Dopaminium nitrate

Gatfaoui, S.; Marouani, H.; Roisnel, T.; Dhaouadi, H.

doi:10.1107/S1600536814008265

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages o571-o572

doi:10.1107/S1600536814008265

Open

access

Dopaminium nitrate

Sofian Gatfaoui,^a Houda Marouani,^a Thierry Roisnel ^b and Hassouna Dhaouadi ^c ^*

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, ^bCentre de Diffractométrie X, UMR 6226 CNRS, Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France, and ^cLaboratoire des Matériaux Utiles, Institut National de Recherche et d'Analyse Physico-chimique, Pole Technologique de Sidi-Thabet, 2020 Tunis, Tunisia
^*Correspondence e-mail: dhaouadihassouna@yahoo.fr

(Received 10 April 2014; accepted 12 April 2014; online 18 April 2014)

The asymmetric unit of the title salt [systematic name: 2-(3,4-dihydroxyphenyl)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 supramolecular network.

CCDC reference: 996988

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_r = 216.20
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.113
S = 1.05
4339 reflections
312 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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⋯O9^iv	0.89 (2)	1.83 (2)	2.7196 (16)	176.6 (19)
N1—H1N⋯O1^iv	0.94 (3)	2.10 (3)	3.0125 (19)	163.3 (19)
N1—H2N⋯O6^v	0.90 (2)	2.10 (2)	2.9893 (17)	172.1 (17)
N1—H3N⋯O8^iv	0.88 (2)	2.26 (2)	2.9867 (17)	139.6 (17)
N1—H3N⋯O2^vi	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⋯O10^vii	0.93 (2)	1.98 (2)	2.9079 (17)	175.7 (18)
N2—H5N⋯O9^vii	0.93 (2)	2.50 (2)	3.1400 (17)	126.3 (15)
N2—H6N⋯O6^viii	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⋯O5^v	0.97	2.40	3.0783 (19)	126
C2—H2A⋯O4	0.97	2.46	3.4090 (19)	166
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y+1, -z; (iii) -x+1, -y+2, -z; (iv) -x+2, -y+1, -z+1; (v) x+1, y, z; (vi) x, y+1, z; (vii) x-1, y, z; (viii) x, y-1, z.

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).

Supporting information

CCDC reference: 996988

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

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

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

checkCIF report

Introduction top

Dopamine is an important regulator of many physiological functions, including control of locomotion, cognition, affect, and neuroendocrine hormone secretion. The dopamine transporter (DAT) plays an important role in calibrating the duration and intensity of dopamine neurotransmission in the central nervous system (Jones et al., 1999). In addition, dopamine is an important signal transmitter between the neurons and muscles (Salamone & Correa, 2002).

Experimental top

Synthesis and crystallization top

An aqueous solution containing 1 mmol of HNO₃ in 10 ml of water was added to 1 mmol of dopamine hydrochloride in 10 ml of water. The obtained solution was stirred for 15 min and then left to stand at room temperature. Colorless single crystals of the title compound were obtained after some days.

Refinement top

The hydrogen atoms bonded to oxygen and nitrogen atoms were located from a difference map and were allowed to refine. The rest of the H atoms were treated as riding, with C—H = 0.97 Å (methylene), or 0.93 Å (methine), with U_iso(H) = 1.2U_eq(C).

Results and discussion top

In this work, we report the preparation and the structural investigation of the dopaminium nitrate, C₈H₁₂NO₂·NO₃ (I).

The asymmetric unit of (I) is composed of two independent dopaminium cations and two independent nitrate anions (Figure 1). The structure of the compound consists of discrete nitrate ions stacked in layers parallel to the (010) plane separated by organic cations (Figure 2). The structural cohesion is established by a three-dimensional network of N—H···O, O—H···O and weak C—H···O hydrogen bonds (Brown, 1976; Blessing, 1986).

Interatomic bond lengths and angles of the nitrate anions spread respectively within the ranges [1.2448 (16)–1.2596 (15) Å] and [119.50 (12)–120.87 (12)°]. These geometrical features have also been noticed in other crystal structures (Marouani et al., 2012; Kefi et al., 2013; Gatfaoui et al., 2013, 2014a, 2014b).

In this atomic arrangement two independent dopaminium cations are present. Examination of the organic cations shows that the bond distances and angles show no significant difference from those obtained in other salt involving the same organic groups (Boghaei et al., 2008). The aromatic rings are planar with an average deviation of 0.0014 Å and form a dihedral angle of 7.81°. The interplanar distance between nearby phenyl rings is in the vicinity of 4.16 Å, a bit longer than required for a medium strength π–π interaction (Janiak, 2000).

The established H-bonds of types O—H···O, N—H···O and C—H···O (Table 1) involve oxygen atoms of the nitrate anions as acceptors, and the protonated nitrogen atoms, carbon and oxygen atoms of dopaminium as donors.

Related literature top

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).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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).

Figures top

	Fig. 1. An ellipsoid plot of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Projection of (I) along the a axis. The H-atoms not involved in H-bonding are omitted. N atoms labelled with their generic names (No symmetry codes applied)

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

Crystal data top

C₈H₁₂NO₂⁺·NO₃⁻	Z = 4
M_r = 216.20	F(000) = 456
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0546P)² + 0.2245P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4339 reflections	Δρ_max = 0.31 e Å⁻³
312 parameters	Δρ_min = −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)

Crystal data top

C₈H₁₂NO₂⁺·NO₃⁻	γ = 82.357 (2)°
M_r = 216.20	V = 953.37 (9) Å³
Triclinic, P1	Z = 4
a = 8.3066 (4) Å	Mo Kα radiation
b = 10.4856 (5) Å	µ = 0.13 mm⁻¹
c = 11.2303 (7) Å	T = 150 K
α = 79.623 (2)°	0.56 × 0.44 × 0.27 mm
β = 89.868 (2)°

Data collection top

Bruker APEXII diffractometer	4339 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	3583 reflections with I > 2σ(I)
T_min = 0.870, T_max = 0.966	R_int = 0.038
10787 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.31 e Å⁻³
4339 reflections	Δρ_min = −0.26 e Å⁻³
312 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O9^iv	0.89 (2)	1.83 (2)	2.7196 (16)	176.6 (19)
N1—H1N···O1^iv	0.94 (3)	2.10 (3)	3.0125 (19)	163.3 (19)
N1—H2N···O6^v	0.90 (2)	2.10 (2)	2.9893 (17)	172.1 (17)
N1—H3N···O8^iv	0.88 (2)	2.26 (2)	2.9867 (17)	139.6 (17)
N1—H3N···O2^vi	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···O10^vii	0.93 (2)	1.98 (2)	2.9079 (17)	175.7 (18)
N2—H5N···O9^vii	0.93 (2)	2.50 (2)	3.1400 (17)	126.3 (15)
N2—H6N···O6^viii	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···O5^v	0.97	2.40	3.0783 (19)	126
C2—H2A···O4	0.97	2.46	3.4090 (19)	166

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z+1; (v) x+1, y, z; (vi) x, y+1, z; (vii) x−1, y, z; (viii) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

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···O9^iv	0.89 (2)	1.83 (2)	2.7196 (16)	176.6 (19)
N1—H1N···O1^iv	0.94 (3)	2.10 (3)	3.0125 (19)	163.3 (19)
N1—H2N···O6^v	0.90 (2)	2.10 (2)	2.9893 (17)	172.1 (17)
N1—H3N···O8^iv	0.88 (2)	2.26 (2)	2.9867 (17)	139.6 (17)
N1—H3N···O2^vi	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···O10^vii	0.93 (2)	1.98 (2)	2.9079 (17)	175.7 (18)
N2—H5N···O9^vii	0.93 (2)	2.50 (2)	3.1400 (17)	126.3 (15)
N2—H6N···O6^viii	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···O5^v	0.97	2.40	3.0783 (19)	126.3
C2—H2A···O4	0.97	2.46	3.4090 (19)	165.7

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z+1; (v) x+1, y, z; (vi) x, y+1, z; (vii) x−1, y, z; (viii) x, y−1, z.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Blessing, R. H. (1986). Acta Cryst. B42, 613–621. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Boghaei, D. M., Baniyaghoob, S., Najafpour, M. M. & McKee, V. (2008). Acta Cryst. E64, o2268. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal impact GbR, Bonn, Germany. Google Scholar
Brown, I. D. (1976). Acta Cryst. A32, 24–31. CrossRef IUCr Journals Web of Science Google Scholar
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gatfaoui, S., Dhaouadi, H., Roisnel, T., Rzaigui, M. & Marouani, H. (2014b). Acta Cryst. E70, o398–o399. CSD CrossRef CAS IUCr Journals Google Scholar
Gatfaoui, S., Marouani, H. & Rzaigui, M. (2013). Acta Cryst. E69, o1453. CSD CrossRef IUCr Journals Google Scholar
Gatfaoui, S., Rzaigui, M. & Marouani, H. (2014a). Acta Cryst. E70, o198. CSD CrossRef IUCr Journals Google Scholar
Janiak, J. (2000). J. Chem. Soc. Dalton Trans. pp. 3885–3896. Web of Science CrossRef Google Scholar
Jones, S. R., Joseph, J. D., Barak, L. S., Caron, M. G. & Wightman, R. M. (1999). J. Neurochem. 73, 2406–2414. Web of Science CrossRef PubMed CAS Google Scholar
Kefi, C., Marouani, H. & Rzaigui, M. (2013). Acta Cryst. E69, o1475. CSD CrossRef IUCr Journals Google Scholar
Marouani, H., Raouafi, N., Toumi Akriche, S., Al-Deyab, S. S. & Rzaigui, M. (2012). Eur. J. Chem. 9, 772–779. CAS Google Scholar
Salamone, J. D. & Correa, M. (2002). Behav. Brain Res. 137, 3–25. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages o571-o572

doi:10.1107/S1600536814008265

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Dopaminium nitrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds