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

Mrvoš-Sermek, D.; Starčević, K.; Karminski-Zamola, G.

doi:10.1107/S1600536806046356

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

D. Mrvoš-Sermek, K. Starčević and G. Karminski-Zamola

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.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046356/gk2028sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046356/gk2028Isup2.hkl Contains datablock I

CCDC reference: 629683

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (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

C₁₅H₁₁NO₃	F(000) = 528
M_r = 253.25	D_x = 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) Å³	Prism, colourless
Z = 4	0.46 × 0.41 × 0.38 mm

Data collection top

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

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: difference Fourier map
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.055P)² + 0.3164P] where P = (F_o² + 2F_c²)/3
3138 reflections	(Δ/σ)_max = 0.001
205 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93 (2)	2.54 (2)	3.121 (2)	120 (1)
C2—H2···Cgⁱ	0.98 (2)	2.65 (2)	3.566 (2)	156 (2)
C2—H2···C10ⁱ	0.97 (2)	2.91 (2)	3.846 (2)	163 (2)
C2—H2···C11ⁱ	0.97 (2)	2.93 (2)	3.889 (3)	170 (2)
C2—H2···C12ⁱ	0.97 (2)	3.03 (2)	3.872 (3)	147 (2)
C2—H2···C13ⁱ	0.97 (2)	3.09 (2)	3.807 (3)	132 (2)
C2—H2···C14ⁱ	0.97 (2)	3.06 (2)	3.756 (3)	130 (2)
C2—H2···C15ⁱ	0.97 (2)	2.97 (2)	3.772 (3)	141 (2)

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

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Supporting information

Key indicators

checkCIF/PLATON results

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