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organic compounds
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2-Aminopyrimidinium picrate
aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, bDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India, cDepartment of Physics, Mangalore University, Mangalagangotri 574 199, India, dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and eInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
*Correspondence e-mail: bolte@chemie.uni-frankfurt.de
The geometric parameters of the title compound, C4H6N3+·C6H2N3O7−, are in the usual ranges. While two nitro groups are almost coplanar with the aromatic picrate ring [dihedral angles 3.0 (2) and 4.4 (3)°], the third is significantly twisted out of this plane [dihedral angle 46.47 (8)°]. Anions and cations are connected via N—H⋯O hydrogen bonds. The molecules crystallize in planes parallel to (11).
Related literature
For related literature, see: Barraclough & Smith (1995); Etter et al. (1990
); Fischer et al. (2007
); Goswami et al. (2000
); Gueiffier et al. (1996
); Katritzky et al. (2003
); Rival et al. (1991
); Sanfilippo et al. (1988
); Scheinbeim & Schempp (1976
); Schlueter et al. (2006
); Tully et al. (1991
); Yathirajan, Bindya et al. (2007a
,b
); Yathirajan, Mayekar et al. (2007
); Yathirajan, Narayana et al. (2007
).
Experimental
Crystal data
|
Data collection
|
Refinement
|
|
Data collection: X-AREA (Stoe & Cie, 2001); cell X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990
); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997
); molecular graphics: PLATON (Spek, 2003
); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536807062599/at2509sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062599/at2509Isup2.hkl
2-Aminopyrimidine (0.95 g, 0.01 mol) was dissolved in 20 ml of ethanol. Picric acid (2.29 g, 0.01 mol) was dissolved in 10 ml of water. Both the solutions were mixed and to this, 5 ml of 5 M HCl was added and stirred for few minutes. The formed complex was filtered, dried and recrystallized from ethanol (m.p.: 413–415 K). Composition: Found (calculated): C 37.01(37.05), H 2.46(2.49), N 25.87% (25.92%).
H atoms were found in a difference map, but those bonded to C were geometrically positioned and refined with fixed individual displacement parameters [Uiso(H) = 1.2 Ueq(C)] using a riding model with C—H = 0.95 Å. The amino H atoms were freely refined.
Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring. A pyrimidine has many properties in common with pyridine, as the number of nitrogen atoms in the ring increases the ring π-electrons become less energetic and electrophilic aromatic substitution gets more difficult while nucleophilic aromatic substitution gets easier. Pyrimidines are important compounds in pharmaceutical chemistry as antiviral agents (Gueiffier et al., 1996), inotropic and β-blocking agents (Barraclough & Smith, 1995), antifungal agents (Rival et al. 1991), benzodiazepine receptor agonists (Tully et al.1991), and calcium channel blockers (Sanfilippo et al., 1988). The synthesis of imidazo[1,2-a]pyrimidines has been widely investigated and one of the most common strategies uses 2-aminopyrimidine as the starting material (Katritzky et al., 2003). The crystal structures of the following compounds have been previously reported, viz; 2-aminopyrimidine (Scheinbeim & Schempp, 1976), 1:1 hetero-assembly of 2-aminopyrimidine and (+)-camphoric acid (Goswami, et al., 2000), 2-aminopyrimidine-succinic acid (1:1) cocrystal (Etter et al., 1990), 5-aminopyrimidine (Schlueter et al., 2006), 5-bromopyrimidin-2(1H)-one (Yathirajan, Narayana, Ashalatha et al., 2007), ethyl 7-methyl-2-[4-(methylsulfanyl)benzylidene]-5-[4-(methylsulfanyl)phenyl]-3-oxo-2, 3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate (Fischer et al., 2007), 2-(4-methylbenzoyloxymethyl)-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1 -yl)tetrahydrofuran-3-yl 4-methylbenzoate (Yathirajan, Mayekar, Sarojini et al., 2007), methyl (4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-5-yl)acetate (Yathirajan, Bindya, Sarojini et al., 2007a), ethyl (4-oxo-1-phenyl-1,4-dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-yl)acetate (Yathirajan, Bindya, Sarojini et al., 2007b). In continuation to our work on of biologically important molecules, we have prepared a new picrate of 2-aminopyrimidine, and its is reported.
Geometric parameters of the title compound are in the usual ranges. Whereas two nitrogroups are almost coplanar with the aromatic picrate ring [dihedral angles 3.0 (2)° and 4.4 (3)°] the third one is significantly twisted [dihedral angle 46.47 (8)°] out of this plane Anions and cations are connected via N—H···O hydrogen bonds. The molecules crystallize in planes parallel to (1 - 2 1).
For related literature, see: Barraclough & Smith (1995); Etter et al. (1990); Fischer et al. (2007); Goswami et al. (2000); Gueiffier et al. (1996); Katritzky et al. (2003); Rival et al. (1991); Sanfilippo et al. (1988); Scheinbeim & Schempp (1976); Schlueter et al. (2006); Tully et al. (1991); Yathirajan, Bindya et al. (2007a,b); Yathirajan, Mayekar et al. (2007); Yathirajan, Narayana et al. (2007).
Data collection: X-AREA (Stoe & Cie, 2001); cell
X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997). ![]() | Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. The hydrogen bonds are shown as dashed lines. |
C4H6N3+·C6H2N3O7− | Z = 2 |
Mr = 324.22 | F(000) = 332 |
Triclinic, P1 | Dx = 1.673 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8803 (7) Å | Cell parameters from 8213 reflections |
b = 8.0025 (10) Å | θ = 3.5–25.8° |
c = 13.8108 (17) Å | µ = 0.15 mm−1 |
α = 88.021 (10)° | T = 173 K |
β = 82.322 (9)° | Plate, yellow |
γ = 88.739 (10)° | 0.26 × 0.22 × 0.09 mm |
V = 643.59 (14) Å3 |
Stoe IPDSII two-circle diffractometer | 1927 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
Graphite monochromator | θmax = 25.6°, θmin = 3.5° |
ω scans | h = −7→7 |
8757 measured reflections | k = −9→9 |
2402 independent reflections | l = −16→16 |
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) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0661P)2] where P = (Fo2 + 2Fc2)/3 |
2402 reflections | (Δ/σ)max < 0.001 |
220 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C4H6N3+·C6H2N3O7− | γ = 88.739 (10)° |
Mr = 324.22 | V = 643.59 (14) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.8803 (7) Å | Mo Kα radiation |
b = 8.0025 (10) Å | µ = 0.15 mm−1 |
c = 13.8108 (17) Å | T = 173 K |
α = 88.021 (10)° | 0.26 × 0.22 × 0.09 mm |
β = 82.322 (9)° |
Stoe IPDSII two-circle diffractometer | 1927 reflections with I > 2σ(I) |
8757 measured reflections | Rint = 0.042 |
2402 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.20 e Å−3 |
2402 reflections | Δρmin = −0.27 e Å−3 |
220 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 | ||
N1 | 0.7277 (3) | 0.40774 (18) | 0.07873 (11) | 0.0279 (3) | |
H1A | 0.799 (3) | 0.422 (2) | 0.0195 (16) | 0.033 (5)* | |
H1B | 0.600 (4) | 0.346 (3) | 0.0984 (15) | 0.039 (5)* | |
C1 | 0.8282 (3) | 0.47463 (18) | 0.14768 (11) | 0.0199 (3) | |
N2 | 0.7333 (2) | 0.45943 (15) | 0.24319 (9) | 0.0206 (3) | |
H2 | 0.604 (4) | 0.400 (3) | 0.2556 (15) | 0.039 (5)* | |
C3 | 0.8321 (3) | 0.52828 (18) | 0.31540 (11) | 0.0229 (3) | |
H3 | 0.7618 | 0.5183 | 0.3814 | 0.027* | |
C4 | 1.0334 (3) | 0.61214 (19) | 0.29261 (11) | 0.0241 (3) | |
H4 | 1.1076 | 0.6609 | 0.3415 | 0.029* | |
C5 | 1.1247 (3) | 0.62249 (18) | 0.19338 (12) | 0.0229 (3) | |
H5 | 1.2654 | 0.6791 | 0.1762 | 0.027* | |
N6 | 1.0274 (2) | 0.55855 (15) | 0.12224 (9) | 0.0228 (3) | |
C11 | 0.2209 (2) | 0.17922 (17) | 0.24085 (11) | 0.0194 (3) | |
C12 | 0.0995 (2) | 0.17467 (18) | 0.33896 (11) | 0.0196 (3) | |
C13 | −0.1064 (2) | 0.09207 (18) | 0.36532 (11) | 0.0201 (3) | |
H13 | −0.1809 | 0.0931 | 0.4307 | 0.024* | |
C14 | −0.2010 (2) | 0.00844 (17) | 0.29461 (11) | 0.0197 (3) | |
C15 | −0.0957 (3) | 0.00409 (18) | 0.19783 (11) | 0.0209 (3) | |
H15 | −0.1612 | −0.0560 | 0.1506 | 0.025* | |
C16 | 0.1043 (2) | 0.08881 (18) | 0.17311 (11) | 0.0197 (3) | |
N11 | 0.1908 (2) | 0.26127 (16) | 0.41664 (10) | 0.0238 (3) | |
N12 | −0.4142 (2) | −0.08122 (16) | 0.32163 (10) | 0.0250 (3) | |
N13 | 0.2118 (2) | 0.08312 (16) | 0.07100 (9) | 0.0226 (3) | |
O11 | 0.41007 (18) | 0.24842 (14) | 0.21384 (8) | 0.0276 (3) | |
O12 | 0.3751 (2) | 0.33240 (17) | 0.39985 (9) | 0.0371 (3) | |
O13 | 0.0778 (2) | 0.2607 (2) | 0.49744 (9) | 0.0534 (4) | |
O14 | −0.5137 (2) | −0.07121 (17) | 0.40512 (9) | 0.0396 (3) | |
O15 | −0.4859 (2) | −0.16322 (15) | 0.25825 (10) | 0.0366 (3) | |
O16 | 0.2234 (2) | −0.05385 (14) | 0.03198 (9) | 0.0323 (3) | |
O17 | 0.2799 (2) | 0.21390 (15) | 0.02874 (9) | 0.0334 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0296 (8) | 0.0360 (8) | 0.0185 (7) | −0.0172 (6) | −0.0015 (6) | −0.0027 (6) |
C1 | 0.0220 (7) | 0.0191 (7) | 0.0183 (7) | −0.0042 (5) | −0.0013 (6) | −0.0009 (6) |
N2 | 0.0207 (6) | 0.0211 (6) | 0.0201 (7) | −0.0059 (5) | −0.0014 (5) | −0.0018 (5) |
C3 | 0.0273 (8) | 0.0228 (7) | 0.0186 (8) | −0.0021 (6) | −0.0026 (6) | −0.0037 (6) |
C4 | 0.0275 (8) | 0.0234 (7) | 0.0227 (8) | −0.0042 (6) | −0.0063 (6) | −0.0054 (6) |
C5 | 0.0226 (7) | 0.0211 (7) | 0.0254 (8) | −0.0073 (6) | −0.0034 (6) | −0.0035 (6) |
N6 | 0.0244 (7) | 0.0235 (6) | 0.0206 (7) | −0.0087 (5) | −0.0015 (5) | −0.0031 (5) |
C11 | 0.0190 (7) | 0.0181 (7) | 0.0215 (8) | −0.0028 (5) | −0.0030 (6) | −0.0020 (6) |
C12 | 0.0205 (7) | 0.0205 (7) | 0.0187 (8) | −0.0034 (6) | −0.0049 (6) | −0.0030 (6) |
C13 | 0.0200 (7) | 0.0199 (7) | 0.0199 (8) | −0.0011 (5) | −0.0007 (6) | 0.0001 (6) |
C14 | 0.0158 (7) | 0.0179 (7) | 0.0255 (8) | −0.0042 (5) | −0.0022 (6) | −0.0012 (6) |
C15 | 0.0221 (7) | 0.0193 (7) | 0.0226 (8) | −0.0019 (5) | −0.0063 (6) | −0.0048 (6) |
C16 | 0.0208 (7) | 0.0208 (7) | 0.0176 (8) | −0.0014 (6) | −0.0025 (6) | −0.0018 (6) |
N11 | 0.0244 (7) | 0.0276 (7) | 0.0196 (7) | −0.0063 (5) | −0.0023 (5) | −0.0039 (5) |
N12 | 0.0193 (6) | 0.0241 (6) | 0.0316 (8) | −0.0048 (5) | −0.0031 (5) | −0.0008 (6) |
N13 | 0.0212 (6) | 0.0270 (7) | 0.0201 (7) | −0.0026 (5) | −0.0035 (5) | −0.0052 (5) |
O11 | 0.0226 (6) | 0.0368 (6) | 0.0233 (6) | −0.0141 (5) | 0.0006 (4) | −0.0050 (5) |
O12 | 0.0342 (7) | 0.0518 (8) | 0.0267 (6) | −0.0260 (6) | −0.0030 (5) | −0.0070 (5) |
O13 | 0.0449 (8) | 0.0925 (12) | 0.0221 (7) | −0.0335 (7) | 0.0095 (6) | −0.0245 (7) |
O14 | 0.0298 (7) | 0.0545 (8) | 0.0322 (7) | −0.0175 (6) | 0.0075 (5) | −0.0038 (6) |
O15 | 0.0306 (6) | 0.0386 (7) | 0.0425 (8) | −0.0170 (5) | −0.0067 (5) | −0.0107 (6) |
O16 | 0.0375 (7) | 0.0321 (6) | 0.0272 (6) | −0.0035 (5) | −0.0006 (5) | −0.0137 (5) |
O17 | 0.0422 (7) | 0.0339 (6) | 0.0227 (6) | −0.0089 (5) | 0.0017 (5) | 0.0014 (5) |
N1—C1 | 1.320 (2) | C12—C13 | 1.392 (2) |
N1—H1A | 0.87 (2) | C12—N11 | 1.4631 (19) |
N1—H1B | 0.91 (2) | C13—C14 | 1.385 (2) |
C1—N6 | 1.3622 (19) | C13—H13 | 0.9500 |
C1—N2 | 1.3643 (19) | C14—C15 | 1.397 (2) |
N2—C3 | 1.3572 (19) | C14—N12 | 1.4568 (18) |
N2—H2 | 0.90 (2) | C15—C16 | 1.368 (2) |
C3—C4 | 1.368 (2) | C15—H15 | 0.9500 |
C3—H3 | 0.9500 | C16—N13 | 1.4682 (19) |
C4—C5 | 1.404 (2) | N11—O13 | 1.2202 (18) |
C4—H4 | 0.9500 | N11—O12 | 1.2262 (17) |
C5—N6 | 1.324 (2) | N12—O14 | 1.2258 (18) |
C5—H5 | 0.9500 | N12—O15 | 1.2349 (17) |
C11—O11 | 1.2588 (18) | N13—O17 | 1.2289 (17) |
C11—C12 | 1.444 (2) | N13—O16 | 1.2345 (17) |
C11—C16 | 1.452 (2) | ||
C1—N1—H1A | 115.1 (13) | C13—C12—N11 | 116.45 (13) |
C1—N1—H1B | 117.1 (13) | C11—C12—N11 | 120.10 (12) |
H1A—N1—H1B | 127.5 (19) | C14—C13—C12 | 118.89 (14) |
N1—C1—N6 | 119.19 (14) | C14—C13—H13 | 120.6 |
N1—C1—N2 | 120.24 (13) | C12—C13—H13 | 120.6 |
N6—C1—N2 | 120.57 (13) | C13—C14—C15 | 122.04 (13) |
C3—N2—C1 | 121.42 (13) | C13—C14—N12 | 119.44 (14) |
C3—N2—H2 | 122.1 (13) | C15—C14—N12 | 118.50 (13) |
C1—N2—H2 | 116.5 (13) | C16—C15—C14 | 118.09 (13) |
N2—C3—C4 | 119.58 (14) | C16—C15—H15 | 121.0 |
N2—C3—H3 | 120.2 | C14—C15—H15 | 121.0 |
C4—C3—H3 | 120.2 | C15—C16—C11 | 124.88 (14) |
C3—C4—C5 | 116.62 (14) | C15—C16—N13 | 117.24 (13) |
C3—C4—H4 | 121.7 | C11—C16—N13 | 117.85 (12) |
C5—C4—H4 | 121.7 | O13—N11—O12 | 121.68 (13) |
N6—C5—C4 | 124.25 (14) | O13—N11—C12 | 118.02 (12) |
N6—C5—H5 | 117.9 | O12—N11—C12 | 120.30 (13) |
C4—C5—H5 | 117.9 | O14—N12—O15 | 123.36 (13) |
C5—N6—C1 | 117.53 (13) | O14—N12—C14 | 118.93 (13) |
O11—C11—C12 | 125.89 (13) | O15—N12—C14 | 117.70 (13) |
O11—C11—C16 | 121.46 (13) | O17—N13—O16 | 123.85 (13) |
C12—C11—C16 | 112.63 (13) | O17—N13—C16 | 118.75 (12) |
C13—C12—C11 | 123.45 (13) | O16—N13—C16 | 117.38 (12) |
N1—C1—N2—C3 | −179.40 (14) | C14—C15—C16—C11 | 2.1 (2) |
N6—C1—N2—C3 | 0.7 (2) | C14—C15—C16—N13 | −179.82 (13) |
C1—N2—C3—C4 | −1.3 (2) | O11—C11—C16—C15 | 176.85 (14) |
N2—C3—C4—C5 | 0.6 (2) | C12—C11—C16—C15 | −1.5 (2) |
C3—C4—C5—N6 | 0.7 (2) | O11—C11—C16—N13 | −1.2 (2) |
C4—C5—N6—C1 | −1.3 (2) | C12—C11—C16—N13 | −179.53 (12) |
N1—C1—N6—C5 | −179.32 (15) | C13—C12—N11—O13 | −2.7 (2) |
N2—C1—N6—C5 | 0.6 (2) | C11—C12—N11—O13 | 176.73 (15) |
O11—C11—C12—C13 | −178.11 (14) | C13—C12—N11—O12 | 177.68 (14) |
C16—C11—C12—C13 | 0.2 (2) | C11—C12—N11—O12 | −2.9 (2) |
O11—C11—C12—N11 | 2.5 (2) | C13—C14—N12—O14 | 4.9 (2) |
C16—C11—C12—N11 | −179.19 (12) | C15—C14—N12—O14 | −176.38 (14) |
C11—C12—C13—C14 | 0.4 (2) | C13—C14—N12—O15 | −175.46 (14) |
N11—C12—C13—C14 | 179.81 (13) | C15—C14—N12—O15 | 3.2 (2) |
C12—C13—C14—C15 | 0.2 (2) | C15—C16—N13—O17 | 133.79 (15) |
C12—C13—C14—N12 | 178.82 (13) | C11—C16—N13—O17 | −48.03 (19) |
C13—C14—C15—C16 | −1.4 (2) | C15—C16—N13—O16 | −44.61 (19) |
N12—C14—C15—C16 | 179.93 (13) | C11—C16—N13—O16 | 133.57 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N6i | 0.87 (2) | 2.09 (2) | 2.958 (2) | 177.0 (18) |
N1—H1B···O11 | 0.91 (2) | 1.97 (2) | 2.7577 (19) | 143.7 (18) |
N1—H1B···O17 | 0.91 (2) | 2.50 (2) | 3.2488 (18) | 140.0 (17) |
N2—H2···O11 | 0.90 (2) | 1.84 (2) | 2.6501 (16) | 148.6 (19) |
N2—H2···O12 | 0.90 (2) | 2.31 (2) | 2.9792 (18) | 131.6 (17) |
Symmetry code: (i) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C4H6N3+·C6H2N3O7− |
Mr | 324.22 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 5.8803 (7), 8.0025 (10), 13.8108 (17) |
α, β, γ (°) | 88.021 (10), 82.322 (9), 88.739 (10) |
V (Å3) | 643.59 (14) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.26 × 0.22 × 0.09 |
Data collection | |
Diffractometer | Stoe IPDSII two-circle |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8757, 2402, 1927 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.608 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.099, 1.01 |
No. of reflections | 2402 |
No. of parameters | 220 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.27 |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N6i | 0.87 (2) | 2.09 (2) | 2.958 (2) | 177.0 (18) |
N1—H1B···O11 | 0.91 (2) | 1.97 (2) | 2.7577 (19) | 143.7 (18) |
N1—H1B···O17 | 0.91 (2) | 2.50 (2) | 3.2488 (18) | 140.0 (17) |
N2—H2···O11 | 0.90 (2) | 1.84 (2) | 2.6501 (16) | 148.6 (19) |
N2—H2···O12 | 0.90 (2) | 2.31 (2) | 2.9792 (18) | 131.6 (17) |
Symmetry code: (i) −x+2, −y+1, −z. |
Acknowledgements
BN thanks Mangalore University for the use of research facilities.
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Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring. A pyrimidine has many properties in common with pyridine, as the number of nitrogen atoms in the ring increases the ring π-electrons become less energetic and electrophilic aromatic substitution gets more difficult while nucleophilic aromatic substitution gets easier. Pyrimidines are important compounds in pharmaceutical chemistry as antiviral agents (Gueiffier et al., 1996), inotropic and β-blocking agents (Barraclough & Smith, 1995), antifungal agents (Rival et al. 1991), benzodiazepine receptor agonists (Tully et al.1991), and calcium channel blockers (Sanfilippo et al., 1988). The synthesis of imidazo[1,2-a]pyrimidines has been widely investigated and one of the most common strategies uses 2-aminopyrimidine as the starting material (Katritzky et al., 2003). The crystal structures of the following compounds have been previously reported, viz; 2-aminopyrimidine (Scheinbeim & Schempp, 1976), 1:1 hetero-assembly of 2-aminopyrimidine and (+)-camphoric acid (Goswami, et al., 2000), 2-aminopyrimidine-succinic acid (1:1) cocrystal (Etter et al., 1990), 5-aminopyrimidine (Schlueter et al., 2006), 5-bromopyrimidin-2(1H)-one (Yathirajan, Narayana, Ashalatha et al., 2007), ethyl 7-methyl-2-[4-(methylsulfanyl)benzylidene]-5-[4-(methylsulfanyl)phenyl]-3-oxo-2, 3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate (Fischer et al., 2007), 2-(4-methylbenzoyloxymethyl)-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1 -yl)tetrahydrofuran-3-yl 4-methylbenzoate (Yathirajan, Mayekar, Sarojini et al., 2007), methyl (4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-5-yl)acetate (Yathirajan, Bindya, Sarojini et al., 2007a), ethyl (4-oxo-1-phenyl-1,4-dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-yl)acetate (Yathirajan, Bindya, Sarojini et al., 2007b). In continuation to our work on picrates of biologically important molecules, we have prepared a new picrate of 2-aminopyrimidine, and its crystal structure is reported.
Geometric parameters of the title compound are in the usual ranges. Whereas two nitrogroups are almost coplanar with the aromatic picrate ring [dihedral angles 3.0 (2)° and 4.4 (3)°] the third one is significantly twisted [dihedral angle 46.47 (8)°] out of this plane Anions and cations are connected via N—H···O hydrogen bonds. The molecules crystallize in planes parallel to (1 - 2 1).