organic compounds
Dopaminium nitrate
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
The 8H12NO2+·NO3−, contains two independent cations and two independent nitrate anions. The 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.
of the title salt [systematic name: 2-(3,4-dihydroxyphenyl)ethanaminium nitrate], CCCDC 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
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Data collection: APEX2 (Bruker, 2006); cell 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
10.1107/S1600536814008265/bg2526sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814008265/bg2526Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814008265/bg2526Isup3.cml
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).
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.
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 Uiso(H) = 1.2Ueq(C).
In this work, we report the preparation and the structural investigation of the dopaminium nitrate, C8H12NO2·NO3 (I).
The
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.
Data collection: APEX2 (Bruker, 2006); cell
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).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) |
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) |
C8H12NO2+·NO3− | γ = 82.357 (2)° |
Mr = 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)° |
Bruker APEXII diffractometer | 4339 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2006) | 3583 reflections with I > 2σ(I) |
Tmin = 0.870, Tmax = 0.966 | Rint = 0.038 |
10787 measured reflections |
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 | Δρmax = 0.31 e Å−3 |
4339 reflections | Δρmin = −0.26 e Å−3 |
312 parameters |
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 |
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. |
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) | 126.3 |
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
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