1,2-Bis(2-furylmethyl-ene)hydrazine.

Crystals of the title compound, C(10)H(8)N(2)O(2), were obtained from a condensation reaction of hydrazine hydrate with furfural. In the crystal structure, the mol-ecule is centrosymmetric and almost planar and the furan rings are parallel by symmetry.

Related literature

For background, see: Casellato & Vigato (1977 ▶); For related structures, see: Fan et al. (2008 ▶); Shan et al. (2004 ▶); Shan, Tian et al. (2008 ▶); Shan, Wang et al. (2008 ▶).

Experimental

Crystal data

C10H8N2O2

M = 188.18

Orthorhombic,

a = 6.877 (2) Å

b = 8.996 (3) Å

c = 15.171 (4) Å

V = 938.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.50 × 0.40 × 0.40 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.954, T max = 0.963

4129 measured reflections

829 independent reflections

677 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.05

829 reflections

65 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030729/hb2802sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030729/hb2802Isup2.hkl

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

C10H8N2O2	F(000) = 392
Mr = 188.18	Dx = 1.332 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5207 reflections
a = 6.877 (2) Å	θ = 2.6–25.3°
b = 8.996 (3) Å	µ = 0.10 mm−1
c = 15.171 (4) Å	T = 298 K
V = 938.6 (5) Å3	Block, yellow
Z = 4	0.50 × 0.40 × 0.40 mm

Bruker SMART 1K CCD diffractometer	829 independent reflections
Radiation source: fine-focus sealed tube	677 reflections with I > 2σ(I)
graphite	Rint = 0.081
ω scans	θmax = 25.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −8→8
Tmin = 0.954, Tmax = 0.963	k = −10→10
4129 measured reflections	l = −18→9

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0662P)2] where P = (Fo2 + 2Fc2)/3
829 reflections	(Δ/σ)max < 0.001
65 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.25 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
C1	−0.0467 (2)	0.88870 (18)	0.18436 (11)	0.0736 (5)
H1	−0.0937	0.8074	0.2157	0.088*
C2	−0.1336 (2)	1.01970 (19)	0.18094 (10)	0.0719 (5)
H2	−0.2492	1.0466	0.2084	0.086*
C3	−0.0168 (2)	1.10963 (17)	0.12769 (10)	0.0642 (5)
H3	−0.0400	1.2085	0.1131	0.077*
C4	0.13456 (19)	1.02755 (14)	0.10149 (8)	0.0529 (4)
C5	0.2964 (2)	1.06191 (15)	0.04628 (9)	0.0566 (4)
H5	0.3049	1.1570	0.0225	0.068*
N1	0.42950 (18)	0.96866 (13)	0.02805 (8)	0.0613 (4)
O1	0.12017 (16)	0.88799 (10)	0.13632 (7)	0.0669 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0695 (10)	0.0698 (11)	0.0815 (11)	−0.0135 (8)	0.0114 (9)	0.0137 (8)
C2	0.0637 (10)	0.0800 (12)	0.0721 (11)	0.0049 (8)	0.0084 (7)	0.0085 (8)
C3	0.0722 (11)	0.0589 (10)	0.0616 (9)	0.0093 (7)	0.0038 (7)	0.0082 (7)
C4	0.0639 (9)	0.0452 (8)	0.0496 (7)	−0.0049 (6)	−0.0044 (6)	0.0007 (6)
C5	0.0690 (10)	0.0485 (8)	0.0522 (8)	−0.0055 (7)	0.0007 (7)	0.0013 (6)
N1	0.0649 (8)	0.0541 (8)	0.0649 (8)	−0.0033 (6)	0.0084 (5)	0.0045 (5)
O1	0.0698 (8)	0.0479 (7)	0.0830 (8)	−0.0029 (5)	0.0078 (5)	0.0057 (4)

C1—C2	1.322 (2)	C3—H3	0.9300
C1—O1	1.359 (2)	C4—O1	1.3657 (16)
C1—H1	0.9300	C4—C5	1.427 (2)
C2—C3	1.397 (2)	C5—N1	1.2721 (18)
C2—H2	0.9300	C5—H5	0.9300
C3—C4	1.3364 (19)	N1—N1i	1.408 (2)
C2—C1—O1	111.39 (14)	C3—C4—O1	109.66 (12)
C2—C1—H1	124.3	C3—C4—C5	131.47 (13)
O1—C1—H1	124.3	O1—C4—C5	118.87 (12)
C1—C2—C3	106.18 (15)	N1—C5—C4	123.10 (13)
C1—C2—H2	126.9	N1—C5—H5	118.4
C3—C2—H2	126.9	C4—C5—H5	118.4
C4—C3—C2	107.45 (14)	C5—N1—N1i	111.29 (15)
C4—C3—H3	126.3	C1—O1—C4	105.32 (12)
C2—C3—H3	126.3
O1—C1—C2—C3	−0.05 (19)	O1—C4—C5—N1	−0.4 (2)
C1—C2—C3—C4	0.23 (18)	C4—C5—N1—N1i	179.64 (14)
C2—C3—C4—O1	−0.32 (17)	C2—C1—O1—C4	−0.14 (18)
C2—C3—C4—C5	179.42 (15)	C3—C4—O1—C1	0.29 (16)
C3—C4—C5—N1	179.91 (15)	C5—C4—O1—C1	−179.49 (12)