Literature DB >> 21754246

1,2-Diphenyl-1H-imidazo[4,5-f][1,10]phenanthroline.

S Rosepriya, A Thiruvalluvar, J Jayabharathi, M Venkatesh Perumal, R J Butcher, J P Jasinski, J A Golen.   

Abstract

In the title compound, C(25)H(16)N(4), the fused ring system is essentially planar [maximum deviation = 0.1012 (15) Å]. The imidazole ring makes dihedral angles of 77.41 (8) and 56.26 (8)° with the phenyl rings attached to nitro-gen and carbon, respectively. The dihedral angle between the two phenyl rings is 65.50 (8)°. Weak C-H⋯π inter-actions are found in the crystal structure.

Entities:  

Year:  2011        PMID: 21754246      PMCID: PMC3099849          DOI: 10.1107/S1600536811010890

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For 1,2-diphenyl-1H-imidazo[4,5-f][1,10]phenanthroline derivatives, see: Hadadzadeh et al. (2006 ▶). For metal complexes of the 1,10-phenanthroline-5,6-dione ligand, see: Goss & Abruna (1985 ▶).

Experimental

Crystal data

C25H16N4 M = 372.42 Triclinic, a = 8.8693 (7) Å b = 10.0637 (6) Å c = 11.8960 (9) Å α = 100.219 (6)° β = 110.310 (7)° γ = 102.475 (6)° V = 934.63 (14) Å3 Z = 2 Cu Kα radiation μ = 0.63 mm−1 T = 170 K 0.43 × 0.38 × 0.26 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.965, T max = 1.000 5832 measured reflections 3522 independent reflections 3121 reflections with I > 2σ(I) R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.117 S = 1.05 3522 reflections 262 parameters H-atom parameters constrained Δρmax = 0.18 e Å−3 Δρmin = −0.17 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010890/hg5009sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010890/hg5009Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H16N4Z = 2
Mr = 372.42F(000) = 388
Triclinic, P1Dx = 1.323 Mg m3
Hall symbol: -P 1Melting point: 579 K
a = 8.8693 (7) ÅCu Kα radiation, λ = 1.54184 Å
b = 10.0637 (6) ÅCell parameters from 3954 reflections
c = 11.8960 (9) Åθ = 4.7–70.6°
α = 100.219 (6)°µ = 0.63 mm1
β = 110.310 (7)°T = 170 K
γ = 102.475 (6)°Block, colourless
V = 934.63 (14) Å30.43 × 0.38 × 0.26 mm
Oxford Diffraction Xcalibur Eos Gemini diffractometer3522 independent reflections
Radiation source: Enhance (Cu) X-ray Source3121 reflections with I > 2σ(I)
graphiteRint = 0.014
Detector resolution: 16.1500 pixels mm-1θmax = 70.7°, θmin = 4.7°
ω scansh = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)k = −12→7
Tmin = 0.965, Tmax = 1.000l = −13→14
5832 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0649P)2 + 0.1268P] where P = (Fo2 + 2Fc2)/3
3522 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.17 e Å3
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.
xyzUiso*/Ueq
N10.44262 (13)0.14038 (11)0.37008 (9)0.0404 (3)
N30.21256 (13)0.07897 (11)0.41050 (10)0.0436 (3)
N100.70826 (15)0.57164 (12)0.72960 (11)0.0510 (4)
N130.4425 (2)0.47849 (14)0.78916 (13)0.0678 (5)
C20.28544 (15)0.04678 (13)0.33444 (12)0.0414 (4)
C40.32764 (16)0.19978 (13)0.49979 (11)0.0407 (4)
C50.47004 (15)0.24080 (13)0.47676 (11)0.0394 (3)
C60.60568 (15)0.36743 (13)0.55079 (11)0.0399 (3)
C70.74828 (17)0.41987 (15)0.52720 (13)0.0503 (4)
C80.86537 (19)0.54488 (16)0.60380 (14)0.0555 (5)
C90.83894 (19)0.61654 (15)0.70255 (13)0.0546 (4)
C110.59107 (17)0.44797 (13)0.65524 (11)0.0425 (4)
C120.44390 (18)0.40051 (14)0.68438 (12)0.0462 (4)
C140.3052 (3)0.4386 (2)0.81063 (19)0.0818 (7)
C150.1641 (3)0.32423 (19)0.73479 (18)0.0710 (7)
C160.1669 (2)0.24145 (16)0.63142 (15)0.0550 (5)
C170.31040 (17)0.27871 (14)0.60500 (12)0.0436 (4)
C180.54455 (15)0.13773 (12)0.29871 (11)0.0392 (3)
C190.68211 (17)0.08736 (15)0.33628 (14)0.0511 (4)
C200.7747 (2)0.08003 (17)0.26423 (16)0.0598 (5)
C210.72777 (19)0.12065 (16)0.15536 (15)0.0584 (5)
C220.5928 (2)0.17260 (17)0.12019 (14)0.0582 (5)
C230.50057 (17)0.18306 (15)0.19273 (13)0.0487 (4)
C240.21038 (15)−0.07711 (13)0.22359 (11)0.0418 (4)
C250.29258 (18)−0.17796 (15)0.21043 (13)0.0515 (4)
C260.2173 (2)−0.29636 (15)0.10929 (14)0.0581 (5)
C270.0601 (2)−0.31457 (15)0.01978 (13)0.0578 (5)
C28−0.02154 (19)−0.21497 (18)0.03113 (14)0.0599 (5)
C290.05283 (17)−0.09633 (16)0.13260 (13)0.0526 (4)
H70.763230.368900.458610.0604*
H80.963070.582010.589650.0666*
H90.920670.704070.754330.0655*
H140.302940.492520.883840.0983*
H150.067900.303950.754260.0852*
H160.073960.160760.578820.0660*
H190.712470.058210.410660.0613*
H200.870500.047070.289550.0718*
H210.789330.112580.104460.0701*
H220.562470.201570.045710.0698*
H230.408540.220910.169610.0584*
H250.40137−0.165340.271490.0618*
H260.27385−0.365360.101300.0697*
H270.00829−0.39617−0.049800.0693*
H28−0.12955−0.22749−0.030920.0718*
H29−0.00436−0.027710.139960.0631*
U11U22U33U12U13U23
N10.0356 (5)0.0448 (5)0.0376 (5)0.0087 (4)0.0158 (4)0.0053 (4)
N30.0372 (5)0.0500 (6)0.0417 (6)0.0100 (4)0.0173 (4)0.0092 (5)
N100.0563 (7)0.0464 (6)0.0427 (6)0.0103 (5)0.0167 (5)0.0069 (5)
N130.0882 (10)0.0568 (7)0.0632 (8)0.0142 (7)0.0476 (8)0.0020 (6)
C20.0353 (6)0.0468 (7)0.0400 (6)0.0102 (5)0.0147 (5)0.0106 (5)
C40.0393 (6)0.0468 (7)0.0387 (6)0.0153 (5)0.0172 (5)0.0122 (5)
C50.0381 (6)0.0456 (6)0.0351 (6)0.0145 (5)0.0148 (5)0.0098 (5)
C60.0379 (6)0.0440 (6)0.0367 (6)0.0135 (5)0.0129 (5)0.0114 (5)
C70.0443 (7)0.0549 (8)0.0470 (7)0.0086 (6)0.0205 (6)0.0060 (6)
C80.0461 (8)0.0567 (8)0.0549 (8)0.0041 (6)0.0197 (6)0.0096 (7)
C90.0547 (8)0.0477 (7)0.0462 (7)0.0039 (6)0.0126 (6)0.0066 (6)
C110.0478 (7)0.0423 (6)0.0361 (6)0.0158 (5)0.0139 (5)0.0112 (5)
C120.0563 (8)0.0456 (7)0.0427 (7)0.0198 (6)0.0241 (6)0.0122 (5)
C140.1087 (15)0.0699 (11)0.0839 (12)0.0187 (10)0.0718 (12)0.0037 (9)
C150.0838 (12)0.0683 (10)0.0838 (12)0.0221 (9)0.0620 (11)0.0180 (9)
C160.0581 (9)0.0587 (8)0.0605 (9)0.0203 (7)0.0360 (7)0.0176 (7)
C170.0476 (7)0.0483 (7)0.0433 (7)0.0203 (6)0.0228 (6)0.0160 (6)
C180.0362 (6)0.0397 (6)0.0395 (6)0.0077 (5)0.0179 (5)0.0050 (5)
C190.0470 (7)0.0592 (8)0.0555 (8)0.0211 (6)0.0243 (6)0.0219 (7)
C200.0510 (8)0.0654 (9)0.0765 (10)0.0258 (7)0.0356 (8)0.0208 (8)
C210.0578 (9)0.0624 (9)0.0638 (9)0.0141 (7)0.0401 (8)0.0112 (7)
C220.0611 (9)0.0690 (9)0.0492 (8)0.0152 (7)0.0288 (7)0.0192 (7)
C230.0441 (7)0.0563 (8)0.0472 (7)0.0166 (6)0.0187 (6)0.0155 (6)
C240.0388 (6)0.0453 (7)0.0379 (6)0.0059 (5)0.0165 (5)0.0097 (5)
C250.0506 (8)0.0487 (7)0.0449 (7)0.0138 (6)0.0091 (6)0.0105 (6)
C260.0726 (10)0.0453 (7)0.0491 (8)0.0184 (7)0.0167 (7)0.0105 (6)
C270.0705 (10)0.0473 (7)0.0386 (7)0.0035 (7)0.0131 (7)0.0068 (6)
C280.0460 (8)0.0730 (10)0.0430 (7)0.0075 (7)0.0072 (6)0.0086 (7)
C290.0414 (7)0.0639 (9)0.0481 (7)0.0149 (6)0.0163 (6)0.0094 (6)
N1—C21.3752 (18)C20—C211.380 (2)
N1—C51.3840 (16)C21—C221.372 (3)
N1—C181.4402 (18)C22—C231.386 (2)
N3—C21.3168 (18)C24—C251.389 (2)
N3—C41.3789 (17)C24—C291.386 (2)
N10—C91.317 (2)C25—C261.380 (2)
N10—C111.3506 (18)C26—C271.379 (2)
N13—C121.356 (2)C27—C281.371 (3)
N13—C141.323 (3)C28—C291.383 (2)
C2—C241.4782 (18)C7—H70.9500
C4—C51.377 (2)C8—H80.9500
C4—C171.4330 (19)C9—H90.9500
C5—C61.4321 (18)C14—H140.9500
C6—C71.403 (2)C15—H150.9500
C6—C111.4204 (18)C16—H160.9500
C7—C81.365 (2)C19—H190.9500
C8—C91.385 (2)C20—H200.9500
C11—C121.468 (2)C21—H210.9500
C12—C171.408 (2)C22—H220.9500
C14—C151.389 (3)C23—H230.9500
C15—C161.369 (3)C25—H250.9500
C16—C171.405 (2)C26—H260.9500
C18—C191.384 (2)C27—H270.9500
C18—C231.3745 (19)C28—H280.9500
C19—C201.381 (2)C29—H290.9500
N10···N132.716 (2)C18···H252.9500
N13···C23i3.290 (2)C18···H72.5900
N13···N102.716 (2)C19···H72.7600
N3···H19ii2.7100C19···H252.9200
N3···H162.7900C20···H29viii3.0900
N3···H20iii2.7900C21···H9ix2.9300
N10···H23i2.7900C24···H15v3.1000
N10···H27iv2.9200C27···H21x3.0600
N10···H28iv2.8500C27···H9vi3.0200
N13···H23i2.9000C27···H27vii2.9500
C4···C8i3.551 (2)C28···H9vi3.0800
C4···C9i3.418 (2)C28···H15v2.9800
C5···C9i3.585 (2)C29···H15v2.8900
C6···C11i3.5427 (19)H7···C182.5900
C7···C183.2173 (19)H7···C192.7600
C7···C12i3.532 (2)H9···C27iv3.0200
C7···C193.497 (2)H9···C28iv3.0800
C8···C17i3.439 (2)H9···C21ix2.9300
C8···C4i3.551 (2)H9···H21ix2.5900
C9···C4i3.418 (2)H15···C24v3.1000
C9···C27iv3.452 (2)H15···C28v2.9800
C9···C5i3.585 (2)H15···C29v2.8900
C11···C26ii3.521 (2)H16···N32.7900
C11···C6i3.5427 (19)H19···N3ii2.7100
C11···C25ii3.551 (2)H19···C4ii2.9700
C12···C7i3.532 (2)H20···N3viii2.7900
C15···C29v3.597 (3)H20···H29viii2.4900
C17···C8i3.439 (2)H21···H29viii2.5100
C18···C73.2173 (19)H21···C27x3.0600
C18···C253.211 (2)H21···H9ix2.5900
C19···C73.497 (2)H23···N10i2.7900
C19···C253.509 (2)H23···N13i2.9000
C23···C243.421 (2)H23···H28xi2.4700
C23···N13i3.290 (2)H25···C182.9500
C24···C233.421 (2)H25···C192.9200
C25···C183.211 (2)H25···C4ii3.0700
C25···C193.509 (2)H25···C12ii3.0200
C25···C11ii3.551 (2)H25···C17ii3.0400
C26···C11ii3.521 (2)H26···C11ii3.0600
C27···C9vi3.452 (2)H26···C12ii3.0300
C27···C27vii3.549 (2)H27···N10vi2.9200
C29···C15v3.597 (3)H27···C9vi2.8500
C4···H25ii3.0700H27···C27vii2.9500
C4···H19ii2.9700H27···H27vii2.5800
C9···H27iv2.8500H28···N10vi2.8500
C11···H26ii3.0600H28···H23xi2.4700
C12···H26ii3.0300H29···C20iii3.0900
C12···H25ii3.0200H29···H20iii2.4900
C17···H25ii3.0400H29···H21iii2.5100
C2—N1—C5106.40 (11)C2—C24—C25121.16 (12)
C2—N1—C18124.47 (10)C2—C24—C29119.87 (13)
C5—N1—C18128.80 (11)C25—C24—C29118.94 (13)
C2—N3—C4104.52 (12)C24—C25—C26120.44 (14)
C9—N10—C11117.80 (13)C25—C26—C27120.03 (16)
C12—N13—C14116.67 (16)C26—C27—C28120.05 (14)
N1—C2—N3112.63 (11)C27—C28—C29120.24 (15)
N1—C2—C24122.78 (12)C24—C29—C28120.30 (15)
N3—C2—C24124.59 (13)C6—C7—H7120.00
N3—C4—C5111.31 (12)C8—C7—H7120.00
N3—C4—C17127.30 (13)C7—C8—H8121.00
C5—C4—C17121.38 (12)C9—C8—H8121.00
N1—C5—C4105.14 (11)N10—C9—H9118.00
N1—C5—C6131.74 (13)C8—C9—H9118.00
C4—C5—C6123.04 (12)N13—C14—H14117.00
C5—C6—C7125.74 (12)C15—C14—H14117.00
C5—C6—C11116.56 (13)C14—C15—H15121.00
C7—C6—C11117.68 (12)C16—C15—H15121.00
C6—C7—C8119.33 (14)C15—C16—H16121.00
C7—C8—C9118.70 (16)C17—C16—H16121.00
N10—C9—C8124.49 (14)C18—C19—H19120.00
N10—C11—C6121.98 (14)C20—C19—H19120.00
N10—C11—C12117.39 (12)C19—C20—H20120.00
C6—C11—C12120.61 (12)C21—C20—H20120.00
N13—C12—C11117.44 (13)C20—C21—H21120.00
N13—C12—C17122.17 (15)C22—C21—H21120.00
C11—C12—C17120.40 (12)C21—C22—H22120.00
N13—C14—C15125.3 (2)C23—C22—H22120.00
C14—C15—C16118.5 (2)C18—C23—H23121.00
C15—C16—C17118.39 (17)C22—C23—H23121.00
C4—C17—C12117.84 (14)C24—C25—H25120.00
C4—C17—C16123.29 (13)C26—C25—H25120.00
C12—C17—C16118.86 (13)C25—C26—H26120.00
N1—C18—C19119.73 (11)C27—C26—H26120.00
N1—C18—C23118.93 (13)C26—C27—H27120.00
C19—C18—C23121.33 (14)C28—C27—H27120.00
C18—C19—C20119.13 (14)C27—C28—H28120.00
C19—C20—C21119.88 (17)C29—C28—H28120.00
C20—C21—C22120.41 (16)C24—C29—H29120.00
C21—C22—C23120.35 (15)C28—C29—H29120.00
C18—C23—C22118.84 (15)
C5—N1—C2—N3−0.73 (15)C4—C5—C6—C112.93 (19)
C5—N1—C2—C24−179.76 (12)C5—C6—C7—C8177.87 (14)
C18—N1—C2—N3−174.58 (12)C11—C6—C7—C8−0.4 (2)
C18—N1—C2—C246.4 (2)C5—C6—C11—N10−177.82 (12)
C2—N1—C5—C40.88 (14)C5—C6—C11—C120.63 (19)
C2—N1—C5—C6−175.82 (14)C7—C6—C11—N100.6 (2)
C18—N1—C5—C4174.37 (12)C7—C6—C11—C12179.08 (13)
C18—N1—C5—C6−2.3 (2)C6—C7—C8—C9−0.3 (2)
C2—N1—C18—C19−104.93 (15)C7—C8—C9—N100.9 (2)
C2—N1—C18—C2373.81 (17)N10—C11—C12—N13−4.9 (2)
C5—N1—C18—C1982.65 (17)N10—C11—C12—C17174.82 (13)
C5—N1—C18—C23−98.62 (16)C6—C11—C12—N13176.55 (13)
C4—N3—C2—N10.24 (15)C6—C11—C12—C17−3.7 (2)
C4—N3—C2—C24179.25 (12)N13—C12—C17—C4−177.04 (14)
C2—N3—C4—C50.35 (15)N13—C12—C17—C163.7 (2)
C2—N3—C4—C17−179.93 (14)C11—C12—C17—C43.2 (2)
C11—N10—C9—C8−0.7 (2)C11—C12—C17—C16−176.00 (14)
C9—N10—C11—C6−0.1 (2)N13—C14—C15—C162.6 (3)
C9—N10—C11—C12−178.58 (13)C14—C15—C16—C17−1.9 (3)
C14—N13—C12—C11176.58 (15)C15—C16—C17—C4179.78 (16)
C14—N13—C12—C17−3.2 (2)C15—C16—C17—C12−1.0 (2)
C12—N13—C14—C150.0 (3)N1—C18—C19—C20177.39 (13)
N1—C2—C24—C2556.56 (19)C23—C18—C19—C20−1.3 (2)
N1—C2—C24—C29−125.55 (15)N1—C18—C23—C22−176.22 (13)
N3—C2—C24—C25−122.35 (16)C19—C18—C23—C222.5 (2)
N3—C2—C24—C2955.54 (19)C18—C19—C20—C21−1.0 (2)
N3—C4—C5—N1−0.78 (15)C19—C20—C21—C222.1 (3)
N3—C4—C5—C6176.28 (12)C20—C21—C22—C23−0.9 (3)
C17—C4—C5—N1179.48 (12)C21—C22—C23—C18−1.4 (2)
C17—C4—C5—C6−3.5 (2)C2—C24—C25—C26176.95 (14)
N3—C4—C17—C12−179.46 (13)C29—C24—C25—C26−1.0 (2)
N3—C4—C17—C16−0.3 (2)C2—C24—C29—C28−177.29 (14)
C5—C4—C17—C120.2 (2)C25—C24—C29—C280.7 (2)
C5—C4—C17—C16179.43 (14)C24—C25—C26—C270.6 (2)
N1—C5—C6—C70.8 (2)C25—C26—C27—C280.1 (3)
N1—C5—C6—C11179.13 (13)C26—C27—C28—C29−0.4 (3)
C4—C5—C6—C7−175.39 (14)C27—C28—C29—C240.0 (2)
Cg4 and Cg6 are the centroids of the C4–C6/C11/C12/C17 and C24–C29 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C15—H15···Cg6v0.952.863.757 (3)157
C25—H25···Cg4ii0.952.753.4835 (16)135
Table 1

Hydrogen-bond geometry (Å, °)

Cg4 and Cg6 are the centroids of the C4–C6/C11/C12/C17 and C24–C29 rings, respectively.

D—H⋯AD—HH⋯ADAD—H⋯A
C15—H15⋯Cg6i0.952.863.757 (3)157
C25—H25⋯Cg4ii0.952.753.4835 (16)135

Symmetry codes: (i) ; (ii) .

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