4866P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.11 | (Δ/σ)max = 0.001 |
| 2788 reflections | Δρmax = 0.23 e Å−3 |
| 173 parameters | Δρmin = −0.28 e Å−3 |
| 1 restraint | Absolute structure: Flack x determined using 1146 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
| Primary atom site location: dual | Absolute structure parameter: 0.004 (7) |
6,7-Dichloro-2-methyl-3-phenylquinoxaline. 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. |
| Refinement. Hydrogen atoms on sp2 and sp3 carbons were placed at calculated positions with a C-H distance of 0.95 Å and 0.98 Å and were included in the refinement in riding motion approximation with Uiso = 1.2Ueq or 1.5Ueq of the carrier atom, respectively. |
6,7-Dichloro-2-methyl-3-phenylquinoxaline. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.37186 (15) | 0.47901 (10) | 0.6000 (4) | 0.0262 (5) | |
| C3 | 0.37034 (16) | 0.56404 (10) | 0.4771 (4) | 0.0284 (5) | |
| C10 | 0.37433 (14) | 0.32221 (9) | 0.4945 (4) | 0.0242 (5) | |
| C15 | 0.42966 (17) | 0.30390 (9) | 0.3437 (3) | 0.0258 (5) | |
| H15 | 0.466810 | 0.327048 | 0.270755 | 0.031* | |
| N1 | 0.37599 (15) | 0.44750 (9) | 0.7518 (3) | 0.0280 (5) | |
| Cl1 | 0.36731 (4) | 0.62940 (2) | 0.51359 (11) | 0.03628 (18) | |
| C13 | 0.37601 (17) | 0.21837 (10) | 0.4054 (4) | 0.0303 (5) | |
| H13 | 0.377408 | 0.183049 | 0.376637 | 0.036* | |
| C6 | 0.37267 (16) | 0.45912 (9) | 0.4161 (4) | 0.0242 (5) | |
| C12 | 0.31946 (17) | 0.23595 (9) | 0.5524 (3) | 0.0306 (5) | |
| H12 | 0.281249 | 0.212716 | 0.622943 | 0.037* | |
| Cl2 | 0.37977 (5) | 0.58627 (2) | 0.10644 (10) | 0.03599 (18) | |
| C4 | 0.37379 (16) | 0.54433 (10) | 0.2935 (4) | 0.0275 (5) | |
| C5 | 0.37397 (16) | 0.49310 (10) | 0.2613 (4) | 0.0267 (5) | |
| H5 | 0.374956 | 0.480307 | 0.136961 | 0.032* | |
| C8 | 0.37819 (16) | 0.39822 (10) | 0.7220 (4) | 0.0250 (5) | |
| C14 | 0.43071 (17) | 0.25251 (10) | 0.3002 (4) | 0.0291 (5) | |
| H14 | 0.468808 | 0.240553 | 0.198416 | 0.035* | |
| N2 | 0.37302 (13) | 0.40786 (8) | 0.3852 (3) | 0.0259 (5) | |
| C2 | 0.36965 (16) | 0.53235 (11) | 0.6280 (4) | 0.0294 (5) | |
| H2 | 0.367700 | 0.545967 | 0.751059 | 0.035* | |
| C9 | 0.37394 (14) | 0.37773 (10) | 0.5335 (4) | 0.0232 (5) | |
| C11 | 0.31853 (16) | 0.28751 (8) | 0.5968 (4) | 0.0276 (4) | |
| H11 | 0.279563 | 0.299277 | 0.697663 | 0.033* | |
| C7 | 0.38880 (19) | 0.36530 (10) | 0.8927 (4) | 0.0299 (5) | |
| H7A | 0.325163 | 0.351482 | 0.927622 | 0.045* | |
| H7B | 0.414578 | 0.385727 | 0.996143 | 0.045* | |
| H7C | 0.433567 | 0.337216 | 0.865550 | 0.045* |
6,7-Dichloro-2-methyl-3-phenylquinoxaline. Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0260 (11) | 0.0266 (13) | 0.0260 (11) | 0.0011 (8) | 0.0006 (10) | −0.0021 (11) |
| C3 | 0.0277 (11) | 0.0226 (13) | 0.0350 (14) | −0.0003 (8) | 0.0032 (9) | −0.0036 (10) |
| C10 | 0.0257 (10) | 0.0242 (11) | 0.0228 (12) | 0.0017 (7) | −0.0034 (8) | −0.0012 (10) |
| C15 | 0.0287 (10) | 0.0266 (11) | 0.0221 (10) | 0.0002 (9) | −0.0007 (8) | 0.0006 (8) |
| N1 | 0.0320 (10) | 0.0285 (11) | 0.0235 (10) | 0.0005 (8) | 0.0006 (7) | −0.0029 (9) |
| Cl1 | 0.0454 (3) | 0.0214 (3) | 0.0421 (4) | −0.0014 (2) | 0.0073 (3) | −0.0051 (2) |
| C13 | 0.0405 (13) | 0.0215 (13) | 0.0289 (13) | 0.0001 (9) | −0.0036 (11) | −0.0014 (10) |
| C6 | 0.0256 (11) | 0.0218 (12) | 0.0252 (11) | 0.0012 (8) | −0.0003 (8) | −0.0007 (10) |
| C12 | 0.0354 (12) | 0.0287 (12) | 0.0278 (13) | −0.0049 (9) | 0.0008 (8) | 0.0018 (8) |
| Cl2 | 0.0506 (3) | 0.0257 (3) | 0.0316 (3) | −0.0025 (2) | −0.0014 (3) | 0.0041 (2) |
| C4 | 0.0281 (11) | 0.0266 (13) | 0.0278 (13) | −0.0002 (9) | −0.0006 (9) | 0.0014 (10) |
| C5 | 0.0303 (12) | 0.0256 (12) | 0.0241 (13) | −0.0006 (9) | −0.0005 (8) | 0.0000 (10) |
| C8 | 0.0249 (11) | 0.0268 (12) | 0.0234 (12) | 0.0001 (8) | 0.0003 (8) | −0.0026 (10) |
| C14 | 0.0332 (11) | 0.0294 (11) | 0.0246 (10) | 0.0028 (10) | 0.0008 (9) | −0.0028 (9) |
| N2 | 0.0281 (10) | 0.0256 (12) | 0.0240 (11) | 0.0018 (7) | −0.0002 (8) | −0.0016 (8) |
| C2 | 0.0346 (12) | 0.0270 (13) | 0.0267 (14) | 0.0006 (8) | 0.0027 (9) | −0.0056 (10) |
| C9 | 0.0225 (9) | 0.0252 (12) | 0.0220 (11) | 0.0005 (7) | 0.0005 (8) | 0.0001 (9) |
| C11 | 0.0292 (10) | 0.0281 (11) | 0.0257 (10) | 0.0000 (8) | 0.0019 (9) | −0.0018 (9) |
| C7 | 0.0374 (12) | 0.0296 (14) | 0.0226 (12) | 0.0005 (10) | −0.0029 (10) | −0.0008 (10) |
6,7-Dichloro-2-methyl-3-phenylquinoxaline. Geometric parameters (Å, º)
| C1—N1 | 1.365 (4) | C6—N2 | 1.364 (3) |
| C1—C6 | 1.415 (4) | C12—H12 | 0.9500 |
| C1—C2 | 1.415 (4) | C12—C11 | 1.390 (3) |
| C3—Cl1 | 1.736 (3) | Cl2—C4 | 1.734 (3) |
| C3—C4 | 1.411 (4) | C4—C5 | 1.364 (4) |
| C3—C2 | 1.362 (4) | C5—H5 | 0.9500 |
| C10—C15 | 1.404 (3) | C8—C9 | 1.451 (4) |
| C10—C9 | 1.484 (3) | C8—C7 | 1.502 (4) |
| C10—C11 | 1.397 (3) | C14—H14 | 0.9500 |
| C15—H15 | 0.9500 | N2—C9 | 1.323 (4) |
| C15—C14 | 1.385 (3) | C2—H2 | 0.9500 |
| N1—C8 | 1.311 (3) | C11—H11 | 0.9500 |
| C13—H13 | 0.9500 | C7—H7A | 0.9800 |
| C13—C12 | 1.386 (4) | C7—H7B | 0.9800 |
| C13—C14 | 1.391 (4) | C7—H7C | 0.9800 |
| C6—C5 | 1.421 (3) | ||
| N1—C1—C6 | 121.0 (2) | C6—C5—H5 | 120.4 |
| N1—C1—C2 | 119.2 (3) | C4—C5—C6 | 119.2 (2) |
| C6—C1—C2 | 119.8 (3) | C4—C5—H5 | 120.4 |
| C4—C3—Cl1 | 120.2 (2) | N1—C8—C9 | 121.0 (2) |
| C2—C3—Cl1 | 119.0 (2) | N1—C8—C7 | 116.0 (2) |
| C2—C3—C4 | 120.8 (2) | C9—C8—C7 | 123.0 (2) |
| C15—C10—C9 | 118.8 (2) | C15—C14—C13 | 120.0 (2) |
| C11—C10—C15 | 118.4 (2) | C15—C14—H14 | 120.0 |
| C11—C10—C9 | 122.7 (2) | C13—C14—H14 | 120.0 |
| C10—C15—H15 | 119.6 | C9—N2—C6 | 117.4 (2) |
| C14—C15—C10 | 120.8 (2) | C1—C2—H2 | 120.2 |
| C14—C15—H15 | 119.6 | C3—C2—C1 | 119.5 (2) |
| C8—N1—C1 | 118.0 (2) | C3—C2—H2 | 120.2 |
| C12—C13—H13 | 120.0 | C8—C9—C10 | 122.6 (2) |
| C12—C13—C14 | 119.9 (2) | N2—C9—C10 | 115.9 (2) |
| C14—C13—H13 | 120.0 | N2—C9—C8 | 121.5 (2) |
| C1—C6—C5 | 119.5 (2) | C10—C11—H11 | 119.7 |
| N2—C6—C1 | 121.0 (2) | C12—C11—C10 | 120.7 (2) |
| N2—C6—C5 | 119.6 (2) | C12—C11—H11 | 119.7 |
| C13—C12—H12 | 119.9 | C8—C7—H7A | 109.5 |
| C13—C12—C11 | 120.1 (2) | C8—C7—H7B | 109.5 |
| C11—C12—H12 | 119.9 | C8—C7—H7C | 109.5 |
| C3—C4—Cl2 | 119.1 (2) | H7A—C7—H7B | 109.5 |
| C5—C4—C3 | 121.2 (2) | H7A—C7—H7C | 109.5 |
| C5—C4—Cl2 | 119.7 (2) | H7B—C7—H7C | 109.5 |
| C1—N1—C8—C9 | −1.5 (3) | C6—N2—C9—C10 | −179.98 (18) |
| C1—N1—C8—C7 | 176.4 (2) | C6—N2—C9—C8 | −2.3 (3) |
| C1—C6—C5—C4 | −0.4 (3) | C12—C13—C14—C15 | 0.8 (4) |
| C1—C6—N2—C9 | −0.9 (3) | Cl2—C4—C5—C6 | 177.70 (17) |
| C3—C4—C5—C6 | −1.3 (3) | C4—C3—C2—C1 | −0.4 (4) |
| C10—C15—C14—C13 | 0.5 (3) | C5—C6—N2—C9 | 178.54 (19) |
| C15—C10—C9—C8 | −139.0 (2) | C14—C13—C12—C11 | −1.1 (4) |
| C15—C10—C9—N2 | 38.6 (3) | N2—C6—C5—C4 | −179.9 (2) |
| C15—C10—C11—C12 | 1.3 (3) | C2—C1—N1—C8 | −179.85 (19) |
| N1—C1—C6—C5 | −176.4 (2) | C2—C1—C6—C5 | 1.7 (3) |
| N1—C1—C6—N2 | 3.1 (3) | C2—C1—C6—N2 | −178.80 (19) |
| N1—C1—C2—C3 | 176.8 (2) | C2—C3—C4—Cl2 | −177.28 (18) |
| N1—C8—C9—C10 | −178.79 (18) | C2—C3—C4—C5 | 1.7 (4) |
| N1—C8—C9—N2 | 3.7 (3) | C9—C10—C15—C14 | −178.8 (2) |
| Cl1—C3—C4—Cl2 | 2.5 (3) | C9—C10—C11—C12 | 178.5 (2) |
| Cl1—C3—C4—C5 | −178.48 (17) | C11—C10—C15—C14 | −1.5 (3) |
| Cl1—C3—C2—C1 | 179.85 (16) | C11—C10—C9—C8 | 43.8 (3) |
| C13—C12—C11—C10 | 0.0 (4) | C11—C10—C9—N2 | −138.6 (2) |
| C6—C1—N1—C8 | −1.7 (3) | C7—C8—C9—C10 | 3.4 (3) |
| C6—C1—C2—C3 | −1.3 (3) | C7—C8—C9—N2 | −174.1 (2) |
6,7-Dichloro-2-methyl-3-phenylquinoxaline. Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C2—H2···Cl2i | 0.95 | 2.76 | 3.704 (3) | 175 |
Symmetry code: (i) x, y, z+1.
References
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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/S2414314626008928/zl4103sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314626008928/zl4103Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314626008928/zl4103Isup3.cml
CCDC reference: 2583897
Additional supporting information: crystallographic information; 3D view; checkCIF report
