1-Phenyl-2-[4-(trifluoro­meth­yl)phen­yl]-1H-benzimidazole

Jayamoorthy, K.; Mohandas, T.; Sakthivel, P.; Jayabharathi, J.

doi:10.1107/S1600536813000834

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o244

doi:10.1107/S1600536813000834

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1-Phenyl-2-[4-(trifluoromethyl)phenyl]-1H-benzimidazole

K. Jayamoorthy,^a T. Mohandas,^b P. Sakthivel ^c ^* and J. Jayabharathi ^a

^aAnnamalai University, Chidambaram, Tamilnadu, India, ^bShri Angalamman College of Engineering And Technology, Siruganoor, Tiruchirappalli, Tamilnadu 621 105, India, and ^cUrumu Dhanalakshmi College, Tiruchirappalli, Tamilnadu 620 019, India
^*Correspondence e-mail: sakthi2udc@yahoo.com

(Received 5 January 2013; accepted 9 January 2013; online 16 January 2013)

In the title molecule, C₂₀H₁₃F₃N₂, the benzimidazole unit is close to being planar [maximum deviation = 0.012 (1) Å] and forms dihedral angles of 31.43 (7) and 61.45 (9)° with the 4-(trifluoromethyl)phenyl and 1-phenyl rings, respectively; the dihedral angle between these rings is 60.94 (10)°. In the crystal, C—H⋯F hydrogen bonds link the molecules into chains along the c-axis direction. The CF₃ group is rotationally disordered with an occupancy ratio of 0.557 (8):0.443 (8) for the F atoms.

Related literature

For the properties of related compounds, see: Bu et al. (1996 ); Cross et al. (1995 ); Fu et al. (2011 ); Zhang et al. (2010 ). For bond lengths and angles in related structures, see: Yoon et al. (2011 ); Kassim et al. (2012 ).

Experimental

Crystal data

C₂₀H₁₃F₃N₂
M_r = 338.32
Triclinic, $[P \overline 1]$
a = 8.7179 (4) Å
b = 9.6796 (5) Å
c = 11.3612 (6) Å
α = 67.654 (2)°
β = 68.123 (2)°
γ = 85.013 (2)°
V = 821.20 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker,2008 ) T_min = 0.960, T_max = 0.986
16592 measured reflections
2889 independent reflections
2338 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.03
2889 reflections
255 parameters
36 restraints
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯F3ⁱ	0.93	2.54	3.429 (6)	160
Symmetry code: (i) x, y, z-1.

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813000834/bv2218sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000834/bv2218Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813000834/bv2218Isup3.cml

checkCIF report

Comment top

Recently much attention has been given by the researchers to crystals containing organic and inorganic ions due to their special structural features and their ferro electric properties (Fu et al., 2011; Zhang et al., 2010).

The imidazole ring can be easily accommodated with functional groups which allows the covalent incorporation of the NLO chromophores into polyimides leading to NLO side chain polymers (Bu et al., 1996).

The NLO property of benzimidazole and its thermal stability in guest host systems have drawn our attention towards this chromophore (Cross et al., 1995).

The asymmetric unit contains the title compound C₂₀H₁₃F₃N₂ in the space group P-1. The benzimidazole ring system in the molecule N1/N2/C8—C14 is essentially planar with maximum deviations of 0.012 (1) for N1. In the molecules the benzimidazole ring N1/N2/C8—C14 makes dihedral angles of 61.45 (9)° and 31.43 (7)° respectively with the phenyl ring C15—C20 and the trifluoromethyl substituted phenyl ring C2—C7.

The torsional angles of C1/C2/C3/C4 and C3/C4/C5/C8 are 178.14° and 179.82° respectively. The molecules are linked into chains by C—H···F hydrogen bond interactions along the c axis.

Bond lengths and bond angles are within normal range and are comparable to related structures (Yoon et al., 2011; Kassim et al., 2012)

Related literature top

For the properties of related compounds, see: Bu et al. (1996); Cross et al. (1995); Fu et al. (2011); Zhang et al. (2010). For bond lengths and angles in related structures, see: Yoon et al. (2011); Kassim et al. (2012).

Experimental top

To pure N-phenyl-o-phenylenediamine(17 mmol,3.128 g) in ethanol (10 ml) was added 4-(trifluoromethyl)-benzaldehyde (17 mmol, 2.38 ml) and ammonium acetate (3 g) were added while the temperature was maintained at 80°C. The reaction mixture was refluxed for 48 h and the reaction completion was monitored by TLC and finally it was extracted with dichloromethane. The separated solid was purified by column chromatography using petroleum ether as the eluent. Yield: 2.87 g (50%). Single crystals were grown in ethanol as solvent within a period of one week.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure and labelling scheme for (I) with displacement ellipsoids for non-H atoms are drawn at the 30% probability level (major component only).
	Fig. 2. A packing diagram for (I) is drawn. Dashed lines indicate the intermolecular hydrogen bonding interactions.

1-Phenyl-2-[4-(trifluoromethyl)phenyl]-1H-benzimidazole top

Crystal data top

C₂₀H₁₃F₃N₂	Z = 2
M_r = 338.32	F(000) = 348
Triclinic, P1	D_x = 1.368 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7179 (4) Å	Cell parameters from 7057 reflections
b = 9.6796 (5) Å	θ = 2.3–27.1°
c = 11.3612 (6) Å	µ = 0.11 mm⁻¹
α = 67.654 (2)°	T = 293 K
β = 68.123 (2)°	Block, colourless
γ = 85.013 (2)°	0.30 × 0.20 × 0.20 mm
V = 821.20 (7) Å³

Data collection top

Bruker Kappa APEXII diffractometer	2889 independent reflections
Radiation source: fine focus sealed tube	2338 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 18.4 pixels mm^-1	θ_max = 25.0°, θ_min = 2.3°
ω and ϕ scan	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker,2008)	k = −11→11
T_min = 0.960, T_max = 0.986	l = −13→13
16592 measured reflections

Refinement top

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: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0469P)² + 0.1406P] where P = (F_o² + 2F_c²)/3
2889 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.15 e Å⁻³
36 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₀H₁₃F₃N₂	γ = 85.013 (2)°
M_r = 338.32	V = 821.20 (7) Å³
Triclinic, P1	Z = 2
a = 8.7179 (4) Å	Mo Kα radiation
b = 9.6796 (5) Å	µ = 0.11 mm⁻¹
c = 11.3612 (6) Å	T = 293 K
α = 67.654 (2)°	0.30 × 0.20 × 0.20 mm
β = 68.123 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	2889 independent reflections
Absorption correction: multi-scan (SADABS; Bruker,2008)	2338 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.986	R_int = 0.032
16592 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	36 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	Δρ_max = 0.15 e Å⁻³
2889 reflections	Δρ_min = −0.14 e Å⁻³
255 parameters

Special details top

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 > σ(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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	−0.1427 (3)	0.2068 (3)	1.5614 (2)	0.0834 (5)
C2	−0.04295 (19)	0.28680 (17)	1.41364 (16)	0.0618 (4)
C3	0.0815 (2)	0.39161 (19)	1.37506 (17)	0.0672 (4)
H3	0.1005	0.4140	1.4414	0.081*
C4	0.17792 (19)	0.46346 (18)	1.23902 (17)	0.0614 (4)
H4	0.2612	0.5346	1.2139	0.074*
C5	0.15171 (17)	0.43049 (15)	1.13943 (15)	0.0523 (4)
C6	0.02360 (19)	0.32742 (17)	1.17905 (16)	0.0590 (4)
H6	0.0027	0.3061	1.1130	0.071*
C7	−0.0730 (2)	0.25634 (18)	1.31517 (17)	0.0635 (4)
H7	−0.1587	0.1876	1.3406	0.076*
C8	0.25824 (17)	0.51116 (15)	0.99601 (15)	0.0524 (4)
C9	0.40857 (19)	0.68454 (16)	0.81207 (16)	0.0575 (4)
C10	0.4994 (2)	0.81574 (18)	0.71278 (18)	0.0711 (5)
H10	0.5086	0.8970	0.7349	0.085*
C11	0.5744 (2)	0.8215 (2)	0.58197 (19)	0.0782 (5)
H11	0.6351	0.9086	0.5140	0.094*
C12	0.5625 (2)	0.7008 (2)	0.54771 (18)	0.0774 (5)
H12	0.6156	0.7090	0.4573	0.093*
C13	0.4747 (2)	0.56999 (19)	0.64349 (17)	0.0682 (5)
H13	0.4676	0.4887	0.6207	0.082*
C14	0.39737 (18)	0.56482 (16)	0.77574 (15)	0.0549 (4)
C15	0.27055 (17)	0.30532 (15)	0.90658 (15)	0.0539 (4)
C16	0.1858 (2)	0.28353 (19)	0.83389 (17)	0.0663 (4)
H16	0.1456	0.3645	0.7795	0.080*
C17	0.1609 (2)	0.1411 (2)	0.8421 (2)	0.0855 (6)
H17	0.1055	0.1259	0.7918	0.103*
C18	0.2174 (3)	0.0223 (2)	0.9239 (3)	0.0940 (7)
H18	0.1999	−0.0738	0.9296	0.113*
C19	0.2999 (2)	0.0440 (2)	0.9977 (2)	0.0926 (7)
H19	0.3362	−0.0377	1.0547	0.111*
C20	0.3294 (2)	0.18642 (18)	0.9882 (2)	0.0743 (5)
H20	0.3882	0.2016	1.0363	0.089*
N1	0.32109 (16)	0.64829 (13)	0.95021 (13)	0.0604 (4)
N2	0.29987 (15)	0.45366 (12)	0.89494 (12)	0.0530 (3)
F1	−0.2223 (12)	0.0892 (8)	1.5887 (4)	0.142 (3)	0.557 (8)
F2	−0.2557 (8)	0.2984 (5)	1.6041 (5)	0.1329 (18)	0.557 (8)
F3	−0.0570 (6)	0.1792 (13)	1.6361 (4)	0.160 (3)	0.557 (8)
F1'	−0.2976 (8)	0.1695 (15)	1.5888 (7)	0.155 (4)	0.443 (8)
F2'	−0.1517 (17)	0.2719 (7)	1.6418 (4)	0.140 (3)	0.443 (8)
F3'	−0.0821 (14)	0.0771 (8)	1.6144 (5)	0.160 (3)	0.443 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.203 (7)	0.116 (3)	0.0732 (19)	−0.092 (4)	−0.010 (3)	−0.018 (3)
F2	0.122 (3)	0.158 (4)	0.084 (2)	0.009 (3)	0.007 (2)	−0.053 (2)
F3	0.141 (3)	0.231 (7)	0.069 (2)	−0.037 (4)	−0.056 (2)	0.013 (4)
N1	0.0698 (8)	0.0499 (7)	0.0627 (8)	0.0024 (6)	−0.0207 (6)	−0.0258 (6)
N2	0.0609 (7)	0.0454 (7)	0.0545 (7)	0.0035 (5)	−0.0201 (6)	−0.0220 (6)
C1	0.0916 (14)	0.0895 (15)	0.0642 (12)	−0.0089 (12)	−0.0223 (11)	−0.0268 (11)
C2	0.0670 (10)	0.0589 (9)	0.0589 (10)	0.0050 (7)	−0.0227 (8)	−0.0224 (8)
C3	0.0728 (10)	0.0776 (11)	0.0603 (10)	0.0032 (8)	−0.0255 (8)	−0.0340 (9)
C4	0.0620 (9)	0.0639 (9)	0.0656 (10)	−0.0008 (7)	−0.0222 (8)	−0.0321 (8)
C5	0.0559 (8)	0.0482 (8)	0.0580 (9)	0.0100 (6)	−0.0232 (7)	−0.0247 (7)
C6	0.0647 (9)	0.0606 (9)	0.0600 (9)	0.0036 (7)	−0.0265 (8)	−0.0278 (8)
C7	0.0651 (9)	0.0593 (9)	0.0648 (10)	−0.0033 (7)	−0.0218 (8)	−0.0227 (8)
C8	0.0570 (8)	0.0473 (8)	0.0590 (9)	0.0084 (6)	−0.0240 (7)	−0.0248 (7)
C9	0.0622 (9)	0.0488 (8)	0.0607 (9)	0.0044 (7)	−0.0212 (7)	−0.0215 (7)
C10	0.0803 (11)	0.0526 (9)	0.0746 (12)	−0.0029 (8)	−0.0221 (9)	−0.0227 (8)
C11	0.0835 (12)	0.0625 (10)	0.0695 (12)	−0.0103 (9)	−0.0175 (9)	−0.0122 (9)
C12	0.0835 (12)	0.0795 (12)	0.0583 (10)	−0.0090 (10)	−0.0138 (9)	−0.0236 (9)
C13	0.0758 (10)	0.0674 (10)	0.0616 (10)	−0.0032 (8)	−0.0189 (8)	−0.0293 (9)
C14	0.0579 (8)	0.0492 (8)	0.0578 (9)	0.0039 (6)	−0.0209 (7)	−0.0206 (7)
C15	0.0528 (8)	0.0470 (8)	0.0604 (9)	0.0042 (6)	−0.0135 (7)	−0.0259 (7)
C16	0.0696 (10)	0.0668 (10)	0.0642 (10)	−0.0043 (8)	−0.0179 (8)	−0.0313 (8)
C17	0.0841 (12)	0.0859 (14)	0.0873 (14)	−0.0208 (11)	−0.0080 (10)	−0.0510 (12)
C18	0.0763 (12)	0.0638 (12)	0.1207 (18)	−0.0121 (10)	0.0082 (12)	−0.0525 (13)
C19	0.0771 (12)	0.0520 (10)	0.1213 (18)	0.0141 (9)	−0.0182 (12)	−0.0242 (11)
C20	0.0694 (10)	0.0558 (10)	0.0954 (13)	0.0136 (8)	−0.0318 (10)	−0.0268 (9)
F3'	0.229 (7)	0.098 (4)	0.084 (3)	0.048 (4)	−0.030 (4)	0.003 (2)
F2'	0.226 (8)	0.108 (4)	0.063 (2)	−0.050 (4)	−0.005 (4)	−0.042 (3)
F1'	0.107 (4)	0.209 (9)	0.089 (3)	−0.058 (4)	−0.023 (2)	0.008 (5)

Geometric parameters (Å, º) top

F1—C1	1.258 (9)	C11—C12	1.387 (3)
F1'—C1	1.319 (8)	C12—C13	1.369 (3)
F2—C1	1.346 (7)	C13—C14	1.382 (2)
F2'—C1	1.270 (8)	C15—C20	1.374 (2)
F3—C1	1.271 (6)	C15—C16	1.373 (2)
F3'—C1	1.328 (9)	C16—C17	1.377 (3)
N1—C8	1.312 (2)	C17—C18	1.363 (4)
N1—C9	1.380 (2)	C18—C19	1.369 (4)
N2—C8	1.3785 (19)	C19—C20	1.381 (3)
N2—C14	1.381 (2)	C3—H3	0.9300
N2—C15	1.428 (2)	C4—H4	0.9300
C1—C2	1.488 (3)	C6—H6	0.9300
C2—C3	1.377 (3)	C7—H7	0.9300
C2—C7	1.375 (2)	C10—H10	0.9300
C3—C4	1.377 (2)	C11—H11	0.9300
C4—C5	1.384 (2)	C12—H12	0.9300
C5—C8	1.469 (2)	C13—H13	0.9300
C5—C6	1.387 (2)	C16—H16	0.9300
C6—C7	1.377 (2)	C17—H17	0.9300
C9—C14	1.392 (2)	C18—H18	0.9300
C9—C10	1.390 (2)	C19—H19	0.9300
C10—C11	1.363 (3)	C20—H20	0.9300

C8—N1—C9	105.22 (13)	N2—C14—C13	131.82 (16)
C8—N2—C14	106.09 (12)	C9—C14—C13	122.50 (15)
C8—N2—C15	129.34 (12)	N2—C15—C16	119.38 (15)
C14—N2—C15	124.15 (12)	N2—C15—C20	119.91 (15)
F1—C1—F2	106.3 (5)	C16—C15—C20	120.70 (16)
F1—C1—F3	109.8 (6)	C15—C16—C17	119.60 (18)
F1—C1—C2	114.8 (3)	C16—C17—C18	120.1 (2)
F2—C1—F3	104.2 (6)	C17—C18—C19	120.2 (2)
F2—C1—C2	108.4 (3)	C18—C19—C20	120.4 (2)
F3—C1—C2	112.5 (3)	C15—C20—C19	118.9 (2)
F1'—C1—C2	114.9 (3)	C2—C3—H3	120.00
F2'—C1—C2	117.1 (4)	C4—C3—H3	120.00
F3'—C1—C2	112.0 (4)	C3—C4—H4	120.00
F1'—C1—F2'	104.8 (8)	C5—C4—H4	120.00
F1'—C1—F3'	103.7 (8)	C5—C6—H6	120.00
F2'—C1—F3'	102.8 (6)	C7—C6—H6	120.00
C1—C2—C3	119.76 (17)	C2—C7—H7	120.00
C1—C2—C7	120.63 (18)	C6—C7—H7	120.00
C3—C2—C7	119.62 (15)	C9—C10—H10	121.00
C2—C3—C4	120.44 (16)	C11—C10—H10	121.00
C3—C4—C5	120.38 (17)	C10—C11—H11	119.00
C4—C5—C6	118.73 (14)	C12—C11—H11	119.00
C4—C5—C8	117.86 (14)	C11—C12—H12	119.00
C6—C5—C8	123.37 (14)	C13—C12—H12	119.00
C5—C6—C7	120.67 (16)	C12—C13—H13	122.00
C2—C7—C6	120.13 (17)	C14—C13—H13	122.00
N1—C8—N2	112.81 (13)	C15—C16—H16	120.00
N1—C8—C5	122.94 (14)	C17—C16—H16	120.00
N2—C8—C5	124.24 (14)	C16—C17—H17	120.00
N1—C9—C10	130.14 (16)	C18—C17—H17	120.00
N1—C9—C14	110.21 (14)	C17—C18—H18	120.00
C10—C9—C14	119.65 (15)	C19—C18—H18	120.00
C9—C10—C11	117.88 (17)	C18—C19—H19	120.00
C10—C11—C12	121.69 (18)	C20—C19—H19	120.00
C11—C12—C13	121.68 (17)	C15—C20—H20	121.00
C12—C13—C14	116.59 (17)	C19—C20—H20	121.00
N2—C14—C9	105.68 (13)

C9—N1—C8—C5	−178.47 (15)	C3—C4—C5—C8	179.82 (16)
C8—N1—C9—C10	179.79 (19)	C6—C5—C8—N1	147.01 (17)
C9—N1—C8—N2	0.13 (19)	C4—C5—C8—N2	150.81 (16)
C8—N1—C9—C14	−0.27 (19)	C8—C5—C6—C7	−179.41 (16)
C8—N2—C14—C9	−0.22 (18)	C4—C5—C6—C7	−1.7 (3)
C15—N2—C14—C9	−173.36 (15)	C4—C5—C8—N1	−30.8 (2)
C14—N2—C15—C20	114.16 (19)	C6—C5—C8—N2	−31.4 (3)
C14—N2—C8—N1	0.06 (19)	C5—C6—C7—C2	−0.2 (3)
C15—N2—C8—C5	−8.7 (3)	N1—C9—C10—C11	−179.91 (19)
C8—N2—C14—C13	179.45 (19)	C14—C9—C10—C11	0.2 (3)
C14—N2—C8—C5	178.63 (15)	N1—C9—C14—N2	0.31 (19)
C8—N2—C15—C20	−57.3 (2)	C10—C9—C14—N2	−179.74 (16)
C15—N2—C8—N1	172.71 (15)	C10—C9—C14—C13	0.6 (3)
C14—N2—C15—C16	−64.8 (2)	N1—C9—C14—C13	−179.40 (16)
C8—N2—C15—C16	123.79 (18)	C9—C10—C11—C12	−0.5 (3)
C15—N2—C14—C13	6.3 (3)	C10—C11—C12—C13	0.1 (3)
F1—C1—C2—C3	−162.7 (5)	C11—C12—C13—C14	0.6 (3)
F1—C1—C2—C7	16.9 (6)	C12—C13—C14—N2	179.49 (18)
F3—C1—C2—C3	−36.2 (7)	C12—C13—C14—C9	−0.9 (3)
F2—C1—C2—C3	78.6 (4)	N2—C15—C16—C17	178.39 (17)
F2—C1—C2—C7	−101.9 (4)	C20—C15—C16—C17	−0.5 (3)
F3—C1—C2—C7	143.4 (6)	N2—C15—C20—C19	−179.86 (19)
C7—C2—C3—C4	−1.4 (3)	C16—C15—C20—C19	−1.0 (3)
C3—C2—C7—C6	1.7 (3)	C15—C16—C17—C18	1.2 (3)
C1—C2—C3—C4	178.2 (2)	C16—C17—C18—C19	−0.3 (4)
C1—C2—C7—C6	−177.9 (2)	C17—C18—C19—C20	−1.2 (4)
C2—C3—C4—C5	−0.5 (3)	C18—C19—C20—C15	1.8 (4)
C3—C4—C5—C6	2.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···F3ⁱ	0.93	2.54	3.429 (6)	160

Symmetry code: (i) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₃F₃N₂
M_r	338.32
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.7179 (4), 9.6796 (5), 11.3612 (6)
α, β, γ (°)	67.654 (2), 68.123 (2), 85.013 (2)
V (Å³)	821.20 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker,2008)
T_min, T_max	0.960, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	16592, 2889, 2338
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.03
No. of reflections	2889
No. of parameters	255
No. of restraints	36
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14

Computer programs: APEX2 (Bruker, 2008), APEX2 and SAINT (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···F3ⁱ	0.9300	2.5400	3.429 (6)	160.00

Symmetry code: (i) x, y, z−1.

References

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Volume 69| Part 2| February 2013| Page o244

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