(E)-N′-(Furan-2-ylmethyl­ene)-4-(quinolin-8-yl­oxy)butanohydrazide

Xie, H.; Meng, S.-M.; Fan, Y.-Q.; Yang, G.-C.

doi:10.1107/S1600536808032674

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2114

doi:10.1107/S1600536808032674

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(E)-N′-(Furan-2-ylmethylene)-4-(quinolin-8-yloxy)butanohydrazide

Hai Xie,^a ^* Shuang-Ming Meng,^a Yue-Qin Fan ^a and Guo-Chen Yang ^a

^aCollege of Chemistry and Chemical Engineering, Shanxi Datong University, Datong, Shanxi 037009, People's Republic of China
^*Correspondence e-mail: haixiedt@126.com

(Received 28 September 2008; accepted 9 October 2008; online 15 October 2008)

In the title molecule, C₁₈H₁₇N₃O₃, the dihedral angle between the mean planes of the furan ring and the quinoline group is 77.4 (2)°. In the crystal structure, intermolecular N—H⋯N hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For general background, see: Cai et al. (2003 ); Chen et al. (2005 ); Park et al. (2006 ); Karmakar et al. (2007 ). For related structures, see: Zheng (2006 ); Zheng, Wu et al. (2006 ); Zheng, Li et al. (2006 ); Zheng et al. (2007 , 2008 ).

Experimental

Crystal data

C₁₈H₁₇N₃O₃
M_r = 323.35
Triclinic, $[P \overline 1]$
a = 8.2685 (17) Å
b = 8.6324 (17) Å
c = 12.765 (3) Å
α = 100.64 (3)°
β = 100.36 (4)°
γ = 109.50 (3)°
V = 814.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.33 × 0.26 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.970, T_max = 0.981
9399 measured reflections
2865 independent reflections
1632 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.193
S = 1.06
2865 reflections
218 parameters
21 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯N1ⁱ	0.86	2.10	2.936 (4)	164
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536808032674/lh2705sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808032674/lh2705Isup2.hkl

checkCIF report

Comment top

Synthsis of 8-Hydroxyquinoline and its derivatives have attracted a great interest due to their interesting biological activities and applications in coordination chemistry (Cai et al., 2003; Chen et al., 2005; Park et al., 2006; Karmakar et al. 2007). Herein, we report the synthesis and crystal structure of the title compound, (I). The molecular structure of (I) is shown in Fig. 1. The conformation along the O1—C10—C11—C12—C13—N2—N3—C14 bond sequence is (-)gauche-trans-trans-(-)gauche-trans. The mean planes of the furan ring and quinoline group make a dihedral angle of 77.4 (2) °. In the crystal structure (Fig. 2), intermolecular N—H···N hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers. Some crystal structures which are closely related to the title compound have already been studied (Zheng, 2006; Zheng, Wu et al.,2006; Zheng, et al.,2007; Zheng, Li et al., 2006; Zheng, et al., 2008.

Related literature top

For general background, see: Cai et al. (2003); Chen et al. (2005); Park et al. (2006); Karmakar et al. (2007). For related structures, see: Zheng (2006); Zheng, Wu et al. (2006); Zheng, Li et al. (2006); Zheng et al. (2007, 2008).

Experimental top

Reagents and solvents used were of commercially available quality. The title complex (I) was synthesized according to the method of Zheng (2006). 4-(Quinolin-8-yloxy)butanohydrazide (0.01 mol), furan-2-carbaldehyde (0.01 mol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask and refluxed for 6 h. After cooling to room temperature, the solid product was separated by filtration. Colourless single crystals suitable for X-ray diffraction study were obtained by slow evaporation of a tetrahydrofuran solution over a period of 2 d.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 with displacement ellipsoids at the 30% probability level.
	Fig. 2. Part of the crystal structure showing hydrogen bonds as dashed lines. H atoms, except for those involved in hydrogen bonds, are not included.

(E)-N'-(Furan-2-ylmethylene)-4-(quinolin-8-yloxy)butanohydrazide top

Crystal data top

C₁₈H₁₇N₃O₃	Z = 2
M_r = 323.35	F(000) = 340
Triclinic, P1	D_x = 1.318 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2685 (17) Å	Cell parameters from 1197 reflections
b = 8.6324 (17) Å	θ = 2.6–20.5°
c = 12.765 (3) Å	µ = 0.09 mm⁻¹
α = 100.64 (3)°	T = 295 K
β = 100.36 (4)°	Block, colorless
γ = 109.50 (3)°	0.33 × 0.26 × 0.21 mm
V = 814.9 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2865 independent reflections
Radiation source: fine-focus sealed tube	1632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.970, T_max = 0.981	k = −10→10
9399 measured reflections	l = −15→15

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)] = 0.058	H-atom parameters constrained
wR(F²) = 0.193	w = 1/[σ²(F_o²) + (0.0865P)² + 0.1859P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2865 reflections	Δρ_max = 0.24 e Å⁻³
218 parameters	Δρ_min = −0.20 e Å⁻³
21 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: 0.015 (6)

Crystal data top

C₁₈H₁₇N₃O₃	γ = 109.50 (3)°
M_r = 323.35	V = 814.9 (4) Å³
Triclinic, P1	Z = 2
a = 8.2685 (17) Å	Mo Kα radiation
b = 8.6324 (17) Å	µ = 0.09 mm⁻¹
c = 12.765 (3) Å	T = 295 K
α = 100.64 (3)°	0.33 × 0.26 × 0.21 mm
β = 100.36 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2865 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1632 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.981	R_int = 0.043
9399 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	21 restraints
wR(F²) = 0.193	H-atom parameters constrained
S = 1.06	Δρ_max = 0.24 e Å⁻³
2865 reflections	Δρ_min = −0.20 e Å⁻³
218 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
N1	0.2058 (3)	0.5842 (4)	0.8792 (2)	0.0700 (8)
N2	−0.0972 (4)	0.3300 (3)	0.3273 (2)	0.0681 (8)
H1	−0.1174	0.3754	0.2743	0.082*
N3	−0.2378 (4)	0.2174 (3)	0.3521 (2)	0.0608 (7)
O1	0.2645 (3)	0.3778 (2)	0.72254 (16)	0.0631 (6)
O2	0.1947 (3)	0.4670 (3)	0.3574 (2)	0.0890 (8)
C16	−0.7219 (5)	0.0732 (5)	0.2779 (3)	0.0811 (10)
H16	−0.7644	0.1349	0.2353	0.097*
C1	0.2775 (4)	0.3409 (4)	0.8220 (3)	0.0682 (9)
C2	0.3186 (5)	0.2071 (5)	0.8455 (4)	0.1060 (15)
H2	0.3394	0.1330	0.7916	0.127*
C3	0.3287 (7)	0.1846 (8)	0.9529 (6)	0.147 (2)
H3	0.3525	0.0920	0.9682	0.176*
C4	0.3056 (7)	0.2905 (10)	1.0325 (5)	0.154 (3)
H4	0.3176	0.2727	1.1026	0.184*
C5	0.2631 (5)	0.4296 (8)	1.0135 (4)	0.1188 (17)
C6	0.2347 (8)	0.5503 (12)	1.0944 (5)	0.164 (3)
H6	0.2409	0.5392	1.1659	0.197*
C7	0.1999 (8)	0.6759 (9)	1.0659 (4)	0.154 (3)
H7	0.1858	0.7570	1.1185	0.185*
C8	0.1837 (5)	0.6903 (6)	0.9582 (3)	0.1034 (15)
H8	0.1556	0.7800	0.9411	0.124*
C9	0.2483 (4)	0.4547 (5)	0.9052 (2)	0.0717 (10)
C10	0.3224 (4)	0.2872 (4)	0.6405 (3)	0.0767 (10)
H10A	0.2543	0.1657	0.6233	0.092*
H10B	0.4470	0.3077	0.6677	0.092*
C11	0.2946 (4)	0.3499 (4)	0.5394 (3)	0.0737 (10)
H11A	0.3515	0.3051	0.4880	0.088*
H11B	0.3517	0.4731	0.5600	0.088*
C12	0.1001 (4)	0.2989 (4)	0.4818 (3)	0.0660 (9)
H12A	0.0446	0.1756	0.4569	0.079*
H12B	0.0413	0.3375	0.5344	0.079*
C13	0.0731 (5)	0.3712 (4)	0.3847 (3)	0.0657 (9)
C14	−0.3915 (4)	0.2060 (4)	0.3007 (2)	0.0617 (8)
H14	−0.3984	0.2746	0.2532	0.074*
C15	−0.5530 (4)	0.0908 (4)	0.3141 (2)	0.0591 (8)
O3	−0.5432 (3)	−0.0227 (3)	0.3737 (2)	0.0872 (8)
C18	−0.7117 (6)	−0.1128 (5)	0.3740 (4)	0.1000 (13)
H18	−0.7433	−0.1998	0.4089	0.120*
C17	−0.8239 (5)	−0.0625 (5)	0.3191 (3)	0.0867 (12)
H17	−0.9466	−0.1055	0.3084	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0610 (17)	0.0779 (18)	0.0552 (16)	0.0069 (14)	0.0221 (13)	0.0102 (14)
N2	0.0650 (18)	0.0685 (17)	0.0741 (17)	0.0177 (14)	0.0275 (14)	0.0316 (14)
N3	0.0621 (17)	0.0560 (15)	0.0643 (15)	0.0150 (13)	0.0258 (13)	0.0206 (12)
O1	0.0712 (14)	0.0671 (13)	0.0592 (13)	0.0337 (11)	0.0168 (10)	0.0224 (10)
O2	0.0729 (17)	0.0872 (17)	0.1058 (19)	0.0133 (13)	0.0390 (14)	0.0396 (14)
C16	0.070 (2)	0.097 (3)	0.073 (2)	0.032 (2)	0.0116 (18)	0.020 (2)
C1	0.0464 (18)	0.068 (2)	0.077 (2)	0.0050 (15)	−0.0011 (15)	0.0366 (19)
C2	0.062 (2)	0.086 (3)	0.154 (4)	0.011 (2)	−0.011 (2)	0.065 (3)
C3	0.086 (3)	0.140 (4)	0.180 (5)	−0.006 (3)	−0.031 (4)	0.122 (4)
C4	0.081 (3)	0.199 (5)	0.126 (4)	−0.028 (3)	−0.024 (3)	0.119 (4)
C5	0.055 (2)	0.178 (4)	0.077 (3)	−0.024 (2)	−0.0051 (19)	0.079 (3)
C6	0.079 (4)	0.269 (8)	0.046 (3)	−0.051 (4)	0.011 (2)	0.031 (4)
C7	0.087 (4)	0.208 (7)	0.067 (4)	−0.039 (4)	0.036 (3)	−0.037 (4)
C8	0.078 (3)	0.109 (3)	0.082 (3)	−0.004 (2)	0.040 (2)	−0.015 (2)
C9	0.0455 (19)	0.092 (3)	0.0510 (19)	−0.0082 (17)	0.0031 (14)	0.0302 (19)
C10	0.061 (2)	0.072 (2)	0.088 (2)	0.0296 (18)	0.0090 (18)	0.0025 (19)
C11	0.058 (2)	0.082 (2)	0.069 (2)	0.0210 (17)	0.0216 (17)	−0.0016 (18)
C12	0.060 (2)	0.0655 (19)	0.069 (2)	0.0189 (16)	0.0242 (16)	0.0123 (16)
C13	0.071 (2)	0.0574 (19)	0.070 (2)	0.0195 (17)	0.0317 (18)	0.0178 (16)
C14	0.067 (2)	0.0621 (19)	0.0605 (18)	0.0215 (16)	0.0234 (16)	0.0245 (15)
C15	0.068 (2)	0.0585 (18)	0.0535 (17)	0.0218 (16)	0.0202 (15)	0.0199 (14)
O3	0.0827 (18)	0.0858 (17)	0.1002 (18)	0.0247 (14)	0.0323 (14)	0.0469 (14)
C18	0.083 (3)	0.092 (3)	0.113 (3)	0.004 (2)	0.046 (3)	0.034 (2)
C17	0.054 (2)	0.096 (3)	0.081 (2)	0.005 (2)	0.0213 (19)	−0.002 (2)

Geometric parameters (Å, º) top

N1—C8	1.314 (4)	C6—C7	1.306 (10)
N1—C9	1.357 (4)	C6—H6	0.9300
N2—C13	1.358 (4)	C7—C8	1.389 (7)
N2—N3	1.374 (3)	C7—H7	0.9300
N2—H1	0.8600	C8—H8	0.9300
N3—C14	1.283 (4)	C10—C11	1.499 (5)
O1—C1	1.360 (4)	C10—H10A	0.9700
O1—C10	1.437 (4)	C10—H10B	0.9700
O2—C13	1.222 (4)	C11—C12	1.517 (4)
C16—C15	1.337 (5)	C11—H11A	0.9700
C16—C17	1.445 (5)	C11—H11B	0.9700
C16—H16	0.9300	C12—C13	1.501 (4)
C1—C2	1.375 (5)	C12—H12A	0.9700
C1—C9	1.419 (5)	C12—H12B	0.9700
C2—C3	1.412 (7)	C14—C15	1.435 (4)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.322 (9)	C15—O3	1.361 (4)
C3—H3	0.9300	O3—C18	1.351 (4)
C4—C5	1.408 (9)	C18—C17	1.300 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C9	1.428 (5)	C17—H17	0.9300
C5—C6	1.436 (9)

C8—N1—C9	117.8 (3)	C1—C9—C5	119.4 (4)
C13—N2—N3	121.3 (3)	O1—C10—C11	107.8 (3)
C13—N2—H1	119.3	O1—C10—H10A	110.2
N3—N2—H1	119.3	C11—C10—H10A	110.2
C14—N3—N2	114.7 (3)	O1—C10—H10B	110.2
C1—O1—C10	118.0 (3)	C11—C10—H10B	110.2
C15—C16—C17	105.0 (3)	H10A—C10—H10B	108.5
C15—C16—H16	127.5	C10—C11—C12	113.4 (3)
C17—C16—H16	127.5	C10—C11—H11A	108.9
O1—C1—C2	124.8 (4)	C12—C11—H11A	108.9
O1—C1—C9	115.0 (3)	C10—C11—H11B	108.9
C2—C1—C9	120.2 (4)	C12—C11—H11B	108.9
C1—C2—C3	118.7 (5)	H11A—C11—H11B	107.7
C1—C2—H2	120.7	C13—C12—C11	113.1 (3)
C3—C2—H2	120.7	C13—C12—H12A	109.0
C4—C3—C2	122.3 (6)	C11—C12—H12A	109.0
C4—C3—H3	118.8	C13—C12—H12B	109.0
C2—C3—H3	118.8	C11—C12—H12B	109.0
C3—C4—C5	121.5 (6)	H12A—C12—H12B	107.8
C3—C4—H4	119.2	O2—C13—N2	119.3 (3)
C5—C4—H4	119.2	O2—C13—C12	123.6 (3)
C4—C5—C9	117.7 (6)	N2—C13—C12	117.1 (3)
C4—C5—C6	125.4 (5)	N3—C14—C15	122.2 (3)
C9—C5—C6	116.8 (6)	N3—C14—H14	118.9
C7—C6—C5	118.9 (6)	C15—C14—H14	118.9
C7—C6—H6	120.5	C16—C15—O3	110.4 (3)
C5—C6—H6	120.5	C16—C15—C14	130.9 (3)
C6—C7—C8	121.1 (7)	O3—C15—C14	118.7 (3)
C6—C7—H7	119.5	C18—O3—C15	106.4 (3)
C8—C7—H7	119.5	C17—C18—O3	111.3 (4)
N1—C8—C7	123.6 (5)	C17—C18—H18	124.4
N1—C8—H8	118.2	O3—C18—H18	124.4
C7—C8—H8	118.2	C18—C17—C16	106.9 (3)
N1—C9—C1	118.9 (3)	C18—C17—H17	126.5
N1—C9—C5	121.7 (4)	C16—C17—H17	126.5

C13—N2—N3—C14	171.9 (3)	C6—C5—C9—N1	−1.4 (5)
C10—O1—C1—C2	−9.5 (4)	C4—C5—C9—C1	−0.4 (5)
C10—O1—C1—C9	169.3 (2)	C6—C5—C9—C1	179.1 (4)
O1—C1—C2—C3	179.6 (3)	C1—O1—C10—C11	179.9 (2)
C9—C1—C2—C3	0.8 (5)	O1—C10—C11—C12	−68.5 (3)
C1—C2—C3—C4	−2.2 (7)	C10—C11—C12—C13	176.4 (3)
C2—C3—C4—C5	2.2 (9)	N3—N2—C13—O2	177.3 (3)
C3—C4—C5—C9	−0.9 (7)	N3—N2—C13—C12	−4.6 (4)
C3—C4—C5—C6	179.6 (5)	C11—C12—C13—O2	−2.9 (4)
C4—C5—C6—C7	178.5 (5)	C11—C12—C13—N2	179.1 (3)
C9—C5—C6—C7	−1.0 (8)	N2—N3—C14—C15	178.1 (3)
C5—C6—C7—C8	2.4 (10)	C17—C16—C15—O3	0.2 (4)
C9—N1—C8—C7	−0.6 (5)	C17—C16—C15—C14	−179.2 (3)
C6—C7—C8—N1	−1.7 (8)	N3—C14—C15—C16	172.0 (3)
C8—N1—C9—C1	−178.4 (3)	N3—C14—C15—O3	−7.3 (4)
C8—N1—C9—C5	2.1 (4)	C16—C15—O3—C18	0.0 (4)
O1—C1—C9—N1	2.0 (4)	C14—C15—O3—C18	179.5 (3)
C2—C1—C9—N1	−179.2 (3)	C15—O3—C18—C17	−0.2 (4)
O1—C1—C9—C5	−178.5 (3)	O3—C18—C17—C16	0.3 (5)
C2—C1—C9—C5	0.4 (4)	C15—C16—C17—C18	−0.2 (4)
C4—C5—C9—N1	179.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N1ⁱ	0.86	2.10	2.936 (4)	164

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇N₃O₃
M_r	323.35
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.2685 (17), 8.6324 (17), 12.765 (3)
α, β, γ (°)	100.64 (3), 100.36 (4), 109.50 (3)
V (Å³)	814.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.33 × 0.26 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.970, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	9399, 2865, 1632
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.193, 1.06
No. of reflections	2865
No. of parameters	218
No. of restraints	21
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.20

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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—H1···N1ⁱ	0.86	2.10	2.936 (4)	164

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

This work was supported by a key grant from the Shanxi Datong University Foundation of Shanxi Province (grant No. 2008K1).

References

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