Literature DB >> 22590354

(E)-Ethyl 2-cyano-3-(furan-2-yl)acrylate.

Rajesh G Kalkhambkar, D Gayathri, Vivek K Gupta, Rajni Kant, Yeon Tae Jeong.   

Abstract

There are two independent mol-ecules in the asymmetric unit of the title compound, C(10)H(9)NO(3), in both of which, all non-H atoms except for the methyl C atom lie nearly in the same plane [maximum deviations = 0.094 (3) and 0.043 (2) Å]. In the crystal, each independent mol-ecules is linked by pairs of C-H⋯O inter-actions, generating inversion dimers with R(2) (2)(10) ring motifs.

Entities:  

Year:  2012        PMID： 22590354      PMCID： PMC3344592          DOI： 10.1107/S1600536812016510

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the synthesis of related compounds, see: Yadav et al. (2004 ▶). For related structures, see: Wang & Jian (2008 ▶); Zhang et al. (2009 ▶); Ye et al. (2009 ▶); Yuvaraj et al. (2011 ▶).

Experimental

Crystal data

C10H9NO3 M = 191.18 Monoclinic, a = 4.6611 (2) Å b = 19.8907 (9) Å c = 20.9081 (9) Å β = 91.988 (4)° V = 1937.28 (15) Å3 Z = 8 Mo Kα radiation μ = 0.10 mm−1 T = 293 K 0.30 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.933, T max = 0.990 12870 measured reflections 4568 independent reflections 2407 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.066 wR(F 2) = 0.209 S = 1.04 4568 reflections 253 parameters H-atom parameters constrained Δρmax = 0.26 e Å−3 Δρmin = −0.24 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016510/is5119sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016510/is5119Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812016510/is5119Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C10H9NO3F(000) = 800
Mr = 191.18Dx = 1.311 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4295 reflections
a = 4.6611 (2) Åθ = 3.6–29.1°
b = 19.8907 (9) ŵ = 0.10 mm−1
c = 20.9081 (9) ÅT = 293 K
β = 91.988 (4)°Needle, pale yellow
V = 1937.28 (15) Å30.30 × 0.20 × 0.10 mm
Z = 8
Oxford Diffraction Xcalibur Sapphire3 diffractometer4568 independent reflections
Radiation source: fine-focus sealed tube2407 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 16.1049 pixels mm-1θmax = 29.2°, θmin = 3.6°
ω scansh = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −26→24
Tmin = 0.933, Tmax = 0.990l = −27→27
12870 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0908P)2 + 0.185P] where P = (Fo2 + 2Fc2)/3
4568 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.24 e Å−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.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
O1A1.1671 (4)0.14995 (9)0.41737 (9)0.0642 (5)
O2A0.5561 (4)0.03506 (10)0.58448 (9)0.0724 (6)
O3A0.8013 (4)0.10818 (9)0.64695 (8)0.0617 (5)
N1A1.2730 (5)0.19852 (12)0.56530 (12)0.0695 (7)
C1A0.9635 (5)0.10093 (13)0.41935 (12)0.0524 (6)
C2A0.9058 (6)0.07717 (15)0.35931 (13)0.0658 (8)
H2A0.77470.04370.34780.079*
C3A1.0809 (7)0.11270 (15)0.31803 (14)0.0709 (8)
H3A1.09000.10740.27400.085*
C4A1.2328 (7)0.15591 (16)0.35497 (14)0.0747 (9)
H4A1.36630.18610.33970.090*
C5A0.8457 (5)0.08207 (13)0.47874 (12)0.0520 (6)
H5A0.71040.04770.47610.062*
C6A0.9001 (5)0.10636 (12)0.53795 (11)0.0468 (6)
C7A0.7339 (6)0.07857 (13)0.59153 (12)0.0516 (6)
C8A0.6382 (7)0.08504 (17)0.70119 (14)0.0781 (9)
H8A10.43520.08350.68940.094*
H8A20.69950.04020.71370.094*
C9A0.6886 (10)0.13165 (19)0.75412 (17)0.1063 (13)
H9A10.58200.11730.79020.159*
H9A20.62740.17590.74130.159*
H9A30.88960.13240.76580.159*
C10A1.1070 (6)0.15760 (13)0.55250 (12)0.0511 (6)
O1B1.1874 (4)0.12570 (9)0.88858 (9)0.0650 (5)
O2B0.5452 (4)−0.07433 (10)0.94337 (10)0.0763 (6)
O3B0.7859 (4)−0.11775 (9)0.86263 (10)0.0737 (6)
N1B1.2343 (6)−0.00911 (12)0.79884 (12)0.0752 (8)
C1B0.9833 (5)0.11024 (13)0.93153 (12)0.0526 (6)
C2B0.9368 (6)0.16376 (14)0.96945 (14)0.0654 (8)
H2B0.80810.16591.00240.078*
C3B1.1182 (7)0.21538 (15)0.95001 (15)0.0717 (8)
H3B1.13400.25840.96720.086*
C4B1.2645 (7)0.19017 (15)0.90153 (17)0.0732 (8)
H4B1.40180.21390.87950.088*
C5B0.8538 (5)0.04531 (13)0.93108 (12)0.0545 (7)
H5B0.72220.03840.96290.065*
C6B0.8908 (5)−0.00742 (13)0.89236 (11)0.0492 (6)
C7B0.7208 (6)−0.06891 (14)0.90287 (13)0.0571 (7)
C8B0.6333 (9)−0.18142 (18)0.86891 (18)0.0999 (12)
H8B10.7679−0.21600.88290.120*
H8B20.4903−0.17690.90130.120*
C9B0.4999 (11)−0.2007 (2)0.8116 (2)0.1386 (19)
H9B10.4030−0.24280.81730.208*
H9B20.6412−0.20570.77960.208*
H9B30.3631−0.16710.79810.208*
C10B1.0847 (6)−0.00751 (13)0.84084 (12)0.0541 (7)
U11U22U33U12U13U23
O1A0.0780 (12)0.0690 (13)0.0461 (11)−0.0191 (10)0.0102 (9)−0.0059 (9)
O2A0.0919 (14)0.0708 (13)0.0550 (12)−0.0275 (11)0.0091 (10)0.0000 (10)
O3A0.0759 (12)0.0698 (12)0.0399 (10)−0.0140 (10)0.0093 (8)−0.0011 (8)
N1A0.0813 (16)0.0642 (16)0.0636 (16)−0.0126 (14)0.0113 (13)−0.0078 (12)
C1A0.0597 (15)0.0511 (15)0.0467 (15)0.0011 (12)0.0061 (11)−0.0023 (11)
C2A0.0812 (19)0.0655 (18)0.0510 (16)−0.0147 (15)0.0053 (14)−0.0076 (13)
C3A0.091 (2)0.079 (2)0.0434 (16)−0.0073 (17)0.0117 (15)−0.0046 (14)
C4A0.095 (2)0.081 (2)0.0499 (17)−0.0172 (17)0.0225 (16)−0.0014 (15)
C5A0.0601 (15)0.0480 (15)0.0480 (15)−0.0011 (12)0.0049 (11)−0.0014 (11)
C6A0.0537 (14)0.0419 (14)0.0450 (14)0.0002 (11)0.0042 (11)−0.0007 (10)
C7A0.0632 (16)0.0495 (15)0.0421 (14)−0.0021 (13)0.0044 (11)0.0029 (11)
C8A0.098 (2)0.091 (2)0.0464 (17)−0.0161 (18)0.0209 (15)0.0028 (15)
C9A0.150 (4)0.111 (3)0.060 (2)−0.021 (3)0.036 (2)−0.0106 (19)
C10A0.0634 (15)0.0515 (16)0.0390 (13)0.0055 (13)0.0098 (11)0.0003 (11)
O1B0.0693 (12)0.0633 (13)0.0633 (13)−0.0045 (10)0.0132 (9)−0.0107 (9)
O2B0.0828 (14)0.0810 (14)0.0665 (14)−0.0095 (11)0.0257 (11)0.0105 (11)
O3B0.1015 (15)0.0592 (12)0.0617 (13)−0.0246 (11)0.0199 (11)−0.0061 (10)
N1B0.0915 (18)0.0755 (18)0.0601 (16)−0.0159 (14)0.0255 (14)−0.0079 (13)
C1B0.0568 (15)0.0572 (17)0.0438 (14)0.0064 (13)0.0024 (11)−0.0014 (11)
C2B0.0736 (18)0.0630 (19)0.0596 (18)0.0083 (15)0.0041 (14)−0.0094 (14)
C3B0.085 (2)0.0586 (18)0.071 (2)0.0061 (16)−0.0049 (16)−0.0118 (15)
C4B0.0759 (19)0.0613 (19)0.083 (2)−0.0098 (16)0.0064 (16)−0.0059 (16)
C5B0.0578 (15)0.0630 (18)0.0429 (15)0.0028 (13)0.0027 (11)0.0000 (12)
C6B0.0553 (14)0.0531 (15)0.0392 (13)−0.0010 (12)0.0028 (10)0.0030 (11)
C7B0.0659 (17)0.0623 (17)0.0433 (15)−0.0005 (14)0.0016 (12)0.0049 (13)
C8B0.151 (3)0.075 (2)0.074 (2)−0.051 (2)0.011 (2)0.0059 (18)
C9B0.220 (5)0.098 (3)0.096 (3)−0.083 (3)−0.014 (3)0.009 (2)
C10B0.0702 (17)0.0485 (15)0.0438 (15)−0.0059 (12)0.0039 (12)−0.0017 (11)
O1A—C4A1.356 (3)O1B—C4B1.357 (3)
O1A—C1A1.362 (3)O1B—C1B1.366 (3)
O2A—C7A1.204 (3)O2B—C7B1.203 (3)
O3A—C7A1.328 (3)O3B—C7B1.327 (3)
O3A—C8A1.461 (3)O3B—C8B1.461 (4)
N1A—C10A1.148 (3)N1B—C10B1.140 (3)
C1A—C2A1.360 (3)C1B—C2B1.349 (4)
C1A—C5A1.425 (3)C1B—C5B1.425 (4)
C2A—C3A1.400 (4)C2B—C3B1.399 (4)
C2A—H2A0.9300C2B—H2B0.9300
C3A—C4A1.341 (4)C3B—C4B1.338 (4)
C3A—H3A0.9300C3B—H3B0.9300
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.345 (3)C5B—C6B1.340 (3)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C10A1.429 (4)C6B—C10B1.430 (3)
C6A—C7A1.490 (3)C6B—C7B1.478 (4)
C8A—C9A1.457 (4)C8B—C9B1.385 (5)
C8A—H8A10.9700C8B—H8B10.9700
C8A—H8A20.9700C8B—H8B20.9700
C9A—H9A10.9600C9B—H9B10.9600
C9A—H9A20.9600C9B—H9B20.9600
C9A—H9A30.9600C9B—H9B30.9600
C4A—O1A—C1A105.8 (2)C4B—O1B—C1B105.5 (2)
C7A—O3A—C8A115.1 (2)C7B—O3B—C8B117.1 (2)
C2A—C1A—O1A109.7 (2)C2B—C1B—O1B109.8 (2)
C2A—C1A—C5A130.0 (3)C2B—C1B—C5B130.0 (3)
O1A—C1A—C5A120.3 (2)O1B—C1B—C5B120.3 (2)
C1A—C2A—C3A107.0 (3)C1B—C2B—C3B107.3 (3)
C1A—C2A—H2A126.5C1B—C2B—H2B126.4
C3A—C2A—H2A126.5C3B—C2B—H2B126.4
C4A—C3A—C2A106.0 (3)C4B—C3B—C2B105.9 (3)
C4A—C3A—H3A127.0C4B—C3B—H3B127.1
C2A—C3A—H3A127.0C2B—C3B—H3B127.1
C3A—C4A—O1A111.5 (3)C3B—C4B—O1B111.5 (3)
C3A—C4A—H4A124.3C3B—C4B—H4B124.2
O1A—C4A—H4A124.3O1B—C4B—H4B124.2
C6A—C5A—C1A129.9 (2)C6B—C5B—C1B130.5 (2)
C6A—C5A—H5A115.1C6B—C5B—H5B114.7
C1A—C5A—H5A115.1C1B—C5B—H5B114.7
C5A—C6A—C10A123.8 (2)C5B—C6B—C10B123.7 (2)
C5A—C6A—C7A118.2 (2)C5B—C6B—C7B118.5 (2)
C10A—C6A—C7A118.0 (2)C10B—C6B—C7B117.9 (2)
O2A—C7A—O3A124.5 (2)O2B—C7B—O3B123.8 (3)
O2A—C7A—C6A123.2 (2)O2B—C7B—C6B124.1 (3)
O3A—C7A—C6A112.2 (2)O3B—C7B—C6B112.1 (2)
C9A—C8A—O3A108.3 (3)C9B—C8B—O3B111.6 (3)
C9A—C8A—H8A1110.0C9B—C8B—H8B1109.3
O3A—C8A—H8A1110.0O3B—C8B—H8B1109.3
C9A—C8A—H8A2110.0C9B—C8B—H8B2109.3
O3A—C8A—H8A2110.0O3B—C8B—H8B2109.3
H8A1—C8A—H8A2108.4H8B1—C8B—H8B2108.0
C8A—C9A—H9A1109.5C8B—C9B—H9B1109.5
C8A—C9A—H9A2109.5C8B—C9B—H9B2109.5
H9A1—C9A—H9A2109.5H9B1—C9B—H9B2109.5
C8A—C9A—H9A3109.5C8B—C9B—H9B3109.5
H9A1—C9A—H9A3109.5H9B1—C9B—H9B3109.5
H9A2—C9A—H9A3109.5H9B2—C9B—H9B3109.5
N1A—C10A—C6A178.8 (3)N1B—C10B—C6B177.9 (3)
C4A—O1A—C1A—C2A0.1 (3)C4B—O1B—C1B—C2B0.1 (3)
C4A—O1A—C1A—C5A−179.9 (2)C4B—O1B—C1B—C5B179.8 (2)
O1A—C1A—C2A—C3A0.1 (3)O1B—C1B—C2B—C3B0.0 (3)
C5A—C1A—C2A—C3A−179.9 (3)C5B—C1B—C2B—C3B−179.7 (3)
C1A—C2A—C3A—C4A−0.3 (3)C1B—C2B—C3B—C4B−0.1 (3)
C2A—C3A—C4A—O1A0.4 (4)C2B—C3B—C4B—O1B0.2 (4)
C1A—O1A—C4A—C3A−0.3 (4)C1B—O1B—C4B—C3B−0.2 (3)
C2A—C1A—C5A—C6A−178.9 (3)C2B—C1B—C5B—C6B177.4 (3)
O1A—C1A—C5A—C6A1.1 (4)O1B—C1B—C5B—C6B−2.2 (4)
C1A—C5A—C6A—C10A−2.1 (4)C1B—C5B—C6B—C10B0.5 (4)
C1A—C5A—C6A—C7A177.5 (2)C1B—C5B—C6B—C7B−179.0 (2)
C8A—O3A—C7A—O2A−1.0 (4)C8B—O3B—C7B—O2B−0.2 (4)
C8A—O3A—C7A—C6A177.8 (2)C8B—O3B—C7B—C6B179.4 (3)
C5A—C6A—C7A—O2A0.8 (4)C5B—C6B—C7B—O2B1.7 (4)
C10A—C6A—C7A—O2A−179.5 (2)C10B—C6B—C7B—O2B−177.8 (3)
C5A—C6A—C7A—O3A−178.0 (2)C5B—C6B—C7B—O3B−177.9 (2)
C10A—C6A—C7A—O3A1.6 (3)C10B—C6B—C7B—O3B2.6 (3)
C7A—O3A—C8A—C9A−167.4 (3)C7B—O3B—C8B—C9B125.3 (4)
D—H···AD—HH···AD···AD—H···A
C5A—H5A···O2Ai0.932.403.242 (3)151
C5B—H5B···O2Bii0.932.463.320 (3)153
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C5A—H5A⋯O2Ai0.932.403.242 (3)151
C5B—H5B⋯O2Bii0.932.463.320 (3)153

Symmetry codes: (i) ; (ii) .

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