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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o26.
Published online 2009 December 4. doi:  10.1107/S160053680905082X
PMCID: PMC2980243

2-(2-{[2-(2-Pyridylcarbon­yl)hydrazono]meth­yl}phen­oxy)acetic acid

Abstract

In the title compound, C15H13N3O4, the pyridine and benzene rings are nearly coplanar [dihedral angle = 4.92 (12)°]. The maximum deviation from the best least-squares plane calculated for the main mol­ecular skeleton is 0.1722 (1) Å for the carbonyl O atom. In the crystal, inter­molecular O—H(...)O hydrogen bonds connect the mol­ecules into a chain, while π–π stacking inter­actions between the pyridine and benzene rings [centroid–centroid distance = 3.9162 (8) Å and offset angle = 27.20°] complete a two-dimensional network.

Related literature

For Schiff bases complexes containing (O-oxyacetic acid)benzaldehyde, see: Wu et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-00o26-scheme1.jpg

Experimental

Crystal data

  • C15H13N3O4
  • M r = 299.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00o26-efi1.jpg
  • a = 8.871 (2) Å
  • b = 9.042 (2) Å
  • c = 17.389 (4) Å
  • β = 94.765 (3)°
  • V = 1390.0 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 296 K
  • 0.16 × 0.15 × 0.04 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1998 [triangle]) T min = 0.983, T max = 0.996
  • 11832 measured reflections
  • 3194 independent reflections
  • 1512 reflections with I > 2σ(I)
  • R int = 0.074

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.125
  • S = 0.99
  • 3194 reflections
  • 200 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; 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/S160053680905082X/kp2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905082X/kp2238Isup2.hkl

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

Acknowledgments

We acknowledge financial support by the Key Laboratory of Non-ferrous Metals and Materials Processing Technology, Ministry of Education, P. R. China.

supplementary crystallographic information

Comment

The molecular structure of (I) (Fig.1) reveals the nearly planar system; the dihedral angle between the pyridine and benzene rings is 4.923°. An intermolecular O–H···O hydrogen bond connects molecules into a chain (Table 1, Fig.2). The pyridine ring (1-x,-1/2+y,1/2-z) is parallel to the benzene ring (-x,-1/2+y,1/2-z) with a perpendicular distance of 3.3239 Å: a centroid–centroid = 3.9162 (8) Å and an offset angle = 27.197° (calculated as the angle between the line through the two centroids of the pyridine ring and the benzene ring and a normal to the pyridine plane. Thus pi–pi stacking interactions complete a two dimensional network (Fig.2).

Experimental

A methanol solution (10 ml) was added to an acetone solution (10 ml) of the 2-(2-methoxyacetic acid)benzaldehyde picoloylhydrazone (0.5 mmol). After stirring at 35\ % for 2 h, crystals of the title compound were obtained by slow evaporation of the mixture at room temperature.

Refinement

H atoms were placed at calculated positions (C–H = 0.93 Å and O—H = 0.82 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2Ueq(C, N) and [Uiso(H) = 1.5Ueq(O)].

Figures

Fig. 1.
The molecular structure of (I), showing 30% probability displacement ellipsoids for non-H atoms. H atoms bound to C and N have been omitted.
Fig. 2.
Partial packing diagram showing a hydrogen-bonded chain running along the a axis.

Crystal data

C15H13N3O4F(000) = 624
Mr = 299.28Dx = 1.430 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1231 reflections
a = 8.871 (2) Åθ = 2.3–20.3°
b = 9.042 (2) ŵ = 0.11 mm1
c = 17.389 (4) ÅT = 296 K
β = 94.765 (3)°Block, colourless
V = 1390.0 (5) Å30.16 × 0.15 × 0.04 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer3194 independent reflections
Radiation source: fine-focus sealed tube1512 reflections with I > 2σ(I)
graphiteRint = 0.074
[var phi] and ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −11→11
Tmin = 0.983, Tmax = 0.996k = −11→10
11832 measured reflectionsl = −22→22

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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0467P)2 + 0.0303P] where P = (Fo2 + 2Fc2)/3
3194 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.19 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
N10.5796 (2)0.6090 (2)0.33901 (11)0.0446 (5)
C20.6090 (3)0.5119 (2)0.39612 (13)0.0353 (6)
C30.7443 (3)0.5054 (3)0.44083 (14)0.0436 (6)
H30.75960.43640.48030.052*
C40.8563 (3)0.6037 (3)0.42557 (15)0.0513 (7)
H40.94880.60270.45490.062*
C50.8296 (3)0.7032 (3)0.36644 (16)0.0538 (7)
H50.90440.76920.35430.065*
C60.4850 (2)0.4041 (3)0.40971 (13)0.0371 (6)
C70.1114 (3)0.3732 (2)0.33134 (13)0.0409 (6)
H70.11030.45550.29930.049*
C8−0.0249 (3)0.2837 (3)0.33563 (14)0.0400 (6)
C9−0.0354 (3)0.1807 (3)0.39414 (15)0.0514 (7)
H90.04650.16690.43040.062*
C10−0.1651 (3)0.0984 (3)0.39943 (16)0.0598 (8)
H10−0.17090.03020.43910.072*
C11−0.2859 (3)0.1183 (3)0.34527 (17)0.0600 (8)
H11−0.37330.06250.34840.072*
C12−0.2790 (3)0.2190 (3)0.28689 (15)0.0497 (7)
H12−0.36110.23090.25060.060*
C13−0.1494 (3)0.3035 (3)0.28189 (14)0.0412 (6)
C14−0.2598 (3)0.4491 (3)0.17649 (14)0.0487 (7)
H14A−0.24420.54710.15590.058*
H14B−0.34840.45310.20560.058*
C15−0.2888 (3)0.3425 (3)0.11069 (14)0.0426 (6)
C10.6908 (3)0.7033 (3)0.32572 (15)0.0541 (7)
H10.67270.77290.28660.065*
N20.3553 (2)0.4263 (2)0.36523 (10)0.0414 (5)
H20.34950.49710.33210.050*
N30.2323 (2)0.3368 (2)0.37230 (11)0.0401 (5)
O10.50069 (18)0.30437 (19)0.45682 (10)0.0563 (5)
O2−0.13215 (17)0.40989 (18)0.22698 (9)0.0486 (5)
O3−0.21338 (19)0.2346 (2)0.10071 (10)0.0603 (5)
O4−0.4074 (2)0.38551 (19)0.06633 (10)0.0612 (6)
H4A−0.42610.32450.03200.092*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0383 (12)0.0473 (13)0.0471 (13)−0.0034 (10)−0.0024 (10)0.0064 (11)
C20.0341 (13)0.0374 (14)0.0346 (14)0.0014 (11)0.0031 (11)−0.0057 (11)
C30.0408 (15)0.0490 (16)0.0399 (14)0.0042 (12)−0.0036 (12)−0.0018 (12)
C40.0336 (14)0.0615 (18)0.0570 (18)−0.0024 (13)−0.0074 (12)−0.0081 (15)
C50.0400 (16)0.0540 (18)0.067 (2)−0.0075 (13)0.0040 (14)−0.0046 (15)
C60.0332 (13)0.0431 (15)0.0343 (14)0.0066 (12)−0.0012 (10)−0.0025 (12)
C70.0373 (14)0.0406 (15)0.0437 (15)−0.0033 (12)−0.0022 (11)−0.0015 (12)
C80.0373 (14)0.0376 (14)0.0450 (15)−0.0018 (11)0.0024 (12)−0.0069 (12)
C90.0504 (17)0.0522 (17)0.0516 (17)−0.0016 (14)0.0030 (13)−0.0037 (14)
C100.0646 (19)0.0526 (18)0.064 (2)−0.0104 (15)0.0133 (16)0.0011 (15)
C110.0496 (18)0.0554 (19)0.077 (2)−0.0225 (14)0.0168 (16)−0.0168 (16)
C120.0350 (15)0.0559 (17)0.0579 (18)−0.0085 (13)0.0024 (13)−0.0154 (15)
C130.0377 (14)0.0415 (15)0.0444 (15)−0.0029 (12)0.0034 (12)−0.0129 (13)
C140.0409 (15)0.0457 (16)0.0571 (17)0.0030 (12)−0.0092 (13)−0.0047 (13)
C150.0388 (14)0.0437 (15)0.0441 (15)−0.0020 (13)−0.0033 (12)−0.0009 (13)
C10.0487 (17)0.0505 (17)0.0626 (19)−0.0043 (14)0.0027 (14)0.0102 (15)
N20.0340 (11)0.0422 (12)0.0460 (12)−0.0027 (10)−0.0082 (9)0.0068 (10)
N30.0322 (11)0.0396 (12)0.0473 (13)−0.0035 (9)−0.0027 (10)−0.0030 (9)
O10.0467 (11)0.0625 (12)0.0580 (12)0.0017 (9)−0.0051 (9)0.0223 (10)
O20.0398 (10)0.0541 (11)0.0496 (11)−0.0060 (8)−0.0093 (8)−0.0013 (9)
O30.0521 (11)0.0617 (13)0.0654 (13)0.0137 (10)−0.0050 (9)−0.0172 (10)
O40.0642 (12)0.0577 (13)0.0569 (13)0.0116 (10)−0.0242 (10)−0.0138 (9)

Geometric parameters (Å, °)

N1—C21.335 (3)C9—H90.9300
N1—C11.338 (3)C10—C111.378 (4)
C2—C31.376 (3)C10—H100.9300
C2—C61.502 (3)C11—C121.369 (3)
C3—C41.375 (3)C11—H110.9300
C3—H30.9300C12—C131.389 (3)
C4—C51.372 (3)C12—H120.9300
C4—H40.9300C13—O21.373 (3)
C5—C11.369 (3)C14—O21.419 (2)
C5—H50.9300C14—C151.502 (3)
C6—O11.219 (3)C14—H14A0.9700
C6—N21.347 (2)C14—H14B0.9700
C7—N31.280 (3)C15—O31.204 (3)
C7—C81.462 (3)C15—O41.311 (3)
C7—H70.9300C1—H10.9300
C8—C91.388 (3)N2—N31.372 (2)
C8—C131.398 (3)N2—H20.8600
C9—C101.380 (3)O4—H4A0.8200
C2—N1—C1116.5 (2)C12—C11—C10120.9 (2)
N1—C2—C3123.7 (2)C12—C11—H11119.6
N1—C2—C6116.3 (2)C10—C11—H11119.6
C3—C2—C6119.9 (2)C11—C12—C13120.1 (2)
C4—C3—C2118.3 (2)C11—C12—H12120.0
C4—C3—H3120.9C13—C12—H12120.0
C2—C3—H3120.9O2—C13—C12124.7 (2)
C5—C4—C3119.1 (2)O2—C13—C8115.3 (2)
C5—C4—H4120.5C12—C13—C8120.0 (2)
C3—C4—H4120.5O2—C14—C15112.85 (19)
C1—C5—C4118.7 (3)O2—C14—H14A109.0
C1—C5—H5120.7C15—C14—H14A109.0
C4—C5—H5120.7O2—C14—H14B109.0
O1—C6—N2122.7 (2)C15—C14—H14B109.0
O1—C6—C2122.8 (2)H14A—C14—H14B107.8
N2—C6—C2114.5 (2)O3—C15—O4125.7 (2)
N3—C7—C8119.2 (2)O3—C15—C14124.6 (2)
N3—C7—H7120.4O4—C15—C14109.7 (2)
C8—C7—H7120.4N1—C1—C5123.7 (3)
C9—C8—C13118.6 (2)N1—C1—H1118.2
C9—C8—C7121.0 (2)C5—C1—H1118.2
C13—C8—C7120.4 (2)C6—N2—N3120.6 (2)
C10—C9—C8121.2 (2)C6—N2—H2119.7
C10—C9—H9119.4N3—N2—H2119.7
C8—C9—H9119.4C7—N3—N2115.7 (2)
C9—C10—C11119.3 (3)C13—O2—C14118.43 (18)
C9—C10—H10120.4C15—O4—H4A109.5
C11—C10—H10120.4
C1—N1—C2—C30.4 (3)C11—C12—C13—O2−178.3 (2)
C1—N1—C2—C6−178.7 (2)C11—C12—C13—C81.2 (4)
N1—C2—C3—C4−0.5 (4)C9—C8—C13—O2178.4 (2)
C6—C2—C3—C4178.5 (2)C7—C8—C13—O20.2 (3)
C2—C3—C4—C5−0.4 (4)C9—C8—C13—C12−1.2 (3)
C3—C4—C5—C11.5 (4)C7—C8—C13—C12−179.4 (2)
N1—C2—C6—O1175.4 (2)O2—C14—C15—O30.0 (4)
C3—C2—C6—O1−3.7 (3)O2—C14—C15—O4−179.8 (2)
N1—C2—C6—N2−4.2 (3)C2—N1—C1—C50.8 (4)
C3—C2—C6—N2176.6 (2)C4—C5—C1—N1−1.7 (4)
N3—C7—C8—C913.7 (3)O1—C6—N2—N31.0 (3)
N3—C7—C8—C13−168.2 (2)C2—C6—N2—N3−179.28 (19)
C13—C8—C9—C100.4 (4)C8—C7—N3—N2−179.88 (19)
C7—C8—C9—C10178.5 (2)C6—N2—N3—C7175.3 (2)
C8—C9—C10—C110.4 (4)C12—C13—O2—C147.3 (3)
C9—C10—C11—C12−0.4 (4)C8—C13—O2—C14−172.3 (2)
C10—C11—C12—C13−0.4 (4)C15—C14—O2—C13−81.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4A···O1i0.821.832.642 (2)171

Symmetry codes: (i) x−1, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2238).

References

  • Bruker (1998). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wu, W. S., Liu, S. X. & Huang, Z. X. (2003). J. Mol. Sci.19, 40–46.

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