N'-[(E)-(5-Methyl-furan-2-yl)methyl-idene]formohydrazide.

The title compound, C(7)H(8)N(2)O(2), is almost planar (r.m.s. deviation for non-H atoms = 0.029 Å). In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate an R(2) (2)(8) ring motif.

Related literature

For related structures, see: Shafiq et al. (2009 ▶); Bai & Jing (2007 ▶); Yao & Jing (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H8N2O2

M = 152.15

Orthorhombic,

a = 10.6433 (14) Å

b = 6.7762 (8) Å

c = 21.129 (3) Å

V = 1523.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.25 × 0.15 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.985, T max = 0.988

7485 measured reflections

1403 independent reflections

655 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.108

S = 1.00

1403 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037064/hb5099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037064/hb5099Isup2.hkl

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

C7H8N2O2	F(000) = 640
Mr = 152.15	Dx = 1.326 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1864 reflections
a = 10.6433 (14) Å	θ = 2.7–25.5°
b = 6.7762 (8) Å	µ = 0.10 mm−1
c = 21.129 (3) Å	T = 296 K
V = 1523.9 (3) Å3	Cut needle, brown
Z = 8	0.25 × 0.15 × 0.13 mm

Bruker Kappa APEXII CCD diffractometer	1403 independent reflections
Radiation source: fine-focus sealed tube	655 reflections with I > 2σ(I)
graphite	Rint = 0.072
Detector resolution: 7.80 pixels mm-1	θmax = 25.5°, θmin = 2.7°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→8
Tmin = 0.985, Tmax = 0.988	l = −23→25
7485 measured 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0376P)2] where P = (Fo2 + 2Fc2)/3
1403 reflections	(Δ/σ)max < 0.001
101 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.56771 (16)	0.2958 (2)	0.15544 (8)	0.0550 (7)
O2	0.66434 (16)	1.0759 (3)	0.01153 (9)	0.0665 (8)
N1	0.5699 (2)	0.6414 (3)	0.08604 (10)	0.0486 (8)
N2	0.56384 (19)	0.8059 (3)	0.04784 (10)	0.0497 (8)
C1	0.5376 (3)	0.1184 (4)	0.18332 (14)	0.0602 (11)
C2	0.4218 (3)	0.0664 (4)	0.16579 (15)	0.0717 (14)
C3	0.3762 (3)	0.2130 (4)	0.12461 (15)	0.0641 (11)
C4	0.4667 (2)	0.3504 (4)	0.11942 (12)	0.0481 (10)
C5	0.4735 (2)	0.5290 (4)	0.08350 (13)	0.0501 (10)
C6	0.6618 (2)	0.9277 (4)	0.04483 (14)	0.0542 (11)
C7	0.6371 (3)	0.0296 (4)	0.22318 (15)	0.0950 (16)
H2	0.37892	−0.04640	0.17850	0.0858*
H2A	0.49724	0.82967	0.02609	0.0596*
H3	0.29823	0.21455	0.10475	0.0770*
H5	0.40630	0.56423	0.05772	0.0599*
H6	0.73203	0.89887	0.06930	0.0651*
H7A	0.61090	−0.09910	0.23690	0.1421*
H7B	0.71316	0.01834	0.19904	0.1421*
H7C	0.65168	0.11181	0.25943	0.1421*

	U11	U22	U33	U12	U13	U23
O1	0.0546 (12)	0.0537 (12)	0.0566 (13)	−0.0005 (9)	0.0025 (11)	0.0096 (10)
O2	0.0620 (14)	0.0531 (12)	0.0845 (17)	−0.0070 (9)	−0.0148 (11)	0.0163 (11)
N1	0.0461 (14)	0.0486 (13)	0.0510 (16)	0.0081 (12)	0.0010 (12)	0.0037 (12)
N2	0.0408 (13)	0.0512 (13)	0.0570 (16)	0.0048 (12)	−0.0071 (12)	0.0094 (12)
C1	0.074 (2)	0.0447 (18)	0.062 (2)	0.0016 (16)	0.0148 (19)	0.0060 (16)
C2	0.080 (2)	0.054 (2)	0.081 (3)	−0.0146 (18)	0.025 (2)	−0.0025 (17)
C3	0.0533 (19)	0.068 (2)	0.071 (2)	−0.0095 (17)	0.0073 (17)	−0.0096 (18)
C4	0.0415 (16)	0.0546 (19)	0.0483 (19)	0.0013 (15)	0.0047 (14)	−0.0011 (15)
C5	0.0416 (16)	0.0567 (18)	0.052 (2)	0.0088 (14)	−0.0007 (14)	0.0003 (15)
C6	0.0454 (18)	0.0562 (18)	0.061 (2)	0.0042 (15)	−0.0088 (16)	−0.0033 (17)
C7	0.116 (3)	0.081 (2)	0.088 (3)	0.018 (2)	−0.004 (2)	0.031 (2)

O1—C1	1.377 (3)	C3—C4	1.344 (4)
O1—C4	1.368 (3)	C4—C5	1.430 (4)
O2—C6	1.227 (3)	C2—H2	0.9300
N1—N2	1.378 (3)	C3—H3	0.9300
N1—C5	1.279 (3)	C5—H5	0.9300
N2—C6	1.331 (3)	C6—H6	0.9300
N2—H2A	0.8600	C7—H7A	0.9600
C1—C2	1.334 (4)	C7—H7B	0.9600
C1—C7	1.481 (4)	C7—H7C	0.9600
C2—C3	1.407 (4)
O1···N1	2.763 (3)	C6···N1i	3.318 (3)
O2···N1i	3.268 (3)	C6···C1iv	3.461 (4)
O2···N2ii	2.848 (3)	C6···O2iii	3.099 (3)
O2···C6i	3.099 (3)	C1···H7Avii	3.0000
O1···H6iii	2.8900	C2···H7Avii	3.0800
O2···H2Aii	2.0000	C6···H2Aii	2.8000
O2···H6i	2.7400	H2A···H5	2.1500
N1···O1	2.763 (3)	H2A···O2ii	2.0000
N1···O2iii	3.268 (3)	H2A···C6ii	2.8000
N1···C6iii	3.318 (3)	H2A···H2Aii	2.5600
N2···C2iv	3.408 (4)	H5···H2A	2.1500
N2···O2ii	2.848 (3)	H6···O1i	2.8900
N1···H6iii	2.7000	H6···O2iii	2.7400
C1···C6v	3.461 (4)	H6···N1i	2.7000
C2···N2v	3.408 (4)	H7A···C1viii	3.0000
C5···C5vi	3.595 (4)	H7A···C2viii	3.0800
C1—O1—C4	106.9 (2)	C1—C2—H2	126.00
N2—N1—C5	114.8 (2)	C3—C2—H2	126.00
N1—N2—C6	119.5 (2)	C2—C3—H3	127.00
N1—N2—H2A	120.00	C4—C3—H3	127.00
C6—N2—H2A	120.00	N1—C5—H5	119.00
C2—C1—C7	135.3 (3)	C4—C5—H5	119.00
O1—C1—C2	109.1 (2)	O2—C6—H6	118.00
O1—C1—C7	115.6 (2)	N2—C6—H6	118.00
C1—C2—C3	107.7 (3)	C1—C7—H7A	109.00
C2—C3—C4	107.0 (3)	C1—C7—H7B	109.00
O1—C4—C5	119.0 (2)	C1—C7—H7C	109.00
O1—C4—C3	109.3 (2)	H7A—C7—H7B	109.00
C3—C4—C5	131.7 (2)	H7A—C7—H7C	109.00
N1—C5—C4	121.5 (2)	H7B—C7—H7C	110.00
O2—C6—N2	123.5 (2)
C4—O1—C1—C2	−0.7 (3)	O1—C1—C2—C3	0.9 (3)
C4—O1—C1—C7	178.2 (2)	C7—C1—C2—C3	−177.7 (3)
C1—O1—C4—C3	0.2 (3)	C1—C2—C3—C4	−0.7 (4)
C1—O1—C4—C5	−178.5 (2)	C2—C3—C4—O1	0.3 (3)
C5—N1—N2—C6	−177.0 (2)	C2—C3—C4—C5	178.8 (3)
N2—N1—C5—C4	178.7 (2)	O1—C4—C5—N1	−2.4 (4)
N1—N2—C6—O2	179.2 (2)	C3—C4—C5—N1	179.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ii	0.86	2.00	2.848 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	2.00	2.848 (3)	169

Symmetry code: (i) .