(1E,2E)-1,2-Bis(2,2-diphenyl-hydrazin-1-yl-idene)ethane.

In the crystal structure of the title compound, C(26)H(22)N(4), the mol-ecule is located on an inversion centre and shows an E configuration with respect to each C=N bond. The dihedral angle between the phenyl rings in the diphenyl-hydrazone group is 83.69 (11)°. These two rings make dihedral angles of 30.53 (15) and 84.53 (16)° with the central N-N=C-C=N-N dihydrazonoethane plane. Inter-molecular C-H⋯π inter-actions are observed.

Related literature

For applications of hydrazones, see: Angell et al. (2006 ▶); Ibañez et al. (2002 ▶). For related structures, see: Clulow et al. (2008 ▶); Mendoza et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C26H22N4

M = 390.48

Monoclinic,

a = 12.2210 (19) Å

b = 5.612 (1) Å

c = 15.731 (3) Å

β = 103.924 (16)°

V = 1047.2 (3) Å3

Z = 2

Cu Kα radiation

μ = 0.58 mm−1

T = 298 K

0.19 × 0.11 × 0.05 mm

Data collection

Oxford Xcalibur Atlas Gemini diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.978, T max = 0.993

3621 measured reflections

1892 independent reflections

1163 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.113

S = 1.01

1892 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810032198/is2589sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032198/is2589Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H22N4	F(000) = 412
Mr = 390.48	Dx = 1.238 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
a = 12.2210 (19) Å	Cell parameters from 864 reflections
b = 5.612 (1) Å	θ = 3.7–68.0°
c = 15.731 (3) Å	µ = 0.58 mm−1
β = 103.924 (16)°	T = 298 K
V = 1047.2 (3) Å3	Prism, colourless
Z = 2	0.19 × 0.11 × 0.05 mm

Oxford Xcalibur Atlas Gemini diffractometer	1892 independent reflections
graphite	1163 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.038
ω scans	θmax = 68.2°, θmin = 4.1°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010)	h = −14→14
Tmin = 0.978, Tmax = 0.993	k = −4→6
3621 measured reflections	l = −18→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.0674P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1892 reflections	Δρmax = 0.13 e Å−3
137 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0134 (9)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
N2	0.09341 (13)	0.1892 (3)	0.46419 (10)	0.0451 (5)
N1	0.20416 (13)	0.2544 (3)	0.48657 (10)	0.0481 (5)
C1	0.23555 (16)	0.4384 (4)	0.43534 (12)	0.0421 (5)
C13	0.05715 (15)	0.0396 (4)	0.51307 (13)	0.0451 (5)
H13	0.1046	−0.0161	0.5646	0.054*
C12	0.27665 (18)	0.3696 (4)	0.63743 (14)	0.0541 (6)
H12	0.2307	0.5037	0.6265	0.065*
C7	0.27471 (15)	0.2080 (4)	0.57158 (12)	0.0415 (5)
C6	0.16000 (18)	0.6077 (4)	0.39339 (13)	0.0494 (5)
H6	0.0859	0.6044	0.3988	0.059*
C2	0.34652 (17)	0.4494 (4)	0.42837 (13)	0.0532 (6)
H2	0.3988	0.3382	0.4574	0.064*
C5	0.1938 (2)	0.7827 (4)	0.34321 (14)	0.0587 (6)
H5	0.1422	0.8956	0.3147	0.07*
C8	0.33966 (18)	0.0069 (4)	0.58755 (15)	0.0572 (6)
H8	0.3374	−0.1049	0.5435	0.069*
C3	0.3793 (2)	0.6255 (4)	0.37837 (15)	0.0623 (7)
H3	0.4538	0.6319	0.3739	0.075*
C4	0.3036 (2)	0.7904 (4)	0.33537 (15)	0.0640 (7)
H4	0.3261	0.9069	0.3011	0.077*
C10	0.4116 (2)	0.1382 (6)	0.73586 (17)	0.0726 (8)
H10	0.4585	0.115	0.7913	0.087*
C9	0.40936 (19)	−0.0277 (5)	0.67093 (19)	0.0722 (8)
H9	0.4544	−0.163	0.6827	0.087*
C11	0.3458 (2)	0.3350 (5)	0.71930 (15)	0.0708 (8)
H11	0.3473	0.4465	0.7633	0.085*

	U11	U22	U33	U12	U13	U23
N2	0.0382 (9)	0.0534 (11)	0.0436 (10)	−0.0137 (8)	0.0099 (7)	−0.0026 (8)
N1	0.0372 (9)	0.0609 (11)	0.0446 (10)	−0.0163 (8)	0.0066 (7)	0.0080 (9)
C1	0.0439 (11)	0.0468 (12)	0.0357 (10)	−0.0134 (10)	0.0096 (8)	−0.0006 (9)
C13	0.0391 (10)	0.0537 (13)	0.0428 (11)	−0.0106 (10)	0.0101 (9)	0.0036 (11)
C12	0.0544 (13)	0.0597 (14)	0.0500 (13)	−0.0014 (12)	0.0161 (10)	0.0011 (12)
C7	0.0352 (10)	0.0470 (12)	0.0438 (11)	−0.0101 (10)	0.0125 (8)	0.0036 (10)
C6	0.0480 (12)	0.0532 (13)	0.0470 (12)	−0.0083 (11)	0.0113 (10)	−0.0035 (11)
C2	0.0461 (12)	0.0587 (14)	0.0564 (13)	−0.0081 (11)	0.0157 (10)	0.0069 (11)
C5	0.0705 (16)	0.0501 (14)	0.0523 (13)	−0.0041 (12)	0.0087 (11)	0.0069 (11)
C8	0.0512 (13)	0.0509 (13)	0.0713 (16)	−0.0074 (12)	0.0184 (12)	0.0017 (13)
C3	0.0574 (14)	0.0731 (16)	0.0640 (15)	−0.0158 (13)	0.0297 (12)	0.0068 (13)
C4	0.0806 (17)	0.0612 (16)	0.0540 (14)	−0.0189 (14)	0.0234 (12)	0.0076 (12)
C10	0.0544 (14)	0.102 (2)	0.0554 (16)	−0.0156 (16)	0.0024 (12)	0.0226 (16)
C9	0.0484 (13)	0.0676 (17)	0.098 (2)	0.0028 (13)	0.0116 (14)	0.0304 (16)
C11	0.0731 (16)	0.092 (2)	0.0463 (14)	−0.0098 (16)	0.0125 (12)	−0.0014 (14)

N2—C13	1.287 (2)	C2—C3	1.381 (3)
N2—N1	1.364 (2)	C2—H2	0.93
N1—C1	1.418 (2)	C5—C4	1.377 (3)
N1—C7	1.430 (2)	C5—H5	0.93
C1—C6	1.377 (3)	C8—C9	1.395 (3)
C1—C2	1.388 (3)	C8—H8	0.93
C13—C13i	1.429 (4)	C3—C4	1.367 (3)
C13—H13	0.93	C3—H3	0.93
C12—C7	1.373 (3)	C4—H4	0.93
C12—C11	1.373 (3)	C10—C11	1.354 (3)
C12—H12	0.93	C10—C9	1.377 (4)
C7—C8	1.368 (3)	C10—H10	0.93
C6—C5	1.384 (3)	C9—H9	0.93
C6—H6	0.93	C11—H11	0.93
C13—N2—N1	118.93 (16)	C4—C5—C6	120.3 (2)
N2—N1—C1	115.85 (16)	C4—C5—H5	119.9
N2—N1—C7	122.01 (14)	C6—C5—H5	119.9
C1—N1—C7	118.63 (15)	C7—C8—C9	118.9 (2)
C6—C1—C2	119.11 (19)	C7—C8—H8	120.5
C6—C1—N1	122.18 (18)	C9—C8—H8	120.5
C2—C1—N1	118.71 (19)	C4—C3—C2	120.8 (2)
N2—C13—C13i	119.0 (2)	C4—C3—H3	119.6
N2—C13—H13	120.5	C2—C3—H3	119.6
C13i—C13—H13	120.5	C3—C4—C5	119.5 (2)
C7—C12—C11	120.6 (2)	C3—C4—H4	120.2
C7—C12—H12	119.7	C5—C4—H4	120.2
C11—C12—H12	119.7	C11—C10—C9	120.2 (2)
C8—C7—C12	120.2 (2)	C11—C10—H10	119.9
C8—C7—N1	120.98 (19)	C9—C10—H10	119.9
C12—C7—N1	118.86 (19)	C10—C9—C8	120.1 (2)
C1—C6—C5	120.3 (2)	C10—C9—H9	119.9
C1—C6—H6	119.8	C8—C9—H9	119.9
C5—C6—H6	119.8	C10—C11—C12	119.9 (2)
C3—C2—C1	120.0 (2)	C10—C11—H11	120.1
C3—C2—H2	120	C12—C11—H11	120.1
C1—C2—H2	120
C13—N2—N1—C1	−173.48 (18)	N1—C1—C6—C5	−179.26 (18)
C13—N2—N1—C7	−14.9 (3)	C6—C1—C2—C3	−1.3 (3)
N2—N1—C1—C6	26.8 (3)	N1—C1—C2—C3	179.48 (18)
C7—N1—C1—C6	−132.5 (2)	C1—C6—C5—C4	−0.6 (3)
N2—N1—C1—C2	−154.06 (18)	C12—C7—C8—C9	−1.5 (3)
C7—N1—C1—C2	46.6 (3)	N1—C7—C8—C9	178.36 (18)
N1—N2—C13—C13i	−176.3 (2)	C1—C2—C3—C4	0.0 (3)
C11—C12—C7—C8	1.7 (3)	C2—C3—C4—C5	1.0 (4)
C11—C12—C7—N1	−178.09 (18)	C6—C5—C4—C3	−0.8 (3)
N2—N1—C7—C8	93.9 (2)	C11—C10—C9—C8	0.4 (4)
C1—N1—C7—C8	−108.1 (2)	C7—C8—C9—C10	0.4 (3)
N2—N1—C7—C12	−86.3 (2)	C9—C10—C11—C12	−0.1 (4)
C1—N1—C7—C12	71.7 (2)	C7—C12—C11—C10	−0.9 (3)
C2—C1—C6—C5	1.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg2ii	0.93	2.85	3.728 (3)	159
C8—H8···Cg1iii	0.93	2.88	3.785 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg2i	0.93	2.85	3.728 (3)	159
C8—H8⋯Cg1ii	0.93	2.88	3.785 (3)	164

Symmetry codes: (i) ; (ii) .