Acta Cryst. (2008). E64, o2268 [ doi:10.1107/S1600536808035666 ]
In the title compound [systematic name: 2-(3,4-dihydroxyphenyl)ethanaminium perchlorate], C8H12NO2+·ClO4-, the cations and anions are linked into three-dimensional structure via intermolecular N-H
O and O-HO hydrogen bonds.
The title compound was prepared by dissolving dopamine hydrochloride (2 mmol, 379 mg) and NaClO4.H2O (2 mmol, 280 mg) in water/HClO4 (1mM, 10 ml). The mixture was stirred for about 2 h at room temperature. This solution yielded colourless crystals of (I) after 10 d.
All H atoms atoms were placed in calculated positions and refined using the riding model approximation, with C—H = 0.95–1.0 Å, O—H = 0.85 Å, N—H = 0.91 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(N). The isotropic displacement parameter of the hydroxy H atoms were fixed to 0.04 Å2
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./cv2470fig1thm.gif)
| Fig. 1. The molecular structure of (I) showing the atomic labels and displacement ellipsoids for non-H atoms drawn at the 50% probability level. |
| C8H12NO2+·ClO4− | Z = 2 |
| Mr = 253.64 | F(000) = 264 |
| Triclinic, P1 | Dx = 1.642 Mg m−3 |
| Hall symbol: -P1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.4925 (3) Å | Cell parameters from 3633 reflections |
| b = 8.2254 (3) Å | θ = 2.4–31.6° |
| c = 8.9524 (4) Å | µ = 0.39 mm−1 |
| α = 106.910 (1)° | T = 150 K |
| β = 94.186 (1)° | Plate, colourless |
| γ = 101.206 (1)° | 0.30 × 0.15 × 0.06 mm |
| V = 512.85 (4) Å3 |
| Bruker APEXII CCD diffractometer | 3146 independent reflections |
| Radiation source: fine-focus sealed tube | 2858 reflections with I > 2σ(I) |
| graphite | Rint = 0.018 |
| φ and ω scans | θmax = 31.7°, θmin = 2.4° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −10→10 |
| Tmin = 0.893, Tmax = 0.977 | k = −12→11 |
| 6199 measured reflections | l = −12→12 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.105 | H-atom parameters constrained |
| S = 1.09 | w = 1/[σ2(Fo2) + (0.0559P)2 + 0.2163P] where P = (Fo2 + 2Fc2)/3 |
| 3146 reflections | (Δ/σ)max < 0.001 |
| 145 parameters | Δρmax = 0.49 e Å−3 |
| 0 restraints | Δρmin = −0.45 e Å−3 |
| C8H12NO2+·ClO4− | γ = 101.206 (1)° |
| Mr = 253.64 | V = 512.85 (4) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.4925 (3) Å | Mo Kα radiation |
| b = 8.2254 (3) Å | µ = 0.39 mm−1 |
| c = 8.9524 (4) Å | T = 150 K |
| α = 106.910 (1)° | 0.30 × 0.15 × 0.06 mm |
| β = 94.186 (1)° |
| Bruker APEXII CCD diffractometer | 3146 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 2858 reflections with I > 2σ(I) |
| Tmin = 0.893, Tmax = 0.977 | Rint = 0.018 |
| 6199 measured reflections | θmax = 31.7° |
| R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
| wR(F2) = 0.105 | Δρmax = 0.49 e Å−3 |
| S = 1.09 | Δρmin = −0.45 e Å−3 |
| 3146 reflections | Absolute structure: ? |
| 145 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.78299 (4) | 0.71277 (4) | 0.38696 (3) | 0.01882 (9) | |
| O11 | 0.78911 (17) | 0.88541 (14) | 0.49463 (13) | 0.0299 (2) | |
| O12 | 0.61768 (16) | 0.59722 (16) | 0.39753 (16) | 0.0370 (3) | |
| O13 | 0.7897 (2) | 0.7193 (2) | 0.23036 (14) | 0.0436 (3) | |
| O14 | 0.93581 (16) | 0.65238 (18) | 0.43983 (14) | 0.0373 (3) | |
| C1 | 0.28726 (18) | 0.78530 (16) | 1.02178 (15) | 0.0185 (2) | |
| C2 | 0.45074 (18) | 0.77363 (16) | 0.95805 (14) | 0.0185 (2) | |
| H2 | 0.5479 | 0.7464 | 1.0135 | 0.022* | |
| C3 | 0.47193 (17) | 0.80155 (16) | 0.81453 (14) | 0.0177 (2) | |
| O1 | 0.63545 (13) | 0.79282 (13) | 0.75554 (11) | 0.02136 (19) | |
| C4 | 0.32907 (18) | 0.84083 (16) | 0.73205 (14) | 0.0188 (2) | |
| O2 | 0.36279 (15) | 0.86353 (13) | 0.58877 (11) | 0.0240 (2) | |
| C5 | 0.16751 (18) | 0.85522 (17) | 0.79484 (16) | 0.0212 (2) | |
| H5 | 0.0713 | 0.8842 | 0.7397 | 0.025* | |
| C6 | 0.14636 (18) | 0.82696 (17) | 0.93990 (16) | 0.0208 (2) | |
| H6 | 0.0352 | 0.8362 | 0.9829 | 0.025* | |
| C7 | 0.2661 (2) | 0.75345 (17) | 1.17802 (15) | 0.0215 (2) | |
| H7A | 0.1522 | 0.7850 | 1.2147 | 0.026* | |
| H7B | 0.3713 | 0.8279 | 1.2575 | 0.026* | |
| C8 | 0.2576 (2) | 0.56300 (17) | 1.16162 (15) | 0.0222 (3) | |
| H8A | 0.1526 | 0.4892 | 1.0815 | 0.027* | |
| H8B | 0.3714 | 0.5320 | 1.1244 | 0.027* | |
| N1 | 0.23650 (15) | 0.52615 (15) | 1.31419 (13) | 0.0200 (2) | |
| H1A | 0.2317 | 0.4112 | 1.2999 | 0.030* | |
| H1B | 0.1310 | 0.5528 | 1.3479 | 0.030* | |
| H1C | 0.3340 | 0.5921 | 1.3875 | 0.030* | |
| H2O | 0.2968 | 0.9273 | 0.5626 | 0.040* | |
| H1O | 0.6356 | 0.8281 | 0.6748 | 0.040* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.01669 (14) | 0.02486 (16) | 0.01828 (15) | 0.00806 (11) | 0.00411 (10) | 0.00922 (11) |
| O11 | 0.0394 (6) | 0.0222 (5) | 0.0305 (5) | 0.0104 (4) | 0.0048 (4) | 0.0096 (4) |
| O12 | 0.0253 (5) | 0.0348 (6) | 0.0453 (7) | −0.0014 (5) | 0.0097 (5) | 0.0083 (5) |
| O13 | 0.0561 (8) | 0.0597 (8) | 0.0200 (5) | 0.0123 (7) | 0.0065 (5) | 0.0201 (5) |
| O14 | 0.0303 (6) | 0.0537 (7) | 0.0342 (6) | 0.0287 (5) | 0.0029 (4) | 0.0113 (5) |
| C1 | 0.0249 (6) | 0.0149 (5) | 0.0170 (5) | 0.0059 (4) | 0.0049 (4) | 0.0058 (4) |
| C2 | 0.0241 (6) | 0.0173 (5) | 0.0166 (5) | 0.0079 (4) | 0.0028 (4) | 0.0070 (4) |
| C3 | 0.0224 (5) | 0.0153 (5) | 0.0168 (5) | 0.0066 (4) | 0.0046 (4) | 0.0052 (4) |
| O1 | 0.0248 (5) | 0.0250 (5) | 0.0206 (4) | 0.0118 (4) | 0.0087 (3) | 0.0114 (4) |
| C4 | 0.0256 (6) | 0.0168 (5) | 0.0150 (5) | 0.0061 (4) | 0.0016 (4) | 0.0059 (4) |
| O2 | 0.0327 (5) | 0.0276 (5) | 0.0174 (4) | 0.0132 (4) | 0.0047 (4) | 0.0116 (4) |
| C5 | 0.0229 (6) | 0.0209 (5) | 0.0213 (6) | 0.0070 (5) | 0.0005 (4) | 0.0079 (5) |
| C6 | 0.0215 (6) | 0.0199 (5) | 0.0229 (6) | 0.0063 (4) | 0.0052 (5) | 0.0079 (5) |
| C7 | 0.0301 (6) | 0.0193 (5) | 0.0194 (6) | 0.0091 (5) | 0.0094 (5) | 0.0085 (4) |
| C8 | 0.0331 (7) | 0.0189 (5) | 0.0168 (5) | 0.0077 (5) | 0.0048 (5) | 0.0077 (4) |
| N1 | 0.0215 (5) | 0.0229 (5) | 0.0208 (5) | 0.0085 (4) | 0.0064 (4) | 0.0118 (4) |
| Cl1—O13 | 1.4225 (11) | O2—H2O | 0.8540 |
| Cl1—O12 | 1.4347 (11) | C5—C6 | 1.3989 (18) |
| Cl1—O14 | 1.4355 (11) | C5—H5 | 0.9500 |
| Cl1—O11 | 1.4559 (11) | C6—H6 | 0.9500 |
| C1—C6 | 1.3939 (18) | C7—C8 | 1.5185 (18) |
| C1—C2 | 1.3968 (18) | C7—H7A | 0.9900 |
| C1—C7 | 1.5099 (17) | C7—H7B | 0.9900 |
| C2—C3 | 1.3842 (16) | C8—N1 | 1.4954 (16) |
| C2—H2 | 0.9500 | C8—H8A | 0.9900 |
| C3—O1 | 1.3753 (15) | C8—H8B | 0.9900 |
| C3—C4 | 1.3975 (18) | N1—H1A | 0.9100 |
| O1—H1O | 0.8537 | N1—H1B | 0.9100 |
| C4—C5 | 1.3826 (19) | N1—H1C | 0.9100 |
| C4—O2 | 1.3828 (15) | ||
| O13—Cl1—O12 | 111.25 (8) | C6—C5—H5 | 120.2 |
| O13—Cl1—O14 | 111.08 (8) | C1—C6—C5 | 120.47 (12) |
| O12—Cl1—O14 | 107.81 (8) | C1—C6—H6 | 119.8 |
| O13—Cl1—O11 | 110.40 (8) | C5—C6—H6 | 119.8 |
| O12—Cl1—O11 | 108.15 (7) | C1—C7—C8 | 110.27 (10) |
| O14—Cl1—O11 | 108.02 (7) | C1—C7—H7A | 109.6 |
| C6—C1—C2 | 119.24 (11) | C8—C7—H7A | 109.6 |
| C6—C1—C7 | 121.09 (11) | C1—C7—H7B | 109.6 |
| C2—C1—C7 | 119.67 (11) | C8—C7—H7B | 109.6 |
| C3—C2—C1 | 120.37 (12) | H7A—C7—H7B | 108.1 |
| C3—C2—H2 | 119.8 | N1—C8—C7 | 111.89 (10) |
| C1—C2—H2 | 119.8 | N1—C8—H8A | 109.2 |
| O1—C3—C2 | 119.37 (11) | C7—C8—H8A | 109.2 |
| O1—C3—C4 | 120.57 (11) | N1—C8—H8B | 109.2 |
| C2—C3—C4 | 120.06 (11) | C7—C8—H8B | 109.2 |
| C3—O1—H1O | 109.3 | H8A—C8—H8B | 107.9 |
| C5—C4—O2 | 124.27 (11) | C8—N1—H1A | 109.5 |
| C5—C4—C3 | 120.16 (11) | C8—N1—H1B | 109.5 |
| O2—C4—C3 | 115.56 (11) | H1A—N1—H1B | 109.5 |
| C4—O2—H2O | 111.4 | C8—N1—H1C | 109.5 |
| C4—C5—C6 | 119.69 (12) | H1A—N1—H1C | 109.5 |
| C4—C5—H5 | 120.2 | H1B—N1—H1C | 109.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1O···O11 | 0.85 | 2.16 | 2.9065 (14) | 146 |
| O2—H2O···O11i | 0.85 | 1.96 | 2.7936 (15) | 164 |
| N1—H1A···O1ii | 0.91 | 2.07 | 2.8822 (14) | 148 |
| N1—H1B···O14iii | 0.91 | 1.93 | 2.8317 (16) | 169 |
| N1—H1C···O12iv | 0.91 | 2.11 | 2.8002 (16) | 132 |
| N1—H1C···O2iv | 0.91 | 2.39 | 3.0512 (16) | 130 |
| Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x−1, y, z+1; (iv) x, y, z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1O···O11 | 0.85 | 2.16 | 2.9065 (14) | 146 |
| O2—H2O···O11i | 0.85 | 1.96 | 2.7936 (15) | 164 |
| N1—H1A···O1ii | 0.91 | 2.07 | 2.8822 (14) | 148 |
| N1—H1B···O14iii | 0.91 | 1.93 | 2.8317 (16) | 169 |
| N1—H1C···O12iv | 0.91 | 2.11 | 2.8002 (16) | 132 |
| N1—H1C···O2iv | 0.91 | 2.39 | 3.0512 (16) | 130 |
| Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x−1, y, z+1; (iv) x, y, z+1. |
We are grateful to the Research Council of Sharif University of Technology and Loughborough University for their financial support.
Bergin, R. & Carlström, D. (1968). Acta Cryst. B24, 1506–1510.
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Giesecke, J. (1980). Acta Cryst. B36, 178–181.
Salamone, J. D. & Correa, M. (2002). Behav. Brain Res. 137, 3–25.
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Many neuro transmitters have been discovered over the past century, such as serotonin, norepinephrine, substance P and dopamine. Dopamine is synthesized in the cenral brain from tyrosine. Dopamine has been considered as an important signal transmitter between the neurons and muscles (Salamone & Correa, 2002). Herewith we present the crystal structure of the title compound (I).
In (I) (Fig. 1), all bond lengths and angles are normal (Giesecke, 1980, Bergin & Carlström, 1968). The torsion angles C6—C1—C7—C8 and C1—C7—C8—N1 are 111.9 (1)° and 179.9 (6)°, respectively, showing that C1—C7—C8—N1 chain is almost fully extended, forming a plane that is nearly orthogonal to the plane of the ring. The crystal packing is stabilized by an extensive network of O—H···O and N—H···O hydrogen bonds (Table 1).