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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

N-(2-Meth­oxy-6-oxo-1,6-di­hydropyrimidin-4-yl)­formamide: hydrogen-bonded sheets of centrosymmetric R22(8) and R64(28) rings

CROSSMARK_Color_square_no_text.svg

aDepartamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain, bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 2 March 2006; accepted 8 March 2006; online 13 April 2006)

Mol­ecules of the title compound, C6H7N3O3, are linked into sheets of centrosymmetric R22(8) and R64(28) rings by two nearly linear N—H⋯O hydrogen bonds [H⋯O = 1.91 and 1.98 Å, N⋯O = 2.786 (3) and 2.862 (3) Å, and N—H⋯O = 175 and 177°].

Comment

With the aim of preparing inter­mediates for the synthesis of new fused pyrimidines, we have applied the formyl­ation procedure using formic acetic anhydride to the preparation of 5-formyl­pyrimidine derivatives (Negrillo et al., 1988[Negrillo, J., Nogueras, M., Sánchez, A. & Melgarejo, M. (1988). Chem. Pharm. Bull. 36, 386-393.]), but when 6-amino-2-methoxy­pyrimidin-4(3H)-one was used as starting material, the title compound, (I)[link] (Fig. 1[link]), was obtained selectively in 73% yield. We report here the mol­ecular and supramolecular structure of (I)[link].

[Scheme 1]

The bond distances within the pyrimidinone ring of (I)[link] (Table 1[link]) provide clear evidence of strong bond fixation. Thus, the N1—C2 bond is very much shorter than any of the C2—N3, N3—C4, N1—C6 or C6—N6 bonds, and the C5—C6 bond is very much shorter than the C4—C5 bond. However, the exocyclic C4—O4 bond is significantly longer than the formyl C61—O6 bond, even though N3—C4 is somewhat longer than N6—C61. This may be connected with the disorder of the H atom bonded to N6, which appears to be spread over a range of N—H distances. The disorder was modelled using two sites for this H atom, one adjacent to N6 with occupancy 0.73 (5) and the other almost midway along an inter­molecular N⋯H⋯O contact with occupancy 0.27 (5). At each of C2, C4 and C6, the two exocyclic bond angles are markedly different, with the maximum difference of nearly 10° at C2. With the exception of the methyl H atoms, the entire mol­ecule is effectively planar.

The supramolecular aggregation is very simple, depending upon just two N—H⋯O hydrogen bonds, both involving the same amidic atom O4 as the acceptor, and both of them almost linear (Table 2[link]). It is striking that atom O4 forms the longer of the two amidic C—O bonds and that neither formyl atom O6 nor methoxy atom O2 acts as an acceptor of hydrogen bonds. The overall supramolecular aggregation is not affected by the partial disorder of H6.

The formation of the two-dimensional supramolecular structure is readily analysed in terms of a centrosymmetric dimer unit as the basic building block. Ring atom N3 in the mol­ecule at (x, y, z) acts as hydrogen-bond donor to amidic atom O4 in the mol­ecule at (1 − x, 1 − y, 1 − z), so forming a centrosymmetric R22(8) (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) dimer centred at ([{1\over 2}], [{1\over 2}], [{1\over 2}]) (Fig. 2[link]). Exocyclic atoms N6 in the mol­ecules at (x, y, z) and (1 − x, 1 − y, 1 − z), which form the dimer centred at ([{1\over 2}], [{1\over 2}], [{1\over 2}]), act as donors to atoms O4 in the mol­ecules at ([{1\over 2}] − x, −[{1\over 2}] + y, [{1\over 2}] − z) and ([{1\over 2}] + x, [{3\over 2}] − y, [{1\over 2}] + z), respectively, which themselves form parts of the R22(8) dimers centred at (0, 0, 0) and (1, 1, 1), respectively. Similarly, atoms O4 in the mol­ecules at (x, y, z) and (1 − x, 1 − y, 1 − z) accept hydrogen bonds from atoms N6 in the mol­ecules at ([{1\over 2}] − x, [{1\over 2}] + y, [{1\over 2}] − z) and ([{1\over 2}] + x, [{1\over 2}] − y, [{1\over 2}] + z), which themselves form parts of the dimers centred at (0, 1, 0) and (1, 0, 1), respectively. Propagation of these two hydrogen bonds then generates a (10[\overline{1}]) sheet built of centrosymmetric R22(8) and R64(28) rings (Fig. 3[link]). There are no direction-specific inter­actions between adjacent sheets.

[Figure 1]
Figure 1
A mol­ecule of compound (I)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. The two sites shown for the H atom bonded to N6 have occupancies of 0.73 (5) and 0.27 (5), respectively (see Comment).
[Figure 2]
Figure 2
Part of the crystal structure of compound (I)[link], showing the formation of an R22(8) dimer centred at ([{1\over 2}], [{1\over 2}], [{1\over 2}]). For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
[Figure 3]
Figure 3
A stereoview of part of the crystal structure of compound (I)[link], showing the formation of a (10[\overline{1}]) sheet of R22(8) and R64(28) rings. For the sake of clarity, atom H6A and H atoms bonded to C atoms have all been omitted.

Experimental

6-Amino-2-methoxy­pyrimidin-4(3H)-one (1.41 g, 10 mmol) was added to a mixture of formic acid (1.33 ml, 40 mmol) and acetic anhydride (4 ml, 40 mmol) and the mixture was heated under reflux for 90 min. The mixed solvents were removed under reduced pressure to give an orange solid, which was recrystallized from ethanol (400 ml) to give a microcrystalline yellow solid. Yellow needles of (I)[link] suitable for single-crystal X-ray diffraction were grown from a solution in dimethyl sulfoxide (yield 73%). Accurate mass by MS (IE 70 eV): m/z found 169.0482, C6H7N3O3 requires 169.0487.

Crystal data
  • C6H7N3O3

  • Mr = 169.15

  • Monoclinic, P 21 /n

  • a = 7.0515 (7) Å

  • b = 9.0031 (12) Å

  • c = 11.237 (2) Å

  • β = 93.690 (11)°

  • V = 711.91 (17) Å3

  • Z = 4

  • Dx = 1.578 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 1627 reflections

  • θ = 5.0–27.5°

  • μ = 0.13 mm−1

  • T = 120 (2) K

  • Block, colourless

  • 0.33 × 0.14 × 0.11 mm

Data collection
  • Nonius KappaCCD area-detector diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan(EVALCCD; Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.])Tmin = 0.962, Tmax = 0.986

  • 9104 measured reflections

  • 1627 independent reflections

  • 905 reflections with I > 2σ(I)

  • Rint = 0.067

  • θmax = 27.5°

  • h = −8 → 9

  • k = −11 → 11

  • l = −14 → 14

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.147

  • S = 1.11

  • 1627 reflections

  • 110 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0612P)2 + 0.3784P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Selected geometric parameters (Å, °)

N1—C2 1.289 (3)
C2—N3 1.353 (3)
N3—C4 1.379 (3)
C4—C5 1.406 (3)
C5—C6 1.357 (3)
C6—N1 1.365 (3)
C2—O2 1.324 (3)
O2—C21 1.452 (3)
C4—O4 1.257 (3)
C6—N6 1.389 (3)
N6—C61 1.361 (3)
C61—O6 1.213 (3)
N1—C6—N6—C61 1.5 (3)
C6—N6—C61—O6 178.4 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3⋯O4i 0.88 1.91 2.786 (3) 175
N6—H6⋯O4ii 0.88 1.98 2.862 (3) 177
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

The space group P21/n was uniquely assigned from the systematic absences. All H atoms were located in difference maps. H atoms bonded to C atoms were treated as riding atoms, with C—H distances of 0.95 (aromatic and formyl) or 0.98 Å (methyl) and with Uiso(H) = 1.2 or 1.5Ueq(C). The H atom bonded to N3 was permitted to ride at the distance deduced from difference maps (0.88 Å), with Uiso(H) = 1.2Ueq(N). The H atom formally bonded to N6 was found to be disordered over two sites, one adjacent to N6 and denoted H6 and the other, denoted H6A, approximately midway between N6 and atom O4 of a neighbouring mol­ecule at ([{1\over 2}] − x, −[{1\over 2}] + y, [{1\over 2}] − z). The coordinates of these two sites were initially refined with the occupancies tied to sum to unity; in the final cycles of refinement, their positions were fixed, with Uiso(H) = 1.2Ueq(N6). The site occupancies for H6 and H6A refined to 0.73 (5) and 0.27 (5), respectively. A difference map calculated with these two sites, H6 and H6A, omitted shows an extended ridge of electron density between these two sites, possibly suggesting a very large amplitude motion of this H atom.

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX (Duisenberg, 1992[Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information


Comment top

With the aim of preparing intermediates for the synthesis of new fused pyrimidines, we have applied the formylation procedure using formic acetic anhydride to the preparation of 5-formylpyrimidine derivatives (Negrillo et al., 1988), but when 6-amino-2-methoxypyrimid-4(3H)-one was used as starting material, the title compound, (I) (Fig. 1), was obtained selectively in 73% yield. We report here the molecular and supramolecular structure of (I).

The bond distances within the pyrimidinone ring of (I) (Table 1) provide clear evidence of strong bond fixation. Thus, the N1—C2 bond is very much shorter than any of the C2—N3, N3—C4, N1—C6 or C6—N6 bonds, and the C5—C6 bond is very much shorter than the C4—C5 bond. However, the exocyclic C4—O4 bond is significantly longer than the formyl C61—O6 bond, even though N3—C4 is somewhat longer than N6—C61. This may be connected with the disorder of the H atom bonded to N6, which appears to be spread over a range of N—H distances. The disorder was modelled using two sites for this H atom, one adjacent to N6 with occupancy 0.73 (5) and the other almost midway along an intermolecular N···H···O contact, with occupancy 0.27 (5). At each of C2, C4 and C6, the two exocyclic bond angles are markedly different, with the maximum difference of nearly 10° at C2. With the exception of the methyl H atoms, the entire molecule is effectively planar.

The supramolecular aggregation is very simple, depending upon just two N—H···O hydrogen bonds, both involving the same amidic atom O4 as the acceptor, and both of them almost linear (Table 2). It is striking that atom O4 forms the longer of the two amidic C—O bonds and that neither the formyl atom O6 nor the methoxy atom O2 acts as an acceptor of hydrogen bonds. The overall supramolecular aggregation is not affected by the partial disorder of H6.

The formation of the two-dimensional supramolecular structure is readily analysed in terms of a centrosymmetric dimer unit as the basic building block. Ring atom N3 in the molecule at (x, y, z) acts as hydrogen-bond donor to amidic atom O4 in the molecule at (1 − x, 1 − y, 1 − z), so forming a centrosymmetric R22(8) (Bernstein et al., 1995) dimer centred at (1/2, 1/2, 1/2) (Fig. 2). Exocyclic atoms N6 in the molecules at (x, y, z) and (1 − x, 1 − y, 1 − z), which form the dimer centred at (1/2, 1/2, 1/2), act as donors to atoms O4 in the molecules at (1/2 − x, −1/2 + y, 1/2 − z) and (1/2 + x, 3/2 − y, 1/2 + z), respectively, which themselves form parts of the R22(8) dimers centred at (0, 0, 0) and (1, 1, 1), respectively. Similarly, atoms O4 in the molecules at (x, y, z) and (1 − x, 1 − y, 1 − z) accept hydrogen bonds from atoms N6 in the molecules at (1/2 − x, 1/2 + y, 1/2 − z) and (1/2 + x, 1/2 − y, 1/2 + z), which themselves form parts of the dimers centred at (0, 1, 0) and (1, 0, 1), respectively. Propagation of these two hydrogen bonds then generates a (101) sheet built of centrosymmetric R22(8) and R46(28) rings (Fig. 3). There are no direction-specific interactions between adjacent sheets.

Experimental top

6-Amino-2-methoxypyrimid-4(3H)-one (1.41 g, 10 mmol) was added to a mixture of formic acid (1.33 ml, 40 mmol) and acetic anhydride (4 ml, 40 mmol) and the mixture was heated under reflux for 90 min. The mixed solvents were removed under reduced pressure to give an orange solid, which was recrystallized from ethanol (400 ml) to give a microcrystalline yellow solid. Yellow needles of (I) suitable for single-crystal X-ray diffraction were grown from a solution in dimethyl sulfoxide (yield 73%). Accurate mass by MS (IE 70 eV): m/z found 169.0482, C6H7N3O3 requires 169.0487.

Refinement top

The space group P21/n was uniquely assigned from the systematic absences. All H atoms were located in difference maps. H atoms bonded to C atoms were treated as riding atoms, with C—H distances of 0.95 (aromatic and formyl) or 0.98 Å (methyl) and with Uiso(H) = 1.2 or 1.5Ueq(C). The H atom bonded to N3 was permitted to ride at the distance deduced from difference maps (0.88 Å), with Uiso(H) = 1.2Ueq(N). The H atom formally bonded to N6 was found to be disordered over two sites, one adjacent to N6 and denoted H6 and the other, denoted H6A, approximately midway between N6 and atom O4 of a neighbouring molecule at (1/2 − x, −1/2 + y, 1/2 − z). The coordinates of these two sites were initially refined with the occupancies tied to sum to unity; in the final cycles of refinement their positions were fixed, with Uiso(H) = 1.2Ueq(N6). The site occupancies for H6 and H6A refined to 0.73 (5) and 0.27 (5), respectively. A difference map calculated with these two sites, H6 and H6A, omitted shows an extended ridge of electron density between these two sites, possibly suggesting a very large amplitude motion of this H atom.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999; program(s) used to refine structure: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A molecule of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. The two sites shown for the H atom bonded to N6 have occupancies 0.73 (5) and 0.27 (5), respectively (see text).
[Figure 2] Fig. 2. Part of the crystal structure of compound (I), showing the formation of an R22(8) dimer centred at (1/2, 1/2, 1/2). For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of compound (I), showing the formation of a (101) sheet of R22(8) and R46(28) rings. For the sake of clarity, atom H6A and H atoms bonded to C atoms have all been omitted.
N-(2-Methoxy-6-oxopyrimidin-4-yl)formamide top
Crystal data top
C6H7N3O3F(000) = 352
Mr = 169.15Dx = 1.578 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1627 reflections
a = 7.0515 (7) Åθ = 5.0–27.5°
b = 9.0031 (12) ŵ = 0.13 mm1
c = 11.237 (2) ÅT = 120 K
β = 93.690 (11)°Block, colourless
V = 711.91 (17) Å30.33 × 0.14 × 0.11 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
905 reflections with I > 2σ(I)
CCD rotation images, thick slices scansRint = 0.067
Absorption correction: multi-scan
(EVALCCD; Duisenberg et al., 2003)
θmax = 27.5°, θmin = 5.0°
Tmin = 0.962, Tmax = 0.986h = 89
9104 measured reflectionsk = 1111
1627 independent reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0612P)2 + 0.3784P]
where P = (Fo2 + 2Fc2)/3
1627 reflections(Δ/σ)max < 0.001
110 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.39 e Å3
Crystal data top
C6H7N3O3V = 711.91 (17) Å3
Mr = 169.15Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.0515 (7) ŵ = 0.13 mm1
b = 9.0031 (12) ÅT = 120 K
c = 11.237 (2) Å0.33 × 0.14 × 0.11 mm
β = 93.690 (11)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
1627 independent reflections
Absorption correction: multi-scan
(EVALCCD; Duisenberg et al., 2003)
905 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.986Rint = 0.067
9104 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 1.11Δρmax = 0.41 e Å3
1627 reflectionsΔρmin = 0.39 e Å3
110 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.3014 (3)0.0726 (2)0.55912 (17)0.0187 (5)
C20.3736 (3)0.1943 (3)0.6021 (2)0.0171 (6)
O20.4187 (2)0.21160 (19)0.71744 (14)0.0221 (5)
C210.3896 (4)0.0828 (3)0.7918 (2)0.0236 (6)
N30.4128 (3)0.3157 (2)0.53714 (17)0.0183 (5)
C40.3762 (3)0.3182 (3)0.4151 (2)0.0181 (6)
O40.4137 (2)0.43389 (18)0.35866 (14)0.0212 (5)
C50.2965 (3)0.1873 (3)0.3653 (2)0.0180 (6)
C60.2627 (3)0.0717 (3)0.4385 (2)0.0170 (6)
N60.1828 (3)0.0589 (2)0.39260 (17)0.0187 (5)
C610.1397 (4)0.1787 (3)0.4596 (2)0.0205 (6)
O60.0661 (3)0.29016 (19)0.41713 (15)0.0268 (5)
H21A0.42770.10660.87500.035*
H21B0.46640.00020.76540.035*
H21C0.25500.05490.78520.035*
H30.46250.39460.57340.022*
H50.26680.18000.28190.022*
H60.15250.06440.31560.022*0.73 (5)
H6A0.12410.07000.26160.022*0.27 (5)
H610.16840.17490.54330.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0206 (11)0.0190 (12)0.0160 (11)0.0007 (9)0.0013 (8)0.0012 (9)
C20.0160 (13)0.0187 (14)0.0164 (12)0.0017 (11)0.0005 (10)0.0007 (10)
O20.0306 (10)0.0214 (10)0.0138 (9)0.0033 (8)0.0016 (7)0.0011 (7)
C210.0305 (15)0.0242 (15)0.0160 (13)0.0019 (12)0.0011 (11)0.0025 (11)
N30.0239 (12)0.0152 (12)0.0156 (11)0.0028 (9)0.0012 (9)0.0003 (8)
C40.0161 (13)0.0218 (14)0.0165 (12)0.0012 (11)0.0022 (10)0.0005 (11)
O40.0290 (10)0.0166 (10)0.0178 (9)0.0028 (8)0.0009 (7)0.0022 (7)
C50.0205 (14)0.0194 (14)0.0136 (12)0.0001 (11)0.0016 (10)0.0001 (10)
C60.0146 (13)0.0210 (14)0.0155 (12)0.0030 (11)0.0000 (9)0.0027 (11)
N60.0249 (12)0.0164 (12)0.0147 (10)0.0010 (10)0.0001 (8)0.0014 (9)
C610.0249 (14)0.0198 (15)0.0170 (13)0.0017 (12)0.0040 (11)0.0005 (11)
O60.0339 (11)0.0208 (11)0.0256 (10)0.0061 (9)0.0022 (8)0.0030 (8)
Geometric parameters (Å, º) top
N1—C21.289 (3)N6—C611.361 (3)
C2—N31.353 (3)C61—O61.213 (3)
N3—C41.379 (3)C21—H21A0.98
C4—C51.406 (3)C21—H21B0.98
C5—C61.357 (3)C21—H21C0.98
C6—N11.365 (3)N3—H30.88
C2—O21.324 (3)C5—H50.95
O2—C211.452 (3)N6—H60.88
C4—O41.257 (3)N6—H6A1.51
C6—N61.389 (3)C61—H610.95
C2—N1—C6115.2 (2)N3—C4—C5115.3 (2)
N1—C2—O2122.1 (2)C6—C5—C4118.9 (2)
N1—C2—N3125.1 (2)C6—C5—H5120.6
O2—C2—N3112.8 (2)C4—C5—H5120.6
C2—O2—C21115.79 (19)C5—C6—N1124.4 (2)
O2—C21—H21A109.5C5—C6—N6120.4 (2)
O2—C21—H21B109.5N1—C6—N6115.1 (2)
H21A—C21—H21B109.5C61—N6—C6124.4 (2)
O2—C21—H21C109.5C61—N6—H6116.8
H21A—C21—H21C109.5C6—N6—H6118.7
H21B—C21—H21C109.5C61—N6—H6A115.5
C2—N3—C4121.2 (2)C6—N6—H6A119.9
C2—N3—H3119.4O6—C61—N6122.9 (2)
C4—N3—H3119.4O6—C61—H61118.5
O4—C4—N3118.9 (2)N6—C61—H61118.5
O4—C4—C5125.8 (2)
C6—N1—C2—O2179.9 (2)N3—C4—C5—C60.1 (3)
C6—N1—C2—N30.4 (4)C4—C5—C6—N10.2 (4)
N1—C2—O2—C212.6 (3)C4—C5—C6—N6179.5 (2)
N3—C2—O2—C21176.9 (2)C2—N1—C6—C50.4 (4)
N1—C2—N3—C40.2 (4)C2—N1—C6—N6179.3 (2)
O2—C2—N3—C4179.7 (2)C5—C6—N6—C61178.2 (2)
C2—N3—C4—O4179.5 (2)N1—C6—N6—C611.5 (3)
C2—N3—C4—C50.1 (3)C6—N6—C61—O6178.4 (2)
O4—C4—C5—C6179.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O4i0.881.912.786 (3)175
N6—H6···O4ii0.881.982.862 (3)177
N6—H6A···O4ii1.511.362.862 (3)173
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC6H7N3O3
Mr169.15
Crystal system, space groupMonoclinic, P21/n
Temperature (K)120
a, b, c (Å)7.0515 (7), 9.0031 (12), 11.237 (2)
β (°) 93.690 (11)
V3)711.91 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.33 × 0.14 × 0.11
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(EVALCCD; Duisenberg et al., 2003)
Tmin, Tmax0.962, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
9104, 1627, 905
Rint0.067
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.147, 1.11
No. of reflections1627
No. of parameters110
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.39

Computer programs: COLLECT (Nonius, 1999), DIRAX (Duisenberg, 1992), EVALCCD (Duisenberg et al., 2003), SIR97 (Altomare et al., 1999, OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
N1—C21.289 (3)C2—O21.324 (3)
C2—N31.353 (3)O2—C211.452 (3)
N3—C41.379 (3)C4—O41.257 (3)
C4—C51.406 (3)C6—N61.389 (3)
C5—C61.357 (3)N6—C611.361 (3)
C6—N11.365 (3)C61—O61.213 (3)
N1—C6—N6—C611.5 (3)C6—N6—C61—O6178.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O4i0.881.912.786 (3)175
N6—H6···O4ii0.881.982.862 (3)177
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y1/2, z+1/2.
 

Acknowledgements

The X-ray data were collected at the Servicios Técnicos de Investigación, University of Jaén. JT, MN and JC thank the Consejería de Educación y Ciencia (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support.

References

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First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
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First citationNegrillo, J., Nogueras, M., Sánchez, A. & Melgarejo, M. (1988). Chem. Pharm. Bull. 36, 386–393.  CrossRef CAS PubMed Web of Science Google Scholar
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First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
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