(E)-N′-(2-Furylmethyl­ene)benzo­hydrazide

doi:10.1107/S1600536809042251

Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2800.

Published online 2009 October 23. doi: 10.1107/S1600536809042251

PMCID: PMC2971411

(E)-N′-(2-Furylmethylene)benzohydrazide

Ming-Zhi Song^a and Chuan-Gang Fan^a^*

^aCollege of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People’s Republic of China

Correspondence e-mail: fanchuangang2009/at/163.com

Received October 13, 2009; Accepted October 14, 2009.

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Abstract

In the title compound, C₁₂H₁₀N₂O₂, the dihedral angle between the benzene and furan rings is 52.54 (7)°. In the crystal, intermolecular N—H (...)

O hydrogen bonds and C—H (...)

π interactions link the molecules.

Related literature

For biological properties of Schiff base ligands, see: Chakraborty et al. (1996

); Jeewoth et al. (1999

). For related crystal structures, see: Fun et al. (2008

); Cui et al. (2009

); Nie (2008

An external file that holds a picture, illustration, etc.
Object name is e-65-o2800-scheme1.jpg Object name is e-65-o2800-scheme1.jpg

Experimental

Crystal data

C₁₂H₁₀N₂O₂
M _r = 214.22
Monoclinic,
a = 12.3955 (11) Å
b = 9.4777 (9) Å
c = 9.6845 (10) Å
β = 110.610 (1)°
V = 1064.93 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.43 × 0.38 × 0.30 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T _min = 0.961, T _max = 0.973
5190 measured reflections
1882 independent reflections
1360 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.103
S = 1.05
1882 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Siemens, 1996

); cell refinement: SAINT (Siemens, 1996

); 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.

Table 1

Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809042251/bq2168sup1.cif

Click here to view.^{(15K, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042251/bq2168Isup2.hkl

Click here to view.^{(93K, hkl)}

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

Acknowledgments

The authors acknowledge the financial support of the Foundation of Binzhou University (No. BZXYLG200609).

supplementary crystallographic information

Comment

Conventionally, Schiff bases derived from a large number of carbonyl compounds and amines. It has been shown that Schiff base compounds have strong anticancer activity (Chakraborty et al., 1996). It has been well known that a series of certain Schiff base compounds, have received considerable attention during the last decades, mainly because their structures or for their biological properties (Jeewoth et al., 1999).

In the compound (I), (Fig. 1), the bond lengths an angles are normal and are comparable to the values observed in similar compounds (Nie et al., 2008; Fun et al., 2008; Cui et al., 2009).

In the crystal structure, the C=N bond length in the molecule is 1.273 (2) ° (C8=N2), showing the double-bond character. Meanwhile, the dihedral angle between the benzene ring (C2-C7) and the furan ring (C9-C12/O2) in the Schiff base molecule is 52.54 (7)°, indicating that the two aromatic ring planes are not coplanar.

Moreover, the crystal supramolecular structure was built from the connections of intermolecular N—H···O hydrogen bonds and C-H···π hydrogen bonding interactions, as shown in Table 1.

Experimental

Benzohydrazide (5.0 mmol), 20 ml ethanol and furfural (5.0 mmol) were mixed in 50 ml flash. After refluxing 3 h, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₁₂H₁₀N₂O₂: C 67.28, H 4.71, N 13.08%; found: C 67.16, H 4.66, N 13.19%.

Figures

Fig. 1.

A view of (I) showing the atomic numbering scheme and 50% probability displacement ellipsoids.

Fig. 2.

A packing of (I) viewed down b-axis showing the N-H..O and C-H···π H-bond interactions with dashed lines. Symmetry codes: (i) x, -y+1/2, z+1/2; (ii) x, y-1, z.

Crystal data

C₁₂H₁₀N₂O₂	F(000) = 448
M_r = 214.22	D_x = 1.336 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1760 reflections
a = 12.3955 (11) Å	θ = 2.8–25.6°
b = 9.4777 (9) Å	µ = 0.09 mm⁻¹
c = 9.6845 (10) Å	T = 298 K
β = 110.610 (1)°	Needle, green
V = 1064.93 (18) Å³	0.43 × 0.38 × 0.30 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1882 independent reflections
Radiation source: fine-focus sealed tube	1360 reflections with I > 2σ(I)
graphite	R_int = 0.032
phi and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.961, T_max = 0.973	k = −11→5
5190 measured reflections	l = −11→11

Refinement

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0444P)² + 0.2066P] where P = (F_o² + 2F_c²)/3
1882 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.20 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 (Å²)

	x	y	z	U_iso*/U_eq
N1	0.23549 (11)	0.22758 (14)	0.10288 (15)	0.0393 (4)
H1	0.2462	0.2263	0.1956	0.047*
N2	0.18065 (12)	0.11622 (15)	0.01303 (15)	0.0394 (4)
O1	0.26227 (11)	0.34211 (13)	−0.08757 (13)	0.0525 (4)
O2	0.05357 (11)	−0.11197 (14)	−0.14345 (14)	0.0552 (4)
C1	0.27183 (14)	0.33810 (18)	0.04323 (18)	0.0369 (4)
C2	0.32908 (13)	0.45449 (17)	0.14650 (18)	0.0357 (4)
C3	0.31657 (15)	0.47508 (18)	0.28218 (19)	0.0439 (4)
H3	0.2698	0.4148	0.3122	0.053*
C4	0.37320 (17)	0.5846 (2)	0.3724 (2)	0.0539 (5)
H4	0.3642	0.5982	0.4628	0.065*
C5	0.44318 (17)	0.6740 (2)	0.3290 (2)	0.0576 (6)
H5	0.4822	0.7468	0.3908	0.069*
C6	0.45522 (16)	0.6555 (2)	0.1942 (2)	0.0553 (5)
H6	0.5019	0.7161	0.1646	0.066*
C7	0.39802 (15)	0.5469 (2)	0.1033 (2)	0.0460 (5)
H7	0.4057	0.5354	0.0118	0.055*
C8	0.17622 (14)	0.00187 (18)	0.07975 (19)	0.0407 (4)
H8	0.2088	−0.0011	0.1821	0.049*
C9	0.12239 (14)	−0.12242 (18)	0.00150 (19)	0.0406 (4)
C10	0.12911 (17)	−0.2579 (2)	0.0460 (2)	0.0574 (5)
H10	0.1701	−0.2924	0.1398	0.069*
C11	0.06160 (19)	−0.3374 (2)	−0.0779 (3)	0.0693 (6)
H11	0.0504	−0.4346	−0.0818	0.083*
C12	0.01745 (18)	−0.2464 (3)	−0.1875 (3)	0.0635 (6)
H12	−0.0316	−0.2708	−0.2817	0.076*

Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0512 (9)	0.0397 (8)	0.0276 (7)	−0.0026 (7)	0.0147 (6)	−0.0027 (6)
N2	0.0459 (8)	0.0386 (8)	0.0341 (8)	−0.0018 (7)	0.0146 (6)	−0.0038 (7)
O1	0.0821 (9)	0.0482 (8)	0.0309 (7)	−0.0056 (7)	0.0245 (6)	−0.0012 (6)
O2	0.0565 (8)	0.0579 (9)	0.0459 (8)	−0.0045 (7)	0.0116 (6)	−0.0062 (7)
C1	0.0414 (9)	0.0386 (10)	0.0318 (9)	0.0061 (8)	0.0142 (7)	0.0030 (8)
C2	0.0383 (9)	0.0362 (9)	0.0332 (9)	0.0047 (7)	0.0134 (7)	0.0017 (8)
C3	0.0554 (11)	0.0432 (10)	0.0381 (10)	−0.0067 (9)	0.0225 (8)	−0.0012 (8)
C4	0.0699 (13)	0.0579 (13)	0.0391 (11)	−0.0131 (10)	0.0257 (10)	−0.0102 (9)
C5	0.0634 (12)	0.0576 (13)	0.0502 (12)	−0.0191 (11)	0.0180 (10)	−0.0126 (10)
C6	0.0571 (12)	0.0598 (13)	0.0522 (12)	−0.0185 (10)	0.0233 (10)	−0.0014 (10)
C7	0.0509 (11)	0.0534 (11)	0.0386 (10)	−0.0041 (9)	0.0218 (9)	0.0008 (9)
C8	0.0451 (10)	0.0430 (10)	0.0338 (9)	0.0013 (8)	0.0136 (8)	−0.0006 (8)
C9	0.0428 (10)	0.0429 (11)	0.0378 (10)	0.0015 (8)	0.0162 (8)	−0.0012 (8)
C10	0.0647 (13)	0.0460 (12)	0.0627 (13)	0.0011 (10)	0.0241 (11)	0.0039 (11)
C11	0.0781 (15)	0.0457 (12)	0.0926 (19)	−0.0118 (12)	0.0406 (14)	−0.0163 (13)
C12	0.0560 (12)	0.0711 (15)	0.0633 (14)	−0.0171 (12)	0.0210 (11)	−0.0292 (13)

Geometric parameters (Å, °)

N1—C1	1.348 (2)	C5—C6	1.376 (3)
N1—N2	1.3844 (19)	C5—H5	0.9300
N1—H1	0.8600	C6—C7	1.377 (3)
N2—C8	1.273 (2)	C6—H6	0.9300
O1—C1	1.2306 (19)	C7—H7	0.9300
O2—C9	1.366 (2)	C8—C9	1.432 (2)
O2—C12	1.368 (2)	C8—H8	0.9300
C1—C2	1.490 (2)	C9—C10	1.348 (3)
C2—C7	1.387 (2)	C10—C11	1.415 (3)
C2—C3	1.390 (2)	C10—H10	0.9300
C3—C4	1.379 (2)	C11—C12	1.327 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.380 (3)	C12—H12	0.9300
C4—H4	0.9300

C1—N1—N2	119.16 (13)	C5—C6—H6	120.1
C1—N1—H1	120.4	C7—C6—H6	120.1
N2—N1—H1	120.4	C6—C7—C2	120.79 (17)
C8—N2—N1	115.43 (14)	C6—C7—H7	119.6
C9—O2—C12	105.68 (16)	C2—C7—H7	119.6
O1—C1—N1	122.65 (16)	N2—C8—C9	121.81 (16)
O1—C1—C2	121.24 (15)	N2—C8—H8	119.1
N1—C1—C2	116.08 (14)	C9—C8—H8	119.1
C7—C2—C3	118.82 (16)	C10—C9—O2	110.11 (16)
C7—C2—C1	117.59 (15)	C10—C9—C8	130.51 (17)
C3—C2—C1	123.59 (15)	O2—C9—C8	119.36 (15)
C4—C3—C2	120.22 (17)	C9—C10—C11	106.54 (19)
C4—C3—H3	119.9	C9—C10—H10	126.7
C2—C3—H3	119.9	C11—C10—H10	126.7
C3—C4—C5	120.23 (18)	C12—C11—C10	106.65 (19)
C3—C4—H4	119.9	C12—C11—H11	126.7
C5—C4—H4	119.9	C10—C11—H11	126.7
C6—C5—C4	120.03 (18)	C11—C12—O2	111.01 (18)
C6—C5—H5	120.0	C11—C12—H12	124.5
C4—C5—H5	120.0	O2—C12—H12	124.5
C5—C6—C7	119.89 (18)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.14	2.972 (2)	163
C10—H10···Cg1ⁱⁱ	0.93	2.85	3.498 (2)	128

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2168).

References

Chakraborty, J. & Patel, R. N. (1996). J. Indian Chem. Soc.73, 191–195.
Cui, C., Meng, Q. & Wang, Y. (2009). Acta Cryst. E65, o2472. [PMC free article] [PubMed]
Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595. [PMC free article] [PubMed]
Jeewoth, T., Bhowon, M. G. & Wah, H. L. K. (1999). Transition Met. Chem.24, 445–448.
Nie, Y. (2008). Acta Cryst. E64, o471. [PMC free article] [PubMed]
Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of
International Union of Crystallography