Literature DB >> 22969596

2-(4-Fluoro-phen-yl)-1-phenyl-1H-benzimidazole.

K Jayamoorthy, S Rosepriya, A Thiruvalluvar, J Jayabharathi, R J Butcher.   

Abstract

In the title mol-ecule, C(19)H(13)FN(2), the benzimidazole unit is close to planar [maximum deviation = 0.0342 (9) Å] and forms dihedral angles of 58.94 (3) and 51.43 (3)° with the phenyl and fluoro-benzene rings, respectively; the dihedral angle between the phenyl and fluoro-benzene rings is 60.17 (6)°. In the crystal, three C-H⋯F hydrogen bonds and two weak C-H⋯π inter-actions involving the fused benzene ring lead to a three-dimensional architecture.

Entities:  

Year:  2012        PMID： 22969596      PMCID： PMC3435725          DOI： 10.1107/S1600536812035155

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For linear and non-linear optical properties of benzimidazole compounds, see: Cross et al. (1995 ▶); Bu et al. (1996 ▶); Dirk et al. (1990 ▶). For a related structure, see: Rosepriya et al. (2011 ▶).

Experimental

Crystal data

C19H13FN2 M = 288.31 Monoclinic, a = 8.7527 (4) Å b = 10.1342 (4) Å c = 17.0211 (6) Å β = 104.187 (4)° V = 1463.75 (11) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 123 K 0.47 × 0.42 × 0.15 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.961, T max = 1.000 13721 measured reflections 7347 independent reflections 5352 reflections with I > 2σ(I) R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.063 wR(F 2) = 0.160 S = 1.04 7347 reflections 199 parameters H-atom parameters constrained Δρmax = 0.52 e Å−3 Δρmin = −0.22 e Å−3 Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035155/tk5141sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035155/tk5141Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812035155/tk5141Isup3.cdx Supplementary material file. DOI: 10.1107/S1600536812035155/tk5141Isup4.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H13FN2F(000) = 600
Mr = 288.31Dx = 1.308 Mg m−3
Monoclinic, P21/nMelting point: 369 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 8.7527 (4) ÅCell parameters from 3202 reflections
b = 10.1342 (4) Åθ = 3.1–37.6°
c = 17.0211 (6) ŵ = 0.09 mm−1
β = 104.187 (4)°T = 123 K
V = 1463.75 (11) Å3Plate, colourless
Z = 40.47 × 0.42 × 0.15 mm
Agilent Xcalibur Ruby Gemini diffractometer7347 independent reflections
Radiation source: Enhance (Mo) X-ray Source5352 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 10.5081 pixels mm-1θmax = 37.7°, θmin = 3.1°
ω scansh = −12→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)k = −12→17
Tmin = 0.961, Tmax = 1.000l = −28→24
13721 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0685P)2 + 0.2726P] where P = (Fo2 + 2Fc2)/3
7347 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.52 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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 > 2σ(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.
xyzUiso*/Ueq
F40.45822 (10)−0.05502 (7)0.23042 (4)0.0296 (2)
N10.25329 (11)0.44506 (9)−0.01000 (5)0.0181 (2)
N30.32447 (11)0.53932 (9)0.11392 (5)0.0204 (2)
C20.30699 (12)0.42744 (10)0.07314 (6)0.0181 (2)
C40.27719 (14)0.77382 (11)0.06432 (7)0.0224 (3)
C50.22041 (14)0.84918 (11)−0.00490 (7)0.0241 (3)
C60.16727 (14)0.79006 (11)−0.08140 (7)0.0242 (3)
C70.17379 (14)0.65470 (11)−0.09192 (6)0.0227 (3)
C80.23331 (12)0.57999 (10)−0.02222 (6)0.0184 (2)
C90.28005 (12)0.63684 (10)0.05527 (6)0.0192 (2)
C110.21724 (12)0.34608 (10)−0.07164 (6)0.0181 (2)
C120.29236 (14)0.34944 (12)−0.13497 (6)0.0250 (3)
C130.25650 (17)0.25270 (14)−0.19472 (7)0.0326 (4)
C140.14865 (18)0.15428 (13)−0.19126 (7)0.0342 (4)
C150.07463 (16)0.15197 (12)−0.12781 (8)0.0296 (3)
C160.10831 (13)0.24826 (11)−0.06771 (6)0.0222 (3)
C210.34251 (12)0.29683 (10)0.11128 (6)0.0184 (2)
C220.43985 (13)0.20730 (11)0.08453 (6)0.0207 (3)
C230.47933 (13)0.08832 (11)0.12460 (6)0.0226 (3)
C240.41834 (13)0.06137 (11)0.19050 (6)0.0216 (3)
C250.31950 (14)0.14570 (11)0.21819 (6)0.0240 (3)
C260.28287 (14)0.26534 (11)0.17816 (6)0.0224 (3)
H40.312070.813170.114910.0269*
H50.217530.94056−0.000490.0289*
H60.126610.84318−0.126210.0290*
H70.140300.61573−0.142710.0273*
H120.365220.41522−0.137270.0299*
H130.305490.25419−0.237410.0391*
H140.125810.08983−0.231330.0410*
H150.002250.08581−0.125470.0355*
H160.058370.24707−0.025380.0266*
H220.478380.227480.039660.0248*
H230.545000.028340.107620.0271*
H250.278860.123320.262040.0288*
H260.218080.325140.195960.0269*
U11U22U33U12U13U23
F40.0397 (4)0.0227 (3)0.0241 (3)0.0008 (3)0.0033 (3)0.0082 (3)
N10.0235 (4)0.0161 (3)0.0140 (3)−0.0019 (3)0.0035 (3)−0.0001 (3)
N30.0259 (4)0.0195 (4)0.0158 (3)−0.0011 (3)0.0051 (3)−0.0005 (3)
C20.0208 (4)0.0193 (4)0.0144 (3)−0.0009 (3)0.0047 (3)0.0010 (3)
C40.0266 (5)0.0188 (4)0.0221 (4)−0.0028 (4)0.0065 (4)−0.0029 (4)
C50.0275 (5)0.0183 (4)0.0280 (5)−0.0008 (4)0.0096 (4)0.0009 (4)
C60.0279 (5)0.0209 (5)0.0235 (4)0.0007 (4)0.0059 (4)0.0055 (4)
C70.0279 (5)0.0217 (5)0.0174 (4)−0.0007 (4)0.0032 (3)0.0028 (3)
C80.0214 (4)0.0170 (4)0.0167 (4)−0.0021 (3)0.0045 (3)0.0002 (3)
C90.0214 (4)0.0197 (4)0.0167 (4)−0.0021 (3)0.0048 (3)−0.0003 (3)
C110.0203 (4)0.0186 (4)0.0148 (3)0.0007 (3)0.0030 (3)−0.0010 (3)
C120.0285 (5)0.0289 (5)0.0192 (4)0.0028 (4)0.0091 (4)0.0010 (4)
C130.0437 (7)0.0362 (7)0.0192 (4)0.0128 (6)0.0102 (5)−0.0029 (4)
C140.0464 (8)0.0263 (6)0.0244 (5)0.0114 (5)−0.0017 (5)−0.0089 (4)
C150.0329 (6)0.0203 (5)0.0307 (5)0.0001 (4)−0.0017 (4)−0.0051 (4)
C160.0236 (5)0.0207 (4)0.0211 (4)−0.0011 (4)0.0034 (3)−0.0015 (4)
C210.0211 (4)0.0194 (4)0.0144 (3)−0.0013 (3)0.0039 (3)0.0009 (3)
C220.0230 (4)0.0222 (5)0.0180 (4)0.0003 (4)0.0073 (3)0.0027 (3)
C230.0244 (5)0.0219 (5)0.0218 (4)0.0019 (4)0.0062 (4)0.0024 (4)
C240.0266 (5)0.0189 (4)0.0170 (4)−0.0022 (4)0.0010 (3)0.0042 (3)
C250.0322 (5)0.0244 (5)0.0167 (4)−0.0023 (4)0.0086 (4)0.0027 (4)
C260.0278 (5)0.0233 (5)0.0178 (4)0.0009 (4)0.0090 (4)0.0008 (3)
F4—C241.3633 (13)C21—C221.3952 (15)
N1—C21.3890 (13)C21—C261.4005 (15)
N1—C81.3877 (14)C22—C231.3867 (15)
N1—C111.4298 (13)C23—C241.3825 (15)
N3—C21.3186 (13)C24—C251.3787 (16)
N3—C91.3908 (13)C25—C261.3893 (15)
C2—C211.4735 (14)C4—H40.9300
C4—C51.3897 (16)C5—H50.9300
C4—C91.3976 (15)C6—H60.9300
C5—C61.4050 (16)C7—H70.9300
C6—C71.3864 (16)C12—H120.9300
C7—C81.3961 (14)C13—H130.9300
C8—C91.4052 (14)C14—H140.9300
C11—C121.3939 (15)C15—H150.9300
C11—C161.3883 (15)C16—H160.9300
C12—C131.3919 (17)C22—H220.9300
C13—C141.384 (2)C23—H230.9300
C14—C151.3891 (19)C25—H250.9300
C15—C161.3920 (17)C26—H260.9300
C2—N1—C8106.15 (8)F4—C24—C25118.13 (9)
C2—N1—C11128.03 (9)C23—C24—C25123.67 (10)
C8—N1—C11125.75 (8)C24—C25—C26117.52 (10)
C2—N3—C9104.91 (8)C21—C26—C25120.69 (10)
N1—C2—N3113.10 (9)C5—C4—H4121.00
N1—C2—C21123.13 (9)C9—C4—H4121.00
N3—C2—C21123.76 (9)C4—C5—H5119.00
C5—C4—C9117.69 (10)C6—C5—H5119.00
C4—C5—C6121.32 (10)C5—C6—H6119.00
C5—C6—C7121.80 (10)C7—C6—H6119.00
C6—C7—C8116.45 (10)C6—C7—H7122.00
N1—C8—C7131.97 (9)C8—C7—H7122.00
N1—C8—C9105.45 (8)C11—C12—H12121.00
C7—C8—C9122.51 (9)C13—C12—H12121.00
N3—C9—C4129.50 (9)C12—C13—H13120.00
N3—C9—C8110.38 (9)C14—C13—H13120.00
C4—C9—C8120.12 (9)C13—C14—H14120.00
N1—C11—C12119.29 (10)C15—C14—H14120.00
N1—C11—C16119.75 (9)C14—C15—H15120.00
C12—C11—C16120.96 (10)C16—C15—H15120.00
C11—C12—C13118.90 (11)C11—C16—H16120.00
C12—C13—C14120.69 (12)C15—C16—H16120.00
C13—C14—C15119.87 (12)C21—C22—H22120.00
C14—C15—C16120.29 (12)C23—C22—H22120.00
C11—C16—C15119.30 (10)C22—C23—H23121.00
C2—C21—C22121.34 (9)C24—C23—H23121.00
C2—C21—C26118.84 (9)C24—C25—H25121.00
C22—C21—C26119.75 (10)C26—C25—H25121.00
C21—C22—C23120.23 (10)C21—C26—H26120.00
C22—C23—C24118.14 (10)C25—C26—H26120.00
F4—C24—C23118.21 (10)
C8—N1—C2—N3−0.88 (13)C6—C7—C8—N1178.40 (12)
C8—N1—C2—C21179.88 (10)C6—C7—C8—C91.94 (17)
C11—N1—C2—N3−178.02 (10)N1—C8—C9—N3−1.25 (12)
C11—N1—C2—C212.74 (17)N1—C8—C9—C4178.72 (10)
C2—N1—C8—C7−175.66 (12)C7—C8—C9—N3176.02 (10)
C2—N1—C8—C91.24 (12)C7—C8—C9—C4−4.00 (17)
C11—N1—C8—C71.56 (19)N1—C11—C12—C13−179.97 (12)
C11—N1—C8—C9178.46 (10)C16—C11—C12—C130.00 (17)
C2—N1—C11—C12−123.95 (12)N1—C11—C16—C15−179.68 (10)
C2—N1—C11—C1656.07 (16)C12—C11—C16—C150.33 (17)
C8—N1—C11—C1259.44 (15)C11—C12—C13—C14−0.32 (19)
C8—N1—C11—C16−120.54 (12)C12—C13—C14—C150.3 (2)
C9—N3—C2—N10.11 (13)C13—C14—C15—C160.1 (2)
C9—N3—C2—C21179.34 (10)C14—C15—C16—C11−0.36 (18)
C2—N3—C9—C4−179.25 (12)C2—C21—C22—C23176.01 (10)
C2—N3—C9—C80.72 (12)C26—C21—C22—C23−0.90 (16)
N1—C2—C21—C2250.81 (15)C2—C21—C26—C25−177.04 (10)
N1—C2—C21—C26−132.26 (11)C22—C21—C26—C25−0.06 (17)
N3—C2—C21—C22−128.35 (12)C21—C22—C23—C240.67 (16)
N3—C2—C21—C2648.58 (16)C22—C23—C24—F4−179.40 (10)
C9—C4—C5—C60.15 (18)C22—C23—C24—C250.53 (17)
C5—C4—C9—N3−177.21 (11)F4—C24—C25—C26178.48 (10)
C5—C4—C9—C82.83 (17)C23—C24—C25—C26−1.45 (17)
C4—C5—C6—C7−2.2 (2)C24—C25—C26—C211.18 (17)
C5—C6—C7—C81.13 (18)
D—H···AD—HH···AD···AD—H···A
C4—H4···F4i0.932.463.3640 (14)164
C7—H7···F4ii0.932.433.3058 (13)157
C26—H26···F4iii0.932.523.4348 (14)166
C16—H16···Cg2iv0.932.753.5443 (12)144
C22—H22···Cg2v0.932.803.5245 (13)136
Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the fused benzene ring (C4–C9).

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C4—H4⋯F4i 0.932.463.3640 (14)164
C7—H7⋯F4ii 0.932.433.3058 (13)157
C26—H26⋯F4iii 0.932.523.4348 (14)166
C16—H16⋯Cg2iv 0.932.753.5443 (12)144
C22—H22⋯Cg2v 0.932.803.5245 (13)136

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

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