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In the crystal structure of the title compound, C9H7N2O, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028368/su6065sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028368/su6065IIsup2.hkl
Contains datablock II

CCDC reference: 232160

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](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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No errors found in this datablock

Computing details top

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).

(II) top
Crystal data top
C9H8N2OF(000) = 336
Mr = 160.17Dx = 1.407 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 316 reflections
a = 3.971 (6) Åθ = 4–31°
b = 11.238 (4) ŵ = 0.10 mm1
c = 16.947 (7) ÅT = 120 K
β = 91.24 (7)°Needle, yellow
V = 756.2 (12) Å30.6 × 0.2 × 0.2 mm
Z = 4
Data collection top
Xcalibur2 CCD (Oxford Diffraction)
diffractometer
Rint = 0.058
ω–2θ scansθmax = 31.7°, θmin = 4.4°
7654 measured reflectionsh = 35
2415 independent reflectionsk = 1616
1491 reflections with I > 2σ(I)l = 2424
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-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 = 0.95Δρmax = 0.51 e Å3
2415 reflectionsΔρmin = 0.30 e Å3
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
xyzUiso*/Ueq
C10.4365 (3)0.13891 (12)0.37845 (8)0.0192 (3)
C20.5288 (4)0.06252 (13)0.31757 (8)0.0231 (3)
H20.47930.01820.32010.028*
C30.6945 (4)0.10841 (14)0.25357 (8)0.0252 (3)
H30.7540.05810.21260.03*
C40.7747 (4)0.22993 (15)0.24938 (9)0.0266 (3)
H40.8830.260.20560.032*
C50.6919 (4)0.30433 (13)0.31066 (8)0.0235 (3)
H50.75030.38440.30860.028*
C60.5208 (3)0.26064 (12)0.37604 (8)0.0197 (3)
C70.1597 (4)0.17082 (12)0.50145 (8)0.0205 (3)
C80.2688 (3)0.29654 (13)0.49596 (8)0.0201 (3)
C90.1768 (4)0.37643 (13)0.56218 (8)0.0240 (3)
H9A0.25930.45520.55220.036*
H9B0.27570.3470.61060.036*
H9C0.06370.37860.56650.036*
N10.2586 (3)0.09875 (10)0.44229 (7)0.0203 (3)
H10.20810.02440.44460.024*
N20.4354 (3)0.33796 (10)0.43683 (7)0.0204 (3)
O10.0144 (3)0.13424 (9)0.55691 (6)0.0278 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0206 (7)0.0185 (6)0.0183 (6)0.0006 (5)0.0023 (5)0.0014 (5)
C20.0263 (7)0.0189 (7)0.0240 (7)0.0009 (5)0.0022 (6)0.0016 (5)
C30.0267 (7)0.0254 (8)0.0236 (7)0.0028 (6)0.0006 (6)0.0034 (6)
C40.0285 (8)0.0288 (8)0.0227 (7)0.0001 (6)0.0031 (6)0.0034 (6)
C50.0248 (7)0.0215 (7)0.0242 (7)0.0028 (6)0.0008 (6)0.0024 (6)
C60.0217 (7)0.0172 (6)0.0200 (6)0.0015 (5)0.0015 (5)0.0012 (5)
C70.0248 (7)0.0167 (7)0.0201 (6)0.0025 (5)0.0012 (5)0.0013 (5)
C80.0229 (7)0.0162 (6)0.0210 (6)0.0037 (5)0.0019 (5)0.0011 (5)
C90.0303 (8)0.0190 (7)0.0227 (7)0.0035 (6)0.0026 (6)0.0016 (5)
N10.0267 (6)0.0126 (5)0.0216 (6)0.0040 (5)0.0009 (5)0.0001 (4)
N20.0239 (6)0.0168 (6)0.0204 (6)0.0023 (5)0.0005 (5)0.0009 (4)
O10.0390 (6)0.0205 (5)0.0241 (5)0.0082 (5)0.0072 (5)0.0007 (4)
Geometric parameters (Å, º) top
C1—N11.381 (2)C6—N21.3953 (18)
C1—C21.397 (2)C7—O11.2487 (18)
C1—C61.409 (2)C7—N11.3537 (18)
C2—C31.381 (2)C7—C81.481 (2)
C2—H20.93C8—N21.2989 (19)
C3—C41.404 (2)C8—C91.489 (2)
C3—H30.93C9—H9A0.96
C4—C51.379 (2)C9—H9B0.96
C4—H40.93C9—H9C0.96
C5—C61.401 (2)N1—H10.86
C5—H50.93
N1—C1—C2121.65 (13)C5—C6—C1118.87 (13)
N1—C1—C6117.77 (12)O1—C7—N1122.33 (13)
C2—C1—C6120.58 (13)O1—C7—C8121.93 (13)
C3—C2—C1119.19 (14)N1—C7—C8115.74 (13)
C3—C2—H2120.4N2—C8—C7123.01 (13)
C1—C2—H2120.4N2—C8—C9120.19 (13)
C2—C3—C4121.03 (13)C7—C8—C9116.80 (12)
C2—C3—H3119.5C8—C9—H9A109.5
C4—C3—H3119.5C8—C9—H9B109.5
C5—C4—C3119.58 (14)H9A—C9—H9B109.5
C5—C4—H4120.2C8—C9—H9C109.5
C3—C4—H4120.2H9A—C9—H9C109.5
C4—C5—C6120.71 (14)H9B—C9—H9C109.5
C4—C5—H5119.6C7—N1—C1123.11 (12)
C6—C5—H5119.6C7—N1—H1118.4
N2—C6—C5119.70 (13)C1—N1—H1118.4
N2—C6—C1121.43 (12)C8—N2—C6118.85 (12)
N1—C1—C2—C3177.37 (12)N1—C7—C8—N23.1 (2)
C6—C1—C2—C32.1 (2)O1—C7—C8—C93.2 (2)
C1—C2—C3—C40.8 (2)N1—C7—C8—C9177.28 (12)
C2—C3—C4—C51.1 (2)O1—C7—N1—C1176.60 (13)
C3—C4—C5—C61.7 (2)C8—C7—N1—C12.9 (2)
C4—C5—C6—N2179.08 (13)C2—C1—N1—C7178.70 (13)
C4—C5—C6—C10.5 (2)C6—C1—N1—C70.8 (2)
N1—C1—C6—N21.5 (2)C7—C8—N2—C61.0 (2)
C2—C1—C6—N2179.00 (12)C9—C8—N2—C6179.37 (12)
N1—C1—C6—C5178.00 (12)C5—C6—N2—C8178.17 (12)
C2—C1—C6—C51.5 (2)C1—C6—N2—C81.3 (2)
O1—C7—C8—N2176.40 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.861.942.792 (4)170
C9—H9A···N2ii0.962.633.560 (6)164
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+1.
 

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