Literature DB >> 21583879

2-(4-Methyl-phen-yl)-1H-anthraceno[1,2-d]imidazole-6,11-dione: a fluorescent chemosensor.

Tiago T Guimarães, Eufrânio N Da Silva Júnior, Carlos Eduardo M Carvalho, Carlos A De Simone, Antonio V Pinto.   

Abstract

In the title compound, C(22)H(14)N(2)O(2), the five rings of the mol-ecule are not coplanar. There is a significant twist between the four fused rings, which have a slightly arched conformation, and the pendant aromatic ring, as seen in the dihedral angle of 13.16 (8)° between the anthraquinonic ring system and the pendant aromatic ring plane.

Entities:  

Year:  2009        PMID： 21583879      PMCID： PMC2977743          DOI： 10.1107/S1600536809013634

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


Related literature

For general background on organic fluoro­phores, see: Czarnik (1994 ▶); Friend et al. (1999 ▶); Joux & Lebaron (2000 ▶); Kasten (1999 ▶); Soukos et al. (2000 ▶); Zhu et al. (2008 ▶). For related structures and applications, see: Peng et al. (2005 ▶); Boiocchi et al. (2004 ▶); Yoshida et al. (2002 ▶).

Experimental

Crystal data

C22H14N2O2 M = 338.35 Orthorhombic, a = 7.3850 (10) Å b = 14.0730 (4) Å c = 30.5630 (9) Å V = 3176.4 (4) Å3 Z = 8 Mo Kα radiation μ = 0.09 mm−1 T = 295 K 0.14 × 0.14 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: none 20847 measured reflections 3643 independent reflections 2282 reflections with I > 2σ(I) R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.060 wR(F 2) = 0.155 S = 1.05 3643 reflections 235 parameters H-atom parameters constrained Δρmax = 0.18 e Å−3 Δρmin = −0.20 e Å−3 Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013634/tk2418sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013634/tk2418Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H14N2O2F(000) = 1408
Mr = 338.35Dx = 1.415 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 14527 reflections
a = 7.385 (1) Åθ = 2.9–27.5°
b = 14.0730 (4) ŵ = 0.09 mm−1
c = 30.5630 (9) ÅT = 295 K
V = 3176.4 (4) Å3Prism, yellow
Z = 80.14 × 0.14 × 0.07 mm
Nonius KappaCCD diffractometer2282 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590Rint = 0.066
horizonally mounted graphite crystalθmax = 27.5°, θmin = 3.0°
Detector resolution: 9 pixels mm-1h = −9→7
CCD rotation images, thick slices scansk = −14→18
20847 measured reflectionsl = −39→38
3643 independent 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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0589P)2 + 1.2992P] where P = (Fo2 + 2Fc2)/3
3643 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.18 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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.
xyzUiso*/Ueq
O10.7524 (2)0.58882 (10)0.24672 (5)0.0537 (4)
O20.4748 (2)0.25831 (11)0.30424 (6)0.0632 (5)
N10.6678 (2)0.53709 (11)0.16053 (6)0.0413 (4)
H1N0.70630.59040.17060.050*
N20.5832 (2)0.42641 (11)0.11186 (6)0.0454 (4)
C10.6423 (3)0.51458 (14)0.11723 (7)0.0420 (5)
C20.5674 (3)0.39056 (14)0.15381 (7)0.0420 (5)
C30.5055 (3)0.30226 (14)0.16831 (8)0.0480 (5)
H30.47090.25560.14840.058*
C40.4967 (3)0.28566 (14)0.21264 (8)0.0476 (5)
H40.45460.22720.22250.057*
C4A0.5494 (3)0.35426 (13)0.24325 (7)0.0406 (5)
C50.5310 (3)0.33481 (15)0.29076 (8)0.0454 (5)
C5A0.5811 (3)0.41206 (14)0.32185 (7)0.0440 (5)
C60.5545 (3)0.39803 (18)0.36653 (8)0.0567 (6)
H60.50560.34120.37660.068*
C70.6007 (3)0.46845 (19)0.39578 (8)0.0632 (7)
H70.57870.45970.42550.076*
C80.6794 (3)0.55197 (18)0.38151 (8)0.0621 (7)
H80.71330.59820.40160.075*
C90.7077 (3)0.56666 (16)0.33750 (8)0.0506 (6)
H90.76090.62280.32790.061*
C9A0.6566 (3)0.49753 (14)0.30745 (7)0.0420 (5)
C100.6808 (3)0.51561 (14)0.26033 (7)0.0399 (5)
C10A0.6161 (3)0.44294 (13)0.22942 (7)0.0380 (5)
C110.6208 (3)0.45918 (13)0.18450 (7)0.0381 (5)
C120.6719 (3)0.58162 (14)0.08136 (7)0.0428 (5)
C130.7054 (3)0.67704 (15)0.08847 (8)0.0504 (6)
H130.71510.69970.11700.060*
C140.7245 (3)0.73941 (16)0.05371 (8)0.0558 (6)
H140.74810.80320.05930.067*
C150.7090 (3)0.70857 (17)0.01088 (8)0.0526 (6)
C160.6790 (3)0.61297 (17)0.00396 (8)0.0595 (6)
H160.67020.5904−0.02460.071*
C170.6617 (3)0.55016 (16)0.03836 (8)0.0560 (6)
H170.64290.48600.03270.067*
C180.7200 (4)0.7767 (2)−0.02702 (9)0.0722 (8)
H18A0.84010.8026−0.02870.108*
H18B0.63450.8273−0.02280.108*
H18C0.69260.7437−0.05370.108*
U11U22U33U12U13U23
O10.0679 (10)0.0417 (8)0.0517 (10)−0.0081 (7)−0.0037 (8)−0.0011 (7)
O20.0776 (11)0.0491 (9)0.0630 (11)−0.0064 (8)0.0067 (9)0.0101 (8)
N10.0463 (9)0.0352 (9)0.0424 (11)−0.0031 (7)−0.0018 (8)−0.0024 (8)
N20.0500 (10)0.0411 (10)0.0452 (11)0.0008 (8)0.0006 (8)−0.0064 (8)
C10.0414 (11)0.0418 (11)0.0427 (13)0.0036 (9)−0.0024 (9)−0.0058 (10)
C20.0402 (10)0.0403 (11)0.0456 (12)0.0030 (9)−0.0003 (9)−0.0045 (10)
C30.0529 (13)0.0362 (11)0.0550 (15)−0.0020 (9)0.0011 (11)−0.0098 (10)
C40.0491 (12)0.0351 (11)0.0586 (15)−0.0019 (9)0.0037 (11)−0.0012 (10)
C4A0.0379 (10)0.0360 (10)0.0478 (13)0.0042 (8)0.0018 (9)0.0012 (10)
C50.0398 (11)0.0414 (12)0.0550 (14)0.0047 (9)0.0035 (10)0.0074 (10)
C5A0.0382 (11)0.0488 (12)0.0452 (13)0.0075 (9)−0.0030 (9)0.0022 (10)
C60.0529 (13)0.0672 (15)0.0499 (15)0.0062 (11)0.0004 (11)0.0078 (13)
C70.0656 (15)0.0835 (19)0.0405 (14)0.0123 (14)−0.0019 (12)0.0012 (13)
C80.0679 (16)0.0670 (16)0.0515 (16)0.0107 (13)−0.0098 (12)−0.0144 (13)
C90.0547 (13)0.0490 (12)0.0482 (14)0.0087 (10)−0.0067 (11)−0.0057 (11)
C9A0.0400 (11)0.0428 (11)0.0432 (13)0.0098 (9)−0.0037 (9)−0.0006 (10)
C100.0391 (10)0.0338 (10)0.0468 (13)0.0044 (9)−0.0032 (9)0.0005 (9)
C10A0.0344 (10)0.0369 (10)0.0426 (12)0.0051 (8)0.0004 (8)−0.0027 (9)
C110.0369 (10)0.0341 (10)0.0435 (12)0.0013 (8)−0.0002 (9)−0.0029 (9)
C120.0431 (11)0.0441 (12)0.0412 (12)0.0005 (9)0.0005 (9)−0.0028 (10)
C130.0598 (14)0.0479 (13)0.0434 (13)−0.0037 (10)−0.0031 (10)−0.0052 (10)
C140.0656 (15)0.0490 (13)0.0526 (15)−0.0101 (11)−0.0020 (11)0.0014 (11)
C150.0445 (12)0.0649 (15)0.0484 (14)−0.0049 (11)0.0024 (10)0.0066 (12)
C160.0709 (16)0.0690 (16)0.0387 (13)−0.0046 (13)0.0007 (11)−0.0036 (12)
C170.0713 (15)0.0505 (13)0.0463 (14)−0.0040 (11)0.0021 (11)−0.0087 (11)
C180.0713 (17)0.0866 (19)0.0587 (17)−0.0103 (14)−0.0009 (13)0.0207 (15)
O1—C101.231 (2)C7—H70.9300
O2—C51.225 (2)C8—C91.377 (3)
N1—C111.364 (2)C8—H80.9300
N1—C11.374 (3)C9—C9A1.390 (3)
N1—H1N0.8600C9—H90.9300
N2—C11.325 (2)C9A—C101.473 (3)
N2—C21.383 (3)C10—C10A1.472 (3)
C1—C121.463 (3)C10A—C111.392 (3)
C2—C31.396 (3)C12—C131.383 (3)
C2—C111.403 (3)C12—C171.389 (3)
C3—C41.376 (3)C13—C141.385 (3)
C3—H30.9300C13—H130.9300
C4—C4A1.399 (3)C14—C151.384 (3)
C4—H40.9300C14—H140.9300
C4A—C10A1.407 (3)C15—C161.380 (3)
C4A—C51.484 (3)C15—C181.506 (3)
C5—C5A1.491 (3)C16—C171.380 (3)
C5A—C61.393 (3)C16—H160.9300
C5A—C9A1.397 (3)C17—H170.9300
C6—C71.378 (3)C18—H18A0.9600
C6—H60.9300C18—H18B0.9600
C7—C81.382 (3)C18—H18C0.9600
C11—N1—C1107.29 (16)C9—C9A—C5A120.2 (2)
C11—N1—H1N126.4C9—C9A—C10119.47 (19)
C1—N1—H1N126.4C5A—C9A—C10120.34 (19)
C1—N2—C2104.75 (17)O1—C10—C10A120.28 (19)
N2—C1—N1112.35 (18)O1—C10—C9A121.81 (19)
N2—C1—C12124.07 (19)C10A—C10—C9A117.91 (18)
N1—C1—C12123.55 (18)C11—C10A—C4A116.79 (18)
N2—C2—C3130.29 (19)C11—C10A—C10120.72 (18)
N2—C2—C11110.19 (17)C4A—C10A—C10122.48 (19)
C3—C2—C11119.5 (2)N1—C11—C10A131.92 (18)
C4—C3—C2118.6 (2)N1—C11—C2105.41 (18)
C4—C3—H3120.7C10A—C11—C2122.65 (18)
C2—C3—H3120.7C13—C12—C17117.9 (2)
C3—C4—C4A121.86 (19)C13—C12—C1122.37 (19)
C3—C4—H4119.1C17—C12—C1119.70 (19)
C4A—C4—H4119.1C12—C13—C14120.9 (2)
C4—C4A—C10A120.6 (2)C12—C13—H13119.6
C4—C4A—C5120.09 (18)C14—C13—H13119.6
C10A—C4A—C5119.33 (18)C15—C14—C13121.2 (2)
O2—C5—C4A121.5 (2)C15—C14—H14119.4
O2—C5—C5A120.7 (2)C13—C14—H14119.4
C4A—C5—C5A117.81 (18)C16—C15—C14117.6 (2)
C6—C5A—C9A119.1 (2)C16—C15—C18120.8 (2)
C6—C5A—C5119.1 (2)C14—C15—C18121.6 (2)
C9A—C5A—C5121.8 (2)C17—C16—C15121.5 (2)
C7—C6—C5A119.9 (2)C17—C16—H16119.2
C7—C6—H6120.0C15—C16—H16119.2
C5A—C6—H6120.0C16—C17—C12120.8 (2)
C6—C7—C8120.8 (2)C16—C17—H17119.6
C6—C7—H7119.6C12—C17—H17119.6
C8—C7—H7119.6C15—C18—H18A109.5
C9—C8—C7120.0 (2)C15—C18—H18B109.5
C9—C8—H8120.0H18A—C18—H18B109.5
C7—C8—H8120.0C15—C18—H18C109.5
C8—C9—C9A120.0 (2)H18A—C18—H18C109.5
C8—C9—H9120.0H18B—C18—H18C109.5
C9A—C9—H9120.0
C2—N2—C1—N10.8 (2)C5A—C9A—C10—C10A2.6 (3)
C2—N2—C1—C12−177.41 (18)C4—C4A—C10A—C112.0 (3)
C11—N1—C1—N2−0.6 (2)C5—C4A—C10A—C11−176.46 (17)
C11—N1—C1—C12177.64 (18)C4—C4A—C10A—C10−177.16 (18)
C1—N2—C2—C3177.6 (2)C5—C4A—C10A—C104.4 (3)
C1—N2—C2—C11−0.7 (2)O1—C10—C10A—C11−5.4 (3)
N2—C2—C3—C4−177.4 (2)C9A—C10—C10A—C11174.48 (17)
C11—C2—C3—C40.8 (3)O1—C10—C10A—C4A173.70 (18)
C2—C3—C4—C4A−0.6 (3)C9A—C10—C10A—C4A−6.4 (3)
C3—C4—C4A—C10A−0.9 (3)C1—N1—C11—C10A−178.3 (2)
C3—C4—C4A—C5177.60 (18)C1—N1—C11—C20.1 (2)
C4—C4A—C5—O22.1 (3)C4A—C10A—C11—N1176.36 (19)
C10A—C4A—C5—O2−179.44 (19)C10—C10A—C11—N1−4.5 (3)
C4—C4A—C5—C5A−177.22 (18)C4A—C10A—C11—C2−1.8 (3)
C10A—C4A—C5—C5A1.2 (3)C10—C10A—C11—C2177.34 (17)
O2—C5—C5A—C6−3.3 (3)N2—C2—C11—N10.4 (2)
C4A—C5—C5A—C6176.00 (18)C3—C2—C11—N1−178.13 (17)
O2—C5—C5A—C9A175.73 (19)N2—C2—C11—C10A179.00 (17)
C4A—C5—C5A—C9A−5.0 (3)C3—C2—C11—C10A0.5 (3)
C9A—C5A—C6—C70.7 (3)N2—C1—C12—C13169.3 (2)
C5—C5A—C6—C7179.74 (19)N1—C1—C12—C13−8.7 (3)
C5A—C6—C7—C8−2.3 (3)N2—C1—C12—C17−8.8 (3)
C6—C7—C8—C91.9 (4)N1—C1—C12—C17173.16 (19)
C7—C8—C9—C9A0.1 (3)C17—C12—C13—C141.2 (3)
C8—C9—C9A—C5A−1.7 (3)C1—C12—C13—C14−177.0 (2)
C8—C9—C9A—C10177.59 (19)C12—C13—C14—C150.7 (4)
C6—C5A—C9A—C91.3 (3)C13—C14—C15—C16−1.8 (3)
C5—C5A—C9A—C9−177.70 (18)C13—C14—C15—C18176.8 (2)
C6—C5A—C9A—C10−178.00 (18)C14—C15—C16—C171.1 (3)
C5—C5A—C9A—C103.0 (3)C18—C15—C16—C17−177.5 (2)
C9—C9A—C10—O13.2 (3)C15—C16—C17—C120.7 (4)
C5A—C9A—C10—O1−177.51 (18)C13—C12—C17—C16−1.9 (3)
C9—C9A—C10—C10A−176.75 (17)C1—C12—C17—C16176.3 (2)
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