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

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

doi:10.1107/S1600536813019351

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages o1293-o1294

doi:10.1107/S1600536813019351

Open

access

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

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

^aShri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli 621 105, India, ^bDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram, India, ^cDepartment of Chemistry, Urumudhanalakshmi College, Tiruchirappalli 620 019, India, and ^dDepartment of Physics, Urumudhanalakshmi College, Tiruchirappalli 620 019, India
^*Correspondence e-mail: sakthi2udc@gmail.com

(Received 6 June 2013; accepted 13 July 2013; online 20 July 2013)

In the title compound, C₂₉H₁₉F₃N₂O, a phenanthroline-fused imidazole tetracyclic system, the fused benzene rings deviate slightly from the central ring and make dihedral angles with this ring of 3.47 (8) and 3.05 (8)°. The trifluoromethylphenyl ring is roughly coplanar with the phenanthroline-fused imidazole tetracyclic system [dihedral angle = 11.02 (6)°], while the methoxyphenyl ring is almost perpendicular [dihedral angle = 87.65 (6)°]. There are intramolecular C—H ⋯π interactions involving the methoxyphenyl ring and the central phenanthroline ring, as well as an intermolecular C—H⋯π interaction involving the phenanthroline ring. In addition, there is an intermolecular π–π interaction involving the central phenanthroline ring and the trifluoromethylphenyl ring [centroid–centroid distance = 3.685 (2) Å], as well as C—H⋯N interactions linking the molecules into dimers.

Related literature

For background to the supramolecular architecture of phenanthroline compounds, see: Lehn (1995 ). For metal sensors, see: Walters et al. (2000 ). For molecular electronics, see: Peng et al. (1997 ). For photo sensitizers see: Hara et al. (2001 ). For a related structure, see: Sathishkumar et al. (2013 ).

Experimental

Crystal data

C₂₉H₁₉F₃N₂O
M_r = 468.46
Monoclinic, P 2₁ /c
a = 11.7063 (9) Å
b = 20.2301 (16) Å
c = 9.5419 (8) Å
β = 99.725 (2)°
V = 2227.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.32 × 0.29 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.956, T_max = 0.999
24449 measured reflections
5128 independent reflections
3511 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.124
S = 1.01
5128 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg are the centroids of the methoxyphenyl and phenthroline rings, repsectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯N2ⁱ	0.95	2.55	3.402 (2)	150
C3—H3⋯Cg1	0.95	2.86	3.719 (2)	154
C10—H10⋯Cg2ⁱⁱ	0.95	2.69	3.419 (2)	136
C17—H17⋯Cg1	0.95	2.74	3.6042 (2)	154
Symmetry codes: (i) -x+1, -y, -z+2; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: ORTEP-3 (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813019351/bv2223sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019351/bv2223Isup2.hkl

checkCIF report

Comment top

The large variety of complexes based on phenanthroline or polypyridyl derivatives allows the formation of many different molecular systems with various applications ranging from metallo-supramolecular chemistry (Lehn, 1995), metal sensors (Walters et al., 2000), molecular electronics (Peng et al., 1997), and photo sensitizers (Hara et al., 2001). Therefore, in the recent years the preparation of phenanthroimidazoles has gained great attention.

In this phenanthroline triclinic ring system, the phenyl rings on either end are slightly deviated from the central ring and make the dihedral angles with this ring of 3.47 (8)° and 3.05 (8)° respectively. The trifluromethyl phenyl ring is almost coplanar with the phenanthroline fused imidazole tetracyclic system (dihedral angle of 11.02 (6)°) while methoxy phenyl ring is almost perpendicular (dihedral angle of 87.65 (6)°).

The maximum deviation of C9 atom from the mean plane of the tetracyclic phenantherene fused imidazole ring is 0.078 (2)° and that of C29 atom from the methoxy phenyl ring is -0.043 (3)°. The C22 atom of the trifluromethyl phenyl ring is deviated by -0.040 (2)°.

There are intramolecular C3—H3 ···π and C17—H17···π (methoxyphenyl ring system) interactions as well as an intermolecular C10—H10···π interaction involving the phenanthroline ring (at the symmetry code x, 1/2 - y, 1/2 + z). There is an intermolecular π–π interaction involving the central ring phenanthroline ring and the trifluoromethyl phenyl ring (Cg···Cg 3.685 Å, 1-x, -y, 2-z). In addition there C—H···N out-of-plane interactions linking the molecules into dimers as shown in Fig. 2.

Related literature top

For background to the supramolecular architecture of phenanthroline compounds, see: Lehn (1995). For metal sensors, see: Walters et al. (2000). For molecular electronics, see: Peng et al. (1997). For photo sensitizers see: Hara et al. (2001). For closely related structures, see: Sathishkumar et al. (2013).

Experimental top

A mixture of phenanthrene-9,10-dione (1.0 g,4.8 mmol), ammonium acetate (1.48 g,19.2 mmol), 4-trifluromethylbenzaldehyde(0.83 g,4.8 mmol) and 4-methoxyaniline (2.95 g,24 mmol) have been refluxed in ethanol (20 mL) at 80°C. The reaction was monitored by TLC and purified by column chromatography using petroleum ether:ethyl acetate (9:1) as the eluent.Yield: 0.74 g (51%)

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: ORTEP-3 (Farrugia, 2012); 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 diagram showing the C-H···N out of plane π interactions linking molecules into dimers.A packing diagram for (I) is shown.

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

Crystal data top

C₂₉H₁₉F₃N₂O	F(000) = 968
M_r = 468.46	D_x = 1.397 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5131 reflections
a = 11.7063 (9) Å	θ = 1.8–27.6°
b = 20.2301 (16) Å	µ = 0.10 mm⁻¹
c = 9.5419 (8) Å	T = 173 K
β = 99.725 (2)°	Block, colourless
V = 2227.2 (3) Å³	0.32 × 0.29 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	5128 independent reflections
Radiation source: fine-focus sealed tube	3511 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Ω and ϕ scan	θ_max = 27.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→14
T_min = 0.956, T_max = 0.999	k = 0→26
24449 measured reflections	l = 0→12

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0514P)² + 0.6328P] where P = (F_o² + 2F_c²)/3
5128 reflections	(Δ/σ)_max < 0.001
317 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₉H₁₉F₃N₂O	V = 2227.2 (3) Å³
M_r = 468.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7063 (9) Å	µ = 0.10 mm⁻¹
b = 20.2301 (16) Å	T = 173 K
c = 9.5419 (8) Å	0.32 × 0.29 × 0.25 mm
β = 99.725 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5128 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3511 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.999	R_int = 0.032
24449 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.01	Δρ_max = 0.18 e Å⁻³
5128 reflections	Δρ_min = −0.24 e Å⁻³
317 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 > 2sigma(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
F1	0.94082 (11)	−0.18352 (6)	0.83630 (17)	0.0945 (5)
F2	1.03787 (11)	−0.09609 (7)	0.88946 (19)	0.1026 (5)
F3	0.97313 (14)	−0.11886 (9)	0.67561 (17)	0.1112 (6)
O1	0.24682 (11)	−0.21387 (6)	0.47694 (14)	0.0615 (4)
N1	0.41440 (11)	0.01373 (6)	0.76779 (13)	0.0381 (3)
N2	0.53956 (11)	0.08671 (6)	0.88301 (14)	0.0414 (3)
C1	0.34962 (13)	0.06745 (7)	0.80056 (16)	0.0375 (3)
C2	0.22709 (13)	0.08118 (8)	0.77095 (16)	0.0404 (4)
C3	0.14290 (15)	0.04019 (9)	0.69130 (19)	0.0516 (4)
H3	0.1656	−0.0009	0.6565	0.062*
C4	0.02892 (16)	0.05872 (11)	0.6633 (2)	0.0625 (5)
H4	−0.0268	0.0306	0.6092	0.075*
C5	−0.00549 (16)	0.11848 (11)	0.7138 (2)	0.0674 (6)
H5	−0.0846	0.1313	0.6938	0.081*
C6	0.07410 (16)	0.15882 (10)	0.7921 (2)	0.0591 (5)
H6	0.0489	0.1995	0.8260	0.071*
C7	0.19225 (14)	0.14223 (8)	0.82452 (17)	0.0439 (4)
C8	0.27615 (14)	0.18711 (8)	0.90664 (17)	0.0435 (4)
C9	0.24350 (17)	0.24581 (9)	0.96904 (19)	0.0546 (4)
H9	0.1637	0.2571	0.9580	0.066*
C10	0.32367 (19)	0.28690 (9)	1.0449 (2)	0.0626 (5)
H10	0.2989	0.3260	1.0861	0.075*
C11	0.44104 (19)	0.27210 (9)	1.0624 (2)	0.0621 (5)
H11	0.4964	0.3011	1.1146	0.075*
C12	0.47650 (16)	0.21546 (8)	1.00403 (18)	0.0519 (4)
H12	0.5568	0.2053	1.0155	0.062*
C13	0.39540 (14)	0.17238 (7)	0.92748 (16)	0.0410 (4)
C14	0.42898 (13)	0.11102 (7)	0.87125 (16)	0.0387 (3)
C15	0.52887 (13)	0.02806 (7)	0.82138 (16)	0.0380 (3)
C16	0.63143 (13)	−0.01355 (7)	0.81555 (16)	0.0388 (3)
C17	0.62932 (15)	−0.07882 (8)	0.76912 (19)	0.0505 (4)
H17	0.5571	−0.1000	0.7379	0.061*
C18	0.73102 (16)	−0.11314 (9)	0.7679 (2)	0.0543 (4)
H18	0.7280	−0.1577	0.7360	0.065*
C19	0.83675 (14)	−0.08351 (8)	0.81246 (18)	0.0467 (4)
C20	0.84057 (15)	−0.01934 (9)	0.8612 (2)	0.0533 (4)
H20	0.9131	0.0013	0.8938	0.064*
C21	0.73894 (15)	0.01501 (8)	0.86267 (19)	0.0494 (4)
H21	0.7426	0.0592	0.8967	0.059*
C22	0.94602 (17)	−0.11998 (10)	0.8042 (2)	0.0606 (5)
C23	0.36937 (13)	−0.04529 (7)	0.69415 (16)	0.0374 (3)
C24	0.36221 (14)	−0.04960 (8)	0.54819 (17)	0.0434 (4)
H24	0.3855	−0.0135	0.4960	0.052*
C25	0.32095 (15)	−0.10681 (8)	0.47918 (18)	0.0482 (4)
H25	0.3165	−0.1102	0.3791	0.058*
C26	0.28607 (13)	−0.15923 (8)	0.55452 (18)	0.0450 (4)
C27	0.29213 (15)	−0.15426 (8)	0.70017 (19)	0.0502 (4)
H27	0.2676	−0.1901	0.7523	0.060*
C28	0.33403 (15)	−0.09708 (8)	0.76958 (18)	0.0460 (4)
H28	0.3384	−0.0936	0.8696	0.055*
C29	0.2023 (2)	−0.26684 (12)	0.5502 (3)	0.0963 (9)
H29A	0.1761	−0.3025	0.4830	0.144*
H29B	0.1369	−0.2510	0.5929	0.144*
H29C	0.2633	−0.2834	0.6251	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0725 (8)	0.0575 (8)	0.1538 (14)	0.0215 (6)	0.0206 (9)	0.0119 (8)
F2	0.0504 (7)	0.0934 (10)	0.1529 (14)	0.0193 (7)	−0.0148 (8)	−0.0329 (9)
F3	0.0985 (11)	0.1497 (14)	0.0970 (11)	0.0515 (10)	0.0497 (9)	0.0126 (10)
O1	0.0598 (8)	0.0564 (8)	0.0657 (8)	−0.0134 (6)	0.0028 (6)	−0.0200 (6)
N1	0.0384 (7)	0.0357 (6)	0.0391 (7)	−0.0013 (5)	0.0033 (5)	−0.0015 (5)
N2	0.0398 (7)	0.0414 (7)	0.0417 (7)	−0.0010 (6)	0.0033 (6)	−0.0023 (6)
C1	0.0414 (8)	0.0365 (8)	0.0347 (8)	−0.0008 (6)	0.0067 (6)	0.0039 (6)
C2	0.0397 (8)	0.0431 (8)	0.0383 (8)	−0.0010 (7)	0.0062 (6)	0.0059 (7)
C3	0.0422 (9)	0.0547 (10)	0.0570 (11)	−0.0020 (8)	0.0058 (8)	−0.0037 (8)
C4	0.0418 (10)	0.0735 (13)	0.0690 (13)	−0.0058 (9)	0.0002 (9)	−0.0066 (10)
C5	0.0391 (10)	0.0775 (14)	0.0831 (15)	0.0087 (10)	0.0035 (9)	0.0001 (12)
C6	0.0470 (10)	0.0600 (11)	0.0709 (13)	0.0087 (9)	0.0118 (9)	−0.0003 (10)
C7	0.0431 (9)	0.0467 (9)	0.0432 (9)	0.0031 (7)	0.0112 (7)	0.0065 (7)
C8	0.0504 (9)	0.0427 (8)	0.0392 (8)	0.0019 (7)	0.0127 (7)	0.0045 (7)
C9	0.0592 (11)	0.0505 (10)	0.0568 (11)	0.0083 (9)	0.0175 (9)	−0.0018 (8)
C10	0.0811 (14)	0.0501 (10)	0.0589 (12)	0.0058 (10)	0.0186 (10)	−0.0136 (9)
C11	0.0718 (13)	0.0532 (11)	0.0610 (12)	−0.0081 (10)	0.0102 (10)	−0.0159 (9)
C12	0.0549 (10)	0.0471 (9)	0.0536 (10)	−0.0038 (8)	0.0083 (8)	−0.0082 (8)
C13	0.0482 (9)	0.0392 (8)	0.0363 (8)	−0.0009 (7)	0.0086 (7)	0.0016 (6)
C14	0.0402 (8)	0.0379 (8)	0.0375 (8)	−0.0014 (7)	0.0054 (6)	0.0020 (6)
C15	0.0391 (8)	0.0395 (8)	0.0344 (8)	−0.0031 (7)	0.0033 (6)	0.0014 (6)
C16	0.0412 (8)	0.0412 (8)	0.0339 (8)	0.0003 (7)	0.0059 (6)	0.0029 (6)
C17	0.0427 (9)	0.0438 (9)	0.0625 (11)	−0.0007 (7)	0.0018 (8)	−0.0029 (8)
C18	0.0524 (10)	0.0424 (9)	0.0665 (12)	0.0042 (8)	0.0053 (9)	−0.0037 (8)
C19	0.0447 (9)	0.0482 (9)	0.0470 (9)	0.0067 (8)	0.0073 (7)	0.0049 (7)
C20	0.0404 (9)	0.0550 (10)	0.0629 (11)	0.0003 (8)	0.0040 (8)	−0.0046 (9)
C21	0.0458 (9)	0.0446 (9)	0.0562 (10)	−0.0001 (8)	0.0041 (8)	−0.0088 (8)
C22	0.0517 (11)	0.0564 (11)	0.0738 (14)	0.0082 (9)	0.0105 (10)	−0.0025 (10)
C23	0.0356 (8)	0.0366 (8)	0.0385 (8)	−0.0016 (6)	0.0023 (6)	−0.0017 (6)
C24	0.0452 (9)	0.0450 (9)	0.0388 (9)	−0.0016 (7)	0.0043 (7)	0.0057 (7)
C25	0.0504 (10)	0.0563 (10)	0.0355 (9)	0.0002 (8)	0.0003 (7)	−0.0043 (7)
C26	0.0357 (8)	0.0465 (9)	0.0503 (10)	−0.0025 (7)	0.0002 (7)	−0.0086 (7)
C27	0.0546 (10)	0.0447 (9)	0.0513 (10)	−0.0127 (8)	0.0091 (8)	0.0011 (8)
C28	0.0541 (10)	0.0470 (9)	0.0370 (8)	−0.0083 (8)	0.0081 (7)	−0.0012 (7)
C29	0.108 (2)	0.0749 (15)	0.112 (2)	−0.0536 (15)	0.0387 (16)	−0.0358 (14)

Geometric parameters (Å, º) top

F1—C22	1.325 (2)	C11—H11	0.9500
F2—C22	1.325 (2)	C12—C13	1.400 (2)
F3—C22	1.319 (2)	C12—H12	0.9500
O1—C26	1.3661 (19)	C13—C14	1.433 (2)
O1—C29	1.425 (3)	C15—C16	1.475 (2)
N1—C15	1.3819 (19)	C16—C21	1.389 (2)
N1—C1	1.3907 (19)	C16—C17	1.392 (2)
N1—C23	1.4395 (19)	C17—C18	1.380 (2)
N2—C15	1.3209 (19)	C17—H17	0.9500
N2—C14	1.371 (2)	C18—C19	1.376 (2)
C1—C14	1.372 (2)	C18—H18	0.9500
C1—C2	1.441 (2)	C19—C20	1.377 (2)
C2—C3	1.408 (2)	C19—C22	1.490 (2)
C2—C7	1.423 (2)	C20—C21	1.380 (2)
C3—C4	1.368 (2)	C20—H20	0.9500
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.386 (3)	C23—C28	1.374 (2)
C4—H4	0.9500	C23—C24	1.384 (2)
C5—C6	1.363 (3)	C24—C25	1.378 (2)
C5—H5	0.9500	C24—H24	0.9500
C6—C7	1.406 (2)	C25—C26	1.381 (2)
C6—H6	0.9500	C25—H25	0.9500
C7—C8	1.464 (2)	C26—C27	1.383 (2)
C8—C13	1.408 (2)	C27—C28	1.381 (2)
C8—C9	1.410 (2)	C27—H27	0.9500
C9—C10	1.366 (3)	C28—H28	0.9500
C9—H9	0.9500	C29—H29A	0.9800
C10—C11	1.388 (3)	C29—H29B	0.9800
C10—H10	0.9500	C29—H29C	0.9800
C11—C12	1.369 (2)

C26—O1—C29	117.39 (15)	N1—C15—C16	127.66 (13)
C15—N1—C1	106.52 (12)	C21—C16—C17	117.66 (15)
C15—N1—C23	127.36 (12)	C21—C16—C15	116.69 (14)
C1—N1—C23	126.12 (13)	C17—C16—C15	125.64 (14)
C15—N2—C14	105.58 (13)	C18—C17—C16	120.74 (16)
C14—C1—N1	105.24 (13)	C18—C17—H17	119.6
C14—C1—C2	122.77 (14)	C16—C17—H17	119.6
N1—C1—C2	131.98 (14)	C19—C18—C17	120.69 (16)
C3—C2—C7	119.22 (15)	C19—C18—H18	119.7
C3—C2—C1	125.09 (15)	C17—C18—H18	119.7
C7—C2—C1	115.66 (14)	C18—C19—C20	119.41 (16)
C4—C3—C2	120.96 (17)	C18—C19—C22	120.21 (16)
C4—C3—H3	119.5	C20—C19—C22	120.36 (16)
C2—C3—H3	119.5	C19—C20—C21	119.95 (16)
C3—C4—C5	120.16 (18)	C19—C20—H20	120.0
C3—C4—H4	119.9	C21—C20—H20	120.0
C5—C4—H4	119.9	C20—C21—C16	121.52 (16)
C6—C5—C4	120.07 (18)	C20—C21—H21	119.2
C6—C5—H5	120.0	C16—C21—H21	119.2
C4—C5—H5	120.0	F3—C22—F2	105.49 (18)
C5—C6—C7	122.25 (18)	F3—C22—F1	105.03 (17)
C5—C6—H6	118.9	F2—C22—F1	106.03 (17)
C7—C6—H6	118.9	F3—C22—C19	112.60 (17)
C6—C7—C2	117.35 (16)	F2—C22—C19	113.69 (17)
C6—C7—C8	121.05 (16)	F1—C22—C19	113.25 (16)
C2—C7—C8	121.58 (14)	C28—C23—C24	120.45 (14)
C13—C8—C9	116.85 (16)	C28—C23—N1	119.65 (13)
C13—C8—C7	120.25 (14)	C24—C23—N1	119.91 (13)
C9—C8—C7	122.90 (16)	C25—C24—C23	119.38 (15)
C10—C9—C8	121.69 (18)	C25—C24—H24	120.3
C10—C9—H9	119.2	C23—C24—H24	120.3
C8—C9—H9	119.2	C24—C25—C26	120.45 (15)
C9—C10—C11	120.66 (17)	C24—C25—H25	119.8
C9—C10—H10	119.7	C26—C25—H25	119.8
C11—C10—H10	119.7	O1—C26—C25	116.18 (15)
C12—C11—C10	119.56 (18)	O1—C26—C27	123.97 (16)
C12—C11—H11	120.2	C25—C26—C27	119.85 (15)
C10—C11—H11	120.2	C28—C27—C26	119.76 (15)
C11—C12—C13	120.53 (18)	C28—C27—H27	120.1
C11—C12—H12	119.7	C26—C27—H27	120.1
C13—C12—H12	119.7	C23—C28—C27	120.10 (15)
C12—C13—C8	120.70 (15)	C23—C28—H28	120.0
C12—C13—C14	121.98 (15)	C27—C28—H28	120.0
C8—C13—C14	117.29 (14)	O1—C29—H29A	109.5
N2—C14—C1	111.17 (13)	O1—C29—H29B	109.5
N2—C14—C13	126.49 (14)	H29A—C29—H29B	109.5
C1—C14—C13	122.31 (14)	O1—C29—H29C	109.5
N2—C15—N1	111.48 (13)	H29A—C29—H29C	109.5
N2—C15—C16	120.86 (13)	H29B—C29—H29C	109.5

C15—N1—C1—C14	0.30 (16)	C8—C13—C14—C1	−0.5 (2)
C23—N1—C1—C14	179.48 (13)	C14—N2—C15—N1	0.87 (17)
C15—N1—C1—C2	179.13 (15)	C14—N2—C15—C16	−179.16 (13)
C23—N1—C1—C2	−1.7 (2)	C1—N1—C15—N2	−0.75 (16)
C14—C1—C2—C3	175.80 (16)	C23—N1—C15—N2	−179.92 (13)
N1—C1—C2—C3	−2.9 (3)	C1—N1—C15—C16	179.28 (14)
C14—C1—C2—C7	−2.3 (2)	C23—N1—C15—C16	0.1 (2)
N1—C1—C2—C7	179.08 (15)	N2—C15—C16—C21	−7.2 (2)
C7—C2—C3—C4	0.9 (3)	N1—C15—C16—C21	172.77 (15)
C1—C2—C3—C4	−177.09 (17)	N2—C15—C16—C17	171.79 (15)
C2—C3—C4—C5	−0.2 (3)	N1—C15—C16—C17	−8.2 (3)
C3—C4—C5—C6	−0.4 (3)	C21—C16—C17—C18	−1.2 (3)
C4—C5—C6—C7	0.2 (3)	C15—C16—C17—C18	179.86 (16)
C5—C6—C7—C2	0.6 (3)	C16—C17—C18—C19	−0.1 (3)
C5—C6—C7—C8	178.84 (18)	C17—C18—C19—C20	1.2 (3)
C3—C2—C7—C6	−1.1 (2)	C17—C18—C19—C22	−177.10 (18)
C1—C2—C7—C6	177.11 (15)	C18—C19—C20—C21	−1.1 (3)
C3—C2—C7—C8	−179.34 (15)	C22—C19—C20—C21	177.20 (17)
C1—C2—C7—C8	−1.2 (2)	C19—C20—C21—C16	−0.1 (3)
C6—C7—C8—C13	−174.43 (15)	C17—C16—C21—C20	1.3 (3)
C2—C7—C8—C13	3.8 (2)	C15—C16—C21—C20	−179.66 (16)
C6—C7—C8—C9	6.1 (2)	C18—C19—C22—F3	80.8 (2)
C2—C7—C8—C9	−175.70 (15)	C20—C19—C22—F3	−97.5 (2)
C13—C8—C9—C10	0.7 (3)	C18—C19—C22—F2	−159.34 (18)
C7—C8—C9—C10	−179.85 (17)	C20—C19—C22—F2	22.4 (3)
C8—C9—C10—C11	0.3 (3)	C18—C19—C22—F1	−38.2 (3)
C9—C10—C11—C12	−0.6 (3)	C20—C19—C22—F1	143.46 (19)
C10—C11—C12—C13	−0.2 (3)	C15—N1—C23—C28	92.07 (19)
C11—C12—C13—C8	1.3 (3)	C1—N1—C23—C28	−86.95 (19)
C11—C12—C13—C14	−176.70 (16)	C15—N1—C23—C24	−87.77 (19)
C9—C8—C13—C12	−1.5 (2)	C1—N1—C23—C24	93.20 (18)
C7—C8—C13—C12	179.04 (15)	C28—C23—C24—C25	−1.0 (2)
C9—C8—C13—C14	176.61 (14)	N1—C23—C24—C25	178.82 (14)
C7—C8—C13—C14	−2.9 (2)	C23—C24—C25—C26	0.5 (3)
C15—N2—C14—C1	−0.67 (17)	C29—O1—C26—C25	−175.49 (19)
C15—N2—C14—C13	177.31 (14)	C29—O1—C26—C27	4.5 (3)
N1—C1—C14—N2	0.23 (17)	C24—C25—C26—O1	−179.80 (15)
C2—C1—C14—N2	−178.74 (13)	C24—C25—C26—C27	0.2 (3)
N1—C1—C14—C13	−177.86 (13)	O1—C26—C27—C28	179.47 (16)
C2—C1—C14—C13	3.2 (2)	C25—C26—C27—C28	−0.6 (3)
C12—C13—C14—N2	−0.2 (2)	C24—C23—C28—C27	0.7 (2)
C8—C13—C14—N2	−178.24 (15)	N1—C23—C28—C27	−179.15 (15)
C12—C13—C14—C1	177.59 (15)	C26—C27—C28—C23	0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···N2ⁱ	0.95	2.55	3.402 (2)	150
C3—H3···Cg1	0.95	2.86	3.719 (2)	154
C10—H10···Cg2ⁱⁱ	0.95	2.69	3.419 (2)	136
C17—H17···Cg1	0.95	2.74	3.6042 (2)	154

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···N2ⁱ	0.9500	2.5500	3.402 (2)	150.00
C3—H3···Cg1	0.9500	2.8600	3.719 (2)	154.00
C10—H10···Cg2ⁱⁱ	0.9500	2.6900	3.419 (2)	136.00
C17—H17···Cg1	0.9500	2.7400	3.6042 (2)	154.00

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

Acknowledgements

The authors thank Dr Babu Varghese, Senior Scientific Officer SAIF, IIT Chennai, India, for carrying out the data collection.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hara, K., Sugihara, H., Tachibana, Y., Islam, A., Yanagida, M., Sayama, K. & Arakawa, H. (2001). Langmuir, 17, 5992–5999. Web of Science CrossRef CAS Google Scholar
Lehn, J. M. (1995). In Supramolecular Chemistry, Concept of Perspectives. Weinheim: VCH. Google Scholar
Peng, Z., Gharavi, A. R. & Yu, L. J. (1997). J. Am. Chem. Soc. 119, 4622–4632. CrossRef CAS Web of Science Google Scholar
Sathishkumar, R., Mohandas, T., Sakthivel, P. & Jayabharathi, J. (2013). Acta Cryst. E69, o367. CSD CrossRef IUCr Journals 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
Walters, K. A., Trouillrt, L., Guillerez, S. & Schanze, K. S. (2000). Inorg. Chem. 39, 5496–5509. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages o1293-o1294

doi:10.1107/S1600536813019351

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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