Literature DB >> 24098268

2-Benzyl-5-meth-oxy-isoindoline-1,3-dione.

Noemi Vila1, María Carmen Costas-Lago, Pedro Besada, Carmen Terán.   

Abstract

The title N-benzyl-phthalimide derivative, C16H13NO3, consists of two planar moieties, viz. the phthalimide system (r.m.s. deviation = 0.007 Å) and the phenyl ring, which make a dihedral angle of 84.7 (6)°. The meth-oxy group is almost coplanar with the phathalimide ring, as shown by the C-C-O-C torsion angle of -171.5 (2)°. In the crystal, the mol-ecules are self-assembled via non-classical C-H⋯O hydrogen bonds, forming a tape motif along [110].

Entities:  

Year:  2013        PMID： 24098268      PMCID： PMC3790449          DOI： 10.1107/S160053681302638X

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


Related literature

For background to the applications of phthalimide derivatives, see: Luzzio (2005 ▶); Barooah & Baruah (2007 ▶); Sharma et al. (2010 ▶); Warzecha et al. (2006 ▶). For different approaches to synthesize N-benzyl­phthalimides, see: Luzzio (2005 ▶); Cao & Alper (2010 ▶); Vidal et al. (2000 ▶). For the synthesis of the title compound, see: Favor et al. (2008 ▶); Haj-Yehia & Khan (2004 ▶). For related structures, see: Warzecha et al. (2006a ▶,b ▶,c ▶); Jiang et al. (2008 ▶).

Experimental

Crystal data

C16H13NO3 M = 267.27 Monoclinic, a = 8.476 (4) Å b = 5.264 (3) Å c = 28.295 (13) Å β = 93.589 (9)° V = 1260.0 (11) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 100 K 0.49 × 0.13 × 0.07 mm

Data collection

Bruker SMART 1000 CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.954, T max = 0.993 5768 measured reflections 2204 independent reflections 1433 reflections with I > 2σ(I) R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.137 S = 1.00 2204 reflections 183 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.27 e Å−3 Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681302638X/fy2100sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302638X/fy2100Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S160053681302638X/fy2100Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H13NO3F(000) = 560
Mr = 267.27Dx = 1.409 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.476 (4) ÅCell parameters from 1091 reflections
b = 5.264 (3) Åθ = 2.6–24.8°
c = 28.295 (13) ŵ = 0.10 mm−1
β = 93.589 (9)°T = 100 K
V = 1260.0 (11) Å3Prism, colourless
Z = 40.49 × 0.13 × 0.07 mm
Bruker SMART 1000 CCD diffractometer2204 independent reflections
Radiation source: fine-focus sealed tube1433 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
φ and ω scansθmax = 25.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→9
Tmin = 0.954, Tmax = 0.993k = −5→6
5768 measured reflectionsl = −33→31
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.137w = 1/[σ2(Fo2) + (0.0548P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2204 reflectionsΔρmax = 0.30 e Å−3
183 parametersΔρmin = −0.27 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.022 (4)
Experimental. 1H NMR (400 MHz, CDCl3) δ p.p.m.: 7.77 (d, J = 8.3 Hz, 1H, H7), 7.44 (m, 2H, H—Ph), 7.31 (m, 4H, H4, 3xH-Ph), 7.16 (dd, J = 8.3 Hz, 2.3 Hz, 1H, H6), 4.85 (s, 2H, CH2), 3.95 (s, 3H, OCH3). 13C MNR (100 MHz, CDCl3) δ p.p.m.: 167.9 (2xCO), 164.7 (C5), 136.5 (C), 134.7 (C), 128.7 (CH—Ar), 128.6 (CH—Ar), 127.8 (CH—Ar), 125.1 (C7), 124.0 (C), 119.7 (C6), 108.2 (C4), 56.1 (CH3), 41.6 (CH2). EMAR (ESI) calcld. for: [C16H14NO3]+ 268.09682; Found: 268.09697
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
C10.3240 (3)0.6996 (5)0.92388 (10)0.0213 (6)
O10.4087 (2)0.5180 (4)0.91838 (6)0.0267 (5)
N20.2352 (3)0.8192 (4)0.88663 (7)0.0211 (6)
C30.1503 (3)1.0257 (5)0.90228 (10)0.0215 (7)
O30.0646 (2)1.1594 (4)0.87683 (7)0.0288 (5)
C3A0.1874 (3)1.0402 (5)0.95430 (9)0.0195 (6)
C40.1349 (3)1.2090 (5)0.98669 (10)0.0231 (7)
H40.06491.34350.97740.028*
C50.1887 (3)1.1749 (5)1.03403 (9)0.0217 (6)
O50.1292 (2)1.3429 (4)1.06478 (6)0.0270 (5)
C60.2935 (3)0.9800 (5)1.04724 (10)0.0230 (7)
H60.33030.96261.07950.028*
C70.3447 (3)0.8103 (5)1.01369 (10)0.0241 (7)
H70.41470.67541.02270.029*
C7A0.2915 (3)0.8428 (5)0.96708 (9)0.0197 (6)
C80.1941 (3)1.3450 (6)1.11298 (10)0.0310 (8)
H8A0.17161.18251.12810.047*
H8B0.14621.48341.13030.047*
H8C0.30871.37041.11340.047*
C90.2351 (3)0.7371 (5)0.83788 (9)0.0232 (7)
H9A0.13270.78450.82150.028*
H9B0.24320.54950.83720.028*
C100.3673 (3)0.8478 (5)0.81074 (9)0.0195 (6)
C110.3994 (3)0.7401 (5)0.76729 (9)0.0232 (7)
H110.34240.59370.75650.028*
C120.5122 (3)0.8419 (6)0.73974 (10)0.0253 (7)
H120.53130.76730.71010.030*
C130.5972 (3)1.0524 (6)0.75539 (10)0.0281 (7)
H130.67531.12310.73660.034*
C140.5679 (3)1.1605 (5)0.79876 (10)0.0277 (7)
H140.62671.30500.80960.033*
C150.4534 (3)1.0593 (5)0.82639 (10)0.0226 (7)
H150.43401.13480.85600.027*
U11U22U33U12U13U23
C10.0199 (14)0.0202 (15)0.0238 (16)−0.0009 (12)0.0017 (12)0.0003 (12)
O10.0280 (11)0.0264 (11)0.0255 (11)0.0068 (10)0.0011 (9)−0.0021 (9)
N20.0249 (13)0.0229 (13)0.0156 (12)0.0022 (10)0.0021 (10)−0.0003 (10)
C30.0205 (14)0.0225 (15)0.0219 (15)0.0000 (13)0.0047 (12)0.0022 (12)
O30.0307 (11)0.0333 (12)0.0222 (11)0.0097 (9)−0.0004 (9)0.0040 (9)
C3A0.0157 (13)0.0227 (15)0.0201 (15)−0.0023 (11)0.0027 (11)0.0035 (12)
C40.0216 (14)0.0237 (15)0.0245 (16)0.0014 (12)0.0058 (12)0.0017 (12)
C50.0202 (14)0.0248 (15)0.0207 (15)−0.0026 (13)0.0059 (12)−0.0024 (13)
O50.0278 (11)0.0317 (11)0.0213 (11)0.0052 (9)0.0000 (9)−0.0049 (9)
C60.0237 (15)0.0268 (16)0.0182 (15)−0.0041 (13)−0.0001 (12)0.0008 (13)
C70.0224 (15)0.0241 (15)0.0257 (16)−0.0017 (12)0.0001 (12)0.0039 (13)
C7A0.0205 (14)0.0192 (14)0.0197 (15)−0.0022 (12)0.0043 (12)0.0020 (12)
C80.0300 (17)0.0402 (19)0.0231 (16)0.0028 (14)0.0029 (13)−0.0070 (14)
C90.0256 (16)0.0252 (16)0.0190 (15)0.0025 (12)0.0017 (12)−0.0026 (12)
C100.0193 (14)0.0223 (15)0.0167 (14)0.0054 (12)−0.0008 (11)0.0005 (12)
C110.0213 (15)0.0257 (16)0.0223 (16)0.0008 (12)−0.0014 (13)−0.0036 (12)
C120.0244 (15)0.0313 (17)0.0202 (15)0.0030 (13)0.0019 (12)−0.0031 (13)
C130.0240 (15)0.0374 (18)0.0232 (16)−0.0008 (14)0.0044 (13)0.0011 (14)
C140.0279 (16)0.0269 (16)0.0279 (17)−0.0027 (13)−0.0026 (13)0.0001 (14)
C150.0247 (15)0.0254 (16)0.0177 (15)0.0034 (13)0.0015 (12)−0.0017 (12)
C1—O11.211 (3)C8—H8A0.9800
C1—N21.405 (3)C8—H8B0.9800
C1—C7A1.476 (4)C8—H8C0.9800
N2—C31.391 (3)C9—C101.514 (4)
N2—C91.445 (3)C9—H9A0.9900
C3—O31.215 (3)C9—H9B0.9900
C3—C3A1.488 (4)C10—C151.388 (4)
C3A—C41.371 (4)C10—C111.396 (4)
C3A—C7A1.396 (4)C11—C121.379 (4)
C4—C51.399 (4)C11—H110.9500
C4—H40.9500C12—C131.379 (4)
C5—O51.359 (3)C12—H120.9500
C5—C61.393 (4)C13—C141.389 (4)
O5—C81.438 (3)C13—H130.9500
C6—C71.393 (4)C14—C151.390 (4)
C6—H60.9500C14—H140.9500
C7—C7A1.378 (4)C15—H150.9500
C7—H70.9500
O1—C1—N2123.4 (2)O5—C8—H8B109.5
O1—C1—C7A130.7 (2)H8A—C8—H8B109.5
N2—C1—C7A105.9 (2)O5—C8—H8C109.5
C3—N2—C1112.0 (2)H8A—C8—H8C109.5
C3—N2—C9124.6 (2)H8B—C8—H8C109.5
C1—N2—C9123.4 (2)N2—C9—C10114.4 (2)
O3—C3—N2124.5 (3)N2—C9—H9A108.7
O3—C3—C3A129.7 (3)C10—C9—H9A108.7
N2—C3—C3A105.9 (2)N2—C9—H9B108.7
C4—C3A—C7A122.4 (2)C10—C9—H9B108.7
C4—C3A—C3129.6 (2)H9A—C9—H9B107.6
C7A—C3A—C3108.0 (2)C15—C10—C11118.6 (3)
C3A—C4—C5117.2 (2)C15—C10—C9122.5 (2)
C3A—C4—H4121.4C11—C10—C9118.8 (2)
C5—C4—H4121.4C12—C11—C10121.3 (3)
O5—C5—C6124.3 (2)C12—C11—H11119.3
O5—C5—C4114.7 (2)C10—C11—H11119.3
C6—C5—C4121.0 (3)C11—C12—C13119.8 (3)
C5—O5—C8118.5 (2)C11—C12—H12120.1
C5—C6—C7120.7 (2)C13—C12—H12120.1
C5—C6—H6119.6C12—C13—C14119.6 (3)
C7—C6—H6119.6C12—C13—H13120.2
C7A—C7—C6118.4 (3)C14—C13—H13120.2
C7A—C7—H7120.8C13—C14—C15120.6 (3)
C6—C7—H7120.8C13—C14—H14119.7
C7—C7A—C3A120.3 (3)C15—C14—H14119.7
C7—C7A—C1131.5 (2)C10—C15—C14120.0 (3)
C3A—C7A—C1108.3 (2)C10—C15—H15120.0
O5—C8—H8A109.5C14—C15—H15120.0
O1—C1—N2—C3−178.9 (3)C6—C7—C7A—C1179.5 (3)
C7A—C1—N2—C30.3 (3)C4—C3A—C7A—C70.5 (4)
O1—C1—N2—C90.3 (4)C3—C3A—C7A—C7−179.5 (2)
C7A—C1—N2—C9179.5 (2)C4—C3A—C7A—C1−179.7 (2)
C1—N2—C3—O3−179.9 (3)C3—C3A—C7A—C10.3 (3)
C9—N2—C3—O30.9 (4)O1—C1—C7A—C7−1.4 (5)
C1—N2—C3—C3A−0.1 (3)N2—C1—C7A—C7179.4 (3)
C9—N2—C3—C3A−179.3 (2)O1—C1—C7A—C3A178.7 (3)
O3—C3—C3A—C4−0.3 (5)N2—C1—C7A—C3A−0.4 (3)
N2—C3—C3A—C4179.9 (3)C3—N2—C9—C1093.1 (3)
O3—C3—C3A—C7A179.6 (3)C1—N2—C9—C10−86.0 (3)
N2—C3—C3A—C7A−0.1 (3)N2—C9—C10—C15−16.9 (3)
C7A—C3A—C4—C5−0.7 (4)N2—C9—C10—C11166.0 (2)
C3—C3A—C4—C5179.3 (3)C15—C10—C11—C12−1.0 (4)
C3A—C4—C5—O5−178.1 (2)C9—C10—C11—C12176.2 (2)
C3A—C4—C5—C61.1 (4)C10—C11—C12—C130.9 (4)
C6—C5—O5—C89.2 (4)C11—C12—C13—C14−0.2 (4)
C4—C5—O5—C8−171.5 (2)C12—C13—C14—C15−0.3 (4)
O5—C5—C6—C7177.8 (2)C11—C10—C15—C140.5 (4)
C4—C5—C6—C7−1.4 (4)C9—C10—C15—C14−176.6 (2)
C5—C6—C7—C7A1.1 (4)C13—C14—C15—C100.1 (4)
C6—C7—C7A—C3A−0.7 (4)
D—H···AD—HH···AD···AD—H···A
C4—H4···O5i0.952.573.505 (3)168
C7—H7···O1ii0.952.403.247 (3)149
C8—H8B···O3i0.982.593.432 (4)144
C15—H15···N20.952.562.884 (4)100
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C4—H4⋯O5i 0.952.573.505 (3)168
C7—H7⋯O1ii 0.952.403.247 (3)149
C8—H8B⋯O3i 0.982.593.432 (4)144

Symmetry codes: (i) ; (ii) .

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Authors:  U Sharma; P Kumar; N Kumar; B Singh
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4.  2-Benzyl-isoindoline-1,3-dione: a monoclinic polymorph.

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5.  Photoinduced decarboxylative benzylation of phthalimide triplets with phenyl acetates: a mechanistic study.

Authors:  Klaus-Dieter Warzecha; Helmut Görner; Axel G Griesbeck
Journal:  J Phys Chem A       Date:  2006-03-16       Impact factor: 2.781

6.  Structure validation in chemical crystallography.

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