Crystal structure of (3E)-3-(2,4-di­nitro­phen­oxy­meth­yl)-4-phenyl­but-3-en-2-one

Caracelli, I.; Maganhi, S.H.; Moran, P.J.S.; Paula, B.R.S. de; Delling, F.N.; Tiekink, E.R.T.

doi:10.1107/S1600536814018819

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1051-o1052

doi:10.1107/S1600536814018819

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Crystal structure of (3E)-3-(2,4-dinitrophenoxymethyl)-4-phenylbut-3-en-2-one

Ignez Caracelli,^a ^* Stella H. Maganhi,^a Paulo J. S. Moran,^b Bruno R. S. de Paula,^b Felix N. Delling ^c and Edward R. T. Tiekink ^d

^aBioMat-Departmento de Física, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, ^bInstituto de Química, Universidade Estadual de Campinas, CP 6154, 13083-970 Campinas, SP, Brazil, ^cDepartmento de Qímica, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: ignez@ufscar.br

Edited by P. C. Healy, Griffith University, Australia (Received 15 August 2014; accepted 19 August 2014; online 23 August 2014)

In the title compound, C₁₇H₁₄N₂O₆, the conformation about the C=C double bond [1.345 (2) Å] is E, with the ketone moiety almost coplanar [C—C—C—C torsion angle = 9.5 (2)°] along with the phenyl ring [C—C—C—C = 5.9 (2)°]. The aromatic rings are almost perpendicular to each other [dihedral angle = 86.66 (7)°]. The 4-nitro moiety is approximately coplanar with the benzene ring to which it is attached [O—N—C—C = 4.2 (2)°], whereas the one in the ortho position is twisted [O—N—C—C = 138.28 (13)°]. The molecules associate via C—H⋯O interactions, involving both O atoms from the 2-nitro group, to form a helical supramolecular chain along [010]. Nitro–nitro N⋯O interactions [2.8461 (19) Å] connect the chains into layers that stack along [001].

Keywords: crystal structure; hydrogen bonding; N⋯O interactions.

CCDC reference: 1020026

1. Related literature

For background to biotransformations mediated by Saccharomyces cerevisiae, see: Rodrigues et al. (2004 ); de Paula et al. (2013 ). For a related structure, see: Zukerman-Schpector et al. (2014 ). For interactions between nitro groups, see: Daszkiewicz (2013 ).

2. Experimental

2.1. Crystal data

C₁₇H₁₄N₂O₆
M_r = 342.30
Monoclinic, P 2₁ /c
a = 12.8459 (6) Å
b = 7.6983 (4) Å
c = 19.4283 (8) Å
β = 122.254 (2)°
V = 1624.82 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 290 K
0.66 × 0.45 × 0.28 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.699, T_max = 0.745
10435 measured reflections
2957 independent reflections
2630 reflections with I > 2σ(I)
R_int = 0.019

2.3. Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.101
S = 1.04
2957 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O5ⁱ	0.93	2.41	3.1375 (18)	135
C16—H16⋯O6ⁱⁱ	0.93	2.58	3.292 (3)	134
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ), QMol (Gans & Shalloway, 2001 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1020026

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814018819/hg5406sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018819/hg5406Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018819/hg5406Isup3.cml

checkCIF report

Structural commentary top

In the context of the study of biotransformation reactions mediated by Saccharomyces cerevisiae, such as the bio-reduction of α-haloketones and enones (Rodrigues et al., 2004), the title compound, (3E)-3-(2,4-dinitrophenoxymethyl)-4-phenylbut-3-en-2- one, (I), as well as its 4-nitrophenylmethyl analogue, i.e. (3E)-3-(4-nitrophenoxymethyl)-4-phenylbut-3-en-2-one, (II), (Zukerman-Schpector et al. 2014), were synthesised to be used as substrates in order to compare their behaviour with that of the 3-halomethyl-4-phenyl-3-buten-2-ones analogues (de Paula et al., 2013). Herein, the crystal structure determination and spectroscopic details of (I) are described.

In (I), the conformation about the C═C double bond [1.345 (2) Å] is E. The ketone moiety almost co-planar [C11–C8–C9–C10 torsion angle = 9.5 (2) °] with the double bond but the phenyl ring is twisted [C8–C11–C12–C17 = -150.23 (16)°]. The aromatic rings are almost perpendicular to each other [dihedral angle = 86.66 (7)°]. The p-nitro moiety is approximately co-planar with the benzene ring to which it is attached [O3–N1–C4–C5 = -175.29 (14) °] while the the one in the o-position is twisted [O5–N2–C2–C3 = -40.76 (17)°].

Fig. 2 shows and overlay diagram of (I) and the inverted molecule of (II) (Zukerman-Schpector et al. 2014). Clearly, the two molecules adopt very similar conformations.

In the crystal packing, molecules associate via C—H···O interactions, whereby the O atoms of the o-nitro group interact with H derived from a benzene or a phenyl ring, leading to a supramolecular helical chain along [0 1 0]; Fig. 2. There also N···O5 interactions [2.8461 (19) Å], i.e. nitro···nitro interactions (Daszkiewicz, 2013), that link the chains into a layer. Layers stack along [0 0 1] without specific intermolecular interactions between them, Fig. 3.

Synthesis and crystallization top

Potassium carbonate (232 mg, 2.4 mmol) and 2,4-dinitrophenol (368 mg, 2 mmol) were added to a solution of 4-nitrophenol (1.53 g, 11 mmol) and 3-bromomethyl-4-phenyl-3-buten-2-one (478 mg, 2 mmol) in dry acetone (4 mL). The reaction mixture was stirred for 16 hours and the filtered. The solvent was evaporated and the residue was purified by column chromatography (hexane/EtOAc, 80:20) to afford the product as a colourless solid in 75% yield. The product was recrystallized by slow evaporation of a 2:1 dichloromethane/hexane mixture. M.pt: 442.2–442.8 K. ¹H NMR (CD₂Cl₂, 400 MHz): δ 2.52 (3H, s), 5.12 (2H, s), 7.41 (d, 1H, J = 9.2 Hz), 7.43-7.56 (5H, m), 7.99 (1H, s), 8.42 (dd, 1H, J = 2.8, 9.2 Hz), 8.72 (d, 1H, J = 2.8 Hz). ¹³C NMR (CD₂Cl₂, 150 MHz): δ 26.2, 64.7, 116.1, 122.3, 129.5, 129.7, 130.2, 130.8, 134.5, 134.6, 139.8, 140.9, 148.1, 157.0, 198.4.

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) = 1.2U_eq(C) and 1.5U_eq(methyl-C).

Related literature top

For background to biotransformations mediated by Saccharomyces cerevisiae, see: Rodrigues et al. (2004); de Paula et al. (2013). For a related structure, see: Zukerman-Schpector et al. (2014). For interactions between nitro groups, see: Daszkiewicz (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), QMol (Gans & Shalloway, 2001) and 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. Overlay diagram of (I), red image, with inverted (II), blue image, drawn so that the C═C—C(phenyl) atoms are overlapped.
	Fig. 3. A view of helical supramolecular chain along [0 1 0]. The C—H···O contacts are shown as orange dashed lines.
	Fig. 4. A view of unit-cell contents in projection down the b axis. The C—H···O and N···O contacts are shown as orange and blue dashed lines, respectively.

(3E)-3-(2,4-Dinitrophenoxymethyl)-4-phenylbut-3-en-2-one top

Crystal data top

C₁₇H₁₄N₂O₆	F(000) = 712
M_r = 342.30	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6161 reflections
a = 12.8459 (6) Å	θ = 2.9–25.3°
b = 7.6983 (4) Å	µ = 0.11 mm⁻¹
c = 19.4283 (8) Å	T = 290 K
β = 122.254 (2)°	Irregular, colourless
V = 1624.82 (14) Å³	0.66 × 0.45 × 0.28 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2957 independent reflections
Radiation source: fine-focus sealed tube	2630 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω and ϕ scans	θ_max = 25.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→15
T_min = 0.699, T_max = 0.745	k = −7→9
10435 measured reflections	l = −23→19

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.047P)² + 0.4196P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2957 reflections	Δρ_max = 0.20 e Å⁻³
228 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0323 (19)

Crystal data top

C₁₇H₁₄N₂O₆	V = 1624.82 (14) Å³
M_r = 342.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.8459 (6) Å	µ = 0.11 mm⁻¹
b = 7.6983 (4) Å	T = 290 K
c = 19.4283 (8) Å	0.66 × 0.45 × 0.28 mm
β = 122.254 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2957 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2630 reflections with I > 2σ(I)
T_min = 0.699, T_max = 0.745	R_int = 0.019
10435 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
2957 reflections	Δρ_min = −0.21 e Å⁻³
228 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
C1	0.93401 (11)	0.15407 (17)	0.37127 (8)	0.0384 (3)
C2	0.99377 (11)	0.00425 (16)	0.36899 (7)	0.0364 (3)
C3	1.08837 (11)	0.01022 (18)	0.35523 (8)	0.0409 (3)
H3	1.1239	−0.0912	0.3510	0.049*
C4	1.12866 (12)	0.17061 (19)	0.34788 (8)	0.0436 (3)
C5	1.07599 (14)	0.3221 (2)	0.35327 (9)	0.0509 (4)
H5	1.1062	0.4292	0.3496	0.061*
C6	0.97836 (14)	0.31403 (18)	0.36410 (10)	0.0494 (4)
H6	0.9418	0.4161	0.3666	0.059*
C7	0.76361 (13)	0.28733 (18)	0.36901 (10)	0.0463 (3)
H7A	0.7331	0.3422	0.3167	0.056*
H7B	0.8140	0.3705	0.4115	0.056*
C8	0.65850 (12)	0.22873 (19)	0.37591 (9)	0.0437 (3)
C9	0.68382 (13)	0.2244 (2)	0.46004 (9)	0.0503 (4)
C10	0.58981 (16)	0.1491 (3)	0.47503 (11)	0.0656 (5)
H10A	0.6229	0.1458	0.5325	0.098*
H10B	0.5694	0.0334	0.4534	0.098*
H10C	0.5171	0.2199	0.4488	0.098*
C11	0.54588 (13)	0.18897 (19)	0.31208 (9)	0.0464 (3)
H11	0.4877	0.1628	0.3251	0.056*
C12	0.50092 (13)	0.18058 (18)	0.22527 (9)	0.0447 (3)
C13	0.57329 (14)	0.1286 (2)	0.19522 (9)	0.0502 (4)
H13	0.6557	0.1012	0.2312	0.060*
C14	0.52360 (15)	0.1174 (2)	0.11257 (10)	0.0568 (4)
H14	0.5729	0.0830	0.0933	0.068*
C15	0.40169 (16)	0.1568 (2)	0.05828 (10)	0.0596 (4)
H15	0.3690	0.1496	0.0026	0.071*
C16	0.32823 (15)	0.2069 (2)	0.08653 (10)	0.0613 (4)
H16	0.2458	0.2337	0.0500	0.074*
C17	0.37725 (14)	0.2172 (2)	0.16927 (10)	0.0539 (4)
H17	0.3268	0.2492	0.1880	0.065*
N1	1.22919 (11)	0.1784 (2)	0.33327 (8)	0.0572 (4)
N2	0.95589 (10)	−0.16711 (15)	0.38003 (7)	0.0443 (3)
O1	0.83551 (8)	0.13359 (12)	0.37729 (6)	0.0459 (3)
O2	0.78088 (11)	0.27977 (19)	0.51669 (7)	0.0716 (4)
O3	1.26869 (11)	0.0420 (2)	0.32347 (8)	0.0767 (4)
O4	1.26880 (12)	0.32170 (19)	0.33128 (9)	0.0825 (4)
O5	0.95090 (13)	−0.28306 (15)	0.33557 (8)	0.0716 (4)
O6	0.93475 (11)	−0.18635 (15)	0.43354 (8)	0.0673 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0332 (6)	0.0384 (7)	0.0442 (7)	−0.0002 (5)	0.0209 (6)	0.0030 (5)
C2	0.0316 (6)	0.0352 (7)	0.0391 (6)	−0.0014 (5)	0.0167 (5)	0.0027 (5)
C3	0.0341 (6)	0.0469 (8)	0.0400 (7)	0.0039 (6)	0.0187 (6)	0.0018 (6)
C4	0.0338 (6)	0.0564 (9)	0.0412 (7)	−0.0039 (6)	0.0204 (6)	0.0042 (6)
C5	0.0478 (8)	0.0461 (8)	0.0605 (9)	−0.0090 (6)	0.0301 (7)	0.0067 (7)
C6	0.0496 (8)	0.0357 (7)	0.0681 (10)	0.0009 (6)	0.0349 (8)	0.0041 (7)
C7	0.0426 (7)	0.0407 (8)	0.0599 (9)	0.0080 (6)	0.0302 (7)	0.0032 (6)
C8	0.0405 (7)	0.0443 (8)	0.0518 (8)	0.0104 (6)	0.0284 (6)	0.0041 (6)
C9	0.0443 (8)	0.0550 (9)	0.0509 (8)	0.0158 (7)	0.0248 (7)	0.0081 (7)
C10	0.0647 (10)	0.0875 (13)	0.0582 (10)	0.0071 (9)	0.0419 (9)	0.0055 (9)
C11	0.0418 (7)	0.0524 (8)	0.0542 (8)	0.0061 (6)	0.0318 (7)	0.0013 (6)
C12	0.0436 (7)	0.0443 (8)	0.0517 (8)	0.0024 (6)	0.0291 (7)	0.0003 (6)
C13	0.0470 (8)	0.0546 (9)	0.0541 (8)	0.0103 (7)	0.0304 (7)	0.0040 (7)
C14	0.0668 (10)	0.0592 (10)	0.0597 (9)	0.0106 (8)	0.0440 (8)	0.0052 (8)
C15	0.0666 (10)	0.0640 (11)	0.0492 (9)	0.0053 (8)	0.0317 (8)	0.0051 (7)
C16	0.0463 (8)	0.0755 (12)	0.0553 (9)	0.0049 (8)	0.0226 (7)	0.0018 (8)
C17	0.0418 (7)	0.0650 (10)	0.0591 (9)	0.0018 (7)	0.0298 (7)	−0.0040 (7)
N1	0.0398 (7)	0.0847 (11)	0.0497 (7)	−0.0076 (7)	0.0256 (6)	0.0055 (7)
N2	0.0342 (6)	0.0364 (6)	0.0536 (7)	0.0010 (5)	0.0177 (5)	0.0058 (5)
O1	0.0380 (5)	0.0394 (5)	0.0685 (6)	0.0048 (4)	0.0339 (5)	0.0072 (4)
O2	0.0542 (7)	0.0928 (10)	0.0513 (7)	0.0044 (6)	0.0170 (6)	0.0071 (6)
O3	0.0611 (7)	0.0984 (10)	0.0919 (9)	0.0169 (7)	0.0550 (7)	0.0151 (8)
O4	0.0699 (8)	0.0988 (11)	0.0971 (10)	−0.0359 (7)	0.0567 (8)	−0.0084 (8)
O5	0.0896 (9)	0.0395 (6)	0.0671 (8)	−0.0070 (6)	0.0294 (7)	−0.0080 (5)
O6	0.0747 (8)	0.0542 (7)	0.0984 (9)	0.0033 (6)	0.0632 (8)	0.0199 (6)

Geometric parameters (Å, º) top

C1—O1	1.3405 (15)	C10—H10A	0.9600
C1—C6	1.3947 (18)	C10—H10B	0.9600
C1—C2	1.3993 (18)	C10—H10C	0.9600
C2—C3	1.3773 (17)	C11—C12	1.464 (2)
C2—N2	1.4610 (16)	C11—H11	0.9300
C3—C4	1.375 (2)	C12—C17	1.394 (2)
C3—H3	0.9300	C12—C13	1.3945 (19)
C4—C5	1.380 (2)	C13—C14	1.378 (2)
C4—N1	1.4638 (17)	C13—H13	0.9300
C5—C6	1.379 (2)	C14—C15	1.376 (2)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—C16	1.376 (2)
C7—O1	1.4565 (16)	C15—H15	0.9300
C7—C8	1.4959 (19)	C16—C17	1.381 (2)
C7—H7A	0.9700	C16—H16	0.9300
C7—H7B	0.9700	C17—H17	0.9300
C8—C11	1.345 (2)	N1—O4	1.2242 (18)
C8—C9	1.487 (2)	N1—O3	1.2242 (19)
C9—O2	1.2176 (19)	N2—O6	1.2156 (16)
C9—C10	1.502 (2)	N2—O5	1.2198 (16)

O1—C1—C6	124.58 (12)	H10A—C10—H10B	109.5
O1—C1—C2	117.72 (11)	C9—C10—H10C	109.5
C6—C1—C2	117.66 (12)	H10A—C10—H10C	109.5
C3—C2—C1	122.31 (12)	H10B—C10—H10C	109.5
C3—C2—N2	117.14 (11)	C8—C11—C12	129.87 (13)
C1—C2—N2	120.55 (11)	C8—C11—H11	115.1
C4—C3—C2	118.04 (12)	C12—C11—H11	115.1
C4—C3—H3	121.0	C17—C12—C13	117.91 (13)
C2—C3—H3	121.0	C17—C12—C11	118.36 (12)
C3—C4—C5	121.58 (12)	C13—C12—C11	123.63 (13)
C3—C4—N1	118.47 (13)	C14—C13—C12	120.53 (14)
C5—C4—N1	119.95 (13)	C14—C13—H13	119.7
C6—C5—C4	119.75 (13)	C12—C13—H13	119.7
C6—C5—H5	120.1	C15—C14—C13	120.61 (14)
C4—C5—H5	120.1	C15—C14—H14	119.7
C5—C6—C1	120.54 (13)	C13—C14—H14	119.7
C5—C6—H6	119.7	C16—C15—C14	119.88 (15)
C1—C6—H6	119.7	C16—C15—H15	120.1
O1—C7—C8	107.14 (11)	C14—C15—H15	120.1
O1—C7—H7A	110.3	C15—C16—C17	119.79 (15)
C8—C7—H7A	110.3	C15—C16—H16	120.1
O1—C7—H7B	110.3	C17—C16—H16	120.1
C8—C7—H7B	110.3	C16—C17—C12	121.26 (14)
H7A—C7—H7B	108.5	C16—C17—H17	119.4
C11—C8—C9	120.33 (12)	C12—C17—H17	119.4
C11—C8—C7	124.35 (13)	O4—N1—O3	123.64 (13)
C9—C8—C7	115.26 (13)	O4—N1—C4	117.88 (15)
O2—C9—C8	120.24 (14)	O3—N1—C4	118.49 (13)
O2—C9—C10	120.09 (14)	O6—N2—O5	124.41 (13)
C8—C9—C10	119.67 (14)	O6—N2—C2	118.65 (12)
C9—C10—H10A	109.5	O5—N2—C2	116.90 (12)
C9—C10—H10B	109.5	C1—O1—C7	117.86 (10)

O1—C1—C2—C3	173.75 (11)	C8—C11—C12—C17	−150.23 (16)
C6—C1—C2—C3	−3.9 (2)	C8—C11—C12—C13	33.5 (2)
O1—C1—C2—N2	−5.24 (18)	C17—C12—C13—C14	1.2 (2)
C6—C1—C2—N2	177.08 (12)	C11—C12—C13—C14	177.53 (15)
C1—C2—C3—C4	3.50 (19)	C12—C13—C14—C15	−0.2 (3)
N2—C2—C3—C4	−177.48 (11)	C13—C14—C15—C16	−0.4 (3)
C2—C3—C4—C5	−0.6 (2)	C14—C15—C16—C17	−0.1 (3)
C2—C3—C4—N1	179.98 (11)	C15—C16—C17—C12	1.1 (3)
C3—C4—C5—C6	−1.8 (2)	C13—C12—C17—C16	−1.7 (2)
N1—C4—C5—C6	177.66 (13)	C11—C12—C17—C16	−178.17 (15)
C4—C5—C6—C1	1.3 (2)	C3—C4—N1—O4	−176.08 (13)
O1—C1—C6—C5	−176.05 (13)	C5—C4—N1—O4	4.5 (2)
C2—C1—C6—C5	1.5 (2)	C3—C4—N1—O3	4.2 (2)
O1—C7—C8—C11	−94.16 (16)	C5—C4—N1—O3	−175.29 (14)
O1—C7—C8—C9	88.75 (14)	C3—C2—N2—O6	137.34 (13)
C11—C8—C9—O2	−171.36 (15)	C1—C2—N2—O6	−43.62 (17)
C7—C8—C9—O2	5.9 (2)	C3—C2—N2—O5	−40.76 (17)
C11—C8—C9—C10	9.5 (2)	C1—C2—N2—O5	138.28 (13)
C7—C8—C9—C10	−173.26 (13)	C6—C1—O1—C7	5.4 (2)
C9—C8—C11—C12	−178.44 (14)	C2—C1—O1—C7	−172.16 (12)
C7—C8—C11—C12	4.6 (2)	C8—C7—O1—C1	178.57 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O5ⁱ	0.93	2.41	3.1375 (18)	135
C16—H16···O6ⁱⁱ	0.93	2.58	3.292 (3)	134

Symmetry codes: (i) x, y+1, z; (ii) −x+1, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O5ⁱ	0.93	2.41	3.1375 (18)	135
C16—H16···O6ⁱⁱ	0.93	2.58	3.292 (3)	134

Symmetry codes: (i) x, y+1, z; (ii) −x+1, 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 (306121/2013-1 to IC), CAPES (808/2009 to IC) and FAPESP (2012/22524-9 to SHM) are acknowledged for financial support.

References

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Volume 70| Part 9| September 2014| Pages o1051-o1052

doi:10.1107/S1600536814018819

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

Crystal structure of (3E)-3-(2,4-di­nitro­phen­­oxy­meth­yl)-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-(2,4-dinitrophenoxymethyl)-4-phenylbut-3-en-2-one