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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 11| November 2015| Page o872
https://doi.org/10.1107/S2056989015019313

Crystal structure of di­ethyl (E)-2-[(benzo­furan-2-yl)methyl­­idene]succinate

Marie-Luis Schirmer,a Anke Spannenberga and Thomas Wernera*

aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
*Correspondence e-mail: Thomas.Werner@catalysis.de

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 6 October 2015; accepted 12 October 2015; online 24 October 2015)

The title compound, C17H18O5, was synthesized by a base-free catalytic Wittig reaction. The mol­ecule consists of a diethyl itaconate unit, which is connected via the C=C double bond to a benzo­furan moiety. The benzo­furan ring system (r.m.s. deviation = 0.007 Å) forms dihedral angles of 79.58 (4) and 12.12 (10)° with the mean planes through the cis and trans eth­oxy­carbonyl groups, respectively. An intra­molecular C—H⋯O hydrogen bond involving the O atom of the benzo­furan moiety is observed. In the crystal, mol­ecules are linked into ribbons running parallel to the b axis by C—H⋯O hydrogen bonds.

CCDC reference: 1430813

Similar articles

1. Related literature

For the synthesis of the title compound and related structures, see: Schirmer et al. (2015[Schirmer, M.-L., Adomeit, S. & Werner, T. (2015). Org. Lett. 17, 3078-3081.]). For related crystal structures of similar compounds corresponding to (benzo­furan)-CH=CR1R2, which only differ in R1 and R2 with at least one electron-withdrawing group, see: Penthala et al. (2012[Penthala, N. R., Parkin, S. & Crooks, P. A. (2012). Acta Cryst. E68, o731.]); Wei et al. (2011[Wei, S., Wei, X.-G., Su, X., You, J. & Ren, Y. (2011). Chem. Eur. J. 17, 5965-5971.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C17H18O5

  • Mr = 302.31

  • Orthorhombic, P 21 21 21

  • a = 7.0974 (4) Å

  • b = 8.0898 (4) Å

  • c = 26.9429 (15) Å

  • V = 1546.97 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 150 K

  • 0.46 × 0.35 × 0.20 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2014[Bruker (2014). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.84, Tmax = 0.98

  • 11102 measured reflections

  • 4020 independent reflections

  • 3645 reflections with I > 2σ(I)

  • Rint = 0.021

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.087

  • S = 1.03

  • 4020 reflections

  • 201 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯O3i 0.95 2.47 3.412 (2) 170
C11—H11A⋯O5ii 0.99 2.52 3.458 (2) 158
C11—H11B⋯O1 0.99 2.30 3.044 (2) 131
Symmetry codes: (i) x+1, y, z; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

Data collection: APEX2 (Bruker, 2014[Bruker (2014). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1430813

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015019313/rz5171sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019313/rz5171Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015019313/rz5171Isup3.cml

checkCIF report


Synthesis and crystallization top

Di­ethyl (E)-2-(benzo­furan-2-yl­methyl­ene) succinate was prepared as previously described by Schirmer et al. (2015). All reagents were purchased from commercial sources and used as received without further purification. The reaction was performed in 5 mL Wheaton screw-top V-Vials® with solid-top cap. The vial was dried in an oven at 120°C before use. Toluene was freshly distilled from sodium/benzo­phenone. Thin layer chromatography was performed on Merck TLC-plates with fluorescence indication (silica type 60, F254), spots were visualized using UV-light. Flash chromatography was performed using silica with a grain size of 40–63 µm from Macherey-Nagel. Benzo­furan-2-carbaldehyde (151 mg, 1.03 mmol) was dissolved in toluene (2 mL). Di­ethyl maleate (197 mg, 1.14 mmol), tri-n-butyl­phosphine (11 mg, 0.054 mmol) and phenyl­silane (113 mg, 1.04 mmol) were added successively to the solution. After stirring for 24 h at 125°C, the reaction mixture was cooled to ambient temperature. The crude product was purified by column chromatography over silica (SiO2) with cyclo­hexane/ethyl acetate (20:1 v/v) as eluents. All residues and volatiles were removed in vacuum (≤1 mbar, 60°C) to afford the olefination product (219 mg, 0.724 mmol, yield 70%, E/Z = 95:5) as colourless solid. Single crystals could be obtained by slow evaporation of a petroleum/di­chloro­methane (4:1 v/v) solution.

Refinement top

H atoms were placed in idealized positions with d(C—H) = 0.95 Å (CH), 0.99 Å (CH2), 0.98 Å (CH3) and refined using a riding model with Uiso(H) fixed at 1.2 Ueq(C) for CH and CH2 and 1.5 Ueq(C) for CH3. A rotating model was used for the methyl groups.

Related literature top

For the synthesis of the title compound and related structures, see: Schirmer et al. (2015). For related crystal structures of similar compounds corresponding to (benzofuran)-CH═CR1R2, which only differ in R1 and R2 with at least one electron-withdrawing group, see: Penthala et al. (2012); Wei et al. (2011).

Structure description top

For the synthesis of the title compound and related structures, see: Schirmer et al. (2015). For related crystal structures of similar compounds corresponding to (benzofuran)-CH═CR1R2, which only differ in R1 and R2 with at least one electron-withdrawing group, see: Penthala et al. (2012); Wei et al. (2011).

Synthesis and crystallization top

Di­ethyl (E)-2-(benzo­furan-2-yl­methyl­ene) succinate was prepared as previously described by Schirmer et al. (2015). All reagents were purchased from commercial sources and used as received without further purification. The reaction was performed in 5 mL Wheaton screw-top V-Vials® with solid-top cap. The vial was dried in an oven at 120°C before use. Toluene was freshly distilled from sodium/benzo­phenone. Thin layer chromatography was performed on Merck TLC-plates with fluorescence indication (silica type 60, F254), spots were visualized using UV-light. Flash chromatography was performed using silica with a grain size of 40–63 µm from Macherey-Nagel. Benzo­furan-2-carbaldehyde (151 mg, 1.03 mmol) was dissolved in toluene (2 mL). Di­ethyl maleate (197 mg, 1.14 mmol), tri-n-butyl­phosphine (11 mg, 0.054 mmol) and phenyl­silane (113 mg, 1.04 mmol) were added successively to the solution. After stirring for 24 h at 125°C, the reaction mixture was cooled to ambient temperature. The crude product was purified by column chromatography over silica (SiO2) with cyclo­hexane/ethyl acetate (20:1 v/v) as eluents. All residues and volatiles were removed in vacuum (≤1 mbar, 60°C) to afford the olefination product (219 mg, 0.724 mmol, yield 70%, E/Z = 95:5) as colourless solid. Single crystals could be obtained by slow evaporation of a petroleum/di­chloro­methane (4:1 v/v) solution.

Refinement details top

H atoms were placed in idealized positions with d(C—H) = 0.95 Å (CH), 0.99 Å (CH2), 0.98 Å (CH3) and refined using a riding model with Uiso(H) fixed at 1.2 Ueq(C) for CH and CH2 and 1.5 Ueq(C) for CH3. A rotating model was used for the methyl groups.

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at 30% probability level.
Diethyl (E)-2-[(1-benzofuran-2-yl)methylidene]succinate top
Crystal data top
C17H18O5Dx = 1.298 Mg m−3
Mr = 302.31Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4958 reflections
a = 7.0974 (4) Åθ = 2.6–28.6°
b = 8.0898 (4) ŵ = 0.10 mm−1
c = 26.9429 (15) ÅT = 150 K
V = 1546.97 (14) Å3Prism, colourless
Z = 40.46 × 0.35 × 0.20 mm
F(000) = 640
Data collection top
Bruker APEXII CCD
diffractometer		4020 independent reflections
Radiation source: fine-focus sealed tube3645 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm-1Rint = 0.021
φ and ω scansθmax = 28.8°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		h = −9→8
Tmin = 0.84, Tmax = 0.98k = −9→10
11102 measured reflectionsl = −35→36
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.0447P)2 + 0.2481P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.25 e Å−3
4020 reflectionsΔρmin = −0.16 e Å−3
201 parametersAbsolute structure: Flack x determined using 1441 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: −0.4 (3)
Crystal data top
C17H18O5V = 1546.97 (14) Å3
Mr = 302.31Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.0974 (4) ŵ = 0.10 mm−1
b = 8.0898 (4) ÅT = 150 K
c = 26.9429 (15) Å0.46 × 0.35 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer		4020 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		3645 reflections with I > 2σ(I)
Tmin = 0.84, Tmax = 0.98Rint = 0.021
11102 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.087Δρmax = 0.25 e Å−3
S = 1.03Δρmin = −0.16 e Å−3
4020 reflectionsAbsolute structure: Flack x determined using 1441 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
201 parametersAbsolute structure parameter: −0.4 (3)
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.1845 (2)0.8258 (2)0.20175 (6)0.0226 (3)
C21.3594 (3)0.9003 (2)0.20151 (7)0.0283 (4)
H21.40740.95510.17300.034*
C31.4612 (3)0.8902 (2)0.24552 (8)0.0317 (4)
H31.58200.94030.24730.038*
C41.3901 (3)0.8079 (2)0.28718 (7)0.0308 (4)
H41.46370.80330.31660.037*
C51.2152 (3)0.7334 (2)0.28647 (6)0.0282 (4)
H51.16770.67770.31490.034*
C61.1097 (2)0.7422 (2)0.24256 (6)0.0235 (3)
C70.9292 (3)0.6833 (2)0.22697 (6)0.0251 (3)
H70.84310.62060.24630.030*
C80.9040 (3)0.7338 (2)0.17946 (6)0.0237 (3)
C90.7443 (3)0.7013 (2)0.14801 (6)0.0231 (3)
H90.65620.62490.16130.028*
C100.6987 (3)0.7607 (2)0.10299 (6)0.0238 (3)
C110.8049 (3)0.8887 (2)0.07369 (6)0.0266 (4)
H11A0.81430.85300.03860.032*
H11B0.93420.89940.08710.032*
C120.7066 (3)1.0538 (2)0.07631 (6)0.0221 (3)
C130.6907 (3)1.3237 (2)0.04296 (7)0.0275 (4)
H13A0.71661.37730.07530.033*
H13B0.55251.31710.03840.033*
C140.7776 (4)1.4218 (3)0.00172 (8)0.0411 (5)
H14A0.91371.43070.00720.062*
H14B0.72191.53260.00100.062*
H14C0.75411.3662−0.03000.062*
C150.5193 (3)0.7059 (2)0.07940 (6)0.0264 (4)
C160.2480 (3)0.5350 (3)0.08479 (7)0.0333 (4)
H16A0.27090.49040.05110.040*
H16B0.15520.62590.08230.040*
C170.1757 (3)0.4019 (3)0.11828 (9)0.0423 (5)
H17A0.26650.31060.11930.063*
H17B0.05470.36120.10570.063*
H17C0.15860.44650.15180.063*
O11.05847 (18)0.82331 (16)0.16268 (4)0.0251 (3)
O20.77290 (18)1.15850 (15)0.04184 (4)0.0255 (3)
O30.5870 (2)1.09132 (17)0.10586 (5)0.0325 (3)
O40.42296 (19)0.59499 (17)0.10627 (5)0.0294 (3)
O50.4678 (2)0.75572 (19)0.03924 (5)0.0382 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0260 (8)0.0202 (8)0.0217 (7)0.0027 (7)0.0028 (6)−0.0030 (6)
C20.0274 (9)0.0263 (9)0.0314 (9)−0.0004 (8)0.0098 (7)−0.0024 (7)
C30.0213 (8)0.0279 (9)0.0460 (10)0.0003 (8)0.0010 (8)−0.0071 (8)
C40.0287 (9)0.0290 (9)0.0349 (9)0.0047 (8)−0.0086 (7)−0.0045 (8)
C50.0316 (9)0.0282 (9)0.0247 (8)0.0011 (8)−0.0019 (7)0.0020 (7)
C60.0244 (8)0.0210 (8)0.0250 (8)0.0004 (7)0.0018 (6)−0.0007 (7)
C70.0263 (8)0.0256 (8)0.0234 (7)−0.0035 (8)−0.0011 (6)0.0041 (7)
C80.0273 (9)0.0205 (8)0.0232 (7)−0.0006 (7)0.0013 (6)0.0011 (6)
C90.0272 (8)0.0196 (8)0.0227 (7)−0.0003 (7)−0.0006 (6)0.0014 (6)
C100.0307 (9)0.0203 (8)0.0205 (7)0.0061 (7)0.0005 (6)−0.0011 (6)
C110.0345 (9)0.0251 (9)0.0202 (7)0.0088 (8)0.0052 (7)0.0034 (7)
C120.0271 (9)0.0218 (8)0.0176 (7)0.0003 (7)−0.0019 (6)−0.0007 (6)
C130.0286 (9)0.0196 (8)0.0343 (9)0.0029 (7)0.0057 (7)0.0000 (7)
C140.0496 (13)0.0254 (10)0.0483 (12)0.0056 (10)0.0184 (10)0.0096 (9)
C150.0338 (9)0.0224 (9)0.0230 (8)0.0098 (7)−0.0032 (7)−0.0045 (6)
C160.0259 (9)0.0382 (11)0.0356 (10)0.0064 (9)−0.0093 (8)−0.0103 (8)
C170.0294 (10)0.0500 (14)0.0475 (12)−0.0045 (10)−0.0053 (9)−0.0038 (10)
O10.0295 (6)0.0262 (6)0.0197 (5)−0.0021 (6)0.0032 (5)0.0010 (5)
O20.0296 (7)0.0208 (6)0.0261 (6)0.0035 (5)0.0068 (5)0.0031 (5)
O30.0433 (8)0.0269 (7)0.0272 (6)0.0057 (6)0.0126 (6)0.0008 (5)
O40.0296 (7)0.0320 (7)0.0266 (6)0.0006 (6)−0.0073 (5)−0.0028 (5)
O50.0503 (9)0.0375 (8)0.0267 (6)0.0075 (7)−0.0135 (6)0.0018 (6)
Geometric parameters (Å, º) top
C1—C21.380 (3)C11—H11A0.9900
C1—O11.381 (2)C11—H11B0.9900
C1—C61.396 (2)C12—O31.203 (2)
C2—C31.391 (3)C12—O21.342 (2)
C2—H20.9500C13—O21.459 (2)
C3—C41.399 (3)C13—C141.498 (3)
C3—H30.9500C13—H13A0.9900
C4—C51.380 (3)C13—H13B0.9900
C4—H40.9500C14—H14A0.9800
C5—C61.402 (2)C14—H14B0.9800
C5—H50.9500C14—H14C0.9800
C6—C71.430 (2)C15—O51.211 (2)
C7—C81.355 (2)C15—O41.340 (2)
C7—H70.9500C16—O41.453 (2)
C8—O11.389 (2)C16—C171.496 (3)
C8—C91.439 (2)C16—H16A0.9900
C9—C101.344 (2)C16—H16B0.9900
C9—H90.9500C17—H17A0.9800
C10—C151.491 (3)C17—H17B0.9800
C10—C111.504 (3)C17—H17C0.9800
C11—C121.509 (2)
C2—C1—O1125.84 (16)H11A—C11—H11B108.1
C2—C1—C6123.88 (16)O3—C12—O2123.10 (16)
O1—C1—C6110.28 (15)O3—C12—C11125.51 (16)
C1—C2—C3115.95 (17)O2—C12—C11111.37 (14)
C1—C2—H2122.0O2—C13—C14107.76 (15)
C3—C2—H2122.0O2—C13—H13A110.2
C2—C3—C4121.64 (17)C14—C13—H13A110.2
C2—C3—H3119.2O2—C13—H13B110.2
C4—C3—H3119.2C14—C13—H13B110.2
C5—C4—C3121.42 (17)H13A—C13—H13B108.5
C5—C4—H4119.3C13—C14—H14A109.5
C3—C4—H4119.3C13—C14—H14B109.5
C4—C5—C6118.00 (17)H14A—C14—H14B109.5
C4—C5—H5121.0C13—C14—H14C109.5
C6—C5—H5121.0H14A—C14—H14C109.5
C1—C6—C5119.10 (16)H14B—C14—H14C109.5
C1—C6—C7105.72 (15)O5—C15—O4123.46 (18)
C5—C6—C7135.18 (16)O5—C15—C10122.67 (18)
C8—C7—C6107.16 (16)O4—C15—C10113.86 (15)
C8—C7—H7126.4O4—C16—C17107.07 (16)
C6—C7—H7126.4O4—C16—H16A110.3
C7—C8—O1111.12 (16)C17—C16—H16A110.3
C7—C8—C9127.21 (17)O4—C16—H16B110.3
O1—C8—C9121.66 (14)C17—C16—H16B110.3
C10—C9—C8130.98 (17)H16A—C16—H16B108.6
C10—C9—H9114.5C16—C17—H17A109.5
C8—C9—H9114.5C16—C17—H17B109.5
C9—C10—C15118.98 (17)H17A—C17—H17B109.5
C9—C10—C11126.78 (17)C16—C17—H17C109.5
C15—C10—C11114.12 (15)H17A—C17—H17C109.5
C10—C11—C12110.69 (15)H17B—C17—H17C109.5
C10—C11—H11A109.5C1—O1—C8105.71 (13)
C12—C11—H11A109.5C12—O2—C13115.07 (13)
C10—C11—H11B109.5C15—O4—C16116.38 (14)
C12—C11—H11B109.5
O1—C1—C2—C3178.71 (17)C9—C10—C11—C12−103.4 (2)
C6—C1—C2—C3−0.8 (3)C15—C10—C11—C1272.54 (18)
C1—C2—C3—C40.5 (3)C10—C11—C12—O315.9 (3)
C2—C3—C4—C5−0.1 (3)C10—C11—C12—O2−165.74 (14)
C3—C4—C5—C60.0 (3)C9—C10—C15—O5178.99 (17)
C2—C1—C6—C50.7 (3)C11—C10—C15—O52.7 (2)
O1—C1—C6—C5−178.89 (15)C9—C10—C15—O4−2.1 (2)
C2—C1—C6—C7−179.37 (17)C11—C10—C15—O4−178.38 (15)
O1—C1—C6—C71.0 (2)C2—C1—O1—C8179.37 (17)
C4—C5—C6—C1−0.3 (3)C6—C1—O1—C8−1.04 (19)
C4—C5—C6—C7179.9 (2)C7—C8—O1—C10.65 (19)
C1—C6—C7—C8−0.6 (2)C9—C8—O1—C1−178.34 (16)
C5—C6—C7—C8179.3 (2)O3—C12—O2—C130.7 (2)
C6—C7—C8—O10.0 (2)C11—C12—O2—C13−177.72 (14)
C6—C7—C8—C9178.90 (17)C14—C13—O2—C12−178.92 (16)
C7—C8—C9—C10171.75 (19)O5—C15—O4—C16−0.2 (3)
O1—C8—C9—C10−9.4 (3)C10—C15—O4—C16−179.08 (14)
C8—C9—C10—C15−178.91 (17)C17—C16—O4—C15174.43 (16)
C8—C9—C10—C11−3.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O3i0.952.473.412 (2)170
C11—H11A···O5ii0.992.523.458 (2)158
C11—H11B···O10.992.303.044 (2)131
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+3/2, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O3i0.952.473.412 (2)170
C11—H11A···O5ii0.992.523.458 (2)158
C11—H11B···O10.992.303.044 (2)131
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+3/2, −z.
 

References

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ISSN: 2056-9890
Volume 71| Part 11| November 2015| Page o872
https://doi.org/10.1107/S2056989015019313
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