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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1706.
Published online 2010 June 18. doi:  10.1107/S1600536810022592
PMCID: PMC3006923

2-Methyl­propan-2-aminium 4-hy­droxy­benzoate

Abstract

In the crystal of the title mol­ecular salt, C4H12N+·C7H5O3 , the cation is linked to three nearby anions by N—H(...)O hydrogen bonds. An O—H(...)O hydrogen bond between anions further consolidates the packing.

Related literature

For a related structure, see: Scholz & Gorls (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1706-scheme1.jpg

Experimental

Crystal data

  • C4H12N+·C7H5O3
  • M r = 211.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1706-efi1.jpg
  • a = 6.8300 (14) Å
  • b = 9.2790 (19) Å
  • c = 19.831 (4) Å
  • β = 99.58 (3)°
  • V = 1239.3 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.10 × 0.09 × 0.08 mm

Data collection

  • Bruker SMART CCD diffractometer
  • 2899 measured reflections
  • 2677 independent reflections
  • 1804 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.168
  • S = 1.04
  • 2677 reflections
  • 149 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2003 [triangle]); cell refinement: SAINT (Bruker, 2003 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022592/hb5493sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022592/hb5493Isup2.hkl

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

supplementary crystallographic information

Experimental

A mixture of 2-methylpropan-2-amine(0.02 mol) and 4-hydroxybenzoic acid (0.02 mol) was stirred in ethanol (30 ml) at 353 K for 3 h to afford the title compound (yield 50%). Colourless bars of (I) were obtained by recrystallization from acetone at room temperature.

Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with N—H and C—H distances of 0.86 and 0.93–0.96 Å, respectively, and with Uiso(H) = 1.2Ueq of the parent atoms.

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.

Crystal data

C4H12N+·C7H5O3F(000) = 456
Mr = 211.26Dx = 1.132 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1804 reflections
a = 6.8300 (14) Åθ = 2.1–27.0°
b = 9.2790 (19) ŵ = 0.08 mm1
c = 19.831 (4) ÅT = 293 K
β = 99.58 (3)°Bar, colorless
V = 1239.3 (4) Å30.10 × 0.09 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer1804 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
graphiteθmax = 27.0°, θmin = 2.1°
phi and ω scansh = 0→8
2899 measured reflectionsk = 0→11
2677 independent reflectionsl = −23→23

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.168w = 1/[σ2(Fo2) + (0.0928P)2 + 0.1735P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2677 reflectionsΔρmax = 0.22 e Å3
149 parametersΔρmin = −0.29 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.59 (3)

Special details

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.

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

xyzUiso*/Ueq
C10.1770 (3)0.81042 (19)0.40216 (9)0.0475 (4)
C20.2054 (2)0.70697 (18)0.34696 (8)0.0435 (4)
C30.3911 (3)0.6882 (2)0.32850 (10)0.0618 (6)
H3A0.49990.73720.35230.074*
C40.4170 (3)0.5976 (3)0.27512 (12)0.0728 (7)
H4A0.54230.58720.26320.087*
C50.2577 (3)0.5225 (2)0.23940 (10)0.0571 (5)
C60.0722 (3)0.5367 (2)0.25849 (10)0.0558 (5)
H6A−0.03510.48430.23590.067*
C70.0470 (2)0.6290 (2)0.31113 (9)0.0513 (5)
H7A−0.07850.63930.32290.062*
O10.00062 (19)0.84869 (15)0.40644 (6)0.0606 (4)
O20.3246 (2)0.85859 (16)0.44198 (7)0.0667 (5)
O30.2922 (2)0.4377 (2)0.18682 (9)0.0863 (6)
H3B0.18650.41870.16220.129*
C80.7450 (4)0.6075 (3)0.50722 (16)0.0949 (9)
H8A0.61090.60400.48320.142*
H8B0.76930.52590.53720.142*
H8C0.83520.60530.47490.142*
C90.6313 (5)0.7601 (4)0.59955 (17)0.1178 (12)
H9A0.64860.85220.62180.177*
H9B0.65630.68500.63310.177*
H9C0.49770.75200.57540.177*
C100.9911 (4)0.7600 (3)0.58411 (13)0.0806 (7)
H10A1.01030.85190.60650.121*
H10B1.07720.75220.55070.121*
H10C1.02130.68450.61730.121*
C110.7764 (3)0.7461 (2)0.54907 (11)0.0632 (6)
N10.7346 (2)0.86993 (18)0.49897 (8)0.0483 (4)
H10.734 (3)0.958 (2)0.5202 (10)0.058*
H20.815 (3)0.869 (2)0.4690 (12)0.058*
H30.608 (3)0.859 (2)0.4718 (10)0.058*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0461 (10)0.0530 (10)0.0442 (8)0.0012 (8)0.0095 (7)0.0012 (7)
C20.0394 (9)0.0475 (9)0.0439 (8)−0.0014 (7)0.0077 (7)0.0004 (7)
C30.0401 (10)0.0804 (13)0.0662 (11)−0.0155 (9)0.0120 (8)−0.0224 (10)
C40.0406 (10)0.1022 (17)0.0781 (14)−0.0061 (10)0.0176 (9)−0.0322 (12)
C50.0449 (10)0.0678 (12)0.0576 (10)0.0055 (8)0.0055 (8)−0.0158 (9)
C60.0394 (9)0.0673 (12)0.0583 (10)−0.0050 (8)0.0008 (7)−0.0132 (9)
C70.0356 (8)0.0661 (11)0.0523 (9)−0.0023 (8)0.0070 (7)−0.0036 (8)
O10.0513 (8)0.0813 (10)0.0505 (7)0.0161 (7)0.0122 (6)−0.0023 (6)
O20.0521 (8)0.0788 (10)0.0674 (9)−0.0015 (7)0.0051 (6)−0.0267 (7)
O30.0537 (8)0.1141 (13)0.0890 (11)0.0104 (8)0.0058 (7)−0.0525 (10)
C80.0918 (18)0.0576 (14)0.127 (2)−0.0112 (12)−0.0065 (16)0.0126 (14)
C90.098 (2)0.161 (3)0.107 (2)0.013 (2)0.0542 (18)0.056 (2)
C100.0671 (14)0.0876 (16)0.0802 (15)0.0001 (12)−0.0078 (12)0.0154 (13)
C110.0545 (11)0.0673 (12)0.0678 (12)−0.0024 (10)0.0105 (9)0.0151 (10)
N10.0421 (8)0.0528 (9)0.0510 (8)−0.0009 (7)0.0108 (7)−0.0036 (7)

Geometric parameters (Å, °)

C1—O21.255 (2)C8—H8A0.9600
C1—O11.272 (2)C8—H8B0.9600
C1—C21.493 (2)C8—H8C0.9600
C2—C31.388 (2)C9—C111.527 (3)
C2—C71.394 (2)C9—H9A0.9600
C3—C41.386 (3)C9—H9B0.9600
C3—H3A0.9300C9—H9C0.9600
C4—C51.384 (3)C10—C111.520 (3)
C4—H4A0.9300C10—H10A0.9600
C5—O31.358 (2)C10—H10B0.9600
C5—C61.388 (3)C10—H10C0.9600
C6—C71.383 (3)C11—N11.515 (2)
C6—H6A0.9300N1—H10.92 (2)
C7—H7A0.9300N1—H20.87 (2)
O3—H3B0.8200N1—H30.94 (2)
C8—C111.527 (3)
O2—C1—O1121.95 (16)H8A—C8—H8C109.5
O2—C1—C2120.11 (16)H8B—C8—H8C109.5
O1—C1—C2117.93 (15)C11—C9—H9A109.5
C3—C2—C7117.80 (15)C11—C9—H9B109.5
C3—C2—C1120.66 (15)H9A—C9—H9B109.5
C7—C2—C1121.53 (15)C11—C9—H9C109.5
C4—C3—C2121.05 (17)H9A—C9—H9C109.5
C4—C3—H3A119.5H9B—C9—H9C109.5
C2—C3—H3A119.5C11—C10—H10A109.5
C5—C4—C3120.47 (18)C11—C10—H10B109.5
C5—C4—H4A119.8H10A—C10—H10B109.5
C3—C4—H4A119.8C11—C10—H10C109.5
O3—C5—C4117.57 (17)H10A—C10—H10C109.5
O3—C5—C6123.22 (17)H10B—C10—H10C109.5
C4—C5—C6119.21 (17)N1—C11—C10107.33 (16)
C7—C6—C5119.93 (16)N1—C11—C8106.78 (18)
C7—C6—H6A120.0C10—C11—C8110.92 (19)
C5—C6—H6A120.0N1—C11—C9107.08 (19)
C6—C7—C2121.50 (16)C10—C11—C9112.0 (2)
C6—C7—H7A119.3C8—C11—C9112.4 (2)
C2—C7—H7A119.3C11—N1—H1113.0 (13)
C5—O3—H3B109.5C11—N1—H2111.4 (13)
C11—C8—H8A109.5H1—N1—H2111.9 (19)
C11—C8—H8B109.5C11—N1—H3110.4 (12)
H8A—C8—H8B109.5H1—N1—H3106.4 (18)
C11—C8—H8C109.5H2—N1—H3103.3 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3B···O1i0.821.832.621 (2)163
N1—H1···O2ii0.92 (2)1.93 (2)2.835 (2)168.2 (18)
N1—H3···O20.94 (2)1.93 (2)2.842 (2)162.2 (18)
N1—H2···O1iii0.87 (2)1.92 (3)2.796 (2)174.7 (19)

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, −y+2, −z+1; (iii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5493).

References

  • Bruker (2003). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Scholz, J. & Gorls, H. (2002). Polyhedron, 21, 305–312.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography