Download citation
Download citation
link to html
Mol­ecules of the title compound, C16H13N5O2, have no inter­nal symmetry despite the symmetric pattern of substitution in the pyrimidine ring. The intra­molecular distances indicate polarization of the electronic structure. There are two intra­molecular N—H...O hydrogen bonds and mol­ecules are linked into centrosymmetric dimers by pairs of three-centre C—H...(O)2 hydrogen bonds. These dimers are linked into chains by means of a π–π stacking inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109029618/gg3208sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109029618/gg3208Isup2.hkl
Contains datablock I

CCDC reference: 749708

Comment top

We report here the molecular and supramolecular structure of the title compound, (I) (Fig. 1), which we compare with the related compounds (II)–(V) (Makarov et al., 1997; Quesada et al., 2003; Glidewell et al., 2003; Quesada et al., 2004).

Despite the presence of three adjacent substituents in the pyrimidine ring, this ring is planar within experimental uncertainty: the maximum deviation from the mean plane of the ring is that of atom N3 [0.007 (2) Å; Fig. 1). This behaviour may be contrasted with that of the close analogue (II) [Cambridge Structural Database (Allen, 2002) refcode RENTUZ; Makarov et al., 1997], where the pyrimidine ring adopts a boat conformation. The maximum deviation from the mean ring plane in (II) is shown by the C atom corresponding to atom C5 in (I) [0.167 (2) Å], while the nitro N atom is displaced by 1.028 (2) Å to one side of the mean ring plane and the two N atoms of the dimethylamino groups are displaced by 0.411 (2) and 0.443 (2) Å, respectively, to the other side of the ring plane. Similarly, in the cation of (III) (Quesada et al., 2003), where the pyrimidine ring adopts a twist-boat conformation, the N atom of the nitro group is displaced by 1.273 (3) Å to one side of the mean plane of the ring, while the N atoms of the two piperidine substituents are displaced by 0.111 (3) and 0.257 (3)Å to the opposite side of the mean plane. Significant distortion from planarity is, in fact quite commonly but not invariably observed in highly substituted pyrimidines, particularly in those carrying three adjacent substituents at positions 4, 5 and 6 (Low et al., 2007; Melguizo et al., 2003; Quesada et al., 2003, 2004; Trilleras et al., 2007, 2009; Cobo et al., 2008).

The molecular conformation in (I) can be defined in terms of a small number of torsion angles (Table 1), which indicate that, while the nitro group and one of the phenyl rings (C61–C66) are essentially coplanar with the pyrimidine ring, the other phenyl ring (C41–C46) is markedly displaced from this plane. Thus, the dihedral angles between the plane of the pyrimidine ring and those of the C41–C46 and C61–C66 rings, respectively, are 60.9 (2) and 1.8 (2)°. Accordingly the molecule has no internal symmetry, even though the pattern of substituents on the pyrimidine ring permits C2v (mm2) molecular symmetry, or either of its sub-groups, C2 or Cs. The fact that the C61–C66 ring is effectively coplanar with the pyrimidine ring indicates that there are no intramolecular factors preventing the adoption of the full molecular symmetry in the crystal. Thus, (I) is an example of a crystal structure in which the molecules exhibit far less than the full molecular symmetry. Perhaps the most familiar example of this phenomenon is benzene, where the unperturbed molecule in the gas-phase has D6h (6/mmm) symmetry (Kimura & Kubo, 1960), but only a centre of inversion is retained in the crystalline state, for both orthorhombic (Cox et al., 1958; Bacon et al., 1964) and monoclinic (Fourme et al., 1971) polymorphs.

The molecule of the dimethoxynitropyrimidine (IV) (Glidewell et al., 2003) exhibits no crystallographic symmetry, but the non-H atoms are effectively coplanar, apart from the nitro group, which is twisted out of the ring plane by some 30°, so that this molecule exhibits approximate but noncrystallographic C2 rotational symmetry. The deviation of the nitro group from the ring plane in (IV) is best attributed to nonbonded electronic repulsions between the O atoms of the nitro group and those of the methoxy groups, in contrast to the attractive N—H···O hydrogen bonds in (I), where the nitro group is effectively coplanar with the pyrimidine ring.

Within the molecule of (I), the C5—N5 bond (Table 1) is very short for its type [mean value (Allen et al., 1987) 1.410 (3) Å, lower quartile value 1.460 Å], while the N—O distances are both long (mean value 1.217 Å, upper quartile value 1.225 Å); similarly, the C4—N4 and C6—N6 bonds are short for their type (mean value 1.353 Å, lower quartile value 1.347 Å), while the C4—C5 and C5—C6 bonds are both long (mean value in pyrimidines 1.387 Å, upper quartile value 1.400 Å). These values indicates that polarized forms such as (Ia) and (Ib) are significant contributors to the overall electronic structure in addition to the delocalized aromatic form (I). The corresponding distances in (II) exhibit an exactly analogous pattern of behaviour, showing firstly that the development of polarized forms involving electronic delocalization from amino groups to nitro groups does not depend upon the presence of a planar molecular skeleton, and secondly, that the energy cost of evading steric clashes between adjacent substituent by rotation of the amino and nitro groups about the exocyclic C—N bonds, with concomitant loss of the delocalization, exceeds that of distorting the formally aromatic ring. Compound (V) (Quesada et al., 2004) is another close analogue of (I), containing two primary amino substituents, but with a nitroso group rather than a nitro group, so that only one intramolecular N—H···O hydrogen bond is present; again the electronic structure is markedly polarized with extensive delocalization involving all three amino substituents.

Each of the two independent N—H bonds participates in an intramolecular hydrogen bond (Table 2), forming two edge-fused S(6) motifs (Bernstein et al., 1995), but the N—H bonds play no role in the intermolecular aggregation. Instead, pairs of molecule are linked into centrosymmetric dimers by means of an asymmetric, but effectively planar, three-centre C—H···(O)2 hydrogen bond, in which the O51i···H66···O52i [symmetry code: (i) -x, -y + 2, -z + 1] angle is 51°, giving a sum of angles at H66 of 359°. The dimer thus contains two concentric and centrosymmetric R22(16) motifs together with two symmetry-related R21(4) rings (Fig. 2). These hydrogen-bonded dimers are linked into a chain by a single ππ stacking interaction. The planes of the pyrimidine ring in the molecule at (x, y, z) and the C61–C66 aryl ring in the molecule at (-x + 1, -y + 1, -z + 1) make a dihedral angle of 1.8 (2)°, with an interplanar spacing of ca 3.36 Å. The corresponding ring-centroid separation is 3.6500 (15) Å, with a ring-centroid offset of ca 1.426 Å. Propagation of this interaction by inversion thus links the hydrogen-bonded dimers centred at (n, 1- n, 1/2), where n represents an integer, into a chain running parallel to the [110] direction (Fig. 2), where pairs of molecules centred across (1/2 + n, 1.2 - n, 1/2), where n again represents an integer, participate in ππ stacking interactions. Two chains of this type, related to one another by the translational symmetry operations, pass through each unit cell, but there are no direction-specific interactions between the chains; in particular C—H···π hydrogen bonds are absent.

It is of interest briefly to compare the one-dimensional supramolecular aggregation in (I) with the corresponding behaviour in the related compounds (II)–(V). In (II) (Makarov et al., 1997), there are no significant direction-specific interactions between the molecules; the closest intermolecular contacts involve methyl C—H bonds. By contrast, in the hydrated salt (III) (Quesada et al., 2003) a combination of three O—H···O hydrogen bonds and three N—H···O hydrogen bonds links the components into a continuous three-dimensional structure, but the anion and solvent components play a dominant role here. Two hydrogen bonds, one each of N—H···O and N—H···N types, link the molecules of (IV) into sheets built from alternating R22(8) ad R66(32) rings (Glidewell et al., 2003). Finally, in (V) (Quesada et al., 2004), two N—H···N hydrogen bonds generate chains of rings, which are linked into sheets by an N—H···O hydrogen bond; these sheets are themselves linked by a C—H···O hydrogen bond to form a three-dimensional structure. Thus in the simple, unsolvated compounds (II), (I), (IV) and (V), the supramolecular structures can be regarded as, respectively, zero-, one-, two- and three-dimensional.

Related literature top

For related literature, see: Allen (2002); Allen et al. (1987); Bacon et al. (1964); Bernstein et al. (1995); Cobo et al. (2008); Cox et al. (1958); Fourme et al. (1971); Glidewell et al. (2003); Kimura & Kubo (1960); Low et al. (2007); Makarov et al. (1997); Melguizo et al. (2003); Quesada et al. (2003, 2004); Trilleras et al. (2007, 2009).

Experimental top

Aniline (2 mmol) was added dropwise to a solution of 4,6-dichloro-5-nitropyrimidine (1 mmol) in tetrahydrofuran (10 ml) containing triethylamine (0.5 ml), and the resulting reaction mixture was then stirred at ambient temperature for 4 h. The mixture was concentrated under reduced pressure, diluted with water and exhaustively extracted with ethyl acetate. The combined organic extracts were washed firstly with aqueous hydrochloric acid (1 mol dm3) and then with brine, and finally dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to yield the product as a yellow solid (yield 98%, m.p. 441–443 K). Crystals suitable for single-crystal X-ray diffraction were obtained from a solution in dimethylsulfoxide.

Refinement top

All H atoms were located in difference maps and then treated as riding atoms in geometrically idealized positions with C—H distances of 0.95 Å and N—H distances of 0.88 Å, and with Uiso(H) values of 1.2Ueq(carrier).

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: Sir2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A stereoview of part of the crystal structure of (I), showing the formation of a chain along [110] built by the π-stacking of hydrogen-bonded dimers. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
5-Nitro-N4,N6-diphenylpyrimidine-4,6-diamine top
Crystal data top
C16H13N5O2F(000) = 640
Mr = 307.31Dx = 1.519 Mg m3
Monoclinic, P21/cMelting point = 441–443 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.9112 (11) ÅCell parameters from 2720 reflections
b = 5.5582 (6) Åθ = 2.8–27.5°
c = 30.665 (3) ŵ = 0.11 mm1
β = 94.541 (10)°T = 120 K
V = 1344.2 (3) Å3Plate, yellow
Z = 40.43 × 0.21 × 0.05 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
3094 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1658 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.8°
ϕ & ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 77
Tmin = 0.931, Tmax = 0.995l = 3939
20376 measured reflections
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0646P)2 + 0.3701P]
where P = (Fo2 + 2Fc2)/3
3094 reflections(Δ/σ)max = 0.001
208 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C16H13N5O2V = 1344.2 (3) Å3
Mr = 307.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.9112 (11) ŵ = 0.11 mm1
b = 5.5582 (6) ÅT = 120 K
c = 30.665 (3) Å0.43 × 0.21 × 0.05 mm
β = 94.541 (10)°
Data collection top
Bruker–Nonius KappaCCD
diffractometer
3094 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
1658 reflections with I > 2σ(I)
Tmin = 0.931, Tmax = 0.995Rint = 0.084
20376 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.08Δρmax = 0.34 e Å3
3094 reflectionsΔρmin = 0.38 e Å3
208 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3389 (3)0.3814 (4)0.42872 (6)0.0229 (5)
C20.3661 (3)0.3644 (5)0.38694 (8)0.0235 (6)
H20.43270.23020.37970.028*
N30.3157 (3)0.5033 (4)0.35383 (6)0.0232 (5)
C40.2250 (3)0.6966 (4)0.36356 (8)0.0203 (6)
C50.1861 (3)0.7393 (4)0.40724 (7)0.0190 (6)
C60.2467 (3)0.5718 (5)0.43984 (8)0.0210 (6)
N40.1781 (3)0.8435 (4)0.33035 (6)0.0242 (5)
H40.11810.97140.33610.029*
C410.2175 (3)0.8092 (5)0.28647 (8)0.0231 (6)
C420.1616 (3)0.6076 (5)0.26331 (8)0.0258 (6)
H410.09850.48700.27680.031*
C430.1981 (3)0.5835 (5)0.22052 (8)0.0297 (7)
H430.16030.44550.20430.036*
C440.2893 (4)0.7583 (5)0.20110 (8)0.0316 (7)
H440.31490.74020.17150.038*
C450.3435 (4)0.9590 (5)0.22427 (9)0.0327 (7)
H450.40661.07930.21070.039*
C460.3068 (3)0.9865 (5)0.26701 (8)0.0268 (6)
H460.34271.12630.28300.032*
N50.0890 (3)0.9413 (4)0.41752 (7)0.0229 (5)
O510.0345 (2)1.0828 (3)0.38809 (5)0.0278 (5)
O520.0566 (2)0.9798 (3)0.45583 (5)0.0268 (5)
N60.2137 (3)0.5944 (4)0.48158 (6)0.0219 (5)
H60.15380.72280.48710.026*
C610.2574 (3)0.4496 (4)0.51860 (8)0.0209 (6)
C620.3513 (3)0.2398 (5)0.51946 (8)0.0249 (6)
H620.39370.18020.49340.030*
C630.3830 (3)0.1181 (5)0.55825 (8)0.0254 (6)
H630.44760.02610.55870.030*
C640.3234 (3)0.2002 (5)0.59642 (8)0.0266 (6)
H640.34600.11380.62300.032*
C650.2297 (3)0.4110 (5)0.59559 (8)0.0246 (6)
H650.18850.47080.62180.029*
C660.1966 (3)0.5333 (5)0.55710 (8)0.0224 (6)
H660.13130.67690.55670.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0234 (12)0.0234 (12)0.0222 (12)0.0020 (10)0.0038 (9)0.0000 (9)
C20.0249 (15)0.0222 (14)0.0236 (15)0.0031 (12)0.0028 (11)0.0005 (11)
N30.0231 (12)0.0242 (12)0.0225 (12)0.0023 (10)0.0020 (9)0.0024 (10)
C40.0177 (13)0.0210 (14)0.0222 (14)0.0017 (12)0.0021 (10)0.0017 (11)
C50.0161 (13)0.0174 (13)0.0236 (14)0.0019 (11)0.0027 (10)0.0005 (11)
C60.0149 (13)0.0242 (14)0.0239 (14)0.0005 (12)0.0011 (10)0.0007 (11)
N40.0276 (13)0.0225 (12)0.0225 (12)0.0050 (10)0.0023 (9)0.0032 (9)
C410.0192 (14)0.0291 (15)0.0210 (14)0.0054 (12)0.0011 (11)0.0047 (11)
C420.0236 (15)0.0263 (15)0.0273 (15)0.0005 (12)0.0011 (11)0.0023 (12)
C430.0304 (16)0.0305 (16)0.0276 (15)0.0063 (14)0.0019 (12)0.0019 (13)
C440.0376 (18)0.0355 (17)0.0224 (14)0.0112 (14)0.0069 (12)0.0023 (13)
C450.0332 (17)0.0327 (17)0.0332 (16)0.0042 (14)0.0087 (13)0.0067 (13)
C460.0282 (15)0.0226 (14)0.0293 (15)0.0026 (12)0.0018 (12)0.0004 (12)
N50.0197 (11)0.0259 (13)0.0230 (12)0.0024 (10)0.0005 (9)0.0001 (10)
O510.0328 (11)0.0253 (10)0.0249 (10)0.0074 (9)0.0002 (8)0.0043 (8)
O520.0323 (11)0.0292 (10)0.0192 (10)0.0032 (9)0.0054 (8)0.0010 (8)
N60.0224 (12)0.0213 (11)0.0220 (12)0.0063 (10)0.0024 (9)0.0015 (9)
C610.0185 (13)0.0207 (14)0.0234 (14)0.0004 (11)0.0002 (10)0.0037 (11)
C620.0262 (15)0.0262 (15)0.0224 (14)0.0027 (13)0.0036 (11)0.0034 (12)
C630.0237 (15)0.0236 (15)0.0290 (15)0.0025 (12)0.0021 (11)0.0012 (12)
C640.0284 (15)0.0276 (15)0.0238 (15)0.0015 (13)0.0009 (12)0.0060 (12)
C650.0251 (15)0.0278 (15)0.0213 (14)0.0018 (12)0.0047 (11)0.0031 (11)
C660.0203 (14)0.0210 (14)0.0258 (14)0.0011 (12)0.0009 (11)0.0010 (11)
Geometric parameters (Å, º) top
N1—C21.319 (3)C43—H430.9500
C2—N31.313 (3)C44—C451.373 (4)
N3—C41.339 (3)C44—H440.9500
C4—C51.418 (3)C45—C461.373 (3)
C5—C61.421 (3)C45—H450.9500
C6—N11.345 (3)C46—H460.9500
C2—H20.9500N6—C611.412 (3)
C4—N41.335 (3)N6—H60.8800
C5—N51.410 (3)C61—C621.382 (4)
N5—O511.248 (2)C61—C661.390 (3)
N5—O521.241 (2)C62—C631.374 (3)
C6—N61.332 (3)C62—H620.9500
N4—C411.418 (3)C63—C641.374 (3)
N4—H40.8800C63—H630.9500
C41—C461.376 (3)C64—C651.385 (4)
C41—C421.381 (4)C64—H640.9500
C42—C431.372 (3)C65—C661.369 (3)
C42—H410.9500C65—H650.9500
C43—C441.373 (4)C66—H660.9500
C2—N1—C6115.9 (2)C44—C45—H45119.9
N3—C2—N1130.3 (2)C46—C45—H45119.9
N3—C2—H2114.9C45—C46—C41119.3 (3)
N1—C2—H2114.9C45—C46—H46120.4
C2—N3—C4115.8 (2)C41—C46—H46120.4
N4—C4—N3116.3 (2)O52—N5—O51119.4 (2)
N4—C4—C5123.4 (2)O52—N5—C5120.4 (2)
N3—C4—C5120.4 (2)O51—N5—C5120.20 (19)
N5—C5—C4120.5 (2)C6—N6—C61131.6 (2)
N5—C5—C6121.6 (2)C6—N6—H6114.2
C4—C5—C6117.9 (2)C61—N6—H6114.2
N6—C6—N1118.0 (2)C62—C61—C66119.2 (2)
N6—C6—C5122.2 (2)C62—C61—N6126.4 (2)
N1—C6—C5119.8 (2)C66—C61—N6114.4 (2)
C4—N4—C41124.9 (2)C63—C62—C61119.5 (2)
C4—N4—H4117.5C63—C62—H62120.2
C41—N4—H4117.5C61—C62—H62120.2
C46—C41—C42120.9 (2)C62—C63—C64121.5 (3)
C46—C41—N4118.3 (2)C62—C63—H63119.3
C42—C41—N4120.8 (2)C64—C63—H63119.3
C43—C42—C41119.2 (2)C63—C64—C65119.0 (2)
C43—C42—H41120.4C63—C64—H64120.5
C41—C42—H41120.4C65—C64—H64120.5
C42—C43—C44120.2 (3)C66—C65—C64120.1 (2)
C42—C43—H43119.9C66—C65—H65120.0
C44—C43—H43119.9C64—C65—H65120.0
C45—C44—C43120.2 (2)C65—C66—C61120.7 (2)
C45—C44—H44119.9C65—C66—H66119.7
C43—C44—H44119.9C61—C66—H66119.7
C44—C45—C46120.2 (3)
C6—N1—C2—N30.8 (4)C41—C42—C43—C440.0 (4)
N1—C2—N3—C41.5 (4)C42—C43—C44—C450.4 (4)
C2—N3—C4—N4177.8 (2)C43—C44—C45—C460.0 (4)
C2—N3—C4—C51.1 (3)C44—C45—C46—C411.0 (4)
N4—C4—C5—N51.9 (4)C42—C41—C46—C451.4 (4)
N3—C4—C5—N5179.3 (2)N4—C41—C46—C45178.7 (2)
N4—C4—C5—C6178.6 (2)C6—C5—N5—O521.2 (3)
N3—C4—C5—C60.2 (4)C6—C5—N5—O51178.5 (2)
C2—N1—C6—N6178.9 (2)N1—C6—N6—C610.6 (4)
C2—N1—C6—C50.3 (3)C5—C6—N6—C61178.6 (2)
N5—C5—C6—N60.9 (4)C6—N6—C61—C620.5 (4)
C4—C5—C6—N6178.7 (2)C4—C5—N5—O52179.2 (2)
N5—C5—C6—N1180.0 (2)C6—N6—C61—C66179.3 (2)
C4—C5—C6—N10.5 (3)C66—C61—C62—C630.0 (4)
N3—C4—N4—C410.2 (4)N6—C61—C62—C63179.8 (2)
C5—C4—N4—C41178.7 (2)C61—C62—C63—C640.0 (4)
C4—N4—C41—C46121.4 (3)C62—C63—C64—C650.2 (4)
C4—N4—C41—C4261.3 (3)C63—C64—C65—C660.5 (4)
C4—C5—N5—O511.0 (3)C64—C65—C66—C610.6 (4)
C46—C41—C42—C431.0 (4)C62—C61—C66—C650.4 (4)
N4—C41—C42—C43178.2 (2)N6—C61—C66—C65179.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O510.881.882.552 (3)132
N6—H6···O520.881.852.569 (3)137
C66—H66···O51i0.952.593.348 (3)137
C66—H66···O52i0.952.433.372 (3)171
Symmetry code: (i) x, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC16H13N5O2
Mr307.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)7.9112 (11), 5.5582 (6), 30.665 (3)
β (°) 94.541 (10)
V3)1344.2 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.43 × 0.21 × 0.05
Data collection
DiffractometerBruker–Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.931, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
20376, 3094, 1658
Rint0.084
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.153, 1.08
No. of reflections3094
No. of parameters208
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.38

Computer programs: COLLECT (Hooft, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), Sir2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top
N1—C21.319 (3)C4—N41.335 (3)
C2—N31.313 (3)C5—N51.410 (3)
N3—C41.339 (3)N5—O511.248 (2)
C4—C51.418 (3)N5—O521.241 (2)
C5—C61.421 (3)C6—N61.332 (3)
C6—N11.345 (3)
N3—C4—N4—C410.2 (4)N1—C6—N6—C610.6 (4)
C4—N4—C41—C4261.3 (3)C6—N6—C61—C620.5 (4)
C4—C5—N5—O511.0 (3)C4—C5—N5—O52179.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O510.881.882.552 (3)132
N6—H6···O520.881.852.569 (3)137
C66—H66···O51i0.952.593.348 (3)137
C66—H66···O52i0.952.433.372 (3)171
Symmetry code: (i) x, y+2, z+1.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds