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The molecules of the title compound, C18H16N4O3, exhibit a very polarized molecular-electronic structure. The mol­ecules are linked into chains by a combination of an asymmetric three-centre N-H...(N,O) hydrogen bond [H...N 2.19, H...O 2.54, N...N 3.041 (4) and N...O 2.977 (4) Å, and N-H...N 168, N-H...O 112 and N...H...O 67°] and an N-H...[pi](arene) interaction [H...Cg 2.67 Å, N...Cg 3.496 (4) Å and N-H...Cg 163°; Cg is a benzyl ring centroid].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102008181/sk1553sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102008181/sk1553Isup2.hkl
Contains datablock I

CCDC reference: 188625

Comment top

We recently reported the molecular and supramolecular structures of a number of 2-amino-benzyloxy-5-nitrosopyrimidines (Quesada et al., 2002). The majority of the compounds in that study contained a 4-amino substituent, derived either from a simple primary amine or from an amino-acid ester. Here, we report the structure of the title compound, (I), an example containing an unsubstituted 2-amino group and a 4-benzyloxy substituent, and we compare the conformation, molecular dimensions and supramolecular aggregation of (I) with those of the related compounds, (II) and (III) (Quesada et al., 2002). \sch

In compound (I) (Fig. 1), the N—C—O—C and C—O—C—C torsion angles (Table 1) defining the orientation of the benzyloxy groups are very similar for the two independent substituents, and indicate that atoms C41, C47, C61 and C67 all lie close to the plane defined by the pyrimidine ring, with both benzyl groups oriented remote from the nitrosyl substituent. The torsion angles around the C41—C47 and C61—C67 bonds are, however, entirely different. In compound (II), for comparison, the two independent N—C—O—C torsion angles indicate a different conformation, which does not even approximately manifest the potential twofold rotation symmetry available to molecules of (II), although atoms C41, C47, C61 and C67 are again close to the plane of the pyrimidine. In (III), the N—C—O—C angles resemble those in (I), but the C6—O6—C67—C61 torsion angle is unlike any of the other analogous angles in this series. In this connection, it is interesting to note that, in compound (IV) (Low et al., 2002), the conformation of the alkoxy substituents is similar to that in (II).

The C2—N2, N3—C4 and C6—N1 bond distances (Table 2) in (I) are all short for their types (Allen et al., 1987). These distances and those in the C-nitroso fragment point to the charge-separated form, (Ia), as an important contributor to the overall molecular-electronic structure, as generally found for substituted 2-amino-5-nitrosopyrimidines (Low et al., 2000; Quesada et al., 2002). By contrast, when the 5-nitroso group is absent, as in (II) and (IV), there is no geometric evidence for any significant polarization of the electronic structure.

The supramolecular aggregation in (I) (Table 3) involves both conventional hydrogen bonds and an N—H···π(arene) hydrogen bond, now a well recognized intermolecular interaction (Malone et al., 1997; Braga et al., 1998). The amino atom N2 in the molecule at (x, y, z) acts as a hydrogen-bond donor, via atom H2A, to nitrosyl atom N5 in the molecule at (x, y - 1, z), so generating by translation a C(7) chain parallel to [010] (Fig. 2). Both the donor atom, N2, and the acceptor atom, N5, in this hydrogen bond carry significant partial charges, and hence this interaction is an example of a resonance-assisted hydrogen bond (Gilli et al., 1994). The same atom H2A at (x, y, z) also makes a rather long contact with atom O4 in the molecule at (x, y - 1, z), so forming a very asymmetric three-centre N—H···(N, O) hydrogen bond, but the H···O contact may well be more adventitious than significant. The other H atom of the amino group, H2B, does not form a conventional hard (Braga et al., 1995) hydrogen bond, but instead forms a nearly linear N—H···π(arene) contact with the centroid, Cg2, of the C41—C46 phenyl ring in the molecule at (x, y - 1, z) (Fig. 2), so that all three contacts may be mutually cooperative.

In view of the N—H···π(arene) interaction found in (I), we have reviewed the supramolecular structures of other substituted 2-amino-6-benzyloxy-5-nitrosopyrimidines (Quesada et al., 2002), and we have now, indeed, identified N—H···π(arene) interactions in three such compounds, (V)-(VII) (Figs. 3–5). In compound (V) (Fig. 3), the amino groups in both independent molecules participate in exactly the same type of asymmetric three-centre N—H···(N,O) hydrogen bond as found in (I), together with an N—H···π(arene) interaction with the centroids Cg1 and Cg2 of the adjacent O6-benzyl rings [for type 1 molecules, H···Cg1ii 2.61 Å, N···Cg1ii 3.418 (2) Å and N—H···Cg1ii 153°; for type 2 molecules, H···Cg2iii 2.50 Å, N···Cgiii 3.318 (2) Å and N—H···Cg2iii 156°; symmetry codes: (ii) -3/2 - x, y - 1/2, 1/2 - z Query initial minus; (iii) 5/2 - x, 1/2 + y, 1/2 - z].

In the P1 polymorph (Quesada et al., 2002) of compound (VI) (Fig. 4), while the hard intermolecular hydrogen bonds formed by each of the two independent molecules are of the two-centre N—H···N type, there are again N—H···π(arene) interactions with the ring centroids, Cg3 and Cg4, in the adjacent benzyl groups [for type 1 molecules, H···Cg3iv 2.79 Å, N···Cg3iv 3.621 (4) Å and N—H···Cg3iv 158°; for type 2 molecules, H···Cg4v 2.68 Å, N···Cg4v 3.546 (4) Å and N—H···Cg4v 170°; symmetry codes: (iv) 1 + x, y, z; (v) x - 1, y, z].

Compound (VII), where Z' = 1, exhibits the same type of asymmetric three-centre N—H···(N,O) hydrogen bonds as found in both (I) and (V), but here the corresponding N—H···Cg5 contact (Fig. 5) is long, although still close to linear [H···Cg5iv 2.91 Å, N···Cg5iv 3.748 (3) Å and N—H···Cg5iv 161°; symmetry code: (iv) 1 + x, y, z].

In all of these examples, the multiple intermolecular contacts appear to be mutually cooperative. However, it is clear that the distinction between genuine attractive interactions and adventitious contacts, or near contacts, is not easy to judge. Nonetheless, the conformation of the benzyloxy group involved in each such putative interaction, which effectively prevents access of any other acceptor to the NH bond in question, is suggestive.

Experimental top

A sample of (I) was synthesized following the published method of Quesada et al. (2000) and Marchal et al. (2002). Compound (IV) (ex Aldrich) was converted to (II) by reaction of sodium benzylate in toluene, and (II) was then nitrosated with isoamyl nitrite in dimethylsulfoxide solution at room temperature. Crystals of (I) for single-crystal X-ray diffraction were grown by slow evaporation of a solution in acetone.

Refinement top

Compound (I) crystallized in the monoclinic system; space group P21/c was uniquely assigned from the systematic absences. H atoms were treated as riding atoms, with C—H = 0.93–0.97 Å and N—H = 0.86 Å. The data were collected at 298 (2) K, where the proportion of data labelled observed is only 0.31, because all attempts to cool the crystals caused irreversible damage; this may underlie the high Rint value and the comparatively low precision in the refined structure.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing formation of a chain along [010]. For the sake of clarity, the unit-cell box has been omitted. The atoms marked with an asterisk (*) or a hash sign (#) are at the symmetry positions (x, y - 1, z) and (x, 1 + y, z), respectively.
[Figure 3] Fig. 3. Part of the crystal structure of (V), showing the hard hydrogen bonds and the N—H···π(arene) interaction formed by type 1 molecules. The atoms marked with an asterisk (*) or a hash sign (#) are at the symmetry positions (3/2 - x, y - 1/2, 1/2 - z) and (x, y - 1, z), respectively.
[Figure 4] Fig. 4. Part of the crystal structure of (VI), showing the N—H···N hydrogen bond and the N—H···π(arene) interaction formed by type 1 molecules. The atoms marked with an asterisk (*) or a hash sign (#) are at the symmetry positions (1 + x, y, z) and (x - 1, y, z), respectively.
[Figure 5] Fig. 5. Part of the crystal structure of (VII), showing the hard hydrogen bonds and the long N—H···π(arene) contact. The atoms marked with an asterisk (*) or a hash sign (#) are at the symmetry positions (1 + x, y, z) and (x - 1, y, z), respectively.
2-Amino-4,6-bis(benzyloxy)-5-nitrosopyrimidine top
Crystal data top
C18H16N4O3F(000) = 704
Mr = 336.35Dx = 1.285 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3895 reflections
a = 11.0731 (5) Åθ = 2.9–27.6°
b = 7.3642 (3) ŵ = 0.09 mm1
c = 22.9129 (11) ÅT = 298 K
β = 111.456 (2)°Needle, blue
V = 1738.94 (13) Å30.25 × 0.10 × 0.08 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
3895 independent reflections
Radiation source: fine-focus sealed X-ray tube1203 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ϕ scans, and ω scans with κ offsetsθmax = 27.6°, θmin = 2.9°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1412
Tmin = 0.975, Tmax = 0.993k = 89
13067 measured reflectionsl = 2529
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 0.90 w = 1/[σ2(Fo2) + (0.0536P)2]
where P = (Fo2 + 2Fc2)/3
3895 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C18H16N4O3V = 1738.94 (13) Å3
Mr = 336.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.0731 (5) ŵ = 0.09 mm1
b = 7.3642 (3) ÅT = 298 K
c = 22.9129 (11) Å0.25 × 0.10 × 0.08 mm
β = 111.456 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
3895 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
1203 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.993Rint = 0.014
13067 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 0.90Δρmax = 0.14 e Å3
3895 reflectionsΔρmin = 0.19 e Å3
226 parameters
Special details top

Experimental. Data collection was carried out at room temperature because the crystals flaked on cooling.

The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G. C. & Holmes, K. C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High-redundancy data were used in the scaling program, hence the 'multi-scan' code word was used.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.2250 (3)0.1634 (3)0.00421 (13)0.0586 (8)
C20.1619 (3)0.1771 (5)0.04435 (17)0.0597 (9)
N20.1348 (3)0.3428 (4)0.05732 (14)0.0861 (11)
N30.1232 (3)0.0393 (3)0.07247 (12)0.0591 (8)
C40.1563 (3)0.1226 (4)0.05998 (15)0.0531 (9)
O40.1272 (2)0.2660 (3)0.08853 (10)0.0641 (7)
C470.0702 (4)0.2280 (4)0.13540 (17)0.0708 (11)
C410.0557 (4)0.4087 (4)0.16239 (17)0.0555 (9)
C420.0578 (4)0.5044 (5)0.13773 (17)0.0667 (10)
C430.0697 (4)0.6740 (5)0.1610 (2)0.0800 (12)
C440.0316 (6)0.7469 (6)0.2091 (2)0.0868 (14)
C450.1440 (5)0.6533 (6)0.2343 (2)0.0903 (13)
C460.1576 (4)0.4845 (5)0.21121 (18)0.0746 (11)
C50.2240 (3)0.1590 (4)0.01983 (14)0.0496 (8)
N50.2524 (3)0.3375 (4)0.01281 (13)0.0610 (8)
O50.3201 (2)0.3712 (3)0.01890 (12)0.0758 (8)
C60.2565 (3)0.0008 (4)0.00656 (15)0.0525 (9)
O60.3226 (2)0.0224 (3)0.04448 (11)0.0660 (7)
C670.3601 (4)0.1411 (5)0.06850 (19)0.0815 (12)
C610.4320 (4)0.0870 (6)0.10946 (18)0.0732 (11)
C620.4577 (4)0.0886 (7)0.11957 (18)0.0896 (13)
C630.5258 (5)0.1308 (9)0.1582 (2)0.1207 (19)
C640.5695 (6)0.0060 (13)0.1862 (3)0.149 (3)
C650.5435 (6)0.1804 (12)0.1766 (3)0.139 (3)
C660.4765 (4)0.2256 (7)0.1381 (2)0.0962 (14)
H2A0.15720.43460.04040.103*
H2B0.09460.35920.08270.103*
H47A0.12630.14900.16790.085*
H47B0.01370.16970.11620.085*
H420.12740.45500.10510.080*
H430.14690.73830.14380.096*
H440.02350.86100.22460.104*
H450.21260.70310.26730.108*
H460.23540.42150.22860.090*
H67A0.28370.21090.09240.098*
H67B0.41490.21560.03410.098*
H620.42930.18180.10040.108*
H630.54170.25140.16500.145*
H640.61640.02120.21150.179*
H650.57140.27260.19640.166*
H660.46120.34660.13150.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.075 (2)0.0408 (17)0.071 (2)0.0046 (13)0.0408 (18)0.0039 (13)
C20.070 (3)0.046 (2)0.070 (3)0.0027 (18)0.035 (2)0.0011 (18)
N20.133 (3)0.044 (2)0.114 (3)0.0095 (17)0.084 (2)0.0049 (16)
N30.075 (2)0.0406 (16)0.073 (2)0.0020 (13)0.0397 (17)0.0021 (13)
C40.064 (3)0.046 (2)0.054 (2)0.0024 (16)0.026 (2)0.0040 (16)
O40.090 (2)0.0469 (13)0.0749 (17)0.0027 (11)0.0532 (15)0.0015 (11)
C470.093 (3)0.060 (2)0.080 (3)0.0021 (18)0.056 (2)0.0045 (18)
C410.067 (3)0.056 (2)0.052 (2)0.002 (2)0.032 (2)0.0024 (17)
C420.066 (3)0.065 (2)0.071 (3)0.004 (2)0.027 (2)0.0012 (19)
C430.081 (3)0.069 (3)0.102 (4)0.016 (2)0.048 (3)0.003 (2)
C440.117 (4)0.075 (3)0.087 (3)0.002 (3)0.060 (3)0.015 (3)
C450.096 (4)0.103 (3)0.075 (3)0.019 (3)0.035 (3)0.026 (3)
C460.069 (3)0.090 (3)0.069 (3)0.014 (2)0.030 (2)0.002 (2)
C50.059 (2)0.043 (2)0.053 (2)0.0006 (15)0.0271 (19)0.0001 (15)
N50.073 (2)0.0544 (18)0.064 (2)0.0029 (15)0.0345 (18)0.0058 (14)
O50.093 (2)0.0624 (16)0.092 (2)0.0045 (13)0.0575 (18)0.0109 (13)
C60.056 (3)0.056 (2)0.052 (2)0.0023 (17)0.027 (2)0.0036 (17)
O60.0816 (19)0.0577 (15)0.0770 (17)0.0058 (12)0.0507 (15)0.0087 (12)
C670.092 (3)0.077 (3)0.098 (3)0.005 (2)0.061 (3)0.024 (2)
C610.061 (3)0.102 (3)0.060 (3)0.002 (2)0.026 (2)0.014 (2)
C620.076 (3)0.133 (4)0.068 (3)0.004 (3)0.037 (3)0.009 (3)
C630.095 (4)0.191 (6)0.089 (4)0.006 (4)0.048 (3)0.037 (4)
C640.082 (4)0.299 (11)0.081 (4)0.033 (6)0.045 (3)0.036 (6)
C650.082 (4)0.272 (9)0.069 (4)0.030 (5)0.037 (3)0.037 (5)
C660.071 (3)0.142 (4)0.077 (3)0.007 (3)0.029 (3)0.036 (3)
Geometric parameters (Å, º) top
C6—N11.306 (4)C43—H430.9300
N1—C21.347 (4)C44—C451.353 (6)
C2—N31.353 (4)C44—H440.9300
N3—C41.310 (4)C45—C461.380 (5)
C4—C51.408 (4)C45—H450.9300
C5—C61.419 (4)C46—H460.9300
C2—N21.316 (4)O6—C671.446 (4)
C4—O41.342 (3)C67—C611.490 (5)
C6—O61.334 (4)C67—H67A0.9700
C5—N51.374 (4)C67—H67B0.9700
N5—O51.245 (3)C61—C621.363 (5)
N2—H2A0.8600C61—C661.397 (5)
N2—H2B0.8600C62—C631.392 (6)
O4—C471.458 (4)C62—H620.9300
C47—C411.500 (4)C63—C641.374 (8)
C47—H47A0.9700C63—H630.9300
C47—H47B0.9700C64—C651.352 (8)
C41—C421.369 (5)C64—H640.9300
C41—C461.383 (5)C65—C661.385 (7)
C42—C431.383 (5)C65—H650.9300
C42—H420.9300C66—H660.9300
C43—C441.362 (5)
C6—N1—C2116.1 (3)C45—C46—H46119.9
N2—C2—N1116.2 (3)C41—C46—H46119.9
N2—C2—N3116.7 (3)N5—C5—C4117.3 (3)
N1—C2—N3127.1 (3)N5—C5—C6129.1 (3)
C2—N2—H2A120.0C4—C5—C6113.6 (3)
C2—N2—H2B120.0O5—N5—C5118.2 (3)
H2A—N2—H2B120.0N1—C6—O6118.8 (3)
C4—N3—C2114.6 (3)N1—C6—C5123.5 (3)
N3—C4—O4118.2 (3)O6—C6—C5117.7 (3)
N3—C4—C5125.1 (3)C6—O6—C67116.8 (3)
O4—C4—C5116.6 (3)O6—C67—C61108.1 (3)
C4—O4—C47117.0 (2)O6—C67—H67A110.1
O4—C47—C41105.9 (2)C61—C67—H67A110.1
O4—C47—H47A110.6O6—C67—H67B110.1
C41—C47—H47A110.6C61—C67—H67B110.1
O4—C47—H47B110.6H67A—C67—H67B108.4
C41—C47—H47B110.6C62—C61—C66118.8 (4)
H47A—C47—H47B108.7C62—C61—C67123.6 (4)
C42—C41—C46118.7 (3)C66—C61—C67117.6 (4)
C42—C41—C47120.4 (4)C61—C62—C63121.0 (5)
C46—C41—C47120.9 (4)C61—C62—H62119.5
C41—C42—C43120.5 (4)C63—C62—H62119.5
C41—C42—H42119.7C64—C63—C62120.0 (6)
C43—C42—H42119.7C64—C63—H63120.0
C44—C43—C42120.1 (4)C62—C63—H63120.0
C44—C43—H43120.0C65—C64—C63119.2 (7)
C42—C43—H43120.0C65—C64—H64120.4
C45—C44—C43120.0 (4)C63—C64—H64120.4
C45—C44—H44120.0C64—C65—C66121.8 (7)
C43—C44—H44120.0C64—C65—H65119.1
C44—C45—C46120.5 (4)C66—C65—H65119.1
C44—C45—H45119.7C65—C66—C61119.2 (5)
C46—C45—H45119.7C65—C66—H66120.4
C45—C46—C41120.1 (4)C61—C66—H66120.4
C6—N1—C2—N2177.3 (3)O4—C4—C5—C6177.4 (3)
C6—N1—C2—N33.0 (5)C4—C5—N5—O5175.0 (3)
N2—C2—N3—C4177.6 (3)C6—C5—N5—O53.0 (5)
N1—C2—N3—C42.6 (5)C2—N1—C6—O6178.0 (3)
C2—N3—C4—O4176.7 (3)C2—N1—C6—C52.1 (5)
C2—N3—C4—C51.5 (5)N5—C5—C6—N1179.2 (3)
N3—C4—O4—C474.9 (4)C4—C5—C6—N11.2 (5)
C5—C4—O4—C47173.4 (3)N5—C5—C6—O61.0 (5)
C4—O4—C47—C41176.4 (3)C4—C5—C6—O6179.0 (3)
O4—C47—C41—C4292.6 (4)N1—C6—O6—C673.0 (4)
O4—C47—C41—C4685.3 (4)C5—C6—O6—C67177.1 (3)
C46—C41—C42—C430.4 (5)C6—O6—C67—C61179.9 (3)
C47—C41—C42—C43177.6 (3)O6—C67—C61—C621.4 (5)
C41—C42—C43—C440.4 (6)O6—C67—C61—C66179.5 (3)
C42—C43—C44—C450.1 (6)C66—C61—C62—C630.7 (7)
C43—C44—C45—C460.6 (7)C67—C61—C62—C63179.7 (4)
C44—C45—C46—C410.5 (6)C61—C62—C63—C640.7 (8)
C42—C41—C46—C450.0 (6)C62—C63—C64—C651.1 (9)
C47—C41—C46—C45178.0 (3)C63—C64—C65—C661.5 (10)
N3—C4—C5—N5179.1 (3)C64—C65—C66—C611.4 (8)
O4—C4—C5—N50.9 (4)C62—C61—C66—C651.0 (6)
N3—C4—C5—C60.8 (5)C67—C61—C66—C65179.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O4i0.862.542.977 (4)112
N2—H2A···N5i0.862.193.041 (4)168
N2—H2B···Cg2i0.862.673.496 (4)163
Symmetry code: (i) x, y1, z.

Experimental details

Crystal data
Chemical formulaC18H16N4O3
Mr336.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)11.0731 (5), 7.3642 (3), 22.9129 (11)
β (°) 111.456 (2)
V3)1738.94 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.25 × 0.10 × 0.08
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.975, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
13067, 3895, 1203
Rint0.014
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.169, 0.90
No. of reflections3895
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.19

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2002), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected bond lengths (Å) top
C6—N11.306 (4)C2—N21.316 (4)
N1—C21.347 (4)C4—O41.342 (3)
C2—N31.353 (4)C6—O61.334 (4)
N3—C41.310 (4)C5—N51.374 (4)
C4—C51.408 (4)N5—O51.245 (3)
C5—C61.419 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O4i0.862.542.977 (4)112
N2—H2A···N5i0.862.193.041 (4)168
N2—H2B···Cg2i0.862.673.496 (4)163
Symmetry code: (i) x, y1, z.
Selected torsion angles (°) for compounds (I), (II) and (III) top
(I)(II)(III)
N1-C6-O6-C67-3.0 (4)-178.4 (2)1.7 (2)
C6-O6-C67-C61177.1 (3)179.2 (2)-81.6 (2)
O6-C67-C61-C62179.9 (3)-6.9 (2)-62.1 (2)
N3-C4-O4-C474.9 (4)-2.4 (2)-1.9 (2)
C4-O4-C47-C41176.4 (3)-176.0 (2)-179.6 (2)
O4-C47-C41-C4292.6 (4)23.7 (2)-11.8 (2)
 

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