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In the crystal structure of the title compound, C12H10N4, the pyridine ring makes a dihedral angle of 1.12 (9)° with the mean plane of the complete almost planar and crystallographically centrosymmetric mol­ecule. There are stacks of parallel mol­ecules along the a-axis direction, with alternate stacks having a herring-bone arrangement relative to each other and an interplanar spacing of 3.551 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007046/qa0228sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007046/qa0228Isup2.hkl
Contains datablock I

CCDC reference: 146108

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).

(I) top
Crystal data top
C12H10N4F(000) = 220
Mr = 210.24Dx = 1.293 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 3.8515 (3) ÅCell parameters from 2605 reflections
b = 11.0201 (8) Åθ = 2.5–28.3°
c = 12.7303 (9) ŵ = 0.08 mm1
β = 92.312 (2)°T = 293 K
V = 539.88 (7) Å3Block, orange
Z = 20.38 × 0.36 × 0.32 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
1065 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 28.4°, θmin = 2.5°
Detector resolution: 8.33 pixels mm-1h = 55
ω scansk = 147
3584 measured reflectionsl = 1616
1325 independent 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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110All H-atom parameters refined
S = 1.25 w = 1/[σ2(Fo2) + (0.0958P)2 + 0.1438P]
where P = (Fo2 + 2Fc2)/3
1325 reflections(Δ/σ)max < 0.001
93 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.20 e Å3
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.

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) top
xyzUiso*/Ueq
N10.0922 (6)0.8462 (2)0.08500 (15)0.0580 (6)
N20.4664 (5)1.00082 (15)0.44528 (12)0.0453 (5)
C10.2637 (5)0.88327 (16)0.29857 (14)0.0380 (5)
C20.3255 (6)0.97260 (19)0.22425 (15)0.0429 (5)
C30.2348 (6)0.9499 (2)0.12006 (17)0.0524 (6)
C40.0341 (7)0.7614 (2)0.15670 (19)0.0547 (6)
C50.1144 (6)0.77541 (19)0.26308 (17)0.0473 (5)
C60.3510 (5)0.90013 (18)0.41100 (15)0.0416 (5)
H20.436 (7)1.049 (3)0.244 (2)0.064 (8)*
H30.276 (7)1.011 (3)0.067 (2)0.061 (7)*
H40.077 (8)0.687 (3)0.129 (2)0.073 (8)*
H50.062 (7)0.708 (3)0.312 (2)0.063 (7)*
H60.318 (6)0.833 (2)0.457 (2)0.056 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0709 (13)0.0645 (13)0.0383 (9)0.0023 (10)0.0024 (8)0.0116 (8)
N20.0617 (11)0.0423 (9)0.0312 (9)0.0022 (7)0.0073 (7)0.0017 (6)
C10.0408 (10)0.0379 (9)0.0352 (9)0.0026 (7)0.0002 (7)0.0025 (7)
C20.0510 (11)0.0404 (10)0.0373 (10)0.0011 (8)0.0003 (8)0.0008 (7)
C30.0658 (14)0.0554 (13)0.0362 (10)0.0042 (10)0.0020 (9)0.0025 (9)
C40.0627 (14)0.0516 (12)0.0497 (12)0.0048 (10)0.0007 (10)0.0166 (10)
C50.0575 (13)0.0392 (10)0.0453 (11)0.0029 (8)0.0028 (9)0.0051 (8)
C60.0522 (11)0.0375 (9)0.0350 (9)0.0016 (8)0.0009 (7)0.0021 (7)
Geometric parameters (Å, º) top
N1—C41.332 (3)C2—C31.381 (3)
N1—C31.337 (3)C2—H20.97 (3)
N2—C61.266 (3)C3—H30.97 (3)
N2—N2i1.407 (3)C4—C51.386 (3)
C1—C51.388 (3)C4—H40.98 (3)
C1—C21.393 (3)C5—H50.99 (3)
C1—C61.469 (3)C6—H60.95 (3)
C4—N1—C3116.7 (2)C2—C3—H3119.9 (17)
C6—N2—N2i112.2 (2)N1—C4—C5123.7 (2)
C5—C1—C2117.64 (18)N1—C4—H4114.9 (18)
C5—C1—C6120.08 (17)C5—C4—H4121.4 (18)
C2—C1—C6122.28 (17)C4—C5—C1119.2 (2)
C3—C2—C1118.75 (19)C4—C5—H5119.0 (16)
C3—C2—H2119.9 (17)C1—C5—H5121.8 (16)
C1—C2—H2121.3 (17)N2—C6—C1120.67 (17)
N1—C3—C2124.1 (2)N2—C6—H6121.4 (16)
N1—C3—H3116.1 (17)C1—C6—H6117.9 (16)
C5—C1—C2—C30.3 (3)C2—C1—C5—C40.0 (3)
C6—C1—C2—C3179.78 (19)C6—C1—C5—C4179.98 (19)
C4—N1—C3—C20.5 (4)N2i—N2—C6—C1179.84 (19)
C1—C2—C3—N10.5 (4)C5—C1—C6—N2175.41 (19)
C3—N1—C4—C50.3 (4)C2—C1—C6—N24.6 (3)
N1—C4—C5—C10.0 (4)
Symmetry code: (i) x+1, y+2, z+1.
 

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