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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1304.
Published online 2009 May 14. doi:  10.1107/S1600536809017462
PMCID: PMC2969601

3-Ammonio-4-hydroxy­benzoate monohydrate

Abstract

The title compound, C7H7NO3·H2O, which crystallized as a hydrate, was obtained from an extraction of the plant species Saussurea atkinsonii of the asteraceae family collected from the hilly area (Ayubia) of Pakistan during the flowering season. The dihedral angle between the benzene ring and the carboxyl­ate group is 25.64 (5)°. In the crystal, the packing is consolidated by N—H(...)O and O—H(...)O hydrogen bonds, as well as weak aromatic π–π stacking [centroid–centroid separation = 3.9365 (9) Å] and C=O(...)π inter­actions.

Related literature

For a related structure, see: Bertasso et al. (2001 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-o1304-scheme1.jpg

Experimental

Crystal data

  • C7H7NO3·H2O
  • M r = 171.15
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1304-efi1.jpg
  • a = 8.7711 (3) Å
  • b = 12.7193 (7) Å
  • c = 12.9289 (6) Å
  • V = 1442.38 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 296 K
  • 0.26 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.971, T max = 0.976
  • 8827 measured reflections
  • 1725 independent reflections
  • 1277 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.118
  • S = 1.06
  • 1725 reflections
  • 127 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017462/hb2969sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017462/hb2969Isup2.hkl

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

Acknowledgments

SU greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a Scholarship under the Indigenous PhD Program (PIN 042–121314-PS2–287).

supplementary crystallographic information

Comment

The medicinal plants are available all over the world. Locally available plant specie Saussurea atkinsonii of asteraceae family was collected from hilly area (Ayubia) of Pakistan during the flowering season. The plant was dried inside room for 20–25 days. The title compound (I), (Fig. 1), is an extract of it in chloroform and methanol. The study of its bio-activity is in progress.

The crystal structure of (II) (4-vinylphenyl 3-amino-4-hydroxybenzoate or bagremycin A (Bertasso et al., 2001), has been reported which contains the aromatic ring along with heavy atoms of the substituants of (I). In the title compound, the bond distances and bond angles are within normal ranges (Allen et al., 1987). The benzene ring A (C1–C6) is planar and is oriented at a dihedral angle of 25.64 (5)° with the CO2 group. The N-atom of ammonium is in plane of the ring A, whereas the O-atom of hydroxy group is at a distance of -0.0580 (21) Å from the same.

There exist intensive intermolecular H-bonding (Table 1), resulting in three-dimensional polymeric network. There also exist CgA···CgAi [symmetry code i = 1 - x, 1 - y, -z] interaction at a distance of 3.9365 (9) Å, where CgA is the centroid of aromatic ring. The molecules may also be stabilized due to C==O···π interaction (Table 1).

Experimental

The Specie Saussurea atkinsonii of asteraceae family was dried inside room for 20–25 days as a whole and grinded. The extract was obtained using soxhlet apparatus in 50% chloroform and 50% methanol and it was subjected to isolation by performing column chromatography and thin layer chromatography. The extract obtained was recrystallized from methanol and light brown rods of (I) were obtained. The water found in the structure was presumably incorporated from the atomsphere.

Refinement

The coordinates of H-atoms of hydroxy, ammonium moiety and water molecule were refined. The other H-atoms were positioned geometrically, with C-H = 0.93 Å for aromatic type and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C, N, O).

Figures

Fig. 1.
View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radius.
Fig. 2.
The partial packing of (I), showing that molecules form three-dimensional polymeric network.

Crystal data

C7H7NO3·H2OF(000) = 720
Mr = 171.15Dx = 1.576 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1725 reflections
a = 8.7711 (3) Åθ = 3.2–28.3°
b = 12.7193 (7) ŵ = 0.13 mm1
c = 12.9289 (6) ÅT = 296 K
V = 1442.38 (11) Å3Rod, light brown
Z = 80.26 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer1752 independent reflections
Radiation source: fine-focus sealed tube1277 reflections with I > 2σ(I)
graphiteRint = 0.033
Detector resolution: 7.40 pixels mm-1θmax = 28.3°, θmin = 3.2°
ω scansh = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −15→16
Tmin = 0.971, Tmax = 0.976l = −11→17
8827 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0684P)2 + 0.0409P] where P = (Fo2 + 2Fc2)/3
1725 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = −0.24 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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)

xyzUiso*/Ueq
O10.69598 (12)0.67023 (9)0.16442 (9)0.0284 (4)
O20.83764 (11)0.53206 (10)0.12269 (9)0.0302 (4)
O30.20823 (11)0.29862 (10)0.11448 (10)0.0319 (4)
N10.48231 (14)0.21872 (11)0.16388 (11)0.0232 (4)
C10.57236 (15)0.50443 (12)0.14203 (11)0.0205 (5)
C20.58869 (15)0.39732 (13)0.15731 (11)0.0203 (4)
C30.46511 (14)0.33137 (12)0.14912 (11)0.0193 (4)
C40.32078 (15)0.37051 (12)0.12444 (12)0.0212 (4)
C50.30300 (15)0.47766 (13)0.11230 (12)0.0241 (5)
C60.42742 (15)0.54444 (13)0.12153 (12)0.0232 (4)
C70.71208 (15)0.57284 (13)0.14299 (11)0.0216 (5)
O40.43081 (12)0.34489 (11)0.45169 (10)0.0308 (4)
H1A0.587 (2)0.2008 (14)0.1721 (12)0.0278*
H1B0.4519 (19)0.1828 (14)0.1034 (15)0.0278*
H1C0.4229 (18)0.1948 (14)0.2189 (14)0.0278*
H20.684030.369740.173250.0243*
H30.119 (2)0.3252 (16)0.0913 (15)0.0383*
H50.207140.505240.097850.0289*
H60.414020.616560.113980.0279*
H410.3898 (19)0.4057 (16)0.4289 (15)0.0369*
H420.381 (2)0.2927 (16)0.4217 (15)0.0369*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0316 (5)0.0154 (7)0.0383 (7)−0.0051 (4)0.0053 (4)−0.0044 (5)
O20.0231 (5)0.0245 (7)0.0430 (7)−0.0032 (5)0.0043 (4)−0.0063 (5)
O30.0193 (5)0.0217 (7)0.0548 (8)−0.0032 (4)−0.0059 (5)0.0000 (6)
N10.0214 (6)0.0150 (8)0.0331 (8)0.0010 (5)0.0027 (5)0.0015 (6)
C10.0236 (7)0.0164 (9)0.0216 (8)−0.0029 (5)0.0013 (5)−0.0026 (6)
C20.0183 (6)0.0190 (9)0.0235 (8)0.0006 (5)0.0011 (5)−0.0006 (6)
C30.0209 (6)0.0142 (9)0.0228 (8)0.0003 (5)0.0018 (5)0.0013 (6)
C40.0195 (6)0.0188 (9)0.0254 (8)−0.0024 (5)−0.0004 (5)−0.0019 (6)
C50.0205 (6)0.0218 (9)0.0300 (9)0.0041 (6)−0.0024 (6)0.0003 (7)
C60.0290 (7)0.0137 (8)0.0270 (8)0.0014 (6)0.0000 (5)0.0005 (7)
C70.0265 (7)0.0169 (9)0.0214 (8)−0.0044 (6)0.0013 (5)−0.0002 (6)
O40.0257 (5)0.0255 (8)0.0412 (7)0.0017 (5)−0.0044 (4)0.0023 (6)

Geometric parameters (Å, °)

O1—C71.277 (2)C1—C71.503 (2)
O2—C71.2453 (17)C1—C61.3948 (19)
O3—C41.3518 (18)C1—C21.384 (2)
O3—H30.904 (18)C2—C31.375 (2)
O4—H410.90 (2)C3—C41.3972 (19)
O4—H420.884 (19)C4—C51.381 (2)
N1—C31.453 (2)C5—C61.388 (2)
N1—H1C0.933 (17)C2—H20.9300
N1—H1A0.952 (18)C5—H50.9300
N1—H1B0.944 (19)C6—H60.9300
C4—O3—H3114.3 (13)O3—C4—C5125.06 (12)
H41—O4—H42107.7 (17)C3—C4—C5118.69 (13)
C3—N1—H1A110.5 (11)O3—C4—C3116.26 (13)
C3—N1—H1B109.8 (11)C4—C5—C6120.36 (13)
H1A—N1—H1B104.4 (14)C1—C6—C5120.64 (15)
H1A—N1—H1C112.1 (14)O1—C7—O2123.20 (14)
C3—N1—H1C111.3 (11)O2—C7—C1118.57 (14)
H1B—N1—H1C108.4 (15)O1—C7—C1118.24 (12)
C2—C1—C6118.72 (13)C3—C2—H2120.00
C2—C1—C7118.97 (12)C1—C2—H2120.00
C6—C1—C7122.24 (14)C4—C5—H5120.00
C1—C2—C3120.53 (13)C6—C5—H5120.00
N1—C3—C2120.64 (12)C1—C6—H6120.00
C2—C3—C4120.97 (14)C5—C6—H6120.00
N1—C3—C4118.38 (12)
C6—C1—C2—C32.1 (2)C1—C2—C3—C40.5 (2)
C7—C1—C2—C3−175.02 (13)N1—C3—C4—O3−1.1 (2)
C2—C1—C6—C5−2.7 (2)N1—C3—C4—C5178.75 (14)
C7—C1—C6—C5174.30 (14)C2—C3—C4—O3177.60 (14)
C2—C1—C7—O1−156.35 (14)C2—C3—C4—C5−2.5 (2)
C2—C1—C7—O223.8 (2)O3—C4—C5—C6−178.25 (15)
C6—C1—C7—O126.7 (2)C3—C4—C5—C61.9 (2)
C6—C1—C7—O2−153.17 (15)C4—C5—C6—C10.7 (2)
C1—C2—C3—N1179.24 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.952 (18)1.945 (18)2.8884 (16)170.4 (14)
N1—H1A···O2i0.952 (18)2.335 (18)2.9008 (18)117.6 (13)
N1—H1B···O4ii0.944 (19)2.001 (19)2.8957 (19)157.4 (16)
N1—H1C···O1iii0.933 (17)1.860 (17)2.7846 (18)170.5 (16)
O3—H3···O4iv0.904 (18)1.760 (18)2.6456 (15)166.0 (19)
O4—H41···O2iv0.90 (2)1.80 (2)2.6945 (18)171.1 (17)
O4—H42···O1iii0.884 (19)2.03 (2)2.9027 (18)168.8 (17)
C6—H6···O3v0.932.553.446 (2)161
C7—O2···CgAvi1.2453 (17)3.4940 (13)3.9313 (16)101.24 (9)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2969).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bertasso, M., Holzenkampfer, M., Zeeck, A., Dall’Antonia, F. & Fiedler, H.-P. (2001). J. Antibiot.54, 730–737.
  • Bruker (2005). SADABS Bruker AXS Inc. Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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