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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2650.
Published online 2010 September 30. doi:  10.1107/S1600536810037943
PMCID: PMC2983270

3-(4-Meth­oxy­phen­yl)pyrido[2,3-b]pyrazine

Abstract

In the title mol­ecule, C14H11N3O, the benzene ring is twisted by 14.0 (2)° from the plane through the fused ring system. In the crystal, π–π inter­actions [centroid–centroid distances = 3.609 (1), 3.639 (1) and 3.735 (1) Å] form stacks of mol­ecules propagating along the b axis. The crystal packing is further stabilized by weak inter­molecular C—H(...)O and C—H(...)N hydrogen bonds.

Related literature

For a related structure, see: Koch et al. (2009 [triangle]). For the pharma­cological properties of quinoxaline compounds, see: Kleim et al. (1995 [triangle]); Abasolo et al. (1987 [triangle]); Rodrigo et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2650-scheme1.jpg

Experimental

Crystal data

  • C14H11N3O
  • M r = 237.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2650-efi1.jpg
  • a = 6.4486 (13) Å
  • b = 7.3265 (15) Å
  • c = 24.216 (6) Å
  • β = 99.31 (3)°
  • V = 1129.0 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 153 K
  • 0.20 × 0.18 × 0.12 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.982, T max = 0.989
  • 9650 measured reflections
  • 2677 independent reflections
  • 2221 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.146
  • S = 1.09
  • 2677 reflections
  • 165 parameters
  • H-atom parameters constrained
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037943/cv2765sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037943/cv2765Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The author is indebted to Beijing Amber Tech Co. Ltd for the offer of some reagents.

supplementary crystallographic information

Comment

Functionalized quinoxalines represent an important class of nitrogen-containing heterocycle which display a broad spectrum of biological activity. Similar structure had been reported by Koch (Koch et al., 2009). Quinoxaline derivatives were found to exhibit antimicrobial (Kleim et al. 1995), antitumor (Abasolo et al.,1987), and antituberculous activity (Rodrigo et al., 2002). Here, we report the synthesis and crystal structure of the title compound, (I) (Fig. 1).

The molecular structure of title compound (I) is as shown in Fig.1. The dihedral angle between the pyrido[2,3-b]pyrazine ring and benzene ring is 14.0 (2)°. The O atom attached to the phenyl ring don't deviate the phenyl ring with an r.m.s deviation of 0.0047 (3) Å. As a result of π-π conjugation, the Csp2-O bond [O1—C9 = 1.3656 (13) Å] is significantly shorter than the Csp3-O bond [O1—C14 = 1.4266 (15) Å]. The crystal structure is stabilized by weak C—H···N and C—H···O intermolecular interactions and π-π interactions between the Cg1 (centroid of N1/C1—C5) and Cg2 (centroid of C1/C2/N3/C6/C7/N2). Selected geometric parameters are shown in Table 1.

Experimental

A suspension of 2-(4-methoxyphenyl)-2-oxoacetaldehyde (2.0 mmol) and pyridine-2,3-diamine (3.0 mmol) in ethanol (5 ml) was stirred at room temperature. The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as light yellow solid in 93% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).

Refinement

All H atoms were positioned geometrically (C—H = 0.95–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2-1.5Ueq of the parent atom.

Figures

Fig. 1.
View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C14H11N3OF(000) = 496
Mr = 237.26Dx = 1.396 Mg m3
Monoclinic, P21/cMelting point: 428 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.4486 (13) ÅCell parameters from 3162 reflections
b = 7.3265 (15) Åθ = 2.6–27.9°
c = 24.216 (6) ŵ = 0.09 mm1
β = 99.31 (3)°T = 153 K
V = 1129.0 (4) Å3Prism, colourless
Z = 40.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer2677 independent reflections
Radiation source: rotating anode2221 reflections with I > 2σ(I)
multilayerRint = 0.034
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.7°
[var phi] and ω scansh = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −9→9
Tmin = 0.982, Tmax = 0.989l = −19→31
9650 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.146w = 1/[σ2(Fo2) + (0.0916P)2 + 0.0926P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
2677 reflectionsΔρmax = 0.39 e Å3
165 parametersΔρmin = −0.27 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.194 (16)

Special details

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.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.71204 (14)0.63090 (12)0.31035 (3)0.0269 (3)
N11.25315 (15)0.85321 (13)0.01789 (4)0.0217 (3)
N21.03617 (15)0.75236 (12)0.07944 (4)0.0194 (3)
N30.73020 (15)0.63878 (13)−0.01163 (4)0.0212 (3)
C11.06896 (17)0.77325 (15)0.02545 (5)0.0180 (3)
C20.91672 (17)0.71404 (15)−0.02001 (5)0.0187 (3)
C30.95826 (18)0.73760 (16)−0.07480 (5)0.0221 (3)
H30.86030.6979−0.10610.027*
C41.14169 (19)0.81838 (16)−0.08199 (5)0.0237 (3)
H41.17340.8377−0.11850.028*
C51.28488 (19)0.87344 (16)−0.03427 (5)0.0228 (3)
H51.41270.9288−0.04020.027*
C60.70072 (18)0.62433 (15)0.04042 (5)0.0211 (3)
H60.57150.57530.04770.025*
C70.85538 (17)0.67952 (15)0.08691 (5)0.0181 (3)
C80.81251 (17)0.65886 (15)0.14497 (5)0.0193 (3)
C90.93848 (19)0.75321 (17)0.18866 (5)0.0245 (3)
H91.05130.82660.18060.029*
C100.90077 (19)0.74085 (17)0.24297 (5)0.0253 (3)
H100.98650.80630.27190.030*
C110.73669 (19)0.63212 (15)0.25539 (5)0.0210 (3)
C120.61082 (19)0.53616 (16)0.21299 (5)0.0235 (3)
H120.49930.46160.22130.028*
C130.65008 (18)0.55069 (16)0.15829 (5)0.0227 (3)
H130.56400.48520.12940.027*
C140.5489 (2)0.52103 (19)0.32631 (5)0.0320 (3)
H14A0.41210.56710.30810.048*
H14B0.55640.52600.36700.048*
H14C0.56620.39450.31470.048*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0318 (5)0.0324 (5)0.0180 (5)−0.0071 (4)0.0082 (3)−0.0017 (3)
N10.0205 (5)0.0225 (5)0.0226 (5)−0.0010 (4)0.0050 (4)−0.0004 (4)
N20.0200 (5)0.0199 (5)0.0185 (5)−0.0010 (4)0.0034 (4)−0.0008 (4)
N30.0191 (5)0.0233 (5)0.0204 (5)−0.0008 (4)0.0013 (4)0.0005 (4)
C10.0182 (5)0.0172 (5)0.0186 (6)0.0012 (4)0.0024 (4)−0.0007 (4)
C20.0189 (5)0.0167 (5)0.0203 (6)0.0017 (4)0.0026 (4)0.0005 (4)
C30.0245 (6)0.0225 (6)0.0185 (6)0.0018 (4)0.0008 (4)0.0003 (4)
C40.0280 (6)0.0241 (6)0.0201 (6)0.0021 (5)0.0069 (4)0.0019 (5)
C50.0218 (6)0.0223 (6)0.0253 (6)−0.0002 (4)0.0069 (4)0.0002 (4)
C60.0183 (5)0.0229 (6)0.0220 (6)−0.0020 (4)0.0029 (4)0.0001 (4)
C70.0185 (5)0.0164 (5)0.0194 (6)0.0005 (4)0.0032 (4)−0.0010 (4)
C80.0203 (5)0.0194 (5)0.0183 (6)−0.0003 (4)0.0032 (4)−0.0011 (4)
C90.0241 (6)0.0278 (6)0.0218 (6)−0.0078 (5)0.0046 (4)−0.0012 (4)
C100.0277 (6)0.0283 (7)0.0192 (6)−0.0066 (5)0.0015 (5)−0.0032 (5)
C110.0244 (6)0.0216 (6)0.0178 (6)0.0007 (4)0.0058 (4)0.0000 (4)
C120.0242 (6)0.0230 (6)0.0247 (6)−0.0053 (4)0.0080 (5)−0.0017 (5)
C130.0247 (6)0.0229 (6)0.0209 (6)−0.0045 (4)0.0048 (4)−0.0041 (4)
C140.0340 (7)0.0412 (8)0.0241 (6)−0.0085 (6)0.0141 (5)−0.0009 (5)

Geometric parameters (Å, °)

O1—C111.3656 (13)C6—H60.9500
O1—C141.4266 (15)C7—C81.4838 (15)
N1—C51.3203 (15)C8—C131.3924 (16)
N1—C11.3630 (14)C8—C91.4069 (16)
N2—C71.3210 (14)C9—C101.3786 (16)
N2—C11.3662 (14)C9—H90.9500
N3—C61.3089 (15)C10—C111.3955 (16)
N3—C21.3678 (15)C10—H100.9500
C1—C21.4192 (16)C11—C121.3921 (17)
C2—C31.4061 (15)C12—C131.3922 (16)
C3—C41.3588 (17)C12—H120.9500
C3—H30.9500C13—H130.9500
C4—C51.4161 (17)C14—H14A0.9800
C4—H40.9500C14—H14B0.9800
C5—H50.9500C14—H14C0.9800
C6—C71.4361 (16)
Cg1···Cg2i3.639 (1)Cg2···Cg2ii3.735 (1)
Cg1···Cg2ii3.609 (1)
C11—O1—C14118.35 (9)C13—C8—C9118.02 (11)
C5—N1—C1116.75 (10)C13—C8—C7122.69 (10)
C7—N2—C1116.94 (10)C9—C8—C7119.28 (10)
C6—N3—C2116.34 (9)C10—C9—C8121.05 (11)
N1—C1—N2116.73 (10)C10—C9—H9119.5
N1—C1—C2122.39 (11)C8—C9—H9119.5
N2—C1—C2120.88 (10)C9—C10—C11120.00 (11)
N3—C2—C3119.72 (10)C9—C10—H10120.0
N3—C2—C1121.51 (11)C11—C10—H10120.0
C3—C2—C1118.75 (11)O1—C11—C12124.73 (11)
C4—C3—C2118.49 (11)O1—C11—C10115.19 (10)
C4—C3—H3120.8C12—C11—C10120.08 (11)
C2—C3—H3120.8C11—C12—C13119.28 (11)
C3—C4—C5119.06 (11)C11—C12—H12120.4
C3—C4—H4120.5C13—C12—H12120.4
C5—C4—H4120.5C12—C13—C8121.56 (11)
N1—C5—C4124.56 (11)C12—C13—H13119.2
N1—C5—H5117.7C8—C13—H13119.2
C4—C5—H5117.7O1—C14—H14A109.5
N3—C6—C7122.78 (11)O1—C14—H14B109.5
N3—C6—H6118.6H14A—C14—H14B109.5
C7—C6—H6118.6O1—C14—H14C109.5
N2—C7—C6121.51 (11)H14A—C14—H14C109.5
N2—C7—C8118.35 (10)H14B—C14—H14C109.5
C6—C7—C8120.13 (10)
C5—N1—C1—N2−179.99 (9)N3—C6—C7—N21.49 (17)
C5—N1—C1—C2−0.10 (17)N3—C6—C7—C8−179.77 (10)
C7—N2—C1—N1178.19 (9)N2—C7—C8—C13−166.08 (10)
C7—N2—C1—C2−1.70 (16)C6—C7—C8—C1315.13 (16)
C6—N3—C2—C3−178.71 (10)N2—C7—C8—C914.63 (16)
C6—N3—C2—C1−0.13 (17)C6—C7—C8—C9−164.15 (11)
N1—C1—C2—N3−178.12 (9)C13—C8—C9—C10−0.79 (17)
N2—C1—C2—N31.77 (17)C7—C8—C9—C10178.54 (10)
N1—C1—C2—C30.47 (17)C8—C9—C10—C110.59 (18)
N2—C1—C2—C3−179.64 (9)C14—O1—C11—C121.36 (17)
N3—C2—C3—C4177.79 (10)C14—O1—C11—C10−179.27 (10)
C1—C2—C3—C4−0.83 (17)C9—C10—C11—O1−179.45 (10)
C2—C3—C4—C50.83 (17)C9—C10—C11—C12−0.05 (18)
C1—N1—C5—C40.10 (17)O1—C11—C12—C13179.06 (10)
C3—C4—C5—N1−0.48 (18)C10—C11—C12—C13−0.28 (17)
C2—N3—C6—C7−1.43 (16)C11—C12—C13—C80.06 (17)
C1—N2—C7—C60.18 (16)C9—C8—C13—C120.46 (17)
C1—N2—C7—C8−178.59 (9)C7—C8—C13—C12−178.84 (10)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···N3iii0.952.543.361 (2)145
C3—H3···O1iv0.952.443.123 (2)129

Symmetry codes: (iii) −x+1, −y+1, −z; (iv) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2765).

References

  • Abasolo, M. I., Gaozza, C. H. & Fernandez, B. M. (1987). J. Heterocycl. Chem.24, 1771–1775.
  • Kleim, J. P., Bender, R., Kirsch, R., Meichsner, C., Paessens, A., Rosner, M., Rubsamen Waigmann, H., Kaiser, R., Wichers, M., Schneweis, K. E., Winkler, I. & Riess, G. (1995). Antimicrob. Agents Chemother.39, 2253–2257. [PMC free article] [PubMed]
  • Koch, P., Schollmeyer, D. & Laufer, S. (2009). Acta Cryst. E65, o2512. [PMC free article] [PubMed]
  • Rigaku/MSC (2005). CrystalClear Rigaku/MSC Inc., The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
  • Rodrigo, G. A., Robinshon, A. E., Hedrera, M. E., Kogan, M., Sicardi, S. M. & Fernaandez, B. M. (2002). Trends Heterocycl. Chem.8, 137–143.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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