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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o341.
Published online 2009 January 17. doi:  10.1107/S1600536809001160
PMCID: PMC2968264

2-(2-Fur­yl)-1H-imidazo[4,5-f][1,10]phenanthroline-3,7-diium dichloride monohydrate

Abstract

The organic cation of the title salt, C17H12N4O2+·2Cl·H2O, is nearly planar, the dihedral angle between two pyridine rings being 2.53 (16)° and that between the pyridinum and furan rings being 4.17 (19)°. Mol­ecules are linked via N—H(...)O, N—H(...)Cl and O—H(...)Cl hydrogen bonds, forming a three-dimensional framework and π–π stacking inter­actions help to stabilize the crystal structure [the imidazole–pyridine and imidazole–benzene centroid–centroid distances are 3.501 (3) and 3.674 (3) Å; respectively].

Related literature

For general background, see: Zhao et al. (2004 [triangle]); Zheng et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o341-scheme1.jpg

Experimental

Crystal data

  • C17H12N4O2+·2Cl·H2O
  • M r = 377.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o341-efi1.jpg
  • a = 4.768 (3) Å
  • b = 17.897 (10) Å
  • c = 19.241 (11) Å
  • β = 92.060 (8)°
  • V = 1641.0 (16) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.42 mm−1
  • T = 293 (2) K
  • 0.23 × 0.18 × 0.15 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.911, T max = 0.940
  • 10782 measured reflections
  • 2859 independent reflections
  • 1886 reflections with I > 2σ(I)
  • R int = 0.058

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.115
  • S = 1.02
  • 2859 reflections
  • 226 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001160/at2707sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001160/at2707Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We acknowledge the support of the National Natural Science Foundation of China (No. 20662003), the International Collaborative Project of the Ministry of Science and Technology (No. 2007400108) and the Foundation of the Governor of Guizhou Province, China.

supplementary crystallographic information

Comment

Recent year, we used different alkyl-substituted glycolurils as the building blocks to synthesize the partially alkyl substituted cucurbit[n]urils (Zhao et al., 2004; Zheng et al., 2005). In this work, we further report the crystal structure of a phenanthroline-substituted semi-glycoluril.

The molecular structure of the title compound (I), consists of organic cations, two Cl- anions and one water molecule (Fig. 1). The organic cation is nearly planar, the dihedral angle between two pyridine rings is 2.53 (16) ° and that one between N4-pyridine ring and furan ring is 4.17 (19)°. Molecules are linked via N1—H1A···O1W, N2—H2A···Cl1, N4—H4···Cl2, O1W—H1WA···Cl2 and O1W—H1WB···Cl2 hydrogen bonds (Table 1) forming a three-dimensional framework. In additional, the π···π stacking interaction occurs between adjacent organic cations, the centroid-to-centroid distance of Cg2 to Cg3iv is 3.501 (3)Å and Cg2 to Cg5iv is 3.674 (3)Å [Cg2, Cg3 and Cg5 is the centroid of the N1-imidazole ring, N3-pyridine ring and C6-benzene ring, respectively. Symmerty codes: (iv) -1 + x, y, z].

Experimental

1,10-Phenanthroline-5,6-dione (1.0 g, 4.75 mmol) and ammonium acetate (3.9 g, 5 mmol) are dissolved in acetic acid glacial (60 mL) at 333 K, after cooling at room temperature, we can get lots of yellow deposits by the neutrlizing with ammonia to pH = 8–9 after 4 h of mixing with furaldhyde (0.8 mL) at 353 K. After the recryslalization in ethanol, the yellow product was dissolved in the dilute hydrochloric acid and red-brown crystals were obtained

after ten days.

Refinement

Water H atoms were located in a difference Fourier synthesis and refined riding in their as-found positions relative to O atoms with Uiso(H) =1.2Ueq(O). All other H atoms were placed in calculated positions and refined as riding, with C—H = 0.93–0.97 Å, N—H = 0.86 Å, and with Uiso(H) = 1.2 Ueq (C, N).

Figures

Fig. 1.
The molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C17H12N4O2+·2Cl·H2OF(000) = 776
Mr = 377.22Dx = 1.527 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2859 reflections
a = 4.768 (3) Åθ = 1.6–25.0°
b = 17.897 (10) ŵ = 0.42 mm1
c = 19.241 (11) ÅT = 293 K
β = 92.060 (8)°Prism, red-brown
V = 1641.0 (16) Å30.23 × 0.18 × 0.15 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer2859 independent reflections
Radiation source: fine-focus sealed tube1886 reflections with I > 2σ(I)
graphiteRint = 0.058
[var phi] and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −5→5
Tmin = 0.911, Tmax = 0.940k = −20→21
10782 measured reflectionsl = −22→22

Refinement

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) = 0.115H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0514P)2] where P = (Fo2 + 2Fc2)/3
2859 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

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)

xyzUiso*/Ueq
C10.2549 (7)0.5257 (2)0.91899 (18)0.0595 (10)
H10.19810.52700.96470.071*
C20.1543 (7)0.57043 (18)0.86872 (17)0.0491 (9)
H20.01840.60730.87280.059*
C30.2960 (6)0.55060 (16)0.80743 (16)0.0439 (8)
H30.27110.57180.76350.053*
C40.4742 (6)0.49469 (16)0.82609 (15)0.0366 (7)
C50.6721 (6)0.45050 (15)0.78964 (15)0.0356 (7)
C60.9978 (6)0.36694 (15)0.76729 (14)0.0334 (7)
C71.2049 (6)0.30919 (15)0.77145 (14)0.0331 (7)
C81.2878 (6)0.26901 (16)0.83160 (16)0.0405 (8)
H81.20620.27860.87390.049*
C91.4924 (6)0.21529 (17)0.82645 (16)0.0465 (8)
H91.55060.18770.86530.056*
C101.6108 (6)0.20276 (16)0.76279 (17)0.0453 (8)
H101.75000.16650.76070.054*
C111.3351 (6)0.29168 (15)0.70909 (14)0.0328 (7)
C121.2531 (6)0.33026 (15)0.64536 (14)0.0320 (7)
C131.3161 (6)0.34323 (16)0.52471 (15)0.0417 (8)
H131.41090.32870.48550.050*
C141.1068 (6)0.39700 (16)0.51891 (15)0.0420 (8)
H141.05770.41770.47580.050*
C150.9734 (6)0.41932 (15)0.57711 (14)0.0376 (7)
H150.83490.45590.57410.045*
C161.0477 (6)0.38639 (15)0.64198 (14)0.0322 (7)
C170.9259 (6)0.40383 (15)0.70643 (14)0.0319 (7)
N31.5391 (5)0.23910 (13)0.70414 (13)0.0412 (6)
N41.3821 (5)0.31224 (12)0.58612 (12)0.0359 (6)
H41.51300.27920.58820.043*
N10.8358 (5)0.39716 (13)0.81854 (11)0.0348 (6)
H1A0.83940.38400.86150.042*
N20.7228 (5)0.45605 (12)0.72179 (12)0.0345 (6)
H2A0.64320.48670.69280.041*
O10.4528 (5)0.47741 (12)0.89489 (11)0.0550 (6)
Cl10.44997 (17)0.56432 (4)0.62293 (4)0.0514 (3)
Cl20.83425 (17)0.20341 (5)0.53339 (5)0.0579 (3)
O1W0.8356 (5)0.35229 (14)0.94806 (11)0.0703 (8)
H1WA0.99930.33700.98030.084*
H1WB0.68400.34000.97510.084*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.053 (2)0.077 (3)0.049 (2)0.008 (2)0.0175 (18)−0.016 (2)
C20.047 (2)0.046 (2)0.055 (2)0.0040 (16)0.0111 (17)−0.0081 (17)
C30.048 (2)0.0404 (19)0.044 (2)0.0041 (16)0.0072 (16)0.0008 (15)
C40.0363 (17)0.0435 (18)0.0304 (17)−0.0035 (15)0.0052 (14)−0.0034 (14)
C50.0371 (18)0.0338 (17)0.0360 (19)−0.0036 (14)0.0023 (14)−0.0014 (13)
C60.0325 (16)0.0372 (17)0.0307 (17)−0.0030 (14)0.0030 (13)−0.0017 (13)
C70.0321 (16)0.0339 (17)0.0331 (18)−0.0038 (13)0.0004 (13)0.0010 (13)
C80.0395 (18)0.0436 (19)0.0387 (18)0.0014 (15)0.0033 (14)0.0035 (15)
C90.051 (2)0.046 (2)0.042 (2)0.0001 (16)−0.0055 (16)0.0126 (15)
C100.0442 (19)0.0371 (19)0.054 (2)0.0061 (15)−0.0062 (17)−0.0002 (16)
C110.0309 (16)0.0328 (17)0.0344 (18)−0.0052 (13)−0.0028 (13)−0.0023 (13)
C120.0302 (16)0.0345 (17)0.0314 (17)−0.0060 (13)0.0043 (13)−0.0048 (13)
C130.049 (2)0.0446 (19)0.0318 (18)−0.0005 (16)0.0065 (15)−0.0037 (14)
C140.053 (2)0.0402 (19)0.0327 (18)−0.0001 (16)0.0047 (15)0.0011 (14)
C150.0422 (18)0.0368 (18)0.0339 (18)0.0011 (14)0.0025 (14)0.0043 (14)
C160.0331 (16)0.0308 (16)0.0329 (17)−0.0045 (13)0.0019 (13)−0.0018 (13)
C170.0332 (16)0.0310 (16)0.0314 (17)−0.0010 (13)0.0010 (13)−0.0022 (13)
N30.0389 (15)0.0349 (15)0.0497 (17)0.0050 (12)−0.0006 (12)−0.0030 (12)
N40.0351 (14)0.0377 (15)0.0349 (15)0.0019 (11)0.0009 (11)−0.0045 (11)
N10.0371 (14)0.0396 (15)0.0281 (14)−0.0006 (12)0.0062 (11)0.0040 (11)
N20.0364 (14)0.0356 (14)0.0315 (15)0.0042 (11)0.0023 (11)0.0033 (11)
O10.0560 (15)0.0699 (16)0.0400 (14)0.0159 (12)0.0122 (11)0.0021 (11)
Cl10.0573 (5)0.0518 (5)0.0452 (5)0.0106 (4)0.0014 (4)0.0082 (4)
Cl20.0407 (5)0.0682 (6)0.0651 (6)0.0031 (4)0.0057 (4)−0.0194 (5)
O1W0.0487 (15)0.120 (2)0.0432 (14)0.0106 (14)0.0133 (11)0.0309 (14)

Geometric parameters (Å, °)

C1—C21.332 (4)C10—N31.336 (4)
C1—O11.373 (4)C10—H100.9300
C1—H10.9300C11—N31.359 (3)
C2—C31.425 (4)C11—C121.449 (4)
C2—H20.9300C12—N41.353 (3)
C3—C41.353 (4)C12—C161.403 (4)
C3—H30.9300C13—N41.333 (3)
C4—O11.367 (3)C13—C141.388 (4)
C4—C51.434 (4)C13—H130.9300
C5—N21.340 (3)C14—C151.367 (4)
C5—N11.341 (3)C14—H140.9300
C6—C171.377 (4)C15—C161.414 (4)
C6—N11.384 (3)C15—H150.9300
C6—C71.429 (4)C16—C171.423 (4)
C7—C111.406 (4)C17—N21.385 (3)
C7—C81.407 (4)N4—H40.8600
C8—C91.376 (4)N1—H1A0.8600
C8—H80.9300N2—H2A0.8600
C9—C101.385 (4)O1W—H1WA1.0173
C9—H90.9300O1W—H1WB0.9323
C2—C1—O1111.5 (3)C7—C11—C12120.1 (3)
C2—C1—H1124.2N4—C12—C16118.0 (3)
O1—C1—H1124.2N4—C12—C11118.8 (3)
C1—C2—C3106.4 (3)C16—C12—C11123.2 (3)
C1—C2—H2126.8N4—C13—C14120.4 (3)
C3—C2—H2126.8N4—C13—H13119.8
C4—C3—C2106.1 (3)C14—C13—H13119.8
C4—C3—H3127.0C15—C14—C13119.4 (3)
C2—C3—H3127.0C15—C14—H14120.3
C3—C4—O1110.9 (3)C13—C14—H14120.3
C3—C4—C5134.1 (3)C14—C15—C16119.5 (3)
O1—C4—C5115.0 (3)C14—C15—H15120.3
N2—C5—N1109.5 (3)C16—C15—H15120.3
N2—C5—C4125.5 (3)C12—C16—C15119.5 (3)
N1—C5—C4125.0 (3)C12—C16—C17115.0 (2)
C17—C6—N1106.9 (2)C15—C16—C17125.5 (3)
C17—C6—C7123.0 (3)C6—C17—N2107.3 (2)
N1—C6—C7130.1 (3)C6—C17—C16122.6 (3)
C11—C7—C8117.9 (3)N2—C17—C16130.1 (2)
C11—C7—C6116.0 (2)C10—N3—C11116.1 (3)
C8—C7—C6126.1 (3)C13—N4—C12123.2 (3)
C9—C8—C7118.5 (3)C13—N4—H4118.4
C9—C8—H8120.8C12—N4—H4118.4
C7—C8—H8120.8C5—N1—C6108.3 (2)
C8—C9—C10119.3 (3)C5—N1—H1A125.8
C8—C9—H9120.3C6—N1—H1A125.8
C10—C9—H9120.3C5—N2—C17108.1 (2)
N3—C10—C9124.6 (3)C5—N2—H2A126.0
N3—C10—H10117.7C17—N2—H2A126.0
C9—C10—H10117.7C4—O1—C1105.1 (2)
N3—C11—C7123.6 (3)H1WA—O1W—H1WB100.9
N3—C11—C12116.3 (3)
O1—C1—C2—C3−0.3 (4)C11—C12—C16—C170.8 (4)
C1—C2—C3—C4−0.2 (4)C14—C15—C16—C12−1.3 (4)
C2—C3—C4—O10.5 (3)C14—C15—C16—C17−179.7 (3)
C2—C3—C4—C5179.6 (3)N1—C6—C17—N20.3 (3)
C3—C4—C5—N2−0.9 (5)C7—C6—C17—N2−179.4 (2)
O1—C4—C5—N2178.1 (3)N1—C6—C17—C16−178.8 (2)
C3—C4—C5—N1178.9 (3)C7—C6—C17—C161.4 (4)
O1—C4—C5—N1−2.0 (4)C12—C16—C17—C6−1.9 (4)
C17—C6—C7—C110.2 (4)C15—C16—C17—C6176.6 (3)
N1—C6—C7—C11−179.5 (3)C12—C16—C17—N2179.2 (3)
C17—C6—C7—C8−179.7 (3)C15—C16—C17—N2−2.3 (5)
N1—C6—C7—C80.6 (5)C9—C10—N3—C110.0 (4)
C11—C7—C8—C90.4 (4)C7—C11—N3—C100.9 (4)
C6—C7—C8—C9−179.6 (3)C12—C11—N3—C10−178.9 (2)
C7—C8—C9—C100.4 (4)C14—C13—N4—C120.2 (4)
C8—C9—C10—N3−0.6 (5)C16—C12—N4—C13−2.5 (4)
C8—C7—C11—N3−1.1 (4)C11—C12—N4—C13178.2 (2)
C6—C7—C11—N3179.0 (2)N2—C5—N1—C6−0.2 (3)
C8—C7—C11—C12178.7 (2)C4—C5—N1—C6179.9 (3)
C6—C7—C11—C12−1.3 (4)C17—C6—N1—C5−0.1 (3)
N3—C11—C12—N4−0.2 (4)C7—C6—N1—C5179.6 (3)
C7—C11—C12—N4180.0 (2)N1—C5—N2—C170.4 (3)
N3—C11—C12—C16−179.4 (2)C4—C5—N2—C17−179.7 (3)
C7—C11—C12—C160.8 (4)C6—C17—N2—C5−0.4 (3)
N4—C13—C14—C151.6 (4)C16—C17—N2—C5178.6 (3)
C13—C14—C15—C16−1.0 (4)C3—C4—O1—C1−0.7 (3)
N4—C12—C16—C153.0 (4)C5—C4—O1—C1−180.0 (3)
C11—C12—C16—C15−177.8 (2)C2—C1—O1—C40.6 (4)
N4—C12—C16—C17−178.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1W0.861.762.618 (3)177
N2—H2A···Cl10.862.122.981 (3)179
N4—H4···Cl2i0.862.333.103 (3)150
O1W—H1WA···Cl2ii1.022.003.011 (3)172
O1W—H1WB···Cl2iii0.932.193.112 (3)173

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2707).

References

  • Bruker, (2005). APPEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhao, Y. J., Xue, S. F., Zhu, Q. J., Tao, Z., Zhang, J. X., Wei, Z. B., Long, L. S., Hu, M. L., Xiao, H. P. & Day, A. I. (2004). Chin. Sci. Bull.49, 1111–1116.
  • Zheng, L. M., Zhu, J. N., Zhang, Y. Q., Tao, Z., Xue, S. F., Zhu, Q. J., Wei, Z. B. & Long, L. S. (2005). Chin. J. Inorg. Chem.21, 1583–1588.

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