organic compounds
2-(4-Fluorophenyl)-1-(4-methylphenyl)-1H-phenanthro[9,10-d]imidazole
aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India, cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
*Correspondence e-mail: thiruvalluvar.a@gmail.com
The phenanthrene tricyclic ring system in the title molecule, C28H19FN2, is slightly skewed with a dihedral angle of 7.50 (6)° between the outer benzene rings. The p-tolyl and fluorobenzene rings are twisted from the attached imidazole ring by 70.40 (7) and 28.33 (7)°, respectively. In the crystal, C—H⋯F hydrogen bonds link the molecules into zigzag chains in [001], and weak C—H⋯π interactions further consolidate the crystal packing.
Experimental
Crystal data
|
Refinement
|
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536812037592/cv5332sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037592/cv5332Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812037592/cv5332Isup3.cdx
The title compound has been synthesized by a mixture of phenanthrene-9,10-dione (1.0 g, 4.8 mmol), ammonium acetate (1.48 g, 19.2 mmol), 4-fluorobenzaldehyde (0.6 g, 4.3 mmol) and 4-methylaniline (2.95 g, 24 mmol). These four components have been refluxed in ethanol (20 ml) at 353 K. The reaction was monitored by TLC and purified by
using petroleum ether: ethyl acetate (9:1) as the Yield: 0.8 g (50%). The compound was dissolved in dimethyl sulfoxide and allowed to slow evaporation, to obtain crystals suitable for X-ray diffraction studies.The H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 and 0.96 Å for Csp2 and methyl H atoms, respectively. Uiso(H) = xUeq(C), where x = 1.5 for methyl H atoms and 1.2 for other C-bound H atoms.
Yuan et al. (2011) have reported synthesis, single-crystal structures, photophysical, electrochemical and mobility properties of four phenanthroimidazole derivatives, namely, 1,2-diphenyl-1H-phenanthro[9,10 -d]imidazole, 2-phenyl-1-p-tolyl-1H-phenanthro[9,10 -d]imidazole, 1-phenyl-2-p-tolyl-1H-phenanthro-[9,10 -d]imidazole and 1,2-di-p-tolyl-1H-phenanthro[9,10 -d]imidazole. Since our research group deals with the hole transport materials and organic light emitting devices, we are interested in the title compound, (I), as a ligand for Iridium complexes.
In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related compounds (Yuan et al., 2011; Rosepriya et al., 2011). The phenanthrene tricycle is stranded with a dihedral angle of 7.50 (6)° between the utmost benzene rings. The p-tolyl and fluorobenzene rings are twisted from the attached imidazole ring at 70.40 (7) and 28.33 (7)°, respectively. The dihedral angle between the p-tolyl and fluorobenzene rings is 66.63 (6) °.
In the crystal, C7—H7···F4 hydrogen bonds (Table 1) link the molecules into zigzag chains in [001] (Fig. 2), and weak C—H···π interactions (Table 1) consolidate further the crystal packing.
For related structures, see: Yuan et al. (2011); Rosepriya et al. (2011).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius. | |
Fig. 2. A portion of the crystal packing viewed down the b axis. Dashed lines indicate C—H···F hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted. |
C28H19FN2 | F(000) = 840 |
Mr = 402.45 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/c | Melting point: 494 K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.54184 Å |
a = 10.1809 (2) Å | Cell parameters from 4975 reflections |
b = 10.7654 (2) Å | θ = 4.1–75.3° |
c = 18.4871 (3) Å | µ = 0.67 mm−1 |
β = 96.115 (1)° | T = 123 K |
V = 2014.68 (6) Å3 | Block, colourless |
Z = 4 | 0.45 × 0.35 × 0.25 mm |
Agilent Xcalibur Ruby Gemini diffractometer | 4054 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 3619 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 75.5°, θmin = 4.4° |
ω scans | h = −11→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −11→13 |
Tmin = 0.753, Tmax = 0.850 | l = −22→13 |
8155 measured reflections |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0517P)2 + 0.6604P] where P = (Fo2 + 2Fc2)/3 |
4054 reflections | (Δ/σ)max = 0.001 |
281 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C28H19FN2 | V = 2014.68 (6) Å3 |
Mr = 402.45 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 10.1809 (2) Å | µ = 0.67 mm−1 |
b = 10.7654 (2) Å | T = 123 K |
c = 18.4871 (3) Å | 0.45 × 0.35 × 0.25 mm |
β = 96.115 (1)° |
Agilent Xcalibur Ruby Gemini diffractometer | 4054 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 3619 reflections with I > 2σ(I) |
Tmin = 0.753, Tmax = 0.850 | Rint = 0.022 |
8155 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.25 e Å−3 |
4054 reflections | Δρmin = −0.22 e Å−3 |
281 parameters |
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 > 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. |
x | y | z | Uiso*/Ueq | ||
F4 | 0.18868 (10) | 0.04100 (8) | −0.00640 (5) | 0.0413 (3) | |
N1 | 0.22790 (10) | 0.50374 (10) | 0.22352 (5) | 0.0213 (3) | |
N3 | 0.32302 (10) | 0.57512 (10) | 0.12764 (6) | 0.0230 (3) | |
C2 | 0.26496 (12) | 0.47886 (12) | 0.15502 (7) | 0.0222 (3) | |
C4 | 0.32401 (12) | 0.66606 (12) | 0.18005 (6) | 0.0213 (3) | |
C5 | 0.26743 (12) | 0.62474 (11) | 0.24026 (6) | 0.0207 (3) | |
C6 | 0.26588 (12) | 0.69804 (12) | 0.30544 (6) | 0.0212 (3) | |
C7 | 0.22497 (13) | 0.65420 (12) | 0.37131 (7) | 0.0253 (3) | |
C8 | 0.23298 (14) | 0.72837 (13) | 0.43239 (7) | 0.0282 (4) | |
C9 | 0.28381 (14) | 0.84865 (13) | 0.43030 (7) | 0.0299 (4) | |
C10 | 0.32612 (13) | 0.89271 (13) | 0.36685 (7) | 0.0273 (4) | |
C11 | 0.31801 (12) | 0.82110 (12) | 0.30268 (7) | 0.0223 (3) | |
C12 | 0.36582 (12) | 0.86934 (12) | 0.23605 (7) | 0.0227 (3) | |
C13 | 0.40522 (13) | 0.99443 (13) | 0.22925 (7) | 0.0266 (4) | |
C14 | 0.44945 (13) | 1.03779 (13) | 0.16616 (8) | 0.0296 (4) | |
C15 | 0.45837 (13) | 0.95801 (14) | 0.10720 (7) | 0.0298 (4) | |
C16 | 0.41987 (13) | 0.83594 (13) | 0.11144 (7) | 0.0260 (4) | |
C17 | 0.37198 (12) | 0.79098 (12) | 0.17515 (7) | 0.0221 (3) | |
C18 | 0.17293 (12) | 0.41523 (12) | 0.27015 (6) | 0.0214 (3) | |
C19 | 0.04292 (13) | 0.42709 (13) | 0.28571 (7) | 0.0258 (4) | |
C20 | −0.00771 (13) | 0.34031 (13) | 0.33123 (7) | 0.0287 (4) | |
C21 | 0.06862 (14) | 0.24164 (13) | 0.36048 (7) | 0.0286 (4) | |
C22 | 0.19820 (14) | 0.23184 (13) | 0.34311 (7) | 0.0286 (4) | |
C23 | 0.25117 (13) | 0.31826 (12) | 0.29870 (7) | 0.0247 (3) | |
C24 | 0.24119 (12) | 0.36103 (12) | 0.11511 (7) | 0.0231 (3) | |
C25 | 0.13499 (13) | 0.28159 (13) | 0.12329 (7) | 0.0276 (4) | |
C26 | 0.11766 (14) | 0.17314 (13) | 0.08261 (7) | 0.0299 (4) | |
C27 | 0.20587 (15) | 0.14662 (13) | 0.03352 (7) | 0.0291 (4) | |
C28 | 0.31057 (14) | 0.22303 (13) | 0.02274 (7) | 0.0297 (4) | |
C29 | 0.32810 (13) | 0.33064 (13) | 0.06400 (7) | 0.0263 (4) | |
C30 | 0.01479 (16) | 0.14695 (15) | 0.41001 (8) | 0.0383 (4) | |
H7 | 0.19202 | 0.57389 | 0.37360 | 0.0303* | |
H8 | 0.20442 | 0.69819 | 0.47518 | 0.0339* | |
H9 | 0.28904 | 0.89866 | 0.47152 | 0.0358* | |
H10 | 0.36123 | 0.97241 | 0.36629 | 0.0327* | |
H13 | 0.40115 | 1.04845 | 0.26821 | 0.0319* | |
H14 | 0.47357 | 1.12073 | 0.16270 | 0.0355* | |
H15 | 0.49032 | 0.98744 | 0.06514 | 0.0357* | |
H16 | 0.42550 | 0.78302 | 0.07213 | 0.0312* | |
H19 | −0.00949 | 0.49204 | 0.26601 | 0.0310* | |
H20 | −0.09428 | 0.34849 | 0.34230 | 0.0344* | |
H22 | 0.25028 | 0.16587 | 0.36171 | 0.0343* | |
H23 | 0.33821 | 0.31109 | 0.28827 | 0.0296* | |
H25 | 0.07540 | 0.30157 | 0.15628 | 0.0331* | |
H26 | 0.04784 | 0.11968 | 0.08852 | 0.0358* | |
H28 | 0.36809 | 0.20301 | −0.01134 | 0.0356* | |
H29 | 0.39843 | 0.38321 | 0.05761 | 0.0315* | |
H30A | −0.07357 | 0.16950 | 0.41836 | 0.0575* | |
H30B | 0.06969 | 0.14470 | 0.45555 | 0.0575* | |
H30C | 0.01404 | 0.06650 | 0.38757 | 0.0575* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F4 | 0.0566 (6) | 0.0297 (4) | 0.0377 (5) | 0.0015 (4) | 0.0052 (4) | −0.0148 (4) |
N1 | 0.0245 (5) | 0.0200 (5) | 0.0198 (5) | −0.0001 (4) | 0.0042 (4) | −0.0014 (4) |
N3 | 0.0239 (5) | 0.0235 (5) | 0.0219 (5) | 0.0008 (4) | 0.0038 (4) | −0.0008 (4) |
C2 | 0.0226 (6) | 0.0242 (6) | 0.0201 (6) | 0.0027 (5) | 0.0037 (4) | −0.0003 (5) |
C4 | 0.0213 (5) | 0.0230 (6) | 0.0196 (5) | 0.0018 (5) | 0.0023 (4) | 0.0005 (5) |
C5 | 0.0209 (5) | 0.0198 (6) | 0.0213 (6) | 0.0009 (5) | 0.0020 (4) | 0.0005 (5) |
C6 | 0.0216 (5) | 0.0219 (6) | 0.0202 (6) | 0.0023 (5) | 0.0021 (4) | −0.0002 (5) |
C7 | 0.0284 (6) | 0.0237 (6) | 0.0241 (6) | −0.0009 (5) | 0.0049 (5) | 0.0008 (5) |
C8 | 0.0342 (7) | 0.0306 (7) | 0.0206 (6) | 0.0003 (5) | 0.0063 (5) | −0.0007 (5) |
C9 | 0.0395 (7) | 0.0275 (7) | 0.0225 (6) | 0.0023 (6) | 0.0030 (5) | −0.0052 (5) |
C10 | 0.0330 (7) | 0.0211 (6) | 0.0276 (6) | −0.0001 (5) | 0.0024 (5) | −0.0022 (5) |
C11 | 0.0226 (6) | 0.0213 (6) | 0.0227 (6) | 0.0026 (5) | 0.0013 (4) | 0.0002 (5) |
C12 | 0.0207 (5) | 0.0228 (6) | 0.0241 (6) | 0.0002 (5) | 0.0005 (4) | 0.0023 (5) |
C13 | 0.0274 (6) | 0.0245 (7) | 0.0275 (6) | −0.0026 (5) | 0.0009 (5) | −0.0001 (5) |
C14 | 0.0289 (6) | 0.0247 (7) | 0.0344 (7) | −0.0052 (5) | −0.0002 (5) | 0.0066 (6) |
C15 | 0.0282 (7) | 0.0346 (7) | 0.0266 (6) | −0.0038 (5) | 0.0033 (5) | 0.0086 (6) |
C16 | 0.0243 (6) | 0.0305 (7) | 0.0230 (6) | −0.0003 (5) | 0.0021 (5) | 0.0028 (5) |
C17 | 0.0189 (5) | 0.0245 (6) | 0.0226 (6) | 0.0012 (5) | 0.0011 (4) | 0.0025 (5) |
C18 | 0.0258 (6) | 0.0204 (6) | 0.0184 (5) | −0.0032 (5) | 0.0039 (4) | −0.0021 (5) |
C19 | 0.0253 (6) | 0.0271 (7) | 0.0251 (6) | 0.0011 (5) | 0.0027 (5) | −0.0011 (5) |
C20 | 0.0241 (6) | 0.0356 (7) | 0.0270 (6) | −0.0064 (5) | 0.0054 (5) | −0.0034 (6) |
C21 | 0.0352 (7) | 0.0285 (7) | 0.0218 (6) | −0.0104 (5) | 0.0021 (5) | −0.0013 (5) |
C22 | 0.0350 (7) | 0.0238 (7) | 0.0267 (6) | 0.0010 (5) | 0.0017 (5) | 0.0019 (5) |
C23 | 0.0255 (6) | 0.0251 (6) | 0.0239 (6) | 0.0002 (5) | 0.0045 (5) | −0.0021 (5) |
C24 | 0.0264 (6) | 0.0230 (6) | 0.0198 (6) | 0.0028 (5) | 0.0017 (4) | −0.0002 (5) |
C25 | 0.0295 (6) | 0.0286 (7) | 0.0252 (6) | −0.0005 (5) | 0.0057 (5) | −0.0048 (5) |
C26 | 0.0338 (7) | 0.0268 (7) | 0.0289 (7) | −0.0032 (5) | 0.0029 (5) | −0.0023 (5) |
C27 | 0.0399 (7) | 0.0221 (6) | 0.0242 (6) | 0.0051 (5) | −0.0013 (5) | −0.0058 (5) |
C28 | 0.0345 (7) | 0.0316 (7) | 0.0237 (6) | 0.0083 (6) | 0.0066 (5) | −0.0030 (5) |
C29 | 0.0274 (6) | 0.0275 (7) | 0.0241 (6) | 0.0027 (5) | 0.0039 (5) | 0.0000 (5) |
C30 | 0.0428 (8) | 0.0407 (8) | 0.0313 (7) | −0.0165 (7) | 0.0031 (6) | 0.0049 (6) |
F4—C27 | 1.3567 (16) | C21—C30 | 1.512 (2) |
N1—C2 | 1.3855 (16) | C22—C23 | 1.3874 (19) |
N1—C5 | 1.3885 (16) | C24—C25 | 1.3993 (18) |
N1—C18 | 1.4377 (16) | C24—C29 | 1.4003 (18) |
N3—C2 | 1.3203 (17) | C25—C26 | 1.3898 (19) |
N3—C4 | 1.3767 (16) | C26—C27 | 1.373 (2) |
C2—C24 | 1.4744 (18) | C27—C28 | 1.378 (2) |
C4—C5 | 1.3803 (16) | C28—C29 | 1.3881 (19) |
C4—C17 | 1.4369 (18) | C7—H7 | 0.9300 |
C5—C6 | 1.4419 (16) | C8—H8 | 0.9300 |
C6—C7 | 1.4097 (17) | C9—H9 | 0.9300 |
C6—C11 | 1.4301 (18) | C10—H10 | 0.9300 |
C7—C8 | 1.3783 (18) | C13—H13 | 0.9300 |
C8—C9 | 1.397 (2) | C14—H14 | 0.9300 |
C9—C10 | 1.3763 (19) | C15—H15 | 0.9300 |
C10—C11 | 1.4098 (18) | C16—H16 | 0.9300 |
C11—C12 | 1.4669 (18) | C19—H19 | 0.9300 |
C12—C13 | 1.4145 (19) | C20—H20 | 0.9300 |
C12—C17 | 1.4136 (18) | C22—H22 | 0.9300 |
C13—C14 | 1.3758 (19) | C23—H23 | 0.9300 |
C14—C15 | 1.398 (2) | C25—H25 | 0.9300 |
C15—C16 | 1.376 (2) | C26—H26 | 0.9300 |
C16—C17 | 1.4077 (18) | C28—H28 | 0.9300 |
C18—C19 | 1.3900 (18) | C29—H29 | 0.9300 |
C18—C23 | 1.3832 (18) | C30—H30A | 0.9600 |
C19—C20 | 1.3925 (19) | C30—H30B | 0.9600 |
C20—C21 | 1.391 (2) | C30—H30C | 0.9600 |
C21—C22 | 1.395 (2) | ||
C2—N1—C5 | 106.52 (10) | C24—C25—C26 | 120.66 (12) |
C2—N1—C18 | 125.54 (10) | C25—C26—C27 | 118.56 (13) |
C5—N1—C18 | 127.60 (10) | F4—C27—C26 | 118.57 (13) |
C2—N3—C4 | 104.97 (11) | F4—C27—C28 | 118.60 (12) |
N1—C2—N3 | 112.04 (11) | C26—C27—C28 | 122.83 (13) |
N1—C2—C24 | 125.28 (11) | C27—C28—C29 | 118.36 (13) |
N3—C2—C24 | 122.66 (11) | C24—C29—C28 | 120.82 (12) |
N3—C4—C5 | 111.47 (11) | C6—C7—H7 | 119.00 |
N3—C4—C17 | 126.74 (11) | C8—C7—H7 | 119.00 |
C5—C4—C17 | 121.76 (11) | C7—C8—H8 | 120.00 |
N1—C5—C4 | 104.98 (10) | C9—C8—H8 | 120.00 |
N1—C5—C6 | 132.14 (11) | C8—C9—H9 | 120.00 |
C4—C5—C6 | 122.70 (11) | C10—C9—H9 | 120.00 |
C5—C6—C7 | 124.70 (12) | C9—C10—H10 | 119.00 |
C5—C6—C11 | 116.11 (10) | C11—C10—H10 | 119.00 |
C7—C6—C11 | 119.07 (11) | C12—C13—H13 | 119.00 |
C6—C7—C8 | 121.11 (12) | C14—C13—H13 | 119.00 |
C7—C8—C9 | 120.28 (12) | C13—C14—H14 | 120.00 |
C8—C9—C10 | 119.58 (12) | C15—C14—H14 | 120.00 |
C9—C10—C11 | 122.22 (13) | C14—C15—H15 | 120.00 |
C6—C11—C10 | 117.73 (11) | C16—C15—H15 | 120.00 |
C6—C11—C12 | 121.03 (11) | C15—C16—H16 | 120.00 |
C10—C11—C12 | 121.21 (12) | C17—C16—H16 | 120.00 |
C11—C12—C13 | 122.30 (12) | C18—C19—H19 | 120.00 |
C11—C12—C17 | 120.29 (11) | C20—C19—H19 | 120.00 |
C13—C12—C17 | 117.41 (12) | C19—C20—H20 | 119.00 |
C12—C13—C14 | 121.32 (12) | C21—C20—H20 | 119.00 |
C13—C14—C15 | 120.45 (13) | C21—C22—H22 | 119.00 |
C14—C15—C16 | 119.98 (12) | C23—C22—H22 | 119.00 |
C15—C16—C17 | 120.15 (12) | C18—C23—H23 | 120.00 |
C4—C17—C12 | 117.65 (11) | C22—C23—H23 | 120.00 |
C4—C17—C16 | 121.66 (12) | C24—C25—H25 | 120.00 |
C12—C17—C16 | 120.66 (12) | C26—C25—H25 | 120.00 |
N1—C18—C19 | 120.22 (11) | C25—C26—H26 | 121.00 |
N1—C18—C23 | 118.94 (11) | C27—C26—H26 | 121.00 |
C19—C18—C23 | 120.85 (12) | C27—C28—H28 | 121.00 |
C18—C19—C20 | 119.04 (12) | C29—C28—H28 | 121.00 |
C19—C20—C21 | 121.32 (12) | C24—C29—H29 | 120.00 |
C20—C21—C22 | 118.12 (12) | C28—C29—H29 | 120.00 |
C20—C21—C30 | 121.79 (13) | C21—C30—H30A | 109.00 |
C22—C21—C30 | 120.09 (13) | C21—C30—H30B | 109.00 |
C21—C22—C23 | 121.49 (13) | C21—C30—H30C | 109.00 |
C18—C23—C22 | 119.18 (12) | H30A—C30—H30B | 109.00 |
C2—C24—C25 | 124.00 (11) | H30A—C30—H30C | 109.00 |
C2—C24—C29 | 117.18 (11) | H30B—C30—H30C | 109.00 |
C25—C24—C29 | 118.76 (12) | ||
C5—N1—C2—N3 | −0.67 (14) | C7—C8—C9—C10 | −0.1 (2) |
C5—N1—C2—C24 | −179.32 (12) | C8—C9—C10—C11 | 1.1 (2) |
C18—N1—C2—N3 | −174.41 (11) | C9—C10—C11—C6 | −1.14 (19) |
C18—N1—C2—C24 | 6.95 (19) | C9—C10—C11—C12 | −178.96 (13) |
C2—N1—C5—C4 | 1.00 (13) | C6—C11—C12—C13 | 173.38 (12) |
C2—N1—C5—C6 | −174.12 (13) | C6—C11—C12—C17 | −5.61 (18) |
C18—N1—C5—C4 | 174.57 (11) | C10—C11—C12—C13 | −8.88 (19) |
C18—N1—C5—C6 | −0.6 (2) | C10—C11—C12—C17 | 172.14 (12) |
C2—N1—C18—C19 | −112.80 (14) | C11—C12—C13—C14 | −179.83 (12) |
C2—N1—C18—C23 | 66.83 (16) | C17—C12—C13—C14 | −0.82 (19) |
C5—N1—C18—C19 | 74.79 (16) | C11—C12—C17—C4 | 3.00 (18) |
C5—N1—C18—C23 | −105.58 (15) | C11—C12—C17—C16 | −178.90 (12) |
C4—N3—C2—N1 | 0.03 (13) | C13—C12—C17—C4 | −176.03 (11) |
C4—N3—C2—C24 | 178.71 (11) | C13—C12—C17—C16 | 2.07 (18) |
C2—N3—C4—C5 | 0.65 (14) | C12—C13—C14—C15 | −1.0 (2) |
C2—N3—C4—C17 | −177.29 (12) | C13—C14—C15—C16 | 1.5 (2) |
N1—C2—C24—C25 | 28.9 (2) | C14—C15—C16—C17 | −0.3 (2) |
N1—C2—C24—C29 | −153.74 (12) | C15—C16—C17—C4 | 176.46 (12) |
N3—C2—C24—C25 | −149.60 (13) | C15—C16—C17—C12 | −1.56 (19) |
N3—C2—C24—C29 | 27.75 (18) | N1—C18—C19—C20 | −179.79 (11) |
N3—C4—C5—N1 | −1.05 (14) | C23—C18—C19—C20 | 0.59 (19) |
N3—C4—C5—C6 | 174.66 (11) | N1—C18—C23—C22 | −179.33 (11) |
C17—C4—C5—N1 | 177.01 (11) | C19—C18—C23—C22 | 0.30 (19) |
C17—C4—C5—C6 | −7.28 (19) | C18—C19—C20—C21 | −0.8 (2) |
N3—C4—C17—C12 | −178.97 (12) | C19—C20—C21—C22 | 0.2 (2) |
N3—C4—C17—C16 | 2.9 (2) | C19—C20—C21—C30 | 179.94 (13) |
C5—C4—C17—C12 | 3.28 (18) | C20—C21—C22—C23 | 0.8 (2) |
C5—C4—C17—C16 | −174.80 (12) | C30—C21—C22—C23 | −179.02 (13) |
N1—C5—C6—C7 | 3.0 (2) | C21—C22—C23—C18 | −1.0 (2) |
N1—C5—C6—C11 | 178.89 (12) | C2—C24—C25—C26 | 178.69 (12) |
C4—C5—C6—C7 | −171.39 (12) | C29—C24—C25—C26 | 1.39 (19) |
C4—C5—C6—C11 | 4.49 (18) | C2—C24—C29—C28 | −178.28 (12) |
C5—C6—C7—C8 | 176.56 (13) | C25—C24—C29—C28 | −0.8 (2) |
C11—C6—C7—C8 | 0.80 (19) | C24—C25—C26—C27 | −0.9 (2) |
C5—C6—C11—C10 | −175.94 (11) | C25—C26—C27—F4 | −179.75 (12) |
C5—C6—C11—C12 | 1.88 (17) | C25—C26—C27—C28 | −0.2 (2) |
C7—C6—C11—C10 | 0.18 (18) | F4—C27—C28—C29 | −179.67 (12) |
C7—C6—C11—C12 | 178.00 (12) | C26—C27—C28—C29 | 0.8 (2) |
C6—C7—C8—C9 | −0.9 (2) | C27—C28—C29—C24 | −0.3 (2) |
Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/C2/N3/C4/C5, C4–C6/C11/C12/C17, C12–C17 and C24–C29 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···F4i | 0.93 | 2.54 | 3.1371 (16) | 122 |
C14—H14···Cg2ii | 0.93 | 2.95 | 3.5613 (15) | 125 |
C20—H20···Cg2iii | 0.93 | 2.84 | 3.4540 (14) | 125 |
C23—H23···Cg3iv | 0.93 | 2.81 | 3.5709 (14) | 140 |
C30—H30A···Cg1iii | 0.96 | 2.91 | 3.4294 (17) | 115 |
C30—H30B···Cg4i | 0.96 | 2.77 | 3.6659 (16) | 155 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C28H19FN2 |
Mr | 402.45 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 123 |
a, b, c (Å) | 10.1809 (2), 10.7654 (2), 18.4871 (3) |
β (°) | 96.115 (1) |
V (Å3) | 2014.68 (6) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.67 |
Crystal size (mm) | 0.45 × 0.35 × 0.25 |
Data collection | |
Diffractometer | Agilent Xcalibur Ruby Gemini |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.753, 0.850 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8155, 4054, 3619 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.106, 1.03 |
No. of reflections | 4054 |
No. of parameters | 281 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.22 |
Computer programs: CrysAlis PRO (Agilent, 2012), SIR2011 (Burla et al., 2012), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).
Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/C2/N3/C4/C5, C4–C6/C11/C12/C17, C12–C17 and C24–C29 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···F4i | 0.93 | 2.54 | 3.1371 (16) | 122 |
C14—H14···Cg2ii | 0.93 | 2.95 | 3.5613 (15) | 125 |
C20—H20···Cg2iii | 0.93 | 2.84 | 3.4540 (14) | 125 |
C23—H23···Cg3iv | 0.93 | 2.81 | 3.5709 (14) | 140 |
C30—H30A···Cg1iii | 0.96 | 2.91 | 3.4294 (17) | 115 |
C30—H30B···Cg4i | 0.96 | 2.77 | 3.6659 (16) | 155 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2. |
Acknowledgements
RS is thankful to the DRDO (F. No. NRB-213/MAT/10–11) for providing a fellowship. JJ is thankful to the DST (No. SR/S1/IC-73/2010), the UGC [F. No. 36–21/2008 (SR)] and the DRDO (F. No. NRB-213/MAT/10–11) for providing funds for this research study. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.
References
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Mallamo, M., Mazzone, A., Polidori, G. & Spagna, R. (2012). J. Appl. Cryst. 45, 357–361. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Rosepriya, S., Venkatesh Perumal, M., Thiruvalluvar, A., Jayabharathi, J., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o1965. Web of Science 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
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
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.
Yuan et al. (2011) have reported synthesis, single-crystal structures, photophysical, electrochemical and mobility properties of four phenanthroimidazole derivatives, namely, 1,2-diphenyl-1H-phenanthro[9,10 -d]imidazole, 2-phenyl-1-p-tolyl-1H-phenanthro[9,10 -d]imidazole, 1-phenyl-2-p-tolyl-1H-phenanthro-[9,10 -d]imidazole and 1,2-di-p-tolyl-1H-phenanthro[9,10 -d]imidazole. Since our research group deals with the hole transport materials and organic light emitting devices, we are interested in the title compound, (I), as a ligand for Iridium complexes.
In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related compounds (Yuan et al., 2011; Rosepriya et al., 2011). The phenanthrene tricycle is stranded with a dihedral angle of 7.50 (6)° between the utmost benzene rings. The p-tolyl and fluorobenzene rings are twisted from the attached imidazole ring at 70.40 (7) and 28.33 (7)°, respectively. The dihedral angle between the p-tolyl and fluorobenzene rings is 66.63 (6) °.
In the crystal, C7—H7···F4 hydrogen bonds (Table 1) link the molecules into zigzag chains in [001] (Fig. 2), and weak C—H···π interactions (Table 1) consolidate further the crystal packing.