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The non-planar mol­ecule of the title compound, C18H20N2, is centrosymmetric about the central point of the ethyl­ene bond and posses E configuration across each azomethine C=N bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602798X/hk2088sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602798X/hk2088Isup2.hkl
Contains datablock I

CCDC reference: 618241

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.056
  • wR factor = 0.165
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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, 2000); cell refinement: SAINT; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

(E,E)—N,N'-Bis(4-tolylmethylidene)ethylenediamine top
Crystal data top
C18H20N2F(000) = 284
Mr = 264.36Dx = 1.162 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 789 reflections
a = 6.842 (2) Åθ = 2.7–26.0°
b = 7.531 (2) ŵ = 0.07 mm1
c = 14.933 (5) ÅT = 298 K
β = 100.801 (7)°Block, colorless
V = 755.8 (4) Å30.42 × 0.28 × 0.16 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1484 independent reflections
Radiation source: fine-focus sealed tube935 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 83.66 pixels mm-1θmax = 26.0°, θmin = 2.7°
ω scansh = 68
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 99
Tmin = 0.971, Tmax = 0.989l = 1817
4098 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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0854P)2 + 0.0506P]
where P = (Fo2 + 2Fc2)/3
1484 reflections(Δ/σ)max < 0.001
92 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.12 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
C10.0514 (3)0.8081 (3)0.79390 (13)0.0562 (6)
H10.03400.77070.85420.067*
C20.2275 (3)0.7733 (3)0.73589 (13)0.0564 (6)
H20.32780.71350.75780.068*
C30.2593 (3)0.8255 (2)0.64504 (13)0.0539 (5)
C40.1078 (3)0.9154 (3)0.61593 (13)0.0582 (6)
H40.12560.95320.55570.070*
C50.0693 (3)0.9509 (2)0.67367 (14)0.0564 (6)
H50.16901.01130.65170.068*
C60.1013 (3)0.8983 (2)0.76387 (13)0.0491 (5)
C70.4517 (3)0.7829 (3)0.58196 (14)0.0741 (7)
H7A0.42440.74350.52440.111*
H7B0.53360.88730.57290.111*
H7C0.51980.69080.60830.111*
C80.2891 (3)0.9364 (2)0.82561 (14)0.0560 (5)
H80.38571.00030.80310.067*
C90.5170 (3)0.9392 (3)0.96206 (14)0.0657 (6)
H9A0.59690.99940.92420.079*
H9B0.58860.83410.98760.079*
N10.3268 (2)0.8878 (2)0.90708 (12)0.0638 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0605 (13)0.0567 (12)0.0507 (11)0.0061 (10)0.0089 (10)0.0052 (9)
C20.0561 (13)0.0555 (12)0.0588 (12)0.0090 (9)0.0143 (10)0.0032 (10)
C30.0554 (12)0.0511 (12)0.0550 (12)0.0038 (9)0.0096 (9)0.0038 (9)
C40.0670 (14)0.0607 (13)0.0488 (11)0.0028 (10)0.0157 (10)0.0054 (10)
C50.0595 (13)0.0522 (12)0.0622 (13)0.0023 (9)0.0234 (10)0.0010 (9)
C60.0495 (11)0.0410 (10)0.0581 (12)0.0002 (8)0.0130 (9)0.0038 (9)
C70.0659 (15)0.0855 (17)0.0669 (14)0.0001 (12)0.0022 (11)0.0001 (12)
C80.0524 (12)0.0457 (11)0.0717 (14)0.0045 (9)0.0161 (10)0.0029 (10)
C90.0543 (12)0.0637 (14)0.0752 (15)0.0064 (10)0.0021 (11)0.0012 (10)
N10.0593 (11)0.0615 (11)0.0667 (12)0.0111 (8)0.0019 (9)0.0006 (9)
Geometric parameters (Å, º) top
C1—C21.371 (2)C6—C81.463 (3)
C1—C61.389 (3)C7—H7A0.9600
C1—H10.9300C7—H7B0.9600
C2—C31.390 (3)C7—H7C0.9600
C2—H20.9300C8—N11.250 (2)
C3—C41.375 (3)C8—H80.9300
C3—C71.502 (3)C9—N11.455 (2)
C4—C51.375 (2)C9—C9i1.509 (4)
C4—H40.9300C9—H9A0.9700
C5—C61.381 (3)C9—H9B0.9700
C5—H50.9300
C2—C1—C6120.95 (18)C1—C6—C8121.17 (18)
C2—C1—H1119.5C3—C7—H7A109.5
C6—C1—H1119.5C3—C7—H7B109.5
C1—C2—C3121.44 (18)H7A—C7—H7B109.5
C1—C2—H2119.3C3—C7—H7C109.5
C3—C2—H2119.3H7A—C7—H7C109.5
C4—C3—C2117.27 (17)H7B—C7—H7C109.5
C4—C3—C7122.04 (19)N1—C8—C6123.51 (19)
C2—C3—C7120.69 (18)N1—C8—H8118.2
C3—C4—C5121.68 (19)C6—C8—H8118.2
C3—C4—H4119.2N1—C9—C9i109.7 (2)
C5—C4—H4119.2N1—C9—H9A109.7
C4—C5—C6121.05 (18)C9i—C9—H9A109.7
C4—C5—H5119.5N1—C9—H9B109.7
C6—C5—H5119.5C9i—C9—H9B109.7
C5—C6—C1117.61 (17)H9A—C9—H9B108.2
C5—C6—C8121.22 (18)C8—N1—C9118.06 (19)
C6—C1—C2—C30.5 (3)C4—C5—C6—C8179.73 (16)
C1—C2—C3—C40.8 (3)C2—C1—C6—C50.2 (3)
C1—C2—C3—C7178.71 (18)C2—C1—C6—C8179.72 (17)
C2—C3—C4—C50.8 (3)C5—C6—C8—N1178.20 (18)
C7—C3—C4—C5178.72 (18)C1—C6—C8—N11.9 (3)
C3—C4—C5—C60.5 (3)C6—C8—N1—C9178.11 (16)
C4—C5—C6—C10.2 (3)C9i—C9—N1—C8115.8 (2)
Symmetry code: (i) x+1, y+2, z+2.
 

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