(1E,2E)-1,2-Bis[(E)-3-phenyl­allyl­idene]­hydrazine

The title compound [alternatively called (E)-3-phenyl­prop-2-enal azine], C₁₈H₁₆N₂, was synthesized by the reaction of hydro­cinnamaldehyde with hydrazine hydrate. The nearly planar mol­ecule is centrosymmetric, with the mid-point of the N-N bond lying at an inversion center.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.094
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT148_ALERT_3_B su on the      a  - Axis is Too Large (x 1000) .         20 Ang.

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
   2 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 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
   2 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

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S1. Comment

The azine derivatives have been investigated in terms of their coordination chemistry and their special properties (Zheng & Zhao, 2006; Kundu et al., 2005; Jiang & Hu, 2004; Trujillo et al., 1997). The synthesis and crystal structure of the title compound (Fig. 1) is reported here.

In the molecule of title molecule, there is an inversion center at the midpoint of the N1—N1A single bond [symmetry code A, -x, -y, -z + 1], and all of the atoms are approximately coplanar. The single N—N bond length is 1.398 (3) Å (Table 1), which is consistent with those found in related azine compounds (Zheng & Zhao, 2006; Zhao et al., 2006). The bond angle of N(1)—C(9)—C(8) is 120.9 (2)°, showing the atom C9 is of sp² hybridization.

Related literature

For related literature, see: Jiang & Hu (2004); Kundu et al. (2005); Trujillo et al. (1997); Zheng & Zhao (2006); Zhao et al. (2006).

S2. Experimental

The title compound was prepared by the reaction of hydrocinncmaladehyde and hydrazine hydrate with a ratio of 2:1 under reflux in the mixture of ethanol and DMF for 2 h. After one week, yellow prismatic crystals were obtained by slow evaporation at room temperature.

S3. Refinement

All H atoms were placed in calculated positions and treated using a riding model with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. View of the molecular structure with displacement ellipsoids drawn at the 30% probability level for non-H atoms. [Symmetry code: (A) -x, -y, -z + 1.]

(1E,2E)-1,2-Bis[(E)-3-phenylallylidene]hydrazine

Crystal data

C18H16N2	F(000) = 276
Mr = 260.33	Dx = 1.172 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1381 reflections
a = 17.11 (2) Å	θ = 3.6–26.0°
b = 5.456 (5) Å	µ = 0.07 mm^−1
c = 7.988 (7) Å	T = 293 K
β = 98.25 (4)°	Prism, yellow
V = 738.0 (13) Å^3	0.55 × 0.21 × 0.12 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID IP diffractometer	844 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 26.0°, θmin = 3.6°
ω scans	h = −21→21
5393 measured reflections	k = −6→6
1381 independent reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0491P)^2] where P = (Fo^2 + 2Fc^2)/3
1381 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.09 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.04070 (6)	−0.0045 (3)	0.49829 (15)	0.0722 (4)
C1	0.26140 (7)	0.4619 (2)	0.34602 (14)	0.0481 (3)
C2	0.32091 (8)	0.3004 (2)	0.41067 (17)	0.0517 (4)
H2A	0.3085	0.1627	0.4701	0.062*
C3	0.39765 (8)	0.3412 (3)	0.38813 (17)	0.0568 (4)
H3A	0.4367	0.2307	0.4321	0.068*
C4	0.41760 (9)	0.5435 (3)	0.30128 (17)	0.0608 (4)
H4A	0.4698	0.5701	0.2863	0.073*
C5	0.35992 (9)	0.7059 (3)	0.23671 (19)	0.0626 (4)
H5A	0.3731	0.8428	0.1773	0.075*
C6	0.28275 (8)	0.6675 (3)	0.25939 (16)	0.0562 (4)
H6A	0.2443	0.7802	0.2164	0.067*
C7	0.17886 (8)	0.4207 (3)	0.36486 (16)	0.0579 (4)
H7A	0.1439	0.5477	0.3309	0.070*
C8	0.14843 (8)	0.2210 (3)	0.42545 (18)	0.0609 (4)
H8A	0.1825	0.0927	0.4619	0.073*
C9	0.06635 (8)	0.1918 (3)	0.43782 (18)	0.0657 (4)
H9A	0.0312	0.3173	0.4014	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0402 (6)	0.0995 (10)	0.0762 (8)	−0.0123 (7)	0.0061 (6)	0.0094 (8)
C1	0.0463 (8)	0.0529 (8)	0.0449 (7)	−0.0053 (6)	0.0062 (5)	−0.0037 (7)
C2	0.0490 (8)	0.0503 (8)	0.0561 (8)	−0.0049 (6)	0.0086 (6)	0.0018 (7)
C3	0.0481 (8)	0.0587 (9)	0.0638 (9)	0.0000 (7)	0.0090 (6)	−0.0045 (7)
C4	0.0531 (9)	0.0677 (11)	0.0644 (9)	−0.0145 (8)	0.0178 (7)	−0.0093 (8)
C5	0.0723 (11)	0.0556 (9)	0.0622 (9)	−0.0185 (8)	0.0178 (8)	0.0014 (7)
C6	0.0616 (9)	0.0504 (9)	0.0561 (8)	−0.0006 (7)	0.0064 (7)	0.0009 (7)
C7	0.0467 (8)	0.0688 (10)	0.0573 (8)	0.0001 (7)	0.0039 (6)	0.0010 (8)
C8	0.0433 (9)	0.0803 (11)	0.0588 (9)	−0.0071 (7)	0.0059 (6)	0.0042 (8)
C9	0.0456 (9)	0.0900 (12)	0.0606 (9)	−0.0084 (8)	0.0042 (6)	0.0028 (9)

Geometric parameters (Å, º)

N1—C9	1.278 (2)	C4—H4A	0.9300
N1—N1^i	1.398 (3)	C5—C6	1.374 (2)
C1—C2	1.389 (2)	C5—H5A	0.9300
C1—C6	1.3944 (19)	C6—H6A	0.9300
C1—C7	1.459 (2)	C7—C8	1.329 (2)
C2—C3	1.369 (2)	C7—H7A	0.9300
C2—H2A	0.9300	C8—C9	1.431 (2)
C3—C4	1.373 (2)	C8—H8A	0.9300
C3—H3A	0.9300	C9—H9A	0.9300
C4—C5	1.371 (2)
C9—N1—N1^i	112.04 (17)	C4—C5—H5A	119.8
C2—C1—C6	117.70 (14)	C6—C5—H5A	119.8
C2—C1—C7	122.21 (14)	C5—C6—C1	120.87 (14)
C6—C1—C7	120.09 (13)	C5—C6—H6A	119.6
C3—C2—C1	120.92 (14)	C1—C6—H6A	119.6
C3—C2—H2A	119.5	C8—C7—C1	126.82 (14)
C1—C2—H2A	119.5	C8—C7—H7A	116.6
C2—C3—C4	120.66 (14)	C1—C7—H7A	116.6
C2—C3—H3A	119.7	C7—C8—C9	123.78 (15)
C4—C3—H3A	119.7	C7—C8—H8A	118.1
C5—C4—C3	119.49 (15)	C9—C8—H8A	118.1
C5—C4—H4A	120.3	N1—C9—C8	120.86 (16)
C3—C4—H4A	120.3	N1—C9—H9A	119.6
C4—C5—C6	120.34 (15)	C8—C9—H9A	119.6
C6—C1—C2—C3	−0.73 (18)	C7—C1—C6—C5	−178.33 (12)
C7—C1—C2—C3	178.68 (12)	C2—C1—C7—C8	−8.1 (2)
C1—C2—C3—C4	0.2 (2)	C6—C1—C7—C8	171.33 (13)
C2—C3—C4—C5	0.0 (2)	C1—C7—C8—C9	−178.97 (12)
C3—C4—C5—C6	0.3 (2)	N1^i—N1—C9—C8	179.17 (13)
C4—C5—C6—C1	−0.9 (2)	C7—C8—C9—N1	−179.57 (14)
C2—C1—C6—C5	1.08 (19)

Symmetry code: (i) −x, −y, −z+1.