2-Phenyl-ethanaminium 4-hy-droxy-benzoate.

In the title salt, C8H12N(+)·C7H5O3 (-), the cation is disordered over two orientations with site occupancies of 0.565 (7) and 0.435 (7). In the anion, the carboxyl-ate group makes the dihedral angle of 4.19 (18)° with the benzene ring. In the crystal, the ions are connected by N-H⋯O and O-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For structures containing p-hy­droxy­benzoate anions, see: Marsh & Spek (2001 ▶); Yang et al. (2010 ▶); Sudhahar et al. (2013 ▶).

Experimental

Crystal data

C8H12N+·C7H5O3 −

M = 259.30

Orthorhombic,

a = 13.0721 (12) Å

b = 17.3426 (16) Å

c = 6.2154 (6) Å

V = 1409.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.36 × 0.30 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 0.980

7327 measured reflections

2561 independent reflections

1671 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.03

2561 reflections

254 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813010787/tk5220sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010787/tk5220Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010787/tk5220Isup3.cml

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

C8H12N+·C7H5O3−	F(000) = 552
Mr = 259.30	Dx = 1.222 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2142 reflections
a = 13.0721 (12) Å	θ = 2.8–25.4°
b = 17.3426 (16) Å	µ = 0.09 mm−1
c = 6.2154 (6) Å	T = 295 K
V = 1409.1 (2) Å3	Block, colourless
Z = 4	0.36 × 0.30 × 0.24 mm

Bruker Kappa APEXII CCD diffractometer	2561 independent reflections
Radiation source: fine-focus sealed tube	1671 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω and φ scan	θmax = 25.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→15
Tmin = 0.970, Tmax = 0.980	k = −20→16
7327 measured reflections	l = −7→7

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.0395P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2561 reflections	Δρmax = 0.12 e Å−3
254 parameters	Δρmin = −0.13 e Å−3
6 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
C1	0.3890 (2)	0.37442 (13)	0.6595 (4)	0.0748 (6)
C2	0.31676 (16)	0.31851 (12)	0.5643 (4)	0.0604 (5)
C3	0.33145 (19)	0.28736 (13)	0.3645 (4)	0.0733 (6)
H3	0.3892	0.3009	0.2856	0.088*
C4	0.26201 (19)	0.23621 (15)	0.2782 (4)	0.0811 (7)
H4	0.2734	0.2158	0.1419	0.097*
C5	0.17637 (18)	0.21509 (13)	0.3907 (4)	0.0694 (6)
C6	0.16109 (19)	0.24534 (15)	0.5906 (4)	0.0816 (7)
H6	0.1037	0.2311	0.6696	0.098*
C7	0.2299 (2)	0.29658 (13)	0.6757 (4)	0.0803 (7)
H7	0.2178	0.3171	0.8115	0.096*
O2	0.46474 (11)	0.39682 (8)	0.5459 (3)	0.0800 (5)
O3	0.11124 (14)	0.16400 (11)	0.2981 (3)	0.1025 (6)
H3A	0.0636	0.1552	0.3803	0.154*
O1	0.3714 (2)	0.40004 (14)	0.8429 (4)	0.1320 (9)
C8	0.8544 (9)	0.4684 (9)	1.1607 (13)	0.082 (3)	0.565 (7)
H8	0.8219	0.5128	1.2091	0.099*	0.565 (7)
C9	0.9437 (12)	0.4412 (8)	1.2649 (19)	0.075 (3)	0.565 (7)
H9	0.9641	0.4615	1.3966	0.090*	0.565 (7)
C10	1.0025 (11)	0.3810 (10)	1.161 (4)	0.100 (5)	0.565 (7)
H10	1.0627	0.3644	1.2264	0.120*	0.565 (7)
C11	0.9770 (14)	0.3519 (11)	0.995 (3)	0.093 (5)	0.565 (7)
H11	1.0153	0.3116	0.9385	0.112*	0.565 (7)
C12	0.8778 (14)	0.3815 (13)	0.871 (2)	0.111 (6)	0.565 (7)
H12	0.8641	0.3676	0.7291	0.133*	0.565 (7)
C13	0.8154 (5)	0.4275 (4)	0.9833 (10)	0.0722 (17)	0.565 (7)
C14	0.7075 (5)	0.4460 (3)	0.9177 (10)	0.090 (2)	0.565 (7)
H14A	0.6711	0.3984	0.8889	0.108*	0.565 (7)
H14B	0.6732	0.4720	1.0355	0.108*	0.565 (7)
C15	0.7036 (4)	0.4958 (4)	0.7234 (8)	0.0794 (18)	0.565 (7)
H15A	0.7303	0.4689	0.5986	0.095*	0.565 (7)
H15B	0.7425	0.5428	0.7449	0.095*	0.565 (7)
N1	0.5880 (8)	0.5137 (6)	0.6959 (15)	0.084 (3)	0.565 (7)
H1A	0.5791	0.5442	0.5824	0.125*	0.565 (7)
H1B	0.5648	0.5372	0.8135	0.125*	0.565 (7)
H1C	0.5538	0.4698	0.6762	0.125*	0.565 (7)
C8A	0.8880 (10)	0.4599 (12)	1.148 (2)	0.098 (5)	0.435 (7)
H8A	0.8524	0.4913	1.2436	0.118*	0.435 (7)
C9A	0.9684 (16)	0.4220 (13)	1.212 (4)	0.115 (10)	0.435 (7)
H9A	0.9893	0.4314	1.3525	0.137*	0.435 (7)
C10A	1.018 (2)	0.378 (2)	1.116 (9)	0.22 (2)	0.435 (7)
H10A	1.0801	0.3586	1.1639	0.262*	0.435 (7)
C11A	0.967 (2)	0.3549 (19)	0.898 (4)	0.104 (7)	0.435 (7)
H11A	0.9950	0.3166	0.8119	0.125*	0.435 (7)
C12A	0.899 (2)	0.3841 (12)	0.852 (4)	0.108 (7)	0.435 (7)
H12A	0.8632	0.3613	0.7397	0.130*	0.435 (7)
C13A	0.8560 (6)	0.4526 (5)	0.9342 (13)	0.0609 (19)	0.435 (7)
C14A	0.7772 (4)	0.4966 (3)	0.8103 (10)	0.072 (2)	0.435 (7)
H14C	0.7680	0.5470	0.8755	0.086*	0.435 (7)
H14D	0.8012	0.5043	0.6642	0.086*	0.435 (7)
C15A	0.6773 (5)	0.4558 (4)	0.8050 (15)	0.0655 (19)	0.435 (7)
H15C	0.6526	0.4460	0.9497	0.079*	0.435 (7)
H15D	0.6834	0.4070	0.7296	0.079*	0.435 (7)
N1A	0.6043 (9)	0.5113 (6)	0.6832 (19)	0.072 (4)	0.435 (7)
H1E	0.5424	0.4902	0.6743	0.108*	0.435 (7)
H1F	0.6284	0.5198	0.5514	0.108*	0.435 (7)
H1D	0.6002	0.5558	0.7541	0.108*	0.435 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0827 (17)	0.0731 (14)	0.0685 (16)	−0.0049 (14)	−0.0114 (14)	0.0053 (14)
C2	0.0601 (13)	0.0590 (12)	0.0620 (13)	0.0042 (11)	−0.0004 (11)	0.0058 (11)
C3	0.0682 (15)	0.0760 (15)	0.0757 (16)	−0.0053 (13)	0.0144 (12)	−0.0077 (13)
C4	0.0795 (17)	0.0930 (18)	0.0707 (16)	−0.0163 (15)	0.0152 (13)	−0.0154 (14)
C5	0.0637 (14)	0.0664 (14)	0.0781 (16)	0.0031 (12)	0.0045 (12)	−0.0060 (12)
C6	0.0730 (15)	0.0774 (15)	0.0944 (19)	−0.0112 (14)	0.0266 (14)	−0.0100 (15)
C7	0.0987 (18)	0.0776 (15)	0.0645 (14)	−0.0058 (15)	0.0200 (14)	−0.0092 (13)
O2	0.0606 (9)	0.0745 (9)	0.1050 (12)	−0.0018 (8)	−0.0089 (10)	−0.0008 (10)
O3	0.0831 (11)	0.1104 (14)	0.1141 (16)	−0.0279 (11)	0.0056 (10)	−0.0291 (12)
O1	0.173 (2)	0.148 (2)	0.0746 (13)	−0.0583 (18)	−0.0001 (14)	−0.0254 (13)
C8	0.071 (7)	0.110 (5)	0.065 (4)	0.046 (5)	−0.002 (4)	−0.018 (3)
C9	0.072 (7)	0.088 (4)	0.065 (5)	0.008 (5)	−0.008 (5)	0.004 (4)
C10	0.039 (5)	0.102 (8)	0.157 (13)	0.012 (5)	−0.020 (6)	0.030 (10)
C11	0.076 (7)	0.071 (6)	0.133 (15)	0.021 (6)	0.040 (9)	0.013 (11)
C12	0.103 (9)	0.133 (11)	0.096 (9)	0.015 (7)	−0.010 (9)	−0.021 (7)
C13	0.067 (4)	0.077 (4)	0.072 (4)	0.009 (3)	0.018 (3)	−0.006 (3)
C14	0.088 (5)	0.111 (4)	0.072 (4)	0.023 (4)	0.023 (3)	0.026 (3)
C15	0.070 (5)	0.101 (4)	0.067 (3)	−0.009 (3)	0.006 (3)	−0.004 (3)
N1	0.047 (3)	0.131 (7)	0.073 (5)	−0.008 (3)	−0.014 (3)	0.031 (4)
C8A	0.060 (9)	0.113 (9)	0.122 (10)	0.036 (8)	0.017 (7)	−0.041 (6)
C9A	0.070 (13)	0.18 (2)	0.097 (12)	0.009 (13)	0.010 (8)	−0.001 (13)
C10A	0.15 (2)	0.19 (2)	0.32 (4)	0.011 (17)	−0.01 (3)	0.00 (3)
C11A	0.085 (9)	0.096 (12)	0.131 (16)	0.024 (7)	0.039 (11)	−0.024 (12)
C12A	0.133 (13)	0.075 (8)	0.116 (11)	0.037 (8)	0.082 (9)	−0.018 (6)
C13A	0.042 (4)	0.072 (5)	0.068 (5)	−0.002 (4)	0.007 (3)	0.003 (3)
C14A	0.058 (4)	0.076 (4)	0.080 (4)	−0.014 (3)	0.000 (3)	0.012 (3)
C15A	0.065 (4)	0.053 (3)	0.079 (5)	−0.008 (3)	−0.005 (4)	0.017 (4)
N1A	0.062 (7)	0.084 (6)	0.069 (6)	−0.017 (4)	0.012 (4)	−0.042 (5)

C1—O1	1.245 (3)	C14—H14B	0.9700
C1—O2	1.277 (3)	C15—N1	1.551 (8)
C1—C2	1.477 (3)	C15—H15A	0.9700
C2—C3	1.368 (3)	C15—H15B	0.9700
C2—C7	1.383 (3)	N1—H1A	0.8900
C3—C4	1.378 (3)	N1—H1B	0.8900
C3—H3	0.9300	N1—H1C	0.8900
C4—C5	1.370 (3)	C8A—C9A	1.30 (3)
C4—H4	0.9300	C8A—C13A	1.401 (11)
C5—O3	1.357 (3)	C8A—H8A	0.9300
C5—C6	1.363 (3)	C9A—C10A	1.16 (5)
C6—C7	1.370 (3)	C9A—H9A	0.9300
C6—H6	0.9300	C10A—C11A	1.56 (6)
C7—H7	0.9300	C10A—H10A	0.9300
O3—H3A	0.8200	C11A—C12A	1.06 (4)
C8—C13	1.407 (9)	C11A—H11A	0.9300
C8—C9	1.415 (19)	C12A—C13A	1.41 (2)
C8—H8	0.9300	C12A—H12A	0.9300
C9—C10	1.45 (3)	C13A—C14A	1.495 (7)
C9—H9	0.9300	C14A—C15A	1.486 (7)
C10—C11	1.20 (3)	C14A—H14C	0.9700
C10—H10	0.9300	C14A—H14D	0.9700
C11—C12	1.60 (2)	C15A—N1A	1.554 (8)
C11—H11	0.9300	C15A—H15C	0.9700
C12—C13	1.34 (2)	C15A—H15D	0.9700
C12—H12	0.9300	N1A—H1E	0.8900
C13—C14	1.503 (8)	N1A—H1F	0.8900
C14—C15	1.485 (6)	N1A—H1D	0.8900
C14—H14A	0.9700
O1—C1—O2	122.8 (2)	C14—C15—H15A	111.0
O1—C1—C2	118.9 (2)	N1—C15—H15A	111.0
O2—C1—C2	118.3 (2)	C14—C15—H15B	111.0
C3—C2—C7	117.4 (2)	N1—C15—H15B	111.0
C3—C2—C1	122.2 (2)	H15A—C15—H15B	109.0
C7—C2—C1	120.3 (2)	C15—N1—H1A	109.5
C2—C3—C4	121.0 (2)	C15—N1—H1B	109.5
C2—C3—H3	119.5	H1A—N1—H1B	109.5
C4—C3—H3	119.5	C15—N1—H1C	109.5
C5—C4—C3	120.8 (2)	H1A—N1—H1C	109.5
C5—C4—H4	119.6	H1B—N1—H1C	109.5
C3—C4—H4	119.6	C9A—C8A—C13A	119.0 (11)
O3—C5—C6	123.1 (2)	C9A—C8A—H8A	120.5
O3—C5—C4	118.1 (2)	C13A—C8A—H8A	120.5
C6—C5—C4	118.8 (2)	C10A—C9A—C8A	129 (3)
C5—C6—C7	120.3 (2)	C10A—C9A—H9A	115.7
C5—C6—H6	119.8	C8A—C9A—H9A	115.7
C7—C6—H6	119.8	C9A—C10A—C11A	112 (3)
C6—C7—C2	121.6 (2)	C9A—C10A—H10A	124.0
C6—C7—H7	119.2	C11A—C10A—H10A	124.0
C2—C7—H7	119.2	C12A—C11A—C10A	118 (3)
C5—O3—H3A	109.5	C12A—C11A—H11A	121.0
C13—C8—C9	119.3 (11)	C10A—C11A—H11A	121.0
C13—C8—H8	120.4	C11A—C12A—C13A	130 (3)
C9—C8—H8	120.4	C11A—C12A—H12A	115.2
C8—C9—C10	118.4 (13)	C13A—C12A—H12A	115.2
C8—C9—H9	120.8	C8A—C13A—C12A	107.5 (13)
C10—C9—H9	120.8	C8A—C13A—C14A	130.5 (9)
C11—C10—C9	122.6 (13)	C12A—C13A—C14A	121.2 (12)
C11—C10—H10	118.7	C15A—C14A—C13A	111.9 (5)
C9—C10—H10	118.7	C15A—C14A—H14C	109.2
C10—C11—C12	120.7 (16)	C13A—C14A—H14C	109.2
C10—C11—H11	119.7	C15A—C14A—H14D	109.2
C12—C11—H11	119.7	C13A—C14A—H14D	109.2
C13—C12—C11	115.7 (11)	H14C—C14A—H14D	107.9
C13—C12—H12	122.2	C14A—C15A—N1A	104.8 (8)
C11—C12—H12	122.2	C14A—C15A—H15C	110.8
C12—C13—C8	119.3 (9)	N1A—C15A—H15C	110.8
C12—C13—C14	123.9 (8)	C14A—C15A—H15D	110.8
C8—C13—C14	116.4 (7)	N1A—C15A—H15D	110.8
C15—C14—C13	112.2 (5)	H15C—C15A—H15D	108.9
C15—C14—H14A	109.2	C15A—N1A—H1E	109.5
C13—C14—H14A	109.2	C15A—N1A—H1F	109.5
C15—C14—H14B	109.2	H1E—N1A—H1F	109.5
C13—C14—H14B	109.2	C15A—N1A—H1D	109.5
H14A—C14—H14B	107.9	H1E—N1A—H1D	109.5
C14—C15—N1	103.8 (6)	H1F—N1A—H1D	109.5
O1—C1—C2—C3	−179.4 (3)	C11—C12—C13—C8	23 (2)
O2—C1—C2—C3	3.5 (3)	C11—C12—C13—C14	−164.8 (12)
O1—C1—C2—C7	1.5 (3)	C9—C8—C13—C12	−22.7 (19)
O2—C1—C2—C7	−175.6 (2)	C9—C8—C13—C14	164.2 (10)
C7—C2—C3—C4	0.1 (3)	C12—C13—C14—C15	−69.6 (14)
C1—C2—C3—C4	−179.0 (2)	C8—C13—C14—C15	103.1 (10)
C2—C3—C4—C5	−0.1 (4)	C13—C14—C15—N1	−175.2 (6)
C3—C4—C5—O3	−179.5 (2)	C13A—C8A—C9A—C10A	−4 (4)
C3—C4—C5—C6	−0.3 (4)	C8A—C9A—C10A—C11A	−10 (5)
O3—C5—C6—C7	179.8 (2)	C9A—C10A—C11A—C12A	6 (5)
C4—C5—C6—C7	0.7 (4)	C10A—C11A—C12A—C13A	14 (5)
C5—C6—C7—C2	−0.8 (4)	C9A—C8A—C13A—C12A	20 (3)
C3—C2—C7—C6	0.4 (3)	C9A—C8A—C13A—C14A	−170.4 (16)
C1—C2—C7—C6	179.4 (2)	C11A—C12A—C13A—C8A	−26 (4)
C13—C8—C9—C10	11.5 (18)	C11A—C12A—C13A—C14A	163 (3)
C8—C9—C10—C11	−2 (2)	C8A—C13A—C14A—C15A	−96.9 (15)
C9—C10—C11—C12	3 (2)	C12A—C13A—C14A—C15A	71.6 (15)
C10—C11—C12—C13	−14 (3)	C13A—C14A—C15A—N1A	176.8 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.89	1.89	2.709 (11)	152
N1—H1B···O2ii	0.89	1.88	2.760 (10)	168
N1—H1C···O2	0.89	1.90	2.752 (11)	159
O3—H3A···O2iii	0.82	1.88	2.674 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.89	1.89	2.709 (11)	152
N1—H1B⋯O2ii	0.89	1.88	2.760 (10)	168
N1—H1C⋯O2	0.89	1.90	2.752 (11)	159
O3—H3A⋯O2iii	0.82	1.88	2.674 (3)	162

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