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In the title compound, C15H11NO3, the dihedral angle between the mean planes of the furan and phenyl rings is 64.7 (1)°. The mol­ecules are linked into infinite chains by C—H...O and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046356/gk2028sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046356/gk2028Isup2.hkl
Contains datablock I

CCDC reference: 629683

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.058
  • wR factor = 0.139
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C5 ... 1.42 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. C10 .. 2.91 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. C11 .. 2.93 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. C12 .. 3.03 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. C13 .. 3.09 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. C14 .. 3.06 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. C15 .. 2.97 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Methyl (E)-3-(5-cyano-2-furyl)-2-phenylacrylate top
Crystal data top
C15H11NO3F(000) = 528
Mr = 253.25Dx = 1.289 Mg m3
Monoclinic, P21/cMelting point: 358 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.2701 (5) ÅCell parameters from 4964 reflections
b = 19.948 (2) Åθ = 2.4–28.9°
c = 10.672 (1) ŵ = 0.09 mm1
β = 102.180 (8)°T = 293 K
V = 1304.8 (2) Å3Prism, colourless
Z = 40.46 × 0.41 × 0.38 mm
Data collection top
Oxford Diffraction Xcalibur2
diffractometer
2918 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Graphite monochromatorθmax = 28.0°, θmin = 4.3°
ω scansh = 88
16533 measured reflectionsk = 2626
3138 independent reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: difference Fourier map
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.055P)2 + 0.3164P]
where P = (Fo2 + 2Fc2)/3
3138 reflections(Δ/σ)max = 0.001
205 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.18 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N11.6961 (3)0.50750 (10)0.3800 (2)0.0918 (6)
O11.21538 (17)0.42841 (5)0.26277 (11)0.0515 (3)
O20.3984 (2)0.30190 (6)0.00806 (15)0.0757 (4)
O30.4870 (2)0.40807 (6)0.03430 (13)0.0668 (4)
C11.4112 (2)0.41414 (8)0.34229 (15)0.0490 (4)
C21.4195 (3)0.34994 (8)0.38060 (16)0.0521 (4)
C31.2185 (3)0.32118 (8)0.32163 (15)0.0491 (4)
C41.0982 (2)0.36966 (7)0.25061 (14)0.0438 (3)
C51.5678 (3)0.46658 (9)0.36372 (18)0.0620 (4)
C60.8832 (2)0.37541 (7)0.16988 (15)0.0469 (3)
C70.7433 (2)0.32587 (7)0.12510 (14)0.0431 (3)
C80.5262 (2)0.34250 (8)0.04422 (14)0.0475 (3)
C90.2818 (3)0.42785 (11)0.0468 (2)0.0759 (6)
H9A0.29230.42480.13500.114*
H9B0.24880.47320.02740.114*
H9C0.16800.39870.03170.114*
C100.7903 (2)0.25307 (7)0.14432 (14)0.0433 (3)
C110.9504 (3)0.22286 (8)0.09217 (17)0.0528 (4)
C120.9901 (3)0.15485 (9)0.10667 (19)0.0601 (4)
C130.8715 (3)0.11639 (9)0.17296 (19)0.0626 (5)
C140.7123 (4)0.14569 (9)0.2259 (2)0.0682 (5)
C150.6711 (3)0.21355 (9)0.21171 (18)0.0593 (4)
H21.539 (3)0.3284 (11)0.441 (2)0.075 (6)*
H31.173 (3)0.2772 (10)0.3290 (17)0.060 (5)*
H60.834 (3)0.4215 (9)0.1477 (16)0.056 (5)*
H111.033 (3)0.2500 (10)0.0467 (18)0.066 (6)*
H121.103 (3)0.1354 (11)0.070 (2)0.075 (6)*
H130.895 (3)0.0691 (11)0.1790 (19)0.071 (6)*
H140.624 (4)0.1183 (13)0.272 (2)0.102 (8)*
H150.558 (4)0.2329 (12)0.246 (2)0.092 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0766 (11)0.0746 (12)0.1183 (16)0.0307 (10)0.0074 (11)0.0052 (11)
O10.0480 (6)0.0378 (5)0.0647 (7)0.0040 (4)0.0025 (5)0.0010 (4)
O20.0558 (7)0.0552 (7)0.1032 (10)0.0070 (6)0.0123 (7)0.0103 (7)
O30.0558 (7)0.0465 (6)0.0857 (9)0.0051 (5)0.0130 (6)0.0025 (6)
C10.0443 (7)0.0483 (8)0.0519 (8)0.0032 (6)0.0046 (6)0.0057 (6)
C20.0511 (8)0.0470 (8)0.0533 (8)0.0021 (7)0.0003 (7)0.0013 (6)
C30.0532 (8)0.0377 (7)0.0534 (8)0.0010 (6)0.0044 (7)0.0003 (6)
C40.0445 (7)0.0355 (7)0.0507 (8)0.0034 (5)0.0088 (6)0.0031 (6)
C50.0565 (10)0.0558 (10)0.0703 (11)0.0093 (8)0.0056 (8)0.0039 (8)
C60.0448 (8)0.0377 (7)0.0562 (8)0.0021 (6)0.0063 (6)0.0009 (6)
C70.0414 (7)0.0400 (7)0.0483 (7)0.0001 (5)0.0105 (6)0.0025 (6)
C80.0451 (8)0.0444 (8)0.0521 (8)0.0010 (6)0.0084 (6)0.0026 (6)
C90.0606 (11)0.0689 (12)0.0862 (14)0.0112 (9)0.0118 (10)0.0155 (10)
C100.0422 (7)0.0377 (7)0.0493 (7)0.0020 (5)0.0079 (6)0.0050 (5)
C110.0486 (8)0.0468 (8)0.0648 (10)0.0012 (7)0.0162 (7)0.0041 (7)
C120.0549 (9)0.0499 (9)0.0752 (11)0.0089 (7)0.0128 (8)0.0084 (8)
C130.0712 (11)0.0407 (8)0.0703 (11)0.0047 (8)0.0020 (9)0.0011 (7)
C140.0859 (13)0.0483 (9)0.0751 (12)0.0056 (9)0.0277 (10)0.0075 (8)
C150.0659 (11)0.0487 (9)0.0706 (11)0.0003 (8)0.0310 (9)0.0014 (7)
Geometric parameters (Å, º) top
N1—C51.134 (2)C7—C101.4874 (19)
O1—C11.3672 (18)C9—H9A0.9600
O1—C41.3749 (17)C9—H9B0.9600
O2—C81.1917 (18)C9—H9C0.9600
O3—C81.3309 (19)C10—C111.384 (2)
O3—C91.445 (2)C10—C151.387 (2)
C1—C21.342 (2)C11—C121.382 (2)
C1—C51.420 (2)C11—H110.95 (2)
C2—C31.406 (2)C12—C131.365 (3)
C2—H20.98 (2)C12—H120.96 (2)
C3—C41.356 (2)C13—C141.377 (3)
C3—H30.93 (2)C13—H130.96 (2)
C4—C61.443 (2)C14—C151.380 (3)
C6—C71.341 (2)C14—H140.98 (3)
C6—H60.982 (18)C15—H150.95 (2)
C7—C81.487 (2)
C1—O1—C4105.86 (11)O3—C9—H9A109.5
C8—O3—C9116.24 (14)O3—C9—H9B109.5
C2—C1—O1111.08 (13)H9A—C9—H9B109.5
C2—C1—C5132.32 (15)O3—C9—H9C109.5
O1—C1—C5116.51 (14)H9A—C9—H9C109.5
C1—C2—C3106.24 (14)H9B—C9—H9C109.5
C1—C2—H2126.6 (12)C11—C10—C15118.48 (14)
C3—C2—H2127.2 (12)C11—C10—C7120.60 (14)
C4—C3—C2107.44 (14)C15—C10—C7120.90 (14)
C4—C3—H3125.1 (12)C12—C11—C10120.74 (16)
C2—C3—H3127.4 (11)C12—C11—H11120.7 (12)
C3—C4—O1109.38 (13)C10—C11—H11118.5 (12)
C3—C4—C6136.91 (14)C13—C12—C11120.30 (17)
O1—C4—C6113.70 (12)C13—C12—H12121.0 (13)
N1—C5—C1178.4 (2)C11—C12—H12118.7 (13)
C7—C6—C4127.79 (14)C12—C13—C14119.70 (16)
C7—C6—H6117.2 (10)C12—C13—H13119.6 (12)
C4—C6—H6115.0 (10)C14—C13—H13120.6 (12)
C6—C7—C8119.50 (13)C13—C14—C15120.44 (18)
C6—C7—C10125.07 (13)C13—C14—H14120.3 (15)
C8—C7—C10115.36 (12)C15—C14—H14119.2 (15)
O2—C8—O3122.41 (14)C14—C15—C10120.34 (17)
O2—C8—C7124.23 (15)C14—C15—H15119.7 (15)
O3—C8—C7113.35 (12)C10—C15—H15119.9 (15)
C4—O1—C1—C20.64 (18)C10—C7—C8—O23.4 (2)
C4—O1—C1—C5176.35 (14)C6—C7—C8—O35.7 (2)
O1—C1—C2—C30.50 (19)C10—C7—C8—O3177.14 (13)
C5—C1—C2—C3175.86 (18)C6—C7—C10—C1164.5 (2)
C1—C2—C3—C40.16 (19)C8—C7—C10—C11112.55 (16)
C2—C3—C4—O10.23 (18)C6—C7—C10—C15117.35 (18)
C2—C3—C4—C6178.79 (18)C8—C7—C10—C1565.65 (19)
C1—O1—C4—C30.52 (17)C15—C10—C11—C120.2 (2)
C1—O1—C4—C6179.45 (13)C7—C10—C11—C12178.09 (15)
C3—C4—C6—C711.7 (3)C10—C11—C12—C130.0 (3)
O1—C4—C6—C7169.78 (15)C11—C12—C13—C140.2 (3)
C4—C6—C7—C8179.03 (14)C12—C13—C14—C150.4 (3)
C4—C6—C7—C104.1 (3)C13—C14—C15—C100.3 (3)
C9—O3—C8—O21.6 (3)C11—C10—C15—C140.0 (3)
C9—O3—C8—C7177.87 (15)C7—C10—C15—C14178.23 (17)
C6—C7—C8—O2173.79 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.93 (2)2.54 (2)3.121 (2)120 (1)
C2—H2···Cgi0.98 (2)2.65 (2)3.566 (2)156 (2)
C2—H2···C10i0.97 (2)2.91 (2)3.846 (2)163 (2)
C2—H2···C11i0.97 (2)2.93 (2)3.889 (3)170 (2)
C2—H2···C12i0.97 (2)3.03 (2)3.872 (3)147 (2)
C2—H2···C13i0.97 (2)3.09 (2)3.807 (3)132 (2)
C2—H2···C14i0.97 (2)3.06 (2)3.756 (3)130 (2)
C2—H2···C15i0.97 (2)2.97 (2)3.772 (3)141 (2)
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

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