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The molecule of the title compound, C10H7N3, excluding the methyl H atoms, is essentially planar, the maximum deviation being 0.067 (2) Å for the C atom of the methyl group. The mol­ecular packing is made up of a network of weak hydrogen-bonding inter­actions involving all the N atoms, which stabilizes the mol­ecules in layers parallel to the ac plane. The inter­layer distance of ca 3.74 Å allows stabilization along the b axis by π–π stacking.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010537/su2008sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010537/su20083sup2.hkl
Contains datablock 3

CCDC reference: 643118

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.048
  • wR factor = 0.124
  • Data-to-parameter ratio = 69.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C8 - C10 .. 10.17 su
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C2 .. 6.85 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C9 .. 6.95 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C8 - C10 ... 1.45 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. N1 .. 2.74 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A .. N2 .. 2.69 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. N3 .. 2.73 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. N3 .. 2.72 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. N3 .. 3.00 Ang. PLAT728_ALERT_1_C D-H..A Calc 165.00, Rep 163.00 Dev... 2.00 Deg. C2 -H2 -N3 1.555 1.555 1.456
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-Methylquinoxaline-2-carbonitrile top
Crystal data top
C10H7N3Z = 2
Mr = 169.19F(000) = 176
Triclinic, P1Dx = 1.330 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.869 (2) ÅCell parameters from 1572 reflections
b = 7.417 (3) Åθ = 3.1–32.1°
c = 9.879 (5) ŵ = 0.08 mm1
α = 72.37 (4)°T = 293 K
β = 71.82 (3)°Prism, yellow
γ = 64.29 (3)°0.10 × 0.01 × 0.01 mm
V = 422.5 (3) Å3
Data collection top
Oxford Diffraction Model?? CCD
diffractometer
2969 independent reflections
Radiation source: Enhance (Mo) X-ray Source2753 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 16.0827 pixels mm-1θmax = 32.1°, θmin = 3.1°
ω scansh = 109
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2006)
k = 1010
Tmin = 0.993, Tmax = 0.997l = 1414
8147 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 0.82 w = 1/[σ2(Fo2) + (0.0679P)2 + 0.2503P]
where P = (Fo2 + 2Fc2)/3
8147 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.16 e Å3
Special details top

Experimental. FT–IR (KBr): 2918, 2849. 2260,1458, 1779, 779 cm-1. 1H NMR (CDCl3, 300 MHz): δ (p.p.m.): 8.13(m, 2H), 7.86 (m, 2H), 2.98(s, 3H).

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. 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 > 2sigma(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) top
xyzUiso*/Ueq
N10.42655 (13)0.26356 (11)0.52161 (9)0.0464 (2)
N20.09803 (12)0.23709 (11)0.42293 (8)0.0470 (2)
C80.28032 (17)0.25762 (14)0.33625 (10)0.0446 (3)
C60.07313 (16)0.23208 (13)0.56572 (10)0.0417 (3)
C10.11807 (17)0.21306 (14)0.66428 (11)0.0527 (3)
H10.22750.20560.63210.063*
C50.23836 (17)0.24272 (13)0.61560 (10)0.0417 (3)
C90.64517 (16)0.30293 (15)0.27669 (10)0.0596 (3)
H9A0.73890.31120.32730.089*
H9B0.59870.42690.20690.089*
H9C0.72530.18980.22760.089*
C70.44581 (16)0.27291 (13)0.38361 (10)0.0430 (3)
C20.14095 (19)0.20578 (15)0.80703 (12)0.0598 (3)
H20.26730.19350.87280.072*
C40.20905 (18)0.23444 (14)0.76361 (10)0.0540 (3)
H40.31670.24120.79810.065*
C30.0224 (2)0.21649 (15)0.85687 (12)0.0607 (3)
H30.00310.21130.95520.073*
C100.30733 (18)0.26221 (16)0.18420 (13)0.0579 (3)
N30.33425 (17)0.26415 (16)0.06474 (11)0.0878 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0484 (5)0.0479 (5)0.0491 (6)0.0214 (4)0.0164 (4)0.0063 (4)
N20.0458 (6)0.0515 (5)0.0482 (6)0.0189 (4)0.0132 (4)0.0115 (4)
C80.0484 (7)0.0480 (6)0.0404 (7)0.0177 (5)0.0143 (5)0.0082 (4)
C60.0412 (7)0.0415 (6)0.0444 (7)0.0147 (5)0.0121 (5)0.0089 (4)
C10.0469 (7)0.0619 (7)0.0535 (7)0.0241 (6)0.0097 (5)0.0122 (5)
C50.0447 (7)0.0403 (6)0.0424 (7)0.0154 (5)0.0136 (5)0.0074 (4)
C90.0527 (7)0.0639 (8)0.0645 (8)0.0269 (6)0.0136 (6)0.0069 (6)
C70.0424 (6)0.0435 (6)0.0456 (7)0.0168 (5)0.0141 (5)0.0059 (5)
C20.0535 (7)0.0617 (7)0.0546 (8)0.0203 (6)0.0023 (6)0.0095 (5)
C40.0656 (8)0.0577 (7)0.0471 (7)0.0258 (6)0.0232 (6)0.0060 (5)
C30.0743 (8)0.0656 (8)0.0419 (6)0.0274 (7)0.0119 (6)0.0086 (5)
C100.0539 (8)0.0737 (8)0.0514 (8)0.0253 (6)0.0121 (6)0.0161 (6)
N30.0904 (8)0.1267 (10)0.0562 (7)0.0429 (7)0.0141 (6)0.0295 (6)
Geometric parameters (Å, º) top
N1—C71.3110 (13)C9—C71.5034 (13)
N1—C51.3765 (12)C9—H9A0.9600
N2—C81.3198 (12)C9—H9B0.9600
N2—C61.3579 (13)C9—H9C0.9600
C8—C71.4142 (14)C2—C31.3977 (16)
C8—C101.4466 (16)C2—H20.9300
C6—C11.4045 (14)C4—C31.3590 (14)
C6—C51.4097 (13)C4—H40.9300
C1—C21.3562 (15)C3—H30.9300
C1—H10.9300C10—N31.1327 (13)
C5—C41.3982 (14)
C7—N1—C5117.17 (9)C7—C9—H9C109.5
C8—N2—C6116.08 (10)H9A—C9—H9C109.5
N2—C8—C7124.16 (9)H9B—C9—H9C109.5
N2—C8—C10116.11 (11)N1—C7—C8120.46 (9)
C7—C8—C10119.73 (9)N1—C7—C9118.84 (11)
N2—C6—C1119.32 (11)C8—C7—C9120.70 (9)
N2—C6—C5120.63 (9)C1—C2—C3121.03 (11)
C1—C6—C5120.05 (10)C1—C2—H2119.5
C2—C1—C6119.08 (11)C3—C2—H2119.5
C2—C1—H1120.5C3—C4—C5119.67 (12)
C6—C1—H1120.5C3—C4—H4120.2
N1—C5—C4119.30 (11)C5—C4—H4120.2
N1—C5—C6121.47 (9)C4—C3—C2120.94 (11)
C4—C5—C6119.23 (10)C4—C3—H3119.5
C7—C9—H9A109.5C2—C3—H3119.5
C7—C9—H9B109.5N3—C10—C8178.22 (13)
H9A—C9—H9B109.5
C6—N2—C8—C70.37 (13)C5—N1—C7—C81.28 (12)
C6—N2—C8—C10179.78 (8)C5—N1—C7—C9177.92 (8)
C8—N2—C6—C1179.23 (9)N2—C8—C7—N11.20 (14)
C8—N2—C6—C51.72 (12)C10—C8—C7—N1178.18 (9)
N2—C6—C1—C2179.25 (9)N2—C8—C7—C9177.98 (9)
C5—C6—C1—C20.19 (14)C10—C8—C7—C92.64 (13)
C7—N1—C5—C4179.26 (9)C6—C1—C2—C30.13 (15)
C7—N1—C5—C60.07 (12)N1—C5—C4—C3179.16 (9)
N2—C6—C5—N11.65 (13)C6—C5—C4—C30.05 (14)
C1—C6—C5—N1179.30 (9)C5—C4—C3—C20.12 (15)
N2—C6—C5—C4179.15 (8)C1—C2—C3—C40.03 (16)
C1—C6—C5—C40.10 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···N1i0.932.743.651 (4)169
C9—H9A···N2ii0.962.693.616 (4)162
C2—H2···N3iii0.932.733.639 (4)163
C4—H4···N3iv0.932.723.435 (2)133
C3—H3···N3iv0.933.003.574 (2)120
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x1, y, z+1; (iv) x, y, z+1.
 

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