Crystal structure of diethyl (E)-2-[(benzo-furan-2-yl)methyl-idene]succinate.

The title compound, C17H18O5, was synthesized by a base-free catalytic Wittig reaction. The mol-ecule consists of a diethyl itaconate unit, which is connected via the C=C double bond to a benzo-furan moiety. The benzo-furan 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 eth-oxy-carbonyl groups, respectively. An intra-molecular C-H⋯O hydrogen bond involving the O atom of the benzo-furan moiety is observed. In the crystal, mol-ecules are linked into ribbons running parallel to the b axis by C-H⋯O hydrogen bonds.

Related literature

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=CR 1 R 2, which only differ in R 1 and R 2 with at least one electron-withdrawing group, see: Penthala et al. (2012 ▸); Wei et al. (2011 ▸).

Experimental

Crystal data

C17H18O5

M = 302.31

Orthorhombic,

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

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.84, T max = 0.98

11102 measured reflections

4020 independent reflections

3645 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 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

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015019313/rz5171sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015019313/rz5171Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015019313/rz5171Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015019313/rz5171fig1.tif

The mol­ecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at 30% probability level.

CCDC reference: 1430813

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H18O5	Dx = 1.298 Mg m−3
Mr = 302.31	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4958 reflections
a = 7.0974 (4) Å	θ = 2.6–28.6°
b = 8.0898 (4) Å	µ = 0.10 mm−1
c = 26.9429 (15) Å	T = 150 K
V = 1546.97 (14) Å3	Prism, colourless
Z = 4	0.46 × 0.35 × 0.20 mm
F(000) = 640

Bruker APEXII CCD diffractometer	4020 independent reflections
Radiation source: fine-focus sealed tube	3645 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm-1	Rint = 0.021
φ and ω scans	θmax = 28.8°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −9→8
Tmin = 0.84, Tmax = 0.98	k = −9→10
11102 measured reflections	l = −35→36

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-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 = 1.03	Δρmax = 0.25 e Å−3
4020 reflections	Δρmin = −0.16 e Å−3
201 parameters	Absolute structure: Flack x determined using 1441 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.4 (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.

	x	y	z	Uiso*/Ueq
C1	1.1845 (2)	0.8258 (2)	0.20175 (6)	0.0226 (3)
C2	1.3594 (3)	0.9003 (2)	0.20151 (7)	0.0283 (4)
H2	1.4074	0.9551	0.1730	0.034*
C3	1.4612 (3)	0.8902 (2)	0.24552 (8)	0.0317 (4)
H3	1.5820	0.9403	0.2473	0.038*
C4	1.3901 (3)	0.8079 (2)	0.28718 (7)	0.0308 (4)
H4	1.4637	0.8033	0.3166	0.037*
C5	1.2152 (3)	0.7334 (2)	0.28647 (6)	0.0282 (4)
H5	1.1677	0.6777	0.3149	0.034*
C6	1.1097 (2)	0.7422 (2)	0.24256 (6)	0.0235 (3)
C7	0.9292 (3)	0.6833 (2)	0.22697 (6)	0.0251 (3)
H7	0.8431	0.6206	0.2463	0.030*
C8	0.9040 (3)	0.7338 (2)	0.17946 (6)	0.0237 (3)
C9	0.7443 (3)	0.7013 (2)	0.14801 (6)	0.0231 (3)
H9	0.6562	0.6249	0.1613	0.028*
C10	0.6987 (3)	0.7607 (2)	0.10299 (6)	0.0238 (3)
C11	0.8049 (3)	0.8887 (2)	0.07369 (6)	0.0266 (4)
H11A	0.8143	0.8530	0.0386	0.032*
H11B	0.9342	0.8994	0.0871	0.032*
C12	0.7066 (3)	1.0538 (2)	0.07631 (6)	0.0221 (3)
C13	0.6907 (3)	1.3237 (2)	0.04296 (7)	0.0275 (4)
H13A	0.7166	1.3773	0.0753	0.033*
H13B	0.5525	1.3171	0.0384	0.033*
C14	0.7776 (4)	1.4218 (3)	0.00172 (8)	0.0411 (5)
H14A	0.9137	1.4307	0.0072	0.062*
H14B	0.7219	1.5326	0.0010	0.062*
H14C	0.7541	1.3662	−0.0300	0.062*
C15	0.5193 (3)	0.7059 (2)	0.07940 (6)	0.0264 (4)
C16	0.2480 (3)	0.5350 (3)	0.08479 (7)	0.0333 (4)
H16A	0.2709	0.4904	0.0511	0.040*
H16B	0.1552	0.6259	0.0823	0.040*
C17	0.1757 (3)	0.4019 (3)	0.11828 (9)	0.0423 (5)
H17A	0.2665	0.3106	0.1193	0.063*
H17B	0.0547	0.3612	0.1057	0.063*
H17C	0.1586	0.4465	0.1518	0.063*
O1	1.05847 (18)	0.82331 (16)	0.16268 (4)	0.0251 (3)
O2	0.77290 (18)	1.15850 (15)	0.04184 (4)	0.0255 (3)
O3	0.5870 (2)	1.09132 (17)	0.10586 (5)	0.0325 (3)
O4	0.42296 (19)	0.59499 (17)	0.10627 (5)	0.0294 (3)
O5	0.4678 (2)	0.75572 (19)	0.03924 (5)	0.0382 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0260 (8)	0.0202 (8)	0.0217 (7)	0.0027 (7)	0.0028 (6)	−0.0030 (6)
C2	0.0274 (9)	0.0263 (9)	0.0314 (9)	−0.0004 (8)	0.0098 (7)	−0.0024 (7)
C3	0.0213 (8)	0.0279 (9)	0.0460 (10)	0.0003 (8)	0.0010 (8)	−0.0071 (8)
C4	0.0287 (9)	0.0290 (9)	0.0349 (9)	0.0047 (8)	−0.0086 (7)	−0.0045 (8)
C5	0.0316 (9)	0.0282 (9)	0.0247 (8)	0.0011 (8)	−0.0019 (7)	0.0020 (7)
C6	0.0244 (8)	0.0210 (8)	0.0250 (8)	0.0004 (7)	0.0018 (6)	−0.0007 (7)
C7	0.0263 (8)	0.0256 (8)	0.0234 (7)	−0.0035 (8)	−0.0011 (6)	0.0041 (7)
C8	0.0273 (9)	0.0205 (8)	0.0232 (7)	−0.0006 (7)	0.0013 (6)	0.0011 (6)
C9	0.0272 (8)	0.0196 (8)	0.0227 (7)	−0.0003 (7)	−0.0006 (6)	0.0014 (6)
C10	0.0307 (9)	0.0203 (8)	0.0205 (7)	0.0061 (7)	0.0005 (6)	−0.0011 (6)
C11	0.0345 (9)	0.0251 (9)	0.0202 (7)	0.0088 (8)	0.0052 (7)	0.0034 (7)
C12	0.0271 (9)	0.0218 (8)	0.0176 (7)	0.0003 (7)	−0.0019 (6)	−0.0007 (6)
C13	0.0286 (9)	0.0196 (8)	0.0343 (9)	0.0029 (7)	0.0057 (7)	0.0000 (7)
C14	0.0496 (13)	0.0254 (10)	0.0483 (12)	0.0056 (10)	0.0184 (10)	0.0096 (9)
C15	0.0338 (9)	0.0224 (9)	0.0230 (8)	0.0098 (7)	−0.0032 (7)	−0.0045 (6)
C16	0.0259 (9)	0.0382 (11)	0.0356 (10)	0.0064 (9)	−0.0093 (8)	−0.0103 (8)
C17	0.0294 (10)	0.0500 (14)	0.0475 (12)	−0.0045 (10)	−0.0053 (9)	−0.0038 (10)
O1	0.0295 (6)	0.0262 (6)	0.0197 (5)	−0.0021 (6)	0.0032 (5)	0.0010 (5)
O2	0.0296 (7)	0.0208 (6)	0.0261 (6)	0.0035 (5)	0.0068 (5)	0.0031 (5)
O3	0.0433 (8)	0.0269 (7)	0.0272 (6)	0.0057 (6)	0.0126 (6)	0.0008 (5)
O4	0.0296 (7)	0.0320 (7)	0.0266 (6)	0.0006 (6)	−0.0073 (5)	−0.0028 (5)
O5	0.0503 (9)	0.0375 (8)	0.0267 (6)	0.0075 (7)	−0.0135 (6)	0.0018 (6)

C1—C2	1.380 (3)	C11—H11A	0.9900
C1—O1	1.381 (2)	C11—H11B	0.9900
C1—C6	1.396 (2)	C12—O3	1.203 (2)
C2—C3	1.391 (3)	C12—O2	1.342 (2)
C2—H2	0.9500	C13—O2	1.459 (2)
C3—C4	1.399 (3)	C13—C14	1.498 (3)
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.380 (3)	C13—H13B	0.9900
C4—H4	0.9500	C14—H14A	0.9800
C5—C6	1.402 (2)	C14—H14B	0.9800
C5—H5	0.9500	C14—H14C	0.9800
C6—C7	1.430 (2)	C15—O5	1.211 (2)
C7—C8	1.355 (2)	C15—O4	1.340 (2)
C7—H7	0.9500	C16—O4	1.453 (2)
C8—O1	1.389 (2)	C16—C17	1.496 (3)
C8—C9	1.439 (2)	C16—H16A	0.9900
C9—C10	1.344 (2)	C16—H16B	0.9900
C9—H9	0.9500	C17—H17A	0.9800
C10—C15	1.491 (3)	C17—H17B	0.9800
C10—C11	1.504 (3)	C17—H17C	0.9800
C11—C12	1.509 (2)
C2—C1—O1	125.84 (16)	H11A—C11—H11B	108.1
C2—C1—C6	123.88 (16)	O3—C12—O2	123.10 (16)
O1—C1—C6	110.28 (15)	O3—C12—C11	125.51 (16)
C1—C2—C3	115.95 (17)	O2—C12—C11	111.37 (14)
C1—C2—H2	122.0	O2—C13—C14	107.76 (15)
C3—C2—H2	122.0	O2—C13—H13A	110.2
C2—C3—C4	121.64 (17)	C14—C13—H13A	110.2
C2—C3—H3	119.2	O2—C13—H13B	110.2
C4—C3—H3	119.2	C14—C13—H13B	110.2
C5—C4—C3	121.42 (17)	H13A—C13—H13B	108.5
C5—C4—H4	119.3	C13—C14—H14A	109.5
C3—C4—H4	119.3	C13—C14—H14B	109.5
C4—C5—C6	118.00 (17)	H14A—C14—H14B	109.5
C4—C5—H5	121.0	C13—C14—H14C	109.5
C6—C5—H5	121.0	H14A—C14—H14C	109.5
C1—C6—C5	119.10 (16)	H14B—C14—H14C	109.5
C1—C6—C7	105.72 (15)	O5—C15—O4	123.46 (18)
C5—C6—C7	135.18 (16)	O5—C15—C10	122.67 (18)
C8—C7—C6	107.16 (16)	O4—C15—C10	113.86 (15)
C8—C7—H7	126.4	O4—C16—C17	107.07 (16)
C6—C7—H7	126.4	O4—C16—H16A	110.3
C7—C8—O1	111.12 (16)	C17—C16—H16A	110.3
C7—C8—C9	127.21 (17)	O4—C16—H16B	110.3
O1—C8—C9	121.66 (14)	C17—C16—H16B	110.3
C10—C9—C8	130.98 (17)	H16A—C16—H16B	108.6
C10—C9—H9	114.5	C16—C17—H17A	109.5
C8—C9—H9	114.5	C16—C17—H17B	109.5
C9—C10—C15	118.98 (17)	H17A—C17—H17B	109.5
C9—C10—C11	126.78 (17)	C16—C17—H17C	109.5
C15—C10—C11	114.12 (15)	H17A—C17—H17C	109.5
C10—C11—C12	110.69 (15)	H17B—C17—H17C	109.5
C10—C11—H11A	109.5	C1—O1—C8	105.71 (13)
C12—C11—H11A	109.5	C12—O2—C13	115.07 (13)
C10—C11—H11B	109.5	C15—O4—C16	116.38 (14)
C12—C11—H11B	109.5
O1—C1—C2—C3	178.71 (17)	C9—C10—C11—C12	−103.4 (2)
C6—C1—C2—C3	−0.8 (3)	C15—C10—C11—C12	72.54 (18)
C1—C2—C3—C4	0.5 (3)	C10—C11—C12—O3	15.9 (3)
C2—C3—C4—C5	−0.1 (3)	C10—C11—C12—O2	−165.74 (14)
C3—C4—C5—C6	0.0 (3)	C9—C10—C15—O5	178.99 (17)
C2—C1—C6—C5	0.7 (3)	C11—C10—C15—O5	2.7 (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—C7	1.0 (2)	C2—C1—O1—C8	179.37 (17)
C4—C5—C6—C1	−0.3 (3)	C6—C1—O1—C8	−1.04 (19)
C4—C5—C6—C7	179.9 (2)	C7—C8—O1—C1	0.65 (19)
C1—C6—C7—C8	−0.6 (2)	C9—C8—O1—C1	−178.34 (16)
C5—C6—C7—C8	179.3 (2)	O3—C12—O2—C13	0.7 (2)
C6—C7—C8—O1	0.0 (2)	C11—C12—O2—C13	−177.72 (14)
C6—C7—C8—C9	178.90 (17)	C14—C13—O2—C12	−178.92 (16)
C7—C8—C9—C10	171.75 (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—C15	174.43 (16)
C8—C9—C10—C11	−3.1 (3)

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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C2H2O3i	0.95	2.47	3.412(2)	170
C11H11AO5ii	0.99	2.52	3.458(2)	158
C11H11BO1	0.99	2.30	3.044(2)	131

Symmetry codes: (i) ; (ii) .