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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o813.
Published online 2008 April 10. doi:  10.1107/S1600536808009082
PMCID: PMC2961225

Ammonium 1-hydr­oxy-2-naphthoate

Abstract

The title compound, NH4 +·C11H7O3 , was obtained by slow evaporation of a 30% ammonia solution of 1-hydr­oxy-2-naphthoic acid. The crystal structure is stabilized by inter­molecular N—H(...)O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For related literature, see: Kickelbick & Schubert (1999 [triangle]); Ohki et al. (1986 [triangle]); Song et al. (2008 [triangle]).

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Object name is e-64-0o813-scheme1.jpg

Experimental

Crystal data

  • NH4 +·C11H7O3
  • M r = 205.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o813-efi1.jpg
  • a = 30.883 (5) Å
  • b = 3.880 (1) Å
  • c = 15.777 (3) Å
  • β = 95.567 (2)°
  • V = 1881.6 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 (2) K
  • 0.23 × 0.23 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.976, T max = 0.979
  • 6728 measured reflections
  • 1915 independent reflections
  • 1351 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.080
  • wR(F 2) = 0.226
  • S = 1.04
  • 1915 reflections
  • 149 parameters
  • 10 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.55 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009082/rz2202sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009082/rz2202Isup2.hkl

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

Acknowledgments

The authors acknowledge Qiqihar University for a research grant.

supplementary crystallographic information

Comment

1-Hydroxynaphthalene-2-carboxylic acid is a widely used ligand for the synthesis of metal complexes (Kickelbick & Schubert, 1999; Ohki et al., 1986; Song et al., 2008). We report herein the crystal structure of the title compound, which was obtained by slow evaporation of a 30% ammonium solution of 1-hydroxynaphthalene-2-carboxylic acid in air.

The compound consists of discrete 1-hydroxynaphthalene-2-carboxylate anions and ammonium cations (Fig. 1). The anion is substantially planar with a mean deviation of 0.015 (3) Å. The crystal structure is stabilized by intermolecular N–H···O hydrogen bonds (Table 1), forming layers parallel to the bc plane (Fig. 2).

Experimental

Single crystals of the title compound were obtained by slow evaporation of a 30% ammonia solution of 1-hydroxynaphthalene-2-carboxylic acid in air.

Refinement

Ammonium H atoms were located from a difference Fourier map and refined isotropically, with N–H distances restrained to 0.90 (1) Å, H···H distances restrained to 1.43 (2) Å, and with Uiso(H) values fixed at 0.08 Å2. All other H atoms were placed in idealized positions and constrained to ride on their parent atoms with C–H distances of 0.93 Å, O–H distance of 0.82 Å, and with Uiso(H) set at 1.2Ueq(C) or 1.5Ueq(O).

Figures

Fig. 1.
The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular hydrogen bond is shown as a dashed line.
Fig. 2.
A perspective view of crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

N1H4+·C11H7O3F000 = 864
Mr = 205.21Dx = 1.449 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1379 reflections
a = 30.883 (5) Åθ = 2.5–24.1º
b = 3.880 (1) ŵ = 0.11 mm1
c = 15.777 (3) ÅT = 298 (2) K
β = 95.567 (2)ºBlock, colourless
V = 1881.6 (7) Å30.23 × 0.23 × 0.20 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer1915 independent reflections
Radiation source: fine-focus sealed tube1351 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.040
T = 298(2) Kθmax = 27.0º
ω scansθmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −38→38
Tmin = 0.976, Tmax = 0.979k = −4→4
6728 measured reflectionsl = −20→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.080H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.226  w = 1/[σ2(Fo2) + (0.1461P)2 + 0.0944P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1915 reflectionsΔρmax = 0.55 e Å3
149 parametersΔρmin = −0.24 e Å3
10 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
O10.42976 (6)1.0366 (6)0.70025 (11)0.0383 (6)
H10.44961.09810.73540.057*
O20.46982 (6)1.1294 (6)0.84111 (13)0.0472 (6)
O30.44313 (7)0.9570 (6)0.95912 (12)0.0486 (7)
N10.46529 (8)0.4511 (7)0.08424 (16)0.0414 (7)
C10.39678 (8)0.9092 (6)0.74083 (16)0.0259 (6)
C20.39995 (8)0.8798 (7)0.82806 (16)0.0281 (6)
C30.36469 (8)0.7397 (7)0.86694 (16)0.0322 (6)
H30.36660.72140.92600.039*
C40.32803 (9)0.6309 (8)0.82012 (17)0.0354 (7)
H40.30520.53920.84740.042*
C50.32420 (8)0.6559 (7)0.73053 (17)0.0291 (6)
C60.28703 (9)0.5425 (7)0.67931 (19)0.0380 (7)
H60.26400.44710.70500.046*
C70.28423 (9)0.5700 (8)0.5933 (2)0.0441 (8)
H70.25940.49310.56060.053*
C80.31858 (10)0.7139 (8)0.55356 (18)0.0424 (8)
H80.31650.73210.49450.051*
C90.35487 (9)0.8268 (8)0.60050 (17)0.0358 (7)
H90.37730.92420.57330.043*
C100.35900 (8)0.7985 (7)0.68970 (16)0.0268 (6)
C110.43967 (9)0.9947 (7)0.88135 (17)0.0321 (7)
H1A0.4533 (9)0.347 (7)0.1262 (14)0.080*
H1B0.4891 (7)0.565 (8)0.1041 (18)0.080*
H1C0.4720 (10)0.291 (6)0.0471 (16)0.080*
H1D0.4467 (8)0.597 (7)0.0576 (18)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0294 (10)0.0542 (14)0.0317 (10)−0.0088 (9)0.0045 (8)0.0017 (9)
O20.0307 (10)0.0587 (15)0.0509 (13)−0.0139 (9)−0.0027 (9)−0.0017 (11)
O30.0537 (13)0.0560 (15)0.0326 (11)−0.0071 (10)−0.0135 (10)−0.0059 (10)
N10.0445 (14)0.0356 (14)0.0439 (14)−0.0050 (11)0.0037 (12)−0.0057 (11)
C10.0240 (12)0.0254 (13)0.0293 (13)0.0014 (9)0.0070 (10)−0.0002 (10)
C20.0273 (13)0.0253 (14)0.0310 (13)0.0001 (10)0.0003 (10)−0.0035 (10)
C30.0371 (14)0.0330 (15)0.0269 (13)−0.0017 (12)0.0057 (11)0.0026 (11)
C40.0329 (14)0.0391 (17)0.0352 (14)−0.0060 (11)0.0085 (12)0.0052 (12)
C50.0246 (12)0.0264 (14)0.0359 (14)0.0022 (10)0.0010 (10)0.0016 (11)
C60.0306 (14)0.0337 (16)0.0488 (16)−0.0029 (11)−0.0010 (12)−0.0043 (13)
C70.0338 (15)0.0469 (19)0.0480 (17)0.0026 (12)−0.0146 (13)−0.0136 (14)
C80.0440 (16)0.0515 (19)0.0289 (14)0.0107 (14)−0.0100 (12)−0.0052 (13)
C90.0343 (14)0.0436 (17)0.0300 (14)0.0060 (12)0.0049 (11)−0.0019 (12)
C100.0263 (12)0.0239 (13)0.0297 (13)0.0024 (10)0.0000 (10)−0.0007 (10)
C110.0346 (14)0.0271 (14)0.0331 (14)−0.0008 (11)−0.0044 (11)−0.0041 (11)

Geometric parameters (Å, °)

O1—C11.349 (3)C3—H30.9300
O1—H10.8200C4—C51.410 (4)
O2—C111.287 (3)C4—H40.9300
O3—C111.230 (3)C5—C61.409 (4)
N1—H1A0.89 (2)C5—C101.418 (4)
N1—H1B0.89 (3)C6—C71.356 (4)
N1—H1C0.89 (2)C6—H60.9300
N1—H1D0.88 (3)C7—C81.400 (4)
C1—C21.375 (4)C7—H70.9300
C1—C101.419 (3)C8—C91.355 (4)
C2—C31.410 (3)C8—H80.9300
C2—C111.487 (3)C9—C101.405 (4)
C3—C41.358 (4)C9—H90.9300
C1—O1—H1109.5C6—C5—C10118.2 (3)
H1A—N1—H1B110.8 (19)C4—C5—C10119.3 (2)
H1A—N1—H1C108 (2)C7—C6—C5121.3 (3)
H1B—N1—H1C110.0 (19)C7—C6—H6119.4
H1A—N1—H1D110 (2)C5—C6—H6119.4
H1B—N1—H1D109 (2)C6—C7—C8120.1 (3)
H1C—N1—H1D108.3 (19)C6—C7—H7119.9
O1—C1—C2121.5 (2)C8—C7—H7119.9
O1—C1—C10117.3 (2)C9—C8—C7120.5 (3)
C2—C1—C10121.2 (2)C9—C8—H8119.8
C1—C2—C3119.0 (2)C7—C8—H8119.8
C1—C2—C11121.1 (2)C8—C9—C10120.8 (3)
C3—C2—C11120.0 (2)C8—C9—H9119.6
C4—C3—C2121.4 (2)C10—C9—H9119.6
C4—C3—H3119.3C9—C10—C5119.1 (2)
C2—C3—H3119.3C9—C10—C1122.4 (2)
C3—C4—C5120.5 (2)C5—C10—C1118.5 (2)
C3—C4—H4119.7O3—C11—O2122.9 (2)
C5—C4—H4119.7O3—C11—C2121.0 (3)
C6—C5—C4122.5 (3)O2—C11—C2116.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.732.463 (3)148
N1—H1A···O1i0.89 (2)2.07 (3)2.920 (3)161 (3)
N1—H1B···O2ii0.89 (3)1.88 (3)2.756 (3)167 (3)
N1—H1C···O3iii0.89 (2)2.04 (2)2.789 (3)141 (3)
N1—H1D···O3iv0.88 (3)2.08 (2)2.821 (3)140 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2202).

References

  • Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Kickelbick, G. & Schubert, U. (1999). J. Chem. Soc. Dalton Trans. pp. 1301–1306.
  • Ohki, Y., Suzuki, Y., Takeuchi, T., Shimoi, M. & Ouchi, A. (1986). Bull. Chem. Soc. Jpn, 59, 1015–1019.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Song, W.-D., Yan, J.-B., Wang, H. & Ji, L.-L. (2008). Acta Cryst. E64, m5.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography