1,2-Bis[4-(1H-imidazol-1-yl)benzyl-idene]hydrazine.

The title compound, C(20)H(16)N(6), is centrosymmetric with the mid-point of the N-N bond located on an inversion center. The imidazole ring is oriented at a dihedral angle of 28.03 (6)° with respect to the attached benzene ring. In the crystal, molecules are linked via C-H⋯N interactions.

Related literature

For a related compound, see: Chen et al. (2005 ▶).

Experimental

Crystal data

C20H16N6

M = 340.39

Monoclinic,

a = 8.1342 (3) Å

b = 7.8172 (3) Å

c = 13.2191 (6) Å

β = 90.259 (4)°

V = 840.55 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.44 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

4180 measured reflections

1695 independent reflections

1249 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.143

S = 1.13

1695 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.17 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202291X/xu5536sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202291X/xu5536Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202291X/xu5536Isup3.cml

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

C20H16N6	F(000) = 356
Mr = 340.39	Dx = 1.345 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7835 reflections
a = 8.1342 (3) Å	θ = 2.9–26.4°
b = 7.8172 (3) Å	µ = 0.09 mm−1
c = 13.2191 (6) Å	T = 293 K
β = 90.259 (4)°	Block, yellow
V = 840.55 (6) Å3	0.44 × 0.20 × 0.15 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	1249 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 26.4°, θmin = 2.9°
Detector resolution: 0 pixels mm-1	h = −10→8
ω scans	k = −9→9
4180 measured reflections	l = −15→16
1695 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.0922P] where P = (Fo2 + 2Fc2)/3
1695 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.03400 (17)	0.26891 (18)	0.65029 (11)	0.0443 (4)
N2	−0.1631 (2)	0.1350 (2)	0.73547 (13)	0.0605 (5)
N3	0.44959 (19)	0.9458 (2)	0.52999 (13)	0.0559 (5)
C1	−0.0938 (2)	0.2826 (2)	0.71607 (15)	0.0529 (5)
H1	−0.1281	0.3856	0.7442	0.063*
C2	−0.0742 (2)	0.0193 (3)	0.67959 (16)	0.0610 (6)
H2	−0.0941	−0.0978	0.6783	0.073*
C3	0.0454 (2)	0.0977 (2)	0.62695 (16)	0.0555 (5)
H3	0.1206	0.0465	0.5836	0.067*
C4	0.1305 (2)	0.4043 (2)	0.61009 (13)	0.0409 (4)
C5	0.1995 (2)	0.3884 (2)	0.51484 (14)	0.0471 (5)
H5	0.1838	0.2888	0.4775	0.057*
C6	0.2917 (2)	0.5209 (2)	0.47552 (15)	0.0497 (5)
H6	0.3385	0.5091	0.4118	0.060*
C7	0.3157 (2)	0.6717 (2)	0.52950 (14)	0.0447 (5)
C8	0.2452 (2)	0.6857 (2)	0.62521 (15)	0.0490 (5)
H8	0.2595	0.7857	0.6623	0.059*
C9	0.1546 (2)	0.5532 (2)	0.66558 (14)	0.0481 (5)
H9	0.1097	0.5635	0.7299	0.058*
C10	0.4159 (2)	0.8068 (2)	0.48435 (16)	0.0516 (5)
H10	0.4567	0.7903	0.4195	0.062*

	U11	U22	U33	U12	U13	U23
N1	0.0431 (8)	0.0387 (8)	0.0513 (9)	0.0015 (6)	0.0069 (7)	0.0030 (7)
N2	0.0615 (11)	0.0520 (10)	0.0681 (12)	−0.0074 (8)	0.0195 (9)	0.0048 (8)
N3	0.0572 (10)	0.0453 (9)	0.0653 (11)	−0.0046 (8)	0.0160 (8)	0.0124 (8)
C1	0.0528 (11)	0.0464 (10)	0.0597 (13)	0.0007 (8)	0.0150 (10)	0.0014 (9)
C2	0.0690 (14)	0.0436 (11)	0.0705 (15)	−0.0099 (10)	0.0131 (11)	0.0013 (10)
C3	0.0615 (12)	0.0402 (10)	0.0650 (13)	0.0000 (9)	0.0147 (10)	−0.0029 (9)
C4	0.0393 (9)	0.0370 (9)	0.0465 (11)	0.0018 (7)	0.0028 (8)	0.0040 (7)
C5	0.0493 (11)	0.0424 (10)	0.0497 (11)	0.0009 (8)	0.0063 (9)	−0.0022 (8)
C6	0.0510 (11)	0.0492 (11)	0.0490 (12)	0.0041 (8)	0.0106 (9)	0.0033 (8)
C7	0.0402 (10)	0.0433 (10)	0.0504 (11)	0.0031 (8)	0.0032 (8)	0.0099 (8)
C8	0.0543 (11)	0.0374 (9)	0.0553 (12)	−0.0006 (8)	0.0044 (9)	−0.0001 (8)
C9	0.0554 (12)	0.0434 (10)	0.0455 (11)	−0.0004 (8)	0.0101 (9)	0.0008 (8)
C10	0.0495 (11)	0.0465 (11)	0.0590 (13)	0.0030 (8)	0.0087 (10)	0.0129 (9)

N1—C1	1.362 (2)	C4—C9	1.389 (2)
N1—C3	1.377 (2)	C5—C6	1.382 (2)
N1—C4	1.422 (2)	C5—H5	0.9300
N2—C1	1.311 (2)	C6—C7	1.391 (3)
N2—C2	1.375 (3)	C6—H6	0.9300
N3—C10	1.273 (2)	C7—C8	1.396 (3)
N3—N3i	1.423 (3)	C7—C10	1.463 (2)
C1—H1	0.9300	C8—C9	1.380 (2)
C2—C3	1.346 (3)	C8—H8	0.9300
C2—H2	0.9300	C9—H9	0.9300
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.386 (2)
C1—N1—C3	105.79 (15)	C6—C5—H5	120.1
C1—N1—C4	127.14 (15)	C4—C5—H5	120.1
C3—N1—C4	127.01 (16)	C5—C6—C7	121.14 (18)
C1—N2—C2	104.24 (17)	C5—C6—H6	119.4
C10—N3—N3i	111.6 (2)	C7—C6—H6	119.4
N2—C1—N1	112.69 (17)	C6—C7—C8	118.32 (16)
N2—C1—H1	123.7	C6—C7—C10	118.64 (18)
N1—C1—H1	123.7	C8—C7—C10	123.03 (18)
C3—C2—N2	111.20 (18)	C9—C8—C7	120.93 (17)
C3—C2—H2	124.4	C9—C8—H8	119.5
N2—C2—H2	124.4	C7—C8—H8	119.5
C2—C3—N1	106.07 (18)	C8—C9—C4	119.92 (18)
C2—C3—H3	127.0	C8—C9—H9	120.0
N1—C3—H3	127.0	C4—C9—H9	120.0
C5—C4—C9	119.88 (16)	N3—C10—C7	122.85 (19)
C5—C4—N1	119.93 (16)	N3—C10—H10	118.6
C9—C4—N1	120.19 (16)	C7—C10—H10	118.6
C6—C5—C4	119.80 (17)
C2—N2—C1—N1	0.5 (2)	N1—C4—C5—C6	179.29 (15)
C3—N1—C1—N2	−0.2 (2)	C4—C5—C6—C7	−0.6 (3)
C4—N1—C1—N2	177.01 (17)	C5—C6—C7—C8	0.5 (3)
C1—N2—C2—C3	−0.6 (2)	C5—C6—C7—C10	179.37 (16)
N2—C2—C3—N1	0.5 (2)	C6—C7—C8—C9	0.3 (3)
C1—N1—C3—C2	−0.2 (2)	C10—C7—C8—C9	−178.54 (16)
C4—N1—C3—C2	−177.38 (16)	C7—C8—C9—C4	−1.0 (3)
C1—N1—C4—C5	−150.06 (18)	C5—C4—C9—C8	0.9 (3)
C3—N1—C4—C5	26.6 (3)	N1—C4—C9—C8	−178.52 (16)
C1—N1—C4—C9	29.3 (3)	N3i—N3—C10—C7	179.27 (17)
C3—N1—C4—C9	−154.04 (18)	C6—C7—C10—N3	−177.13 (17)
C9—C4—C5—C6	−0.1 (3)	C8—C7—C10—N3	1.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N2ii	0.93	2.60	3.453 (2)	153
C6—H6···N2iii	0.93	2.59	3.421 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N2i	0.93	2.60	3.453 (2)	153
C6—H6⋯N2ii	0.93	2.59	3.421 (3)	149

Symmetry codes: (i) ; (ii) .