Tetra-ethyl-ammonium 4-hy-droxy-benzoate monohydrate.

In the title compound, C(8)H(20)N(+)·C(7)H(5)O(3) (-)·H(2)O, the carboxyl-ate group is slightly out of the plane of the parent benzene ring, the C-C-C-O torsion angles being 2.3 (2) and 2.0 (2)°. The carboxyl-ate group and the hy-droxy group form O-H⋯O hydrogen bonds, generating a head-to-tail chain along the b axis. Neighbouring hydrogen-bonded chains are linked by the water mol-ecule, generating two independent O-H⋯O donor hydrogen bonds. The carboxyl-ate group thus constructs a hydrogen-bonded host layer parallel to (10[Formula: see text]). The tetra-ethyl-ammonium cation is contained between these layers, forming a sandwich-like structure with an approximate inter-layer distance of 10.03 Å.

Related literature

p-Hy­droxy­benzoic acid has been found to inter­act with varied cations, such as dec­yl(trimeth­yl)ammonium and hexa­methonium, to form different crystal structures, see: Marsh & Spek (2001 ▶); Yang et al. (2010 ▶).

Experimental

Crystal data

C8H20N+·C7H5O3 −·H2O

M = 285.38

Monoclinic,

a = 9.6082 (10) Å

b = 16.2610 (16) Å

c = 10.4478 (10) Å

β = 96.378 (1)°

V = 1622.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.66 × 0.37 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.947, T max = 0.984

7411 measured reflections

3774 independent reflections

2730 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.181

S = 1.06

3774 reflections

182 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.19 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024044/fj2433sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024044/fj2433Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024044/fj2433Isup3.cml

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

C8H20N+·C7H5O3−·H2O	F(000) = 624
Mr = 285.38	Dx = 1.168 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2665 reflections
a = 9.6082 (10) Å	θ = 3.1–27.5°
b = 16.2610 (16) Å	µ = 0.08 mm−1
c = 10.4478 (10) Å	T = 296 K
β = 96.378 (1)°	Block, colorless
V = 1622.2 (3) Å3	0.66 × 0.37 × 0.20 mm
Z = 4

Bruker SMART APEX diffractometer	3774 independent reflections
Radiation source: fine-focus sealed tube	2730 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 27.7°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→12
Tmin = 0.947, Tmax = 0.984	k = −21→16
7411 measured reflections	l = −12→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.181	w = 1/[σ2(Fo2) + (0.0974P)2 + 0.3052P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3774 reflections	Δρmax = 0.35 e Å−3
182 parameters	Δρmin = −0.19 e Å−3
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (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
C1	0.18857 (16)	0.99878 (8)	0.16322 (14)	0.0403 (3)
C2	0.14101 (18)	0.92648 (9)	0.10187 (15)	0.0455 (4)
H2A	0.0914	0.9286	0.0203	0.055*
C3	0.16740 (16)	0.85171 (9)	0.16210 (15)	0.0418 (4)
H3A	0.1363	0.8037	0.1197	0.050*
C4	0.23956 (15)	0.84650 (9)	0.28496 (14)	0.0378 (3)
C5	0.28608 (17)	0.91927 (9)	0.34473 (14)	0.0425 (4)
H5A	0.3344	0.9173	0.4269	0.051*
C6	0.26236 (17)	0.99454 (9)	0.28514 (15)	0.0432 (4)
H6A	0.2958	1.0424	0.3266	0.052*
C7	0.26794 (17)	0.76486 (9)	0.35068 (16)	0.0459 (4)
C8	0.3736 (2)	0.18451 (12)	0.6489 (2)	0.0616 (5)
H8A	0.4666	0.1638	0.6772	0.074*
H8B	0.3597	0.1803	0.5558	0.074*
C9	0.3679 (3)	0.27388 (14)	0.6854 (3)	0.0901 (8)
H9A	0.4380	0.3038	0.6459	0.135*
H9B	0.3850	0.2792	0.7773	0.135*
H9C	0.2770	0.2957	0.6562	0.135*
C10	0.2876 (3)	0.13132 (17)	0.8501 (2)	0.0807 (7)
H10A	0.2722	0.1871	0.8782	0.097*
H10B	0.2170	0.0967	0.8824	0.097*
C11	0.4301 (3)	0.1034 (3)	0.9102 (3)	0.1159 (11)
H11A	0.4337	0.1059	1.0023	0.174*
H11B	0.5008	0.1386	0.8820	0.174*
H11C	0.4462	0.0478	0.8844	0.174*
C12	0.1202 (2)	0.15932 (15)	0.6641 (2)	0.0728 (6)
H12A	0.1101	0.2136	0.7003	0.087*
H12B	0.0550	0.1231	0.7008	0.087*
C13	0.0797 (3)	0.1640 (2)	0.5198 (3)	0.1107 (11)
H13A	−0.0148	0.1837	0.5028	0.166*
H13B	0.0863	0.1103	0.4828	0.166*
H13C	0.1418	0.2009	0.4824	0.166*
C14	0.2893 (3)	0.04401 (13)	0.6544 (2)	0.0742 (6)
H14A	0.3847	0.0273	0.6828	0.089*
H14B	0.2791	0.0457	0.5611	0.089*
C15	0.1902 (4)	−0.02043 (18)	0.6972 (4)	0.1230 (13)
H15A	0.2104	−0.0727	0.6607	0.185*
H15B	0.0954	−0.0051	0.6684	0.185*
H15C	0.2019	−0.0243	0.7894	0.185*
O1	0.15893 (14)	1.07037 (7)	0.10032 (11)	0.0582 (4)
H1A	0.2006	1.1118	0.1392	0.087*
O2	0.33056 (16)	0.76395 (8)	0.46118 (13)	0.0680 (4)
O3	0.22788 (15)	0.70078 (7)	0.28835 (14)	0.0638 (4)
N1	0.26670 (15)	0.12929 (9)	0.70443 (14)	0.0503 (4)
O1W	0.5320 (2)	0.14390 (11)	0.3390 (2)	0.0996 (7)
H1WA	0.4672	0.1691	0.2931	0.149*
H1WB	0.5733	0.1776	0.3931	0.149*

	U11	U22	U33	U12	U13	U23
C1	0.0476 (8)	0.0300 (7)	0.0427 (8)	−0.0005 (6)	0.0027 (6)	0.0021 (6)
C2	0.0564 (9)	0.0385 (8)	0.0393 (8)	−0.0032 (7)	−0.0053 (7)	0.0000 (6)
C3	0.0492 (8)	0.0299 (7)	0.0451 (8)	−0.0055 (6)	0.0000 (6)	−0.0037 (6)
C4	0.0400 (7)	0.0301 (7)	0.0430 (8)	−0.0015 (5)	0.0034 (6)	0.0004 (6)
C5	0.0515 (9)	0.0348 (7)	0.0395 (8)	−0.0012 (6)	−0.0033 (6)	−0.0005 (6)
C6	0.0562 (9)	0.0284 (7)	0.0434 (8)	−0.0030 (6)	−0.0008 (7)	−0.0045 (6)
C7	0.0498 (9)	0.0318 (7)	0.0542 (9)	−0.0047 (6)	−0.0030 (7)	0.0046 (6)
C8	0.0608 (11)	0.0550 (10)	0.0710 (12)	−0.0007 (8)	0.0169 (9)	0.0034 (9)
C9	0.107 (2)	0.0529 (13)	0.109 (2)	−0.0090 (12)	0.0082 (15)	−0.0034 (12)
C10	0.0904 (16)	0.0989 (18)	0.0554 (12)	0.0158 (13)	0.0194 (11)	0.0025 (11)
C11	0.107 (2)	0.166 (3)	0.0718 (16)	0.019 (2)	−0.0044 (14)	0.0254 (19)
C12	0.0571 (11)	0.0777 (15)	0.0860 (15)	0.0130 (10)	0.0190 (10)	0.0032 (11)
C13	0.0775 (17)	0.160 (3)	0.0901 (19)	0.0169 (18)	−0.0113 (14)	0.0174 (19)
C14	0.0847 (15)	0.0489 (11)	0.0935 (16)	0.0037 (10)	0.0303 (12)	−0.0080 (10)
C15	0.129 (3)	0.0585 (15)	0.190 (4)	−0.0202 (16)	0.057 (3)	−0.0009 (18)
O1	0.0822 (9)	0.0318 (6)	0.0553 (7)	−0.0057 (5)	−0.0164 (6)	0.0071 (5)
O2	0.0993 (11)	0.0417 (7)	0.0567 (8)	−0.0127 (6)	−0.0194 (7)	0.0118 (6)
O3	0.0779 (9)	0.0287 (6)	0.0770 (9)	−0.0041 (5)	−0.0254 (7)	0.0012 (5)
N1	0.0538 (8)	0.0479 (8)	0.0519 (8)	0.0078 (6)	0.0181 (6)	−0.0004 (6)
O1W	0.0941 (12)	0.0703 (11)	0.1225 (15)	0.0175 (9)	−0.0410 (11)	−0.0246 (10)

C1—O1	1.3515 (17)	C10—H10A	0.9700
C1—C6	1.389 (2)	C10—H10B	0.9700
C1—C2	1.392 (2)	C11—H11A	0.9600
C2—C3	1.379 (2)	C11—H11B	0.9600
C2—H2A	0.9300	C11—H11C	0.9600
C3—C4	1.392 (2)	C12—N1	1.505 (2)
C3—H3A	0.9300	C12—C13	1.516 (4)
C4—C5	1.389 (2)	C12—H12A	0.9700
C4—C7	1.505 (2)	C12—H12B	0.9700
C5—C6	1.381 (2)	C13—H13A	0.9600
C5—H5A	0.9300	C13—H13B	0.9600
C6—H6A	0.9300	C13—H13C	0.9600
C7—O2	1.241 (2)	C14—N1	1.506 (2)
C7—O3	1.2658 (19)	C14—C15	1.516 (4)
C8—C9	1.505 (3)	C14—H14A	0.9700
C8—N1	1.526 (2)	C14—H14B	0.9700
C8—H8A	0.9700	C15—H15A	0.9600
C8—H8B	0.9700	C15—H15B	0.9600
C9—H9A	0.9600	C15—H15C	0.9600
C9—H9B	0.9600	O1—H1A	0.8614
C9—H9C	0.9600	O1W—H1WA	0.8477
C10—C11	1.511 (4)	O1W—H1WB	0.8531
C10—N1	1.513 (3)
O1—C1—C6	123.17 (13)	C10—C11—H11A	109.5
O1—C1—C2	117.58 (13)	C10—C11—H11B	109.5
C6—C1—C2	119.25 (13)	H11A—C11—H11B	109.5
C3—C2—C1	120.01 (13)	C10—C11—H11C	109.5
C3—C2—H2A	120.0	H11A—C11—H11C	109.5
C1—C2—H2A	120.0	H11B—C11—H11C	109.5
C2—C3—C4	121.45 (13)	N1—C12—C13	115.08 (19)
C2—C3—H3A	119.3	N1—C12—H12A	108.5
C4—C3—H3A	119.3	C13—C12—H12A	108.5
C5—C4—C3	117.73 (13)	N1—C12—H12B	108.5
C5—C4—C7	120.89 (13)	C13—C12—H12B	108.5
C3—C4—C7	121.38 (13)	H12A—C12—H12B	107.5
C6—C5—C4	121.60 (13)	C12—C13—H13A	109.5
C6—C5—H5A	119.2	C12—C13—H13B	109.5
C4—C5—H5A	119.2	H13A—C13—H13B	109.5
C5—C6—C1	119.96 (13)	C12—C13—H13C	109.5
C5—C6—H6A	120.0	H13A—C13—H13C	109.5
C1—C6—H6A	120.0	H13B—C13—H13C	109.5
O2—C7—O3	123.84 (14)	N1—C14—C15	114.5 (2)
O2—C7—C4	118.63 (13)	N1—C14—H14A	108.6
O3—C7—C4	117.51 (14)	C15—C14—H14A	108.6
C9—C8—N1	115.27 (19)	N1—C14—H14B	108.6
C9—C8—H8A	108.5	C15—C14—H14B	108.6
N1—C8—H8A	108.5	H14A—C14—H14B	107.6
C9—C8—H8B	108.5	C14—C15—H15A	109.5
N1—C8—H8B	108.5	C14—C15—H15B	109.5
H8A—C8—H8B	107.5	H15A—C15—H15B	109.5
C8—C9—H9A	109.5	C14—C15—H15C	109.5
C8—C9—H9B	109.5	H15A—C15—H15C	109.5
H9A—C9—H9B	109.5	H15B—C15—H15C	109.5
C8—C9—H9C	109.5	C1—O1—H1A	112.5
H9A—C9—H9C	109.5	C12—N1—C14	111.59 (17)
H9B—C9—H9C	109.5	C12—N1—C10	106.87 (15)
C11—C10—N1	115.1 (2)	C14—N1—C10	111.14 (17)
C11—C10—H10A	108.5	C12—N1—C8	110.52 (15)
N1—C10—H10A	108.5	C14—N1—C8	106.31 (14)
C11—C10—H10B	108.5	C10—N1—C8	110.46 (17)
N1—C10—H10B	108.5	H1WA—O1W—H1WB	108.8
H10A—C10—H10B	107.5
O1—C1—C2—C3	−179.51 (15)	C3—C4—C7—O3	2.3 (2)
C6—C1—C2—C3	−0.1 (3)	C13—C12—N1—C14	−59.8 (3)
C1—C2—C3—C4	0.9 (3)	C13—C12—N1—C10	178.5 (2)
C2—C3—C4—C5	−0.8 (2)	C13—C12—N1—C8	58.3 (3)
C2—C3—C4—C7	179.84 (15)	C15—C14—N1—C12	−58.3 (3)
C3—C4—C5—C6	−0.1 (2)	C15—C14—N1—C10	60.9 (3)
C7—C4—C5—C6	179.22 (15)	C15—C14—N1—C8	−178.9 (2)
C4—C5—C6—C1	1.0 (3)	C11—C10—N1—C12	−179.8 (2)
O1—C1—C6—C5	178.56 (15)	C11—C10—N1—C14	58.2 (3)
C2—C1—C6—C5	−0.9 (2)	C11—C10—N1—C8	−59.5 (3)
C5—C4—C7—O2	2.0 (2)	C9—C8—N1—C12	57.8 (2)
C3—C4—C7—O2	−178.72 (16)	C9—C8—N1—C14	179.1 (2)
C5—C4—C7—O3	−176.97 (16)	C9—C8—N1—C10	−60.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3i	0.86	1.74	2.5984 (16)	175
O1W—H1WA···O3ii	0.85	2.04	2.850 (2)	161
O1W—H1WB···O2iii	0.85	1.94	2.781 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3i	0.86	1.74	2.5984 (16)	175
O1W—H1WA⋯O3ii	0.85	2.04	2.850 (2)	161
O1W—H1WB⋯O2iii	0.85	1.94	2.781 (2)	169

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