Dopaminium nitrate.

THE ASYMMETRIC UNIT OF THE TITLE SALT [SYSTEMATIC NAME: 2-(3,4-di-hydroxy-phen-yl)ethanaminium nitrate], C8H12NO2 (+)·NO3 (-), contains two independent cations and two independent nitrate anions. The crystal structure consists of discrete nitrate ions stacked in layers parallel to (010). These layers are linked via the dopaminium cations by O-H⋯O, N-H⋯O and weak C-H⋯O hydrogen bonds, forming a three-dimensional supra-molecular network.

Related literature

For pharmacological properties of dopamine, see: Jones et al. (1999 ▶); Salamone & Correa (2002 ▶). For related structures, see: Gatfaoui et al. (2013 ▶, 2014a ▶, 2014b ▶); Marouani et al. (2012 ▶); Kefi et al. (2013 ▶). For the perchlorate salt of the title cation, see: Boghaei et al. (2008 ▶). For background to hydrogen bonding and aromatic π–π stacking inter­actions, see: Brown (1976 ▶); Blessing (1986 ▶); Janiak (2000 ▶).

Experimental

Crystal data

C8H12NO2 +·NO3 −

M = 216.20

Triclinic,

a = 8.3066 (4) Å

b = 10.4856 (5) Å

c = 11.2303 (7) Å

α = 79.623 (2)°

β = 89.868 (2)°

γ = 82.357 (2)°

V = 953.37 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 150 K

0.56 × 0.44 × 0.27 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.870, T max = 0.966

10787 measured reflections

4339 independent reflections

3583 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 1.05

4339 reflections

312 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and CRYSCAL (T. Roisnel, local program).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814008265/bg2526sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008265/bg2526Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008265/bg2526Isup3.cml

CCDC reference: 996988

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H12NO2+·NO3−	Z = 4
Mr = 216.20	F(000) = 456
Triclinic, P1	Dx = 1.506 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3066 (4) Å	Cell parameters from 3958 reflections
b = 10.4856 (5) Å	θ = 2.5–27.5°
c = 11.2303 (7) Å	µ = 0.13 mm−1
α = 79.623 (2)°	T = 150 K
β = 89.868 (2)°	Prism, colorless
γ = 82.357 (2)°	0.56 × 0.44 × 0.27 mm
V = 953.37 (9) Å3

Bruker APEXII diffractometer	3583 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −10→10
Tmin = 0.870, Tmax = 0.966	k = −13→13
10787 measured reflections	l = −14→14
4339 independent reflections

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.2245P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4339 reflections	Δρmax = 0.31 e Å−3
312 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.061 (4)

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
O1	0.88256 (15)	0.20879 (11)	0.45485 (10)	0.0270 (3)
O2	0.89365 (13)	0.15989 (10)	0.22563 (10)	0.0231 (3)
O3	0.52188 (13)	0.78884 (10)	0.05973 (9)	0.0218 (2)
O4	0.50913 (13)	0.84937 (9)	0.28522 (10)	0.0199 (2)
O5	0.13563 (13)	0.88517 (10)	0.00083 (10)	0.0240 (3)
O6	0.23349 (13)	1.02198 (11)	0.09420 (10)	0.0247 (3)
O7	0.27175 (12)	1.03129 (10)	−0.09879 (9)	0.0212 (2)
O8	1.24531 (13)	0.01122 (10)	0.58958 (10)	0.0240 (3)
O9	1.39421 (14)	0.14414 (11)	0.48499 (10)	0.0283 (3)
O10	1.24180 (13)	0.03858 (11)	0.39320 (10)	0.0264 (3)
N1	1.03491 (17)	0.87415 (12)	0.27899 (14)	0.0202 (3)
N2	0.47018 (16)	0.13341 (12)	0.21268 (13)	0.0181 (3)
N3	0.21404 (14)	0.97956 (11)	−0.00085 (11)	0.0170 (3)
N4	1.29264 (14)	0.06439 (11)	0.48912 (11)	0.0189 (3)
C1	1.02008 (18)	0.74577 (14)	0.24467 (15)	0.0226 (3)
H1A	1.1233	0.6897	0.2606	0.027*
H1B	0.9964	0.7590	0.1584	0.027*
C2	0.89005 (19)	0.67827 (14)	0.31175 (16)	0.0252 (4)
H2A	0.7850	0.7292	0.2887	0.030*
H2B	0.9067	0.6732	0.3980	0.030*
C3	0.89030 (17)	0.54144 (14)	0.28525 (14)	0.0204 (3)
C4	0.88790 (18)	0.43580 (14)	0.38027 (14)	0.0208 (3)
H4	0.8855	0.4503	0.4596	0.025*
C5	0.88905 (17)	0.30931 (14)	0.35856 (13)	0.0187 (3)
C6	0.89502 (16)	0.28653 (13)	0.23989 (14)	0.0175 (3)
C7	0.89493 (18)	0.39103 (14)	0.14486 (14)	0.0211 (3)
H7	0.8966	0.3767	0.0655	0.025*
C8	0.89233 (18)	0.51738 (15)	0.16758 (15)	0.0226 (3)
H8	0.8919	0.5868	0.1030	0.027*
C9	0.49926 (16)	0.26836 (13)	0.22214 (13)	0.0163 (3)
H9A	0.5741	0.2984	0.1602	0.020*
H9B	0.5490	0.2672	0.3005	0.020*
C10	0.34207 (17)	0.36269 (13)	0.20725 (14)	0.0191 (3)
H10A	0.2969	0.3709	0.1262	0.023*
H10B	0.2634	0.3298	0.2648	0.023*
C11	0.37719 (16)	0.49492 (13)	0.22873 (14)	0.0178 (3)
C12	0.42284 (16)	0.58718 (13)	0.13394 (13)	0.0177 (3)
H12	0.4214	0.5706	0.0553	0.021*
C13	0.47037 (16)	0.70326 (13)	0.15462 (13)	0.0160 (3)
C14	0.46516 (16)	0.73132 (13)	0.27195 (13)	0.0159 (3)
C15	0.41976 (17)	0.64019 (14)	0.36697 (13)	0.0199 (3)
H15	0.4173	0.6580	0.4452	0.024*
C16	0.37771 (18)	0.52191 (14)	0.34542 (14)	0.0207 (3)
H16	0.3497	0.4604	0.4098	0.025*
H1N	1.070 (3)	0.864 (2)	0.360 (2)	0.053 (7)*
H2N	1.098 (2)	0.9221 (19)	0.2291 (18)	0.033 (5)*
H3N	0.941 (2)	0.9239 (19)	0.2786 (17)	0.034 (5)*
H4N	0.565 (2)	0.0765 (17)	0.2227 (16)	0.028 (5)*
H5N	0.402 (2)	0.1015 (19)	0.2728 (19)	0.035 (5)*
H6N	0.424 (2)	0.1300 (17)	0.1380 (18)	0.028 (5)*
H1O	0.857 (3)	0.142 (2)	0.429 (2)	0.053 (7)*
H2O	0.887 (2)	0.154 (2)	0.147 (2)	0.043 (6)*
H3O	0.578 (3)	0.845 (2)	0.0863 (19)	0.047 (6)*
H4O	0.538 (2)	0.8496 (19)	0.361 (2)	0.040 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0489 (7)	0.0187 (6)	0.0161 (6)	−0.0126 (5)	0.0031 (5)	−0.0042 (4)
O2	0.0371 (6)	0.0168 (5)	0.0170 (6)	−0.0066 (4)	0.0011 (5)	−0.0051 (4)
O3	0.0335 (6)	0.0192 (5)	0.0148 (5)	−0.0108 (4)	0.0025 (5)	−0.0032 (4)
O4	0.0293 (6)	0.0146 (5)	0.0168 (6)	−0.0056 (4)	−0.0013 (4)	−0.0040 (4)
O5	0.0315 (6)	0.0245 (6)	0.0198 (6)	−0.0165 (5)	0.0031 (5)	−0.0054 (4)
O6	0.0280 (6)	0.0328 (6)	0.0181 (6)	−0.0118 (5)	0.0017 (5)	−0.0117 (5)
O7	0.0263 (5)	0.0209 (5)	0.0172 (6)	−0.0081 (4)	0.0057 (4)	−0.0018 (4)
O8	0.0325 (6)	0.0241 (6)	0.0175 (6)	−0.0111 (4)	0.0084 (5)	−0.0043 (4)
O9	0.0385 (6)	0.0309 (6)	0.0200 (6)	−0.0218 (5)	0.0027 (5)	−0.0046 (5)
O10	0.0323 (6)	0.0329 (6)	0.0181 (6)	−0.0137 (5)	0.0002 (5)	−0.0082 (5)
N1	0.0240 (7)	0.0153 (6)	0.0222 (7)	−0.0058 (5)	0.0039 (6)	−0.0034 (5)
N2	0.0231 (6)	0.0141 (6)	0.0176 (7)	−0.0031 (5)	0.0019 (5)	−0.0039 (5)
N3	0.0166 (5)	0.0187 (6)	0.0159 (6)	−0.0028 (4)	−0.0006 (5)	−0.0031 (5)
N4	0.0230 (6)	0.0173 (6)	0.0172 (7)	−0.0051 (5)	0.0033 (5)	−0.0037 (5)
C1	0.0250 (7)	0.0161 (7)	0.0296 (9)	−0.0070 (6)	0.0078 (6)	−0.0089 (6)
C2	0.0281 (8)	0.0179 (7)	0.0316 (9)	−0.0076 (6)	0.0107 (7)	−0.0071 (6)
C3	0.0178 (7)	0.0189 (7)	0.0265 (8)	−0.0072 (5)	0.0052 (6)	−0.0059 (6)
C4	0.0251 (7)	0.0211 (7)	0.0195 (8)	−0.0093 (6)	0.0063 (6)	−0.0080 (6)
C5	0.0214 (7)	0.0184 (7)	0.0172 (7)	−0.0066 (5)	0.0030 (6)	−0.0030 (6)
C6	0.0172 (6)	0.0169 (7)	0.0198 (8)	−0.0046 (5)	0.0007 (6)	−0.0053 (6)
C7	0.0233 (7)	0.0250 (8)	0.0167 (7)	−0.0080 (6)	0.0013 (6)	−0.0045 (6)
C8	0.0259 (8)	0.0185 (7)	0.0233 (8)	−0.0083 (6)	0.0022 (6)	0.0004 (6)
C9	0.0167 (6)	0.0133 (6)	0.0195 (7)	−0.0044 (5)	0.0008 (6)	−0.0030 (5)
C10	0.0179 (7)	0.0149 (7)	0.0251 (8)	−0.0027 (5)	−0.0003 (6)	−0.0044 (6)
C11	0.0152 (6)	0.0133 (6)	0.0247 (8)	−0.0006 (5)	−0.0001 (6)	−0.0036 (6)
C12	0.0191 (7)	0.0181 (7)	0.0169 (7)	−0.0014 (5)	0.0004 (6)	−0.0066 (6)
C13	0.0169 (6)	0.0145 (6)	0.0150 (7)	−0.0005 (5)	−0.0002 (5)	−0.0002 (5)
C14	0.0171 (6)	0.0125 (6)	0.0184 (7)	−0.0006 (5)	−0.0011 (5)	−0.0044 (5)
C15	0.0259 (7)	0.0199 (7)	0.0138 (7)	−0.0030 (6)	0.0021 (6)	−0.0033 (6)
C16	0.0242 (7)	0.0164 (7)	0.0203 (8)	−0.0033 (6)	0.0029 (6)	0.0005 (6)

O1—C5	1.3738 (18)	C2—H2A	0.9700
O1—H1O	0.86 (2)	C2—H2B	0.9700
O2—C6	1.3674 (16)	C3—C8	1.389 (2)
O2—H2O	0.89 (2)	C3—C4	1.395 (2)
O3—C13	1.3709 (17)	C4—C5	1.3899 (19)
O3—H3O	0.89 (2)	C4—H4	0.9300
O4—C14	1.3693 (16)	C5—C6	1.395 (2)
O4—H4O	0.89 (2)	C6—C7	1.385 (2)
O5—N3	1.2526 (15)	C7—C8	1.391 (2)
O6—N3	1.2467 (15)	C7—H7	0.9300
O7—N3	1.2592 (15)	C8—H8	0.9300
O8—N4	1.2522 (15)	C9—C10	1.5196 (18)
O9—N4	1.2596 (15)	C9—H9A	0.9700
O10—N4	1.2448 (16)	C9—H9B	0.9700
N1—C1	1.4856 (18)	C10—C11	1.5147 (18)
N1—H1N	0.94 (3)	C10—H10A	0.9700
N1—H2N	0.90 (2)	C10—H10B	0.9700
N1—H3N	0.88 (2)	C11—C16	1.390 (2)
N2—C9	1.4889 (17)	C11—C12	1.392 (2)
N2—H4N	0.915 (19)	C12—C13	1.3862 (19)
N2—H5N	0.93 (2)	C12—H12	0.9300
N2—H6N	0.93 (2)	C13—C14	1.400 (2)
C1—C2	1.497 (2)	C14—C15	1.386 (2)
C1—H1A	0.9700	C15—C16	1.394 (2)
C1—H1B	0.9700	C15—H15	0.9300
C2—C3	1.5166 (19)	C16—H16	0.9300
C5—O1—H1O	109.1 (15)	O1—C5—C6	121.11 (13)
C6—O2—H2O	111.0 (13)	C4—C5—C6	119.73 (13)
C13—O3—H3O	110.9 (14)	O2—C6—C7	124.11 (13)
C14—O4—H4O	111.6 (13)	O2—C6—C5	116.37 (13)
C1—N1—H1N	111.3 (13)	C7—C6—C5	119.46 (13)
C1—N1—H2N	113.2 (12)	C6—C7—C8	120.29 (14)
H1N—N1—H2N	110.9 (18)	C6—C7—H7	119.9
C1—N1—H3N	113.0 (12)	C8—C7—H7	119.9
H1N—N1—H3N	102.2 (18)	C3—C8—C7	121.00 (14)
H2N—N1—H3N	105.6 (17)	C3—C8—H8	119.5
C9—N2—H4N	111.3 (11)	C7—C8—H8	119.5
C9—N2—H5N	110.8 (12)	N2—C9—C10	111.48 (11)
H4N—N2—H5N	106.3 (16)	N2—C9—H9A	109.3
C9—N2—H6N	112.1 (11)	C10—C9—H9A	109.3
H4N—N2—H6N	107.8 (16)	N2—C9—H9B	109.3
H5N—N2—H6N	108.3 (16)	C10—C9—H9B	109.3
O6—N3—O5	119.78 (12)	H9A—C9—H9B	108.0
O6—N3—O7	120.57 (11)	C11—C10—C9	108.97 (11)
O5—N3—O7	119.65 (12)	C11—C10—H10A	109.9
O10—N4—O8	120.87 (12)	C9—C10—H10A	109.9
O10—N4—O9	119.50 (12)	C11—C10—H10B	109.9
O8—N4—O9	119.63 (12)	C9—C10—H10B	109.9
N1—C1—C2	112.95 (12)	H10A—C10—H10B	108.3
N1—C1—H1A	109.0	C16—C11—C12	118.72 (13)
C2—C1—H1A	109.0	C16—C11—C10	120.30 (13)
N1—C1—H1B	109.0	C12—C11—C10	120.75 (13)
C2—C1—H1B	109.0	C13—C12—C11	121.16 (13)
H1A—C1—H1B	107.8	C13—C12—H12	119.4
C1—C2—C3	111.68 (12)	C11—C12—H12	119.4
C1—C2—H2A	109.3	O3—C13—C12	119.41 (13)
C3—C2—H2A	109.3	O3—C13—C14	121.02 (12)
C1—C2—H2B	109.3	C12—C13—C14	119.57 (13)
C3—C2—H2B	109.3	O4—C14—C15	123.85 (13)
H2A—C2—H2B	107.9	O4—C14—C13	116.47 (12)
C8—C3—C4	118.26 (13)	C15—C14—C13	119.67 (13)
C8—C3—C2	121.71 (14)	C14—C15—C16	120.06 (14)
C4—C3—C2	120.03 (14)	C14—C15—H15	120.0
C5—C4—C3	121.22 (14)	C16—C15—H15	120.0
C5—C4—H4	119.4	C11—C16—C15	120.73 (13)
C3—C4—H4	119.4	C11—C16—H16	119.6
O1—C5—C4	119.15 (13)	C15—C16—H16	119.6
N1—C1—C2—C3	−173.68 (13)	N2—C9—C10—C11	175.05 (12)
C1—C2—C3—C8	−49.6 (2)	C9—C10—C11—C16	−86.05 (16)
C1—C2—C3—C4	130.67 (15)	C9—C10—C11—C12	88.48 (16)
C8—C3—C4—C5	0.6 (2)	C16—C11—C12—C13	0.9 (2)
C2—C3—C4—C5	−179.61 (13)	C10—C11—C12—C13	−173.70 (12)
C3—C4—C5—O1	−178.42 (13)	C11—C12—C13—O3	176.89 (12)
C3—C4—C5—C6	0.9 (2)	C11—C12—C13—C14	−3.1 (2)
O1—C5—C6—O2	0.1 (2)	O3—C13—C14—O4	1.94 (19)
C4—C5—C6—O2	−179.17 (13)	C12—C13—C14—O4	−178.10 (12)
O1—C5—C6—C7	177.44 (13)	O3—C13—C14—C15	−177.00 (13)
C4—C5—C6—C7	−1.9 (2)	C12—C13—C14—C15	3.0 (2)
O2—C6—C7—C8	178.41 (13)	O4—C14—C15—C16	−179.61 (13)
C5—C6—C7—C8	1.3 (2)	C13—C14—C15—C16	−0.7 (2)
C4—C3—C8—C7	−1.2 (2)	C12—C11—C16—C15	1.3 (2)
C2—C3—C8—C7	179.05 (13)	C10—C11—C16—C15	175.98 (13)
C6—C7—C8—C3	0.2 (2)	C14—C15—C16—C11	−1.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O8i	0.86 (2)	1.96 (2)	2.7871 (15)	163 (2)
O2—H2O···O5ii	0.89 (2)	1.80 (2)	2.6863 (16)	169.7 (19)
O3—H3O···O7iii	0.89 (2)	1.94 (2)	2.8017 (15)	164 (2)
O4—H4O···O9iv	0.89 (2)	1.83 (2)	2.7196 (16)	176.6 (19)
N1—H1N···O1iv	0.94 (3)	2.10 (3)	3.0125 (19)	163.3 (19)
N1—H2N···O6v	0.90 (2)	2.10 (2)	2.9893 (17)	172.1 (17)
N1—H3N···O8iv	0.88 (2)	2.26 (2)	2.9867 (17)	139.6 (17)
N1—H3N···O2vi	0.88 (2)	2.42 (2)	3.0223 (16)	126.6 (15)
N2—H4N···O7ii	0.92 (2)	2.28 (2)	3.0020 (16)	135.2 (15)
N2—H4N···O8i	0.92 (2)	2.59 (2)	3.2672 (18)	131.3 (14)
N2—H5N···O10vii	0.93 (2)	1.98 (2)	2.9079 (17)	175.7 (18)
N2—H5N···O9vii	0.93 (2)	2.50 (2)	3.1400 (17)	126.3 (15)
N2—H6N···O6viii	0.93 (2)	2.17 (2)	2.8608 (17)	130.2 (15)
N2—H6N···O3ii	0.93 (2)	2.30 (2)	3.0236 (17)	134.5 (14)
C1—H1B···O5v	0.97	2.40	3.0783 (19)	126
C2—H2A···O4	0.97	2.46	3.4090 (19)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O8i	0.86 (2)	1.96 (2)	2.7871 (15)	163 (2)
O2—H2O⋯O5ii	0.89 (2)	1.80 (2)	2.6863 (16)	169.7 (19)
O3—H3O⋯O7iii	0.89 (2)	1.94 (2)	2.8017 (15)	164 (2)
O4—H4O⋯O9iv	0.89 (2)	1.83 (2)	2.7196 (16)	176.6 (19)
N1—H1N⋯O1iv	0.94 (3)	2.10 (3)	3.0125 (19)	163.3 (19)
N1—H2N⋯O6v	0.90 (2)	2.10 (2)	2.9893 (17)	172.1 (17)
N1—H3N⋯O8iv	0.88 (2)	2.26 (2)	2.9867 (17)	139.6 (17)
N1—H3N⋯O2vi	0.88 (2)	2.42 (2)	3.0223 (16)	126.6 (15)
N2—H4N⋯O7ii	0.92 (2)	2.28 (2)	3.0020 (16)	135.2 (15)
N2—H4N⋯O8i	0.92 (2)	2.59 (2)	3.2672 (18)	131.3 (14)
N2—H5N⋯O10vii	0.93 (2)	1.98 (2)	2.9079 (17)	175.7 (18)
N2—H5N⋯O9vii	0.93 (2)	2.50 (2)	3.1400 (17)	126.3 (15)
N2—H6N⋯O6viii	0.93 (2)	2.17 (2)	2.8608 (17)	130.2 (15)
N2—H6N⋯O3ii	0.93 (2)	2.30 (2)	3.0236 (17)	134.5 (14)
C1—H1B⋯O5v	0.97	2.40	3.0783 (19)	126
C2—H2A⋯O4	0.97	2.46	3.4090 (19)	166

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .