Crystal structure of 4-(3-carb-oxy-pro-pan-amido)-2-hy-droxy-benzoic acid mono-hydrate.

In the title hydrate, C11H11NO6·H2O, the organic mol-ecule is approximately planar (r.m.s. deviation for the non-H atoms = 0.129 Å) and an intra-molecular O-H⋯O hydrogen bond closes an S(6) ring. In the crystal, the benzoic acid group participates in an O-H⋯O hydrogen bond to the water mol-ecule and accepts a similar bond from another water mol-ecule. The other -CO2H group forms a carb-oxy-lic acid inversion dimer, thereby forming an R 2 (2)(8) loop. These bonds, along with N-H⋯O and C-H⋯O inter-actions, generate a three-dimensional network.

Related literature

For related structures, see: Gowda et al. (2009 ▶, 2011 ▶); Jia et al. (2012 ▶); Saraswathi et al. (2011 ▶).

Experimental

Crystal data

C11H11NO6·H2O

M = 271.22

Monoclinic,

a = 25.2516 (19) Å

b = 8.4656 (5) Å

c = 12.4732 (10) Å

β = 117.446 (3)°

V = 2366.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.28 × 0.24 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.964, T max = 0.983

9402 measured reflections

2556 independent reflections

1738 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.122

S = 1.02

2556 reflections

181 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814024581/hb7310sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814024581/hb7310Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814024581/hb7310Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814024581/hb7310fig1.tif

View of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

PLATON . DOI: 10.1107/S1600536814024581/hb7310fig2.tif

The partial packing (PLATON; Spek, 2009), which shows that mol­ecules form dimers which are inter­linked to three-dimensional polymeric network.

CCDC reference: 1033346

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H11NO6·H2O	F(000) = 1136
Mr = 271.22	Dx = 1.523 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.2516 (19) Å	Cell parameters from 1738 reflections
b = 8.4656 (5) Å	θ = 2.6–27.0°
c = 12.4732 (10) Å	µ = 0.13 mm−1
β = 117.446 (3)°	T = 296 K
V = 2366.3 (3) Å3	Plate, colourless
Z = 8	0.28 × 0.24 × 0.16 mm

Bruker Kappa APEXII CCD diffractometer	2556 independent reflections
Radiation source: fine-focus sealed tube	1738 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 7.80 pixels mm-1	θmax = 27.0°, θmin = 2.6°
ω scans	h = −32→32
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.964, Tmax = 0.983	l = −15→15
9402 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.9039P] where P = (Fo2 + 2Fc2)/3
2556 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.22 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
O1	0.45356 (6)	−0.2827 (2)	0.78347 (15)	0.0561 (5)
H1	0.4765	−0.3404	0.8379	0.084*
O2	0.39232 (6)	−0.35291 (17)	0.85809 (13)	0.0452 (4)
O3	0.28556 (6)	−0.22986 (16)	0.76254 (12)	0.0378 (4)
H3	0.3133	−0.2845	0.8098	0.057*
O4	0.14489 (7)	0.0630 (2)	0.42736 (15)	0.0607 (5)
O5	−0.01362 (6)	0.3599 (2)	0.08989 (17)	0.0658 (6)
H5	−0.0287	0.4249	0.0352	0.099*
O6	0.06897 (6)	0.43838 (18)	0.08601 (14)	0.0494 (4)
N1	0.22758 (6)	0.07905 (19)	0.40306 (14)	0.0340 (4)
H1A	0.2411	0.1192	0.3571	0.041*
C1	0.40152 (9)	−0.2813 (2)	0.78284 (18)	0.0347 (5)
C2	0.35583 (8)	−0.1892 (2)	0.68505 (17)	0.0301 (4)
C3	0.29976 (8)	−0.1667 (2)	0.67907 (16)	0.0281 (4)
C4	0.25635 (8)	−0.0780 (2)	0.58744 (16)	0.0292 (4)
H4	0.2194	−0.0624	0.5852	0.035*
C5	0.26845 (8)	−0.0126 (2)	0.49906 (17)	0.0288 (4)
C6	0.32402 (9)	−0.0373 (2)	0.50317 (19)	0.0378 (5)
H6	0.3320	0.0051	0.4433	0.045*
C7	0.36652 (9)	−0.1230 (2)	0.59436 (19)	0.0383 (5)
H7	0.4035	−0.1379	0.5964	0.046*
C8	0.17030 (9)	0.1135 (2)	0.37201 (19)	0.0364 (5)
C9	0.13998 (9)	0.2187 (2)	0.26307 (18)	0.0381 (5)
H9A	0.1433	0.1717	0.1955	0.046*
H9B	0.1600	0.3203	0.2800	0.046*
C10	0.07507 (9)	0.2429 (2)	0.22904 (19)	0.0412 (5)
H10A	0.0548	0.1417	0.2065	0.049*
H10B	0.0720	0.2808	0.2993	0.049*
C11	0.04396 (9)	0.3559 (2)	0.12818 (18)	0.0367 (5)
O7	0.54172 (8)	−0.4497 (2)	0.94112 (17)	0.0565 (5)
H7A	0.5638 (13)	−0.464 (3)	0.914 (3)	0.085*
H7B	0.5480 (14)	−0.501 (4)	0.991 (3)	0.085*

	U11	U22	U33	U12	U13	U23
O1	0.0331 (8)	0.0803 (12)	0.0558 (11)	0.0224 (8)	0.0212 (8)	0.0336 (9)
O2	0.0410 (9)	0.0564 (9)	0.0380 (9)	0.0118 (7)	0.0181 (7)	0.0180 (7)
O3	0.0376 (8)	0.0478 (8)	0.0336 (8)	0.0106 (7)	0.0213 (7)	0.0120 (6)
O4	0.0362 (9)	0.0880 (12)	0.0641 (11)	0.0175 (8)	0.0284 (8)	0.0389 (10)
O5	0.0295 (9)	0.0899 (14)	0.0719 (13)	0.0136 (8)	0.0181 (9)	0.0463 (10)
O6	0.0346 (8)	0.0602 (10)	0.0530 (10)	0.0090 (7)	0.0199 (8)	0.0229 (8)
N1	0.0254 (9)	0.0424 (9)	0.0339 (10)	0.0059 (7)	0.0133 (8)	0.0122 (8)
C1	0.0309 (11)	0.0383 (11)	0.0343 (11)	0.0058 (9)	0.0147 (9)	0.0034 (9)
C2	0.0281 (10)	0.0325 (10)	0.0283 (10)	0.0038 (8)	0.0118 (8)	0.0032 (8)
C3	0.0316 (10)	0.0289 (9)	0.0257 (10)	−0.0002 (8)	0.0148 (8)	−0.0014 (8)
C4	0.0235 (10)	0.0335 (10)	0.0313 (11)	0.0024 (8)	0.0133 (9)	−0.0013 (8)
C5	0.0255 (10)	0.0290 (10)	0.0294 (10)	0.0022 (8)	0.0105 (8)	0.0018 (8)
C6	0.0328 (11)	0.0473 (12)	0.0385 (12)	0.0067 (9)	0.0207 (10)	0.0135 (10)
C7	0.0295 (11)	0.0479 (12)	0.0421 (12)	0.0088 (9)	0.0203 (10)	0.0128 (10)
C8	0.0335 (11)	0.0388 (11)	0.0385 (12)	0.0020 (9)	0.0180 (10)	0.0058 (9)
C9	0.0335 (11)	0.0411 (11)	0.0379 (12)	0.0055 (9)	0.0149 (10)	0.0085 (9)
C10	0.0325 (11)	0.0482 (13)	0.0416 (12)	0.0067 (10)	0.0159 (10)	0.0106 (10)
C11	0.0295 (11)	0.0424 (12)	0.0371 (12)	0.0045 (9)	0.0143 (10)	0.0039 (9)
O7	0.0420 (10)	0.0775 (13)	0.0557 (11)	0.0260 (9)	0.0273 (9)	0.0329 (9)

O1—C1	1.310 (2)	C4—C5	1.388 (3)
O1—H1	0.8200	C4—H4	0.9300
O2—C1	1.226 (2)	C5—C6	1.396 (3)
O3—C3	1.357 (2)	C6—C7	1.359 (3)
O3—H3	0.8200	C6—H6	0.9300
O4—C8	1.217 (2)	C7—H7	0.9300
O5—C11	1.305 (2)	C8—C9	1.505 (3)
O5—H5	0.8200	C9—C10	1.506 (3)
O6—C11	1.212 (2)	C9—H9A	0.9700
N1—C8	1.346 (2)	C9—H9B	0.9700
N1—C5	1.400 (2)	C10—C11	1.485 (3)
N1—H1A	0.8600	C10—H10A	0.9700
C1—C2	1.459 (3)	C10—H10B	0.9700
C2—C7	1.396 (3)	O7—H7A	0.78 (3)
C2—C3	1.396 (3)	O7—H7B	0.72 (3)
C3—C4	1.385 (3)
C1—O1—H1	109.5	C5—C6—H6	119.9
C3—O3—H3	109.5	C6—C7—C2	121.31 (18)
C11—O5—H5	109.5	C6—C7—H7	119.3
C8—N1—C5	129.57 (16)	C2—C7—H7	119.3
C8—N1—H1A	115.2	O4—C8—N1	122.57 (19)
C5—N1—H1A	115.2	O4—C8—C9	122.59 (18)
O2—C1—O1	122.28 (18)	N1—C8—C9	114.84 (17)
O2—C1—C2	123.24 (18)	C8—C9—C10	111.69 (17)
O1—C1—C2	114.48 (17)	C8—C9—H9A	109.3
C7—C2—C3	118.18 (17)	C10—C9—H9A	109.3
C7—C2—C1	121.20 (17)	C8—C9—H9B	109.3
C3—C2—C1	120.62 (17)	C10—C9—H9B	109.3
O3—C3—C4	117.26 (16)	H9A—C9—H9B	107.9
O3—C3—C2	121.68 (16)	C11—C10—C9	114.12 (17)
C4—C3—C2	121.05 (16)	C11—C10—H10A	108.7
C3—C4—C5	119.45 (17)	C9—C10—H10A	108.7
C3—C4—H4	120.3	C11—C10—H10B	108.7
C5—C4—H4	120.3	C9—C10—H10B	108.7
C4—C5—C6	119.77 (17)	H10A—C10—H10B	107.6
C4—C5—N1	123.71 (16)	O6—C11—O5	122.79 (19)
C6—C5—N1	116.52 (17)	O6—C11—C10	124.11 (18)
C7—C6—C5	120.22 (18)	O5—C11—C10	113.09 (18)
C7—C6—H6	119.9	H7A—O7—H7B	111 (3)
O2—C1—C2—C7	−173.4 (2)	C8—N1—C5—C6	175.30 (19)
O1—C1—C2—C7	6.1 (3)	C4—C5—C6—C7	−1.0 (3)
O2—C1—C2—C3	5.8 (3)	N1—C5—C6—C7	179.09 (18)
O1—C1—C2—C3	−174.74 (18)	C5—C6—C7—C2	0.5 (3)
C7—C2—C3—O3	178.72 (17)	C3—C2—C7—C6	0.8 (3)
C1—C2—C3—O3	−0.5 (3)	C1—C2—C7—C6	180.0 (2)
C7—C2—C3—C4	−1.6 (3)	C5—N1—C8—O4	−1.2 (4)
C1—C2—C3—C4	179.23 (17)	C5—N1—C8—C9	179.15 (18)
O3—C3—C4—C5	−179.20 (16)	O4—C8—C9—C10	−3.5 (3)
C2—C3—C4—C5	1.1 (3)	N1—C8—C9—C10	176.14 (17)
C3—C4—C5—C6	0.2 (3)	C8—C9—C10—C11	175.35 (17)
C3—C4—C5—N1	−179.88 (17)	C9—C10—C11—O6	−9.3 (3)
C8—N1—C5—C4	−4.6 (3)	C9—C10—C11—O5	171.72 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O7	0.82	1.81	2.605 (2)	163
O3—H3···O2	0.82	1.89	2.6099 (19)	146
O5—H5···O6i	0.82	1.80	2.618 (2)	174
N1—H1A···O3ii	0.86	2.18	3.035 (2)	173
C10—H10B···O5iii	0.97	2.53	3.424 (3)	153
O7—H7A···O4iv	0.78 (3)	2.15 (3)	2.854 (2)	151 (3)
O7—H7B···O2v	0.72 (3)	2.17 (3)	2.827 (2)	152 (3)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1O7	0.82	1.81	2.605(2)	163
O3H3O2	0.82	1.89	2.6099(19)	146
O5H5O6i	0.82	1.80	2.618(2)	174
N1H1AO3ii	0.86	2.18	3.035(2)	173
C10H10BO5iii	0.97	2.53	3.424(3)	153
O7H7AO4iv	0.78(3)	2.15(3)	2.854(2)	151(3)
O7H7BO2v	0.72(3)	2.17(3)	2.827(2)	152(3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .