1-(4-Methyl­phen­yl)-2-[4-(trifluoro­methyl)phen­yl]-1H-phenanthro[9,10-d]imida­zole

Mohandas, T.; Sathishkumar, R.; Jayabharathi, J.; Pasupathy, A.; Sakthivel, P.

doi:10.1107/S1600536813009471

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o710

https://doi.org/10.1107/S1600536813009471

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1-(4-Methylphenyl)-2-[4-(trifluoromethyl)phenyl]-1H-phenanthro[9,10-d]imidazole

T. Mohandas,^a R. Sathishkumar,^b J. Jayabharathi,^b A. Pasupathy ^c and P. Sakthivel ^d ^*

^aDepartment of Physics, Shri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli 621 105, India, ^bAnnamalai University, Annamalainagar, Chidambaram, India, ^cDepartment of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli, Tamilnadu, India, and ^dDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli, Tamilnadu, India
^*Correspondence e-mail: sakthi2udc@gmail.com

(Received 29 March 2013; accepted 7 April 2013; online 13 April 2013)

In the title compound, C₂₉H₁₉F₃N₂, the tetracyclic ring system is essentially planar [maximum deviation from the best plane = 0.076 (1) Å] and makes dihedral angles of 78.10 (5) and 33.71 (4)° with the methylphenyl and fluorophenyl rings, respectively. An intramolecular C—H⋯π interaction occurs. In the crystal, pairs of C—H⋯π interactions link inversion-related molecules.

Related literature

For background to organic electroluminescent materials and devices, see: Adachi et al. (1995 ); Loy et al. (2002 ) and for the photophysical, electrochemical and mobility properties of phenanthroimidazole derivatives, see: Yuan et al. (2011 ). For applications of imidazole and phenanthrolene derivatives, see: Moylan et al. (1993 ); Bu et al. (1996 ); Wang et al. (2002 ).

Experimental

Crystal data

C₂₉H₁₉F₃N₂
M_r = 452.46
Triclinic, $[P \overline 1]$
a = 8.113 (3) Å
b = 11.733 (5) Å
c = 12.713 (2) Å
α = 76.397 (1)°
β = 73.490 (2)°
γ = 86.185 (5)°
V = 1127.7 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.967, T_max = 0.977
22540 measured reflections
22540 independent reflections
14735 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.236
S = 1.04
22540 reflections
310 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C15–C20 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg1	0.93	2.84	3.698 (2)	155
C26—H26⋯Cg2ⁱ	0.93	2.86	3.487 (2)	125
Symmetry code: (i) -x+1, -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: https://doi.org/10.1107/S1600536813009471/go2084sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009471/go2084Isup2.hkl

checkCIF report

Comment top

The optical and conductive properties of the conjugated materials containing imidazole and phenanthroline heterocycles have found in many applications (Moylan et al.,1993, Bu et al.,1996, Wang et al.,2002).

The 1H-phenanthro[9,10 - d]imidazole is a promising building block in the field of molecular materials. It has many desirable properties such as good heat stability, ease of introduction into molecules used as chromophores, fluorescent in nature and readily tunable absorption wavelengths.

The study of organic electroluminescent materials and devices (Loy et al., 2002, Adachi et al., 1995) is therefore of great importance. The photophysical, electrochemical and mobility properties of phenanthroimidazole derivatives have been reported (Yuan et al., 2011).

As our research group deals with organic light emitting devices, we are interested in the title compound (I), Figure 1, as a ligand for inorganic complexes.

The dihedral angle between the phenanthrene moiety and the flourobenzene ring is 33.71 (4)° and to that of the benzene ring of methylphenyl is 78.10 (5)°. The dihedral angle between methylphenyl and benzene ring of trifluorobenzene ring is 72.60 (5)°. The maximum deviation of C12 atom from the mean plane of phenanthrotetracyclic system is 0.076 (1)°. The crystal structure is stabilized by C—H···π interactions. One of these, C12–H12···Cg1 is an intramolecular interaction. The other, C26–H26···Cg2 links the molecules into centrosymmetically related pairs across the centre-of-symmetry at (0.5, 0, 0.5), Figure 2. Cg1 and Cg2 are the centres of gravity of the benzene rings C15–C20 and C8–C13 respectively.

Related literature top

For background to organic electroluminescent materials and devices, see: Adachi et al. (1995); Loy et al. (2002) and for the photophysical, electrochemical and mobility properties of phenanthroimidazole derivatives, see: Yuan et al. (2011). For applications of imidazole and phenanthrolene derivatives, see: Moylan et al. (1993); Bu et al. (1996); Wang et al. (2002).

Experimental top

A mixture of phenanthrene-9,10-dione (1.0 g, 4.8 mmol), ammonium acetate (1.48 g,19.2 mmol), 4-trifluoromethylbenzaldehyde (0.83 g, 4.8 mmol) and 4-methyl aniline (2.56 g, 24 mmol) were refluxed in ethanol (20 ml) at 80°C. The reaction was monitored by TLC and purified by column chromotography using petroleum ether: ethyl acetate (9:1) as the eluent. Yield: 0.69 g (52%). The compound was dissolved in dimethyl sulfoxide and allowed and slow evaporation produced crystal suitable for X-ray diffraction.

Structure description top

As our research group deals with organic light emitting devices, we are interested in the title compound (I), Figure 1, as a ligand for inorganic complexes.

For background to organic electroluminescent materials and devices, see: Adachi et al. (1995); Loy et al. (2002) and for the photophysical, electrochemical and mobility properties of phenanthroimidazole derivatives, see: Yuan et al. (2011). For applications of imidazole and phenanthrolene derivatives, see: Moylan et al. (1993); Bu et al. (1996); Wang et al. (2002).

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.
	Fig. 2. A packing diagram for (I) showing the intramolecular interaction and the centrosymmetrically linked pair of molecules. Dashed lines indicate C—H···π interactions. Hydrogen atoms not involved in the interactions are omitted for clarity.

1-(4-Methylphenyl)-2-[4-(trifluoromethyl)phenyl]-1H-phenanthro[9,10-d]imidazole top

Crystal data top

C₂₉H₁₉F₃N₂	Z = 2
M_r = 452.46	F(000) = 468
Triclinic, P1	D_x = 1.332 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.113 (3) Å	Cell parameters from 6741 reflections
b = 11.733 (5) Å	θ = 2.6–27.5°
c = 12.713 (2) Å	µ = 0.10 mm⁻¹
α = 76.397 (1)°	T = 293 K
β = 73.490 (2)°	Block, colourless
γ = 86.185 (5)°	0.35 × 0.30 × 0.25 mm
V = 1127.7 (7) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	22540 independent reflections
Radiation source: Rotating Anode	14735 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
Detector resolution: 18.4 pixels mm^-1	θ_max = 27.6°, θ_min = 2.6°
ω and φ scan	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −15→14
T_min = 0.967, T_max = 0.977	l = −16→16
22540 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H-atom parameters constrained
wR(F²) = 0.236	w = 1/[σ²(F_o²) + (0.1257P)² + 0.462P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
22540 reflections	Δρ_max = 0.72 e Å⁻³
310 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (2)

Crystal data top

C₂₉H₁₉F₃N₂	γ = 86.185 (5)°
M_r = 452.46	V = 1127.7 (7) Å³
Triclinic, P1	Z = 2
a = 8.113 (3) Å	Mo Kα radiation
b = 11.733 (5) Å	µ = 0.10 mm⁻¹
c = 12.713 (2) Å	T = 293 K
α = 76.397 (1)°	0.35 × 0.30 × 0.25 mm
β = 73.490 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	22540 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	14735 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.977	R_int = 0.000
22540 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.236	H-atom parameters constrained
S = 1.04	Δρ_max = 0.72 e Å⁻³
22540 reflections	Δρ_min = −0.38 e Å⁻³
310 parameters

Special details top

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 > 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)
N1	0.20865 (14)	0.08289 (9)	0.54048 (8)	0.0456 (3)
N2	0.30849 (14)	−0.01502 (9)	0.40358 (9)	0.0482 (3)
F1	0.02200 (19)	−0.51343 (12)	0.86107 (14)	0.1730 (7)
F2	0.2485 (3)	−0.56334 (10)	0.75953 (12)	0.2022 (10)
F3	0.2496 (2)	−0.49122 (12)	0.88779 (13)	0.1697 (7)
C1	0.30932 (17)	0.10375 (11)	0.35746 (11)	0.0464 (3)
C2	0.36035 (17)	0.15914 (12)	0.24009 (11)	0.0486 (3)
C3	0.4141 (2)	0.09473 (13)	0.15691 (11)	0.0596 (4)
H3	0.4196	0.0134	0.1774	0.071*
C4	0.4590 (2)	0.15053 (15)	0.04533 (12)	0.0721 (5)
H4	0.4975	0.1074	−0.0098	0.086*
C5	0.4467 (2)	0.27171 (15)	0.01490 (13)	0.0788 (5)
H5	0.4732	0.3096	−0.0609	0.095*
C6	0.3962 (2)	0.33553 (14)	0.09526 (13)	0.0706 (5)
H6	0.3908	0.4168	0.0731	0.085*
C7	0.35215 (18)	0.28235 (12)	0.21037 (12)	0.0545 (4)
C8	0.29676 (19)	0.34923 (12)	0.29833 (13)	0.0565 (4)
C9	0.2970 (2)	0.47253 (13)	0.27083 (16)	0.0762 (5)
H9	0.3272	0.5118	0.1954	0.091*
C10	0.2539 (3)	0.53619 (14)	0.35226 (17)	0.0856 (6)
H10	0.2552	0.6177	0.3318	0.103*
C11	0.2086 (2)	0.48010 (15)	0.46402 (17)	0.0793 (5)
H11	0.1806	0.5240	0.5188	0.095*
C12	0.2043 (2)	0.36048 (13)	0.49576 (14)	0.0639 (4)
H12	0.1731	0.3238	0.5719	0.077*
C13	0.24672 (18)	0.29210 (11)	0.41417 (12)	0.0518 (4)
C14	0.25034 (17)	0.16657 (11)	0.43936 (11)	0.0461 (3)
C15	0.14817 (18)	0.10502 (11)	0.65183 (11)	0.0470 (3)
C16	−0.02091 (18)	0.13450 (12)	0.69267 (12)	0.0570 (4)
H16	−0.0972	0.1383	0.6495	0.068*
C17	−0.0763 (2)	0.15835 (13)	0.79825 (13)	0.0644 (4)
H17	−0.1906	0.1789	0.8255	0.077*
C18	0.0345 (2)	0.15247 (12)	0.86492 (12)	0.0600 (4)
C19	0.2023 (2)	0.12097 (14)	0.82111 (12)	0.0675 (4)
H19	0.2790	0.1155	0.8643	0.081*
C20	0.26054 (19)	0.09732 (12)	0.71578 (11)	0.0555 (4)
H20	0.3746	0.0764	0.6884	0.067*
C21	0.24755 (16)	−0.02465 (11)	0.51342 (10)	0.0445 (3)
C22	0.22638 (17)	−0.13928 (11)	0.59353 (10)	0.0454 (3)
C23	0.09865 (19)	−0.16471 (12)	0.69527 (12)	0.0555 (4)
H23	0.0233	−0.1060	0.7173	0.067*
C24	0.0823 (2)	−0.27559 (13)	0.76375 (12)	0.0591 (4)
H24	−0.0045	−0.2918	0.8312	0.071*
C25	0.1960 (2)	−0.36339 (13)	0.73183 (12)	0.0576 (4)
C26	0.3215 (2)	−0.33900 (12)	0.63148 (12)	0.0586 (4)
H26	0.3970	−0.3978	0.6098	0.070*
C27	0.33689 (18)	−0.22880 (11)	0.56271 (11)	0.0529 (4)
H27	0.4224	−0.2138	0.4946	0.063*
C28	−0.0263 (3)	0.18059 (16)	0.97975 (13)	0.0901 (6)
H28A	−0.1454	0.2025	0.9946	0.135*	0.50
H28B	0.0403	0.2443	0.9817	0.135*	0.50
H28C	−0.0124	0.1129	1.0360	0.135*	0.50
H28D	0.0671	0.1706	1.0135	0.135*	0.50
H28E	−0.1186	0.1288	1.0265	0.135*	0.50
H28F	−0.0659	0.2603	0.9722	0.135*	0.50
C29	0.1800 (3)	−0.48202 (16)	0.80656 (16)	0.0830 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0526 (7)	0.0431 (6)	0.0404 (6)	0.0026 (5)	−0.0128 (5)	−0.0092 (5)
N2	0.0554 (7)	0.0463 (7)	0.0405 (6)	0.0003 (5)	−0.0133 (5)	−0.0057 (5)
F1	0.1158 (11)	0.1110 (11)	0.2194 (16)	−0.0340 (9)	−0.0277 (11)	0.0896 (10)
F2	0.367 (3)	0.0503 (7)	0.1142 (11)	0.0110 (11)	0.0252 (13)	0.0111 (7)
F3	0.2296 (18)	0.1301 (11)	0.1480 (12)	−0.0230 (11)	−0.1189 (13)	0.0590 (10)
C1	0.0484 (8)	0.0454 (8)	0.0450 (8)	0.0007 (6)	−0.0172 (6)	−0.0045 (6)
C2	0.0484 (8)	0.0518 (8)	0.0429 (8)	−0.0007 (6)	−0.0156 (6)	−0.0015 (6)
C3	0.0719 (10)	0.0596 (9)	0.0441 (8)	0.0011 (8)	−0.0168 (7)	−0.0050 (7)
C4	0.0875 (12)	0.0794 (12)	0.0426 (9)	−0.0001 (9)	−0.0152 (8)	−0.0044 (8)
C5	0.0981 (13)	0.0792 (12)	0.0445 (9)	−0.0052 (10)	−0.0149 (9)	0.0097 (9)
C6	0.0820 (12)	0.0586 (10)	0.0581 (10)	−0.0039 (9)	−0.0176 (9)	0.0110 (8)
C7	0.0524 (8)	0.0528 (9)	0.0529 (9)	−0.0007 (7)	−0.0184 (7)	0.0034 (7)
C8	0.0567 (9)	0.0459 (8)	0.0637 (10)	0.0038 (7)	−0.0212 (7)	−0.0019 (7)
C9	0.0920 (13)	0.0489 (9)	0.0813 (12)	0.0034 (9)	−0.0274 (10)	0.0008 (9)
C10	0.1043 (15)	0.0442 (9)	0.1030 (15)	0.0082 (9)	−0.0270 (12)	−0.0106 (10)
C11	0.0918 (13)	0.0540 (10)	0.0950 (14)	0.0075 (9)	−0.0260 (11)	−0.0248 (10)
C12	0.0709 (10)	0.0519 (9)	0.0712 (10)	0.0038 (8)	−0.0226 (8)	−0.0158 (8)
C13	0.0527 (8)	0.0455 (8)	0.0589 (9)	0.0025 (6)	−0.0205 (7)	−0.0095 (7)
C14	0.0468 (8)	0.0449 (8)	0.0466 (8)	0.0016 (6)	−0.0168 (6)	−0.0063 (6)
C15	0.0560 (8)	0.0429 (7)	0.0425 (7)	−0.0014 (6)	−0.0140 (6)	−0.0096 (6)
C16	0.0530 (9)	0.0649 (10)	0.0577 (9)	0.0030 (7)	−0.0184 (7)	−0.0197 (8)
C17	0.0598 (10)	0.0636 (10)	0.0640 (10)	0.0012 (8)	−0.0041 (8)	−0.0196 (8)
C18	0.0795 (11)	0.0528 (9)	0.0442 (8)	−0.0029 (8)	−0.0106 (8)	−0.0116 (7)
C19	0.0757 (11)	0.0799 (11)	0.0527 (9)	0.0025 (9)	−0.0278 (8)	−0.0149 (8)
C20	0.0553 (9)	0.0637 (9)	0.0485 (8)	0.0041 (7)	−0.0178 (7)	−0.0115 (7)
C21	0.0468 (8)	0.0444 (8)	0.0416 (8)	−0.0004 (6)	−0.0135 (6)	−0.0064 (6)
C22	0.0507 (8)	0.0443 (8)	0.0421 (7)	−0.0025 (6)	−0.0162 (6)	−0.0066 (6)
C23	0.0559 (9)	0.0547 (9)	0.0510 (8)	0.0014 (7)	−0.0078 (7)	−0.0114 (7)
C24	0.0620 (9)	0.0619 (10)	0.0449 (8)	−0.0093 (8)	−0.0062 (7)	−0.0037 (7)
C25	0.0696 (10)	0.0521 (9)	0.0487 (9)	−0.0115 (8)	−0.0211 (8)	0.0024 (7)
C26	0.0629 (9)	0.0486 (9)	0.0598 (9)	0.0036 (7)	−0.0161 (8)	−0.0057 (7)
C27	0.0543 (9)	0.0500 (8)	0.0476 (8)	−0.0019 (7)	−0.0085 (7)	−0.0043 (7)
C28	0.1210 (16)	0.0905 (13)	0.0543 (10)	−0.0028 (11)	−0.0119 (10)	−0.0219 (9)
C29	0.1007 (15)	0.0612 (12)	0.0729 (12)	−0.0114 (11)	−0.0208 (11)	0.0111 (10)

Geometric parameters (Å, º) top

N1—C21	1.3781 (17)	C13—C14	1.4319 (18)
N1—C14	1.3909 (16)	C15—C20	1.3698 (18)
N1—C15	1.4398 (16)	C15—C16	1.3739 (19)
N2—C21	1.3222 (15)	C16—C17	1.3780 (19)
N2—C1	1.3785 (16)	C16—H16	0.9300
F1—C29	1.303 (2)	C17—C18	1.388 (2)
F2—C29	1.259 (2)	C17—H17	0.9300
F3—C29	1.291 (2)	C18—C19	1.379 (2)
C1—C14	1.3738 (17)	C18—C28	1.510 (2)
C1—C2	1.4312 (17)	C19—C20	1.3751 (19)
C2—C3	1.3963 (19)	C19—H19	0.9300
C2—C7	1.4077 (19)	C20—H20	0.9300
C3—C4	1.3692 (19)	C21—C22	1.4706 (18)
C3—H3	0.9300	C22—C27	1.3889 (18)
C4—C5	1.388 (2)	C22—C23	1.3906 (18)
C4—H4	0.9300	C23—C24	1.3757 (19)
C5—C6	1.361 (2)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.391 (2)
C6—C7	1.4006 (19)	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.369 (2)
C7—C8	1.466 (2)	C25—C29	1.479 (2)
C8—C9	1.406 (2)	C26—C27	1.3710 (18)
C8—C13	1.419 (2)	C26—H26	0.9300
C9—C10	1.369 (2)	C27—H27	0.9300
C9—H9	0.9300	C28—H28A	0.9600
C10—C11	1.372 (2)	C28—H28B	0.9600
C10—H10	0.9300	C28—H28C	0.9600
C11—C12	1.366 (2)	C28—H28D	0.9600
C11—H11	0.9300	C28—H28E	0.9600
C12—C13	1.4107 (19)	C28—H28F	0.9600
C12—H12	0.9300

C21—N1—C14	106.48 (10)	C19—C18—C28	121.62 (16)
C21—N1—C15	126.81 (10)	C17—C18—C28	121.34 (16)
C14—N1—C15	126.58 (10)	C20—C19—C18	122.35 (14)
C21—N2—C1	104.85 (10)	C20—C19—H19	118.8
C14—C1—N2	111.39 (11)	C18—C19—H19	118.8
C14—C1—C2	122.18 (12)	C15—C20—C19	119.07 (14)
N2—C1—C2	126.42 (12)	C15—C20—H20	120.5
C3—C2—C7	120.44 (12)	C19—C20—H20	120.5
C3—C2—C1	122.02 (13)	N2—C21—N1	112.13 (11)
C7—C2—C1	117.53 (13)	N2—C21—C22	121.79 (11)
C4—C3—C2	120.45 (15)	N1—C21—C22	126.08 (11)
C4—C3—H3	119.8	C27—C22—C23	118.28 (13)
C2—C3—H3	119.8	C27—C22—C21	117.48 (12)
C3—C4—C5	119.65 (16)	C23—C22—C21	124.18 (12)
C3—C4—H4	120.2	C24—C23—C22	120.89 (13)
C5—C4—H4	120.2	C24—C23—H23	119.6
C6—C5—C4	120.40 (14)	C22—C23—H23	119.6
C6—C5—H5	119.8	C23—C24—C25	119.79 (13)
C4—C5—H5	119.8	C23—C24—H24	120.1
C5—C6—C7	121.88 (15)	C25—C24—H24	120.1
C5—C6—H6	119.1	C26—C25—C24	119.57 (13)
C7—C6—H6	119.1	C26—C25—C29	120.74 (15)
C6—C7—C2	117.13 (14)	C24—C25—C29	119.69 (15)
C6—C7—C8	122.83 (14)	C25—C26—C27	120.67 (14)
C2—C7—C8	120.03 (12)	C25—C26—H26	119.7
C9—C8—C13	117.68 (15)	C27—C26—H26	119.7
C9—C8—C7	121.00 (14)	C26—C27—C22	120.79 (13)
C13—C8—C7	121.28 (13)	C26—C27—H27	119.6
C10—C9—C8	121.66 (16)	C22—C27—H27	119.6
C10—C9—H9	119.2	C18—C28—H28A	109.5
C8—C9—H9	119.2	C18—C28—H28B	109.5
C9—C10—C11	120.19 (16)	H28A—C28—H28B	109.5
C9—C10—H10	119.9	C18—C28—H28C	109.5
C11—C10—H10	119.9	H28A—C28—H28C	109.5
C12—C11—C10	120.74 (17)	H28B—C28—H28C	109.5
C12—C11—H11	119.6	C18—C28—H28D	109.5
C10—C11—H11	119.6	H28A—C28—H28D	141.1
C11—C12—C13	120.61 (15)	H28B—C28—H28D	56.3
C11—C12—H12	119.7	H28C—C28—H28D	56.3
C13—C12—H12	119.7	C18—C28—H28E	109.5
C12—C13—C8	119.10 (13)	H28A—C28—H28E	56.3
C12—C13—C14	124.56 (13)	H28B—C28—H28E	141.1
C8—C13—C14	116.29 (13)	H28C—C28—H28E	56.3
C1—C14—N1	105.14 (11)	H28D—C28—H28E	109.5
C1—C14—C13	122.53 (12)	C18—C28—H28F	109.5
N1—C14—C13	132.28 (12)	H28A—C28—H28F	56.3
C20—C15—C16	120.59 (13)	H28B—C28—H28F	56.3
C20—C15—N1	119.52 (12)	H28C—C28—H28F	141.1
C16—C15—N1	119.88 (12)	H28D—C28—H28F	109.5
C15—C16—C17	119.35 (14)	H28E—C28—H28F	109.5
C15—C16—H16	120.3	F2—C29—F3	103.88 (19)
C17—C16—H16	120.3	F2—C29—F1	107.1 (2)
C16—C17—C18	121.58 (15)	F3—C29—F1	101.85 (18)
C16—C17—H17	119.2	F2—C29—C25	115.41 (17)
C18—C17—H17	119.2	F3—C29—C25	113.42 (16)
C19—C18—C17	117.04 (13)	F1—C29—C25	113.81 (17)

C21—N2—C1—C14	0.56 (15)	C12—C13—C14—N1	3.7 (2)
C21—N2—C1—C2	−178.25 (12)	C8—C13—C14—N1	−178.95 (13)
C14—C1—C2—C3	−177.56 (13)	C21—N1—C15—C20	74.53 (17)
N2—C1—C2—C3	1.1 (2)	C14—N1—C15—C20	−100.77 (15)
C14—C1—C2—C7	1.5 (2)	C21—N1—C15—C16	−105.97 (15)
N2—C1—C2—C7	−179.81 (12)	C14—N1—C15—C16	78.73 (17)
C7—C2—C3—C4	−0.3 (2)	C20—C15—C16—C17	1.1 (2)
C1—C2—C3—C4	178.76 (14)	N1—C15—C16—C17	−178.39 (11)
C2—C3—C4—C5	−1.6 (2)	C15—C16—C17—C18	−0.5 (2)
C3—C4—C5—C6	2.3 (3)	C16—C17—C18—C19	−0.4 (2)
C4—C5—C6—C7	−1.1 (3)	C16—C17—C18—C28	179.00 (13)
C5—C6—C7—C2	−0.7 (2)	C17—C18—C19—C20	0.7 (2)
C5—C6—C7—C8	−179.74 (15)	C28—C18—C19—C20	−178.69 (13)
C3—C2—C7—C6	1.4 (2)	C16—C15—C20—C19	−0.8 (2)
C1—C2—C7—C6	−177.69 (12)	N1—C15—C20—C19	178.68 (12)
C3—C2—C7—C8	−179.54 (13)	C18—C19—C20—C15	−0.1 (2)
C1—C2—C7—C8	1.4 (2)	C1—N2—C21—N1	0.06 (14)
C6—C7—C8—C9	−4.6 (2)	C1—N2—C21—C22	−179.98 (11)
C2—C7—C8—C9	176.33 (13)	C14—N1—C21—N2	−0.64 (15)
C6—C7—C8—C13	177.54 (14)	C15—N1—C21—N2	−176.70 (12)
C2—C7—C8—C13	−1.5 (2)	C14—N1—C21—C22	179.41 (11)
C13—C8—C9—C10	1.2 (3)	C15—N1—C21—C22	3.3 (2)
C7—C8—C9—C10	−176.67 (16)	N2—C21—C22—C27	28.74 (18)
C8—C9—C10—C11	−0.1 (3)	N1—C21—C22—C27	−151.30 (13)
C9—C10—C11—C12	−0.6 (3)	N2—C21—C22—C23	−148.34 (14)
C10—C11—C12—C13	0.2 (3)	N1—C21—C22—C23	31.6 (2)
C11—C12—C13—C8	1.0 (2)	C27—C22—C23—C24	0.1 (2)
C11—C12—C13—C14	178.22 (14)	C21—C22—C23—C24	177.17 (12)
C9—C8—C13—C12	−1.6 (2)	C22—C23—C24—C25	0.8 (2)
C7—C8—C13—C12	176.25 (13)	C23—C24—C25—C26	−1.1 (2)
C9—C8—C13—C14	−179.10 (13)	C23—C24—C25—C29	178.93 (14)
C7—C8—C13—C14	−1.2 (2)	C24—C25—C26—C27	0.5 (2)
N2—C1—C14—N1	−0.94 (14)	C29—C25—C26—C27	−179.52 (14)
C2—C1—C14—N1	177.93 (11)	C25—C26—C27—C22	0.4 (2)
N2—C1—C14—C13	176.67 (11)	C23—C22—C27—C26	−0.7 (2)
C2—C1—C14—C13	−4.5 (2)	C21—C22—C27—C26	−177.97 (12)
C21—N1—C14—C1	0.93 (13)	C26—C25—C29—F2	−20.8 (3)
C15—N1—C14—C1	177.00 (12)	C24—C25—C29—F2	159.2 (2)
C21—N1—C14—C13	−176.36 (13)	C26—C25—C29—F3	98.9 (2)
C15—N1—C14—C13	−0.3 (2)	C24—C25—C29—F3	−81.2 (2)
C12—C13—C14—C1	−173.14 (14)	C26—C25—C29—F1	−145.31 (19)
C8—C13—C14—C1	4.16 (19)	C24—C25—C29—F1	34.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C15–C20 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg1	0.93	2.84	3.698 (2)	155
C26—H26···Cg2ⁱ	0.93	2.86	3.487 (2)	125

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₉H₁₉F₃N₂
M_r	452.46
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.113 (3), 11.733 (5), 12.713 (2)
α, β, γ (°)	76.397 (1), 73.490 (2), 86.185 (5)
V (Å³)	1127.7 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.967, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	22540, 22540, 14735
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.236, 1.04
No. of reflections	22540
No. of parameters	310
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.38

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

Cg1 and Cg2 are the centroids of the C15–C20 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg1	0.9300	2.8400	3.698 (2)	155
C26—H26···Cg2ⁱ	0.9300	2.8600	3.487 (2)	125

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

PS and AP thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the data collection.

References

Adachi, C., Nagai, K. & Tamoto, N. (1995). Appl. Phys. Lett. 66, 2679–2681. CrossRef CAS Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bu, X. R., Li, H., Derveer, D. V. & Mintz, E. A. (1996). Tetrahedron Lett. 37, 7331–7334. CSD CrossRef CAS Web of Science Google Scholar
Loy, D. E., Koene, B. E. & Thompson, M. E. (2002). Adv. Funct. Mater. 12, 245–249. Web of Science CrossRef CAS Google Scholar
Moylan, C. R., Miller, R. D., Twieg, R. J., Betterton, K. M., Lee, V. Y., Matray, T. J. & Nguyen, C. (1993). Chem. Mater. 5, 1499–1508. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, S., Zhao, L., Xu, Z., Wu, C. & Cheng, S. (2002). Mater. Lett. 56, 1035–1038. Web of Science CrossRef CAS Google Scholar
Yuan, Y., Li, D., Zhang, X., Zhao, X., Liu, Y., Zhang, J. & Wang, Y. (2011). New J. Chem. 35, 1534–1540. Web of Science CSD CrossRef CAS Google Scholar

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

1-(4-Methyl­phen­yl)-2-[4-(tri­fluoro­methyl)phen­yl]-1H-phenanthro[9,10-d]imida­zole

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Experimental

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organic compounds

1-(4-Methylphenyl)-2-[4-(trifluoromethyl)phenyl]-1H-phenanthro[9,10-d]imidazole