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Acta Cryst. (2009). E65, o2260    [ doi:10.1107/S1600536809033698 ]

N'-(2-Furylmethylene)nicotinohydrazide

H. Qian, Z. Yin, C. Zhang and Z. Yao

Abstract top

The asymmetric unit of the title compound, C11H9N3O2, contains two independent molecules: the dihedral angles between the pyridine ring and the furyl ring are 17.00 (16) and 34.12 (15)°. The crystal structure involves intermolecular C-H...O, N-H...N and N-H...O hydrogen bonds.

Comment top

The chemistry of Schiff bases has attracted a great deal of interest in recent years. These compounds play an important role in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of our in the study of the coordination chemistry of Schiff bases, we synthesized the title compound and determined its crystal structure.

The molecular structure is shown in Fig.1. Each molecule is not planar, making the dihedral angle of 17.00 (16) and 34.12 (15)° between pyridine and furyl rings, respectively. In the crystal structure, molecules are linked through intermolecular C—H···O, N—H···N and N—H···O hydrogen bonds, forming a network.

Related literature top

For the role played by Schiff bases in the development of various

proteins and enzymes, see: Kahwa et al. (1986); Santos et al. (2001).

Experimental top

Pyridine-4-carboxylic acid hydrazide (1 mmol, 0.137 g) was dissolved in anhydrous ethanol (15 ml), The mixture was stirred for several minutes at 351 K. Furan-2-carbaldehyde (1 mmol, 0.96 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from methanol. Pink single crystals of (I) was obtained after 3 d.

Refinement top

All H atoms were positioned geometrically and refined as riding with C—H = 0.93(aromatic) and N—H = 0.86Å, with Uiso(H) = 1.2Ueq(CH, NH).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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
[Figure 1] Fig. 1. the ORTEP plot of (I). Displacement ellipsoids are drawn at the 30% probability level.
N'-(2-Furylmethylene)nicotinohydrazide top
Crystal data top
C11H9N3O2F(000) = 896
Mr = 215.21Dx = 1.347 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 2878 reflections
a = 17.4363 (3) Åθ = 2.4–26.0°
b = 16.9143 (3) ŵ = 0.10 mm−1
c = 7.9639 (1) ÅT = 296 K
β = 115.326 (1)°Block, pink
V = 2122.99 (6) Å30.34 × 0.24 × 0.15 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer		2443 independent reflections
Radiation source: fine-focus sealed tube1908 reflections with I > 2σ(I)
graphiteRint = 0.026
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −22→15
Tmin = 0.964, Tmax = 0.981k = −20→21
9336 measured reflectionsl = −7→10
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0488P)2]
where P = (Fo2 + 2Fc2)/3
2443 reflections(Δ/σ)max = 0.006
290 parametersΔρmax = 0.10 e Å−3
2 restraintsΔρmin = −0.16 e Å−3
Crystal data top
C11H9N3O2V = 2122.99 (6) Å3
Mr = 215.21Z = 8
Monoclinic, CcMo Kα radiation
a = 17.4363 (3) ŵ = 0.10 mm−1
b = 16.9143 (3) ÅT = 296 K
c = 7.9639 (1) Å0.34 × 0.24 × 0.15 mm
β = 115.326 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2443 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		1908 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.981Rint = 0.026
9336 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.086Δρmax = 0.10 e Å−3
S = 1.06Δρmin = −0.16 e Å−3
2443 reflectionsAbsolute structure: ?
290 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
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
N10.20002 (12)0.30973 (11)0.8151 (3)0.0512 (4)
N20.15397 (11)0.29763 (11)0.6278 (2)0.0500 (4)
H2A0.11010.32620.56530.060*
O40.52299 (10)−0.06828 (10)0.4681 (3)0.0659 (5)
N40.45709 (11)−0.21482 (11)0.4338 (2)0.0505 (5)
N50.40911 (11)−0.14890 (11)0.3504 (3)0.0522 (5)
H5A0.3552−0.15320.28550.063*
C60.17831 (13)0.24079 (13)0.5439 (3)0.0503 (5)
C170.44693 (14)−0.07807 (13)0.3711 (3)0.0490 (5)
O10.27842 (12)0.33154 (12)1.1928 (2)0.0715 (5)
O20.23970 (12)0.19833 (11)0.6284 (3)0.0763 (6)
C70.12722 (13)0.23106 (12)0.3412 (3)0.0461 (5)
O30.53896 (10)−0.35845 (9)0.5715 (2)0.0622 (4)
C180.39031 (13)−0.01116 (13)0.2696 (3)0.0478 (5)
C150.45280 (14)−0.35168 (14)0.4952 (3)0.0532 (5)
C50.17080 (15)0.36173 (14)0.8885 (3)0.0539 (6)
H5B0.12170.38920.81430.065*
C160.41431 (15)−0.27691 (14)0.4225 (3)0.0553 (6)
H16A0.3554−0.27380.36440.066*
C40.21241 (16)0.37849 (14)1.0833 (4)0.0572 (6)
C80.07516 (16)0.28882 (14)0.2286 (3)0.0589 (6)
H8A0.07190.33660.28290.071*
N30.02917 (18)0.28065 (15)0.0467 (3)0.0813 (7)
C210.28729 (18)0.10962 (16)0.0818 (4)0.0692 (7)
H21A0.25200.15150.01950.083*
C110.13288 (17)0.16115 (14)0.2577 (4)0.0650 (7)
H11A0.16780.12060.32830.078*
N60.26106 (14)0.03697 (14)0.0239 (3)0.0773 (7)
C140.41892 (19)−0.42120 (16)0.5088 (5)0.0781 (8)
H14A0.3614−0.43240.46660.094*
C190.41546 (17)0.06558 (14)0.3224 (4)0.0628 (6)
H19A0.46760.07590.42140.075*
C220.31279 (16)−0.02186 (15)0.1181 (4)0.0651 (7)
H22A0.2956−0.07340.07930.078*
C30.1971 (2)0.43309 (15)1.1883 (5)0.0737 (8)
H3B0.15540.47201.14650.088*
C90.0358 (2)0.2127 (2)−0.0274 (4)0.0796 (8)
H9A0.00360.2059−0.15430.095*
C200.36299 (19)0.12676 (15)0.2276 (4)0.0705 (7)
H20A0.37880.17890.26210.085*
C130.4863 (2)−0.47379 (17)0.5986 (5)0.0821 (9)
H13A0.4821−0.52630.62820.098*
C120.5564 (2)−0.43447 (15)0.6328 (4)0.0706 (7)
H12A0.6107−0.45570.69110.085*
C10.3036 (2)0.3593 (2)1.3692 (4)0.0870 (9)
H1B0.34820.33831.47320.104*
C100.0865 (2)0.15199 (17)0.0696 (4)0.0729 (8)
H10A0.08970.10560.01020.087*
C20.2564 (2)0.4201 (2)1.3734 (5)0.0848 (9)
H2B0.26140.44851.47760.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0387 (9)0.0551 (10)0.0519 (11)0.0008 (8)0.0119 (9)0.0000 (8)
N20.0347 (9)0.0544 (10)0.0500 (10)0.0077 (8)0.0078 (8)0.0012 (8)
O40.0354 (8)0.0574 (9)0.0832 (12)−0.0024 (7)0.0045 (8)−0.0060 (8)
N40.0369 (9)0.0520 (11)0.0563 (11)0.0020 (8)0.0137 (9)0.0018 (8)
N50.0318 (9)0.0514 (11)0.0601 (12)0.0021 (8)0.0070 (8)0.0029 (8)
C60.0331 (11)0.0486 (12)0.0574 (13)0.0030 (9)0.0080 (10)−0.0008 (10)
C170.0360 (11)0.0504 (12)0.0527 (12)−0.0015 (9)0.0115 (10)−0.0065 (9)
O10.0645 (11)0.0809 (12)0.0594 (10)0.0077 (10)0.0171 (9)−0.0046 (9)
O20.0533 (10)0.0745 (11)0.0689 (11)0.0264 (9)−0.0046 (9)−0.0126 (9)
C70.0331 (10)0.0472 (11)0.0530 (12)−0.0021 (9)0.0138 (10)0.0000 (9)
O30.0452 (9)0.0555 (9)0.0781 (11)0.0037 (8)0.0189 (9)0.0055 (8)
C180.0370 (11)0.0504 (12)0.0522 (12)−0.0014 (9)0.0154 (10)−0.0022 (9)
C150.0411 (12)0.0536 (13)0.0572 (13)−0.0022 (10)0.0138 (11)0.0001 (10)
C50.0457 (12)0.0527 (12)0.0616 (15)0.0026 (10)0.0214 (12)0.0041 (10)
C160.0355 (11)0.0578 (14)0.0616 (14)−0.0020 (10)0.0104 (10)0.0026 (11)
C40.0527 (14)0.0565 (13)0.0638 (14)−0.0025 (11)0.0264 (12)0.0006 (11)
C80.0576 (15)0.0628 (14)0.0552 (14)0.0096 (12)0.0232 (12)0.0058 (11)
N30.0926 (19)0.0879 (16)0.0512 (12)0.0251 (14)0.0192 (12)0.0123 (12)
C210.0615 (17)0.0575 (15)0.0865 (19)0.0119 (13)0.0298 (15)0.0192 (13)
C110.0587 (15)0.0573 (13)0.0621 (15)0.0076 (12)0.0097 (12)−0.0028 (11)
N60.0512 (13)0.0676 (14)0.0881 (16)0.0060 (11)0.0060 (12)0.0147 (12)
C140.0587 (16)0.0559 (15)0.113 (2)−0.0062 (13)0.0302 (17)0.0049 (14)
C190.0551 (14)0.0523 (14)0.0685 (15)−0.0050 (11)0.0145 (12)−0.0060 (11)
C220.0495 (14)0.0530 (13)0.0729 (16)−0.0022 (11)0.0073 (13)0.0017 (12)
C30.081 (2)0.0624 (15)0.086 (2)−0.0060 (14)0.0431 (18)−0.0135 (14)
C90.080 (2)0.094 (2)0.0501 (14)0.0059 (17)0.0138 (15)0.0000 (14)
C200.0716 (18)0.0484 (13)0.0849 (19)−0.0006 (13)0.0272 (16)0.0019 (12)
C130.082 (2)0.0527 (15)0.110 (3)0.0018 (15)0.0400 (19)0.0111 (15)
C120.0660 (17)0.0595 (15)0.0796 (17)0.0141 (13)0.0246 (14)0.0079 (13)
C10.078 (2)0.107 (3)0.0601 (18)−0.015 (2)0.0146 (16)−0.0101 (16)
C100.0745 (18)0.0722 (18)0.0628 (16)−0.0057 (15)0.0206 (14)−0.0127 (13)
C20.103 (2)0.082 (2)0.082 (2)−0.0289 (18)0.052 (2)−0.0266 (16)
Geometric parameters (Å, °) top
N1—C51.277 (3)C8—N31.329 (3)
N1—N21.374 (3)C8—H8A0.9300
N2—C61.339 (3)N3—C91.319 (4)
N2—H2A0.8600C21—N61.323 (4)
O4—C171.227 (3)C21—C201.365 (4)
N4—C161.269 (3)C21—H21A0.9300
N4—N51.382 (2)C11—C101.374 (4)
N5—C171.343 (3)C11—H11A0.9300
N5—H5A0.8600N6—C221.337 (3)
C6—O21.224 (3)C14—C131.401 (4)
C6—C71.482 (3)C14—H14A0.9300
C17—C181.492 (3)C19—C201.374 (4)
O1—C41.363 (3)C19—H19A0.9300
O1—C11.363 (4)C22—H22A0.9300
C7—C81.374 (3)C3—C21.409 (5)
C7—C111.380 (3)C3—H3B0.9300
O3—C151.363 (3)C9—C101.360 (4)
O3—C121.363 (3)C9—H9A0.9300
C18—C191.377 (3)C20—H20A0.9300
C18—C221.386 (3)C13—C121.315 (4)
C15—C141.341 (4)C13—H13A0.9300
C15—C161.433 (3)C12—H12A0.9300
C5—C41.432 (4)C1—C21.327 (5)
C5—H5B0.9300C1—H1B0.9300
C16—H16A0.9300C10—H10A0.9300
C4—C31.346 (4)C2—H2B0.9300
C5—N1—N2115.95 (18)N6—C21—H21A118.0
C6—N2—N1119.08 (17)C20—C21—H21A118.0
C6—N2—H2A120.5C10—C11—C7119.5 (2)
N1—N2—H2A120.5C10—C11—H11A120.3
C16—N4—N5114.65 (17)C7—C11—H11A120.3
C17—N5—N4119.75 (17)C21—N6—C22116.5 (2)
C17—N5—H5A120.1C15—C14—C13107.2 (3)
N4—N5—H5A120.1C15—C14—H14A126.4
O2—C6—N2122.4 (2)C13—C14—H14A126.4
O2—C6—C7120.7 (2)C20—C19—C18119.5 (2)
N2—C6—C7116.88 (18)C20—C19—H19A120.3
O4—C17—N5122.6 (2)C18—C19—H19A120.3
O4—C17—C18121.7 (2)N6—C22—C18124.3 (2)
N5—C17—C18115.71 (18)N6—C22—H22A117.8
C4—O1—C1105.7 (2)C18—C22—H22A117.8
C8—C7—C11117.3 (2)C4—C3—C2106.9 (3)
C8—C7—C6123.6 (2)C4—C3—H3B126.5
C11—C7—C6119.08 (19)C2—C3—H3B126.5
C15—O3—C12105.9 (2)N3—C9—C10124.3 (3)
C19—C18—C22117.0 (2)N3—C9—H9A117.8
C19—C18—C17119.9 (2)C10—C9—H9A117.8
C22—C18—C17123.1 (2)C21—C20—C19118.8 (2)
C14—C15—O3109.3 (2)C21—C20—H20A120.6
C14—C15—C16131.3 (2)C19—C20—H20A120.6
O3—C15—C16119.4 (2)C12—C13—C14106.7 (2)
N1—C5—C4121.1 (2)C12—C13—H13A126.7
N1—C5—H5B119.5C14—C13—H13A126.7
C4—C5—H5B119.5C13—C12—O3110.9 (3)
N4—C16—C15122.9 (2)C13—C12—H12A124.5
N4—C16—H16A118.6O3—C12—H12A124.5
C15—C16—H16A118.6C2—C1—O1111.3 (3)
C3—C4—O1109.9 (2)C2—C1—H1B124.4
C3—C4—C5131.7 (3)O1—C1—H1B124.4
O1—C4—C5118.4 (2)C9—C10—C11118.1 (3)
N3—C8—C7124.0 (2)C9—C10—H10A121.0
N3—C8—H8A118.0C11—C10—H10A121.0
C7—C8—H8A118.0C1—C2—C3106.2 (3)
C9—N3—C8116.8 (2)C1—C2—H2B126.9
N6—C21—C20123.9 (2)C3—C2—H2B126.9
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O4i0.862.263.080 (2)161
N2—H2A···N4i0.862.513.112 (3)128
N5—H5A···O2ii0.862.012.843 (3)162
C8—H8A···O4i0.932.563.433 (3)156
C16—H16A···O2ii0.932.453.228 (3)141
C22—H22A···O2ii0.932.433.260 (3)149
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x, −y, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O4i0.862.263.080 (2)161
N2—H2A···N4i0.862.513.112 (3)128
N5—H5A···O2ii0.862.012.843 (3)162
C8—H8A···O4i0.932.563.433 (3)156
C16—H16A···O2ii0.932.453.228 (3)141
C22—H22A···O2ii0.932.433.260 (3)149
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x, −y, z−1/2.
Acknowledgements top

The authors would like to express their deep appreciation to the Startup Fund for PhDs of the Natural Scientific Research of Zhengzhou University of Light Industry (No.2005001) and the Fund for Natural Scientific Research of Zhengzhou University of Light Industry (000455).

references
References top

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Kahwa, I. A., Selbin, I., Hsieh, T. C. Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185.

Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838-844.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.