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

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

doi:10.1107/S1600536809009544

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o816

doi:10.1107/S1600536809009544

Open

access

2-[(4-Chlorobenzoyl)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 14 March 2009; accepted 16 March 2009; online 25 March 2009)

In the title compound, C₁₀H₉ClN₂O₃·H₂O, the water molecule is a hydrogen-bond donor to the amide and carbonyl O atoms of two acid molecules; it is also a hydrogen-bond acceptor to the acid OH group and the amide H atom. The hydrogen-bonding interactions give rise to a two-dimensional array.

Related literature

For the structure of 2-[(4-methylbenzoyl)hydrazono]propionic acid monohydrate, see: Wong et al. (2009 ).

Experimental

Crystal data

C₁₀H₉ClN₂O₃·H₂O
M_r = 258.66
Triclinic, P 1
a = 6.6516 (1) Å
b = 6.9345 (1) Å
c = 7.0988 (1) Å
α = 73.833 (1)°
β = 80.182 (1)°
γ = 61.613 (1)°
V = 276.39 (1) Å³
Z = 1
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 118 K
0.45 × 0.35 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.858, T_max = 0.949
2247 measured reflections
1965 independent reflections
1952 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.070
S = 1.00
1965 reflections
171 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.33 e Å⁻³
Absolute structure: Flack (1983 ), 733 Friedel pairs
Flack parameter: 0.02 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O1W	0.83 (1)	1.92 (3)	2.659 (2)	147 (4)
O1W—H11⋯O2ⁱ	0.84 (1)	1.96 (1)	2.784 (2)	165 (2)
O1W—H12⋯O3	0.84 (1)	1.98 (1)	2.809 (2)	172 (2)
N1—H1N⋯O1Wⁱⁱ	0.88 (1)	2.48 (2)	3.3596 (18)	177 (2)
Symmetry codes: (i) x, y-1, z; (ii) x-1, y+1, z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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: pubCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009544/tk2398sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009544/tk2398Isup2.hkl

checkCIF report

Related literature top

For 2-[(4-methylbenzoyl)hydrazono]propionic acid monohydrate, see: Wong et al. (2009).

Experimental top

4-Chlorobenzoylhydrazide (0.85 g, 0.005 mol) and pyruvic acid (0.43 g, 0.005 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, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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: pubCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₀H₉N₂O₃^.H₂O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₁₀H₉ClN₂O₃·H₂O	Z = 1
M_r = 258.66	F(000) = 134
Triclinic, P1	D_x = 1.554 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6516 (1) Å	Cell parameters from 2199 reflections
b = 6.9345 (1) Å	θ = 3.0–28.2°
c = 7.0988 (1) Å	µ = 0.35 mm⁻¹
α = 73.833 (1)°	T = 118 K
β = 80.182 (1)°	Irregular block, colorless
γ = 61.613 (1)°	0.45 × 0.35 × 0.15 mm
V = 276.39 (1) Å³

Data collection top

Bruker SMART APEX diffractometer	1965 independent reflections
Radiation source: fine-focus sealed tube	1952 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.858, T_max = 0.949	k = −8→8
2247 measured 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)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.0628P)² + 0.0013P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
1965 reflections	Δρ_max = 0.20 e Å⁻³
171 parameters	Δρ_min = −0.33 e Å⁻³
7 restraints	Absolute structure: Flack (1983), 733 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (3)

Crystal data top

C₁₀H₉ClN₂O₃·H₂O	γ = 61.613 (1)°
M_r = 258.66	V = 276.39 (1) Å³
Triclinic, P1	Z = 1
a = 6.6516 (1) Å	Mo Kα radiation
b = 6.9345 (1) Å	µ = 0.35 mm⁻¹
c = 7.0988 (1) Å	T = 118 K
α = 73.833 (1)°	0.45 × 0.35 × 0.15 mm
β = 80.182 (1)°

Data collection top

Bruker SMART APEX diffractometer	1965 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1952 reflections with I > 2σ(I)
T_min = 0.858, T_max = 0.949	R_int = 0.011
2247 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.070	Δρ_max = 0.20 e Å⁻³
S = 1.00	Δρ_min = −0.33 e Å⁻³
1965 reflections	Absolute structure: Flack (1983), 733 Friedel pairs
171 parameters	Absolute structure parameter: 0.02 (3)
7 restraints

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

	x	y	z	U_iso*/U_eq
Cl1	0.50015 (5)	0.49992 (5)	0.49993 (4)	0.02415 (12)
O1	2.0776 (2)	0.41172 (18)	−0.23906 (16)	0.0184 (2)
O2	1.9975 (2)	0.76916 (19)	−0.31287 (18)	0.0221 (3)
O3	1.5700 (2)	0.18182 (19)	0.11932 (19)	0.0228 (3)
O1W	1.9830 (2)	0.06405 (18)	−0.10712 (18)	0.0216 (2)
N1	1.4403 (2)	0.5584 (2)	−0.0003 (2)	0.0168 (3)
N2	1.6543 (2)	0.5201 (2)	−0.07703 (19)	0.0154 (3)
C1	1.9322 (3)	0.6250 (3)	−0.2491 (2)	0.0161 (3)
C2	1.6887 (3)	0.6861 (2)	−0.1806 (2)	0.0165 (3)
C3	1.5134 (3)	0.9273 (3)	−0.2314 (3)	0.0279 (4)
H3A	1.3862	0.9390	−0.2937	0.042*
H3B	1.5830	1.0164	−0.3222	0.042*
H3C	1.4562	0.9845	−0.1115	0.042*
C4	1.4131 (3)	0.3718 (3)	0.1048 (2)	0.0169 (3)
C5	1.1830 (3)	0.4130 (3)	0.2013 (2)	0.0158 (3)
C6	1.1356 (3)	0.2284 (3)	0.2676 (2)	0.0197 (3)
H6	1.2483	0.0845	0.2492	0.024*
C7	0.9270 (3)	0.2526 (3)	0.3596 (2)	0.0200 (3)
H7	0.8955	0.1268	0.4045	0.024*
C8	0.7637 (3)	0.4649 (3)	0.3852 (2)	0.0187 (3)
C9	0.8072 (3)	0.6496 (3)	0.3209 (2)	0.0194 (3)
H9	0.6934	0.7934	0.3385	0.023*
C10	1.0168 (3)	0.6238 (2)	0.2310 (2)	0.0184 (3)
H10	1.0483	0.7497	0.1891	0.022*
H1O	2.032 (8)	0.321 (6)	−0.244 (7)	0.115 (18)*
H11	1.970 (4)	−0.004 (3)	−0.182 (3)	0.029 (5)*
H12	1.855 (2)	0.111 (4)	−0.048 (3)	0.028 (6)*
H1N	1.318 (3)	0.689 (2)	−0.024 (3)	0.013 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0181 (2)	0.0375 (2)	0.02137 (18)	−0.01711 (17)	0.00484 (13)	−0.00835 (14)
O1	0.0136 (6)	0.0172 (5)	0.0225 (6)	−0.0068 (4)	0.0026 (4)	−0.0041 (4)
O2	0.0191 (6)	0.0202 (5)	0.0283 (6)	−0.0120 (5)	0.0068 (5)	−0.0066 (4)
O3	0.0183 (6)	0.0153 (5)	0.0309 (6)	−0.0077 (4)	0.0049 (5)	−0.0028 (4)
O1W	0.0183 (6)	0.0182 (5)	0.0274 (6)	−0.0087 (5)	0.0051 (5)	−0.0067 (4)
N1	0.0140 (7)	0.0163 (6)	0.0188 (6)	−0.0074 (5)	0.0021 (5)	−0.0027 (5)
N2	0.0120 (7)	0.0196 (6)	0.0160 (6)	−0.0082 (5)	0.0032 (5)	−0.0064 (5)
C1	0.0167 (8)	0.0171 (6)	0.0156 (6)	−0.0087 (6)	0.0011 (6)	−0.0044 (5)
C2	0.0165 (8)	0.0158 (7)	0.0176 (7)	−0.0080 (6)	0.0008 (6)	−0.0038 (5)
C3	0.0177 (8)	0.0165 (7)	0.0415 (10)	−0.0060 (6)	0.0068 (7)	−0.0028 (6)
C4	0.0154 (8)	0.0191 (7)	0.0173 (7)	−0.0093 (6)	0.0014 (6)	−0.0044 (5)
C5	0.0137 (8)	0.0178 (7)	0.0153 (7)	−0.0081 (6)	0.0014 (6)	−0.0026 (5)
C6	0.0197 (8)	0.0195 (7)	0.0206 (7)	−0.0105 (6)	0.0010 (6)	−0.0036 (5)
C7	0.0213 (9)	0.0222 (7)	0.0212 (7)	−0.0147 (7)	0.0018 (6)	−0.0044 (6)
C8	0.0143 (8)	0.0279 (8)	0.0151 (7)	−0.0123 (7)	0.0019 (6)	−0.0030 (6)
C9	0.0168 (8)	0.0191 (7)	0.0182 (7)	−0.0064 (6)	−0.0003 (6)	−0.0016 (5)
C10	0.0176 (8)	0.0187 (7)	0.0185 (7)	−0.0098 (6)	0.0018 (6)	−0.0023 (5)

Geometric parameters (Å, º) top

Cl1—C8	1.7363 (18)	C3—H3B	0.9800
O1—C1	1.3161 (19)	C3—H3C	0.9800
O1—H1O	0.829 (10)	C4—C5	1.493 (2)
O2—C1	1.219 (2)	C5—C6	1.399 (2)
O3—C4	1.220 (2)	C5—C10	1.400 (2)
O1W—H11	0.842 (9)	C6—C7	1.382 (2)
O1W—H12	0.836 (10)	C6—H6	0.9500
N1—N2	1.360 (2)	C7—C8	1.393 (2)
N1—C4	1.379 (2)	C7—H7	0.9500
N1—H1N	0.878 (9)	C8—C9	1.383 (2)
N2—C2	1.281 (2)	C9—C10	1.380 (3)
C1—C2	1.495 (2)	C9—H9	0.9500
C2—C3	1.497 (2)	C10—H10	0.9500
C3—H3A	0.9800

C1—O1—H1O	120 (3)	N1—C4—C5	116.93 (13)
H11—O1W—H12	103 (2)	C6—C5—C10	119.14 (15)
N2—N1—C4	116.41 (12)	C6—C5—C4	117.42 (14)
N2—N1—H1N	124.6 (14)	C10—C5—C4	123.44 (14)
C4—N1—H1N	118.6 (14)	C7—C6—C5	120.85 (14)
C2—N2—N1	119.24 (13)	C7—C6—H6	119.6
O2—C1—O1	119.90 (16)	C5—C6—H6	119.6
O2—C1—C2	121.04 (14)	C6—C7—C8	118.77 (14)
O1—C1—C2	119.06 (13)	C6—C7—H7	120.6
N2—C2—C1	114.38 (13)	C8—C7—H7	120.6
N2—C2—C3	126.56 (16)	C9—C8—C7	121.30 (17)
C1—C2—C3	119.03 (14)	C9—C8—Cl1	119.04 (13)
C2—C3—H3A	109.5	C7—C8—Cl1	119.67 (13)
C2—C3—H3B	109.5	C10—C9—C8	119.64 (15)
H3A—C3—H3B	109.5	C10—C9—H9	120.2
C2—C3—H3C	109.5	C8—C9—H9	120.2
H3A—C3—H3C	109.5	C9—C10—C5	120.28 (14)
H3B—C3—H3C	109.5	C9—C10—H10	119.9
O3—C4—N1	121.63 (16)	C5—C10—H10	119.9
O3—C4—C5	121.44 (15)

C4—N1—N2—C2	178.11 (13)	N1—C4—C5—C10	−16.0 (2)
N1—N2—C2—C1	177.31 (11)	C10—C5—C6—C7	0.7 (2)
N1—N2—C2—C3	−0.7 (2)	C4—C5—C6—C7	179.58 (13)
O2—C1—C2—N2	−164.68 (14)	C5—C6—C7—C8	0.0 (2)
O1—C1—C2—N2	15.00 (19)	C6—C7—C8—C9	−0.1 (2)
O2—C1—C2—C3	13.5 (2)	C6—C7—C8—Cl1	179.90 (11)
O1—C1—C2—C3	−166.78 (14)	C7—C8—C9—C10	−0.6 (2)
N2—N1—C4—O3	−3.7 (2)	Cl1—C8—C9—C10	179.43 (11)
N2—N1—C4—C5	175.94 (11)	C8—C9—C10—C5	1.3 (2)
O3—C4—C5—C6	−15.2 (2)	C6—C5—C10—C9	−1.3 (2)
N1—C4—C5—C6	165.12 (13)	C4—C5—C10—C9	179.82 (13)
O3—C4—C5—C10	163.61 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1W	0.83 (1)	1.92 (3)	2.659 (2)	147 (4)
O1W—H11···O2ⁱ	0.84 (1)	1.96 (1)	2.784 (2)	165 (2)
O1W—H12···O3	0.84 (1)	1.98 (1)	2.809 (2)	172 (2)
N1—H1N···O1Wⁱⁱ	0.88 (1)	2.48 (2)	3.3596 (18)	177 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₉ClN₂O₃·H₂O
M_r	258.66
Crystal system, space group	Triclinic, P1
Temperature (K)	118
a, b, c (Å)	6.6516 (1), 6.9345 (1), 7.0988 (1)
α, β, γ (°)	73.833 (1), 80.182 (1), 61.613 (1)
V (Å³)	276.39 (1)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.45 × 0.35 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.858, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	2247, 1965, 1952
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.070, 1.00
No. of reflections	1965
No. of parameters	171
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.33
Absolute structure	Flack (1983), 733 Friedel pairs
Absolute structure parameter	0.02 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1W	0.83 (1)	1.92 (3)	2.659 (2)	147 (4)
O1W—H11···O2ⁱ	0.84 (1)	1.96 (1)	2.784 (2)	165 (2)
O1W—H12···O3	0.84 (1)	1.98 (1)	2.809 (2)	172 (2)
N1—H1N···O1Wⁱⁱ	0.88 (1)	2.48 (2)	3.3596 (18)	177 (2)

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

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
Wong, H. W., Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, o419. Web of Science CSD CrossRef IUCr Journals Google Scholar