(E)-4-[2-(2-Hy­droxy­benzo­yl)­hydra­zin­ylidene]penta­noic acid

Qiao, Y.; Cui, J.; Pan, Z.; Liu, P.; Yin, H.

doi:10.1107/S1600536811033988

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2415

doi:10.1107/S1600536811033988

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(E)-4-[2-(2-Hydroxybenzoyl)hydrazinylidene]pentanoic acid

Yanling Qiao,^a Jichun Cui,^a ^* Zhaoling Pan,^b Peipei Liu ^c and Handong Yin ^c

^aShandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China, ^bLinyi No. 1 Middle School, Linyi 276003, People's Republic of China, and ^cCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: jchcui@163.com

(Received 25 June 2011; accepted 19 August 2011; online 27 August 2011)

The title molecule, C₁₂H₁₄N₂O₄, adopts a trans configuration with respect to the C=N double bond. The amino group is involved in an intramolecular N—H⋯O hydrogen bond. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into doubled sheets parallel to the (101) plane.

Related literature

For the synthesis and structures of some organotin(IV) complexes of related tridentate hydrazone ligands, see: Yin et al. (2008 ).

Experimental

Crystal data

C₁₂H₁₄N₂O₄
M_r = 250.25
Monoclinic, C 2/c
a = 24.445 (2) Å
b = 8.4683 (8) Å
c = 13.1204 (12) Å
β = 118.560 (1)°
V = 2385.6 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.45 × 0.20 × 0.17 mm

Data collection

Bruker SMART 1000 diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.954, T_max = 0.982
5738 measured reflections
2092 independent reflections
1013 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.114
S = 1.00
2092 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2ⁱ	0.82	1.91	2.679 (3)	155
O1—H1⋯O3ⁱⁱ	0.82	1.80	2.570 (3)	155
N2—H2⋯O4	0.86	1.95	2.635 (3)	136
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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 I, global. DOI: 10.1107/S1600536811033988/cv5127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033988/cv5127Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033988/cv5127Isup3.cml

checkCIF report

Comment top

Recently, we have reported some organotin(IV) complexes with hydrazone ligands (Yin et al., 2008). As an extension of our work on the structural characterization of hydrazone compounds, the title compound, (I), is reported here.

In the title compound, (I), the N1═C4 bond length of 1.276 (3) Å is a typical double bond value, while the N2—C6 [1.337 (3) Å] and N1—N2 [1.390 (3) Å] bonds are intermediate between double and single bonds because of conjugation effects in the molecule.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into doubled sheets parallel to (101) plane.

Related literature top

For the synthesis and structures of some organotin(IV) complexes of related tridentate hydrazone ligands, see: Yin et al. (2008).

Experimental top

Compound (I) was synthesized by the reaction of 2-hydroxybenzohydrazide (10 mmol) with 4-oxopentanoic acid (10 mmol). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution.

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 of (I), showing 50% probability displacement ellipsoids. Dashed line denotes hydrogen bond.
	Fig. 2. A portion of the crystal packing, showing hydrogen-bonded (dashed lines) two-dimensional network. H atoms have been omitted for clarity.

(E)-4-[2-(2-Hydroxybenzoyl)hydrazinylidene]pentanoic acid top

Crystal data top

C₁₂H₁₄N₂O₄	F(000) = 1056
M_r = 250.25	D_x = 1.394 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 24.445 (2) Å	Cell parameters from 770 reflections
b = 8.4683 (8) Å	θ = 2.6–20.7°
c = 13.1204 (12) Å	µ = 0.11 mm⁻¹
β = 118.560 (1)°	T = 298 K
V = 2385.6 (4) Å³	Block, colourless
Z = 8	0.45 × 0.20 × 0.17 mm

Data collection top

Bruker SMART 1000 diffractometer	2092 independent reflections
Radiation source: fine-focus sealed tube	1013 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −28→14
T_min = 0.954, T_max = 0.982	k = −10→9
5738 measured reflections	l = −15→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0385P)²] where P = (F_o² + 2F_c²)/3
2092 reflections	(Δ/σ)_max < 0.001
164 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₂H₁₄N₂O₄	V = 2385.6 (4) Å³
M_r = 250.25	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.445 (2) Å	µ = 0.11 mm⁻¹
b = 8.4683 (8) Å	T = 298 K
c = 13.1204 (12) Å	0.45 × 0.20 × 0.17 mm
β = 118.560 (1)°

Data collection top

Bruker SMART 1000 diffractometer	2092 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1013 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.982	R_int = 0.062
5738 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.00	Δρ_max = 0.23 e Å⁻³
2092 reflections	Δρ_min = −0.26 e Å⁻³
164 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.39247 (9)	0.4503 (3)	0.29554 (19)	0.0352 (6)
N2	0.45430 (9)	0.4964 (3)	0.34082 (18)	0.0351 (6)
H2	0.4823	0.4263	0.3536	0.042*
O1	0.18399 (10)	0.3011 (3)	0.2303 (2)	0.0700 (7)
H1	0.1496	0.2591	0.2013	0.105*
O2	0.17818 (9)	0.2415 (2)	0.0602 (2)	0.0586 (7)
O3	0.43347 (9)	0.7535 (2)	0.35295 (18)	0.0528 (6)
O4	0.57296 (8)	0.4200 (2)	0.43211 (16)	0.0447 (6)
H4	0.6050	0.3692	0.4522	0.067*
C1	0.20548 (13)	0.2976 (3)	0.1566 (3)	0.0429 (8)
C2	0.26898 (12)	0.3703 (3)	0.2044 (3)	0.0485 (9)
H2A	0.2796	0.4225	0.2774	0.058*
H2B	0.2689	0.4491	0.1506	0.058*
C3	0.31687 (12)	0.2454 (3)	0.2235 (3)	0.0445 (8)
H3A	0.3143	0.1641	0.2732	0.053*
H3B	0.3062	0.1969	0.1494	0.053*
C4	0.38293 (12)	0.3024 (3)	0.2768 (2)	0.0367 (8)
C5	0.43127 (12)	0.1791 (3)	0.3004 (3)	0.0488 (9)
H5A	0.4466	0.1895	0.2456	0.073*
H5B	0.4133	0.0763	0.2931	0.073*
H5C	0.4651	0.1924	0.3776	0.073*
C6	0.47095 (13)	0.6478 (4)	0.3649 (2)	0.0352 (7)
C7	0.53770 (12)	0.6864 (3)	0.4048 (2)	0.0333 (7)
C8	0.58579 (12)	0.5776 (3)	0.4357 (2)	0.0337 (7)
C9	0.64610 (13)	0.6295 (4)	0.4698 (2)	0.0461 (8)
H9	0.6779	0.5562	0.4897	0.055*
C10	0.65900 (15)	0.7874 (4)	0.4743 (3)	0.0570 (10)
H10	0.6994	0.8208	0.4969	0.068*
C11	0.61268 (15)	0.8956 (4)	0.4456 (3)	0.0583 (10)
H11	0.6215	1.0029	0.4492	0.070*
C12	0.55293 (13)	0.8455 (3)	0.4115 (2)	0.0457 (8)
H12	0.5217	0.9205	0.3922	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0219 (14)	0.0424 (16)	0.0391 (16)	−0.0016 (11)	0.0127 (11)	0.0005 (12)
N2	0.0233 (13)	0.0326 (14)	0.0479 (16)	−0.0001 (11)	0.0160 (12)	−0.0001 (12)
O1	0.0452 (14)	0.0932 (19)	0.0764 (18)	−0.0259 (12)	0.0329 (13)	−0.0195 (15)
O2	0.0395 (13)	0.0633 (16)	0.0669 (17)	−0.0156 (11)	0.0206 (12)	−0.0133 (13)
O3	0.0373 (12)	0.0370 (13)	0.0851 (17)	0.0070 (10)	0.0301 (12)	0.0027 (12)
O4	0.0293 (11)	0.0377 (13)	0.0612 (15)	0.0056 (9)	0.0167 (10)	0.0010 (11)
C1	0.0274 (18)	0.0371 (19)	0.061 (3)	0.0012 (14)	0.0184 (18)	0.0041 (18)
C2	0.0297 (17)	0.0404 (18)	0.070 (2)	−0.0044 (14)	0.0190 (16)	0.0016 (17)
C3	0.0279 (17)	0.0460 (19)	0.057 (2)	−0.0046 (14)	0.0180 (16)	−0.0035 (16)
C4	0.0302 (17)	0.0376 (19)	0.042 (2)	−0.0009 (14)	0.0172 (15)	0.0004 (15)
C5	0.0409 (19)	0.0369 (18)	0.070 (2)	−0.0001 (14)	0.0278 (17)	−0.0053 (16)
C6	0.0304 (17)	0.040 (2)	0.0349 (19)	0.0011 (15)	0.0157 (14)	0.0011 (15)
C7	0.0273 (16)	0.0350 (18)	0.0343 (18)	−0.0020 (13)	0.0122 (14)	−0.0014 (14)
C8	0.0319 (17)	0.0339 (18)	0.0371 (19)	−0.0036 (14)	0.0179 (15)	−0.0028 (14)
C9	0.0299 (18)	0.054 (2)	0.054 (2)	−0.0030 (15)	0.0196 (17)	−0.0033 (17)
C10	0.038 (2)	0.069 (3)	0.058 (2)	−0.0189 (19)	0.0188 (18)	−0.005 (2)
C11	0.053 (2)	0.047 (2)	0.067 (3)	−0.0174 (18)	0.022 (2)	−0.0002 (18)
C12	0.042 (2)	0.039 (2)	0.049 (2)	−0.0028 (15)	0.0163 (17)	0.0008 (16)

Geometric parameters (Å, º) top

N1—C4	1.276 (3)	C3—H3B	0.9700
N1—N2	1.390 (3)	C4—C5	1.494 (3)
N2—C6	1.337 (3)	C5—H5A	0.9600
N2—H2	0.8600	C5—H5B	0.9600
O1—C1	1.303 (3)	C5—H5C	0.9600
O1—H1	0.8200	C6—C7	1.492 (3)
O2—C1	1.209 (3)	C7—C12	1.390 (3)
O3—C6	1.236 (3)	C7—C8	1.393 (3)
O4—C8	1.366 (3)	C8—C9	1.392 (3)
O4—H4	0.8200	C9—C10	1.368 (4)
C1—C2	1.501 (4)	C9—H9	0.9300
C2—C3	1.507 (3)	C10—C11	1.363 (4)
C2—H2A	0.9700	C10—H10	0.9300
C2—H2B	0.9700	C11—C12	1.374 (4)
C3—C4	1.500 (3)	C11—H11	0.9300
C3—H3A	0.9700	C12—H12	0.9300

C4—N1—N2	114.8 (2)	H5A—C5—H5B	109.5
C6—N2—N1	121.1 (2)	C4—C5—H5C	109.5
C6—N2—H2	119.5	H5A—C5—H5C	109.5
N1—N2—H2	119.5	H5B—C5—H5C	109.5
C1—O1—H1	109.5	O3—C6—N2	122.8 (3)
C8—O4—H4	109.5	O3—C6—C7	120.4 (3)
O2—C1—O1	124.6 (3)	N2—C6—C7	116.8 (2)
O2—C1—C2	122.8 (3)	C12—C7—C8	117.4 (3)
O1—C1—C2	112.5 (3)	C12—C7—C6	116.7 (2)
C1—C2—C3	110.3 (2)	C8—C7—C6	125.9 (3)
C1—C2—H2A	109.6	O4—C8—C9	120.7 (2)
C3—C2—H2A	109.6	O4—C8—C7	119.2 (2)
C1—C2—H2B	109.6	C9—C8—C7	120.1 (3)
C3—C2—H2B	109.6	C10—C9—C8	120.6 (3)
H2A—C2—H2B	108.1	C10—C9—H9	119.7
C4—C3—C2	115.4 (2)	C8—C9—H9	119.7
C4—C3—H3A	108.4	C11—C10—C9	120.1 (3)
C2—C3—H3A	108.4	C11—C10—H10	120.0
C4—C3—H3B	108.4	C9—C10—H10	120.0
C2—C3—H3B	108.4	C10—C11—C12	119.7 (3)
H3A—C3—H3B	107.5	C10—C11—H11	120.1
N1—C4—C5	126.3 (2)	C12—C11—H11	120.1
N1—C4—C3	117.5 (2)	C11—C12—C7	122.1 (3)
C5—C4—C3	116.2 (2)	C11—C12—H12	119.0
C4—C5—H5A	109.5	C7—C12—H12	119.0
C4—C5—H5B	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2ⁱ	0.82	1.91	2.679 (3)	155
O1—H1···O3ⁱⁱ	0.82	1.80	2.570 (3)	155
N2—H2···O4	0.86	1.95	2.635 (3)	136

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄N₂O₄
M_r	250.25
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	24.445 (2), 8.4683 (8), 13.1204 (12)
β (°)	118.560 (1)
V (Å³)	2385.6 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.45 × 0.20 × 0.17

Data collection
Diffractometer	Bruker SMART 1000 diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.954, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	5738, 2092, 1013
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.114, 1.00
No. of reflections	2092
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2ⁱ	0.82	1.91	2.679 (3)	155.1
O1—H1···O3ⁱⁱ	0.82	1.80	2.570 (3)	154.9
N2—H2···O4	0.86	1.95	2.635 (3)	136.1

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

Acknowledgements

The authors acknowledge the National Natural Foundation of China (grant No. 20771053) and the Scientific Research Fund of Liaocheng University (grant No. X09039).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yin, H., Cui, J. & Qiao, Y. (2008). Polyhedron, 27, 2157–2166. Web of Science CSD CrossRef CAS Google Scholar