Dimethyl-ammonium 4-hy-droxy-benzoate.

In the crystal structure of the title compound, C(2)H(8)N(+)·C(7)H(5)O(3) (-), the anions and cations are linked by O-H⋯O and N-H⋯O hydrogen bonds into layers parallel to the ac plane.

Related literature

For related structures, see: Hemamalini et al. (2011 ▶). Chitradevi et al. (2009 ▶).

Experimental

Crystal data

C2H8N+·C7H5O3 −

M = 183.20

Orthorhombic,

a = 10.2980 (8) Å

b = 10.0586 (9) Å

c = 19.2595 (17) Å

V = 1995.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.18 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.987

9496 measured reflections

2394 independent reflections

1673 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.143

S = 1.04

2394 reflections

122 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.27 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016145/bt5869sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016145/bt5869Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016145/bt5869Isup3.cml

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

C2H8N+·C7H5O3−	F(000) = 784
Mr = 183.20	Dx = 1.220 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 10382 reflections
a = 10.2980 (8) Å	θ = 2.1–28.2°
b = 10.0586 (9) Å	µ = 0.09 mm−1
c = 19.2595 (17) Å	T = 295 K
V = 1995.0 (3) Å3	Block, colourless
Z = 8	0.18 × 0.16 × 0.14 mm

Bruker Kappa APEXII diffractometer	2394 independent reflections
Radiation source: fine-focus sealed tube	1673 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω and φ scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.984, Tmax = 0.987	k = −12→12
9496 measured reflections	l = −24→23

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.4306P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2394 reflections	Δρmax = 0.29 e Å−3
122 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.051 (4)

	x	y	z	Uiso*/Ueq
C1	1.07130 (13)	0.17170 (15)	0.67576 (7)	0.0411 (4)
C2	1.01976 (15)	0.06187 (15)	0.71025 (8)	0.0454 (4)
H2	0.9527	0.0140	0.6897	0.055*
C3	1.06624 (15)	0.02280 (16)	0.77417 (8)	0.0489 (4)
H3	1.0315	−0.0518	0.7959	0.059*
C4	1.16481 (14)	0.09434 (17)	0.80639 (8)	0.0463 (4)
C5	1.21388 (15)	0.20718 (16)	0.77404 (8)	0.0479 (4)
H5	1.2774	0.2579	0.7959	0.058*
C6	1.16815 (14)	0.24402 (15)	0.70933 (8)	0.0453 (4)
H6	1.2028	0.3187	0.6877	0.054*
C8	1.02545 (14)	0.21186 (16)	0.60471 (8)	0.0446 (4)
C9	1.3600 (3)	0.0899 (2)	0.54792 (15)	0.1060 (10)
H9A	1.4478	0.0611	0.5406	0.159*
H9B	1.3047	0.0507	0.5134	0.159*
H9C	1.3318	0.0627	0.5933	0.159*
C10	1.4471 (2)	0.3010 (3)	0.58929 (11)	0.0863 (7)
H10A	1.4299	0.2755	0.6364	0.129*
H10B	1.4385	0.3956	0.5848	0.129*
H10C	1.5338	0.2750	0.5770	0.129*
N1	1.35343 (14)	0.23451 (14)	0.54264 (7)	0.0525 (4)
H1A	1.2726	0.2616	0.5533	0.063*
H1B	1.3698	0.2589	0.4985	0.063*
O1	1.20733 (12)	0.05085 (14)	0.86889 (6)	0.0650 (4)
H1	1.2727	0.0922	0.8800	0.098*
O2	0.91717 (11)	0.16686 (14)	0.58397 (6)	0.0603 (4)
O3	1.09461 (11)	0.28636 (13)	0.56856 (6)	0.0590 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0336 (7)	0.0454 (8)	0.0441 (8)	0.0053 (6)	0.0039 (6)	−0.0005 (6)
C2	0.0371 (8)	0.0468 (9)	0.0524 (9)	−0.0036 (6)	−0.0020 (6)	−0.0028 (7)
C3	0.0422 (8)	0.0487 (9)	0.0557 (9)	−0.0063 (7)	0.0003 (7)	0.0073 (7)
C4	0.0363 (8)	0.0561 (9)	0.0465 (8)	0.0000 (7)	0.0001 (6)	0.0050 (7)
C5	0.0386 (8)	0.0518 (9)	0.0534 (9)	−0.0072 (7)	−0.0047 (6)	−0.0014 (7)
C6	0.0383 (8)	0.0442 (8)	0.0533 (9)	−0.0022 (6)	0.0027 (6)	0.0034 (6)
C8	0.0349 (8)	0.0524 (9)	0.0467 (8)	0.0063 (6)	0.0049 (6)	0.0011 (7)
C9	0.130 (2)	0.0600 (14)	0.128 (2)	0.0119 (14)	0.0553 (19)	0.0005 (14)
C10	0.0676 (13)	0.125 (2)	0.0665 (13)	−0.0039 (13)	−0.0052 (11)	−0.0110 (13)
N1	0.0505 (8)	0.0579 (9)	0.0492 (8)	0.0060 (6)	0.0098 (6)	0.0028 (6)
O1	0.0531 (7)	0.0878 (10)	0.0541 (7)	−0.0161 (6)	−0.0109 (5)	0.0198 (6)
O2	0.0446 (7)	0.0909 (10)	0.0454 (6)	−0.0114 (6)	−0.0022 (5)	0.0078 (6)
O3	0.0462 (7)	0.0713 (8)	0.0596 (7)	−0.0017 (6)	0.0014 (5)	0.0190 (6)

C1—C6	1.394 (2)	C8—O2	1.2680 (19)
C1—C2	1.394 (2)	C9—N1	1.460 (3)
C1—C8	1.503 (2)	C9—H9A	0.9600
C2—C3	1.378 (2)	C9—H9B	0.9600
C2—H2	0.9300	C9—H9C	0.9600
C3—C4	1.390 (2)	C10—N1	1.478 (3)
C3—H3	0.9300	C10—H10A	0.9600
C4—O1	1.3535 (19)	C10—H10B	0.9600
C4—C5	1.390 (2)	C10—H10C	0.9600
C5—C6	1.383 (2)	N1—H1A	0.9000
C5—H5	0.9300	N1—H1B	0.9000
C6—H6	0.9300	O1—H1	0.8200
C8—O3	1.2464 (19)
C6—C1—C2	117.72 (14)	O2—C8—C1	117.85 (14)
C6—C1—C8	120.46 (14)	N1—C9—H9A	109.5
C2—C1—C8	121.82 (14)	N1—C9—H9B	109.5
C3—C2—C1	121.30 (14)	H9A—C9—H9B	109.5
C3—C2—H2	119.4	N1—C9—H9C	109.5
C1—C2—H2	119.4	H9A—C9—H9C	109.5
C2—C3—C4	120.30 (15)	H9B—C9—H9C	109.5
C2—C3—H3	119.8	N1—C10—H10A	109.5
C4—C3—H3	119.8	N1—C10—H10B	109.5
O1—C4—C5	123.02 (14)	H10A—C10—H10B	109.5
O1—C4—C3	117.76 (14)	N1—C10—H10C	109.5
C5—C4—C3	119.21 (14)	H10A—C10—H10C	109.5
C6—C5—C4	119.93 (14)	H10B—C10—H10C	109.5
C6—C5—H5	120.0	C9—N1—C10	112.2 (2)
C4—C5—H5	120.0	C9—N1—H1A	109.2
C5—C6—C1	121.47 (14)	C10—N1—H1A	109.2
C5—C6—H6	119.3	C9—N1—H1B	109.2
C1—C6—H6	119.3	C10—N1—H1B	109.2
O3—C8—O2	122.76 (15)	H1A—N1—H1B	107.9
O3—C8—C1	119.39 (14)	C4—O1—H1	109.5
C6—C1—C2—C3	−2.5 (2)	C4—C5—C6—C1	1.2 (2)
C8—C1—C2—C3	177.33 (14)	C2—C1—C6—C5	1.3 (2)
C1—C2—C3—C4	1.2 (2)	C8—C1—C6—C5	−178.54 (14)
C2—C3—C4—O1	−179.52 (15)	C6—C1—C8—O3	18.5 (2)
C2—C3—C4—C5	1.4 (2)	C2—C1—C8—O3	−161.34 (15)
O1—C4—C5—C6	178.38 (15)	C6—C1—C8—O2	−162.06 (15)
C3—C4—C5—C6	−2.5 (2)	C2—C1—C8—O2	18.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.90	1.87	2.7614 (18)	169
O1—H1···O2i	0.82	1.81	2.6183 (17)	171
N1—H1B···O2ii	0.90	1.82	2.7131 (17)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.90	1.87	2.7614 (18)	169
O1—H1⋯O2i	0.82	1.81	2.6183 (17)	171
N1—H1B⋯O2ii	0.90	1.82	2.7131 (17)	170

Symmetry codes: (i) ; (ii) .