2-[4-(Tri­fluoro­meth­yl)phen­yl]-1H-benzimidazole

In the title compound, C₁₄H₉F₃N₂, the mean planes of the benzimidazole ring system and the tri­fluoro­methyl-substituted benzene ring form a dihedral angle of 30.1 (1)°. In the crystal, mol­ecules are linked by N—H...N hydrogen bonds into chains along [010]. Weak C—H...F hydrogen bonds and a weak C—H...π inter­action connect the chains into a two-dimensional network parallel to (001).

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.056
• wR factor = 0.159
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  F1      ..       2.57 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C14 H9 F3 N2
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      5.304 Check
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1 Note

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Why ?
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT242_ALERT_2_G Low       Ueq as Compared to Neighbors for .....        C14 Check
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          1 Why ?
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

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S1. Comment

Benzimidazole and its derivatives are regarded as a promising class of bio-active heterocyclic compounds that exhibit a range of biological activities such as antibacterial (Ozden et al., 2004), anticancer (Easman et al.,2001), anti-HIV and anti-inflammatory (Ansari & Lal 2009; Thakurdesai et al., 2007). In addition, compounds which contain fluorine have special bioactivity (Ulrich, 2004). The bond lengths and bond angles of the benzimidazole moiety in the title compound are in good agreement with those observed in related structures (Jian et al., 2006; Rashid, et al., 2007; Rosepriya et al., 2011). The title compound is closely related to our previously reported compounds (Fathima et al., 2013; Krishnamurthy et al., 2013). The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the benzimidazole ring system and the trifluoro-substituted benzene ring is 30.1 (1)°. In the crystal structure, molecules are linked by N—H···N hydrogen bonds to form chains parallel to [010]. In addition, weak C—H···F hydrogen bonds and a weak C—H···π interaction connect chains into a two-dimensional network parallel to (001) (Fig. 2). The weak C—H···π interaction involves the centroid of the N1/C5/C6/N2/C7 ring (Table 1). In addition, the crystal packing involves the presence of short F···F contacts of 2.915 (3) Å.

Related literature

For therapeutic and medicinal properties of benzimidazole derivatives, see: Ozden et al. (2004); Easman et al. (2001); Thakurdesai et al. (2007); Ansari & Lal (2009). For the bioactivity of fluorine-containing compounds, see: Ulrich (2004). For related structures, see: Jian et al. (2006); Rosepriya et al. (2011); Fathima et al. (2013); Krishnamurthy et al. (2013); Rashid et al. (2007).

S2. Experimental

A mixture of 4-(trifluoromethyl)bezaldehyde (20 mmol, 0.35 g) and o-phenyldiamine (20 mmol, 0.22 g) in benzene (5.0 ml) was refluxed for 6 hrs on a water bath. The reaction mixture was cooled. The solid separated, was filtered and dried (yield: 0.38 g, 78% and m.p. 538 K). The title compound was dissolved in ethyl acetate and kept aside for slow evaporation to obtain pale yellow crystals suitable for X-ray diffraction studies.

S3. Refinement

The H atoms were placed in calculated positions and refined in a riding-model approximation with C—H = 0.93 Å, N—H = 0.86 Å and with U_iso(H) = 1.2U_eq(N/C).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure showing hydrogen bonds with dotted lines. H-atoms not involved in hydrogen bonding have been excluded. The atoms labeled C13, N1 and C12 are related by the symmetry operators: -0.5+x, 1.5-y, -z; 1.5-x, 0.5+y, z and 0.5-x, -0.5+y, z, respectively.

2-[4-(Trifluoromethyl)phenyl]-1H-benzimidazole

Crystal data

C14H9F3N2	F(000) = 1072
Mr = 262.23	Dx = 1.518 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1671 reflections
a = 9.2292 (9) Å	θ = 2.7–27.0°
b = 9.8117 (10) Å	µ = 0.13 mm^−1
c = 25.347 (2) Å	T = 296 K
V = 2295.2 (4) Å^3	Block, yellow
Z = 8	0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer	2501 independent reflections
Radiation source: fine-focus sealed tube	1671 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→11
Tmin = 0.978, Tmax = 0.980	k = −12→12
13079 measured reflections	l = −32→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H-atom parameters constrained
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0847P)^2 + 2.1194P] where P = (Fo^2 + 2Fc^2)/3
2501 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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.

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

	x	y	z	Uiso*/Ueq
N1	0.7803 (2)	0.34060 (19)	−0.15282 (8)	0.0231 (5)
H1	0.7333	0.2656	−0.1490	0.028*
N2	0.8319 (2)	0.56324 (19)	−0.14790 (8)	0.0226 (5)
F1	0.13831 (19)	0.43903 (16)	−0.01444 (8)	0.0575 (6)
F2	0.09362 (17)	0.6088 (2)	−0.06475 (7)	0.0547 (6)
F3	0.20033 (18)	0.63865 (18)	0.00860 (7)	0.0495 (5)
C1	1.0744 (3)	0.5460 (3)	−0.19449 (10)	0.0266 (6)
H1A	1.0979	0.6380	−0.1922	0.032*
C2	1.1659 (3)	0.4549 (3)	−0.21894 (10)	0.0282 (6)
H2	1.2515	0.4866	−0.2339	0.034*
C3	1.1332 (3)	0.3152 (2)	−0.22181 (9)	0.0271 (6)
H3	1.1975	0.2567	−0.2387	0.033*
C4	1.0077 (3)	0.2629 (2)	−0.20016 (9)	0.0251 (5)
H4	0.9867	0.1703	−0.2014	0.030*
C5	0.9137 (2)	0.3561 (2)	−0.17622 (9)	0.0221 (5)
C6	0.9454 (2)	0.4960 (2)	−0.17332 (9)	0.0225 (5)
C7	0.7369 (2)	0.4661 (2)	−0.13685 (9)	0.0220 (5)
C8	0.5975 (2)	0.4891 (2)	−0.11017 (9)	0.0229 (5)
C9	0.4787 (3)	0.4059 (3)	−0.12079 (10)	0.0303 (6)
H9	0.4874	0.3348	−0.1449	0.036*
C10	0.3482 (3)	0.4286 (3)	−0.09573 (11)	0.0316 (6)
H10	0.2691	0.3729	−0.1029	0.038*
C11	0.3353 (3)	0.5344 (2)	−0.05983 (10)	0.0261 (6)
C12	0.4518 (3)	0.6180 (2)	−0.04903 (9)	0.0274 (6)
H12	0.4422	0.6892	−0.0251	0.033*
C13	0.5836 (3)	0.5953 (2)	−0.07410 (9)	0.0252 (5)
H13	0.6625	0.6512	−0.0668	0.030*
C14	0.1920 (3)	0.5553 (3)	−0.03327 (10)	0.0292 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0221 (10)	0.0181 (10)	0.0291 (11)	−0.0002 (8)	0.0020 (8)	0.0001 (8)
N2	0.0218 (10)	0.0200 (10)	0.0261 (11)	−0.0003 (8)	0.0011 (8)	−0.0008 (8)
F1	0.0508 (11)	0.0331 (10)	0.0887 (15)	−0.0011 (8)	0.0391 (10)	0.0039 (9)
F2	0.0301 (9)	0.0918 (15)	0.0422 (10)	0.0208 (9)	0.0039 (7)	0.0117 (9)
F3	0.0369 (10)	0.0623 (12)	0.0493 (10)	−0.0021 (8)	0.0102 (7)	−0.0253 (8)
C1	0.0237 (12)	0.0237 (13)	0.0325 (14)	−0.0018 (10)	0.0010 (10)	0.0015 (10)
C2	0.0226 (12)	0.0305 (14)	0.0315 (14)	−0.0013 (10)	0.0050 (10)	0.0051 (11)
C3	0.0264 (13)	0.0268 (13)	0.0283 (13)	0.0057 (10)	0.0013 (10)	−0.0019 (10)
C4	0.0268 (12)	0.0210 (12)	0.0275 (13)	0.0021 (10)	−0.0014 (10)	0.0004 (9)
C5	0.0204 (12)	0.0231 (12)	0.0228 (12)	0.0015 (9)	−0.0018 (9)	0.0009 (9)
C6	0.0220 (12)	0.0224 (12)	0.0230 (12)	0.0036 (9)	−0.0025 (9)	0.0005 (9)
C7	0.0215 (12)	0.0220 (12)	0.0226 (12)	0.0017 (9)	−0.0037 (10)	−0.0015 (9)
C8	0.0219 (12)	0.0220 (12)	0.0248 (12)	0.0015 (9)	−0.0009 (9)	0.0023 (9)
C9	0.0265 (13)	0.0255 (13)	0.0390 (15)	−0.0012 (10)	0.0022 (11)	−0.0092 (10)
C10	0.0248 (13)	0.0322 (15)	0.0378 (15)	−0.0050 (11)	0.0007 (11)	−0.0071 (11)
C11	0.0248 (13)	0.0253 (13)	0.0282 (13)	0.0026 (10)	0.0021 (10)	0.0007 (10)
C12	0.0306 (13)	0.0235 (13)	0.0282 (13)	0.0012 (10)	0.0028 (10)	−0.0051 (9)
C13	0.0255 (12)	0.0226 (12)	0.0274 (13)	−0.0024 (10)	−0.0006 (10)	−0.0014 (9)
C14	0.0299 (13)	0.0246 (13)	0.0332 (14)	0.0015 (10)	0.0017 (11)	−0.0005 (10)

Geometric parameters (Å, º)

N1—C7	1.357 (3)	C4—C5	1.399 (3)
N1—C5	1.375 (3)	C4—H4	0.9300
N1—H1	0.8600	C5—C6	1.406 (3)
N2—C7	1.325 (3)	C7—C8	1.471 (3)
N2—C6	1.395 (3)	C8—C13	1.393 (3)
F1—C14	1.332 (3)	C8—C9	1.393 (3)
F2—C14	1.318 (3)	C9—C10	1.379 (4)
F3—C14	1.342 (3)	C9—H9	0.9300
C1—C2	1.377 (3)	C10—C11	1.386 (3)
C1—C6	1.395 (3)	C10—H10	0.9300
C1—H1A	0.9300	C11—C12	1.380 (3)
C2—C3	1.405 (4)	C11—C14	1.498 (3)
C2—H2	0.9300	C12—C13	1.391 (3)
C3—C4	1.380 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C7—N1—C5	107.02 (19)	C13—C8—C9	119.5 (2)
C7—N1—H1	126.5	C13—C8—C7	119.8 (2)
C5—N1—H1	126.5	C9—C8—C7	120.7 (2)
C7—N2—C6	104.73 (18)	C10—C9—C8	120.2 (2)
C2—C1—C6	117.9 (2)	C10—C9—H9	119.9
C2—C1—H1A	121.0	C8—C9—H9	119.9
C6—C1—H1A	121.0	C9—C10—C11	119.9 (2)
C1—C2—C3	121.7 (2)	C9—C10—H10	120.1
C1—C2—H2	119.2	C11—C10—H10	120.1
C3—C2—H2	119.2	C12—C11—C10	120.6 (2)
C4—C3—C2	121.5 (2)	C12—C11—C14	121.2 (2)
C4—C3—H3	119.3	C10—C11—C14	118.3 (2)
C2—C3—H3	119.3	C11—C12—C13	119.8 (2)
C3—C4—C5	116.7 (2)	C11—C12—H12	120.1
C3—C4—H4	121.6	C13—C12—H12	120.1
C5—C4—H4	121.6	C12—C13—C8	120.0 (2)
N1—C5—C4	132.1 (2)	C12—C13—H13	120.0
N1—C5—C6	105.74 (19)	C8—C13—H13	120.0
C4—C5—C6	122.2 (2)	F2—C14—F1	107.5 (2)
N2—C6—C1	130.7 (2)	F2—C14—F3	106.0 (2)
N2—C6—C5	109.3 (2)	F1—C14—F3	105.1 (2)
C1—C6—C5	120.0 (2)	F2—C14—C11	113.0 (2)
N2—C7—N1	113.2 (2)	F1—C14—C11	111.8 (2)
N2—C7—C8	124.5 (2)	F3—C14—C11	112.9 (2)
N1—C7—C8	122.3 (2)
C6—C1—C2—C3	−1.3 (4)	N1—C7—C8—C13	150.3 (2)
C1—C2—C3—C4	−0.1 (4)	N2—C7—C8—C9	149.8 (2)
C2—C3—C4—C5	1.2 (3)	N1—C7—C8—C9	−30.0 (3)
C7—N1—C5—C4	−179.0 (2)	C13—C8—C9—C10	−0.1 (4)
C7—N1—C5—C6	−0.3 (2)	C7—C8—C9—C10	−179.7 (2)
C3—C4—C5—N1	177.6 (2)	C8—C9—C10—C11	0.0 (4)
C3—C4—C5—C6	−1.0 (3)	C9—C10—C11—C12	0.3 (4)
C7—N2—C6—C1	179.2 (2)	C9—C10—C11—C14	−179.7 (2)
C7—N2—C6—C5	−0.6 (2)	C10—C11—C12—C13	−0.4 (4)
C2—C1—C6—N2	−178.2 (2)	C14—C11—C12—C13	179.6 (2)
C2—C1—C6—C5	1.5 (3)	C11—C12—C13—C8	0.3 (4)
N1—C5—C6—N2	0.5 (2)	C9—C8—C13—C12	−0.1 (4)
C4—C5—C6—N2	179.4 (2)	C7—C8—C13—C12	179.6 (2)
N1—C5—C6—C1	−179.2 (2)	C12—C11—C14—F2	106.1 (3)
C4—C5—C6—C1	−0.3 (3)	C10—C11—C14—F2	−73.9 (3)
C6—N2—C7—N1	0.4 (3)	C12—C11—C14—F1	−132.4 (3)
C6—N2—C7—C8	−179.4 (2)	C10—C11—C14—F1	47.6 (3)
C5—N1—C7—N2	−0.1 (3)	C12—C11—C14—F3	−14.1 (3)
C5—N1—C7—C8	179.7 (2)	C10—C11—C14—F3	165.8 (2)
N2—C7—C8—C13	−29.9 (3)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the N1/C5/C6/N2/C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^i	0.86	2.07	2.914 (3)	165
C12—H12···F1^ii	0.93	2.57	3.374 (3)	144
C13—H13···F3^iii	0.93	2.55	3.275 (4)	134
C2—H2···Cg^iv	0.93	2.94	3.700 (3)	140

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) −x+1/2, y+1/2, z; (iii) x+1/2, −y+3/2, −z; (iv) x+1/2, y, −z+1/2.