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

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COMMUNICATIONS
ISSN: 2056-9890

4-Methyl-6-phenyl­pyrimidin-2-amine

aQingdao University of Science and Technology, Qingdao 266061, People's Republic of China
*Correspondence e-mail: zjli126@126.com

(Received 24 December 2007; accepted 25 March 2008; online 29 March 2008)

The title compound, C11H11N3, was synthesized as part of our research into functionalized pyrimidines. It crystallizes with two independent mol­ecules in the asymmetric unit that differ only in the twist between the two aromatic rings; the torsion angles between the rings are 29.9 (2) and 45.1 (2)°. The crystal packing is dominated by inter­molecular N—H⋯N hydrogen bonds between independent and equivalent mol­ecules, forming an infinite three-dimensional network.

Related literature

For biological activity, see: Zhu & Yang (2005[Zhu, W. M. & Yang, A. M. (2005). Appl. Chem. Ind. 34, 360-361.]); Sherrington & Taskinen (2001[Sherrington, D. C. & Taskinen, K. A. (2001). Chem. Soc. Rev. 30, 83-93.]); Ligthart et al. (2005[Ligthart, G. B. W. L., Ohkawa, H., Sijbesma, R. P. & Meijer, E. W. (2005). J. Am. Chem. Soc. 127, 810-811.]). For a similar structure, see: Fun et al. (2006[Fun, H.-K., Goswami, S., Jana, S. & Chantrapromma, S. (2006). Acta Cryst. E62, o5332-o5334.]).

[Scheme 1]

Experimental

Crystal data
  • C11H11N3

  • Mr = 185.23

  • Monoclinic, P 21 /c

  • a = 14.0558 (11) Å

  • b = 9.3808 (7) Å

  • c = 18.5227 (12) Å

  • β = 125.950 (4)°

  • V = 1977.1 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 273 (2) K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART 1K CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.977, Tmax = 0.985

  • 17472 measured reflections

  • 3619 independent reflections

  • 2760 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.113

  • S = 1.04

  • 3619 reflections

  • 256 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯N3i 0.86 2.38 3.1918 (18) 157
N1—H1B⋯N6i 0.86 2.35 3.2095 (18) 175
N4—H4C⋯N2i 0.86 2.29 3.1474 (19) 176
N4—H4B⋯N5ii 0.86 2.24 3.0834 (18) 166
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information


Comment top

Pyrimidines are broadly used in the preparation of pesticides and medications (Zhu & Yang, 2005). Functionalized pyrimidines are important for the synthesis of purine- and pteridine-related compounds and also for multiple hydrogen-bonding interactions that play a role in molecular recognition and supramolecular chemistry (Sherrington & Taskinen, 2001; Ligthart et al., 2005). In the title compound, (I), (fig. 1) there are two molecules per asymmetric unit that differ only in the twist between the two aromatic rings with dihedral angles between the phenyl and pyrimidine rings of 29.41 (2)° 46.32 (3)°. Bond lengths and angles for (I) are generally normal (Fun et al., 2006).

In the packing there are intermolecular N—H···N hydrogen bonds that link each independent molecule to related self molecules as well as to the second molecule in the asymmetric unit to create an infinite network of hydrogen bonded molecules (Table 1, Fig. 2).

Related literature top

For biological activity, see: Zhu & Yang (2005); Sherrington & Taskinen (2001); Ligthart et al. (2005). For a similar structure, see: Fun et al. (2006).

Experimental top

The single crystals of the title compound were obtained by reaction of 1-phenylbutane-1,3-dione(0.2 mmol) with guanidine nitrate(0.2 mmol) by refluxing in DMF(50 ml). The product (yied 89%) was stirred in the DMF and single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from DMF at room temperature.

Refinement top

H atoms were fixed geometrically and allowed to ride on their attached atoms, with N—H=0.86, C—H=0.93 or 0.96 Å, and with Uiso(H) values set at 1.5 Ueq(C)(for CH3) or 1.2 Ueq(C)(for CH2, aromatic CH and NH2).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top
[Figure 1] Fig. 1. The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The packing of (I), showing one layer of molecules connected by N—H···N hydrogen bonds (dashed lines).
(I) top
Crystal data top
C11H11N3F(000) = 784
Mr = 185.23Dx = 1.245 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 512 reflections
a = 14.0558 (11) Åθ = 2–22°
b = 9.3808 (7) ŵ = 0.08 mm1
c = 18.5227 (12) ÅT = 273 K
β = 125.950 (4)°Block, colorless
V = 1977.1 (2) Å30.30 × 0.20 × 0.20 mm
Z = 8
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
3619 independent reflections
Radiation source: fine-focus sealed tube2760 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
thin–slice ω scansθmax = 25.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1416
Tmin = 0.977, Tmax = 0.985k = 1111
17472 measured reflectionsl = 2220
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0535P)2 + 0.393P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3619 reflectionsΔρmax = 0.21 e Å3
256 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0088 (13)
Crystal data top
C11H11N3V = 1977.1 (2) Å3
Mr = 185.23Z = 8
Monoclinic, P21/cMo Kα radiation
a = 14.0558 (11) ŵ = 0.08 mm1
b = 9.3808 (7) ÅT = 273 K
c = 18.5227 (12) Å0.30 × 0.20 × 0.20 mm
β = 125.950 (4)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
3619 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
2760 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.985Rint = 0.033
17472 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.04Δρmax = 0.21 e Å3
3619 reflectionsΔρmin = 0.16 e Å3
256 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
N11.09631 (12)0.10203 (14)0.46842 (9)0.0492 (4)
H1A1.07750.10720.50490.059*
H1B1.15900.14340.48100.059*
N21.06247 (11)0.02652 (14)0.33737 (9)0.0445 (3)
N30.93111 (10)0.03294 (12)0.37592 (8)0.0371 (3)
C10.69500 (14)0.10273 (16)0.31097 (10)0.0428 (4)
H1C0.72760.02320.34780.051*
C20.59049 (15)0.1585 (2)0.28979 (12)0.0537 (4)
H2B0.55310.11610.31230.064*
C30.54156 (17)0.2762 (2)0.23573 (13)0.0661 (5)
H3B0.47180.31430.22230.079*
C40.59617 (19)0.3378 (2)0.20139 (14)0.0711 (6)
H4A0.56270.41680.16420.085*
C50.70011 (16)0.28266 (19)0.22208 (12)0.0557 (5)
H5A0.73630.32490.19860.067*
C60.75185 (13)0.16463 (15)0.27758 (10)0.0395 (4)
C70.86232 (13)0.10283 (14)0.29811 (10)0.0370 (3)
C80.89113 (14)0.11063 (17)0.23828 (11)0.0462 (4)
H8A0.84350.15980.18470.055*
C91.02765 (13)0.02917 (15)0.39158 (10)0.0371 (3)
C100.99219 (14)0.04372 (18)0.26026 (11)0.0457 (4)
C111.02670 (19)0.0447 (3)0.19755 (13)0.0730 (6)
H11A1.11080.04760.23110.109*
H11B0.99370.12710.15970.109*
H11C0.99770.04000.16160.109*
N40.66133 (12)0.04458 (13)0.54000 (9)0.0466 (4)
H4B0.61900.02400.53770.056*
H4C0.73660.03630.57220.056*
N50.49149 (11)0.17062 (13)0.44429 (9)0.0440 (3)
N60.68078 (11)0.26712 (12)0.49771 (8)0.0379 (3)
C120.78707 (15)0.46852 (17)0.44133 (12)0.0494 (4)
H12A0.79970.37410.43390.059*
C130.85244 (17)0.5759 (2)0.43871 (13)0.0597 (5)
H13A0.90800.55330.42850.072*
C140.83596 (17)0.7156 (2)0.45107 (13)0.0644 (5)
H14A0.88090.78710.44990.077*
C150.75362 (19)0.74936 (19)0.46501 (15)0.0683 (6)
H15A0.74290.84380.47400.082*
C160.68603 (17)0.64335 (17)0.46588 (13)0.0566 (5)
H16A0.62860.66740.47380.068*
C170.70284 (13)0.50159 (15)0.45505 (10)0.0404 (4)
C180.62748 (13)0.38817 (15)0.45327 (10)0.0387 (4)
C190.50733 (14)0.40570 (17)0.40489 (11)0.0471 (4)
H19A0.47210.49190.37700.057*
C200.60975 (13)0.16496 (15)0.49325 (10)0.0376 (3)
C210.44081 (14)0.29142 (17)0.39901 (11)0.0475 (4)
C220.30886 (16)0.2934 (2)0.33834 (15)0.0744 (6)
H22A0.27870.22620.35930.112*
H22B0.28230.26810.27900.112*
H22C0.28120.38720.33790.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0443 (8)0.0635 (8)0.0430 (8)0.0156 (6)0.0274 (7)0.0176 (7)
N20.0398 (7)0.0573 (8)0.0382 (8)0.0040 (6)0.0239 (7)0.0047 (6)
N30.0349 (7)0.0422 (6)0.0335 (7)0.0002 (5)0.0196 (6)0.0031 (5)
C10.0399 (9)0.0490 (8)0.0359 (9)0.0024 (7)0.0202 (8)0.0030 (7)
C20.0455 (10)0.0717 (11)0.0479 (10)0.0032 (9)0.0296 (9)0.0102 (9)
C30.0497 (11)0.0876 (14)0.0552 (12)0.0223 (10)0.0275 (10)0.0005 (10)
C40.0712 (13)0.0751 (13)0.0652 (13)0.0330 (11)0.0391 (12)0.0220 (10)
C50.0577 (11)0.0579 (10)0.0533 (11)0.0135 (8)0.0335 (10)0.0141 (8)
C60.0377 (8)0.0430 (8)0.0328 (8)0.0007 (6)0.0179 (7)0.0014 (6)
C70.0351 (8)0.0379 (7)0.0334 (8)0.0026 (6)0.0175 (7)0.0012 (6)
C80.0432 (9)0.0582 (9)0.0353 (9)0.0052 (7)0.0220 (8)0.0109 (7)
C90.0345 (8)0.0403 (7)0.0341 (8)0.0017 (6)0.0187 (7)0.0013 (6)
C100.0414 (9)0.0617 (10)0.0351 (9)0.0007 (7)0.0230 (8)0.0039 (7)
C110.0642 (13)0.1156 (17)0.0521 (12)0.0198 (12)0.0414 (11)0.0190 (11)
N40.0396 (7)0.0426 (7)0.0574 (9)0.0040 (6)0.0284 (7)0.0128 (6)
N50.0377 (7)0.0477 (7)0.0461 (8)0.0007 (6)0.0243 (7)0.0095 (6)
N60.0385 (7)0.0396 (6)0.0385 (7)0.0002 (5)0.0242 (6)0.0026 (5)
C120.0520 (10)0.0467 (9)0.0570 (11)0.0015 (7)0.0363 (9)0.0049 (7)
C130.0559 (11)0.0681 (11)0.0666 (13)0.0038 (9)0.0425 (10)0.0081 (9)
C140.0619 (12)0.0561 (11)0.0710 (13)0.0176 (9)0.0367 (11)0.0032 (9)
C150.0769 (14)0.0424 (9)0.0895 (16)0.0120 (9)0.0510 (13)0.0080 (9)
C160.0621 (11)0.0473 (9)0.0710 (12)0.0024 (8)0.0449 (10)0.0038 (8)
C170.0416 (8)0.0405 (8)0.0381 (9)0.0007 (6)0.0229 (7)0.0038 (6)
C180.0429 (9)0.0397 (8)0.0378 (9)0.0014 (6)0.0260 (8)0.0023 (6)
C190.0448 (10)0.0448 (8)0.0519 (10)0.0071 (7)0.0286 (9)0.0139 (7)
C200.0391 (8)0.0406 (7)0.0366 (8)0.0011 (6)0.0243 (7)0.0016 (6)
C210.0399 (9)0.0543 (9)0.0481 (10)0.0049 (7)0.0258 (8)0.0125 (8)
C220.0415 (10)0.0858 (14)0.0792 (15)0.0059 (10)0.0261 (11)0.0336 (12)
Geometric parameters (Å, º) top
N1—C91.3459 (19)N4—C201.3467 (19)
N1—H1A0.8600N4—H4B0.8600
N1—H1B0.8600N4—H4C0.8600
N2—C101.339 (2)N5—C211.339 (2)
N2—C91.3509 (19)N5—C201.3484 (19)
N3—C91.3426 (19)N6—C181.3431 (18)
N3—C71.3437 (18)N6—C201.3510 (18)
C1—C21.382 (2)C12—C131.383 (2)
C1—C61.392 (2)C12—C171.384 (2)
C1—H1C0.9300C12—H12A0.9300
C2—C31.374 (3)C13—C141.373 (3)
C2—H2B0.9300C13—H13A0.9300
C3—C41.379 (3)C14—C151.363 (3)
C3—H3B0.9300C14—H14A0.9300
C4—C51.375 (3)C15—C161.382 (2)
C4—H4A0.9300C15—H15A0.9300
C5—C61.391 (2)C16—C171.386 (2)
C5—H5A0.9300C16—H16A0.9300
C6—C71.483 (2)C17—C181.488 (2)
C7—C81.387 (2)C18—C191.380 (2)
C8—C101.378 (2)C19—C211.384 (2)
C8—H8A0.9300C19—H19A0.9300
C10—C111.499 (2)C21—C221.502 (2)
C11—H11A0.9600C22—H22A0.9600
C11—H11B0.9600C22—H22B0.9600
C11—H11C0.9600C22—H22C0.9600
C9—N1—H1A120.0C20—N4—H4B120.0
C9—N1—H1B120.0C20—N4—H4C120.0
H1A—N1—H1B120.0H4B—N4—H4C120.0
C10—N2—C9116.07 (13)C21—N5—C20116.55 (13)
C9—N3—C7116.30 (12)C18—N6—C20115.84 (12)
C2—C1—C6120.52 (15)C13—C12—C17120.02 (16)
C2—C1—H1C119.7C13—C12—H12A120.0
C6—C1—H1C119.7C17—C12—H12A120.0
C3—C2—C1120.35 (17)C14—C13—C12120.58 (17)
C3—C2—H2B119.8C14—C13—H13A119.7
C1—C2—H2B119.8C12—C13—H13A119.7
C2—C3—C4119.81 (17)C15—C14—C13119.89 (16)
C2—C3—H3B120.1C15—C14—H14A120.1
C4—C3—H3B120.1C13—C14—H14A120.1
C5—C4—C3120.12 (18)C14—C15—C16120.07 (17)
C5—C4—H4A119.9C14—C15—H15A120.0
C3—C4—H4A119.9C16—C15—H15A120.0
C4—C5—C6120.95 (18)C15—C16—C17120.81 (17)
C4—C5—H5A119.5C15—C16—H16A119.6
C6—C5—H5A119.5C17—C16—H16A119.6
C5—C6—C1118.24 (15)C12—C17—C16118.59 (15)
C5—C6—C7121.01 (14)C12—C17—C18120.67 (14)
C1—C6—C7120.72 (13)C16—C17—C18120.65 (14)
N3—C7—C8121.26 (14)N6—C18—C19121.89 (13)
N3—C7—C6116.84 (13)N6—C18—C17117.21 (13)
C8—C7—C6121.83 (14)C19—C18—C17120.86 (13)
C10—C8—C7118.27 (14)C18—C19—C21118.12 (14)
C10—C8—H8A120.9C18—C19—H19A120.9
C7—C8—H8A120.9C21—C19—H19A120.9
N3—C9—N1117.08 (13)N4—C20—N5116.82 (13)
N3—C9—N2126.34 (13)N4—C20—N6117.13 (13)
N1—C9—N2116.58 (13)N5—C20—N6126.02 (13)
N2—C10—C8121.75 (14)N5—C21—C19121.31 (14)
N2—C10—C11117.25 (15)N5—C21—C22116.64 (15)
C8—C10—C11120.99 (15)C19—C21—C22121.98 (15)
C10—C11—H11A109.5C21—C22—H22A109.5
C10—C11—H11B109.5C21—C22—H22B109.5
H11A—C11—H11B109.5H22A—C22—H22B109.5
C10—C11—H11C109.5C21—C22—H22C109.5
H11A—C11—H11C109.5H22A—C22—H22C109.5
H11B—C11—H11C109.5H22B—C22—H22C109.5
C6—C1—C2—C30.3 (2)C17—C12—C13—C141.1 (3)
C1—C2—C3—C40.9 (3)C12—C13—C14—C150.8 (3)
C2—C3—C4—C50.8 (3)C13—C14—C15—C160.6 (3)
C3—C4—C5—C60.0 (3)C14—C15—C16—C171.7 (3)
C4—C5—C6—C10.7 (3)C13—C12—C17—C160.0 (3)
C4—C5—C6—C7178.44 (17)C13—C12—C17—C18176.76 (16)
C2—C1—C6—C50.5 (2)C15—C16—C17—C121.4 (3)
C2—C1—C6—C7178.31 (14)C15—C16—C17—C18178.14 (17)
C9—N3—C7—C80.6 (2)C20—N6—C18—C191.1 (2)
C9—N3—C7—C6176.50 (12)C20—N6—C18—C17178.59 (13)
C5—C6—C7—N3153.34 (15)C12—C17—C18—N645.1 (2)
C1—C6—C7—N328.9 (2)C16—C17—C18—N6138.24 (16)
C5—C6—C7—C829.6 (2)C12—C17—C18—C19132.43 (17)
C1—C6—C7—C8148.13 (15)C16—C17—C18—C1944.2 (2)
N3—C7—C8—C100.5 (2)N6—C18—C19—C213.4 (2)
C6—C7—C8—C10176.46 (14)C17—C18—C19—C21174.05 (15)
C7—N3—C9—N1178.71 (13)C21—N5—C20—N4179.01 (14)
C7—N3—C9—N20.8 (2)C21—N5—C20—N62.9 (2)
C10—N2—C9—N30.9 (2)C18—N6—C20—N4177.49 (13)
C10—N2—C9—N1178.64 (14)C18—N6—C20—N54.5 (2)
C9—N2—C10—C80.7 (2)C20—N5—C21—C192.0 (2)
C9—N2—C10—C11178.21 (16)C20—N5—C21—C22174.92 (16)
C7—C8—C10—N20.6 (2)C18—C19—C21—N55.0 (3)
C7—C8—C10—C11178.35 (17)C18—C19—C21—C22171.76 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N3i0.862.383.1918 (18)157
N1—H1B···N6i0.862.353.2095 (18)175
N4—H4C···N2i0.862.293.1474 (19)176
N4—H4B···N5ii0.862.243.0834 (18)166
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC11H11N3
Mr185.23
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)14.0558 (11), 9.3808 (7), 18.5227 (12)
β (°) 125.950 (4)
V3)1977.1 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 1K CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.977, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
17472, 3619, 2760
Rint0.033
(sin θ/λ)max1)0.604
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.113, 1.04
No. of reflections3619
No. of parameters256
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.16

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N3i0.862.383.1918 (18)156.6
N1—H1B···N6i0.862.353.2095 (18)174.6
N4—H4C···N2i0.862.293.1474 (19)176.4
N4—H4B···N5ii0.862.243.0834 (18)166.2
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z+1.
 

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province (grant No. Y2005F08).

References

First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFun, H.-K., Goswami, S., Jana, S. & Chantrapromma, S. (2006). Acta Cryst. E62, o5332–o5334.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLigthart, G. B. W. L., Ohkawa, H., Sijbesma, R. P. & Meijer, E. W. (2005). J. Am. Chem. Soc. 127, 810–811.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSherrington, D. C. & Taskinen, K. A. (2001). Chem. Soc. Rev. 30, 83–93.  Web of Science CrossRef CAS Google Scholar
First citationZhu, W. M. & Yang, A. M. (2005). Appl. Chem. Ind. 34, 360–361.  CAS Google Scholar

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