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The title compound, C20H24N2, (I), has crystallographic Ci symmetry, with the central C-C bond located on a centre of inversion. The dihedral angle between the central 1,4-di­aza­buta-1,3-diene moiety and the attached substituted phenyl ring is 64.0 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024085/lh6130sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024085/lh6130Isup2.hkl
Contains datablock I

CCDC reference: 227023

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.047
  • wR factor = 0.125
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: PLATON (Spek, 1990).

(I) top
Crystal data top
C20H24N2F(000) = 316
Mr = 292.41Dx = 1.118 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4522 reflections
a = 13.486 (1) Åθ = 1–25°
b = 4.403 (1) ŵ = 0.07 mm1
c = 15.435 (1) ÅT = 173 K
β = 108.65 (1)°Block, orange yellow
V = 868.4 (2) Å30.32 × 0.30 × 0.28 mm
Z = 2
Data collection top
Siemens CCD three-circle
diffractometer
1167 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Graphite monochromatorθmax = 25.4°, θmin = 1.6°
ω scansh = 1616
11184 measured reflectionsk = 55
1597 independent reflectionsl = 1818
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0577P)2 + 0.332P]
where P = (Fo2 + 2Fc2)/3
1597 reflections(Δ/σ)max < 0.001
104 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

Experimental. ;

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*/UeqOcc. (<1)
N10.10943 (11)0.6428 (3)0.58628 (10)0.0340 (4)
C10.04460 (13)0.4495 (4)0.53846 (11)0.0324 (4)
H10.05420.23940.55270.039*
C110.19712 (12)0.5314 (4)0.65946 (11)0.0283 (4)
C120.20598 (13)0.6245 (4)0.74896 (11)0.0290 (4)
C130.29109 (13)0.5201 (4)0.82056 (11)0.0310 (4)
H130.29720.57870.88130.037*
C140.36739 (13)0.3331 (4)0.80626 (11)0.0315 (4)
C150.35822 (13)0.2550 (4)0.71676 (11)0.0330 (4)
H150.41110.13310.70590.040*
C160.27403 (13)0.3495 (4)0.64233 (11)0.0309 (4)
C1210.12395 (14)0.8237 (4)0.76667 (13)0.0402 (5)
H12A0.14630.88200.83130.060*
H12B0.05770.71240.75160.060*
H12C0.11441.00650.72870.060*
C1410.45753 (14)0.2138 (5)0.88530 (12)0.0418 (5)
H14A0.48360.37580.93040.063*0.64 (2)
H14B0.51390.14550.86260.063*0.64 (2)
H14C0.43340.04300.91400.063*0.64 (2)
H14D0.47030.00040.87430.063*0.36 (2)
H14E0.44010.23070.94210.063*0.36 (2)
H14F0.52060.33320.89070.063*0.36 (2)
C1610.26935 (15)0.2573 (5)0.54641 (12)0.0420 (5)
H16A0.21890.09150.52520.063*
H16B0.33870.18930.54680.063*
H16C0.24740.43160.50520.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0313 (8)0.0322 (8)0.0296 (8)0.0019 (7)0.0027 (6)0.0032 (7)
C10.0321 (9)0.0278 (9)0.0303 (9)0.0013 (8)0.0000 (8)0.0029 (8)
C110.0262 (9)0.0267 (9)0.0259 (9)0.0052 (7)0.0004 (7)0.0023 (7)
C120.0277 (9)0.0268 (9)0.0304 (9)0.0068 (7)0.0063 (7)0.0002 (7)
C130.0336 (10)0.0344 (10)0.0218 (8)0.0072 (8)0.0041 (7)0.0011 (7)
C140.0280 (9)0.0362 (10)0.0245 (9)0.0054 (8)0.0001 (7)0.0035 (8)
C150.0269 (9)0.0391 (11)0.0308 (10)0.0015 (8)0.0061 (8)0.0009 (8)
C160.0297 (9)0.0350 (10)0.0235 (9)0.0046 (8)0.0022 (7)0.0000 (8)
C1210.0381 (10)0.0403 (11)0.0414 (11)0.0011 (9)0.0114 (9)0.0028 (9)
C1410.0351 (10)0.0532 (12)0.0287 (10)0.0005 (9)0.0018 (8)0.0040 (9)
C1610.0397 (11)0.0560 (13)0.0259 (10)0.0029 (9)0.0045 (8)0.0028 (9)
Geometric parameters (Å, º) top
N1—C11.273 (2)C16—C1611.517 (2)
N1—C111.436 (2)C121—H12A0.9800
C1—C1i1.463 (3)C121—H12B0.9800
C1—H10.9500C121—H12C0.9800
C11—C161.401 (2)C141—H14A0.9800
C11—C121.409 (2)C141—H14B0.9800
C12—C131.392 (2)C141—H14C0.9800
C12—C1211.504 (2)C141—H14D0.9800
C13—C141.389 (3)C141—H14E0.9800
C13—H130.9500C141—H14F0.9800
C14—C151.390 (2)C161—H16A0.9800
C14—C1411.514 (2)C161—H16B0.9800
C15—C161.396 (2)C161—H16C0.9800
C15—H150.9500
C1—N1—C11117.88 (15)C14—C141—H14A109.5
N1—C1—C1i120.1 (2)C14—C141—H14B109.5
N1—C1—H1120.0H14A—C141—H14B109.5
C1i—C1—H1120.0C14—C141—H14C109.5
C16—C11—C12121.04 (15)H14A—C141—H14C109.5
C16—C11—N1121.35 (15)H14B—C141—H14C109.5
C12—C11—N1117.54 (16)C14—C141—H14D109.5
C13—C12—C11118.17 (16)H14A—C141—H14D141.1
C13—C12—C121121.06 (16)H14B—C141—H14D56.3
C11—C12—C121120.75 (15)H14C—C141—H14D56.3
C14—C13—C12122.26 (16)C14—C141—H14E109.5
C14—C13—H13118.9H14A—C141—H14E56.3
C12—C13—H13118.9H14B—C141—H14E141.1
C13—C14—C15117.99 (15)H14C—C141—H14E56.3
C13—C14—C141121.47 (16)H14D—C141—H14E109.5
C15—C14—C141120.54 (17)C14—C141—H14F109.5
C14—C15—C16122.32 (17)H14A—C141—H14F56.3
C14—C15—H15118.8H14B—C141—H14F56.3
C16—C15—H15118.8H14C—C141—H14F141.1
C15—C16—C11118.14 (15)H14D—C141—H14F109.5
C15—C16—C161119.52 (16)H14E—C141—H14F109.5
C11—C16—C161122.34 (15)C16—C161—H16A109.5
C12—C121—H12A109.5C16—C161—H16B109.5
C12—C121—H12B109.5H16A—C161—H16B109.5
H12A—C121—H12B109.5C16—C161—H16C109.5
C12—C121—H12C109.5H16A—C161—H16C109.5
H12A—C121—H12C109.5H16B—C161—H16C109.5
H12B—C121—H12C109.5
C11—N1—C1—C1i178.4 (2)C12—C13—C14—C141178.02 (17)
C1—N1—C11—C1664.7 (2)C13—C14—C15—C162.1 (3)
C1—N1—C11—C12118.49 (18)C141—C14—C15—C16177.21 (17)
C16—C11—C12—C132.7 (2)C14—C15—C16—C110.5 (3)
N1—C11—C12—C13179.49 (14)C14—C15—C16—C161179.65 (17)
C16—C11—C12—C121179.04 (16)C12—C11—C16—C151.9 (2)
N1—C11—C12—C1212.2 (2)N1—C11—C16—C15178.61 (16)
C11—C12—C13—C141.0 (3)C12—C11—C16—C161177.15 (17)
C121—C12—C13—C14179.29 (16)N1—C11—C16—C1610.5 (3)
C12—C13—C14—C151.3 (3)
Symmetry code: (i) x, y+1, z+1.
 

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