Supramolecular structures of five 5-(aryl­methyl­ene)-1,3-dimethyl­pyrimidine-2,4,6(1H,3H,5H)-triones: isolated mol­ecules, hydrogen-bonded chains and chains of fused hydrogen-bonded rings

Rezende, M.C.; Dominguez, M.; Wardell, J.L.; Skakle, J.M.S.; Low, J.N.; Glidewell, C.

doi:10.1107/S0108270105008498

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 61| Part 5| May 2005| Pages o306-o311

doi:10.1107/S0108270105008498

Supramolecular structures of five 5-(arylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones: isolated molecules, hydrogen-bonded chains and chains of fused hydrogen-bonded rings

Marcos C. Rezende,^a Moisés Dominguez,^a James L. Wardell,^b Janet M. S. Skakle,^c John N. Low ^c and Christopher Glidewell ^d ^*

^aFacultad de Química y Biología, Universidad de Santiago, Casilla 40, Correo 33, Santiago, Chile, ^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 14 March 2005; accepted 16 March 2005; online 23 April 2005)

In each of the five title compounds, namely 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₁₃H₁₂N₂O₃, (I), 5-(3-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₁₄H₁₄N₂O₄, (II), 5-(4-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₁₄H₁₄N₂O₄, (III), 5-[4-(dimethylamino)benzylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₁₅H₁₇N₃O₃, (IV), and 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₂₁H₂₈N₂O₄, (V), which crystallizes with Z′ = 2 in P $[\overline{1}]$ , there is a very wide C—C—C angle at the methine C atom linking the two rings, ranging from 137.1 (2)° in (I) to 139.14 (14)° in (III). There is evidence for intramolecular charge separation in (IV) and, to a lesser degree, in (III). The molecules of (I)–(III) are linked by pairs of C—H⋯O hydrogen bonds into chains of edge-fused rings, with alternating R₂²(14) and R₂²(16) rings in (I), alternating R₂²(14) and R₄⁴(20) rings in (II), with two types of R₂²(16) rings alternating in (III). The molecules in (IV) are linked by a single C—H⋯O hydrogen bond into simple C(8) chains, but there are no direction-specific intermolecular interactions in (V).

Comment

The title compounds, (I)–(V), were initially prepared as part of a study of solvatochromism (Rezende et al., 2001 , 2004 ), and it was considered necessary to determine their molecular and supramolecular structures for subsequent comparison with their NMR and solvatochromic behaviour.

Compounds (I)–(IV) (Figs. 1–4 ) all crystallize with Z′ = 1, but compound (V) (Fig. 5) crystallizes with Z′ = 2 in space group P $[\overline{1}]$ ; the two independent molecules are very close to being mirror images of one another, but a careful search for possible additional symmetry revealed none. In each of compounds (I)–(V), the molecules are nearly planar, as shown by the leading torsion angles (Table 1), and there are short intramolecular C—H⋯O contacts to both O4 and O6 (Table 2). Of these, the dimensions of that involving O6 are suggestive of a genuine hydrogen bond. However, the bond angles at C5 and C57 give a strong indication that the H57⋯O4 contact is repulsive: the C—C—C angles at C57 are, in all cases, particularly large for fragments of this type. Similarly, the bond angles at C51 are more consistent with a repulsive H52⋯O6 contact than with a significantly attractive contact. However, it is noteworthy that these repulsive contacts are accommodated by distortion of the skeletal bond angles in preference to an evasive rotation around the C51—C57 bond, which would appear at first sight to represent a far less energy-costly resolution. In each of the methoxy compounds, viz. (II) and (III), the methoxy C atom is nearly coplanar with the adjacent aryl ring and the exocyclic bond angles at the aryl C atom ipso to the methoxy substituent, viz. C53 in (II) and C54 in (III), show the usual deviations from 120°.

Whereas in compounds (I) and (II), the C—C distances in the aryl rings are consistent with classically delocalized π electrons, in compounds (III) and, particularly, (IV), there is evidence for a significant contribution from polarized charge-separated forms. Thus in (IV), the C52—C53 and C55—C56 distances are significantly less than the remaining distances in the aryl ring. Likewise, the C51—C57 bond in (IV) is the shortest such bond observed in this series, while C57—C5 is the longest. The C4—O4 and C6—O6 bonds are also longer in (IV) than in (I)–(III). Finally, the C54—N54 distance is less than the quartile value (1.363 Å; Allen et al., 1987 ) for bonds of this type. Taken all together, these observations provide evidence for the contribution of the polarized forms (IVa) and (IVb) to the overall molecular–electronic structure. There are similar, although weaker, indications for the contribution of similar forms in (III), not only from the distances within the aryl ring but also, in particular, the fact that the C51—C57 bond is shorter in (III) than in the isomeric compound (II), while C57—C5 is longer in (III) than in (II). In addition, the C54—O54 bond in (III) is somewhat shorter than the C53—O53 bond in (II). In compound (V), the indications for charge-separation are very weak, at best.

In each of compounds (I) and (II), the heterocyclic ring shows a small but significant deviation from planarity, with a total puckering amplitude Q (Cremer & Pople, 1975 ) of 0.105 (2) Å in (I) and 0.075 (2) Å in (II). The ring-puckering parameters for the atom sequence N1–C2–N3–C4–C5–C6 are θ = 51.9 (11)° and φ = 276.7 (16)° for (I), and θ = 137.2 (11)° and φ = 45.9 (17)° for (II). The best single description for both of these rings is thus as half-chair conformers (Evans & Boeyens, 1989 ). In the two independent molecules in compound (V), the heterocyclic rings have effectively identical total puckering amplitudes, viz. 0.115 (3) Å in molecule 1 (Fig. 5a) and 0.114 (3) Å in molecule 2 (Fig. 5b). The ring-puckering parameters for the atom sequences Nn1–Cn2–Nn3–Cn4–Cn5–Cn6 (where n = 1 or 2) are θ = 70.0 (15)° and φ = 16.7 (14)° when n = 1, and θ = 109.5 (15)° and φ = 193.5 (14)° when n = 2, emphasizing the nearly enantiomorphous character of the two molecules in the selected asymmetric unit. The best single descriptor for these ring conformations is screw-boat, for which ideally θ = 67.5° and φ = (60k + 30)°. By contrast, the heterocyclic rings in compounds (III) and (IV) are effectively planar.

In compounds (I)–(III), the molecules are linked by pairs of C—H⋯O hydrogen bonds (Table 2) into chains of edge-fused rings, but the details of these interactions are different in each case, as are the structures of the resulting chains. In compound (I) (Fig. 1), aryl atoms C53 and C56 in the molecule at (x, y, z) act as hydrogen-bond donors to, respectively, atom O6 in the molecule at (1 − x, 1 − y, 1 − z) and O4 in the molecule at (1 − x, −y, 1 − z), so generating by inversion a chain of edge-fused rings running parallel to the [010] direction. There are R₂²(16) (Bernstein et al., 1995 ) rings centred at ( $[{1\over 2}]$ , $[{1\over 2}]$ + n, $[{1\over 2}]$ ) (n = zero or integer) and R₂²(14) rings centred at ( $[{1\over 2}]$ , n, $[{1\over 2}]$ ) (n = zero or integer) (Fig. 6). Two chains of this type pass through each unit cell, centred along the lines ( $[{1\over 2}]$ , y, $[{1\over 2}]$ ) and (0, y, 0), but there are no direction-specific interactions between adjacent chains.

In compound (II) (Fig. 2), aryl atom C56 in the molecule at (x, y, z) acts as hydrogen-bond donor to atom O4 in the molecule at (1 − x, 1 − y, 1 − z), so generating by inversion an R₂²(14) ring analogous to that in compound (I), although now centred at ( $[{1\over 2}]$ , $[{1\over 2}]$ , $[{1\over 2}]$ ) (Fig. 6). At the same time, atom C54 at (x, y, z) acts as donor to atom O2 in the molecule at (x − 2, 1 + y, z), so generating by translation a C(11) chain running parallel to the [ $[\overline{2}]$ 10] direction. The combination of the two hydrogen bonds then generates a [ $[\overline{2}]$ 10] chain of centrosymmetric edge-fused R₂²(14) and R₄⁴(20) rings. Of the four molecules which participate in the formation of an R₄⁴(20) ring, two act as double donors and two as double acceptors of hydrogen bonds (Fig. 7). Again, there are no direction-specific interactions between adjacent chains.

The chain formation in compound (III) is rather different from that in the isomeric compound, (II). In (III), aryl atoms C53 and C55 in the molecule at (x, y, z) act as hydrogen-bond donors to, respectively, atoms O6 and O4 in the molecules at (1 − x, −y, 1 − z) and (−x, 1 − y, 1 − z), so generating by inversion a chain of edge-fused rings along [1 $[\overline{1}]$ 0] in which there are two distinct types of centrosymmetric R₂²(16) ring (Fig. 8), one involving O4 as the sole hydrogen-bond acceptor and the other involving O6 only.

In contrast with the chain formation in compounds (I)–(III), that in compound (IV) (Fig. 4) depends upon just one intermolecular C—H⋯O hydrogen bond. Atom C53 in the molecule at (x, y, z) acts as hydrogen-bond donor to atom O4 in the molecule at (x, y, z − 1), thereby generating by translation a simple C(8) chain running parallel to the [001] direction (Fig. 9). Two such chains, antiparallel to one another, pass through each unit cell, but there are no direction-specific interactions between adjacent chains.

In compound (V), there are no direction-specific intermolecular interactions. In particular, neither of the hydroxyl groups participates in hydrogen-bond formation, because of the steric shielding provided by the two adjacent tert-butyl substituents. The nearest plausible donor/acceptor atoms to O154 and O254 are, respectively, O154 at (1 − x, −y, 1 − z), with O⋯Oⁱ and O⋯Hⁱ distances of 3.391 (2) and 3.56 Å, respectively, and O254 at (2 − x, 1 − y, 1 − z), with O⋯Oⁱⁱ and O⋯Hⁱⁱ distances of 3.010 (2) and 2.91 Å, respectively [symmetry codes: (i) 1 − x, −y, 1 − z; (ii) 2 − x, 1 − y, 1 − z].

Figure 1
The molecule of compound (I)

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

Figure 2
The molecule of compound (II)

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

Figure 3
The molecule of compound (III)

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

Figure 4
The molecule of compound (IV)

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

Figure 5
The independent molecules of compound (V)

, showing the atom-labelling schemes for (a) molecule 1 and (b) molecule 2. Displacement ellipsoids are drawn at the 30% probability level.

Figure 6
A stereoview of part of the crystal structure of compound (I)

, showing the formation of a [010] chain of alternating R₂²(14) and R₂²(16) rings. For the sake of clarity, the H atoms not involved in these motifs have been omitted.

Figure 7
A stereoview of part of the crystal structure of compound (II)

, showing the formation of a [ $[\overline{2}]$ 10] chain of alternating R₂²(14) and R₄⁴(20) rings. For the sake of clarity, the H atoms not involved in these motifs have been omitted.

Figure 8
A stereoview of part of the crystal structure of compound (III)

, showing the formation of a [1 $[\overline{1}]$ 0] chain containing two types of R₂²(16) ring. For the sake of clarity, the H atoms not involved in these motifs have been omitted.

Figure 9
Part of the crystal structure of compound (IV)

, showing the formation of a C(8) chain along [001]. For the sake of clarity, the H atoms not involved in this motif have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, y, z − 1) and (x, y, 1 + z), respectively.

Experimental

For the preparation of compounds (I)–(V), mixtures of N,N′-dimethylbarbituric acid (0.50 g, 3.2 mmol) and the appropriate arylaldehyde (3.2 mmol) in glacial acetic acid (4 ml) were heated under reflux for 2 h, cooled and filtered. The resulting solids were washed with diethyl ether (5 ml). Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of solutions in acetic acid for (I) and (II), in acetonitrile for (III) and (IV), or in ethanol for (V). For (I), m.p. 430–432 K (literature value 430–431 K; Suzuki et al., 1976 ); for (II), m.p. 406–408 K; for (III), m.p. 416–418 K (literature value 417–418 K; Suzuki et al., 1976); for (IV), m.p. 497–499 K (literature value 497–499 K; Rezende et al., 2001); for (V), m.p. 467–469 K.

Compound (I)

Crystal data

C₁₃H₁₂N₂O₃
M_r = 244.25
Monoclinic, P 2₁ /n
a = 6.1293 (3) Å
b = 13.9633 (8) Å
c = 13.2727 (8) Å
β = 97.688 (4)°
V = 1125.74 (11) Å³
Z = 4
D_x = 1.441 Mg m⁻³
Mo Kα radiation
Cell parameters from 2573 reflections
θ = 2.9–27.6°
μ = 0.10 mm⁻¹
T = 120 (2) K
Plate, colourless
0.34 × 0.25 × 0.09 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003 )T_min = 0.954, T_max = 0.991
12 444 measured reflections
2573 independent reflections
1885 reflections with I > 2σ(I)
R_int = 0.050
θ_max = 27.6°
h = −7 → 7
k = −18 → 16
l = −17 → 17

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.201, S = 1.05
2573 reflections
165 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.1092P)² + 0.6873P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Compound (II)

Crystal data

C₁₄H₁₄N₂O₄
M_r = 274.27
Triclinic, $[P \overline 1]$
a = 5.6946 (2) Å
b = 8.2994 (3) Å
c = 14.0411 (5) Å
α = 73.5580 (17)°
β = 87.393 (2)°
γ = 77.037 (2)°
V = 620.13 (4) Å³
Z = 2
D_x = 1.469 Mg m⁻³
Mo Kα radiation
Cell parameters from 2847 reflections
θ = 3.0–27.5°
μ = 0.11 mm⁻¹
T = 120 (2) K
Block, colourless
0.52 × 0.34 × 0.16 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)T_min = 0.953, T_max = 0.983
14 859 measured reflections
2847 independent reflections
2331 reflections with I > 2σ(I)
R_int = 0.034
θ_max = 27.5°
h = −7 → 7
k = −10 → 10
l = −18 → 18

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.132, S = 1.11
2847 reflections
184 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0732P)² + 0.1975P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Compound (III)

Crystal data

C₁₄H₁₄N₂O₄
M_r = 274.27
Triclinic, $[P \overline 1]$
a = 7.5906 (6) Å
b = 8.2989 (7) Å
c = 10.3010 (10) Å
α = 92.544 (6)°
β = 93.074 (5)°
γ = 104.456 (6)°
V = 626.33 (10) Å³
Z = 2
D_x = 1.454 Mg m⁻³
Mo Kα radiation
Cell parameters from 2860 reflections
θ = 3.1–27.5°
μ = 0.11 mm⁻¹
T = 120 (2) K
Block, yellow
0.48 × 0.44 × 0.34 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)T_min = 0.947, T_max = 0.964
10 553 measured reflections
2860 independent reflections
2173 reflections with I > 2σ(I)
R_int = 0.034
θ_max = 27.5°
h = −9 → 9
k = −10 → 10
l = −13 → 13

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.136, S = 1.06
2860 reflections
184 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0773P)² + 0.1359P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Compound (IV)

Crystal data

C₁₅H₁₇N₃O₃
M_r = 287.32
Triclinic, $[P \overline 1]$
a = 8.6187 (2) Å
b = 8.8451 (3) Å
c = 9.0566 (3) Å
α = 82.2980 (18)°
β = 84.465 (2)°
γ = 82.365 (2)°
V = 675.94 (4) Å³
Z = 2
D_x = 1.412 Mg m⁻³
Mo Kα radiation
Cell parameters from 3073 reflections
θ = 3.1–27.5°
μ = 0.10 mm⁻¹
T = 120 (2) K
Block, orange
0.40 × 0.30 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)T_min = 0.955, T_max = 0.980
13 410 measured reflections
3073 independent reflections
2698 reflections with I > 2σ(I)
R_int = 0.027
θ_max = 27.5°
h = −11 → 11
k = −11 → 11
l = −11 → 11

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108, S = 1.05
3073 reflections
194 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0577P)² + 0.2209P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.009
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Compound (V)

Crystal data

C₂₁H₂₈N₂O₄
M_r = 372.45
Triclinic, $[P \overline 1]$
a = 9.6040 (3) Å
b = 11.6691 (4) Å
c = 17.2905 (6) Å
α = 97.4860 (16)°
β = 92.5540 (18)°
γ = 90.006 (2)°
V = 1919.29 (11) Å³
Z = 4
D_x = 1.289 Mg m⁻³
Mo Kα radiation
Cell parameters from 8856 reflections
θ = 3.1–27.7°
μ = 0.09 mm⁻¹
T = 120 (2) K
Plate, colourless
0.15 × 0.10 × 0.03 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)T_min = 0.967, T_max = 0.997
39 965 measured reflections
8856 independent reflections
6116 reflections with I > 2σ(I)
R_int = 0.068
θ_max = 27.7°
h = −12 → 12
k = −15 → 15
l = −22 → 22

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.179, S = 1.05
8856 reflections
503 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0747P)² + 1.5268P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.42 e Å⁻³

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

Parameter	(I)	(II)	(III)	(IV)	(V), molecule 1	(V), molecule 2
n	nil	nil	nil	nil	1	2
Cn2—On2	1.211 (3)	1.2160 (18)	1.2166 (18)	1.2189 (14)	1.219 (3)	1.216 (3)
Cn4—On4	1.219 (3)	1.2235 (17)	1.2204 (18)	1.2273 (14)	1.217 (3)	1.224 (3)
Cn6—On6	1.211 (3)	1.2234 (18)	1.2157 (19)	1.2250 (14)	1.223 (3)	1.217 (3)
Cn5—Cn57	1.362 (3)	1.3627 (19)	1.366 (2)	1.3814 (16)	1.364 (3)	1.367 (3)
Cn57—Cn51	1.447 (3)	1.4658 (19)	1.449 (2)	1.4295 (15)	1.457 (3)	1.453 (3)
Cn51—Cn52	1.403 (3)	1.4065 (19)	1.410 (2)	1.4179 (15)	1.396 (3)	1.397 (3)
Cn52—Cn53	1.391 (3)	1.390 (2)	1.378 (2)	1.3751 (16)	1.396 (3)	1.393 (3)
Cn53—Cn54	1.387 (3)	1.396 (2)	1.402 (2)	1.4191 (16)	1.406 (3)	1.406 (3)
Cn54—Cn55	1.383 (4)	1.385 (2)	1.388 (2)	1.4211 (15)	1.414 (3)	1.412 (3)
Cn55—Cn56	1.397 (3)	1.392 (2)	1.384 (2)	1.3709 (16)	1.382 (3)	1.385 (3)
Cn56—Cn51	1.405 (3)	1.404 (2)	1.404 (2)	1.4202 (16)	1.401 (3)	1.400 (3)
Cn53—On53		1.3679 (17)
Cn54—On54			1.3578 (17)		1.367 (3)	1.369 (3)
Cn54—Nn54				1.3545 (14)
Cn5—Cn4—On4	123.6 (2)	122.83 (13)	123.49 (13)	123.61 (11)	127.7 (2)	123.5 (2)
Cn5—Cn6—On6	124.5 (2)	124.95 (13)	124.00 (14)	125.54 (10)	124.6 (2)	125.1 (2)
Cn4—Cn5—Cn57	115.23 (19)	114.14 (12)	114.26 (13)	114.20 (10)	113.2 (2)	113.4 (2)
Cn6—Cn5—Cn57	125.99 (19)	127.41 (13)	126.71 (13)	126.83 (10)	128.0 (2)	127.7 (2)
Cn5—Cn57—Cn51	137.1 (2)	137.62 (13)	139.14 (14)	138.79 (10)	138.5(2	138.5 (2)
Cn57—Cn51—Cn52	127.2 (2)	126.34 (13)	128.25 (14)	128.58 (10)	127.1 (2)	127.2 (2)
Cn52—Cn53—On53		123.31 (13)
Cn54—Cn53—On53		115.69 (13)
Cn53—Cn54—On54			115.72 (13)		121.2 (2)	118.9 (2)
Cn55—Cn54—On54			124.18 (14)		115.8 (2)	118.3 (2)
Cn5—Cn57—Cn51—Cn52	−14.6 (2)	4.1 (3)	6.1 (3)	0.9 (2)	4.5 (5)	−4.6 (5)
Cn52—Cn53—On53—Cn531		−2.1 (2)
Cn53—Cn54—On54—Cn541			176.86 (13)

Table 2
Hydrogen bonds and short intramolecular contacts (Å, °) for compounds (I)–(V)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
Compound (I)
C52—H52⋯O6	0.95	2.17	2.867 (3)	130
C53—H53⋯O6ⁱ	0.95	2.47	3.399 (3)	167
C56—H56⋯O4ⁱⁱ	0.95	2.40	3.310 (3)	159
C57—H57⋯O4	0.95	2.28	2.751 (3)	110

Compound (II)
C52—H52⋯O6	0.95	2.07	2.855 (2)	139
C54—H54⋯O2ⁱⁱⁱ	0.95	2.38	3.334 (2)	178
C56—H56⋯O4ⁱ	0.95	2.38	3.313 (2)	168
C57—H57⋯O4	0.95	2.24	2.727 (2)	111

Compound (III)
C52—H52⋯O6	0.95	2.11	2.889 (2)	138
C53—H53⋯O6ⁱⁱ	0.95	2.52	3.387 (2)	152
C55—H55⋯O4^iv	0.95	2.39	3.261 (2)	152
C57—H57⋯O4	0.95	2.23	2.729 (2)	112

Compound (IV)
C52—H52⋯O6	0.95	2.09	2.895 (2)	141
C53—H53⋯O4^v	0.95	2.53	3.381 (2)	149
C57—H57⋯O4	0.95	2.24	2.731 (2)	111

Compound (V)
C152—H152⋯O16	0.95	2.08	2.889 (3)	143
C157—H157⋯O14	0.95	2.21	2.709 (3)	112
C252—H252⋯O26	0.95	2.08	2.892 (3)	143
C257—H257⋯O24	0.95	2.22	2.716 (3)	112
Symmetry codes: (i) 1-x, 1-y, 1-z; (ii) 1-x, -y, 1-z; (iii) x-2, 1 + y, z; (iv) -x, 1-y, 1-z; (v) x, y, z-1.

For compound (I), the space group P2₁/n was uniquely assigned from the systematic absences. Crystals of compounds (II)–(IV) are triclinic and for each compound, the space group P $[\overline{1}]$ was selected and then confirmed by the structure analysis. All H atoms were located in difference maps and subsequently treated as riding atoms, with C—H distances of 0.95 (aromatic) or 0.98 Å (methyl) and O—H distances of 0.84 Å, and with U_iso(H) = 1.2U_eq(C,O) or 1.5U_eq(C_methyl). There are several short intramolecular H⋯H contacts in both molecules of (V); these all involve contacts between a hydroxyl H atom and a H atom in a tert-butyl group.

For all compounds, data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; structure solution: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); structure refinement: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); publication software: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I, II, III, IV, V. DOI: 10.1107/S0108270105008498/sk1828sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270105008498/sk1828Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S0108270105008498/sk1828IIsup3.hkl

Structure factors: contains datablock III. DOI: 10.1107/S0108270105008498/sk1828IIIsup4.hkl

Structure factors: contains datablock IV. DOI: 10.1107/S0108270105008498/sk1828IVsup5.hkl

Structure factors: contains datablock V. DOI: 10.1107/S0108270105008498/sk1828Vsup6.hkl

Comment top

The title compounds, (I)–(V), were initially prepared as part of a study of solvatochromism (Rezende et al., 2001, 2004), and it was considered necessary to determine their molecular and supramolecular structures for subsequent comparison with their NMR and solvatochromic behaviour.

Compounds (I)–(IV) (Figs. 1–4) all crystallize with Z' = 1, but compound (V) (Fig. 5) crystallizes with Z' = 2 in space group P1; the two independent molecules are very close to being mirror images of one another, but a careful search for possible additional symmetry revealed none. In each of the compounds (I)–(V), the molecules are nearly planar, as shown by the leading torsion angles (Table 1), and there are short intramolecular C—H···O contacts to both O4 and O6 (Table 2). Of these, the dimension of that involving O6 are suggestive of a genuine hydrogen bond. However, the bond angles at C5 and C57 give a strong indication that the H57···O4 contact is repulsive: the C—C—C angles at C57 are, in all cases, particularly large for fragments of this type. Similarly, the bond angles at C51 are more consistent with a repulsive H52···O6 contact than with a significantly attractive contact. However, it is noteworthy that these repulsive contacts are accommodated by distortion of the skeletal bond angles in preference to an evasive rotation around the C51—C57 bond, which would appear at first sight to represent a far less energy-costly resolution. In each of the methoxy compounds, (II) and (III), the methoxy C atom is nearly coplanar with the adjacent aryl ring and the exocyclic bond angles at the aryl C atom ipso to the methoxy substituent, C53 in (II) and C54 in (III), show the usual deviations from 120°.

Whereas in compounds (I) and (II), the C—C distances in the aryl rings are consistent with classically delocalized π electrons, in compounds (III) and, particularly, (IV), there is evidence for a significant contribution from polarized charge-separated forms. Thus in (IV), the C52—C53 and C55—C56 distances are significantly less than the remaining distances in the aryl ring. Likewise, the C51—C57 bond in (IV) is the shortest such bond observed in this series, while C57—C5 is the shortest [text missing? C5—C57 is shortest in (I)]. The C4—O4 and C6—O6 bonds are also longer in (IV) than in (I)– III). Finally, the C54—N54 distance is less than the quartile value [1.363 Å; Allen et al., 1987)] for bonds of this type. Taken all together, these observations provide evidence for the contribution of the polarized forms (IVa) and (IVb) to the overall molecular-electronic structure. There are similar, although weaker, indications for the contribution of similar forms in (III), not only from the distances within the aryl ring but also, in particular, the C51—C57 bond is shorter in (III) than in the isomeric compound (II), while C57—C5 is longer in (III) than in (II). In addition, the C54—O54 bond in (III) is somewhat shorter than the C53—O53 bond in (II). In compound (V), the indications for charge-separation are very weak, at best.

In each of compounds (I) and (II), the heterocyclic ring shows a small but significant deviation from planarity, with total puckering amplitudes Q (Cremer & Pople, 1975) of 0.105 (2) Å in (I) and 0.075 (2) Å in (II). The ring-puckering parameters for the atom sequence N1/C2/N3/C4–C6 are θ = 51.9 (11)° and ϕ = 276.7 (16)° for (I), and θ = 137.2 (11)° and ϕ = 45.9 (17)° for (II). The best single description for both of these rings is thus as half-chair conformers (Evans & Boeyens, 1989). In the two independent molecules in compound (V), the heterocyclic rings have effectively identical total puckering amplitudes, 0.115 (3) Å in molecule 1 (Fig. 5a) and 0.114 (3) Å in molecule 2 (Fig. 5b). The ring-puckering parameters for the atom sequences Nn1/Cn2/Nn3/Cn4–Cn6 (where n = 1 or 2) are θ = 70.0 (15)° and ϕ = 16.7 (14)° when n = 1, and θ = 109.5 (15)° and ϕ = 193.5 (14) when n = 2, emphasizing the nearly enantiomorphous character of the two molecules in the selected asymmetric unit. The best single descriptor for these ring conformations is screw-boat, for which ideally θ = 67.5° and ϕ = (60k + 30)°. By contrast, the heterocyclic rings in compounds (III) and (IV) are effectively planar.

In compounds (I)–(III), the molecules are linked by pairs of C—H···O hydrogen bonds (Table 2) into chains of edge-fused rings, but the details of these interactions are different in each case, as are the structures of the resulting chains. In compound (I) (Fig. 1), the aryl atoms C53 and C56 in the molecule at (x, y, z) act as hydrogen-bond donors to, respectively, atoms O6 in the molecule at (1 − x, 1 − y, 1 − z) and O4 in the molecule at (1 − x, −y, 1 − z), so generating by inversion a chain of edge-fused rings running parallel to the [010] direction. There are R₂²(16) (Bernstein et al., 1995) rings centred at (1/2, 1/2 + n, 1/2) (n = zero or integer) and R₂²(14) rings centred at (1/2, n, 1/2) (n = zero or integer) (Fig. 6). Two chains of this type pass through each unit cell, centred along the lines (1/2, y, 1/2) and (0, y, 0), but there are no direction-specific interactions between adjacent chains.

In compound (II) (Fig. 2), the aryl atom C56 in the molecule at (x, y, z) acts as hydrogen-bond donor to atom O4 in the molecule at (1 − x, 1 − y, 1 − z), so generating by inversion an R₂²(14) ring analogous to that in compound (I), although now centred at (1/2, 1/2, 1/2) (Fig. 6). At the same time, atom C54 at (x, y, z) acts as donor to atom O2 in the molecule at (x − 2, 1 + y, z), so generating by translation a C(11) chain running parallel to the [210] direction. The combination of the two hydrogen bonds then generates a [210] chain of centrosymmetric edge-fused R₂²(14) and R₄⁴(20) rings. Of the four molecules which participate in the formation of an R₄⁴(20) ring, two act as double donors and two as double acceptors of hydrogen bonds (Fig. 7). Again, there are no direction-specific interactions between adjacent chains.

The chain formation in compound (III) is rather different from that in the isomeric compound, (II). In (III), aryl atoms C53 and C55 in the molecule at (x, y, z) act as hydrogen-bond donors to, respectively, atoms O6 and O4 in the molecules at (1 − x, −y, 1 − z) and (−x, 1 − y, 1 − z), so generating by inversion a chain of edge-fused rings along [110] in which there are two distinct types of centrosymmetric R₂²(16) ring (Fig. 8), one involving O4 as the sole hydrogen-bond acceptor and the other involving O6 only.

In contrast with the chain formation in compounds (I)–(III), that in compound (IV) (Fig. 4) depends upon just one intermolecular C—H···O hydrogen bond. Atom C53 in the molecule at (x, y, z) acts as hydrogen-bond donor to atom O4 in the molecule at (x, y, z − 1), thereby generating by translation a simple C(8) chain running parallel to the [001] direction (Fig. 9). Two such chains, antiparallel to one another, pass through each unit cell, but there are no direction-specific interactions between adjacent chains.

In compound (V), there are no direction-specific intermolecular interactions. In particular, neither of the hydroxyl groups participates in hydrogen-bond formation, because of the steric shielding provided by the two adjacent tert-butyl substituents. The nearest plausible donor/acceptor atoms to O154 and O254 are, respectively, O154 at (1 − x, −y, 1 − z), with O···Oⁱ and O····Hⁱ distances of 3.391 (2) and 3.56 Å, respectively, and O254 at (2 − x, 1 − y, 1 − z), with O···Oⁱⁱ and O···Hⁱⁱ distances of 3.010 (2) and 2.91 Å, respectively [symmetry codes: (i) 1 − x, −y, 1 − z; (ii) 2 − x, 1 − y, 1 − z].

Experimental top

For the preparation of compounds (I)–(V), a mixture of N,N'-dimethylbarbituric acid (0.50 g, 3.2 mmol) and the appropriate arylaldehyde (3.2 mmol) in glacial acetic acid (4 ml) was heated under reflux for 2 h, cooled and filtered. The resulting solids were washed with diethyl ether (5 ml). Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of solutions in acetic acid, for (I) and (II), in acetonitrile, for (III) and (IV), or in ethanol, for (V). For (I), m.p. 430–432 K (literature value 430–431 K; Suzuki et al., 1976). For (II), m.p. 406–408 K. For (III), m.p. 416–418 K (literature value 417–418 K; Suzuki et al., 1976). For (IV), m.p. 497–499 K (literature value 497–499 K; Rezende et al., 2001). For (V), 467–469 K.

Computing details top

For all compounds, data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL 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. The molecule of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecule of compound (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. The molecule of compound (III), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 4. The molecule of compound (IV), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 5. The independent molecules of compound (V), showing the atom-labelling scheme. (a) Molecule 1. (b) Molecule 2. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 6. A stereoview of part of the crystal structure of compound (I), showing the formation of an [010] chain of alternating R₂²(14) and R₂²(16) rings. For the sake of clarity, the H atoms not involved in these motifs have been omitted.
	Fig. 7. A stereoview of part of the crystal structure of compound (II), showing the formation of a [210] chain of alternating R₂²(14) and R₄⁴(20) rings. For the sake of clarity, the H atoms not involved in these motifs have been omitted.
	Fig. 8. A stereoview of part of the crystal structure of compound (III), showing the formation of a [110] chain containing two types of R₂²(16) ring. For the sake of clarity, the H atoms not involved in these motifs have been omitted.
	Fig. 9. Part of the crystal structure of compound (IV), showing the formation of a C(8) chain along [001]. For the sake of clarity, the H atoms not involved in this motif have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, y, z − 1) and (x, y, 1 + z), respectively.

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

Crystal data top

C₁₃H₁₂N₂O₃	F(000) = 512
M_r = 244.25	D_x = 1.441 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2573 reflections
a = 6.1293 (3) Å	θ = 2.9–27.6°
b = 13.9633 (8) Å	µ = 0.10 mm⁻¹
c = 13.2727 (8) Å	T = 120 K
β = 97.688 (4)°	Plate, colourless
V = 1125.74 (11) Å³	0.34 × 0.25 × 0.09 mm
Z = 4

Data collection top

Bruker-Nonius KappaCCD area-detector diffractometer	2573 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1885 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.6°, θ_min = 2.9°
ϕ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −18→16
T_min = 0.954, T_max = 0.991	l = −17→17
12444 measured reflections

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.201	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1092P)² + 0.6873P] where P = (F_o² + 2F_c²)/3
2573 reflections	(Δ/σ)_max < 0.001
165 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₃H₁₂N₂O₃	V = 1125.74 (11) Å³
M_r = 244.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.1293 (3) Å	µ = 0.10 mm⁻¹
b = 13.9633 (8) Å	T = 120 K
c = 13.2727 (8) Å	0.34 × 0.25 × 0.09 mm
β = 97.688 (4)°

Data collection top

Bruker-Nonius KappaCCD area-detector diffractometer	2573 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1885 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.991	R_int = 0.050
12444 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.201	H-atom parameters constrained
S = 1.05	Δρ_max = 0.47 e Å⁻³
2573 reflections	Δρ_min = −0.30 e Å⁻³
165 parameters

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

	x	y	z	U_iso*/U_eq
O2	1.2148 (3)	0.19028 (12)	0.26161 (13)	0.0339 (5)
O4	0.7185 (3)	0.02451 (12)	0.41526 (15)	0.0395 (5)
O6	0.6561 (3)	0.35847 (12)	0.36333 (13)	0.0361 (5)
N1	0.9475 (3)	0.27629 (14)	0.32313 (14)	0.0253 (4)
N3	0.9667 (3)	0.10727 (13)	0.33945 (15)	0.0273 (5)
C1	1.0414 (4)	0.36476 (17)	0.28781 (19)	0.0337 (6)
C2	1.0535 (4)	0.19140 (15)	0.30520 (16)	0.0245 (5)
C3	1.0792 (4)	0.01715 (17)	0.3206 (2)	0.0383 (6)
C4	0.7840 (4)	0.10227 (16)	0.39016 (18)	0.0274 (5)
C5	0.6803 (4)	0.19450 (14)	0.41238 (17)	0.0238 (5)
C6	0.7532 (4)	0.28282 (16)	0.36596 (16)	0.0248 (5)
C51	0.3792 (4)	0.25359 (16)	0.52018 (16)	0.0249 (5)
C52	0.4022 (4)	0.35324 (17)	0.52969 (19)	0.0336 (6)
C53	0.2543 (4)	0.40674 (18)	0.57740 (19)	0.0362 (6)
C54	0.0833 (4)	0.36195 (17)	0.61757 (18)	0.0334 (6)
C55	0.0607 (4)	0.26355 (17)	0.61115 (17)	0.0297 (5)
C56	0.2075 (4)	0.20982 (16)	0.56350 (16)	0.0254 (5)
C57	0.5201 (4)	0.18825 (15)	0.47403 (17)	0.0265 (5)
H1A	0.9657	0.3813	0.2203	0.051*
H1B	1.1985	0.3553	0.2840	0.051*
H1C	1.0227	0.4168	0.3355	0.051*
H3A	1.1202	−0.0166	0.3851	0.057*
H3B	1.2120	0.0313	0.2896	0.057*
H3C	0.9803	−0.0232	0.2745	0.057*
H52	0.5200	0.3845	0.5033	0.040*
H53	0.2705	0.4743	0.5825	0.043*
H54	−0.0181	0.3989	0.6495	0.040*
H55	−0.0554	0.2327	0.6393	0.036*
H56	0.1916	0.1422	0.5601	0.031*
H57	0.4939	0.1237	0.4914	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0327 (10)	0.0353 (10)	0.0358 (9)	−0.0040 (7)	0.0122 (8)	−0.0012 (7)
O4	0.0447 (10)	0.0189 (9)	0.0602 (12)	−0.0014 (7)	0.0266 (9)	0.0002 (8)
O6	0.0417 (10)	0.0232 (9)	0.0458 (10)	0.0064 (7)	0.0150 (8)	0.0079 (7)
N1	0.0262 (10)	0.0239 (10)	0.0266 (9)	−0.0028 (7)	0.0060 (8)	0.0029 (8)
N3	0.0290 (10)	0.0216 (10)	0.0332 (10)	−0.0001 (7)	0.0106 (8)	−0.0033 (8)
C1	0.0362 (13)	0.0270 (13)	0.0392 (13)	−0.0042 (10)	0.0095 (11)	0.0061 (10)
C2	0.0246 (11)	0.0254 (12)	0.0234 (10)	−0.0033 (8)	0.0031 (9)	−0.0033 (8)
C3	0.0418 (14)	0.0244 (13)	0.0520 (16)	0.0033 (10)	0.0188 (12)	−0.0046 (11)
C4	0.0289 (12)	0.0215 (12)	0.0327 (12)	−0.0019 (9)	0.0082 (10)	−0.0019 (9)
C5	0.0241 (11)	0.0190 (11)	0.0278 (11)	−0.0019 (8)	0.0020 (9)	−0.0018 (8)
C6	0.0280 (12)	0.0233 (11)	0.0235 (10)	0.0019 (9)	0.0044 (9)	−0.0010 (8)
C51	0.0259 (11)	0.0240 (11)	0.0248 (10)	0.0001 (9)	0.0031 (9)	−0.0008 (8)
C52	0.0421 (14)	0.0227 (12)	0.0390 (13)	−0.0033 (10)	0.0158 (11)	−0.0018 (10)
C53	0.0503 (16)	0.0211 (12)	0.0404 (14)	−0.0007 (11)	0.0177 (12)	−0.0042 (10)
C54	0.0379 (14)	0.0310 (13)	0.0326 (12)	0.0063 (10)	0.0094 (10)	0.0002 (10)
C55	0.0300 (12)	0.0326 (13)	0.0272 (11)	−0.0033 (10)	0.0062 (9)	−0.0008 (10)
C56	0.0247 (11)	0.0255 (12)	0.0263 (11)	−0.0016 (8)	0.0040 (9)	0.0005 (9)
C57	0.0269 (12)	0.0228 (12)	0.0297 (12)	−0.0049 (8)	0.0032 (10)	−0.0016 (8)

Geometric parameters (Å, º) top

N1—C2	1.388 (3)	C5—C6	1.474 (3)
N1—C6	1.390 (3)	C57—C51	1.447 (3)
N1—C1	1.466 (3)	C57—H57	0.95
C1—H1A	0.98	C51—C52	1.403 (3)
C1—H1B	0.98	C51—C56	1.405 (3)
C1—H1C	0.98	C52—C53	1.391 (3)
C2—O2	1.211 (3)	C52—H52	0.95
C2—N3	1.391 (3)	C53—C54	1.387 (3)
N3—C4	1.383 (3)	C53—H53	0.95
N3—C3	1.472 (3)	C54—C55	1.383 (4)
C3—H3A	0.98	C54—H54	0.95
C3—H3B	0.98	C55—C56	1.387 (3)
C3—H3C	0.98	C55—H55	0.95
C4—O4	1.219 (3)	C56—H56	0.95
C4—C5	1.483 (3)	C6—O6	1.211 (3)
C5—C57	1.362 (3)

C2—N1—C6	124.94 (19)	C6—C5—C4	118.8 (2)
C2—N1—C1	116.89 (19)	C5—C57—C51	137.1 (2)
C6—N1—C1	118.05 (19)	C5—C57—H57	111.4
N1—C1—H1A	109.5	C51—C57—H57	111.4
N1—C1—H1B	109.5	C52—C51—C56	117.8 (2)
H1A—C1—H1B	109.5	C52—C51—C57	127.2 (2)
N1—C1—H1C	109.5	C56—C51—C57	114.9 (2)
H1A—C1—H1C	109.5	C53—C52—C51	120.7 (2)
H1B—C1—H1C	109.5	C53—C52—H52	119.7
O2—C2—N1	121.60 (19)	C51—C52—H52	119.7
O2—C2—N3	121.20 (19)	C54—C53—C52	120.3 (2)
N1—C2—N3	117.2 (2)	C54—C53—H53	119.8
C4—N3—C2	124.87 (19)	C52—C53—H53	119.8
C4—N3—C3	117.88 (19)	C55—C54—C53	120.0 (2)
C2—N3—C3	117.25 (18)	C55—C54—H54	120.0
N3—C3—H3A	109.5	C53—C54—H54	120.0
N3—C3—H3B	109.5	C54—C55—C56	120.0 (2)
H3A—C3—H3B	109.5	C54—C55—H55	120.0
N3—C3—H3C	109.5	C56—C55—H55	120.0
H3A—C3—H3C	109.5	C55—C56—C51	121.2 (2)
H3B—C3—H3C	109.5	C55—C56—H56	119.4
O4—C4—N3	119.7 (2)	C51—C56—H56	119.4
O4—C4—C5	123.6 (2)	O6—C6—N1	119.3 (2)
N3—C4—C5	116.69 (19)	O6—C6—C5	124.5 (2)
C57—C5—C6	125.99 (19)	N1—C6—C5	116.13 (19)
C57—C5—C4	115.23 (19)

C6—N1—C2—O2	175.1 (2)	C5—C57—C51—C52	−14.6 (4)
C1—N1—C2—O2	−0.6 (3)	C5—C57—C51—C56	168.4 (2)
C6—N1—C2—N3	−4.9 (3)	C56—C51—C52—C53	−2.2 (3)
C1—N1—C2—N3	179.35 (19)	C57—C51—C52—C53	−179.2 (2)
O2—C2—N3—C4	179.7 (2)	C51—C52—C53—C54	0.9 (4)
N1—C2—N3—C4	−0.3 (3)	C52—C53—C54—C55	0.6 (4)
O2—C2—N3—C3	0.1 (3)	C53—C54—C55—C56	−0.7 (3)
N1—C2—N3—C3	−179.9 (2)	C54—C55—C56—C51	−0.7 (3)
C2—N3—C4—O4	178.6 (2)	C52—C51—C56—C55	2.1 (3)
C3—N3—C4—O4	−1.8 (3)	C57—C51—C56—C55	179.5 (2)
C2—N3—C4—C5	−2.4 (3)	C2—N1—C6—O6	−168.2 (2)
C3—N3—C4—C5	177.2 (2)	C1—N1—C6—O6	7.6 (3)
O4—C4—C5—C57	7.5 (3)	C2—N1—C6—C5	11.9 (3)
N3—C4—C5—C57	−171.50 (19)	C1—N1—C6—C5	−172.33 (18)
O4—C4—C5—C6	−171.4 (2)	C57—C5—C6—O6	−12.6 (4)
N3—C4—C5—C6	9.6 (3)	C4—C5—C6—O6	166.2 (2)
C6—C5—C57—C51	−3.9 (4)	C57—C5—C6—N1	167.3 (2)
C4—C5—C57—C51	177.3 (2)	C4—C5—C6—N1	−14.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C52—H52···O6	0.95	2.17	2.867 (3)	130
C53—H53···O6ⁱ	0.95	2.47	3.399 (3)	167
C56—H56···O4ⁱⁱ	0.95	2.40	3.310 (3)	159
C57—H57···O4	0.95	2.28	2.751 (3)	110

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

(II) 5-(3-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione top

Crystal data top

C₁₄H₁₄N₂O₄	Z = 2
M_r = 274.27	F(000) = 288
Triclinic, P1	D_x = 1.469 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6946 (2) Å	Cell parameters from 2847 reflections
b = 8.2994 (3) Å	θ = 3.0–27.5°
c = 14.0411 (5) Å	µ = 0.11 mm⁻¹
α = 73.5580 (17)°	T = 120 K
β = 87.393 (2)°	Block, colourless
γ = 77.037 (2)°	0.52 × 0.34 × 0.16 mm
V = 620.13 (4) Å³

Data collection top

Bruker-Nonius KappaCCD area-detector diffractometer	2847 independent reflections
Radiation source: Bruker-Nonius FR91 rotating anode	2331 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −10→10
T_min = 0.953, T_max = 0.983	l = −18→18
14859 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0732P)² + 0.1975P] where P = (F_o² + 2F_c²)/3
2847 reflections	(Δ/σ)_max < 0.001
184 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₄	γ = 77.037 (2)°
M_r = 274.27	V = 620.13 (4) Å³
Triclinic, P1	Z = 2
a = 5.6946 (2) Å	Mo Kα radiation
b = 8.2994 (3) Å	µ = 0.11 mm⁻¹
c = 14.0411 (5) Å	T = 120 K
α = 73.5580 (17)°	0.52 × 0.34 × 0.16 mm
β = 87.393 (2)°

Data collection top

Bruker-Nonius KappaCCD area-detector diffractometer	2847 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2331 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.983	R_int = 0.034
14859 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.11	Δρ_max = 0.40 e Å⁻³
2847 reflections	Δρ_min = −0.40 e Å⁻³
184 parameters

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

	x	y	z	U_iso*/U_eq
O2	1.42349 (19)	0.21216 (14)	0.78350 (8)	0.0229 (3)
O4	0.80218 (19)	0.39336 (14)	0.56112 (8)	0.0219 (3)
O6	0.7348 (2)	0.52516 (15)	0.87014 (8)	0.0283 (3)
O53	0.08023 (19)	0.94132 (14)	0.88183 (8)	0.0229 (3)
N1	1.0794 (2)	0.37772 (15)	0.82361 (9)	0.0176 (3)
N3	1.1177 (2)	0.31209 (15)	0.66925 (9)	0.0163 (3)
C1	1.1908 (3)	0.3609 (2)	0.91947 (11)	0.0247 (3)
C2	1.2196 (3)	0.29547 (18)	0.76031 (11)	0.0171 (3)
C3	1.2724 (3)	0.22538 (19)	0.60310 (11)	0.0201 (3)
C4	0.8841 (2)	0.39762 (17)	0.63921 (10)	0.0157 (3)
C5	0.7429 (2)	0.49534 (17)	0.70532 (10)	0.0156 (3)
C6	0.8439 (3)	0.47119 (18)	0.80436 (11)	0.0174 (3)
C51	0.3264 (2)	0.71755 (17)	0.69376 (10)	0.0158 (3)
C52	0.3138 (3)	0.77225 (18)	0.78032 (10)	0.0170 (3)
C53	0.1066 (3)	0.88322 (18)	0.79916 (10)	0.0174 (3)
C54	−0.0896 (3)	0.94345 (19)	0.73268 (11)	0.0194 (3)
C55	−0.0746 (3)	0.89307 (19)	0.64622 (11)	0.0208 (3)
C56	0.1309 (3)	0.78161 (18)	0.62601 (11)	0.0184 (3)
C57	0.5276 (2)	0.59645 (17)	0.66543 (10)	0.0161 (3)
C531	0.2769 (3)	0.8772 (2)	0.95262 (11)	0.0248 (3)
H1A	1.1457	0.2654	0.9705	0.037*
H1B	1.1344	0.4681	0.9383	0.037*
H1C	1.3665	0.3382	0.9135	0.037*
H3A	1.2997	0.1003	0.6317	0.030*
H3B	1.4272	0.2601	0.5958	0.030*
H3C	1.1929	0.2581	0.5378	0.030*
H31A	0.3122	0.7510	0.9733	0.037*
H31B	0.2331	0.9201	1.0107	0.037*
H52	0.4466	0.7334	0.8258	0.020*
H31C	0.4197	0.9167	0.9222	0.037*
H54	−0.2314	1.0180	0.7466	0.023*
H55	−0.2062	0.9351	0.6001	0.025*
H56	0.1389	0.7488	0.5662	0.022*
H57	0.5002	0.5854	0.6016	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0157 (5)	0.0248 (6)	0.0249 (6)	0.0015 (4)	−0.0008 (4)	−0.0064 (4)
O4	0.0203 (5)	0.0267 (6)	0.0201 (6)	−0.0004 (4)	−0.0006 (4)	−0.0126 (4)
O6	0.0270 (6)	0.0344 (6)	0.0184 (6)	0.0106 (5)	−0.0033 (4)	−0.0120 (5)
O53	0.0222 (6)	0.0268 (6)	0.0184 (5)	0.0043 (4)	−0.0003 (4)	−0.0119 (4)
N1	0.0156 (6)	0.0198 (6)	0.0164 (6)	0.0001 (5)	−0.0015 (5)	−0.0066 (5)
N3	0.0142 (6)	0.0166 (6)	0.0178 (6)	0.0004 (5)	0.0015 (5)	−0.0072 (5)
C1	0.0228 (8)	0.0313 (8)	0.0188 (7)	0.0006 (6)	−0.0052 (6)	−0.0093 (6)
C2	0.0163 (7)	0.0155 (7)	0.0186 (7)	−0.0033 (5)	0.0014 (5)	−0.0037 (5)
C3	0.0186 (7)	0.0204 (7)	0.0214 (7)	−0.0003 (5)	0.0051 (6)	−0.0100 (6)
C4	0.0143 (7)	0.0150 (6)	0.0178 (7)	−0.0020 (5)	0.0013 (5)	−0.0055 (5)
C5	0.0154 (7)	0.0156 (7)	0.0162 (7)	−0.0020 (5)	0.0013 (5)	−0.0064 (5)
C6	0.0170 (7)	0.0154 (7)	0.0178 (7)	0.0008 (5)	−0.0013 (5)	−0.0049 (5)
C51	0.0151 (7)	0.0146 (6)	0.0177 (7)	−0.0022 (5)	0.0013 (5)	−0.0054 (5)
C52	0.0167 (7)	0.0176 (7)	0.0159 (7)	−0.0010 (5)	−0.0003 (5)	−0.0053 (5)
C53	0.0194 (7)	0.0166 (7)	0.0156 (7)	−0.0024 (5)	0.0022 (5)	−0.0052 (5)
C54	0.0149 (7)	0.0194 (7)	0.0229 (7)	−0.0001 (5)	0.0019 (5)	−0.0074 (6)
C55	0.0158 (7)	0.0226 (7)	0.0232 (7)	0.0003 (6)	−0.0040 (5)	−0.0080 (6)
C56	0.0179 (7)	0.0191 (7)	0.0189 (7)	−0.0017 (5)	−0.0007 (5)	−0.0080 (6)
C57	0.0167 (7)	0.0168 (7)	0.0161 (7)	−0.0035 (5)	0.0002 (5)	−0.0067 (5)
C531	0.0258 (8)	0.0283 (8)	0.0193 (7)	0.0016 (6)	−0.0021 (6)	−0.0109 (6)

Geometric parameters (Å, º) top

N1—C6	1.3862 (18)	C57—H57	0.95
N1—C2	1.3885 (18)	C51—C56	1.404 (2)
N1—C1	1.4715 (18)	C51—C52	1.4065 (19)
C1—H1A	0.98	C52—C53	1.390 (2)
C1—H1B	0.98	C52—H52	0.95
C1—H1C	0.98	C53—O53	1.3679 (17)
C2—O2	1.2160 (18)	C53—C54	1.396 (2)
C2—N3	1.3864 (19)	O53—C531	1.4353 (18)
N3—C4	1.3820 (18)	C531—H31A	0.98
N3—C3	1.4751 (17)	C531—H31B	0.98
C3—H3A	0.98	C531—H31C	0.98
C3—H3B	0.98	C54—C55	1.385 (2)
C3—H3C	0.98	C54—H54	0.95
C4—O4	1.2235 (17)	C55—C56	1.392 (2)
C4—C5	1.4937 (19)	C55—H55	0.95
C5—C57	1.3627 (19)	C56—H56	0.95
C5—C6	1.4723 (19)	C6—O6	1.2234 (18)
C57—C51	1.4658 (19)

C6—N1—C2	125.38 (12)	C51—C57—H57	111.2
C6—N1—C1	117.89 (12)	C56—C51—C52	118.89 (13)
C2—N1—C1	116.73 (12)	C56—C51—C57	114.77 (12)
N1—C1—H1A	109.5	C52—C51—C57	126.34 (13)
N1—C1—H1B	109.5	C53—C52—C51	119.89 (13)
H1A—C1—H1B	109.5	C53—C52—H52	120.1
N1—C1—H1C	109.5	C51—C52—H52	120.1
H1A—C1—H1C	109.5	O53—C53—C52	123.31 (13)
H1B—C1—H1C	109.5	O53—C53—C54	115.69 (13)
O2—C2—N3	121.17 (13)	C52—C53—C54	120.99 (13)
O2—C2—N1	121.56 (13)	C53—O53—C531	116.67 (11)
N3—C2—N1	117.27 (12)	O53—C531—H31A	109.5
C4—N3—C2	124.70 (12)	O53—C531—H31B	109.5
C4—N3—C3	119.28 (12)	H31A—C531—H31B	109.5
C2—N3—C3	115.98 (11)	O53—C531—H31C	109.5
N3—C3—H3A	109.5	H31A—C531—H31C	109.5
N3—C3—H3B	109.5	H31B—C531—H31C	109.5
H3A—C3—H3B	109.5	C55—C54—C53	119.07 (13)
N3—C3—H3C	109.5	C55—C54—H54	120.5
H3A—C3—H3C	109.5	C53—C54—H54	120.5
H3B—C3—H3C	109.5	C54—C55—C56	120.89 (14)
O4—C4—N3	120.32 (13)	C54—C55—H55	119.6
O4—C4—C5	122.83 (13)	C56—C55—H55	119.6
N3—C4—C5	116.85 (12)	C55—C56—C51	120.22 (13)
C57—C5—C6	127.41 (13)	C55—C56—H56	119.9
C57—C5—C4	114.14 (12)	C51—C56—H56	119.9
C6—C5—C4	118.43 (12)	O6—C6—N1	118.46 (13)
C5—C57—C51	137.62 (13)	O6—C6—C5	124.95 (13)
C5—C57—H57	111.2	N1—C6—C5	116.59 (12)

C6—N1—C2—O2	−178.17 (13)	C56—C51—C52—C53	2.2 (2)
C1—N1—C2—O2	0.8 (2)	C57—C51—C52—C53	−177.57 (13)
C6—N1—C2—N3	1.8 (2)	C51—C52—C53—O53	179.66 (13)
C1—N1—C2—N3	−179.22 (12)	C51—C52—C53—C54	−0.8 (2)
O2—C2—N3—C4	176.89 (13)	C52—C53—O53—C531	−2.1 (2)
N1—C2—N3—C4	−3.1 (2)	C54—C53—O53—C531	178.26 (13)
O2—C2—N3—C3	−0.9 (2)	O53—C53—C54—C55	178.71 (13)
N1—C2—N3—C3	179.14 (12)	C52—C53—C54—C55	−0.9 (2)
C2—N3—C4—O4	−173.64 (13)	C53—C54—C55—C56	1.1 (2)
C3—N3—C4—O4	4.0 (2)	C54—C55—C56—C51	0.4 (2)
C2—N3—C4—C5	7.3 (2)	C52—C51—C56—C55	−2.0 (2)
C3—N3—C4—C5	−175.00 (12)	C57—C51—C56—C55	177.77 (13)
O4—C4—C5—C57	−7.9 (2)	C2—N1—C6—O6	174.09 (13)
N3—C4—C5—C57	171.13 (12)	C1—N1—C6—O6	−4.8 (2)
O4—C4—C5—C6	170.89 (13)	C2—N1—C6—C5	−5.0 (2)
N3—C4—C5—C6	−10.09 (19)	C1—N1—C6—C5	176.08 (12)
C6—C5—C57—C51	3.0 (3)	C57—C5—C6—O6	8.5 (2)
C4—C5—C57—C51	−178.34 (15)	C4—C5—C6—O6	−170.06 (14)
C5—C57—C51—C56	−175.64 (16)	C57—C5—C6—N1	−172.45 (13)
C5—C57—C51—C52	4.1 (3)	C4—C5—C6—N1	8.95 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C52—H52···O6	0.95	2.07	2.855 (2)	139
C54—H54···O2ⁱ	0.95	2.38	3.334 (2)	178
C56—H56···O4ⁱⁱ	0.95	2.38	3.313 (2)	168
C57—H57···O4	0.95	2.24	2.727 (2)	111

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

(III) 5-(4-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione top

Crystal data top

C₁₄H₁₄N₂O₄	Z = 2
M_r = 274.27	F(000) = 288
Triclinic, P1	D_x = 1.454 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5906 (6) Å	Cell parameters from 2860 reflections
b = 8.2989 (7) Å	θ = 3.1–27.5°
c = 10.301 (1) Å	µ = 0.11 mm⁻¹
α = 92.544 (6)°	T = 120 K
β = 93.074 (5)°	Block, yellow
γ = 104.456 (6)°	0.48 × 0.44 × 0.34 mm
V = 626.33 (10) Å³

Data collection top

Bruker-Nonius KappaCCD area-detector diffractometer	2860 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2173 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −10→10
T_min = 0.947, T_max = 0.964	l = −13→13
10553 measured reflections

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) = 0.136	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0773P)² + 0.1359P] where P = (F_o² + 2F_c²)/3
2860 reflections	(Δ/σ)_max < 0.001
184 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₄	γ = 104.456 (6)°
M_r = 274.27	V = 626.33 (10) Å³
Triclinic, P1	Z = 2
a = 7.5906 (6) Å	Mo Kα radiation
b = 8.2989 (7) Å	µ = 0.11 mm⁻¹
c = 10.301 (1) Å	T = 120 K
α = 92.544 (6)°	0.48 × 0.44 × 0.34 mm
β = 93.074 (5)°

Data collection top

Bruker-Nonius KappaCCD area-detector diffractometer	2860 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2173 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.964	R_int = 0.034
10553 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.06	Δρ_max = 0.27 e Å⁻³
2860 reflections	Δρ_min = −0.24 e Å⁻³
184 parameters

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

	x	y	z	U_iso*/U_eq
O2	0.80386 (15)	0.66484 (13)	0.02844 (11)	0.0316 (3)
O4	0.28789 (15)	0.68329 (14)	0.22215 (11)	0.0324 (3)
O6	0.6058 (2)	0.27431 (18)	0.31566 (15)	0.0602 (5)
O54	0.06981 (15)	−0.02267 (13)	0.75913 (10)	0.0300 (3)
N1	0.70274 (16)	0.46844 (15)	0.17228 (12)	0.0243 (3)
N3	0.54470 (16)	0.67320 (15)	0.12473 (12)	0.0237 (3)
C1	0.8602 (2)	0.4008 (2)	0.14631 (17)	0.0316 (4)
C2	0.6911 (2)	0.60604 (18)	0.10441 (14)	0.0238 (3)
C3	0.5412 (2)	0.82590 (19)	0.05854 (16)	0.0300 (4)
C4	0.4109 (2)	0.61423 (18)	0.21020 (14)	0.0244 (3)
C5	0.4288 (2)	0.46904 (17)	0.28419 (14)	0.0236 (3)
C6	0.5818 (2)	0.3956 (2)	0.26236 (16)	0.0301 (4)
C51	0.2466 (2)	0.29635 (17)	0.46490 (14)	0.0230 (3)
C52	0.3482 (2)	0.18855 (18)	0.51359 (14)	0.0256 (3)
C53	0.2848 (2)	0.08393 (19)	0.61038 (14)	0.0262 (3)
C54	0.1182 (2)	0.08340 (18)	0.66308 (14)	0.0241 (3)
C55	0.0146 (2)	0.18777 (18)	0.61722 (14)	0.0259 (3)
C56	0.0794 (2)	0.29082 (19)	0.51902 (15)	0.0262 (3)
C57	0.2951 (2)	0.41808 (18)	0.36788 (14)	0.0245 (3)
C541	−0.0955 (2)	−0.0211 (2)	0.82071 (16)	0.0314 (4)
H1A	0.8576	0.3705	0.0531	0.047*
H1B	0.8544	0.3017	0.1958	0.047*
H1C	0.9734	0.4852	0.1728	0.047*
H3A	0.4287	0.8583	0.0759	0.045*
H3B	0.5459	0.8054	−0.0355	0.045*
H3C	0.6467	0.9158	0.0911	0.045*
H52	0.4617	0.1880	0.4792	0.031*
H53	0.3546	0.0116	0.6416	0.031*
H54A	−0.0867	0.0908	0.8595	0.047*
H54B	−0.1135	−0.1013	0.8889	0.047*
H54C	−0.1991	−0.0519	0.7557	0.047*
H55	−0.0983	0.1885	0.6525	0.031*
H56	0.0076	0.3609	0.4868	0.031*
H57	0.2073	0.4817	0.3601	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0319 (6)	0.0319 (6)	0.0339 (6)	0.0085 (5)	0.0155 (5)	0.0137 (5)
O4	0.0325 (6)	0.0333 (6)	0.0379 (6)	0.0161 (5)	0.0123 (5)	0.0154 (5)
O6	0.0683 (9)	0.0632 (9)	0.0758 (10)	0.0488 (8)	0.0510 (8)	0.0516 (8)
O54	0.0361 (6)	0.0305 (6)	0.0265 (6)	0.0097 (5)	0.0130 (5)	0.0134 (5)
N1	0.0242 (6)	0.0258 (7)	0.0256 (6)	0.0083 (5)	0.0087 (5)	0.0092 (5)
N3	0.0255 (6)	0.0231 (6)	0.0240 (6)	0.0062 (5)	0.0064 (5)	0.0102 (5)
C1	0.0292 (8)	0.0339 (9)	0.0373 (9)	0.0144 (7)	0.0129 (7)	0.0133 (7)
C2	0.0254 (7)	0.0234 (7)	0.0223 (7)	0.0048 (6)	0.0049 (6)	0.0044 (6)
C3	0.0337 (8)	0.0271 (8)	0.0327 (8)	0.0101 (7)	0.0091 (7)	0.0156 (7)
C4	0.0247 (7)	0.0247 (7)	0.0248 (7)	0.0064 (6)	0.0054 (6)	0.0065 (6)
C5	0.0263 (8)	0.0223 (7)	0.0230 (7)	0.0059 (6)	0.0069 (6)	0.0075 (6)
C6	0.0338 (8)	0.0317 (8)	0.0295 (8)	0.0128 (7)	0.0137 (7)	0.0133 (6)
C51	0.0257 (8)	0.0216 (7)	0.0219 (7)	0.0049 (6)	0.0055 (6)	0.0033 (6)
C52	0.0267 (7)	0.0280 (8)	0.0238 (7)	0.0083 (6)	0.0066 (6)	0.0062 (6)
C53	0.0306 (8)	0.0266 (8)	0.0239 (7)	0.0104 (6)	0.0061 (6)	0.0063 (6)
C54	0.0307 (8)	0.0208 (7)	0.0202 (7)	0.0036 (6)	0.0068 (6)	0.0053 (6)
C55	0.0279 (8)	0.0252 (8)	0.0260 (8)	0.0066 (6)	0.0102 (6)	0.0060 (6)
C56	0.0296 (8)	0.0243 (8)	0.0271 (8)	0.0092 (6)	0.0076 (6)	0.0064 (6)
C57	0.0253 (7)	0.0246 (7)	0.0250 (8)	0.0077 (6)	0.0053 (6)	0.0052 (6)
C541	0.0358 (9)	0.0319 (8)	0.0267 (8)	0.0054 (7)	0.0133 (7)	0.0091 (6)

Geometric parameters (Å, º) top

N1—C2	1.3839 (19)	C57—H57	0.95
N1—C6	1.3907 (19)	C51—C56	1.404 (2)
N1—C1	1.4737 (19)	C51—C52	1.410 (2)
C1—H1A	0.98	C52—C53	1.378 (2)
C1—H1B	0.98	C52—H52	0.95
C1—H1C	0.98	C53—C54	1.402 (2)
C2—O2	1.2166 (18)	C53—H53	0.95
C2—N3	1.3832 (19)	C54—O54	1.3578 (17)
N3—C4	1.3898 (19)	C54—C55	1.388 (2)
N3—C3	1.4707 (18)	O54—C541	1.4389 (19)
C3—H3A	0.98	C541—H54A	0.98
C3—H3B	0.98	C541—H54B	0.98
C3—H3C	0.98	C541—H54C	0.98
C4—O4	1.2204 (18)	C55—C56	1.384 (2)
C4—C5	1.484 (2)	C55—H55	0.95
C5—C57	1.366 (2)	C56—H56	0.95
C5—C6	1.462 (2)	C6—O6	1.2157 (19)
C57—C51	1.449 (2)

C2—N1—C6	125.06 (13)	C51—C57—H57	110.4
C2—N1—C1	115.35 (12)	C56—C51—C52	116.95 (13)
C6—N1—C1	119.58 (12)	C56—C51—C57	114.76 (13)
N1—C1—H1A	109.5	C52—C51—C57	128.25 (14)
N1—C1—H1B	109.5	C53—C52—C51	120.84 (14)
H1A—C1—H1B	109.5	C53—C52—H52	119.6
N1—C1—H1C	109.5	C51—C52—H52	119.6
H1A—C1—H1C	109.5	C52—C53—C54	120.54 (14)
H1B—C1—H1C	109.5	C52—C53—H53	119.7
O2—C2—N3	121.06 (14)	C54—C53—H53	119.7
O2—C2—N1	121.46 (14)	O54—C54—C55	124.18 (14)
N3—C2—N1	117.48 (13)	O54—C54—C53	115.72 (13)
C2—N3—C4	124.62 (13)	C55—C54—C53	120.11 (13)
C2—N3—C3	116.66 (12)	C54—O54—C541	117.61 (12)
C4—N3—C3	118.52 (12)	O54—C541—H54A	109.5
N3—C3—H3A	109.5	O54—C541—H54B	109.5
N3—C3—H3B	109.5	H54A—C541—H54B	109.5
H3A—C3—H3B	109.5	O54—C541—H54C	109.5
N3—C3—H3C	109.5	H54A—C541—H54C	109.5
H3A—C3—H3C	109.5	H54B—C541—H54C	109.5
H3B—C3—H3C	109.5	C56—C55—C54	118.59 (14)
O4—C4—N3	119.63 (13)	C56—C55—H55	120.7
O4—C4—C5	123.49 (13)	C54—C55—H55	120.7
N3—C4—C5	116.88 (13)	C55—C56—C51	122.96 (14)
C57—C5—C6	126.71 (13)	C55—C56—H56	118.5
C57—C5—C4	114.26 (13)	C51—C56—H56	118.5
C6—C5—C4	119.03 (13)	O6—C6—N1	119.07 (15)
C5—C57—C51	139.14 (14)	O6—C6—C5	124.00 (14)
C5—C57—H57	110.4	N1—C6—C5	116.91 (13)

C6—N1—C2—O2	178.78 (14)	C56—C51—C52—C53	−0.3 (2)
C1—N1—C2—O2	0.4 (2)	C57—C51—C52—C53	177.41 (15)
C6—N1—C2—N3	−2.1 (2)	C51—C52—C53—C54	−0.4 (2)
C1—N1—C2—N3	179.48 (12)	C52—C53—C54—O54	−179.10 (13)
O2—C2—N3—C4	−179.56 (13)	C52—C53—C54—C55	0.5 (2)
N1—C2—N3—C4	1.3 (2)	C55—C54—O54—C541	−2.7 (2)
O2—C2—N3—C3	−4.8 (2)	C53—C54—O54—C541	176.86 (13)
N1—C2—N3—C3	176.04 (12)	O54—C54—C55—C56	179.73 (14)
C2—N3—C4—O4	179.29 (14)	C53—C54—C55—C56	0.1 (2)
C3—N3—C4—O4	4.7 (2)	C54—C55—C56—C51	−0.9 (2)
C2—N3—C4—C5	0.1 (2)	C52—C51—C56—C55	1.0 (2)
C3—N3—C4—C5	−174.53 (12)	C57—C51—C56—C55	−177.01 (13)
O4—C4—C5—C57	0.0 (2)	C2—N1—C6—O6	179.76 (16)
N3—C4—C5—C57	179.14 (13)	C1—N1—C6—O6	−1.9 (2)
O4—C4—C5—C6	179.98 (14)	C2—N1—C6—C5	1.3 (2)
N3—C4—C5—C6	−0.9 (2)	C1—N1—C6—C5	179.70 (13)
C6—C5—C57—C51	3.7 (3)	C57—C5—C6—O6	1.9 (3)
C4—C5—C57—C51	−176.31 (17)	C4—C5—C6—O6	−178.14 (17)
C5—C57—C51—C56	−176.12 (18)	C57—C5—C6—N1	−179.81 (14)
C5—C57—C51—C52	6.1 (3)	C4—C5—C6—N1	0.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C52—H52···O6	0.95	2.11	2.889 (2)	138
C53—H53···O6ⁱ	0.95	2.52	3.387 (2)	152
C55—H55···O4ⁱⁱ	0.95	2.39	3.261 (2)	152
C57—H57···O4	0.95	2.23	2.729 (2)	112

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

(IV) 5-[4-(dimethylamino)benzylidene]-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 = 1.412 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6187 (2) Å	Cell parameters from 3073 reflections
b = 8.8451 (3) Å	θ = 3.1–27.5°
c = 9.0566 (3) Å	µ = 0.10 mm⁻¹
α = 82.2980 (18)°	T = 120 K
β = 84.465 (2)°	Block, orange
γ = 82.365 (2)°	0.40 × 0.30 × 0.20 mm
V = 675.94 (4) Å³

Data collection top

Bruker-Nonius KappaCCD area-detector diffractometer	3073 independent reflections
Radiation source: Bruker-Nonius FR91 rotating anode	2698 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −11→11
T_min = 0.955, T_max = 0.980	l = −11→11
13410 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0577P)² + 0.2209P] where P = (F_o² + 2F_c²)/3
3073 reflections	(Δ/σ)_max = 0.009
194 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₅H₁₇N₃O₃	γ = 82.365 (2)°
M_r = 287.32	V = 675.94 (4) Å³
Triclinic, P1	Z = 2
a = 8.6187 (2) Å	Mo Kα radiation
b = 8.8451 (3) Å	µ = 0.10 mm⁻¹
c = 9.0566 (3) Å	T = 120 K
α = 82.2980 (18)°	0.40 × 0.30 × 0.20 mm
β = 84.465 (2)°

Data collection top

Bruker-Nonius KappaCCD area-detector diffractometer	3073 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2698 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.980	R_int = 0.027
13410 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.05	Δρ_max = 0.28 e Å⁻³
3073 reflections	Δρ_min = −0.27 e Å⁻³
194 parameters

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

	x	y	z	U_iso*/U_eq
O2	0.20702 (10)	1.01028 (10)	0.69826 (10)	0.0262 (2)
O4	0.65055 (10)	0.67888 (10)	0.76453 (9)	0.0254 (2)
O6	0.42780 (11)	0.78374 (11)	0.29651 (10)	0.0294 (2)
N1	0.32498 (11)	0.90026 (11)	0.49595 (10)	0.0185 (2)
N3	0.43121 (11)	0.84618 (11)	0.72988 (10)	0.0197 (2)
N54	0.95303 (12)	0.28701 (11)	0.00057 (11)	0.0209 (2)
C1	0.20256 (14)	0.98431 (14)	0.40472 (14)	0.0243 (3)
C2	0.31355 (13)	0.92388 (13)	0.64509 (13)	0.0188 (2)
C3	0.42493 (16)	0.87893 (16)	0.88508 (13)	0.0276 (3)
C4	0.55241 (13)	0.74064 (13)	0.67884 (12)	0.0184 (2)
C5	0.55605 (13)	0.71125 (13)	0.52207 (12)	0.0170 (2)
C6	0.43704 (13)	0.79591 (13)	0.42844 (12)	0.0183 (2)
C51	0.73387 (13)	0.52767 (13)	0.35161 (12)	0.0176 (2)
C52	0.67780 (14)	0.55360 (13)	0.20713 (13)	0.0208 (2)
C53	0.74808 (14)	0.47471 (13)	0.09256 (13)	0.0208 (2)
C54	0.88152 (13)	0.36372 (12)	0.11323 (12)	0.0180 (2)
C55	0.93787 (13)	0.33510 (13)	0.25798 (13)	0.0203 (2)
C56	0.86589 (13)	0.41446 (13)	0.37098 (13)	0.0192 (2)
C57	0.67536 (13)	0.60081 (13)	0.48077 (12)	0.0178 (2)
C541	1.08832 (15)	0.17140 (14)	0.02688 (14)	0.0260 (3)
C542	0.89585 (15)	0.31354 (15)	−0.14836 (13)	0.0242 (3)
H1A	0.2475	1.0098	0.3022	0.036*
H1B	0.1600	1.0792	0.4468	0.036*
H1C	0.1182	0.9202	0.4041	0.036*
H3A	0.4534	0.9823	0.8866	0.041*
H3B	0.4989	0.8034	0.9401	0.041*
H3C	0.3183	0.8730	0.9322	0.041*
H52	0.5891	0.6276	0.1889	0.025*
H53	0.7064	0.4949	−0.0024	0.025*
H54A	1.1703	0.2179	0.0662	0.039*
H54B	1.1291	0.1323	−0.0673	0.039*
H54C	1.0563	0.0865	0.0994	0.039*
H54D	0.7986	0.2668	−0.1464	0.036*
H54E	0.9753	0.2673	−0.2193	0.036*
H54F	0.8752	0.4243	−0.1793	0.036*
H55	1.0260	0.2605	0.2766	0.024*
H56	0.9061	0.3927	0.4666	0.023*
H57	0.7367	0.5620	0.5624	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0253 (4)	0.0280 (5)	0.0243 (4)	0.0047 (4)	−0.0009 (3)	−0.0077 (3)
O4	0.0251 (4)	0.0327 (5)	0.0180 (4)	0.0042 (4)	−0.0079 (3)	−0.0044 (3)
O6	0.0292 (5)	0.0384 (5)	0.0192 (4)	0.0116 (4)	−0.0099 (4)	−0.0092 (4)
N1	0.0177 (5)	0.0197 (5)	0.0174 (5)	0.0012 (4)	−0.0032 (4)	−0.0021 (4)
N3	0.0212 (5)	0.0233 (5)	0.0148 (5)	−0.0002 (4)	−0.0023 (4)	−0.0048 (4)
N54	0.0207 (5)	0.0234 (5)	0.0184 (5)	0.0020 (4)	−0.0028 (4)	−0.0057 (4)
C1	0.0211 (6)	0.0263 (6)	0.0240 (6)	0.0061 (5)	−0.0064 (5)	−0.0029 (5)
C2	0.0192 (5)	0.0185 (5)	0.0189 (5)	−0.0029 (4)	−0.0008 (4)	−0.0032 (4)
C3	0.0315 (7)	0.0351 (7)	0.0169 (6)	0.0001 (5)	−0.0025 (5)	−0.0091 (5)
C4	0.0183 (5)	0.0205 (5)	0.0167 (5)	−0.0029 (4)	−0.0024 (4)	−0.0018 (4)
C5	0.0166 (5)	0.0197 (5)	0.0150 (5)	−0.0026 (4)	−0.0023 (4)	−0.0021 (4)
C6	0.0170 (5)	0.0198 (5)	0.0179 (5)	−0.0008 (4)	−0.0024 (4)	−0.0027 (4)
C51	0.0163 (5)	0.0186 (5)	0.0177 (5)	−0.0019 (4)	−0.0023 (4)	−0.0010 (4)
C52	0.0205 (5)	0.0228 (6)	0.0179 (5)	0.0022 (4)	−0.0042 (4)	−0.0014 (4)
C53	0.0216 (6)	0.0230 (6)	0.0169 (5)	0.0013 (5)	−0.0047 (4)	−0.0009 (4)
C54	0.0185 (5)	0.0179 (5)	0.0179 (5)	−0.0029 (4)	−0.0016 (4)	−0.0022 (4)
C55	0.0199 (5)	0.0206 (5)	0.0200 (6)	0.0022 (4)	−0.0059 (4)	−0.0026 (4)
C56	0.0195 (5)	0.0200 (5)	0.0177 (5)	0.0004 (4)	−0.0058 (4)	−0.0010 (4)
C57	0.0173 (5)	0.0204 (5)	0.0157 (5)	−0.0028 (4)	−0.0037 (4)	0.0000 (4)
C541	0.0251 (6)	0.0263 (6)	0.0265 (6)	0.0060 (5)	−0.0045 (5)	−0.0100 (5)
C542	0.0267 (6)	0.0285 (6)	0.0173 (5)	−0.0007 (5)	−0.0025 (5)	−0.0050 (4)

Geometric parameters (Å, º) top

N1—C2	1.3864 (14)	C51—C56	1.4202 (16)
N1—C6	1.3996 (14)	C52—C53	1.3751 (16)
N1—C1	1.4641 (14)	C52—H52	0.95
C1—H1A	0.98	C53—C54	1.4191 (16)
C1—H1B	0.98	C53—H53	0.95
C1—H1C	0.98	C54—N54	1.3545 (14)
C2—O2	1.2189 (14)	C54—C55	1.4211 (15)
C2—N3	1.3835 (15)	N54—C542	1.4594 (15)
C3—N3	1.4673 (14)	N54—C541	1.4607 (15)
C3—H3A	0.98	C541—H54A	0.98
C3—H3B	0.98	C541—H54B	0.98
C3—H3C	0.98	C541—H54C	0.98
N3—C4	1.3927 (15)	C542—H54D	0.98
C4—O4	1.2273 (14)	C542—H54E	0.98
C4—C5	1.4739 (15)	C542—H54F	0.98
C5—C57	1.3814 (16)	C55—C56	1.3709 (16)
C5—C6	1.4579 (15)	C55—H55	0.95
C57—C51	1.4295 (15)	C56—H56	0.95
C57—H57	0.95	C6—O6	1.2250 (14)
C51—C52	1.4179 (15)

C2—N1—C6	125.52 (10)	C53—C52—C51	121.91 (11)
C2—N1—C1	116.76 (9)	C53—C52—H52	119.0
C6—N1—C1	117.58 (9)	C51—C52—H52	119.0
N1—C1—H1A	109.5	C52—C53—C54	121.40 (10)
N1—C1—H1B	109.5	C52—C53—H53	119.3
H1A—C1—H1B	109.5	C54—C53—H53	119.3
N1—C1—H1C	109.5	N54—C54—C53	121.88 (10)
H1A—C1—H1C	109.5	N54—C54—C55	120.80 (10)
H1B—C1—H1C	109.5	C53—C54—C55	117.33 (10)
O2—C2—N3	121.71 (11)	C54—N54—C542	121.60 (10)
O2—C2—N1	121.89 (11)	C54—N54—C541	120.30 (10)
N3—C2—N1	116.40 (10)	C542—N54—C541	118.08 (9)
N3—C3—H3A	109.5	N54—C541—H54A	109.5
N3—C3—H3B	109.5	N54—C541—H54B	109.5
H3A—C3—H3B	109.5	H54A—C541—H54B	109.5
N3—C3—H3C	109.5	N54—C541—H54C	109.5
H3A—C3—H3C	109.5	H54A—C541—H54C	109.5
H3B—C3—H3C	109.5	H54B—C541—H54C	109.5
C2—N3—C4	124.94 (10)	N54—C542—H54D	109.5
C2—N3—C3	116.42 (10)	N54—C542—H54E	109.5
C4—N3—C3	118.65 (10)	H54D—C542—H54E	109.5
O4—C4—N3	119.10 (10)	N54—C542—H54F	109.5
O4—C4—C5	123.61 (11)	H54D—C542—H54F	109.5
N3—C4—C5	117.29 (10)	H54E—C542—H54F	109.5
C57—C5—C6	126.83 (10)	C56—C55—C54	120.43 (11)
C57—C5—C4	114.20 (10)	C56—C55—H55	119.8
C6—C5—C4	118.96 (10)	C54—C55—H55	119.8
C5—C57—C51	138.79 (10)	C55—C56—C51	122.98 (10)
C5—C57—H57	110.6	C55—C56—H56	118.5
C51—C57—H57	110.6	C51—C56—H56	118.5
C52—C51—C56	115.94 (10)	O6—C6—N1	117.78 (10)
C52—C51—C57	128.58 (10)	O6—C6—C5	125.54 (10)
C56—C51—C57	115.48 (10)	N1—C6—C5	116.69 (10)

C6—N1—C2—O2	−175.54 (10)	C57—C51—C52—C53	179.25 (11)
C1—N1—C2—O2	0.01 (16)	C51—C52—C53—C54	−0.46 (18)
C6—N1—C2—N3	5.57 (17)	C52—C53—C54—N54	−179.01 (11)
C1—N1—C2—N3	−178.88 (10)	C52—C53—C54—C55	1.21 (17)
O2—C2—N3—C4	176.96 (11)	C53—C54—N54—C542	−0.48 (17)
N1—C2—N3—C4	−4.16 (16)	C55—C54—N54—C542	179.30 (10)
O2—C2—N3—C3	−2.79 (17)	C53—C54—N54—C541	−178.81 (11)
N1—C2—N3—C3	176.10 (10)	C55—C54—N54—C541	0.96 (17)
C2—N3—C4—O4	179.89 (10)	N54—C54—C55—C56	179.27 (10)
C3—N3—C4—O4	−0.37 (16)	C53—C54—C55—C56	−0.94 (17)
C2—N3—C4—C5	0.73 (16)	C54—C55—C56—C51	−0.07 (18)
C3—N3—C4—C5	−179.53 (10)	C52—C51—C56—C55	0.82 (17)
O4—C4—C5—C57	3.43 (16)	C57—C51—C56—C55	−179.01 (10)
N3—C4—C5—C57	−177.45 (10)	C2—N1—C6—O6	177.03 (11)
O4—C4—C5—C6	−177.46 (11)	C1—N1—C6—O6	1.52 (16)
N3—C4—C5—C6	1.67 (15)	C2—N1—C6—C5	−3.32 (17)
C6—C5—C57—C51	0.7 (2)	C1—N1—C6—C5	−178.84 (9)
C4—C5—C57—C51	179.69 (13)	C57—C5—C6—O6	−1.9 (2)
C5—C57—C51—C52	0.9 (2)	C4—C5—C6—O6	179.14 (11)
C5—C57—C51—C56	−179.29 (13)	C57—C5—C6—N1	178.51 (10)
C56—C51—C52—C53	−0.55 (17)	C4—C5—C6—N1	−0.48 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C52—H52···O6	0.95	2.09	2.895 (2)	141
C53—H53···O4ⁱ	0.95	2.53	3.381 (2)	149
C57—H57···O4	0.95	2.24	2.731 (2)	111

Symmetry code: (i) x, y, z−1.

(V) 5-[3,5-di-tert-butyl-4-hydroxybenzylidene]-1,3-dimethylpyrimidine- 2,4,6(1H,3H,5H)-trione top

Crystal data top

C₂₁H₂₈N₂O₄	Z = 4
M_r = 372.45	F(000) = 800
Triclinic, P1	D_x = 1.289 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6040 (3) Å	Cell parameters from 8856 reflections
b = 11.6691 (4) Å	θ = 3.1–27.7°
c = 17.2905 (6) Å	µ = 0.09 mm⁻¹
α = 97.4860 (16)°	T = 120 K
β = 92.5540 (18)°	Plate, colourless
γ = 90.006 (2)°	0.15 × 0.10 × 0.03 mm
V = 1919.29 (11) Å³

Data collection top

Bruker-Nonius KappaCCD area-detector diffractometer	8856 independent reflections
Radiation source: Bruker-Nonius FR91 rotating anode	6116 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.7°, θ_min = 3.1°
ϕ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −15→15
T_min = 0.967, T_max = 0.997	l = −22→22
39965 measured reflections

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0747P)² + 1.5268P] where P = (F_o² + 2F_c²)/3
8856 reflections	(Δ/σ)_max < 0.001
503 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₂₁H₂₈N₂O₄	γ = 90.006 (2)°
M_r = 372.45	V = 1919.29 (11) Å³
Triclinic, P1	Z = 4
a = 9.6040 (3) Å	Mo Kα radiation
b = 11.6691 (4) Å	µ = 0.09 mm⁻¹
c = 17.2905 (6) Å	T = 120 K
α = 97.4860 (16)°	0.15 × 0.10 × 0.03 mm
β = 92.5540 (18)°

Data collection top

Bruker-Nonius KappaCCD area-detector diffractometer	8856 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	6116 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.997	R_int = 0.068
39965 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.05	Δρ_max = 0.47 e Å⁻³
8856 reflections	Δρ_min = −0.42 e Å⁻³
503 parameters

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

	x	y	z	U_iso*/U_eq
O12	0.7077 (2)	0.13004 (18)	−0.17598 (11)	0.0384 (5)
O14	0.37508 (19)	0.23145 (17)	−0.00358 (11)	0.0362 (5)
O16	0.77518 (19)	0.02010 (17)	0.06284 (11)	0.0350 (4)
O154	0.57647 (17)	0.02617 (16)	0.41750 (10)	0.0278 (4)
N11	0.7265 (2)	0.06075 (18)	−0.05909 (12)	0.0268 (5)
N13	0.5390 (2)	0.17927 (18)	−0.08993 (12)	0.0272 (5)
C11	0.8516 (3)	−0.0028 (3)	−0.08424 (17)	0.0393 (7)
C12	0.6622 (3)	0.1244 (2)	−0.11189 (14)	0.0282 (6)
C13	0.4561 (3)	0.2335 (2)	−0.14836 (15)	0.0347 (6)
C14	0.4862 (3)	0.1843 (2)	−0.01632 (15)	0.0263 (5)
C15	0.5708 (2)	0.1302 (2)	0.04306 (14)	0.0228 (5)
C16	0.6972 (3)	0.0675 (2)	0.01920 (14)	0.0259 (5)
C151	0.5461 (2)	0.1113 (2)	0.19224 (14)	0.0223 (5)
C152	0.6621 (2)	0.05066 (19)	0.21618 (14)	0.0219 (5)
C153	0.6779 (2)	0.02111 (19)	0.29172 (14)	0.0208 (5)
C154	0.5707 (2)	0.05327 (19)	0.34287 (13)	0.0212 (5)
C155	0.4529 (2)	0.1170 (2)	0.32182 (14)	0.0221 (5)
C156	0.4446 (2)	0.14450 (19)	0.24639 (14)	0.0216 (5)
C157	0.5158 (2)	0.1451 (2)	0.11505 (14)	0.0229 (5)
C531	0.8086 (2)	−0.0437 (2)	0.31671 (14)	0.0243 (5)
C532	0.9117 (3)	−0.0630 (2)	0.25124 (16)	0.0334 (6)
C533	0.7702 (3)	−0.1643 (2)	0.33773 (16)	0.0302 (6)
C534	0.8878 (3)	0.0277 (2)	0.38685 (16)	0.0297 (6)
C551	0.3397 (2)	0.1549 (2)	0.37969 (14)	0.0230 (5)
C552	0.2212 (2)	0.2194 (2)	0.34188 (15)	0.0274 (5)
C553	0.2728 (3)	0.0480 (2)	0.40766 (16)	0.0295 (6)
C554	0.4017 (3)	0.2356 (2)	0.44972 (15)	0.0316 (6)
O22	0.7640 (2)	0.62967 (18)	−0.17663 (11)	0.0379 (5)
O24	1.12450 (19)	0.73157 (17)	−0.00405 (11)	0.0366 (5)
O26	0.73439 (19)	0.52023 (17)	0.06211 (10)	0.0342 (4)
O254	0.98200 (18)	0.52583 (16)	0.41712 (10)	0.0300 (4)
N21	0.7640 (2)	0.56069 (18)	−0.05950 (12)	0.0258 (5)
N23	0.9465 (2)	0.67948 (18)	−0.09033 (12)	0.0260 (5)
C21	0.6347 (3)	0.4968 (3)	−0.08484 (17)	0.0384 (7)
C22	0.8201 (3)	0.6242 (2)	−0.11278 (14)	0.0266 (5)
C23	1.0195 (3)	0.7336 (2)	−0.14897 (15)	0.0330 (6)
C24	1.0108 (3)	0.6840 (2)	−0.01701 (14)	0.0257 (5)
C25	0.9358 (2)	0.6300 (2)	0.04244 (14)	0.0232 (5)
C26	0.8055 (3)	0.5676 (2)	0.01895 (14)	0.0252 (5)
C251	0.9846 (2)	0.61063 (19)	0.19149 (14)	0.0211 (5)
C252	0.8722 (2)	0.55038 (19)	0.21561 (13)	0.0207 (5)
C253	0.8678 (2)	0.52121 (19)	0.29108 (14)	0.0210 (5)
C254	0.9822 (2)	0.5542 (2)	0.34276 (13)	0.0219 (5)
C255	1.0972 (2)	0.61689 (19)	0.32165 (13)	0.0209 (5)
C256	1.0944 (2)	0.6437 (2)	0.24588 (14)	0.0217 (5)
C257	1.0025 (2)	0.6444 (2)	0.11460 (14)	0.0225 (5)
C631	0.7412 (2)	0.4561 (2)	0.31593 (14)	0.0236 (5)
C632	0.6289 (3)	0.4348 (2)	0.24965 (15)	0.0305 (6)
C633	0.7836 (3)	0.3369 (2)	0.33841 (16)	0.0300 (6)
C634	0.6727 (3)	0.5286 (2)	0.38463 (15)	0.0296 (6)
C651	1.2204 (2)	0.6555 (2)	0.37934 (14)	0.0239 (5)
C652	1.3332 (3)	0.7181 (2)	0.34047 (15)	0.0279 (5)
C653	1.2917 (3)	0.5506 (2)	0.40860 (17)	0.0321 (6)
C654	1.1696 (3)	0.7406 (2)	0.44770 (15)	0.0307 (6)
H11A	0.9339	0.0464	−0.0703	0.059*
H11B	0.8445	−0.0249	−0.1409	0.059*
H11C	0.8599	−0.0725	−0.0583	0.059*
H13A	0.3637	0.1971	−0.1559	0.052*
H13B	0.5030	0.2235	−0.1979	0.052*
H13C	0.4462	0.3161	−0.1303	0.052*
H32A	0.9372	0.0116	0.2354	0.050*
H32B	0.8683	−0.1123	0.2064	0.050*
H32C	0.9955	−0.1007	0.2700	0.050*
H33A	0.7255	−0.2106	0.2920	0.045*
H33B	0.7058	−0.1555	0.3805	0.045*
H33C	0.8549	−0.2032	0.3540	0.045*
H34A	0.9709	−0.0145	0.4017	0.045*
H34B	0.8268	0.0404	0.4311	0.045*
H34C	0.9157	0.1024	0.3721	0.045*
H52A	0.1515	0.2427	0.3805	0.041*
H52B	0.1776	0.1686	0.2979	0.041*
H52C	0.2589	0.2883	0.3230	0.041*
H53A	0.3440	0.0062	0.4350	0.044*
H53B	0.2332	−0.0029	0.3625	0.044*
H53C	0.1988	0.0730	0.4432	0.044*
H54A	0.4437	0.3032	0.4314	0.047*
H54B	0.4733	0.1944	0.4772	0.047*
H54C	0.3279	0.2609	0.4853	0.047*
H152	0.7322	0.0290	0.1801	0.026*
H154	0.6500	−0.0097	0.4265	0.033*
H156	0.3669	0.1877	0.2306	0.026*
H157	0.4340	0.1907	0.1148	0.027*
H21A	0.5544	0.5464	−0.0718	0.058*
H21B	0.6298	0.4279	−0.0582	0.058*
H21C	0.6335	0.4737	−0.1414	0.058*
H23A	1.0324	0.8162	−0.1310	0.049*
H23B	0.9642	0.7236	−0.1984	0.049*
H23C	1.1106	0.6972	−0.1567	0.049*
H32D	0.5488	0.3954	0.2678	0.046*
H32E	0.6671	0.3865	0.2050	0.046*
H32F	0.5990	0.5089	0.2338	0.046*
H33D	0.8552	0.3471	0.3810	0.045*
H33E	0.8208	0.2895	0.2931	0.045*
H33F	0.7019	0.2984	0.3555	0.045*
H34D	0.6358	0.6000	0.3676	0.044*
H34E	0.7422	0.5478	0.4276	0.044*
H34F	0.5964	0.4842	0.4024	0.044*
H52D	1.2921	0.7844	0.3186	0.042*
H52E	1.3724	0.6648	0.2986	0.042*
H52F	1.4073	0.7452	0.3794	0.042*
H53D	1.3717	0.5767	0.4437	0.048*
H53E	1.3238	0.4984	0.3640	0.048*
H53F	1.2253	0.5098	0.4368	0.048*
H54D	1.2476	0.7619	0.4853	0.046*
H54E	1.0958	0.7040	0.4734	0.046*
H54F	1.1331	0.8102	0.4279	0.046*
H252	0.7965	0.5286	0.1795	0.025*
H254	0.9094	0.4897	0.4249	0.036*
H256	1.1701	0.6863	0.2301	0.026*
H257	1.0846	0.6899	0.1144	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O12	0.0445 (11)	0.0478 (12)	0.0242 (10)	−0.0030 (9)	0.0062 (8)	0.0073 (9)
O14	0.0399 (11)	0.0439 (12)	0.0262 (10)	0.0153 (9)	0.0019 (8)	0.0101 (8)
O16	0.0377 (10)	0.0417 (11)	0.0279 (10)	0.0135 (8)	0.0086 (8)	0.0106 (8)
O154	0.0244 (9)	0.0398 (10)	0.0211 (9)	0.0068 (7)	0.0009 (7)	0.0117 (7)
N11	0.0286 (11)	0.0287 (11)	0.0234 (11)	0.0019 (9)	0.0049 (8)	0.0031 (9)
N13	0.0344 (12)	0.0250 (11)	0.0223 (11)	−0.0023 (9)	−0.0041 (9)	0.0058 (8)
C11	0.0380 (15)	0.0505 (18)	0.0300 (15)	0.0125 (13)	0.0118 (12)	0.0038 (13)
C12	0.0347 (14)	0.0315 (14)	0.0184 (12)	−0.0082 (11)	0.0036 (10)	0.0023 (10)
C13	0.0483 (16)	0.0333 (14)	0.0231 (13)	−0.0030 (12)	−0.0064 (12)	0.0090 (11)
C14	0.0310 (13)	0.0218 (12)	0.0255 (13)	0.0015 (10)	0.0002 (10)	0.0008 (10)
C15	0.0262 (12)	0.0193 (11)	0.0230 (12)	−0.0007 (9)	0.0015 (9)	0.0032 (9)
C16	0.0325 (13)	0.0235 (12)	0.0222 (13)	−0.0022 (10)	0.0037 (10)	0.0038 (10)
C151	0.0240 (12)	0.0197 (11)	0.0229 (12)	−0.0020 (9)	−0.0015 (9)	0.0023 (9)
C152	0.0237 (12)	0.0184 (11)	0.0234 (12)	0.0005 (9)	0.0041 (9)	0.0006 (9)
C153	0.0223 (11)	0.0182 (11)	0.0217 (12)	−0.0027 (9)	−0.0008 (9)	0.0023 (9)
C154	0.0241 (12)	0.0202 (11)	0.0198 (12)	−0.0021 (9)	−0.0003 (9)	0.0046 (9)
C155	0.0227 (11)	0.0207 (11)	0.0227 (12)	−0.0036 (9)	−0.0016 (9)	0.0034 (9)
C156	0.0217 (11)	0.0198 (11)	0.0235 (12)	0.0021 (9)	0.0001 (9)	0.0035 (9)
C157	0.0261 (12)	0.0214 (12)	0.0210 (12)	0.0017 (9)	−0.0007 (9)	0.0032 (9)
C531	0.0234 (12)	0.0241 (12)	0.0259 (13)	0.0023 (9)	0.0012 (9)	0.0049 (10)
C532	0.0287 (13)	0.0386 (15)	0.0343 (15)	0.0107 (11)	0.0052 (11)	0.0095 (12)
C533	0.0325 (14)	0.0252 (13)	0.0332 (15)	0.0050 (10)	−0.0023 (11)	0.0068 (11)
C534	0.0231 (12)	0.0320 (14)	0.0338 (15)	0.0013 (10)	−0.0006 (10)	0.0046 (11)
C551	0.0212 (11)	0.0259 (12)	0.0224 (12)	0.0024 (9)	0.0002 (9)	0.0056 (10)
C552	0.0247 (12)	0.0329 (14)	0.0254 (13)	0.0071 (10)	0.0040 (10)	0.0062 (11)
C553	0.0246 (12)	0.0347 (14)	0.0308 (14)	−0.0017 (11)	0.0025 (10)	0.0098 (11)
C554	0.0313 (14)	0.0331 (14)	0.0284 (14)	0.0018 (11)	0.0009 (11)	−0.0028 (11)
O22	0.0427 (11)	0.0488 (12)	0.0227 (10)	0.0029 (9)	−0.0067 (8)	0.0087 (8)
O24	0.0383 (11)	0.0477 (12)	0.0248 (10)	−0.0134 (9)	−0.0014 (8)	0.0100 (8)
O26	0.0344 (10)	0.0428 (11)	0.0265 (10)	−0.0139 (8)	−0.0050 (8)	0.0110 (8)
O254	0.0320 (10)	0.0394 (10)	0.0207 (9)	−0.0048 (8)	0.0008 (7)	0.0115 (8)
N21	0.0275 (11)	0.0275 (11)	0.0217 (11)	−0.0004 (8)	−0.0038 (8)	0.0021 (8)
N23	0.0330 (11)	0.0264 (11)	0.0198 (10)	0.0024 (9)	0.0024 (8)	0.0071 (8)
C21	0.0359 (15)	0.0494 (18)	0.0286 (15)	−0.0097 (13)	−0.0083 (12)	0.0034 (13)
C22	0.0323 (13)	0.0284 (13)	0.0188 (12)	0.0071 (10)	−0.0011 (10)	0.0032 (10)
C23	0.0460 (16)	0.0333 (14)	0.0220 (13)	0.0031 (12)	0.0078 (11)	0.0103 (11)
C24	0.0295 (13)	0.0262 (13)	0.0215 (12)	0.0007 (10)	0.0011 (10)	0.0037 (10)
C25	0.0271 (12)	0.0230 (12)	0.0197 (12)	0.0028 (10)	−0.0017 (9)	0.0042 (9)
C26	0.0306 (13)	0.0236 (12)	0.0214 (12)	0.0006 (10)	−0.0031 (10)	0.0047 (10)
C251	0.0242 (12)	0.0178 (11)	0.0213 (12)	0.0006 (9)	−0.0001 (9)	0.0025 (9)
C252	0.0227 (11)	0.0182 (11)	0.0206 (12)	0.0018 (9)	−0.0019 (9)	0.0014 (9)
C253	0.0216 (11)	0.0187 (11)	0.0227 (12)	0.0023 (9)	0.0008 (9)	0.0024 (9)
C254	0.0258 (12)	0.0242 (12)	0.0160 (11)	0.0013 (9)	0.0014 (9)	0.0041 (9)
C255	0.0243 (12)	0.0182 (11)	0.0203 (12)	0.0043 (9)	0.0009 (9)	0.0029 (9)
C256	0.0219 (11)	0.0214 (12)	0.0221 (12)	0.0007 (9)	0.0027 (9)	0.0031 (9)
C257	0.0243 (12)	0.0207 (11)	0.0229 (12)	−0.0005 (9)	0.0013 (9)	0.0041 (9)
C631	0.0246 (12)	0.0234 (12)	0.0236 (12)	−0.0013 (9)	0.0009 (9)	0.0057 (10)
C632	0.0278 (13)	0.0350 (14)	0.0299 (14)	−0.0095 (11)	−0.0013 (10)	0.0102 (11)
C633	0.0346 (14)	0.0256 (13)	0.0309 (14)	−0.0054 (11)	0.0036 (11)	0.0075 (11)
C634	0.0269 (13)	0.0313 (14)	0.0311 (14)	−0.0016 (10)	0.0034 (10)	0.0053 (11)
C651	0.0235 (12)	0.0285 (13)	0.0198 (12)	−0.0007 (10)	−0.0013 (9)	0.0044 (10)
C652	0.0257 (12)	0.0331 (14)	0.0247 (13)	−0.0054 (10)	−0.0033 (10)	0.0048 (11)
C653	0.0249 (13)	0.0360 (15)	0.0368 (16)	0.0008 (11)	−0.0031 (11)	0.0122 (12)
C654	0.0334 (14)	0.0340 (14)	0.0235 (13)	−0.0033 (11)	−0.0010 (10)	0.0003 (11)

Geometric parameters (Å, º) top

N11—C12	1.376 (3)	N21—C22	1.383 (3)
N11—C16	1.387 (3)	N21—C26	1.389 (3)
N11—C11	1.465 (3)	N21—C21	1.468 (3)
C11—H11A	0.98	C21—H21A	0.98
C11—H11B	0.98	C21—H21B	0.98
C11—H11C	0.98	C21—H21C	0.98
C12—O12	1.219 (3)	C22—O22	1.216 (3)
C12—N13	1.389 (3)	C22—N23	1.390 (3)
N13—C14	1.385 (3)	N23—C24	1.380 (3)
N13—C13	1.466 (3)	N23—C23	1.466 (3)
C13—H13A	0.98	C23—H23A	0.98
C13—H13B	0.98	C23—H23B	0.98
C13—H13C	0.98	C23—H23C	0.98
C14—O14	1.217 (3)	C24—O24	1.224 (3)
C14—C15	1.485 (3)	C24—C25	1.486 (3)
C15—C157	1.364 (3)	C25—C257	1.367 (3)
C15—C16	1.465 (3)	C25—C26	1.462 (3)
C16—O16	1.223 (3)	C26—O26	1.217 (3)
C157—C151	1.457 (3)	C257—C251	1.453 (3)
C157—H157	0.95	C257—H257	0.95
C151—C152	1.396 (3)	C251—C252	1.397 (3)
C151—C156	1.401 (3)	C251—C256	1.400 (3)
C152—C153	1.396 (3)	C252—C253	1.393 (3)
C152—H152	0.95	C252—H252	0.95
C153—C154	1.406 (3)	C253—C254	1.406 (3)
C153—C531	1.540 (3)	C253—C631	1.540 (3)
C531—C532	1.531 (4)	C631—C632	1.534 (3)
C531—C533	1.548 (3)	C631—C634	1.539 (4)
C531—C534	1.548 (3)	C631—C633	1.543 (3)
C532—H32A	0.98	C632—H32D	0.98
C532—H32B	0.98	C632—H32E	0.98
C532—H32C	0.98	C632—H32F	0.98
C533—H33A	0.98	C633—H33D	0.98
C533—H33B	0.98	C633—H33E	0.98
C533—H33C	0.98	C633—H33F	0.98
C534—H34A	0.98	C634—H34D	0.98
C534—H34B	0.98	C634—H34E	0.98
C534—H34C	0.98	C634—H34F	0.98
C154—O154	1.367 (3)	C254—O254	1.369 (3)
C154—C155	1.414 (3)	C254—C255	1.412 (3)
O154—H154	0.8395	O254—H254	0.8394
C155—C156	1.382 (3)	C255—C256	1.385 (3)
C155—C551	1.537 (3)	C255—C651	1.542 (3)
C551—C554	1.532 (3)	C651—C652	1.534 (3)
C551—C552	1.533 (3)	C651—C653	1.534 (3)
C551—C553	1.545 (3)	C651—C654	1.539 (4)
C552—H52A	0.98	C652—H52D	0.98
C552—H52B	0.98	C652—H52E	0.98
C552—H52C	0.98	C652—H52F	0.98
C553—H53A	0.98	C653—H53D	0.98
C553—H53B	0.98	C653—H53E	0.98
C553—H53C	0.98	C653—H53F	0.98
C554—H54A	0.98	C654—H54D	0.98
C554—H54B	0.98	C654—H54E	0.98
C554—H54C	0.98	C654—H54F	0.98
C156—H156	0.95	C256—H256	0.95

C12—N11—C16	125.2 (2)	C22—N21—C26	125.4 (2)
C12—N11—C11	116.7 (2)	C22—N21—C21	116.5 (2)
C16—N11—C11	117.2 (2)	C26—N21—C21	117.2 (2)
N11—C11—H11A	109.5	N21—C21—H21A	109.5
N11—C11—H11B	109.5	N21—C21—H21B	109.5
H11A—C11—H11B	109.5	H21A—C21—H21B	109.5
N11—C11—H11C	109.5	N21—C21—H21C	109.5
H11A—C11—H11C	109.5	H21A—C21—H21C	109.5
H11B—C11—H11C	109.5	H21B—C21—H21C	109.5
O12—C12—N11	122.2 (2)	O22—C22—N21	122.1 (2)
O12—C12—N13	121.0 (2)	O22—C22—N23	121.5 (2)
N11—C12—N13	116.8 (2)	N21—C22—N23	116.4 (2)
C14—N13—C12	124.4 (2)	C24—N23—C22	124.5 (2)
C14—N13—C13	117.0 (2)	C24—N23—C23	117.3 (2)
C12—N13—C13	118.6 (2)	C22—N23—C23	118.1 (2)
N13—C13—H13A	109.5	N23—C23—H23A	109.5
N13—C13—H13B	109.5	N23—C23—H23B	109.5
H13A—C13—H13B	109.5	H23A—C23—H23B	109.5
N13—C13—H13C	109.5	N23—C23—H23C	109.5
H13A—C13—H13C	109.5	H23A—C23—H23C	109.5
H13B—C13—H13C	109.5	H23B—C23—H23C	109.5
O14—C14—N13	119.4 (2)	O24—C24—N23	119.3 (2)
O14—C14—C15	123.7 (2)	O24—C24—C25	123.5 (2)
N13—C14—C15	117.0 (2)	N23—C24—C25	117.1 (2)
C157—C15—C16	128.0 (2)	C257—C25—C26	127.7 (2)
C157—C15—C14	113.2 (2)	C257—C25—C24	113.4 (2)
C16—C15—C14	118.8 (2)	C26—C25—C24	118.9 (2)
O16—C16—N11	119.0 (2)	O26—C26—N21	118.8 (2)
O16—C16—C15	124.6 (2)	O26—C26—C25	125.1 (2)
N11—C16—C15	116.4 (2)	N21—C26—C25	116.1 (2)
C15—C157—C151	138.5 (2)	C25—C257—C251	138.5 (2)
C15—C157—H157	110.7	C25—C257—H257	110.7
C151—C157—H157	110.7	C251—C257—H257	110.7
C152—C151—C156	118.6 (2)	C252—C251—C256	118.3 (2)
C152—C151—C157	127.1 (2)	C252—C251—C257	127.2 (2)
C156—C151—C157	114.3 (2)	C256—C251—C257	114.5 (2)
C153—C152—C151	121.7 (2)	C253—C252—C251	122.0 (2)
C153—C152—H152	119.1	C253—C252—H252	119.0
C151—C152—H152	119.1	C251—C252—H252	119.0
C152—C153—C154	117.3 (2)	C252—C253—C254	117.4 (2)
C152—C153—C531	120.4 (2)	C252—C253—C631	120.5 (2)
C154—C153—C531	122.3 (2)	C254—C253—C631	122.1 (2)
C532—C531—C153	111.6 (2)	C632—C631—C634	106.6 (2)
C532—C531—C533	107.0 (2)	C632—C631—C253	111.53 (19)
C153—C531—C533	111.14 (19)	C634—C631—C253	110.12 (19)
C532—C531—C534	106.3 (2)	C632—C631—C633	107.1 (2)
C153—C531—C534	110.59 (19)	C634—C631—C633	110.2 (2)
C533—C531—C534	110.1 (2)	C253—C631—C633	111.14 (19)
C531—C532—H32A	109.5	C631—C632—H32D	109.5
C531—C532—H32B	109.5	C631—C632—H32E	109.5
H32A—C532—H32B	109.5	H32D—C632—H32E	109.5
C531—C532—H32C	109.5	C631—C632—H32F	109.5
H32A—C532—H32C	109.5	H32D—C632—H32F	109.5
H32B—C532—H32C	109.5	H32E—C632—H32F	109.5
C531—C533—H33A	109.5	C631—C633—H33D	109.5
C531—C533—H33B	109.5	C631—C633—H33E	109.5
H33A—C533—H33B	109.5	H33D—C633—H33E	109.5
C531—C533—H33C	109.5	C631—C633—H33F	109.5
H33A—C533—H33C	109.5	H33D—C633—H33F	109.5
H33B—C533—H33C	109.5	H33E—C633—H33F	109.5
C531—C534—H34A	109.5	C631—C634—H34D	109.5
C531—C534—H34B	109.5	C631—C634—H34E	109.5
H34A—C534—H34B	109.5	H34D—C634—H34E	109.5
C531—C534—H34C	109.5	C631—C634—H34F	109.5
H34A—C534—H34C	109.5	H34D—C634—H34F	109.5
H34B—C534—H34C	109.5	H34E—C634—H34F	109.5
O154—C154—C153	121.2 (2)	O254—C254—C253	118.9 (2)
O154—C154—C155	115.8 (2)	O254—C254—C255	118.3 (2)
C153—C154—C155	123.0 (2)	C253—C254—C255	122.8 (2)
C154—O154—H154	110.8	C254—O254—H254	112.0
C156—C155—C154	116.7 (2)	C256—C255—C254	116.8 (2)
C156—C155—C551	121.2 (2)	C256—C255—C651	120.7 (2)
C154—C155—C551	122.0 (2)	C254—C255—C651	122.5 (2)
C554—C551—C552	107.9 (2)	C652—C651—C653	106.1 (2)
C554—C551—C155	110.38 (19)	C652—C651—C654	107.1 (2)
C552—C551—C155	111.81 (19)	C653—C651—C654	111.2 (2)
C554—C551—C553	110.1 (2)	C652—C651—C255	111.66 (19)
C552—C551—C553	106.50 (19)	C653—C651—C255	110.7 (2)
C155—C551—C553	110.1 (2)	C654—C651—C255	109.96 (19)
C551—C552—H52A	109.5	C651—C652—H52D	109.5
C551—C552—H52B	109.5	C651—C652—H52E	109.5
H52A—C552—H52B	109.5	H52D—C652—H52E	109.5
C551—C552—H52C	109.5	C651—C652—H52F	109.5
H52A—C552—H52C	109.5	H52D—C652—H52F	109.5
H52B—C552—H52C	109.5	H52E—C652—H52F	109.5
C551—C553—H53A	109.5	C651—C653—H53D	109.5
C551—C553—H53B	109.5	C651—C653—H53E	109.5
H53A—C553—H53B	109.5	H53D—C653—H53E	109.5
C551—C553—H53C	109.5	C651—C653—H53F	109.5
H53A—C553—H53C	109.5	H53D—C653—H53F	109.5
H53B—C553—H53C	109.5	H53E—C653—H53F	109.5
C551—C554—H54A	109.5	C651—C654—H54D	109.5
C551—C554—H54B	109.5	C651—C654—H54E	109.5
H54A—C554—H54B	109.5	H54D—C654—H54E	109.5
C551—C554—H54C	109.5	C651—C654—H54F	109.5
H54A—C554—H54C	109.5	H54D—C654—H54F	109.5
H54B—C554—H54C	109.5	H54E—C654—H54F	109.5
C155—C156—C151	122.7 (2)	C255—C256—C251	122.8 (2)
C155—C156—H156	118.7	C255—C256—H256	118.6
C151—C156—H156	118.7	C251—C256—H256	118.6

C16—N11—C12—O12	167.0 (2)	C26—N21—C22—O22	−166.8 (2)
C11—N11—C12—O12	−1.4 (4)	C21—N21—C22—O22	1.8 (4)
C16—N11—C12—N13	−15.3 (3)	C26—N21—C22—N23	14.9 (4)
C11—N11—C12—N13	176.3 (2)	C21—N21—C22—N23	−176.6 (2)
O12—C12—N13—C14	−174.9 (2)	O22—C22—N23—C24	175.0 (2)
N11—C12—N13—C14	7.4 (3)	N21—C22—N23—C24	−6.6 (4)
O12—C12—N13—C13	6.7 (4)	O22—C22—N23—C23	−7.1 (4)
N11—C12—N13—C13	−171.0 (2)	N21—C22—N23—C23	171.3 (2)
C12—N13—C14—O14	−177.7 (2)	C22—N23—C24—O24	177.5 (2)
C13—N13—C14—O14	0.7 (3)	C23—N23—C24—O24	−0.4 (4)
C12—N13—C14—C15	2.1 (3)	C22—N23—C24—C25	−2.6 (4)
C13—N13—C14—C15	−179.5 (2)	C23—N23—C24—C25	179.5 (2)
O14—C14—C15—C157	−3.9 (3)	O24—C24—C25—C257	3.7 (4)
N13—C14—C15—C157	176.2 (2)	N23—C24—C25—C257	−176.2 (2)
O14—C14—C15—C16	175.0 (2)	O24—C24—C25—C26	−175.3 (2)
N13—C14—C15—C16	−4.9 (3)	N23—C24—C25—C26	4.8 (3)
C12—N11—C16—O16	−168.9 (2)	C22—N21—C26—O26	169.1 (2)
C11—N11—C16—O16	−0.6 (3)	C21—N21—C26—O26	0.6 (4)
C12—N11—C16—C15	12.4 (3)	C22—N21—C26—C25	−12.5 (4)
C11—N11—C16—C15	−179.3 (2)	C21—N21—C26—C25	179.0 (2)
C157—C15—C16—O16	−1.6 (4)	C257—C25—C26—O26	1.6 (4)
C14—C15—C16—O16	179.7 (2)	C24—C25—C26—O26	−179.6 (2)
C157—C15—C16—N11	177.0 (2)	C257—C25—C26—N21	−176.7 (2)
C14—C15—C16—N11	−1.8 (3)	C24—C25—C26—N21	2.1 (3)
C16—C15—C157—C151	−1.2 (5)	C26—C25—C257—C251	1.1 (5)
C14—C15—C157—C151	177.6 (3)	C24—C25—C257—C251	−177.7 (3)
C15—C157—C151—C152	4.5 (5)	C25—C257—C251—C252	−4.6 (5)
C15—C157—C151—C156	−175.2 (3)	C25—C257—C251—C256	175.5 (3)
C156—C151—C152—C153	1.1 (3)	C256—C251—C252—C253	−1.0 (3)
C157—C151—C152—C153	−178.6 (2)	C257—C251—C252—C253	179.0 (2)
C151—C152—C153—C154	1.0 (3)	C251—C252—C253—C254	−0.4 (3)
C151—C152—C153—C531	−178.8 (2)	C251—C252—C253—C631	179.2 (2)
C152—C153—C531—C532	2.5 (3)	C252—C253—C631—C632	−1.8 (3)
C154—C153—C531—C532	−177.3 (2)	C254—C253—C631—C632	177.8 (2)
C152—C153—C531—C533	−116.9 (2)	C252—C253—C631—C634	−119.9 (2)
C154—C153—C531—C533	63.4 (3)	C254—C253—C631—C634	59.6 (3)
C152—C153—C531—C534	120.6 (2)	C252—C253—C631—C633	117.6 (2)
C154—C153—C531—C534	−59.2 (3)	C254—C253—C631—C633	−62.8 (3)
C152—C153—C154—O154	178.9 (2)	C252—C253—C254—O254	−179.3 (2)
C531—C153—C154—O154	−1.3 (3)	C631—C253—C254—O254	1.1 (3)
C152—C153—C154—C155	−2.5 (3)	C252—C253—C254—C255	1.5 (3)
C531—C153—C154—C155	177.3 (2)	C631—C253—C254—C255	−178.1 (2)
O154—C154—C155—C156	−179.52 (19)	O254—C254—C255—C256	179.7 (2)
C153—C154—C155—C156	1.8 (3)	C253—C254—C255—C256	−1.1 (3)
O154—C154—C155—C551	0.9 (3)	O254—C254—C255—C651	−0.9 (3)
C153—C154—C155—C551	−177.7 (2)	C253—C254—C255—C651	178.4 (2)
C156—C155—C551—C554	−117.9 (2)	C256—C255—C651—C652	−2.6 (3)
C154—C155—C551—C554	61.7 (3)	C254—C255—C651—C652	177.9 (2)
C156—C155—C551—C552	2.2 (3)	C256—C255—C651—C653	−120.6 (2)
C154—C155—C551—C552	−178.2 (2)	C254—C255—C651—C653	60.0 (3)
C156—C155—C551—C553	120.4 (2)	C256—C255—C651—C654	116.1 (2)
C154—C155—C551—C553	−60.1 (3)	C254—C255—C651—C654	−63.3 (3)
C154—C155—C156—C151	0.4 (3)	C254—C255—C256—C251	−0.5 (3)
C551—C155—C156—C151	180.0 (2)	C651—C255—C256—C251	−179.9 (2)
C152—C151—C156—C155	−1.8 (3)	C252—C251—C256—C255	1.5 (3)
C157—C151—C156—C155	177.9 (2)	C257—C251—C256—C255	−178.5 (2)

Experimental details

	(I)	(II)	(III)	(IV)
Crystal data
Chemical formula	C₁₃H₁₂N₂O₃	C₁₄H₁₄N₂O₄	C₁₄H₁₄N₂O₄	C₁₅H₁₇N₃O₃
M_r	244.25	274.27	274.27	287.32
Crystal system, space group	Monoclinic, P2₁/n	Triclinic, P1	Triclinic, P1	Triclinic, P1
Temperature (K)	120	120	120	120
a, b, c (Å)	6.1293 (3), 13.9633 (8), 13.2727 (8)	5.6946 (2), 8.2994 (3), 14.0411 (5)	7.5906 (6), 8.2989 (7), 10.301 (1)	8.6187 (2), 8.8451 (3), 9.0566 (3)
α, β, γ (°)	90, 97.688 (4), 90	73.5580 (17), 87.393 (2), 77.037 (2)	92.544 (6), 93.074 (5), 104.456 (6)	82.2980 (18), 84.465 (2), 82.365 (2)
V (Å³)	1125.74 (11)	620.13 (4)	626.33 (10)	675.94 (4)
Z	4	2	2	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.10	0.11	0.11	0.10
Crystal size (mm)	0.34 × 0.25 × 0.09	0.52 × 0.34 × 0.16	0.48 × 0.44 × 0.34	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker-Nonius KappaCCD area-detector diffractometer	Bruker-Nonius KappaCCD area-detector diffractometer	Bruker-Nonius KappaCCD area-detector diffractometer	Bruker-Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)	Multi-scan (SADABS; Sheldrick, 2003)	Multi-scan (SADABS; Sheldrick, 2003)	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.954, 0.991	0.953, 0.983	0.947, 0.964	0.955, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	12444, 2573, 1885	14859, 2847, 2331	10553, 2860, 2173	13410, 3073, 2698
R_int	0.050	0.034	0.034	0.027
(sin θ/λ)_max (Å⁻¹)	0.652	0.650	0.650	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.201, 1.05	0.040, 0.132, 1.11	0.046, 0.136, 1.06	0.039, 0.108, 1.05
No. of reflections	2573	2847	2860	3073
No. of parameters	165	184	184	194
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)	0.47, −0.30	0.40, −0.40	0.27, −0.24	0.28, −0.27

	(V)
Crystal data
Chemical formula	C₂₁H₂₈N₂O₄
M_r	372.45
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	9.6040 (3), 11.6691 (4), 17.2905 (6)
α, β, γ (°)	97.4860 (16), 92.5540 (18), 90.006 (2)
V (Å³)	1919.29 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.15 × 0.10 × 0.03

Data collection
Diffractometer	Bruker-Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.967, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	39965, 8856, 6116
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.654

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.179, 1.05
No. of reflections	8856
No. of parameters	503
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.42

Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997) and COLLECT, 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, mol 1)	(V, mol 2)
n =	nil	nil	nil	nil	1	2
Cn2-On2	1.211 (3)	1.2160 (18)	1.2166 (18)	1.2189 (14)	1.219 (3)	1.216 (3)
Cn4-On4	1.219 (3)	1.2235 (17)	1.2204 (18)	1.2273 (14)	1.217 (3)	1.224 (3)
Cn6-On6	1.211 (3)	1.2234 (18)	1.2157 (19)	1.2250 (14)	1.223 (3)	1.217 (3)
Cn5-Cn57	1.362 (3)	1.3627 (19)	1.366 (2)	1.3814 (16)	1.364 (3)	1.367 (3)
Cn57-Cn51	1.447 (3)	1.4658 (19)	1.449 (2)	1.4295 (15)	1.457 (3)	1.453 (3)
Cn51-Cn52	1.403 (3)	1.4065 (19)	1.410 (2)	1.4179 (15)	1.396 (3)	1.397 (3)
Cn52-Cn53	1.391 (3)	1.390 (2)	1.378 (2)	1.3751 (16)	1.396 (3)	1.393 (3)
Cn53-Cn54	1.387 (3)	1.396 (2)	1.402 (2)	1.4191 (16)	1.406 (3)	1.406 (3)
Cn54-Cn55	1.383 (4)	1.385 (2)	1.388 (2)	1.4211 (15)	1.414 (3)	1.412 (3)
Cn55-Cn56	1.397 (3)	1.392 (2)	1.384 (2)	1.3709 (16)	1.382 (3)	1.385 (3)
Cn56-Cn51	1.405 (3)	1.404 (2)	1.404 (2)	1.4202 (16)	1.401 (3)	1.400 (3)
Cn53-On53		1.3679 (17)
Cn54-On54			1.3578 (17)		1.367 (3)	1.369 (3)
Cn54-N54				1.3545 (14)
Cn5-Cn4-On4
	123.6 (2)	122.83 (13)	123.49 (13)	123.61 (11)	127.7 (2)	123.5 (2)
Cn5-Cn6-On6
	124.5 (2)	124.95 (13)	124.00 (14)	125.54 (10)	124.6 (2)	125.1 (2)
Cn4-Cn5-Cn57
	115.23 (19)	114.14 (12)	114.26 (13)	114.20 (10)	113.2 (2)	113.4 (2)
Cn6-Cn5-Cn57
	125.99 (19)	127.41 (13)	126.71 (13)	126.83 (10)	128.0 (2)	127.7 (2)
Cn5-Cn57-Cn51
	137.1 (2)	137.62 (13)	139.14 (14)	138.79 (10)	138.5(2	138.5 (2)
Cn57-Cn51-Cn52
	127.2 (2)	126.34 (13)	128.25 (14)	128.58 (10)	127.1 (2)	127.2 (2)
Cn52-Cn53-On53		123.31 (13)
Cn54-Cn53-On53		115.69 (13)
Cn53-Cn54-On54			115.72 (13)		121.2 (2)	118.9 (2)
Cn55-Cn54-On54			124.18 (14)		115.8 (2)	118.3 (2)
Cn5-Cn57-Cn51-Cn52
	-14.6 (2)	4.1 (3)	6.1 (3)	0.9 (2)	4.5 (5)	-4.6 (5)
Cn52-Cn53-On53-Cn531		-2.1 (2)
Cn53-Cn54-On54-Cn541			176.86 (13)

Hydrogen bonds and short intramolecular contacts (Å, °) for compounds (I)–(V) top

Compound	D-H···A	D-H	H···A	D···A	D-H···A
(I)	C52-H52···O6	0.95	2.17	2.867 (3)	130
	C53-H53···O6ⁱ	0.95	2.47	3.399 (3)	167
	C56-H56···O4ⁱⁱ	0.95	2.40	3.310 (3)	159
	C57-H57···O4	0.95	2.28	2.751 (3)	110
(II)	C52-H52···O6	0.95	2.07	2.855 (2)	139
	C54-H54···O2ⁱⁱⁱ	0.95	2.38	3.334 (2)	178
	C56-H56···O4ⁱ	0.95	2.38	3.313 (2)	168
	C57-H57···O4	0.95	2.24	2.727 (2)	111
(III)	C52-H52···O6	0.95	2.11	2.889 (2)	138
	C53-H53···O6ⁱⁱ	0.95	2.52	3.387 (2)	152
	C55-H55···O4^iv	0.95	2.39	3.261 (2)	152
	C57-H57···O4	0.95	2.23	2.729 (2)	112
(IV)	C52-H52···O6	0.95	2.09	2.895 (2)	141
	C53-H53···O4^v	0.95	2.53	3.381 (2)	149
	C57-H57···O4	0.95	2.24	2.731 (2)	111
(V)	C152-H152···O16	0.95	2.08	2.889 (3)	143
	C157-H157···O14	0.95	2.21	2.709 (3)	112
	C252-H252···O26	0.95	2.08	2.892 (3)	143
	C257-H257···O24	0.95	2.22	2.716 (3)	112

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

Acknowledgements

The X-ray data 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. 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
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
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Evans, D. G. & Boeyens, J. C. A. (1989). Acta Cryst. B45, 581–590. CrossRef CAS Web of Science 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
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Rezende, M. C., Campodonico, P., Abuin, E. & Kossanyi, J. (2001). Spectrochim. Acta A, 57, 1183–1190. CrossRef CAS Google Scholar
Rezende, M. C., Flores, P., Guerrero, J. & Villarroel, L. (2004). Spectrochim. Acta A, 60, 1637–1640. CrossRef Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2003). SADABS. Version 2.10. 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
Suzuki, K., Fukawa, H., Okugawa, T. & Sekiya, M. (1976). Chem. Pharm. Bull. 24, 607–612. CrossRef CAS 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 61| Part 5| May 2005| Pages o306-o311

doi:10.1107/S0108270105008498

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

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

Supramolecular structures of five 5-(aryl­methyl­ene)-1,3-di­methyl­pyrimidine-2,4,6(1H,3H,5H)-triones: isolated mol­ecules, hydrogen-bonded chains and chains of fused hydrogen-bonded rings

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

Supramolecular structures of five 5-(arylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones: isolated molecules, hydrogen-bonded chains and chains of fused hydrogen-bonded rings