N′-[(5-Methyl­furan-2-yl)methyl­ene]isonicotinohydrazide

Liu, L.; Jian, F.-F.

doi:10.1107/S1600536808037276

organic compounds

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Volume 64| Part 12| December 2008| Page o2370

doi:10.1107/S1600536808037276

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N′-[(5-Methylfuran-2-yl)methylene]isonicotinohydrazide

Li Liu ^a and Fang-Fang Jian ^a ^*

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 28 October 2008; accepted 11 November 2008; online 20 November 2008)

The title compound, C₁₂H₁₁N₃O₂, was prepared by the reaction of isonicotinohydrazide and 5-methylfuran-2-carbaldehyde. The pyridine ring makes a dihedral angle of 46.90 (9)° with the mean plane of the furan ring. The crystal packing is stabilized by a bifurcated intermolecular N—H⋯(N,O) interaction.

Related literature

For general background, see: Cimerman et al. (1997 ). For bond-length data, see: Chiu et al. (1998 ).

Experimental

Crystal data

C₁₂H₁₁N₃O₂
M_r = 229.24
Tetragonal, I 4₁ /a
a = 17.313 (3) Å
c = 15.749 (5) Å
V = 4720.5 (18) Å³
Z = 16
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.25 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
14901 measured reflections
2911 independent reflections
2151 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.117
S = 1.04
2911 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.86	2.18	2.9083 (19)	143
N2—H2A⋯N3ⁱ	0.86	2.58	3.3255 (19)	146
Symmetry code: (i) $[-y+{\script{5\over 4}}, x-{\script{1\over 4}}, z-{\script{1\over 4}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037276/at2662sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037276/at2662Isup2.hkl

checkCIF report

Comment top

Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Cimerman et al., 1997). As part of our search for new schiff base compounds we synthesized the title compound (I), and describe its structure here.

In the title compound (I) (Fig. 1), the C12—N3 bond length of 1.2812 (17)Å is comparable with C—N double bond [1.284 (2) Å] reported (Chiu et al., 1998). The pyridine ring (N1/C1–C5) makes a dihedral angle of 46.90 (9)°, with the plane of the furan ring (O2/C6–C9).

The crsytal packing is stabilized by intermolecular N—H···O, N—H···N hydrogen bonds (Table 1, Fig. 2).

Related literature top

For general background, see: Cimerman et al. (1997). For bond-length data, see: Chiu et al. (1998).

Experimental top

A mixture of the isonicotinohydrazide (0.1 mol), and 5-methylfuran-2-carbaldehyde (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.082 mol, yield 82%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme.

N'-[(5-Methylfuran-2-yl)methylene]isonicotinohydrazide top

Crystal data top

C₁₂H₁₁N₃O₂	D_x = 1.290 Mg m⁻³
M_r = 229.24	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 4665 reflections
Hall symbol: -I 4ad	θ = 2.9–27.2°
a = 17.313 (3) Å	µ = 0.09 mm⁻¹
c = 15.749 (5) Å	T = 273 K
V = 4720.5 (18) Å³	Block, yellow
Z = 16	0.25 × 0.20 × 0.19 mm
F(000) = 1920

Data collection top

Bruker SMART CCD area-detector diffractometer	2151 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 28.3°, θ_min = 1.8°
ϕ and ω scans	h = −16→23
14901 measured reflections	k = −22→22
2911 independent reflections	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0456P)² + 2.257P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2911 reflections	Δρ_max = 0.17 e Å⁻³
155 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (3)

Crystal data top

C₁₂H₁₁N₃O₂	Z = 16
M_r = 229.24	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.09 mm⁻¹
a = 17.313 (3) Å	T = 273 K
c = 15.749 (5) Å	0.25 × 0.20 × 0.19 mm
V = 4720.5 (18) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2151 reflections with I > 2σ(I)
14901 measured reflections	R_int = 0.028
2911 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.04	Δρ_max = 0.17 e Å⁻³
2911 reflections	Δρ_min = −0.14 e Å⁻³
155 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

	x	y	z	U_iso*/U_eq
O2	0.58347 (5)	0.51303 (5)	0.10958 (6)	0.0482 (3)
N3	0.72302 (6)	0.49350 (7)	0.03623 (7)	0.0427 (3)
C12	0.67464 (8)	0.53721 (7)	−0.00223 (9)	0.0423 (3)
H12A	0.6866	0.5578	−0.0552	0.051*
N2	0.79076 (6)	0.47620 (7)	−0.00603 (7)	0.0443 (3)
H2A	0.7980	0.4901	−0.0578	0.053*
C8	0.60143 (8)	0.55421 (7)	0.03726 (8)	0.0417 (3)
O1	0.83833 (7)	0.42110 (8)	0.11302 (7)	0.0750 (4)
C4	0.91448 (8)	0.41092 (8)	−0.01179 (8)	0.0442 (3)
C11	0.84487 (8)	0.43670 (9)	0.03721 (8)	0.0460 (3)
C9	0.51105 (8)	0.53616 (9)	0.13450 (10)	0.0513 (4)
C7	0.54259 (8)	0.60254 (8)	0.01805 (10)	0.0505 (4)
H7A	0.5402	0.6366	−0.0276	0.061*
C3	0.91374 (8)	0.39635 (10)	−0.09860 (9)	0.0531 (4)
H3B	0.8696	0.4056	−0.1307	0.064*
N1	1.04629 (8)	0.35518 (10)	−0.09513 (9)	0.0736 (5)
C5	0.98256 (9)	0.39741 (11)	0.03194 (10)	0.0640 (5)
H5A	0.9853	0.4061	0.0901	0.077*
C2	0.98006 (9)	0.36780 (11)	−0.13609 (10)	0.0650 (5)
H2B	0.9784	0.3566	−0.1938	0.078*
C6	0.48512 (9)	0.59116 (9)	0.08124 (11)	0.0561 (4)
H6A	0.4382	0.6170	0.0851	0.067*
C1	1.04634 (10)	0.37078 (13)	−0.01203 (12)	0.0758 (6)
H1B	1.0920	0.3633	0.0180	0.091*
C10	0.47813 (11)	0.49172 (12)	0.20700 (12)	0.0760 (6)
H10A	0.4277	0.5113	0.2203	0.114*
H10B	0.5112	0.4971	0.2556	0.114*
H10C	0.4743	0.4382	0.1918	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0471 (5)	0.0516 (6)	0.0459 (6)	0.0050 (4)	0.0087 (4)	0.0080 (4)
N3	0.0440 (6)	0.0466 (6)	0.0374 (6)	0.0030 (5)	0.0080 (5)	0.0042 (5)
C12	0.0482 (7)	0.0410 (7)	0.0377 (7)	−0.0013 (5)	0.0043 (5)	0.0035 (5)
N2	0.0455 (6)	0.0564 (7)	0.0309 (5)	0.0060 (5)	0.0089 (4)	0.0086 (5)
C8	0.0469 (7)	0.0390 (7)	0.0393 (7)	−0.0019 (5)	0.0027 (5)	0.0022 (5)
O1	0.0740 (8)	0.1156 (10)	0.0355 (6)	0.0391 (7)	0.0150 (5)	0.0225 (6)
C4	0.0432 (7)	0.0547 (8)	0.0346 (7)	0.0036 (6)	0.0027 (5)	0.0012 (6)
C11	0.0493 (8)	0.0564 (8)	0.0324 (7)	0.0078 (6)	0.0065 (5)	0.0053 (6)
C9	0.0462 (8)	0.0537 (8)	0.0540 (9)	0.0000 (6)	0.0107 (6)	−0.0028 (7)
C7	0.0529 (8)	0.0440 (7)	0.0545 (9)	0.0040 (6)	0.0006 (6)	0.0051 (6)
C3	0.0429 (7)	0.0785 (10)	0.0379 (7)	0.0050 (7)	−0.0012 (6)	−0.0047 (7)
N1	0.0497 (8)	0.1162 (13)	0.0550 (8)	0.0166 (8)	0.0024 (6)	−0.0196 (8)
C5	0.0577 (9)	0.0961 (13)	0.0381 (8)	0.0182 (9)	−0.0062 (7)	−0.0109 (8)
C2	0.0546 (9)	0.1006 (13)	0.0399 (8)	0.0090 (9)	0.0034 (7)	−0.0151 (8)
C6	0.0468 (8)	0.0544 (9)	0.0672 (10)	0.0085 (6)	0.0047 (7)	−0.0014 (7)
C1	0.0483 (9)	0.1212 (16)	0.0579 (10)	0.0220 (10)	−0.0099 (7)	−0.0188 (10)
C10	0.0718 (12)	0.0839 (13)	0.0722 (12)	0.0022 (9)	0.0292 (9)	0.0134 (10)

Geometric parameters (Å, º) top

O2—C9	1.3735 (16)	C7—C6	1.421 (2)
O2—C8	1.3793 (16)	C7—H7A	0.9300
N3—C12	1.2812 (17)	C3—C2	1.383 (2)
N3—N2	1.3813 (15)	C3—H3B	0.9300
C12—C8	1.4421 (18)	N1—C2	1.334 (2)
C12—H12A	0.9300	N1—C1	1.336 (2)
N2—C11	1.3450 (17)	C5—C1	1.383 (2)
N2—H2A	0.8600	C5—H5A	0.9300
C8—C7	1.3526 (19)	C2—H2B	0.9300
O1—C11	1.2293 (16)	C6—H6A	0.9300
C4—C5	1.385 (2)	C1—H1B	0.9300
C4—C3	1.3904 (19)	C10—H10A	0.9600
C4—C11	1.4990 (18)	C10—H10B	0.9600
C9—C6	1.346 (2)	C10—H10C	0.9600
C9—C10	1.490 (2)

C9—O2—C8	106.92 (11)	C2—C3—C4	118.50 (14)
C12—N3—N2	117.08 (11)	C2—C3—H3B	120.7
N3—C12—C8	119.42 (12)	C4—C3—H3B	120.7
N3—C12—H12A	120.3	C2—N1—C1	116.18 (14)
C8—C12—H12A	120.3	C1—C5—C4	119.14 (14)
C11—N2—N3	117.23 (11)	C1—C5—H5A	120.4
C11—N2—H2A	121.4	C4—C5—H5A	120.4
N3—N2—H2A	121.4	N1—C2—C3	124.47 (14)
C7—C8—O2	109.55 (12)	N1—C2—H2B	117.8
C7—C8—C12	133.77 (13)	C3—C2—H2B	117.8
O2—C8—C12	116.66 (11)	C9—C6—C7	107.52 (13)
C5—C4—C3	117.78 (13)	C9—C6—H6A	126.2
C5—C4—C11	118.59 (12)	C7—C6—H6A	126.2
C3—C4—C11	123.56 (12)	N1—C1—C5	123.88 (15)
O1—C11—N2	122.64 (12)	N1—C1—H1B	118.1
O1—C11—C4	120.56 (13)	C5—C1—H1B	118.1
N2—C11—C4	116.79 (11)	C9—C10—H10A	109.5
C6—C9—O2	109.43 (13)	C9—C10—H10B	109.5
C6—C9—C10	135.66 (15)	H10A—C10—H10B	109.5
O2—C9—C10	114.68 (14)	C9—C10—H10C	109.5
C8—C7—C6	106.55 (13)	H10A—C10—H10C	109.5
C8—C7—H7A	126.7	H10B—C10—H10C	109.5
C6—C7—H7A	126.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.18	2.9083 (19)	143
N2—H2A···N3ⁱ	0.86	2.58	3.3255 (19)	146

Symmetry code: (i) −y+5/4, x−1/4, z−1/4.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁N₃O₂
M_r	229.24
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	273
a, c (Å)	17.313 (3), 15.749 (5)
V (Å³)	4720.5 (18)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14901, 2911, 2151
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.117, 1.04
No. of reflections	2911
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.14

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.18	2.9083 (19)	143
N2—H2A···N3ⁱ	0.86	2.58	3.3255 (19)	146

Symmetry code: (i) −y+5/4, x−1/4, z−1/4.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chiu, P., Chen, B. & Cheng, K. F. (1998). Tetrahedron Lett. 39, 9229–9232. Web of Science CSD CrossRef CAS Google Scholar
Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2370

doi:10.1107/S1600536808037276

Open

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