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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3164.
Published online 2010 November 13. doi:  10.1107/S1600536810045666
PMCID: PMC3011630

2-Benzoyl-1H-benzimidazole

Abstract

In the title compound, C14H10N2O, the benzoyl ring and benzimidazole ring system are aligned at a dihedral angle of 50.2 (2)°. In the crystal, inter­molecular N—H(...)N hydrogen bonds between adjacent imidazole groups generate supra­molecular C(4) chains running along the b axis.

Related literature

For phototropism of 2-acetyl­benzimidazole and 2-benzoyl­benzimidazole, see: Chowdhury et al. (2005 [triangle]). For the crystal structure of 2-acetyl­benzimidazole, see: Yang et al. (2006 [triangle]).

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Object name is e-66-o3164-scheme1.jpg

Experimental

Crystal data

  • C14H10N2O
  • M r = 222.24
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3164-efi1.jpg
  • a = 14.7356 (8) Å
  • b = 9.9530 (12) Å
  • c = 15.7981 (12) Å
  • V = 2317.0 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.40 × 0.40 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 10324 measured reflections
  • 2658 independent reflections
  • 1885 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.115
  • S = 1.01
  • 2658 reflections
  • 159 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045666/xu5084sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045666/xu5084Isup2.hkl

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

Acknowledgments

We thank Beijing Normal University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Acetyl-2-benzimidazole and benzoyl-2-benzimidazole are reported to exhibit excited-state prototropism in solvents at different pH levels (Chowdhury et al., 2005). Acetyl-2-benzimidazole exists in the solid state as an N–H···O hydrogen bonded dimer; the molecule is essentially planar (Yang et al., 2006). With the larger phenyl ring in place of the methyl group, the aromatic analog (Scheme I) requires rotation of the aromatic ring in order to reduce strain; this is reflected in the 50.2 (2) ° dihedral angle between the phenyl and benzimidazolyl rings (Fig. 1). Adjacent molecules are linked into a chan by N–H···O hydrogen bonds (Fig. 2).

Experimental

The compound was synthesized by using a literature procedure (Chowdhury et al., 2005), and crystals were grown from a methanol solution of the compound.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C).

The amino H-atom was located in a difference Fourier map and was refined isotropically.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C14H11N2O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Hydrogen-bonded chain structure.

Crystal data

C14H10N2OF(000) = 928
Mr = 222.24Dx = 1.274 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2496 reflections
a = 14.7356 (8) Åθ = 2.8–26.7°
b = 9.9530 (12) ŵ = 0.08 mm1
c = 15.7981 (12) ÅT = 293 K
V = 2317.0 (4) Å3Block, colorless
Z = 80.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer1885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
graphiteθmax = 27.5°, θmin = 2.8°
ω scansh = −10→19
10324 measured reflectionsk = −12→11
2658 independent reflectionsl = −15→20

Refinement

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 atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115w = 1/[σ2(Fo2) + (0.0549P)2 + 0.2609P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
2658 reflectionsΔρmax = 0.16 e Å3
159 parametersΔρmin = −0.13 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0093 (12)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.38338 (7)0.51103 (10)0.45822 (7)0.0647 (3)
N10.23286 (7)0.52044 (10)0.35142 (7)0.0456 (3)
H10.2500 (10)0.6048 (17)0.3643 (9)0.066 (4)*
N20.22405 (7)0.29711 (9)0.35955 (7)0.0450 (3)
C10.16927 (9)0.48272 (12)0.29302 (8)0.0446 (3)
C20.11547 (10)0.55500 (15)0.23652 (9)0.0609 (4)
H20.11890.64810.23280.073*
C30.05747 (12)0.48239 (18)0.18687 (10)0.0733 (5)
H30.02070.52740.14830.088*
C40.05192 (13)0.34275 (18)0.19233 (10)0.0767 (5)
H40.01110.29720.15770.092*
C50.10482 (11)0.27110 (15)0.24714 (10)0.0647 (4)
H50.10110.17790.25010.078*
C60.16460 (9)0.34273 (12)0.29846 (8)0.0453 (3)
C70.26312 (9)0.40660 (11)0.38936 (7)0.0411 (3)
C80.33717 (9)0.41037 (12)0.45261 (8)0.0444 (3)
C90.35378 (9)0.28972 (13)0.50523 (8)0.0471 (3)
C100.28375 (11)0.21174 (15)0.53695 (9)0.0613 (4)
H100.22380.23260.52400.074*
C110.30339 (17)0.10285 (19)0.58787 (11)0.0904 (7)
H110.25660.05200.61100.108*
C120.3922 (2)0.0697 (2)0.60441 (13)0.1081 (8)
H120.4052−0.00530.63730.130*
C130.46157 (16)0.1462 (2)0.57286 (13)0.0942 (7)
H130.52140.12240.58400.113*
C140.44330 (11)0.25789 (16)0.52484 (9)0.0632 (4)
H140.49040.31190.50550.076*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0593 (6)0.0444 (6)0.0904 (8)−0.0143 (5)−0.0074 (5)0.0005 (5)
N10.0576 (7)0.0243 (5)0.0551 (6)−0.0016 (5)0.0001 (5)0.0018 (5)
N20.0574 (7)0.0269 (5)0.0506 (6)−0.0008 (4)−0.0037 (5)0.0015 (4)
C10.0526 (7)0.0335 (6)0.0477 (7)0.0013 (5)0.0040 (6)0.0032 (5)
C20.0731 (10)0.0441 (8)0.0656 (9)0.0079 (7)−0.0038 (8)0.0136 (7)
C30.0784 (11)0.0751 (11)0.0663 (9)0.0043 (9)−0.0174 (9)0.0174 (9)
C40.0894 (13)0.0752 (12)0.0656 (9)−0.0134 (10)−0.0262 (9)0.0048 (9)
C50.0858 (11)0.0455 (8)0.0630 (8)−0.0114 (7)−0.0168 (8)0.0004 (7)
C60.0561 (8)0.0329 (6)0.0469 (6)−0.0008 (5)−0.0013 (6)0.0019 (5)
C70.0486 (7)0.0273 (6)0.0475 (6)−0.0014 (5)0.0044 (5)0.0009 (5)
C80.0437 (7)0.0354 (6)0.0543 (7)−0.0020 (5)0.0046 (6)−0.0045 (6)
C90.0559 (8)0.0403 (7)0.0450 (6)−0.0009 (6)−0.0049 (6)−0.0037 (6)
C100.0725 (10)0.0583 (9)0.0531 (8)−0.0141 (7)−0.0062 (7)0.0077 (7)
C110.1331 (19)0.0743 (12)0.0637 (10)−0.0338 (12)−0.0211 (11)0.0238 (9)
C120.160 (2)0.0778 (14)0.0864 (13)−0.0021 (15)−0.0520 (15)0.0288 (11)
C130.1035 (16)0.0826 (14)0.0967 (14)0.0211 (12)−0.0447 (12)0.0051 (12)
C140.0632 (9)0.0625 (9)0.0641 (9)0.0056 (7)−0.0151 (7)−0.0065 (7)

Geometric parameters (Å, °)

O1—C81.2146 (14)C5—H50.9300
N1—C71.3571 (15)C7—C81.4800 (18)
N1—C11.3677 (17)C8—C91.4809 (18)
N1—H10.900 (17)C9—C101.3851 (19)
N2—C71.3195 (15)C9—C141.392 (2)
N2—C61.3802 (16)C10—C111.380 (2)
C1—C21.3938 (19)C10—H100.9300
C1—C61.3977 (17)C11—C121.375 (3)
C2—C31.367 (2)C11—H110.9300
C2—H20.9300C12—C131.369 (3)
C3—C41.395 (2)C12—H120.9300
C3—H30.9300C13—C141.372 (2)
C4—C51.366 (2)C13—H130.9300
C4—H40.9300C14—H140.9300
C5—C61.3933 (19)
C7—N1—C1107.09 (10)N2—C7—C8125.70 (11)
C7—N1—H1125.9 (10)N1—C7—C8121.28 (10)
C1—N1—H1127.0 (10)O1—C8—C7118.92 (12)
C7—N2—C6104.76 (10)O1—C8—C9122.35 (12)
N1—C1—C2132.85 (12)C7—C8—C9118.71 (10)
N1—C1—C6105.42 (11)C10—C9—C14119.88 (13)
C2—C1—C6121.73 (13)C10—C9—C8122.30 (13)
C3—C2—C1116.76 (14)C14—C9—C8117.79 (13)
C3—C2—H2121.6C11—C10—C9119.64 (17)
C1—C2—H2121.6C11—C10—H10120.2
C2—C3—C4121.88 (15)C9—C10—H10120.2
C2—C3—H3119.1C12—C11—C10119.92 (19)
C4—C3—H3119.1C12—C11—H11120.0
C5—C4—C3121.72 (15)C10—C11—H11120.0
C5—C4—H4119.1C13—C12—C11120.55 (18)
C3—C4—H4119.1C13—C12—H12119.7
C4—C5—C6117.55 (14)C11—C12—H12119.7
C4—C5—H5121.2C12—C13—C14120.36 (19)
C6—C5—H5121.2C12—C13—H13119.8
N2—C6—C5129.77 (12)C14—C13—H13119.8
N2—C6—C1109.86 (11)C13—C14—C9119.56 (17)
C5—C6—C1120.36 (12)C13—C14—H14120.2
N2—C7—N1112.86 (11)C9—C14—H14120.2
C7—N1—C1—C2179.42 (14)C1—N1—C7—C8176.10 (11)
C7—N1—C1—C6−0.39 (14)N2—C7—C8—O1160.44 (13)
N1—C1—C2—C3−179.47 (15)N1—C7—C8—O1−14.80 (19)
C6—C1—C2—C30.3 (2)N2—C7—C8—C9−17.95 (19)
C1—C2—C3—C40.2 (2)N1—C7—C8—C9166.81 (11)
C2—C3—C4—C5−0.6 (3)O1—C8—C9—C10142.64 (14)
C3—C4—C5—C60.5 (3)C7—C8—C9—C10−39.03 (18)
C7—N2—C6—C5−179.18 (15)O1—C8—C9—C14−35.36 (19)
C7—N2—C6—C1−0.19 (14)C7—C8—C9—C14142.97 (12)
C4—C5—C6—N2178.85 (14)C14—C9—C10—C110.0 (2)
C4—C5—C6—C10.0 (2)C8—C9—C10—C11−177.95 (14)
N1—C1—C6—N20.37 (14)C9—C10—C11—C12−2.2 (3)
C2—C1—C6—N2−179.47 (12)C10—C11—C12—C132.0 (3)
N1—C1—C6—C5179.46 (13)C11—C12—C13—C140.6 (3)
C2—C1—C6—C5−0.4 (2)C12—C13—C14—C9−2.8 (3)
C6—N2—C7—N1−0.06 (14)C10—C9—C14—C132.5 (2)
C6—N2—C7—C8−175.65 (11)C8—C9—C14—C13−179.45 (14)
C1—N1—C7—N20.29 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.90 (2)1.95 (2)2.829 (2)164 (1)

Symmetry codes: (i) −x+1/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5084).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chowdhury, P., Panja, S., Chatterjee, A., Bhattacharya, P. & Chakravorti, S. (2005). J. Photochem. Photobiol. A, 170, 131–141.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.
  • Yang, X.-Y., Li, Y., Li, Y., Li, X.-M. & Zhang, S.-S. (2006). Acta Cryst. E62, o1936–o1937.

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