(E)-N′-[(5-Methyl­furan-2-yl)methyl­ene]­furan-2-carbohydrazide

In the title compound, C₁₁H₁₀N₂O₃, the dihedral angle between the two furan rings is 4.2 (2)°. Inter­molecular N—H...O and C—H...O hydrogen bonds link the mol­ecules into a two-dimensional network. Strong π–π stacking inter­actions are present between inversion-related furan rings, with a centroid-to-centroid distance of 3.4866 (14) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.126
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al.,2001). As part of an investigation of the coordination properties of Schiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).

In the molecular structure of the compound (I) (Fig. 1), the geometric parameters are normal. The O1/C2—C5 furan ring is planar, with an r.m.s. deviation for the fitted atoms of 0.004 Å, as is the furan ring O3/C8—C11, with an r.m.s. deviation of 0.003 Å. The dihedral angle between these two planes is 4.2 (2)°. The O2/C7/N2/N1/C6 plane (r.m.s. deviation 0.035 Å) forms dihedral angles of 3.1 (1)° and 5.1 (1)°, respectively, with the O1/C2—C5 and O3/C8—C11 furan rings.

Intermolecular N—H···O hydrogen bonds link the molecules into chains running along the b axis. These chains are cross-linked via C—H···O hydrogen bonds (Table 1) forming a two-dimensional network structure, as illustrated in Fig. 2. In addition, π-π stacking interactions involving the inversion-related O3/C8—C11 furan rings, with a centroid-to-centroid distance of 3.4866 (14) Å is observed.

Related literature

For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).

S2. Experimental

An anhydrous ethanol solution (50 ml) of 5-methylfuran-2-carbaldehyde (1.10 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of furan-2-carbohydrazide (1.26 g, 10 mmol), and the mixture was stirred at 350 K for 6 h under N₂, yielding a colourless precipitate. The product was isolated, recrystallized from anhydrous ethanol and then dried in vacuo to give pure compound (I) in 92% yield. Colourless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an anhydrous ethanol solution.

S3. Refinement

H atoms were included in calculated positions [N—H = 0.86 Å, C—H = 0.93 (aromatic) or 0.96 Å (methyl)] and refined using a riding model, with U_iso(H) = 1.2U_eq(C, N) or 1.5U_eq(C) for methyl H atoms.

Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of (I), viwed down the b axis. Hydrogen bonds are indicated by dashed lines.

(E)-N'-[(5-Methylfuran-2-yl)methylene]furan-2-carbohydrazide

Crystal data

C11H10N2O3	F(000) = 912
Mr = 218.21	Dx = 1.323 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8064 reflections
a = 11.402 (2) Å	θ = 1.8–27.4°
b = 7.9941 (16) Å	µ = 0.10 mm^−1
c = 24.039 (5) Å	T = 293 K
V = 2191.1 (7) Å^3	Block, colourless
Z = 8	0.14 × 0.10 × 0.06 mm

Data collection

Rigaku Saturn diffractometer	1931 independent reflections
Radiation source: rotating anode	1673 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.044
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.986, Tmax = 0.994	k = −9→8
12318 measured reflections	l = −28→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0628P)^2 + 0.3175P] where P = (Fo^2 + 2Fc^2)/3
1931 reflections	(Δ/σ)max = 0.001
146 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.82709 (12)	0.11965 (16)	0.75358 (5)	0.0600 (4)
O2	0.61482 (11)	0.07779 (15)	0.57388 (5)	0.0553 (4)
O3	0.67924 (12)	0.45165 (16)	0.49989 (5)	0.0633 (4)
N1	0.75995 (13)	0.22824 (19)	0.64816 (5)	0.0504 (4)
N2	0.73032 (13)	0.29844 (18)	0.59727 (5)	0.0506 (4)
H2	0.7579	0.3945	0.5878	0.061*
C1	0.8569 (2)	−0.0544 (4)	0.83485 (10)	0.1005 (9)
H1A	0.9007	−0.0553	0.8690	0.151*
H1B	0.8811	−0.1468	0.8120	0.151*
H1C	0.7748	−0.0642	0.8429	0.151*
C2	0.87878 (18)	0.1036 (3)	0.80507 (8)	0.0669 (6)
C3	0.9411 (2)	0.2403 (3)	0.81651 (9)	0.0780 (7)
H3	0.9849	0.2594	0.8485	0.094*
C4	0.9284 (2)	0.3510 (3)	0.77109 (9)	0.0749 (6)
H4	0.9612	0.4570	0.7677	0.090*
C5	0.85954 (16)	0.2732 (2)	0.73358 (7)	0.0550 (5)
C6	0.81970 (16)	0.3244 (2)	0.67981 (7)	0.0532 (5)
H6	0.8379	0.4315	0.6674	0.064*
C7	0.65803 (15)	0.2147 (2)	0.56285 (7)	0.0450 (4)
C8	0.63024 (15)	0.2980 (2)	0.51031 (7)	0.0480 (4)
C9	0.55807 (19)	0.2560 (3)	0.46885 (7)	0.0618 (5)
H9	0.5140	0.1585	0.4662	0.074*
C10	0.5615 (2)	0.3884 (3)	0.42979 (8)	0.0738 (6)
H10	0.5208	0.3943	0.3963	0.089*
C11	0.6341 (2)	0.5024 (3)	0.45028 (8)	0.0730 (6)
H11	0.6519	0.6034	0.4330	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0632 (8)	0.0663 (9)	0.0505 (8)	0.0005 (6)	−0.0081 (6)	0.0187 (6)
O2	0.0660 (8)	0.0460 (7)	0.0538 (8)	−0.0036 (6)	0.0003 (6)	0.0027 (5)
O3	0.0770 (9)	0.0610 (9)	0.0520 (8)	−0.0064 (7)	−0.0096 (6)	0.0144 (6)
N1	0.0594 (9)	0.0488 (9)	0.0431 (8)	0.0021 (7)	−0.0040 (7)	0.0120 (7)
N2	0.0634 (9)	0.0434 (8)	0.0449 (8)	−0.0035 (7)	−0.0054 (7)	0.0119 (6)
C1	0.0980 (18)	0.125 (2)	0.0788 (16)	0.0043 (16)	−0.0065 (14)	0.0576 (16)
C2	0.0590 (12)	0.0928 (16)	0.0490 (11)	0.0119 (11)	−0.0041 (9)	0.0228 (11)
C3	0.0727 (14)	0.112 (2)	0.0490 (12)	0.0048 (14)	−0.0152 (10)	0.0068 (12)
C4	0.0829 (15)	0.0836 (16)	0.0583 (13)	−0.0145 (12)	−0.0127 (11)	0.0051 (11)
C5	0.0606 (11)	0.0566 (11)	0.0479 (10)	−0.0004 (9)	−0.0040 (9)	0.0099 (8)
C6	0.0633 (11)	0.0492 (11)	0.0472 (10)	−0.0014 (9)	−0.0032 (9)	0.0069 (8)
C7	0.0503 (9)	0.0429 (10)	0.0420 (9)	0.0062 (8)	0.0050 (7)	0.0011 (7)
C8	0.0575 (10)	0.0445 (10)	0.0422 (9)	0.0057 (8)	0.0025 (8)	0.0008 (7)
C9	0.0807 (13)	0.0561 (12)	0.0487 (11)	0.0034 (10)	−0.0073 (10)	−0.0061 (8)
C10	0.1039 (17)	0.0730 (14)	0.0445 (11)	0.0125 (13)	−0.0174 (11)	−0.0015 (10)
C11	0.1045 (18)	0.0669 (14)	0.0477 (11)	0.0048 (13)	−0.0100 (11)	0.0181 (10)

Geometric parameters (Å, º)

O1—C5	1.369 (2)	C3—C4	1.413 (3)
O1—C2	1.377 (2)	C3—H3	0.93
O2—C7	1.229 (2)	C4—C5	1.347 (3)
O3—C11	1.361 (2)	C4—H4	0.93
O3—C8	1.372 (2)	C5—C6	1.430 (2)
N1—C6	1.278 (2)	C6—H6	0.93
N1—N2	1.3876 (18)	C7—C8	1.463 (2)
N2—C7	1.346 (2)	C8—C9	1.335 (2)
N2—H2	0.86	C9—C10	1.415 (3)
C1—C2	1.473 (3)	C9—H9	0.93
C1—H1A	0.96	C10—C11	1.326 (3)
C1—H1B	0.96	C10—H10	0.93
C1—H1C	0.96	C11—H11	0.93
C2—C3	1.332 (3)
C5—O1—C2	106.47 (16)	C4—C5—O1	109.64 (17)
C11—O3—C8	105.83 (15)	C4—C5—C6	131.16 (19)
C6—N1—N2	114.29 (15)	O1—C5—C6	119.21 (16)
C7—N2—N1	119.33 (15)	N1—C6—C5	122.38 (17)
C7—N2—H2	120.3	N1—C6—H6	118.8
N1—N2—H2	120.3	C5—C6—H6	118.8
C2—C1—H1A	109.5	O2—C7—N2	123.75 (15)
C2—C1—H1B	109.5	O2—C7—C8	120.33 (16)
H1A—C1—H1B	109.5	N2—C7—C8	115.91 (16)
C2—C1—H1C	109.5	C9—C8—O3	109.85 (16)
H1A—C1—H1C	109.5	C9—C8—C7	131.57 (18)
H1B—C1—H1C	109.5	O3—C8—C7	118.48 (15)
C3—C2—O1	109.71 (18)	C8—C9—C10	106.88 (19)
C3—C2—C1	133.9 (2)	C8—C9—H9	126.6
O1—C2—C1	116.4 (2)	C10—C9—H9	126.6
C2—C3—C4	107.44 (19)	C11—C10—C9	106.52 (18)
C2—C3—H3	126.3	C11—C10—H10	126.7
C4—C3—H3	126.3	C9—C10—H10	126.7
C5—C4—C3	106.7 (2)	C10—C11—O3	110.90 (19)
C5—C4—H4	126.6	C10—C11—H11	124.5
C3—C4—H4	126.6	O3—C11—H11	124.5
C6—N1—N2—C7	−173.65 (15)	N1—N2—C7—O2	0.6 (3)
C5—O1—C2—C3	−0.3 (2)	N1—N2—C7—C8	179.41 (14)
C5—O1—C2—C1	−179.49 (19)	C11—O3—C8—C9	0.0 (2)
O1—C2—C3—C4	0.8 (3)	C11—O3—C8—C7	−176.96 (16)
C1—C2—C3—C4	179.8 (3)	O2—C7—C8—C9	3.0 (3)
C2—C3—C4—C5	−1.0 (3)	N2—C7—C8—C9	−175.80 (18)
C3—C4—C5—O1	0.8 (3)	O2—C7—C8—O3	179.23 (15)
C3—C4—C5—C6	−178.7 (2)	N2—C7—C8—O3	0.4 (2)
C2—O1—C5—C4	−0.3 (2)	O3—C8—C9—C10	0.4 (2)
C2—O1—C5—C6	179.21 (17)	C7—C8—C9—C10	176.85 (19)
N2—N1—C6—C5	−179.21 (16)	C8—C9—C10—C11	−0.7 (3)
C4—C5—C6—N1	175.4 (2)	C9—C10—C11—O3	0.7 (3)
O1—C5—C6—N1	−4.0 (3)	C8—O3—C11—C10	−0.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2^i	0.86	2.09	2.902 (2)	157
C9—H9···O2^ii	0.93	2.58	3.473 (3)	161

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+1, −y, −z+1.