N′-[4-(Dimethyl­amino)­benzyl­idene]furan-2-carbohydrazide

Li, Y.-F.; Meng, F.-Y.

doi:10.1107/S1600536810037244

organic compounds

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Volume 66| Part 10| October 2010| Page o2696

doi:10.1107/S1600536810037244

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N′-[4-(Dimethylamino)benzylidene]furan-2-carbohydrazide

Yu-Feng Li ^a ^* and Fan-Yong Meng ^b

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bWeifang Middle School, Weifang 261061, People's Republic of China
^*Correspondence e-mail: liyufeng8111@163.com

(Received 12 September 2010; accepted 17 September 2010; online 30 September 2010)

The title compound, C₁₄H₁₅N₃O₂, was prepared by the reaction of 4-(dimethylamino)benzaldehyde and furan-2-carbohydrazide. The dihedral angle between the benzene ring and the furan ring is 25.59 (19)°. In the crystal, molecules are linked by intermolecular N—H⋯O hydrogen bonds, forming chains along [010].

Related literature

For the applications of this class of Schiff base compounds, see: Habermehl et al. (2006 ); Nataliya et al. (2007 ). For a related structure, see: Li & Jian (2010 ).

Experimental

Crystal data

C₁₄H₁₅N₃O₂
M_r = 257.29
Orthorhombic, P b c a
a = 10.866 (2) Å
b = 7.9654 (16) Å
c = 30.620 (6) Å
V = 2650.2 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
18964 measured reflections
2394 independent reflections
986 reflections with I > 2σ(I)
R_int = 0.172

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.143
S = 0.75
2394 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.10	2.933 (3)	163
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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/S1600536810037244/lh5131sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037244/lh5131Isup2.hkl

checkCIF report

Comment top

Schiff bases bearing additional donor groups represent an important class of heteropolydentate ligands capable of forming mono-, bi-, and polynuclear complexes with metals in coordination chemistry (Nataliya et al., 2007). They are important intermediates which have many interesting properties (Habermehl et al., 2006). As part of our search for new schiff base compounds we synthesized the title compound (I), and the crystal structure is presented herein. The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the benzene ring and the furan ring is 25.59 (19)°. In the crystal structure molecules are linked by intermolecular N-H···O hydrogen bonds to form one-dimensional chains along [010]. The bond lengths and angles agree with those observed in a related structure (Li & Jian, 2010).

Related literature top

For the applications of this class of Schiff base compounds, see: Habermehl et al. (2006); Nataliya et al. (2007). For a related structure, see: Li & Jian (2010).

Experimental top

A mixture of 4-(dimethylamino)benzaldehyde (0.1 mol), and furan-2-carbohydrazide (0.1 mol) was stirred in refluxing ethanol (20 mL) for 2 h to afford the title compound (0.089 mol, yield 89%). Single crystals suitable for X-ray measurements were obtained by recrystallization of solution of the title compound in 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 the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

N'-[4-(Dimethylamino)benzylidene]furan-2-carbohydrazide top

Crystal data top

C₁₄H₁₅N₃O₂	F(000) = 1088
M_r = 257.29	D_x = 1.290 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 986 reflections
a = 10.866 (2) Å	θ = 3.2–25.3°
b = 7.9654 (16) Å	µ = 0.09 mm⁻¹
c = 30.620 (6) Å	T = 293 K
V = 2650.2 (9) Å³	Block, colorless
Z = 8	0.22 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	986 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.172
Graphite monochromator	θ_max = 25.3°, θ_min = 3.2°
ϕ and ω scans	h = −13→13
18964 measured reflections	k = −8→9
2394 independent reflections	l = −36→36

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 0.75	w = 1/[σ²(F_o²) + (0.0687P)²] where P = (F_o² + 2F_c²)/3
2394 reflections	(Δ/σ)_max = 0.002
196 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₄H₁₅N₃O₂	V = 2650.2 (9) Å³
M_r = 257.29	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.866 (2) Å	µ = 0.09 mm⁻¹
b = 7.9654 (16) Å	T = 293 K
c = 30.620 (6) Å	0.22 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	986 reflections with I > 2σ(I)
18964 measured reflections	R_int = 0.172
2394 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 0.75	Δρ_max = 0.15 e Å⁻³
2394 reflections	Δρ_min = −0.16 e Å⁻³
196 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
N2	0.2524 (2)	0.2706 (3)	0.07906 (7)	0.0526 (7)
H2A	0.2085	0.3518	0.0691	0.063*
N1	0.2357 (2)	0.2125 (3)	0.12126 (7)	0.0522 (7)
C9	0.2087 (3)	0.1579 (4)	0.25849 (9)	0.0565 (9)
H9A	0.2642	0.0921	0.2740	0.068*
O2	0.39675 (19)	0.0722 (3)	0.06431 (6)	0.0592 (6)
C7	0.1388 (2)	0.2646 (4)	0.18944 (8)	0.0440 (7)
C10	0.1164 (3)	0.2436 (4)	0.28088 (9)	0.0513 (8)
O1	0.3004 (2)	0.4211 (3)	0.00187 (6)	0.0778 (8)
C12	0.0460 (3)	0.3471 (4)	0.21190 (9)	0.0527 (8)
H12A	−0.0101	0.4112	0.1962	0.063*
C11	0.0337 (3)	0.3379 (4)	0.25639 (9)	0.0544 (9)
H11A	−0.0300	0.3949	0.2702	0.065*
C5	0.3391 (3)	0.1974 (4)	0.05371 (9)	0.0496 (8)
N3	0.1068 (3)	0.2355 (4)	0.32592 (8)	0.0705 (9)
C6	0.1552 (3)	0.2950 (4)	0.14317 (9)	0.0487 (8)
H6A	0.1070	0.3751	0.1292	0.058*
C14	0.1968 (7)	0.1475 (9)	0.35123 (15)	0.0956 (16)
C8	0.2191 (3)	0.1689 (4)	0.21414 (9)	0.0517 (8)
H8A	0.2819	0.1105	0.2002	0.062*
C2	0.3436 (4)	0.4699 (6)	−0.03795 (11)	0.0939 (14)
H2B	0.3175	0.5649	−0.0529	0.113*
C4	0.3625 (3)	0.2785 (4)	0.01224 (9)	0.0533 (9)
C1	0.4275 (4)	0.3640 (5)	−0.05229 (11)	0.0846 (13)
H1B	0.4701	0.3704	−0.0786	0.101*
C13	0.0192 (5)	0.3396 (9)	0.34859 (14)	0.0881 (15)
C3	0.4401 (3)	0.2390 (4)	−0.01997 (10)	0.0698 (10)
H3A	0.4925	0.1467	−0.0209	0.084*
H13A	0.025 (4)	0.306 (5)	0.3795 (14)	0.127 (16)*
H13B	−0.057 (5)	0.330 (7)	0.3362 (15)	0.15 (2)*
H14A	0.202 (4)	0.030 (7)	0.3405 (13)	0.13 (2)*
H13C	0.038 (6)	0.456 (8)	0.3456 (16)	0.18 (3)*
H14B	0.168 (4)	0.141 (6)	0.3805 (17)	0.148 (19)*
H14C	0.273 (7)	0.198 (11)	0.352 (2)	0.24 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0640 (17)	0.0533 (18)	0.0406 (13)	0.0055 (14)	0.0054 (12)	0.0084 (12)
N1	0.0624 (17)	0.0508 (18)	0.0435 (14)	−0.0018 (14)	0.0053 (12)	0.0071 (12)
C9	0.069 (2)	0.048 (2)	0.0520 (18)	0.0090 (17)	0.0001 (16)	0.0086 (15)
O2	0.0723 (15)	0.0515 (16)	0.0537 (13)	0.0078 (12)	0.0064 (11)	0.0064 (11)
C7	0.0477 (18)	0.041 (2)	0.0434 (16)	0.0008 (15)	0.0062 (13)	0.0015 (14)
C10	0.0603 (19)	0.049 (2)	0.0442 (16)	−0.0075 (16)	0.0075 (15)	−0.0022 (16)
O1	0.105 (2)	0.074 (2)	0.0543 (14)	0.0284 (16)	0.0211 (13)	0.0159 (12)
C12	0.055 (2)	0.049 (2)	0.0538 (19)	0.0067 (16)	−0.0031 (15)	0.0056 (15)
C11	0.050 (2)	0.062 (2)	0.0518 (18)	0.0065 (17)	0.0087 (15)	−0.0008 (15)
C5	0.060 (2)	0.046 (2)	0.0423 (17)	−0.0045 (18)	0.0037 (15)	−0.0013 (14)
N3	0.090 (2)	0.077 (2)	0.0447 (15)	0.0085 (18)	0.0055 (15)	−0.0008 (15)
C6	0.0541 (19)	0.042 (2)	0.0501 (18)	−0.0054 (16)	0.0021 (15)	0.0044 (14)
C14	0.130 (5)	0.101 (5)	0.055 (3)	0.018 (4)	−0.016 (3)	0.010 (3)
C8	0.060 (2)	0.042 (2)	0.0536 (19)	0.0105 (16)	0.0087 (15)	0.0031 (14)
C2	0.130 (4)	0.093 (4)	0.058 (2)	0.029 (3)	0.029 (2)	0.034 (2)
C4	0.068 (2)	0.046 (2)	0.0462 (18)	0.0010 (17)	0.0017 (15)	0.0016 (15)
C1	0.116 (3)	0.086 (3)	0.052 (2)	0.021 (3)	0.024 (2)	0.013 (2)
C13	0.092 (4)	0.122 (5)	0.051 (2)	0.000 (3)	0.016 (2)	−0.018 (2)
C3	0.086 (3)	0.066 (3)	0.058 (2)	0.012 (2)	0.0147 (18)	0.0049 (18)

Geometric parameters (Å, º) top

N2—C5	1.352 (4)	C5—C4	1.447 (4)
N2—N1	1.384 (3)	N3—C14	1.431 (5)
N2—H2A	0.8600	N3—C13	1.441 (5)
N1—C6	1.283 (3)	C6—H6A	0.9300
C9—C8	1.366 (4)	C14—H14A	0.99 (5)
C9—C10	1.393 (4)	C14—H14B	0.95 (5)
C9—H9A	0.9300	C14—H14C	0.92 (7)
O2—C5	1.222 (3)	C8—H8A	0.9300
C7—C8	1.384 (4)	C2—C1	1.317 (5)
C7—C12	1.385 (4)	C2—H2B	0.9300
C7—C6	1.448 (4)	C4—C3	1.336 (4)
C10—C11	1.391 (4)	C1—C3	1.410 (5)
C10—N3	1.385 (3)	C1—H1B	0.9300
O1—C4	1.359 (4)	C13—H13A	0.99 (4)
O1—C2	1.363 (4)	C13—H13B	0.92 (5)
C12—C11	1.371 (4)	C13—H13C	0.95 (6)
C12—H12A	0.9300	C3—H3A	0.9300
C11—H11A	0.9300

C5—N2—N1	118.9 (3)	C7—C6—H6A	119.7
C5—N2—H2A	120.6	N3—C14—H14A	109 (3)
N1—N2—H2A	120.6	N3—C14—H14B	108 (3)
C6—N1—N2	114.0 (3)	H14A—C14—H14B	106 (4)
C8—C9—C10	121.2 (3)	N3—C14—H14C	115 (5)
C8—C9—H9A	119.4	H14A—C14—H14C	112 (6)
C10—C9—H9A	119.4	H14B—C14—H14C	107 (4)
C8—C7—C12	116.7 (3)	C9—C8—C7	121.7 (3)
C8—C7—C6	123.3 (3)	C9—C8—H8A	119.1
C12—C7—C6	119.8 (3)	C7—C8—H8A	119.1
C11—C10—C9	117.7 (3)	C1—C2—O1	110.7 (3)
C11—C10—N3	120.9 (3)	C1—C2—H2B	124.6
C9—C10—N3	121.4 (3)	O1—C2—H2B	124.6
C4—O1—C2	106.0 (3)	C3—C4—O1	109.7 (3)
C11—C12—C7	122.6 (3)	C3—C4—C5	130.8 (3)
C11—C12—H12A	118.7	O1—C4—C5	119.4 (3)
C7—C12—H12A	118.7	C2—C1—C3	106.6 (3)
C12—C11—C10	120.1 (3)	C2—C1—H1B	126.7
C12—C11—H11A	119.9	C3—C1—H1B	126.7
C10—C11—H11A	119.9	N3—C13—H13A	105 (3)
O2—C5—N2	123.8 (3)	N3—C13—H13B	111 (3)
O2—C5—C4	120.5 (3)	H13A—C13—H13B	116 (4)
N2—C5—C4	115.7 (3)	N3—C13—H13C	112 (4)
C10—N3—C14	120.7 (3)	H13A—C13—H13C	110 (4)
C10—N3—C13	120.2 (3)	H13B—C13—H13C	103 (5)
C14—N3—C13	118.2 (4)	C4—C3—C1	106.9 (3)
N1—C6—C7	120.7 (3)	C4—C3—H3A	126.6
N1—C6—H6A	119.7	C1—C3—H3A	126.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.10	2.933 (3)	163

Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅N₃O₂
M_r	257.29
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	10.866 (2), 7.9654 (16), 30.620 (6)
V (Å³)	2650.2 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18964, 2394, 986
R_int	0.172
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.143, 0.75
No. of reflections	2394
No. of parameters	196
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

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···O2ⁱ	0.86	2.10	2.933 (3)	163.0

Symmetry code: (i) −x+1/2, y+1/2, z.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Habermehl, N. C., Angus, P. M. & Kilah, N. L. (2006). Inorg. Chem. 45, 1445–1462. Web of Science CSD CrossRef PubMed CAS Google Scholar
Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1720. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nataliya, E. B., Marina, D. R. & Yuir, A. U. (2007). Chem. Rev. 107, 46–79. PubMed 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 66| Part 10| October 2010| Page o2696

doi:10.1107/S1600536810037244

Open

access