2-[(4-Methyl­benzo­yl)hydrazono]­propionic acid monohydrate

Wong, H.W.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536809003067

organic compounds

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Volume 65| Part 2| February 2009| Page o419

doi:10.1107/S1600536809003067

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2-[(4-Methylbenzoyl)hydrazono]propionic acid monohydrate

Hon Wee Wong,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 21 January 2009; accepted 24 January 2009; online 31 January 2009)

In the title compound, C₁₁H₁₂N₂O₃·H₂O, the water molecule is a hydrogen-bond donor to the double-bond amide and the carbonyl O atoms of two acid molecules; it is also a hydrogen-bond acceptor to the acid –OH and amide –NH– groups. These hydrogen-bonding interactions give rise to a layer structure, with the layers parallel to the ab plane.

Related literature

The deprotonated anion of 2-aroylhydrazonopropionic acid furnishes a number of metal complexes; see, for example: Wu, Chen et al. (2006 ); Liu et al. (2007 ); Wu & Zeng (2007 ); Wu et al. (2006a ,b ); Yang et al. (2004 ); Yin & Chen (2006 ); Zhai et al. (2007 ).

Experimental

Crystal data

C₁₁H₁₂N₂O₃·H₂O
M_r = 238.24
Monoclinic, P 2₁
a = 6.8464 (1) Å
b = 11.9753 (2) Å
c = 7.0005 (1) Å
β = 102.169 (1)°
V = 561.06 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
5272 measured reflections
1335 independent reflections
1211 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.083
S = 1.02
1335 reflections
172 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: 1126 Friedel pairs were merged

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1W	0.83 (2)	2.03 (2)	2.777 (2)	149 (3)
O1W—H11⋯O3	0.84 (2)	1.97 (2)	2.794 (2)	165 (4)
O1W—H12⋯O2ⁱ	0.84 (2)	2.00 (1)	2.829 (2)	168 (3)
N2—H2⋯O1Wⁱⁱ	0.87 (2)	2.35 (1)	3.210 (2)	168 (3)
Symmetry codes: (i) $[-x+3, y-{\script{1\over 2}}, -z+2]$ ; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003067/cv2513sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003067/cv2513Isup2.hkl

checkCIF report

Related literature top

The deprotonated anion of 2-aroylhydrazonopropionic acid furnishes a number of metal complexes; see, for example: Wu, Chen et al. (2006); Liu et al. (2007); Wu & Zeng (2007); Wu et al. (2006a,b); Yang et al. (2004); Yin & Chen (2006); Zhai et al. (2007).

Experimental top

4-Toluihydrazide (1 g, 0.007 mol) and pyruvic acid (0.6 g, 0.007 mol) were dissolved in methanol (30 ml). The solution was heated for 3 h; slow evaporation of the solvent gave colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Displacement ellipsoids plot (Barbour, 2001) of the title compound at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

2-[(4-Methylbenzoyl)hydrazono]propionic acid monohydrate top

Crystal data top

C₁₁H₁₂N₂O₃·H₂O	F(000) = 252
M_r = 238.24	D_x = 1.410 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1743 reflections
a = 6.8464 (1) Å	θ = 3.0–26.9°
b = 11.9753 (2) Å	µ = 0.11 mm⁻¹
c = 7.0005 (1) Å	T = 100 K
β = 102.169 (1)°	Irregular block, colourless
V = 561.06 (2) Å³	0.20 × 0.10 × 0.10 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	1211 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −8→8
5272 measured reflections	k = −14→15
1335 independent reflections	l = −9→9

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.0559P)² + 0.0248P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
1335 reflections	Δρ_max = 0.19 e Å⁻³
172 parameters	Δρ_min = −0.16 e Å⁻³
5 restraints	Absolute structure: 1126 Friedel pairs were merged
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₁H₁₂N₂O₃·H₂O	V = 561.06 (2) Å³
M_r = 238.24	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.8464 (1) Å	µ = 0.11 mm⁻¹
b = 11.9753 (2) Å	T = 100 K
c = 7.0005 (1) Å	0.20 × 0.10 × 0.10 mm
β = 102.169 (1)°

Data collection top

Bruker SMART APEX diffractometer	1211 reflections with I > 2σ(I)
5272 measured reflections	R_int = 0.029
1335 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	5 restraints
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.19 e Å⁻³
1335 reflections	Δρ_min = −0.16 e Å⁻³
172 parameters	Absolute structure: 1126 Friedel pairs were merged

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.

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

	x	y	z	U_iso*/U_eq
O1	1.4450 (2)	0.99988 (13)	0.8798 (3)	0.0255 (4)
O2	1.2160 (2)	1.13156 (13)	0.8463 (2)	0.0269 (4)
O3	1.2831 (2)	0.64501 (13)	0.7200 (2)	0.0260 (4)
O1W	1.6032 (2)	0.78718 (13)	0.8663 (3)	0.0251 (4)
N1	1.1624 (2)	0.84748 (15)	0.7821 (3)	0.0192 (4)
N2	1.0279 (3)	0.76060 (15)	0.7458 (3)	0.0202 (4)
C1	1.2584 (3)	1.03349 (18)	0.8395 (3)	0.0204 (5)
C2	1.0961 (3)	0.94692 (18)	0.7861 (3)	0.0183 (4)
C3	0.8847 (3)	0.98625 (18)	0.7447 (3)	0.0232 (5)
H3A	0.8131	0.9412	0.6686	0.035*
H3B	0.8400	0.9951	0.8651	0.035*
H3C	0.8754	1.0568	0.6777	0.035*
C4	1.1067 (3)	0.65752 (18)	0.7236 (3)	0.0198 (4)
C5	0.9684 (3)	0.56054 (18)	0.7054 (3)	0.0178 (4)
C6	0.7608 (3)	0.5709 (2)	0.6510 (3)	0.0218 (4)
H6	0.7018	0.6422	0.6192	0.026*
C7	0.6408 (3)	0.47675 (19)	0.6437 (3)	0.0231 (5)
H7	0.4998	0.4845	0.6067	0.028*
C8	0.7226 (3)	0.37199 (18)	0.6891 (3)	0.0214 (5)
C9	0.9315 (3)	0.3617 (2)	0.7379 (3)	0.0221 (5)
H9A	0.9904	0.2901	0.7659	0.026*
C10	1.0524 (3)	0.45480 (19)	0.7457 (3)	0.0202 (4)
H10	1.1936	0.4467	0.7787	0.024*
C11	0.5927 (3)	0.27036 (19)	0.6870 (4)	0.0288 (5)
H11A	0.6157	0.2411	0.7985	0.043*
H11B	0.4542	0.2924	0.6689	0.043*
H11C	0.6071	0.2211	0.5815	0.043*
H11	1.496 (3)	0.755 (3)	0.813 (5)	0.059 (10)*
H12	1.653 (4)	0.748 (2)	0.963 (3)	0.052 (10)*
H1	1.445 (5)	0.9307 (9)	0.867 (5)	0.056 (11)*
H2	0.906 (2)	0.773 (2)	0.761 (4)	0.031 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0193 (8)	0.0198 (9)	0.0371 (10)	−0.0029 (6)	0.0049 (7)	−0.0031 (7)
O2	0.0234 (7)	0.0182 (8)	0.0384 (9)	−0.0001 (6)	0.0047 (7)	−0.0028 (7)
O3	0.0171 (7)	0.0206 (8)	0.0416 (9)	−0.0005 (6)	0.0094 (6)	−0.0039 (7)
O1W	0.0205 (7)	0.0208 (8)	0.0331 (10)	−0.0018 (6)	0.0036 (7)	0.0028 (7)
N1	0.0186 (9)	0.0171 (9)	0.0218 (9)	−0.0017 (7)	0.0042 (7)	0.0008 (7)
N2	0.0139 (8)	0.0165 (9)	0.0301 (10)	−0.0001 (7)	0.0048 (7)	−0.0012 (7)
C1	0.0198 (10)	0.0212 (11)	0.0202 (11)	−0.0033 (8)	0.0043 (8)	−0.0013 (8)
C2	0.0167 (9)	0.0179 (10)	0.0209 (10)	−0.0012 (8)	0.0054 (8)	−0.0004 (8)
C3	0.0174 (10)	0.0189 (11)	0.0329 (13)	0.0007 (8)	0.0044 (9)	0.0033 (9)
C4	0.0200 (10)	0.0186 (10)	0.0207 (10)	−0.0004 (8)	0.0041 (8)	0.0004 (9)
C5	0.0170 (10)	0.0169 (10)	0.0201 (10)	0.0010 (8)	0.0049 (8)	−0.0013 (8)
C6	0.0205 (10)	0.0204 (10)	0.0240 (11)	0.0024 (9)	0.0036 (8)	−0.0003 (9)
C7	0.0159 (10)	0.0238 (11)	0.0289 (12)	0.0017 (9)	0.0034 (8)	−0.0049 (9)
C8	0.0225 (11)	0.0216 (11)	0.0211 (11)	−0.0046 (9)	0.0068 (8)	−0.0057 (9)
C9	0.0260 (11)	0.0154 (10)	0.0254 (11)	0.0042 (9)	0.0067 (9)	0.0005 (8)
C10	0.0160 (9)	0.0214 (11)	0.0226 (11)	0.0021 (8)	0.0030 (8)	−0.0004 (9)
C11	0.0282 (11)	0.0228 (12)	0.0370 (14)	−0.0050 (10)	0.0110 (10)	−0.0044 (10)

Geometric parameters (Å, º) top

O1—C1	1.312 (3)	C4—C5	1.487 (3)
O1—H1	0.83 (2)	C5—C10	1.395 (3)
O2—C1	1.213 (3)	C5—C6	1.397 (3)
O3—C4	1.222 (2)	C6—C7	1.390 (3)
O1W—H11	0.84 (2)	C6—H6	0.9500
O1W—H12	0.82 (2)	C7—C8	1.383 (3)
N1—C2	1.277 (3)	C7—H7	0.9500
N1—N2	1.377 (2)	C8—C9	1.404 (3)
N2—C4	1.369 (3)	C8—C11	1.506 (3)
N2—H2	0.87 (2)	C9—C10	1.383 (3)
C1—C2	1.508 (3)	C9—H9A	0.9500
C2—C3	1.491 (3)	C10—H10	0.9500
C3—H3A	0.8400	C11—H11A	0.8400
C3—H3B	0.9620	C11—H11B	0.9663
C3—H3C	0.9620	C11—H11C	0.9662

C1—O1—H1	108 (2)	C6—C5—C4	123.14 (19)
H11—O1W—H12	106 (3)	C7—C6—C5	119.8 (2)
C2—N1—N2	118.80 (17)	C7—C6—H6	120.1
C4—N2—N1	116.00 (17)	C5—C6—H6	120.1
C4—N2—H2	124.9 (19)	C8—C7—C6	121.34 (19)
N1—N2—H2	118.1 (19)	C8—C7—H7	119.3
O2—C1—O1	121.2 (2)	C6—C7—H7	119.3
O2—C1—C2	120.35 (19)	C7—C8—C9	118.5 (2)
O1—C1—C2	118.40 (18)	C7—C8—C11	121.41 (19)
N1—C2—C3	128.72 (19)	C9—C8—C11	120.1 (2)
N1—C2—C1	113.55 (17)	C10—C9—C8	120.6 (2)
C3—C2—C1	117.73 (19)	C10—C9—H9A	119.7
C2—C3—H3A	109.5	C8—C9—H9A	119.7
C2—C3—H3B	109.9	C9—C10—C5	120.40 (18)
H3A—C3—H3B	112.0	C9—C10—H10	119.8
C2—C3—H3C	109.5	C5—C10—H10	119.8
H3A—C3—H3C	106.6	C8—C11—H11A	109.5
H3B—C3—H3C	109.3	C8—C11—H11B	110.0
O3—C4—N2	121.82 (19)	H11A—C11—H11B	102.8
O3—C4—C5	121.12 (19)	C8—C11—H11C	110.2
N2—C4—C5	117.06 (17)	H11A—C11—H11C	115.2
C10—C5—C6	119.3 (2)	H11B—C11—H11C	108.8
C10—C5—C4	117.61 (17)

C2—N1—N2—C4	173.5 (2)	N2—C4—C5—C6	20.0 (3)
N2—N1—C2—C3	−3.9 (3)	C10—C5—C6—C7	2.0 (3)
N2—N1—C2—C1	176.43 (17)	C4—C5—C6—C7	−177.78 (19)
O2—C1—C2—N1	179.1 (2)	C5—C6—C7—C8	−0.1 (3)
O1—C1—C2—N1	−1.5 (3)	C6—C7—C8—C9	−1.8 (3)
O2—C1—C2—C3	−0.6 (3)	C6—C7—C8—C11	178.2 (2)
O1—C1—C2—C3	178.78 (19)	C7—C8—C9—C10	1.8 (3)
N1—N2—C4—O3	−5.9 (3)	C11—C8—C9—C10	−178.2 (2)
N1—N2—C4—C5	173.67 (17)	C8—C9—C10—C5	0.1 (3)
O3—C4—C5—C10	19.8 (3)	C6—C5—C10—C9	−2.0 (3)
N2—C4—C5—C10	−159.73 (19)	C4—C5—C10—C9	177.77 (19)
O3—C4—C5—C6	−160.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1W	0.83 (2)	2.03 (2)	2.777 (2)	149 (3)
O1W—H11···O3	0.84 (2)	1.97 (2)	2.794 (2)	165 (4)
O1W—H12···O2ⁱ	0.84 (2)	2.00 (1)	2.829 (2)	168 (3)
N2—H2···O1Wⁱⁱ	0.87 (2)	2.35 (1)	3.210 (2)	168 (3)

Symmetry codes: (i) −x+3, y−1/2, −z+2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N₂O₃·H₂O
M_r	238.24
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	6.8464 (1), 11.9753 (2), 7.0005 (1)
β (°)	102.169 (1)
V (Å³)	561.06 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5272, 1335, 1211
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.083, 1.02
No. of reflections	1335
No. of parameters	172
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16
Absolute structure	1126 Friedel pairs were merged

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1W	0.83 (2)	2.03 (2)	2.777 (2)	149 (3)
O1W—H11···O3	0.84 (2)	1.97 (2)	2.794 (2)	165 (4)
O1W—H12···O2ⁱ	0.84 (2)	2.00 (1)	2.829 (2)	168 (3)
N2—H2···O1Wⁱⁱ	0.87 (2)	2.35 (1)	3.210 (2)	168 (3)

Symmetry codes: (i) −x+3, y−1/2, −z+2; (ii) x−1, y, z.

Acknowledgements

The autors thank the University of Malaya (grant Nos. FS339/2008A and PS206/2008A) for supporting this study.

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