Ammonium 1-hydr­oxy-2-naphthoate

Bi, Y.; Han, C.-L.

doi:10.1107/S1600536808009082

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o813

doi:10.1107/S1600536808009082

Open

access

Ammonium 1-hydroxy-2-naphthoate

Ye Bi ^a and Cheng-Li Han ^a ^*

^aCollege of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, People's Republic of China
^*Correspondence e-mail: chengli_han@126.com

(Received 18 March 2008; accepted 3 April 2008; online 10 April 2008)

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 ); Ohki et al. (1986 ); Song et al. (2008 ).

Experimental

Crystal data

NH₄⁺·C₁₁H₇O₃⁻
M_r = 205.21
Monoclinic, C 2/c
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 ) 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[F² > 2σ(F²)] = 0.080
wR(F²) = 0.226
S = 1.04
1915 reflections
149 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.73	2.463 (3)	148
N1—H1A⋯O1ⁱ	0.89 (2)	2.07 (3)	2.920 (3)	161 (3)
N1—H1B⋯O2ⁱⁱ	0.89 (3)	1.88 (3)	2.756 (3)	167 (3)
N1—H1C⋯O3ⁱⁱⁱ	0.89 (2)	2.04 (2)	2.789 (3)	141 (3)
N1—H1D⋯O3^iv	0.88 (3)	2.08 (2)	2.821 (3)	140 (3)
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+2, -z+1; (iii) x, y-1, z-1; (iv) x, y, z-1.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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

	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.

Ammonium 1-hydroxy-2-naphthoate top

Crystal data top

NH₄⁺·C₁₁H₇O₃⁻	F(000) = 864
M_r = 205.21	D_x = 1.449 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1379 reflections
a = 30.883 (5) Å	θ = 2.5–24.1°
b = 3.880 (1) Å	µ = 0.11 mm⁻¹
c = 15.777 (3) Å	T = 298 K
β = 95.567 (2)°	Block, colourless
V = 1881.6 (7) Å³	0.23 × 0.23 × 0.20 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	1915 independent reflections
Radiation source: fine-focus sealed tube	1351 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 27.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −38→38
T_min = 0.976, T_max = 0.979	k = −4→4
6728 measured reflections	l = −20→19

Refinement top

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.226	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.1461P)² + 0.0944P] where P = (F_o² + 2F_c²)/3
1915 reflections	(Δ/σ)_max < 0.001
149 parameters	Δρ_max = 0.55 e Å⁻³
10 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

NH₄⁺·C₁₁H₇O₃⁻	V = 1881.6 (7) Å³
M_r = 205.21	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.883 (5) Å	µ = 0.11 mm⁻¹
b = 3.880 (1) Å	T = 298 K
c = 15.777 (3) Å	0.23 × 0.23 × 0.20 mm
β = 95.567 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1915 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1351 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.979	R_int = 0.040
6728 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	10 restraints
wR(F²) = 0.226	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.55 e Å⁻³
1915 reflections	Δρ_min = −0.24 e Å⁻³
149 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

	x	y	z	U_iso*/U_eq
O1	0.42976 (6)	1.0366 (6)	0.70025 (11)	0.0383 (6)
H1	0.4496	1.0981	0.7354	0.057*
O2	0.46982 (6)	1.1294 (6)	0.84111 (13)	0.0472 (6)
O3	0.44313 (7)	0.9570 (6)	0.95912 (12)	0.0486 (7)
N1	0.46529 (8)	0.4511 (7)	0.08424 (16)	0.0414 (7)
C1	0.39678 (8)	0.9092 (6)	0.74083 (16)	0.0259 (6)
C2	0.39995 (8)	0.8798 (7)	0.82806 (16)	0.0281 (6)
C3	0.36469 (8)	0.7397 (7)	0.86694 (16)	0.0322 (6)
H3	0.3666	0.7214	0.9260	0.039*
C4	0.32803 (9)	0.6309 (8)	0.82012 (17)	0.0354 (7)
H4	0.3052	0.5392	0.8474	0.042*
C5	0.32420 (8)	0.6559 (7)	0.73053 (17)	0.0291 (6)
C6	0.28703 (9)	0.5425 (7)	0.67931 (19)	0.0380 (7)
H6	0.2640	0.4471	0.7050	0.046*
C7	0.28423 (9)	0.5700 (8)	0.5933 (2)	0.0441 (8)
H7	0.2594	0.4931	0.5606	0.053*
C8	0.31858 (10)	0.7139 (8)	0.55356 (18)	0.0424 (8)
H8	0.3165	0.7321	0.4945	0.051*
C9	0.35487 (9)	0.8268 (8)	0.60050 (17)	0.0358 (7)
H9	0.3773	0.9242	0.5733	0.043*
C10	0.35900 (8)	0.7985 (7)	0.68970 (16)	0.0268 (6)
C11	0.43967 (9)	0.9947 (7)	0.88135 (17)	0.0321 (7)
H1A	0.4533 (9)	0.347 (7)	0.1262 (14)	0.080*
H1B	0.4891 (7)	0.565 (8)	0.1041 (18)	0.080*
H1C	0.4720 (10)	0.291 (6)	0.0471 (16)	0.080*
H1D	0.4467 (8)	0.597 (7)	0.0576 (18)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0294 (10)	0.0542 (14)	0.0317 (10)	−0.0088 (9)	0.0045 (8)	0.0017 (9)
O2	0.0307 (10)	0.0587 (15)	0.0509 (13)	−0.0139 (9)	−0.0027 (9)	−0.0017 (11)
O3	0.0537 (13)	0.0560 (15)	0.0326 (11)	−0.0071 (10)	−0.0135 (10)	−0.0059 (10)
N1	0.0445 (14)	0.0356 (14)	0.0439 (14)	−0.0050 (11)	0.0037 (12)	−0.0057 (11)
C1	0.0240 (12)	0.0254 (13)	0.0293 (13)	0.0014 (9)	0.0070 (10)	−0.0002 (10)
C2	0.0273 (13)	0.0253 (14)	0.0310 (13)	0.0001 (10)	0.0003 (10)	−0.0035 (10)
C3	0.0371 (14)	0.0330 (15)	0.0269 (13)	−0.0017 (12)	0.0057 (11)	0.0026 (11)
C4	0.0329 (14)	0.0391 (17)	0.0352 (14)	−0.0060 (11)	0.0085 (12)	0.0052 (12)
C5	0.0246 (12)	0.0264 (14)	0.0359 (14)	0.0022 (10)	0.0010 (10)	0.0016 (11)
C6	0.0306 (14)	0.0337 (16)	0.0488 (16)	−0.0029 (11)	−0.0010 (12)	−0.0043 (13)
C7	0.0338 (15)	0.0469 (19)	0.0480 (17)	0.0026 (12)	−0.0146 (13)	−0.0136 (14)
C8	0.0440 (16)	0.0515 (19)	0.0289 (14)	0.0107 (14)	−0.0100 (12)	−0.0052 (13)
C9	0.0343 (14)	0.0436 (17)	0.0300 (14)	0.0060 (12)	0.0049 (11)	−0.0019 (12)
C10	0.0263 (12)	0.0239 (13)	0.0297 (13)	0.0024 (10)	0.0000 (10)	−0.0007 (10)
C11	0.0346 (14)	0.0271 (14)	0.0331 (14)	−0.0008 (11)	−0.0044 (11)	−0.0041 (11)

Geometric parameters (Å, º) top

O1—C1	1.349 (3)	C3—H3	0.9300
O1—H1	0.8200	C4—C5	1.410 (4)
O2—C11	1.287 (3)	C4—H4	0.9300
O3—C11	1.230 (3)	C5—C6	1.409 (4)
N1—H1A	0.89 (2)	C5—C10	1.418 (4)
N1—H1B	0.89 (3)	C6—C7	1.356 (4)
N1—H1C	0.89 (2)	C6—H6	0.9300
N1—H1D	0.88 (3)	C7—C8	1.400 (4)
C1—C2	1.375 (4)	C7—H7	0.9300
C1—C10	1.419 (3)	C8—C9	1.355 (4)
C2—C3	1.410 (3)	C8—H8	0.9300
C2—C11	1.487 (3)	C9—C10	1.405 (4)
C3—C4	1.358 (4)	C9—H9	0.9300

C1—O1—H1	109.5	C6—C5—C10	118.2 (3)
H1A—N1—H1B	110.8 (19)	C4—C5—C10	119.3 (2)
H1A—N1—H1C	108 (2)	C7—C6—C5	121.3 (3)
H1B—N1—H1C	110.0 (19)	C7—C6—H6	119.4
H1A—N1—H1D	110 (2)	C5—C6—H6	119.4
H1B—N1—H1D	109 (2)	C6—C7—C8	120.1 (3)
H1C—N1—H1D	108.3 (19)	C6—C7—H7	119.9
O1—C1—C2	121.5 (2)	C8—C7—H7	119.9
O1—C1—C10	117.3 (2)	C9—C8—C7	120.5 (3)
C2—C1—C10	121.2 (2)	C9—C8—H8	119.8
C1—C2—C3	119.0 (2)	C7—C8—H8	119.8
C1—C2—C11	121.1 (2)	C8—C9—C10	120.8 (3)
C3—C2—C11	120.0 (2)	C8—C9—H9	119.6
C4—C3—C2	121.4 (2)	C10—C9—H9	119.6
C4—C3—H3	119.3	C9—C10—C5	119.1 (2)
C2—C3—H3	119.3	C9—C10—C1	122.4 (2)
C3—C4—C5	120.5 (2)	C5—C10—C1	118.5 (2)
C3—C4—H4	119.7	O3—C11—O2	122.9 (2)
C5—C4—H4	119.7	O3—C11—C2	121.0 (3)
C6—C5—C4	122.5 (3)	O2—C11—C2	116.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.73	2.463 (3)	148
N1—H1A···O1ⁱ	0.89 (2)	2.07 (3)	2.920 (3)	161 (3)
N1—H1B···O2ⁱⁱ	0.89 (3)	1.88 (3)	2.756 (3)	167 (3)
N1—H1C···O3ⁱⁱⁱ	0.89 (2)	2.04 (2)	2.789 (3)	141 (3)
N1—H1D···O3^iv	0.88 (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.

Experimental details

Crystal data
Chemical formula	NH₄⁺·C₁₁H₇O₃⁻
M_r	205.21
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	30.883 (5), 3.880 (1), 15.777 (3)
β (°)	95.567 (2)
V (Å³)	1881.6 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.23 × 0.23 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.976, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	6728, 1915, 1351
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.226, 1.04
No. of reflections	1915
No. of parameters	149
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.24

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.73	2.463 (3)	148
N1—H1A···O1ⁱ	0.89 (2)	2.07 (3)	2.920 (3)	161 (3)
N1—H1B···O2ⁱⁱ	0.89 (3)	1.88 (3)	2.756 (3)	167 (3)
N1—H1C···O3ⁱⁱⁱ	0.89 (2)	2.04 (2)	2.789 (3)	141 (3)
N1—H1D···O3^iv	0.88 (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.

Acknowledgements

The authors acknowledge Qiqihar University for a research grant.

References

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