Dimethyl­ammonium 4-hy­droxy­benzoate

Sornamurthy, B.M.; Peramaiyan, G.; Chakkaravarthi, G.; Kumar, R.M.; Manivannan, V.

doi:10.1107/S1600536812016145

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1445

doi:10.1107/S1600536812016145

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Dimethylammonium 4-hydroxybenzoate

B. M. Sornamurthy,^a G. Peramaiyan,^a G. Chakkaravarthi,^b ^* R. Mohan Kumar ^a and V. Manivannan ^c

^aDepartment of Physics, Presidency College, Chennai 600 005, India, ^bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^cDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 1 April 2012; accepted 13 April 2012; online 21 April 2012)

In the crystal structure of the title compound, C₂H₈N⁺·C₇H₅O₃⁻, 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_r = 183.20
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.143
S = 1.04
2394 reflections
122 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812016145/bt5869sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812016145/bt5869Isup3.cml

checkCIF report

Comment top

The goemetric parameters of the title compound (Fig. 1) are comparable with those in related structures (Hemamalini et al., 2011; Chitradevi et al., 2009).

The molecular structure is stabilized by intramolecular N—H···O hydrogen bond and the crystal structure is formed by weak intermolecular O—H···O and N-H···O (Fig. 2 & Table 1) interactions.

Related literature top

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

Experimental top

A solution of p-hydroxybenzoic acid (0.138g, 1 mmol) in 10 ml ethanol was added with stirring to a solution of dimethylamine (0.450g, 1 mmol) in 10 ml of distilled water at 303 K. After some time, a white precipitate was obtained. The white precipitate was dissolved in ethanol and colourless single crystals suitable for X-ray diffraction were obtained by slow evaporation of the ethanol solution.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down b axis. Intermolecular Hydrogen bond is shown as dashed line. H atoms not involved in hydrogen bonding have been omitted.

Dimethylammonium 4-hydroxybenzoate top

Crystal data top

C₂H₈N⁺·C₇H₅O₃⁻	F(000) = 784
M_r = 183.20	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0681P)² + 0.4306P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2394 reflections	Δρ_max = 0.29 e Å⁻³
122 parameters	Δρ_min = −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)

Crystal data top

C₂H₈N⁺·C₇H₅O₃⁻	V = 1995.0 (3) Å³
M_r = 183.20	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.2980 (8) Å	µ = 0.09 mm⁻¹
b = 10.0586 (9) Å	T = 295 K
c = 19.2595 (17) Å	0.18 × 0.16 × 0.14 mm

Data collection top

Bruker Kappa APEXII diffractometer	2394 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1673 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.987	R_int = 0.036
9496 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
2394 reflections	Δρ_min = −0.27 e Å⁻³
122 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, y, −z+3/2; (ii) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂H₈N⁺·C₇H₅O₃⁻
M_r	183.20
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	10.2980 (8), 10.0586 (9), 19.2595 (17)
V (Å³)	1995.0 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.18 × 0.16 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.984, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	9496, 2394, 1673
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.143, 1.04
No. of reflections	2394
No. of parameters	122
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.27

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, y, −z+3/2; (ii) x+1/2, −y+1/2, −z+1.

Acknowledgements

The authors wish to acknowledge the SAIF, IIT, Madras, for the data collection.

References

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