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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1448

5H-Imidazo[4,5-f][1,10]phenanthroline

aCollege of Food Science and Technology, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China, and bCollege of Science, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China
*Correspondence e-mail: songwd60@163.com

(Received 5 April 2012; accepted 16 April 2012; online 21 April 2012)

The title mol­ecule, C13H8N4, is is essentially planar [r.m.s. deviation for all non-H atoms = 0.025 (3) Å]. In the crystal, mol­ecules are connected through one weak bifurcated N—H⋯(N,N) hydrogen bond and three ππ stacking inter­actions between pyridine and imidazole rings [centroid–centroid distance = 3.631 (8) Å] and between pyridine and benzene rings [centroid–centroid distances = 3.675 (5) and 3.666 (2) Å].

Related literature

For our previous work based on 1,10-phenanthroline as anauxiliary ligand, see: Song et al. (2009[Song, W.-D., Wang, H., Hu, S.-W., Qin, P.-W. & Li, S.-J. (2009). Acta Cryst. E65, m701.]); Hao et al. (2008[Hao, X.-M., Gu, C.-S., Song, W.-D. & Liu, J.-W. (2008). Acta Cryst. E64, m1052.]). For background to 1,10-phenanthroline complexes, see: Chesnut et al. (1999[Chesnut, D.-J., Haushalter, R.-C. & Zubieta, J. (1999). Inorg. Chim. Acta, 292, 41-51.]).

[Scheme 1]

Experimental

Crystal data
  • C13H8N4

  • Mr = 220.23

  • Orthorhombic, P b c a

  • a = 14.569 (2) Å

  • b = 7.8623 (12) Å

  • c = 17.042 (3) Å

  • V = 1952.1 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.26 × 0.18 × 0.16 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.985

  • 5772 measured reflections

  • 1756 independent reflections

  • 1025 reflections with I > 2σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.123

  • S = 1.00

  • 1756 reflections

  • 186 parameters

  • All H-atom parameters refined

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H8⋯N1i 0.92 (3) 2.47 (3) 3.104 (3) 126 (2)
N3—H8⋯N2i 0.92 (3) 2.18 (3) 3.017 (3) 150 (2)
Symmetry code: (i) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

(1,10)phenanthroline is widely used to synthetize metal-complex as a auxiliary ligand. In our laboratory earlier studies, we have successfully obtained some metal-complex with (1,10)phenanthroline.We report here the crystal structure of the title compound, Fig. 1. The title compound, is essentially planar (r.m.s. deviation for all non-H atoms = 0.025 (3)Å). In the crystal the molecules are connected through one weak bifurcated N—H···N hydrogen bonds, Fig. 2, Table 1 and π-π stacking interactions between pyridine and imidazole rings [distance centroid – centroid 3.631 (8) Å] and between pyridine and benzene rings [distance centroid–centroid 3.675 (5); 3.666 (2) Å] respectively.

Related literature top

For our previous work based on 1,10-phenanthroline as anauxiliary ligand, see: Song et al. (2009); Hao et al. (2008). For background to 1,10-phenanthroline complexes, see: Chesnut et al. (1999).

Experimental top

Imidazo(4,5-f)(1,10)phenanthroline was purchased from Jinan Henghua science and technology limited company and recristallized of an alkaline solution.

Refinement top

All H-atoms in this structure were located from differences Fourier syntheses and were refined isotropically.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular configuration and atom numbering scheme for the title complex showing 30% probability ellipsoids.
[Figure 2] Fig. 2. Part of the crystal structure showing one dimensional chain along (100).
5H-Imidazo[4,5-f][1,10]phenanthroline top
Crystal data top
C13H8N4F(000) = 912
Mr = 220.23Dx = 1.499 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 799 reflections
a = 14.569 (2) Åθ = 2.2–27.5°
b = 7.8623 (12) ŵ = 0.10 mm1
c = 17.042 (3) ÅT = 296 K
V = 1952.1 (5) Å3Block, yellow
Z = 80.26 × 0.18 × 0.16 mm
Data collection top
Bruker APEXII CCD
diffractometer
1756 independent reflections
Radiation source: fine-focus sealed tube1025 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
ϕ and ω scansθmax = 25.2°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 1710
Tmin = 0.980, Tmax = 0.985k = 99
5772 measured reflectionsl = 2020
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123All H-atom parameters refined
S = 1.00 w = 1/[σ2(Fo2) + (0.0606P)2]
where P = (Fo2 + 2Fc2)/3
1756 reflections(Δ/σ)max < 0.001
186 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C13H8N4V = 1952.1 (5) Å3
Mr = 220.23Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 14.569 (2) ŵ = 0.10 mm1
b = 7.8623 (12) ÅT = 296 K
c = 17.042 (3) Å0.26 × 0.18 × 0.16 mm
Data collection top
Bruker APEXII CCD
diffractometer
1756 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
1025 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.985Rint = 0.053
5772 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.123All H-atom parameters refined
S = 1.00Δρmax = 0.18 e Å3
1756 reflectionsΔρmin = 0.15 e Å3
186 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N20.08583 (13)0.0741 (3)0.18218 (11)0.0428 (6)
C130.17857 (16)0.0868 (3)0.18200 (12)0.0349 (6)
C40.22247 (15)0.1620 (3)0.25102 (12)0.0347 (6)
N10.16716 (13)0.2161 (3)0.30974 (10)0.0423 (6)
C50.31923 (15)0.1740 (3)0.25518 (12)0.0355 (6)
N30.46339 (14)0.1051 (3)0.17574 (13)0.0471 (6)
N40.39502 (14)0.0018 (3)0.06803 (11)0.0449 (6)
C110.09449 (19)0.0623 (4)0.05615 (15)0.0487 (7)
C120.04717 (19)0.0004 (3)0.12071 (16)0.0494 (7)
C30.20665 (19)0.2840 (3)0.37251 (14)0.0460 (7)
C20.30087 (18)0.3045 (3)0.38092 (14)0.0439 (7)
C10.35746 (19)0.2504 (3)0.32252 (13)0.0416 (6)
C60.37040 (15)0.1101 (3)0.18996 (12)0.0365 (6)
C70.4727 (2)0.0392 (3)0.10225 (15)0.0514 (7)
C80.32970 (16)0.0437 (3)0.12418 (12)0.0373 (6)
C90.23250 (15)0.0280 (3)0.11878 (12)0.0356 (6)
C100.18762 (19)0.0478 (3)0.05489 (14)0.0445 (7)
H70.5396 (16)0.027 (3)0.0759 (12)0.042 (6)*
H60.2264 (16)0.088 (3)0.0121 (15)0.056 (8)*
H40.0192 (17)0.012 (3)0.1232 (13)0.045 (7)*
H10.4230 (16)0.270 (3)0.3229 (13)0.051 (8)*
H50.0590 (16)0.125 (3)0.0140 (15)0.063 (8)*
H30.1640 (15)0.322 (3)0.4153 (13)0.046 (7)*
H20.3235 (16)0.353 (3)0.4266 (14)0.053 (7)*
H80.5057 (19)0.136 (4)0.2135 (18)0.074 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0304 (12)0.0574 (14)0.0407 (12)0.0012 (10)0.0020 (9)0.0005 (10)
C130.0326 (13)0.0403 (15)0.0318 (12)0.0009 (11)0.0029 (11)0.0052 (10)
C40.0343 (13)0.0379 (14)0.0319 (11)0.0024 (12)0.0035 (11)0.0054 (10)
N10.0396 (12)0.0519 (14)0.0355 (11)0.0021 (10)0.0037 (10)0.0001 (9)
C50.0350 (14)0.0389 (14)0.0326 (12)0.0016 (11)0.0027 (11)0.0075 (10)
N30.0308 (12)0.0644 (15)0.0462 (13)0.0046 (11)0.0024 (11)0.0001 (11)
N40.0334 (12)0.0646 (15)0.0368 (11)0.0021 (11)0.0034 (10)0.0000 (10)
C110.0435 (17)0.0584 (18)0.0441 (15)0.0023 (14)0.0125 (13)0.0028 (13)
C120.0326 (15)0.0651 (19)0.0505 (15)0.0029 (14)0.0084 (13)0.0022 (13)
C30.0488 (17)0.0546 (18)0.0346 (14)0.0041 (13)0.0018 (12)0.0029 (11)
C20.0511 (17)0.0462 (16)0.0344 (13)0.0027 (13)0.0045 (12)0.0036 (11)
C10.0403 (15)0.0443 (15)0.0403 (14)0.0014 (13)0.0053 (13)0.0029 (11)
C60.0305 (13)0.0445 (15)0.0344 (12)0.0013 (11)0.0015 (10)0.0047 (11)
C70.0401 (17)0.0647 (19)0.0495 (15)0.0122 (15)0.0068 (14)0.0010 (13)
C80.0335 (14)0.0447 (16)0.0338 (12)0.0021 (12)0.0013 (11)0.0039 (10)
C90.0375 (14)0.0372 (14)0.0321 (12)0.0020 (11)0.0006 (10)0.0048 (10)
C100.0471 (17)0.0518 (17)0.0346 (13)0.0026 (14)0.0025 (12)0.0009 (11)
Geometric parameters (Å, º) top
N2—C121.326 (3)C11—C101.362 (4)
N2—C131.355 (3)C11—C121.387 (4)
C13—C91.411 (3)C11—H51.01 (3)
C13—C41.464 (3)C12—H40.97 (2)
C4—N11.353 (3)C3—C21.390 (4)
C4—C51.415 (3)C3—H31.00 (2)
N1—C31.327 (3)C2—C11.360 (3)
C5—C11.410 (3)C2—H20.93 (2)
C5—C61.429 (3)C1—H10.97 (2)
N3—C71.362 (3)C6—C81.372 (3)
N3—C61.377 (3)C7—H71.08 (2)
N3—H80.92 (3)C8—C91.424 (3)
N4—C71.314 (3)C9—C101.403 (3)
N4—C81.396 (3)C10—H60.98 (3)
C12—N2—C13117.0 (2)C2—C3—H3120.2 (13)
N2—C13—C9122.2 (2)C1—C2—C3119.2 (2)
N2—C13—C4117.63 (19)C1—C2—H2121.8 (15)
C9—C13—C4120.2 (2)C3—C2—H2119.0 (15)
N1—C4—C5122.4 (2)C2—C1—C5119.3 (2)
N1—C4—C13117.4 (2)C2—C1—H1123.0 (14)
C5—C4—C13120.16 (19)C5—C1—H1117.5 (14)
C3—N1—C4117.7 (2)C8—C6—N3105.7 (2)
C1—C5—C4117.6 (2)C8—C6—C5122.9 (2)
C1—C5—C6125.2 (2)N3—C6—C5131.3 (2)
C4—C5—C6117.2 (2)N4—C7—N3114.5 (2)
C7—N3—C6105.7 (2)N4—C7—H7124.9 (11)
C7—N3—H8132.4 (17)N3—C7—H7120.5 (11)
C6—N3—H8121.7 (17)C6—C8—N4111.3 (2)
C7—N4—C8102.7 (2)C6—C8—C9121.0 (2)
C10—C11—C12118.6 (2)N4—C8—C9127.7 (2)
C10—C11—H5122.6 (13)C10—C9—C13118.2 (2)
C12—C11—H5118.7 (13)C10—C9—C8123.4 (2)
N2—C12—C11124.8 (2)C13—C9—C8118.4 (2)
N2—C12—H4115.4 (14)C11—C10—C9119.2 (2)
C11—C12—H4119.7 (14)C11—C10—H6124.2 (14)
N1—C3—C2123.9 (2)C9—C10—H6116.6 (14)
N1—C3—H3115.9 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H8···N1i0.92 (3)2.47 (3)3.104 (3)126 (2)
N3—H8···N2i0.92 (3)2.18 (3)3.017 (3)150 (2)
Symmetry code: (i) x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H8N4
Mr220.23
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)14.569 (2), 7.8623 (12), 17.042 (3)
V3)1952.1 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.26 × 0.18 × 0.16
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.980, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
5772, 1756, 1025
Rint0.053
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.123, 1.00
No. of reflections1756
No. of parameters186
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.18, 0.15

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H8···N1i0.92 (3)2.47 (3)3.104 (3)126 (2)
N3—H8···N2i0.92 (3)2.18 (3)3.017 (3)150 (2)
Symmetry code: (i) x+1/2, y, z+1/2.
 

Acknowledgements

We acknowledge the Public Science and Technology Research Funds Projects of Ocean (grant No. 2000905021), the Guangdong Oceanic Fisheries Technology Promotion Project [grant No. A2009003–018(c)], the Guangdong Chinese Academy of Science Comprehensive Strategic Cooperation Project (grant No. 2009B091300121) and the Guangdong Province Key Project in the Field of Social Development [grant No. A2009011–007(c)].

References

First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChesnut, D.-J., Haushalter, R.-C. & Zubieta, J. (1999). Inorg. Chim. Acta, 292, 41–51.  Web of Science CSD CrossRef CAS Google Scholar
First citationHao, X.-M., Gu, C.-S., Song, W.-D. & Liu, J.-W. (2008). Acta Cryst. E64, m1052.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSong, W.-D., Wang, H., Hu, S.-W., Qin, P.-W. & Li, S.-J. (2009). Acta Cryst. E65, m701.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1448
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