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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 7| July 2014| Page o760
https://doi.org/10.1107/S1600536814012963

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

M. S. Krishnamurthya and Noor Shahina Beguma*

aDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, Karnataka, India
*Correspondence e-mail: noorsb@rediffmail.com

(Received 15 May 2014; accepted 4 June 2014; online 11 June 2014)

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).

CCDC reference: 1006709

Related literature

For therapeutic and medicinal properties of benzimidazole derivatives, see: Ozden et al. (2004[Ozden, S., Karatas, H., Yildiz, S. & Goker, H. (2004). Arch. Pharm. 337, 556-562.]); Easman et al. (2001[Easman, J., Puerstinger, G., Roth, T., Fiebig, H. H., Jenny, M., Jaeger, W., Heinisch, G. & Hofmann, J. (2001). Int. J. Cancer, 94, 89-96.]); Thakurdesai et al. (2007[Thakurdesai, P. A., Wadodkar, S. G. & Chopade, C. T. (2007). Pharmacol. Online, 1, 314-329.]); Ansari & Lal (2009[Ansari, K. F. & Lal, C. (2009). E. J. Med. Chem. 44, 4028-4033.]). For the bioactivity of fluorine-containing compounds, see: Ulrich (2004[Ulrich, H. (2004). US Patent No. 2 004 033 897.]). For related structures, see: Jian et al. (2006[Jian, F.-F., Yu, H.-Q., Qiao, Y.-B., Zhao, P.-S. & Xiao, H.-L. (2006). Acta Cryst. E62, o5194-o5195.]); Rosepriya et al. (2011[Rosepriya, S., Thiruvalluvar, A., Jayamoorthy, K., Jayabharathi, J. & Linden, A. (2011). Acta Cryst. E67, o3519.]); Fathima et al. (2013[Fathima, N., Krishnamurthy, M. S. & Begum, N. S. (2013). Acta Cryst. E69, o264.]); Krishnamurthy et al. (2013[Krishnamurthy, M. S., Fathima, N., Nagarajaiah, H. & Begum, N. S. (2013). Acta Cryst. E69, o1689.]); Rashid et al. (2007[Rashid, N., Tahir, M. K., Kanwal, S., Yusof, N. M. & Yamin, B. M. (2007). Acta Cryst. E63, o1402-o1403.]).

[Scheme 1]

Experimental

Crystal data

  • C14H9F3N2

  • Mr = 262.23

  • Orthorhombic, P b c a

  • a = 9.2292 (9) Å

  • b = 9.8117 (10) Å

  • c = 25.347 (2) Å

  • V = 2295.2 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 296 K

  • 0.18 × 0.16 × 0.16 mm
Data collection

  • Bruker SMART APEX CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker Axs Inc., Madison, Wisconcin, USA.]) Tmin = 0.978, Tmax = 0.980

  • 13079 measured reflections

  • 2501 independent reflections

  • 1671 reflections with I > 2σ(I)

  • Rint = 0.070
Refinement

  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.159

  • S = 0.90

  • 2501 reflections

  • 172 parameters

  • H-atom parameters constrained

  • Δρmax = 0.55 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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⋯N2i 0.86 2.07 2.914 (3) 165
C12—H12⋯F1ii 0.93 2.57 3.374 (3) 144
C13—H13⋯F3iii 0.93 2.55 3.275 (4) 134
C2—H2⋯Cgiv 0.93 2.94 3.700 (3) 140
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (iii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (iv) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker Axs Inc., Madison, Wisconcin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker Axs Inc., Madison, Wisconcin, USA.]); data reduction: SAINT-Plus; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information

CCDC reference: 1006709

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536814012963/lh5706sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814012963/lh5706Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814012963/lh5706Isup3.cml

checkCIF report


Comment top

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 top

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).

Experimental top

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.

Refinement top

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 Uiso(H) = 1.2Ueq(N/C).

Structure description top

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.

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).

Computing details top

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 top
[Figure 1] 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.
[Figure 2] 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 top
Crystal data top
C14H9F3N2F(000) = 1072
Mr = 262.23Dx = 1.518 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1671 reflections
a = 9.2292 (9) Åθ = 2.7–27.0°
b = 9.8117 (10) ŵ = 0.13 mm−1
c = 25.347 (2) ÅT = 296 K
V = 2295.2 (4) Å3Block, yellow
Z = 80.18 × 0.16 × 0.16 mm
Data collection top
Bruker SMART APEX CCD detector
diffractometer		2501 independent reflections
Radiation source: fine-focus sealed tube1671 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
ω scansθmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −11→11
Tmin = 0.978, Tmax = 0.980k = −12→12
13079 measured reflectionsl = −32→23
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 0.90 w = 1/[σ2(Fo2) + (0.0847P)2 + 2.1194P]
where P = (Fo2 + 2Fc2)/3
2501 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.55 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Crystal data top
C14H9F3N2V = 2295.2 (4) Å3
Mr = 262.23Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 9.2292 (9) ŵ = 0.13 mm−1
b = 9.8117 (10) ÅT = 296 K
c = 25.347 (2) Å0.18 × 0.16 × 0.16 mm
Data collection top
Bruker SMART APEX CCD detector
diffractometer		2501 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		1671 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.980Rint = 0.070
13079 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 0.90Δρmax = 0.55 e Å−3
2501 reflectionsΔρmin = −0.33 e Å−3
172 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.7803 (2)0.34060 (19)−0.15282 (8)0.0231 (5)
H10.73330.2656−0.14900.028*
N20.8319 (2)0.56324 (19)−0.14790 (8)0.0226 (5)
F10.13831 (19)0.43903 (16)−0.01444 (8)0.0575 (6)
F20.09362 (17)0.6088 (2)−0.06475 (7)0.0547 (6)
F30.20033 (18)0.63865 (18)0.00860 (7)0.0495 (5)
C11.0744 (3)0.5460 (3)−0.19449 (10)0.0266 (6)
H1A1.09790.6380−0.19220.032*
C21.1659 (3)0.4549 (3)−0.21894 (10)0.0282 (6)
H21.25150.4866−0.23390.034*
C31.1332 (3)0.3152 (2)−0.22181 (9)0.0271 (6)
H31.19750.2567−0.23870.033*
C41.0077 (3)0.2629 (2)−0.20016 (9)0.0251 (5)
H40.98670.1703−0.20140.030*
C50.9137 (2)0.3561 (2)−0.17622 (9)0.0221 (5)
C60.9454 (2)0.4960 (2)−0.17332 (9)0.0225 (5)
C70.7369 (2)0.4661 (2)−0.13685 (9)0.0220 (5)
C80.5975 (2)0.4891 (2)−0.11017 (9)0.0229 (5)
C90.4787 (3)0.4059 (3)−0.12079 (10)0.0303 (6)
H90.48740.3348−0.14490.036*
C100.3482 (3)0.4286 (3)−0.09573 (11)0.0316 (6)
H100.26910.3729−0.10290.038*
C110.3353 (3)0.5344 (2)−0.05983 (10)0.0261 (6)
C120.4518 (3)0.6180 (2)−0.04903 (9)0.0274 (6)
H120.44220.6892−0.02510.033*
C130.5836 (3)0.5953 (2)−0.07410 (9)0.0252 (5)
H130.66250.6512−0.06680.030*
C140.1920 (3)0.5553 (3)−0.03327 (10)0.0292 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0221 (10)0.0181 (10)0.0291 (11)−0.0002 (8)0.0020 (8)0.0001 (8)
N20.0218 (10)0.0200 (10)0.0261 (11)−0.0003 (8)0.0011 (8)−0.0008 (8)
F10.0508 (11)0.0331 (10)0.0887 (15)−0.0011 (8)0.0391 (10)0.0039 (9)
F20.0301 (9)0.0918 (15)0.0422 (10)0.0208 (9)0.0039 (7)0.0117 (9)
F30.0369 (10)0.0623 (12)0.0493 (10)−0.0021 (8)0.0102 (7)−0.0253 (8)
C10.0237 (12)0.0237 (13)0.0325 (14)−0.0018 (10)0.0010 (10)0.0015 (10)
C20.0226 (12)0.0305 (14)0.0315 (14)−0.0013 (10)0.0050 (10)0.0051 (11)
C30.0264 (13)0.0268 (13)0.0283 (13)0.0057 (10)0.0013 (10)−0.0019 (10)
C40.0268 (12)0.0210 (12)0.0275 (13)0.0021 (10)−0.0014 (10)0.0004 (9)
C50.0204 (12)0.0231 (12)0.0228 (12)0.0015 (9)−0.0018 (9)0.0009 (9)
C60.0220 (12)0.0224 (12)0.0230 (12)0.0036 (9)−0.0025 (9)0.0005 (9)
C70.0215 (12)0.0220 (12)0.0226 (12)0.0017 (9)−0.0037 (10)−0.0015 (9)
C80.0219 (12)0.0220 (12)0.0248 (12)0.0015 (9)−0.0009 (9)0.0023 (9)
C90.0265 (13)0.0255 (13)0.0390 (15)−0.0012 (10)0.0022 (11)−0.0092 (10)
C100.0248 (13)0.0322 (15)0.0378 (15)−0.0050 (11)0.0007 (11)−0.0071 (11)
C110.0248 (13)0.0253 (13)0.0282 (13)0.0026 (10)0.0021 (10)0.0007 (10)
C120.0306 (13)0.0235 (13)0.0282 (13)0.0012 (10)0.0028 (10)−0.0051 (9)
C130.0255 (12)0.0226 (12)0.0274 (13)−0.0024 (10)−0.0006 (10)−0.0014 (9)
C140.0299 (13)0.0246 (13)0.0332 (14)0.0015 (10)0.0017 (11)−0.0005 (10)
Geometric parameters (Å, º) top
N1—C71.357 (3)C4—C51.399 (3)
N1—C51.375 (3)C4—H40.9300
N1—H10.8600C5—C61.406 (3)
N2—C71.325 (3)C7—C81.471 (3)
N2—C61.395 (3)C8—C131.393 (3)
F1—C141.332 (3)C8—C91.393 (3)
F2—C141.318 (3)C9—C101.379 (4)
F3—C141.342 (3)C9—H90.9300
C1—C21.377 (3)C10—C111.386 (3)
C1—C61.395 (3)C10—H100.9300
C1—H1A0.9300C11—C121.380 (3)
C2—C31.405 (4)C11—C141.498 (3)
C2—H20.9300C12—C131.391 (3)
C3—C41.380 (3)C12—H120.9300
C3—H30.9300C13—H130.9300
C7—N1—C5107.02 (19)C13—C8—C9119.5 (2)
C7—N1—H1126.5C13—C8—C7119.8 (2)
C5—N1—H1126.5C9—C8—C7120.7 (2)
C7—N2—C6104.73 (18)C10—C9—C8120.2 (2)
C2—C1—C6117.9 (2)C10—C9—H9119.9
C2—C1—H1A121.0C8—C9—H9119.9
C6—C1—H1A121.0C9—C10—C11119.9 (2)
C1—C2—C3121.7 (2)C9—C10—H10120.1
C1—C2—H2119.2C11—C10—H10120.1
C3—C2—H2119.2C12—C11—C10120.6 (2)
C4—C3—C2121.5 (2)C12—C11—C14121.2 (2)
C4—C3—H3119.3C10—C11—C14118.3 (2)
C2—C3—H3119.3C11—C12—C13119.8 (2)
C3—C4—C5116.7 (2)C11—C12—H12120.1
C3—C4—H4121.6C13—C12—H12120.1
C5—C4—H4121.6C12—C13—C8120.0 (2)
N1—C5—C4132.1 (2)C12—C13—H13120.0
N1—C5—C6105.74 (19)C8—C13—H13120.0
C4—C5—C6122.2 (2)F2—C14—F1107.5 (2)
N2—C6—C1130.7 (2)F2—C14—F3106.0 (2)
N2—C6—C5109.3 (2)F1—C14—F3105.1 (2)
C1—C6—C5120.0 (2)F2—C14—C11113.0 (2)
N2—C7—N1113.2 (2)F1—C14—C11111.8 (2)
N2—C7—C8124.5 (2)F3—C14—C11112.9 (2)
N1—C7—C8122.3 (2)
C6—C1—C2—C3−1.3 (4)N1—C7—C8—C13150.3 (2)
C1—C2—C3—C4−0.1 (4)N2—C7—C8—C9149.8 (2)
C2—C3—C4—C51.2 (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—N1177.6 (2)C8—C9—C10—C110.0 (4)
C3—C4—C5—C6−1.0 (3)C9—C10—C11—C120.3 (4)
C7—N2—C6—C1179.2 (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—C13179.6 (2)
C2—C1—C6—C51.5 (3)C11—C12—C13—C80.3 (4)
N1—C5—C6—N20.5 (2)C9—C8—C13—C12−0.1 (4)
C4—C5—C6—N2179.4 (2)C7—C8—C13—C12179.6 (2)
N1—C5—C6—C1−179.2 (2)C12—C11—C14—F2106.1 (3)
C4—C5—C6—C1−0.3 (3)C10—C11—C14—F2−73.9 (3)
C6—N2—C7—N10.4 (3)C12—C11—C14—F1−132.4 (3)
C6—N2—C7—C8−179.4 (2)C10—C11—C14—F147.6 (3)
C5—N1—C7—N2−0.1 (3)C12—C11—C14—F3−14.1 (3)
C5—N1—C7—C8179.7 (2)C10—C11—C14—F3165.8 (2)
N2—C7—C8—C13−29.9 (3)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the N1/C5/C6/N2/C7 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.862.072.914 (3)165
C12—H12···F1ii0.932.573.374 (3)144
C13—H13···F3iii0.932.553.275 (4)134
C2—H2···Cgiv0.932.943.700 (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.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the N1/C5/C6/N2/C7 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.862.072.914 (3)165
C12—H12···F1ii0.932.573.374 (3)144
C13—H13···F3iii0.932.553.275 (4)134
C2—H2···Cgiv0.932.943.700 (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.
 

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ISSN: 2056-9890
Volume 70| Part 7| July 2014| Page o760
https://doi.org/10.1107/S1600536814012963
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