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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1744.
Published online 2009 July 4. doi:  10.1107/S1600536809024957
PMCID: PMC2977343

(Z)-N′-(4-Hydr­oxy-4-methyl­pentan-2-yl­idene)-2-(8-quinol­yloxy)acetohydrazide

Abstract

The title compound, C17H21N3O3, has a Z configuration about the N=N double bond. The molecular conformation is stabilized by intramolecular N—H(...)O and O—H(...)N hydrogen bonds.

Related literature

For the potential pharmacological and anti­tumor properties of acidamide compounds, see: Harrop et al. (2003 [triangle]); Ren et al. (2002 [triangle]). For related structures, see: Lei et al. (2008 [triangle]); Yang et al. (2007 [triangle]).

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Object name is e-65-o1744-scheme1.jpg

Experimental

Crystal data

  • C17H21N3O3
  • M r = 315.37
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1744-efi1.jpg
  • a = 9.3297 (12) Å
  • b = 10.1621 (13) Å
  • c = 18.213 (2) Å
  • V = 1726.7 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 273 K
  • 0.20 × 0.18 × 0.15 mm

Data collection

  • Rigaku Saturn 724+ CCD detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 [triangle]) T min = 0.983, T max = 0.987
  • 9084 measured reflections
  • 1761 independent reflections
  • 1593 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.101
  • S = 1.04
  • 1761 reflections
  • 212 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: CrystalClear (Rigaku, 2000 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024957/fj2222sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024957/fj2222Isup2.hkl

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

Acknowledgments

This work was supported by Jilin University.

supplementary crystallographic information

Comment

Acidamide compounds have been found to possess potential pharmacological and antitumor properties (Harrop et al.,2003; Ren et al.,2002). Up to now, a scant few of Acidamide compounds have been appeared (Lei et al.,2008; Yang et al.,2007). As a further study of such compounds, we report here the structure of the title compound.

In the molecule of (I) (Fig. 1), the bond lengths and angles are within normal ranges. In the crystal structure, intramolecular O—H···N and N—H···O hydrogen bonds (Table 1) seem to be effective in the stabilization of the structure.

Experimental

3-hydroxy-3-methylbutanal (0.1 mmol, 10.2 mg) and 2-(quinolin-8-yloxy)acetohydrazide (0.1 mmol, 21.7 mg) were dissolved in methanol(20 ml). Then the mixture was stirred and refluxed for 1 h, and cooled to room temperature. After keeping the solution in air for about two weeks, yellow block crystals of the title compound were abtained. yield: 60% (based on 2-(quinolin-8-yloxy)acetohydrazide). Anal calcd for C17H21N3O3: C, 64.74%; H, 6.71%; N, 13.32%. Found: C, 64.46%; H, 6.48%; N, 13.59%.

Refinement

H atoms of OH and NH groups were located in difference syntheses and constrained to ride on its parent atom [O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O) (for OH); N—H = 0.86 Å and Uiso(H) = 1.2Ueq(N) (for NH)]. The remaining H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.2 for aromatic and methylene H atoms, and x = 1.5 for methyl H atoms.

Friedel data were measured by MoKa radiation, but as there are no atoms heavier than Si, the absolute structure cannot been determined reliably and Friedel-pair data were averaged.

Figures

Fig. 1.
The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres. The O—H···N and N—H···O intramolecular hydrogen bond ...
Fig. 2.
The crystal packing for (I).

Crystal data

C17H21N3O3F(000) = 672
Mr = 315.37Dx = 1.213 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4517 reflections
a = 9.3297 (12) Åθ = 2.2–24.9°
b = 10.1621 (13) ŵ = 0.09 mm1
c = 18.213 (2) ÅT = 273 K
V = 1726.7 (4) Å3Block, colorless
Z = 40.20 × 0.18 × 0.15 mm

Data collection

Rigaku Saturn 724+ CCD detector diffractometer1761 independent reflections
Radiation source: fine-focus sealed tube1593 reflections with I > 2σ(I)
graphiteRint = 0.025
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 2.2°
ω scansh = −11→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)k = −12→11
Tmin = 0.983, Tmax = 0.987l = −20→21
9084 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0681P)2 + 0.1302P] where P = (Fo2 + 2Fc2)/3
1761 reflections(Δ/σ)max = 0.001
212 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = −0.16 e Å3

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)

xyzUiso*/Ueq
O1−0.14080 (16)−0.04549 (14)0.89142 (8)0.0517 (4)
O2−0.0517 (2)−0.26572 (17)1.03499 (9)0.0689 (5)
O30.06563 (17)0.17486 (16)0.93454 (10)0.0610 (4)
H30.05650.14300.89340.091*
N1−0.0639 (2)0.1419 (2)0.79583 (10)0.0575 (5)
N20.03984 (19)−0.06920 (18)0.99886 (10)0.0520 (4)
H20.0391−0.00950.96540.062*
N30.1400 (2)−0.06223 (19)1.05559 (10)0.0570 (5)
C1−0.0301 (3)0.2370 (3)0.74871 (15)0.0738 (7)
H10.05750.27910.75510.089*
C2−0.1156 (4)0.2780 (3)0.69090 (14)0.0781 (8)
H2A−0.08600.34580.66010.094*
C3−0.2431 (3)0.2174 (3)0.68019 (13)0.0717 (8)
H3A−0.30140.24250.64120.086*
C4−0.2882 (3)0.1155 (2)0.72835 (12)0.0578 (6)
C5−0.4203 (3)0.0503 (3)0.72093 (14)0.0721 (7)
H5−0.48270.07290.68320.087*
C6−0.4560 (3)−0.0455 (3)0.76902 (15)0.0750 (7)
H6−0.5429−0.08920.76320.090*
C7−0.3655 (3)−0.0816 (3)0.82796 (13)0.0628 (6)
H7−0.3934−0.14690.86070.075*
C8−0.2363 (2)−0.0194 (2)0.83633 (11)0.0478 (5)
C9−0.1937 (2)0.0816 (2)0.78632 (11)0.0488 (5)
C10−0.1728 (2)−0.1518 (2)0.94005 (12)0.0542 (5)
H10A−0.1828−0.23260.91220.065*
H10B−0.2628−0.13490.96490.065*
C11−0.0544 (2)−0.1672 (2)0.99604 (11)0.0492 (5)
C120.2509 (3)0.0078 (2)1.04208 (14)0.0640 (6)
C130.2906 (3)0.0687 (3)0.96876 (16)0.0684 (7)
H13A0.26990.00510.93050.082*
H13B0.39320.08410.96840.082*
C140.2151 (3)0.1985 (3)0.94902 (19)0.0747 (8)
C150.3571 (4)0.0213 (3)1.10411 (19)0.1010 (12)
H15A0.4434−0.02521.09200.151*
H15B0.3167−0.01491.14820.151*
H15C0.37860.11271.11170.151*
C160.2178 (4)0.2961 (3)1.0126 (3)0.1322 (18)
H16A0.16060.26291.05230.198*
H16B0.17970.37910.99650.198*
H16C0.31470.30801.02900.198*
C170.2846 (4)0.2557 (5)0.8806 (3)0.156 (2)
H17A0.23520.33460.86650.234*
H17B0.27920.19270.84130.234*
H17C0.38320.27570.89060.234*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0499 (8)0.0465 (8)0.0587 (8)−0.0073 (7)−0.0036 (7)0.0125 (7)
O20.0794 (11)0.0569 (9)0.0705 (10)−0.0125 (9)−0.0105 (9)0.0225 (8)
O30.0504 (8)0.0505 (9)0.0819 (10)−0.0052 (7)−0.0098 (8)0.0055 (8)
N10.0578 (11)0.0573 (11)0.0576 (10)−0.0058 (10)0.0067 (9)0.0118 (9)
N20.0524 (10)0.0476 (9)0.0559 (9)−0.0032 (8)−0.0013 (8)0.0081 (8)
N30.0623 (11)0.0507 (10)0.0580 (10)−0.0003 (9)−0.0067 (9)−0.0015 (9)
C10.0736 (17)0.0745 (17)0.0733 (15)−0.0074 (14)0.0140 (14)0.0225 (14)
C20.089 (2)0.0799 (18)0.0652 (15)0.0027 (17)0.0173 (15)0.0288 (14)
C30.086 (2)0.0785 (17)0.0504 (12)0.0184 (16)0.0044 (13)0.0145 (12)
C40.0641 (14)0.0624 (14)0.0468 (11)0.0124 (11)0.0033 (10)−0.0003 (10)
C50.0668 (15)0.0862 (19)0.0634 (13)0.0068 (15)−0.0140 (12)0.0047 (15)
C60.0607 (14)0.0828 (18)0.0814 (16)−0.0112 (14)−0.0151 (13)0.0023 (15)
C70.0557 (14)0.0650 (14)0.0677 (13)−0.0069 (12)−0.0026 (11)0.0073 (12)
C80.0501 (11)0.0445 (10)0.0487 (10)0.0018 (9)0.0024 (9)−0.0001 (8)
C90.0541 (12)0.0448 (10)0.0475 (10)0.0065 (10)0.0069 (9)−0.0008 (9)
C100.0549 (12)0.0460 (11)0.0616 (12)−0.0079 (10)0.0025 (10)0.0130 (10)
C110.0518 (11)0.0444 (11)0.0513 (10)−0.0004 (10)0.0060 (9)0.0059 (9)
C120.0616 (13)0.0463 (11)0.0839 (15)0.0000 (11)−0.0131 (13)0.0044 (11)
C130.0457 (12)0.0603 (13)0.0992 (17)−0.0002 (11)−0.0014 (13)0.0088 (14)
C140.0490 (13)0.0541 (13)0.121 (2)−0.0120 (11)−0.0157 (15)0.0222 (15)
C150.105 (3)0.0767 (19)0.121 (2)−0.0196 (19)−0.051 (2)0.0065 (19)
C160.100 (3)0.0574 (17)0.239 (5)0.0046 (17)−0.081 (3)−0.032 (2)
C170.064 (2)0.174 (4)0.231 (5)−0.028 (2)−0.006 (3)0.137 (4)

Geometric parameters (Å, °)

O1—C81.368 (2)C7—C81.370 (3)
O1—C101.429 (2)C7—H70.9300
O2—C111.228 (3)C8—C91.429 (3)
O3—C141.440 (3)C10—C111.512 (3)
O3—H30.8200C10—H10A0.9700
N1—C11.331 (3)C10—H10B0.9700
N1—C91.368 (3)C12—C151.508 (4)
N2—C111.329 (3)C12—C131.518 (4)
N2—N31.395 (3)C13—C141.538 (4)
N2—H20.8600C13—H13A0.9700
N3—C121.280 (3)C13—H13B0.9700
C1—C21.385 (4)C14—C171.520 (5)
C1—H10.9300C14—C161.525 (5)
C2—C31.354 (4)C15—H15A0.9600
C2—H2A0.9300C15—H15B0.9600
C3—C41.421 (4)C15—H15C0.9600
C3—H3A0.9300C16—H16A0.9600
C4—C51.406 (4)C16—H16B0.9600
C4—C91.418 (3)C16—H16C0.9600
C5—C61.351 (4)C17—H17A0.9600
C5—H50.9300C17—H17B0.9600
C6—C71.414 (4)C17—H17C0.9600
C6—H60.9300
C8—O1—C10117.74 (16)C11—C10—H10B109.6
C14—O3—H3109.5H10A—C10—H10B108.2
C1—N1—C9117.0 (2)O2—C11—N2125.1 (2)
C11—N2—N3120.64 (17)O2—C11—C10119.26 (19)
C11—N2—H2119.7N2—C11—C10115.61 (17)
N3—N2—H2119.7N3—C12—C15115.9 (2)
C12—N3—N2115.31 (18)N3—C12—C13126.4 (2)
N1—C1—C2124.9 (3)C15—C12—C13117.5 (2)
N1—C1—H1117.5C12—C13—C14116.3 (2)
C2—C1—H1117.5C12—C13—H13A108.2
C3—C2—C1118.6 (3)C14—C13—H13A108.2
C3—C2—H2A120.7C12—C13—H13B108.2
C1—C2—H2A120.7C14—C13—H13B108.2
C2—C3—C4120.2 (2)H13A—C13—H13B107.4
C2—C3—H3A119.9O3—C14—C17109.0 (3)
C4—C3—H3A119.9O3—C14—C16105.3 (3)
C5—C4—C9120.2 (2)C17—C14—C16111.5 (3)
C5—C4—C3122.9 (2)O3—C14—C13110.1 (2)
C9—C4—C3116.9 (2)C17—C14—C13108.9 (3)
C6—C5—C4119.6 (2)C16—C14—C13111.9 (3)
C6—C5—H5120.2C12—C15—H15A109.5
C4—C5—H5120.2C12—C15—H15B109.5
C5—C6—C7122.1 (3)H15A—C15—H15B109.5
C5—C6—H6119.0C12—C15—H15C109.5
C7—C6—H6119.0H15A—C15—H15C109.5
C8—C7—C6119.4 (2)H15B—C15—H15C109.5
C8—C7—H7120.3C14—C16—H16A109.5
C6—C7—H7120.3C14—C16—H16B109.5
O1—C8—C7124.42 (19)H16A—C16—H16B109.5
O1—C8—C9115.21 (18)C14—C16—H16C109.5
C7—C8—C9120.4 (2)H16A—C16—H16C109.5
N1—C9—C4122.4 (2)H16B—C16—H16C109.5
N1—C9—C8119.15 (19)C14—C17—H17A109.5
C4—C9—C8118.4 (2)C14—C17—H17B109.5
O1—C10—C11110.08 (17)H17A—C17—H17B109.5
O1—C10—H10A109.6C14—C17—H17C109.5
C11—C10—H10A109.6H17A—C17—H17C109.5
O1—C10—H10B109.6H17B—C17—H17C109.5
C11—N2—N3—C12159.0 (2)C5—C4—C9—C8−0.1 (3)
C9—N1—C1—C2−0.6 (4)C3—C4—C9—C8179.3 (2)
N1—C1—C2—C3−0.5 (5)O1—C8—C9—N11.0 (3)
C1—C2—C3—C41.0 (4)C7—C8—C9—N1−179.8 (2)
C2—C3—C4—C5178.9 (3)O1—C8—C9—C4−179.09 (18)
C2—C3—C4—C9−0.4 (3)C7—C8—C9—C40.1 (3)
C9—C4—C5—C6−0.5 (4)C8—O1—C10—C11178.94 (17)
C3—C4—C5—C6−179.8 (3)N3—N2—C11—O2−9.8 (3)
C4—C5—C6—C71.1 (4)N3—N2—C11—C10169.88 (18)
C5—C6—C7—C8−1.1 (4)O1—C10—C11—O2−168.6 (2)
C10—O1—C8—C75.2 (3)O1—C10—C11—N211.7 (3)
C10—O1—C8—C9−175.65 (17)N2—N3—C12—C15177.3 (2)
C6—C7—C8—O1179.5 (2)N2—N3—C12—C13−7.7 (3)
C6—C7—C8—C90.4 (3)N3—C12—C13—C1481.1 (3)
C1—N1—C9—C41.3 (3)C15—C12—C13—C14−104.0 (3)
C1—N1—C9—C8−178.8 (2)C12—C13—C14—O3−69.5 (3)
C5—C4—C9—N1179.8 (2)C12—C13—C14—C17171.0 (3)
C3—C4—C9—N1−0.8 (3)C12—C13—C14—C1647.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···N10.822.102.820 (3)146
N2—H2···O30.861.972.753 (2)151

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2222).

References

  • Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun pp. 410–411. [PubMed]
  • Lei, J.-T., Jiang, Y.-X., Tao, L.-Y., Huang, S.-S. & Zhang, H.-L. (2008). Acta Cryst. E64, o909. [PMC free article] [PubMed]
  • Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem.45, 410–419. [PubMed]
  • Rigaku (2000). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yang, D. S. (2007). J. Chem. Crystallogr.37, 343–348.

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