Crystal structure of (3E)-3-[(4-nitro­phen­oxy)­meth­yl]-4-phenyl­but-3-en-2-one

Zukerman-Schpector, J.; Maganhi, S.H.; Moran, P.J.S.; Paula, B.R.S. de; Nucci Jr, P.R.; Tiekink, E.R.T.

doi:10.1107/S1600536814018327

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1020-o1021

doi:10.1107/S1600536814018327

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Crystal structure of (3E)-3-[(4-nitrophenoxy)methyl]-4-phenylbut-3-en-2-one

Julio Zukerman-Schpector,^a ^* Stella H. Maganhi,^b Paulo J. S. Moran,^c Bruno R. S. de Paula,^c Paulo R. Nucci Jr ^d and Edward R. T. Tiekink ^e

^aDepartmento 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

Edited by P. C. Healy, Griffith University, Australia (Received 10 August 2014; accepted 11 August 2014; online 16 August 2014)

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

C₁₇H₁₅NO₄
M_r = 297.30
Monoclinic, P 2₁ /c
a = 12.769 (3) Å
b = 9.4607 (2) Å
c = 13.0022 (4) Å
β = 108.145 (1)°
V = 1492.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 290 K
0.52 × 0.23 × 0.12 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.686, T_max = 0.745
9377 measured reflections
2667 independent reflections
2118 reflections with I > 2σ(I)
R_int = 0.021

2.3. Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.113
S = 1.06
2667 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: 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

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814018327/hg5405sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018327/hg5405Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018327/hg5405Isup3.cml

checkCIF report

Structural commentary top

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 crystal structure 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 symmetry operation: x, 3/2-y, -1/2+z] to form a supramolecular layer in the bc plane, Fig. 2.

Synthesis and crystallization top

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 column chromatography (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): 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.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with U_iso(H) = 1.2–1.5U_eq(C).

Related literature top

For background to biotransformations mediated by Saccharomyces cerevisiae, see: Rodrigues et al. (2004); de Paula et al. (2013).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top

	Fig. 1. The molecular structure of the title showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of unit-cell contents in projection down the c axis. The C—H···O and π—π contacts are shown as orange and purple dashed lines, respectively.

(I) top

Crystal data top

C₁₇H₁₅NO₄	F(000) = 624
M_r = 297.30	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	2667 independent reflections
Radiation source: fine-focus sealed tube	2118 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω and ϕ scans	θ_max = 25.2°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→15
T_min = 0.686, T_max = 0.745	k = −11→8
9377 measured reflections	l = −15→13

Refinement top

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(F_o²) + (0.0515P)² + 0.3426P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2667 reflections	Δρ_max = 0.16 e Å⁻³
201 parameters	Δρ_min = −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)

Crystal data top

C₁₇H₁₅NO₄	V = 1492.6 (4) Å³
M_r = 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)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2667 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2118 reflections with I > 2σ(I)
T_min = 0.686, T_max = 0.745	R_int = 0.021
9377 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.06	Δρ_max = 0.16 e Å⁻³
2667 reflections	Δρ_min = −0.12 e Å⁻³
201 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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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Volume 70| Part 9| September 2014| Pages o1020-o1021

doi:10.1107/S1600536814018327

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (3E)-3-[(4-nitro­phen­­oxy)­meth­yl]-4-phenyl­but-3-en-2-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (3E)-3-[(4-nitrophenoxy)methyl]-4-phenylbut-3-en-2-one