Ammonium salicylate: a synchrotron study.

The structure of the title salt, NH(4) (+)·C(7)H(5)O(3) (-), is stabilized by substantial hydrogen bonding between ammonium cations and salicylate anions that links the components into a two-dimensional array.

Related literature

For background to organic scintillators, see: Brooks (1979 ▶); Kaschuck et al. (2002 ▶); Kachuk & Esposito (2005 ▶). For the structures of salicylate salts, see: Wiesbrock & Schmidbaur (2003a ▶,b ▶); Dinnebier et al. (2002 ▶). For hydrogen bonding in salicylate compounds, see: Gellert & Hsu (1983 ▶); Drake et al. (1993 ▶).

Experimental

Crystal data

NH4 +·C7H5O3 −

M = 155.15

Monoclinic,

a = 6.0768 (6) Å

b = 20.089 (2) Å

c = 6.3353 (7) Å

β = 102.768 (1)°

V = 754.28 (14) Å3

Z = 4

Synchrotron radiation

λ = 0.77490 Å

μ = 0.13 mm−1

T = 150 K

0.40 × 0.20 × 0.06 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.950, T max = 0.992

7758 measured reflections

2274 independent reflections

1939 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.150

S = 1.10

2274 reflections

136 parameters

All H-atom parameters refined

Δρmax = 0.36 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029857/tk2513sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029857/tk2513Isup2.hkl

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

NH4+·C7H5O3−	F(000) = 328
Mr = 155.15	Dx = 1.366 Mg m−3
Monoclinic, P21/n	Synchrotron radiation, λ = 0.77490 Å
Hall symbol: -P 2yn	Cell parameters from 3198 reflections
a = 6.0768 (6) Å	θ = 3.8–33.5°
b = 20.089 (2) Å	µ = 0.13 mm−1
c = 6.3353 (7) Å	T = 150 K
β = 102.768 (1)°	Plate, colorless
V = 754.28 (14) Å3	0.40 × 0.20 × 0.06 mm
Z = 4

Bruker APEXII diffractometer	2274 independent reflections
Radiation source: 11.3.1 ALS, LBNL, CA	1939 reflections with I > 2σ(I)
Si (111)	Rint = 0.053
ω scans	θmax = 33.8°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→8
Tmin = 0.950, Tmax = 0.992	k = −27→28
7758 measured reflections	l = −9→8

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	All H-atom parameters refined
S = 1.10	w = 1/[σ2(Fo2) + (0.0888P)2 + 0.043P] where P = (Fo2 + 2Fc2)/3
2274 reflections	(Δ/σ)max = 0.006
136 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.24 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 > 2σ(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	0.75801 (14)	0.09351 (5)	0.40962 (13)	0.0303 (2)
O2	0.24729 (14)	0.05282 (4)	0.06590 (12)	0.0292 (2)
O3	1.12089 (13)	0.03981 (4)	0.36657 (12)	0.0283 (2)
N4	0.47360 (16)	0.05050 (5)	−0.26977 (15)	0.0245 (2)
C1	0.76231 (17)	0.12776 (5)	0.22639 (17)	0.0233 (2)
C2	0.5922 (2)	0.17478 (6)	0.1553 (2)	0.0312 (3)
C3	0.5876 (2)	0.21026 (6)	−0.0326 (2)	0.0347 (3)
C4	0.7494 (2)	0.19945 (6)	−0.1538 (2)	0.0328 (3)
C5	0.91906 (19)	0.15315 (5)	−0.08247 (18)	0.0273 (3)
C6	0.92866 (16)	0.11662 (5)	0.10730 (16)	0.0211 (2)
C7	1.11200 (16)	0.06636 (5)	0.18209 (15)	0.0217 (2)
H1	0.884 (3)	0.0660 (9)	0.429 (3)	0.048 (5)*
H2	0.482 (3)	0.1790 (8)	0.247 (2)	0.033 (4)*
H3	0.461 (4)	0.2423 (10)	−0.088 (3)	0.061 (5)*
H4	0.742 (3)	0.2241 (9)	−0.283 (3)	0.042 (4)*
H5	1.036 (3)	0.1449 (8)	−0.165 (2)	0.036 (4)*
H6	0.368 (3)	0.0433 (8)	−0.397 (3)	0.046 (5)*
H7	0.563 (3)	0.0162 (8)	−0.212 (2)	0.038 (4)*
H8	0.399 (3)	0.0624 (9)	−0.162 (3)	0.045 (4)*
H9	0.563 (3)	0.0840 (10)	−0.297 (3)	0.051 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0288 (4)	0.0397 (5)	0.0258 (4)	0.0077 (3)	0.0131 (3)	0.0051 (3)
O2	0.0235 (4)	0.0393 (5)	0.0276 (4)	0.0052 (3)	0.0119 (3)	0.0037 (3)
O3	0.0232 (4)	0.0406 (5)	0.0217 (4)	0.0055 (3)	0.0063 (3)	0.0075 (3)
N4	0.0232 (4)	0.0297 (5)	0.0214 (4)	0.0017 (3)	0.0064 (3)	0.0013 (3)
C1	0.0224 (5)	0.0229 (5)	0.0251 (5)	−0.0007 (3)	0.0063 (4)	−0.0025 (3)
C2	0.0279 (5)	0.0271 (5)	0.0399 (6)	0.0057 (4)	0.0102 (5)	−0.0013 (4)
C3	0.0319 (6)	0.0226 (5)	0.0475 (7)	0.0041 (4)	0.0038 (5)	0.0056 (5)
C4	0.0310 (6)	0.0273 (5)	0.0383 (6)	−0.0021 (4)	0.0039 (5)	0.0117 (4)
C5	0.0247 (5)	0.0291 (5)	0.0280 (5)	−0.0030 (4)	0.0059 (4)	0.0060 (4)
C6	0.0187 (4)	0.0217 (4)	0.0223 (4)	−0.0018 (3)	0.0033 (3)	0.0000 (3)
C7	0.0179 (4)	0.0271 (5)	0.0200 (4)	−0.0004 (3)	0.0041 (3)	0.0004 (3)

O1—C1	1.3547 (13)	C2—C3	1.3826 (18)
O1—H1	0.931 (19)	C2—H2	0.985 (17)
O2—C7i	1.2487 (13)	C3—C4	1.3915 (19)
O3—C7	1.2749 (12)	C3—H3	1.00 (2)
N4—H6	0.925 (18)	C4—C5	1.3878 (16)
N4—H7	0.902 (17)	C4—H4	0.952 (18)
N4—H8	0.933 (19)	C5—C6	1.3988 (14)
N4—H9	0.91 (2)	C5—H5	0.981 (17)
C1—C2	1.3991 (15)	C6—C7	1.5007 (14)
C1—C6	1.4065 (14)	C7—O2ii	1.2487 (13)
C1—O1—H1	104.0 (11)	C2—C3—H3	120.0 (12)
H6—N4—H7	118.3 (15)	C4—C3—H3	119.1 (12)
H6—N4—H8	108.8 (16)	C5—C4—C3	119.32 (11)
H7—N4—H8	104.2 (14)	C5—C4—H4	121.2 (11)
H6—N4—H9	106.2 (15)	C3—C4—H4	119.4 (11)
H7—N4—H9	108.3 (17)	C4—C5—C6	121.22 (11)
H8—N4—H9	111.1 (15)	C4—C5—H5	120.8 (9)
O1—C1—C2	117.78 (10)	C6—C5—H5	118.0 (9)
O1—C1—C6	122.07 (9)	C5—C6—C1	118.63 (9)
C2—C1—C6	120.14 (10)	C5—C6—C7	120.76 (9)
C3—C2—C1	119.88 (11)	C1—C6—C7	120.61 (9)
C3—C2—H2	125.3 (9)	O2ii—C7—O3	123.32 (9)
C1—C2—H2	114.8 (9)	O2ii—C7—C6	120.00 (9)
C2—C3—C4	120.81 (10)	O3—C7—C6	116.68 (9)
O1—C1—C2—C3	−179.03 (10)	C2—C1—C6—C5	−0.29 (15)
C6—C1—C2—C3	0.11 (17)	O1—C1—C6—C7	−0.95 (15)
C1—C2—C3—C4	0.53 (18)	C2—C1—C6—C7	179.95 (9)
C2—C3—C4—C5	−0.99 (18)	C5—C6—C7—O2ii	−5.84 (15)
C3—C4—C5—C6	0.81 (17)	C1—C6—C7—O2ii	173.93 (9)
C4—C5—C6—C1	−0.18 (16)	C5—C6—C7—O3	173.62 (9)
C4—C5—C6—C7	179.59 (10)	C1—C6—C7—O3	−6.62 (14)
O1—C1—C6—C5	178.82 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.93 (2)	1.66 (2)	2.523 (1)	153 (2)
N4—H6···O3iii	0.92 (2)	1.87 (2)	2.787 (1)	169 (2)
N4—H7···O2iv	0.90 (2)	1.91 (2)	2.808 (1)	175 (1)
N4—H8···O2	0.93 (2)	1.88 (2)	2.776 (1)	159 (2)
N4—H9···O1v	0.91 (2)	2.42 (2)	3.068 (1)	128 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.93 (2)	1.66 (2)	2.523 (1)	153 (2)
N4—H6⋯O3i	0.92 (2)	1.87 (2)	2.787 (1)	169 (2)
N4—H7⋯O2ii	0.90 (2)	1.91 (2)	2.808 (1)	175 (1)
N4—H8⋯O2	0.93 (2)	1.88 (2)	2.776 (1)	159 (2)
N4—H9⋯O1iii	0.91 (2)	2.42 (2)	3.068 (1)	128 (2)

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