Dopaminium perchlorate

Boghaei, D.M.; Baniyaghoob, S.; Najafpour, M.M.; McKee, V.

doi:10.1107/S1600536808035666

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2268

doi:10.1107/S1600536808035666

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Dopaminium perchlorate

Davar M. Boghaei,^a ^* Sahar Baniyaghoob,^a Mohammad Mahdi Najafpour ^a and Vickie McKee ^b

^aDepartment of Chemistry, Sharif University of Technology, PO Box 11155-8639, Tehran, Iran, and ^bDepartment of Chemistry, Loughborough University, Leicestershire LE11 3TU, England
^*Correspondence e-mail: dboghaei@sharif.edu

(Received 20 October 2008; accepted 30 October 2008; online 8 November 2008)

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 ); Giesecke (1980 ). For details of the pharmacological properties of dopamine, see Salamone & Correa (2002 ).

Experimental

Crystal data

C₈H₁₂NO₂⁺·ClO₄⁻
M_r = 253.64
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.105
S = 1.08
3146 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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⋯O12^iv	0.91	2.11	2.8002 (16)	132
N1—H1C⋯O2^iv	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.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035666/cv2470sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

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).

Figures top

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

2-(3,4-dihydroxyphenyl)ethanaminium perchlorate top

Crystal data top

C₈H₁₂NO₂⁺·ClO₄⁻	Z = 2
M_r = 253.64	F(000) = 264
Triclinic, P1	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	3146 independent reflections
Radiation source: fine-focus sealed tube	2858 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 31.7°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→10
T_min = 0.893, T_max = 0.977	k = −12→11
6199 measured reflections	l = −12→12

Refinement top

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(F_o²) + (0.0559P)² + 0.2163P] where P = (F_o² + 2F_c²)/3
3146 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₈H₁₂NO₂⁺·ClO₄⁻	γ = 101.206 (1)°
M_r = 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)°

Data collection top

Bruker APEXII CCD diffractometer	3146 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2858 reflections with I > 2σ(I)
T_min = 0.893, T_max = 0.977	R_int = 0.018
6199 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.09	Δρ_max = 0.49 e Å⁻³
3146 reflections	Δρ_min = −0.45 e Å⁻³
145 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···O12^iv	0.91	2.11	2.8002 (16)	132
N1—H1C···O2^iv	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.

Experimental details

Crystal data
Chemical formula	C₈H₁₂NO₂⁺·ClO₄⁻
M_r	253.64
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	7.4925 (3), 8.2254 (3), 8.9524 (4)
α, β, γ (°)	106.910 (1), 94.186 (1), 101.206 (1)
V (Å³)	512.85 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.30 × 0.15 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.893, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	6199, 3146, 2858
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.740

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.105, 1.09
No. of reflections	3146
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.45

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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···O12^iv	0.91	2.11	2.8002 (16)	132
N1—H1C···O2^iv	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.

Acknowledgements

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

References

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Giesecke, J. (1980). Acta Cryst. B36, 178–181. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
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Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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