4-[(2-Carb-oxy-eth-yl)amino]-benzoic acid monohydrate.

In the title compound, C(10)H(11)NO(4)·H(2)O, the carboxyl group is twisted at a dihedral angle of 6.1 (3)° with respect to the benzene ring. In the crystal, the organic mol-ecules 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 mol-ecules form [100] chains linked by O-H⋯O hydrogen bonds. The organic mol-ecule and water chains are cross-linked by N-H⋯O(water) and O(water)-H⋯O hydrogen bonds, generating (001) sheets.

Related literature

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

Experimental

Crystal data

C10H11NO4·H2O

M = 227.21

Orthorhombic,

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 ▶) T min = 0.944, T max = 0.989

15116 measured reflections

2401 independent reflections

2059 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 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

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009518/hb6663sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812009518/hb6663Isup3.cml

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

C10H11NO4·H2O	F(000) = 960
Mr = 227.21	Dx = 1.435 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4011 reflections
a = 4.9387 (19) Å	θ = 2.3–27.4°
b = 19.700 (7) Å	µ = 0.12 mm−1
c = 21.616 (8) Å	T = 298 K
V = 2103.1 (14) Å3	Prism, colourless
Z = 8	0.50 × 0.20 × 0.10 mm

Rigaku AFC-7S Mercury diffractometer	2401 independent reflections
Radiation source: Rotating Anode	2059 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.037
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 2.8°
CCD_Profile_fitting scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −25→17
Tmin = 0.944, Tmax = 0.989	l = −27→28
15116 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-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 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
O4	0.0461 (3)	0.17797 (7)	0.60257 (7)	0.0513 (4)
O3	0.2084 (3)	0.20433 (7)	0.69553 (7)	0.0560 (4)
O1	0.9408 (3)	0.60527 (7)	0.68389 (8)	0.0552 (4)
C2	0.7123 (4)	0.51980 (9)	0.62835 (9)	0.0386 (4)
O2	1.0540 (3)	0.58943 (8)	0.58500 (7)	0.0570 (4)
C8	−0.0056 (4)	0.33809 (9)	0.67078 (9)	0.0397 (4)
H8A	−0.1384	0.3739	0.6760	0.048*
H8B	0.0950	0.3338	0.7091	0.048*
C7	0.5435 (4)	0.50574 (9)	0.67792 (9)	0.0381 (4)
H6	0.5525	0.5327	0.7132	0.046*
N7	0.1779 (3)	0.35565 (8)	0.62101 (7)	0.0420 (4)
C6	0.3618 (4)	0.45234 (9)	0.67594 (9)	0.0382 (4)
H5	0.2502	0.4438	0.7097	0.046*
C5	0.3452 (4)	0.41113 (9)	0.62324 (9)	0.0369 (4)
C10	0.0490 (4)	0.21407 (9)	0.65073 (9)	0.0395 (4)
C9	−0.1486 (4)	0.27183 (10)	0.65677 (10)	0.0427 (5)
H9A	−0.2760	0.2618	0.6897	0.051*
H9B	−0.2500	0.2764	0.6186	0.051*
C4	0.5114 (4)	0.42647 (10)	0.57240 (9)	0.0447 (5)
H4	0.4999	0.4004	0.5366	0.054*
C3	0.6909 (4)	0.47976 (10)	0.57507 (9)	0.0450 (5)
H3	0.7995	0.4893	0.5410	0.054*
C1	0.9125 (4)	0.57462 (9)	0.63300 (9)	0.0403 (4)
O5	0.1077 (4)	0.28799 (9)	0.49724 (8)	0.0680 (5)
H1	0.3415	0.1673	0.6803	0.082*
H5A	0.1216	0.3062	0.4601	0.082*
H5B	0.2810	0.2725	0.4992	0.082*
H2	1.1723	0.6267	0.5907	0.082*
H7	0.1518	0.3363	0.5801	0.059 (7)*

	U11	U22	U33	U12	U13	U23
O4	0.0567 (9)	0.0465 (8)	0.0507 (9)	0.0084 (6)	−0.0045 (7)	−0.0030 (6)
O3	0.0587 (9)	0.0514 (8)	0.0578 (10)	0.0159 (7)	−0.0138 (7)	−0.0084 (7)
O1	0.0605 (10)	0.0455 (8)	0.0597 (10)	−0.0115 (7)	−0.0070 (7)	−0.0042 (7)
C2	0.0365 (9)	0.0352 (9)	0.0441 (10)	−0.0001 (7)	−0.0031 (7)	0.0057 (7)
O2	0.0542 (9)	0.0586 (9)	0.0583 (10)	−0.0170 (7)	−0.0009 (7)	0.0130 (7)
C8	0.0384 (9)	0.0364 (9)	0.0444 (10)	0.0031 (7)	0.0034 (8)	−0.0010 (7)
C7	0.0408 (9)	0.0322 (9)	0.0412 (10)	0.0028 (7)	−0.0032 (8)	−0.0012 (7)
N7	0.0443 (9)	0.0409 (8)	0.0407 (9)	−0.0052 (7)	0.0030 (7)	−0.0046 (6)
C6	0.0381 (9)	0.0366 (9)	0.0401 (10)	0.0021 (7)	0.0020 (7)	0.0007 (7)
C5	0.0354 (9)	0.0340 (8)	0.0414 (10)	0.0026 (7)	−0.0020 (7)	0.0020 (7)
C10	0.0386 (9)	0.0339 (9)	0.0460 (11)	−0.0030 (7)	0.0019 (8)	0.0044 (7)
C9	0.0344 (9)	0.0407 (10)	0.0530 (11)	−0.0004 (7)	0.0003 (8)	−0.0001 (8)
C4	0.0487 (11)	0.0481 (11)	0.0372 (10)	−0.0052 (9)	0.0023 (8)	−0.0043 (8)
C3	0.0447 (10)	0.0510 (11)	0.0392 (10)	−0.0048 (8)	0.0029 (8)	0.0049 (8)
C1	0.0394 (9)	0.0375 (9)	0.0441 (10)	0.0004 (7)	−0.0030 (8)	0.0065 (8)
O5	0.0777 (12)	0.0765 (12)	0.0498 (10)	−0.0008 (10)	0.0038 (8)	0.0037 (8)

O4—C10	1.261 (2)	C7—H6	0.9300
O3—C10	1.263 (2)	N7—C5	1.371 (2)
O3—H1	1.0351	N7—H7	0.9720
O1—C1	1.262 (2)	C6—C5	1.401 (3)
C2—C7	1.386 (3)	C6—H5	0.9300
C2—C3	1.400 (3)	C5—C4	1.404 (3)
C2—C1	1.468 (3)	C10—C9	1.505 (3)
O2—C1	1.284 (2)	C9—H9A	0.9700
O2—H2	0.9458	C9—H9B	0.9700
C8—N7	1.448 (3)	C4—C3	1.375 (3)
C8—C9	1.515 (3)	C4—H4	0.9300
C8—H8A	0.9700	C3—H3	0.9300
C8—H8B	0.9700	O5—H5A	0.8817
C7—C6	1.383 (3)	O5—H5B	0.9095
C10—O3—H1	105.0	N7—C5—C4	119.75 (17)
C7—C2—C3	118.57 (17)	C6—C5—C4	118.51 (17)
C7—C2—C1	119.96 (17)	O4—C10—O3	123.67 (18)
C3—C2—C1	121.45 (17)	O4—C10—C9	119.40 (17)
C1—O2—H2	114.0	O3—C10—C9	116.92 (17)
N7—C8—C9	110.43 (16)	C10—C9—C8	111.50 (15)
N7—C8—H8A	109.6	C10—C9—H9A	109.3
C9—C8—H8A	109.6	C8—C9—H9A	109.3
N7—C8—H8B	109.6	C10—C9—H9B	109.3
C9—C8—H8B	109.6	C8—C9—H9B	109.3
H8A—C8—H8B	108.1	H9A—C9—H9B	108.0
C6—C7—C2	121.22 (17)	C3—C4—C5	120.54 (18)
C6—C7—H6	119.4	C3—C4—H4	119.7
C2—C7—H6	119.4	C5—C4—H4	119.7
C5—N7—C8	122.78 (15)	C4—C3—C2	120.87 (18)
C5—N7—H7	115.1	C4—C3—H3	119.6
C8—N7—H7	119.9	C2—C3—H3	119.6
C7—C6—C5	120.24 (17)	O1—C1—O2	122.35 (18)
C7—C6—H5	119.9	O1—C1—C2	119.08 (17)
C5—C6—H5	119.9	O2—C1—C2	118.57 (17)
N7—C5—C6	121.71 (17)	H5A—O5—H5B	96.1

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

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) ; (ii) ; (iii) ; (iv) .