(E) Quinoline 4 carbaldehyde oxime

organic papers

Acta Cryst.(2007). E63, o329–o330 doi:10.1107/S1600536806053426 Zhouet al. _C

10H8N2O

o329

Acta Crystallographica Section E Structure Reports Online

ISSN 1600-5368

(

E

)-Quinoline-4-carbaldehyde oxime

Fu-Hui Zhou,aHong-Bin Zhao,a* Xiao-Dan Gu,bZhi-Gang Licand Jing-Wei Xuc*

a_{Department of Organic Chemistry, The College}

of Chemistry, Xiangtan University, Hunan 411105, People’s Republic of China,

b_{Department of Applied Chemistry, The College}

of Chemistry, Xiangtan University, Hunan 411105, People’s Republic of China, and

c

National Analytical Research Center of Electrochemistry and Spectroscopy, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, People’s Republic of China

Correspondence e-mail:

[email protected], [email protected]

Key indicators

Single-crystal X-ray study T= 293 K

Mean(C–C) = 0.002 A˚ Rfactor = 0.047 wRfactor = 0.134

Data-to-parameter ratio = 14.1

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 7 December 2006 Accepted 10 December 2006

#2007 International Union of Crystallography

All rights reserved

The title compound, C10H8N2O, exists as the Eisomer. The crystal packing is stabilized by intermolecular O—H N and C—H N hydrogen bonds, as well as–stacking.

Comment

The title compound, (I), was synthesized to support our ongoing drug development program. Its structure is shown in Fig. 1. The molecule exists as theEisomer.

In the structure there are two kinds of intermolecular hydrogen bonds, namely O—H N and C—H N (Table 1). These generate a dimericR2

2(7) motif (Bernsteinet al., 1995), and assemble these dimers into one-dimensional supra-molecular chains (Fig. 2). The chains are arranged in an antiparallel fashion and are stabilized by–stacking inter-actions between the quinoline rings at (x,y,z) and (x+ 1.272,

y+ 0.321, z+ 3.342) with centroid-to-centroid distances of 3.590 (2) A˚ .

Figure 1

Experimental

Compound (I) was prepared according to a known procedure (Ginsburg & Wilson, 1957). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution at room temperature.

Crystal data

C10H8N2O Mr= 172.18

Monoclinic,P21=c a= 8.161 (2) A˚

b= 15.746 (4) A˚

c= 7.1509 (18) A˚

= 110.826 (4)

V= 858.8 (4) A˚3

Z= 4

Dx= 1.332 Mg m

3

MoKradiation

= 0.09 mm1 T= 293 (2) K Prism, colorless 0.250.150.10 mm

Data collection

Bruker SMART APEX diffractometer

’and!scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996)

Tmin= 0.978,Tmax= 0.991

4737 measured reflections 1688 independent reflections 1441 reflections withI> 2(I)

Rint= 0.015

max= 26.1

Refinement

Refinement onF2 R[F2_{> 2(F}2_{)] = 0.047} wR(F2) = 0.134

S= 1.04 1688 reflections 120 parameters

H-atom parameters constrained

w= 1/[2

(Fo2) + (0.0805P)2

+ 0.1178P]

whereP= (Fo2+ 2Fc2)/3

(/)max< 0.001

max= 0.17 e A˚

3

min=0.22 e A˚

3

Extinction correction:SHELXL97

Extinction coefficient: 0.051 (7)

Table 1

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

O1—H1 N1i

0.82 1.97 2.782 (2) 171 C10—H10 N2ii 0.93 2.56 3.377 (3) 146

Symmetry codes: (i)xþ1;y1

2;zþ12; (ii)xþ1;yþ12;zþ12.

The hydroxy H atom was located in a difference Fourier map and refined as riding in its as-found relative position, with Uiso(H) =

1.5Ueq(O), while other H atoms were placed in calculated positions

(C—H = 0.93 A˚ ) and refined in riding mode, withUiso(H) = 1.2Ueq(C)

Data collection:SMART(Bruker, 1998); cell refinement:SAINT

(Bruker, 2003); data reduction:SAINT; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:

SHELXTL (Bruker, 1997); software used to prepare material for publication:SHELXTL.

This work is supported by the National Analytical Research Center of Electrochemistry and Spectroscopy, Changchun Institute of Applied Chemistry, Changchun, China.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995).Angew. Chem. Int. Ed. Engl.34, 1555–1573.

Bruker (1997).SHELXTLReference Manual. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (1998).SMART Software Reference Manual. Version 5.0. Bruker AXS Inc., Madison, Wisconsion, USA.

Bruker (2003).SAINT Software Reference Manual. Version 6. Bruker AXS Inc., Madison, Wisconsion, USA.

Ginsburg, S. & Wilson, I. R. (1957).J. Am. Chem. Soc.79, 481–483. Sheldrick, G. M. (1996).SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of

Go¨ttingen, Germany.

Figure 2

supporting information

sup-1 Acta Cryst. (2007). E63, o329–o330

supporting information

Acta Cryst. (2007). E63, o329–o330 [https://doi.org/10.1107/S1600536806053426]

(

E

)-Quinoline-4-carbaldehyde oxime

Fu-Hui Zhou, Hong-Bin Zhao, Xiao-Dan Gu, Zhi-Gang Li and Jing-Wei Xu

(E)-Quinoline-4-carbaldehyde oxime

Crystal data

C10H8N2O

Mr = 172.18

Monoclinic, P21/c

Hall symbol: -P 2ybc

a = 8.161 (2) Å

b = 15.746 (4) Å

c = 7.1509 (18) Å

β = 110.826 (4)°

V = 858.8 (4) Å3

Z = 4

F(000) = 360

Dx = 1.332 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2173 reflections

θ = 2.6–26.1°

µ = 0.09 mm−1

T = 293 K Prism, colorless 0.25 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

φ and ω scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996)

Tmin = 0.978, Tmax = 0.991

4737 measured reflections 1688 independent reflections 1441 reflections with I > 2σ(I)

Rint = 0.015

θmax = 26.1°, θmin = 2.6°

h = −10→8

k = −17→19

l = −7→8

Refinement

Refinement on F2

Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.047}

wR(F2_{) = 0.134}

S = 1.04 1688 reflections 120 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2_(F

o2) + (0.0805P)2 + 0.1178P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

Extinction correction: SHELXL97, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2θ)]-1/4

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 F}2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

N1 0.54839 (15) 0.28890 (7) 0.17710 (18) 0.0482 (3) N2 0.33039 (16) −0.00720 (7) 0.1929 (2) 0.0536 (4) O1 0.22115 (14) −0.07671 (6) 0.1716 (2) 0.0734 (4)

H1 0.2804 −0.1191 0.2164 0.110*

C1 0.26701 (17) 0.22135 (8) 0.13337 (18) 0.0392 (3) C2 0.37347 (18) 0.29438 (8) 0.14897 (19) 0.0425 (3) C3 0.34699 (17) 0.14002 (8) 0.14489 (19) 0.0421 (3) C4 0.52148 (18) 0.13711 (9) 0.1682 (2) 0.0482 (4)

H4 0.5768 0.0851 0.1733 0.058*

C5 0.61525 (18) 0.21239 (9) 0.1841 (2) 0.0492 (4)

H5 0.7333 0.2083 0.2009 0.059*

C6 0.24744 (19) 0.06138 (9) 0.1333 (2) 0.0519 (4)

H6 0.1255 0.0619 0.0831 0.062*

C7 0.08872 (18) 0.23349 (9) 0.1088 (2) 0.0469 (4)

H7 0.0167 0.1865 0.0977 0.056*

C8 0.02109 (19) 0.31323 (10) 0.1013 (2) 0.0535 (4)

H8 −0.0959 0.3201 0.0872 0.064*

C9 0.1267 (2) 0.38488 (10) 0.1147 (2) 0.0577 (4)

H9 0.0789 0.4389 0.1085 0.069*

C10 0.2987 (2) 0.37606 (9) 0.1369 (2) 0.0535 (4)

H10 0.3672 0.4240 0.1441 0.064*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

supporting information

sup-3 Acta Cryst. (2007). E63, o329–o330

C9 0.0632 (9) 0.0401 (8) 0.0634 (9) 0.0147 (7) 0.0147 (7) 0.0021 (6) C10 0.0596 (9) 0.0349 (7) 0.0606 (9) −0.0004 (6) 0.0148 (7) 0.0009 (6)

Geometric parameters (Å, º)

N1—C5 1.3161 (17) C4—C5 1.3934 (18)

N1—C2 1.3716 (18) C4—H4 0.9300

N2—C6 1.2653 (18) C5—H5 0.9300

N2—O1 1.3854 (15) C6—H6 0.9300

O1—H1 0.8200 C7—C8 1.3648 (19)

C1—C7 1.415 (2) C7—H7 0.9300

C1—C2 1.4215 (18) C8—C9 1.402 (2)

C1—C3 1.4263 (17) C8—H8 0.9300

C2—C10 1.4132 (19) C9—C10 1.362 (2)

C3—C4 1.3744 (19) C9—H9 0.9300

C3—C6 1.4670 (18) C10—H10 0.9300

C5—N1—C2 117.32 (11) C4—C5—H5 117.7

C6—N2—O1 113.02 (12) N2—C6—C3 118.83 (13)

N2—O1—H1 109.5 N2—C6—H6 120.6

C7—C1—C2 118.24 (11) C3—C6—H6 120.6

C7—C1—C3 123.89 (12) C8—C7—C1 120.85 (13)

C2—C1—C3 117.87 (12) C8—C7—H7 119.6

N1—C2—C10 118.08 (12) C1—C7—H7 119.6

N1—C2—C1 122.39 (12) C7—C8—C9 120.50 (13)

C10—C2—C1 119.53 (13) C7—C8—H8 119.8

C4—C3—C1 118.03 (11) C9—C8—H8 119.8

C4—C3—C6 120.51 (11) C10—C9—C8 120.57 (13)

C1—C3—C6 121.45 (12) C10—C9—H9 119.7

C3—C4—C5 119.78 (12) C8—C9—H9 119.7

C3—C4—H4 120.1 C9—C10—C2 120.31 (13)

C5—C4—H4 120.1 C9—C10—H10 119.8

N1—C5—C4 124.57 (13) C2—C10—H10 119.8

N1—C5—H5 117.7

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

O1—H1···N1i _{0.82 1.97 2.782 (2) 171}

C10—H10···N2ii _{0.93 2.56 3.377 (3) 146}