5-(1-Hydroxy­ethyl­idene)-1,3-di­methyl­pyrimidine-2,4,6(1H,3H,5H)-trione and four amino derivatives

Silva, E.T. da; Ribiero, R.S.; Lima, E.L.S.; Wardell, J.L.; Skakle, J.M.S.; Low, J.N.; Glidewell, C.

doi:10.1107/S0108270104028859

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 61| Part 1| January 2005| Pages o15-o20

doi:10.1107/S0108270104028859

5-(1-Hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione and four amino derivatives

Emerson T. da Silva,^a Rodrigo S. Ribiero,^a Edson L. S. Lima,^a James L. Wardell,^b Janet M. S. Skakle,^c John N. Low ^c and Christopher Glidewell ^d ^*

^aInstituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil, ^bInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil, ^cDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^dSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 5 November 2004; accepted 8 November 2004; online 11 December 2004)

In the structures of 5-(1-hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₈H₁₀N₂O₄, (I), 1,3-dimethyl-5-[1-(propylamino)ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione, C₁₁H₁₇N₃O₃, (II), and 5-[1-(2,2-dimethoxyethylamino)ethylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₁₂H₁₉N₃O₅, (III), there are no direction-specific intermolecular interactions. The molecules in 5-[1-(benzylamino)ethylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₁₅H₁₇N₃O₃, (IV), are linked into chains of edge-fused rings by a combination of one C—H⋯O hydrogen bond and one C—H⋯π(arene) hydrogen bond, while the molecules in 5-(1-hydrazinoethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₈H₁₂N₄O₃, (V), are linked into a continuous framework structure by three distinct N—H⋯O hydrogen bonds, each involving a different O-atom acceptor. Each of compounds (I)–(V) contains an intramolecular hydrogen bond, of the O—H⋯O type in (I) and of the N—H⋯O type in (II)–(V).

Comment

It has recently been reported (da Silva & Lima, 2003 ) that the title compound, (I), which is the enol tautomer of 1,3-dimethyl-5-acetylbarbituric acid, reacts readily with primary amines to form enamines. We report here the structures of (I), of three representative enamine derivatives, (II)–(IV), and of the hydrazine derivative (V) (Figs. 1 –5).

The bond distances in (I) (Table 1), in particular the C4—O4 and C51—O51 distances on the one hand and the C4—C5 and C5—C51 distances on the other, clearly demonstrate the enol constitution, consistent with the location of atom H51 as deduced from a difference map. In each of compounds (II)–(V), atom N51 has a planar configuration, and the C51—N51 distances are all typical of their type (Allen et al., 1987 ). Atom N52 in (V) has a distinctly pyramidal coordination environment, with a sum of bond angles, based on H-atom coordinates derived from difference maps, of 328.8°. The N51—N52 distance in (V) corresponds closely to the mean value of 1.420 Å for >N—N< distances where the coordination of one N atom is planar and that of the other is pyramidal.

There is an intramolecular hydrogen bond in each of (I)–(V), of O—H⋯O type in (I) and of N—H⋯O type in (II)–(V) (Table 2). There are no direction-specific intermolecular interactions in (I)–(III), but the molecules in (IV) and (V) are linked by intermolecular hydrogen bonds (Table 2) into supramolecular structures that are one- and three-dimensional, respectively.

The one-dimensional supramolecular structure of (IV) is generated by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds (Table 2). Aryl atom C514 in the molecule at (x, y, z) acts as a hydrogen-bond donor to carbonyl atom O4 in the molecule at (1 − x, 1 − y, 1 − z), so generating a centrosymmetric R₂²(22) ring (Bernstein et al., 1995 ) centred at ( $[1\over2]$ , $[1\over2]$ , $[1\over2]$ ) (Fig. 6). In addition, methylene atom C53 in the molecule at (x, y, z) acts as a hydrogen-bond donor to the C511–C516 aryl ring in the molecule at (1 − x, −y, 1 − z), so generating a second centrosymmetric ring, this time centred at ( $[1\over2]$ , 0, $[1\over2]$ ). The combination of these two centrosymmetric motifs thus generates a chain of edge-fused rings running parallel to the [010] direction, with the larger rings centred at ( $[1\over2]$ , $[1\over2]$ + n, $[1\over2]$ ) (n = zero or integer) and the smaller rings centred at ( $[1\over2]$ , n, $[1\over2]$ ) (n = zero or integer) (Fig. 6).

The three-dimensional supramolecular structure of (V) is of some complexity but can readily be analysed in terms of a series of one-dimensional substructures and their simple combinations. In the first substructure, atom N52 in the molecule at (x, y, z) acts as a hydrogen-bond donor, via atom H52D, to atom O4 in the molecule at (− $[1\over2]$ + x, $[1\over2]$ − y, −z), so producing a C(7) chain running parallel to the [100] direction and generated by the 2₁ screw axis along (x, $[1\over4]$ , 0) (Fig. 7). In the second substructure, atom N52 at (x, y, z) acts as a donor, via atom H52E, to atom O2 in the molecule at (2 − x, − $[1\over2]$ + y, $[1\over2]$ − z), so producing a C(9) chain running parallel to the [010] direction, now generated by the 2₁ screw axis along (1, y, $[1\over4]$ ) (Fig. 8).

Each of these chains, along [100] and [010], respectively, utilizes just one N—H⋯O hydrogen bond, but the combination of these two interactions produces a third chain motif, running parallel to the [001] direction. Atom N52 in the molecule at (− $[1\over2]$ + x, $[1\over2]$ − y, −z) acts as a hydrogen-bond donor, via atom H52E, to atom O2 in the molecule at ( $[3\over2]$ − x, 1 − y, − $[1\over2]$ + z), while atom N52 at ( $[3\over2]$ − x, 1 − y, − $[1\over2]$ + z) acts as a donor, via atom H52D, to atom O4 at (2 − x, $[1\over2]$ + y, − $[1\over2]$ − z); finally, atom N52 at (2 − x, $[1\over2]$ + y, − $[1\over2]$ − z) acts as a donor, via atom H52E, to atom O2 in the molecule at (x, y, −1 + z). In this manner a C₂²(16) chain is generated along [001] (Fig. 9).

These three chain motifs (Figs. 7 –9) together produce a three-dimensional framework structure, which is generated solely by the action of 2₁ screw axes and which utilizes only half of the molecules within the unit cell. There is, accordingly, a second such framework present, which is interwoven with the first framework and related to it by inversion. These two three-dimensional substructures are, however, linked by the final N—H⋯O hydrogen bond; this is, in fact, one component of an effectively planar three-centre N—H⋯(O)₂ system (Table 2). Atom N51 in the molecule at (x, y, z) acts as a donor, not only intramolecularly to atom O4 but also to atom O6 in the molecule at (x, $[1\over2]$ − y, − $[1\over2]$ + z), so producing a C(6) chain running parallel to the [001] direction and generated by the c-glide plane at y = $[1\over4]$ (Fig. 10). This final motif suffices to link the two frameworks and hence to link all of the molecules into a single three-dimensional structure.

Figure 1
The molecule of (I

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
The molecule of (II

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 3
The molecule of (III

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 4
The molecule of (IV

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 5
The molecule of (V

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 6
A stereoview of part of the crystal structure of (IV

), showing the formation of a chain of edge-fused rings along [010]. For clarity, H atoms not involved in the motifs shown have been omitted.

Figure 7
Part of the crystal structure of (V

), showing the formation of a C(7) chain along [100]. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (− $[1\over2]$ + x, $[1\over2]$ − y, −z) and (−1 + x, y, z), respectively.

Figure 8
Part of the crystal structure of (V

), showing the formation of a C(9) chain along [010]. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (2 − x, − $[1\over2]$ + y, $[1\over2]$ − z) and (2 − x, $[1\over2]$ + y, $[1\over2]$ − z), respectively.

Figure 9
A stereoview of part of the crystal structure of (V

), showing the formation of a C₂²(16) chain along [001]. For clarity, H atoms bonded to C atoms have been omitted.

Figure 10
Part of the crystal structure of (V

), showing the formation of a C(6) chain along [001]. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*), a hash (#) or an ampersand (&) are at the symmetry positions (x, $[1\over2]$ − y, $[1\over2]$ + z), (x, y, 1 + z) and (x, $[1\over2]$ − y, − $[1\over2]$ + z), respectively.

Experimental

Samples of compounds (I)–(V) were prepared as described by da Silva & Lima (2003). Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of solutions in ethanol.

Compound (I)

Crystal data

C₈H₁₀N₂O₄
M_r = 198.18
Monoclinic, P2₁/c
a = 8.6066 (5) Å
b = 9.1751 (5) Å
c = 11.9799 (7) Å
β = 109.321 (2)°
V = 892.73 (9) Å³
Z = 4
D_x = 1.475 Mg m⁻³
Mo Kα radiation
Cell parameters from 3198 reflections
θ = 2.9–32.5°
μ = 0.12 mm⁻¹
T = 291 (2) K
Block, colourless
0.52 × 0.33 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
φ–ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.934, T_max = 0.976
7606 measured reflections
3198 independent reflections
1926 reflections with I > 2σ(I)
R_int = 0.022
θ_max = 32.5°
h = −13 → 5
k = −13 → 9
l = −18 → 18

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.207
S = 1.03
3198 reflections
131 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.102P)² + 0.1435P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Compound (II)

Crystal data

C₁₁H₁₇N₃O₃
M_r = 239.28
Monoclinic, Pn
a = 4.1085 (3) Å
b = 8.4497 (5) Å
c = 17.1272 (11) Å
β = 94.721 (2)°
V = 592.56 (7) Å³
Z = 2
D_x = 1.341 Mg m⁻³
Mo Kα radiation
Cell parameters from 2129 reflections
θ = 2.4–32.5°
μ = 0.10 mm⁻¹
T = 291 (2) K
Lath, colourless
0.49 × 0.40 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
φ–ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.931, T_max = 0.988
5869 measured reflections
2129 independent reflections
1671 reflections with I > 2σ(I)
R_int = 0.022
θ_max = 32.5°
h = −6 → 6
k = −12 → 12
l = −17 → 25

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.126
S = 1.01
2129 reflections
158 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0836P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Compound (III)

Crystal data

C₁₂H₁₉N₃O₅
M_r = 285.30
Trigonal, $[R\overline 3]$
a = 18.4577 (4) Å
c = 19.7736 (4) Å
V = 5834.1 (2) Å³
Z = 18
D_x = 1.462 Mg m⁻³
Mo Kα radiation
Cell parameters from 2965 reflections
θ = 3.1–27.5°
μ = 0.12 mm⁻¹
T = 120 (2) K
Block, colourless
0.40 × 0.40 × 0.30 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ–ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.950, T_max = 0.966
14 896 measured reflections
2965 independent reflections
2329 reflections with I > 2σ(I)
R_int = 0.033
θ_max = 27.5°
h = −19 → 23
k = −23 → 19
l = −22 → 25

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.115
S = 1.11
2965 reflections
186 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0597P)² + 2.9334P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Compound (IV)

Crystal data

C₁₅H₁₇N₃O₃
M_r = 287.32
Triclinic, $[P\overline 1]$
a = 7.0696 (5) Å
b = 9.0734 (7) Å
c = 11.9214 (8) Å
α = 70.995 (2)°
β = 82.084 (2)°
γ = 84.729 (2)°
V = 715.23 (9) Å³
Z = 2
D_x = 1.334 Mg m⁻³
Mo Kα radiation
Cell parameters from 3241 reflections
θ = 2.4–27.5°
μ = 0.10 mm⁻¹
T = 291 (2) K
Plate, colourless
0.40 × 0.34 × 0.06 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
φ–ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.959, T_max = 0.994
6134 measured reflections
3241 independent reflections
1951 reflections with I > 2σ(I)
R_int = 0.022
θ_max = 27.5°
h = −9 → 8
k = −11 → 11
l = −15 → 14

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.167
S = 1.02
3241 reflections
193 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.091P)² + 0.0203P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Compound (V)

Crystal data

C₈H₁₂N₄O₃
M_r = 212.22
Orthorhombic, Pbca
a = 7.9669 (5) Å
b = 17.2670 (11) Å
c = 13.6223 (9) Å
V = 1873.9 (2) Å³
Z = 8
D_x = 1.504 Mg m⁻³
Mo Kα radiation
Cell parameters from 2160 reflections
θ = 2.4–32.5°
μ = 0.12 mm⁻¹
T = 291 (2) K
Needle, colourless
0.60 × 0.07 × 0.06 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
φ–ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.928, T_max = 0.993
13 048 measured reflections
2160 independent reflections
1284 reflections with I > 2σ(I)
R_int = 0.057
θ_max = 27.5°
h = −10 → 9
k = −22 → 20
l = −17 → 17

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.129
S = 0.94
2160 reflections
139 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0725P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Selected bond distances (Å) for compounds (I)–(V)

	(I)	(II)	(III)	(IV)	(V)
C2—O2	1.208 (2)	1.219 (2)	1.2211 (18)	1.218 (2)	1.221 (2)
C4—O4	1.253 (2)	1.232 (2)	1.2442 (16)	1.239 (2)	1.239 (2)
C4—C5	1.437 (2)	1.440 (2)	1.4422 (18)	1.439 (2)	1.435 (2)
C5—C51	1.396 (2)	1.427 (2)	1.4308 (18)	1.422 (2)	1.429 (3)
C51—O51	1.311 (2)	–	–	–	–
C51—N51	–	1.313 (2)	1.3172 (17)	1.314 (2)	1.312 (2)
N51—N52	–	–	–	–	1.415 (2)
C6—O6	1.225 (2)	1.223 (2)	1.2278 (16)	1.222 (2)	1.224 (2)

Table 2
Hydrogen-bond parameters (Å, °) for compounds (I)–(V)

Compound	D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
(I)	O51—H51⋯O4	0.82	1.70	2.450 (2)	151

(II)	N51—H51⋯O4	0.86	1.85	2.563 (2)	139

(III)	N51—H51⋯O4	0.88	1.86	2.5829 (14)	139

(IV)	N51—H51⋯O4	0.86	1.85	2.559 (2)	139
	C514—H514⋯O4ⁱ	0.93	2.48	3.392 (2)	168
	C53—H53B⋯Cgⁱⁱ	0.97	2.66	3.557 (2)	154

(V)	N51—H51⋯O4	0.86	1.92	2.600 (2)	135
	N51—H51⋯O6ⁱⁱⁱ	0.86	2.35	2.974 (2)	129
	N52—H52D⋯O4^iv	0.86	2.45	3.230 (2)	152
	N52—H52E⋯O2^v	0.86	2.32	3.144 (2)	159
Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 1 - x, -y, 1 - z; (iii) $[x, {{1}\over{2}} - y, -{{1}\over{2}} + z]$ ; (iv) $[-{{1}\over{2}} + x, {{1}\over{2}} - y, -z]$ ; (v) $[2 - x, -{{1}\over{2}} + y, {{1}\over{2}} - z]$ . Note: Cg is the centroid of the C511–C516 ring.

For (I) and (V), space groups P2₁/c and Pbca, respectively, were uniquely assigned from the systematic absences. For (II), the systematic absences permitted Pn and P2/n as possible space groups; Pn was selected and confirmed by the structure analysis. For (III), the systematic absences permitted R3 and $[R\overline3]$ as possible space groups; $[R\overline3]$ was selected and confirmed by the structure analysis. Crystals of (IV) are triclinic; space group $[P\overline1]$ was selected and confirmed by the structure analysis. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.98 (CH₃), 0.99 (CH₂) or 1.00 Å (aliphatic CH) and N—H distances of 0.88 Å (at 120 K), and with C—H distances of 0.93 (aromatic), 0.96 (CH₃) or 0.97 Å (CH₂), N—H distances of 0.86 Å and O—H distances of 0.82 Å (at 291 K) [U_iso(H) = 1.2U_eq(C,N,O) or 1.5U_eq(C_methyl)]. In the absence of significant anomalous dispersion, the Flack (1983 ) parameter for (II) was inconclusive (Flack & Bernardinelli, 2000 ); it was therefore not possible to determine the correct orientation of the structure with respect to the polar axis directions (Jones, 1986 ) and, accordingly, Friedel pairs were merged prior to the final refinements.

For compounds (I), (II), (IV) and (V), data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

For compound (III), data collection: COLLECT (Hooft, 1999 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97; program(s) used to refine structure: OSCAIL and SHELXL97; molecular graphics: PLATON; software used to prepare material for publication: SHELXL97 and PRPKAPPA.

Supporting information

Crystal structure: contains datablocks global, I, II, III, IV, V. DOI: 10.1107/S0108270104028859/sk1792sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270104028859/sk1792Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S0108270104028859/sk1792IIsup3.hkl

Structure factors: contains datablock III. DOI: 10.1107/S0108270104028859/sk1792IIIsup4.hkl

Structure factors: contains datablock IV. DOI: 10.1107/S0108270104028859/sk1792IVsup5.hkl

Structure factors: contains datablock V. DOI: 10.1107/S0108270104028859/sk1792Vsup6.hkl

Comment top

It has recently been reported (da Silva & Lima, 2003) that the title compound, (I), which is the enol tautomer of 1,3-dimethyl-5-acetylbarbituric acid, reacts readily with primary amines to form enamines. We report here the structures of (I), of three representative enamine derivatives, (II)–(IV), and of the hydrazine derivative (V) (Figs. 1–5).

The bond distances in (I) (Table 1), in particular the C4—O4 and C51—O51 distances on the one hand and the C4—C5 and C5—C51 distances on the other, clearly demonstrate the enol constitution, consistent with the location of atom H51 as deduced from a difference map. In each of compounds (II)–(V), atom N51 has a planar configuration, and the C51—N51 distances are all typical of their type (Allen et al., 1987). Atom N52 in (V) has a distinctly pyramidal coordination environment, with a sum of bond angles, based on H-atom coordinates derived from difference maps, of 328.8°. The N51—N52 distance in (V) corresponds closely to the mean value of 1.420 Å for >N—N< distances where one N is planar and the other is pyramidal.

There is an intramolecular hydrogen bond in each of (I)–(V), of O—H···O type in (I) and of N—H···O type in (II)–(V) (Table 2). There are no direction-specific intermolecular interactions in (I)–(III), but the molecules in (IV) and (V) are linked by intermolecular hydrogen bonds (Table 2) into supramolecular structures that are one-dimensional and three-dimensional, respectively.

The one-dimensional supramolecular structure of (IV) is generated by a combination of C—H···O and C—H···π(arene) hydrogen bonds (Table 2). Aryl atom C514 in the molecule at (x, y, z) acts as a hydrogen-bond donor to carbonyl atom O4 in the molecule at (1 − x, 1 − y, 1 − z), so generating a centrosymmetric R²₂(22) ring (Bernstein et al., 1995) centred at (1/2, 1/2, 1/2) (Fig. 6). In addition, methylene atom C53 in the molecule at (x, y, z) acts as a hydrogen-bond donor to the C511–C516 aryl ring in the molecule at (1 − x, −y, 1 − z), so generating a second centrosymmetric ring, this time centred at (1/2, 0, 1/2). The combination of these two centrosymmetric motifs thus generates a chain of edge-fused rings running parallel to the [010] direction, with the larger rings centred at (1/2, 0.5 + n, 1/2) (n = zero or integer) and the smaller rings centred at (1/2, n, 1/2) (n = zero or integer) (Fig. 6).

The three-dimensional supramolecular structure of (V) is of some complexity but can readily be analysed in terms of a series of one-dimensional substructures and their simple combinations. In the first substructure, atom N52 in the molecule at (x, y, z) acts as a hydrogen-bond donor, via atom H52D, to atom O4 in the molecule at (−0.5 + x, 0.5 − y, −z), so producing a C(7) chain running parallel to the [100] direction and generated by the 2₁ screw axis along (x, 1/4, 0) (Fig. 7). In the second substructure, atom N52 at (x, y, z) acts as a donor, via atom H52E, to atom O2 in the molecule at (2 − x, −0.5 + y, 0.5 − z), so producing a C(9) chain running parallel to the [010] direction, now generated by the 2₁ screw axis along (1, y, 1/4) (Fig. 8).

Each of these chains, along [100] and [010], respectively, utilizes just one N—H···O hydrogen bond, but the combination of these two interactions produces a third chain motif, running parallel to the [001] direction. Atom N52 in the molecule at (−0.5 + x, 0.5 − y, −z) acts as a hydrogen-bond donor, via atom H52E, to atom O2 in the molecule at (1.5 − x, 1 − y, −0.5 + z), while atom N52 at (1.5 − x, 1 − y, −0.5 + z) acts as a donor, via atom H52D, to atom O4 at (2 − x, 0.5 + y, −0.5 − z); finally, atom N52 at (2 − x, 0.5 + y, −0.5 − z) acts as a donor, via atom H52E, to atom O2 in the molecule at (x, y, −1 + z). In this manner a C²₂(16) chain is generated along [001] (Fig. 9).

These three chain motifs (Figs. 7–9) together produce a three-dimensional framework structure, which is generated solely by the action of 2₁ screw axes and which utilizes only half of the molecules within the unit cell. There is, accordingly, a second such framework present, which is interwoven with the first framework and related to it by inversion. These two three-dimensional substructures are, however, linked by the final N—H···O hydrogen bond; this is, in fact, one component of an effectively planar three-centre N—H···(O)₂ system (Table 2). Atom N51 in the molecule at (x, y, z) acts as a donor, not only intramolecularly to atom O4 but also to atom O6 in the molecule at (x, 0.5 − y, −0.5 + z), so producing a C(6) chain running parallel to the [001] direction and generated by the c-glide plane at y = 0.25 (Fig. 10). This final motif suffices to link the two frameworks and hence to link all of the molecules into a single three-dimensional structure.

Experimental top

Samples of compounds (I)–(V) were prepared as described by da Silva & Lima (2003). Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of solutions in ethanol.

Computing details top

Data collection: SMART (Bruker, 2000) for (I), (II), (IV), (V); COLLECT (Hooft, 1999) for (III). Cell refinement: SAINT (Bruker, 2000) for (I), (II), (IV), (V); DENZO (Otwinowski & Minor, 1997) and COLLECT for (III). Data reduction: SAINT for (I), (II), (IV), (V); DENZO and COLLECT for (III). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) for (I), (II), (IV), (V); OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997) for (III). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for (I), (II), (IV), (V); OSCAIL and SHELXL97 (Sheldrick, 1997) for (III). For all compounds, molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. The molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecule of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. The molecule of (III), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 4. The molecule of (IV), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 5. The molecule of (V), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 6. A stereoview of part of the crystal structure of (IV), showing the formation of a chain of edge-fused rings along [010]. For clarity, H atoms not involved in the motifs shown have been omitted.
	Fig. 7. Part of the crystal structure of (V), showing the formation of a C(7) chain along [100]. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (−0.5 + x, 0.5 − y, −z) and (−1 + x, y, z), respectively.
	Fig. 8. Part of the crystal structure of (V), showing the formation of a C(9) chain along [010]. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (2 − x, −0.5 + y, 0.5 − z) and (2 − x, 0.5 + y, 0.5 − z), respectively.
	Fig. 9. A stereoview of part of the crystal structure of (V) showing the formation of a C²₂(16) chain along [001]. For clarity, H atoms bonded to C atoms have been omitted.
	Fig. 10. Part of the crystal structure of (V), showing the formation of a C(6) chain along [001]. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*), a hash (#) or an ampersand (&) are at the symmetry positions (x, 0.5 − y, 0.5 + z), (x, y, 1 + z) and (x, 0.5 − y, −0.5 + z), respectively.

(I) 5-(1-hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione top

Crystal data top

C₈H₁₀N₂O₄	F(000) = 416
M_r = 198.18	D_x = 1.475 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3198 reflections
a = 8.6066 (5) Å	θ = 2.9–32.5°
b = 9.1751 (5) Å	µ = 0.12 mm⁻¹
c = 11.9799 (7) Å	T = 291 K
β = 109.321 (2)°	Block, colourless
V = 892.73 (9) Å³	0.52 × 0.33 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area detector diffractometer	3198 independent reflections
Radiation source: fine-focus sealed X-ray tube	1926 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ–ω scans	θ_max = 32.5°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→5
T_min = 0.934, T_max = 0.976	k = −13→9
7606 measured reflections	l = −18→18

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.207	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.102P)² + 0.1435P] where P = (F_o² + 2F_c²)/3
3198 reflections	(Δ/σ)_max < 0.001
131 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₈H₁₀N₂O₄	V = 892.73 (9) Å³
M_r = 198.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6066 (5) Å	µ = 0.12 mm⁻¹
b = 9.1751 (5) Å	T = 291 K
c = 11.9799 (7) Å	0.52 × 0.33 × 0.20 mm
β = 109.321 (2)°

Data collection top

Bruker SMART 1000 CCD area detector diffractometer	3198 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1926 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.976	R_int = 0.022
7606 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.207	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
3198 reflections	Δρ_min = −0.22 e Å⁻³
131 parameters

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

	x	y	z	U_iso*/U_eq
O2	0.15848 (17)	0.66714 (19)	0.48681 (14)	0.0761 (5)
O4	0.68888 (18)	0.78399 (16)	0.54571 (13)	0.0641 (4)
O6	0.54580 (17)	0.41371 (16)	0.76817 (12)	0.0621 (4)
O51	0.91332 (17)	0.66835 (18)	0.70291 (15)	0.0707 (4)
N1	0.35333 (16)	0.53851 (16)	0.62581 (11)	0.0446 (3)
N3	0.42439 (18)	0.72019 (15)	0.51240 (11)	0.0458 (3)
C1	0.2236 (2)	0.4511 (2)	0.64934 (18)	0.0617 (5)
C2	0.3024 (2)	0.64364 (19)	0.53906 (14)	0.0471 (4)
C3	0.3700 (3)	0.8321 (2)	0.42007 (18)	0.0667 (6)
C4	0.5885 (2)	0.70517 (18)	0.57344 (14)	0.0444 (4)
C5	0.63903 (19)	0.59883 (17)	0.66653 (13)	0.0411 (3)
C6	0.51627 (19)	0.51007 (18)	0.69328 (13)	0.0425 (3)
C51	0.8064 (2)	0.5875 (2)	0.73124 (16)	0.0519 (4)
C52	0.8796 (3)	0.4923 (3)	0.8341 (2)	0.0829 (7)
H1A	0.2426	0.4487	0.7329	0.092*
H1B	0.2258	0.3536	0.6208	0.092*
H1C	0.1181	0.4942	0.6096	0.092*
H3A	0.3564	0.9232	0.4552	0.100*
H3B	0.2670	0.8034	0.3630	0.100*
H3C	0.4511	0.8430	0.3816	0.100*
H51	0.8649	0.7195	0.6459	0.085*
H52A	0.9958	0.5104	0.8662	0.124*
H52B	0.8610	0.3922	0.8100	0.124*
H52C	0.8296	0.5122	0.8933	0.124*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0438 (7)	0.0855 (11)	0.0813 (10)	0.0029 (7)	−0.0032 (7)	0.0159 (8)
O4	0.0652 (8)	0.0593 (9)	0.0717 (8)	−0.0110 (6)	0.0279 (7)	0.0061 (7)
O6	0.0570 (8)	0.0644 (9)	0.0614 (8)	0.0033 (6)	0.0148 (6)	0.0214 (6)
O51	0.0449 (7)	0.0780 (11)	0.0866 (11)	−0.0101 (7)	0.0181 (7)	−0.0055 (8)
N1	0.0394 (6)	0.0488 (8)	0.0436 (6)	−0.0028 (5)	0.0111 (5)	0.0003 (6)
N3	0.0535 (8)	0.0400 (7)	0.0394 (6)	0.0001 (6)	0.0093 (5)	0.0010 (5)
C1	0.0452 (9)	0.0730 (13)	0.0675 (11)	−0.0100 (8)	0.0195 (8)	0.0068 (10)
C2	0.0446 (8)	0.0466 (9)	0.0433 (7)	0.0001 (7)	0.0055 (6)	−0.0022 (6)
C3	0.0771 (13)	0.0550 (12)	0.0570 (10)	0.0007 (10)	0.0074 (9)	0.0169 (8)
C4	0.0495 (8)	0.0405 (8)	0.0429 (7)	−0.0026 (6)	0.0149 (6)	−0.0058 (6)
C5	0.0400 (7)	0.0413 (8)	0.0406 (7)	0.0007 (6)	0.0115 (6)	−0.0063 (6)
C6	0.0425 (7)	0.0449 (9)	0.0385 (7)	0.0013 (6)	0.0111 (6)	−0.0031 (6)
C51	0.0418 (8)	0.0545 (10)	0.0560 (9)	0.0021 (7)	0.0115 (7)	−0.0122 (7)
C52	0.0533 (11)	0.0963 (19)	0.0807 (14)	0.0117 (12)	−0.0027 (10)	0.0147 (13)

Geometric parameters (Å, º) top

C1—N1	1.475 (2)	C3—H3C	0.96
C1—H1A	0.96	C4—O4	1.253 (2)
C1—H1B	0.96	C4—C5	1.437 (2)
C1—H1C	0.96	C5—C51	1.396 (2)
C2—O2	1.208 (2)	C5—C6	1.451 (2)
C2—N1	1.379 (2)	C51—O51	1.311 (2)
C2—N3	1.386 (2)	C51—C52	1.471 (3)
N1—C6	1.392 (2)	C52—H52A	0.96
N3—C4	1.365 (2)	C52—H52B	0.96
N3—C3	1.468 (2)	C52—H52C	0.96
C3—H3A	0.96	O51—H51	0.82
C3—H3B	0.96	C6—O6	1.225 (2)

N1—C1—H1A	109.5	H3B—C3—H3C	109.5
N1—C1—H1B	109.5	O4—C4—N3	118.79 (16)
H1A—C1—H1B	109.5	O4—C4—C5	122.64 (16)
N1—C1—H1C	109.5	N3—C4—C5	118.58 (14)
H1A—C1—H1C	109.5	C51—C5—C4	118.29 (15)
H1B—C1—H1C	109.5	C51—C5—C6	121.90 (15)
O2—C2—N1	122.10 (17)	C4—C5—C6	119.79 (14)
O2—C2—N3	121.02 (16)	O51—C51—C5	119.85 (17)
N1—C2—N3	116.87 (14)	O51—C51—C52	114.22 (17)
C2—N1—C6	125.24 (14)	C5—C51—C52	125.93 (19)
C2—N1—C1	116.88 (14)	C51—C52—H52A	109.5
C6—N1—C1	117.88 (14)	C51—C52—H52B	109.5
C4—N3—C2	123.62 (14)	H52A—C52—H52B	109.5
C4—N3—C3	119.31 (16)	C51—C52—H52C	109.5
C2—N3—C3	116.83 (15)	H52A—C52—H52C	109.5
N3—C3—H3A	109.5	H52B—C52—H52C	109.5
N3—C3—H3B	109.5	C51—O51—H51	109.5
H3A—C3—H3B	109.5	O6—C6—N1	119.06 (15)
N3—C3—H3C	109.5	O6—C6—C5	125.24 (15)
H3A—C3—H3C	109.5	N1—C6—C5	115.70 (14)

O2—C2—N1—C6	−176.89 (16)	O4—C4—C5—C6	−179.38 (15)
N3—C2—N1—C6	4.3 (2)	N3—C4—C5—C6	0.2 (2)
O2—C2—N1—C1	2.3 (3)	C4—C5—C51—O51	−2.9 (2)
N3—C2—N1—C1	−176.53 (15)	C6—C5—C51—O51	179.03 (15)
O2—C2—N3—C4	175.60 (17)	C4—C5—C51—C52	175.76 (19)
N1—C2—N3—C4	−5.6 (2)	C6—C5—C51—C52	−2.3 (3)
O2—C2—N3—C3	1.2 (3)	C2—N1—C6—O6	179.79 (15)
N1—C2—N3—C3	−179.98 (15)	C1—N1—C6—O6	0.7 (2)
C2—N3—C4—O4	−176.93 (15)	C2—N1—C6—C5	−1.0 (2)
C3—N3—C4—O4	−2.7 (2)	C1—N1—C6—C5	179.91 (15)
C2—N3—C4—C5	3.4 (2)	C51—C5—C6—O6	−4.2 (3)
C3—N3—C4—C5	177.67 (15)	C4—C5—C6—O6	177.80 (15)
O4—C4—C5—C51	2.5 (2)	C51—C5—C6—N1	176.61 (14)
N3—C4—C5—C51	−177.85 (14)	C4—C5—C6—N1	−1.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O51—H51···O4	0.82	1.70	2.450 (2)	151

(II) 1,3-dimethyl-5-(1-propylaminoethylidene)pyrimidine-2,4,6(1H,3H,5H)-trione top

Crystal data top

C₁₁H₁₇N₃O₃	F(000) = 256
M_r = 239.28	D_x = 1.341 Mg m⁻³
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 2129 reflections
a = 4.1085 (3) Å	θ = 2.4–32.5°
b = 8.4497 (5) Å	µ = 0.10 mm⁻¹
c = 17.1272 (11) Å	T = 291 K
β = 94.721 (2)°	Lath, colourless
V = 592.56 (7) Å³	0.49 × 0.40 × 0.12 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD area detector diffractometer	2129 independent reflections
Radiation source: fine-focus sealed X-ray tube	1671 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ–ω scans	θ_max = 32.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→6
T_min = 0.931, T_max = 0.988	k = −12→12
5869 measured reflections	l = −17→25

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0836P)²] where P = (F_o² + 2F_c²)/3
2129 reflections	(Δ/σ)_max < 0.001
158 parameters	Δρ_max = 0.19 e Å⁻³
2 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₁H₁₇N₃O₃	V = 592.56 (7) Å³
M_r = 239.28	Z = 2
Monoclinic, Pn	Mo Kα radiation
a = 4.1085 (3) Å	µ = 0.10 mm⁻¹
b = 8.4497 (5) Å	T = 291 K
c = 17.1272 (11) Å	0.49 × 0.40 × 0.12 mm
β = 94.721 (2)°

Data collection top

Bruker SMART 1000 CCD area detector diffractometer	2129 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1671 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.988	R_int = 0.022
5869 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	2 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
2129 reflections	Δρ_min = −0.27 e Å⁻³
158 parameters

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

	x	y	z	U_iso*/U_eq
O2	−0.1487 (6)	0.6297 (2)	0.17114 (12)	0.0757 (5)
O4	0.3625 (4)	0.24030 (15)	0.31415 (9)	0.0539 (4)
O6	0.4409 (5)	0.77604 (17)	0.39406 (12)	0.0691 (5)
N1	0.1514 (5)	0.70039 (19)	0.28271 (11)	0.0493 (4)
N3	0.1034 (4)	0.43561 (19)	0.24510 (9)	0.0442 (3)
N51	0.7094 (4)	0.30194 (18)	0.44180 (10)	0.0442 (3)
C1	0.0685 (8)	0.8679 (3)	0.26797 (17)	0.0705 (7)
C2	0.0236 (5)	0.5912 (2)	0.22940 (12)	0.0497 (4)
C3	−0.0342 (6)	0.3140 (3)	0.19047 (13)	0.0560 (5)
C4	0.3062 (4)	0.3832 (2)	0.30920 (10)	0.0404 (3)
C5	0.4315 (4)	0.50075 (19)	0.36465 (10)	0.0381 (3)
C6	0.3515 (5)	0.6659 (2)	0.35116 (11)	0.0447 (4)
C51	0.6311 (4)	0.4518 (2)	0.43250 (10)	0.0395 (3)
C52	0.7544 (6)	0.5641 (3)	0.49526 (13)	0.0553 (5)
C53	0.8946 (5)	0.2300 (2)	0.50958 (11)	0.0467 (4)
C54	0.9653 (6)	0.0585 (2)	0.49084 (13)	0.0519 (4)
C55	1.1227 (6)	−0.0276 (3)	0.56190 (16)	0.0629 (6)
H1A	0.0733	0.8902	0.2131	0.106*
H1B	0.2243	0.9339	0.2974	0.106*
H1C	−0.1462	0.8888	0.2838	0.106*
H31	−0.2070	0.3594	0.1565	0.084*
H32	−0.1192	0.2284	0.2195	0.084*
H33	0.1336	0.2749	0.1597	0.084*
H51	0.6452	0.2392	0.4041	0.053*
H52A	0.8360	0.5056	0.5408	0.083*
H52B	0.5797	0.6318	0.5085	0.083*
H52C	0.9270	0.6271	0.4769	0.083*
H53A	0.7692	0.2356	0.5551	0.056*
H53B	1.0978	0.2868	0.5213	0.056*
H54A	0.7630	0.0058	0.4729	0.062*
H54B	1.1096	0.0543	0.4488	0.062*
H55A	1.3038	0.0333	0.5846	0.094*
H55B	1.1988	−0.1293	0.5463	0.094*
H55C	0.9653	−0.0412	0.5998	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0973 (14)	0.0687 (10)	0.0557 (9)	0.0106 (10)	−0.0264 (9)	0.0048 (8)
O4	0.0752 (9)	0.0374 (6)	0.0465 (7)	−0.0018 (6)	−0.0104 (7)	−0.0063 (6)
O6	0.0995 (13)	0.0378 (6)	0.0661 (10)	0.0002 (7)	−0.0177 (9)	−0.0089 (7)
N1	0.0659 (10)	0.0376 (7)	0.0436 (8)	0.0027 (6)	0.0003 (7)	0.0023 (6)
N3	0.0546 (9)	0.0446 (7)	0.0324 (7)	−0.0011 (6)	−0.0037 (6)	−0.0037 (5)
N51	0.0538 (9)	0.0413 (7)	0.0359 (7)	−0.0004 (6)	−0.0056 (6)	−0.0009 (6)
C1	0.0965 (19)	0.0411 (10)	0.0715 (16)	0.0122 (10)	−0.0069 (14)	0.0109 (10)
C2	0.0570 (11)	0.0520 (10)	0.0394 (9)	0.0032 (8)	−0.0010 (8)	0.0014 (7)
C3	0.0695 (12)	0.0555 (10)	0.0407 (9)	−0.0065 (9)	−0.0091 (8)	−0.0098 (8)
C4	0.0489 (9)	0.0404 (7)	0.0313 (7)	−0.0024 (7)	0.0005 (6)	−0.0037 (6)
C5	0.0471 (9)	0.0339 (6)	0.0329 (7)	−0.0024 (6)	0.0017 (6)	−0.0019 (5)
C6	0.0550 (10)	0.0381 (7)	0.0410 (9)	−0.0009 (7)	0.0031 (7)	−0.0012 (7)
C51	0.0431 (9)	0.0419 (8)	0.0333 (7)	−0.0034 (6)	0.0028 (6)	−0.0030 (6)
C52	0.0680 (13)	0.0511 (10)	0.0443 (10)	0.0017 (9)	−0.0098 (9)	−0.0139 (8)
C53	0.0512 (10)	0.0492 (10)	0.0381 (9)	0.0006 (7)	−0.0065 (7)	0.0022 (7)
C54	0.0567 (11)	0.0488 (9)	0.0486 (10)	0.0036 (8)	−0.0054 (8)	0.0004 (8)
C55	0.0680 (13)	0.0561 (12)	0.0616 (13)	0.0076 (10)	−0.0127 (10)	0.0096 (10)

Geometric parameters (Å, º) top

N1—C2	1.372 (3)	C51—N51	1.313 (2)
N1—C6	1.406 (3)	C51—C52	1.491 (2)
N1—C1	1.473 (2)	N51—C53	1.467 (2)
C1—H1A	0.96	N51—H51	0.86
C1—H1B	0.96	C52—H52A	0.96
C1—H1C	0.96	C52—H52B	0.96
C2—O2	1.219 (3)	C52—H52C	0.96
C2—N3	1.376 (3)	C53—C54	1.517 (3)
N3—C4	1.394 (2)	C53—H53A	0.97
N3—C3	1.471 (2)	C53—H53B	0.97
C3—H31	0.96	C54—C55	1.516 (3)
C3—H32	0.96	C54—H54A	0.97
C3—H33	0.96	C54—H54B	0.97
C4—O4	1.232 (2)	C55—H55A	0.96
C4—C5	1.440 (2)	C55—H55B	0.96
C5—C51	1.427 (2)	C55—H55C	0.96
C5—C6	1.448 (2)	C6—O6	1.223 (2)

C2—N1—C6	125.53 (16)	C51—N51—C53	127.00 (16)
C2—N1—C1	117.50 (19)	C51—N51—H51	116.5
C6—N1—C1	116.96 (18)	C53—N51—H51	116.5
N1—C1—H1A	109.5	C51—C52—H52A	109.5
N1—C1—H1B	109.5	C51—C52—H52B	109.5
H1A—C1—H1B	109.5	H52A—C52—H52B	109.5
N1—C1—H1C	109.5	C51—C52—H52C	109.5
H1A—C1—H1C	109.5	H52A—C52—H52C	109.5
H1B—C1—H1C	109.5	H52B—C52—H52C	109.5
O2—C2—N1	121.99 (19)	N51—C53—C54	108.92 (16)
O2—C2—N3	121.9 (2)	N51—C53—H53A	109.9
N1—C2—N3	116.13 (16)	C54—C53—H53A	109.9
C2—N3—C4	125.05 (15)	N51—C53—H53B	109.9
C2—N3—C3	118.03 (17)	C54—C53—H53B	109.9
C4—N3—C3	116.91 (16)	H53A—C53—H53B	108.3
N3—C3—H31	109.5	C55—C54—C53	111.39 (18)
N3—C3—H32	109.5	C55—C54—H54A	109.3
H31—C3—H32	109.5	C53—C54—H54A	109.3
N3—C3—H33	109.5	C55—C54—H54B	109.3
H31—C3—H33	109.5	C53—C54—H54B	109.3
H32—C3—H33	109.5	H54A—C54—H54B	108.0
O4—C4—N3	117.53 (14)	C54—C55—H55A	109.5
O4—C4—C5	125.17 (15)	C54—C55—H55B	109.5
N3—C4—C5	117.30 (15)	H55A—C55—H55B	109.5
C51—C5—C4	119.18 (15)	C54—C55—H55C	109.5
C51—C5—C6	121.14 (15)	H55A—C55—H55C	109.5
C4—C5—C6	119.68 (15)	H55B—C55—H55C	109.5
N51—C51—C5	119.80 (15)	O6—C6—N1	117.97 (16)
N51—C51—C52	117.45 (17)	O6—C6—C5	125.76 (18)
C5—C51—C52	122.74 (16)	N1—C6—C5	116.26 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N51—H51···O4	0.86	1.85	2.563 (2)	139

(III) 5-[1-(2,2-dimethoxyethylamino)ethylidene]-1,3-dimethylpyrimidine- 2,4,6(1H,3H,5H)-trione top

Crystal data top

C₁₂H₁₉N₃O₅	D_x = 1.462 Mg m⁻³
M_r = 285.30	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 2965 reflections
Hall symbol: -R 3	θ = 3.1–27.5°
a = 18.4577 (4) Å	µ = 0.12 mm⁻¹
c = 19.7736 (4) Å	T = 120 K
V = 5834.1 (2) Å³	Block, colourless
Z = 18	0.40 × 0.40 × 0.30 mm
F(000) = 2736

Data collection top

Nonius KappaCCD area detector diffractometer	2965 independent reflections
Radiation source: fine-focus sealed X-ray tube	2329 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ–ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −19→23
T_min = 0.950, T_max = 0.966	k = −23→19
14896 measured reflections	l = −22→25

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0597P)² + 2.9334P] where P = (F_o² + 2F_c²)/3
2965 reflections	(Δ/σ)_max < 0.001
186 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₂H₁₉N₃O₅	Z = 18
M_r = 285.30	Mo Kα radiation
Trigonal, R3	µ = 0.12 mm⁻¹
a = 18.4577 (4) Å	T = 120 K
c = 19.7736 (4) Å	0.40 × 0.40 × 0.30 mm
V = 5834.1 (2) Å³

Data collection top

Nonius KappaCCD area detector diffractometer	2965 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2329 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.966	R_int = 0.033
14896 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.11	Δρ_max = 0.35 e Å⁻³
2965 reflections	Δρ_min = −0.30 e Å⁻³
186 parameters

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

	x	y	z	U_iso*/U_eq
O2	−0.15632 (6)	0.33916 (6)	0.09144 (5)	0.0206 (2)
O4	−0.05233 (6)	0.61636 (6)	0.05752 (5)	0.0193 (2)
O6	0.12518 (6)	0.50353 (6)	0.09788 (5)	0.0216 (3)
O51	0.08471 (6)	0.83411 (6)	−0.02294 (5)	0.0182 (2)
O52	0.08356 (6)	0.85482 (6)	0.09012 (5)	0.0205 (2)
N1	−0.01542 (7)	0.42417 (7)	0.09841 (6)	0.0149 (3)
N3	−0.10321 (7)	0.47955 (7)	0.07858 (6)	0.0152 (3)
N51	0.10694 (7)	0.71932 (7)	0.06069 (6)	0.0159 (3)
C1	−0.00815 (9)	0.35043 (8)	0.11368 (7)	0.0187 (3)
C2	−0.09556 (8)	0.40959 (8)	0.08972 (7)	0.0154 (3)
C3	−0.18752 (8)	0.46736 (9)	0.07052 (7)	0.0203 (3)
C4	−0.03586 (8)	0.56031 (8)	0.07096 (6)	0.0143 (3)
C5	0.04738 (8)	0.57301 (8)	0.07892 (7)	0.0142 (3)
C6	0.05812 (8)	0.50185 (8)	0.09210 (7)	0.0147 (3)
C51	0.11810 (8)	0.65554 (8)	0.07353 (7)	0.0145 (3)
C52	0.20607 (8)	0.67348 (9)	0.08217 (7)	0.0181 (3)
C53	0.17286 (8)	0.80644 (8)	0.05238 (8)	0.0185 (3)
C54	0.13520 (8)	0.86096 (8)	0.03604 (7)	0.0173 (3)
C55	0.13239 (9)	0.85833 (9)	−0.08419 (7)	0.0225 (3)
C56	0.05569 (10)	0.91427 (9)	0.08661 (8)	0.0245 (3)
H1A	−0.0514	0.3150	0.1464	0.028*
H1B	0.0472	0.3682	0.1329	0.028*
H1C	−0.0154	0.3187	0.0720	0.028*
H3A	−0.2289	0.4104	0.0844	0.030*
H3B	−0.1967	0.4757	0.0230	0.030*
H3C	−0.1933	0.5078	0.0988	0.030*
H51	0.0550	0.7085	0.0567	0.019*
H52A	0.2222	0.6523	0.0429	0.027*
H52B	0.2100	0.6459	0.1232	0.027*
H52C	0.2437	0.7340	0.0861	0.027*
H53A	0.2109	0.8105	0.0154	0.022*
H53B	0.2060	0.8264	0.0945	0.022*
H54	0.1808	0.9204	0.0305	0.021*
H55A	0.1735	0.9182	−0.0826	0.034*
H55B	0.0949	0.8469	−0.1228	0.034*
H55C	0.1615	0.8264	−0.0892	0.034*
H56A	0.1042	0.9708	0.0832	0.037*
H56B	0.0238	0.9101	0.1275	0.037*
H56C	0.0200	0.9027	0.0468	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0158 (5)	0.0150 (5)	0.0263 (6)	0.0041 (4)	−0.0012 (4)	−0.0007 (4)
O4	0.0167 (5)	0.0171 (5)	0.0272 (6)	0.0108 (4)	−0.0021 (4)	0.0001 (4)
O6	0.0149 (5)	0.0202 (5)	0.0323 (6)	0.0108 (4)	−0.0009 (4)	0.0014 (4)
O51	0.0147 (5)	0.0192 (5)	0.0190 (5)	0.0071 (4)	−0.0007 (4)	0.0000 (4)
O52	0.0247 (6)	0.0197 (5)	0.0199 (5)	0.0131 (5)	0.0030 (4)	0.0026 (4)
N1	0.0144 (6)	0.0131 (6)	0.0180 (6)	0.0075 (5)	−0.0006 (5)	−0.0004 (4)
N3	0.0104 (5)	0.0154 (6)	0.0200 (6)	0.0066 (5)	−0.0006 (5)	0.0001 (5)
N51	0.0119 (6)	0.0137 (6)	0.0209 (6)	0.0056 (5)	−0.0001 (5)	0.0004 (5)
C1	0.0201 (7)	0.0145 (7)	0.0229 (7)	0.0096 (6)	−0.0010 (6)	0.0003 (6)
C2	0.0152 (7)	0.0167 (7)	0.0135 (6)	0.0075 (6)	−0.0002 (5)	−0.0010 (5)
C3	0.0130 (7)	0.0207 (7)	0.0273 (8)	0.0085 (6)	−0.0013 (6)	0.0012 (6)
C4	0.0144 (7)	0.0145 (7)	0.0130 (6)	0.0064 (6)	−0.0003 (5)	−0.0011 (5)
C5	0.0129 (7)	0.0145 (7)	0.0146 (6)	0.0064 (5)	−0.0006 (5)	−0.0007 (5)
C6	0.0146 (7)	0.0157 (7)	0.0132 (6)	0.0073 (5)	−0.0003 (5)	−0.0017 (5)
C51	0.0154 (7)	0.0160 (7)	0.0118 (6)	0.0076 (6)	0.0005 (5)	−0.0008 (5)
C52	0.0141 (7)	0.0175 (7)	0.0214 (7)	0.0071 (6)	−0.0004 (6)	0.0009 (6)
C53	0.0133 (7)	0.0143 (7)	0.0243 (7)	0.0041 (6)	−0.0008 (6)	0.0031 (6)
C54	0.0149 (7)	0.0150 (7)	0.0188 (7)	0.0052 (6)	−0.0011 (5)	0.0008 (6)
C55	0.0221 (8)	0.0239 (8)	0.0203 (7)	0.0106 (7)	0.0014 (6)	0.0012 (6)
C56	0.0294 (8)	0.0233 (8)	0.0263 (8)	0.0171 (7)	0.0005 (6)	−0.0005 (6)

Geometric parameters (Å, º) top

N1—C2	1.3756 (17)	C52—H52B	0.98
N1—C6	1.4027 (17)	C52—H52C	0.98
N1—C1	1.4644 (17)	N51—C53	1.4617 (16)
C1—H1A	0.98	N51—H51	0.88
C1—H1B	0.98	C53—C54	1.5166 (19)
C1—H1C	0.98	C53—H53A	0.99
C2—O2	1.2211 (16)	C53—H53B	0.99
C2—N3	1.3851 (17)	C54—O52	1.3990 (17)
N3—C4	1.3918 (16)	C54—O51	1.4185 (16)
N3—C3	1.4655 (17)	C54—H54	1.00
C3—H3A	0.98	O51—C55	1.4312 (17)
C3—H3B	0.98	C55—H55A	0.98
C3—H3C	0.98	C55—H55B	0.98
C4—O4	1.2442 (16)	C55—H55C	0.98
C4—C5	1.4422 (18)	O52—C56	1.4275 (17)
C5—C51	1.4308 (18)	C56—H56A	0.98
C5—C6	1.4467 (18)	C56—H56B	0.98
C51—N51	1.3172 (17)	C56—H56C	0.98
C51—C52	1.4959 (18)	C6—O6	1.2278 (16)
C52—H52A	0.98

C2—N1—C6	125.82 (11)	H52A—C52—H52C	109.5
C2—N1—C1	115.68 (11)	H52B—C52—H52C	109.5
C6—N1—C1	118.48 (11)	C51—N51—C53	126.06 (11)
N1—C1—H1A	109.5	C51—N51—H51	117.0
N1—C1—H1B	109.5	C53—N51—H51	117.0
H1A—C1—H1B	109.5	N51—C53—C54	110.38 (11)
N1—C1—H1C	109.5	N51—C53—H53A	109.6
H1A—C1—H1C	109.5	C54—C53—H53A	109.6
H1B—C1—H1C	109.5	N51—C53—H53B	109.6
O2—C2—N1	122.02 (12)	C54—C53—H53B	109.6
O2—C2—N3	121.98 (12)	H53A—C53—H53B	108.1
N1—C2—N3	116.01 (11)	O52—C54—O51	107.34 (10)
C2—N3—C4	124.25 (11)	O52—C54—C53	107.64 (11)
C2—N3—C3	118.01 (11)	O51—C54—C53	112.48 (11)
C4—N3—C3	117.64 (11)	O52—C54—H54	109.8
N3—C3—H3A	109.5	O51—C54—H54	109.8
N3—C3—H3B	109.5	C53—C54—H54	109.8
H3A—C3—H3B	109.5	C54—O51—C55	113.12 (10)
N3—C3—H3C	109.5	O51—C55—H55A	109.5
H3A—C3—H3C	109.5	O51—C55—H55B	109.5
H3B—C3—H3C	109.5	H55A—C55—H55B	109.5
O4—C4—N3	117.06 (11)	O51—C55—H55C	109.5
O4—C4—C5	124.86 (12)	H55A—C55—H55C	109.5
N3—C4—C5	118.08 (11)	H55B—C55—H55C	109.5
C51—C5—C4	119.70 (12)	C54—O52—C56	113.15 (10)
C51—C5—C6	120.92 (12)	O52—C56—H56A	109.5
C4—C5—C6	119.37 (11)	O52—C56—H56B	109.5
N51—C51—C5	119.92 (12)	H56A—C56—H56B	109.5
N51—C51—C52	117.49 (12)	O52—C56—H56C	109.5
C5—C51—C52	122.59 (12)	H56A—C56—H56C	109.5
C51—C52—H52A	109.5	H56B—C56—H56C	109.5
C51—C52—H52B	109.5	O6—C6—N1	117.75 (12)
H52A—C52—H52B	109.5	O6—C6—C5	126.00 (12)
C51—C52—H52C	109.5	N1—C6—C5	116.25 (11)

C6—N1—C2—O2	174.79 (12)	C6—C5—C51—C52	−1.1 (2)
C1—N1—C2—O2	−3.37 (19)	C5—C51—N51—C53	−178.62 (12)
C6—N1—C2—N3	−4.91 (19)	C52—C51—N51—C53	1.6 (2)
C1—N1—C2—N3	176.92 (11)	C51—N51—C53—C54	178.30 (12)
O2—C2—N3—C4	−174.82 (12)	N51—C53—C54—O52	60.54 (14)
N1—C2—N3—C4	4.88 (19)	N51—C53—C54—O51	−57.51 (15)
O2—C2—N3—C3	1.62 (19)	O52—C54—O51—C55	163.79 (10)
N1—C2—N3—C3	−178.68 (11)	C53—C54—O51—C55	−77.99 (14)
C2—N3—C4—O4	176.16 (12)	O51—C54—O52—C56	−68.98 (13)
C3—N3—C4—O4	−0.29 (18)	C53—C54—O52—C56	169.72 (11)
C2—N3—C4—C5	−3.67 (19)	C2—N1—C6—O6	−176.12 (12)
C3—N3—C4—C5	179.88 (12)	C1—N1—C6—O6	2.00 (18)
O4—C4—C5—C51	2.1 (2)	C2—N1—C6—C5	3.60 (19)
N3—C4—C5—C51	−178.08 (11)	C1—N1—C6—C5	−178.28 (11)
O4—C4—C5—C6	−177.72 (12)	C51—C5—C6—O6	−2.1 (2)
N3—C4—C5—C6	2.09 (19)	C4—C5—C6—O6	177.69 (13)
C4—C5—C51—N51	−0.65 (19)	C51—C5—C6—N1	178.17 (11)
C6—C5—C51—N51	179.17 (12)	C4—C5—C6—N1	−2.00 (18)
C4—C5—C51—C52	179.12 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N51—H51···O4	0.88	1.86	2.5829 (14)	139

(IV) 5-[1-(benzylamino)ethylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione top

Crystal data top

C₁₅H₁₇N₃O₃	Z = 2
M_r = 287.32	F(000) = 304
Triclinic, P1	D_x = 1.334 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0696 (5) Å	Cell parameters from 3241 reflections
b = 9.0734 (7) Å	θ = 2.4–27.5°
c = 11.9214 (8) Å	µ = 0.10 mm⁻¹
α = 70.995 (2)°	T = 291 K
β = 82.084 (2)°	Plate, colourless
γ = 84.729 (2)°	0.40 × 0.34 × 0.06 mm
V = 715.23 (9) Å³

Data collection top

Bruker SMART 1000 CCD area detector diffractometer	3241 independent reflections
Radiation source: fine-focus sealed X-ray tube	1951 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ–ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→8
T_min = 0.959, T_max = 0.994	k = −11→11
6134 measured reflections	l = −15→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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.091P)² + 0.0203P] where P = (F_o² + 2F_c²)/3
3241 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₇N₃O₃	γ = 84.729 (2)°
M_r = 287.32	V = 715.23 (9) Å³
Triclinic, P1	Z = 2
a = 7.0696 (5) Å	Mo Kα radiation
b = 9.0734 (7) Å	µ = 0.10 mm⁻¹
c = 11.9214 (8) Å	T = 291 K
α = 70.995 (2)°	0.40 × 0.34 × 0.06 mm
β = 82.084 (2)°

Data collection top

Bruker SMART 1000 CCD area detector diffractometer	3241 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1951 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.994	R_int = 0.022
6134 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.02	Δρ_max = 0.17 e Å⁻³
3241 reflections	Δρ_min = −0.19 e Å⁻³
193 parameters

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

	x	y	z	U_iso*/U_eq
O2	0.8283 (2)	0.77351 (17)	−0.24671 (13)	0.0730 (4)
O4	0.63770 (18)	0.53917 (14)	0.14349 (11)	0.0585 (4)
O6	0.8917 (2)	0.24754 (18)	−0.11249 (13)	0.0806 (5)
N1	0.86528 (19)	0.50943 (18)	−0.17581 (13)	0.0518 (4)
N3	0.72782 (19)	0.65292 (16)	−0.05138 (13)	0.0476 (4)
N51	0.6979 (2)	0.24520 (17)	0.24030 (13)	0.0521 (4)
C1	0.9526 (3)	0.5053 (3)	−0.29394 (17)	0.0709 (6)
C2	0.8089 (2)	0.6526 (2)	−0.16369 (16)	0.0511 (4)
C3	0.6678 (3)	0.8033 (2)	−0.03372 (19)	0.0619 (5)
C4	0.7087 (2)	0.5200 (2)	0.04795 (15)	0.0439 (4)
C5	0.7713 (2)	0.37156 (19)	0.03285 (15)	0.0434 (4)
C6	0.8448 (2)	0.3650 (2)	−0.08449 (16)	0.0519 (5)
C51	0.7615 (2)	0.2346 (2)	0.13415 (16)	0.0461 (4)
C52	0.8242 (3)	0.0738 (2)	0.12950 (19)	0.0637 (5)
C53	0.6938 (3)	0.1173 (2)	0.35324 (18)	0.0682 (6)
C511	0.6304 (3)	0.1765 (2)	0.45713 (16)	0.0556 (5)
C512	0.4584 (3)	0.2565 (3)	0.4644 (2)	0.0773 (7)
C513	0.3990 (5)	0.3072 (3)	0.5603 (2)	0.1066 (10)
C514	0.5105 (6)	0.2763 (3)	0.6516 (2)	0.1050 (11)
C515	0.6786 (5)	0.1941 (3)	0.6460 (2)	0.1036 (9)
C516	0.7404 (4)	0.1456 (3)	0.5486 (2)	0.0815 (7)
H1A	0.8602	0.4749	−0.3331	0.106*
H1B	1.0601	0.4313	−0.2849	0.106*
H1C	0.9946	0.6069	−0.3411	0.106*
H3A	0.7571	0.8294	0.0098	0.093*
H3B	0.5430	0.7966	0.0106	0.093*
H3C	0.6638	0.8826	−0.1099	0.093*
H51	0.6547	0.3356	0.2436	0.063*
H52A	0.9400	0.0401	0.1663	0.096*
H52B	0.8465	0.0757	0.0478	0.096*
H52C	0.7262	0.0029	0.1715	0.096*
H53A	0.8204	0.0665	0.3614	0.082*
H53B	0.6068	0.0406	0.3532	0.082*
H512	0.3809	0.2769	0.4035	0.093*
H513	0.2823	0.3629	0.5637	0.128*
H514	0.4707	0.3114	0.7166	0.126*
H515	0.7534	0.1701	0.7086	0.124*
H516	0.8580	0.0913	0.5449	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0895 (10)	0.0666 (9)	0.0558 (9)	−0.0082 (7)	−0.0048 (7)	−0.0099 (8)
O4	0.0739 (9)	0.0535 (7)	0.0511 (8)	0.0048 (6)	0.0021 (6)	−0.0266 (6)
O6	0.1209 (12)	0.0690 (9)	0.0574 (9)	0.0218 (9)	−0.0046 (8)	−0.0370 (8)
N1	0.0508 (8)	0.0632 (9)	0.0445 (8)	−0.0015 (7)	−0.0022 (6)	−0.0232 (7)
N3	0.0460 (8)	0.0468 (8)	0.0523 (9)	−0.0013 (6)	−0.0044 (6)	−0.0195 (7)
N51	0.0638 (9)	0.0452 (8)	0.0472 (9)	0.0005 (6)	0.0014 (7)	−0.0186 (7)
C1	0.0775 (13)	0.0909 (15)	0.0446 (11)	−0.0001 (11)	0.0026 (9)	−0.0269 (11)
C2	0.0468 (10)	0.0603 (11)	0.0488 (11)	−0.0064 (8)	−0.0071 (8)	−0.0190 (9)
C3	0.0681 (12)	0.0488 (10)	0.0708 (13)	0.0008 (9)	−0.0053 (10)	−0.0237 (10)
C4	0.0385 (8)	0.0502 (10)	0.0473 (10)	−0.0018 (7)	−0.0048 (7)	−0.0214 (8)
C5	0.0389 (8)	0.0491 (9)	0.0476 (10)	0.0002 (7)	−0.0045 (7)	−0.0236 (8)
C6	0.0505 (10)	0.0621 (11)	0.0492 (10)	0.0055 (8)	−0.0071 (8)	−0.0276 (9)
C51	0.0422 (9)	0.0508 (9)	0.0513 (10)	−0.0026 (7)	−0.0029 (7)	−0.0253 (8)
C52	0.0780 (13)	0.0493 (11)	0.0647 (13)	0.0002 (9)	0.0046 (10)	−0.0253 (10)
C53	0.0942 (15)	0.0506 (11)	0.0534 (12)	0.0007 (10)	0.0070 (10)	−0.0148 (9)
C511	0.0737 (12)	0.0431 (9)	0.0454 (10)	−0.0057 (8)	0.0010 (9)	−0.0101 (8)
C512	0.0902 (16)	0.0839 (16)	0.0578 (13)	0.0197 (12)	−0.0098 (11)	−0.0285 (12)
C513	0.156 (3)	0.0869 (18)	0.0659 (16)	0.0353 (17)	0.0115 (17)	−0.0301 (14)
C514	0.208 (3)	0.0581 (14)	0.0511 (14)	−0.0167 (18)	0.0160 (18)	−0.0295 (12)
C515	0.171 (3)	0.0832 (19)	0.0654 (17)	−0.0254 (19)	−0.0359 (18)	−0.0219 (15)
C516	0.0927 (16)	0.0799 (16)	0.0713 (15)	−0.0004 (12)	−0.0211 (13)	−0.0194 (13)

Geometric parameters (Å, º) top

N1—C2	1.371 (2)	C52—H52B	0.96
N1—C6	1.409 (2)	C52—H52C	0.96
N1—C1	1.469 (2)	N51—C53	1.462 (2)
C1—H1A	0.96	N51—H51	0.86
C1—H1B	0.96	C53—C511	1.503 (3)
C1—H1C	0.96	C53—H53A	0.97
C2—O2	1.218 (2)	C53—H53B	0.97
C2—N3	1.383 (2)	C511—C512	1.365 (3)
N3—C4	1.389 (2)	C511—C516	1.366 (3)
N3—C3	1.464 (2)	C512—C513	1.367 (3)
C3—H3A	0.96	C512—H512	0.93
C3—H3B	0.96	C513—C514	1.372 (4)
C3—H3C	0.96	C513—H513	0.93
C4—O4	1.239 (2)	C514—C515	1.349 (4)
C4—C5	1.439 (2)	C514—H514	0.93
C5—C51	1.422 (2)	C515—C516	1.375 (4)
C5—C6	1.442 (2)	C515—H515	0.93
C51—N51	1.314 (2)	C516—H516	0.93
C51—C52	1.501 (2)	C6—O6	1.222 (2)
C52—H52A	0.96

C2—N1—C6	125.47 (15)	C51—C52—H52C	109.5
C2—N1—C1	117.56 (17)	H52A—C52—H52C	109.5
C6—N1—C1	116.97 (16)	H52B—C52—H52C	109.5
N1—C1—H1A	109.5	C51—N51—C53	125.94 (15)
N1—C1—H1B	109.5	C51—N51—H51	117.0
H1A—C1—H1B	109.5	C53—N51—H51	117.0
N1—C1—H1C	109.5	N51—C53—C511	110.86 (15)
H1A—C1—H1C	109.5	N51—C53—H53A	109.5
H1B—C1—H1C	109.5	C511—C53—H53A	109.5
O2—C2—N1	122.34 (17)	N51—C53—H53B	109.5
O2—C2—N3	121.41 (18)	C511—C53—H53B	109.5
N1—C2—N3	116.25 (16)	H53A—C53—H53B	108.1
C2—N3—C4	124.21 (15)	C512—C511—C516	118.6 (2)
C2—N3—C3	118.22 (15)	C512—C511—C53	120.74 (19)
C4—N3—C3	117.47 (14)	C516—C511—C53	120.6 (2)
N3—C3—H3A	109.5	C511—C512—C513	120.7 (2)
N3—C3—H3B	109.5	C511—C512—H512	119.7
H3A—C3—H3B	109.5	C513—C512—H512	119.7
N3—C3—H3C	109.5	C512—C513—C514	120.4 (3)
H3A—C3—H3C	109.5	C512—C513—H513	119.8
H3B—C3—H3C	109.5	C514—C513—H513	119.8
O4—C4—N3	116.84 (15)	C515—C514—C513	119.1 (2)
O4—C4—C5	124.92 (16)	C515—C514—H514	120.4
N3—C4—C5	118.24 (14)	C513—C514—H514	120.4
C51—C5—C4	119.34 (15)	C514—C515—C516	120.6 (3)
C51—C5—C6	121.38 (15)	C514—C515—H515	119.7
C4—C5—C6	119.28 (16)	C516—C515—H515	119.7
N51—C51—C5	119.82 (16)	C511—C516—C515	120.6 (2)
N51—C51—C52	116.09 (17)	C511—C516—H516	119.7
C5—C51—C52	124.08 (16)	C515—C516—H516	119.7
C51—C52—H52A	109.5	O6—C6—N1	116.95 (16)
C51—C52—H52B	109.5	O6—C6—C5	126.76 (18)
H52A—C52—H52B	109.5	N1—C6—C5	116.29 (15)

C6—N1—C2—O2	−178.99 (16)	C52—C51—N51—C53	3.9 (3)
C1—N1—C2—O2	0.3 (3)	C51—N51—C53—C511	174.11 (16)
C6—N1—C2—N3	0.9 (2)	N51—C53—C511—C512	57.3 (3)
C1—N1—C2—N3	−179.77 (14)	N51—C53—C511—C516	−125.4 (2)
O2—C2—N3—C4	−177.32 (16)	C516—C511—C512—C513	1.1 (4)
N1—C2—N3—C4	2.8 (2)	C53—C511—C512—C513	178.5 (2)
O2—C2—N3—C3	−0.9 (2)	C511—C512—C513—C514	−0.9 (4)
N1—C2—N3—C3	179.20 (15)	C512—C513—C514—C515	−0.6 (4)
C2—N3—C4—O4	178.08 (14)	C513—C514—C515—C516	1.8 (4)
C3—N3—C4—O4	1.7 (2)	C512—C511—C516—C515	0.1 (4)
C2—N3—C4—C5	−2.1 (2)	C53—C511—C516—C515	−177.3 (2)
C3—N3—C4—C5	−178.50 (14)	C514—C515—C516—C511	−1.6 (4)
O4—C4—C5—C51	−3.1 (3)	C2—N1—C6—O6	175.44 (17)
N3—C4—C5—C51	177.09 (14)	C1—N1—C6—O6	−3.9 (3)
O4—C4—C5—C6	177.62 (16)	C2—N1—C6—C5	−4.9 (3)
N3—C4—C5—C6	−2.2 (2)	C1—N1—C6—C5	175.78 (15)
C4—C5—C51—N51	−0.9 (2)	C51—C5—C6—O6	5.7 (3)
C6—C5—C51—N51	178.43 (15)	C4—C5—C6—O6	−175.00 (18)
C4—C5—C51—C52	−179.47 (16)	C51—C5—C6—N1	−173.94 (14)
C6—C5—C51—C52	−0.2 (3)	C4—C5—C6—N1	5.4 (2)
C5—C51—N51—C53	−174.85 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N51—H51···O4	0.86	1.85	2.559 (2)	139
C514—H514···O4ⁱ	0.93	2.48	3.392 (3)	168
C53—H53B···Cgⁱⁱ	0.97	2.66	3.557 (2)	154

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

(V) 5-(1-hydrazinoethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione top

Crystal data top

C₈H₁₂N₄O₃	F(000) = 896
M_r = 212.22	D_x = 1.504 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2160 reflections
a = 7.9669 (5) Å	θ = 2.4–32.5°
b = 17.2670 (11) Å	µ = 0.12 mm⁻¹
c = 13.6223 (9) Å	T = 291 K
V = 1873.9 (2) Å³	Needle, colourless
Z = 8	0.60 × 0.07 × 0.06 mm

Data collection top

Bruker SMART 1000 CCD area detector diffractometer	2160 independent reflections
Radiation source: fine-focus sealed X-ray tube	1284 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ϕ–ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→9
T_min = 0.928, T_max = 0.993	k = −22→20
13048 measured reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0725P)²] where P = (F_o² + 2F_c²)/3
2160 reflections	(Δ/σ)_max < 0.001
139 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₈H₁₂N₄O₃	V = 1873.9 (2) Å³
M_r = 212.22	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.9669 (5) Å	µ = 0.12 mm⁻¹
b = 17.2670 (11) Å	T = 291 K
c = 13.6223 (9) Å	0.60 × 0.07 × 0.06 mm

Data collection top

Bruker SMART 1000 CCD area detector diffractometer	2160 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1284 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.993	R_int = 0.057
13048 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 0.94	Δρ_max = 0.19 e Å⁻³
2160 reflections	Δρ_min = −0.17 e Å⁻³
139 parameters

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

	x	y	z	U_iso*/U_eq
O2	1.1589 (2)	0.49967 (9)	0.32501 (11)	0.0694 (5)
O4	0.95239 (17)	0.34103 (8)	0.08980 (9)	0.0480 (4)
O6	0.8848 (2)	0.28577 (8)	0.42741 (9)	0.0595 (5)
N1	1.0322 (2)	0.38828 (9)	0.37377 (11)	0.0435 (4)
N3	1.0478 (2)	0.42123 (8)	0.20775 (11)	0.0407 (4)
N51	0.7788 (2)	0.21905 (8)	0.13666 (11)	0.0410 (4)
N52	0.6755 (2)	0.15632 (9)	0.10817 (12)	0.0500 (5)
C1	1.0836 (3)	0.40278 (13)	0.47556 (14)	0.0610 (6)
C2	1.0841 (3)	0.44030 (11)	0.30366 (14)	0.0458 (5)
C3	1.1006 (3)	0.47600 (12)	0.13169 (16)	0.0584 (6)
C4	0.9650 (2)	0.35372 (10)	0.17898 (13)	0.0366 (4)
C5	0.8996 (2)	0.30411 (10)	0.25437 (13)	0.0358 (4)
C6	0.9330 (2)	0.32237 (10)	0.35578 (13)	0.0405 (5)
C51	0.8036 (2)	0.23712 (10)	0.22909 (12)	0.0358 (4)
C52	0.7317 (3)	0.18395 (11)	0.30431 (14)	0.0500 (5)
H1A	1.1780	0.4374	0.4762	0.091*
H1B	1.1145	0.3547	0.5061	0.091*
H1C	0.9921	0.4257	0.5110	0.091*
H3A	1.0309	0.5213	0.1344	0.088*
H3B	1.0901	0.4521	0.0684	0.088*
H3C	1.2155	0.4905	0.1425	0.088*
H51	0.8269	0.2462	0.0919	0.049*
H52A	0.6597	0.1469	0.2729	0.075*
H52B	0.6681	0.2134	0.3511	0.075*
H52C	0.8211	0.1573	0.3374	0.075*
H52D	0.6436	0.1692	0.0501	0.060*
H52E	0.7278	0.1128	0.1102	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0871 (13)	0.0579 (9)	0.0630 (10)	−0.0173 (9)	−0.0086 (9)	−0.0125 (8)
O4	0.0618 (9)	0.0551 (8)	0.0271 (7)	−0.0058 (7)	0.0024 (6)	0.0026 (6)
O6	0.0877 (12)	0.0613 (9)	0.0295 (7)	0.0035 (8)	0.0081 (7)	0.0049 (6)
N1	0.0502 (10)	0.0498 (10)	0.0304 (8)	0.0079 (8)	−0.0039 (7)	−0.0051 (7)
N3	0.0477 (10)	0.0375 (8)	0.0370 (9)	0.0012 (7)	−0.0012 (7)	0.0026 (6)
N51	0.0412 (10)	0.0450 (9)	0.0370 (9)	−0.0030 (7)	0.0043 (7)	−0.0009 (7)
N52	0.0514 (11)	0.0471 (9)	0.0516 (10)	−0.0036 (8)	−0.0036 (8)	−0.0054 (8)
C1	0.0727 (16)	0.0764 (14)	0.0338 (12)	0.0033 (13)	−0.0074 (10)	−0.0113 (10)
C2	0.0487 (13)	0.0446 (11)	0.0442 (12)	0.0074 (10)	−0.0027 (9)	−0.0053 (9)
C3	0.0752 (16)	0.0477 (12)	0.0524 (13)	−0.0108 (11)	−0.0024 (12)	0.0103 (9)
C4	0.0369 (11)	0.0402 (10)	0.0328 (10)	0.0079 (8)	0.0021 (8)	0.0015 (8)
C5	0.0388 (10)	0.0399 (9)	0.0287 (9)	0.0076 (9)	0.0020 (8)	0.0022 (7)
C6	0.0469 (12)	0.0438 (11)	0.0308 (10)	0.0138 (9)	0.0029 (8)	0.0004 (8)
C51	0.0334 (10)	0.0411 (10)	0.0330 (10)	0.0114 (8)	0.0042 (7)	0.0026 (7)
C52	0.0539 (13)	0.0508 (12)	0.0453 (11)	−0.0009 (10)	0.0019 (10)	0.0126 (9)

Geometric parameters (Å, º) top

N1—C2	1.375 (3)	C4—C5	1.435 (2)
N1—C6	1.407 (2)	C5—C51	1.429 (2)
N1—C1	1.467 (2)	C5—C6	1.442 (2)
C1—H1A	0.96	C51—N51	1.312 (2)
C1—H1B	0.96	C51—C52	1.490 (2)
C1—H1C	0.96	N51—N52	1.415 (2)
C2—O2	1.221 (2)	N51—H51	0.86
C2—N3	1.378 (2)	C52—H52A	0.96
N3—C4	1.396 (2)	C52—H52B	0.96
N3—C3	1.465 (2)	C52—H52C	0.96
C3—H3A	0.96	N52—H52D	0.86
C3—H3B	0.96	N52—H52E	0.86
C3—H3C	0.96	C6—O6	1.224 (2)
C4—O4	1.239 (2)

C2—N1—C6	125.19 (16)	N3—C4—C5	117.98 (15)
C2—N1—C1	117.47 (17)	C51—C5—C4	120.34 (16)
C6—N1—C1	117.34 (16)	C51—C5—C6	120.46 (16)
N1—C1—H1A	109.5	C4—C5—C6	119.20 (17)
N1—C1—H1B	109.5	N51—C51—C5	120.30 (15)
H1A—C1—H1B	109.5	N51—C51—C52	117.09 (16)
N1—C1—H1C	109.5	C5—C51—C52	122.59 (16)
H1A—C1—H1C	109.5	C51—N51—N52	122.21 (15)
H1B—C1—H1C	109.5	C51—N51—H51	118.9
O2—C2—N1	121.99 (19)	N52—N51—H51	118.9
O2—C2—N3	121.92 (18)	C51—C52—H52A	109.5
N1—C2—N3	116.09 (18)	C51—C52—H52B	109.5
C2—N3—C4	124.40 (15)	H52A—C52—H52B	109.5
C2—N3—C3	117.15 (17)	C51—C52—H52C	109.5
C4—N3—C3	118.45 (15)	H52A—C52—H52C	109.5
N3—C3—H3A	109.5	H52B—C52—H52C	109.5
N3—C3—H3B	109.5	N51—N52—H52D	103.1
H3A—C3—H3B	109.5	N51—N52—H52E	112.2
N3—C3—H3C	109.5	H52D—N52—H52E	113.5
H3A—C3—H3C	109.5	O6—C6—N1	117.07 (17)
H3B—C3—H3C	109.5	O6—C6—C5	126.34 (19)
O4—C4—N3	117.49 (15)	N1—C6—C5	116.59 (16)
O4—C4—C5	124.53 (17)

C6—N1—C2—O2	174.12 (18)	N3—C4—C5—C6	−4.9 (2)
C1—N1—C2—O2	−5.6 (3)	C4—C5—C51—N51	2.1 (3)
C6—N1—C2—N3	−6.4 (3)	C6—C5—C51—N51	−177.40 (16)
C1—N1—C2—N3	173.91 (17)	C4—C5—C51—C52	−179.57 (17)
O2—C2—N3—C4	179.01 (18)	C6—C5—C51—C52	0.9 (3)
N1—C2—N3—C4	−0.5 (3)	C5—C51—N51—N52	−175.71 (15)
O2—C2—N3—C3	−1.0 (3)	C52—C51—N51—N52	5.9 (3)
N1—C2—N3—C3	179.53 (17)	C2—N1—C6—O6	−173.49 (18)
C2—N3—C4—O4	−174.45 (17)	C1—N1—C6—O6	6.2 (3)
C3—N3—C4—O4	5.5 (3)	C2—N1—C6—C5	7.1 (3)
C2—N3—C4—C5	5.9 (3)	C1—N1—C6—C5	−173.19 (17)
C3—N3—C4—C5	−174.11 (17)	C51—C5—C6—O6	−0.9 (3)
O4—C4—C5—C51	−4.0 (3)	C4—C5—C6—O6	179.56 (18)
N3—C4—C5—C51	175.62 (15)	C51—C5—C6—N1	178.40 (15)
O4—C4—C5—C6	175.52 (17)	C4—C5—C6—N1	−1.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N51—H51···O4	0.86	1.92	2.600 (2)	135
N51—H51···O6ⁱ	0.86	2.35	2.974 (2)	129
N52—H52D···O4ⁱⁱ	0.86	2.45	3.230 (2)	152
N52—H52E···O2ⁱⁱⁱ	0.86	2.33	3.144 (2)	159

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

Experimental details

	(I)	(II)	(III)	(IV)
Crystal data
Chemical formula	C₈H₁₀N₂O₄	C₁₁H₁₇N₃O₃	C₁₂H₁₉N₃O₅	C₁₅H₁₇N₃O₃
M_r	198.18	239.28	285.30	287.32
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, Pn	Trigonal, R3	Triclinic, P1
Temperature (K)	291	291	120	291
a, b, c (Å)	8.6066 (5), 9.1751 (5), 11.9799 (7)	4.1085 (3), 8.4497 (5), 17.1272 (11)	18.4577 (4), 18.4577 (4), 19.7736 (4)	7.0696 (5), 9.0734 (7), 11.9214 (8)
α, β, γ (°)	90, 109.321 (2), 90	90, 94.721 (2), 90	90, 90, 120	70.995 (2), 82.084 (2), 84.729 (2)
V (Å³)	892.73 (9)	592.56 (7)	5834.1 (2)	715.23 (9)
Z	4	2	18	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.12	0.10	0.12	0.10
Crystal size (mm)	0.52 × 0.33 × 0.20	0.49 × 0.40 × 0.12	0.40 × 0.40 × 0.30	0.40 × 0.34 × 0.06

Data collection
Diffractometer	Bruker SMART 1000 CCD area detector diffractometer	Bruker SMART 1000 CCD area detector diffractometer	Nonius KappaCCD area detector diffractometer	Bruker SMART 1000 CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)	Multi-scan (SADABS; Bruker, 2000)	Multi-scan (SADABS; Bruker, 2000)	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.934, 0.976	0.931, 0.988	0.950, 0.966	0.959, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	7606, 3198, 1926	5869, 2129, 1671	14896, 2965, 2329	6134, 3241, 1951
R_int	0.022	0.022	0.033	0.022
(sin θ/λ)_max (Å⁻¹)	0.757	0.756	0.650	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.207, 1.03	0.046, 0.126, 1.01	0.042, 0.115, 1.11	0.054, 0.167, 1.02
No. of reflections	3198	2129	2965	3241
No. of parameters	131	158	186	193
No. of restraints	0	2	0	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.22	0.19, −0.27	0.35, −0.30	0.17, −0.19

	(V)
Crystal data
Chemical formula	C₈H₁₂N₄O₃
M_r	212.22
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	291
a, b, c (Å)	7.9669 (5), 17.2670 (11), 13.6223 (9)
α, β, γ (°)	90, 90, 90
V (Å³)	1873.9 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.60 × 0.07 × 0.06

Data collection
Diffractometer	Bruker SMART 1000 CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.928, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	13048, 2160, 1284
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.129, 0.94
No. of reflections	2160
No. of parameters	139
No. of restraints	0
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: SMART (Bruker, 2000), COLLECT (Hooft, 1999), SAINT (Bruker, 2000), DENZO (Otwinowski & Minor, 1997) and COLLECT, SAINT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected bond distances (Å) for compounds (I)–(V) top

Parameter	(I)	(II)	(III)	(IV)	(V)
C2-O2	1.208 (2)	1.219 (2)	1.2211 (18)	1.218 (2)	1.221 (2)
C4-O4	1.253 (2)	1.232 (2)	1.2442 (16)	1.239 (2)	1.239 (2)
C4-C5	1.437 (2)	1.440 (2)	1.4422 (18)	1.439 (2)	1.435 (2)
C5-C51	1.396 (2)	1.427 (2)	1.4308 (18)	1.422 (2)	1.429 (3)
C51-O51	1.311 (2)
C51-N51		1.313 (2)	1.3172 (17)	1.314 (2)	1.312 (2)
N51-N52					1.415 (2)
C6-O6	1.225 (2)	1.223 (2)	1.2278 (16)	1.222 (2)	1.224 (2)

Hydrogen bond parameters (Å, °) for compounds (I)–(V) top

Compound	D-H···A	D-H	H···A	D···A	D-H···A
(I)	O51-H51···O4	0.82	1.70	2.450 (2)	151
(II)	N51-H51···O4	0.86	1.85	2.563 (2)	139
(III)	N51-H51···O4	0.88	1.86	2.5829 (14)	139
(IV)	N51-H51···O4	0.86	1.85	2.559 (2)	139
	C514-H514···O4ⁱ	0.93	2.48	3.392 (2)	168
	C53-H53B···Cgⁱⁱ	0.97	2.66	3.557 (2)	154
(V)	N51-H51···O4	0.86	1.92	2.600 (2)	135
	N51-H51 O6ⁱⁱⁱ	0.86	2.35	2.974 (2)	129
	N52-H52D···O4^iv	0.86	2.45	3.230 (2)	152
	N52-H52E···O2^v	0.86	2.32	3.144 (2)	159

Symmetry codes: i (1 − x, 1 − y, 1 − z); ii (1 − x, −y, 1 − z); iii (x, 0.5 − y, −0.5 + z); iv (−0.5 + x, 0.5 − y, −z); v (2 − x, −0.5 + y, 0.5 − z)

Cg is centroid of ring C511-C516

Acknowledgements

X-ray data for (I), (II), (IV) and (V) were collected at the University of Aberdeen and the authors thank the university for funding the purchase of the diffractometer. X-ray data for (III) were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England; the authors thank the staff of the service for all their help and advice. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work. ELSL thanks the International Foundation for Science and JLW thanks CNPq and FAPERJ for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 61| Part 1| January 2005| Pages o15-o20

doi:10.1107/S0108270104028859

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

5-(1-Hy­droxy­ethyl­­idene)-1,3-di­methyl­pyrimidine-2,4,6(1H,3H,5H)-trione and four amino derivatives

Comment

Experimental

Compound (I)

Crystal data

Data collection

Refinement

Compound (II)

Crystal data

Data collection

Refinement

Compound (III)

Crystal data

Data collection

Refinement

Compound (IV)

Crystal data

Data collection

Refinement

Compound (V)

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-(1-Hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione and four amino derivatives