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The title compound, C15H11N3O, (I), was obtained by the air oxidation of 3,5-diphenyl-4,5-dihydro-1,2,4-triazin-6(1H)-one. In the crystal structure, (I) forms centrosymmetric hydrogen-bonded dimers through pairs of N—H...N hydrogen bonds. The mol­ecular structure of (I) deviates somewhat from planarity in the crystalline state, whereas a density functional theory (DFT) study predicts a completely planar conformation (Cs point-group symmetry) for the isolated mol­ecule. The solid-state conformation of (I) is stabilized by intra­molecular hydrogen bonds, viz. one C—H...O inter­action, which forms a six-membered ring, and three C—H...N inter­actions that each form five-membered rings. To estimate the influence of the intra­molecular hydrogen-bonded rings on the aromaticity of the phenyl rings, the HOMA (harmonic oscillator model of aromaticity) descriptor of π-electron delocalization has been calculated for conformations of (I) with and without intra­molecular hydrogen bonds. In the planar conformation of (I), the HOMA values for both benzene rings are lower than in hypothetical conformations without intra­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112008384/ky3010sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112008384/ky3010Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270112008384/ky3010Isup3.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108270112008384/ky3010sup4.pdf
Supplementary material

CCDC reference: 879436

Comment top

1,2,4-Triazine derivatives display a broad spectrum of biological activity and have numerous applications in many fields. They are thus compounds of general interest (Neunhoeffer, 1996). They are applied in medicine as potential antibacterial and antifungal agents, in the agrochemical industry as plant-protection materials, and as components of commercial dyes (Abdel Hamide, 1997; Freidinger et al., 1993; Ackerman, 2007; Bettati et al., 2002). A wide range of synthetic procedures have been reported for the related 1,2,4-triazin-6-ones. They are commonly prepared from acid hydrazides (Zhao et al., 2003), amides (Blass et al., 2002) or iminoesters (Martinez-Teipel et al., 2001; Kammoun et al., 2000), or from small heterocyclic azirine structures (Nishiwaki & Saito, 1970). Recently, whilst investigating the reactions of optically active α-aminocarboxylic acid hydrazides with triethyl orthoesters, we obtained two groups of products: five-membered 2-(1-amino-1-phenylmethyl)-1,3,4-oxadiazoles and six-membered 5-substituted 3-phenyl-1,2,4-triazin-6-ones (Kudelko et al., 2011). One of the by-products, separated from the post-reaction mixture in low yields, was the title compound, (I). A literature survey revealed that similar compounds are usually constructed via oxidation of the appropriate 4,5-dihydro-1,2,4-triazin-6(1H)-ones with the use of mild oxidizing agents such as 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ, Miesel, 1982). We believe that (I) was formed by the air-oxidation of 4,5-dihydro-3,5-diphenyl-1,2,4-triazin-6(1H)-one, as it was exposed to the atmosphere whilst standing in ethanol solution for 10 d. A search of the Cambridge Structural Database (CSD; ConQuest Version 1.13; Allen, 2002) afforded only a few examples of 3,5-disubstituted-1,2,4-triazin-6(1H)-one derivatives (Buscemi et al., 2006; Garg & Stoltz, 2005; Sanudo et al., 2006; Trávníček et al., 1995). Therefore, the synthesis and structural characterization of (I) are reported herein.

The molecular structure of (I) and the atomic numbering scheme are presented in Fig. 1 and the packing arrangement in the crystal state is presented in Fig. 2. The main intermolecular interaction consists of centrosymmetric dimers formed by pairs of N—H···O hydrogen bonds (Table 2). The molecular structure of (I) consists of three rings: A (the phenyl ring containing atoms C8–C13), B (the triazine ring containing atoms N1/N2/C3/N4/C5/C6) and C (the phenyl ring containing atoms from C14–C19). These are nearly coplanar in the crystalline state, with angles between the ring planes for A/B and B/C being similar [8.6 (2) and 8.4 (2)°, respectively]. The A and C planes are arranged in a mutually cis position. The twists (described by torsion angles) around the C3—C14 and C5—C8 bonds are less than 10°. These small deformations from planarity probably result from the intermolecular interactions present in the crystal lattice. A density functional theory (DFT) study predicts a completely planar conformation (Cs point-group symmetry) as the preferred one for the isolated molecule of (I). See Supplementary materials for further details of the DFT calculations.

The near planarity of the system favours the formation of intramolecular hydrogen bonds and π-electron delocalization. The molecular structure of (I) contains four weak intramolecular hydrogen bonds (Fig. 1, Table 2); one C—H···O interaction, which forms a six-membered ring, and three C—H···N interactions that form five-membered rings, denoted quasi-rings. The resulting rings can be investigated as molecular patterns of intramolecular resonance assisted by hydrogen bonds. The position of the extra ring formed by the substituent interacting through the hydrogen bond is found to influence both the strength of that hydrogen bond and the local aromaticity of the polycyclic aromatic hydrocarbon skeleton. Relatively speaking, a greater loss of aromaticity of the ipso-ring (phenyl ring) can be observed for these kinked-like structures because of the greater participation of π-electrons from the ipso-ring in the formation of the quasi-ring (Krygowski et al., 2010; Palusiak et al., 2009).

The harmonic oscillator model of aromaticity (HOMA) is a leading method for the quantitative determination of cyclic π-electron delocalization in chemical compounds. It is based on the geometric criterion of aromaticity, which stipulates that bond lengths in aromatic systems lie between values that are typical for single and double bonds (Kruszewski & Krygowski, 1973; Krygowski, 1993). Therefore, HOMA = 0 for a model non-aromatic system (e.g. the Kekulé structure of benzene) and HOMA = 1 for a system with all bonds equal to the optimal value, assumed to be realised for fully aromatic systems. The HOMA value (based on B3LYP/6-311++G** optimized geometries) calculated for ring A (0.960) is lower than that of ring C (0.979). This loss of aromaticity of ring A is caused by both the electron-withdrawing properties of the neighbouring carbonyl group and the above-mentioned interactions with the quasi-rings formed by intramolecular hydrogen bonds, in particular by C13—H13···O7. Breaking the intramolecular hydrogen bonds by a twist of 90° around the C5—C8 bond results in an increase in energy of 5.65 kcal mol-1 (1 kcal mol-1 = 4.184 kJ mol-1), based on the B3LYP/6–311++G** calculations, as well as an increase in the aromaticity of ring A (HOMA = 0.989). The aromaticity of ring C remains almost unchanged (HOMA = 0.978).

Similar sequences of values were obtained for a twist about the C3—C14 bond. In this case the increase in energy is 5.22 kcal mol-1, and the HOMA value rises to 0.988 for ring C and decreases to 0.958 for ring A. Finally, in a hypothetical conformation without intramolecular hydrogen bonds, viz. with both phenyl groups perpendicular to the triazine ring, the energy is higher by 11.75 kcal mol-1 and the HOMA index takes the same value for rings A and C (0.989).

Note that there are no significant differences between the values of the bond lengths and angles of (I) in the solid state and those found for the calculated planar structure; the differences do not exceed 0.02 Å for bond distances and 2° for bond angles. All bond distances and angles are normal (Table 1) and are in good agreement with the geometry of 3,5-disubstituted-1,2,4-triazin-6(1H)-one derivatives (Buscemi et al., 2006; Garg & Stoltz, 2005; Sanudo et al., 2006; Trávníček et al., 1995).

Related literature top

For related literature, see: Abdel (1997); Ackerman (2007); Allen (2002); Becke (1988, 1993); Bettati et al. (2002); Blass et al. (2002); Buscemi et al. (2006); Camparini et al. (1978); Freidinger et al. (1993); Frisch (2010); Garg & Stoltz (2005); Kammoun et al. (2000); Kruszewski & Krygowski (1973); Krygowski (1993); Krygowski et al. (2010); Kudelko et al. (2011); Lee et al. (1988); Martinez-Teipel, Michelotti, Kelly, Weaver, Acholla, Beshah & Teixido (2001); Miesel (1982); Neunhoeffer (1996); Nishiwaki & Saito (1970); Palusiak et al. (2009); Sanudo et al. (2006); Trávníček et al. (1995); Zhao et al. (2003).

Experimental top

D-(-)-α-Phenylglycine hydrazide (3.30 g, 20 mmol) was added to a mixture of triethyl orthobenzoate (4.57 g, 20 mmol) and 0.1 g p-toluenesulfonic acid in xylene (20 ml) and kept under reflux for 3 h (monitored by thin-layer chromatography). After cooling, the mixture was washed with water (30 ml), dried over MgSO4 and then concentrated under reduced pressure. The oily residue was subjected to column chromatography (silica gel, eluent: hexane–AcOEt, 1:2 v/v), yielding 3,5-diphenyl-4,5-dihydro-1,2,4-triazin-6(1H)-one (2.60 g). This crude product was dissolved in ethanol (50 ml) and left in solution for 10 d at room temperature. Yellow needles of (I) were filtered off and dried in air [yield 0.35 g, 14%; m.p. 494–495 K, reference 491–493 K (Camparini et al., 1978)].

Based on the solid-state geometry, the molecular structure of (I) was optimized using standard density functional theory (DFT) employing the B3LYP hybrid function (Becke, 1988; 1993; Lee et al., 1988) at the 6-311++G** level of theory. All species corresponded to minima at the B3LYP/6-311++G** level with no imaginary frequencies. All calculations were performed using the GAUSSIAN09 program package (Frisch et al., 2010). Further details are given in the Supplementary material.

Refinement top

All H atoms were generated in idealized positions and then refined in riding mode. For aromatic C atoms, C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). For the amine NH group, N—H = 0.86 Å and Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate intramolecular hydrogen bonds.
[Figure 2] Fig. 2. A packing diagram for (I), showing the N1—H1···O7i hydrogen bonds as dashed lines. [Symmetry code: (i) -x + 1, -y + 2, -z + 1.]
3,5-Diphenyl-1,2,4-triazin-6(1H)-one top
Crystal data top
C15H11N3OF(000) = 1040
Mr = 249.27Dx = 1.333 Mg m3
Monoclinic, C2/cMelting point: 495 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 22.975 (5) ÅCell parameters from 2174 reflections
b = 5.5835 (10) Åθ = 3.5–25.0°
c = 21.550 (5) ŵ = 0.09 mm1
β = 116.06 (3)°T = 293 K
V = 2483.5 (9) Å3Plate, colourless
Z = 80.22 × 0.18 × 0.15 mm
Data collection top
Oxford Xcalibur
diffractometer
703 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.084
Graphite monochromatorθmax = 25.0°, θmin = 3.5°
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1h = 2727
ω scansk = 56
7417 measured reflectionsl = 2525
2174 independent 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.050H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.005P)2]
where P = (Fo2 + 2Fc2)/3
2174 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C15H11N3OV = 2483.5 (9) Å3
Mr = 249.27Z = 8
Monoclinic, C2/cMo Kα radiation
a = 22.975 (5) ŵ = 0.09 mm1
b = 5.5835 (10) ÅT = 293 K
c = 21.550 (5) Å0.22 × 0.18 × 0.15 mm
β = 116.06 (3)°
Data collection top
Oxford Xcalibur
diffractometer
703 reflections with I > 2σ(I)
7417 measured reflectionsRint = 0.084
2174 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.050H-atom parameters constrained
S = 0.96Δρmax = 0.14 e Å3
2174 reflectionsΔρmin = 0.15 e Å3
172 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.44615 (14)0.8833 (5)0.41540 (14)0.0605 (8)
H10.44780.98980.44490.073*
N20.39386 (14)0.8916 (5)0.35228 (17)0.0639 (9)
C30.39204 (17)0.7233 (7)0.30839 (17)0.0466 (10)
N40.43901 (13)0.5557 (5)0.32306 (13)0.0506 (8)
C50.48875 (18)0.5468 (6)0.38142 (18)0.0429 (9)
C60.49620 (18)0.7238 (7)0.43659 (18)0.0520 (10)
O70.54187 (10)0.7374 (4)0.49572 (10)0.0723 (8)
C80.53908 (17)0.3675 (7)0.39300 (17)0.0464 (9)
C90.52554 (16)0.1926 (6)0.34245 (17)0.0637 (11)
H90.48560.19320.30380.076*
C100.5702 (2)0.0194 (6)0.34868 (18)0.0698 (11)
H100.56010.09490.31410.084*
C110.6302 (2)0.0123 (7)0.4058 (2)0.0844 (14)
H110.66040.10550.41030.101*
C120.64313 (19)0.1846 (8)0.45502 (19)0.0870 (14)
H120.68320.18430.49350.104*
C130.59834 (19)0.3603 (7)0.44954 (17)0.0754 (12)
H130.60860.47370.48440.090*
C140.33639 (16)0.7274 (7)0.24217 (17)0.0511 (10)
C150.29077 (18)0.9059 (6)0.22270 (18)0.0622 (10)
H150.29671.03350.25260.075*
C160.23607 (18)0.9021 (7)0.1598 (2)0.0746 (12)
H160.20621.02640.14790.089*
C170.22605 (17)0.7126 (7)0.11469 (17)0.0732 (12)
H170.18950.70630.07240.088*
C180.27223 (18)0.5333 (6)0.13456 (18)0.0764 (12)
H180.26640.40450.10510.092*
C190.32689 (17)0.5412 (6)0.19740 (18)0.0670 (11)
H190.35740.41900.20930.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.065 (2)0.071 (3)0.046 (2)0.0064 (19)0.0255 (19)0.0181 (18)
N20.055 (2)0.070 (2)0.063 (2)0.0054 (18)0.0222 (18)0.0133 (19)
C30.047 (3)0.048 (3)0.046 (3)0.013 (2)0.021 (2)0.016 (2)
N40.0455 (19)0.064 (2)0.0406 (19)0.0046 (17)0.0171 (16)0.0003 (17)
C50.057 (3)0.038 (3)0.043 (2)0.004 (2)0.030 (2)0.001 (2)
C60.061 (3)0.048 (3)0.059 (3)0.007 (2)0.037 (2)0.003 (3)
O70.0738 (19)0.0888 (19)0.0481 (16)0.0022 (15)0.0211 (13)0.0169 (15)
C80.052 (2)0.054 (3)0.031 (2)0.005 (2)0.016 (2)0.000 (2)
C90.065 (3)0.069 (3)0.064 (3)0.012 (2)0.035 (2)0.000 (2)
C100.088 (3)0.071 (3)0.063 (3)0.005 (3)0.045 (3)0.003 (3)
C110.086 (4)0.097 (4)0.083 (4)0.013 (3)0.048 (3)0.025 (3)
C120.074 (3)0.113 (4)0.064 (3)0.013 (3)0.021 (3)0.011 (3)
C130.076 (3)0.089 (3)0.054 (3)0.008 (3)0.022 (2)0.001 (2)
C140.045 (3)0.050 (3)0.057 (3)0.001 (2)0.022 (2)0.005 (2)
C150.074 (3)0.062 (3)0.055 (3)0.012 (2)0.033 (2)0.000 (2)
C160.082 (3)0.078 (3)0.074 (3)0.008 (3)0.043 (3)0.002 (3)
C170.067 (3)0.083 (3)0.064 (3)0.009 (3)0.023 (2)0.006 (3)
C180.073 (3)0.068 (3)0.074 (3)0.005 (3)0.019 (2)0.020 (2)
C190.054 (3)0.069 (3)0.065 (3)0.005 (2)0.014 (2)0.020 (2)
Geometric parameters (Å, º) top
N1—C61.365 (3)C11—C121.364 (4)
N1—N21.364 (3)C11—H110.9300
N1—H10.8600C12—C131.389 (4)
N2—C31.321 (3)C12—H120.9300
C3—N41.357 (3)C13—H130.9300
C3—C141.438 (4)C14—C191.369 (3)
N4—C51.276 (3)C14—C151.371 (3)
C5—C81.466 (4)C15—C161.386 (4)
C5—C61.497 (4)C15—H150.9300
C6—O71.247 (3)C16—C171.386 (4)
C8—C131.372 (4)C16—H160.9300
C8—C91.393 (3)C17—C181.383 (4)
C9—C101.372 (3)C17—H170.9300
C9—H90.9300C18—C191.385 (4)
C10—C111.388 (4)C18—H180.9300
C10—H100.9300C19—H190.9300
C6—N1—N2126.8 (3)C10—C11—H11121.2
C6—N1—H1116.6C11—C12—C13122.1 (4)
N2—N1—H1116.6C11—C12—H12119.0
C3—N2—N1115.3 (3)C13—C12—H12119.0
N2—C3—N4123.5 (3)C8—C13—C12120.4 (4)
N2—C3—C14115.7 (4)C8—C13—H13119.8
N4—C3—C14120.8 (4)C12—C13—H13119.8
C5—N4—C3122.2 (3)C19—C14—C15118.2 (3)
N4—C5—C8119.5 (4)C19—C14—C3119.0 (4)
N4—C5—C6119.8 (4)C15—C14—C3122.8 (4)
C8—C5—C6120.6 (3)C16—C15—C14122.1 (4)
O7—C6—N1120.6 (4)C16—C15—H15119.0
O7—C6—C5127.1 (4)C14—C15—H15119.0
N1—C6—C5112.3 (3)C15—C16—C17119.8 (4)
C13—C8—C9117.9 (4)C15—C16—H16120.1
C13—C8—C5124.9 (4)C17—C16—H16120.1
C9—C8—C5117.2 (3)C16—C17—C18117.8 (4)
C10—C9—C8121.1 (4)C16—C17—H17121.1
C10—C9—H9119.4C18—C17—H17121.1
C8—C9—H9119.4C17—C18—C19121.5 (4)
C9—C10—C11121.0 (4)C17—C18—H18119.3
C9—C10—H10119.5C19—C18—H18119.3
C11—C10—H10119.5C18—C19—C14120.6 (4)
C12—C11—C10117.5 (4)C18—C19—H19119.7
C12—C11—H11121.2C14—C19—H19119.7
C6—N1—N2—C31.2 (5)C8—C9—C10—C110.3 (5)
N1—N2—C3—N41.6 (5)C9—C10—C11—C120.5 (5)
N1—N2—C3—C14178.8 (3)C10—C11—C12—C130.7 (6)
N2—C3—N4—C50.7 (5)C9—C8—C13—C120.7 (5)
C14—C3—N4—C5179.7 (3)C5—C8—C13—C12178.9 (3)
C3—N4—C5—C8177.5 (3)C11—C12—C13—C80.9 (5)
C3—N4—C5—C60.7 (5)N2—C3—C14—C19171.6 (3)
N2—N1—C6—O7179.0 (3)N4—C3—C14—C198.8 (5)
N2—N1—C6—C50.1 (4)N2—C3—C14—C155.8 (5)
N4—C5—C6—O7179.9 (4)N4—C3—C14—C15173.8 (3)
C8—C5—C6—O71.8 (5)C19—C14—C15—C160.1 (5)
N4—C5—C6—N11.0 (4)C3—C14—C15—C16177.3 (3)
C8—C5—C6—N1177.1 (3)C14—C15—C16—C170.5 (6)
N4—C5—C8—C13170.8 (3)C15—C16—C17—C180.5 (5)
C6—C5—C8—C137.3 (5)C16—C17—C18—C190.0 (5)
N4—C5—C8—C98.9 (4)C17—C18—C19—C140.6 (5)
C6—C5—C8—C9173.0 (3)C15—C14—C19—C180.7 (5)
C13—C8—C9—C100.5 (4)C3—C14—C19—C18176.9 (3)
C5—C8—C9—C10179.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O7i0.861.932.787 (3)171
C13—H13···O70.932.212.871 (5)127
C15—H15···N20.932.452.757 (5)99
C9—H9···N40.932.412.740 (5)101
C19—H19···N40.932.462.801 (5)102
Symmetry code: (i) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC15H11N3O
Mr249.27
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)22.975 (5), 5.5835 (10), 21.550 (5)
β (°) 116.06 (3)
V3)2483.5 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.22 × 0.18 × 0.15
Data collection
DiffractometerOxford Xcalibur
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7417, 2174, 703
Rint0.084
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.050, 0.96
No. of reflections2174
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.15

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
N1—C61.365 (3)C3—N41.357 (3)
N1—N21.364 (3)N4—C51.276 (3)
N2—C31.321 (3)C5—C61.497 (4)
C6—N1—N2126.8 (3)C5—N4—C3122.2 (3)
C3—N2—N1115.3 (3)N4—C5—C6119.8 (4)
N2—C3—N4123.5 (3)N1—C6—C5112.3 (3)
N4—C5—C8—C13170.8 (3)N2—C3—C14—C19171.6 (3)
C6—C5—C8—C137.3 (5)N4—C3—C14—C198.8 (5)
N4—C5—C8—C98.9 (4)N2—C3—C14—C155.8 (5)
C6—C5—C8—C9173.0 (3)N4—C3—C14—C15173.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O7i0.861.932.787 (3)170.5
C13—H13···O70.932.212.871 (5)126.9
C15—H15···N20.932.452.757 (5)99.2
C9—H9···N40.932.412.740 (5)100.8
C19—H19···N40.932.462.801 (5)101.5
Symmetry code: (i) x+1, y+2, z+1.
 

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