In the crystal structure of the title compound, C
9H
7N
2O, one-dimensional chains of planarmolecules are interlocked at a dihedral angle of about 30° and display weak aromatic interactions, consistent with π–π stacking. The distance between quinoxaline rings in two neighbouring planes is 3.972 (6) Å. Within a chain, molecular dimers, which are held together by a pair of strong intermolecular N—H
O hydrogen-bonding interactions at a distance of 2.792 (4) Å, are linked by weak ditopic hydrogen-bonding interactions C—H
N at a distance of 3.560 (6) Å.
Supporting information
CCDC reference: 232160
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.058
- wR factor = 0.167
- Data-to-parameter ratio = 22.2
checkCIF/PLATON results
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Data collection: CrysAlis CCD 170 (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD 170; data reduction: CrysAlis RED 170 (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C9H8N2O | F(000) = 336 |
Mr = 160.17 | Dx = 1.407 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 316 reflections |
a = 3.971 (6) Å | θ = 4–31° |
b = 11.238 (4) Å | µ = 0.10 mm−1 |
c = 16.947 (7) Å | T = 120 K |
β = 91.24 (7)° | Needle, yellow |
V = 756.2 (12) Å3 | 0.6 × 0.2 × 0.2 mm |
Z = 4 | |
Data collection top
Xcalibur2 CCD (Oxford Diffraction) diffractometer | Rint = 0.058 |
ω–2θ scans | θmax = 31.7°, θmin = 4.4° |
7654 measured reflections | h = −3→5 |
2415 independent reflections | k = −16→16 |
1491 reflections with I > 2σ(I) | l = −24→24 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.058 | w = 1/[σ2(Fo2) + (0.0984P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.167 | (Δ/σ)max = 0.001 |
S = 0.95 | Δρmax = 0.51 e Å−3 |
2415 reflections | Δρmin = −0.30 e Å−3 |
109 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4365 (3) | 0.13891 (12) | 0.37845 (8) | 0.0192 (3) | |
C2 | 0.5288 (4) | 0.06252 (13) | 0.31757 (8) | 0.0231 (3) | |
H2 | 0.4793 | −0.0182 | 0.3201 | 0.028* | |
C3 | 0.6945 (4) | 0.10841 (14) | 0.25357 (8) | 0.0252 (3) | |
H3 | 0.754 | 0.0581 | 0.2126 | 0.03* | |
C4 | 0.7747 (4) | 0.22993 (15) | 0.24938 (9) | 0.0266 (3) | |
H4 | 0.883 | 0.26 | 0.2056 | 0.032* | |
C5 | 0.6919 (4) | 0.30433 (13) | 0.31066 (8) | 0.0235 (3) | |
H5 | 0.7503 | 0.3844 | 0.3086 | 0.028* | |
C6 | 0.5208 (3) | 0.26064 (12) | 0.37604 (8) | 0.0197 (3) | |
C7 | 0.1597 (4) | 0.17082 (12) | 0.50145 (8) | 0.0205 (3) | |
C8 | 0.2688 (3) | 0.29654 (13) | 0.49596 (8) | 0.0201 (3) | |
C9 | 0.1768 (4) | 0.37643 (13) | 0.56218 (8) | 0.0240 (3) | |
H9A | 0.2593 | 0.4552 | 0.5522 | 0.036* | |
H9B | 0.2757 | 0.347 | 0.6106 | 0.036* | |
H9C | −0.0637 | 0.3786 | 0.5665 | 0.036* | |
N1 | 0.2586 (3) | 0.09875 (10) | 0.44229 (7) | 0.0203 (3) | |
H1 | 0.2081 | 0.0244 | 0.4446 | 0.024* | |
N2 | 0.4354 (3) | 0.33796 (10) | 0.43683 (7) | 0.0204 (3) | |
O1 | −0.0144 (3) | 0.13424 (9) | 0.55691 (6) | 0.0278 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0206 (7) | 0.0185 (6) | 0.0183 (6) | −0.0006 (5) | −0.0023 (5) | 0.0014 (5) |
C2 | 0.0263 (7) | 0.0189 (7) | 0.0240 (7) | 0.0009 (5) | −0.0022 (6) | −0.0016 (5) |
C3 | 0.0267 (7) | 0.0254 (8) | 0.0236 (7) | 0.0028 (6) | 0.0006 (6) | −0.0034 (6) |
C4 | 0.0285 (8) | 0.0288 (8) | 0.0227 (7) | 0.0001 (6) | 0.0031 (6) | 0.0034 (6) |
C5 | 0.0248 (7) | 0.0215 (7) | 0.0242 (7) | −0.0028 (6) | 0.0008 (6) | 0.0024 (6) |
C6 | 0.0217 (7) | 0.0172 (6) | 0.0200 (6) | −0.0015 (5) | −0.0015 (5) | 0.0012 (5) |
C7 | 0.0248 (7) | 0.0167 (7) | 0.0201 (6) | −0.0025 (5) | −0.0012 (5) | 0.0013 (5) |
C8 | 0.0229 (7) | 0.0162 (6) | 0.0210 (6) | −0.0037 (5) | −0.0019 (5) | 0.0011 (5) |
C9 | 0.0303 (8) | 0.0190 (7) | 0.0227 (7) | −0.0035 (6) | 0.0026 (6) | −0.0016 (5) |
N1 | 0.0267 (6) | 0.0126 (5) | 0.0216 (6) | −0.0040 (5) | 0.0009 (5) | 0.0001 (4) |
N2 | 0.0239 (6) | 0.0168 (6) | 0.0204 (6) | −0.0023 (5) | 0.0005 (5) | 0.0009 (4) |
O1 | 0.0390 (6) | 0.0205 (5) | 0.0241 (5) | −0.0082 (5) | 0.0072 (5) | −0.0007 (4) |
Geometric parameters (Å, º) top
C1—N1 | 1.381 (2) | C6—N2 | 1.3953 (18) |
C1—C2 | 1.397 (2) | C7—O1 | 1.2487 (18) |
C1—C6 | 1.409 (2) | C7—N1 | 1.3537 (18) |
C2—C3 | 1.381 (2) | C7—C8 | 1.481 (2) |
C2—H2 | 0.93 | C8—N2 | 1.2989 (19) |
C3—C4 | 1.404 (2) | C8—C9 | 1.489 (2) |
C3—H3 | 0.93 | C9—H9A | 0.96 |
C4—C5 | 1.379 (2) | C9—H9B | 0.96 |
C4—H4 | 0.93 | C9—H9C | 0.96 |
C5—C6 | 1.401 (2) | N1—H1 | 0.86 |
C5—H5 | 0.93 | | |
| | | |
N1—C1—C2 | 121.65 (13) | C5—C6—C1 | 118.87 (13) |
N1—C1—C6 | 117.77 (12) | O1—C7—N1 | 122.33 (13) |
C2—C1—C6 | 120.58 (13) | O1—C7—C8 | 121.93 (13) |
C3—C2—C1 | 119.19 (14) | N1—C7—C8 | 115.74 (13) |
C3—C2—H2 | 120.4 | N2—C8—C7 | 123.01 (13) |
C1—C2—H2 | 120.4 | N2—C8—C9 | 120.19 (13) |
C2—C3—C4 | 121.03 (13) | C7—C8—C9 | 116.80 (12) |
C2—C3—H3 | 119.5 | C8—C9—H9A | 109.5 |
C4—C3—H3 | 119.5 | C8—C9—H9B | 109.5 |
C5—C4—C3 | 119.58 (14) | H9A—C9—H9B | 109.5 |
C5—C4—H4 | 120.2 | C8—C9—H9C | 109.5 |
C3—C4—H4 | 120.2 | H9A—C9—H9C | 109.5 |
C4—C5—C6 | 120.71 (14) | H9B—C9—H9C | 109.5 |
C4—C5—H5 | 119.6 | C7—N1—C1 | 123.11 (12) |
C6—C5—H5 | 119.6 | C7—N1—H1 | 118.4 |
N2—C6—C5 | 119.70 (13) | C1—N1—H1 | 118.4 |
N2—C6—C1 | 121.43 (12) | C8—N2—C6 | 118.85 (12) |
| | | |
N1—C1—C2—C3 | 177.37 (12) | N1—C7—C8—N2 | 3.1 (2) |
C6—C1—C2—C3 | −2.1 (2) | O1—C7—C8—C9 | 3.2 (2) |
C1—C2—C3—C4 | 0.8 (2) | N1—C7—C8—C9 | −177.28 (12) |
C2—C3—C4—C5 | 1.1 (2) | O1—C7—N1—C1 | 176.60 (13) |
C3—C4—C5—C6 | −1.7 (2) | C8—C7—N1—C1 | −2.9 (2) |
C4—C5—C6—N2 | −179.08 (13) | C2—C1—N1—C7 | −178.70 (13) |
C4—C5—C6—C1 | 0.5 (2) | C6—C1—N1—C7 | 0.8 (2) |
N1—C1—C6—N2 | 1.5 (2) | C7—C8—N2—C6 | −1.0 (2) |
C2—C1—C6—N2 | −179.00 (12) | C9—C8—N2—C6 | 179.37 (12) |
N1—C1—C6—C5 | −178.00 (12) | C5—C6—N2—C8 | 178.17 (12) |
C2—C1—C6—C5 | 1.5 (2) | C1—C6—N2—C8 | −1.3 (2) |
O1—C7—C8—N2 | −176.40 (13) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 1.94 | 2.792 (4) | 170 |
C9—H9A···N2ii | 0.96 | 2.63 | 3.560 (6) | 164 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y+1, −z+1. |