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

Torre, J.M. de la; Nogueras, M.; Cobo, J.; Low, J.N.; Glidewell, C.

doi:10.1107/S0108270106008663

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 62| Part 5| May 2006| Pages o256-o258

doi:10.1107/S0108270106008663

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

José M. de la Torre,^a Manuel Nogueras,^a Justo Cobo,^a John N. Low ^b and Christopher Glidewell ^c ^*

^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 ), but when 6-amino-2-methoxypyrimidin-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 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 ) dimer centred at ( $[{1\over 2}]$ , $[{1\over 2}]$ , $[{1\over 2}]$ ) (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 ( $[{1\over 2}]$ , $[{1\over 2}]$ , $[{1\over 2}]$ ), 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). There are no direction-specific interactions between adjacent sheets.

Figure 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 of 0.73 (5) and 0.27 (5), respectively (see Comment).

Figure 2
Part of the crystal structure of compound (I)

, 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
A stereoview of part of the crystal structure of compound (I)

, 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) 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
M_r = 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
D_x = 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 )T_min = 0.962, T_max = 0.986
9104 measured reflections
1627 independent reflections
905 reflections with I > 2σ(I)
R_int = 0.067
θ_max = 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(F_o²) + (0.0612P)² + 0.3784P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.41 e Å⁻³
Δρ_min = −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	D⋯A	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 U_iso(H) = 1.2 or 1.5U_eq(C). The H atom bonded to N3 was permitted to ride at the distance deduced from difference maps (0.88 Å), with U_iso(H) = 1.2U_eq(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 U_iso(H) = 1.2U_eq(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 ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270106008663/gg3008sup1.cif

Structure factors: contains datablock jtr67a. DOI: 10.1107/S0108270106008663/gg3008Isup2.hkl

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.

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

	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).
	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).
	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

C₆H₇N₃O₃	F(000) = 352
M_r = 169.15	D_x = 1.578 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1627 reflections
a = 7.0515 (7) Å	θ = 5.0–27.5°
b = 9.0031 (12) Å	µ = 0.13 mm⁻¹
c = 11.237 (2) Å	T = 120 K
β = 93.690 (11)°	Block, colourless
V = 711.91 (17) Å³	0.33 × 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 scans	R_int = 0.067
Absorption correction: multi-scan (EVALCCD; Duisenberg et al., 2003)	θ_max = 27.5°, θ_min = 5.0°
T_min = 0.962, T_max = 0.986	h = −8→9
9104 measured reflections	k = −11→11
1627 independent reflections	l = −14→14

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0612P)² + 0.3784P] where P = (F_o² + 2F_c²)/3
1627 reflections	(Δ/σ)_max < 0.001
110 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₆H₇N₃O₃	V = 711.91 (17) Å³
M_r = 169.15	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.0515 (7) Å	µ = 0.13 mm⁻¹
b = 9.0031 (12) Å	T = 120 K
c = 11.237 (2) Å	0.33 × 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)
T_min = 0.962, T_max = 0.986	R_int = 0.067
9104 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.11	Δρ_max = 0.41 e Å⁻³
1627 reflections	Δρ_min = −0.39 e Å⁻³
110 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.3014 (3)	0.0726 (2)	0.55912 (17)	0.0187 (5)
C2	0.3736 (3)	0.1943 (3)	0.6021 (2)	0.0171 (6)
O2	0.4187 (2)	0.21160 (19)	0.71744 (14)	0.0221 (5)
C21	0.3896 (4)	0.0828 (3)	0.7918 (2)	0.0236 (6)
N3	0.4128 (3)	0.3157 (2)	0.53714 (17)	0.0183 (5)
C4	0.3762 (3)	0.3182 (3)	0.4151 (2)	0.0181 (6)
O4	0.4137 (2)	0.43389 (18)	0.35866 (14)	0.0212 (5)
C5	0.2965 (3)	0.1873 (3)	0.3653 (2)	0.0180 (6)
C6	0.2627 (3)	0.0717 (3)	0.4385 (2)	0.0170 (6)
N6	0.1828 (3)	−0.0589 (2)	0.39260 (17)	0.0187 (5)
C61	0.1397 (4)	−0.1787 (3)	0.4596 (2)	0.0205 (6)
O6	0.0661 (3)	−0.29016 (19)	0.41713 (15)	0.0268 (5)
H21A	0.4277	0.1066	0.8750	0.035*
H21B	0.4664	−0.0002	0.7654	0.035*
H21C	0.2550	0.0549	0.7852	0.035*
H3	0.4625	0.3946	0.5734	0.022*
H5	0.2668	0.1800	0.2819	0.022*
H6	0.1525	−0.0644	0.3156	0.022*	0.73 (5)
H6A	0.1241	−0.0700	0.2616	0.022*	0.27 (5)
H61	0.1684	−0.1749	0.5433	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0206 (11)	0.0190 (12)	0.0160 (11)	−0.0007 (9)	−0.0013 (8)	−0.0012 (9)
C2	0.0160 (13)	0.0187 (14)	0.0164 (12)	0.0017 (11)	0.0005 (10)	−0.0007 (10)
O2	0.0306 (10)	0.0214 (10)	0.0138 (9)	−0.0033 (8)	−0.0016 (7)	0.0011 (7)
C21	0.0305 (15)	0.0242 (15)	0.0160 (13)	−0.0019 (12)	0.0011 (11)	0.0025 (11)
N3	0.0239 (12)	0.0152 (12)	0.0156 (11)	−0.0028 (9)	−0.0012 (9)	−0.0003 (8)
C4	0.0161 (13)	0.0218 (14)	0.0165 (12)	0.0012 (11)	0.0022 (10)	0.0005 (11)
O4	0.0290 (10)	0.0166 (10)	0.0178 (9)	−0.0028 (8)	−0.0009 (7)	0.0022 (7)
C5	0.0205 (14)	0.0194 (14)	0.0136 (12)	−0.0001 (11)	−0.0016 (10)	−0.0001 (10)
C6	0.0146 (13)	0.0210 (14)	0.0155 (12)	0.0030 (11)	0.0000 (9)	−0.0027 (11)
N6	0.0249 (12)	0.0164 (12)	0.0147 (10)	−0.0010 (10)	0.0001 (8)	−0.0014 (9)
C61	0.0249 (14)	0.0198 (15)	0.0170 (13)	0.0017 (12)	0.0040 (11)	−0.0005 (11)
O6	0.0339 (11)	0.0208 (11)	0.0256 (10)	−0.0061 (9)	0.0022 (8)	−0.0030 (8)

Geometric parameters (Å, º) top

N1—C2	1.289 (3)	N6—C61	1.361 (3)
C2—N3	1.353 (3)	C61—O6	1.213 (3)
N3—C4	1.379 (3)	C21—H21A	0.98
C4—C5	1.406 (3)	C21—H21B	0.98
C5—C6	1.357 (3)	C21—H21C	0.98
C6—N1	1.365 (3)	N3—H3	0.88
C2—O2	1.324 (3)	C5—H5	0.95
O2—C21	1.452 (3)	N6—H6	0.88
C4—O4	1.257 (3)	N6—H6A	1.51
C6—N6	1.389 (3)	C61—H61	0.95

C2—N1—C6	115.2 (2)	N3—C4—C5	115.3 (2)
N1—C2—O2	122.1 (2)	C6—C5—C4	118.9 (2)
N1—C2—N3	125.1 (2)	C6—C5—H5	120.6
O2—C2—N3	112.8 (2)	C4—C5—H5	120.6
C2—O2—C21	115.79 (19)	C5—C6—N1	124.4 (2)
O2—C21—H21A	109.5	C5—C6—N6	120.4 (2)
O2—C21—H21B	109.5	N1—C6—N6	115.1 (2)
H21A—C21—H21B	109.5	C61—N6—C6	124.4 (2)
O2—C21—H21C	109.5	C61—N6—H6	116.8
H21A—C21—H21C	109.5	C6—N6—H6	118.7
H21B—C21—H21C	109.5	C61—N6—H6A	115.5
C2—N3—C4	121.2 (2)	C6—N6—H6A	119.9
C2—N3—H3	119.4	O6—C61—N6	122.9 (2)
C4—N3—H3	119.4	O6—C61—H61	118.5
O4—C4—N3	118.9 (2)	N6—C61—H61	118.5
O4—C4—C5	125.8 (2)

C6—N1—C2—O2	−179.9 (2)	N3—C4—C5—C6	−0.1 (3)
C6—N1—C2—N3	−0.4 (4)	C4—C5—C6—N1	−0.2 (4)
N1—C2—O2—C21	2.6 (3)	C4—C5—C6—N6	179.5 (2)
N3—C2—O2—C21	−176.9 (2)	C2—N1—C6—C5	0.4 (4)
N1—C2—N3—C4	0.2 (4)	C2—N1—C6—N6	−179.3 (2)
O2—C2—N3—C4	179.7 (2)	C5—C6—N6—C61	−178.2 (2)
C2—N3—C4—O4	179.5 (2)	N1—C6—N6—C61	1.5 (3)
C2—N3—C4—C5	0.1 (3)	C6—N6—C61—O6	178.4 (2)
O4—C4—C5—C6	−179.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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
N6—H6A···O4ⁱⁱ	1.51	1.36	2.862 (3)	173

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₆H₇N₃O₃
M_r	169.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	7.0515 (7), 9.0031 (12), 11.237 (2)
β (°)	93.690 (11)
V (Å³)	711.91 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.33 × 0.14 × 0.11

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (EVALCCD; Duisenberg et al., 2003)
T_min, T_max	0.962, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	9104, 1627, 905
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.147, 1.11
No. of reflections	1627
No. of parameters	110
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—C2	1.289 (3)	C2—O2	1.324 (3)
C2—N3	1.353 (3)	O2—C21	1.452 (3)
N3—C4	1.379 (3)	C4—O4	1.257 (3)
C4—C5	1.406 (3)	C6—N6	1.389 (3)
C5—C6	1.357 (3)	N6—C61	1.361 (3)
C6—N1	1.365 (3)	C61—O6	1.213 (3)

N1—C6—N6—C61	1.5 (3)	C6—N6—C61—O6	178.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, y−1/2, −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

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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bernstein, 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
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92–96. CrossRef CAS Web of Science IUCr Journals Google Scholar
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220–229. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada. Google Scholar
McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland. Google Scholar
Negrillo, J., Nogueras, M., Sánchez, A. & Melgarejo, M. (1988). Chem. Pharm. Bull. 36, 386–393. CrossRef CAS PubMed Web of Science Google Scholar
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 62| Part 5| May 2006| Pages o256-o258

doi:10.1107/S0108270106008663

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search term		doi		Advanced search
Author		volume	page

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