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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2341.
Published online 2009 September 5. doi:  10.1107/S1600536809034540
PMCID: PMC2970201

(4-Hydroxy­phen­yl)methanaminium 2-(4-sulfanylphen­yl)acetate

Abstract

In the title mol­ecular salt, C7H10NO+·C8H7O2S, the crystal structure is stabilized by inter­molecular N—H(...)O, O—H(...)N and C—H(...)O hydrogen bonds.

Related literature

For related mol­ecular salts, see: Xia et al. (2003 [triangle]); He et al. (2008 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-o2341-scheme1.jpg

Experimental

Crystal data

  • C7H10NO+·C8H7O2S
  • M r = 291.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2341-efi1.jpg
  • a = 6.545 (5) Å
  • b = 14.792 (12) Å
  • c = 14.868 (11) Å
  • β = 104.78 (4)°
  • V = 1391.8 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 293 K
  • 0.32 × 0.28 × 0.26 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.927, T max = 0.940
  • 6838 measured reflections
  • 2447 independent reflections
  • 1895 reflections with I > 2σ(I)
  • R int = 0.061
  • ??? standard reflections every ??? reflections intensity decay: ???%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.182
  • S = 1.11
  • 2447 reflections
  • 191 parameters
  • 22 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); 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/S1600536809034540/hb5068sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034540/hb5068Isup2.hkl

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

Acknowledgments

This project was supported by the Education Commission of Hubei Province (D20091703) and the Natural Science Foundation of Hubei Province (2008CDB038).

supplementary crystallographic information

Comment

There has been much research interest in the intermolecular interactions between carboxylic acid and amine. (Xia et al., 2003; He et al., 2008). The title compound (I) is presented in Fig.1, all bond lengths are within normal ranges (Allen et al., 1987) (Table 1). The carboxylate cation and aminium anion are linked via N—H···O, O—H···N and C—H···O intermolecular hydrogen bonds (Table 2) into three network along the a axis. (Fig. 2).

Experimental

A mixture of 2-(4-mercaptophenyl)acetic acid (336 mg, 2 mmol), and 4-(aminomethyl)phenol (246 mg, 2 mmol) was stirred in methanol (10 ml) for 1 h. After keeping the solution in air for 3 d, colourless blocks of (I) were formed.

Refinement

All the H atoms, except for H1A, H1B and H1C attached to N1, H1D attached to S1, were placed in idealized positions (C—H = 0.93–0.97 Å, O—H = 0.82 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(O). Atoms H1A, H1B and H1C and H1D were located from a difference map and their positions were freely refined.

Figures

Fig. 1.
The molecular structure of (I) showing 35% probability displacement ellipsoids.
Fig. 2.
The packing of (I), showing intermolecular hydrogen bonds (dashed lines) along the a axis.

Crystal data

C7H10NO+·C8H7O2SF(000) = 616
Mr = 291.37Dx = 1.391 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1267 reflections
a = 6.545 (5) Åθ = 2.4–24.4°
b = 14.792 (12) ŵ = 0.24 mm1
c = 14.868 (11) ÅT = 293 K
β = 104.78 (4)°Block, colourless
V = 1391.8 (19) Å30.32 × 0.28 × 0.26 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer2447 independent reflections
Radiation source: fine-focus sealed tube1895 reflections with I > 2σ(I)
graphiteRint = 0.061
ω/2θ scansθmax = 25.0°, θmin = 2.0°
Absorption correction: ψ scan (North et al., 1968)h = −7→7
Tmin = 0.927, Tmax = 0.940k = −17→17
6838 measured reflectionsl = −14→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H atoms treated by a mixture of independent and constrained refinement
S = 1.11w = 1/[σ2(Fo2) + (0.1018P)2 + 0.3741P] where P = (Fo2 + 2Fc2)/3
2447 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.38 e Å3
22 restraintsΔρmin = −0.45 e Å3

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
S10.76277 (18)0.46123 (6)0.14786 (7)0.0712 (4)
O11.3152 (3)0.89080 (12)−0.02444 (14)0.0493 (5)
O21.0949 (3)0.85420 (13)0.06100 (13)0.0495 (5)
C10.9143 (5)0.53974 (18)0.1055 (2)0.0491 (7)
C20.8159 (5)0.59649 (19)0.0354 (2)0.0511 (7)
H20.67110.59230.00960.061*
C30.9338 (5)0.65976 (19)0.0038 (2)0.0482 (7)
H3A0.86690.6986−0.04380.058*
C41.1530 (5)0.66758 (18)0.04140 (18)0.0425 (6)
C51.2476 (5)0.60815 (19)0.1105 (2)0.0490 (7)
H51.39310.61050.13540.059*
C61.1284 (6)0.54461 (19)0.1435 (2)0.0542 (8)
H61.19350.50550.19120.065*
C71.2790 (5)0.73591 (19)0.0050 (2)0.0501 (7)
H7A1.26290.7240−0.06060.060*
H7B1.42690.72730.03640.060*
C81.2232 (4)0.83435 (18)0.01580 (18)0.0385 (6)
O30.6854 (4)0.88722 (13)0.17658 (14)0.0603 (6)
H3B0.70230.87650.12480.090*
N10.7229 (4)0.56517 (17)0.46681 (18)0.0451 (6)
C90.6981 (5)0.8088 (2)0.22552 (19)0.051
C100.5344 (5)0.7868 (2)0.2620 (2)0.0560 (8)
H100.41830.82490.25470.067*
C110.5448 (5)0.7067 (2)0.3100 (2)0.0494 (7)
H110.43380.68970.33480.059*
C120.7227 (4)0.65084 (18)0.32159 (17)0.0423 (6)
C130.8840 (5)0.6771 (2)0.28458 (19)0.0479 (7)
H131.00240.64020.29270.058*
C140.8762 (5)0.7568 (2)0.23553 (19)0.0525 (7)
H140.98640.77440.21040.063*
C150.7290 (6)0.5601 (2)0.3675 (2)0.0561 (8)
H15A0.60970.52450.33340.067*
H15B0.85700.52900.36370.067*
H1B0.719 (5)0.5117 (15)0.4910 (19)0.054 (9)*
H1C0.851 (5)0.585 (4)0.496 (3)0.13 (2)*
H1A0.616 (4)0.594 (2)0.473 (3)0.080 (13)*
H1D0.719 (10)0.455 (4)0.229 (2)0.18 (2)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.1102 (8)0.0416 (5)0.0790 (6)−0.0173 (5)0.0555 (6)−0.0050 (4)
O10.0561 (12)0.0336 (11)0.0632 (12)−0.0046 (9)0.0246 (10)−0.0015 (9)
O20.0546 (12)0.0400 (11)0.0605 (12)0.0055 (9)0.0269 (10)−0.0029 (9)
C10.074 (2)0.0309 (15)0.0500 (16)−0.0040 (13)0.0295 (15)−0.0075 (12)
C20.0570 (18)0.0426 (17)0.0537 (16)−0.0055 (13)0.0144 (14)−0.0068 (13)
C30.0542 (18)0.0389 (16)0.0494 (16)0.0002 (13)0.0092 (13)0.0027 (12)
C40.0561 (17)0.0292 (14)0.0457 (14)−0.0001 (12)0.0192 (12)−0.0055 (11)
C50.0552 (18)0.0382 (15)0.0513 (16)0.0052 (13)0.0097 (13)−0.0038 (12)
C60.079 (2)0.0376 (17)0.0454 (15)0.0083 (15)0.0148 (15)0.0061 (12)
C70.0582 (18)0.0348 (15)0.0645 (18)0.0005 (13)0.0290 (14)−0.0042 (12)
C80.0390 (14)0.0337 (14)0.0422 (13)−0.0005 (11)0.0094 (11)−0.0037 (11)
O30.0993 (17)0.0344 (11)0.0446 (11)0.0015 (11)0.0138 (11)0.0139 (8)
N10.0511 (15)0.0340 (13)0.0545 (14)−0.0007 (12)0.0211 (12)0.0041 (11)
C90.0710.0390.041−0.0020.0110.000
C100.065 (2)0.0479 (19)0.0520 (16)0.0133 (15)0.0091 (14)−0.0038 (14)
C110.0512 (17)0.0486 (17)0.0516 (16)−0.0018 (14)0.0192 (13)−0.0057 (13)
C120.0546 (16)0.0352 (14)0.0374 (13)−0.0009 (12)0.0124 (12)−0.0066 (11)
C130.0521 (17)0.0464 (17)0.0472 (15)0.0062 (13)0.0163 (13)−0.0046 (12)
C140.0578 (18)0.0570 (19)0.0468 (15)−0.0053 (15)0.0208 (13)−0.0036 (13)
C150.082 (2)0.0366 (16)0.0501 (16)−0.0017 (15)0.0187 (15)−0.0030 (12)

Geometric parameters (Å, °)

S1—C11.746 (3)O3—H3B0.8200
S1—H1D1.31 (2)N1—C151.490 (4)
O1—C81.266 (3)N1—H1B0.872 (18)
O2—C81.237 (3)N1—H1C0.89 (2)
C1—C21.365 (4)N1—H1A0.845 (19)
C1—C61.373 (5)C9—C101.358 (5)
C2—C31.370 (4)C9—C141.373 (5)
C2—H20.9300C10—C111.376 (4)
C3—C41.405 (4)C10—H100.9300
C3—H3A0.9300C11—C121.402 (4)
C4—C51.374 (4)C11—H110.9300
C4—C71.491 (4)C12—C131.366 (4)
C5—C61.389 (4)C12—C151.501 (4)
C5—H50.9300C13—C141.380 (4)
C6—H60.9300C13—H130.9300
C7—C81.520 (4)C14—H140.9300
C7—H7A0.9700C15—H15A0.9700
C7—H7B0.9700C15—H15B0.9700
O3—C91.361 (4)
C1—S1—H1D131 (3)C15—N1—H1C104 (4)
C2—C1—C6121.0 (3)H1B—N1—H1C102 (4)
C2—C1—S1118.9 (3)C15—N1—H1A112 (3)
C6—C1—S1120.0 (2)H1B—N1—H1A107 (3)
C1—C2—C3119.0 (3)H1C—N1—H1A119 (5)
C1—C2—H2120.5C10—C9—O3118.1 (3)
C3—C2—H2120.5C10—C9—C14123.9 (3)
C2—C3—C4121.8 (3)O3—C9—C14118.0 (3)
C2—C3—H3A119.1C9—C10—C11118.3 (3)
C4—C3—H3A119.1C9—C10—H10120.9
C5—C4—C3117.7 (3)C11—C10—H10120.9
C5—C4—C7121.3 (3)C10—C11—C12120.1 (3)
C3—C4—C7121.0 (3)C10—C11—H11120.0
C4—C5—C6120.7 (3)C12—C11—H11120.0
C4—C5—H5119.6C13—C12—C11119.1 (3)
C6—C5—H5119.6C13—C12—C15120.2 (3)
C1—C6—C5119.8 (3)C11—C12—C15120.6 (3)
C1—C6—H6120.1C12—C13—C14121.9 (3)
C5—C6—H6120.1C12—C13—H13119.1
C4—C7—C8116.2 (2)C14—C13—H13119.1
C4—C7—H7A108.2C9—C14—C13116.8 (3)
C8—C7—H7A108.2C9—C14—H14121.6
C4—C7—H7B108.2C13—C14—H14121.6
C8—C7—H7B108.2N1—C15—C12113.7 (2)
H7A—C7—H7B107.4N1—C15—H15A108.8
O2—C8—O1124.8 (2)C12—C15—H15A108.8
O2—C8—C7120.0 (2)N1—C15—H15B108.8
O1—C8—C7115.2 (2)C12—C15—H15B108.8
C9—O3—H3B109.4H15A—C15—H15B107.7
C15—N1—H1B112 (2)
C6—C1—C2—C3−0.8 (4)C4—C7—C8—O1−172.5 (2)
S1—C1—C2—C3178.3 (2)O3—C9—C10—C11178.8 (2)
C1—C2—C3—C40.2 (4)C14—C9—C10—C11−1.6 (5)
C2—C3—C4—C51.2 (4)C9—C10—C11—C121.0 (4)
C2—C3—C4—C7179.0 (3)C10—C11—C12—C130.0 (4)
C3—C4—C5—C6−1.9 (4)C10—C11—C12—C15−175.3 (3)
C7—C4—C5—C6−179.8 (3)C11—C12—C13—C14−0.5 (4)
C2—C1—C6—C50.0 (4)C15—C12—C13—C14174.8 (3)
S1—C1—C6—C5−179.0 (2)C10—C9—C14—C131.1 (4)
C4—C5—C6—C11.3 (4)O3—C9—C14—C13−179.3 (2)
C5—C4—C7—C8−119.7 (3)C12—C13—C14—C90.0 (4)
C3—C4—C7—C862.5 (4)C13—C12—C15—N1120.6 (3)
C4—C7—C8—O27.1 (4)C11—C12—C15—N1−64.2 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.85 (2)1.99 (2)2.782 (4)156 (4)
N1—H1C···O2ii0.89 (2)1.87 (2)2.752 (4)169 (5)
N1—H1B···O1iii0.87 (2)1.89 (2)2.749 (4)171 (3)
O3—H3B···N1iv0.822.543.267 (4)149
C6—H6···O3iii0.932.603.521 (4)171

Symmetry codes: (i) x−1, −y+3/2, z+1/2; (ii) x, −y+3/2, z+1/2; (iii) −x+2, y−1/2, −z+1/2; (iv) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5068).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • He, Q., Jennings, M. C., Rohani, S., Zhu, J. & Gomaa, H. (2008). Acta Cryst. E64, o559. [PMC free article] [PubMed]
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xia, J., Wang, X.-J., Sun, X.-J., Zhu, H.-L. & Wang, D.-Q. (2003). Z. Kristallogr. New Cryst. Struct.218, 247–248.

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