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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2268.
Published online 2008 November 8. doi:  10.1107/S1600536808035666
PMCID: PMC2959864

Dopaminium perchlorate

Abstract

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—H(...)O hydrogen bonds.

Related literature

For related crystal structures, see: Bergin & Carlström (1968 [triangle]); Giesecke (1980 [triangle]). For details of the pharmacological properties of dopamine, see Salamone & Correa (2002 [triangle]).

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Object name is e-64-o2268-scheme1.jpg

Experimental

Crystal data

  • C8H12NO2 +·ClO4
  • M r = 253.64
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2268-efi1.jpg
  • a = 7.4925 (3) Å
  • b = 8.2254 (3) Å
  • c = 8.9524 (4) Å
  • α = 106.910 (1)°
  • β = 94.186 (1)°
  • γ = 101.206 (1)°
  • V = 512.85 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.39 mm−1
  • T = 150 (2) K
  • 0.30 × 0.15 × 0.06 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.893, T max = 0.977
  • 6199 measured reflections
  • 3146 independent reflections
  • 2858 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.105
  • S = 1.08
  • 3146 reflections
  • 145 parameters
  • H-atom parameters constrained
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [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 I, global. DOI: 10.1107/S1600536808035666/cv2470sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035666/cv2470Isup2.hkl

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

Acknowledgments

We are grateful to the Research Council of Sharif University of Technology and Loughborough University for their financial support.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

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

Figures

Fig. 1.
The molecular structure of (I) showing the atomic labels and displacement ellipsoids for non-H atoms drawn at the 50% probability level.

Crystal data

C8H12NO2+·ClO4Z = 2
Mr = 253.64F000 = 264
Triclinic, P1Dx = 1.642 Mg m3
Hall symbol: -P1Mo Kα radiation λ = 0.71073 Å
a = 7.4925 (3) ÅCell parameters from 3633 reflections
b = 8.2254 (3) Åθ = 2.4–31.6º
c = 8.9524 (4) ŵ = 0.39 mm1
α = 106.910 (1)ºT = 150 (2) K
β = 94.186 (1)ºPlate, colourless
γ = 101.206 (1)º0.30 × 0.15 × 0.06 mm
V = 512.85 (4) Å3

Data collection

Bruker APEXII CCD diffractometer3146 independent reflections
Radiation source: fine-focus sealed tube2858 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.018
T = 150(2) Kθmax = 31.7º
[var phi] and ω scansθmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −10→10
Tmin = 0.893, Tmax = 0.977k = −12→11
6199 measured reflectionsl = −12→12

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.105  w = 1/[σ2(Fo2) + (0.0559P)2 + 0.2163P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
3146 reflectionsΔρmax = 0.49 e Å3
145 parametersΔρmin = −0.45 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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
Cl10.78299 (4)0.71277 (4)0.38696 (3)0.01882 (9)
O110.78911 (17)0.88541 (14)0.49463 (13)0.0299 (2)
O120.61768 (16)0.59722 (16)0.39753 (16)0.0370 (3)
O130.7897 (2)0.7193 (2)0.23036 (14)0.0436 (3)
O140.93581 (16)0.65238 (18)0.43983 (14)0.0373 (3)
C10.28726 (18)0.78530 (16)1.02178 (15)0.0185 (2)
C20.45074 (18)0.77363 (16)0.95805 (14)0.0185 (2)
H20.54790.74641.01350.022*
C30.47193 (17)0.80155 (16)0.81453 (14)0.0177 (2)
O10.63545 (13)0.79282 (13)0.75554 (11)0.02136 (19)
C40.32907 (18)0.84083 (16)0.73205 (14)0.0188 (2)
O20.36279 (15)0.86353 (13)0.58877 (11)0.0240 (2)
C50.16751 (18)0.85522 (17)0.79484 (16)0.0212 (2)
H50.07130.88420.73970.025*
C60.14636 (18)0.82696 (17)0.93990 (16)0.0208 (2)
H60.03520.83620.98290.025*
C70.2661 (2)0.75345 (17)1.17802 (15)0.0215 (2)
H7A0.15220.78501.21470.026*
H7B0.37130.82791.25750.026*
C80.2576 (2)0.56300 (17)1.16162 (15)0.0222 (3)
H8A0.15260.48921.08150.027*
H8B0.37140.53201.12440.027*
N10.23650 (15)0.52615 (15)1.31419 (13)0.0200 (2)
H1A0.23170.41121.29990.030*
H1B0.13100.55281.34790.030*
H1C0.33400.59211.38750.030*
H2O0.29680.92730.56260.040*
H1O0.63560.82810.67480.040*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.01669 (14)0.02486 (16)0.01828 (15)0.00806 (11)0.00411 (10)0.00922 (11)
O110.0394 (6)0.0222 (5)0.0305 (5)0.0104 (4)0.0048 (4)0.0096 (4)
O120.0253 (5)0.0348 (6)0.0453 (7)−0.0014 (5)0.0097 (5)0.0083 (5)
O130.0561 (8)0.0597 (8)0.0200 (5)0.0123 (7)0.0065 (5)0.0201 (5)
O140.0303 (6)0.0537 (7)0.0342 (6)0.0287 (5)0.0029 (4)0.0113 (5)
C10.0249 (6)0.0149 (5)0.0170 (5)0.0059 (4)0.0049 (4)0.0058 (4)
C20.0241 (6)0.0173 (5)0.0166 (5)0.0079 (4)0.0028 (4)0.0070 (4)
C30.0224 (5)0.0153 (5)0.0168 (5)0.0066 (4)0.0046 (4)0.0052 (4)
O10.0248 (5)0.0250 (5)0.0206 (4)0.0118 (4)0.0087 (3)0.0114 (4)
C40.0256 (6)0.0168 (5)0.0150 (5)0.0061 (4)0.0016 (4)0.0059 (4)
O20.0327 (5)0.0276 (5)0.0174 (4)0.0132 (4)0.0047 (4)0.0116 (4)
C50.0229 (6)0.0209 (5)0.0213 (6)0.0070 (5)0.0005 (4)0.0079 (5)
C60.0215 (6)0.0199 (5)0.0229 (6)0.0063 (4)0.0052 (5)0.0079 (5)
C70.0301 (6)0.0193 (5)0.0194 (6)0.0091 (5)0.0094 (5)0.0085 (4)
C80.0331 (7)0.0189 (5)0.0168 (5)0.0077 (5)0.0048 (5)0.0077 (4)
N10.0215 (5)0.0229 (5)0.0208 (5)0.0085 (4)0.0064 (4)0.0118 (4)

Geometric parameters (Å, °)

Cl1—O131.4225 (11)O2—H2O0.8540
Cl1—O121.4347 (11)C5—C61.3989 (18)
Cl1—O141.4355 (11)C5—H50.9500
Cl1—O111.4559 (11)C6—H60.9500
C1—C61.3939 (18)C7—C81.5185 (18)
C1—C21.3968 (18)C7—H7A0.9900
C1—C71.5099 (17)C7—H7B0.9900
C2—C31.3842 (16)C8—N11.4954 (16)
C2—H20.9500C8—H8A0.9900
C3—O11.3753 (15)C8—H8B0.9900
C3—C41.3975 (18)N1—H1A0.9100
O1—H1O0.8537N1—H1B0.9100
C4—C51.3826 (19)N1—H1C0.9100
C4—O21.3828 (15)
O13—Cl1—O12111.25 (8)C6—C5—H5120.2
O13—Cl1—O14111.08 (8)C1—C6—C5120.47 (12)
O12—Cl1—O14107.81 (8)C1—C6—H6119.8
O13—Cl1—O11110.40 (8)C5—C6—H6119.8
O12—Cl1—O11108.15 (7)C1—C7—C8110.27 (10)
O14—Cl1—O11108.02 (7)C1—C7—H7A109.6
C6—C1—C2119.24 (11)C8—C7—H7A109.6
C6—C1—C7121.09 (11)C1—C7—H7B109.6
C2—C1—C7119.67 (11)C8—C7—H7B109.6
C3—C2—C1120.37 (12)H7A—C7—H7B108.1
C3—C2—H2119.8N1—C8—C7111.89 (10)
C1—C2—H2119.8N1—C8—H8A109.2
O1—C3—C2119.37 (11)C7—C8—H8A109.2
O1—C3—C4120.57 (11)N1—C8—H8B109.2
C2—C3—C4120.06 (11)C7—C8—H8B109.2
C3—O1—H1O109.3H8A—C8—H8B107.9
C5—C4—O2124.27 (11)C8—N1—H1A109.5
C5—C4—C3120.16 (11)C8—N1—H1B109.5
O2—C4—C3115.56 (11)H1A—N1—H1B109.5
C4—O2—H2O111.4C8—N1—H1C109.5
C4—C5—C6119.69 (12)H1A—N1—H1C109.5
C4—C5—H5120.2H1B—N1—H1C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O···O110.852.162.9065 (14)146
O2—H2O···O11i0.851.962.7936 (15)164
N1—H1A···O1ii0.912.072.8822 (14)148
N1—H1B···O14iii0.911.932.8317 (16)169
N1—H1C···O12iv0.912.112.8002 (16)132
N1—H1C···O2iv0.912.393.0512 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2470).

References

  • Bergin, R. & Carlström, D. (1968). Acta Cryst. B24, 1506–1510. [PubMed]
  • 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. [PubMed]
  • Sheldrick, G. M. (2003). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • 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