N'-[4-(Dimethyl-amino)-benzyl-idene]furan-2-carbohydrazide.

The title compound, C(14)H(15)N(3)O(2), was prepared by the reaction of 4-(dimethyl-amino)-benzaldehyde and furan-2-carbohydrazide. The dihedral angle between the benzene ring and the furan ring is 25.59 (19)°. In the crystal, mol-ecules are linked by inter-molecular 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 = 257.29

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.143

S = 0.75

2394 reflections

196 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037244/lh5131sup1.cif

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

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

C14H15N3O2	F(000) = 1088
Mr = 257.29	Dx = 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

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

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(Fo2) + (0.0687P)2] where P = (Fo2 + 2Fc2)/3
2394 reflections	(Δ/σ)max = 0.002
196 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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

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

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) .