organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1,2-Bis[4-(1H-imidazol-1-yl)benzyl­­idene]hydrazine

aState Key Lab. Base of Novel Functional Materials and Preparation Science, Institute of Solid Materials Chemistry, Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, People's Republic of China
*Correspondence e-mail: leikeweipublic@hotmail.com

(Received 7 May 2012; accepted 19 May 2012; online 31 May 2012)

The title compound, C20H16N6, 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[Chen, C. L., Goforth, A. M., Smith, M. D., Su, C. Y. & Loye, H. C. (2005). Inorg. Chem. 44, 8762-8769.]).

[Scheme 1]

Experimental

Crystal data
  • C20H16N6

  • Mr = 340.39

  • Monoclinic, P 21 /n

  • 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)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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) [-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The molecular structure of the title compound is illustrated in Fig. 1. The molecular structures is central symmetry. The bond lengths and bond angles in are within normal ranges. The N3—N3 bond length of 1.423 (3)%A is a slightly smaller than the normal length. The N3—C10 bond length is 1.273 (2)%A. The dihedral angle between the imidazole and benzene rings is 28.03 (6) Å

Related literature top

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

Experimental top

Hydrazine monohydrate (20 mmol, 1.08 g) and 4-imidazole benzaldehyde (40 mmol, 6.88 g) were dissolved in ethanol and the solution was refluxed for 2 h. After evaporation, a crude product was recrystallized twice from DMF and methanol to give a pure pale yellow product (Chen et al., 2005). Yield: 85.2%. Calcd. for C20H20N6: C, 69.75; H, 5.85; N, 24.40; Found: C, 69.88; H, 5.73; N, 24.67%.

Refinement top

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms (C—H = 0.93 Å) and Uiso(H) values equal to 1.2Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
1,2-Bis[4-(1H-imidazol-1-yl)benzylidene]hydrazine top
Crystal data top
C20H16N6F(000) = 356
Mr = 340.39Dx = 1.345 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7835 reflections
a = 8.1342 (3) Åθ = 2.9–26.4°
b = 7.8172 (3) ŵ = 0.09 mm1
c = 13.2191 (6) ÅT = 293 K
β = 90.259 (4)°Block, yellow
V = 840.55 (6) Å30.44 × 0.20 × 0.15 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1249 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 26.4°, θmin = 2.9°
Detector resolution: 0 pixels mm-1h = 108
ω scansk = 99
4180 measured reflectionsl = 1516
1695 independent 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-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 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C20H16N6V = 840.55 (6) Å3
Mr = 340.39Z = 2
Monoclinic, P21/nMo Kα radiation
a = 8.1342 (3) ŵ = 0.09 mm1
b = 7.8172 (3) ÅT = 293 K
c = 13.2191 (6) Å0.44 × 0.20 × 0.15 mm
β = 90.259 (4)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1249 reflections with I > 2σ(I)
4180 measured reflectionsRint = 0.022
1695 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.13Δρmax = 0.12 e Å3
1695 reflectionsΔρmin = 0.17 e Å3
118 parameters
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
N10.03400 (17)0.26891 (18)0.65029 (11)0.0443 (4)
N20.1631 (2)0.1350 (2)0.73547 (13)0.0605 (5)
N30.44959 (19)0.9458 (2)0.52999 (13)0.0559 (5)
C10.0938 (2)0.2826 (2)0.71607 (15)0.0529 (5)
H10.12810.38560.74420.063*
C20.0742 (2)0.0193 (3)0.67959 (16)0.0610 (6)
H20.09410.09780.67830.073*
C30.0454 (2)0.0977 (2)0.62695 (16)0.0555 (5)
H30.12060.04650.58360.067*
C40.1305 (2)0.4043 (2)0.61009 (13)0.0409 (4)
C50.1995 (2)0.3884 (2)0.51484 (14)0.0471 (5)
H50.18380.28880.47750.057*
C60.2917 (2)0.5209 (2)0.47552 (15)0.0497 (5)
H60.33850.50910.41180.060*
C70.3157 (2)0.6717 (2)0.52950 (14)0.0447 (5)
C80.2452 (2)0.6857 (2)0.62521 (15)0.0490 (5)
H80.25950.78570.66230.059*
C90.1546 (2)0.5532 (2)0.66558 (14)0.0481 (5)
H90.10970.56350.72990.058*
C100.4159 (2)0.8068 (2)0.48435 (16)0.0516 (5)
H100.45670.79030.41950.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0431 (8)0.0387 (8)0.0513 (9)0.0015 (6)0.0069 (7)0.0030 (7)
N20.0615 (11)0.0520 (10)0.0681 (12)0.0074 (8)0.0195 (9)0.0048 (8)
N30.0572 (10)0.0453 (9)0.0653 (11)0.0046 (8)0.0160 (8)0.0124 (8)
C10.0528 (11)0.0464 (10)0.0597 (13)0.0007 (8)0.0150 (10)0.0014 (9)
C20.0690 (14)0.0436 (11)0.0705 (15)0.0099 (10)0.0131 (11)0.0013 (10)
C30.0615 (12)0.0402 (10)0.0650 (13)0.0000 (9)0.0147 (10)0.0029 (9)
C40.0393 (9)0.0370 (9)0.0465 (11)0.0018 (7)0.0028 (8)0.0040 (7)
C50.0493 (11)0.0424 (10)0.0497 (11)0.0009 (8)0.0063 (9)0.0022 (8)
C60.0510 (11)0.0492 (11)0.0490 (12)0.0041 (8)0.0106 (9)0.0033 (8)
C70.0402 (10)0.0433 (10)0.0504 (11)0.0031 (8)0.0032 (8)0.0099 (8)
C80.0543 (11)0.0374 (9)0.0553 (12)0.0006 (8)0.0044 (9)0.0001 (8)
C90.0554 (12)0.0434 (10)0.0455 (11)0.0004 (8)0.0101 (9)0.0008 (8)
C100.0495 (11)0.0465 (11)0.0590 (13)0.0030 (8)0.0087 (10)0.0129 (9)
Geometric parameters (Å, º) top
N1—C11.362 (2)C4—C91.389 (2)
N1—C31.377 (2)C5—C61.382 (2)
N1—C41.422 (2)C5—H50.9300
N2—C11.311 (2)C6—C71.391 (3)
N2—C21.375 (3)C6—H60.9300
N3—C101.273 (2)C7—C81.396 (3)
N3—N3i1.423 (3)C7—C101.463 (2)
C1—H10.9300C8—C91.380 (2)
C2—C31.346 (3)C8—H80.9300
C2—H20.9300C9—H90.9300
C3—H30.9300C10—H100.9300
C4—C51.386 (2)
C1—N1—C3105.79 (15)C6—C5—H5120.1
C1—N1—C4127.14 (15)C4—C5—H5120.1
C3—N1—C4127.01 (16)C5—C6—C7121.14 (18)
C1—N2—C2104.24 (17)C5—C6—H6119.4
C10—N3—N3i111.6 (2)C7—C6—H6119.4
N2—C1—N1112.69 (17)C6—C7—C8118.32 (16)
N2—C1—H1123.7C6—C7—C10118.64 (18)
N1—C1—H1123.7C8—C7—C10123.03 (18)
C3—C2—N2111.20 (18)C9—C8—C7120.93 (17)
C3—C2—H2124.4C9—C8—H8119.5
N2—C2—H2124.4C7—C8—H8119.5
C2—C3—N1106.07 (18)C8—C9—C4119.92 (18)
C2—C3—H3127.0C8—C9—H9120.0
N1—C3—H3127.0C4—C9—H9120.0
C5—C4—C9119.88 (16)N3—C10—C7122.85 (19)
C5—C4—N1119.93 (16)N3—C10—H10118.6
C9—C4—N1120.19 (16)C7—C10—H10118.6
C6—C5—C4119.80 (17)
C2—N2—C1—N10.5 (2)N1—C4—C5—C6179.29 (15)
C3—N1—C1—N20.2 (2)C4—C5—C6—C70.6 (3)
C4—N1—C1—N2177.01 (17)C5—C6—C7—C80.5 (3)
C1—N2—C2—C30.6 (2)C5—C6—C7—C10179.37 (16)
N2—C2—C3—N10.5 (2)C6—C7—C8—C90.3 (3)
C1—N1—C3—C20.2 (2)C10—C7—C8—C9178.54 (16)
C4—N1—C3—C2177.38 (16)C7—C8—C9—C41.0 (3)
C1—N1—C4—C5150.06 (18)C5—C4—C9—C80.9 (3)
C3—N1—C4—C526.6 (3)N1—C4—C9—C8178.52 (16)
C1—N1—C4—C929.3 (3)N3i—N3—C10—C7179.27 (17)
C3—N1—C4—C9154.04 (18)C6—C7—C10—N3177.13 (17)
C9—C4—C5—C60.1 (3)C8—C7—C10—N31.7 (3)
Symmetry code: (i) x+1, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···N2ii0.932.603.453 (2)153
C6—H6···N2iii0.932.593.421 (3)149
Symmetry codes: (ii) x1/2, y+1/2, z+3/2; (iii) x+1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC20H16N6
Mr340.39
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)8.1342 (3), 7.8172 (3), 13.2191 (6)
β (°) 90.259 (4)
V3)840.55 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.44 × 0.20 × 0.15
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4180, 1695, 1249
Rint0.022
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.143, 1.13
No. of reflections1695
No. of parameters118
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.12, 0.17

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···N2i0.932.603.453 (2)153
C6—H6···N2ii0.932.593.421 (3)149
Symmetry codes: (i) x1/2, y+1/2, z+3/2; (ii) x+1/2, y+1/2, z1/2.
 

Acknowledgements

This project was sponsored by the K. C. Wong Magna Fund in Ningbo University, the Talent Fund of Ningbo Municipal Natural Science Foundation (No. 2010 A610187) and the Talent Fund of Ningbo University, China (No. Xkl09070).

References

First citationChen, C. L., Goforth, A. M., Smith, M. D., Su, C. Y. & Loye, H. C. (2005). Inorg. Chem. 44, 8762–8769.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2004). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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