Ammonium 4-(4-carb-oxy-phen-oxy)benzoate.

The anions of the title salt, NH(4) (+)·HO(2)CC(6)H(4)-O-C(6)H(4)CO(2) (-), are linked by inter-molecular -CO(2)H⋯O(2)C- hydrogen bonds, forming a polyanionic chain in the crystal; adjacent chains are connected through the ammonium cation into a layer structure, with the ammonium cation serving as hydrogen-bond donor to four carboxyl-ate O atoms. The cation and anion both lie on special positions of 2 site symmetry. In the anion, the rings make a dihedral angle of 65.3 (1)°. The acid H atom is disordered about the special position.

Related literature

For the crystal structures of two modifications of ­oxy-4,4′-bis­(benzoic acid), see: Dey & Desiraju (2005 ▶); Potts et al. (2007 ▶).

Experimental

Crystal data

NH4 +·C14H9O5 −

M = 275.25

Orthorhombic,

a = 6.1916 (1) Å

b = 28.5483 (6) Å

c = 7.1123 (1) Å

V = 1257.17 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.50 × 0.40 × 0.30 mm

Data collection

Bruker SMART APEX diffractometer

3444 measured reflections

1434 independent reflections

1279 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.146

S = 1.04

1434 reflections

102 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.42 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048841/hg2754sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048841/hg2754Isup2.hkl

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

NH4+·C14H9O5−	F(000) = 576
Mr = 275.25	Dx = 1.454 Mg m−3
Orthorhombic, Pnna	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2bc	Cell parameters from 2311 reflections
a = 6.1916 (1) Å	θ = 2.9–27.6°
b = 28.5483 (6) Å	µ = 0.11 mm−1
c = 7.1123 (1) Å	T = 293 K
V = 1257.17 (4) Å3	Block, colorless
Z = 4	0.50 × 0.40 × 0.30 mm

Bruker SMART APEX diffractometer	1279 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
graphite	θmax = 27.5°, θmin = 2.9°
ω scans	h = −6→8
3444 measured reflections	k = −36→29
1434 independent reflections	l = −9→5

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) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0922P)2 + 0.4317P] where P = (Fo2 + 2Fc2)/3
1434 reflections	(Δ/σ)max = 0.001
102 parameters	Δρmax = 0.30 e Å−3
6 restraints	Δρmin = −0.42 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.83559 (19)	0.46053 (3)	0.15346 (17)	0.0429 (4)
H1	0.748 (8)	0.4828 (15)	0.140 (6)	0.10 (2)*	0.50
O2	0.5981 (2)	0.43933 (4)	0.37136 (18)	0.0536 (4)
O3	1.1215 (2)	0.2500	0.2500	0.0325 (4)
C1	0.7477 (2)	0.43024 (5)	0.26451 (19)	0.0320 (3)
C2	0.8424 (2)	0.38203 (4)	0.25651 (17)	0.0266 (3)
C3	0.7341 (2)	0.34508 (5)	0.34202 (18)	0.0302 (3)
H3	0.6034	0.3506	0.4026	0.036*
C4	0.8184 (2)	0.30004 (5)	0.33813 (18)	0.0304 (3)
H4	0.7450	0.2754	0.3950	0.036*
C5	1.0136 (2)	0.29244 (4)	0.24811 (16)	0.0254 (3)
C6	1.1244 (2)	0.32879 (5)	0.16242 (18)	0.0292 (3)
H6	1.2555	0.3232	0.1027	0.035*
C7	1.0374 (2)	0.37357 (4)	0.16673 (18)	0.0298 (3)
H7	1.1105	0.3981	0.1089	0.036*
N1	0.2500	0.5000	0.2884 (4)	0.0503 (5)
H11	0.3506 (16)	0.5123 (6)	0.2161 (16)	0.060*
H12	0.308 (3)	0.4771 (5)	0.355 (2)	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0450 (7)	0.0203 (5)	0.0633 (8)	0.0051 (4)	0.0098 (5)	0.0037 (4)
O2	0.0553 (8)	0.0374 (6)	0.0681 (8)	0.0191 (5)	0.0230 (6)	0.0050 (5)
O3	0.0327 (7)	0.0164 (6)	0.0485 (8)	0.000	0.000	−0.0001 (5)
C1	0.0339 (7)	0.0233 (6)	0.0387 (7)	0.0044 (5)	−0.0013 (5)	−0.0041 (5)
C2	0.0321 (7)	0.0194 (6)	0.0284 (6)	0.0019 (5)	−0.0005 (5)	−0.0016 (4)
C3	0.0309 (7)	0.0269 (7)	0.0329 (7)	0.0015 (5)	0.0058 (5)	−0.0014 (5)
C4	0.0366 (7)	0.0223 (6)	0.0323 (7)	−0.0030 (5)	0.0062 (5)	0.0024 (5)
C5	0.0328 (7)	0.0167 (6)	0.0266 (6)	0.0011 (4)	−0.0016 (5)	−0.0020 (4)
C6	0.0308 (7)	0.0219 (6)	0.0350 (7)	0.0006 (5)	0.0070 (5)	−0.0013 (5)
C7	0.0360 (8)	0.0183 (6)	0.0352 (7)	−0.0012 (5)	0.0062 (5)	0.0019 (4)
N1	0.0342 (10)	0.0516 (12)	0.0651 (13)	0.0082 (9)	0.000	0.000

O1—C1	1.2914 (18)	C3—H3	0.9300
O1—H1	0.841 (10)	C4—C5	1.385 (2)
O2—C1	1.2260 (18)	C4—H4	0.9300
O3—C5i	1.3833 (13)	C5—C6	1.3852 (18)
O3—C5	1.3833 (13)	C6—C7	1.3876 (17)
C1—C2	1.4973 (17)	C6—H6	0.9300
C2—C7	1.3867 (19)	C7—H7	0.9300
C2—C3	1.3902 (18)	N1—H11	0.881 (7)
C3—C4	1.3880 (18)	N1—H12	0.882 (8)
C1—O1—H1	108 (4)	C5—C4—H4	120.6
C5i—O3—C5	122.29 (15)	C3—C4—H4	120.6
O2—C1—O1	123.76 (13)	O3—C5—C4	123.65 (11)
O2—C1—C2	120.94 (13)	O3—C5—C6	114.94 (12)
O1—C1—C2	115.30 (12)	C4—C5—C6	121.19 (11)
C7—C2—C3	119.32 (11)	C5—C6—C7	119.25 (12)
C7—C2—C1	121.23 (12)	C5—C6—H6	120.4
C3—C2—C1	119.45 (12)	C7—C6—H6	120.4
C4—C3—C2	120.83 (12)	C2—C7—C6	120.55 (12)
C4—C3—H3	119.6	C2—C7—H7	119.7
C2—C3—H3	119.6	C6—C7—H7	119.7
C5—C4—C3	118.86 (12)	H11—N1—H12	108.6 (10)
O2—C1—C2—C7	−166.60 (14)	C5i—O3—C5—C6	−151.57 (12)
O1—C1—C2—C7	12.97 (19)	C3—C4—C5—O3	174.06 (11)
O2—C1—C2—C3	12.8 (2)	C3—C4—C5—C6	−0.17 (19)
O1—C1—C2—C3	−167.60 (13)	O3—C5—C6—C7	−174.86 (10)
C7—C2—C3—C4	−0.1 (2)	C4—C5—C6—C7	−0.15 (19)
C1—C2—C3—C4	−179.57 (12)	C3—C2—C7—C6	−0.20 (19)
C2—C3—C4—C5	0.3 (2)	C1—C2—C7—C6	179.23 (12)
C5i—O3—C5—C4	33.86 (10)	C5—C6—C7—C2	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1ii	0.84 (1)	1.70 (3)	2.490 (2)	156 (6)
N1—H11···O1ii	0.88 (1)	2.14 (1)	2.962 (2)	155 (1)
N1—H12···O2	0.88 (1)	2.10 (2)	2.827 (1)	139 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1i	0.84 (1)	1.70 (3)	2.490 (2)	156 (6)
N1—H11⋯O1i	0.88 (1)	2.14 (1)	2.962 (2)	155 (1)
N1—H12⋯O2	0.88 (1)	2.10 (2)	2.827 (1)	139 (2)

Symmetry code: (i) .