Methyl (E)-3-(5-cyano-2-fur­yl)-2-phenyl­acrylate

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.

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

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Computing details

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

Crystal data

C15H11NO3	F(000) = 528
Mr = 253.25	Dx = 1.289 Mg m^−3
Monoclinic, P21/c	Melting point: 358 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.2701 (5) Å	Cell parameters from 4964 reflections
b = 19.948 (2) Å	θ = 2.4–28.9°
c = 10.672 (1) Å	µ = 0.09 mm^−1
β = 102.180 (8)°	T = 293 K
V = 1304.8 (2) Å^3	Prism, colourless
Z = 4	0.46 × 0.41 × 0.38 mm

Data collection

Oxford Diffraction Xcalibur2 diffractometer	2918 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 28.0°, θmin = 4.3°
ω scans	h = −8→8
16533 measured reflections	k = −26→26
3138 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: difference Fourier map
wR(F^2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 0.3164P] where P = (Fo^2 + 2Fc^2)/3
3138 reflections	(Δ/σ)max = 0.001
205 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	1.6961 (3)	0.50750 (10)	0.3800 (2)	0.0918 (6)
O1	1.21538 (17)	0.42841 (5)	0.26277 (11)	0.0515 (3)
O2	0.3984 (2)	0.30190 (6)	−0.00806 (15)	0.0757 (4)
O3	0.4870 (2)	0.40807 (6)	0.03430 (13)	0.0668 (4)
C1	1.4112 (2)	0.41414 (8)	0.34229 (15)	0.0490 (4)
C2	1.4195 (3)	0.34994 (8)	0.38060 (16)	0.0521 (4)
C3	1.2185 (3)	0.32118 (8)	0.32163 (15)	0.0491 (4)
C4	1.0982 (2)	0.36966 (7)	0.25061 (14)	0.0438 (3)
C5	1.5678 (3)	0.46658 (9)	0.36372 (18)	0.0620 (4)
C6	0.8832 (2)	0.37541 (7)	0.16988 (15)	0.0469 (3)
C7	0.7433 (2)	0.32587 (7)	0.12510 (14)	0.0431 (3)
C8	0.5262 (2)	0.34250 (8)	0.04422 (14)	0.0475 (3)
C9	0.2818 (3)	0.42785 (11)	−0.0468 (2)	0.0759 (6)
H9A	0.2923	0.4248	−0.1350	0.114*
H9B	0.2488	0.4732	−0.0274	0.114*
H9C	0.1680	0.3987	−0.0317	0.114*
C10	0.7903 (2)	0.25307 (7)	0.14432 (14)	0.0433 (3)
C11	0.9504 (3)	0.22286 (8)	0.09217 (17)	0.0528 (4)
C12	0.9901 (3)	0.15485 (9)	0.10667 (19)	0.0601 (4)
C13	0.8715 (3)	0.11639 (9)	0.17296 (19)	0.0626 (5)
C14	0.7123 (4)	0.14569 (9)	0.2259 (2)	0.0682 (5)
C15	0.6711 (3)	0.21355 (9)	0.21171 (18)	0.0593 (4)
H2	1.539 (3)	0.3284 (11)	0.441 (2)	0.075 (6)*
H3	1.173 (3)	0.2772 (10)	0.3290 (17)	0.060 (5)*
H6	0.834 (3)	0.4215 (9)	0.1477 (16)	0.056 (5)*
H11	1.033 (3)	0.2500 (10)	0.0467 (18)	0.066 (6)*
H12	1.103 (3)	0.1354 (11)	0.070 (2)	0.075 (6)*
H13	0.895 (3)	0.0691 (11)	0.1790 (19)	0.071 (6)*
H14	0.624 (4)	0.1183 (13)	0.272 (2)	0.102 (8)*
H15	0.558 (4)	0.2329 (12)	0.246 (2)	0.092 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0766 (11)	0.0746 (12)	0.1183 (16)	−0.0307 (10)	0.0074 (11)	−0.0052 (11)
O1	0.0480 (6)	0.0378 (5)	0.0647 (7)	−0.0040 (4)	0.0025 (5)	0.0010 (4)
O2	0.0558 (7)	0.0552 (7)	0.1032 (10)	−0.0070 (6)	−0.0123 (7)	−0.0103 (7)
O3	0.0558 (7)	0.0465 (6)	0.0857 (9)	0.0051 (5)	−0.0130 (6)	0.0025 (6)
C1	0.0443 (7)	0.0483 (8)	0.0519 (8)	−0.0032 (6)	0.0046 (6)	−0.0057 (6)
C2	0.0511 (8)	0.0470 (8)	0.0533 (8)	0.0021 (7)	−0.0003 (7)	−0.0013 (6)
C3	0.0532 (8)	0.0377 (7)	0.0534 (8)	−0.0010 (6)	0.0044 (7)	0.0003 (6)
C4	0.0445 (7)	0.0355 (7)	0.0507 (8)	−0.0034 (5)	0.0088 (6)	−0.0031 (6)
C5	0.0565 (10)	0.0558 (10)	0.0703 (11)	−0.0093 (8)	0.0056 (8)	−0.0039 (8)
C6	0.0448 (8)	0.0377 (7)	0.0562 (8)	0.0021 (6)	0.0063 (6)	0.0009 (6)
C7	0.0414 (7)	0.0400 (7)	0.0483 (7)	0.0001 (5)	0.0105 (6)	−0.0025 (6)
C8	0.0451 (8)	0.0444 (8)	0.0521 (8)	−0.0010 (6)	0.0084 (6)	−0.0026 (6)
C9	0.0606 (11)	0.0689 (12)	0.0862 (14)	0.0112 (9)	−0.0118 (10)	0.0155 (10)
C10	0.0422 (7)	0.0377 (7)	0.0493 (7)	−0.0020 (5)	0.0079 (6)	−0.0050 (5)
C11	0.0486 (8)	0.0468 (8)	0.0648 (10)	−0.0012 (7)	0.0162 (7)	−0.0041 (7)
C12	0.0549 (9)	0.0499 (9)	0.0752 (11)	0.0089 (7)	0.0128 (8)	−0.0084 (8)
C13	0.0712 (11)	0.0407 (8)	0.0703 (11)	0.0047 (8)	0.0020 (9)	0.0011 (7)
C14	0.0859 (13)	0.0483 (9)	0.0751 (12)	−0.0056 (9)	0.0277 (10)	0.0075 (8)
C15	0.0659 (11)	0.0487 (9)	0.0706 (11)	−0.0003 (8)	0.0310 (9)	−0.0014 (7)

Geometric parameters (Å, º)

N1—C5	1.134 (2)	C7—C10	1.4874 (19)
O1—C1	1.3672 (18)	C9—H9A	0.9600
O1—C4	1.3749 (17)	C9—H9B	0.9600
O2—C8	1.1917 (18)	C9—H9C	0.9600
O3—C8	1.3309 (19)	C10—C11	1.384 (2)
O3—C9	1.445 (2)	C10—C15	1.387 (2)
C1—C2	1.342 (2)	C11—C12	1.382 (2)
C1—C5	1.420 (2)	C11—H11	0.95 (2)
C2—C3	1.406 (2)	C12—C13	1.365 (3)
C2—H2	0.98 (2)	C12—H12	0.96 (2)
C3—C4	1.356 (2)	C13—C14	1.377 (3)
C3—H3	0.93 (2)	C13—H13	0.96 (2)
C4—C6	1.443 (2)	C14—C15	1.380 (3)
C6—C7	1.341 (2)	C14—H14	0.98 (3)
C6—H6	0.982 (18)	C15—H15	0.95 (2)
C7—C8	1.487 (2)
C1—O1—C4	105.86 (11)	O3—C9—H9A	109.5
C8—O3—C9	116.24 (14)	O3—C9—H9B	109.5
C2—C1—O1	111.08 (13)	H9A—C9—H9B	109.5
C2—C1—C5	132.32 (15)	O3—C9—H9C	109.5
O1—C1—C5	116.51 (14)	H9A—C9—H9C	109.5
C1—C2—C3	106.24 (14)	H9B—C9—H9C	109.5
C1—C2—H2	126.6 (12)	C11—C10—C15	118.48 (14)
C3—C2—H2	127.2 (12)	C11—C10—C7	120.60 (14)
C4—C3—C2	107.44 (14)	C15—C10—C7	120.90 (14)
C4—C3—H3	125.1 (12)	C12—C11—C10	120.74 (16)
C2—C3—H3	127.4 (11)	C12—C11—H11	120.7 (12)
C3—C4—O1	109.38 (13)	C10—C11—H11	118.5 (12)
C3—C4—C6	136.91 (14)	C13—C12—C11	120.30 (17)
O1—C4—C6	113.70 (12)	C13—C12—H12	121.0 (13)
N1—C5—C1	178.4 (2)	C11—C12—H12	118.7 (13)
C7—C6—C4	127.79 (14)	C12—C13—C14	119.70 (16)
C7—C6—H6	117.2 (10)	C12—C13—H13	119.6 (12)
C4—C6—H6	115.0 (10)	C14—C13—H13	120.6 (12)
C6—C7—C8	119.50 (13)	C13—C14—C15	120.44 (18)
C6—C7—C10	125.07 (13)	C13—C14—H14	120.3 (15)
C8—C7—C10	115.36 (12)	C15—C14—H14	119.2 (15)
O2—C8—O3	122.41 (14)	C14—C15—C10	120.34 (17)
O2—C8—C7	124.23 (15)	C14—C15—H15	119.7 (15)
O3—C8—C7	113.35 (12)	C10—C15—H15	119.9 (15)
C4—O1—C1—C2	−0.64 (18)	C10—C7—C8—O2	−3.4 (2)
C4—O1—C1—C5	176.35 (14)	C6—C7—C8—O3	−5.7 (2)
O1—C1—C2—C3	0.50 (19)	C10—C7—C8—O3	177.14 (13)
C5—C1—C2—C3	−175.86 (18)	C6—C7—C10—C11	−64.5 (2)
C1—C2—C3—C4	−0.16 (19)	C8—C7—C10—C11	112.55 (16)
C2—C3—C4—O1	−0.23 (18)	C6—C7—C10—C15	117.35 (18)
C2—C3—C4—C6	−178.79 (18)	C8—C7—C10—C15	−65.65 (19)
C1—O1—C4—C3	0.52 (17)	C15—C10—C11—C12	0.2 (2)
C1—O1—C4—C6	179.45 (13)	C7—C10—C11—C12	−178.09 (15)
C3—C4—C6—C7	−11.7 (3)	C10—C11—C12—C13	0.0 (3)
O1—C4—C6—C7	169.78 (15)	C11—C12—C13—C14	−0.2 (3)
C4—C6—C7—C8	179.03 (14)	C12—C13—C14—C15	0.4 (3)
C4—C6—C7—C10	−4.1 (3)	C13—C14—C15—C10	−0.3 (3)
C9—O3—C8—O2	−1.6 (3)	C11—C10—C15—C14	0.0 (3)
C9—O3—C8—C7	177.87 (15)	C7—C10—C15—C14	178.23 (17)
C6—C7—C8—O2	173.79 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2^i	0.93 (2)	2.54 (2)	3.121 (2)	120 (1)
C2—H2···Cg^i	0.98 (2)	2.65 (2)	3.566 (2)	156 (2)
C2—H2···C10^i	0.97 (2)	2.91 (2)	3.846 (2)	163 (2)
C2—H2···C11^i	0.97 (2)	2.93 (2)	3.889 (3)	170 (2)
C2—H2···C12^i	0.97 (2)	3.03 (2)	3.872 (3)	147 (2)
C2—H2···C13^i	0.97 (2)	3.09 (2)	3.807 (3)	132 (2)
C2—H2···C14^i	0.97 (2)	3.06 (2)	3.756 (3)	130 (2)
C2—H2···C15^i	0.97 (2)	2.97 (2)	3.772 (3)	141 (2)

Symmetry code: (i) x+1, −y+1/2, z+1/2.