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

Liu, B.-Y.; Liu, Z.; Wang, G.-R.

doi:10.1107/S160053680905082X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o26

doi:10.1107/S160053680905082X

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

Bao-Yu Liu,^a ^* Zheng Liu ^a and Guo-Rui Wang ^a

^aCollege of Chemical and Biological Engineering (Guilin University of Technology), Guilin 541004, People's Republic of China
^*Correspondence e-mail: lisa4.6@163.com

(Received 3 November 2009; accepted 25 November 2009; online 4 December 2009)

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 ).

Experimental

Crystal data

C₁₅H₁₃N₃O₄
M_r = 299.28
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.125
S = 0.99
3194 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.20 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
O4—H4A⋯O1ⁱ	0.82	1.83	2.642 (2)	171
Symmetry code: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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/S160053680905082X/kp2238sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 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.

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

Crystal data top

C₁₅H₁₃N₃O₄	F(000) = 624
M_r = 299.28	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1231 reflections
a = 8.871 (2) Å	θ = 2.3–20.3°
b = 9.042 (2) Å	µ = 0.11 mm⁻¹
c = 17.389 (4) Å	T = 296 K
β = 94.765 (3)°	Block, colourless
V = 1390.0 (5) Å³	0.16 × 0.15 × 0.04 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3194 independent reflections
Radiation source: fine-focus sealed tube	1512 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→11
T_min = 0.983, T_max = 0.996	k = −11→10
11832 measured reflections	l = −22→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0467P)² + 0.0303P] where P = (F_o² + 2F_c²)/3
3194 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₃N₃O₄	V = 1390.0 (5) Å³
M_r = 299.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.871 (2) Å	µ = 0.11 mm⁻¹
b = 9.042 (2) Å	T = 296 K
c = 17.389 (4) Å	0.16 × 0.15 × 0.04 mm
β = 94.765 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3194 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1512 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.996	R_int = 0.074
11832 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 0.99	Δρ_max = 0.20 e Å⁻³
3194 reflections	Δρ_min = −0.20 e Å⁻³
200 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	0.5796 (2)	0.6090 (2)	0.33901 (11)	0.0446 (5)
C2	0.6090 (3)	0.5119 (2)	0.39612 (13)	0.0353 (6)
C3	0.7443 (3)	0.5054 (3)	0.44083 (14)	0.0436 (6)
H3	0.7596	0.4364	0.4803	0.052*
C4	0.8563 (3)	0.6037 (3)	0.42557 (15)	0.0513 (7)
H4	0.9488	0.6027	0.4549	0.062*
C5	0.8296 (3)	0.7032 (3)	0.36644 (16)	0.0538 (7)
H5	0.9044	0.7692	0.3543	0.065*
C6	0.4850 (2)	0.4041 (3)	0.40971 (13)	0.0371 (6)
C7	0.1114 (3)	0.3732 (2)	0.33134 (13)	0.0409 (6)
H7	0.1103	0.4555	0.2993	0.049*
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)
H9	0.0465	0.1669	0.4304	0.062*
C10	−0.1651 (3)	0.0984 (3)	0.39943 (16)	0.0598 (8)
H10	−0.1709	0.0302	0.4391	0.072*
C11	−0.2859 (3)	0.1183 (3)	0.34527 (17)	0.0600 (8)
H11	−0.3733	0.0625	0.3484	0.072*
C12	−0.2790 (3)	0.2190 (3)	0.28689 (15)	0.0497 (7)
H12	−0.3611	0.2309	0.2506	0.060*
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	−0.2442	0.5471	0.1559	0.058*
H14B	−0.3484	0.4531	0.2056	0.058*
C15	−0.2888 (3)	0.3425 (3)	0.11069 (14)	0.0426 (6)
C1	0.6908 (3)	0.7033 (3)	0.32572 (15)	0.0541 (7)
H1	0.6727	0.7729	0.2866	0.065*
N2	0.3553 (2)	0.4263 (2)	0.36523 (10)	0.0414 (5)
H2	0.3495	0.4971	0.3321	0.050*
N3	0.2323 (2)	0.3368 (2)	0.37230 (11)	0.0401 (5)
O1	0.50069 (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	−0.4261	0.3245	0.0320	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0383 (12)	0.0473 (13)	0.0471 (13)	−0.0034 (10)	−0.0024 (10)	0.0064 (11)
C2	0.0341 (13)	0.0374 (14)	0.0346 (14)	0.0014 (11)	0.0031 (11)	−0.0057 (11)
C3	0.0408 (15)	0.0490 (16)	0.0399 (14)	0.0042 (12)	−0.0036 (12)	−0.0018 (12)
C4	0.0336 (14)	0.0615 (18)	0.0570 (18)	−0.0024 (13)	−0.0074 (12)	−0.0081 (15)
C5	0.0400 (16)	0.0540 (18)	0.067 (2)	−0.0075 (13)	0.0040 (14)	−0.0046 (15)
C6	0.0332 (13)	0.0431 (15)	0.0343 (14)	0.0066 (12)	−0.0012 (10)	−0.0025 (12)
C7	0.0373 (14)	0.0406 (15)	0.0437 (15)	−0.0033 (12)	−0.0022 (11)	−0.0015 (12)
C8	0.0373 (14)	0.0376 (14)	0.0450 (15)	−0.0018 (11)	0.0024 (12)	−0.0069 (12)
C9	0.0504 (17)	0.0522 (17)	0.0516 (17)	−0.0016 (14)	0.0030 (13)	−0.0037 (14)
C10	0.0646 (19)	0.0526 (18)	0.064 (2)	−0.0104 (15)	0.0133 (16)	0.0011 (15)
C11	0.0496 (18)	0.0554 (19)	0.077 (2)	−0.0225 (14)	0.0168 (16)	−0.0168 (16)
C12	0.0350 (15)	0.0559 (17)	0.0579 (18)	−0.0085 (13)	0.0024 (13)	−0.0154 (15)
C13	0.0377 (14)	0.0415 (15)	0.0444 (15)	−0.0029 (12)	0.0034 (12)	−0.0129 (13)
C14	0.0409 (15)	0.0457 (16)	0.0571 (17)	0.0030 (12)	−0.0092 (13)	−0.0047 (13)
C15	0.0388 (14)	0.0437 (15)	0.0441 (15)	−0.0020 (13)	−0.0033 (12)	−0.0009 (13)
C1	0.0487 (17)	0.0505 (17)	0.0626 (19)	−0.0043 (14)	0.0027 (14)	0.0102 (15)
N2	0.0340 (11)	0.0422 (12)	0.0460 (12)	−0.0027 (10)	−0.0082 (9)	0.0068 (10)
N3	0.0322 (11)	0.0396 (12)	0.0473 (13)	−0.0035 (9)	−0.0027 (10)	−0.0030 (9)
O1	0.0467 (11)	0.0625 (12)	0.0580 (12)	0.0017 (9)	−0.0051 (9)	0.0223 (10)
O2	0.0398 (10)	0.0541 (11)	0.0496 (11)	−0.0060 (8)	−0.0093 (8)	−0.0013 (9)
O3	0.0521 (11)	0.0617 (13)	0.0654 (13)	0.0137 (10)	−0.0050 (9)	−0.0172 (10)
O4	0.0642 (12)	0.0577 (13)	0.0569 (13)	0.0116 (10)	−0.0242 (10)	−0.0138 (9)

Geometric parameters (Å, º) top

N1—C2	1.335 (3)	C9—H9	0.9300
N1—C1	1.338 (3)	C10—C11	1.378 (4)
C2—C3	1.376 (3)	C10—H10	0.9300
C2—C6	1.502 (3)	C11—C12	1.369 (3)
C3—C4	1.375 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.389 (3)
C4—C5	1.372 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—O2	1.373 (3)
C5—C1	1.369 (3)	C14—O2	1.419 (2)
C5—H5	0.9300	C14—C15	1.502 (3)
C6—O1	1.219 (3)	C14—H14A	0.9700
C6—N2	1.347 (2)	C14—H14B	0.9700
C7—N3	1.280 (3)	C15—O3	1.204 (3)
C7—C8	1.462 (3)	C15—O4	1.311 (3)
C7—H7	0.9300	C1—H1	0.9300
C8—C9	1.388 (3)	N2—N3	1.372 (2)
C8—C13	1.398 (3)	N2—H2	0.8600
C9—C10	1.380 (3)	O4—H4A	0.8200

C2—N1—C1	116.5 (2)	C12—C11—C10	120.9 (2)
N1—C2—C3	123.7 (2)	C12—C11—H11	119.6
N1—C2—C6	116.3 (2)	C10—C11—H11	119.6
C3—C2—C6	119.9 (2)	C11—C12—C13	120.1 (2)
C4—C3—C2	118.3 (2)	C11—C12—H12	120.0
C4—C3—H3	120.9	C13—C12—H12	120.0
C2—C3—H3	120.9	O2—C13—C12	124.7 (2)
C5—C4—C3	119.1 (2)	O2—C13—C8	115.3 (2)
C5—C4—H4	120.5	C12—C13—C8	120.0 (2)
C3—C4—H4	120.5	O2—C14—C15	112.85 (19)
C1—C5—C4	118.7 (3)	O2—C14—H14A	109.0
C1—C5—H5	120.7	C15—C14—H14A	109.0
C4—C5—H5	120.7	O2—C14—H14B	109.0
O1—C6—N2	122.7 (2)	C15—C14—H14B	109.0
O1—C6—C2	122.8 (2)	H14A—C14—H14B	107.8
N2—C6—C2	114.5 (2)	O3—C15—O4	125.7 (2)
N3—C7—C8	119.2 (2)	O3—C15—C14	124.6 (2)
N3—C7—H7	120.4	O4—C15—C14	109.7 (2)
C8—C7—H7	120.4	N1—C1—C5	123.7 (3)
C9—C8—C13	118.6 (2)	N1—C1—H1	118.2
C9—C8—C7	121.0 (2)	C5—C1—H1	118.2
C13—C8—C7	120.4 (2)	C6—N2—N3	120.6 (2)
C10—C9—C8	121.2 (2)	C6—N2—H2	119.7
C10—C9—H9	119.4	N3—N2—H2	119.7
C8—C9—H9	119.4	C7—N3—N2	115.7 (2)
C9—C10—C11	119.3 (3)	C13—O2—C14	118.43 (18)
C9—C10—H10	120.4	C15—O4—H4A	109.5
C11—C10—H10	120.4

C1—N1—C2—C3	0.4 (3)	C11—C12—C13—O2	−178.3 (2)
C1—N1—C2—C6	−178.7 (2)	C11—C12—C13—C8	1.2 (4)
N1—C2—C3—C4	−0.5 (4)	C9—C8—C13—O2	178.4 (2)
C6—C2—C3—C4	178.5 (2)	C7—C8—C13—O2	0.2 (3)
C2—C3—C4—C5	−0.4 (4)	C9—C8—C13—C12	−1.2 (3)
C3—C4—C5—C1	1.5 (4)	C7—C8—C13—C12	−179.4 (2)
N1—C2—C6—O1	175.4 (2)	O2—C14—C15—O3	0.0 (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—C5	0.8 (4)
C3—C2—C6—N2	176.6 (2)	C4—C5—C1—N1	−1.7 (4)
N3—C7—C8—C9	13.7 (3)	O1—C6—N2—N3	1.0 (3)
N3—C7—C8—C13	−168.2 (2)	C2—C6—N2—N3	−179.28 (19)
C13—C8—C9—C10	0.4 (4)	C8—C7—N3—N2	−179.88 (19)
C7—C8—C9—C10	178.5 (2)	C6—N2—N3—C7	175.3 (2)
C8—C9—C10—C11	0.4 (4)	C12—C13—O2—C14	7.3 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O1ⁱ	0.82	1.83	2.642 (2)	171

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₃O₄
M_r	299.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.871 (2), 9.042 (2), 17.389 (4)
β (°)	94.765 (3)
V (Å³)	1390.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.16 × 0.15 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.983, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	11832, 3194, 1512
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.125, 0.99
No. of reflections	3194
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), 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
O4—H4A···O1ⁱ	0.82	1.83	2.642 (2)	170.9

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

Acknowledgements

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

References

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Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Wu, W. S., Liu, S. X. & Huang, Z. X. (2003). J. Mol. Sci. 19, 40–46. CAS Google Scholar