(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

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

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808032674/lh2705sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808032674/lh2705Isup2.hkl Contains datablock I

CCDC reference: 665463

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.007 Å
R factor = 0.058
wR factor = 0.193
Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   295.000
            Value of melting point given =     0.000
PLAT213_ALERT_2_C Atom C6      has ADP max/min Ratio .............       3.10 prola
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     --  C15     ..       5.97 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.28
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       2.50 Sigma
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         21

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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).