Dopaminium perchlorate.

IN THE TITLE COMPOUND [SYSTEMATIC NAME: 2-(3,4-dihydroxy-phen-yl)ethanaminium perchlorate], C(8)H(12)NO(2) (+)·ClO(4) (-), the cations and anions are linked into three-dimensional structure via inter-molecular 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 = 253.64

Triclinic,

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[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 ▶); 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.

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

C8H12NO2+·ClO4–	Z = 2
Mr = 253.64	F000 = 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 = 2.4–31.6º
c = 8.9524 (4) Å	µ = 0.39 mm−1
α = 106.910 (1)º	T = 150 (2) K
β = 94.186 (1)º	Plate, colourless
γ = 101.206 (1)º	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)
Monochromator: graphite	Rint = 0.018
T = 150(2) K	θmax = 31.7º
φ and ω scans	θmin = 2.4º
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	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-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 reflections	Δρmax = 0.49 e Å−3
145 parameters	Δρmin = −0.45 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	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

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⋯O12iv	0.91	2.11	2.8002 (16)	132
N1—H1C⋯O2iv	0.91	2.39	3.0512 (16)	130

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .