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

Abstract

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,

• a = 6.8464 (1) Å

• b = 11.9753 (2) Å

• c = 7.0005 (1) Å

• β = 102.169 (1)°

• V = 561.06 (2) ų

• 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[F ² > 2σ(F ²)] = 0.030

• wR(F ²) = 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

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 ▶).

Supplementary Material

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

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) ; (ii) .

supplementary crystallographic information

Experimental

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.

Refinement

Carbon-bound H atoms were placed in calculated positions (C—H 0.93–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The methyl H atoms were rotated to fit the electron density.

The oxygen- and nitrogen-bound H atoms were located in a difference Fourier map, and were refined with distance restraints [N—H 0.88 (2) and O—H 0.84 (2) Å]; their temperature factors were freely refined.

Figures

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.

Crystal data

C11H12N2O3·H2O	F(000) = 252
Mr = 238.24	Dx = 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

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

Refinement

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(Fo2) + (0.0559P)2 + 0.0248P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
1335 reflections	Δρmax = 0.19 e Å−3
172 parameters	Δρmin = −0.16 e Å−3
5 restraints	Absolute structure: 1126 Friedel pairs were merged
Primary atom site location: structure-invariant direct methods

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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.