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Mol­ecules of the title compound, C16H14N2, are located on a crystallographic mirror plane with one half-mol­ecule in the asymmetric unit. The mol­ecules are held together in the crystal structure by π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050525/bt2213sup1.cif
Contains datablocks I, 794

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050525/bt2213Isup2.hkl
Contains datablock I

CCDC reference: 629453

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.117
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C3 .. 6.16 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C4 .. 5.88 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C3 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C4 ... 1.44 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C16H14N2F(000) = 496
Mr = 234.29Dx = 1.192 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 1567 reflections
a = 11.1480 (2) Åθ = 3.2–25.0°
b = 7.0072 (2) ŵ = 0.07 mm1
c = 16.7188 (4) ÅT = 298 K
V = 1306.01 (5) Å3Needle, colourless
Z = 40.25 × 0.20 × 0.15 mm
Data collection top
Smart CCD
diffractometer
1399 independent reflections
Radiation source: fine-focus sealed tube1062 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ω scanθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan
SADABS (Bruker, 1997)
h = 1213
Tmin = 0.983, Tmax = 0.989k = 88
10458 measured reflectionsl = 2016
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0615P)2 + 0.1377P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
1399 reflectionsΔρmax = 0.18 e Å3
108 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.008 (2)
Special details top

Experimental. 1H NMR (CDCl3, δ, p.p.m.): 8.31 (d, 2H, J = 5.4 Hz), 7.88–7.95 (m, 3H), 1.45 (s, 9H).

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
N10.67990 (15)0.25000.27160 (10)0.0717 (5)
N20.81811 (14)0.25000.48887 (11)0.0729 (6)
H14B0.11690.25000.78330.109*
H14A0.22650.14200.74640.109*
C10.61659 (15)0.25000.32500 (10)0.0501 (5)
C20.71716 (15)0.25000.48083 (10)0.0482 (4)
C30.53742 (14)0.25000.39309 (9)0.0404 (4)
C40.58906 (13)0.25000.47134 (9)0.0391 (4)
C50.41579 (14)0.25000.38425 (9)0.0419 (4)
H50.38300.25000.33310.050*
C60.51555 (14)0.25000.53673 (9)0.0410 (4)
H60.54960.25000.58750.049*
C70.33891 (13)0.25000.45124 (9)0.0378 (4)
C80.38993 (13)0.25000.52944 (8)0.0373 (4)
C90.21278 (14)0.25000.44446 (10)0.0470 (4)
H90.17750.25000.39410.056*
C100.31335 (14)0.25000.59644 (9)0.0424 (4)
H100.34710.25000.64730.051*
C110.14235 (15)0.25000.51082 (10)0.0487 (4)
H110.05950.25000.50460.058*
C120.19093 (14)0.25000.58935 (10)0.0434 (4)
C130.10586 (15)0.25000.66087 (11)0.0555 (5)
C140.1737 (2)0.25000.74021 (12)0.0857 (8)
C150.02692 (14)0.0720 (2)0.65696 (10)0.0830 (5)
H15A0.07650.03990.65890.124*
H15B0.01810.07270.60800.124*
H15C0.02730.07140.70160.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0641 (11)0.1037 (14)0.0473 (10)0.0000.0148 (8)0.000
N20.0378 (9)0.0898 (13)0.0909 (13)0.0000.0049 (8)0.000
C10.0482 (10)0.0611 (11)0.0410 (10)0.0000.0015 (8)0.000
C20.0425 (10)0.0544 (10)0.0476 (10)0.0000.0004 (7)0.000
C30.0423 (9)0.0436 (9)0.0353 (8)0.0000.0038 (7)0.000
C40.0351 (8)0.0419 (8)0.0404 (9)0.0000.0015 (6)0.000
C50.0450 (9)0.0500 (9)0.0307 (8)0.0000.0045 (7)0.000
C60.0406 (9)0.0491 (9)0.0332 (8)0.0000.0070 (7)0.000
C70.0374 (8)0.0411 (8)0.0350 (8)0.0000.0028 (6)0.000
C80.0385 (8)0.0396 (8)0.0337 (8)0.0000.0016 (6)0.000
C90.0408 (9)0.0614 (11)0.0389 (9)0.0000.0082 (7)0.000
C100.0433 (9)0.0512 (9)0.0329 (8)0.0000.0014 (7)0.000
C110.0348 (8)0.0615 (11)0.0500 (10)0.0000.0007 (7)0.000
C120.0419 (9)0.0452 (9)0.0432 (9)0.0000.0051 (7)0.000
C130.0480 (10)0.0676 (12)0.0510 (11)0.0000.0157 (8)0.000
C140.0701 (14)0.143 (2)0.0436 (11)0.0000.0209 (10)0.000
C150.0759 (10)0.0846 (11)0.0884 (12)0.0192 (8)0.0334 (8)0.0052 (9)
Geometric parameters (Å, º) top
N1—C11.138 (2)C9—H90.9300
N2—C21.133 (2)C10—C121.370 (2)
C1—C31.440 (2)C10—H100.9300
C2—C41.437 (2)C11—C121.420 (2)
C3—C51.364 (2)C11—H110.9300
C3—C41.429 (2)C12—C131.526 (2)
C4—C61.366 (2)C13—C141.527 (3)
C5—C71.410 (2)C13—C151.5278 (18)
C5—H50.9300C13—C15i1.5278 (18)
C6—C81.406 (2)C14—H14B0.9595
C6—H60.9300C14—H14A0.9637
C7—C91.411 (2)C15—H15A0.9600
C7—C81.426 (2)C15—H15B0.9600
C8—C101.408 (2)C15—H15C0.9600
C9—C111.359 (2)
N1—C1—C3179.47 (18)C12—C10—H10118.8
N2—C2—C4179.52 (19)C8—C10—H10118.8
C5—C3—C4119.97 (14)C9—C11—C12122.30 (15)
C5—C3—C1121.57 (14)C9—C11—H11118.9
C4—C3—C1118.46 (14)C12—C11—H11118.9
C6—C4—C3119.39 (14)C10—C12—C11117.38 (14)
C6—C4—C2120.52 (14)C10—C12—C13123.46 (15)
C3—C4—C2120.09 (14)C11—C12—C13119.16 (14)
C3—C5—C7121.20 (14)C12—C13—C14111.89 (14)
C3—C5—H5119.4C12—C13—C15108.93 (10)
C7—C5—H5119.4C14—C13—C15108.82 (11)
C4—C6—C8121.88 (14)C12—C13—C15i108.93 (10)
C4—C6—H6119.1C14—C13—C15i108.82 (11)
C8—C6—H6119.1C15—C13—C15i109.44 (17)
C5—C7—C9122.82 (14)C13—C14—H14B109.0
C5—C7—C8119.07 (14)C13—C14—H14A113.3
C9—C7—C8118.11 (14)H14B—C14—H14A108.8
C6—C8—C10122.34 (13)C13—C15—H15A109.5
C6—C8—C7118.48 (13)C13—C15—H15B109.5
C10—C8—C7119.18 (14)H15A—C15—H15B109.5
C11—C9—C7120.68 (14)C13—C15—H15C109.5
C11—C9—H9119.7H15A—C15—H15C109.5
C7—C9—H9119.7H15B—C15—H15C109.5
C12—C10—C8122.35 (14)
Symmetry code: (i) x, y+1/2, z.
 

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