organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1445

Di­methyl­ammonium 4-hy­dr­oxy­benzoate

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[Hemamalini, M., Goh, J. H. & Fun, H.-K. (2011). Acta Cryst. E67, o3121.]). Chitradevi et al. (2009[Chitradevi, A., Athimoolam, S., Sridhar, B. & Bahadur, S. A. (2009). Acta Cryst. E65, o3041-o3042.]).

[Scheme 1]

Experimental

Crystal data
  • C2H8N+·C7H5O3

  • Mr = 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[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.984, Tmax = 0.987

  • 9496 measured reflections

  • 2394 independent reflections

  • 1673 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

All H atoms were located in a difference map, but positioned geometrically with O—H = 0.82Å, N—H = 0.90Å and C—H = 0.93–0.97 Å and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(Cmethyl,O).

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
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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+·C7H5O3F(000) = 784
Mr = 183.20Dx = 1.220 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 10382 reflections
a = 10.2980 (8) Åθ = 2.1–28.2°
b = 10.0586 (9) ŵ = 0.09 mm1
c = 19.2595 (17) ÅT = 295 K
V = 1995.0 (3) Å3Block, colourless
Z = 80.18 × 0.16 × 0.14 mm
Data collection top
Bruker Kappa APEXII
diffractometer
2394 independent reflections
Radiation source: fine-focus sealed tube1673 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω and ϕ scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1312
Tmin = 0.984, Tmax = 0.987k = 1212
9496 measured reflectionsl = 2423
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-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 reflectionsΔρmax = 0.29 e Å3
122 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.051 (4)
Crystal data top
C2H8N+·C7H5O3V = 1995.0 (3) Å3
Mr = 183.20Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 10.2980 (8) ŵ = 0.09 mm1
b = 10.0586 (9) ÅT = 295 K
c = 19.2595 (17) Å0.18 × 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)
Tmin = 0.984, Tmax = 0.987Rint = 0.036
9496 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.04Δρmax = 0.29 e Å3
2394 reflectionsΔρmin = 0.27 e Å3
122 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.07130 (13)0.17170 (15)0.67576 (7)0.0411 (4)
C21.01976 (15)0.06187 (15)0.71025 (8)0.0454 (4)
H20.95270.01400.68970.055*
C31.06624 (15)0.02280 (16)0.77417 (8)0.0489 (4)
H31.03150.05180.79590.059*
C41.16481 (14)0.09434 (17)0.80639 (8)0.0463 (4)
C51.21388 (15)0.20718 (16)0.77404 (8)0.0479 (4)
H51.27740.25790.79590.058*
C61.16815 (14)0.24402 (15)0.70933 (8)0.0453 (4)
H61.20280.31870.68770.054*
C81.02545 (14)0.21186 (16)0.60471 (8)0.0446 (4)
C91.3600 (3)0.0899 (2)0.54792 (15)0.1060 (10)
H9A1.44780.06110.54060.159*
H9B1.30470.05070.51340.159*
H9C1.33180.06270.59330.159*
C101.4471 (2)0.3010 (3)0.58929 (11)0.0863 (7)
H10A1.42990.27550.63640.129*
H10B1.43850.39560.58480.129*
H10C1.53380.27500.57700.129*
N11.35343 (14)0.23451 (14)0.54264 (7)0.0525 (4)
H1A1.27260.26160.55330.063*
H1B1.36980.25890.49850.063*
O11.20733 (12)0.05085 (14)0.86889 (6)0.0650 (4)
H11.27270.09220.88000.098*
O20.91717 (11)0.16686 (14)0.58397 (6)0.0603 (4)
O31.09461 (11)0.28636 (13)0.56856 (6)0.0590 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0336 (7)0.0454 (8)0.0441 (8)0.0053 (6)0.0039 (6)0.0005 (6)
C20.0371 (8)0.0468 (9)0.0524 (9)0.0036 (6)0.0020 (6)0.0028 (7)
C30.0422 (8)0.0487 (9)0.0557 (9)0.0063 (7)0.0003 (7)0.0073 (7)
C40.0363 (8)0.0561 (9)0.0465 (8)0.0000 (7)0.0001 (6)0.0050 (7)
C50.0386 (8)0.0518 (9)0.0534 (9)0.0072 (7)0.0047 (6)0.0014 (7)
C60.0383 (8)0.0442 (8)0.0533 (9)0.0022 (6)0.0027 (6)0.0034 (6)
C80.0349 (8)0.0524 (9)0.0467 (8)0.0063 (6)0.0049 (6)0.0011 (7)
C90.130 (2)0.0600 (14)0.128 (2)0.0119 (14)0.0553 (19)0.0005 (14)
C100.0676 (13)0.125 (2)0.0665 (13)0.0039 (13)0.0052 (11)0.0110 (13)
N10.0505 (8)0.0579 (9)0.0492 (8)0.0060 (6)0.0098 (6)0.0028 (6)
O10.0531 (7)0.0878 (10)0.0541 (7)0.0161 (6)0.0109 (5)0.0198 (6)
O20.0446 (7)0.0909 (10)0.0454 (6)0.0114 (6)0.0022 (5)0.0078 (6)
O30.0462 (7)0.0713 (8)0.0596 (7)0.0017 (6)0.0014 (5)0.0190 (6)
Geometric parameters (Å, º) top
C1—C61.394 (2)C8—O21.2680 (19)
C1—C21.394 (2)C9—N11.460 (3)
C1—C81.503 (2)C9—H9A0.9600
C2—C31.378 (2)C9—H9B0.9600
C2—H20.9300C9—H9C0.9600
C3—C41.390 (2)C10—N11.478 (3)
C3—H30.9300C10—H10A0.9600
C4—O11.3535 (19)C10—H10B0.9600
C4—C51.390 (2)C10—H10C0.9600
C5—C61.383 (2)N1—H1A0.9000
C5—H50.9300N1—H1B0.9000
C6—H60.9300O1—H10.8200
C8—O31.2464 (19)
C6—C1—C2117.72 (14)O2—C8—C1117.85 (14)
C6—C1—C8120.46 (14)N1—C9—H9A109.5
C2—C1—C8121.82 (14)N1—C9—H9B109.5
C3—C2—C1121.30 (14)H9A—C9—H9B109.5
C3—C2—H2119.4N1—C9—H9C109.5
C1—C2—H2119.4H9A—C9—H9C109.5
C2—C3—C4120.30 (15)H9B—C9—H9C109.5
C2—C3—H3119.8N1—C10—H10A109.5
C4—C3—H3119.8N1—C10—H10B109.5
O1—C4—C5123.02 (14)H10A—C10—H10B109.5
O1—C4—C3117.76 (14)N1—C10—H10C109.5
C5—C4—C3119.21 (14)H10A—C10—H10C109.5
C6—C5—C4119.93 (14)H10B—C10—H10C109.5
C6—C5—H5120.0C9—N1—C10112.2 (2)
C4—C5—H5120.0C9—N1—H1A109.2
C5—C6—C1121.47 (14)C10—N1—H1A109.2
C5—C6—H6119.3C9—N1—H1B109.2
C1—C6—H6119.3C10—N1—H1B109.2
O3—C8—O2122.76 (15)H1A—N1—H1B107.9
O3—C8—C1119.39 (14)C4—O1—H1109.5
C6—C1—C2—C32.5 (2)C4—C5—C6—C11.2 (2)
C8—C1—C2—C3177.33 (14)C2—C1—C6—C51.3 (2)
C1—C2—C3—C41.2 (2)C8—C1—C6—C5178.54 (14)
C2—C3—C4—O1179.52 (15)C6—C1—C8—O318.5 (2)
C2—C3—C4—C51.4 (2)C2—C1—C8—O3161.34 (15)
O1—C4—C5—C6178.38 (15)C6—C1—C8—O2162.06 (15)
C3—C4—C5—C62.5 (2)C2—C1—C8—O218.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.901.872.7614 (18)169
O1—H1···O2i0.821.812.6183 (17)171
N1—H1B···O2ii0.901.822.7131 (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 formulaC2H8N+·C7H5O3
Mr183.20
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)295
a, b, c (Å)10.2980 (8), 10.0586 (9), 19.2595 (17)
V3)1995.0 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.18 × 0.16 × 0.14
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.984, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
9496, 2394, 1673
Rint0.036
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.143, 1.04
No. of reflections2394
No. of parameters122
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1A···O30.901.872.7614 (18)169
O1—H1···O2i0.821.812.6183 (17)171
N1—H1B···O2ii0.901.822.7131 (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

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChitradevi, A., Athimoolam, S., Sridhar, B. & Bahadur, S. A. (2009). Acta Cryst. E65, o3041–o3042.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationHemamalini, M., Goh, J. H. & Fun, H.-K. (2011). Acta Cryst. E67, o3121.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1445
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