Diethyl-ammonium 4-hy-droxy-benzoate.

In the crystal structure of the title compound, C(4)H(12)N(+)·C(7)H(5)O(3) (-), the cations and anions are linked by N-H⋯O and O-H⋯O hydrogen bonds, leading to the formation of a three-dimensional network.

Related literature

Hydrogen bonds in co-crystals have been widely used to design and synthesize one-, two- and three-dimensional supra­molecular compounds, see: Aakeroÿ et al. (2002 ▶). 4-Hy­­droxy­benzoic acid is a good hydrogen bond donor and can form co-crystals with other organic mol­ecules, see: Vishweshwar et al. (2003 ▶).

Experimental

Crystal data

C4H12N+·C7H5O3 −

M = 211.26

Orthorhombic,

a = 12.1270 (13) Å

b = 10.6829 (11) Å

c = 17.6066 (15) Å

V = 2281.0 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.43 × 0.41 × 0.20 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.963, T max = 0.982

8818 measured reflections

2016 independent reflections

1155 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.130

S = 1.06

2016 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040523/fl2305sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040523/fl2305Isup2.hkl

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

C4H12N+·C7H5O3−	F(000) = 912
Mr = 211.26	Dx = 1.230 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4113 reflections
a = 12.1270 (13) Å	θ = 2.4–27.4°
b = 10.6829 (11) Å	µ = 0.09 mm−1
c = 17.6066 (15) Å	T = 298 K
V = 2281.0 (4) Å3	Prism, colourless
Z = 8	0.43 × 0.41 × 0.20 mm

Rigaku Mercury diffractometer	2016 independent reflections
Radiation source: fine-focus sealed tube	1155 reflections with I > 2σ(I)
graphite	Rint = 0.048
ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −7→14
Tmin = 0.963, Tmax = 0.982	k = −12→9
8818 measured reflections	l = −20→20

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0464P)2 + 0.8922P] where P = (Fo2 + 2Fc2)/3
2016 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 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 > 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.

	x	y	z	Uiso*/Ueq
N1	0.15290 (17)	0.4229 (2)	0.46227 (12)	0.0500 (6)
H1A	0.1303	0.3844	0.5050	0.060*
H1B	0.0985	0.4747	0.4474	0.060*
O1	0.39118 (14)	0.74534 (19)	0.59243 (10)	0.0538 (5)
O2	0.49892 (17)	0.9105 (2)	0.58731 (11)	0.0685 (6)
O3	0.75558 (15)	0.59440 (17)	0.83491 (10)	0.0597 (6)
H3	0.7969	0.6470	0.8534	0.090*
C1	0.4739 (2)	0.8063 (3)	0.61463 (14)	0.0449 (7)
C2	0.54591 (19)	0.7521 (2)	0.67521 (13)	0.0371 (6)
C3	0.62071 (19)	0.8261 (2)	0.71431 (13)	0.0420 (6)
H3A	0.6239	0.9113	0.7038	0.050*
C4	0.69034 (19)	0.7768 (2)	0.76835 (13)	0.0417 (6)
H4	0.7389	0.8286	0.7944	0.050*
C5	0.68774 (19)	0.6501 (2)	0.78369 (13)	0.0412 (6)
C6	0.61259 (19)	0.5748 (2)	0.74597 (14)	0.0451 (7)
H6	0.6095	0.4896	0.7567	0.054*
C7	0.54265 (19)	0.6254 (2)	0.69286 (13)	0.0420 (6)
H7	0.4922	0.5740	0.6683	0.050*
C8	0.2517 (3)	0.4991 (3)	0.48039 (17)	0.0638 (8)
H8A	0.2304	0.5662	0.5144	0.077*
H8B	0.2791	0.5368	0.4340	0.077*
C9	0.3426 (2)	0.4254 (3)	0.51642 (18)	0.0724 (9)
H9A	0.3139	0.3792	0.5588	0.109*
H9B	0.3992	0.4815	0.5337	0.109*
H9C	0.3730	0.3684	0.4799	0.109*
C10	0.1689 (2)	0.3275 (3)	0.40308 (15)	0.0575 (8)
H10A	0.2266	0.2702	0.4187	0.069*
H10B	0.1924	0.3679	0.3565	0.069*
C11	0.0657 (3)	0.2559 (3)	0.3885 (2)	0.0845 (11)
H11A	0.0446	0.2118	0.4338	0.127*
H11B	0.0780	0.1969	0.3483	0.127*
H11C	0.0080	0.3126	0.3742	0.127*

	U11	U22	U33	U12	U13	U23
N1	0.0416 (13)	0.0629 (15)	0.0456 (12)	0.0035 (11)	0.0090 (10)	0.0040 (11)
O1	0.0427 (11)	0.0719 (13)	0.0467 (11)	−0.0014 (10)	−0.0083 (9)	0.0082 (9)
O2	0.0711 (14)	0.0676 (14)	0.0668 (13)	−0.0052 (11)	−0.0119 (11)	0.0315 (11)
O3	0.0530 (11)	0.0591 (12)	0.0670 (12)	−0.0036 (10)	−0.0217 (10)	0.0170 (10)
C1	0.0431 (16)	0.0561 (18)	0.0356 (14)	0.0077 (14)	0.0067 (12)	0.0044 (13)
C2	0.0336 (13)	0.0426 (15)	0.0352 (13)	0.0021 (12)	0.0047 (11)	0.0047 (11)
C3	0.0465 (15)	0.0369 (15)	0.0426 (14)	−0.0032 (12)	0.0029 (13)	0.0063 (12)
C4	0.0405 (15)	0.0444 (16)	0.0402 (14)	−0.0072 (12)	−0.0015 (12)	0.0011 (12)
C5	0.0359 (14)	0.0486 (16)	0.0390 (13)	0.0030 (12)	0.0003 (12)	0.0070 (12)
C6	0.0424 (15)	0.0390 (15)	0.0539 (16)	−0.0020 (13)	−0.0045 (13)	0.0076 (13)
C7	0.0350 (14)	0.0441 (16)	0.0467 (15)	−0.0049 (12)	−0.0022 (12)	0.0005 (13)
C8	0.067 (2)	0.0595 (19)	0.0652 (19)	−0.0111 (16)	0.0033 (16)	−0.0082 (16)
C9	0.0508 (19)	0.092 (2)	0.074 (2)	−0.0046 (18)	−0.0058 (16)	−0.0123 (19)
C10	0.0637 (19)	0.0506 (18)	0.0584 (17)	0.0002 (15)	0.0068 (15)	−0.0044 (14)
C11	0.076 (2)	0.086 (3)	0.091 (3)	−0.018 (2)	−0.028 (2)	−0.003 (2)

N1—C10	1.470 (3)	C6—C7	1.373 (3)
N1—C8	1.483 (3)	C6—H6	0.9300
N1—H1A	0.9000	C7—H7	0.9300
N1—H1B	0.9000	C8—C9	1.495 (4)
O1—C1	1.259 (3)	C8—H8A	0.9700
O2—C1	1.249 (3)	C8—H8B	0.9700
O3—C5	1.358 (3)	C9—H9A	0.9600
O3—H3	0.8200	C9—H9B	0.9600
C1—C2	1.495 (3)	C9—H9C	0.9600
C2—C3	1.386 (3)	C10—C11	1.489 (4)
C2—C7	1.388 (3)	C10—H10A	0.9700
C3—C4	1.377 (3)	C10—H10B	0.9700
C3—H3A	0.9300	C11—H11A	0.9600
C4—C5	1.381 (3)	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C5—C6	1.385 (3)
C10—N1—C8	115.2 (2)	C6—C7—H7	119.4
C10—N1—H1A	108.5	C2—C7—H7	119.4
C8—N1—H1A	108.5	N1—C8—C9	113.4 (2)
C10—N1—H1B	108.5	N1—C8—H8A	108.9
C8—N1—H1B	108.5	C9—C8—H8A	108.9
H1A—N1—H1B	107.5	N1—C8—H8B	108.9
C5—O3—H3	109.5	C9—C8—H8B	108.9
O2—C1—O1	122.3 (2)	H8A—C8—H8B	107.7
O2—C1—C2	118.6 (3)	C8—C9—H9A	109.5
O1—C1—C2	119.1 (2)	C8—C9—H9B	109.5
C3—C2—C7	117.6 (2)	H9A—C9—H9B	109.5
C3—C2—C1	121.0 (2)	C8—C9—H9C	109.5
C7—C2—C1	121.4 (2)	H9A—C9—H9C	109.5
C4—C3—C2	121.8 (2)	H9B—C9—H9C	109.5
C4—C3—H3A	119.1	N1—C10—C11	111.6 (2)
C2—C3—H3A	119.1	N1—C10—H10A	109.3
C3—C4—C5	119.7 (2)	C11—C10—H10A	109.3
C3—C4—H4	120.1	N1—C10—H10B	109.3
C5—C4—H4	120.1	C11—C10—H10B	109.3
O3—C5—C4	123.1 (2)	H10A—C10—H10B	108.0
O3—C5—C6	117.6 (2)	C10—C11—H11A	109.5
C4—C5—C6	119.4 (2)	C10—C11—H11B	109.5
C7—C6—C5	120.3 (2)	H11A—C11—H11B	109.5
C7—C6—H6	119.9	C10—C11—H11C	109.5
C5—C6—H6	119.9	H11A—C11—H11C	109.5
C6—C7—C2	121.2 (2)	H11B—C11—H11C	109.5
O2—C1—C2—C3	16.5 (3)	C3—C4—C5—C6	−1.9 (4)
O1—C1—C2—C3	−164.2 (2)	O3—C5—C6—C7	−179.2 (2)
O2—C1—C2—C7	−161.6 (2)	C4—C5—C6—C7	1.1 (4)
O1—C1—C2—C7	17.7 (3)	C5—C6—C7—C2	0.5 (4)
C7—C2—C3—C4	0.5 (3)	C3—C2—C7—C6	−1.3 (4)
C1—C2—C3—C4	−177.6 (2)	C1—C2—C7—C6	176.8 (2)
C2—C3—C4—C5	1.1 (4)	C10—N1—C8—C9	−66.5 (3)
C3—C4—C5—O3	178.5 (2)	C8—N1—C10—C11	−179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.90	2.15	2.873 (3)	137
N1—H1A···O1i	0.90	2.16	3.022 (3)	162
N1—H1B···O2ii	0.90	1.83	2.724 (3)	174
O3—H3···O1iii	0.82	1.82	2.635 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.90	2.15	2.873 (3)	137
N1—H1A⋯O1i	0.90	2.16	3.022 (3)	162
N1—H1B⋯O2ii	0.90	1.83	2.724 (3)	174
O3—H3⋯O1iii	0.82	1.82	2.635 (3)	170

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