organic compounds
1-(4-Fluorobenzyl)-2-(pyridin-2-yl)-1H-benzimidazole
aDepartment of Physics, Faculty of Education, Dicle University, 21280, Diyarbakır, Turkey, bDepartment of Physics, Institute of Sciences, Dicle University, 21280, Diyarbakır, Turkey, and cDepartment of Chemistry, Faculty of Science & Art, Harran University, 63300, Şanlıurfa, Turkey
*Correspondence e-mail: omer.celik@dicle.edu.tr
In the title compound, C19H14FN3, the dihedral angles between the benzimidazole unit (r.m.s. deviation= 0.017 Å) and the pyridine and benzene rings are 24.46 (4) and 81.87 (3)°, respectively. In the crystal, molecules are stacked along the a-axis direction by C—H⋯π interactions.
CCDC reference: 992223
Related literature
For the use of 2-(2-pyridyl)benzimidazole in coordination chemistry, see: Boca et al. (1997); De Castro et al. (1991); Khalil et al. (2001); Maekawa et al. (1994). For deprotonation of the NH group in 2-(2-pyridyl)benzimidazole, see: Chiswell et al. (1964); Harkins et al. (1956); Haga (1983). For functionalization of 2-(2-pyridyl)benzimidazole, see: Ali et al. (1998); Hossain et al. (2001); Sahin et al. (2010). For related structures, see: Çelik et al. (2007, 2009).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
CCDC reference: 992223
10.1107/S1600536814005947/bq2393sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005947/bq2393Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005947/bq2393Isup3.cml
A solution of the 2-pyridiylbenzimidazole (1.95 g, 10.0 mmol) in toluene (10 ml) and KOH was added (616 mg, 11.0 mmol) and stirred at 60 °C for 4 h. To this reaction mixture 4-florobenzyl bromide (1.89 g, 10.0 mmol) was added, then heated at this temperature for 24 h. Then volatiles were evaporated in vacuum to dryness. The residue was dissolved in CH2Cl2 and filtered via cannula on celite. The desired product was obtained after concentration of CH2Cl2 (15 ml) and then precipitating with hexane (30 ml). The off-white solid obtained in 80% yield. M.p. 94 °C. 1H NMR (400 MHz, CDCl3, δ p.p.m.): 6.13 (s, 2H, N—CH2); 6.90–6.94 (t, J = 8.0 Hz, 2H, Ar—CH); 7.15–7.18 (m, 2H, Ar—CH); 7.26–7.32 (m, 4H, Ar—CH); 7.81–7.86 (m, 2H, Ar—CH); 8.44 (d, J = 8.0 Hz, 1H, Ar—CH); 8.62 (d, J = 4.0 Hz, 1H, Ar—CH). 13C NMR (100.56 MHz, CDCl3, δ p.p.m.): 110.2; 115.1; 120.1; 122.2; 123.8; 124.3; 128.0; 142.2; 148.5; 150.1; 161.4. 19F NMR (376.266 MHz, CDCl3, δ p.p.m.): - 115.59.
Data collection: APEX2 (Bruker, 2007); cell
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: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).C19H14FN3 | F(000) = 632 |
Mr = 303.33 | Dx = 1.323 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 0 reflections |
a = 4.7363 (5) Å | θ = 2.4–26.7° |
b = 15.4102 (17) Å | µ = 0.09 mm−1 |
c = 20.953 (2) Å | T = 296 K |
β = 95.363 (8)° | Stick, orange |
V = 1522.6 (3) Å3 | 0.2 × 0.2 × 0.2 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 3133 independent reflections |
Radiation source: sealed tube | 2355 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ϕ and ω scans | θmax = 26.7°, θmin = 2.4° |
Absorption correction: multi-scan (Blessing, 1995) | h = −5→5 |
Tmin = 0.984, Tmax = 0.984 | k = −19→18 |
13325 measured reflections | l = −26→22 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: mixed |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0502P)2 + 0.1779P] where P = (Fo2 + 2Fc2)/3 |
3133 reflections | (Δ/σ)max = 0.001 |
208 parameters | Δρmax = 0.14 e Å−3 |
1 restraint | Δρmin = −0.17 e Å−3 |
C19H14FN3 | V = 1522.6 (3) Å3 |
Mr = 303.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.7363 (5) Å | µ = 0.09 mm−1 |
b = 15.4102 (17) Å | T = 296 K |
c = 20.953 (2) Å | 0.2 × 0.2 × 0.2 mm |
β = 95.363 (8)° |
Bruker APEXII CCD diffractometer | 3133 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 2355 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 0.984 | Rint = 0.027 |
13325 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 1 restraint |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 0.93 | Δρmax = 0.14 e Å−3 |
3133 reflections | Δρmin = −0.17 e Å−3 |
208 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.3612 (2) | 0.95634 (7) | 0.32306 (5) | 0.0598 (3) | |
N2 | 0.1288 (2) | 1.03423 (7) | 0.24400 (6) | 0.0669 (3) | |
C14 | 0.3980 (3) | 0.81860 (8) | 0.38380 (6) | 0.0574 (3) | |
C6 | 0.0419 (3) | 1.05982 (8) | 0.30241 (7) | 0.0629 (3) | |
C5 | 0.1882 (3) | 1.01343 (8) | 0.35209 (7) | 0.0607 (3) | |
C13 | 0.5514 (3) | 0.89547 (9) | 0.35911 (7) | 0.0661 (4) | |
H13A | 0.6512 | 0.9256 | 0.3951 | 0.079* | |
H13B | 0.6915 | 0.8750 | 0.3317 | 0.079* | |
C7 | 0.3181 (3) | 0.97274 (8) | 0.25818 (7) | 0.0602 (3) | |
C17 | 0.1266 (4) | 0.67652 (9) | 0.42898 (8) | 0.0785 (4) | |
F | −0.0115 (3) | 0.60689 (7) | 0.45190 (6) | 0.1195 (4) | |
C1 | −0.1590 (3) | 1.12201 (9) | 0.31618 (9) | 0.0762 (4) | |
H1 | −0.2638 | 1.1521 | 0.2836 | 0.091* | |
C4 | 0.1534 (3) | 1.02938 (10) | 0.41615 (8) | 0.0719 (4) | |
H4 | 0.2555 | 0.9989 | 0.4490 | 0.086* | |
C15 | 0.2114 (3) | 0.76997 (10) | 0.34407 (7) | 0.0736 (4) | |
H15 | 0.1766 | 0.7856 | 0.3012 | 0.088* | |
N3 | 0.5846 (3) | 0.85244 (9) | 0.22169 (7) | 0.0831 (4) | |
C19 | 0.4444 (3) | 0.79317 (11) | 0.44710 (7) | 0.0770 (4) | |
H19 | 0.5696 | 0.8248 | 0.4749 | 0.092* | |
C16 | 0.0746 (4) | 0.69844 (11) | 0.36643 (8) | 0.0856 (5) | |
H16 | −0.0506 | 0.6661 | 0.3391 | 0.103* | |
C8 | 0.4713 (3) | 0.93024 (9) | 0.20851 (7) | 0.0635 (4) | |
C11 | 0.7609 (4) | 0.85310 (15) | 0.11857 (10) | 0.0983 (6) | |
H11 | 0.8632 | 0.8251 | 0.0889 | 0.118* | |
C2 | −0.1960 (4) | 1.13709 (10) | 0.37944 (10) | 0.0835 (5) | |
H2 | −0.3286 | 1.1781 | 0.3897 | 0.100* | |
C18 | 0.3089 (4) | 0.72168 (11) | 0.47001 (8) | 0.0865 (5) | |
H18 | 0.3423 | 0.7050 | 0.5127 | 0.104* | |
C3 | −0.0396 (4) | 1.09246 (11) | 0.42858 (9) | 0.0818 (5) | |
H3 | −0.0664 | 1.1056 | 0.4709 | 0.098* | |
C9 | 0.4926 (4) | 0.97168 (11) | 0.15093 (8) | 0.0861 (5) | |
H9 | 0.4076 | 1.0254 | 0.1428 | 0.103* | |
C12 | 0.7260 (4) | 0.81593 (13) | 0.17637 (10) | 0.0989 (6) | |
H12 | 0.8060 | 0.7615 | 0.1848 | 0.119* | |
C10 | 0.6421 (5) | 0.93216 (14) | 0.10555 (9) | 0.1017 (6) | |
H10 | 0.6613 | 0.9593 | 0.0665 | 0.122* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0538 (6) | 0.0525 (6) | 0.0728 (7) | −0.0057 (5) | 0.0044 (5) | −0.0023 (5) |
N2 | 0.0652 (7) | 0.0542 (6) | 0.0812 (8) | −0.0007 (6) | 0.0058 (6) | 0.0017 (5) |
C14 | 0.0518 (7) | 0.0561 (7) | 0.0633 (8) | 0.0052 (6) | −0.0008 (6) | −0.0061 (6) |
C6 | 0.0578 (7) | 0.0471 (7) | 0.0847 (9) | −0.0100 (6) | 0.0115 (7) | −0.0031 (6) |
C5 | 0.0533 (7) | 0.0503 (7) | 0.0792 (9) | −0.0144 (6) | 0.0099 (6) | −0.0060 (6) |
C13 | 0.0524 (7) | 0.0691 (9) | 0.0748 (9) | −0.0043 (6) | −0.0048 (6) | −0.0033 (7) |
C7 | 0.0565 (7) | 0.0506 (7) | 0.0730 (9) | −0.0085 (6) | 0.0037 (6) | −0.0018 (6) |
C17 | 0.1041 (12) | 0.0522 (8) | 0.0826 (10) | 0.0003 (8) | 0.0259 (9) | −0.0004 (7) |
F | 0.1701 (11) | 0.0738 (6) | 0.1201 (9) | −0.0228 (7) | 0.0432 (8) | 0.0116 (6) |
C1 | 0.0679 (9) | 0.0543 (8) | 0.1076 (12) | −0.0041 (7) | 0.0143 (8) | −0.0013 (8) |
C4 | 0.0684 (9) | 0.0682 (9) | 0.0801 (10) | −0.0188 (8) | 0.0117 (7) | −0.0090 (7) |
C15 | 0.0845 (10) | 0.0723 (9) | 0.0620 (8) | −0.0157 (8) | −0.0036 (7) | −0.0007 (7) |
N3 | 0.0868 (9) | 0.0744 (9) | 0.0890 (9) | 0.0175 (7) | 0.0135 (7) | −0.0045 (7) |
C19 | 0.0821 (10) | 0.0777 (10) | 0.0679 (9) | 0.0005 (8) | −0.0102 (7) | −0.0059 (7) |
C16 | 0.1046 (12) | 0.0715 (10) | 0.0801 (10) | −0.0271 (9) | 0.0046 (9) | −0.0079 (8) |
C8 | 0.0572 (8) | 0.0603 (8) | 0.0726 (9) | −0.0070 (6) | 0.0036 (6) | −0.0066 (7) |
C11 | 0.0899 (12) | 0.1126 (15) | 0.0951 (13) | 0.0017 (12) | 0.0224 (10) | −0.0276 (11) |
C2 | 0.0741 (10) | 0.0606 (9) | 0.1198 (14) | −0.0072 (8) | 0.0304 (10) | −0.0160 (9) |
C18 | 0.1154 (13) | 0.0768 (11) | 0.0666 (9) | 0.0084 (10) | 0.0046 (9) | 0.0092 (8) |
C3 | 0.0811 (11) | 0.0713 (10) | 0.0966 (12) | −0.0190 (9) | 0.0276 (9) | −0.0210 (9) |
C9 | 0.1051 (13) | 0.0737 (10) | 0.0802 (10) | −0.0003 (9) | 0.0134 (9) | 0.0007 (8) |
C12 | 0.0997 (13) | 0.0955 (13) | 0.1023 (13) | 0.0277 (11) | 0.0142 (11) | −0.0161 (11) |
C10 | 0.1226 (16) | 0.1067 (15) | 0.0795 (11) | −0.0147 (13) | 0.0283 (11) | −0.0091 (10) |
N1—C7 | 1.3790 (17) | C4—H4 | 0.9300 |
N1—C5 | 1.3815 (17) | C15—C16 | 1.382 (2) |
N1—C13 | 1.4612 (17) | C15—H15 | 0.9300 |
N2—C7 | 1.3192 (17) | N3—C8 | 1.3319 (19) |
N2—C6 | 1.3845 (18) | N3—C12 | 1.336 (2) |
C14—C15 | 1.3778 (18) | C19—C18 | 1.383 (2) |
C14—C19 | 1.381 (2) | C19—H19 | 0.9300 |
C14—C13 | 1.5065 (19) | C16—H16 | 0.9300 |
C6—C5 | 1.393 (2) | C8—C9 | 1.377 (2) |
C6—C1 | 1.399 (2) | C11—C10 | 1.359 (3) |
C5—C4 | 1.389 (2) | C11—C12 | 1.364 (3) |
C13—H13A | 0.9700 | C11—H11 | 0.9300 |
C13—H13B | 0.9700 | C2—C3 | 1.392 (2) |
C7—C8 | 1.4765 (19) | C2—H2 | 0.9300 |
C17—C18 | 1.353 (2) | C18—H18 | 0.9300 |
C17—C16 | 1.354 (2) | C3—H3 | 0.9300 |
C17—F | 1.3671 (18) | C9—C10 | 1.379 (2) |
C1—C2 | 1.373 (2) | C9—H9 | 0.9300 |
C1—H1 | 0.9300 | C12—H12 | 0.9300 |
C4—C3 | 1.376 (2) | C10—H10 | 0.9300 |
C7—N1—C5 | 106.14 (11) | C16—C15—H15 | 119.2 |
C7—N1—C13 | 130.90 (12) | C8—N3—C12 | 116.78 (15) |
C5—N1—C13 | 122.93 (12) | C14—C19—C18 | 121.46 (14) |
C7—N2—C6 | 104.92 (12) | C14—C19—H19 | 119.3 |
C15—C14—C19 | 117.49 (13) | C18—C19—H19 | 119.3 |
C15—C14—C13 | 121.54 (12) | C17—C16—C15 | 118.58 (15) |
C19—C14—C13 | 120.95 (12) | C17—C16—H16 | 120.7 |
N2—C6—C5 | 110.25 (12) | C15—C16—H16 | 120.7 |
N2—C6—C1 | 129.90 (14) | N3—C8—C9 | 122.55 (15) |
C5—C6—C1 | 119.85 (14) | N3—C8—C7 | 117.91 (13) |
N1—C5—C4 | 131.82 (14) | C9—C8—C7 | 119.54 (14) |
N1—C5—C6 | 105.78 (12) | C10—C11—C12 | 118.21 (18) |
C4—C5—C6 | 122.37 (14) | C10—C11—H11 | 120.9 |
N1—C13—C14 | 112.85 (10) | C12—C11—H11 | 120.9 |
N1—C13—H13A | 109.0 | C1—C2—C3 | 121.54 (15) |
C14—C13—H13A | 109.0 | C1—C2—H2 | 119.2 |
N1—C13—H13B | 109.0 | C3—C2—H2 | 119.2 |
C14—C13—H13B | 109.0 | C17—C18—C19 | 118.58 (15) |
H13A—C13—H13B | 107.8 | C17—C18—H18 | 120.7 |
N2—C7—N1 | 112.87 (12) | C19—C18—H18 | 120.7 |
N2—C7—C8 | 121.89 (13) | C4—C3—C2 | 121.72 (16) |
N1—C7—C8 | 125.19 (13) | C4—C3—H3 | 119.1 |
C18—C17—C16 | 122.33 (15) | C2—C3—H3 | 119.1 |
C18—C17—F | 118.58 (15) | C8—C9—C10 | 118.93 (17) |
C16—C17—F | 119.09 (16) | C8—C9—H9 | 120.5 |
C2—C1—C6 | 117.76 (16) | C10—C9—H9 | 120.5 |
C2—C1—H1 | 121.1 | N3—C12—C11 | 124.37 (18) |
C6—C1—H1 | 121.1 | N3—C12—H12 | 117.8 |
C3—C4—C5 | 116.67 (16) | C11—C12—H12 | 117.8 |
C3—C4—H4 | 121.7 | C11—C10—C9 | 119.15 (18) |
C5—C4—H4 | 121.7 | C11—C10—H10 | 120.4 |
C14—C15—C16 | 121.56 (14) | C9—C10—H10 | 120.4 |
C14—C15—H15 | 119.2 | ||
C7—N2—C6—C5 | 1.27 (14) | C19—C14—C15—C16 | 0.1 (2) |
C7—N2—C6—C1 | −178.94 (13) | C13—C14—C15—C16 | 178.76 (15) |
C7—N1—C5—C4 | −176.42 (14) | C15—C14—C19—C18 | −0.1 (2) |
C13—N1—C5—C4 | 1.7 (2) | C13—C14—C19—C18 | −178.73 (14) |
C7—N1—C5—C6 | 1.84 (13) | C18—C17—C16—C15 | −0.5 (3) |
C13—N1—C5—C6 | 179.92 (11) | F—C17—C16—C15 | 178.77 (15) |
N2—C6—C5—N1 | −1.96 (14) | C14—C15—C16—C17 | 0.2 (3) |
C1—C6—C5—N1 | 178.22 (11) | C12—N3—C8—C9 | 0.9 (2) |
N2—C6—C5—C4 | 176.50 (12) | C12—N3—C8—C7 | −178.95 (14) |
C1—C6—C5—C4 | −3.32 (19) | N2—C7—C8—N3 | −158.51 (13) |
C7—N1—C13—C14 | −106.39 (15) | N1—C7—C8—N3 | 24.2 (2) |
C5—N1—C13—C14 | 76.04 (15) | N2—C7—C8—C9 | 21.6 (2) |
C15—C14—C13—N1 | 50.84 (18) | N1—C7—C8—C9 | −155.75 (14) |
C19—C14—C13—N1 | −130.59 (14) | C6—C1—C2—C3 | 0.1 (2) |
C6—N2—C7—N1 | −0.06 (15) | C16—C17—C18—C19 | 0.6 (3) |
C6—N2—C7—C8 | −177.69 (11) | F—C17—C18—C19 | −178.74 (15) |
C5—N1—C7—N2 | −1.16 (14) | C14—C19—C18—C17 | −0.2 (3) |
C13—N1—C7—N2 | −179.03 (12) | C5—C4—C3—C2 | 1.1 (2) |
C5—N1—C7—C8 | 176.39 (12) | C1—C2—C3—C4 | −1.9 (2) |
C13—N1—C7—C8 | −1.5 (2) | N3—C8—C9—C10 | −1.4 (3) |
N2—C6—C1—C2 | −177.38 (14) | C7—C8—C9—C10 | 178.46 (15) |
C5—C6—C1—C2 | 2.40 (19) | C8—N3—C12—C11 | 0.1 (3) |
N1—C5—C4—C3 | 179.55 (13) | C10—C11—C12—N3 | −0.7 (3) |
C6—C5—C4—C3 | 1.5 (2) | C12—C11—C10—C9 | 0.2 (3) |
Cg is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···Cgi | 0.97 | 2.94 | 3.486 (2) | 117 |
Symmetry code: (i) x−1, y, z. |
Cg is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···Cgi | 0.970 | 2.9345 | 3.486 (2) | 117.17 |
Symmetry code: (i) x−1, y, z. |
Acknowledgements
The authors are indebted to the X-ray laboratory of Dicle University Scientific and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer.
References
Ali, M. M., Sato, H., Haga, M., Tanaka, K., Yoshimura, A. & Ohno, T. (1998). Inorg. Chem. 37, 6176–6180. Web of Science CrossRef CAS Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Boca, R., Baran, P., Dlhan, L., Sima, J., Wiesinger, G., Renz, F., El-Ayaan, U. & Linert, W. (1997). Polyhedron, 16, 47–55. CrossRef CAS Web of Science Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Çelik, Ö., Kasumov, V. T. & Şahin, E. (2009). Acta Cryst. E65, o2786. Web of Science CSD CrossRef IUCr Journals Google Scholar
Çelik, Ö., Ulusoy, M., Taş, E. & Íde, S. (2007). Anal. Sci. 23, 185–186. Google Scholar
Chiswell, B., Lions, F. & Morris, B. S. (1964). Inorg. Chem. 3, 110–114. CrossRef CAS Web of Science Google Scholar
De Castro, B., Freire, C., Domingues, D. & Gomes, J. (1991). Polyhedron, 10, 2541–2549. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Haga, M. (1983). Inorg. Chim. Acta, 75, 29–35. CrossRef CAS Web of Science Google Scholar
Harkins, T. R., Walter, J. L., Harris, O. E. & Freiser, H. (1956). J. Am. Chem. Soc. 78, 260–264. CrossRef CAS Web of Science Google Scholar
Hossain, M. D., Haga, M., Gholamkhass, B., Nozaki, K., Tsushima, M., Ikeda, N. & Ohno, T. (2001). Collect Czech. Chem. Commun, 66, 307–337. Web of Science CrossRef CAS Google Scholar
Khalil, M. M. H., Ali, S. A. & Ramadan, R. M. (2001). Spectrochim. Acta Part A, 57, 1017–1024. Web of Science CrossRef Google Scholar
Maekawa, M., Munakata, M., Kuroda-Sowa, T. & Hachiya, K. (1994). Inorg. Chim. Acta, 227, 137–143. CrossRef CAS Web of Science Google Scholar
Sahin, C., Ulusoy, M., Zafer, C., Ozsoy, C., Varlikli, C., Dittrich, T., Cetinkaya, B. & Icli, S. (2010). Dyes Pigm. 84, 88–94. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The N—N type ligand system, 2-(2-pyridyl)benzimidazole has a venerable history in coordination chemistry (Harkins et al., 1956; Chiswell et al., 1964; De Castro et al., 1991; Maekawa et al., 1994; Khalil et al., 2001; Boca et al., 1997). Many of the reported complexes of 2-(2-pyridyl) benzimidazole have been of interest because of the possibility of deprotonation of the NH group of the imidazole unit, converting the ligand from neutral to anionic form with different properties (Harkins et al., 1956; Chiswell et al., 1964; Haga, 1983). The functionalization of 2-(2-pyridyl)benzimidazole at the externally directed NH position allows simple incorporation of 2-(2-pyridyl)benzimidazole units (Sahin et al., 2010; Hossain et al., 2001; Ali et al., 1998).
The molecular structure of title compound is shown in Figure 1. In the compound, the bond lengths of F—C17, N3—C12 and C1—C2 are 1.3671 (18) Å, 1.336 (2) Å and 1.373 (2) Å, respectively. C18—C17—F and N3—C8—C7 bond angles are 118.58 (13)° and 117.91 (13)°. F—C17—C18—C19 and C12—N3—C8—C7 torsion angles are -178.74 (15)° and -178.95 (14)°. Similar results are observed in the study of (Çelik et al., 2009; Çelik et al., 2007).
In the title compound, (Fig. 1), four planes were named as P1(N1/C5/C6/N2/C7), P2(N3/C8/C9/C10/C11/C12), P3(C1/C2/C3/C4/C5/C6), P4(C14/C15/C16/C17/C18/C19) and P5(N1/C5/C4/C3/C2/C1/C6/N2/C7). The five- and six-membered rings (N1/C5/C6/N2/C7) and (C1—C6) of the benzimidazole groups are almost co-planar with maximum deviations of -0.011Å for C5 and -0.017 Å for C6, respectively. Moreover the maximum deviations from P2 plane of C8, P4 plane of C17 and P5 plane of N2 are -0.007 Å, -0.003 Å and -0.034 Å, respectively.
In the compound, dihedral angles between P1—P2, P1—P3, P1—P4, P1—P5, P2—P3, P2—P4, P2—P5, P3—P4, P3—P5 and P4—P5 are 23.37 (5)°, 2.29 (5)°, 81.87 (3)°, 1.18 (4)°, 25.51 (5)°, and 73.68 (4)°, 24.46 (4)°, 81.94 (4)°, 1.11 (4)° and 81.87 (3)° respectively.
There is intermolecular C—H···Cg(π) type hydrogen bonds interactions in the crystal structure with the contact distances of 2.9345 Å between acceptor and donor atom and π-ring system defined as C1–C6 ring (Table 1.) and the molecules are stacked along a-axis with these C—H···π type hydrogen-bond interactions (Figure 2.).