Literature DB >> 22590374

1-(Anthracen-1-yl)pyrrolidine-2,5-dione.

Sanaz Khorasani1, Manuel A Fernandes.   

Abstract

In the mol-ecular structure of title compound, C(18)H(13)NO(2), the succinimide ring is orientated away from the plane of the anthracene moiety by 71.94 (4)°. The crystal structure features three different types of inter-molecular inter-actions, viz. C-H⋯O, C-H⋯π and π-π bonds. Mol-ecules along the b axis stack on each other as a result of π-π inter-actions which have a centroid-centroid distance of 3.6780 (15) Å, while C-H⋯π inter-actions are present between neigbouring stacks. Also, acting between the stacks are the C-H⋯O inter-actions between the aromatic H atoms of the anthracene and the O atoms of the succinimide.

Entities:  

Year:  2012        PMID： 22590374      PMCID： PMC3344612          DOI： 10.1107/S160053681201536X

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


Related literature

For studies of regio- and sterio-selectivity of substituted anthracenes in Diels–Alder reactions, see: Singh & Ningombom (2010 ▶); Alston et al. (1979 ▶); Meek et al. (1960 ▶); Kaplan & Conroy (1963 ▶); Verma & Singh (1977 ▶). For a study involving NMR experiments, see: Hubbard et al. (1992 ▶).

Experimental

Crystal data

C18H13NO2 M = 275.29 Orthorhombic, a = 18.4179 (9) Å b = 5.7697 (4) Å c = 12.4403 (6) Å V = 1321.98 (13) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 173 K 0.49 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer 10655 measured reflections 1667 independent reflections 1258 reflections with I > 2σ(I) R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.088 S = 0.95 1667 reflections 190 parameters 1 restraint H-atom parameters constrained Δρmax = 0.17 e Å−3 Δρmin = −0.19 e Å−3 Data collection: APEX2 (Bruker 2005 ▶); cell refinement: SAINT (Bruker 2005 ▶); 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, 1997 ▶) and SCHAKAL99 (Keller, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201536X/rk2341sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201536X/rk2341Isup2.hkl Supplementary material file. DOI: 10.1107/S160053681201536X/rk2341Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H13NO2F(000) = 576
Mr = 275.29Dx = 1.383 Mg m−3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2466 reflections
a = 18.4179 (9) Åθ = 2.8–26.7°
b = 5.7697 (4) ŵ = 0.09 mm−1
c = 12.4403 (6) ÅT = 173 K
V = 1321.98 (13) Å3Plate, brown
Z = 40.49 × 0.15 × 0.10 mm
Bruker APEXII CCD diffractometer1258 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.081
Graphite monochromatorθmax = 28.0°, θmin = 2.2°
φ– and ω–scansh = −24→24
10655 measured reflectionsk = −7→7
1667 independent reflectionsl = −16→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 0.95w = 1/[σ2(Fo2) + (0.0468P)2] where P = (Fo2 + 2Fc2)/3
1667 reflections(Δ/σ)max = 0.002
190 parametersΔρmax = 0.17 e Å−3
1 restraintΔρmin = −0.19 e Å−3
Geometry. All s.u.'s (except s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1−0.12512 (12)1.0166 (5)0.33781 (19)0.0300 (6)
C2−0.13405 (14)1.2022 (5)0.40282 (19)0.0348 (7)
H2−0.17621.29580.39590.042*
C3−0.08086 (14)1.2588 (5)0.4816 (2)0.0369 (7)
H3−0.08701.39140.52590.044*
C4−0.02145 (13)1.1223 (5)0.4929 (2)0.0373 (7)
H40.01311.15850.54710.045*
C5−0.00952 (13)0.9262 (5)0.42571 (18)0.0313 (6)
C60.05236 (13)0.7881 (5)0.43475 (19)0.0340 (7)
H60.08690.82310.48910.041*
C70.06517 (13)0.6010 (5)0.3669 (2)0.0331 (6)
C80.12738 (13)0.4548 (5)0.3779 (2)0.0393 (7)
H80.16180.48600.43290.047*
C90.13797 (14)0.2722 (6)0.3111 (2)0.0420 (7)
H90.17950.17640.32000.050*
C100.08711 (14)0.2228 (6)0.2274 (2)0.0429 (7)
H100.09520.09610.18010.051*
C110.02709 (13)0.3575 (5)0.2156 (2)0.0351 (7)
H11−0.00650.32290.15990.042*
C120.01350 (12)0.5483 (5)0.28448 (18)0.0300 (6)
C13−0.04932 (12)0.6848 (5)0.27515 (19)0.0298 (6)
H13−0.08370.64960.22060.036*
C14−0.06241 (12)0.8710 (5)0.34406 (18)0.0280 (6)
C15−0.19237 (13)1.1049 (5)0.16742 (19)0.0324 (6)
C16−0.24985 (14)0.9892 (5)0.1008 (2)0.0409 (7)
H16A−0.23020.94400.02980.049*
H16B−0.29171.09430.08980.049*
C17−0.27266 (14)0.7749 (5)0.1650 (2)0.0394 (7)
H17A−0.32500.78130.18280.047*
H17B−0.26300.63160.12360.047*
C18−0.22734 (12)0.7812 (5)0.2656 (2)0.0328 (6)
N1−0.17925 (10)0.9652 (4)0.25776 (16)0.0301 (5)
O1−0.16111 (10)1.2847 (4)0.14866 (14)0.0409 (5)
O2−0.23048 (9)0.6519 (4)0.34224 (15)0.0415 (5)
U11U22U33U12U13U23
C10.0272 (12)0.0376 (16)0.0252 (11)−0.0043 (11)0.0015 (9)0.0022 (13)
C20.0324 (13)0.0423 (18)0.0298 (13)0.0020 (12)0.0038 (10)0.0024 (14)
C30.0414 (15)0.0417 (18)0.0278 (12)−0.0020 (13)0.0027 (11)−0.0064 (13)
C40.0360 (14)0.051 (2)0.0253 (12)−0.0075 (13)0.0000 (11)−0.0014 (14)
C50.0294 (12)0.0421 (17)0.0223 (11)−0.0043 (12)0.0000 (10)0.0022 (12)
C60.0275 (12)0.0484 (19)0.0260 (12)−0.0051 (12)−0.0050 (10)0.0036 (14)
C70.0280 (12)0.0402 (18)0.0312 (13)−0.0038 (12)0.0001 (10)0.0069 (13)
C80.0262 (12)0.050 (2)0.0419 (14)−0.0011 (13)−0.0026 (11)0.0111 (15)
C90.0290 (13)0.0429 (19)0.0541 (17)0.0058 (13)0.0047 (13)0.0080 (16)
C100.0365 (15)0.0420 (19)0.0503 (17)0.0007 (14)0.0099 (13)−0.0003 (17)
C110.0320 (14)0.0402 (18)0.0333 (13)−0.0010 (13)0.0013 (10)−0.0016 (13)
C120.0260 (12)0.0353 (17)0.0287 (12)−0.0020 (11)0.0030 (9)0.0051 (13)
C130.0258 (11)0.0403 (18)0.0235 (11)−0.0061 (11)0.0000 (9)0.0032 (13)
C140.0261 (11)0.0361 (16)0.0217 (11)−0.0054 (11)0.0019 (9)0.0022 (12)
C150.0279 (12)0.0426 (17)0.0267 (12)0.0034 (12)0.0039 (9)0.0004 (13)
C160.0381 (13)0.052 (2)0.0326 (12)−0.0054 (14)−0.0045 (10)0.0022 (14)
C170.0344 (13)0.0445 (18)0.0393 (14)−0.0035 (12)−0.0058 (11)0.0011 (14)
C180.0260 (12)0.0367 (16)0.0357 (13)0.0043 (11)0.0009 (10)0.0031 (14)
N10.0257 (9)0.0377 (13)0.0269 (9)0.0010 (9)−0.0007 (8)0.0015 (10)
O10.0431 (10)0.0482 (13)0.0313 (9)−0.0103 (10)0.0025 (8)0.0046 (9)
O20.0349 (9)0.0453 (12)0.0443 (11)−0.0037 (9)−0.0026 (8)0.0134 (10)
C1—C21.352 (4)C10—C111.359 (4)
C1—C141.430 (3)C10—H100.9500
C1—N11.440 (3)C11—C121.418 (4)
C2—C31.423 (4)C11—H110.9500
C2—H20.9500C12—C131.405 (3)
C3—C41.355 (4)C13—C141.395 (3)
C3—H30.9500C13—H130.9500
C4—C51.424 (4)C15—O11.209 (3)
C4—H40.9500C15—N11.404 (3)
C5—C61.395 (4)C15—C161.501 (4)
C5—C141.443 (3)C16—C171.531 (4)
C6—C71.390 (4)C16—H16A0.9900
C6—H60.9500C16—H16B0.9900
C7—C81.429 (4)C17—C181.505 (3)
C7—C121.432 (3)C17—H17A0.9900
C8—C91.357 (4)C17—H17B0.9900
C8—H80.9500C18—O21.211 (3)
C9—C101.430 (4)C18—N11.386 (3)
C9—H90.9500
C2—C1—C14122.1 (2)C12—C11—H11119.3
C2—C1—N1119.5 (2)C13—C12—C11122.1 (2)
C14—C1—N1118.4 (2)C13—C12—C7119.2 (2)
C1—C2—C3120.6 (3)C11—C12—C7118.7 (2)
C1—C2—H2119.7C14—C13—C12121.6 (2)
C3—C2—H2119.7C14—C13—H13119.2
C4—C3—C2119.6 (3)C12—C13—H13119.2
C4—C3—H3120.2C13—C14—C1123.9 (2)
C2—C3—H3120.2C13—C14—C5119.1 (2)
C3—C4—C5121.7 (2)C1—C14—C5117.0 (2)
C3—C4—H4119.2O1—C15—N1124.4 (2)
C5—C4—H4119.2O1—C15—C16127.7 (2)
C6—C5—C4122.2 (2)N1—C15—C16107.9 (2)
C6—C5—C14118.8 (2)C15—C16—C17105.4 (2)
C4—C5—C14119.0 (2)C15—C16—H16A110.7
C7—C6—C5122.2 (2)C17—C16—H16A110.7
C7—C6—H6118.9C15—C16—H16B110.7
C5—C6—H6118.9C17—C16—H16B110.7
C6—C7—C8122.4 (2)H16A—C16—H16B108.8
C6—C7—C12119.1 (2)C18—C17—C16105.2 (2)
C8—C7—C12118.4 (3)C18—C17—H17A110.7
C9—C8—C7121.0 (3)C16—C17—H17A110.7
C9—C8—H8119.5C18—C17—H17B110.7
C7—C8—H8119.5C16—C17—H17B110.7
C8—C9—C10120.5 (3)H17A—C17—H17B108.8
C8—C9—H9119.8O2—C18—N1123.9 (2)
C10—C9—H9119.8O2—C18—C17127.8 (2)
C11—C10—C9119.8 (3)N1—C18—C17108.3 (2)
C11—C10—H10120.1C18—N1—C15112.7 (2)
C9—C10—H10120.1C18—N1—C1123.5 (2)
C10—C11—C12121.5 (3)C15—N1—C1123.7 (2)
C10—C11—H11119.3
C14—C1—C2—C3−0.6 (4)C2—C1—C14—C13−176.7 (2)
N1—C1—C2—C3−179.1 (2)N1—C1—C14—C131.8 (3)
C1—C2—C3—C4−1.4 (4)C2—C1—C14—C51.9 (3)
C2—C3—C4—C51.9 (4)N1—C1—C14—C5−179.5 (2)
C3—C4—C5—C6178.3 (3)C6—C5—C14—C13−1.4 (3)
C3—C4—C5—C14−0.4 (4)C4—C5—C14—C13177.3 (2)
C4—C5—C6—C7−177.9 (2)C6—C5—C14—C1179.8 (2)
C14—C5—C6—C70.8 (4)C4—C5—C14—C1−1.4 (3)
C5—C6—C7—C8−178.1 (3)O1—C15—C16—C17−177.3 (2)
C5—C6—C7—C120.4 (4)N1—C15—C16—C173.5 (3)
C6—C7—C8—C9179.4 (3)C15—C16—C17—C180.6 (3)
C12—C7—C8—C90.9 (4)C16—C17—C18—O2175.4 (3)
C7—C8—C9—C100.4 (4)C16—C17—C18—N1−4.5 (3)
C8—C9—C10—C11−1.0 (4)O2—C18—N1—C15−172.7 (2)
C9—C10—C11—C120.3 (4)C17—C18—N1—C157.2 (3)
C10—C11—C12—C13−178.2 (3)O2—C18—N1—C13.1 (4)
C10—C11—C12—C71.1 (4)C17—C18—N1—C1−177.0 (2)
C6—C7—C12—C13−0.9 (3)O1—C15—N1—C18173.9 (2)
C8—C7—C12—C13177.6 (2)C16—C15—N1—C18−6.9 (3)
C6—C7—C12—C11179.9 (2)O1—C15—N1—C1−1.8 (4)
C8—C7—C12—C11−1.6 (4)C16—C15—N1—C1177.4 (2)
C11—C12—C13—C14179.4 (2)C2—C1—N1—C18−107.2 (3)
C7—C12—C13—C140.2 (3)C14—C1—N1—C1874.2 (3)
C12—C13—C14—C1179.6 (2)C2—C1—N1—C1568.1 (3)
C12—C13—C14—C50.9 (3)C14—C1—N1—C15−110.5 (3)
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.952.383.234 (3)149
C6—H6···O1ii0.952.493.357 (3)152
C9—H9···O2iii0.952.533.465 (3)167
C13—H13···O1iv0.952.703.471 (3)139
C17—H17A···Cg2v0.992.923.709 (3)138
Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C7–C12 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C2—H2⋯O2i0.952.383.234 (3)149
C6—H6⋯O1ii0.952.493.357 (3)152
C9—H9⋯O2iii0.952.533.465 (3)167
C13—H13⋯O1iv0.952.703.471 (3)139
C17—H17A⋯Cg2v0.992.923.709 (3)138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

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