organic compounds
6-Amino-2,5-bis(pivaloylamino)pyrimidin-4(3H)-one dihydrate
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
*Correspondence e-mail: hkfun@usm.my
The 14H23N5O3·2H2O, contains two crystallographically independent 6-amino-2,5-bis(pivaloylamino)pyrimidin-4(3H)-one molecules (A and B) with similar geometry and four water molecules. In both independent molecules, one of the amide groups is almost coplanar with the pyrimidine ring [dihedral angle of 12.85 (9) in A and 12.30 (10)° in B], whereas the other amide group is significantly twisted away from it [dihedral angle is 72.18 (7) in A and 71.29 (7)° in B]. In each independent molecule, an intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. Molecules A and B are linked into chains along the a axis by N—H⋯O and C—H⋯O hydrogen bonds. Adjacent chains are linked into a two-dimensional network parallel to the ac plane by water molecules via N—H⋯O and O—H⋯O hydrogen bonds.
of the title compound, CRelated literature
For general background on substituted pyrimidines, see: Lednicer & Mitscher (1977); Blackburn & Gait (1996); VanAllan (1976); Goswami et al. (2007); Brown (1988). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536809019461/ci2809sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809019461/ci2809Isup2.hkl
2,5,6-Triaminopyrimidine-4-(3H)-one dihydrochloride (200mg, 0.93mmol) was heated with pivalic anhydride (1 ml) at 393 K for 6 h in the presence of a catalytic amount of 4-dimethylaminopyridine (DMAP) (10 mol%). After the formation of a major amount of dipivaloyl product as monitored by TLC, the solid residue was washed with petroleum ether to remove the excess pivalic anhydride. The solid residue was purified through silica gel (100–200 mesh) δ(p.p.m.): 11.61 (bs, 1H), 8.27 (bs, 1H), 7.64 (bs, 1H), 5.35 (bs, 2H), 1.28 (s, 9H), 1.24 (s, 9H). LC—MS: m/z (%): 310.4[(M+H)+,40], 292.3 (100), 186.3.
eluting 3% methanol in chloroform to get the pure crystalline solid. Single crystals were grown by slow evaporation of a chloroform solution (m.p. 523-525 K). IR: 3416, 3217, 2965, 2873,1645, 1568, 1488, 1438, 1240, 1176, 763 cm-1. 1H NMR (CDCl3, 400 MHz):H atoms were positioned geometrically (N-H = 0.86 Å and C-H = 0.93–0.96 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(methyl C). A rotating–group model was used for the methyl groups. The H atoms of the water molecules were located in a difference Fourier map and constrained to ride on their parent atom, with Uiso(H) = 1.5Ueq(O). The crystal was a pseudo-merohedral triplet with ratio 0.764 (5):0.155 (5):0.081 (5). The refined BASF parameters are 0.155 (5) and 0.081 (5).
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Dashed lines indicate hydrogen bonding. | |
Fig. 2. Part of the crystal packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonding. |
C14H23N5O3·2H2O | Z = 4 |
Mr = 345.41 | F(000) = 744 |
Triclinic, P1 | Dx = 1.262 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5560 (3) Å | Cell parameters from 8925 reflections |
b = 14.1008 (6) Å | θ = 3.1–32.5° |
c = 18.0713 (6) Å | µ = 0.10 mm−1 |
α = 71.079 (2)° | T = 100 K |
β = 89.988 (2)° | Block, colourless |
γ = 86.682 (3)° | 0.57 × 0.19 × 0.09 mm |
V = 1817.98 (12) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 10525 independent reflections |
Radiation source: fine-focus sealed tube | 8199 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
ϕ and ω scans | θmax = 30.0°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −10→10 |
Tmin = 0.947, Tmax = 0.991 | k = −18→19 |
10525 measured reflections | l = 0→25 |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0332P)2 + 1.7967P] where P = (Fo2 + 2Fc2)/3 |
10525 reflections | (Δ/σ)max = 0.001 |
447 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C14H23N5O3·2H2O | γ = 86.682 (3)° |
Mr = 345.41 | V = 1817.98 (12) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.5560 (3) Å | Mo Kα radiation |
b = 14.1008 (6) Å | µ = 0.10 mm−1 |
c = 18.0713 (6) Å | T = 100 K |
α = 71.079 (2)° | 0.57 × 0.19 × 0.09 mm |
β = 89.988 (2)° |
Bruker SMART APEXII CCD area-detector diffractometer | 10525 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 8199 reflections with I > 2σ(I) |
Tmin = 0.947, Tmax = 0.991 | Rint = 0.000 |
10525 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.42 e Å−3 |
10525 reflections | Δρmin = −0.35 e Å−3 |
447 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
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 | ||
O1A | 1.0113 (2) | 0.26217 (11) | 0.14678 (9) | 0.0172 (3) | |
O2A | 0.9781 (2) | −0.00932 (11) | 0.11107 (8) | 0.0163 (3) | |
O3A | 1.2104 (2) | −0.26095 (12) | 0.29920 (9) | 0.0211 (3) | |
N1A | 0.7981 (2) | 0.15883 (12) | 0.14173 (9) | 0.0126 (3) | |
H1AA | 0.6995 | 0.1522 | 0.1207 | 0.015* | |
N2A | 0.9705 (2) | −0.00908 (12) | 0.33668 (9) | 0.0124 (3) | |
N3A | 1.0445 (2) | −0.08254 (12) | 0.24031 (9) | 0.0126 (3) | |
H3AA | 1.0950 | −0.1334 | 0.2306 | 0.015* | |
N4A | 1.1220 (2) | −0.16358 (12) | 0.37291 (9) | 0.0129 (3) | |
H4AA | 1.1299 | −0.1587 | 0.4190 | 0.016* | |
N5A | 0.8070 (2) | 0.14048 (13) | 0.30396 (10) | 0.0151 (3) | |
H5AA | 0.8136 | 0.1356 | 0.3526 | 0.018* | |
H5AB | 0.7506 | 0.1916 | 0.2712 | 0.018* | |
C1A | 0.8701 (3) | 0.24963 (15) | 0.11802 (11) | 0.0121 (4) | |
C2A | 0.8808 (3) | 0.07412 (14) | 0.20033 (11) | 0.0121 (4) | |
C3A | 0.8843 (3) | 0.06879 (14) | 0.27938 (11) | 0.0120 (4) | |
C4A | 1.0438 (3) | −0.08141 (14) | 0.31492 (11) | 0.0126 (4) | |
C5A | 0.9655 (3) | −0.00353 (15) | 0.17828 (11) | 0.0120 (4) | |
C6A | 1.1882 (3) | −0.25228 (15) | 0.36395 (11) | 0.0137 (4) | |
C7A | 1.2277 (3) | −0.33855 (15) | 0.44031 (12) | 0.0154 (4) | |
C8A | 1.2899 (3) | −0.43211 (17) | 0.42020 (13) | 0.0211 (5) | |
H8AA | 1.1995 | −0.4482 | 0.3896 | 0.032* | |
H8AB | 1.3124 | −0.4874 | 0.4676 | 0.032* | |
H8AC | 1.3967 | −0.4196 | 0.3907 | 0.032* | |
C9A | 1.3758 (4) | −0.31103 (18) | 0.48672 (14) | 0.0228 (5) | |
H9AA | 1.3385 | −0.2512 | 0.4983 | 0.034* | |
H9AB | 1.4811 | −0.2995 | 0.4561 | 0.034* | |
H9AC | 1.4001 | −0.3652 | 0.5347 | 0.034* | |
C10A | 1.0576 (3) | −0.35827 (17) | 0.48821 (13) | 0.0217 (5) | |
H10A | 0.9629 | −0.3673 | 0.4562 | 0.033* | |
H10B | 1.0265 | −0.3021 | 0.5056 | 0.033* | |
H10C | 1.0771 | −0.4178 | 0.5328 | 0.033* | |
C11A | 0.7768 (3) | 0.33580 (15) | 0.05214 (12) | 0.0152 (4) | |
C12A | 0.9017 (4) | 0.3536 (2) | −0.01777 (14) | 0.0334 (6) | |
H12A | 0.8555 | 0.4103 | −0.0604 | 0.050* | |
H12B | 0.9102 | 0.2951 | −0.0340 | 0.050* | |
H12C | 1.0172 | 0.3666 | −0.0026 | 0.050* | |
C13A | 0.7607 (4) | 0.42818 (17) | 0.07890 (17) | 0.0278 (5) | |
H13A | 0.6818 | 0.4161 | 0.1222 | 0.042* | |
H13B | 0.7147 | 0.4852 | 0.0365 | 0.042* | |
H13C | 0.8754 | 0.4413 | 0.0948 | 0.042* | |
C14A | 0.5943 (3) | 0.31374 (17) | 0.02795 (14) | 0.0226 (5) | |
H14A | 0.5179 | 0.2988 | 0.0722 | 0.034* | |
H14B | 0.6054 | 0.2572 | 0.0093 | 0.034* | |
H14C | 0.5447 | 0.3714 | −0.0129 | 0.034* | |
O1B | 0.5105 (2) | 0.26137 (11) | 0.21892 (9) | 0.0177 (3) | |
O2B | 0.4795 (2) | −0.01130 (11) | 0.39406 (8) | 0.0160 (3) | |
O3B | 0.7098 (2) | −0.26303 (12) | 0.33417 (9) | 0.0213 (3) | |
N1B | 0.3005 (2) | 0.15684 (12) | 0.27823 (10) | 0.0124 (3) | |
H1BA | 0.2027 | 0.1501 | 0.3032 | 0.015* | |
N2B | 0.4710 (2) | −0.01103 (12) | 0.16825 (9) | 0.0124 (3) | |
N3B | 0.5460 (2) | −0.08400 (12) | 0.30196 (9) | 0.0125 (3) | |
H3BA | 0.5972 | −0.1345 | 0.3374 | 0.015* | |
N4B | 0.6226 (2) | −0.16539 (13) | 0.21065 (10) | 0.0135 (3) | |
H4BA | 0.6310 | −0.1607 | 0.1622 | 0.016* | |
N5B | 0.3072 (2) | 0.13860 (13) | 0.12500 (10) | 0.0143 (3) | |
H5BA | 0.3129 | 0.1333 | 0.0790 | 0.017* | |
H5BB | 0.2512 | 0.1899 | 0.1319 | 0.017* | |
C1B | 0.3719 (3) | 0.24772 (15) | 0.25544 (11) | 0.0123 (4) | |
C2B | 0.3819 (3) | 0.07227 (14) | 0.26221 (11) | 0.0124 (4) | |
C3B | 0.3855 (3) | 0.06723 (14) | 0.18588 (11) | 0.0113 (3) | |
C4B | 0.5443 (3) | −0.08344 (14) | 0.22681 (11) | 0.0118 (4) | |
C5B | 0.4673 (3) | −0.00523 (15) | 0.32382 (11) | 0.0129 (4) | |
C6B | 0.6886 (3) | −0.25413 (15) | 0.26499 (12) | 0.0149 (4) | |
C7B | 0.7303 (3) | −0.34013 (16) | 0.23251 (12) | 0.0162 (4) | |
C8B | 0.7917 (4) | −0.43431 (17) | 0.30020 (14) | 0.0226 (5) | |
H8BA | 0.7000 | −0.4511 | 0.3382 | 0.034* | |
H8BB | 0.8970 | −0.4216 | 0.3242 | 0.034* | |
H8BC | 0.8165 | −0.4892 | 0.2805 | 0.034* | |
C9B | 0.8798 (4) | −0.31215 (18) | 0.17286 (14) | 0.0232 (5) | |
H9BA | 0.8418 | −0.2534 | 0.1302 | 0.035* | |
H9BB | 0.9078 | −0.3669 | 0.1534 | 0.035* | |
H9BC | 0.9832 | −0.2987 | 0.1978 | 0.035* | |
C10B | 0.5631 (3) | −0.36058 (17) | 0.19338 (14) | 0.0231 (5) | |
H10D | 0.5312 | −0.3038 | 0.1481 | 0.035* | |
H10E | 0.4676 | −0.3716 | 0.2297 | 0.035* | |
H10F | 0.5858 | −0.4191 | 0.1779 | 0.035* | |
C11B | 0.2801 (3) | 0.33333 (16) | 0.27831 (12) | 0.0150 (4) | |
C12B | 0.4114 (4) | 0.3547 (2) | 0.33506 (17) | 0.0323 (6) | |
H12D | 0.4266 | 0.2970 | 0.3813 | 0.049* | |
H12E | 0.3659 | 0.4114 | 0.3491 | 0.049* | |
H12F | 0.5235 | 0.3691 | 0.3102 | 0.049* | |
C13B | 0.2533 (3) | 0.42518 (17) | 0.20411 (14) | 0.0214 (5) | |
H13D | 0.1719 | 0.4108 | 0.1689 | 0.032* | |
H13E | 0.3650 | 0.4404 | 0.1791 | 0.032* | |
H13F | 0.2062 | 0.4817 | 0.2180 | 0.032* | |
C14B | 0.1021 (4) | 0.30911 (17) | 0.31798 (15) | 0.0236 (5) | |
H14D | 0.0220 | 0.2929 | 0.2833 | 0.035* | |
H14E | 0.0533 | 0.3663 | 0.3305 | 0.035* | |
H14F | 0.1191 | 0.2529 | 0.3651 | 0.035* | |
O1W | 0.8987 (2) | 0.12286 (11) | 0.47888 (8) | 0.0179 (3) | |
H1W1 | 0.8648 | 0.0614 | 0.4942 | 0.027* | |
H2W1 | 1.0149 | 0.1036 | 0.4798 | 0.027* | |
O2W | 0.2630 (2) | 0.06473 (13) | 0.48386 (9) | 0.0219 (3) | |
H1W2 | 0.3371 | 0.0602 | 0.4483 | 0.033* | |
H2W2 | 0.3376 | 0.0610 | 0.5230 | 0.033* | |
O3W | 0.2385 (2) | 0.93480 (13) | 0.01760 (9) | 0.0225 (3) | |
H1W3 | 0.1642 | 0.9417 | −0.0197 | 0.034* | |
H2W3 | 0.1705 | 0.9430 | 0.0559 | 0.034* | |
O4W | 0.6016 (2) | 0.87651 (11) | 0.04160 (9) | 0.0181 (3) | |
H1W4 | 0.6432 | 0.9365 | 0.0213 | 0.027* | |
H2W4 | 0.4873 | 0.8911 | 0.0321 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0161 (7) | 0.0141 (7) | 0.0198 (7) | −0.0005 (6) | −0.0036 (6) | −0.0033 (6) |
O2A | 0.0219 (8) | 0.0187 (7) | 0.0083 (6) | 0.0010 (6) | −0.0016 (5) | −0.0050 (5) |
O3A | 0.0304 (9) | 0.0205 (8) | 0.0122 (7) | 0.0059 (7) | −0.0003 (6) | −0.0064 (6) |
N1A | 0.0131 (8) | 0.0133 (8) | 0.0096 (7) | −0.0008 (6) | −0.0027 (6) | −0.0013 (6) |
N2A | 0.0155 (8) | 0.0121 (8) | 0.0091 (7) | 0.0010 (6) | −0.0006 (6) | −0.0032 (6) |
N3A | 0.0166 (9) | 0.0113 (7) | 0.0098 (7) | 0.0017 (6) | 0.0001 (6) | −0.0038 (6) |
N4A | 0.0181 (9) | 0.0128 (8) | 0.0076 (7) | 0.0011 (6) | −0.0022 (6) | −0.0034 (6) |
N5A | 0.0211 (9) | 0.0140 (8) | 0.0099 (7) | 0.0028 (7) | −0.0001 (6) | −0.0039 (6) |
C1A | 0.0135 (9) | 0.0124 (9) | 0.0104 (8) | 0.0001 (7) | 0.0030 (7) | −0.0039 (7) |
C2A | 0.0139 (9) | 0.0117 (8) | 0.0093 (8) | −0.0004 (7) | −0.0003 (7) | −0.0016 (6) |
C3A | 0.0122 (9) | 0.0121 (8) | 0.0115 (8) | −0.0020 (7) | 0.0008 (7) | −0.0034 (7) |
C4A | 0.0144 (9) | 0.0121 (9) | 0.0101 (8) | −0.0021 (7) | −0.0001 (7) | −0.0018 (7) |
C5A | 0.0130 (9) | 0.0123 (9) | 0.0100 (8) | −0.0011 (7) | −0.0006 (7) | −0.0025 (7) |
C6A | 0.0161 (10) | 0.0127 (9) | 0.0117 (8) | 0.0008 (7) | −0.0024 (7) | −0.0036 (7) |
C7A | 0.0212 (11) | 0.0116 (9) | 0.0123 (8) | 0.0031 (8) | −0.0009 (7) | −0.0028 (7) |
C8A | 0.0267 (12) | 0.0162 (10) | 0.0195 (10) | 0.0064 (9) | −0.0036 (9) | −0.0060 (8) |
C9A | 0.0289 (13) | 0.0181 (10) | 0.0203 (10) | 0.0041 (9) | −0.0108 (9) | −0.0058 (8) |
C10A | 0.0285 (12) | 0.0152 (10) | 0.0176 (10) | 0.0022 (9) | 0.0055 (9) | −0.0008 (8) |
C11A | 0.0162 (10) | 0.0114 (9) | 0.0134 (9) | 0.0014 (7) | 0.0011 (7) | 0.0020 (7) |
C12A | 0.0294 (14) | 0.0379 (14) | 0.0190 (11) | 0.0033 (11) | 0.0085 (10) | 0.0091 (10) |
C13A | 0.0262 (13) | 0.0136 (10) | 0.0416 (14) | 0.0029 (9) | −0.0079 (11) | −0.0068 (10) |
C14A | 0.0252 (12) | 0.0180 (10) | 0.0197 (10) | 0.0009 (9) | −0.0074 (9) | 0.0003 (8) |
O1B | 0.0167 (8) | 0.0150 (7) | 0.0211 (7) | −0.0010 (6) | 0.0034 (6) | −0.0054 (6) |
O2B | 0.0196 (8) | 0.0199 (7) | 0.0100 (6) | 0.0030 (6) | −0.0009 (5) | −0.0078 (5) |
O3B | 0.0317 (9) | 0.0179 (7) | 0.0140 (7) | 0.0072 (6) | −0.0030 (6) | −0.0061 (6) |
N1B | 0.0126 (8) | 0.0126 (8) | 0.0144 (7) | 0.0003 (6) | 0.0023 (6) | −0.0077 (6) |
N2B | 0.0147 (8) | 0.0128 (8) | 0.0109 (7) | 0.0001 (6) | 0.0002 (6) | −0.0057 (6) |
N3B | 0.0163 (9) | 0.0116 (7) | 0.0096 (7) | 0.0020 (6) | −0.0005 (6) | −0.0039 (6) |
N4B | 0.0189 (9) | 0.0134 (8) | 0.0099 (7) | 0.0019 (7) | 0.0003 (6) | −0.0065 (6) |
N5B | 0.0188 (9) | 0.0136 (8) | 0.0112 (7) | 0.0028 (6) | −0.0018 (6) | −0.0055 (6) |
C1B | 0.0147 (10) | 0.0115 (9) | 0.0109 (8) | 0.0016 (7) | −0.0033 (7) | −0.0045 (7) |
C2B | 0.0141 (9) | 0.0123 (9) | 0.0131 (8) | −0.0008 (7) | 0.0005 (7) | −0.0075 (7) |
C3B | 0.0111 (9) | 0.0118 (8) | 0.0115 (8) | −0.0015 (7) | −0.0005 (7) | −0.0046 (7) |
C4B | 0.0120 (9) | 0.0120 (8) | 0.0128 (8) | −0.0008 (7) | 0.0012 (7) | −0.0060 (7) |
C5B | 0.0136 (9) | 0.0144 (9) | 0.0128 (8) | −0.0017 (7) | 0.0026 (7) | −0.0072 (7) |
C6B | 0.0149 (10) | 0.0137 (9) | 0.0167 (9) | 0.0006 (7) | 0.0012 (7) | −0.0061 (7) |
C7B | 0.0213 (11) | 0.0139 (9) | 0.0151 (9) | 0.0025 (8) | −0.0003 (8) | −0.0077 (7) |
C8B | 0.0314 (13) | 0.0146 (10) | 0.0207 (10) | 0.0058 (9) | −0.0015 (9) | −0.0052 (8) |
C9B | 0.0279 (13) | 0.0197 (11) | 0.0213 (10) | 0.0055 (9) | 0.0072 (9) | −0.0070 (8) |
C10B | 0.0278 (13) | 0.0183 (10) | 0.0254 (11) | 0.0016 (9) | −0.0080 (9) | −0.0104 (9) |
C11B | 0.0182 (10) | 0.0127 (9) | 0.0156 (9) | 0.0024 (8) | −0.0023 (8) | −0.0072 (7) |
C12B | 0.0392 (16) | 0.0310 (13) | 0.0356 (14) | 0.0070 (11) | −0.0154 (12) | −0.0244 (11) |
C13B | 0.0234 (12) | 0.0134 (10) | 0.0259 (11) | 0.0010 (8) | 0.0008 (9) | −0.0048 (8) |
C14B | 0.0283 (13) | 0.0164 (10) | 0.0272 (11) | 0.0030 (9) | 0.0100 (10) | −0.0092 (9) |
O1W | 0.0225 (8) | 0.0167 (7) | 0.0140 (7) | 0.0023 (6) | 0.0011 (6) | −0.0049 (5) |
O2W | 0.0174 (8) | 0.0347 (9) | 0.0155 (7) | 0.0048 (7) | 0.0001 (6) | −0.0119 (6) |
O3W | 0.0190 (8) | 0.0352 (9) | 0.0148 (7) | 0.0039 (7) | −0.0031 (6) | −0.0111 (6) |
O4W | 0.0209 (8) | 0.0176 (7) | 0.0162 (7) | 0.0037 (6) | −0.0026 (6) | −0.0067 (6) |
O1A—C1A | 1.233 (3) | N1B—C2B | 1.422 (2) |
O2A—C5A | 1.247 (2) | N1B—H1BA | 0.86 |
O3A—C6A | 1.226 (2) | N2B—C4B | 1.305 (3) |
N1A—C1A | 1.358 (2) | N2B—C3B | 1.372 (2) |
N1A—C2A | 1.426 (2) | N3B—C4B | 1.355 (2) |
N1A—H1AA | 0.86 | N3B—C5B | 1.397 (2) |
N2A—C4A | 1.302 (3) | N3B—H3BA | 0.86 |
N2A—C3A | 1.372 (3) | N4B—C6B | 1.382 (3) |
N3A—C4A | 1.354 (2) | N4B—C4B | 1.382 (2) |
N3A—C5A | 1.403 (2) | N4B—H4BA | 0.86 |
N3A—H3AA | 0.86 | N5B—C3B | 1.336 (2) |
N4A—C6A | 1.378 (3) | N5B—H5BA | 0.86 |
N4A—C4A | 1.387 (2) | N5B—H5BB | 0.86 |
N4A—H4AA | 0.86 | C1B—C11B | 1.529 (3) |
N5A—C3A | 1.335 (3) | C2B—C3B | 1.404 (3) |
N5A—H5AA | 0.86 | C2B—C5B | 1.407 (3) |
N5A—H5AB | 0.86 | C6B—C7B | 1.527 (3) |
C1A—C11A | 1.534 (3) | C7B—C8B | 1.533 (3) |
C2A—C5A | 1.403 (3) | C7B—C10B | 1.535 (3) |
C2A—C3A | 1.406 (3) | C7B—C9B | 1.539 (3) |
C6A—C7A | 1.531 (3) | C8B—H8BA | 0.96 |
C7A—C8A | 1.527 (3) | C8B—H8BB | 0.96 |
C7A—C10A | 1.538 (3) | C8B—H8BC | 0.96 |
C7A—C9A | 1.538 (3) | C9B—H9BA | 0.96 |
C8A—H8AA | 0.96 | C9B—H9BB | 0.96 |
C8A—H8AB | 0.96 | C9B—H9BC | 0.96 |
C8A—H8AC | 0.96 | C10B—H10D | 0.96 |
C9A—H9AA | 0.96 | C10B—H10E | 0.96 |
C9A—H9AB | 0.96 | C10B—H10F | 0.96 |
C9A—H9AC | 0.96 | C11B—C14B | 1.527 (3) |
C10A—H10A | 0.96 | C11B—C13B | 1.536 (3) |
C10A—H10B | 0.96 | C11B—C12B | 1.537 (3) |
C10A—H10C | 0.96 | C12B—H12D | 0.96 |
C11A—C14A | 1.526 (3) | C12B—H12E | 0.96 |
C11A—C13A | 1.528 (3) | C12B—H12F | 0.96 |
C11A—C12A | 1.539 (3) | C13B—H13D | 0.96 |
C12A—H12A | 0.96 | C13B—H13E | 0.96 |
C12A—H12B | 0.96 | C13B—H13F | 0.96 |
C12A—H12C | 0.96 | C14B—H14D | 0.96 |
C13A—H13A | 0.96 | C14B—H14E | 0.96 |
C13A—H13B | 0.96 | C14B—H14F | 0.96 |
C13A—H13C | 0.96 | O1W—H1W1 | 0.87 |
C14A—H14A | 0.96 | O1W—H2W1 | 0.90 |
C14A—H14B | 0.96 | O2W—H1W2 | 0.87 |
C14A—H14C | 0.96 | O2W—H2W2 | 0.89 |
O1B—C1B | 1.229 (3) | O3W—H1W3 | 0.85 |
O2B—C5B | 1.247 (2) | O3W—H2W3 | 0.89 |
O3B—C6B | 1.225 (3) | O4W—H1W4 | 0.88 |
N1B—C1B | 1.357 (3) | O4W—H2W4 | 0.88 |
C1A—N1A—C2A | 122.09 (17) | C2B—N1B—H1BA | 118.9 |
C1A—N1A—H1AA | 119.0 | C4B—N2B—C3B | 116.57 (16) |
C2A—N1A—H1AA | 119.0 | C4B—N3B—C5B | 122.21 (17) |
C4A—N2A—C3A | 116.50 (16) | C4B—N3B—H3BA | 118.9 |
C4A—N3A—C5A | 122.14 (17) | C5B—N3B—H3BA | 118.9 |
C4A—N3A—H3AA | 118.9 | C6B—N4B—C4B | 126.21 (17) |
C5A—N3A—H3AA | 118.9 | C6B—N4B—H4BA | 116.9 |
C6A—N4A—C4A | 126.41 (17) | C4B—N4B—H4BA | 116.9 |
C6A—N4A—H4AA | 116.8 | C3B—N5B—H5BA | 120.0 |
C4A—N4A—H4AA | 116.8 | C3B—N5B—H5BB | 120.0 |
C3A—N5A—H5AA | 120.0 | H5BA—N5B—H5BB | 120.0 |
C3A—N5A—H5AB | 120.0 | O1B—C1B—N1B | 121.35 (18) |
H5AA—N5A—H5AB | 120.0 | O1B—C1B—C11B | 119.82 (18) |
O1A—C1A—N1A | 120.91 (18) | N1B—C1B—C11B | 118.79 (18) |
O1A—C1A—C11A | 120.20 (18) | C3B—C2B—C5B | 119.80 (17) |
N1A—C1A—C11A | 118.84 (18) | C3B—C2B—N1B | 121.26 (17) |
C5A—C2A—C3A | 119.52 (17) | C5B—C2B—N1B | 118.87 (17) |
C5A—C2A—N1A | 119.35 (17) | N5B—C3B—N2B | 115.08 (17) |
C3A—C2A—N1A | 121.09 (17) | N5B—C3B—C2B | 122.54 (18) |
N5A—C3A—N2A | 114.99 (17) | N2B—C3B—C2B | 122.38 (17) |
N5A—C3A—C2A | 122.35 (18) | N2B—C4B—N3B | 124.38 (18) |
N2A—C3A—C2A | 122.64 (18) | N2B—C4B—N4B | 117.28 (17) |
N2A—C4A—N3A | 124.42 (18) | N3B—C4B—N4B | 118.33 (17) |
N2A—C4A—N4A | 117.21 (17) | O2B—C5B—N3B | 117.56 (18) |
N3A—C4A—N4A | 118.35 (17) | O2B—C5B—C2B | 127.85 (18) |
O2A—C5A—N3A | 117.72 (18) | N3B—C5B—C2B | 114.59 (17) |
O2A—C5A—C2A | 127.59 (18) | O3B—C6B—N4B | 122.21 (18) |
N3A—C5A—C2A | 114.70 (17) | O3B—C6B—C7B | 122.76 (19) |
O3A—C6A—N4A | 121.84 (18) | N4B—C6B—C7B | 115.02 (17) |
O3A—C6A—C7A | 123.05 (18) | C6B—C7B—C8B | 108.78 (17) |
N4A—C6A—C7A | 115.10 (17) | C6B—C7B—C10B | 109.49 (19) |
C8A—C7A—C6A | 108.48 (17) | C8B—C7B—C10B | 109.59 (19) |
C8A—C7A—C10A | 109.87 (19) | C6B—C7B—C9B | 109.57 (18) |
C6A—C7A—C10A | 109.06 (18) | C8B—C7B—C9B | 109.16 (19) |
C8A—C7A—C9A | 109.16 (19) | C10B—C7B—C9B | 110.22 (19) |
C6A—C7A—C9A | 109.61 (18) | C7B—C8B—H8BA | 109.5 |
C10A—C7A—C9A | 110.63 (18) | C7B—C8B—H8BB | 109.5 |
C7A—C8A—H8AA | 109.5 | H8BA—C8B—H8BB | 109.5 |
C7A—C8A—H8AB | 109.5 | C7B—C8B—H8BC | 109.5 |
H8AA—C8A—H8AB | 109.5 | H8BA—C8B—H8BC | 109.5 |
C7A—C8A—H8AC | 109.5 | H8BB—C8B—H8BC | 109.5 |
H8AA—C8A—H8AC | 109.5 | C7B—C9B—H9BA | 109.5 |
H8AB—C8A—H8AC | 109.5 | C7B—C9B—H9BB | 109.5 |
C7A—C9A—H9AA | 109.5 | H9BA—C9B—H9BB | 109.5 |
C7A—C9A—H9AB | 109.5 | C7B—C9B—H9BC | 109.5 |
H9AA—C9A—H9AB | 109.5 | H9BA—C9B—H9BC | 109.5 |
C7A—C9A—H9AC | 109.5 | H9BB—C9B—H9BC | 109.5 |
H9AA—C9A—H9AC | 109.5 | C7B—C10B—H10D | 109.5 |
H9AB—C9A—H9AC | 109.5 | C7B—C10B—H10E | 109.5 |
C7A—C10A—H10A | 109.5 | H10D—C10B—H10E | 109.5 |
C7A—C10A—H10B | 109.5 | C7B—C10B—H10F | 109.5 |
H10A—C10A—H10B | 109.5 | H10D—C10B—H10F | 109.5 |
C7A—C10A—H10C | 109.5 | H10E—C10B—H10F | 109.5 |
H10A—C10A—H10C | 109.5 | C14B—C11B—C1B | 114.60 (18) |
H10B—C10A—H10C | 109.5 | C14B—C11B—C13B | 109.37 (19) |
C14A—C11A—C13A | 109.63 (19) | C1B—C11B—C13B | 108.17 (17) |
C14A—C11A—C1A | 114.71 (17) | C14B—C11B—C12B | 109.6 (2) |
C13A—C11A—C1A | 107.86 (18) | C1B—C11B—C12B | 104.75 (18) |
C14A—C11A—C12A | 109.2 (2) | C13B—C11B—C12B | 110.2 (2) |
C13A—C11A—C12A | 110.5 (2) | C11B—C12B—H12D | 109.5 |
C1A—C11A—C12A | 104.87 (18) | C11B—C12B—H12E | 109.5 |
C11A—C12A—H12A | 109.5 | H12D—C12B—H12E | 109.5 |
C11A—C12A—H12B | 109.5 | C11B—C12B—H12F | 109.5 |
H12A—C12A—H12B | 109.5 | H12D—C12B—H12F | 109.5 |
C11A—C12A—H12C | 109.5 | H12E—C12B—H12F | 109.5 |
H12A—C12A—H12C | 109.5 | C11B—C13B—H13D | 109.5 |
H12B—C12A—H12C | 109.5 | C11B—C13B—H13E | 109.5 |
C11A—C13A—H13A | 109.5 | H13D—C13B—H13E | 109.5 |
C11A—C13A—H13B | 109.5 | C11B—C13B—H13F | 109.5 |
H13A—C13A—H13B | 109.5 | H13D—C13B—H13F | 109.5 |
C11A—C13A—H13C | 109.5 | H13E—C13B—H13F | 109.5 |
H13A—C13A—H13C | 109.5 | C11B—C14B—H14D | 109.5 |
H13B—C13A—H13C | 109.5 | C11B—C14B—H14E | 109.5 |
C11A—C14A—H14A | 109.5 | H14D—C14B—H14E | 109.5 |
C11A—C14A—H14B | 109.5 | C11B—C14B—H14F | 109.5 |
H14A—C14A—H14B | 109.5 | H14D—C14B—H14F | 109.5 |
C11A—C14A—H14C | 109.5 | H14E—C14B—H14F | 109.5 |
H14A—C14A—H14C | 109.5 | H1W1—O1W—H2W1 | 93.9 |
H14B—C14A—H14C | 109.5 | H1W2—O2W—H2W2 | 100.6 |
C1B—N1B—C2B | 122.25 (17) | H1W3—O3W—H2W3 | 103.4 |
C1B—N1B—H1BA | 118.9 | H1W4—O4W—H2W4 | 100.7 |
C2A—N1A—C1A—O1A | −0.1 (3) | C2B—N1B—C1B—O1B | 0.7 (3) |
C2A—N1A—C1A—C11A | 177.39 (17) | C2B—N1B—C1B—C11B | −177.27 (17) |
C1A—N1A—C2A—C5A | −106.0 (2) | C1B—N1B—C2B—C3B | −70.7 (3) |
C1A—N1A—C2A—C3A | 71.8 (3) | C1B—N1B—C2B—C5B | 106.3 (2) |
C4A—N2A—C3A—N5A | 178.46 (18) | C4B—N2B—C3B—N5B | −178.07 (18) |
C4A—N2A—C3A—C2A | −2.9 (3) | C4B—N2B—C3B—C2B | 2.5 (3) |
C5A—C2A—C3A—N5A | 179.67 (19) | C5B—C2B—C3B—N5B | −179.83 (19) |
N1A—C2A—C3A—N5A | 1.9 (3) | N1B—C2B—C3B—N5B | −2.9 (3) |
C5A—C2A—C3A—N2A | 1.2 (3) | C5B—C2B—C3B—N2B | −0.4 (3) |
N1A—C2A—C3A—N2A | −176.57 (19) | N1B—C2B—C3B—N2B | 176.56 (18) |
C3A—N2A—C4A—N3A | 2.1 (3) | C3B—N2B—C4B—N3B | −2.3 (3) |
C3A—N2A—C4A—N4A | −176.13 (18) | C3B—N2B—C4B—N4B | 176.55 (17) |
C5A—N3A—C4A—N2A | 0.5 (3) | C5B—N3B—C4B—N2B | 0.0 (3) |
C5A—N3A—C4A—N4A | 178.75 (18) | C5B—N3B—C4B—N4B | −178.80 (18) |
C6A—N4A—C4A—N2A | 172.1 (2) | C6B—N4B—C4B—N2B | −172.0 (2) |
C6A—N4A—C4A—N3A | −6.3 (3) | C6B—N4B—C4B—N3B | 6.9 (3) |
C4A—N3A—C5A—O2A | 177.46 (19) | C4B—N3B—C5B—O2B | −178.21 (19) |
C4A—N3A—C5A—C2A | −2.3 (3) | C4B—N3B—C5B—C2B | 2.0 (3) |
C3A—C2A—C5A—O2A | −178.3 (2) | C3B—C2B—C5B—O2B | 178.5 (2) |
N1A—C2A—C5A—O2A | −0.5 (3) | N1B—C2B—C5B—O2B | 1.4 (3) |
C3A—C2A—C5A—N3A | 1.4 (3) | C3B—C2B—C5B—N3B | −1.8 (3) |
N1A—C2A—C5A—N3A | 179.19 (17) | N1B—C2B—C5B—N3B | −178.80 (17) |
C4A—N4A—C6A—O3A | 12.3 (3) | C4B—N4B—C6B—O3B | −12.1 (3) |
C4A—N4A—C6A—C7A | −166.52 (19) | C4B—N4B—C6B—C7B | 167.13 (19) |
O3A—C6A—C7A—C8A | −1.9 (3) | O3B—C6B—C7B—C8B | 2.4 (3) |
N4A—C6A—C7A—C8A | 176.91 (19) | N4B—C6B—C7B—C8B | −176.8 (2) |
O3A—C6A—C7A—C10A | −121.5 (2) | O3B—C6B—C7B—C10B | 122.1 (2) |
N4A—C6A—C7A—C10A | 57.3 (2) | N4B—C6B—C7B—C10B | −57.1 (2) |
O3A—C6A—C7A—C9A | 117.2 (2) | O3B—C6B—C7B—C9B | −116.9 (2) |
N4A—C6A—C7A—C9A | −64.0 (2) | N4B—C6B—C7B—C9B | 63.9 (2) |
O1A—C1A—C11A—C14A | −173.80 (19) | O1B—C1B—C11B—C14B | 175.6 (2) |
N1A—C1A—C11A—C14A | 8.7 (3) | N1B—C1B—C11B—C14B | −6.4 (3) |
O1A—C1A—C11A—C13A | −51.3 (3) | O1B—C1B—C11B—C13B | 53.3 (3) |
N1A—C1A—C11A—C13A | 131.2 (2) | N1B—C1B—C11B—C13B | −128.7 (2) |
O1A—C1A—C11A—C12A | 66.4 (3) | O1B—C1B—C11B—C12B | −64.3 (2) |
N1A—C1A—C11A—C12A | −111.1 (2) | N1B—C1B—C11B—C12B | 113.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4A—H4AA···O1Wi | 0.86 | 2.07 | 2.918 (2) | 167 |
N4B—H4BA···O4Wii | 0.86 | 2.08 | 2.920 (2) | 166 |
N5B—H5BA···O4Wiii | 0.86 | 2.32 | 3.160 (2) | 166 |
N5B—H5BB···O1Aiv | 0.86 | 2.09 | 2.861 (2) | 149 |
O1W—H1W1···O2Wv | 0.87 | 2.00 | 2.857 (2) | 167 |
O1W—H2W1···O2Wvi | 0.90 | 1.92 | 2.819 (2) | 178 |
O2W—H2W2···O2Bv | 0.89 | 1.96 | 2.824 (2) | 162 |
O3W—H1W3···O2Aiii | 0.86 | 1.91 | 2.722 (2) | 158 |
O3W—H2W3···O2Avii | 0.89 | 1.97 | 2.833 (2) | 162 |
O4W—H1W4···O3Wviii | 0.88 | 1.99 | 2.865 (2) | 174 |
N3A—H3AA···O3A | 0.86 | 1.98 | 2.633 (2) | 132 |
N5A—H5AA···O1W | 0.86 | 2.32 | 3.163 (2) | 167 |
N5A—H5AB···O1B | 0.86 | 2.08 | 2.854 (2) | 149 |
N3B—H3BA···O3B | 0.86 | 1.97 | 2.632 (2) | 132 |
O2W—H1W2···O2B | 0.87 | 1.91 | 2.717 (2) | 154 |
O4W—H2W4···O3W | 0.88 | 1.93 | 2.811 (2) | 173 |
C14A—H14A···O1B | 0.96 | 2.53 | 3.355 (3) | 144 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y−1, z; (iii) −x+1, −y+1, −z; (iv) x−1, y, z; (v) −x+1, −y, −z+1; (vi) x+1, y, z; (vii) x−1, y+1, z; (viii) −x+1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C14H23N5O3·2H2O |
Mr | 345.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 7.5560 (3), 14.1008 (6), 18.0713 (6) |
α, β, γ (°) | 71.079 (2), 89.988 (2), 86.682 (3) |
V (Å3) | 1817.98 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.57 × 0.19 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.947, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10525, 10525, 8199 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.162, 1.11 |
No. of reflections | 10525 |
No. of parameters | 447 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.42, −0.35 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N4A—H4AA···O1Wi | 0.86 | 2.07 | 2.918 (2) | 167 |
N4B—H4BA···O4Wii | 0.86 | 2.08 | 2.920 (2) | 166 |
N5B—H5BA···O4Wiii | 0.86 | 2.32 | 3.160 (2) | 166 |
N5B—H5BB···O1Aiv | 0.86 | 2.09 | 2.861 (2) | 149 |
O1W—H1W1···O2Wv | 0.87 | 2.00 | 2.857 (2) | 167 |
O1W—H2W1···O2Wvi | 0.90 | 1.92 | 2.819 (2) | 178 |
O2W—H2W2···O2Bv | 0.89 | 1.96 | 2.824 (2) | 162 |
O3W—H1W3···O2Aiii | 0.86 | 1.91 | 2.722 (2) | 158 |
O3W—H2W3···O2Avii | 0.89 | 1.97 | 2.833 (2) | 162 |
O4W—H1W4···O3Wviii | 0.88 | 1.99 | 2.865 (2) | 174 |
N3A—H3AA···O3A | 0.86 | 1.98 | 2.633 (2) | 132 |
N5A—H5AA···O1W | 0.86 | 2.32 | 3.163 (2) | 167 |
N5A—H5AB···O1B | 0.86 | 2.08 | 2.854 (2) | 149 |
N3B—H3BA···O3B | 0.86 | 1.97 | 2.632 (2) | 132 |
O2W—H1W2···O2B | 0.87 | 1.91 | 2.717 (2) | 154 |
O4W—H2W4···O3W | 0.88 | 1.93 | 2.811 (2) | 173 |
C14A—H14A···O1B | 0.96 | 2.53 | 3.355 (3) | 144 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y−1, z; (iii) −x+1, −y+1, −z; (iv) x−1, y, z; (v) −x+1, −y, −z+1; (vi) x+1, y, z; (vii) x−1, y+1, z; (viii) −x+1, −y+2, −z. |
Footnotes
‡Thomson Reuters ResearcherID: A-3561-2009.
Acknowledgements
HKF and KB thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. KB thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. SG thanks DST (SR/S1/OC-13/2005), Government of India, for financial support. AH and MD thank the CSIR, Government of India, for research fellowships.
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Various drugs and biologically active molecules contain substituted pyrimidines (Lednicer & Mitscher, 1977). Adenine, uracil, thyamine are pyrimidine-based bases in nucleic acids (Blackburn & Gait, 1996). 2 5,6-Triamino-3H- pyrimidin-4-one dihydrochloride (VanAllan, 1976; Goswami et al. 2007) is an important component for the synthesis of pterin molecules (Brown, 1988). The title compound was selectively synthesized by the reaction of 2,5,6-triamino-3H-pyrimidin-4-one dihydrochloride with pivalic anhydride and its crystal structure is reported here.
There are two crystallographically independent 6-amino-2,5-dipivaloyl-3H-pyrimidin-4-one molecules, A and B, and four water molecules in the asymmetric unit of the title compound (Fig 1). Molecules A and B have similar geometry. The bond lengths (Allen et al., 1987) and angles are normal. In both A and B, one of the amide groups is almost coplanar with the pyrimidine ring (dihedral angle is 12.85 (9)° in A and 12.30 (10)° in B) whereas the other is significantly twisted away from the pyrimidine ring (dihedral angle is 72.18 (7)° in A and 71.29 (07)° in B) In each independent molecule, an intramolecular N—H···O hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995).
The independent molecules are linked into chains along the a axis by N—H···O and C—H···O hydrogen bonds. The adjacent chains are linked into a two-dimensional network parallel to the ac plane (Fig.2) by water molecules via N—H···O and O—H···O hydrogen bonds (Table 1).