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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o1098
doi:10.1107/S1600536812009518

4-[(2-Carb­­oxy­eth­yl)amino]­benzoic acid monohydrate

Chunman Jia,a Shangwen Chena and Wenbing Yuana*

aKey Laboratory of Tropical Biological Resources of the Ministry of Education, Hainan University, Haikou 570228, People's Republic of China
*Correspondence e-mail: wbyuan@fjirsm.ac.cn

(Received 27 February 2012; accepted 4 March 2012; online 17 March 2012)

In the title compound, C10H11NO4·H2O, the carboxyl group is twisted at a dihedral angle of 6.1 (3)° with respect to the benzene ring. In the crystal, the organic mol­ecules are linked by pairs of O—H⋯O hydrogen bonds involving both carboxyl groups, forming zigzag chains propagating along the b-axis direction. The water mol­ecules form [100] chains linked by O—H⋯O hydrogen bonds. The organic mol­ecule and water chains are cross-linked by N—H⋯Owater and Owater—H⋯O hydrogen bonds, generating (001) sheets.

Related literature

For synthetic background, see: Kurd & Hayao (1952[Kurd, C. D. & Hayao, S. (1952). J. Am. Chem. Soc. 74, 5889-5893.]); Yong et al. (2004[Yong, G. P., Wang, Z. Y. & Cui, Y. (2004). Eur. J. Inorg. Chem. 21, 4317-4323.]).

[Scheme 1]

Experimental

Crystal data

  • C10H11NO4·H2O

  • Mr = 227.21

  • Orthorhombic, P b c a

  • a = 4.9387 (19) Å

  • b = 19.700 (7) Å

  • c = 21.616 (8) Å

  • V = 2103.1 (14) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 298 K

  • 0.50 × 0.20 × 0.10 mm
Data collection

  • Rigaku AFC-7S Mercury diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.944, Tmax = 0.989

  • 15116 measured reflections

  • 2401 independent reflections

  • 2059 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.167

  • S = 1.09

  • 2401 reflections

  • 146 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N7—H7⋯O5 0.97 2.04 3.009 (2) 175
O2—H2⋯O4i 0.95 1.74 2.662 (2) 165
O3—H1⋯O1ii 1.04 1.63 2.622 (2) 159
O5—H5A⋯O2iii 0.88 2.44 3.103 (2) 133
O5—H5A⋯O4iv 0.88 2.52 3.129 (2) 127
O5—H5B⋯O5iv 0.91 2.01 2.890 (2) 163
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]; (iii) -x+1, -y+1, -z+1; (iv) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812009518/hb6663sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009518/hb6663Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009518/hb6663Isup3.cml

checkCIF report


Comment top

The N-substitute β-alanine derivatives, as chelating or bridging muti-caboxylate ligands, have been applied to synthesis various novel metal-organic coordination polymers(Yong et al. 2004). It was firstly reported the reaction of propiolactone with aniline derivatives to synthesis the title compound I (Kurd & Hayao 1952). The molecular structure of the title compound I is shown in Fig. 1.

In the compound I, the carboxyl group attached to the benzene ring is twisted from its plane at 6.05 (29)°. For this compound, there are four main hydrongen bonds, and their distances are 2.622(O3—H1···O1i), 2.662(O2—H2···O4iv), 2.889(O5—H5B···O5iii) and 3.009(N7—H7···O5)Å, respectively. Throngh the intermolecular hydrogen bonds(O3—H1···O1i, O2—H2···O4iv) in carboxyl groups, generating R22(8) loops, two title compound I moleculars connect together and form a Z-type one-dimensional polymer. The crystal waters form the water chains in the structure via hydrogen bonds(O5—H5B···O5iii). Morever, there are hydrogen bonds N7—H7···O5 between the crystal waters and compounds. As a result, all these hydrogen bonds connect the title compond I molculars into a layer (Fig. 2).

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

Related literature top

For synthetic background, see: Kurd & Hayao (1952); Yong et al. (2004).

Experimental top

The title compound (I) was prepared using a slightly modified published procedure (Yong et al. 2004). A solution of KOH (11.2 g, 0.2 mol) in water (60 ml) was added dropwise to a solution of 3-chloropropanonic acid (10.9 g, 0.1 mol) in water (50 ml). To the resulting alkline solution, p-aminobenzonic(13.7 g, 0.1 mol) was slowly added, and the mixture was refluxed for 36 h. The solution was filtered and cooled to room temperature, then acidified with HCl solution until the desired white precipitated, which were collected by filtration. Pure compound (I) was obstained by crystallizing from methanol. Colourless blocks of (I) were obstained by slow evaporation of methanol solution.

Refinement top

H atoms were positioned geometrically (C–H = 0.95–0.99 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.2 Ueq(C).

Structure description top

The N-substitute β-alanine derivatives, as chelating or bridging muti-caboxylate ligands, have been applied to synthesis various novel metal-organic coordination polymers(Yong et al. 2004). It was firstly reported the reaction of propiolactone with aniline derivatives to synthesis the title compound I (Kurd & Hayao 1952). The molecular structure of the title compound I is shown in Fig. 1.

In the compound I, the carboxyl group attached to the benzene ring is twisted from its plane at 6.05 (29)°. For this compound, there are four main hydrongen bonds, and their distances are 2.622(O3—H1···O1i), 2.662(O2—H2···O4iv), 2.889(O5—H5B···O5iii) and 3.009(N7—H7···O5)Å, respectively. Throngh the intermolecular hydrogen bonds(O3—H1···O1i, O2—H2···O4iv) in carboxyl groups, generating R22(8) loops, two title compound I moleculars connect together and form a Z-type one-dimensional polymer. The crystal waters form the water chains in the structure via hydrogen bonds(O5—H5B···O5iii). Morever, there are hydrogen bonds N7—H7···O5 between the crystal waters and compounds. As a result, all these hydrogen bonds connect the title compond I molculars into a layer (Fig. 2).

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

For synthetic background, see: Kurd & Hayao (1952); Yong et al. (2004).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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
[Figure 1] Fig. 1. Ellipsoid plot.
[Figure 2] Fig. 2. Packing diagram.
4-[(2-Carboxyethyl)amino]benzoic acid monohydrate top
Crystal data top
C10H11NO4·H2OF(000) = 960
Mr = 227.21Dx = 1.435 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4011 reflections
a = 4.9387 (19) Åθ = 2.3–27.4°
b = 19.700 (7) ŵ = 0.12 mm−1
c = 21.616 (8) ÅT = 298 K
V = 2103.1 (14) Å3Prism, colourless
Z = 80.50 × 0.20 × 0.10 mm
Data collection top
Rigaku AFC-7S Mercury
diffractometer		2401 independent reflections
Radiation source: Rotating Anode2059 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.037
Detector resolution: 28.5714 pixels mm-1θmax = 27.5°, θmin = 2.8°
CCD_Profile_fitting scansh = −6→6
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −25→17
Tmin = 0.944, Tmax = 0.989l = −27→28
15116 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0855P)2 + 0.7233P]
where P = (Fo2 + 2Fc2)/3
2401 reflections(Δ/σ)max < 0.001
146 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C10H11NO4·H2OV = 2103.1 (14) Å3
Mr = 227.21Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 4.9387 (19) ŵ = 0.12 mm−1
b = 19.700 (7) ÅT = 298 K
c = 21.616 (8) Å0.50 × 0.20 × 0.10 mm
Data collection top
Rigaku AFC-7S Mercury
diffractometer		2401 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		2059 reflections with I > 2σ(I)
Tmin = 0.944, Tmax = 0.989Rint = 0.037
15116 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.167H-atom parameters constrained
S = 1.09Δρmax = 0.21 e Å−3
2401 reflectionsΔρmin = −0.29 e Å−3
146 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
xyzUiso*/Ueq
O40.0461 (3)0.17797 (7)0.60257 (7)0.0513 (4)
O30.2084 (3)0.20433 (7)0.69553 (7)0.0560 (4)
O10.9408 (3)0.60527 (7)0.68389 (8)0.0552 (4)
C20.7123 (4)0.51980 (9)0.62835 (9)0.0386 (4)
O21.0540 (3)0.58943 (8)0.58500 (7)0.0570 (4)
C8−0.0056 (4)0.33809 (9)0.67078 (9)0.0397 (4)
H8A−0.13840.37390.67600.048*
H8B0.09500.33380.70910.048*
C70.5435 (4)0.50574 (9)0.67792 (9)0.0381 (4)
H60.55250.53270.71320.046*
N70.1779 (3)0.35565 (8)0.62101 (7)0.0420 (4)
C60.3618 (4)0.45234 (9)0.67594 (9)0.0382 (4)
H50.25020.44380.70970.046*
C50.3452 (4)0.41113 (9)0.62324 (9)0.0369 (4)
C100.0490 (4)0.21407 (9)0.65073 (9)0.0395 (4)
C9−0.1486 (4)0.27183 (10)0.65677 (10)0.0427 (5)
H9A−0.27600.26180.68970.051*
H9B−0.25000.27640.61860.051*
C40.5114 (4)0.42647 (10)0.57240 (9)0.0447 (5)
H40.49990.40040.53660.054*
C30.6909 (4)0.47976 (10)0.57507 (9)0.0450 (5)
H30.79950.48930.54100.054*
C10.9125 (4)0.57462 (9)0.63300 (9)0.0403 (4)
O50.1077 (4)0.28799 (9)0.49724 (8)0.0680 (5)
H10.34150.16730.68030.082*
H5A0.12160.30620.46010.082*
H5B0.28100.27250.49920.082*
H21.17230.62670.59070.082*
H70.15180.33630.58010.059 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0567 (9)0.0465 (8)0.0507 (9)0.0084 (6)−0.0045 (7)−0.0030 (6)
O30.0587 (9)0.0514 (8)0.0578 (10)0.0159 (7)−0.0138 (7)−0.0084 (7)
O10.0605 (10)0.0455 (8)0.0597 (10)−0.0115 (7)−0.0070 (7)−0.0042 (7)
C20.0365 (9)0.0352 (9)0.0441 (10)−0.0001 (7)−0.0031 (7)0.0057 (7)
O20.0542 (9)0.0586 (9)0.0583 (10)−0.0170 (7)−0.0009 (7)0.0130 (7)
C80.0384 (9)0.0364 (9)0.0444 (10)0.0031 (7)0.0034 (8)−0.0010 (7)
C70.0408 (9)0.0322 (9)0.0412 (10)0.0028 (7)−0.0032 (8)−0.0012 (7)
N70.0443 (9)0.0409 (8)0.0407 (9)−0.0052 (7)0.0030 (7)−0.0046 (6)
C60.0381 (9)0.0366 (9)0.0401 (10)0.0021 (7)0.0020 (7)0.0007 (7)
C50.0354 (9)0.0340 (8)0.0414 (10)0.0026 (7)−0.0020 (7)0.0020 (7)
C100.0386 (9)0.0339 (9)0.0460 (11)−0.0030 (7)0.0019 (8)0.0044 (7)
C90.0344 (9)0.0407 (10)0.0530 (11)−0.0004 (7)0.0003 (8)−0.0001 (8)
C40.0487 (11)0.0481 (11)0.0372 (10)−0.0052 (9)0.0023 (8)−0.0043 (8)
C30.0447 (10)0.0510 (11)0.0392 (10)−0.0048 (8)0.0029 (8)0.0049 (8)
C10.0394 (9)0.0375 (9)0.0441 (10)0.0004 (7)−0.0030 (8)0.0065 (8)
O50.0777 (12)0.0765 (12)0.0498 (10)−0.0008 (10)0.0038 (8)0.0037 (8)
Geometric parameters (Å, º) top
O4—C101.261 (2)C7—H60.9300
O3—C101.263 (2)N7—C51.371 (2)
O3—H11.0351N7—H70.9720
O1—C11.262 (2)C6—C51.401 (3)
C2—C71.386 (3)C6—H50.9300
C2—C31.400 (3)C5—C41.404 (3)
C2—C11.468 (3)C10—C91.505 (3)
O2—C11.284 (2)C9—H9A0.9700
O2—H20.9458C9—H9B0.9700
C8—N71.448 (3)C4—C31.375 (3)
C8—C91.515 (3)C4—H40.9300
C8—H8A0.9700C3—H30.9300
C8—H8B0.9700O5—H5A0.8817
C7—C61.383 (3)O5—H5B0.9095
C10—O3—H1105.0N7—C5—C4119.75 (17)
C7—C2—C3118.57 (17)C6—C5—C4118.51 (17)
C7—C2—C1119.96 (17)O4—C10—O3123.67 (18)
C3—C2—C1121.45 (17)O4—C10—C9119.40 (17)
C1—O2—H2114.0O3—C10—C9116.92 (17)
N7—C8—C9110.43 (16)C10—C9—C8111.50 (15)
N7—C8—H8A109.6C10—C9—H9A109.3
C9—C8—H8A109.6C8—C9—H9A109.3
N7—C8—H8B109.6C10—C9—H9B109.3
C9—C8—H8B109.6C8—C9—H9B109.3
H8A—C8—H8B108.1H9A—C9—H9B108.0
C6—C7—C2121.22 (17)C3—C4—C5120.54 (18)
C6—C7—H6119.4C3—C4—H4119.7
C2—C7—H6119.4C5—C4—H4119.7
C5—N7—C8122.78 (15)C4—C3—C2120.87 (18)
C5—N7—H7115.1C4—C3—H3119.6
C8—N7—H7119.9C2—C3—H3119.6
C7—C6—C5120.24 (17)O1—C1—O2122.35 (18)
C7—C6—H5119.9O1—C1—C2119.08 (17)
C5—C6—H5119.9O2—C1—C2118.57 (17)
N7—C5—C6121.71 (17)H5A—O5—H5B96.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···O50.972.043.009 (2)175
O2—H2···O4i0.951.742.662 (2)165
O3—H1···O1ii1.041.632.622 (2)159
O5—H5A···O2iii0.882.443.103 (2)133
O5—H5A···O4iv0.882.523.129 (2)127
O5—H5B···O5iv0.912.012.890 (2)163
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+3/2, y−1/2, z; (iii) −x+1, −y+1, −z+1; (iv) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formulaC10H11NO4·H2O
Mr227.21
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)4.9387 (19), 19.700 (7), 21.616 (8)
V (Å3)2103.1 (14)
Z8
Radiation typeMo Kα
µ (mm−1)0.12
Crystal size (mm)0.50 × 0.20 × 0.10
Data collection
DiffractometerRigaku AFC-7S Mercury
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.944, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections		15116, 2401, 2059
Rint0.037
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.167, 1.09
No. of reflections2401
No. of parameters146
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.21, −0.29

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···O50.972.043.009 (2)175
O2—H2···O4i0.951.742.662 (2)165
O3—H1···O1ii1.041.632.622 (2)159
O5—H5A···O2iii0.882.443.103 (2)133
O5—H5A···O4iv0.882.523.129 (2)127
O5—H5B···O5iv0.912.012.890 (2)163
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+3/2, y−1/2, z; (iii) −x+1, −y+1, −z+1; (iv) x+1/2, −y+1/2, −z+1.
 

Acknowledgements

The authors would like to acknowledge the NSFC grants (grant Nos. 20761003, 21061005), the Hainan Natural Science Foundation (grant No. 210011), the Education Department of Hainan Province (grant No. Hjkj2008–23) and Hainan University (grant No. qnjj1169) for financial support.

References

First citationKurd, C. D. & Hayao, S. (1952). J. Am. Chem. Soc. 74, 5889–5893.  Google Scholar
 First citationRigaku (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationYong, G. P., Wang, Z. Y. & Cui, Y. (2004). Eur. J. Inorg. Chem. 21, 4317–4323.  Web of Science CSD CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o1098
doi:10.1107/S1600536812009518
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