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ISSN: 2056-9890

2-Phenyl-2-(pyridin-2-yl)hexa­hydro­pyrimidine

aDepartment of Chemistry, Box 2117, Sam Houston State University, Huntsville, TX 77341, USA
*Correspondence e-mail: norman@shsu.edu

(Received 29 October 2010; accepted 8 November 2010; online 13 November 2010)

The title compound, C15H17N3, was prepared by reaction of benzoyl­pyridine and hexahydropyrimidine. The 1,3-diazinane ring adopts a chair conformation with one N—H group axial and the other equatorial. The axial N—H group participates in very weak hydrogen bonding to the lone pair of electrons of the N atom with the equatorial H atom producing a very weakly hydrogen-bonded dimer. The pyridine N atom accepts an inter­nal hydrogen bond from the equatorial H atom. The phenyl ring adopts an equatorial position while the pyridine ring is axial. The phenyl ring exhibits a slight twist (ca 25°) relative to the hexahydropyrimidine ring. The pyridine ring stacks with symmetry-related pyridine rings.

Related literature

For recent reports of the structures of other hexahydropyrimidines, see: Al-Resayes (2009[Al-Resayes, S. (2009). Acta Cryst. E65, o1874.]); Song et al. (2010[Song, X.-P., Li, G.-C., Wu, C.-Z. & Yang, F.-L. (2010). Acta Cryst. E66, o1083.]) and references therein. For general structural parameters for organic mol­ecules, see: Allen et al. (1987[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.]). For the extinction correction, see: Zachariasen (1968[Zachariasen, W. H. (1968). Acta Cryst. A24, 212-216.]).

[Scheme 1]

Experimental

Crystal data
  • C15H17N3

  • Mr = 239.32

  • Triclinic, [P \overline 1]

  • a = 8.2173 (2) Å

  • b = 9.0211 (2) Å

  • c = 9.1481 (3) Å

  • α = 97.277 (1)°

  • β = 94.216 (1)°

  • γ = 112.036 (1)°

  • V = 618.11 (3) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 0.61 mm−1

  • T = 90 K

  • 0.31 × 0.24 × 0.22 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.823, Tmax = 0.897

  • 6458 measured reflections

  • 2159 independent reflections

  • 1992 reflections with I > 3σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.166

  • S = 1.03

  • 2159 reflections

  • 169 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H16⋯N1 0.90 (1) 2.365 (13) 2.7696 (12) 107.1 (10)
N2—H17⋯N3i 0.91 (1) 3.25 (1) 4.1179 (13) 160.2 (10)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: TEXSAN for Windows (Molecular Structure Corporation, 1999[Molecular Structure Corporation. (1999). TEXSAN for Windows. MSC, The Woodlands, Texas, USA.]); molecular graphics: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: TEXSAN for Windows.

Supporting information


Comment top

During the course of an attempted preparation of a dinucleating ligand ([N,N'-bis(pyridin-2-yl)benzylidene]- propane-1,3-diamine) by reaction of two equivalents of 2-benzoylpyridine with 1,3-diaminopropane, the title compound formed instead.

The 1,3-diazinane ring adopts a chair conformation with the pyridine ring in the axial position. The pyridine nitrogen (N1) accepts an internal hydrogen bond from N3, a situation similar to that found in 2-methyl-2-(2-pyridyl)1,3-diazinane (Al-Resayes, 2009). N3 has its hydrogen atom (H16) in an equatorial position. The other amine nitrogen (N2) has its hydrogen atom (H17) in an axial position. H17 forms what appears to be a very long, very weak hydrogen bond to N3 in an adjacent molecule (1 - x, -y, 1 - z) (N2···N3 4.118 Å). H17 of that adjacent molecule hydrogen bonds to N3 of the original molecule, producing a very weakly hydrogen bonded dimeric pair. This is shown in Figure 2.

A more significant packing interaction is aromatic ring stacking of adjacent pyridine rings. This is shown in Figure 3 with the adjacent molecule at (-x, -y, 2 - z).

The phenyl ring is twisted out of the plane defined by N2, N3, C13 and C15 of the 1,3-diazinane ring by 25.1 °. This twist removes the potential steric strain between H9 of the phenyl ring and the equatorial internally hydrogen bonded H16. The phenyl ring is nearly coplanar with the C15, N3, C6 portion of the 1,3-diazinane ring (the dihedral angle is 173.9 °).

The distances within the title compound are very similar to those found in 2-methyl-2-(2-pyridyl)1,3-diazinane (Al-Resayes, 2009). Interestingly, in both compounds, the C4—C5 distance is the longest within the pyridyl ring, and in the title complex, the C7—C8 distance is the longest within the phenyl ring. Both of these bonds are relatively near N2, and are longer than the typical range (Allen et al., 1987).

Related literature top

For recent reports of the structures of other 1,3-diazinanes, see: Al-Resayes (2009); Song et al. (2010) and references therein. For general structural parameters for organic molecules, see: Allen et al. (1987). For the extinction correction, see: Zachariasen (1968).

Experimental top

2-Benzoylpyridine (3.66 g, 20.0 mmol) was dissolved in 15 ml anhydrous ethanol. 1,3-Diaminopropane (0.835 ml, 10.0 mmol) was added and the resultant mixture was refluxed for about six and a half hours. The light brown solution was concentrated on a rotary evaporator to a light brown syrup. The syrup was allowed to stand for four weeks affording a relatively large mass of colorless crystals intermixed with a brownish semisolid material. This mixture was washed repeatedly with anhydrous ethanol at 0 ° C and decanted to remove the brownish material. The washed crystalline mass was dissolved in warm (35 ° C) anhydrous ethanol and refrigerated. After three days, colorless, cuboidal crystals were observed and proved suitable for X-ray data collection.

Refinement top

The two N—H hydrogen atoms were located in difference maps. Their positions were refined giving N—H distances around 0.90 Å. All of the remaining hydrogen atoms were placed in calculated Positions (E—H of 0.95 Å) and were refined using a riding model. All hydrogen atoms were assigned thermal parameters 1.2 times larger than the corresponding Ueq of the covalently bonded atoms.

Structure description top

During the course of an attempted preparation of a dinucleating ligand ([N,N'-bis(pyridin-2-yl)benzylidene]- propane-1,3-diamine) by reaction of two equivalents of 2-benzoylpyridine with 1,3-diaminopropane, the title compound formed instead.

The 1,3-diazinane ring adopts a chair conformation with the pyridine ring in the axial position. The pyridine nitrogen (N1) accepts an internal hydrogen bond from N3, a situation similar to that found in 2-methyl-2-(2-pyridyl)1,3-diazinane (Al-Resayes, 2009). N3 has its hydrogen atom (H16) in an equatorial position. The other amine nitrogen (N2) has its hydrogen atom (H17) in an axial position. H17 forms what appears to be a very long, very weak hydrogen bond to N3 in an adjacent molecule (1 - x, -y, 1 - z) (N2···N3 4.118 Å). H17 of that adjacent molecule hydrogen bonds to N3 of the original molecule, producing a very weakly hydrogen bonded dimeric pair. This is shown in Figure 2.

A more significant packing interaction is aromatic ring stacking of adjacent pyridine rings. This is shown in Figure 3 with the adjacent molecule at (-x, -y, 2 - z).

The phenyl ring is twisted out of the plane defined by N2, N3, C13 and C15 of the 1,3-diazinane ring by 25.1 °. This twist removes the potential steric strain between H9 of the phenyl ring and the equatorial internally hydrogen bonded H16. The phenyl ring is nearly coplanar with the C15, N3, C6 portion of the 1,3-diazinane ring (the dihedral angle is 173.9 °).

The distances within the title compound are very similar to those found in 2-methyl-2-(2-pyridyl)1,3-diazinane (Al-Resayes, 2009). Interestingly, in both compounds, the C4—C5 distance is the longest within the pyridyl ring, and in the title complex, the C7—C8 distance is the longest within the phenyl ring. Both of these bonds are relatively near N2, and are longer than the typical range (Allen et al., 1987).

For recent reports of the structures of other 1,3-diazinanes, see: Al-Resayes (2009); Song et al. (2010) and references therein. For general structural parameters for organic molecules, see: Allen et al. (1987). For the extinction correction, see: Zachariasen (1968).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN for Windows (Molecular Structure Corporation, 1999); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN for Windows (Molecular Structure Corporation, 1999).

Figures top
[Figure 1] Fig. 1. Perspective drawing of the title compound with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Perspective drawing of two molecules of the title compound emphasizing the weak hydrogen bonding interaction.
[Figure 3] Fig. 3. Perspective drawing of two molecules of the title Compound emphasizing pyridine ring stacking.
2-Phenyl-2-(pyridin-2-yl)-hexahydropyrimidine top
Crystal data top
C15H17N3Z = 2
Mr = 239.32F(000) = 256.00
Triclinic, P1Dx = 1.286 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.5418 Å
a = 8.2173 (2) ÅCell parameters from 5072 reflections
b = 9.0211 (2) Åθ = 4.9–68.4°
c = 9.1481 (3) ŵ = 0.61 mm1
α = 97.277 (1)°T = 90 K
β = 94.216 (1)°Fragment, colorless
γ = 112.036 (1)°0.31 × 0.24 × 0.22 mm
V = 618.11 (3) Å3
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
2159 independent reflections
Radiation source: fine-focus sealed tube2159 reflections with I > 10σ(I)
Graphite monochromatorRint = 0.022
ω and φ scansθmax = 68.4°, θmin = 4.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 99
Tmin = 0.823, Tmax = 0.897k = 1010
6458 measured reflectionsl = 1010
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.049Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00563|Fo|2]
wR(F2) = 0.166(Δ/σ)max = 0.010
S = 1.03Δρmax = 0.27 e Å3
2159 reflectionsΔρmin = 0.18 e Å3
169 parametersExtinction correction: Zachariasen (1968), equ(3) Acta Cryst.(1968) A24, p. 213
0 restraintsExtinction coefficient: 0.000012 (5)
Crystal data top
C15H17N3γ = 112.036 (1)°
Mr = 239.32V = 618.11 (3) Å3
Triclinic, P1Z = 2
a = 8.2173 (2) ÅCu Kα radiation
b = 9.0211 (2) ŵ = 0.61 mm1
c = 9.1481 (3) ÅT = 90 K
α = 97.277 (1)°0.31 × 0.24 × 0.22 mm
β = 94.216 (1)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
2159 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
2159 reflections with I > 10σ(I)
Tmin = 0.823, Tmax = 0.897Rint = 0.022
6458 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.27 e Å3
2159 reflectionsΔρmin = 0.18 e Å3
169 parameters
Special details top

Refinement. Refinement of F2. The weighted R-factor wR and goodness of fit are based on F2, conventional R-factors R are based on F. R-factors based on F2 are statistically about twice as large as those based on F.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.25511 (12)0.17532 (11)0.94163 (10)0.0178 (2)
N20.30025 (12)0.06793 (11)0.55486 (10)0.0164 (3)
N30.51826 (11)0.16009 (11)0.77508 (11)0.0160 (2)
C10.1439 (2)0.2173 (1)1.02090 (13)0.0193 (3)
C20.0223 (1)0.20332 (13)0.96108 (13)0.0190 (3)
C30.07658 (13)0.14186 (13)0.81117 (13)0.0186 (3)
C40.0366 (1)0.09780 (13)0.72750 (12)0.0167 (3)
C50.2016 (1)0.11659 (12)0.79702 (12)0.0147 (3)
C60.33262 (13)0.06232 (13)0.71334 (12)0.0150 (3)
C70.28971 (13)0.11566 (13)0.72936 (12)0.0145 (3)
C80.1246 (1)0.23417 (13)0.66514 (12)0.0175 (3)
C90.0792 (1)0.39534 (13)0.68074 (12)0.0193 (3)
C100.1985 (2)0.44127 (13)0.76044 (13)0.0205 (3)
C110.3625 (1)0.3247 (1)0.82420 (12)0.0197 (3)
C120.4078 (1)0.16293 (13)0.80897 (12)0.0173 (3)
C130.3650 (2)0.2339 (1)0.52058 (12)0.0187 (3)
C140.5560 (1)0.33528 (13)0.58810 (13)0.0207 (3)
C150.5755 (1)0.32995 (13)0.75312 (13)0.0185 (3)
H10.18080.25891.12380.023*
H20.09690.23511.02130.023*
H30.18980.13010.76650.022*
H40.00250.05550.62450.020*
H50.04280.20380.61030.021*
H60.03330.47440.63700.023*
H70.16790.55150.77110.025*
H80.44440.35550.87860.024*
H90.52020.08410.85330.021*
H100.35720.22770.41570.023*
H110.29190.28600.55820.023*
H120.63250.29260.54170.025*
H130.58620.44430.57330.025*
H140.50400.37810.80040.022*
H150.69580.38780.79470.022*
H160.521 (2)0.160 (2)0.874 (2)0.016*
H170.350 (2)0.008 (2)0.503 (2)0.016*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0186 (5)0.0184 (5)0.0161 (5)0.0069 (4)0.0032 (4)0.0029 (4)
N20.0170 (5)0.0190 (5)0.0150 (5)0.0088 (4)0.0049 (4)0.0020 (4)
N30.0135 (5)0.0165 (5)0.0171 (5)0.0051 (4)0.0017 (4)0.0022 (4)
C10.0217 (6)0.0206 (5)0.0157 (6)0.0080 (5)0.0058 (5)0.0021 (4)
C20.0181 (5)0.0179 (5)0.0234 (6)0.0080 (4)0.0099 (5)0.0046 (5)
C30.0154 (5)0.0172 (5)0.0236 (6)0.0058 (4)0.0048 (5)0.0049 (5)
C40.0162 (5)0.0155 (5)0.0173 (6)0.0048 (4)0.0028 (4)0.0028 (4)
C50.0147 (5)0.0129 (5)0.0167 (6)0.0047 (4)0.0048 (4)0.0036 (4)
C60.0118 (5)0.0167 (6)0.0158 (6)0.0050 (4)0.0017 (4)0.0021 (4)
C70.0140 (5)0.0172 (6)0.0129 (5)0.0064 (4)0.0059 (4)0.0012 (4)
C80.0166 (6)0.0211 (6)0.0144 (6)0.0074 (5)0.0045 (4)0.0005 (5)
C90.0164 (5)0.0206 (6)0.0166 (6)0.0031 (5)0.0060 (4)0.0014 (5)
C100.0268 (6)0.0153 (5)0.0193 (6)0.0073 (5)0.0097 (5)0.0020 (4)
C110.0220 (6)0.0215 (6)0.0192 (6)0.0118 (5)0.0064 (5)0.0035 (5)
C120.0166 (5)0.0191 (6)0.0160 (6)0.0071 (5)0.0042 (5)0.0010 (5)
C130.0189 (6)0.0231 (6)0.0183 (6)0.0107 (5)0.0071 (5)0.0071 (5)
C140.0191 (6)0.0192 (6)0.0261 (7)0.0081 (5)0.0092 (5)0.0071 (5)
C150.0144 (5)0.0162 (5)0.0254 (6)0.0058 (4)0.0051 (5)0.0038 (5)
Geometric parameters (Å, º) top
N1—C11.339 (2)C7—C81.401 (1)
N1—C51.337 (2)C8—H50.95
N2—H170.91 (1)C8—C91.388 (2)
N2—C61.465 (1)C9—H60.95
N2—C131.4730 (13)C9—C101.393 (2)
N3—H160.90 (1)C10—H70.95
N3—C61.4702 (12)C10—C111.388 (2)
N3—C151.4699 (13)C11—H80.95
C1—H10.95C11—C121.393 (2)
C1—C21.387 (2)C12—H90.95
C2—H20.95C13—H100.95
C2—C31.385 (2)C13—H110.95
C3—H30.95C13—C141.523 (1)
C3—C41.383 (2)C14—H130.95
C4—H40.95C14—H120.95
C4—C51.395 (2)C14—C151.515 (2)
C5—C61.551 (1)C15—H150.95
C6—C71.538 (1)C15—H140.95
C7—C121.392 (2)
N1···C11i3.373 (1)N3···C3iv3.389 (1)
N1···C2ii3.498 (2)C1···C2ii3.572 (2)
N1···C12i3.501 (2)C2···C8ii3.582 (2)
N2···C4iii3.381 (2)C9···C9v3.484 (2)
C5—N1—C1117.65 (9)H5—C8—C7119.6
H17—N2—C6108.9 (8)C9—C8—C7120.82 (10)
H17—N2—C13110.7 (8)H6—C9—C8120.0
C6—N2—C13113.36 (8)H6—C9—C10120.0
H16—N3—C6104.7 (8)C8—C9—C10120.06 (10)
H16—N3—C15107.2 (8)H7—C10—C11120.2
C6—N3—C15112.82 (9)H7—C10—C9120.2
H1—C1—N1118.2C11—C10—C9119.5 (1)
H1—C1—C2118.2H8—C11—C10119.8
N1—C1—C2123.62 (10)H8—C11—C12119.8
H2—C2—C3120.9C10—C11—C12120.40 (10)
H2—C2—C1120.9H9—C12—C7119.7
C3—C2—C1118.23 (10)H9—C12—C11119.7
H3—C3—C4120.5C7—C12—C11120.60 (10)
H3—C3—C2120.5H10—C13—H11109.5
C4—C3—C2118.97 (10)H10—C13—N2108.6
H4—C4—C3120.6H10—C13—C14108.6
H4—C4—C5120.6H11—C13—N2108.6
C3—C4—C5118.85 (10)H11—C13—C14108.6
N1—C5—C4122.68 (10)N2—C13—C14113.03 (9)
N1—C5—C6115.06 (9)H13—C14—H12109.5
C4—C5—C6122.19 (9)H13—C14—C15109.5
N2—C6—N3111.48 (9)H13—C14—C13109.5
N2—C6—C7107.67 (8)H12—C14—C15109.5
N2—C6—C5109.10 (8)H12—C14—C13109.5
N3—C6—C7109.07 (9)C15—C14—C13109.24 (9)
N3—C6—C5112.26 (8)H15—C15—H14109.5
C7—C6—C5107.06 (8)H15—C15—N3109.6
C12—C7—C8118.61 (10)H15—C15—C14109.6
C12—C7—C6122.22 (10)H14—C15—N3109.6
C8—C7—C6119.15 (10)H14—C15—C14109.6
H5—C8—C9119.6N3—C15—C14109.21 (9)
N1—C1—C2—C30.3 (2)C2—C3—C4—C50.1 (2)
N1—C5—C4—C30.1 (2)C3—C4—C5—C6176.89 (9)
N1—C5—C6—N2155.92 (9)C4—C5—C6—C789.2 (1)
N1—C5—C6—N331.8 (1)C5—C6—N2—C1374.1 (1)
N1—C5—C6—C787.8 (1)C5—C6—N3—C1566.4 (1)
N2—C6—N3—C1556.4 (1)C5—C6—C7—C864.4 (1)
N2—C6—C5—C427.1 (1)C5—C6—C7—C12114.0 (1)
N2—C6—C7—C852.8 (1)C6—N2—C13—C1450.1 (1)
N2—C6—C7—C12128.9 (1)C6—N3—C15—C1460.0 (1)
N2—C13—C14—C1552.8 (1)C6—C7—C8—C9178.20 (8)
N3—C6—N2—C1350.5 (1)C6—C7—C12—C11178.39 (9)
N3—C6—C5—C4151.2 (1)C7—C6—N2—C13170.05 (8)
N3—C6—C7—C8173.95 (9)C7—C6—N3—C15175.14 (8)
N3—C6—C7—C127.7 (1)C7—C8—C9—C100.3 (2)
N3—C15—C14—C1356.7 (1)C7—C12—C11—C100.2 (2)
C1—N1—C5—C40.1 (2)C8—C7—C12—C110.1 (2)
C1—N1—C5—C6177.08 (9)C8—C9—C10—C110.2 (2)
C1—C2—C3—C40.3 (2)C9—C8—C7—C120.2 (2)
C2—C1—N1—C50.1 (2)C9—C10—C11—C120.1 (2)
Symmetry codes: (i) x+1, y, z+2; (ii) x, y, z+2; (iii) x, y, z+1; (iv) x+1, y, z; (v) x, y1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H16···N10.90 (1)2.365 (13)2.7696 (12)107.1 (10)
N2—H17···N3vi0.91 (1)3.25 (1)4.1179 (13)160.2 (10)
Symmetry code: (vi) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC15H17N3
Mr239.32
Crystal system, space groupTriclinic, P1
Temperature (K)90
a, b, c (Å)8.2173 (2), 9.0211 (2), 9.1481 (3)
α, β, γ (°)97.277 (1), 94.216 (1), 112.036 (1)
V3)618.11 (3)
Z2
Radiation typeCu Kα
µ (mm1)0.61
Crystal size (mm)0.31 × 0.24 × 0.22
Data collection
DiffractometerBruker Kappa APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.823, 0.897
No. of measured, independent and
observed [I > 10σ(I)] reflections
6458, 2159, 2159
Rint0.022
(sin θ/λ)max1)0.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.166, 1.03
No. of reflections2159
No. of parameters169
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.18

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SIR92 (Altomare et al., 1993), TEXSAN for Windows (Molecular Structure Corporation, 1999), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H16···N10.90 (1)2.365 (13)2.7696 (12)107.1 (10)
N2—H17···N3i0.91 (1)3.25 (1)4.1179 (13)160.2 (10)
Symmetry code: (i) x+1, y, z+1.
 

Acknowledgements

We would like to thank Frank Fronczek for the data collection and the Louisiana Board of Regents Support Fund and the Robert A. Welch Foundation (x − 0011) for financial support.

References

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