organic compounds
E)-3-[(4-nitrophenoxy)methyl]-4-phenylbut-3-en-2-one
of (3aDepartmento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, bDepartmento de Física, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, cInstituto de Química, Universidade Estadual de Campinas, CP 6154, 13083-970 Campinas, SP, Brazil, dPrograma de Pós Graduacão em Biotecnologia, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, and eDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: julio@power.ufscar.br
In the title compound, C17H15NO4, the conformation about the C=C double bond [1.348 (2) Å] is E with the ketone group almost co-planar [C—C—C—C torsion angle = 7.2 (2)°] but the phenyl group twisted away [C—C—C—C = 160.93 (17)°]. The terminal aromatic rings are almost perpendicular to each other [dihedral angle = 81.61 (9)°] giving the molecule an overall U-shape. The crystal packing feature benzene-C—H⋯O(ketone) contacts that lead to supramolecular helical chains along the b axis. These are connected by π–π interactions between benzene and phenyl rings [inter-centroid distance = 3.6648 (14) Å], resulting in the formation of a supramolecular layer in the bc plane.
Keywords: crystal structure; hydrogen bonding; π–π interactions.
CCDC reference: 1018885
1. Related literature
For background to biotransformations mediated by Saccharomyces cerevisiae, see: Rodrigues et al. (2004); de Paula et al. (2013).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (Chemaxon, 2010) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 1018885
10.1107/S1600536814018327/hg5405sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814018327/hg5405Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814018327/hg5405Isup3.cml
As part of a continuing interest in biotransformations mediated by Saccharomyces cerevisiae, such as the bio-reduction of α-haloketones and enones (Rodrigues et al., 2004), the title compound, (3E)-3-[(4-nitrophenoxy)methyl]-4-phenylbut-3-en-2- one, was synthesised to be used as a substrate in order to compare its behaviour with that of 3-halomethyl-4-phenyl-3-buten-2-ones analogues (de Paula et al., 2013). Herein, the determination and spectroscopic details are described.
The conformation about the ethene bond in the title compound, Fig. 1, is E. The ketone group is almost co-planar with the double bond as seen in the C11—C8—C9—C10 torsion angle of 7.2 (2)° but the phenyl group is twisted away [C8—C11—C12—C17 160.93 (17)°]. The nitro group is co-planar with the benzene ring to which it is attached [O3—N—C4—C5 = 177.32 (17)°]. The terminal aromatic rings are almost perpendicular [dihedral angle = 81.61 (9)°] to each other so that overall the molecule has the shape of the letter U.
In the crystal packing, C5—H···O2 contacts, Table 1, lead to supramolecular helical chains along the b axis and these are connected by π—π interactions between benzene and phenyl rings [inter-centroid distance = 3.6648 (14) Å; inter-planar angle = 2.70 (9)° for x, 3/2-y, -1/2+z] to form a supramolecular layer in the bc plane, Fig. 2.
Potassium carbonate (1.66 g, 12 mmol) was added to a solution of 4-nitrophenol (1.53 g, 11 mmol) and 3-bromomethyl-4-phenyl-3-buten-2-one (2.39 g, 10 mmol) in acetone (10 mL). The reaction mixture was stirred for 6 h. Then, water (100 mL) was added and the product extracted with dichloromethane (3 x 50 mL). The organic layer was washed with brine, and dried over sodium sulfate. The solvent was removed under reduced pressure and the product purified by δ 2.54 (3H, s), 4.93 (2H, s), 6.99-8.21 (9H, m), 7.92 (1H, s). 13C NMR (CDCl3, 100 MHz) δ 26.0, 62.3, 114.9, 125.9, 128.9, 129.6, 130.1, 134.1, 135.0, 141.8, 146.3, 163.5, 198.2. ESI±HRMS ((M+H)+) calcd.: 298.1079; found: 298.1049.
(hexane/ethyl acetate, 8:2) to afford 3-[(4-nitrophenoxy)methyl]-4-phenyl-3-buten-2-one as a colourless solid. The product was recrystallized by slow evaporation of a 1:4 mixture of hexane and dichloromethane. The crystallised isomer, was shown by crystallography to be the E isomer; M.pt: 398.6–399.6 K. 1H NMR (CDCl3, 400 MHz):Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (Chemaxon, 2010) and publCIF (Westrip, 2010).C17H15NO4 | F(000) = 624 |
Mr = 297.30 | Dx = 1.323 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3883 reflections |
a = 12.769 (3) Å | θ = 2.7–25.1° |
b = 9.4607 (2) Å | µ = 0.10 mm−1 |
c = 13.0022 (4) Å | T = 290 K |
β = 108.145 (1)° | Irregular, colourless |
V = 1492.6 (4) Å3 | 0.52 × 0.23 × 0.12 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 2667 independent reflections |
Radiation source: fine-focus sealed tube | 2118 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω and ϕ scans | θmax = 25.2°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→15 |
Tmin = 0.686, Tmax = 0.745 | k = −11→8 |
9377 measured reflections | l = −15→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0515P)2 + 0.3426P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2667 reflections | Δρmax = 0.16 e Å−3 |
201 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0115 (17) |
C17H15NO4 | V = 1492.6 (4) Å3 |
Mr = 297.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.769 (3) Å | µ = 0.10 mm−1 |
b = 9.4607 (2) Å | T = 290 K |
c = 13.0022 (4) Å | 0.52 × 0.23 × 0.12 mm |
β = 108.145 (1)° |
Bruker Kappa APEXII CCD diffractometer | 2667 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2118 reflections with I > 2σ(I) |
Tmin = 0.686, Tmax = 0.745 | Rint = 0.021 |
9377 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.16 e Å−3 |
2667 reflections | Δρmin = −0.12 e Å−3 |
201 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.18817 (9) | 0.97520 (13) | 0.36449 (8) | 0.0543 (3) | |
O2 | 0.07283 (12) | 1.20609 (17) | 0.47397 (12) | 0.0841 (5) | |
O3 | 0.28681 (13) | 1.06055 (17) | −0.07967 (11) | 0.0831 (5) | |
O4 | 0.16374 (15) | 0.90131 (18) | −0.12490 (11) | 0.0920 (5) | |
N | 0.22052 (14) | 0.98328 (17) | −0.05788 (12) | 0.0623 (4) | |
C1 | 0.19856 (12) | 0.98711 (17) | 0.26230 (12) | 0.0448 (4) | |
C2 | 0.27428 (14) | 1.07139 (18) | 0.23691 (13) | 0.0522 (4) | |
H2 | 0.3210 | 1.1291 | 0.2893 | 0.063* | |
C3 | 0.28067 (14) | 1.06981 (18) | 0.13101 (14) | 0.0538 (4) | |
H3 | 0.3328 | 1.1257 | 0.1139 | 0.065* | |
C4 | 0.21123 (13) | 0.98717 (17) | 0.05269 (12) | 0.0483 (4) | |
C5 | 0.13386 (14) | 0.90499 (19) | 0.07617 (13) | 0.0541 (4) | |
H5 | 0.0858 | 0.8499 | 0.0227 | 0.065* | |
C6 | 0.12779 (14) | 0.90476 (19) | 0.18155 (13) | 0.0528 (4) | |
H6 | 0.0755 | 0.8485 | 0.1981 | 0.063* | |
C7 | 0.24741 (14) | 1.07108 (18) | 0.44897 (12) | 0.0503 (4) | |
H7A | 0.2314 | 1.1681 | 0.4251 | 0.060* | |
H7B | 0.3261 | 1.0557 | 0.4664 | 0.060* | |
C8 | 0.21127 (13) | 1.04372 (17) | 0.54754 (12) | 0.0473 (4) | |
C9 | 0.11652 (14) | 1.13064 (19) | 0.55156 (14) | 0.0559 (4) | |
C10 | 0.07616 (17) | 1.1245 (2) | 0.64904 (16) | 0.0726 (6) | |
H10A | 0.0178 | 1.1918 | 0.6405 | 0.109* | |
H10B | 0.1358 | 1.1466 | 0.7131 | 0.109* | |
H10C | 0.0492 | 1.0313 | 0.6555 | 0.109* | |
C11 | 0.25497 (13) | 0.94713 (18) | 0.62529 (12) | 0.0475 (4) | |
H11 | 0.2227 | 0.9440 | 0.6803 | 0.057* | |
C12 | 0.34410 (13) | 0.84741 (17) | 0.63703 (12) | 0.0459 (4) | |
C13 | 0.38193 (14) | 0.80114 (19) | 0.55154 (14) | 0.0550 (4) | |
H13 | 0.3484 | 0.8336 | 0.4815 | 0.066* | |
C14 | 0.46774 (15) | 0.7087 (2) | 0.57213 (15) | 0.0612 (5) | |
H14 | 0.4936 | 0.6793 | 0.5162 | 0.073* | |
C15 | 0.51684 (15) | 0.65826 (19) | 0.67625 (16) | 0.0611 (5) | |
H15 | 0.5762 | 0.5964 | 0.6894 | 0.073* | |
C16 | 0.47913 (15) | 0.69833 (19) | 0.76078 (15) | 0.0608 (5) | |
H16 | 0.5117 | 0.6624 | 0.8300 | 0.073* | |
C17 | 0.39348 (15) | 0.79129 (18) | 0.74136 (13) | 0.0531 (4) | |
H17 | 0.3673 | 0.8180 | 0.7977 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0564 (7) | 0.0642 (7) | 0.0451 (6) | −0.0149 (6) | 0.0200 (5) | −0.0061 (5) |
O2 | 0.0779 (10) | 0.0976 (11) | 0.0751 (9) | 0.0393 (9) | 0.0214 (7) | 0.0182 (8) |
O3 | 0.0911 (11) | 0.0998 (11) | 0.0756 (9) | −0.0136 (9) | 0.0507 (8) | 0.0119 (8) |
O4 | 0.1264 (13) | 0.1010 (12) | 0.0552 (8) | −0.0303 (11) | 0.0376 (8) | −0.0145 (8) |
N | 0.0741 (11) | 0.0658 (10) | 0.0540 (9) | 0.0029 (9) | 0.0300 (8) | 0.0076 (8) |
C1 | 0.0415 (8) | 0.0499 (9) | 0.0447 (8) | 0.0009 (7) | 0.0157 (7) | 0.0023 (7) |
C2 | 0.0462 (9) | 0.0575 (10) | 0.0518 (9) | −0.0100 (8) | 0.0135 (7) | −0.0011 (8) |
C3 | 0.0481 (9) | 0.0578 (10) | 0.0591 (10) | −0.0071 (8) | 0.0221 (8) | 0.0081 (8) |
C4 | 0.0495 (9) | 0.0511 (9) | 0.0481 (8) | 0.0033 (8) | 0.0208 (7) | 0.0057 (7) |
C5 | 0.0525 (10) | 0.0609 (10) | 0.0489 (9) | −0.0106 (8) | 0.0160 (7) | −0.0052 (8) |
C6 | 0.0478 (9) | 0.0622 (10) | 0.0518 (9) | −0.0138 (8) | 0.0203 (7) | −0.0042 (8) |
C7 | 0.0500 (9) | 0.0507 (9) | 0.0492 (9) | −0.0047 (8) | 0.0139 (7) | −0.0037 (7) |
C8 | 0.0444 (9) | 0.0505 (9) | 0.0458 (8) | −0.0007 (7) | 0.0124 (7) | −0.0064 (7) |
C9 | 0.0490 (10) | 0.0609 (11) | 0.0543 (10) | 0.0056 (9) | 0.0111 (8) | −0.0054 (8) |
C10 | 0.0601 (12) | 0.0882 (15) | 0.0759 (12) | 0.0178 (11) | 0.0303 (10) | −0.0007 (11) |
C11 | 0.0457 (9) | 0.0556 (9) | 0.0421 (8) | −0.0020 (8) | 0.0149 (7) | −0.0065 (7) |
C12 | 0.0434 (9) | 0.0458 (8) | 0.0475 (8) | −0.0036 (7) | 0.0127 (7) | −0.0038 (7) |
C13 | 0.0553 (10) | 0.0597 (10) | 0.0502 (9) | 0.0060 (9) | 0.0166 (8) | −0.0012 (8) |
C14 | 0.0585 (11) | 0.0613 (11) | 0.0695 (11) | 0.0063 (9) | 0.0282 (9) | −0.0033 (9) |
C15 | 0.0475 (10) | 0.0535 (10) | 0.0817 (13) | 0.0032 (8) | 0.0193 (9) | 0.0038 (9) |
C16 | 0.0577 (11) | 0.0582 (11) | 0.0610 (10) | 0.0024 (9) | 0.0104 (8) | 0.0111 (8) |
C17 | 0.0568 (10) | 0.0517 (10) | 0.0506 (9) | −0.0025 (8) | 0.0164 (7) | 0.0007 (7) |
O1—C1 | 1.3804 (17) | C8—C11 | 1.348 (2) |
O1—C7 | 1.4436 (19) | C8—C9 | 1.477 (2) |
O2—C9 | 1.220 (2) | C9—C10 | 1.511 (3) |
O3—N | 1.217 (2) | C10—H10A | 0.9600 |
O4—N | 1.222 (2) | C10—H10B | 0.9600 |
N—C4 | 1.479 (2) | C10—H10C | 0.9600 |
C1—C2 | 1.371 (2) | C11—C12 | 1.449 (2) |
C1—C6 | 1.391 (2) | C11—H11 | 0.9300 |
C2—C3 | 1.405 (2) | C12—C17 | 1.409 (2) |
C2—H2 | 0.9300 | C12—C13 | 1.412 (2) |
C3—C4 | 1.368 (2) | C13—C14 | 1.362 (2) |
C3—H3 | 0.9300 | C13—H13 | 0.9300 |
C4—C5 | 1.364 (2) | C14—C15 | 1.388 (3) |
C5—C6 | 1.396 (2) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | C15—C16 | 1.383 (3) |
C6—H6 | 0.9300 | C15—H15 | 0.9300 |
C7—C8 | 1.514 (2) | C16—C17 | 1.364 (2) |
C7—H7A | 0.9700 | C16—H16 | 0.9300 |
C7—H7B | 0.9700 | C17—H17 | 0.9300 |
C1—O1—C7 | 119.76 (12) | O2—C9—C8 | 117.72 (16) |
O3—N—O4 | 121.10 (16) | O2—C9—C10 | 121.91 (16) |
O3—N—C4 | 118.91 (16) | C8—C9—C10 | 120.37 (15) |
O4—N—C4 | 119.97 (15) | C9—C10—H10A | 109.5 |
C2—C1—O1 | 124.46 (14) | C9—C10—H10B | 109.5 |
C2—C1—C6 | 119.02 (14) | H10A—C10—H10B | 109.5 |
O1—C1—C6 | 116.50 (13) | C9—C10—H10C | 109.5 |
C1—C2—C3 | 119.38 (15) | H10A—C10—H10C | 109.5 |
C1—C2—H2 | 120.3 | H10B—C10—H10C | 109.5 |
C3—C2—H2 | 120.3 | C8—C11—C12 | 130.43 (15) |
C4—C3—C2 | 120.91 (15) | C8—C11—H11 | 114.8 |
C4—C3—H3 | 119.5 | C12—C11—H11 | 114.8 |
C2—C3—H3 | 119.5 | C17—C12—C13 | 118.71 (15) |
C5—C4—C3 | 120.38 (15) | C17—C12—C11 | 116.61 (14) |
C5—C4—N | 119.08 (15) | C13—C12—C11 | 124.66 (14) |
C3—C4—N | 120.53 (15) | C14—C13—C12 | 119.73 (16) |
C4—C5—C6 | 119.06 (15) | C14—C13—H13 | 120.1 |
C4—C5—H5 | 120.5 | C12—C13—H13 | 120.1 |
C6—C5—H5 | 120.5 | C13—C14—C15 | 120.28 (17) |
C1—C6—C5 | 121.22 (15) | C13—C14—H14 | 119.9 |
C1—C6—H6 | 119.4 | C15—C14—H14 | 119.9 |
C5—C6—H6 | 119.4 | C16—C15—C14 | 121.17 (17) |
O1—C7—C8 | 108.12 (13) | C16—C15—H15 | 119.4 |
O1—C7—H7A | 110.1 | C14—C15—H15 | 119.4 |
C8—C7—H7A | 110.1 | C17—C16—C15 | 119.14 (17) |
O1—C7—H7B | 110.1 | C17—C16—H16 | 120.4 |
C8—C7—H7B | 110.1 | C15—C16—H16 | 120.4 |
H7A—C7—H7B | 108.4 | C16—C17—C12 | 120.90 (16) |
C11—C8—C9 | 120.21 (15) | C16—C17—H17 | 119.5 |
C11—C8—C7 | 125.92 (15) | C12—C17—H17 | 119.5 |
C9—C8—C7 | 113.82 (14) | ||
C7—O1—C1—C2 | 10.0 (2) | O1—C7—C8—C9 | −90.67 (16) |
C7—O1—C1—C6 | −171.34 (14) | C11—C8—C9—O2 | −172.68 (17) |
O1—C1—C2—C3 | 176.97 (15) | C7—C8—C9—O2 | 5.0 (2) |
C6—C1—C2—C3 | −1.7 (2) | C11—C8—C9—C10 | 7.2 (2) |
C1—C2—C3—C4 | 1.1 (3) | C7—C8—C9—C10 | −175.10 (16) |
C2—C3—C4—C5 | 0.3 (3) | C9—C8—C11—C12 | 177.64 (16) |
C2—C3—C4—N | −178.36 (15) | C7—C8—C11—C12 | 0.2 (3) |
O3—N—C4—C5 | 177.32 (17) | C8—C11—C12—C17 | 160.93 (17) |
O4—N—C4—C5 | −4.2 (3) | C8—C11—C12—C13 | −20.7 (3) |
O3—N—C4—C3 | −4.0 (3) | C17—C12—C13—C14 | −2.8 (3) |
O4—N—C4—C3 | 174.52 (17) | C11—C12—C13—C14 | 178.89 (16) |
C3—C4—C5—C6 | −1.0 (3) | C12—C13—C14—C15 | 1.0 (3) |
N—C4—C5—C6 | 177.68 (15) | C13—C14—C15—C16 | 1.0 (3) |
C2—C1—C6—C5 | 1.0 (3) | C14—C15—C16—C17 | −1.3 (3) |
O1—C1—C6—C5 | −177.76 (15) | C15—C16—C17—C12 | −0.6 (3) |
C4—C5—C6—C1 | 0.4 (3) | C13—C12—C17—C16 | 2.6 (2) |
C1—O1—C7—C8 | 174.07 (13) | C11—C12—C17—C16 | −178.98 (16) |
O1—C7—C8—C11 | 86.91 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O2i | 0.93 | 2.45 | 3.140 (2) | 131 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O2i | 0.93 | 2.45 | 3.140 (2) | 131 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
Acknowledgements
We thank Professor Regina H. A. Santos from IQSC–USP for the data collection. The Brazilian agencies CNPq (305626/2013–2 to JZ-S), CAPES (808/2009 to JZ-S) and FAPESP (2012/22524–9 to SHM) are acknowledged for financial support.
References
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